COMPOUND, MATERIAL FOR ORGANIC ELECTROLUMINESCENT DEVICES, ORGANIC ELECTROLUMINESCENT DEVICE, AND ELECTRONIC APPARATUS

Provided are: a compound capable of further improving the performance of organic EL devices, an organic electroluminescent device having more improved device performance, and an electronic apparatus including such an organic electroluminescent device. Precisely provided are: a compound represented by the following formula (1):   wherein the symbols are as defined in the description, an organic electroluminescent device containing the compound, and an electronic apparatus including such an organic electroluminescent device.

CROSS-REFERENCE TO RELATED APPLICATION

The present application is based on, and claims priority from, Japanese Patent Application No. 2021-029027, filed Feb. 25, 2021. The content of the application is incorporated herein by reference in its entirety.

FIELD OF THE INVENTION

The present invention relates to a compound, a material for organic electroluminescent devices, an organic electroluminescent device, and an electronic apparatus including the organic luminescent device.

BACKGROUND OF THE INVENTION

In general, an organic electroluminescent device (which may be hereinafter referred to as an “organic EL device”) is constituted by an anode, a cathode, and an organic layer intervening between the anode and the cathode. In application of a voltage between both the electrodes, electrons from the cathode side and holes from the anode side are injected into a light emitting region, and the injected electrons and holes are recombined in the light emitting region to generate an excited state, which then returns to the ground state to emit light. Accordingly, development of a material that efficiently transports electrons or holes into the light emitting region, and promotes recombination of the electrons and holes is important for providing a high-performance organic EL device.

PTLs 1 to 5 describe compounds used for a material for organic electroluminescent devices.

CITATION LIST

Patent Literature

Technical Problem

Various compounds for organic EL devices have been reported, but a compound that further enhances the capability of an organic EL device has been still demanded.

The present invention has been made for solving the problem, and an object thereof is to provide a compound that further improves the capability of an organic EL device, an organic EL device having a further improved device capability, and an electronic apparatus including the organic EL device.

Solution to Problem

As a result of the continued investigations by the present inventors on the capabilities of organic EL devices containing the compounds described in PTLs 1 to 5, it has been found that an organic EL device containing a compound represented by the following formula (1) shows a further improved capability.

In one embodiment, the present invention provides a compound represented by the following formula (1):

wherein

the carbon atom ** constitutes a 6-membered ring along with Y1to Y5,

Y1to Y5each independently represent a nitrogen atom or CR, and two or more selected from Y1to Y5are nitrogen atoms, in the case where plural CR's exist, R's in the plural CR's are the same as or different from each other,

R, R1to R6, R7to R10, Ara, and Arbeach independently represent a hydrogen atom or a substituent A, one selected from R7to R10is a single bond bonding to *a,

the substituent A is

a halogen atom,
a nitro group,
a cyano group,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
a group represented by —Si(R901)(R9022)(R903),
a group represented by —O—(R904),
a group represented by —S—(R905),
a group represented by —N(R906)(R907),
a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or
a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

in the case where two or more R901's exist, the two or more R901's are the same as or different from each other,

in the case where two or more R902's exist, the two or more R902's are the same as or different from each other,

in the case where two or more R903's exist, the two or more R903's are the same as or different from each other,

in the case where two or more R904's exist, the two or more R904's are the same as or different from each other,

in the case where two or more R905's exist, the two or more R905's are the same as or different from each other,

in the case where two or more R906's exist, the two or more R906's are the same as or different from each other,

in the case where two or more R907's exist, the two or more R907's are the same as or different from each other,

R1to R6, and R7to R10not bonding to *a do not bond to each other to form a cyclic structure,

in the case where plural CR's exist, two neighboring R's bond to each other to form a substituted or unsubstituted cyclic structure, or do not bond to each other and therefore do not form a cyclic structure,

L1represents a substituted or unsubstituted, (2+p)-valent aromatic hydrocarbon ring having 6 to 12 ring carbon atoms,

L2represents a substituted or unsubstituted, (2+q)-valent aromatic hydrocarbon ring having 6 to 12 ring carbon atoms,

when L1is a (2+p)-valent residue of a naphthalene, L2is not a (2+q)-valent residue of a naphthalene, and when L2is a (2+q)-valent residue of a naphthalene, L1is not a (2+p)-valent residue of a naphthalene,

m represents 0 or 1,

n represents 0 or 1, provided that

when m and n are 0, the carbon ** bonds to *a,

when m is 0 and n is 1, L2bonds to *a and the carbon atom **,

when n is 0 and m is 1, L1bonds to *a and the carbon atom **,

q represents 0, 1, 2 or 3, provided that

when p is 2 or more, the plural Arn's are the same as or different from each other,

when q is 2 or more, the plural Arn's are the same as or different from each other.

In another embodiment, the present invention provides a material for an organic EL device containing the compound represented by the formula (1).

In still another embodiment, the present invention provides an organic electroluminescent device having an anode, a cathode, and organic layers between the anode and the cathode, the organic layers including a light emitting layer, at least one layer of the organic layers containing the compound represented by the formula (1).

In a further embodiment, the present invention provides an electronic apparatus including the organic electroluminescent device.

Advantageous Effects of the Invention

An organic EL device containing the compound represented by the formula (1) shows an improved device capability.

DESCRIPTION OF EMBODIMENTS

Definitions

In the description herein, the hydrogen atom encompasses isotopes thereof having different numbers of neutrons, i.e., a light hydrogen atom (protium), a heavy hydrogen atom (deuterium), and tritium.

In the description herein, the bonding site where the symbol, such as “R”, or “D” representing a deuterium atom is not shown is assumed to have a hydrogen atom, i.e., a protium atom, a deuterium atom, or a tritium atom, bonded thereto.

In the description herein, the number of ring carbon atoms shows the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure including atoms bonded to form a ring (such as a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). In the case where the ring is substituted by a substituent, the carbon atom contained in the substituent is not included in the number of ring carbon atoms. The same definition is applied to the “number of ring carbon atoms” described hereinafter unless otherwise indicated. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. For example, 9,9-diphenylfluorenyl group has 13 ring carbon atoms, and 9,9′-spirobifluorenyl group has 25 ring carbon atoms.

In the case where a benzene ring has, for example, an alkyl group substituted thereon as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the benzene ring. Accordingly, a benzene ring having an alkyl group substituted thereon has 6 ring carbon atoms. In the case where a naphthalene ring has, for example, an alkyl group substituted thereon as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Accordingly, a naphthalene ring having an alkyl group substituted thereon has 10 ring carbon atoms.

In the description herein, the number of ring atoms shows the number of atoms constituting the ring itself of a compound having a structure including atoms bonded to form a ring (such as a monocyclic ring, a condensed ring, and a set of rings) (such as a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). The atom that does not constitute the ring (such as a hydrogen atom terminating the bond of the atom constituting the ring) and, in the case where the ring is substituted by a substituent, the atom contained in the substituent are not included in the number of ring atoms. The same definition is applied to the “number of ring atoms” described hereinafter unless otherwise indicated. For example, a pyridine ring has 6 ring atoms, a quinazoline ring has 10 ring atoms, and a furan ring has 5 ring atoms. For example, the number of hydrogen atoms bonded to a pyridine ring or atoms constituting a substituent is not included in the number of ring atoms of the pyridine ring. Accordingly, a pyridine ring having a hydrogen atom or a substituent bonded thereto has 6 ring atoms. For example, the number of hydrogen atoms bonded to carbon atoms of a quinazoline ring or atoms constituting a substituent is not included in the number of ring atoms of the quinazoline ring. Accordingly, a quinazoline ring having a hydrogen atom or a substituent bonded thereto has 10 ring atoms.

In the description herein, the expression “having XX to YY carbon atoms” in the expression “substituted or unsubstituted ZZ group having XX to YY carbon atoms” means the number of carbon atoms of the unsubstituted ZZ group, and, in the case where the ZZ group is substituted, the number of carbon atoms of the substituent is not included. Herein, “YY” is larger than “XX”, “XX” represents an integer of 1 or more, and “YY” represents an integer of 2 or more.

In the description herein, the expression “having XX to YY atoms” in the expression “substituted or unsubstituted ZZ group having XX to YY atoms” means the number of atoms of the unsubstituted ZZ group, and, in the case where the ZZ group is substituted, the number of atoms of the substituent is not included. Herein, “YY” is larger than “XX”, “XX” represents an integer of 1 or more, and “YY” represents an integer of 2 or more.

In the description herein, an unsubstituted ZZ group means the case where the “substituted or unsubstituted ZZ group” is an “unsubstituted ZZ group”, and a substituted ZZ group means the case where the “substituted or unsubstituted ZZ group” is a “substituted ZZ group”.

In the description herein, the expression “unsubstituted” in the expression “substituted or unsubstituted ZZ group” means that hydrogen atoms in the ZZ group are not substituted by a substituent. The hydrogen atoms in the “unsubstituted ZZ group” each are a protium atom, a deuterium atom, or a tritium atom.

In the description herein, the expression “substituted” in the expression “substituted or unsubstituted ZZ group” means that one or more hydrogen atom in the ZZ group is substituted by a substituent. The expression “substituted” in the expression “BB group substituted by an AA group” similarly means that one or more hydrogen atom in the BB group is substituted by the AA group.

Substituents in Description

The substituents described in the description herein will be explained.

In the description herein, the number of ring carbon atoms of the “unsubstituted aryl group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise indicated in the description.

In the description herein, the number of ring atoms of the “unsubstituted heterocyclic group” is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise indicated in the description.

In the description herein, the number of carbon atoms of the “unsubstituted alkyl group” is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise indicated in the description.

In the description herein, the number of carbon atoms of the “unsubstituted alkenyl group” is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise indicated in the description.

In the description herein, the number of carbon atoms of the “unsubstituted alkynyl group” is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise indicated in the description.

In the description herein, the number of ring carbon atoms of the “unsubstituted cycloalkyl group” is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise indicated in the description.

In the description herein, the number of ring carbon atoms of the “unsubstituted arylene group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise indicated in the description.

In the description herein, the number of ring atoms of the “unsubstituted divalent heterocyclic group” is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise indicated in the description.

In the description herein, the number of carbon atoms of the “unsubstituted alkylene group” is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise indicated in the description.

Substituted or Unsubstituted Aryl Group

In the description herein, specific examples (set of specific examples G1) of the “substituted or unsubstituted aryl group” include the unsubstituted aryl groups (set of specific examples G1A) and the substituted aryl groups (set of specific examples G1B) shown below. (Herein, the unsubstituted aryl group means the case where the “substituted or unsubstituted aryl group” is an “unsubstituted aryl group”, and the substituted aryl group means the case where the “substituted or unsubstituted aryl group” is a “substituted aryl group”.) In the description herein, the simple expression “aryl group” encompasses both the “unsubstituted aryl group” and the “substituted aryl group”.

The “substituted aryl group” means a group formed by substituting one or more hydrogen atom of the “unsubstituted aryl group” by a substituent. Examples of the “substituted aryl group” include groups formed by one or more hydrogen atom of each of the “unsubstituted aryl groups” in the set of specific examples G1A by a substituent, and the examples of the substituted aryl groups in the set of specific examples GIB. The examples of the “unsubstituted aryl group” and the examples of the “substituted aryl group” enumerated herein are mere examples, and the “substituted aryl group” in the description herein encompasses groups formed by substituting a hydrogen atom bonded to the carbon atom of the aryl group itself of each of the “substituted aryl groups” in the set of specific examples G1B by a substituent, and groups formed by substituting a hydrogen atom of the substituent of each of the “substituted aryl groups” in the set of specific examples G1B by a substituent.

Unsubstituted Aryl Group (Set of Specific Examples G1A):

a phenyl group,

a perylenyl group, and

monovalent aryl groups derived by removing one hydrogen atom from each of the ring structures represented by the following general formulae (TEMP-1) to (TEMP-15):

Substituted Aryl Group (Set of Specific Examples G1B):

a naphthylphenyl group, and

groups formed by substituting one or more hydrogen atom of each of monovalent aryl groups derived from the ring structures represented by the general formulae (TEMP-1) to (TEMP-15) by a substituent.

Substituted or Unsubstituted Heterocyclic Group

In the description herein, the “heterocyclic group” means a cyclic group containing at least one hetero atom in the ring atoms. Specific examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom.

In the description herein, the “heterocyclic group” is a monocyclic group or a condensed ring group.

In the description herein, the “heterocyclic group” is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

In the description herein, specific examples (set of specific examples G2) of the “substituted or unsubstituted heterocyclic group” include the unsubstituted heterocyclic groups (set of specific examples G2A) and the substituted heterocyclic groups (set of specific examples G2B) shown below. (Herein, the unsubstituted heterocyclic group means the case where the “substituted or unsubstituted heterocyclic group” is an “unsubstituted heterocyclic group”, and the substituted heterocyclic group means the case where the “substituted or unsubstituted heterocyclic group” is a “substituted heterocyclic group”.) In the description herein, the simple expression “heterocyclic group” encompasses both the “unsubstituted heterocyclic group” and the “substituted heterocyclic group”.

The “substituted heterocyclic group” means a group formed by substituting one or more hydrogen atom of the “unsubstituted heterocyclic group” by a substituent. Specific examples of the “substituted heterocyclic group” include groups formed by substituting a hydrogen atom of each of the “unsubstituted heterocyclic groups” in the set of specific examples G2A by a substituent, and the examples of the substituted heterocyclic groups in the set of specific examples G2B. The examples of the “unsubstituted heterocyclic group” and the examples of the “substituted heterocyclic group” enumerated herein are mere examples, and the “substituted heterocyclic group” in the description herein encompasses groups formed by substituting a hydrogen atom bonded to the ring atom of the heterocyclic group itself of each of the “substituted heterocyclic groups” in the set of specific examples G2B by a substituent, and groups formed by substituting a hydrogen atom of the substituent of each of the “substituted heterocyclic groups” in the set of specific examples G2B by a substituent.

The set of specific examples G2A includes, for example, the unsubstituted heterocyclic group containing a nitrogen atom (set of specific examples G2A1), the unsubstituted heterocyclic group containing an oxygen atom (set of specific examples G2A2), the unsubstituted heterocyclic group containing a sulfur atom (set of specific examples G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from each of the ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (set of specific examples G2A4).

The set of specific examples G2B includes, for example, the substituted heterocyclic groups containing a nitrogen atom (set of specific examples G2B1), the substituted heterocyclic groups containing an oxygen atom (set of specific examples G2B2), the substituted heterocyclic groups containing a sulfur atom (set of specific examples G2B3), and groups formed by substituting one or more hydrogen atom of each of monovalent heterocyclic groups derived from the ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) by a substituent (set of specific examples G2B4).

Unsubstituted Heterocyclic Group Containing Nitrogen Atom (Set of Specific Examples G2A1):

a pyridyl group,

an azacarbazolyl group, and

Unsubstituted Heterocyclic Group Containing Oxygen Atom (Set of Specific Examples G2A2):

an azanaphthobenzofuranyl group, and

Unsubstituted Heterocyclic Group Containing Sulfur Atom (Set of Specific Examples G2A3):

an azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and

Monovalent Heterocyclic Group Derived by Removing One Hydrogen Atom from Ring Structures Represented by General Formulae (TEMP-16) to (TEMP-33) (Set of Specific Examples G2A4)

In the general formulae (TEMP-16) to (TEMP-33), XAand YAeach independently represent an oxygen atom, a sulfur atom, NH, or CH2, provided that at least one of XAand YArepresents an oxygen atom, a sulfur atom, or NH.

In the general formulae (TEMP-16) to (TEMP-33), in the case where at least one of XAand YArepresents NH or CH2, the monovalent heterocyclic groups derived from the ring structures represented by the general formulae (TEMP-16) to (TEMP-33) include monovalent groups formed by removing one hydrogen atom from the NH or CH2.

Substituted Heterocyclic Group Containing Nitrogen Atom (Set of Specific Examples G2B1):

a phenylquinazolinyl group, and

Substituted Heterocyclic Group Containing Oxygen Atom (Set of Specific Examples G2B2):

a t-butyldibenzofuranyl group, and

a monovalent residual group of spiro[9H-xanthene-9,9′-[9H]fluorene].

Substituted Heterocyclic Group Containing Sulfur Atom (Set of Specific Examples G2B3):

a t-butyldibenzothiophenyl group, and

a monovalent residual group of spiro[9H-thioxanthene-9,9′-[9H]fluorene].

Group Formed by Substituting One or More Hydrogen Atom of Monovalent Heterocyclic Group Derived from Ring Structures Represented by General Formulae (TEMP-16) to (TEMP-33) by Substituent (Set of Specific Examples G2B4)

The “one or more hydrogen atom of the monovalent heterocyclic group” means one or more hydrogen atom selected from the hydrogen atom bonded to the ring carbon atom of the monovalent heterocyclic group, the hydrogen atom bonded to the nitrogen atom in the case where at least one of XAand YArepresents NH, and the hydrogen atom of the methylene group in the case where one of XAand YArepresents CH2.

Substituted or Unsubstituted Alkyl Group

In the description herein, specific examples (set of specific examples G3) of the “substituted or unsubstituted alkyl group” include the unsubstituted alkyl groups (set of specific examples G3A) and the substituted alkyl groups (set of specific examples G3B) shown below. (Herein, the unsubstituted alkyl group means the case where the “substituted or unsubstituted alkyl group” is an “unsubstituted alkyl group”, and the substituted alkyl group means the case where the “substituted or unsubstituted alkyl group” is a “substituted alkyl group”.) In the description herein, the simple expression “alkyl group” encompasses both the “unsubstituted alkyl group” and the “substituted alkyl group”.

The “substituted alkyl group” means a group formed by substituting one or more hydrogen atom of the “unsubstituted alkyl group” by a substituent. Specific examples of the “substituted alkyl group” include groups formed by substituting one or more hydrogen atom of each of the “unsubstituted alkyl groups” (set of specific examples G3A) by a substituent, and the examples of the substituted alkyl groups (set of specific examples G3B). In the description herein, the alkyl group in the “unsubstituted alkyl group” means a chain-like alkyl group. Accordingly, the “unsubstituted alkyl group” encompasses an “unsubstituted linear alkyl group” and an “unsubstituted branched alkyl group”. The examples of the “unsubstituted alkyl group” and the examples of the “substituted alkyl group” enumerated herein are mere examples, and the “substituted alkyl group” in the description herein encompasses groups formed by substituting a hydrogen atom of the alkyl group itself of each of the “substituted alkyl groups” in the set of specific examples G3B by a substituent, and groups formed by substituting a hydrogen atom of the substituent of each of the “substituted alkyl groups” in the set of specific examples G3B by a substituent.

Unsubstituted Alkyl Group (Set of Specific Examples G3A):

a methyl group,

an ethyl group,

an isopropyl group,

a s-butyl group, and

Substituted Alkyl Group (Set of Specific Examples G3B):

a 2,2,2-trifluoroethyl group, and

a trifluoromethyl group.

Substituted or Unsubstituted Alkenyl Group

In the description herein, specific examples (set of specific examples G4) of the “substituted or unsubstituted alkenyl group” include the unsubstituted alkenyl groups (set of specific examples G4A) and the substituted alkenyl groups (set of specific examples G4B) shown below. (Herein, the unsubstituted alkenyl group means the case where the “substituted or unsubstituted alkenyl group” is an “unsubstituted alkenyl group”, and the substituted alkenyl group means the case where the “substituted or unsubstituted alkenyl group” is a “substituted alkenyl group”.) In the description herein, the simple expression “alkenyl group” encompasses both the “unsubstituted alkenyl group” and the “substituted alkenyl group”.

The “substituted alkenyl group” means a group formed by substituting one or more hydrogen atom of the “unsubstituted alkenyl group” by a substituent. Specific examples of the “substituted alkenyl group” include the “unsubstituted alkenyl groups” (set of specific examples G4A) that each have a substituent, and the examples of the substituted alkenyl groups (set of specific examples G4B). The examples of the “unsubstituted alkenyl group” and the examples of the “substituted alkenyl group” enumerated herein are mere examples, and the “substituted alkenyl group” in the description herein encompasses groups formed by substituting a hydrogen atom of the alkenyl group itself of each of the “substituted alkenyl groups” in the set of specific examples G4B by a substituent, and groups formed by substituting a hydrogen atom of the substituent of each of the “substituted alkenyl groups” in the set of specific examples G4B by a substituent.

Unsubstituted Alkenyl Group (Set of Specific Examples G4A):

a vinyl group,

a 2-butenyl group, and

Substituted Alkenyl Group (Set of Specific Examples G4B):

a 2-methylallyl group, and

Substituted or Unsubstituted Alkynyl Group

In the description herein, specific examples (set of specific examples G5) of the “substituted or unsubstituted alkynyl group” include the unsubstituted alkynyl group (set of specific examples G5A) shown below. (Herein, the unsubstituted alkynyl group means the case where the “substituted or unsubstituted alkynyl group” is an “unsubstituted alkynyl group”.) In the description herein, the simple expression “alkynyl group” encompasses both the “unsubstituted alkynyl group” and the “substituted alkynyl group”.

The “substituted alkynyl group” means a group formed by substituting one or more hydrogen atom of the “unsubstituted alkynyl group” by a substituent. Specific examples of the “substituted alkenyl group” include groups formed by substituting one or more hydrogen atom of the “unsubstituted alkynyl group” (set of specific examples G5A) by a substituent.

Unsubstituted Alkynyl Group (Set of Specific Examples G5A):

Substituted or Unsubstituted Cycloalkyl Group

In the description herein, specific examples (set of specific examples G6) of the “substituted or unsubstituted cycloalkyl group” include the unsubstituted cycloalkyl groups (set of specific examples G6A) and the substituted cycloalkyl group (set of specific examples G6B) shown below. (Herein, the unsubstituted cycloalkyl group means the case where the “substituted or unsubstituted cycloalkyl group” is an “unsubstituted cycloalkyl group”, and the substituted cycloalkyl group means the case where the “substituted or unsubstituted cycloalkyl group” is a “substituted cycloalkyl group”.) In the description herein, the simple expression “cycloalkyl group” encompasses both the “unsubstituted cycloalkyl group” and the “substituted cycloalkyl group”.

The “substituted cycloalkyl group” means a group formed by substituting one or more hydrogen atom of the “unsubstituted cycloalkyl group” by a substituent. Specific examples of the “substituted cycloalkyl group” include groups formed by substituting one or more hydrogen atom of each of the “unsubstituted cycloalkyl groups” (set of specific examples G6A) by a substituent, and the example of the substituted cycloalkyl group (set of specific examples G6B). The examples of the “unsubstituted cycloalkyl group” and the examples of the “substituted cycloalkyl group” enumerated herein are mere examples, and the “substituted cycloalkyl group” in the description herein encompasses groups formed by substituting one or more hydrogen atom bonded to the carbon atoms of the cycloalkyl group itself of the “substituted cycloalkyl group” in the set of specific examples G6B by a substituent, and groups formed by substituting a hydrogen atom of the substituent of the “substituted cycloalkyl group” in the set of specific examples G6B by a substituent.

Unsubstituted Cycloalkyl Group (Set of Specific Examples G6A):

a cyclohexyl group,

a 1-norbornyl group, and

Substituted Cycloalkyl Group (Set of Specific Examples G6B):

Group represented by —Si(R901)(R902)(R903)

In the description herein, specific examples (set of specific examples G7) of the group represented by —Si(R901)(R902)(R903) include:

—Si(G3)(G3)(G3), and

G1 represents the “substituted or unsubstituted aryl group” described in the set of specific examples G1,

G2 represents the “substituted or unsubstituted heterocyclic group” described in the set of specific examples G2,

G3 represents the “substituted or unsubstituted alkyl group” described in the set of specific examples G3, and

G6 represents the “substituted or unsubstituted cycloalkyl group” described in the set of specific examples G6.

Plural groups represented by G1 in —Si(G1)(G1)(G1) are the same as or different from each other.

Plural groups represented by G2 in —Si(G1)(G2)(G2) are the same as or different from each other.

Plural groups represented by G1 in —Si(G1)(G1)(G2) are the same as or different from each other.

Plural groups represented by G2 in —Si(G2)(G2)(G2) are the same as or different from each other.

Plural groups represented by G3 in —Si(G3)(G3)(G3) are the same as or different from each other.

Plural groups represented by G6 in —Si(G6)(G6)(G6) are the same as or different from each other.

Group Represented by —O—(R904)

In the description herein, specific examples (set of specific examples G8) of the group represented by —O—(R904) include:

—O(G3), and

G1 represents the “substituted or unsubstituted aryl group” described in the set of specific examples G1,

G2 represents the “substituted or unsubstituted heterocyclic group” described in the set of specific examples G2,

G3 represents the “substituted or unsubstituted alkyl group” described in the set of specific examples G3, and

G6 represents the “substituted or unsubstituted cycloalkyl group” described in the set of specific examples G6.

Group Represented by —S—(R905)

In the description herein, specific examples (set of specific examples G9) of the group represented by —S—(R905) include:

—S(G3), and

G1 represents the “substituted or unsubstituted aryl group” described in the set of specific examples G1,

G2 represents the “substituted or unsubstituted heterocyclic group” described in the set of specific examples G2,

G3 represents the “substituted or unsubstituted alkyl group” described in the set of specific examples G3, and

G6 represents the “substituted or unsubstituted cycloalkyl group” described in the set of specific examples G6.

Group Represented by —N(R906)(R907)

In the description herein, specific examples (set of specific examples G10) of the group represented by —N(R906)(R907) include:

—N(G3)(G3), and

G1 represents the “substituted or unsubstituted aryl group” described in the set of specific examples G1,

G2 represents the “substituted or unsubstituted heterocyclic group” described in the set of specific examples G2,

G3 represents the “substituted or unsubstituted alkyl group” described in the set of specific examples G3, and

G6 represents the “substituted or unsubstituted cycloalkyl group” described in the set of specific examples G6.

Plural groups represented by G1 in —N(G1)(G1) are the same as or different from each other.

Plural groups represented by G2 in —N(G2)(G2) are the same as or different from each other.

Plural groups represented by G3 in —N(G3)(G3) are the same as or different from each other.

Plural groups represented by G6 in —N(G6)(G6) are the same as or different from each other.

Halogen Atom

In the description herein, specific examples (set of specific examples G11) of the “halogen atom” include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

Substituted or Unsubstituted Fluoroalkyl Group

In the description herein, the “substituted or unsubstituted fluoroalkyl group” means a group formed by substituting at least one hydrogen atom bonded to the carbon atom constituting the alkyl group in the “substituted or unsubstituted alkyl group” by a fluorine atom, and encompasses a group formed by substituting all the hydrogen atoms bonded to the carbon atoms constituting the alkyl group in the “substituted or unsubstituted alkyl group” by fluorine atoms (i.e., a perfluoroalkyl group). The number of carbon atoms of the “unsubstituted fluoroalkyl group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise indicated in the description. The “substituted fluoroalkyl group” means a group formed by substituting one or more hydrogen atom of the “fluoroalkyl group” by a substituent. In the description herein, the “substituted fluoroalkyl group” encompasses a group formed by substituting one or more hydrogen atom bonded to the carbon atom of the alkyl chain in the “substituted fluoroalkyl group” by a substituent, and a group formed by substituting one or more hydrogen atom of the substituent in the “substituted fluoroalkyl group” by a substituent. Specific examples of the “unsubstituted fluoroalkyl group” include examples of groups formed by substituting one or more hydrogen atom in each of the “alkyl group” (set of specific examples G3) by a fluorine atom.

Substituted or Unsubstituted Haloalkyl Group

In the description herein, the “substituted or unsubstituted haloalkyl group” means a group formed by substituting at least one hydrogen atom bonded to the carbon atom constituting the alkyl group in the “substituted or unsubstituted alkyl group” by a halogen atom, and encompasses a group formed by substituting all the hydrogen atoms bonded to the carbon atoms constituting the alkyl group in the “substituted or unsubstituted alkyl group” by halogen atoms. The number of carbon atoms of the “unsubstituted haloalkyl group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise indicated in the description. The “substituted haloalkyl group” means a group formed by substituting one or more hydrogen atom of the “haloalkyl group” by a substituent. In the description herein, the “substituted haloalkyl group” encompasses a group formed by substituting one or more hydrogen atom bonded to the carbon atom of the alkyl chain in the “substituted haloalkyl group” by a substituent, and a group formed by substituting one or more hydrogen atom of the substituent in the “substituted haloalkyl group” by a substituent. Specific examples of the “unsubstituted haloalkyl group” include examples of groups formed by substituting one or more hydrogen atom in each of the “alkyl group” (set of specific examples G3) by a halogen atom. A haloalkyl group may be referred to as a halogenated alkyl group in some cases.

Substituted or Unsubstituted Alkoxy Group

In the description herein, specific examples of the “substituted or unsubstituted alkoxy group” include a group represented by —O(G3), wherein G3 represents the “substituted or unsubstituted alkyl group” described in the set of specific examples G3. The number of carbon atoms of the “unsubstituted alkoxy group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise indicated in the description.

Substituted or Unsubstituted Alkylthio Group

In the description herein, specific examples of the “substituted or unsubstituted alkylthio group” include a group represented by —S(G3), wherein G3 represents the “substituted or unsubstituted alkyl group” described in the set of specific examples G3. The number of carbon atoms of the “unsubstituted alkylthio group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise indicated in the description.

Substituted or Unsubstituted Aryloxy Group

In the description herein, specific examples of the “substituted or unsubstituted aryloxy group” include a group represented by —O(G1), wherein G1 represents the “substituted or unsubstituted aryl group” described in the set of specific examples G1. The number of ring carbon atoms of the “unsubstituted aryloxy group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise indicated in the description.

Substituted or Unsubstituted Arylthio Group

In the description herein, specific examples of the “substituted or unsubstituted arylthio group” include a group represented by —S(G1), wherein G1 represents the “substituted or unsubstituted aryl group” described in the set of specific examples G1. The number of ring carbon atoms of the “unsubstituted arylthio group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise indicated in the description.

Substituted or Unsubstituted Trialkylsilyl Group

In the description herein, specific examples of the “trialkylsilyl group” include a group represented by —Si(G3)(G3)(G3), wherein G3 represents the “substituted or unsubstituted alkyl group” described in the set of specific examples G3. Plural groups represented by G3 in —Si(G3)(G3)(G3) are the same as or different from each other. The number of carbon atoms of each of alkyl groups of the “substituted or unsubstituted trialkylsilyl group” is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise indicated in the description.

Substituted or Unsubstituted Aralkyl Group

In the description herein, specific examples of the “substituted or unsubstituted aralkyl group” include a group represented by -(G3)-(G1), wherein G3 represents the “substituted or unsubstituted alkyl group” described in the set of specific examples G3, and G1 represents the “substituted or unsubstituted aryl group” described in the set of specific examples G1. Accordingly, the “aralkyl group” is a group formed by substituting a hydrogen atom of an “alkyl group” by an “aryl group” as a substituent, and is one embodiment of the “substituted alkyl group”. The “unsubstituted aralkyl group” is an “unsubstituted alkyl group” that is substituted by an “unsubstituted aryl group”, and the number of carbon atoms of the “unsubstituted aralkyl group” is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise indicated in the description.

In the description herein, the carbazolyl group is specifically any one of the following groups unless otherwise indicated in the description.

In the description herein, the (9-phenyl)carbazolyl group is specifically any one of the following groups unless otherwise indicated in the description.

In the general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding site.

In the description herein, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any one of the following groups unless otherwise indicated in the description.

In the general formulae (TEMP-34) to (TEMP-41), represents a bonding site.

In the description herein, the substituted or unsubstituted alkyl group is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, and isobutyl group, a t-butyl group, or the like unless otherwise indicated in the description.

Substituted or Unsubstituted Arylene Group

In the description herein, the “substituted or unsubstituted arylene group” is a divalent group derived by removing one hydrogen atom on the aryl ring from the “substituted or unsubstituted aryl group” described above unless otherwise indicated in the description. Specific examples (set of specific examples G12) of the “substituted or unsubstituted arylene group” include divalent groups derived by removing one hydrogen atom on the aryl ring from the “substituted or unsubstituted aryl groups” described in the set of specific examples G1.

Substituted or Unsubstituted Divalent Heterocyclic Group

In the description herein, the “substituted or unsubstituted divalent heterocyclic group” is a divalent group derived by removing one hydrogen atom on the heterocyclic ring from the “substituted or unsubstituted heterocyclic group” described above unless otherwise indicated in the description. Specific examples (set of specific examples G13) of the “substituted or unsubstituted divalent heterocyclic group” include divalent groups derived by removing one hydrogen atom on the heterocyclic ring from the “substituted or unsubstituted heterocyclic groups” described in the set of specific examples G2.

Substituted or Unsubstituted Alkylene Group

In the description herein, the “substituted or unsubstituted alkylene group” is a divalent group derived by removing one hydrogen atom on the alkyl chain from the “substituted or unsubstituted alkyl group” described above unless otherwise indicated in the description. Specific examples (set of specific examples G14) of the “substituted or unsubstituted alkylene group” include divalent groups derived by removing one hydrogen atom on the alkyl chain from the “substituted or unsubstituted alkyl groups” described in the set of specific examples G3.

In the description herein, the substituted or unsubstituted arylene group is preferably any one of the groups represented by the following general formulae (TEMP-42) to (TEMP-68) unless otherwise indicated in the description.

In the general formulae (TEMP-42) to (TEMP-52), Q1to Q10each independently represent a hydrogen atom or a substituent.

In the general formulae (TEMP-42) to (TEMP-52), * represents a bonding site.

In the general formulae (TEMP-53) to (TEMP-62), Q1to Q10each independently represent a hydrogen atom or a substituent.

The formulae Q9and Q10may be bonded to each other to form a ring via a single bond.

In the general formulae (TEMP-53) to (TEMP-62), * represents a bonding site.

In the general formulae (TEMP-63) to (TEMP-68), Q1to Q8each independently represent a hydrogen atom or a substituent.

In the general formulae (TEMP-63) to (TEMP-68), * represents a bonding site.

In the description herein, the substituted or unsubstituted divalent heterocyclic group is preferably the groups represented by the following general formulae (TEMP-69) to (TEMP-102) unless otherwise indicated in the description.

In the general formulae (TEMP-69) to (TEMP-82), Q1to Q9each independently represent a hydrogen atom or a substituent.

In the general formulae (TEMP-83) to (TEMP-102), Q1to Q8each independently represent a hydrogen atom or a substituent.

The above are the explanation of the “substituents in the description herein”.

Case Forming Ring by Bonding

In the description herein, the case where “one or more combinations of combinations each including adjacent two or more each are bonded to each other to form a substituted or unsubstituted monocyclic ring, or each are bonded to each other to form a substituted or unsubstituted condensed ring, or each are not bonded to each other” means a case where “one or more combinations of combinations each including adjacent two or more each are bonded to each other to form a substituted or unsubstituted monocyclic ring”, a case where “one or more combinations of combinations each including adjacent two or more each are bonded to each other to form a substituted or unsubstituted condensed ring”, and a case where “one or more combinations of combinations each including adjacent two or more each are not bonded to each other”.

In the description herein, the case where “one or more combinations of combinations each including adjacent two or more each are bonded to each other to form a substituted or unsubstituted monocyclic ring” and the case where “one or more combinations of combinations each including adjacent two or more each are bonded to each other to form a substituted or unsubstituted condensed ring” (which may be hereinafter collectively referred to as a “case forming a ring by bonding”) will be explained below. The cases will be explained for the anthracene compound represented by the following general formula (TEMP-103) having an anthracene core skeleton as an example.

For example, in the case where “one or more combinations of combinations each including adjacent two or more each are bonded to each other to form a ring” among R921to R930, the combinations each including adjacent two as one combination include a combination of R921and R922, a combination of R922and R923, a combination of R923and R924, a combination of R924and R930, a combination of R930and R925, a combination of R925and R926, a combination of R926and R927, a combination of R927and R928, a combination of R928and R929, and a combination of R929and R921.

The “one or more combinations” mean that two or more combinations each including adjacent two or more may form rings simultaneously. For example, in the case where R921and R922are bonded to each other to form a ring QA, and simultaneously R925and R926are bonded to each other to form a ring QB, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-104).

The case where the “combination including adjacent two or more forms rings” encompasses not only the case where adjacent two included in the combination are bonded as in the aforementioned example, but also the case where adjacent three or more included in the combination are bonded. For example, this case means that R921and R922are bonded to each other to form a ring QA, R922and R923are bonded to each other to form a ring QC, and adjacent three (R921, R922, and R923) included in the combination are bonded to each other to form rings, which are condensed to the anthracene core skeleton, and in this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), the ring QAand the ring QCshare R922.

The formed “monocyclic ring” or “condensed ring” may be a saturated ring or an unsaturated ring in terms of structure of the formed ring itself. In the case where the “one combination including adjacent two” forms a “monocyclic ring” or a “condensed ring”, the “monocyclic ring” or the “condensed ring” may form a saturated ring or an unsaturated ring. For example, the ring QAand the ring QBformed in the general formula (TEMP-104) each are a “monocyclic ring” or a “condensed ring”. The ring QAand the ring QCformed in the general formula (TEMP-105) each are a “condensed ring”. The ring QAand the ring QCin the general formula (TEMP-105) form a condensed ring through condensation of the ring QAand the ring QC. In the case where the ring QAin the general formula (TMEP-104) is a benzene ring, the ring QAis a monocyclic ring. In the case where the ring QAin the general formula (TMEP-104) is a naphthalene ring, the ring QAis a condensed ring.

The “unsaturated ring” means an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The “saturated ring” means an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring.

Specific examples of the aromatic hydrocarbon ring include the structures formed by terminating the groups exemplified as the specific examples in the set of specific examples G1 with a hydrogen atom.

Specific examples of the aromatic heterocyclic ring include the structures formed by terminating the aromatic heterocyclic groups exemplified as the specific examples in the set of specific examples G2 with a hydrogen atom.

Specific examples of the aliphatic hydrocarbon ring include the structures formed by terminating the groups exemplified as the specific examples in the set of specific examples G6 with a hydrogen atom.

The expression “to form a ring” means that the ring is formed only with the plural atoms of the core structure or with the plural atoms of the core structure and one or more arbitrary element. For example, the ring QAformed by bonding R921and R922each other shown in the general formula (TEMP-104) means a ring formed with the carbon atom of the anthracene skeleton bonded to R921, the carbon atom of the anthracene skeleton bonded to R922, and one or more arbitrary element. As a specific example, in the case where the ring QAis formed with R921and R922, and in the case where a monocyclic unsaturated ring is formed with the carbon atom of the anthracene skeleton bonded to R921, the carbon atom of the anthracene skeleton bonded to R922, and four carbon atoms, the ring formed with R921and R922is a benzene ring.

Herein, the “arbitrary element” is preferably at least one kind of an element selected from the group consisting of a carbon element, a nitrogen element, an oxygen element, and a sulfur element, unless otherwise indicated in the description. For the arbitrary element (for example, for a carbon element or a nitrogen element), a bond that does not form a ring may be terminated with a hydrogen atom or the like, and may be substituted by an “arbitrary substituent” described later. In the case where an arbitrary element other than a carbon element is contained, the formed ring is a heterocyclic ring.

The number of the “one or more arbitrary element” constituting the monocyclic ring or the condensed ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and further preferably 3 or more and 5 or less, unless otherwise indicated in the description.

What is preferred between the “monocyclic ring” and the “condensed ring” is the “monocyclic ring” unless otherwise indicated in the description.

What is preferred between the “saturated ring” and the “unsaturated ring” is the “unsaturated ring” unless otherwise indicated in the description.

The “monocyclic ring” is preferably a benzene ring unless otherwise indicated in the description.

The “unsaturated ring” is preferably a benzene ring unless otherwise indicated in the description.

In the case where the “one or more combinations of combinations each including adjacent two or more” each are “bonded to each other to form a substituted or unsubstituted monocyclic ring”, or each are “bonded to each other to form a substituted or unsubstituted condensed ring”, it is preferred that the one or more combinations of combinations each including adjacent two or more each are bonded to each other to form a substituted or unsubstituted “unsaturated ring” containing the plural atoms of the core skeleton and 1 or more and 15 or less at least one kind of an element selected from the group consisting of a carbon element, a nitrogen element, an oxygen element, and a sulfur element, unless otherwise indicated in the description.

In the case where the “monocyclic ring” or the “condensed ring” has a substituent, the substituent is, for example, an “arbitrary substituent” described later. In the case where the “monocyclic ring” or the “condensed ring” has a substituent, specific examples of the substituent include the substituents explained in the section “Substituents in Description” described above.

In the case where the “saturated ring” or the “unsaturated ring” has a substituent, the substituent is, for example, an “arbitrary substituent” described later. In the case where the “monocyclic ring” or the “condensed ring” has a substituent, specific examples of the substituent include the substituents explained in the section “Substituents in Description” described above.

The above are the explanation of the case where “one or more combinations of combinations each including adjacent two or more” each are “bonded to each other to form a substituted or unsubstituted monocyclic ring”, and the case where “one or more combinations of combinations each including adjacent two or more” each are “bonded to each other to form a substituted or unsubstituted condensed ring” (i.e., the “case forming a ring by bonding”).

Substituent for “Substituted or Unsubstituted”

In one embodiment in the description herein, the substituent for the case of “substituted or unsubstituted” (which may be hereinafter referred to as an “arbitrary substituent”) is, for example, a group selected from the group consisting of

an unsubstituted alkyl group having 1 to 50 carbon atoms,

an unsubstituted alkenyl group having 2 to 50 carbon atoms,

an unsubstituted alkynyl group having 2 to 50 carbon atoms,

an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a halogen atom, a cyano group, a nitro group,

an unsubstituted aryl group having 6 to 50 ring carbon atoms, and

an unsubstituted heterocyclic group having 5 to 50 ring atoms,

a hydrogen atom,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

In the case where two or more groups each represented by R901exist, the two or more groups each represented by R901are the same as or different from each other,

in the case where two or more groups each represented by R902exist, the two or more groups each represented by R902are the same as or different from each other,

in the case where two or more groups each represented by R903exist, the two or more groups each represented by R903are the same as or different from each other,

in the case where two or more groups each represented by R904exist, the two or more groups each represented by R904are the same as or different from each other,

in the case where two or more groups each represented by R905exist, the two or more groups each represented by R905are the same as or different from each other,

in the case where two or more groups each represented by R906exist, the two or more groups each represented by R906are the same as or different from each other, and

in the case where two or more groups each represented by R907exist, the two or more groups each represented by R907are the same as or different from each other.

In one embodiment, the substituent for the case of “substituted or unsubstituted” may be a group selected from the group consisting of

an alkyl group having 1 to 50 carbon atoms,

an aryl group having 6 to 50 ring carbon atoms, and

a heterocyclic group having 5 to 50 ring atoms.

In one embodiment, the substituent for the case of “substituted or unsubstituted” may be a group selected from the group consisting of

an alkyl group having 1 to 18 carbon atoms,

an aryl group having 6 to 18 ring carbon atoms, and

a heterocyclic group having 5 to 18 ring atoms.

The specific examples of the groups for the arbitrary substituent described above are the specific examples of the substituent described in the section “Substituents in Description” described above.

In the description herein, the arbitrary adjacent substituents may form a “saturated ring” or an “unsaturated ring”, preferably form a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, and more preferably form a benzene ring, unless otherwise indicated.

In the description herein, the arbitrary substituent may further have a substituent unless otherwise indicated in the description. The definition of the substituent that the arbitrary substituent further has may be the same as the arbitrary substituent.

In the description herein, a numerical range shown by “AA to BB” means a range including the numerical value AA as the former of “AA to BB” as the lower limit value and the numerical value BB as the latter of “AA to BB” as the upper limit value.

The compound of the present invention will be described below.

The compound of one embodiment of the present invention is represented by the following formula (1).

In the following description, the compounds of the present invention represented by the formula (1) and the subordinate formulae of the formula (1) described later each may be referred simply to as an “inventive compound (1)” or an “inventive compound”.

The symbols in the formula (1) and the subordinate formulae of the formula (1) described later will be explained below. The same symbols have the same meanings.

In the formula (1),

the carbon atom ** constitutes a 6-membered ring along with Y1to Y5,

Y1to Y5each independently represent a nitrogen atom or CR, and two or more selected from Y1to Y5are nitrogen atoms. In the case where plural CR's exist, R's in the plural CR's are the same as or different from each other.

Preferably, two or three selected from Y1to Y5are nitrogen atoms.

In the formula (1),

R, R1to R6, R7to R10, Ara, and Arbeach independently represent a hydrogen atom or a substituent A, and one selected from R7to R10is a single bond bonding to *a.

In the formula (1), preferably, one selected from R7to R9is a single bond bonding to *a. In other words, it is preferable that any one of the 8- to 10-positions of the benzoxanthene ring that the compound represented by the formula (1) has bonds to *a. More preferably, R9is a single bond bonding to *a (namely, *a bonds to the 10-position of the benzoxanthene ring).

a halogen atom,
a nitro group,
a cyano group,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
a group represented by —Si(R901)(R902)(R903),
a group represented by —O—(R904),
a group represented by —S—(R905),
a group represented by —N(R906)(R907),
a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or
a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

in the case where two or more R901's exist, the two or more R901's are the same as or different from each other,

in the case where two or more R902's exist, the two or more R902's are the same as or different from each other,

in the case where two or more R903's exist, the two or more R903's are the same as or different from each other,

in the case where two or more R904's exist, the two or more R904's are the same as or different from each other,

in the case where two or more R905's exist, the two or more R905's are the same as or different from each other,

in the case where two or more R906's exist, the two or more R906's are the same as or different from each other,

in the case where two or more R907's exist, the two or more R907's are the same as or different from each other.

Preferably, R1to R6, R7to R10, Ara, and Arbeach independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, more preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, even more preferably a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and further more preferably a hydrogen atom.

In the case where plural CR's exist, preferably, at least one R is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, more preferably two R's each are a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. In the case where plural CR's exist, one R may be a hydrogen atom, namely, plural CR's may include a methine group (CH).

Details of the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms that R, R1to R6, R7to R10, Ara, and Arbrepresent are described in the section of “Substituents in Description” described above.

The unsubstituted aryl group that R, R1to R6, R7to R10, Ara, and Arbrepresent is preferably a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a phenanthrenyl group, a triphenylenyl group, or a fluorenyl group, more preferably a phenyl group, a biphenyl group, or a naphthyl group, even more preferably a phenyl group.

Details of the substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms that R, R1to R6, R7to R10, Ara, and Arnrepresent are described in the section of “Substituents in Description” described above.

The unsubstituted heterocyclic group that R, R1to R6, R7to R10, Ara, and Arbrepresent is preferably a dibenzofuranyl group, a dibenzothiophenyl group, or a pyridyl group, more preferably a dibenzofuranyl group or a dibenzothiophenyl group.

Details of the halogen atom that R, R1to R6, R7to R10, Ara, and Arbrepresent are described in the section of “Substituents in Description” described above, and a fluorine atom is preferred.

Details of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms that R, R1to R6, R7to R10, Ara, and Arbrepresent are described in the section of “Substituents in Description” described above.

The unsubstituted alkyl group that R, R1to R6, R7to R10, Ara, and Arnrepresent is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, or a t-butyl group, more preferably a methyl group, an ethyl group, an isopropyl group, or a t-butyl group, even more preferably a methyl group or a t-butyl group.

Details of the substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms that R, R1to R6, R7to R10, Ara, and Arnrepresent are described in the section of “Substituents in Description” described above.

Details of the substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms that R, R1to R6, R7to R10, Ara, and Arbrepresent are described in the section of “Substituents in Description” described above.

Details of the substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms that R, R1to R6, R7to R10, Ara, and Arbrepresent are described in the section of “Substituents in Description” described above.

The unsubstituted cycloalkyl group that R, R1to R6, R7to R10, Ara, and Arbrepresent is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, or a 2-norbornyl group, more preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, even more preferably a cyclopentyl group or a cyclohexyl group.

Details of the group —Si(R901)(R902)(R903), the group —O—(R904), the group —S—(R905) and the group —N(R906)(R907) that R, R1to R6, and R7to R10represent are described in the section of “Substituents in Description” described above.

R1to R6, and R7to R10not bonding to *a do not bond to each other to form a cyclic structure,

In the case where plural CR's exist, two neighboring R's bond to each other to form a substituted or unsubstituted cyclic structure, or do not bond to each other and therefore do not form a cyclic structure,

In one or more pairs selected from two neighboring CR's, details of an arbitrary substituted or unsubstituted ring formed by the neighboring two R's bonding to each other are described in the section of “Substituents in Description” described above, and the ring is selected from a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic heterocyclic ring and a substituted or unsubstituted nonaromatic heterocyclic ring.

Examples of the aromatic hydrocarbon ring include a benzene ring, a biphenylene ring, a naphthalene ring, and a fluorene ring, and a naphthalene ring and a fluorene ring are preferred.

Examples of the aliphatic hydrocarbon ring include a cyclopentene ring, a cyclopentadiene ring, a cyclohexene ring, a cyclohexadiene ring, and a hydrocarbon ring formed by partially hydrogenating the above-mentioned aromatic hydrocarbon ring.

Examples of the aromatic heterocyclic ring include a pyrrole ring, a furan ring, a thiophene ring, a pyridine ring, an imidazole ring, a pyrazole ring, an indole ring, an isoindole ring, a benzofuran ring, an isobenzofuran ring, a benzothiophene ring, a benzimidazole ring, an indazole ring, a dibenzofuran ring, a naphthobenzofuran ring, a dibenzothiophene ring, a naphthobenzothiophene ring, a carbazole ring, and a benzocarbazole ring, and a dibenzofuran ring and a dibenzothiophene ring are preferred.

Examples of the nonaromatic heterocyclic group include a hetero ring formed by partially hydrogenating the above-mentioned aromatic heterocyclic ring.

In the present invention, in one or more pairs selected from neighboring two CR's, the neighboring two R's may not bond to each other to form a substituted or unsubstituted ring.

L1represents a substituted or unsubstituted, (2+p)-valent aromatic hydrocarbon ring having 6 to 12 ring carbon atoms,

L2represents a substituted or unsubstituted, (2+q)-valent aromatic hydrocarbon ring having 6 to 12 ring carbon atoms,

when L1is a (2+p)-valent residue of a naphthalene, L2is not a (2+q)-valent residue of a naphthalene, and when L2is a (2+q)-valent residue of a naphthalene, L1is not a (2+p)-valent residue of a naphthalene,

m represents 0 or 1,

n represents 0 or 1, provided that

when m and n are 0, the carbon ** bonds to *a,

when m is 0 and n is 1, L2bonds to *a and the carbon atom **,

when n is 0 and m is 1, L1bonds to *a and the carbon atom **.

q represents 0, 1, 2 or 3, provided that

when p is 2 or more, the plural Ara's are the same as or different from each other,

when q is 2 or more, the plural Arb's are the same as or different from each other.

The substituted or unsubstituted, (2+q)-valent aromatic hydrocarbon ring having 6 to 12 ring carbon atoms that L2represents is preferably each independently a substituted or unsubstituted (2+q)-valent residue of a compound selected from benzene, biphenyl, naphthalene and fluorene.

More preferably, the substituted or unsubstituted, (2+q)-valent aromatic hydrocarbon ring having 6 to 12 ring carbon atoms that L2represents is each independently a substituted or unsubstituted (2+q)-valent residue of a compound selected from benzene, biphenyl and naphthalene.

The substituted or unsubstituted, (2+p)-valent aromatic hydrocarbon ring having 6 to 12 ring carbon atoms that L1represents is preferably each independently a substituted or unsubstituted (2+p)-valent residue of a compound selected from benzene, biphenyl, naphthalene and fluorene.

More preferably, the substituted or unsubstituted, (2+p)-valent aromatic hydrocarbon ring having 6 to 12 ring carbon atoms that L1represents is each independently a substituted or unsubstituted (2+p)-valent residue of a compound selected from benzene, biphenyl and naphthalene.

The inventive compound (1) represented by the formula (1) is preferably represented by the following formula (1-a), formula (1-b) or formula (1-c).

The inventive compound (1) represented by the formula (1) is preferably represented by the following formula (1-1).

In the formula (1-1), R1to R10, L1, Ara, Y1to Y5, p, and *a are as defined in the formula (1).

In the formula (1-1), preferably, any one of R7to R9is a single bond bonding to *a.

The inventive compound (1) represented by the formula (1) is preferably represented by the following formula (1-1-a), formula (1-1-b) or formula (1-1-c).

In the formulae (1-1-a) to (1-1-c), R1to R10, L1, Ara, Y1to Y5, and p are as defined in the formula (1).

The inventive compound (1) represented by the formula (1) is preferably represented by the following formula (1-2).

In the formula (1-2), R1to R10, Y1to Y5, and *a are as defined in the formula (1).

In the formula (1-2), preferably any one of R7to R9is a single bond bonding to *a.

The inventive compound (1) represented by the formula (1) is preferably represented by the following formula (1-2-a), formula (1-2-b) or formula (1-2-c).

In the formulae (1-2-a) to (1-2-c), R1to R10, and Y1to Y5are as defined in the formula (1).

The inventive compound (1) represented by the formula (1) is preferably represented by the following formula (1-11), formula (1-12) or formula (1-13).

In the formulae (1-11) to (1-13),

R1to R10, Y1to Y5, and *a are as defined in the formula (1).

In the formula (1-11),

one selected from R11to R16bonds to *b, the other one selected from R11to R16bonds to *c, one selected from R21to R26bonds to *d, the other one selected from R21to R26bonds to *e.

In the formula (1-12),

one selected from R31to R36bonds to *b1, the other one selected from R31to R36bonds to *c1, one selected from R41to R48bonds to *d1, the other one selected from R41to R48bonds to *e.

In the formula (1-13),

one selected from R51to R58bonds to *b2, the other one selected from R51to R58bonds to *c2, one selected from R61to R68bonds to *d2, the other one selected from R61to R68bonds to *e.

R11to R16not bonding to *b and *c, R21to R26not bonding to *d and *e, R31to R36not bonding to *b1 and *c1, R41to R48not bonding to *d1 and *e, R51to R58not bonding to *b2 and *c2, and R61to R66not bonding to *d2 and *e each are independently a hydrogen atom or the substituent A.

In the formula (1-11), R11to R16that are not a single bond bonding to *b and are not a single bond bonding to *c, and R21to R26that are not a single bond bonding to *d and are not a single bond bonding to *e, in the formula (1-12), R31to R36that are not a single bond bonding to *b1 and are not a single bond bonding to *c1, and R41to R48that are not a single bond bonding to *d1 and are not a single bond bonding to *e, and in the formula (1-13), R51to R58that are not a single bond bonding to *b2 and are not a single bond bonding to *c2, and R61to R66that are not a single bond bonding to *d2 and are not a single bond bonding to *e are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, more preferably a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, even more preferably a hydrogen atom.

Details of the groups represented by R11to R16, R21to R26, R31to R36, R41to R48, R51to R58, and R61to R66are the same as the details of the corresponding groups described relative to R, R1to R6, R7to R10, Ara, and Arb, and the preferred groups of the former are all the same as those of the latter.

In the formulae (1-11) to (1-13), m1 to m3 and n1 to n3 each independently represent 0 or 1, provided that:

when m1 and n1 are 0, *b bonds to *e,

when m1 is 0 and n1 is 1, *b bonds to *c,

when m1 is 1 and n1 is 0, *d bonds to *e.

When m2 and n2 are 0, *b1 bonds to *e,

when m2 is 0 and n2 is 1, *b1 bonds to *c1,

when m2 is 1 and n2 is 0, *d1 bonds to *e.

When m3 and n3 are 0, *b2 bonds to *e,

when m3 is 0 and n3 is 1, *b2 bonds to *c2,

when m3 is 1 and n3 is 0, *d2 bonds to *e.

In the formula (1-11),

when m1 and n1 are 0, *b bonds to *e, and preferably, any one of R7to R9is a single bond bonding to *a.

When m1 is 1 and n1 is 0, *d bonds to *e, and in one embodiment, Ru is a single bond bonding to *b, any one of R12to R14is a single bond bonding to *c, and preferably R13or R14is a single bond bonding to *c. In these embodiments, preferably any one of R7to R9is a single bond bonding to *a.

When m1 is 0 and n1 is 1, *c bonds to *b, and in one embodiment, R21is a single bond bonding to *d, any one of R22to R24is a single bond bonding to *e, and preferably R23or R24is a single bond bonding to *e. In these embodiments, preferably, any one of R7to R9is a single bond bonding to *a.

When m1 and n1 are 1, in one embodiment, Ru is a single bond bonding to *b, any one of R12to R14is a single bond bonding to *c, R21is a single bond bonding to *d, any one of R22to R24is a single bond bonding to *e, and preferably11is a single bond bonding to *b, R13or R14is a single bond bonding to *c, R21is a single bond bonding to *d, any one of R23or R24is a single bond bonding to *e. In these embodiments, preferably, any one of R7to R9is a single bond bonding to *a.

In the formula (1-12),

when m2 and n2 are 0, *b1 bonds to *e, and preferably any one of R7to R9is a single bond bonding to *a.

When m2 is 1 and n2 is 0, *d1 bonds to *e, and in one embodiment, R31is a single bond bonding to *b1, any one of R32to R34is a single bond bonding to *c1, preferably, R33or R34is a single bond bonding to *c1. In these embodiments, preferably any one of R7to R9is a single bond bonding to *a.

When m2 is 0 and n2 is 1, *c1 bonds to *b1, and in one embodiment, R41is a single bond bonding to *d1, any one of R42to R48is a single bond bonding to *e, preferably R44is a single bond bonding to *e. In another embodiment, R42is a single bond bonding to *d1, any one of R41and R43to R48is a single bond bonding to *e, preferably R46is a single bond bonding to *e. In these embodiments, preferably, any one of R7to R9is a single bond bonding to *a.

When m2 and n2 are 1, in one embodiment, R31is a single bond bonding to *b1, any one of R32to R34is a single bond bonding to *c1, R41bonds to *d1, any one of R42to R48is a single bond bonding to *e, preferably R33or R34is a single bond bonding to *c1, R44is a single bond bonding to *e. In another embodiment, R31is a single bond bonding to *b1, any one of R32to R34is a single bond bonding to *c1, R42is a single bond bonding to *d1, any one of R41and R43to R48is a single bond bonding to *e, and preferably R33or R34is a single bond bonding to *c1, R46is a single bond bonding to *e. In these embodiments, preferably, any one of R7to R9is a single bond bonding to *a.

In the formula (1-13),

when m3 and n3 are 0, *b2 bonds to *e, preferably any one of R7to R9is a single bond bonding to *a.

When m3 is 0 and n3 is 1, *c2 bonds to *b2, and in one embodiment, R61is a single bond bonding to *d2, any one of R62to R64is a single bond bonding to *e, preferably R63or R64is a single bond bonding to *e. In these embodiments, preferably, any one of R7to R9is a single bond bonding to *a.

When m3 is 1 and n3 is 0, *d2 bonds to *e, and in one embodiment, R51is a single bond bonding to *b2, any one of R52to R58is a single bond bonding to *c2, preferably R54is a single bond bonding to *c2. In another embodiment, R52is a single bond bonding to *b2, any one of R51and R53to R58is a single bond bonding to *c2, preferably R56is a single bond bonding to *c2. In these embodiments, preferably, any one of R7to R9is a single bond bonding to *a.

When m3 and n3 are 1, in one embodiment, R61is a single bond bonding to *d2, any one of R62to R64is a single bond bonding to *e, R51bonds to *b2, any one of R52to R58is a single bond bonding to *c2, preferably R63or R64is a single bond bonding to *e, R54is a single bond bonding to *c2. In another embodiment, R61is a single bond bonding to *d2, any one of R62to R64is a single bond bonding to *e, R52is a single bond bonding to *b2, any one of R51and R53to R58is a single bond bonding to *c2, preferably R63or R64is a single bond bonding to *e, R56is a single bond bonding to *c2. In these embodiments, preferably, any one of R7to R9is a single bond bonding to *a.

The inventive compound (1) represented by the formula (1) is preferably represented by the following formula (1-14) or formula (1-15).

In the formula (1-14) and the formula (1-15),

R1to R10, Y1to Y5, and *a are as defined in the formula (1).

In the formula (1-14),

one selected from R71to R76bonds to *b3, and the other one selected from R71to R76bonds to *e.

In the formula (1-15),

one selected from R81to R88bonds to *b4, and the other one selected from R81to R88bonds to *e.

R71to R76not bonding to *b4 and *e, and R81to R88not bonding to *b4 and *e each independently represent a hydrogen atom and the substituent A.

In the formula (1-14) and the formula (1-15), m4 and m5 each independently represent 0 or 1.

In the formula (1-14), R71to R76that are not a single bond bonding to *b3 and are not a single bond bonding to *e, and in the formula (1-15), R81to R88that are not a single bond bonding to *b4 and are not a single bond bonding to *e are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, more preferably a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, even more preferably a hydrogen atom.

Details of the groups represented by R71to R78and R81to R88are the same as the details of the corresponding groups described relative to R, R1to R6, R7to R10, Ara, and Arb, and the preferred groups of the former are all the same as those of the latter.

In the formula (1-14),

when m4 is 0, *b3 bonds to *e, and preferably, any one of R7to R9is a single bond bonding to *a.

When m4 is 1, in one embodiment, R71is a single bond bonding to *b3, any one of R72to R74is a single bond bonding to *e, preferably R73or R74is a single bond bonding to *e. In these embodiments, preferably, any one of R7to R9is a single bond bonding to *a.

In the formula (1-15),

when m5 is 0, *b4 bonds to *e, and preferably any one of R7to R9is a single bond bonding to *a.

When m5 is 1, in one embodiment, R81is a single bond bonding to *b4, any one of R82to R88is a single bond bonding to *e, preferably R84is a single bond bonding to *e. In another embodiment, R82is a single bond bonding to *b4, any one of R81and R83to R88is a single bond bonding to *e, preferably R86is a single bond bonding to *e. In these embodiments, preferably, any one of R7to R9is a single bond bonding to *a.

The inventive compound (1) represented by the formula (1) is preferably represented by the following formula (1-21).

Preferably, *a bonds to any one of the 8- to 10-positions of the benzoxanthene ring that the compound represented by the formula (1-21) has.

The inventive compound (1) represented by the formula (1) is preferably represented by the following formula (1-22), formula (1-23) or formula (1-24).

In the formulae (1-22) to (1-24),

Y1to Y5and *a are as defined in the formula (1),

m1 to m3, n1 to n3, *b to *b2, *c to c2, *d to *d2, and *e are as defined in the formulae (1-11) to (1-13).

Preferably, *a bonds to any one of the 8- to 10-positions of the benzoxanthene ring that the compound represented by any of the formulae (1-22) to (1-24) has.

In the formula (1-22),

when m1 is 1, preferably, *b and *c bond to the benzene ring so as to be in the meta-position or the para-position to each other,

when n1 is 1, preferably, *d and *e bond to the benzene ring so as to be in the meta-position or the para-position to each other.

In the formula (1-23),

when m2 is 1, preferably, *b1 and *c1 bond to the benzene ring so as to be in the meta-position or the para-position to each other,

when n2 is 1, preferably, *d1 and *e bond to the naphthalene ring so as to be in the 1-position and the 4-position or in the 2-position and the 6-position to each other.

In the formula (1-24),

when m3 is 1, preferably, *b2 and *c2 bond to the naphthalene ring so as to be in the 1-position and the 4-position or in the 2-position and the 6-position to each other,

when n3 is 1, preferably, *d2 and *e bond to the benzene ring so as to be in the meta-position or the para-position to each other.

The inventive compound (1) represented by the formula (1) is preferably represented by the following formula (1-22-a), formula (1-22-b) or formula (1-22-c).

In the formulae (1-22-a) to (1-22-c), Y1to Y5, m1, n1, *b, *c, *d, and *e are as defined in the formula (1) and the formula (1-22).

In the formulae (1-22-a) to (1-22-c),

when m1 is 1, preferably, *b and *c bond to the benzene ring so as to be in the meta-position or the para-position to each other,

when n1 is 1, preferably, *d and *e bond to the benzene ring so as to be in the meta-position or the para-position to each other.

The inventive compound (1) represented by the formula (1) is preferably represented by the following formula (1-23-a), formula (1-23-b) or formula (1-23-c).

In the formulae (1-23-a) to (1-23-c), Y1to Y5, m2, n2, *b1, *c1, *d1, and *e are as defined in the formula (1) and the formula (1-23).

In the formulae (1-23-a) to (1-23-c),

when m2 is 1, preferably, *b1 and *c1 bond to the benzene ring so as to be in the meta-position or the para-position to each other,

when n2 is 1, preferably, *d1 and *e bond to the naphthalene ring so as to be in the 1-position and the 4-position or in the 2-position and the 6-position to each other.

The inventive compound (1) represented by the formula (1) is preferably represented by the following formula (1-24-a), formula (1-24-b) or formula (1-24-c).

In the formulae (1-24-a) to (1-24-c), Y1to Y5, m3, n3, *b2, *c2, *d2, and *e are as defined in the formula (1) and the formula (1-24).

In the formulae (1-24-a) to (1-24-c),

when m3 is 1, preferably, *b2 and *c2 bond to the naphthalene ring so as to be in the 1-position and the 4-position or in the 2-position and the 6-position to each other,

when n3 is 1, preferably, *d2 and *e bond to the benzene ring so as to be in the meta-position or the para-position to each other.

The inventive compound (1) represented by the formula (1) is preferably represented by the following formula (1-25) or formula (1-26).

In the formulae (1-25) and (1-26),

Y1to Y5and *a are as defined in the formula (1).

m4, m5, *b3, *b4, and *e are as defined in the formulae (1-14) and (1-15).

Preferably, *a bonds to any one of the 8- to 10-positions of the benzoxanthene ring that the compound represented by the formulae (1-14) and (1-15) has.

In the formula (1-25), when m4 is 1, preferably, *b3 and *e bond to the benzene ring so as to be in the meta-position or the para-position to each other.

In the formula (1-26), when m5 is 1, preferably, *b4 and *e bond to the naphthalene ring so as to be in the 1-position and the 4-position or in the 2-position and the 6-position to each other.

The inventive compound (1) represented by the formula (1) is preferably represented by the following formula (1-25-a), formula (1-25-b) or formula (1-25-c).

In the formulae (1-25-a) to (1-25-c), Y1to Y5, m4, *b3, and *e are as defined in the formula (1) and the formula (1-25).

In the formulae (1-25-a) to (1-25-c), when m4 is 1, preferably, *b3 and *e bond to the benzene ring so as to be in the meta-position or the para-position to each other.

The inventive compound (1) represented by the formula (1) is preferably represented by the following formula (1-26-a), formula (1-26-b) or formula (1-26-c).

In the formulae (1-26-a) to (1-26-c), Y1to Y5, m5, *b4, and *e are as defined in the formula (1) and the formula (1-26).

In the formulae (1-26-a) to (1-26-c), when m5 is 1, preferably, *b4 and *e bond to the naphthalene ring so as to be in the 1-position and the 4-position or in the 2-position and the 6-position to each other.

As embodiments of the present invention,

(1-1) R1to R6may be all hydrogen atoms,
(1-2) R7to R10that are not a single bond bonding to *a may be all hydrogen atoms,
(1-3) R's may be all hydrogen atoms,
(1-4) Ara's may be all hydrogen atoms,
(1-5) Arb's may be all hydrogen atoms,
(1-6) In the formula (1-11), R11to R16that are not a single bond bonding to *b and *c may be all hydrogen atoms,
(1-7) In the formula (1-11), R21to R26that are not a single bond bonding to *d and *e may be all hydrogen atoms,
(1-8) In the formula (1-12), R31to R36that are not a single bond bonding to *b1 and *c1 may be all hydrogen atoms,
(1-9) In the formula (1-12), R41to R48that are not a single bond bonding to *d1 and *e may be all hydrogen atoms,
(1-10) In the formula (1-13), R51to R58that are not a single bond bonding to *b2 and *c2 may be all hydrogen atoms,
(1-11) In the formula (1-13), R61to R66that are not a single bond bonding to *d2 and *e may be all hydrogen atoms,
(1-12) In the formula (1-14), R71to R76that are not a single bond bonding to *b3 and *e may be all hydrogen atoms,
(1-13) In the formula (1-15), R81to R88that are not a single bond bonding to *b4 and *e may be all hydrogen atoms.

As described above, the “hydrogen atom” referred in the description herein encompasses a protium atom, a deuterium atom, and a tritium atom. Accordingly, the inventive compound may contain a naturally-derived deuterium atom.

A deuterium atom may be intentionally introduced into the inventive compound by using a deuterated compound as a part or the whole of the raw material. Accordingly, in one embodiment of the present invention, the inventive compound contains at least one deuterium atom. That is, the inventive compound (1) may be a compound represented by the formula (1) in which at least one hydrogen atom contained in the compound is a deuterium atom.

In the compound represented by the formula (1),

at least one hydrogen atom selected from:

a hydrogen atom that the 6-membered ring formed of the carbon atom ** and Y1to Y5to constitute the formula (1) has;

a hydrogen atom that the substituted or unsubstituted (2+p)-valent aromatic hydrocarbon ring having 6 to 12 ring carbon atoms represented by L1has; and

a hydrogen atom that the substituted or unsubstituted (2+q)-valent aromatic hydrocarbon ring having 6 to 12 ring carbon atoms represented by L2has,

may be a deuterium atom.

The deuteration rate of the inventive compound depends on the deuteration rate of the raw material compound used. Even when a raw material having a predetermined deuteration rate is used, a naturally-derived protium isotope may be contained in a certain ratio. Accordingly, an embodiment of the deuteration rate of the inventive compound shown below includes the proportion for which a minor amount of a naturally-derived isotope is taken into consideration, relative to the proportion determined by counting the number of the deuterium atoms merely represented by a chemical formula.

The deuteration rate of the inventive compound is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, further more preferably 10% or more, further more preferably 50% or more.

The inventive compound may be a mixture of a deuterated compound and a non-deuterated compound, or a mixture of two or more compounds having different deuteration rates from each other. The deuteration rate of the mixture is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, further more preferably 10% or more, further more preferably 50% or more, and is less than 100%.

The proportion of the number of the deuterium atoms to the number of all the hydrogen atoms in the inventive compound is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, further more preferably 10% or more, and is 100% or less.

Details of the substituent (arbitrary substituent) in the expression “substituted or unsubstituted” included in the definitions of the aforementioned formulae are the same as in the “substituent in the expression ‘substituted or unsubstituted’”.

The inventive compound can be readily produced by a person skilled in the art with reference to the following synthesis examples and the known synthesis methods.

Specific examples of the inventive compound will be described below, but the inventive compound is not limited to the following example compounds.

In the following examples, D represents a deuterium atom.

Material for Organic EL Devices

The material for organic EL devices of the present invention contains the inventive compound. The content of the inventive compound in the material for organic EL devices of the present invention may be 1% by mass or more (including 100%), and is preferably 10% by mass or more (including 100%), more preferably 50% by mass or more (including 100%), further preferably 80% by mass or more (including 100%), still further preferably 90% by mass or more (including 100%). The material for organic EL devices of the present invention is useful for the production of an organic EL device.

Organic EL Device

The organic EL device of the present invention includes an anode, a cathode, and organic layers intervening between the anode and the cathode. The organic layers include a light emitting layer, and at least one layer of the organic layers contains the inventive compound.

Examples of the organic layer containing the inventive compound include a hole transporting zone (such as a hole injecting layer, a hole transporting layer, an electron blocking layer, and an exciton blocking layer) intervening between the anode and the light emitting layer, the light emitting layer, a space layer, and an electron transporting zone (such as an electron injecting layer, an electron transporting layer, and a hole blocking layer) intervening between the cathode and the light emitting layer, but are not limited thereto.

The inventive compound is preferably used as a material for the electron transporting zone or the light emitting layer in a fluorescent or phosphorescent EL device, and contained in an electron transporting zone. More preferably, the inventive compound is used as a material for an electron transporting layer or a hole blocking layer, especially preferably as a material for a first electron transporting layer, a second electron transporting layer or a hole blocking layer, and is contained in these layers.

The organic EL device of the present invention may be a fluorescent or phosphorescent light emission-type monochromatic light emitting device or a fluorescent/phosphorescent hybrid-type white light emitting device, and may be a simple type having a single light emitting unit or a tandem type having a plurality of light emitting units. Above all, the fluorescent light emission-type device is preferred. The “light emitting unit” referred to herein refers to a minimum unit that emits light through recombination of injected holes and electrons, which includes organic layers among which at least one layer is a light emitting layer.

For example, as a representative device configuration of the simple type organic EL device, the following device configuration may be exemplified.

The light emitting unit may be a multilayer type having a plurality of phosphorescent light emitting layers or fluorescent light emitting layers. In this case, a space layer may intervene between the light emitting layers for the purpose of preventing excitons generated in the phosphorescent light emitting layer from diffusing into the fluorescent light emitting layer. Representative layer configurations of the simple type light emitting unit are described below. Layers in parentheses are optional.

The phosphorescent and fluorescent light emitting layers may emit emission colors different from each other, respectively. Specifically, in the light emitting unit (f), a layer configuration, such as (hole injecting layer/) hole transporting layer/first phosphorescent light emitting layer (red light emission)/second phosphorescent light emitting layer (green light emission)/space layer/fluorescent light emitting layer (blue light emission)/electron transporting layer, may be exemplified.

An electron blocking layer may be properly provided between each light emitting layer and the hole transporting layer or the space layer. A hole blocking layer may be properly provided between each light emitting layer and the electron transporting layer. The employment of the electron blocking layer or the hole blocking layer allows to improve the emission efficiency by trapping electrons or holes within the light emitting layer and increasing the probability of charge recombination in the light emitting layer.

As a representative device configuration of the tandem type organic EL device, the following device configuration may be exemplified.

For example, each of the first light emitting unit and the second light emitting unit may be independently selected from the above-described light emitting units.

The intermediate layer is also generally referred to as an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron withdrawing layer, a connecting layer, or an intermediate insulating layer, and a known material configuration can be used, in which electrons are supplied to the first light emitting unit, and holes are supplied to the second light emitting unit.

FIG. 1is a schematic illustration showing an example of the configuration of the organic EL device of the present invention. The organic EL device1of this example includes a substrate2, an anode3, a cathode4, and a light emitting unit10disposed between the anode3and the cathode4. The light emitting unit10includes a light emitting layer5. A hole transporting zone6(such as a hole injecting layer and a hole transporting layer) is provided between the light emitting layer5and the anode3, and an electron transporting zone7(such as an electron injecting layer and an electron transporting layer) is provided between the light emitting layer5and the cathode4. In addition, an electron blocking layer (which is not shown in the figure) may be provided on the side of the anode3of the light emitting layer5, and a hole blocking layer (which is not shown in the figure) may be provided on the side of the cathode4of the light emitting layer5. According to the configuration, electrons and holes are trapped in the light emitting layer5, thereby enabling one to further increase the production efficiency of excitons in the light emitting layer5.

FIG. 2is a schematic illustration showing another configuration of the organic EL device of the present invention. An organic EL device11includes the substrate2, the anode3, the cathode4, and a light emitting unit20disposed between the anode3and the cathode4. The light emitting unit20includes the light emitting layer5. A hole transporting zone disposed between the anode3and the light emitting layer5is formed of a hole injecting layer6a, a first hole transporting layer6band a second hole transporting layer6c. A hole transporting zone disposed between the light emitting layer and the cathode4is formed of a first electron transporting layer7aand a second electron transporting layer7b.

In the present invention, a host combined with a fluorescent dopant material (a fluorescent emitting material) is referred to as a fluorescent host, and a host combined with a phosphorescent dopant material is referred to as a phosphorescent host. The fluorescent host and the phosphorescent host are not distinguished from each other merely by the molecular structures thereof. Specifically, the phosphorescent host means a material that forms a phosphorescent light emitting layer containing a phosphorescent dopant, but does not mean unavailability as a material that forms a fluorescent light emitting layer. The same also applies to the fluorescent host.

Substrate

The substrate is used as a support of the organic EL device. Examples of the substrate include a plate of glass, quartz, and plastic. In addition, a flexible substrate may be used. Examples of the flexible substrate include a plastic substrate made of polycarbonate, polyarylate, polyether sulfone, polypropylene, polyester, polyvinyl fluoride, or polyvinyl chloride. In addition, an inorganic vapor deposition film can be used.

Anode

It is preferred that a metal, an alloy, an electrically conductive compound, or a mixture thereof which has a high work function (specifically 4.0 eV or more) is used for the anode formed on the substrate. Specific examples thereof include indium oxide-tin oxide (ITO: Indium Tin Oxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene. Besides, examples there include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of the metals (for example, titanium nitride).

These materials are usually deposited by a sputtering method. For example, through a sputtering method, it is possible to form indium oxide-zinc oxide by using a target in which 1 to 10 wt % of zinc oxide is added to indium oxide, and to form indium oxide containing tungsten oxide and zinc oxide by using a target containing 0.5 to 5 wt % of tungsten oxide and 0.1 to 1 wt % of zinc oxide with respect to indium oxide. Besides, the manufacturing may be performed by a vacuum vapor deposition method, a coating method, an inkjet method, a spin coating method, or the like.

The hole injecting layer formed in contact with the anode is formed by using a material that facilitates hole injection regardless of a work function of the anode, and thus, it is possible to use materials generally used as an electrode material (for example, metals, alloys, electrically conductive compounds, or mixtures thereof, elements belonging to Group 1 or 2 of the periodic table of the elements).

It is also possible to use elements belonging to Group 1 or 2 of the periodic table of the elements, which are materials having low work functions, that is, alkali metals, such as lithium (L1) and cesium (Cs), alkaline earth metals, such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (such as MgAg and AlLi), and rare earth metals, such as europium (Eu), and ytterbium (Yb) and alloys containing these. When the anode is formed by using the alkali metals, the alkaline earth metals, and alloys containing these, a vacuum vapor deposition method or a sputtering method can be used. Further, when a silver paste or the like is used, a coating method, an inkjet method, or the like can be used.

Hole Injecting Layer

The hole injecting layer is a layer containing a material having a high hole injection capability (a hole injecting material) and is provided between the anode and the light emitting layer, or between the hole transporting layer, if exists, and the anode.

Furthermore, it is also preferred to use an acceptor material, such as a hexaazatriphenylene (HAT) compound represented by formula (K).

In the aforementioned formula, R21to R26each independently represent a cyano group, —CONH2, a carboxy group, or —COOR27(R27represents an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms). In addition, adjacent two selected from R21and R22, R23and R24, and R25and R26may be bonded to each other to form a group represented by —CO—O—CO—.

Examples of R27include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, a cyclopentyl group, and a cyclohexyl group.

Hole Transporting Layer

The hole transporting layer is a layer containing a material having a high hole transporting capability (a hole transporting material) and is provided between the anode and the light emitting layer, or between the hole injecting layer, if exists, and the light emitting layer.

The hole transporting layer may have a single layer structure or a multilayer structure including two or more layers. For example, the hole transporting layer may have a two-layer structure including a first hole transporting layer (anode side) and a second hole transporting layer (cathode side). In one embodiment of the present invention, the hole transporting layer having a single layer structure is preferably disposed adjacent to the light emitting layer, and the hole transporting layer that is closest to the cathode in the multilayer structure, such as the second hole transporting layer in the two-layer structure, is preferably disposed adjacent to the light emitting layer. In another embodiment of the present invention, an electron blocking layer described later and the like may be disposed between the hole transporting layer having a single layer structure and the light emitting layer, or between the hole transporting layer that is closest to the light emitting layer in the multilayer structure and the light emitting layer.

As the hole transporting material, for example, an aromatic amine compound, a carbazole derivative, an anthracene derivative, and the like can be used.

However, compounds other than those as mentioned above can also be used so long as they are compounds high in the hole transporting capability rather than in the electron transporting capability.

Dopant Material of Light Emitting Layer

The light emitting layer is a layer containing a material having a high light emitting property (a dopant material), and various materials can be used. For example, a fluorescent emitting material or a phosphorescent emitting material can be used as the dopant material. The fluorescent emitting material is a compound that emits light from a singlet excited state, and the phosphorescent emitting material is a compound that emits from a light triplet excited state.

Examples of a blue-based fluorescent emitting material that can be used for the light emitting layer include a pyrene derivative, a styrylamine derivative, a chrysene derivative, a fluoranthene derivative, a fluorene derivative, a diamine derivative, and a triarylamine derivative. Specific examples thereof include N,N′-bis[4-(9H-carbazole-9-yl)phenyl]-N,N′-diphenylstilbene-4,4′-diamine (abbreviation: YGA2S), 4-(9H-carbazole-9-yl)-4′-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), and 4-(10-phenyl-9-anthryl)-4′-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBAPA).

Examples of a red-based fluorescent emitting material that can be used for the light emitting layer include a tetracene derivative and a diamine derivative. Specific examples thereof include N,N,N′,N′-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD) and 7,14-diphenyl-N,N,N′,N′-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD).

In one embodiment of the present invention, the light emitting layer contains a fluorescent emitting material (fluorescent dopant material).

Examples of a blue-based phosphorescent emitting material that can be used for the light emitting layer include a metal complex, such as an iridium complex, an osmium complex, and a platinum complex. Specific examples thereof include bis[2-(4′,6′-difluorophenyl)pyridinato-N,C2′]iridium(III)tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4′,6′-difluorophenyl)pyridinato-N,C2′]iridium(III)picolinate (abbreviation: FIrpic), bis[2-(3′,5′bistrifluoromethylphenyl)pyridinato-N,C2′]iridium(III)picolinate (abbreviation: Ir(CF3ppy)2(pic)), and bis[2-(4′,6′-difluorophenyl)pyridinato-N,C2′]iridium(III)acetylacetonate (abbreviation: FIracac).

Examples of a green-based phosphorescent emitting material that can be used for the light emitting layer include an iridium complex. Examples thereof include tris(2-phenylpyridinato-N,C2′)iridium(III) (abbreviation: Ir(ppy)3), bis(2-phenylpyridinato-N,C2′)iridium(III)acetylacetonate (abbreviation: Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazolato)iridium(III)acetylacetonate (abbreviation: Ir(pbi)2(acac)), and bis(benzo[h]quinolinato)iridium(III)acetylacetonate (abbreviation: Ir(bzq)2(acac)).

Examples of a red-based phosphorescent emitting material that can be used for the light emitting layer include a metal complex, such as an iridium complex, a platinum complex, a terbium complex, and a europium complex. Specific examples thereof include organic metal complexes, such as bis[2-(2′-benzo[4,5-a]thienyl)pyridinato-N,C3′]iridium(III)acetylacetonate (abbreviation: Ir(btp)2(acac)), bis(1-phenylisoquinolinato-N,C2′)iridium(III)acetylacetonate (abbreviation: Ir(piq)2(acac)), (acetylacetonate)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: Ir(Fcdpq)2(acac)), and 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrinplatinum(II) (abbreviation: PtOEP).

Rare earth metal complexes, such as tris(acetylacetonate) (monophenanthroline)terbium(III) (abbreviation: Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propanedionate)(monophenanthroline)europium(III) (abbreviation: Eu(DBM)3(Phen)), and tris[1-(2-thenoyl)-3,3,3-trifluoroacetonate](monophenanthroline)europium(III) (abbreviation: Eu(TTA)3(Phen)), emit light from rare earth metal ions (electron transition between different multiplicities), and thus may be used as the phosphorescent emitting material.

In one embodiment of the present invention, the light emitting layer contains a phosphorescent emitting material (phosphorescent dopant material).

Host Material of Light Emitting Layer

The light emitting layer may have a configuration in which the aforementioned dopant material is dispersed in another material (a host material). The host material is preferably a material that has a higher lowest unoccupied orbital level (LUMO level) and a lower highest occupied orbital level (HOMO level) than the dopant material.

Examples of the host material include:

(1) a metal complex, such as an aluminum complex, a beryllium complex, and a zinc complex,

(2) a heterocyclic compound, such as an oxadiazole derivative, a benzimidazole derivative, and a phenanthroline derivative,

(3) a fused aromatic compound, such as a carbazole derivative, an anthracene derivative, a phenanthrene derivative, a pyrene derivative, and a chrysene derivative, or

(4) an aromatic amine compound, such as a triarylamine derivative and a fused polycyclic aromatic amine derivative.

For example,

In particular, in the case of a blue fluorescent device, it is preferred to use the following anthracene compounds as the host material.

Electron Transporting Layer

The electron transporting layer is a layer containing a material having a high electron transporting capability (an electron transporting material) and is provided between the light emitting layer and the cathode, or between the electron injecting layer, if exists, and the light emitting layer. The inventive compound can be used alone in the electron transporting layer or can be used as a combination with the following compounds therein.

The electron transporting layer may have a single layer structure or a multilayer structure including two or more layers. For example, the electron transporting layer may have a two-layer structure including a first electron transporting layer (anode side) and a second electron transporting layer (cathode side). In one embodiment of the present invention, the electron transporting layer having a single layer structure is preferably disposed adjacent to the light emitting layer, and the electron transporting layer that is closest to the anode in the multilayer structure, such as the first electron transporting layer in the two-layer structure, is preferably disposed adjacent to the light emitting layer. In another embodiment of the present invention, a hole blocking layer described later and the like may be disposed between the electron transporting layer having a single layer structure and the light emitting layer, or between the electron transporting layer that is closest to the light emitting layer in the multilayer structure and the light emitting layer.

In the electron transporting layer having a two-layer structure, one or both of the first electron transporting layer and the second electron transporting layer may contain the inventive compound.

In one embodiment of the present invention, the inventive compound is contained only in the first electron transporting layer, and in another embodiment thereof, the inventive compound is contained only in the second electron transporting layer, and in still another embodiment thereof, the inventive compound is contained in the first electron transporting layer and the second electron transporting layer.

In one embodiment of the present invention, the inventive compound contained in one or both of the first electron transporting layer and the second electron transporting layer is preferably a protium compound from the viewpoint of production cost.

The protium compound is the inventive compound where all hydrogen atoms are protium atoms.

Accordingly, the present invention includes an organic EL device where one or both of the first electron transporting layer and the second electron transporting layer contain the inventive compound of substantially a protium compound alone. The “inventive compound of substantially a protium compound alone” means that the content ratio of a protium compound relative to the total amount of the inventive compound is 90 mol % or more, preferably 95 mol % or more, more preferably 99 mol % or more (each inclusive of 100%).

Examples of the material which can be used for the electron transporting layer include:

(1) a metal complex, such as an aluminum complex, a beryllium complex, and a zinc complex;

(2) a heteroaromatic compound, such as an imidazole derivative, a benzimidazole derivative, an azine derivative, a carbazole derivative, and a phenanthroline derivative; and

Examples of the high-molecular weight compound include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy).

The materials are materials having an electron mobility of 10−6cm2/Vs or more. Materials other than those as mentioned above may also be used in the electron transporting layer so long as they are materials high in the electron transporting capability rather than in the hole transporting capability.

Electron Injecting Layer

The electron injecting layer is a layer containing a material having a high electron injection capability. For the electron injecting layer, alkali metals, such as lithium (Li) and cesium (Cs), alkaline earth metals, such as magnesium (Mg), calcium (Ca), and strontium (Sr), rare earth metals, such as europium (Eu) and ytterbium (Yb), and compounds containing these metals can be used. Examples of the compounds include an alkali metal oxide, an alkali metal halide, an alkali metal-containing organic complex, an alkaline earth metal oxide, an alkaline earth metal halide, an alkaline earth metal-containing organic complex, a rare earth metal oxide, a rare earth metal halide, and a rare earth metal-containing organic complex. These compounds may be used as a mixture of a plurality thereof.

In addition, a material having an electron transporting capability, in which an alkali metal, an alkaline earth metal, or a compound thereof is contained, specifically Alq in which magnesium (Mg) is contained may be used. In this case, electron injection from the cathode can be more efficiently performed.

Otherwise, in the electron injecting layer, a composite material obtained by mixing an organic compound with an electron donor may be used. Such a composite material is excellent in the electron injection capability and the electron transporting capability because the organic compound receives electrons from the electron donor. In this case, the organic compound is preferably a material excellent in transporting received electrons, and specifically, examples thereof include a material constituting the aforementioned electron transporting layer (such as a metal complex and a heteroaromatic compound). As the electron donor, a material having an electron donation property for the organic compound may be used. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, and examples thereof include lithium, cesium, magnesium, calcium, erbium, and ytterbium. In addition, an alkali metal oxide or an alkaline earth metal oxide is preferred, and examples thereof include lithium oxide, calcium oxide, and barium oxide. In addition, a Lewis base, such as magnesium oxide, can also be used. In addition, an organic compound, such as tetrathiafulvalene (abbreviation: TTF), can also be used.

In other words, the electron transporting zone including the electron injecting layer may contain one or more selected from the group consisting of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, an alkaline earth metal oxide, an alkaline earth metal halide, a rare earth metal oxide, a rare earth metal halide, an alkali metal-containing organic complex, an alkaline earth metal-containing organic complex, and a rare earth metal-containing organic complex.

Cathode

It is preferred that a metal, an alloy, an electrically conductive compound, or a mixture thereof which has a low work function (specifically 3.8 eV or less) is used for the cathode. Specific examples of such a cathode material include elements belonging to group 1 or 2 of the periodic table of the elements, that is, alkali metals, such as lithium (Li) and cesium (Cs), alkaline earth metals, such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (such as MgAg, and AlLi), and rare earth metals, such as europium (Eu), and ytterbium (Yb) and alloys containing these.

When the cathode is formed by using the alkali metals, the alkaline earth metals, and the alloys containing these, a vacuum vapor deposition method or a sputtering method can be adopted. In addition, when a silver paste or the like is used, a coating method, an inkjet method, of the like can be adopted.

By providing the electron injecting layer, the cathode can be formed using various conductive materials, such as Al, Ag, ITO, graphene, and indium oxide-tin oxide containing silicon or silicon oxide regardless of the magnitude of a work function. Such a conductive material can be deposited by using a sputtering method, an inkjet method, a spin coating method, or the like.

Insulating Layer

The organic EL device applies an electric field to an ultrathin film, and thus, pixel defects are likely to occur due to leaks or short-circuiting. In order to prevent this, an insulating layer formed of an insulating thin film layer may be inserted between a pair of electrodes.

Examples of the material used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, and vanadium oxide. A mixture or a laminate of these may also be used.

Space Layer

The space layer is, for example, a layer provided between a fluorescent light emitting layer and a phosphorescent light emitting layer for the purpose of preventing excitons generated in the phosphorescent light emitting layer from diffusing into the fluorescent light emitting layer, or adjusting a carrier balance, in the case where the fluorescent light emitting layers and the phosphorescent light emitting layers are stacked. The space layer can also be provided among the plurality of phosphorescent light emitting layers.

Since the space layer is provided between the light emitting layers, a material having both an electron transporting capability and a hole transporting capability is preferred. Also, one having a triplet energy of 2.6 eV or more is preferred in order to prevent triplet energy diffusion in the adjacent phosphorescent light emitting layer. Examples of the material used for the space layer include the same as those used for the hole transporting layer as described above.

Blocking Layer

The blocking layer such as the electron blocking layer, the hole blocking layer, or the exciton blocking layer may be provided adjacent to the light emitting layer. The electron blocking layer is a layer that prevents electrons from leaking from the light emitting layer to the hole transporting layer, and the hole blocking layer is a layer that prevents holes from leaking from the light emitting layer to the electron transporting layer. The exciton blocking layer has a function of preventing excitons generated in the light emitting layer from diffusing into the surrounding layers, and trapping the excitons within the light emitting layer.

In one embodiment of the present invention, the electron transporting zone includes the hole blocking layer on the cathode side, and the hole blocking layer contains the inventive compound. In one embodiment of the present invention, the hole blocking layer is adjacent to the light emitting layer.

Each layer of the organic EL device may be formed by a conventionally known vapor deposition method, a coating method, or the like. For example, formation can be performed by a known method using a vapor deposition method such as a vacuum vapor deposition method, or a molecular beam vapor deposition method (MBE method), or a coating method using a solution of a compound for forming a layer, such as a dipping method, a spin-coating method, a casting method, a bar-coating method, and a roll-coating method.

The film thickness of each layer is not particularly limited, but is typically 5 nm to 10 μm, and more preferably 10 nm to 0.2 μm because in general, when the film thickness is too small, defects such as pinholes are likely to occur, and conversely, when the film thickness is too large, a high driving voltage is required and the efficiency decreases.

The organic EL device can be used for electronic apparatuses, such as display components of an organic EL panel module and the like, displays of a television, a mobile phone, a personal computer, and the like, and light emitters of lightings and vehicular lamps.

EXAMPLES

The present invention is hereunder described in more detail by reference to Examples, but it should be construed that the present invention is not limited to the following Examples.

Inventive Compounds Used for Production of Organic EL Devices (I-1) to (I-6) of Examples 1 to 6 and Organic EL Devices (II-1) to (II-6) of Examples 7 to 12

Compounds Used for Production of Organic EL Devices (I-A) to (I-C) of Comparative Examples 1 to 3 and Organic EL Devices (II-A) to (II-C) of Comparative Examples 4 to 6

Other Compounds Used for Production of Organic EL Devices (I-1) to (I-6) and Organic EL Devices (II-1) to (II-6)

Example 1: Production of Organic EL Device (I-1)

A glass substrate of 25 mm×75 mm×1.1 mm provided with an ITO transparent electrode (anode) (manufactured by GEOMATEC Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then subjected to UV ozone cleaning for 30 minutes. The film thickness of the ITO was 130 nm.

The cleaned glass substrate provided with the ITO transparent electrode lines was mounted on a substrate holder of a vacuum vapor deposition apparatus, and firstly, Compound HT-1 and Compound HI-1 were vapor co-deposited on the surface having the transparent electrode formed thereon, so as to cover the transparent electrode, resulting in a hole injecting layer with a film thickness of 10 nm. The mass ratio of Compound HT-1 to Compound HI-1 (HT-1/HI-1) was 97/3.

Subsequently, on this hole injecting layer, Compound HT-1 was vapor deposited to form a first hole transporting layer with a film thickness of 80 nm.

Subsequently, on this first hole transporting layer, Compound EBL-1 was vapor deposited to form a second hole transporting layer with a film thickness of 5 nm.

Subsequently, on this second hole transporting layer, Compound BH-1 (host material) and Compound BD-1 (dopant material) were vapor co-deposited to form a light emitting layer with a film thickness of 25 nm. The mass ratio of Compound BH-1 to Compound BD-1 (BH-1/BD-1) was 96/4.

Subsequently, on this light emitting layer, Compound HBL-1 was vapor deposited to form a first electron transporting layer with a film thickness of 5 nm.

Subsequently, on this first electron transporting layer, Compound 1 and Liq were vapor co-deposited to form a second electron transporting layer with a film thickness of 20 nm. The mass ratio of Compound 1 to Liq (Compound 1/Liq) was 50/50.

Subsequently, on this electron transporting layer, Yb was vapor deposited to form an electron injecting electrode with a film thickness of 1 nm.

Then, on this electron injecting electrode, metal Al was vapor deposited to form a metal cathode with a film thickness of 50 nm.

The layer configuration of the organic EL device (I-1) of Example 1 thus obtained was as follows.

In the layer configuration, the numeral in parentheses indicates the film thickness (nm), and the ratio is a mass ratio.

Measurement of External Quantum Efficiency (EQE)

The resulting organic EL device was driven at room temperature with DC direct current at a current density of 10 mA/cm2, and the luminance thereof was measured with a spectral radiance meter “CS-1000” (by Konica Minolta, Inc. From the found data, the external quantum efficiency was (%) derived. The results are shown in Table 1.

Measurement of Device Lifetime (LT95)

The resulting organic EL device was driven at room temperature with direct current at a current density of 50 mA/cm2, and the period of time until the luminance was reduced to 95% of the initial luminance was measured, and was defined as LT95 (95% lifetime). The results are shown in Table 1.

Example 2: Production of Organic EL Device (I-2)

An organic EL device (I-2) was produced in the same manner as in Example 1, except that Compound 1 as the first electron transporting layer material was changed to Compound 2, and the external quantum efficiency and LT95 thereof were measured. The results are shown in Table 1.

Example 3: Production of Organic EL Device (I-3)

An organic EL device (I-3) was produced in the same manner as in Example 1, except that Compound 1 as the first electron transporting layer material was changed to Compound 3, and the external quantum efficiency and LT95 thereof were measured. The results are shown in Table 1.

Example 4: Production of Organic EL Device (I-4)

An organic EL device (I-4) was produced in the same manner as in Example 1, except that Compound 1 as the first electron transporting layer material was changed to Compound 4, and the external quantum efficiency and LT95 thereof were measured. The results are shown in Table 1.

Example 5: Production of Organic EL Device (I-5)

An organic EL device (I-5) was produced in the same manner as in Example 1, except that Compound 1 as the first electron transporting layer material was changed to Compound 5, and the external quantum efficiency and LT95 thereof were measured. The results are shown in Table 1.

Example 6: Production of Organic EL Device (I-6)

An organic EL device (I-6) was produced in the same manner as in Example 1, except that Compound 1 as the first electron transporting layer material was changed to Compound 6, and the external quantum efficiency and LT95 thereof were measured. The results are shown in Table 1.

Comparative Example 1: Production of Organic EL Device (I-A)

An organic EL device (I-A) was produced in the same manner as in Example 1, except that Compound 1 as the first electron transporting layer material was changed to Compound A, and the external quantum efficiency and LT95 thereof were measured. The results are shown in Table 1.

Comparative Example 2: Production of Organic EL Device (I-B)

An organic EL device (I-B) was produced in the same manner as in Example 1, except that Compound 1 as the first electron transporting layer material was changed to Compound B, and the external quantum efficiency and LT95 thereof were measured. The results are shown in Table 1.

Comparative Example 3: Production of Organic EL Device (I-C)

An organic EL device (I-C) was produced in the same manner as in Example 1, except that Compound 1 as the first electron transporting layer material was changed to Compound C, and the external quantum efficiency and LT95 thereof were measured. The results are shown in Table 1.

From the results in Table 1, it is known that the compound of the present invention provides an organic EL device having a high external quantum efficiency and a prolonged device lifetime.

Example 7: Production of Organic EL Device (II-1)

A glass substrate of 25 mm×75 mm×1.1 mm provided with an ITO transparent electrode (anode) (by GEOMATEC Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then subjected to UV ozone cleaning for 30 minutes. The film thickness of the ITO was 130 nm.

The cleaned glass substrate provided with the ITO transparent electrode was mounted on a substrate holder of a vacuum vapor deposition apparatus, and firstly, Compound HT-2 and Compound HI-1 were vapor co-deposited on the surface having the transparent electrode formed thereon, so as to cover the transparent electrode, resulting in a hole injecting layer with a film thickness of 10 nm. The mass ratio of Compound HT-2 to Compound HI-1 (HT-2/HI-1) was 97/3.

Subsequently, on this hole injecting layer, Compound HT-2 was vapor deposited to form a first hole transporting layer with a film thickness of 80 nm.

Subsequently, on this first hole transporting layer, Compound EBL-1 was vapor deposited to form a second hole transporting layer with a film thickness of 5 nm.

Subsequently, on this second hole transporting layer, Compound BH-2 (host material) and Compound BD-1 (dopant material) were vapor co-deposited to form a light emitting layer with a film thickness of 25 nm. The mass ratio of Compound BH-2 to Compound BD-1 (BH-2/BD-1) was 96/4.

Subsequently, on this light emitting layer, Compound HBL-1 was vapor deposited to form a first electron transporting layer with a film thickness of 5 nm.

Subsequently, on this first electron transporting layer, Compound 1 and Liq were vapor co-deposited to form a second electron transporting layer with a film thickness of 20 nm. The mass ratio of Compound 1 to Liq (Compound 1/Liq) was 50/50.

Subsequently, on this second electron transporting layer, Yb was vapor deposited to form an electron injecting electrode with a film thickness of 1 nm.

Then, on this electron injecting electrode, metal Al was vapor deposited to form a metal cathode with a film thickness of 50 nm.

The external quantum efficiency and LT95 of the thus-produced organic EL device (II-1) of Example 4 were measured in the same manner as in Example 1. The results are shown in Table 2. The layer configuration of the organic EL device (II-1) of Example 4 is shown below.

In the layer configuration, the numeral in parentheses indicates the film thickness (nm), and the ratio is a mass ratio.

Example 8: Production of Organic EL Device (II-2)

An organic EL device (II-2) was produced in the same manner as in Example 4, except that Compound 1 as the first electron transporting layer material was changed to Compound 2, and the external quantum efficiency and LT95 thereof were measured. The results are shown in Table 2.

Example 9: Production of Organic EL Device (11-3)

An organic EL device (II-3) was produced in the same manner as in Example 4, except that Compound 1 as the first electron transporting layer material was changed to Compound 3, and the external quantum efficiency and LT95 thereof were measured. The results are shown in Table 2.

Example 10: Production of Organic EL Device (II-4)

An organic EL device (II-4) was produced in the same manner as in Example 7, except that Compound 1 as the first electron transporting layer material was changed to Compound 4, and the external quantum efficiency and LT95 thereof were measured. The results are shown in Table 2.

Example 11: Production of Organic EL Device (II-5)

An organic EL device (II-5) was produced in the same manner as in Example 7, except that Compound 1 as the first electron transporting layer material was changed to Compound 5, and the external quantum efficiency and LT95 thereof were measured. The results are shown in Table 2.

Example 12: Production of Organic EL Device (II-6)

An organic EL device (II-6) was produced in the same manner as in Example 7, except that Compound 1 as the first electron transporting layer material was changed to Compound 6, and the external quantum efficiency and LT95 thereof were measured. The results are shown in Table 2.

Comparative Example 4: Production of Organic EL Device (II-A)

An organic EL device (II-A) was produced in the same manner as in Example 7, except that Compound 1 as the first electron transporting layer material was changed to Compound A, and the external quantum efficiency and LT95 thereof were measured. The results are shown in Table 2.

Comparative Example 5: Production of Organic EL Device (II-B)

An organic EL device (II-B) was produced in the same manner as in Example 7, except that Compound 1 as the first electron transporting layer material was changed to Compound B, and the external quantum efficiency and LT95 thereof were measured. The results are shown in Table 2.

Comparative Example 6: Production of Organic EL Device (II-C)

An organic EL device (II-C) was produced in the same manner as in Example 7, except that Compound 1 as the first electron transporting layer material was changed to Compound C, and the external quantum efficiency and LT95 thereof were measured. The results are shown in Table 2.

From the results in Table 2, it is known that the compound of the present invention provides an organic EL device having a high external quantum efficiency and a prolonged device lifetime.

Compounds Synthesized in Synthesis Examples

Synthesis Example 1: Synthesis of Compound 1

(I-1) Synthesis of Intermediate B

Intermediate A (10.0 g) synthesized according to the method described in WO2015/122711A1, bis(pinacolato)diboron (12.1 g), Pd2(dba)3(0.73 g), XPhos (1.5 g), and potassium acetate (7.8 g) were added to 1,4-dioxane (200 mL), and an argon gas was introduced into the resulting suspension for 5 minutes. With stirring in an argon atmosphere, this was heated at 90° C. for 24 hours. The solvent was evaporated away from the reaction solution, and toluene and water were added to separate and collect an organic phase. The organic phase was concentrated, and the resulting residue was subjected to column chromatography to give 8.5 g of Intermediate B. The yield was 62%.

(I-2) Synthesis of Compound 1

Intermediate B (3.0 g) and 4-(biphenyl-4-yl)-6-(4-bromophenyl)-2-phenylpyrimidine (3.4 g) were added to 1,2-dimethoxyethane (70 mL), and an argon gas was introduced into the solution for 5 minutes. To this, PdCl2(Amphos)2(0.21 g) and an aqueous solution of sodium carbonate (2 M, 10 mL) were added, and with stirring in an argon atmosphere, this was heated at 75° C. for 24 hours. The solvent was evaporated away from the reaction solution, and the resulting solid was purified through silica gel column chromatography (developing solvent: toluene) and recrystallization with toluene to give Compound 1 as a white solid (3.2 g, yield 72%).

As a result of mass spectrometry, m/e=600 relative to the molecular weight 600.72, and the compound was identified as the target product.

Synthesis Example 2: Synthesis of Compound 2

Intermediate B (2.26 g) and 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine (2.5 g) were used, and under the condition in (1-2) in Synthesis Example 1, Compound 2 was produced as a white solid (2.9 g, yield 76%).

As a result of mass spectrometry, m/e=524 relative to the molecular weight 524.62, and the compound was identified as the target product.

Synthesis Example 3: Synthesis of Compound 3

Intermediate B (3.0 g) and 2-(biphenyl-4-yl)-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine (3.3 g) were used, and under the condition in (1-2) in Synthesis Example 1, Compound 3 was produced as a white solid (3.6 g, yield 76%).

As a result of mass spectrometry, m/e=601 relative to the molecular weight 601.71, and the compound was identified as the target product.

Synthesis Example 4: Synthesis of Compound 4

Intermediate B (3.0 g) and 2-(biphenyl-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.3 g) were used, and under the condition in (1-2) in Synthesis Example 1, Compound 4 was produced as a white solid (3.3 g, yield 65%).

As a result of mass spectrometry, m/e=525 relative to the molecular weight 525.61, and the compound was identified as the target product.

Synthesis Example 5: Synthesis of Compound 5

Intermediate B (4.5 g) and Intermediate C (synthesized according to the method disclosed in WO2019/017616, 3.3 g) were used, and under the condition in (1-2) in Synthesis Example 1, Compound 5 was produced as a white solid (3.6 g, yield 62%).

As a result of mass spectrometry, m/e=601 relative to the molecular weight 601.71, and the compound was identified as the target product.

Synthesis Example 6: Synthesis of Compound 6

Intermediate B (3.0 g) and Intermediate D (CAS RN 275876-18-0, 3.3 g) were used, and under the condition in (1-2) in Synthesis Example 1, Compound 6 was produced as a white solid (2.3 g, yield 49%).

As a result of mass spectrometry, m/e=534 relative to the molecular weight 534.67, and the compound was identified as the target product.

REFERENCE SIGNS LIST