COMPOUND FOR ORGANIC OPTOELECTRONIC DEVICE, COMPOSITION FOR ORGANIC OPTOELECTRONIC DEVICE, ORGANIC OPTOELECTRONIC DEVICE AND DISPLAY DEVICE

A compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device, the compound being represented by Chemical Formula 1:

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean Patent Application No. 10-2021-0080242, filed in the Korean Intellectual Property Office on Jun. 21, 2021, and Korean Patent Application No. 10-2022-0075165, filed in the Korean Intellectual Property Office on Jun. 20, 2022, the entire contents of which are incorporated herein by reference.

BACKGROUND

Embodiments relate to a compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device.

2. Description of the Related Art

An organic optoelectronic device (e.g., organic optoelectronic diode) is a device capable of converting electrical energy and optical energy to each other.

Organic optoelectronic devices may be divided into two types according to a principle of operation. One is a photoelectric device that generates electrical energy by separating excitons formed by light energy into electrons and holes, and transferring the electrons and holes to different electrodes, respectively and the other is light emitting device that generates light energy from electrical energy by supplying voltage or current to the electrodes.

Examples of the organic optoelectronic device include an organic photoelectric device, an organic light emitting diode, an organic solar cell, and an organic photo conductor drum.

Among them, organic light emitting diodes (OLEDs) are attracting much attention in recent years due to increasing demands for flat panel display devices. The organic light emitting diode is a device that converts electrical energy into light, and the performance of the organic light emitting diode is greatly influenced by an organic material between electrodes.

SUMMARY

The embodiments may be realized by providing a compound for an organic optoelectronic device, the compound being represented by Chemical Formula 1:

wherein, in Chemical Formula 1, X1is O or S, L1to L4are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group, R1to R3are each independently hydrogen, deuterium, or a substituted or unsubstituted C1 to C10 alkyl group, Ar1to Ar3are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, m1 an integer of 1 to 4, m2 is 1, m3 an integer of 1 to 3, and * is a linking carbon.

The embodiments may be realized by providing a composition for an organic optoelectronic device, the composition including a first compound; and a second compound, wherein the first compound is the compound for an organic optoelectronic device according to an embodiment, and the second compound is represented by Chemical Formula 2:

in Chemical Formula 2, X2is O, S, N-La-Ra, CRbRc, or SiRdRe, Lais a single bond or a substituted or unsubstituted C6 to C12 arylene group, Ra, Rb, Rc, Rd, Re, and R4are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, m4 is an integer 1 to 4, and A is a ring of Group III,

in Group III, * is a linking carbon, X3is O or S, R5to R12are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, m5, m7, m10, and m12 are each independently an integer of 1 to 4, m6, m8, m9, and m11 are each independently 1 or 2, and at least one of Ra and R4to R12is a group represented by Chemical Formula a,

in Chemical Formula a, Z1to Z3are each independently N or CRf, at least two of Z1to Z3are N, Rfis hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group, L5to L7are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group, Ar4and Ar5are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and * is a linking point.

The embodiments may be realized by providing an organic optoelectronic device including an anode and a cathode facing each other, and at least one organic layer between the anode and the cathode, wherein the at least one organic layer includes the compound for an organic optoelectronic device according to an embodiment.

The embodiments may be realized by providing an organic optoelectronic device including an anode and a cathode facing each other, at least one organic layer between the anode and the cathode, wherein the at least one organic layer includes the composition for an organic optoelectronic device according to an embodiment.

The embodiments may be realized by providing a display device including the organic optoelectronic device according to an embodiment.

DETAILED DESCRIPTION

As used herein, when a definition is not otherwise provided, “substituted” refers to replacement of at least one hydrogen of a substituent or a compound by deuterium, a halogen, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, a cyano group, or a combination thereof.

In one example, “substituted” refers to replacement of at least one hydrogen of a substituent or a compound by deuterium, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, or a cyano group. In addition, in specific examples, “substituted” refers to replacement of at least one hydrogen of a substituent or a compound by deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a cyano group. In addition, in specific examples, “substituted” refers to replacement of at least one hydrogen of a substituent or a compound by deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, or a cyano group. In addition, in specific examples, “substituted” refers to replacement of at least one hydrogen of a substituent or a compound by deuterium, a cyano group, a methyl group, an ethyl group, a propyl group, a butyl group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

“Unsubstituted” refers to non-replacement of a hydrogen atom by another substituent and remaining of the hydrogen atom.

In the present specification, “hydrogen substitution (—H)” may include “deuterium substitution (-D)” or “tritium substitution (-T).”

As used herein, when a definition is not otherwise provided, “hetero” refers to one including one to three heteroatoms selected from N, O, S, P, and Si, and remaining carbons in one functional group.

As used herein, “aryl group” refers to a group including at least one hydrocarbon aromatic moiety, and may include a group in which all elements of the hydrocarbon aromatic moiety have p-orbitals which form conjugation, for example a phenyl group, a naphthyl group, and the like, a group in which two or more hydrocarbon aromatic moieties may be linked by a sigma bond, for example a biphenyl group, a terphenyl group, a quarterphenyl group, and the like, and a group in which two or more hydrocarbon aromatic moieties are fused directly or indirectly to provide a non-aromatic fused ring, for example, a fluorenyl group, and the like.

The aryl group may include a monocyclic, polycyclic or fused ring polycyclic (i.e., rings sharing adjacent pairs of carbon atoms) functional group.

As used herein, “heterocyclic group” is a generic concept of a heteroaryl group, and may include at least one heteroatom selected from N, O, S, P, and Si instead of carbon (C) in a cyclic compound such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof. When the heterocyclic group is a fused ring, the entire ring or each ring of the heterocyclic group may include one or more heteroatoms.

For example, “heteroaryl group” refers to an aryl group including at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryl groups are linked by a sigma bond directly, or when the heteroaryl group includes two or more rings, the two or more rings may be fused. When the heteroaryl group is a fused ring, each ring may include one to three heteroatoms.

More specifically, the substituted or unsubstituted C6 to C30 aryl group may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furanyl group, or a combination thereof, but is not limited thereto.

More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group may be a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzthiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzonaphthofuranyl group, a substituted or unsubstituted benzonaphthothiophenyl group, a substituted or unsubstituted benzofuranofluorenyl group, a substituted or unsubstituted benzothiophenefluorenyl group, or a combination thereof, but is not limited thereto.

In the present specification, hole characteristics refer to an ability to donate an electron to form a hole when an electric field is applied and that a hole formed in the anode may be easily injected into the light emitting layer and transported in the light emitting layer due to conductive characteristics according to the highest occupied molecular orbital (HOMO) level.

In addition, electron characteristics refer to an ability to accept an electron when an electric field is applied and that electron formed in the cathode may be easily injected into the light emitting layer and transported in the light emitting layer due to conductive characteristics according to the lowest unoccupied molecular orbital (LUMO) level.

Hereinafter, a compound for an organic optoelectronic device according to an embodiment is described.

The compound for an organic optoelectronic device according to an embodiment may be represented by, e.g., Chemical Formula 1.

In Chemical Formula 1, X1may be, e.g., O or S. As used herein, the term “or” is not an exclusive term, e.g., “A or B” would include A, B, or A and B.

L1to L4may each independently be or include, e.g., a single bond or a substituted or unsubstituted C6 to C30 arylene group.

R1to R3may each independently be or include, e.g., hydrogen, deuterium or a substituted or unsubstituted C1 to C10 alkyl group.

Ar1to Ar3may each independently be or include, e.g., a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

m1 may be, e.g., an integer of 1 to 4.

m3 may be, e.g., an integer of 1 to 3.

* is a linking point or linking carbon. As used herein, the term “linking carbon” refers to a shared carbon at which fused rings are linked. For example, the *s may be adjacent carbons of the R2-containing ring to form a fused ring structure.

The compound represented by Chemical Formula 1 may have a more stable T1 energy level and excellent thermal stability by having a benzon[b]naphtho[2,1-d]furan or benzo[b]naphtho[1,2-d]furan backbone to help realize long life-span characteristics. The compound may have more stable HOMO energy as a dopant by including a substituted or unsubstituted amine group at the 2nd position, and a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group at the 7th position and thus may have improved hole-transporting characteristics of the luminous efficiency to help exhibit high luminous efficiency and life-span characteristics. By introducing a substituent at the 7th position, the HOMO energy may be further stabilized, and Tg (glass transition temperature) may be improved by creating a structure having steric hindrance, thereby improving device processability.

In an implementation, the compound represented by Chemical Formula 1 may be represented by, e.g., Chemical Formula 1A or Chemical Formula 1B.

In Chemical Formula 1A and Chemical Formula 1B, X1, L1to L4, Ar1to Ar3, R1to R3, m1, and m3 may be the same as those described above.

In an implementation, Ar1may be, e.g., a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzosilolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

In an implementation, L1may be, e.g., a single bond or a substituted or unsubstituted phenyl group.

In an implementation, the moiety -L1-Ar1may be, e.g., a moiety of Group I.

In Group I,

D is deuterium,

m13 may be, e.g., an integer of 0 to 5,

m14 may be, e.g., an integer of 0 to 4,

m15 may be, e.g., an integer of 0 to 7,

m16 may be, e.g., an integer of 0 to 2,

m17 may be, e.g., an integer of 0 to 3,

m18 may be, e.g., an integer of 0 to 6, and

* is a linking point.

In the definitions of m13 to m18, 0 means that all hydrogen atoms are not substituted with deuterium and remain as hydrogen atoms, e.g., “unsubstituted”.

In an implementation, Ar2and Ar3may each independently be, e.g., a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzosilolyl group, a substituted or unsubstituted benzonaphthofuranyl group, a substituted or unsubstituted benzonaphthothiophenyl group, a substituted or unsubstituted benzoxazolyl group, or a substituted or unsubstituted phenanthrooxazolyl group.

In an implementation, L3and L4may each independently be, e.g., a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

In an implementation, moieties -L3-Ar2and -L4-Ar3may each independently be, e.g., a moiety of Group II.

In Group II,

D is deuterium,

m19 may be, e.g., an integer of 0 to 5,

m20 may be, e.g., an integer of 0 to 4,

m21 may be, e.g., an integer of 0 to 7,

m22 may be, e.g., an integer of 0 to 6,

m23 may be, e.g., an integer of 0 to 2,

m24 may be, e.g., an integer of 0 to 3, and

* is a linking point.

In the definitions of m19 to m24, 0 means that all hydrogen atoms are not substituted with deuterium and remain as hydrogen atoms, e.g., “unsubstituted”.

In an implementation, Ar1may be, e.g., a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

In an implementation, Ar2and Ar3may each independently be, e.g., a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group.

In an implementation, the compound represented by Chemical Formula 1 may be, e.g., a compound of Group 1.

In an implementation, Chemical Formula 1 may be represented by, e.g., Chemical Formula 1A.

A composition for an organic optoelectronic device according to another embodiment may include, e.g., a first compound, and a second compound, wherein the first compound may be the aforementioned compound for an organic optoelectronic device and the second compound may be a compound for an organic optoelectronic device represented by Chemical Formula 2.

Lamay be or may include, e.g., a single bond or a substituted or unsubstituted C6 to C12 arylene group.

m4 may be, e.g., an integer of 1 to 4.

A may be, e.g., a ring of Group III.

In Group III, * is a linking point.

R5to R12may each independently be or include, e.g., hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group.

m5, m7, m10, and m12 may each independently be, e.g., an integer of 1 to 4.

In an implementation, at least one of Raand R4to R12may be, e.g., a group represented by Chemical Formula a.

In Chemical Formula a, Z1to Z3may each independently be, e.g., N or CRf. In an implementation, at least two of Z1to Z3may be N.

Rfmay be or may include, e.g., hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group.

L5to L7may each independently be or include, e.g., a single bond or a substituted or unsubstituted C6 to C30 arylene group.

Ar4and Ar5may each independently be or include, e.g., a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group.

* is a linking point.

The second compound may have, e.g., a structure substituted with a nitrogen-containing 6-membered ring.

The second compound may effectively extend an LUMO energy band by being substituted with a nitrogen-containing 6-membered ring, and when used in the light emitting layer together with the aforementioned first compound, a balance of holes and electrons may be increased to help improve luminous efficiency and life-span characteristics of a device including the same, and to help lower a driving voltage.

In an implementation, ring A of the second compound may be a ring of Group II, and the second compound may be, e.g., represented by one of Chemical Formula 2-I to Chemical Formula 2-X.

In Chemical Formula 2-I, Z1to Z3, R4, R5, L5to L7, Ar4, Ar5, m4, and m5 may be defined the same as those described above.

In Chemical Formula 2-II to Chemical Formula 2-V, X2, Z1to Z3, R4to R7, L5to L7, Ar4, Ar5, and m5 to m7 may be defined the same as those described above.

m4′ may be, e.g., an integer of 1 to 3.

m7′ may be, e.g., an integer of 1 to 3.

m10′ may be, e.g., an integer of 1 to 3.

m4′ may be, e.g., an integer of 1 to 3.

In an implementation, the second compound may be represented by, e.g., Chemical Formula 2-II, Chemical Formula 2-III, or Chemical Formula 2-VI.

In an implementation, the second compound may be represented by, e.g., Chemical Formula 2-II-3, Chemical Formula 2-III-1, Chemical Formula 2-VI-1, or Chemical Formula 2-VI-3.

In Chemical Formula 2-II-3, Chemical Formula 2-III-1, Chemical Formula 2-VI-1, and Chemical Formula 2-VI-3, X2, Z1to Z3, R4to R7, L5to L7, Ar4, Ar5, m4 to m7, m4′, and m7′ may be defined the same as those described above.

In an implementation, Ar4and Ar5may each independently be, e.g., a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group.

In an implementation, Ar4and Ar5may each independently be, e.g., a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

In an implementation, L5to L7may each independently be, e.g., a single bond, a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenylene group.

In an implementation, L5may be, e.g., a single bond or a substituted or unsubstituted phenylene group. In an implementation, L6and L7may each independently be, e.g., a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

In an implementation, L5may be a single bond and L6and L7may each independently be a single bond or a substituted or unsubstituted phenylene group.

In an implementation, R4to R12may each independently be, e.g., hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a substituted or unsubstituted C2 to C18 heterocyclic group.

In an implementation, R4to R12may each independently be, e.g., hydrogen, deuterium, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

In an implementation, X2may be, e.g., O, S, CRbRc, or SiRdRe, in which Rb, Rc, Rd, and Re may each independently be, e.g., a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C20 aryl group.

In an implementation, Rb, Rc, Rd, and Re may each independently be, e.g., a substituted or unsubstituted methyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

In an implementation, the second compound may be, e.g., a compound of Group 2.

In an implementation, the composition for an organic optoelectronic device may include, e.g., the first compound represented by Chemical Formula 1 A or Chemical Formula 1B and the second compound represented by one of Chemical Formula 2-II-3, Chemical Formula 2-III-1, and Chemical Formula 2-VI-3.

The first compound and the second compound may be included (e.g., mixed) in a weight ratio of about 1:99 to about 99:1. Within the range, a desirable weight ratio may be adjusted using an electron transport capability of the first compound and a hole transport capability of the second compound to realize bipolar characteristics and thus to improve efficiency and life-span. Within the range, they may be, e.g., included in a weight ratio of about 10:90 to about 90:10, or about 20:80 to about 80:20, e.g., a weight ratio of about 20:80 to about 70:30, about 20:80 to about 60:40, and about 30:70 to about 60:40. In an implementation, they may be included in a weight ratio of about 40:60, about 50:50, or about 60:40.

One or more compounds may be further included in addition to the aforementioned first and second compounds.

The aforementioned compound for an organic optoelectronic device or composition for an organic optoelectronic device may be a composition that further includes a dopant.

The dopant may be, e.g., a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant, and may be, e.g., a red or green phosphorescent dopant.

The dopant is a material mixed with the compound or composition for an organic optoelectronic device in a small amount to cause light emission and may be generally a material such as a metal complex that emits light by multiple excitation into a triplet or more. The dopant may be, e.g., an inorganic, organic, or organic-inorganic compound, and one or more types thereof may be used.

Examples of the dopant may include a phosphorescent dopant and examples of the phosphorescent dopant may include an organic metal compound including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. In an implementation, the phosphorescent dopant may be, e.g., a compound represented by Chemical Formula Z.

In Chemical Formula Z, M may be a metal, and L8and X4may each independently be ligands forming a complex compound with M.

In an implementation, the ligands represented by L8and X4may be ligands of Group A.

In Group A,

R300to R302may each independently be, e.g., hydrogen, deuterium, a C1 to C30 alkyl group that is substituted or unsubstituted with a halogen, a C6 to C30 aryl group that is substituted or unsubstituted with a C1 to C30 alkyl, or a halogen, and

R303to R324may each independently be, e.g., hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 amino group, a substituted or unsubstituted C6 to C30 arylamino group, SFs, a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group.

In an implementation, it may include a dopant represented by Chemical Formula V.

In Chemical Formula V,

at least one of R101to R116may be a functional group represented by Chemical Formula V-1,

L100may be a bidentate ligand of a monovalent anion, and is a ligand that coordinates to iridium through a lone pair of electrons of carbon or heteroatom,

m15 and m16 may each independently be an integer of 0 to 3, and

m15+m16 may be an integer of 1 to 3.

In Chemical Formula V-1,

* is a linking site.

In an implementation, a dopant represented by Chemical Formula Z-1 may be included.

In Chemical Formula Z-1, rings A, B, C, and D may each independently be, e.g., a 5-membered or 6-membered carbocyclic or heterocyclic ring;

The dopant according to an embodiment may be a platinum complex, and may be, e.g., represented by Chemical Formula VI.

In Chemical Formula VI,

at least one of R117to R131may be —SiR132R133R134or a tert-butyl group.

Hereinafter, an organic optoelectronic device including the aforementioned compound for an organic optoelectronic device or composition for an organic optoelectronic device is described.

The organic optoelectronic device may be a suitable device to convert electrical energy into photoenergy and vice versa, e.g., an organic photoelectric device, an organic light emitting diode, an organic solar cell, or an organic photo-conductor drum.

Herein, an organic light emitting diode as one example of an organic optoelectronic device is described referring to the drawing.

TheFIG.1sa cross-sectional view illustrating an organic light emitting diode according to an embodiment.

Referring to the FIGURE, an organic light emitting diode100according to an embodiment may include an anode120and a cathode110facing each other and an organic layer105between the anode120and cathode110.

The anode120may be made of a conductor having a large work function to help hole injection, and may be, e.g., a metal, a metal oxide, or a conductive polymer. The anode120may be, e.g., a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or the like or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), or the like; a combination of a metal and an oxide such as ZnO and Al or SnO2and Sb; a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDOT), polypyrrole, or polyaniline.

The cathode110may be made of a conductor having a small work function to help electron injection, and may be, e.g., a metal, a metal oxide, or a conductive polymer. The cathode110may be, e.g., a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum silver, tin, lead, cesium, barium, or the like, or an alloy thereof; a multi-layer structure material such as LiF/Al, LiO2/Al, LiF/Ca, LiF/Al, or BaF2/Ca.

The organic layer105may include the aforementioned compound for an organic optoelectronic device or composition for an organic optoelectronic device.

The organic layer105may include a light emitting layer130and the light emitting layer130may include the aforementioned compound for an organic optoelectronic device or composition for an organic optoelectronic device.

The composition for an organic optoelectronic device further including the dopant may be, e.g., a red light emitting composition.

The light emitting layer130may include, e.g., the aforementioned compound for an organic optoelectronic device or composition for an organic optoelectronic device as each phosphorescent host.

The organic layer may further include a charge transport region in addition to the light emitting layer.

The charge transport region may be, e.g., a hole transport region140.

The hole transport region140may further increase hole injection and/or hole mobility between the anode120and the light emitting layer130and block electrons. In an implementation, the hole transport region140may include a hole transport layer between the anode120and the light emitting layer130, and a hole transport auxiliary layer between the light emitting layer130and the hole transport layer and a compound of Group B may be included in at least one of the hole transport layer and the hole transport auxiliary layer.

In the hole transport region, other suitable compounds may be used in addition to the compound.

In addition, the charge transport region may be, e.g., an electron transport region150.

The electron transport region150may further increase electron injection and/or electron mobility and block holes between the cathode110and the light emitting layer130.

In an implementation, the electron transport region150may include an electron transport layer between the cathode110and the light emitting layer130, and an electron transport auxiliary layer between the light emitting layer130and the electron transport layer, and a compound of Group C may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

An embodiment may include an organic light emitting diode including a light emitting layer as an organic layer.

Another embodiment may provide an organic light emitting diode including a light emitting layer and a hole transport region as an organic layer.

Another embodiment may provide an organic light emitting diode including a light emitting layer and an electron transport region as an organic layer.

As shown in the FIGURE, the organic light emitting diode according to the embodiment may include a hole transport region140and an electron transport region150in addition to the light emitting layer130as the organic layer105.

In an implementation, the organic light emitting diode may further include an electron injection layer, a hole injection layer, or the like, in addition to the light emitting layer as the aforementioned organic layer.

The organic light emitting diode100may be produced by forming an anode or a cathode on a substrate, forming an organic layer using a dry film formation method such as a vacuum deposition method (evaporation), sputtering, plasma plating, and ion plating, and forming a cathode or an anode thereon.

The organic light emitting diode may be applied to an organic light emitting display device.

Hereinafter, starting materials and reactants used in examples and synthesis examples were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., or Tokyo chemical industry, as far as there in no particular comment or were synthesized by suitable methods.

(Preparation of Compound for Organic Optoelectronic Device)

Synthesis Example 1: Synthesis of Compound 1-2

50.0 g (174.84 mmol) of 2,3-dibromonaphthalene, 37.26 g (192.33 mmol) of (5-chloro-2-fluorophenyl)boronic acid, 6.06 g (5.25 mmol) of Pd(PPh3)4, and 48.33 g (349.69 mmol) of K2CO3were suspended in 800 mL of THF/400 mL of distilled water in a round-bottomed flask and then, stirred under reflux for 12 hours. When a reaction was completed, the resultant was concentrated and extracted with methylene chloride, and an organic layer therefrom was silica gel-columned, obtaining 35.0 g (Yield: 60%) of Intermediate 1-2-1.

19.1 g (56.92 mmol) of Intermediate 1-2-1 and 4.03 g (57.48 mmol) of NaSCH3were suspended in 400 mL of DMF, and then, 20.91 g (186.34 mmol) of potassium tert-butoxide was added thereto and then, stirred at 100° C. for 12 hours. When a reaction was completed, 500 mL of distilled water was added thereto and then, extracted with EA. An organic layer therefrom was silica gel-columned, obtaining 12.0 g (Yield: 58%) of Intermediate 1-2-2.

44.63 g (122.73 mmol) of Intermediate 1-2-2 was dissolved in 300 mL of acetic acid and then, slowly added to 22.6 mL (368.19 mmol) of H2O2at 0° C. and then, stirred at ambient temperature for 12 hours. When a reaction was completed, after removing the solvent, the residue was extracted with EA and washed with distilled water. The solvent was concentrated and dried, obtaining 45 g (Yield: 97%) of Intermediate 1-2-3.

51.87 g (136.63 mmol) of Intermediate 1-2-3 was dissolved in 600 mL of methylene chloride, and 46.83 mL (273.26 mmol) of triflic anhydride was slowly added thereto at 0° C. The obtained mixture was stirred at ambient temperature for 4 hours, and 111 mL (1366.3 mmol) of pyridine was slowly added thereto at 0° C. When a reaction was completed, after removing the solvent, the residue was extracted with methylene chloride and washed with distilled water. The solvent was concentrated and then, recrystallized with toluene, obtaining 24.0 g (Yield: 51%) of Intermediate 1-2-4.

24.16 g (69.50 mmol) of Intermediate 1-2-4, 10.17 g (83.39 mmol) of phenylboronic acid, 2.41 g (2.08 mmol) of Pd(PPh3)4, and 19.21 g (138.99 mmol) of K2CO3were suspended in 350 mL of THF/400 mL of distilled water and then, stirred under reflux for 12 hours. When a reaction was completed, the resultant was concentrated and extracted with methylene chloride, and an organic layer therefrom was silica gel columned, obtaining 16.7 g (Yield: 70%) of Intermediate 1-2-5.

16.79 g (42.52 mmol) of Intermediate 1-2-5, 15.07 g (51.02 mmol) of Intermediate 1-2-6, 6.13 g (20.19 mmol) of NaOtBu, and 3.35 g (50%, 8.29 mmol) of PtBu3were dissolved in 250 mL of xylene, and 2.53 g (2.76 mmol) of Pd2(dba)3was added thereto and then, stirred under reflux under a nitrogen atmosphere for 12 hours. When a reaction was completed, the resultant was extracted with xylene and distilled water, and an organic layer therefrom was concentrated. The organic layer was silica gel-columned, obtaining 25.0 g (Yield: 90%) of Compound 1-2.

Synthesis Example 2: Synthesis of Compound 1-4

Compound 1-4 (7.2 g, Yield: 83%) was synthesized in the same manner as the 6th step of Synthesis Example 1 except that Intermediate 1-2-5 and Intermediate 1-4-1 were used in an equivalent ratio of 1:1.2.

Synthesis Example 3: Synthesis of Compound 1-21

Compound 1-21 (6.0 g, Yield: 88%) was synthesized in the same manner as the 6th step of Synthesis Example 1 except that Intermediate 1-2-5 and Intermediate 1-21-1 were used in an equivalent ratio of 1:1.2.

Synthesis Example 4: Synthesis of Compound 1-33

Compound 1-33 (8.0 g, Yield: 82%) was synthesized in the same manner as the 6th step of Synthesis Example 1 except that Intermediate 1-2-5 and Intermediate 1-33-1 were used in an equivalent ratio of 1:1.2.

Synthesis Example 5: Synthesis of Compound 1-42

Intermediate 1-42-1 (42.0 g, Yield: 60%) was synthesized in the same manner as the lth step of Synthesis Example 1 except that 1-bromo-2-iodonaphthalene and (5-chloro-2-fluorophenyl)boronic acid were used in an equivalent ratio of 1:1.1.

Intermediate 1-42-2 (25.0 g, Yield: 55%) was synthesized in the same manner as the 2nd step of Synthesis Example 1 except that Intermediate 1-42-1 was used.

Intermediate 1-42-3 (24.0 g, Yield: 90%) was synthesized in the same manner as the 2nd step of Synthesis Example 1 except that Intermediate 1-42-2 was used.

Intermediate 1-42-4 (11.0 g, Yield: 51%) was synthesized in the same manner as the 4th step of Synthesis Example 1 except that Intermediate 1-42-3 was used.

Intermediate 1-42-5 (15.0 g, Yield: 72%) was synthesized in the same manner as the 5th step of Synthesis Example 1 except that Intermediate 1-42-4 and an intermediate of phenylboronic acid were used in an equivalent ratio of 1:1.2.

Compound 1-42 (8.5 g, Yield: 81%) was synthesized in the same manner as the 6th step of Synthesis Example 1 except that Intermediate 1-42-5 and Intermediate 1-2-6 were used in an equivalent ratio of 1:1.2.

Synthesis Example 6: Synthesis of Compound 1-55

30.0 g (110.98 mmol) of Intermediate 1-55-1, 34.61 g (166.46 mmol) of 2-bromo-4-chloro-1-fluorobenzene, and 108.47 g (332.93 mmol) of Cs2CO3were suspended in 100 mL of NMP and then, stirred for 12 hours at 155° C. When a reaction was completed, 500 mL of distilled water was added thereto and then, extracted with EA. An organic layer therefrom was silica gel columned, obtaining 30.0 g (Yield: 59%) of Intermediate 1-55-2.

25.0 g (54.38 mmol) of Intermediate 1-55-2, 3.14 g (2.72 mmol) of Pd(PPh3)4, and 10.67 g (108.75 mmol) of KOAc were suspended in 200 mL of DMA and then, stirred for 12 hours at 160° C. When a reaction was completed, the resultant was concentrated and then, extracted with methylene chloride, and an organic layer therefrom was silica gel-columned, obtaining 17.0 g (Yield: 83%) of Intermediate 1-55-3.

Compound 1-55 (7.5 g, Yield: 76%) was synthesized in the same manner as the 6th step of Synthesis Example 1 except that Intermediate 1-55-3 and Intermediate 1-2-6 were used in an equivalent ratio of 1:1.2.

Synthesis Example 7: Synthesis of Compound 1-57

Intermediate 1-57-1 (18.0 g, Yield: 78%) was synthesized in the same manner as the 5th step of Synthesis Example 1 except that Intermediate 1-2-4 and 2-(dibenzo[b,d]furan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane were used in an equivalent ratio of 1:1.2

Compound 1-57 (8.2 g, Yield: 77%) was synthesized in the same manner as the 6th step of Synthesis Example 1 except that Intermediate 1-57-1 and Intermediate 1-2-6 were used in an equivalent ratio of 1:1.2.

Synthesis Example 8: Synthesis of Compound 1-59

Intermediate 1-59-1 (17.0 g, Yield: 81%) was synthesized in the same manner as the 5th step of Synthesis Example 1 except that Intermediate 1-2-4 and 1-naphthaleneboronic acid were used in an equivalent ratio of 1:1.2.

Compound 1-59 (7.5 g, Yield: 80%) was synthesized in the same manner as the 6th step of Synthesis Example 1 except that Intermediate 1-59-1 and Intermediate 1-2-6 were used in an equivalent ratio of 1:1.2.

Synthesis Example 9: Synthesis of Compound 1-67

Compound 1-67 (8.6 g, Yield: 77%) was synthesized in the same manner as the 6th step of Synthesis Example 1 except that Intermediate 1-59-1 and Intermediate 1-67-1 were used in an equivalent ratio of 1:1.2.

Synthesis Example 10: Synthesis of Compound 1-81

Intermediate 1-81-1 (26.0 g, Yield: 79%) was synthesized in the same manner as the 5th step of Synthesis Example 1 except that Intermediate 1-2-4 and 2-(dibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane were used in an equivalent ratio of 1:1.2.

Compound 1-81 (7.2 g, Yield: 80%) was synthesized in the same manner as the 5th step of Synthesis Example 1 except that Intermediate 1-81-1 and Intermediate 1-2-6 were used in an equivalent ratio of 1:1.2.

Comparative Synthesis Example 1: Synthesis of Compound Y1

31.47 g (124.55 mmol) of 7-chloronaphtho[1,2-b]benzofuran was dissolved in 400 mL of DMF in a round-bottomed flask, and 26.60 g (149.46 mmol) of NBS was slowly added thereto. The obtained mixture was stirred at ambient temperature for 12 hours, and 500 mL of methanol was added thereto to form a precipitate. The obtained solid was filtered with a glass filter to obtain 36.4 g (Yield: 88%) of Intermediate Y1-1.

16.88 g (50.91 mmol) of Intermediate Y1-1, 18.0 g (61.09 mmol) of Intermediate 1-2-6, 7.33 g (76.36 mmol) of NaOtBu, and 3.71 g (50%, 9.16 mmol) of PtBu3were dissolved in 250 mL of xylene, and 2.79 g (3.05 mmol) of Pd2(dba)3was added thereto and then, stirred under reflux for 12 hours under a nitrogen atmosphere. When a reaction was completed, after extraction with xylene and distilled water, an organic layer therefrom was concentrated. The organic layer was silica gel-columned, obtaining 25.0 g (Yield: 90%) of Intermediate Y1-2.

13.93 g (25.52 mmol) of Intermediate Y1-2, 4.04 g (33.18 mmol) of phenylboronic acid, 1.16 g (1.28 mmol) of Pd2(dba)3, and 16.63 g (51.04 mmol) of Cs2CO3were suspended in 100 mL of dioxane and then, stirred at 130° C. for 12 hours. When a reaction was completed, the resultant was concentrated and extracted with methylene chloride, and an organic layer therefrom was silica gel-columned, obtaining 10.0 g (Yield: 67%) of Compound Y1.

Comparative Synthesis Example 2: Synthesis of Compound Y2

15.00 g (45.24 mmol) of Intermediate Y1-1, 662 g (54.28 mmol) of phenylboronic acid, 1.57 g (1.36 mmol) of Pd(PPh3)4, and 12.50 g (90.47 mmol) of K2CO3were suspended in 200 mL of THF/100 mL of distilled water in a round-bottomed flask and stirred under reflux for 12 hours. When a reaction was completed, the resultant was concentrated and extracted with methylene chloride, and an organic layer therefrom was silica gel columned, obtaining 12.5 g (Yield: 84%) of Intermediate Y2-1.

12.30 g (37.43 mmol) of Intermediate Y2-1, 13.27 g (44.92 mmol) of Intermediate 1-2-6, 5.39 g (56.15 mmol) of NaOtBu, and 2.73 g (50%, 2.25 mmol) of PtBu3were dissolved in 200 mL of xylene, and 2.06 g (2.25 mmol) of Pd2(dba)3was added thereto and then, stirred under reflux for 12 hours under a nitrogen atmosphere. When a reaction was completed, after extraction with xylene and distilled water, an organic layer was concentrated. The organic layer was silica gel-columned, obtaining 18.0 g (Yield: 82%) of Compound Y2.

Synthesis Example 11: Synthesis of Compound A-3

22.6 g (100 mmol) of 2,4-dichloro-6-phenyl-1,3,5-triazine was added to 200 mL of tetrahydrofuran and 100 mL of distilled water in a round-bottomed flask, 0.9 equivalent of dibenzofuran-3-boronic acid (CAS No.: 395087-89-5), 0.03 equivalent of tetrakis(triphenylphosphine)palladium, and 2 equivalent of potassium carbonate were added thereto and then, heated under reflux under a nitrogen atmosphere. After 6 hours, the reaction solution was cooled, after removing an aqueous layer, an organic layer therefrom was dried under a reduced pressure. A solid therefrom was washed with water and hexane, recrystallized with 200 mL of toluene, obtaining 21.4 g (Yield: 60%) of Intermediate Int-39.

50.0 g (261.16 mmol) of 1-bromo-4-chloro-benzene, 44.9 g (261.16 mmol) of 2-naphthalene boronic acid, 9.1 g (7.83 mmol) of tetrakis(triphenylphosphine)palladium, and 71.2 g (522.33 mmol) of potassium carbonate were dissolved in 1,000 mL of tetrahydrofuran and 500 mL of distilled water in a round-bottomed flask and stirred under reflux under a nitrogen atmosphere. After 6 hours, the reaction solution was cooled, and after removing an aqueous layer, an organic layer therefrom was dried under a reduced pressure. The obtained solid was washed with water and hexane and recrystallized with 200 mL of toluene, obtaining 55.0 g (Yield: 88%) of Intermediate Int-40.

100.0 g (418.92 mmol) of Intermediate Int-40 was added to 1000 mL of DMF in a round-bottomed flask, and 17.1 g (20.95 mmol) of dichlorodiphenylphosphinoferrocene palladium, 127.7 g (502.70 mmol) of bis(pinacolato)diboron, and 123.3 g (1256.76 mmol) of potassium acetate were added thereto and then, stirred under reflux for 12 hours under a nitrogen atmosphere. The reaction solution was cooled and then, added dropwise to 2 L of water to catch a solid. The obtained solid was dissolved in boiling toluene and then, filtered through silica gel, and a filtrate therefrom was concentrated. The concentrated solid was stirred with a small amount of hexane and then, filtered, obtaining 28.5 g (Yield: 70%) of Intermediate Int-41.

10.0 g (27.95 mmol) of Intermediate Int-41, 11.1 g (33.54 mmol) of Intermediate Int-39, 1.0 g (0.84 mmol) of tetrakis(triphenylphosphine)palladium, and 7.7 g (55.90 mmol) of potassium carbonate were dissolved in 150 mL of tetrahydrofuran and 75 mL of distilled water in a round-bottomed flask and then, stirred under reflux under a nitrogen atmosphere. After 12 hours, the reaction solution was cooled, and after removing an aqueous layer, an organic layer therefrom was dried under a reduced pressure. A solid obtained therefrom was washed with water and methanol and recrystallized with 200 mL of toluene, obtaining 13.4 g (Yield: 91%) of Compound A-3.

Synthesis Example 12: Synthesis of Compound A-71

2,4-dichloro-6-phenyl-1,3,5-triazine and 1-phenyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-dibenzofuran were used respectively by 1.0 equivalent to synthesize Intermediate Int-42 in the same manner as the 1ststep of Synthesis Example 11.

Intermediate Int-42 and Intermediate Int-41 were used respectively by 1.0 equivalent to synthesize Compound A-71 in the same method as the 4thstep of Synthesis Example 11.

Synthesis Example 13: Synthesis of Compound A-61

21.95 g (135.53 mmol) of 2-benzofuranylboronic acid, 26.77 g (121.98 mmol) of 2-bromo-5-chlorobenzaldehyde, 2.74 g (12.20 mmol) of Pd(OAc)2, and 25.86 g (243.96 mmol) of Na2CO3were suspended in 200 ml of acetone/220 ml of distilled water in a round-bottomed flask and then, stirred for 12 hours at ambient temperature. When a reaction was completed, the resultant was concentrated and extracted with methylene chloride, and an organic layer therefrom was silica gel-columned, obtaining 21.4 g (Yield: 68%) of Intermediate Int-43.

20.4 g (79.47 mmol) of Intermediate Int-43 and 29.97 g (87.42 mmol) of (methoxymethyl)triphenylphosphonium chloride were suspended in 400 ml of THF, and 10.70 g (95.37 mmol) of potassium tert-butoxide was added thereto and then, stirred for 12 hours at ambient temperature. When a reaction was completed, 400 ml of distilled water was added thereto for extraction, an organic layer therefrom was concentrated and re-extracted with methylene chloride, magnesium sulfate was added to the organic layer and then, stirred for 30 minutes and filtered, and a filtrate therefrom was concentrated. Subsequently, 100 ml of methylene chloride was added to the concentrated filtrate again, and 10 ml of methanesulfonic acid was added thereto and then, stirred for 1 hour.

When a reaction was completed, a solid produced therein was filtered and dried with distilled water and methyl alcohol, obtaining 21.4 g (Yield: 65%) of Intermediate Int-44.

Intermediate Int-45 and Intermediate Int-46 were used respectively by 1.0 equivalent in the same manner as the 4th step of Synthesis Example 11, synthesizing Compound A-61.

Synthesis Example 14: Synthesis of Compound A-17 Synthesis

Intermediate Int-47 and Intermediate Int-48 were used respectively by 1.0 equivalent in the same manner as the 4th step of Synthesis Example 11, synthesizing Compound A-17.

Synthesis Example 15: Synthesis of Compound A-37

Intermediate Int-47 and Intermediate Int-46 were used respectively by 1.0 equivalent in the same manner as the 4th step of Synthesis Example 11, synthesizing Compound A-37.

Synthesis of Synthesis Examples 16 to 20

Each compound was synthesized in the same manner as the 4thstep of Synthesis Example 11 except that Int C shown in Table 1 was used instead of Int-41 of Synthesis Example 11, and Int D shown in Table 1 was used instead of Int-39.

(Manufacture of Organic Light Emitting Diode)

A glass substrate coated with ITO (Indium tin oxide) at a thickness of 1,500 Å was washed with distilled water. After washing with the distilled water, the glass substrate was ultrasonically washed with isopropyl alcohol, acetone, or methanol, a and dried and then, moved to a plasma cleaner, cleaned by using oxygen plasma for 10 minutes, and moved to a vacuum depositor. This obtained ITO transparent electrode was used as an anode, Compound A doped with 3% NDP-9 (available from Novaled) was vacuum-deposited on the ITO substrate to form a 100 Å-thick hole injection layer, and Compound A was deposited on the hole transport layer to form a 1,300 Å-thick hole transport layer. On the hole transport layer, Compound B was deposited at a thickness of 700 Å to form a hole transport auxiliary layer. On the hole transport auxiliary layer, a 400 Å-thick light emitting layer was formed by using Compound 1-2 obtained in Synthesis Example 1 and doping 2 wt % of [Ir(piq)2acac] as a dopant by vacuum-deposition. Subsequently, on the light emitting layer, Compound C was deposited at a thickness of 50 Å to form an electron transport auxiliary layer and Compound D and LiQ were simultaneously vacuum-deposited in a weight ratio of 1:1 to from a 300 Å-thick electron transport layer. On the electron transport layer, LiQ and Al were sequentially vacuum-deposited to be 15 Å-thick and 1,200 Å-thick, manufacturing an organic light emitting diode.

A glass substrate coated with ITO (Indium tin oxide) at a thickness of 1,500 Å was washed with distilled water. After washing with the distilled water, the glass substrate was ultrasonically washed with isopropyl alcohol, acetone, or methanol, and dried and then, moved to a plasma cleaner, cleaned by using oxygen plasma for 10 minutes, and moved to a vacuum depositor. This obtained ITO transparent electrode was used as an anode, Compound A doped with 3% NDP-9 (available from Novaled) was vacuum-deposited on the ITO substrate to form a 100 Å-thick hole injection layer, and Compound A was deposited on the hole transport layer to form a 1,300 Å-thick hole transport layer. On the hole transport layer, Compound B was deposited at a thickness of 700 Å to form a hole transport auxiliary layer. On the hole transport auxiliary layer, a 400 Å-thick light emitting layer was formed by simultaneously using Compound 1-2 of Synthesis Example 1 and Compound A-17 of Synthesis Example 14 as a host and doping 2 wt % of [Ir(piq)2acac] as a dopant by vacuum-deposition. Compound 1-2 and Compound A-17 were used in a weight ratio of 5:5. Subsequently, on the light emitting layer, Compound C was deposited at a thickness of 50 Å to form an electron transport auxiliary layer and Compound D and LiQ was simultaneously vacuum-deposited in a weight ratio of 1:1 to from a 300 Å-thick electron transport layer. On the electron transport layer, LiQ and Al were sequentially vacuum-deposited to be 15 Å-thick and 1,200 Å-thick, manufacturing an organic light emitting diode.

Examples 3 to 7 and Comparative Examples 1 and 2

Diodes of Examples 3 to 7 and Comparative Examples 1 and 2 were respectively manufactured according to the same method as Example 1 except that the host was changed as shown in Table 2.

Examples 8 to 16 and Comparative Examples 3 and 4

Diodes according to Example 8 to 16 and Comparative Example 3 and 4 were manufactured according to the same method as Example 2 except that the host was changed into a single host, as shown in Table 3.

Evaluations

Luminous efficiency and life-span characteristics of the organic light emitting diodes according to Examples 1 to 16 and Comparative Examples 1 to 4 were evaluated.

Specific measurement methods are as follows, and the results are shown in Tables 2 and 3.

(1) Measurement of Current Density Change Depending on Voltage Change

The obtained organic light emitting diodes were measured regarding a current value flowing in the unit device, while increasing the voltage from 0 V to 10 V using a current-voltage meter (Keithley 2400), and the measured current value was divided by area to provide the results.

(2) Measurement of Luminance Change Depending on Voltage Change

Luminance was measured by using a luminance meter (Minolta Cs-1000A), while the voltage of the organic light emitting diodes was increased from 0 V to 10 V.

(3) Measurement of Luminous Efficiency

The luminous efficiency (cd/A) of the same current density (10 mA/cm2) was calculated using the luminance, current density, and voltage measured from the (1) and (2).

The relative values based on the luminous efficiency of Comparative Example 1 were calculated and shown in Table 2.

The relative values based on the luminous efficiency of Comparative Example 3 were calculated and shown in Table 3.

T95 life-spans of the diodes according to Examples 1 to 16 and Comparative Examples 1 to 4 were measured as a time when their luminance decreased down to 95% relative to the initial luminance (cd/m2) after emitting light with 6,000 cd/m2as the initial luminance (cd/m2) and measuring their luminance decreases depending on a time with a Polanonix life-span measurement system.

The relative values based on the T95 life-span of Comparative Example 1 were calculated and shown in Table 2.

The relative values based on the T95 life-span of Comparative Example 3 were calculated and shown in Table 3.

Referring to Table 2, when the compounds of the Examples were applied as a host, efficiency and life-spans were improved, compared to the case where a comparative compound is applied. In addition, referring to Table 3, when a mixture of a first host and a second host according to the Examples was applied, overall efficiency and life-spans were greatly improved.

One or more embodiments may provide a compound for an organic optoelectronic device capable of implementing a high efficiency and long life-span organic optoelectronic device.