Organic light-emitting device

An organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, the organic layer including an emission layer, wherein the organic layer includes a first compound represented by Formula 1 and a second compound represented by Formula 501. The organic light-emitting device including the first compound and the second compound may have low driving voltage, high efficiency, and high luminance.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean Patent Application No. 10-2015-0181074, filed on Dec. 17, 2015, in the Korean Intellectual Property Office, the entire content of which is incorporated herein by reference.

BACKGROUND

One or more aspects of embodiments of the present disclosure relate to an organic light-emitting device.

2. Description of the Related Art

Organic light-emitting devices are self-emission devices that have wide viewing angles, high contrast ratios, short response times, and excellent brightness, driving voltage, and response speed characteristics, and can produce full-color images.

SUMMARY

One or more aspects of embodiments of the present disclosure are directed towards an organic light-emitting device that includes a first compound and a second compound represented by the Formulae provided herein.

According to one or more embodiments, an organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, the organic layer including an emission layer,

wherein the organic layer includes a first compound represented by Formula 1 and a second compound represented by Formula 501:

In Formulae 1, 2A, 2B, and 501,ring A1and ring A2may each independently be selected from a benzene ring, a naphthalene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, a quinazoline ring, and a cinnoline ring,ring A3may be a group represented by Formula 2A or a group represented by Formula 2B,X1may be N-[(L11)a11-(R11)b11], O, or S,X2may be N-[(L12)a12-(R12)b12], O, or S,Ar501may be selected from a substituted or unsubstituted C5-C30carbocyclic group and a substituted or unsubstituted C2-C30heterocyclic group,L1and L2may each independently be a substituted or unsubstituted condensed polycyclic group having three or more carbocyclic groups condensed with each other,a1 and a2 may each independently be an integer selected from 1 to 5, wherein when a1 is two or more, two or more L1(s) may be identical to or different from each other; and when a2 is two or more, two or more L2(s) may be identical to or different from each other,L11, L12, and L501to L503may each independently be selected from a substituted or unsubstituted C3-C10cycloalkylene group, a substituted or unsubstituted C1-C10heterocycloalkylene group, a substituted or unsubstituted C3-C10cycloalkenylene group, a substituted or unsubstituted C1-C10heterocycloalkenylene group, a substituted or unsubstituted C6-C60arylene group, a substituted or unsubstituted C1-C60heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,a11, a12, and xd1 to xd3 may each independently be an integer selected from 0 to 5, wherein when a11 is two or more, two or more L11(s) may be identical to or different from each other; when a12 is two or more, two or more L12(s) may be identical to or different from each other; when xd1 is two or more, two or more L501(s) may be identical to or different from each other; when xd2 is two or more, two or more L502(s) may be identical to or different from each other; and when xd3 is two or more, two or more L503(s) may be identical to or different from each other,R1to R6, R11to R13, R501, and R502may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C1-C60alkyl group, a substituted or unsubstituted C2-C60alkenyl group, a substituted or unsubstituted C2-C60alkynyl group, a substituted or unsubstituted C1-C60alkoxy group, a substituted or unsubstituted C3-C10cycloalkyl group, a substituted or unsubstituted C1-C10heterocycloalkyl group, a substituted or unsubstituted C3-C10cycloalkenyl group, a substituted or unsubstituted C1-C10heterocycloalkenyl group, a substituted or unsubstituted C6-C60aryl group, a substituted or unsubstituted C6-C60aryloxy group, a substituted or unsubstituted C6-C60arylthio group, a substituted or unsubstituted C1-C60heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), and —P(═O)(Q1)(Q2),b1, b2, b5, b6, b11, and b12 may each independently be an integer selected from 0 to 4,b3 and b4 may each independently be an integer selected from 0 to 6,b13 may be 0, 1, or 2,c1 and c2 may each independently be an integer selected from 0 to 4, and the sum of c1 and c2 (c1+c2) may be 1 or greater,xd4 may be an integer selected from 1 to 6, andat least one substituent of the substituted condensed polycyclic group having three or more carbocyclic groups condensed with each other, the substituted C5-C30carbocyclic group, the substituted C2-C30heterocyclic group, the substituted C3-C10cycloalkylene group, the substituted C1-C10heterocycloalkylene group, the substituted C3-C10cycloalkenylene group, the substituted C1-C10heterocycloalkenylene group, the substituted C6-C60arylene group, the substituted C1-C60heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic condensed heteropolycyclic group, the substituted C1-C60alkyl group, the substituted C2-C60alkenyl group, the substituted C2-C60alkynyl group, the substituted C1-C60alkoxy group, the substituted C3-C10cycloalkyl group, the substituted C1-C10heterocycloalkyl group, the substituted C3-C10cycloalkenyl group, the substituted C1-C10heterocycloalkenyl group, the substituted C6-C60aryl group, the substituted C6-C60aryloxy group, the substituted C6-C60arylthio group, the substituted C1-C60heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from the group consisting of:deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60alkyl group, a C2-C60alkenyl group, a C2-C60alkynyl group, and a C1-C60alkoxy group;a C1-C60alkyl group, a C2-C60alkenyl group, a C2-C60alkynyl group, and a C1-C60alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C3-C10cycloalkyl group, a C1-C10heterocycloalkyl group, a C3-C10cycloalkenyl group, a C1-C10heterocycloalkenyl group, a C6-C60aryl group, a C6-C60aryloxy group, a C6-C60arylthio group, a C1-C60heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), and —P(═O)(Q11)(Q12);a C3-C10cycloalkyl group, a C1-C10heterocycloalkyl group, a C3-C10cycloalkenyl group, a C1-C10heterocycloalkenyl group, a C6-C60aryl group, a C6-C60aryloxy group, a C6-C60arylthio group, a C1-C60heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;a C3-C10cycloalkyl group, a C1-C10heterocycloalkyl group, a C3-C10cycloalkenyl group, a C1-C10heterocycloalkenyl group, a C6-C60aryl group, a C6-C60aryloxy group, a C6-C60arylthio group, a C1-C60heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60alkyl group, a C2-C60alkenyl group, a C2-C60alkynyl group, a C1-C60alkoxy group, a C3-C10cycloalkyl group, a C1-C10heterocycloalkyl group, a C3-C10cycloalkenyl group, a C1-C10heterocycloalkenyl group, a C6-C60aryl group, a C6-C60aryloxy group, a C6-C60arylthio group, a C1-C60heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), and —P(═O)(Q21)(Q22); and—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32),wherein Q1to Q3, Q11to Q13, Q21to Q23, and Q31to Q33may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60alkyl group, a C2-C60alkenyl group, a C2-C60alkynyl group, a C1-C60alkoxy group, a C3-C10cycloalkyl group, a C1-C10heterocycloalkyl group, a C3-C10cycloalkenyl group, a C1-C10heterocycloalkenyl group, a C6-C60aryl group, a C1-C60heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.

In the organic light-emitting device, the emission layer may include a host and a dopant, wherein the first compound may be included in the host, and the second compound may be included in the dopant.

DETAILED DESCRIPTION

An organic light-emitting device according to an embodiment may include a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, the organic layer including an emission layer, wherein the organic layer may include a first compound represented by Formula 1 and a second compound represented by Formula 501:

Ring A1and ring A2in Formula 1 may each be fused with a neighboring 5-membered ring, while sharing at least two ring-forming carbon atoms therewith. In Formula 1, ring A1and ring A2may each independently be selected from a benzene ring, a naphthalene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, a quinazoline ring, and a cinnoline ring.

For example, ring A1and ring A2in Formula 1 may each independently be selected from a benzene ring, a naphthalene ring, a pyridine ring, a quinoline ring, and an isoquinoline ring.

In various embodiments, in Formula 1,ring A1may be a benzene ring or a pyridine ring; and ring A2may be selected from a benzene ring, a naphthalene ring, a pyridine ring, a quinoline ring, and an isoquinoline ring, orring A1may be selected from a naphthalene ring, a quinoline ring, and an isoquinoline ring; and ring A2may be a benzene ring or a pyridine ring,but embodiments of the present disclosure are not limited thereto.Ring A3in Formula 1 may be fused with two neighboring 5-membered rings, while sharing at least two ring-forming carbon atoms with each of the two neighboring 5-membered rings. In Formula 1, ring A3may be a group represented by Formula 2A or a group represented by Formula 2B:

R13and b13in Formula 2A and X2in Formula 2B are the same as described throughout the present specification.

In various embodiments, A3in Formula 1 may be a group represented by Formula 2A, but is not limited thereto.

For example, X1in Formula 1 may be O or S.

Ar501in Formula 501 may be selected from a substituted or unsubstituted C5-C30carbocyclic group and a substituted or unsubstituted C2-C30heterocyclic group.

For example, Ar501in Formula 501 may be a substituted or unsubstituted condensed polycyclic ring having three or more carbocyclic groups condensed (e.g., fused) with each other.

In various embodiments, Ar501in Formula 501 may be selected from the group consisting of:a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a benzopyrene group, a benzochrysene group, and a benzotriphenylene group; anda fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a benzopyrene group, a benzochrysene group, and a benzotriphenylene group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an am idino group, a hydrazino group, a hydrazono group, a C1-C20alkyl group, a C1-C20alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a naphthyl group, and —Si(Q31)(Q32)(Q33),wherein Q31to Q33may each independently be selected from a C1-C10alkyl group, a C1-C10alkoxy group, a phenyl group, and a naphthyl group.L1and L2in Formula 1 may each independently be a substituted or unsubstituted condensed polycyclic group having three or more carbocyclic groups condensed (e.g., fused) with each other. In some embodiments, L1and L2each independently include carbon atoms as ring-forming atoms and do not include a heteroatom (e.g., N, O, S, P, or the like). Accordingly, L1and L2do not include groups that have less than three carbocyclic groups condensed with each other (e.g., L1and L2do not include a naphthylene group that has only two carbocyclic groups condensed with each other), or groups that include a heteroatom as a ring-forming atom (e.g., L1and L2do not include a pyridinylene group that includes N as a ring-forming atom).

In various embodiments, L1and L2in Formula 1 may each independently be selected from the group consisting of:a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, and a perylenylene group; anda phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, and a perylenylene group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an am idino group, a hydrazino group, a hydrazono group, a C1-C20alkyl group, a C1-C20alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and —Si(Q31)(Q32)(Q33),wherein Q31to Q33may each independently be selected from a C1-C10alkyl group, a C1-C10alkoxy group, a phenyl group, and a naphthyl group.a1 and a2 in Formula 1 may each independently be an integer selected from 1 to 5, wherein when a1 is two or more, two or more L1(s) may be identical to or different from each other, and when a2 is two or more, two or more L2(s) may be identical to or different from each other. That is, in Formula 1, “L1” is included in the group represented by *-[(L1)a1-(R1)b1] and “L2” is included in the group represented by *-[(L2)a2-(R2)b2].

In various embodiments, a1 and a2 in Formula 1 may each independently be 1 or 2, or may each independently be 1, but a1 and a2 are not limited thereto.L11, L12, and L501to L503in the Formulae described above may each independently be selected from a substituted or unsubstituted C3-C10cycloalkylene group, a substituted or unsubstituted C1-C10heterocycloalkylene group, a substituted or unsubstituted C3-C10cycloalkenylene group, a substituted or unsubstituted C1-C10heterocycloalkenylene group, a substituted or unsubstituted C6-C60arylene group, a substituted or unsubstituted C1-C60heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.

In various embodiments, L1and L2may each independently be selected from groups represented by Formulae 3-8, 3-9, 3-25, and 3-35 to 3-41, and L11, L12, and L501to L503may each independently be selected from groups represented by Formulae 3-1 to 3-41:

In Formulae 3-1 to 3-41,Y1may be selected from O, S, C(Z3)(Z4), N(Z5), and Si(Z6)(Z7),Z1to Z7may each independently be selected from hydrogen, deuterium, —F, —CI, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, and —Si(Q31)(Q32)(Q33),wherein Q31to Q33may each independently be selected from a C1-C10alkyl group, a C1-C10alkoxy group, a phenyl group, and a naphthyl group,d2 may be an integer selected from 0 to 2,d3 may be an integer selected from 0 to 3,d4 may be an integer selected from 0 to 4,d5 may be an integer selected from 0 to 5,d6 may be an integer selected from 0 to 6,d8 may be an integer selected from 0 to 8, and* and *′ each independently indicate a binding site to a neighboring atom.

In various embodiments, L1and L2may each independently be selected from groups represented by Formulae 4-11, 4-13, 4-27, and 4-29 to 4-35, and L11, L12, and L501to L503may each independently be selected from Formulae 4-1 to 4-35, but L1, L2L11, L12, and L501to L503are not limited thereto:

In Formulae 4-1 to 4-35, * and *′ each independently indicate a binding atom to a neighboring atom, and “D” may refer to deuterium.

a11, a12, and xd1 to xd3 may each independently be an integer selected from 0 to 5, wherein when a11 is two or more, two or more L11(s) may be identical to or different from each other; when a12 is two or more, two or more L12(s) may be identical to or different from each other; when xd1 is two or more, two or more L501(s) may be identical to or different from each other; when xd2 is two or more, two or more L502(s) may be identical to or different from each other; and xd3 is two or more, two or more L503(s) may be identical to or different from each other.

In various embodiments, a11, a12, and xd1 to xd3 in the Formulae described above may each independently be 0, 1, or 2, or may each independently be 0 or 1, but are not limited thereto.

In various embodiments, R1to R6, R11to R13, and R501and R502in the Formulae described above may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C10alkyl group, a C1-C10alkoxy group, a group represented by any of Formulae 5-1 to 5-75, and —Si(Q1)(Q2)(Q3), wherein Q1to Q3may each independently be selected from a C1-C10alkyl group, a C1-C10alkoxy group, a phenyl group, and a naphthyl group:

In Formulae 5-1 to 5-75,Y31may be selected from O, S, C(Z33)(Z34), N(Z35), and Si(Z36)(Z37),Z31to Z37may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, a biphenyl group, a terphenyl group, and —Si(Q31)(Q32)(Q33),wherein Q31to Q33may each independently be selected from a C1-C10alkyl group, a C1-C10alkoxy group, a phenyl group, and a naphthyl group,e2 may be an integer selected from 0 to 2,e3 may be an integer selected from 0 to 3,e4 may be an integer selected from 0 to 4,e5 may be an integer selected from 0 to 5,e6 may be an integer selected from 0 to 6,e7 may be an integer selected from 0 to 7,e9 may be an integer selected from 0 to 9, and* indicates a binding site to a neighboring atom.

In various embodiments, R1to R6, R11to R13, R501, and R502in the Formulae described above may each independently be selected from hydrogen, deuterium, —F, —CI, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C10alkyl group, a C1-C10alkoxy group, a group represented by any of Formulae 6-1 to 6-43, a group represented by any of Formulae 10-1 to 10-117, and —Si(Q1)(Q2)(Q3), wherein Q1to Q3may each independently be selected from a C1-C10alkyl group, a C1-C10alkoxy group, a phenyl group, and a naphthyl group, but R1to R6, R11to R13, R501, and R502are not limited thereto:

In Formulae 6-1 to 6-43 and 10-1 to 10-117, * indicates a binding site to a neighboring atom, and “D” may refer to deuterium.

In various embodiments, in the Formulae described above,R3to R6and R13may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, a naphthyl group, and —Si(Q1)(Q2)(Q3), andR1, R2, R11, R12, R501, and R502may each independently be selected from a substituted or unsubstituted C3-C10cycloalkyl group, a substituted or unsubstituted C1-C10heterocycloalkyl group, a substituted or unsubstituted C3-C10cycloalkenyl group, a substituted or unsubstituted C1-C10heterocycloalkenyl group, a substituted or unsubstituted C6-C60aryl group, a substituted or unsubstituted C6-C60aryloxy group, a substituted or unsubstituted C6-C60arylthio group, a substituted or unsubstituted C1-C60heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group (e.g., R1, R2, R11, R12, R501, and R502may each independently be selected from groups represented by Formulae 5-1 to 5-75 or groups represented by Formulae 6-1 to 6-43 and 10-1 to 10-117).

In various embodiments, in the Formulae described above,R3to R6and R13may each be hydrogen, andR1, R2, R11, R12, R501, and R502may each independently be selected from groups represented by Formulae 5-1 to 5-75 (e.g., groups represented by Formulae 6-1 to 6-43 and 10-1 to 10-117), but are not limited thereto.b1, b2, b5, b6, b11, and b12 in the Formulae described above may each independently be an integer selected from 0 to 4, b3 and b4 may each independently be an integer selected from 0 to 6, and b13 may be 0, 1, or 2.

For example, b1, b2, b11, and b12 in the Formulae described above may each independently be 0, 1, or 2, or may each independently be 1 or 2.

In various embodiments, b1, b2, b11, and b12 in the Formulae described above may be 1, but are not limited thereto.b3 to b6 and b13 in the Formulae described above may each independently be 0, 1, or 2, or may each independently be 0 or 1, but are not limited thereto.c1 and c2 in Formula 1 may each independently be an integer selected from 0 to 4, and the sum of c1 and c2 (c1+c2) may be 1 or greater. That is, in Formula 1, at least one selected from the group represented by *-[(L1)a1-(R1)b1] and the group represented by *-[(L2)a2-(R2)b2] is present.

In various embodiments, in Formula 1, the sum of c1 and c2 (c1+c2) may be 1 or 2.

In various embodiments, in Formula 1,c1 may be 1 and c2 may be 0,c1 may be 1 and c2 may be 1, orc1 may be 0 and c2 may be 1, but embodiments are not limited thereto.xd4 in Formula 501 may be an integer selected from 1 to 6. For example, xd4 in Formula 501 may be 2, 3, or 4, but is not limited thereto. In various embodiments, xd4 in Formula 501 may be 2.

In various embodiments, the first compound may be represented by one selected from Formulae 1A to 1E:

For example, in Formulae 1A to 1E,ring A1may be a benzene ring or a pyridine ring, and ring A2may be selected from a benzene ring, a naphthalene ring, a pyridine ring, a quinoline ring, and an isoquinoline ring; or ring A1may be selected from a naphthalene ring, a quinoline ring, and an isoquinoline ring, and ring A2may be a benzene ring or a pyridine ring,X1and X2may each independently be O or S,L1and L2may each independently be selected from groups represented by Formulae 3-8, 3-9, 3-25, and 3-35 to 3-41 (e.g., groups represented by Formulae 4-11, 4-13, 4-27, and 4-29 to 4-35),a1 and a2 may each independently be 1 or 2,R1and R2may each independently be selected from groups represented by Formulae 5-1 to 5-75 (e.g., groups represented by Formulae 6-1 to 6-43 and 10-1 to 10-117),b1 and b2 may each independently be 1 or 2,R3to R6and R13may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, a naphthyl group, and —Si(Q1)(Q2)(Q3),wherein Q1to Q3may each independently be selected from a C1-C10alkyl group, a C1-C10alkoxy group, a phenyl group, and a naphthyl group,b3 to b6 and b13 may each independently be 0, 1, or 2, andc1 may be 1 and c2 may be 0; c1 may be 1 and c2 may be 1; or c1 may be 0 and c2 may be 1, but embodiments are not limited thereto.

In various embodiments, the first compound may be represented by one selected from Formulae 1-1 to 1-7:

In Formulae 1-1 to 1-7,ring A3, X1, L1, L2, a1, a2, R1, R2, R5, R6, b1, b2, b5, b6, c1, and c2 are the same as described above,X21may be N or C(R21); X22may be N or C(R22); X23may be N or C(R23), X24may be N or C(R24); X25may be N or C(R25); X26may be N or C(R26); X31may be N or C(R31); X32may be N or C(R32); X33may be N or C(R33); X34may be N or C(R34); X35may be N or C(R35); and X36may be N or C(R36),descriptions of R21to R26may each independently be the same as the description provided above in connection with R3, anddescriptions of R31to R36may each independently be the same as the description provided above in connection with R4.

In various embodiments,none or one selected from X21to X24in Formulae 1-1 to 1-4 may be N,none or one selected from X31to X34in Formulae 1-1 and 1-5 to 1-7 may be N,none or one selected X21to X26in Formulae 1-5 to 1-7 may be N, andnone or one selected from X31to X36in Formulae 1-2 to 1-4 may be N.

For example, ring A3in Formulae 1-1 to 1-7 may be a group represented by Formula 2A.

In various embodiments, in Formulae 1-1 to 1-7,X1and X2may each independently be O or S,L1and L2may each independently be selected from groups represented by Formulae 3-8, 3-9, 3-25, and 3-35 to 3-41 (e.g., groups represented by Formulae 4-11, 4-13, 4-27, and 4-29 to 4-35),a1 and a2 may each independently be 1 or 2,R1and R2may each independently be selected from groups represented by Formulae 5-1 to 5-75 (e.g., groups represented by Formulae 6-1 to 6-43 and 10-1 to 10-117),b1 and b2 may each independently be 1 or 2,R21to R26, R31to R36, R5, and R6may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, a naphthyl group, and —Si(Q1)(Q2)(Q3),wherein Q1to Q3may each independently be selected from a C1-C10alkyl group, a C1-C10alkoxy group, a phenyl group, and a naphthyl group,b5 and b6 may each independently be 0, 1, or 2, andc1 may be 1 and c2 may be 0; c1 may be 1 and c2 may be 1; or c1 may be 0 and c2 may be 1, but embodiments of the present disclosure are not limited thereto.

In various embodiments, the first compound may be represented by one selected from Formulae 1(1) to 1(24), but is not limited thereto:

In Formulae 1(1) to 1(24),X1, L1, L2, a1, a2, R1to R6, R13, b1 to b6, b13, c1, and c2 are the same as described above,ba3 and bb3 may each independently be an integer selected from 0 to 3,ba4 and bb4 may each independently be an integer selected from 0 to 4,ba5 and bb5 may each independently be an integer selected from 0 to 5, andba6 and bb6 may each independently be an integer selected from 0 to 6.

In various embodiments, in Formulae 1(1) to 1(24),X1and X2may each independently be O or S,L1and L2may each independently be selected from groups represented by Formulae 3-8, 3-9, 3-25, and 3-35 to 3-41 (e.g., groups represented by Formulae 4-11, 4-13, 4-27, and 4-29 to 4-35),a1 and a2 may each independently be 1 or 2,R1and R2may be each independently be selected from groups represented by Formulae 5-1 to 5-75 (e.g., groups represented by Formulae 6-1 to 6-43 and 10-1 to 10-117),b1 and b2 may each independently be 1 or 2,R3to R6and R13may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, a naphthyl group, and —Si(Q1)(Q2)(Q3),wherein Q1to Q3may each independently be selected from a C1-C10alkyl group, a C1-C10alkoxy group, a phenyl group, and a naphthyl group,ba3, bb3, ba4, bb4, ba5, bb5, ba6, bb6, b5, and b6 may each independently be 0, 1, or 2, andc1 may be 1 and c2 may be 0; c1 may be 1 and c2 may be 1; or c1 may be 0 and c2 may be 1, but embodiments are not limited thereto.

In various embodiments, the first compound may be represented by one selected from Formulae 1A-1 to 1A-3, but is not limited thereto:

For example, ring A1and ring A2in Formulae 1A-1 to 1A-3 may each independently be selected from a benzene ring, a naphthalene ring, a pyridine ring, a quinoline ring, and an isoquinoline ring,X1may be O or S,R1may be selected from groups represented by Formulae 5-1 to 5-75 (e.g., groups represented by Formulae 6-1 to 6-43 and 10-1 to 10-117),R3to R6, R13, Z1, and Z2may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, and a naphthyl group, andb3 to b6, b13, d4, and d5 may each independently be 0, 1, or 2, but are not limited thereto.

In various embodiments, the second compound may be represented by one selected from Formulae 501-1 to 501-4:

In Formulae 501-1 to 501-4,L501to L503, xd1 to xd3, R501, and R502are the same as described above,descriptions of L504to L506may each independently be the same as the description provided above in connection with L501,descriptions of xd4 and xd5 may each independently be the same as the description provided above in connection with xd1,description of xd6 may be the same as the description provided above in connection with xd3, anddescriptions of R511to R516may each independently be the same as the description provided above in connection with R3.

For example, in Formulae 501-1 and 501-4,L501to L506may each independently be selected from groups represented by Formulae 3-1 to 3-41 (e.g., groups represented by Formulae 4-1 to 4-35),xd1 to xd6 may each independently be 0 or 1,R501and R502may each independently be selected from groups represented by Formulae 5-1 to 5-75 (e.g., groups represented by Formulae 6-1 to 6-43 and groups represented by Formulae 10-1 to 10-117), andR511to R516may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C10alkyl group, a C1-C10alkoxy group, a phenyl group, a naphthyl group, and —Si(Q1)(Q2)(Q3),wherein Q1to Q3may each independently be selected from a C1-C10alkyl group, a C1-C10alkoxy group, a phenyl group, and a naphthyl group.

For example, the first compound may include at least one selected from Compounds 1 to 60, and the second compound may include at least one selected from Compounds 101 to 112, but the first compound and the second compound are not limited thereto:

Since the first compound represented by Formula 1 has a spiro-bifluorene-based condensed-ring core, it may be possible to prevent or reduce degradation of the first compound that may be caused by electrons. Accordingly, an electronic device, for example, an organic light-emitting device, which includes the first compound represented by Formula 1, may have a long lifespan. Also, since the first compound represented by Formula 1 has a relatively high triplet energy (T1), a probability of annihilation between triplet excitons in the emission layer including the first compound represented by Formula 1 may increase, thereby increasing a triplet-triplet annihilation (TTA) effect. Accordingly, an electronic device, for example, an organic light-emitting device, which includes the first compound represented by Formula 1, may have high efficiency.

Also, in the first compound represented by Formula 1, L1and L2may each independently be a substituted or unsubstituted condensed polycyclic group that has three or more carbocyclic groups condensed with each other and does not include a heteroatom, and a1 and a2 (respectively indicating the number of L1(s) and the number of L(s)) are not zero. That is, in Formula 1, “L1” is included in the group represented by *-[(L1)a1-(R1)b1] and “L2” is included in the group represented by *-[(L2)a2-(R2)b2]. Also, in Formula 1, the sum of c1 and c2 (c1+c2) may be one or greater. That is, in Formula 1, at least one selected from the group represented by *-[(L1)a1-(R1)b1] and the group represented by *-[(L2)a2-(R2)b2] is present. Thus, for example, when the first compound represented by Formula 1 is used as the host in the emission layer of the organic light-emitting device, a suitable energy level between the host and the dopant may be effectively adjusted, thereby achieving an efficient energy transfer between the host and the dopant. Accordingly, an electronic device, for example, an organic light-emitting device, which includes the first compound represented by Formula 1, may have high efficiency.

Further, an organic light-emitting device including both the first compound and the second compound represented by Formula 501 may have high efficiency and high luminance.

For example, both the first compound and the second compound may be included in the emission layer of the organic light-emitting device. In some embodiments, the first compound included in the emission layer may act as the host, and the second compound included in the emission layer may act as the dopant (e.g., a fluorescent dopant).

In various embodiments, an amount of the first compound in the emission layer may be greater than an amount of the second compound.

In various embodiments, an amount of the second compound in the emission layer may be in a range of about 0.01 to about 15 parts by weight based on 100 parts by weight of the first compound, but is not limited thereto. When the amount of the second compound is within the above range, it may be possible to implement an organic light-emitting device having high efficiency and high luminance without (or substantially without) emission quenching.

The first compound represented by Formula 1 may be synthesized by using any suitable organic synthesis method. Synthesis methods for the first compound should become apparent to one of ordinary skill in the art by referring to the examples described below.

In various embodiments, in the organic light-emitting device,the first electrode may be an anode,the second electrode may be a cathode, andthe organic layer may include a hole transport region between the first electrode and the emission layer, and an electron transport region between the emission layer and the second electrode.

The hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or a combination thereof, andthe electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

The term “first compound”, as used herein, may refer to i) a single compound represented by Formula 1 (e.g., Compound 1), or ii) a mixture of two or more different compounds represented by Formula 1 (e.g., a mixture of Compounds 1 and 2).

The term “second compound”, as used herein, may refer to i) a single compound represented by Formula 501 (e.g., Compound 107), or ii) a mixture of two or more different compounds represented by Formula 501 (e.g., a mixture of Compound 107 and 111).

The term “organic layer”, as used herein, may refer to a single layer and/or a plurality of layers between the first electrode and the second electrode of an organic light-emitting device. A material included in the “organic layer” is not limited to an organic material.

FIG.1is a schematic view of an organic light-emitting device10according to an embodiment. The organic light-emitting device10includes a first electrode110, an organic layer150, and a second electrode190.

Hereinafter, the structure of the organic light-emitting device10according to an embodiment and a method of manufacturing the organic light-emitting device10will be described in connection withFIG.1.

First Electrode110

InFIG.1, a substrate may be additionally disposed (e.g., positioned) under the first electrode110or above the second electrode190. The substrate may be a glass substrate or a plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and/or water-resistance.

The first electrode110may be formed by depositing or sputtering a material for forming the first electrode110on the substrate. When the first electrode110is an anode, the material for forming the first electrode110may be selected from materials with a high work function to facilitate hole injection.

The first electrode110may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode110is a transmissive electrode, a material for forming the first electrode110may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and a combination thereof, but is not limited thereto. When the first electrode110is a semi-transmissive electrode or a reflective electrode, as a material for forming the first electrode110, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or a combination thereof may be used. However, the material for forming the first electrode110is not limited thereto.

The organic layer150may be disposed (e.g., positioned) on the first electrode110. The organic layer150may include an emission layer.

Hole Transport Region in Organic Layer150

The hole transport region may include at least one layer selected from a hole injection layer (HIL), a hole transport layer (HTL), an emission auxiliary layer, and an electron blocking layer (EBL).

For example, the hole transport region may have a single-layered structure including a single layer including a plurality of different materials, or a multi-layered structure having a structure of hole injection layer/hole transport layer, hole injection layer/hole transport layer/emission auxiliary layer, hole injection layer/emission auxiliary layer, hole transport layer/emission auxiliary layer or hole injection layer/hole transport layer/electron blocking layer, wherein for each structure, constituting layers are sequentially stacked from the first electrode110in this stated order, but the structure of the hole transport region is not limited thereto.

In Formulae 201 and 202,L201to L204may each independently be selected from a substituted or unsubstituted C3-C10cycloalkylene group, a substituted or unsubstituted C1-C10heterocycloalkylene group, a substituted or unsubstituted C3-C10cycloalkenylene group, a substituted or unsubstituted C1-C10heterocycloalkenylene group, a substituted or unsubstituted C6-C60arylene group, a substituted or unsubstituted C1-C60heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,L205may be selected from *—O—*′, *—S—*′, *—N(Q201)-*′, a substituted or unsubstituted C1-C20alkylene group, a substituted or unsubstituted C2-C20alkenylene group, a substituted or unsubstituted C3-C10cycloalkylene group, a substituted or unsubstituted C1-C10heterocycloalkylene group, a substituted or unsubstituted C3-C10cycloalkenylene group, a substituted or unsubstituted C1-C10heterocycloalkenylene group, a substituted or unsubstituted C6-C60arylene group, a substituted or unsubstituted C1-C60heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,xa1 to xa4 may each independently be an integer selected from 0 to 3,xa5 may be an integer selected from 1 to 10, andR201to R204and Q201may each independently be selected from a substituted or unsubstituted C3-C10cycloalkyl group, a substituted or unsubstituted C1-C10heterocycloalkyl group, a substituted or unsubstituted C3-C10cycloalkenyl group, a substituted or unsubstituted C1-C10heterocycloalkenyl group, a substituted or unsubstituted C6-C60aryl group, a substituted or unsubstituted C6-C60aryloxy group, a substituted or unsubstituted C6-C60arylthio group, a substituted or unsubstituted C1-C60heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

For example, in Formula 202, R201and R202may optionally be linked to each other via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group, and R203and R204may optionally be linked to each other via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group.

In various embodiments, in Formula 202, i) R201and R202may be connected (e.g., linked) to each other via a single bond, and/or ii) R203and R204may be connected (e.g., linked) to each other via a single bond.

For example, the compound represented by Formula 201 may be represented by Formula 201A(1), but is not limited thereto:

For example, the compound represented by Formula 201 may be represented by Formula 201A-1, but is not limited thereto:

In various embodiments, the compound represented by Formula 202 may be represented by Formula 202A:

In various embodiments, the compound represented by Formula 202 may be represented by Formula 202A-1:

The hole transport region may include at least one compound selected from Compounds HT1 to HT39, but is not limited thereto:

The emission auxiliary layer may increase light-emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted by an emission layer, and the electron blocking layer may block or reduce the flow of electrons from an electron transport region. The emission auxiliary layer and the electron blocking layer may include any of the materials as described above.

In one embodiment, the p-dopant may have a lowest unoccupied molecular orbital (LUMO) of −3.5 eV or less.

The p-dopant may include at least one selected from a quinone derivative, a metal oxide, and a cyano group-containing compound, but embodiments are not limited thereto.

For example, the p-dopant may include at least one selected from the group consisting of:quinone derivatives, such as TCNQ (tetracyanoquinodimethane) and/or F4-TCNQ (2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane);metal oxides, such as tungsten oxide and/or molybdenum oxide;HAT-CN (1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile); anda compound represented by Formula 221,but is not limited thereto:

When the organic light-emitting device10is a full color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer, according to a sub pixel. In various embodiments, the emission layer may have a stacked structure of two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers contact each other or are separated from each other. In various embodiments, the emission layer may include two or more materials selected from a red-light emission material, a green-light emission material, and a blue-light emission material, in which the two or more materials are mixed with each other in a single layer to emit white light. The emission layer may include a host and a dopant. The host may include the first compound represented by Formula 1 and the dopant may include the second compound represented by Formula 501. In various embodiments, the host may be the first compound and the dopant may be the second compound.

An amount of the dopant in the emission layer may be, for example, in a range of about 0.01 to about 15 parts by weight based on 100 parts by weight of the host, but is not limited thereto.

Electron Transport Region in Organic Layer150

The electron transport region may include at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer (ETL), and an electron injection layer, but is not limited thereto.

For example, the electron transport region may have a structure of electron transport layer/electron injection layer, a structure of hole blocking layer/electron transport layer/electron injection layer, a structure of electron control layer/electron transport layer/electron injection layer, or a structure of buffer layer/electron transport layer/electron injection layer, wherein in each of these structures, constituting layers are sequentially stacked in this stated order from an emission layer. However, the structure of the electron transport layer is not limited thereto.

The electron transport region (e.g., a buffer layer, a hole blocking layer, an electron control layer, and/or an electron transport layer in the electron transport region) may include a metal-free compound containing at least one π electron-depleted nitrogen-containing ring.

The “π electron-depleted nitrogen-containing ring” as used herein may refer to a C1-C60heterocyclic group having at least one *—N═*′ moiety as a ring-forming moiety.

For example, the “π electron-depleted nitrogen-containing ring” may be i) a 5-membered to 7-membered hetero-monocyclic group having at least one *—N═*′ moiety, ii) a hetero-polycyclic group in which two or more 5-membered to 7-membered hetero-monocyclic groups each having at least one *—N═*′ moiety are condensed (e.g., fused) with each other, or iii) a hetero-polycyclic group in which at least one selected from 5-membered to 7-membered hetero-monocyclic groups, each having at least one *—N═*′ moiety, is condensed (e.g., fused) with at least one C5-C60carbocyclic group.

For example, the electron transport region may include a compound represented by Formula 601:
[Ar601]xe11-[(L601)xe1-R601]xe21.  Formula 601

In Formula 601,Ar6o1may be a substituted or unsubstituted C5-C60carbocyclic group or a substituted or unsubstituted C1-C60heterocyclic group,xe11 may be 1, 2, or 3,L601may be selected from a substituted or unsubstituted C3-C10cycloalkylene group, a substituted or unsubstituted C1-C10heterocycloalkylene group, a substituted or unsubstituted C3-C10cycloalkenylene group, a substituted or unsubstituted C1-C10heterocycloalkenylene group, a substituted or unsubstituted C6-C60arylene group, a substituted or unsubstituted C1-C60heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,xe1 may be an integer selected from 0 to 5,R601may be selected from a substituted or unsubstituted C3-C10cycloalkyl group, a substituted or unsubstituted C1-C10heterocycloalkyl group, a substituted or unsubstituted C3-C10cycloalkenyl group, a substituted or unsubstituted C1-C10heterocycloalkenyl group, a substituted or unsubstituted C6-C60aryl group, a substituted or unsubstituted C6-C60aryloxy group, a substituted or unsubstituted C6-C60arylthio group, a substituted or unsubstituted C1-C60heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q601)(Q602)(Q603), —C(═O)(Q601), —S(═O)2(Q601), and —P(═O)(Q601)(Q602),wherein Q601to Q603may each independently be selected from a C1-C10alkyl group, a C1-C10alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, andxe21 may be an integer selected from 1 to 5.

In various embodiments, at least one selected from xe11 number of Ar601(s) and xe21 number of R601(s) may include the π electron-depletion nitrogen-containing ring described above.

When xe11 in Formula 601 is two or more, two or more Ar601(s) may be connected (e.g., linked) to each other via a single bond.

In various embodiments, Ar601in Formula 601 may be an anthracene group.

In various embodiments, Compound represented by Formula 601 may be represented by Formula 601-1:

In Formula 601-1,X614may be N or C(R614); X615may be N or C(R615); X616may be N or C(R616); and at least one selected from X614to X616may be N,descriptions of L611to L613may each independently be the same as the description provided above in connection with L601,descriptions of xe611 to xe613 may each independently be the same as the description provided above in connection with xe1,descriptions of R611to R613may each independently be the same as the description provided above in connection with R601, andR614to R616may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an am idino group, a hydrazino group, a hydrazono group, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

The electron transport region may include at least one compound selected from Compounds ET1 to ET36, but is not limited thereto:

In various embodiments, the electron transport region may include at least one compound selected from BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline), Alq3, BAlq, TAZ (3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole), and NTAZ.

The thickness of the buffer layer, the hole blocking layer, and the electron control layer may each independently be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. When the thicknesses of the buffer layer, the hole blocking layer, and/or the electron control layer are within any of these ranges, excellent (or suitable) hole blocking characteristics or electron control characteristics may be obtained without a substantial increase in driving voltage.

A thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer is within any of the ranges described above, the electron transport layer may have satisfactory (or suitable) electron transport characteristics without a substantial increase in driving voltage.

The electron transport region (e.g., the electron transport layer in the electron transport region) may further include, in addition to the materials described above, a metal-containing material.

The metal-containing material may include at least one selected from alkaline metal complex and alkaline earth-metal complex. The alkaline metal complex may include a metal ion selected from a Li ion, a Na ion, a K ion, a Rb ion, and a Cs ion; and the alkaline earth-metal complex may include a metal ion selected from a Be ion, a Mg ion, a Ca ion, a Sr ion, and a Ba ion. A ligand coordinated with the metal ion of the alkaline metal complex and the alkaline earth-metal complex may each independently be selected from a hydroxy-quinoline, a hydroxy-isoquinoline, a hydroxy-benzoquinoline, a hydroxy-acridine, a hydroxy-phenanthridine, a hydroxy-phenylan oxazole, a hydroxy-phenylthiazole, a hydroxy-diphenylan oxadiazole, a hydroxy-diphenylthiadiazole, a hydroxy-phenylpyridine, a hydroxy-phenylbenzoimidazole, a hydroxy-phenylbenzothiazole, a bipyridine, a phenanthroline, and a cyclopentadiene, but is not limited thereto.

For example, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (LiQ) and/or Compound ET-D2:

The electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode190. The electron injection layer may directly contact the second electrode190.

The electron injection layer may include alkaline metal, alkaline earth metal, rare-earth-metal, alkaline metal compound, alkaline earth-metal compound, rare-earth metal compound, alkaline metal complex, alkaline earth-metal complex, rare-earth metal complex or a combination thereof.

The alkaline metal may be selected from Li, Na, K, Rb, and Cs. In one embodiment, the alkaline metal may be Li, Na, or Cs. In various embodiments, the alkaline metal may be Li or Cs, but is not limited thereto.

The rare-earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.

The alkaline metal compound, the alkaline earth-metal compound, and the rare-earth metal compound may be selected from oxides and halides (e.g., fluorides, chlorides, bromides, and/or iodides) of the alkaline metal, the alkaline earth-metal and rare-earth metal, respectively.

The alkaline metal compound may be selected from alkaline metal oxides (such as Li2O, Cs2O, and/or K2O), and alkaline metal halides (such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and/or KI). In one embodiment, the alkaline metal compound may be selected from LiF, Li2O, NaF, LiI, NaI, CsI, and KI, but is not limited thereto.

The alkaline earth-metal compound may be selected from alkaline earth-metal oxides (such as BaO, SrO, CaO, BaxSr1-xO (0<x<1), and/or BaxCa1-xO (0<x<1)). In one embodiment, the alkaline earth-metal compound may be selected from BaO, SrO, and CaO, but is not limited thereto.

The rare-earth metal compound may be selected from YbF3, ScF3, ScO3, Y2O3, Ce2O3, GdF3, and TbF3. In one embodiment, the rare-earth metal compound may be selected from YbF3, ScF3, TbF3, YbI3, ScI3, and TbI3, but is not limited thereto.

The alkaline metal complex, the alkaline earth-metal complex, and the rare-earth metal complex may include ions of alkaline metal, alkaline earth-metal, and rare-earth metal, respectively, as described above; a ligand coordinated with a metal ion of the alkaline metal complex, the alkaline earth-metal complex, or the rare-earth metal complex may each independently be selected from a hydroxy-quinoline, a hydroxy-isoquinoline, a hydroxy-benzoquinoline, a hydroxy-acridine, a hydroxy-phenanthridine, a hydroxy-phenyl oxazole, a hydroxy-phenylthiazole, a hydroxy-diphenyl oxadiazole, a hydroxy-diphenylthiadiazole, a hydroxy-phenylpyridine, a hydroxy-phenylbenzoimidazole, a hydroxy-phenylbenzothiazole, a bipyridine, a phenanthroline, and a cyclopentadiene, but is not limited thereto.

The electron injection layer may include alkaline metal, alkaline earth metal, rare-earth-metal, alkaline metal compound, alkaline earth-metal compound, rare-earth metal compound, alkaline metal complex, alkaline earth-metal complex, rare-earth metal complex or a combination thereof, as described above. In various embodiments, the electron injection layer may further include an organic material. When the electron injection layer further includes an organic material, alkaline metal, alkaline earth metal, rare-earth-metal, alkaline metal compound, alkaline earth-metal compound, rare-earth metal compound, alkaline metal complex, alkaline earth-metal complex, rare-earth metal complex, or a combination thereof may be homogeneously or non-homogeneously dispersed in a matrix including the organic material.

A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within any of the ranges described above, the electron injection layer may have satisfactory (or suitable) electron injection characteristics without a substantial increase in driving voltage.

The second electrode190may be disposed (e.g., positioned) on the organic layer150having such the structure according to embodiments of the present disclosure. The second electrode190may be a cathode (that is an electron injection electrode), and in this regard, a material for forming the second electrode190may be a material having a low work function, for example, a metal, an alloy, an electrically conductive compound, or a mixture thereof.

The second electrode190may include at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ITO, and IZO, but is not limited thereto. The second electrode190may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

An organic light-emitting device20ofFIG.2includes a first capping layer210, a first electrode110, an organic layer150, and a second electrode190which are sequentially stacked in this stated order; an organic light-emitting device30ofFIG.3includes a first electrode110, an organic layer150, a second electrode190, and a second capping layer220which are sequentially stacked in this stated order; and an organic light-emitting device40ofFIG.4includes a first capping layer210, a first electrode110, an organic layer150, a second electrode190, and a second capping layer220which are sequentially stacked in this stated order.

RegardingFIGS.2to4, descriptions of the first electrode110, the organic layer150, and the second electrode190may be understood by referring to the descriptions thereof presented in connection withFIG.1.

In the organic layer150of each of the organic light-emitting devices20and40, light generated in an emission layer may pass through the first electrode110(which may be a semi-transmissive electrode or a transmissive electrode) and the first capping layer210toward the outside; and in the organic layer150of each of the organic light-emitting devices30and40, light generated in an emission layer may pass through the second electrode190(which may be a semi-transmissive electrode or a transmissive electrode) and the second capping layer220toward the outside.

The first capping layer210and/or the second capping layer220may increase external luminescent efficiency according to the principle of constructive interference.

The first capping layer210and the second capping layer220may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or a composite capping layer including an organic material and an inorganic material.

At least one selected from the first capping layer210and the second capping layer220may each independently include at least one material selected from carbocyclic compounds, heterocyclic compounds, amine-based compounds, porphine derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkaline metal complexes, and alkaline earth metal-based complexes. The carbocyclic compound, the heterocyclic compound, and the amine-based compound may each independently be optionally substituted with a substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In various embodiments, at least one selected from the first capping layer210and the second capping layer220may each independently include an amine-based compound.

In various embodiments, at least one selected from the first capping layer210and the second capping layer220may each independently include the compound represented by Formula 201 or the compound represented by Formula 202.

In various embodiments, at least one selected from the first capping layer210and the second capping layer220may each independently include a compound selected from Compounds HT28 to HT33 and Compounds CP1 to CP5, but is not limited thereto:

Hereinbefore, the organic light-emitting device according to an embodiment has been described in connection withFIGS.1-4. However, embodiments of the present disclosure are not limited thereto.

Layers constituting the hole transport region, the emission layer, and layers constituting the electron transport region may each independently be formed by using one or more suitable methods such as vacuum deposition, spin coating, casting, a Langmuir-Blodgett (LB) method, ink-jet printing, laser-printing, and/or laser-induced thermal imaging.

When the respective layers of the hole transport region, the emission layer, and the respective layers of the electron transport region are formed by deposition, the deposition may be performed at a deposition temperature of about 100 to about 500° C., at a vacuum degree of about 10−8to about 10−3torr, and at a deposition rate of about 0.01 to about 100 Å/sec, by taking into account a compound for forming the layer to be deposited, and the structure of the layer to be formed.

When layers constituting the hole transport region, the emission layer, and layers constituting the electron transport region are formed by spin coating, the spin coating may be performed at a coating speed of about 2,000 rpm to about 5,000 rpm and at a heat treatment temperature of about 80° C. to 200° C., by taking into account a compound to be included in the to-be-formed layer, and the structure of the to-be-formed layer.

General Definition of Substituents

The term “C1-C10heterocycloalkyl group,” as used herein, may refer to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, and 1 to 10 carbon atoms, and non-limiting examples thereof include a tetrahydrofuranyl group and a tetrahydrothiophenyl group.

The term “C1-C10heterocycloalkylene group,” as used herein, may refer to a divalent group having the same structure as the C1-C10heterocycloalkyl group.

The term “C6-C60aryloxy group,” as used herein, may refer to a group represented by —OA102(wherein A102is the C6-C60aryl group), and the term C6-C60arylthio group used herein may refer to a group represented by —SA103(wherein A103is the C6-C60aryl group).

The term “monovalent non-aromatic condensed polycyclic group,” as used herein, may refer to a monovalent group that has two or more rings condensed (e.g., fused) with each other, only carbon atoms as ring-forming atoms (e.g., 8 to 60 carbon atoms), and non-aromaticity in the entire molecular structure (e.g., does not have overall aromaticity). A non-limiting example of the monovalent non-aromatic condensed polycyclic group is a fluorenyl group. The term “divalent non-aromatic condensed polycyclic group,” used herein, may refer to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group,” as used herein, may refer to a monovalent group that has two or more rings condensed (e.g., fused) to each other, has at least one heteroatom selected from N, O, Si, P, and S, other than carbon atoms (e.g., 1 to 60 carbon atoms), as a ring-forming atom, and has non-aromaticity in the entire molecular structure (e.g., does not have overall aromaticity). A non-limiting example of the monovalent non-aromatic condensed heteropolycyclic group is a carbazolyl group. The term “divalent non-aromatic condensed heteropolycyclic group,” used herein, may refer to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

The term “C5-C60carbocyclic group,” as used herein, may refer to a monocyclic or polycyclic group having 5 to 60 carbon atoms in which only carbon atoms are ring-forming atoms. The term “C5-C60carbocyclic group,” as used herein may refer to an aromatic carbocyclic group or a non-aromatic carbocyclic group. The term “C5-C60carbocyclic group,” as used herein, may refer to a ring (such as a benzene ring), a monovalent group (such as a phenyl group), or a divalent group (such as a phenylene group). In various embodiments, depending on the number of substituents connected to the C5-C60carbocyclic group, the C5-C60carbocyclic group may be a trivalent group or a quadrivalent group.

The term “C1-C60heterocyclic group,” as used herein, may refer to a group having the same structure as the C1-C60carbocyclic group, except that as a ring-form ing atom, at least one heteroatom selected from N, O, Si, P, and S is used, in addition to carbon atoms (e.g., the number of carbon atoms may be in a range of 1 to 60).

It will be understood that if a substituent that appears in the present disclosure is not expressly defined above, the definition of the substituent is consistent with a general definition thereof, unless stated otherwise.

The term “Ph”, as used herein, may refer to a phenyl group; the term “Me”, as used herein, may refer to a methyl group; the term “Et”, as used herein, may refer to an ethyl group; the terms “ter-Bu” or “But”, as used herein, may refer to a tert-butyl group; the term “OMe,” as used herein may refer to a methoxy group, and “D” as used herein may refer to deuterium.

The term “biphenyl group” used therein may refer to a monovalent group having two benzene rings linked to each other via a single bond. For example, “biphenyl group” may refer to “a phenyl group substituted with a phenyl group.” The “biphenyl group” may be “a substituted phenyl group” having “a C6-C60aryl group” as a substituent.

The “terphenyl group” used herein may refer to a monovalent group having three benzene rings in which adjacent benzenes are linked to each other via a single bond. For example, “terphenyl group” may refer to “a phenyl group substituted with a biphenyl group.” The “terphenyl group” may be “a substituted phenyl group” having “a C6-C60aryl group substituted with a C6-C60aryl group” as a substituent.

* and *′ used herein, unless defined otherwise, each independently refer to a binding site to a neighboring atom in a corresponding formula.

Hereinafter, a compound according to embodiments of the present disclosure and an organic light-emitting device according to embodiments will be described in more detail with reference to Synthesis Examples and Examples. However, these examples are provided for illustrative purposes only, and should not in any sense be interpreted as limiting the scope of the present disclosure. The expression “B was used instead of A” used in describing Synthesis Examples may refer to a molar equivalent of A being identical (or substantially identical) to a molar equivalent of B.

EXAMPLES

Synthesis Example 1: Synthesis of Compound 1

Synthesis Example 2: Synthesis of Compound 2

0.65 g (yield=70%) of Compound 2 (7′-(10-phenylanthracen-9-yl)spiro[benzo[b]fluoreno[2,3-d]thiophene-11,5′-indeno[1,2-c]pyridine]) was prepared in the same (or substantially the same) manner as in Synthesis Example 1, except that 7′-bromospiro[benzo[b]fluoreno[2,3-d]thiophene-11,5′-indeno[1,2-c]pyridine] was used instead of 7′-bromospiro[fluoreno[3,2-b]benzofuran-11,5′-indeno[1,2-c]pyridine].

Synthesis Example 3: Synthesis of Compound 7

0.68 g (yield=70%) of Compound 7 (7′-(10-(naphthalen-1-yl)anthracen-9-yl)spiro[fluoreno[3,2-b]benzofuran-11,5′-indeno[1,2-c]pyridine]) was prepared in the same (or substantially the same) manner as in Synthesis Example 1, except that 0.49 g (1.1 eq, 1.43 mmol) of (10-naphthalen-1-yl)anthracen-9-yl)boronic acid was used instead of (10-phenylanthracen-9-yl)boronic acid.

Synthesis Example 4: Synthesis of Compound 8

0.70 g (yield=70%) of Compound 8 (7′-(10-(naphthalen-1-yl)anthracen-9-yl)spiro[benzo[b]fluoreno[2,3-d]thiophene-11,5′-indeno[1,2-c]pyridine]) was prepared in the same (or substantially the same) manner as in Synthesis Example 2, except that 0.49 g (1.1 eq, 1.43 mmol) of (10-naphthalene-1-yl)anthracen-9-yl)boronic acid was used instead of (10-phenylanthracen-9-yl)boronic acid.

As a substrate and an anode, a Corning 150/cm2(1,200 Å) ITO glass substrate was cut to a size of 50 mm×50 mm×0.7 mm, and then, sonicated with isopropyl alcohol and pure water, each for 5 minutes, and then washed by irradiation of ultraviolet ray for 30 minutes and ozone, and the resultant glass substrate was placed in a vacuum deposition apparatus.

2-TNATA was vacuum-deposited on the ITO anode to form a hole injection layer having a thickness of 600 Å, and 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 300 Å.

Compound 1 (as a host) and Compound 107 (as a dopant) were co-deposited on the hole transport layer at a weight ratio of 97:3 to form an emission layer having a thickness of 20 nm.

Compound ET1 was deposited on the emission layer to form an electron transport layer having a thickness of 300 Å, LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and Al was vacuum-deposited on the electron injection layer to form a cathode having a thickness of 3,000 Å, thereby completing the manufacture of an organic light-emitting device.

Examples 2 to 6 and Comparative Examples 1 to 4

Organic light-emitting devices were manufactured in the same (or substantially the same) manner in Example 1, except that compounds as shown in Table 1 were respectively used as a host and a dopant in forming an emission layer, instead of Compound 1 and/or Compound 107.

Evaluation Example 1

The driving voltage, current density, luminance, and efficiency of the organic light-emitting devices of Examples 1 to 6 and Comparative Examples 1 to 4 were evaluated by using Keithley SMU 236 meter and a PR650 luminance measuring meter. Results thereof are shown in Table 1.

Referring to the results shown in Table 1, it can be seen that the organic light-emitting devices of Examples 1 to 6 had low driving voltage, high luminance, and high efficiency, compared to those of the organic light-emitting devices of Comparative Examples 1 to 4.

According to embodiments of the present disclosure, an organic light-emitting device including the first compound and the second compound may have low driving voltage, high efficiency, and high luminance.

It will be understood that when an element such as a layer, film, region, or substrate is referred to as being “on” another element, it can be directly on the other element or intervening elements may also be present. In contrast, when an element is referred to as being “directly on” or “directly contacting” another element, there are no intervening elements present.