US2020243773A1PendingUtilityA1
Organic light-emitting device
Assignee: SAMSUNG ELECTRONICS CO LTDPriority: Sep 30, 2015Filed: Apr 13, 2020Published: Jul 30, 2020
Est. expirySep 30, 2035(~9.2 yrs left)· nominal 20-yr term from priority
Inventors:Hyun Sik ChaeSoonok JeonHosuk KangHiroshi MiyazakiSooghang IhnSeongik HongMasaki NumataSunghan KimRafael Gomez-BombarelliMartin B.Z. ForsytheJorge Aguilera-IparraguirreAlan Aspuru-GuzikTimothy D. Hirzel
H10K 2101/20H10K 85/654C07D 403/10C07D 209/82C07D 403/14C09K 11/06C09K 2211/1029C07D 209/88H10K 85/6572H10K 50/11H10K 2101/10H10K 2101/30H10K 50/81H10K 85/636H10K 2101/40H10K 85/60H10K 50/82H10K 50/121C09K 2211/1044C09K 2211/1014C09K 2211/1007H05B 33/20C09K 11/025H05B 33/14H01L 2251/552H01L 51/0061H01L 51/5221H01L 51/005H01L 51/0072H01L 51/0067
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Claims
Abstract
An organic light-emitting device including a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises an emission layer, and wherein the organic layer comprises a first compound represented by Formula 1 and a second compound having the lowest excited triplet energy level greater than 2.73 electron volts: wherein in Formula 1, R 11 to R 33 are the same as described in the specification.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . An organic light-emitting device comprising:
a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises an emission layer, and wherein the organic layer comprises a first compound represented by Formula 1 and a second compound having the lowest excited triplet energy level greater than 2.73 electron volts:
wherein, in Formulae 1 and 9-2,
R 11 to R 14 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 1 -C 60 alkylthio group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), and groups represented by Formula 9-2,
provided that at least one selected from R 11 to R 14 is selected from groups represented by Formula 9-2,
R 15 to R 33 and R 91 to R 100 are each independently 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 C 1 -C 60 alkyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 1 -C 60 alkylthio group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), and —P(═O)(Q 1 )(Q 2 ),
a11 is selected from 1, 2, and 3,
L 91 is selected from a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
a91 is selected from 0, 1, and 2,
wherein Q 1 to Q 3 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, and
* indicates a binding site to an adjacent atom.
2 . The organic light-emitting device of claim 1 , wherein a difference between the highest occupied molecular orbital energy level of the first compound and the highest occupied molecular orbital energy level of the second compound is in a range of about 0 electron volts or greater to about 0.1 electron volts or less.
3 . The organic light-emitting device of claim 1 , wherein the emission layer comprises the first compound and the second compound.
4 . The organic light-emitting device of claim 1 , wherein the lowest excited triplet energy level of the second compound is greater than the lowest excited triplet energy level of the first compound.
5 . The organic light-emitting device of claim 4 , wherein the lowest excited triplet energy level of the first compound is about 2.7 electron volts or less.
6 . The organic light-emitting device of claim 1 , wherein a difference ΔE ST1 between the lowest excited triplet energy level of the first compound and the lowest excited singlet energy level of the first compound is in a range of about 0 electron volts or greater to about 0.34 electron volts or less.
7 . The organic light-emitting device of claim 1 , wherein R 11 and R 14 are each independently 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 C 1 -C 60 alkyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 1 -C 60 alkylthio group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), and —P(═O)(Q 1 )(Q 2 ), and
R 12 and R 13 are each independently 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 C 1 -C 60 alkyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 1 -C 60 alkylthio group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), and groups represented by Formula 9-2,
provided that at least one selected from R 12 and R 13 is selected from groups represented by Formula 9-2.
8 . The organic light-emitting device of claim 1 , wherein R 11 to R 14 are each independently 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 C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 1 -C 20 alkylthio group, a phenyl group, a biphenyl group, a terphenyl 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-bifluorenyl 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 thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group and —N(Q 1 )(Q 2 );
a phenyl group, a biphenyl group, a terphenyl 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-bifluorenyl 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 thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl 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 C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 1 -C 20 alkylthio group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C 1 -C 10 alkyl group, a phenyl group substituted with —F, 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-bifluorenyl 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 thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, and —N(Q 31 )(Q 32 ); and
groups represented by Formula 9-2,
provided that at least one selected from R 11 to R 14 is selected from groups represented by Formula 9-2,
wherein Q 1 , Q 2 , Q 31 , and Q 32 are each independently selected from a C 1 -C 20 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl 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-bifluorenyl 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 thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group.
9 . The organic light-emitting device of claim 1 , wherein R 11 to R 14 are each independently selected from hydrogen, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, and —N(Q 1 )(Q 2 );
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, and —N(Q 31 )(Q 32 ); and
groups represented by Formula 9-2,
provided that at least one selected from R 11 to R 14 is selected from groups represented by Formula 9-2,
wherein Q 1 , Q 2 , Q 31 , and Q 32 are each independently selected from a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group.
10 . The organic light-emitting device of claim 1 , wherein R 15 to R 33 and R 91 to R 100 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 1 -C 20 alkylthio group, a phenyl group, a biphenyl group, a terphenyl 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-bifluorenyl 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 thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, and —N(Q 1 )(Q 2 ); and
a phenyl group, a biphenyl group, a terphenyl 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-bifluorenyl 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 thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl 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 C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 1 -C 20 alkylthio group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C 1 -C 10 alkyl group, a phenyl group substituted with —F, 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 thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, and —N(Q 31 )(Q 32 ),
wherein Q 1 , Q 2 , Q 31 , and Q 32 are each independently selected from a C 1 -C 20 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl 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-bifluorenyl 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 thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group.
11 . The organic light-emitting device of claim 1 , wherein R 15 to R 33 and R 91 to R 100 are each independently selected from hydrogen, a cyano group, a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, and —N(Q 1 )(Q 2 ); and
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group, each substituted with at least one selected from deuterium, —F, -Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, and —N(Q 31 )(Q 32 ),
wherein Q 1 , Q 2 , Q 31 , and Q 32 are each independently selected from a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group.
12 . The organic light-emitting device of claim 1 , wherein R 91 to R 100 are each independently selected from hydrogen, a cyano group, a C 1 -C 20 alkyl group, a carbazolyl group, and —N(Q 1 )(Q 2 ); and
a carbazolyl group substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a carbazolyl group, and —N(Q 31 )(Q 32 ),
wherein Q 1 , Q 2 , Q 31 , and Q 32 are each independently selected from a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, and a carbazolyl group.
13 . The organic light-emitting device of claim 1 , wherein the first compound is represented by one of Formula 1-2:
wherein, in Formula 1-2,
R 11 to R 33 and a11 are the same as in Formula 1, and
R 91 to R 100 , L 91 , and a91 are the same as in Formula 9-2.
14 . The organic light-emitting device of claim 1 , wherein the first compound is selected from compounds:
15 . The organic light-emitting device of claim 1 , wherein the second compound is selected from a compound comprising a carbazole ring and a phosphine oxide compound.
16 . The organic light-emitting device of claim 1 , wherein the second compound is represented by Formulae 2:
wherein, in Formulae 2, 3-1, and 3-2,
Ar 21 and Ar 22 are each independently selected from *-(L 22 ) a22 -[Si(Q 1 )(Q 2 )(Q 3 )], *-(L 22 ) a22 -[P(═O)(Q 1 )(Q 2 )], groups represented by Formula 3-1, and groups represented by Formula 3-2,
L 21 and L 22 are each independently selected from a single bond, *—O—*′, *—S—*′, *—[Si(Q 1 )(Q 2 )]-*′, *—[P(═O)(Q 1 )]-*′, a phenylene group, a pyridinylene group, a pyrimidinylene group, a pyrazinylene group, a pyridazinylene group, a triazinylene group, a naphthylene group, a fluorenylene group, a carbazolylene group, a dibenzofuranylene group, and a dibenzothiophenylene group; and
a phenylene group, a pyridinylene group, a pyrimidinylene group, a pyrazinylene group, a pyridazinylene group, a triazinylene group, a naphthylene group, a fluorenylene group, a carbazolylene group, a dibenzofuranylene group, and a dibenzothiophenylene 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 C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a C 1 -C 10 alkyl group substituted with —F, a phenyl group, a phenyl group substituted with —F, a phenyl group substituted with a cyano group, a phenyl group substituted with a C 1 -C 10 alkyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, —Si(Q 31 )(Q 32 )(Q 33 ), and —P(═O)(Q 31 )(Q 32 ),
a21 and a22 are each independently selected from 0, 1, 2, 3, 4, and 5,
A 31 and A 32 are each independently selected from a benzene group, a naphthalene group, a fluorene group, a benzofluorene group, a carbazole group, a benzocarbazole group, a dibenzofuran group, a benzonaphthofuran group, a dibenzothiophene group, and a benzonapthothiophene group,
R 31 to R 33 are each independently 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 C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), and —P(═O)(Q 1 )(Q 2 ),
b31 and b32 are each independently selected from 1, 2, 3, 4, 5, 6, 7, and 8,
wherein Q 1 to Q 3 and Q 31 to Q 33 are each independently 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 C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, and
* and *′ each indicate a binding site to an adjacent atom.
17 . The organic light-emitting device of claim 16 , wherein Ar 21 and Ar 22 are each independently selected from *-(L 22 ) a22 -[Si(Q 1 )(Q 2 )(Q 3 )], *-(L 22 ) a22 -[P(═O)(Q 1 )(Q 2 )], and groups represented by Formulae 3-11 to 3-15:
wherein, in Formulae 3-11 to 3-15,
R 31a to R 31d are each the same as R 31 defined herein in relation to Formula 3-1,
R 32a to R 32d are each the same as R 32 defined herein in relation to 3-1,
R 33 is the same as R 33 defined herein in relation to Formula 3-2, and
* indicates a binding site to an adjacent atom.
18 . The organic light-emitting device of claim 16 , wherein L 21 and L 22 are each independently selected from a single bond, *—O—*′, *—S—*′, *—[Si(Q 1 )(Q 2 )]-*′, *—[P(═O)(Q 1 )]-*′ and groups represented by Formulae 4-1 to 4-32:
wherein, in Formulae 4-1 to 4-32,
X 41 is selected from C(R 43 )(R 44 ), N(R 43 ), O, and S,
R 41 to R 44 are each independently 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 C 1 -C 10 alkyl group, a C 1 -C 10 alkyl group substituted with —F, a phenyl group, a phenyl group substituted with —F, a phenyl group substituted with a cyano group, a phenyl group substituted with a C 1 -C 10 alkyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, —Si(Q 31 )(Q 32 )(Q 33 ), and —P(═O)(Q 31 )(Q 32 ),
wherein Q 1 to Q 3 and Q 31 to Q 33 are each independently selected from hydrogen, a C 1 -C 10 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group,
b41 is selected from 1, 2, 3, and 4,
b42 is selected from 1, 2, and 3,
b43 is selected from 1 and 2, and
* and *′ each indicate a binding site to an adjacent atom.
19 . The organic light-emitting device of claim 16 , wherein R 31 to R 33 are each independently 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 C 1 -C 10 alkyl group, a C 1 -C 10 alkyl group substituted with —F, a phenyl group, a phenyl group substituted with —F, a phenyl group substituted with a cyano group, a phenyl group substituted with a C 1 -C 10 alkyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, —Si(Q 1 )(Q 2 )(Q 3 ), and —P(═O)(Q 1 )(Q 2 ),
wherein Q 1 to Q 3 are each independently selected from hydrogen, a C 1 -C 10 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
20 . The organic light-emitting device of claim 1 , wherein the second compound is selected from Compounds H1 to H17:Cited by (0)
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