US 11,696,499 B2
Organic light-emitting device
Hwan-Hee Cho, Yongin-si (KR); Myeong-Suk Kim, Yongin-si (KR); Sung-Wook Kim, Yongin-si (KR); Se-Hun Kim, Yongin-si (KR); and Jin-Soo Hwang, Yongin-si (KR)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Filed by SAMSUNG DISPLAY CO., LTD., Yongin-si (KR)
Filed on May 4, 2020, as Appl. No. 16/866,460.
Application 16/866,460 is a continuation of application No. 15/293,174, filed on Oct. 13, 2016.
Claims priority of application No. 10-2016-0057130 (KR), filed on May 10, 2016.
Prior Publication US 2020/0266362 A1, Aug. 20, 2020
This patent is subject to a terminal disclaimer.
Int. Cl. H01L 51/54 (2006.01); H01L 51/00 (2006.01); C09K 11/02 (2006.01); C09K 11/06 (2006.01); H01L 51/50 (2006.01)
CPC H01L 51/0072 (2013.01) [C09K 11/025 (2013.01); C09K 11/06 (2013.01); H01L 51/0054 (2013.01); H01L 51/0067 (2013.01); H01L 51/0071 (2013.01); H01L 51/0085 (2013.01); H01L 51/5004 (2013.01); C09K 2211/1007 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/185 (2013.01); H01L 51/006 (2013.01); H01L 51/0061 (2013.01); H01L 51/0073 (2013.01); H01L 51/0074 (2013.01); H01L 51/5016 (2013.01); H01L 51/5024 (2013.01); H01L 51/5056 (2013.01); H01L 2251/5384 (2013.01); H01L 2251/552 (2013.01)] 16 Claims
 
1. An organic light-emitting device comprising:
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 comprising an emission layer,
wherein the organic layer comprises a first compound, a second compound, a third compound, and a fourth compound, and
the first compound to the fourth compound satisfy Equations 1 to 8:
E1,LUMO≥E2,LUMO+0.15 electron volts (eV)  Equation 1
E1,HOMO≥E2,HOMO+0.15 eV  Equation 2
E1,T1≥E4,T1  Equation 3
E2,T1≥E4,T1  Equation 4
E3,T1≥E4,T1  Equation 5
E3,LUMO≥E2,LUMO+0.1 eV  Equation 6
−5.6 eV≥E3,HOMO  Equation 7
Egap1≥Egap3,  Equation 8
wherein, in Equations 1 to 8,
E1,LUMO indicates a lowest unoccupied molecular orbital (LUMO) energy level of the first compound,
E2,LUMO indicates a LUMO energy level of the second compound,
E3,LUMO indicates a LUMO energy level of the third compound,
E1,HOMO indicates a highest occupied molecular orbital (HOMO) energy level of the first compound,
E2,HOMO indicates a HOMO energy level of the second compound,
E3,HOMO indicates a HOMO energy level of the third compound,
E1,T1 indicates a lowest excited triplet energy level of the first compound,
E2,T1 indicates a lowest excited triplet energy level of the second compound,
E3,T1 indicates a lowest excited triplet energy level of the third compound,
E4,T1 indicates a lowest excited triplet energy level of the fourth compound,
Egap1 indicates a gap between the LUMO energy level of the first compound and the HOMO energy level of the first compound, and
Egap3 indicates a gap between the LUMO energy level of the third compound and the HOMO energy level of the third compound,
wherein
the third compound is represented by Formula 4:

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wherein, in Formulae 4 and 5,
A51 is selected from a benzene group, a naphthalene group, a fluorene group, a phenanthrene group, an anthracene group, a triphenylene group, a pyrene group, a chrysene group, a furan group, a thiophene group, a pyrrole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a 2,6-naphthyridine group, a 1,8-naphthyridine group, a 1,5-naphthyridine group, a 1,6-naphthyridine group, a 1,7-naphthyridine group, a 2,7-naphthyridine group, a quinoxaline group, a quinazoline group, a benzofuran group, a benzothiophene group, a dibenzofuran group, a dibenzothiophene group, and a carbazole group
X51 is selected from N and CR51,
L41 to L43 are each independently selected from the group consisting of:
a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubicenylene group, a coronenylene group, an ovalenylene group, a pyrrolylene group, a thiophenylene group, a furanylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an isoindolylene group, an indolylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, a benzofuranylene group, a benzothiophenylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a dibenzosilolylene group, a benzocarbazolylene group, and a dibenzocarbazolylene group; and
a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubicenylene group, a coronenylene group, an ovalenylene group, a pyrrolylene group, a thiophenylene group, a furanylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an isoindolylene group, an indolylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, a benzofuranylene group, a benzothiophenylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, dibenzosilolylene group, a benzocarbazolylene group, and a dibenzocarbazolylene 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-C20 alkyl group, a C1-C20 alkoxy 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 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 phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl 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, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32),
wherein Q31 to Q33 are each independently selected from hydrogen, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, a tert-butyl group, a phenyl group, a biphenyl group, and a terphenyl group,
a41 to a43 are each independently selected from 0, 1, 2, 3, 4, and 5,
at least one selected from L41 to L43 is a group represented by Formula 5, provided that L41 to L43 are not a carbazolylene group and are not a benzofluorenylene group,
wherein when L41 is a group represented by Formula 5, a41 is selected from 1, 2, 3, 4, and 5; when L42 is a group represented by Formula 5, a42 is selected from 1, 2, 3, 4, and 5; and when L43 is a group represented by Formula 5, a43 is selected from 1, 2, 3, 4, and 5,
R41 to R43 are each independently a hole transporting group or an electron transporting group, provided that R41 to R43 are not a carbazolyl group and are not a benzofluorenyl group,
R51 and R52 are each independently a hole transporting group,
at least one selected from R41 to R43 is represented by one selected from Formula 4a and 4b:

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wherein, in Formulae 4a and 4b,
X41 is selected from N(R401), C(R401)(R402), Si(R401)(R402), O, and S,
X42 is selected from N, C(R403), and Si(R403),
A41 to A44 are each independently selected from a benzene group, a naphthalene group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a 2,6-naphthyridine group, a 1,8-naphthyridine group, a 1,5-naphthyridine group, a 1,6-naphthyridine group, a 1,7-naphthyridine group, a 2,7-naphthyridine group, a quinoxaline group, and a quinazoline group,
descriptions of R44 to R47 and R401 to R403 are each independently the same as the descriptions provided below in connection with Z11 to Z14, Z31 to Z34, Z41 to Z44, and Z51 to Z56,
b44 to b47 are each independently selected from 1, 2, 3, and 4, and
R401 and R402 are optionally bound to form a saturated or unsaturated ring,
wherein when A41 and A42 are both a benzene group, X41 is selected from C(R401)(R402), Si(R401)(R402), O, and S, and
when A43 and A44 are both a benzene group, X42 is selected from C(R403) and Si(R403), and
wherein when one of A41 and A42 is a benzene group, the other is not a naphthalene group, and
when one of A43 and A44 is a benzene group, the other is not a naphthalene group,
b52 is selected from 1, 2, 3, and 4, and
* indicates a binding site to an adjacent atom, and
the first compound is represented by one of Formulae 1-1, 2-1, 2-2, and 3-1, and
the second compound is represented by one of Formulae 1-2, 2-3, 2-4, and 3-2:

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wherein, in Formulae 1-1, 1-2, 2-1 to 2-4, 3-1, and 3-2,
A11 to A14 and A21 to A23, are each independently selected from a benzene group, a naphthalene group, a fluorene group, a phenanthrene group, an anthracene group, a triphenylene group, a pyrene group, a chrysene group, a furan group, a thiophene group, a pyrrole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a 2,6-naphthyridine group, a 1,8-naphthyridine group, a 1,5-naphthyridine group, a 1,6-naphthyridine group, a 1,7-naphthyridine group, a 2,7-naphthyridine group, a quinoxaline group, a quinazoline group, a benzofuran group, a benzothiophene group, a dibenzofuran group, a dibenzothiophene group, and a carbazole group,
X11 is selected from O, S, N[(L12)a12-R12], C[(L12)a12-R12](R17), Si[(L12)a12-R12](R17), P[(L12)a12-R12], B[(L12)a12-R12], and P(═O)[(L12)a12-R12],
X12 is selected from O, S, N[(L15)a15-R19], C[(L15)a15-R19](R20), Si[(L15)a15-R19](R20), P[(L15)a15-R19], B[(L15)a15-R19], and P(═O)[(L15)a15-R19],
X21 is selected from N[(L21)a21-R21], C[(L21)a21-R21](R23), O, and S,
X22 is selected from N[(L22)a22-R22], C[(L22)a22-R22](R24), O, and S,
X71 is selected from N[(L71)a71-R71], C[(L71)a71-R71](R73), O, and S,
X72 is selected from N[(L72)a72-R72], C[(L72)a72-R72](R74), O, and S,
R12 and R17 are optionally bound to form a saturated or unsaturated ring,
R19 and R20 are optionally bound to form a saturated or unsaturated ring,
L11 to L13, L31 to L33, L71, and L72 are each independently selected from the group consisting of:
a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a dibenzosilolylene group, a benzocarbazolylene group, and a dibenzocarbazolylene group; and
a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a dibenzosilolylene group, a benzocarbazolylene group, and a dibenzocarbazolylene group, each substituted with at least one selected from deuterium, —F, a cyano group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a methoxy group, an ethoxy group, an n-propoxy group, an iso-propoxy group, an n-butoxy group, a sec-butoxy group, an iso-butoxy group, a tert-butoxy 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 phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, —N(Q31)(Q32), —Si(Q31)(Q32)(Q33), and —B(Q31)(Q32), and
L14, L15, L21, L22, and L61 to L63 are each independently selected from the group consisting of:
a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a thiophenylene group, a furanylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a carbazolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a dibenzosilolylene group, a benzocarbazolylene group, and a dibenzocarbazolylene group; and
a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a thiophenylene group, a furanylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a carbazolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a dibenzosilolylene group, a benzocarbazolylene group, and a dibenzocarbazolylene group, each substituted with at least one selected from deuterium, —F, a cyano group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a methoxy group, an ethoxy group, an n-propoxy group, an iso-propoxy group, an n-butoxy group, a sec-butoxy group, an iso-butoxy group, a tert-butoxy 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 phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a thiophenyl group, a furanyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, —N(Q31)(Q32), —Si(Q31)(Q32)(Q33), and —B(Q31)(Q32),
wherein Q31 to Q33 are each independently selected from a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group,
a11 to a15, a21, a22, a31 to a33, a61 to a63, a71, and a72 are each independently selected from 0, 1, 2, 3, 4, and 5,
R11 to R17, R31 to R36, and R71 to R77 are each independently a hole transporting group,
R18 to R27 and R61 to R66 are each independently a hole transporting group or an electron transporting group,
b13 to b16, b25 to b27, b43 to b48, and b75 to b77 are each independently selected from 1, 2, 3, and 4,
n31 to n33 and n61 to n63 are each independently selected from 0, 1, 2, 3, and 4,
* indicates a binding site to an adjacent atom,
wherein the hole transporting group is selected from a C1-C20 alkyl group, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), and a group represented by any of Formulae 5-1 to 5-19:

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wherein, in Formulae 5-1 to 5-19,
Y11 is selected from O, S, C(Z13)(Z14), N(Z13), and Si(Z13)(Z14),
Z11 to Z14 are each independently selected from the group consisting of:
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-C20 alkyl group, a C1-C20 alkoxy 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 benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, an isobenzothiazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32); and
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a carbazolyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group, each substituted with at least one selected from a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a carbazolyl group, a fluorenyl group, —Si(Q21)(Q22)(Q23), and —N(Q21)(Q22),
wherein Q1 to Q3, Q21 to Q23, and Q31 to Q33 are each independently selected from a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group,
e2 is an integer selected from 1 and 2, e3 is an integer selected from 1 to 3, e4 is an integer selected from 1 to 4, e5 is an integer selected from 1 to 5, e6 is an integer selected from 1 to 6, e7 is an integer selected from 1 to 7, e9 is an integer selected from 1 to 9, and
* indicates a binding site to an adjacent atom, and
the electron transporting group is selected from —CN, —CF3, and a group represented by any of Formulae 6-1 to 6-128:

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wherein, in Formulae 6-1 to 6-128,
Y31 is selected from O, S, C(Z33)(Z34), N(Z33), and Si(Z33)(Z34),
Y41 is N or C(Z41), Y42 is N or C(Z42), Y43 is N or C(Z43), Y44 is N or C(Z44), Y51 is N or C(Z51), Y52 is N or C(Z52), Y53 is N or C(Z53), Y54 is N or C(Z54), Y55 is N or C(Z55), Y56 is N or C(Z56),
at least one selected from Y41 to Y43 and Y51 to Y54 in Formulae 6-118 to 6-121 is N, at least one selected from Y41 to Y44 and Y51 to Y54 in Formula 6-122 is N, at least one selected from Y41 to Y43 and Y51 to Y56 in Formula 6-123 is N,
Z31 to Z34, Z41 to Z44, and Z51 to Z56 are each independently selected from the group consisting of:
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-C20 alkyl group, a C1-C20 alkoxy 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 pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl 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 indolyl group, an isoindolyl 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 phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl 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 dibenzosilolyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32); and
a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, and a quinazolinyl group, each substituted with at least one selected from a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a fluorenyl group, —Si(Q21)(Q22)(Q23), and —N(Q21)(Q22),
Z61 is selected from hydrogen, a cyano group, —F, and —CF3, and at least one Z61 is selected from a cyano group, —F, and —CF3,
wherein Q21 to Q23 and Q31 to Q33 are each independently selected from a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, and a quinazolinyl group,
e2 is an integer selected from 1 and 2, e3 is an integer selected from 1 to 3, e4 is an integer selected from 1 to 4, e5 is an integer selected from 1 to 5, e6 is an integer selected from 1 to 6, e7 is an integer selected from 1 to 7, and
* indicates a binding site to an adjacent atom.