Carbazole-based compound and organic light-emitting device including the same
A carbazole compound represented by Formula 1: wherein in Formula 1, groups X 1 to X 8 , X 11 to X 19 , and R 41 to R 43 are the same as in the specification.
1. A carbazole compound represented by Formula 1:
wherein in the Formulae 1, 2A(2), 2B, 2C, and 2D,
X 1 is N or C(R 1 ), X 2 is N or C(R 2 ), X 3 is N or C(R 3 ), X 4 is N or C(R 4 ), X 5 is N or C(R 5 ), X 6 is N or C(R 6 ), X 7 is N or C(R 7 ), X 8 is N or C(R 8 ), X 11 is N or C(R 11 ), X 12 is N or C(R 12 ), X 13 is N or C(R 13 ), X 14 is N or C(R 14 ), X 15 is N or C(R 5 ), X 16 is N or C(R 16 ), X 17 is N or C(R 7 ), X 18 is N or C(R 8 ), X 19 is C(R 19 ) wherein R 19 is a hydrogen, X 22 is N, C or C(R 22 ), X 23 is N, C or C(R 23 ), X 24 is N, C or C(R 24 ), X 25 is N, C or C(R 25 ), X 26 is N, C or C(R 26 ), X 31 is N, C or C(R 31 ), X 32 is N, C or C(R 32 ), X 33 is N, C or C(R 33 ), X 34 is N, C or C(R 34 ), and X 35 is N, C or C(R 35 ),
provided that at least one selected from X 1 to X 8 and X 11 to X 18 is N,
provided that when X 22 is C, X 22 is connected to a carbon of a phenyl group of Formula 2B, when X 23 is C, X 23 is connected to a carbon of a phenyl group of Formula 2B, when X 24 is C, X 24 is connected to a carbon of a phenyl group of Formula 2B, when X 25 is C, X 25 is connected to a carbon of a phenyl group of Formula 2B, when X 26 is C, X 26 is connected to a carbon of a phenyl group of Formula 2B, when X 31 is C, X 31 is connected to a carbon of a phenyl group of Formulae 2C and 2D, when X 32 is C, X 32 is connected to a carbon of a phenyl group of Formulae 2C and 2D, when X 33 is C, X 33 is connected to a carbon of a phenyl group of Formulae 2C and 2D, when X 34 is C, X 34 is connected to a carbon of a phenyl group of Formulae 2C and 2D, when X 35 is C, X 35 is connected to a carbon of a phenyl group of Formulae 2C and 2D, one selected from X 22 to X 26 in Formula 2B is C, and one selected from X 31 to X 35 in Formulae 2C and 2D is C,
R 1 to R 8 , R 11 to R 18 , R 21 to R 27 , and R 31 to R 38 are each independently selected from
a hydrogen, a deuterium, —F, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group;
a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group, each substituted with at least one selected from a deuterium, —F, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof and a phosphoric acid group or a salt thereof;
a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;
a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group and a dibenzothiophenyl group, each substituted with at least one selected from a deuterium, —F, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q 1 )(Q 2 )(Q 3 ); and
—Si(Q 11 )(Q 12 )(Q 13 ),
a1, a3, and a5 are each independently an integer selected from 1 to 4, and a2, a4 and a6 are each independently an integer selected from 1 to 5,
each of R 22 to R 26 is not a cyano group,
at least one of groups R 27 in the number of a2 in Formula 2B is a cyano group, at least one selected from R 31 to R 35 , groups R 36 in the number of a3 and groups R 37 in the number of a4 in Formula 2C is a cyano group, and at least one selected from R 31 to R 35 , groups R 36 in the number of a3, groups R 37 in the number of a5, and groups R 38 in the number of a6 in Formula 2D is a cyano group,
R 41 to R 43 are each independently selected from
groups represented by Formulae 2A(2), 2B, 2C, and 2D;
a hydrogen, a deuterium, —F, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group;
a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group, each substituted with at least one selected from a deuterium, —F, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof and a phosphoric acid group or a salt thereof;
a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;
a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group and a dibenzothiophenyl group, each substituted with at least one selected from a deuterium, —F, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q 21 )(Q 22 )(Q 23 ); and
—Si(Q 31 )(Q 32 )(Q 33 ),
at least one selected from R 41 to R 43 is a group represented by one of Formulae 2A(2), 2B, 2C, and 2D, and
Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 are each independently selected from a hydrogen, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.
2. The carbazole compound of claim 1 , wherein
R 1 to R 8 , R 11 to R 18 , R 21 to R 27 , and R 31 to R 38 are each independently selected from
a hydrogen, a deuterium, —F, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 10 alkyl group, and a C 1 -C 10 alkoxy group;
a C 1 -C 10 alkyl group and a C 1 -C 10 alkoxy group, each substituted with at least one selected from a deuterium, —F, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof and a phosphoric acid group or a salt thereof;
a phenyl group and a pyridinyl group;
a phenyl group and a pyridinyl group, each substituted with at least one selected from a deuterium, —F, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a pyridinyl group, and —Si(Q 1 )(Q 2 )(Q 3 ); and
—Si(Q 11 )(Q 12 )(Q 13 ),
a1 to a6 are each independently an integer selected from 1 to 3,
Q 1 to Q 3 and Q 11 to Q 13 are each independently selected from a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a naphthyl group and a pyridinyl group,
R 22 to R 26 are not a cyano group, and
at least one of groups R 27 in the number of a2 in Formula 2B is a cyano group, at least one selected from R 31 to R 35 , groups R 36 in the number of a3 and groups R 37 in the number of a4 in Formula 2C is a cyano group, and at least one selected from R 31 to R 35 , groups R 36 in the number of a3, groups R 37 in the number of a5, and groups R 38 in the number of a6 in Formula 2D is a cyano group.
3. The carbazole compound of claim 1 , wherein
R 41 to R 43 are each independently selected from
groups represented by Formulae 2A(2), 2B, 2C, and 2D;
a hydrogen, a deuterium, —F, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 10 alkyl group, and a C 1 -C 10 alkoxy group;
a C 1 -C 10 alkyl group and a C 1 -C 10 alkoxy group, each substituted with at least one selected from a deuterium, —F, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof and a phosphoric acid group or a salt thereof;
a phenyl group and a pyridinyl group;
a phenyl group and a pyridinyl group, each substituted with at least one selected from a deuterium, —F, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a pyridinyl group, and —Si(Q 21 )(Q 22 )(Q 23 ); and
—Si(Q 31 )(Q 32 )(Q 33 ),
at least one selected from R 41 to R 43 is a group represented by one of Formulae 2A(2), 2B, 2C, and 2D,
Q 21 to Q 23 and Q 31 to Q 33 are each independently selected from a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a naphthyl group and a pyridinyl group.
4. The carbazole compound of claim 1 , wherein
R 42 in Formula 1 is represented by one of Formulae 2A(2), 2B, 2C, and 2D.
5. The carbazole compound of claim 1 , wherein
at least one selected from X 3 , X 7 , X 13 , and X 17 in Formula 1 is C(CN).
6. The carbazole compound of claim 1 , wherein
the carbazole compound is represented by one of Formulae 1A to 1F:
wherein in Formulae 1A to 2F,
X 5 is N or C(R 5 ), and X 6 is N or C(R 6 ) wherein at least one of X 5 and X 6 is N,
R 1 to R 8 and R 11 to R 18 are each independently selected from
a hydrogen, a deuterium, —F, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 10 alkyl group, and a C 1 -C 10 alkoxy group;
a C 1 -C 10 alkyl group and a C 1 -C 10 alkoxy group, each substituted with at least one selected from a deuterium, —F, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof and a phosphoric acid group or a salt thereof;
a phenyl group and a pyridinyl group;
a phenyl group and a pyridinyl group, each substituted with at least one selected from a deuterium, —F, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a pyridinyl group, and —Si(Q 1 )(Q 2 )(Q 3 ); and
—Si(Q 11 )(Q 12 )(Q 13 ),
Q 1 to Q 3 and Q 11 to Q 13 are each independently selected from a hydrogen, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, and
X 19 , R 41 , R 42 , and R 43 are the same as in claim 1 .
7. The carbazole compound of claim 1 , wherein
in Formulae 2A(2), 2B, 2C, and 2D,
R 21 to R 27 and R 31 to R 38 are each independently selected from
a hydrogen, a deuterium, —F, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group;
a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group, each substituted with at least one selected from a deuterium, —F, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof, and
—Si(Q 11 )(Q 12 )(Q 13 ), and
a1 to a6 are each independently 1 or 2.
8. The carbazole compound of claim 1 , wherein the group represented by Formula 2A(2) comprises a group represented by one of Formulae 2A-1 to 2A-7:
9. The carbazole compound of claim 1 , wherein
the group represented by Formula 2B comprises a group represented by one of Formulae 2B-1 to 2B-7:
wherein X 22 to X 26 in Formulae 2B-1 to 2B-7 are the same as in claim 1 .
10. The carbazole compound of claim 1 , wherein
the group represented by Formula 2B comprises a group represented by one of Formulae 2B(1) to 2B(13):
wherein R 22 to R 27 and a2 in Formulae 2B(1) to 2B(13) are the same as in claim 1 .
11. The carbazole compound of claim 1 , wherein
the group represented by Formula 2B comprises a group represented by one of Formulae 2B(1)-1 to 2B(13)-1, 2B(1)-2 to 2B(13)-2, 2B(1)-3 to 2B(13)-3, 2B(1)-4 to 2B(13)-4, 2B(1)-5 to 2B(13)-5, 2B(1)-6 to 2B(13)-6, and 2B(1)-7 to 2B(13)-7:
wherein R 22 to R 26 in Formulae 2B(1)-1 to 2B(13)-1, 2B(1)-2 to 2B(13)-2, 2B(1)-3 to 2B(13)-3, 2B(1)-4 to 2B(13)-4, 2B(1)-5 to 2B(13)-5, 2B(1)-6 to 2B(13)-6, and 2B(1)-7 to 2B(13)-7 are the same as in claim 1 .
12. The carbazole compound of claim 1 , wherein
the group represented by Formula 2C comprises a group represented by one of Formulae 2C-1 to 2C-9, and 2C-1(1) to 2C-9(1):
wherein X 31 to X 35 , R 36 , R 37 , a3, and a4 in Formulae 2C-1 to 2C-9, and 2C-1(1) to 2C-9(1) are the same as in claim 1 .
13. The carbazole compound of claim 1 , wherein
the group represented by Formula 2C comprises a group represented by one of Formulae 2C(1) to 2C(9):
wherein X 31 to X 35 , R 36 , R 37 , a3, and a4 in Formulae 2C(1) to 2C(9) are the same as in claim 1 .
14. The carbazole compound of claim 1 , wherein
the group represented by Formula 2D comprises a group represented by one of Formulae 2D-1 to 2D-12 and 2D-1(1) to 2D-12(1):
wherein X 31 to X 35 , R 36 , R 37 , R 38 , a3, a5, and a6 in Formulae 2D-1 to 2D-12 and 2D-1(1) to 2D-12(1) are the same as in claim 1 .
15. The carbazole compound of claim 1 , wherein
the group represented by Formula 2D comprises a group represented by one of Formulae 2D(1) to 2D(27):
descriptions of X 31 to X 35 , R 36 , R 37 , R 38 , a3, a5, and a6 in Formulae 2D(1) to 2D(27) are the same as recited in claim 1 .
16. The carbazole compound of claim 1 , wherein
R 42 in Formula 1 is represented by one of Formulae 2A-1 to 2A-7, 3B-1 to 3B-12, 3C-1 to 3C-6, and 3D-1 to 3D-6:
17. A carbazole compound selected from Compounds 10 to 18, 37 to 72, 79 to 90, 97 to 108, 127 to 171, and 181 to 202:
18. 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 at least one carbazole compound of claim 1 .
19. The organic light-emitting device of claim 18 , wherein the emission layer comprises the at least one carbazole compound represented by Formula 1.
20. The organic light-emitting device of claim 18 , wherein the emission layer comprises the at least one carbazole compound represented by Formula 1 and a phosphorescent dopant.