Organic light-emitting device, and delayed fluorescent material and compound used therefor
An organic light-emitting device containing a compound represented by the following general formula in a light light-emitting layer has a high light-emission efficiency. The ring containing Y 1 , Y 2 and Y 3 represent a triazine ring or a pyrimidine ring; Z 1 , Z 2 and R 1 to R 8 represent a hydrogen atom or a substituent; and at least one of R 1 to R 8 represents a diarylamino group or a carbazolyl group. The compound represented by the general formula (1) contains at least two carbazole structures in the molecule thereof.
1. An organic light-emitting device containing a substrate having thereon a light-emitting layer containing a compound represented by the following formula (3) as a light-emitting material emitting light from the organic light-emitting device:
wherein in the formula (3), Y 1 , Y 2 and Y 3 all represent nitrogen atoms;
represents a hydrogen atom or a substituent selected from the group consisting of
(1) an alkyl group having from 1 to 20 carbon atoms,
(2) an aryl group having from 6 to 30 carbon atoms,
(3) a heteroaryl group having from 3 to 30 carbon atoms,
(4) a diarylamino group having from 12 to 30 carbon atoms,
(5) a carbazolyl group having from 12 to 30 carbon atoms,
(6) an alkyl group having from 1 to 20 carbon atoms, which is substituted by (2), (3), (4) and/or (5),
(7) an aryl group having from 6 to 30 carbon atoms, which is substituted by (1), (3), (4) and/or (5),
(8) a heteroaryl group having from 3 to 30 carbon atoms, which is substituted by (1), (2), (4) and/or (5),
(9) a diarylamino group having from 12 to 30 carbon atoms, which is substituted by (1), (2), (3) and/or (5), and
(10) a carbazolyl group having from 12 to 30 carbon atoms, which is substituted by (1), (2), (3) and/or (4); and
R 1 to R 8 and R 11 to R 18 each independently represent a hydrogen atom or a substituent selected independently from the group consisting of
(1) an alkyl group having from 1 to 20 carbon atoms,
(2) an aryl group having from 6 to 30 carbon atoms,
(3) a heteroaryl group having from 3 to 30 carbon atoms,
(4) a diarylamino group having from 12 to 30 carbon atoms,
(5) a carbazolyl group having from 12 to 30 carbon atoms,
(6) an alkyl group having from 1 to 20 carbon atoms, which is substituted by (2), (3), (4) and/or (5),
(7) an aryl group having from 6 to 30 carbon atoms, which is substituted by (1), (3), (4) and/or (5),
(8) a heteroaryl group having from 3 to 30 carbon atoms, which is substituted by (1), (2), (4) and/or (5),
(9) a diarylamino group having from 12 to 30 carbon atoms, which is substituted by (1), (2), (3) and/or (5), and
(10) a carbazolyl group having from 12 to 30 carbon atoms, which is substituted by (1), (2), (3) and/or (4),
provided that at least one of R 1 to R 8 and at least one of R 11 to R 18 each independently represent (4), (5), (9) or (10).
2. The organic light-emitting device according to claim 1 , which emits delayed fluorescent light.
3. The organic light-emitting device according to claim 1 , which is an organic electroluminescent device.
4. A delayed fluorescent emitter consisting of a compound represented by the following formula (3):
wherein in the formula (3), Y 1 , Y 2 and Y 3 all represent nitrogen atoms;
Z 2 represents a hydrogen atom or a substituent selected from the group consisting of:
(1) an alkyl group having from 1 to 20 carbon atoms,
(2) an aryl group having from 6 to 30 carbon atoms,
(3) a heteroaryl group having from 3 to 30 carbon atoms,
(4) a diarylamino group having from 12 to 30 carbon atoms,
(5) a carbazolyl group having from 12 to 30 carbon atoms,
(6) an alkyl group having from 1 to 20 carbon atoms, which is substituted by (2), (3), (4) and/or (5),
(7) an aryl group having from 6 to 30 carbon atoms, which is substituted by (1), (3), (4) and/or (5),
(8) a heteroaryl group having from 3 to 30 carbon atoms, which is substituted by (1), (2), (4) and/or (5),
(9) a diarylamino group having from 12 to 30 carbon atoms, which is substituted by (1), (2), (3) and/or (5), and
(10) a carbazolyl group having from 12 to 30 carbon atoms, which is substituted by (1), (2), (3) and/or (4); and
R 1 to R 8 and R 11 to R 18 each independently represent a hydrogen atom or a substituent selected independently from the group consisting of:
(1) an alkyl group having from 1 to 20 carbon atoms,
(2) an aryl group having from 6 to 30 carbon atoms,
(3) a heteroaryl group having from 3 to 30 carbon atoms,
(4) a diarylamino group having from 12 to 30 carbon atoms,
(5) a carbazolyl group having from 12 to 30 carbon atoms,
(6) an alkyl group having from 1 to 20 carbon atoms, which is substituted by (2), (3), (4) and/or (5),
(7) an aryl group having from 6 to 30 carbon atoms, which is substituted by (1), (3), (4) and/or (5),
(8) a heteroaryl group having from 3 to 30 carbon atoms, which is substituted by (1), (2), (4) and/or (5),
(9) a diarylamino group having from 12 to 30 carbon atoms, which is substituted by (1), (2), (3) and/or (5), and
(10) a carbazolyl group having from 12 to 30 carbon atoms, which is substituted by (1), (2), (3) and/or (4),
provided that at least one of R 1 to R 8 and at least one of R 11 to R 18 each independently represent (4), (5), (9) or (10).
5. A compound represented by the following formula (11):
wherein in the formula (11), Y 1 , Y 2 and Y 3 all represent nitrogen atoms;
Z 2 ′ represents a hydrogen atom or a substituent that is bonded via a carbon atom (provided that the substituent does not contain a boron atom), said substituent being selected from the group consisting of
(1) an alkyl group having from 1 to 20 carbon atoms,
(2) an aryl group having from 6 to 40 carbon atoms,
(3) a cyano substituted aryl group having from 6 to 40 carbon atoms,
(4) a monocyclic heteroaryl group having from 3 to 5 carbon atoms,
(5) a diarylamino group having from 12 to 40 carbon atoms,
(6) an alkyl group having from 1 to 20 carbon atoms, which is substituted by (2), (3), (4) and/or (5),
(7) an aryl group having from 6 to 40 carbon atoms, which is substituted by (1), (3), (4) and/or (5),
(8) a cyano substituted aryl group having from 6 to 40 carbon atoms, which is substituted by (1), (2), (4) and/or (5),
(9) a monocyclic heteroaryl group having from 3 to 5 carbon atoms, which is substituted by (1), (2), (3) and/or (5), and
(10) a diarylamino group having from 12 to 40 carbon atoms, which is substituted by (1), (2), (3) and/or (4); and
R 1 to R 8 and R 11 to R 18 each independently represent a hydrogen atom or a substituent selected independently from the group consisting of
(1) an alkyl group having from 1 to 20 carbon atoms,
(2) an aryl group having from 6 to 40 carbon atoms,
(3) a cyano substituted aryl group having from 6 to 40 carbon atoms,
(4) a monocyclic heteroaryl group having from 3 to 5 carbon atoms,
(5) a diarylamino group having from 12 to 40 carbon atoms,
(6) an alkyl group having from 1 to 20 carbon atoms, which is substituted by (2), (3), (4) and/or (5),
(7) an aryl group having from 6 to 40 carbon atoms, which is substituted by (1), (3), (4) and/or (5),
(8) a cyano substituted aryl group having from 6 to 40 carbon atoms, which is substituted by (1), (2), (4) and/or (5),
(9) a monocyclic heteroaryl group having from 3 to 5 carbon atoms, which is substituted by (1), (2), (3) and/or (5), and
(10) a diarylamino group having from 12 to 40 carbon atoms, which is substituted by (1), (2), (3) and/or (4),
provided that at least one of R 1 to R 8 and at least one of R 11 to R 18 each independently represent (4), (5), (9) or (10).
6. The compound according to claim 5 , which is represented by the following formula (12):
wherein in the formula (12), Y 1 , Y 2 and Y 3 all represent nitrogen atoms;
Z 2 ′ represents a hydrogen atom, or a substituent selected from the group consisting of:
(1) an alkyl group having from 1 to 20 carbon atoms,
(2) an aryl group having from 6 to 40 carbon atoms,
(3) a cyano substituted aryl group having from 6 to 40 carbon atoms,
(4) a monocyclic heteroaryl group having from 3 to 5 carbon atoms,
(5) a diarylamino group having from 12 to 40 carbon atoms,
(6) an alkyl group having from 1 to 20 carbon atoms, which is substituted by (2), (3), (4) and/or (5),
(7) an aryl group having from 6 to 40 carbon atoms, which is substituted by (1), (3), (4) and/or (5),
(8) a cyano substituted aryl group having from 6 to 40 carbon atoms, which is substituted by (1), (2), (4) and/or (5),
(9) a monocyclic heteroaryl group having from 3 to 5 carbon atoms, which is substituted by (1), (2), (3) and/or (5), and
(10) a diarylamino group having from 12 to 40 carbon atoms, which is substituted by (1), (2), (3) and/or (4);
and R 3 , R 6 , R 13 and R 16 each independently represent a hydrogen atom or a substituent independently selected from the group consisting of
(1) an alkyl group having from 1 to 20 carbon atoms,
(2) an aryl group having from 6 to 40 carbon atoms,
(3) a cyano substituted aryl group having from 6 to 40 carbon atoms,
(4) a monocyclic heteroaryl group having from 3 to 5 carbon atoms,
(5) a diarylamino group having from 12 to 40 carbon atoms,
(6) an alkyl group having from 1 to 20 carbon atoms, which is substituted by (2), (3), (4) and/or (5),
(7) an aryl group having from 6 to 40 carbon atoms, which is substituted by (1), (3), (4) and/or (5),
(8) a cyano substituted aryl group having from 6 to 40 carbon atoms, which is substituted by (1), (2), (4) and/or (5),
(9) a monocyclic heteroaryl group having from 3 to 5 carbon atoms, which is substituted by (1), (2), (3) and/or (5), and
(10) a diarylamino group having from 12 to 40 carbon atoms, which is substituted by (1), (2), (3) and/or (4),
provided that at least one of R 3 and R 6 and at least one of R 13 and R 16 each independently represent (4), (5), (9) or (10).