IP Library Patent Application 14762269
Patent Application
App. No. 14/762,269

LIGHT EMITTING MATERIAL AND ORGANIC LIGHT EMITTING DEVICE USING SAME

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Patent No.
US None
App. No.
14/762,269
Abstract

An organic light emitting device containing a compound represented by the following general formula in a light emitting layer have a high light emission efficiency. In the general formula (1), R 1 and R 2 represent carbazolyl, aryl, heteroaryl, alkyl or cycloalkyl; R 5 and R 6 represent alkyl; R 7 , R 8 and R 9 represent aryl, alkyl or carbazolyl; R 10 represents carbazolyl which may be substituted with carbazolyl, aryl, heteroaryl, alkyl or cycloalkyl; n1, n2, n6 and n7 represent an integer of from 0 to 4; n5 represents an integer of from 0 to 3; n8 and n9 represent an integer of from 0 to 5; and n10 represents 0 or 1.

Claims (88)

1 . A light emitting material containing a compound represented by the following general formula (1):

wherein in the general formula (1),

R 1 and R 2 each independently represent a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group or a substituted or unsubstituted cycloalkyl group;

R 5 and R 6 each independently represent a substituted or unsubstituted alkyl group;

R 7 , R 8 and R 9 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted alkyl group or a substituted or unsubstituted carbazolyl group;

R 10 represents a carbazolyl group which may be substituted with a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group or a substituted or unsubstituted cycloalkyl group;

n1, n2, n6 and n7 each independently represent an integer of from 0 to 4;

n5 represents an integer of from 0 to 3;

n8 and n9 each independently represent an integer of from 0 to 5; and

n10 represents 0 or 1,

provided that when n1, n2 and n5 to n9 each represent an integer of 2 or more, plural groups represented by R 1 , R 2 and R 5 to R 9 corresponding to n1, n2 and n5 to n9 respectively each may be the same as or different from each other.

2 . The light emitting material according to claim 1 , wherein the compound represented by the general formula (1) is a compound represented by the following general formula (2):

wherein in the general formula (2),

R 1 and R 2 each independently represent a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group or a substituted or unsubstituted cycloalkyl group;

R 5 and R 6 each independently represent a substituted or unsubstituted alkyl group;

R 7 , R 8 and R 9 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted alkyl group or a substituted or unsubstituted carbazolyl group;

n1, n2, n6 and n7 each independently represent an integer of from 0 to 4;

n5 represents an integer of from 0 to 3; and

n8 and n9 each independently represent an integer of from 0 to 5,

provided that when n1, n2 and n5 to n9 each represent an integer of 2 or more, plural groups represented by R 1 , R 2 and R 5 to R 9 corresponding to n1, n2 and n5 to n9 respectively each may be the same as or different from each other.

3 . The light emitting material according to claim 1 , wherein the compound represented by the general formula (1) is a compound represented by the following general formula (3):

wherein in the general formula (3),

R 1 to R 4 each independently represent a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group or a substituted or unsubstituted cycloalkyl group;

R 5 and R 6 each independently represent a substituted or unsubstituted alkyl group;

R 7 , R 8 and R 9 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted alkyl group or a substituted or unsubstituted carbazolyl group;

n1 to n4 and n7 each independently represent an integer of from 0 to 4;

n5 and n6 each represent an integer of from 0 to 3; and

n8 and n9 each independently represent an integer of from 0 to 5,

provided that when n1 to n9 each represent an integer of 2 or more, plural groups represented by R 1 to R 9 corresponding to n1 to n9 respectively each may be the same as or different from each other.

4 . The light emitting material according to claim 1 , wherein the light emitting material emits delayed fluorescent light.

5 . The light emitting material according to claim 2 , wherein in the general formula (2), n6 represents 0.

6 . The light emitting material according to claim 2 , wherein in the general formula (2), n1 represents an integer of from 1 to 4.

7 . The light emitting material according to claim 6 , wherein in the general formula (2), R 1 is bonded to the 3-position of the carbazolyl group.

8 . The light emitting material according to claim 6 , wherein in the general formula (2), n2 represents an integer of from 1 to 4.

9 . The light emitting material according to claim 8 , wherein in the general formula (2), R 2 is bonded to the 6-position of the carbazolyl group.

10 . The light emitting material according to claim 1 , wherein in the general formula (1), R 1 and R 2 each independently represent a substituted or unsubstituted 9-carbazolyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, an alkyl group having from 1 to 6 carbon atoms or a cycloalkyl group having from 5 to 7 carbon atoms.

11 . The light emitting material according to claim 1 , wherein in the general formula (1), R 1 and R 2 each independently represent a 9-carbazolyl group, a phenyl group, a tolyl group, a dimethylphenyl group, a trimethylphenyl group, a biphenyl group, a pyridyl group, a pyrrolyl group, a tert-butyl group or a cyclohexyl group.

12 . The light emitting material according to claim 2 , wherein in the general formula (2), both n1 and n2 represent 0.

13 . The light emitting material according to claim 3 , wherein in the general formula (3), at least one of n1 to n4 represents an integer of from 1 to 4.

14 . The light emitting material according to claim 3 , wherein in the general formula (3), n1 to n4 each independently represent an integer of from 1 to 4.

15 . The light emitting material according to claim 3 , wherein in the general formula (3), R 1 to R 4 each independently represent a substituted or unsubstituted 9-carbazolyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, an alkyl group having from 1 to 6 carbon atoms or a cycloalkyl group having from 5 to 7 carbon atoms.

16 . The light emitting material according to claim 3 , wherein in the general formula (3), R 1 to R 4 each independently represent a 9-carbazolyl group, a phenyl group, a tolyl group, a dimethylphenyl group, a trimethylphenyl group, a biphenyl group, a pyridyl group, a pyrrolyl group, a tert-butyl group or a cyclohexyl group.

17 . The light emitting material according to claim 3 , wherein in the general formula (3), both n5 and n6 represent 0.

18 . The light emitting material according to claim 1 , wherein in the general formula (1), all of n7, n8 and n9 represent 0.

19 . A delayed fluorescence emitter having a structure represented by the following general formula (1):

wherein in the general formula (1),

R 1 and R 2 each independently represent a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group or a substituted or unsubstituted cycloalkyl group;

R 5 and R 6 each independently represent a substituted or unsubstituted alkyl group;

R 7 , R 8 and R 9 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted alkyl group or a substituted or unsubstituted carbazolyl group;

R 10 represents a carbazolyl group which may be substituted with a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group or a substituted or unsubstituted cycloalkyl group;

n1, n2, n6 and n7 each independently represent an integer of from 0 to 4;

n5 represents an integer of from 0 to 3;

n8 and n9 each independently represent an integer of from 0 to 5; and

n10 represents 0 or 1,

provided that when n1, n2 and n5 to n9 each represent an integer of 2 or more, plural groups represented by R 1 , R 2 and R 5 to R 9 corresponding to n1, n2 and n5 to n9 respectively each may be the same as or different from each other.

20 . A compound represented by the following general formula (2):

wherein in the general formula (2),

R 1 and R 2 each independently represent a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group or a substituted or unsubstituted cycloalkyl group;

R 5 and R 6 each independently represent a substituted or unsubstituted alkyl group;

R 7 , R 8 and R 9 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted alkyl group or a substituted or unsubstituted carbazolyl group;

n1, n2, n6 and n7 each independently represent an integer of from 0 to 4, provided that when n1 is 2, then R1 is not an unsubstituted carbazolyl group;

n5 represents an integer of from 0 to 3; and

n8 and n9 each independently represent an integer of from 0 to 5,

provided that when n1, n2 and n5 to n9 each represent an integer of 2 or more, plural groups represented by R 1 , R 2 and R 5 to R 9 corresponding to n1, n2 and n5 to n9 respectively each may be the same as or different from each other.

21 . The compound according to claim 20 , wherein the general formula (2) is represented by the following general formula (4):

wherein in the general formula (4),

R 11 to R 14 each independently represent a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group or a substituted or unsubstituted cycloalkyl group;

R 15 and R 16 each independently represent an alkyl group;

R 17 , R 18 and R 19 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted alkyl group or a substituted or unsubstituted carbazolyl group;

n11 to n14 and n17 each independently represent an integer of from 0 to 4;

n15 and n16 each represent an integer of from 0 to 3; and

n18 and n19 each independently represent an integer of from 0 to 5,

provided that

at least one of n11 to n14 represents an integer of from 1 to 4, and

when n11 to n19 each represent an integer of 2 or more, plural groups represented by R 11 to R 19 corresponding to n11 to n19 respectively each may be the same as or different from each other.

22 . An organic light emitting device containing a substrate having thereon a light emitting layer containing a light emitting material represented by the following general formula (1):

wherein in the general formula (1),

R 1 and R 2 each independently represent a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group or a substituted or unsubstituted cycloalkyl group;

R 5 and R 6 each independently represent a substituted or unsubstituted alkyl group;

R 7 , R 8 and R 9 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted alkyl group or a substituted or unsubstituted carbazolyl group;

R 10 represents a carbazolyl group which may be substituted with a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group or a substituted or unsubstituted cycloalkyl group;

n1, n2, n6 and n7 each independently represent an integer of from 0 to 4;

n5 represents an integer of from 0 to 3;

n8 and n9 each independently represent an integer of from 0 to 5; and

n10 represents 0 or 1,

provided that when n1, n2 and n5 to n9 each represent an integer of 2 or more, plural groups represented by R 1 , R 2 and R 5 to R 9 corresponding to n1, n2 and n5 to n9 respectively each may be the same as or different from each other.

23 . The organic light emitting device according to claim 22 , wherein the organic light emitting device emits delayed fluorescent light.

24 . The organic light emitting device according to claim 22 , wherein the organic light emitting device is an organic electroluminescent device.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 4, 2016
From: KYUSHU UNIVERSITY, NATIONAL UNIVERSITY
To: KYULUX, INC.
Reel/Frame 039930/0751 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 21, 2015
From: HIRATA, SHUZO; SAKAI, YUMI; MASUI, KENSUKE; SHIZU, KATSUYUKI; TANAKA, HIROYUKI; ADACHI, CHIHAYA
To: KYUSHU UNIVERSITY NATIONAL UNIVERSITY CORPORATION
Reel/Frame 036388/0360 →