IP Library Granted Patent US 8,957,236
Granted Patent B2
US 8,957,236 · App. 14/128,665 · Granted Feb 17, 2015

Compound and organic device employing same

Inventors: Qisheng Zhang (Fukuoka, JP); Chihaya Adachi (Fukuoka, JP); Shigeyuki Matsunami (Fukuoka, JP); Kei Sakanoue (Fukuoka, JP)
Assignee: Kyushu University National University Corporation
H01L51/005C07F9/5045C07F9/5325C07F9/5329C07F9/5728C07F9/582C07F9/65517C07F9/655354C07F15/0033H01L51/009H01L51/0091C09K11/06H05B33/14H01L51/0085H01L51/5016C09K2211/1007C09K2211/1014H01L51/5072
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Quick Facts
Patent No.
US 8,957,236
App. No.
14/128,665
Granted
Feb 17, 2015
Kind
B2
Abstract

The compounds represented by the following general formula have excellent properties as a charge transport material. In the formula, R 1 to R 3 represent a substituent, n1 and n2 indicate an integer of from 0 to 5, n3 indicates an integer of from 0 to 4, X represents a linking group of —O—, —S—, —SO 2 —, —CS—, —R 4 —, —C(R 5 )(R 6 )—, —PO(R 7 )—, —Si(R 8 )(R 9 )—, >PO—, >Si(R 10 )— or >Si<, m is an integer of from 2 to 4, R 4 represents an aliphatic cyclic linking group, and R 5 to R 10 represent a hydrogen atom, an alkyl group, an aryl group, etc.

Claims (28)

1. A compound represented by the following general formula (1):

wherein R 1 , R 2 and R 3 each independently represent a substituent, n1 and n2 each independently indicate an integer of from 0 to 5, n3 indicates an integer of from 0 to 4, X represents a linking group having any of the following structures, m is equal to the valence of the linking group X and indicates an integer of from 2 to 4;

wherein R 5 and R 6 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; R 8 , R 9 and R 10 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; at least one of R 8 and R 9 is a hydrogen atom, or a substituted or unsubstituted alkyl group; provided that when X is —O—, this links at the 3,3′-positions of the triphenylphosphine oxide structure of the general formula (1).

2. A compound according to claim 1 , which is represented by the following general formula (2 ):

wherein R 11 ,R 12 , R 13 , R 21 , R 22 and R 23 each independently represent a substituent, n11, n12, n21 and n22 each independently indicate an integer of from 0 to 5, n13 and n23 each independently indicate an integer of from 0 to 4, X 11 represents a linking group having any of the following structures;

wherein R 5 and R 6 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; R 8 and R 9 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; at least one of R 8 and R 9 is a hydrogen atom, or a substituted or unsubstituted alkyl group; provided that when X is —O—, this links at the 3,3′-positions of the triphenylphosphine oxide structure of the general formula (1).

3. A compound according to claim 1 , which is represented by the following general formula (2-1):

wherein R 11 ,R 12 , R 13 , R 21 , R 22 and R 23 each independently represent a substituent, n11, n12, n21 and n22 each independently indicate an integer of from 0 to 5, n13 and n23 each independently indicate an integer of from 0 to 4, X 21 represents a linking group having any of the following structures;

wherein R 5 and R 6 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; R 8 and R 9 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; at least one of R 8 and R 9 is a hydrogen atom, or a substituted or unsubstituted alkyl group.

4. A compound according to claim 1 , which is represented by the following general formula (2-2):

wherein R 11 ,R 12 , R 13 , R 21 , R 22 and R 23 each independently represent a substituent, n11, n12, n21 and n22 each independently indicate an integer of from 0 to 5, n13 and n23 each independently indicate an integer of from 0 to 4, X 22 represents a linking group having any of the following structures;

wherein R 5 and R 6 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; R 8 and R 9 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; at least one of R 8 and R 9 is a hydrogen atom, or a substituted or unsubstituted alkyl group.

5. A compound according to claim 1 , which is represented by the following general formula (2-3):

wherein R 11 , R 12 , R 13 , R 21 , R 22 and R 23 each independently represent a substituent, n11, n12, n21 and n22 each independently indicate an integer of from 0 to 5, n13 and n23 each independently indicate an integer of from 0 to 4, X 23 represents a linking group having any of the following structures;

wherein R 5 and R 6 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; R 8 and R 9 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; at least one of R 8 and R 9 is a hydrogen atom, or a substituted or unsubstituted alkyl group.

6. The compound according to claim 1 , wherein the linking group has the following structure

7. The compound according to claim 1 , wherein the linking group has the following structure

8. The compound according to claim 1 , which has a lowest excited triplet energy level at 77°K of not lower than 2.80 eV.

9. The compound according to claim 1 , which has a lowest excited triplet energy level at 77°K of not lower than 2.95 eV.

10. A charge transport material comprising a compound represented by the following formula (1):

wherein R 1 , R 2 and R 3 each independently represent a substituent, n1 and n2 each independently indicate an integer of from 0 to 5, n3 indicates an integer of from 0 to 4, X represents a linking group having any of the following structures, m is equal to the valence of the linking group X and indicates an integer of from 2 to 4;

wherein R 4 represents a substituted or unsubstituted aliphatic cyclic linking group; R 5 and R 6 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; R 8 , R 9 and R 10 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; at least one of R 8 and R 9 is a hydrogen atom, or a substituted or unsubstituted alkyl group; provided that when X is —O—, this links at the 3,3′-positions of the triphenylphosphine oxide structure of the general formula (1).

11. An organic device using a compound represented by the following formula (1):

wherein R 1 , R 2 and R 3 each independently represent a substituent, n1 and n2 each independently indicate an integer of from 0 to 5, n3 indicates an integer of from 0 to 4, X represents a linking group having any of the following structures, m is equal to the valence of the linking group X and indicates an integer of from 2 to 4;

wherein R 4 represents a substituted or unsubstituted aliphatic cyclic linking group; R 5 and R 6 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; R 8 , R 9 and R 10 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; at least one of R 8 and R 9 is a hydrogen atom, or a substituted or unsubstituted alkyl group; provided that when X is —O—, this links at the 3,3′-positions of the triphenylphosphine oxide structure of the general formula (1).

12. An organic electroluminescence element using a compound represented by the following formula (1):

wherein R 1 , R 2 and R 3 each independently represent a substituent, n1 and n2 each independently indicate an integer of from 0 to 5, n3 indicates an integer of from 0 to 4, X represents a linking group having any of the following structures, m is equal to the valence of the linking group X and indicates an integer of from 2 to 4;

wherein R 4 represents a substituted or unsubstituted aliphatic cyclic linking group; R 5 and R 6 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; R 8 , R 9 and R 10 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; at least one of R 8 and R 9 is a hydrogen atom, or a substituted or unsubstituted alkyl group; provided that when X is —O—, this links at the 3,3′-positions of the triphenylphosphine oxide structure of the general formula (1).

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 Dec 23, 2013
From: ZHANG, QISHENG; ADACHI, CHIHAYA; MATSUNAMI, SHIGEYUKI; SAKANOUE, KEI
To: KYUSHU UNIVERSITY NATIONAL UNIVERSITY CORPORATION
Reel/Frame 031844/0201 →
Priority Claims (2)
JP 2011-140046 · Jun 24, 2011 · national
JP 2011-140047 · Jun 24, 2011 · national
Continuity (1)
Related Publication 20140135530A1 · May 15, 2014