IP Library Granted Patent US 9,306,176
Granted Patent B2
US 9,306,176 · App. 13/747,795 · Granted Apr 5, 2016

Organic electroluminescent device; a charge transporting material for the organic electroluminescent device; and a luminescent device, a display device and a lighting system using the organic electroluminescent device

Inventors: Saki Takada (Kanagawa, JP); Yosuke Yamamoto (Kanagawa, JP); Kousuke Watanabe (Kanagawa, JP); Yuichiro Itai (Kanagawa, JP)
Assignee: UDC Ireland Limited
H01L51/0072C07D487/06C09K11/06H01L51/5016H05B33/14C09K2211/1011C09K2211/1029C09K2211/185H01L51/0085
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Quick Facts
Patent No.
US 9,306,176
App. No.
13/747,795
Granted
Apr 5, 2016
Kind
B2
Abstract

An organic electroluminescent element comprising a substrate; a pair of electrodes including an anode and a cathode, disposed on the substrate; and at least one organic layer including a light emitting layer, disposed between the electrodes, wherein the light emitting layer includes a compound represented by the following general formula: wherein: R 1 , R 2 , and R 19 ; R 11 to R 18 ; and A 1 to A 4 are as defined in the specification.

Claims (48)

1. An organic electroluminescent element comprising a substrate; a pair of electrodes including an anode and a cathode, disposed on the substrate; and at least one organic layer including a light emitting layer, disposed between the electrodes, wherein the light emitting layer includes a compound represented by the following general formula (1):

wherein: R 1 , R 2 , and R 19 each independently represent a hydrogen atom, a phenyl group, a monovalent oligoaryl group having the number of rings of from 2 to 10, or a monovalent fused polycyclic aromatic hydrocarbon group having the number of rings of from 2 to 6, provided that at least one of R 1 , R 2 , and R 19 represents a monovalent oligoaryl group having the number of rings of from 2 to 10 or a monovalent fused polycyclic aromatic hydrocarbon group having the number of rings of from 2 to 6, and that the phenyl group, the monovalent oligoaryl group having the number of rings of from 2 to 10, and the monovalent fused polycyclic aromatic hydrocarbon group having the number of rings of from 2 to 6 do not have an amino group as a substituent;

R 11 to R 18 each independently represent a hydrogen atom or a substituent; and

A 1 to A 4 each independently represent a nitrogen atom or a carbon atom, provided that when A 1 to A 4 are a nitrogen atom, R 1 and R 11 to R 13 connecting to the nitrogen atom do not exist;

wherein when only one of R 1 and R 2 is a p-phenylene, then the p-phenylene is p-phenylene-R 40 , wherein R 40 is an oligoaryl number of rings of from m 1 to 4, or a monovalent fused polycyclic aromatic hydrocarbon group having the number of rings of from 1 to 4; and

with the proviso that when R 1 and R 2 are H, R 19 cannot be an oligoaryl group having 3 or more rings.

2. The organic electroluminescent element according to claim 1 , wherein the compound represented by the general formula (1) is a compound represented by the following general formula (2):

wherein: R 1 and R 2 each independently represent a hydrogen atom, a phenyl group, a monovalent oligoaryl group having the number of rings of from 2 to 10, or a monovalent fused polycyclic aromatic hydrocarbon group having the number of rings of from 2 to 6, provided that at least one of R 1 and R 2 represents a monovalent oligoaryl group having the number of rings of from 2 to 10 or a monovalent fused polycyclic aromatic hydrocarbon group having the number of rings of from 2 to 6, and that the phenyl group, the monovalent oligoaryl group having the number of rings of from 2 to 10, and the monovalent fused polycyclic aromatic hydrocarbon group having the number of rings of from 2 to 6 do not have an amino group as a substituent; and R 11 to R 18 each independently represent a hydrogen atom or a substituent.

3. The organic electroluminescent element according to claim 1 , wherein the compound represented by the general formula (1) is a compound represented by the following general formula (3):

wherein: R 2 represents a hydrogen atom, a phenyl group, a monovalent oligoaryl group having the number of rings of from 2 to 10, or a monovalent fused polycyclic aromatic hydrocarbon group having the number of rings of from 2 to 6, and the phenyl group, the monovalent oligoaryl group having the number of rings of from 2 to 10, and the monovalent fused polycyclic aromatic hydrocarbon group having the number of rings of from 2 to 6 do not have an amino group as a substituent; and

R 11 to R 18 , R 21 to R 25 , and R 31 to R 35 each independently represent a hydrogen atom or a substituent, provided that R 2 represents a monovalent oligoaryl group having the number of rings of from 2 to 10 or a monovalent fused polycyclic aromatic hydrocarbon group having the number of rings of from 2 to 6, at least one of R 21 to R 25 and R 31 to R 35 represents an aryl group, or two or more of R 21 to R 25 or two or more of R 31 to R 35 are bound to each other to form a fused polycyclic aromatic hydrocarbon ring having the number of rings of from 2 to 6.

4. The organic electroluminescent element according to claim 1 , wherein the compound represented by the general formula (1) is a compound represented by the following general formula (4):

wherein:

R 1 , R 2 , and R 19 each independently represent a hydrogen atom, a phenyl group, a monovalent oligoaryl group having the number of rings of from 2 to 10, or a monovalent fused polycyclic aromatic hydrocarbon group having the number of rings of from 2 to 6, provided that at least one of R′, R 2 , and R 19 represents a group selected from the following general formulae (CH-1) to (CH-11), and that the phenyl group, the monovalent oligoaryl group having the number of rings of from 2 to 10, and the monovalent fused polycyclic aromatic hydrocarbon group having the number of rings of from 2 to 6 do not have an amino group as a substituent;

with the proviso that when R 1 and R 2 are H, R 19 cannot be an oligoaryl group having 3 or more rings

and R 11 to R 18 each independently represent a hydrogen atom or a substituent;

wherein: * represents a binding site.

5. The organic electroluminescent element according to claim 1 , wherein, in the general formula (1), the group represented by R 1 or R 2 is a group containing only one p-phenylene-R 40 group, wherein R 40 represents an oligoaryl group having the number of rings of from 1 to 4, or a monovalent fused polycyclic aromatic hydrocarbon group having the number of rings of from 1 to 4.

6. The organic electroluminescent element according to claim 1 , wherein the light emitting layer further contains a phosphorescent material.

7. The organic electroluminescent element according to claim 6 , wherein the phosphorescent material is an iridium complex.

8. The organic electroluminescent element according to claim 7 , wherein the iridium complex is represented by the following general formula (E-1):

wherein: Z 1 and Z 2 each independently represent a carbon atom or a nitrogen atom; A 1 represents an atomic group for forming a 5- or 6-membered heterocyclic ring together with Z 1 and the nitrogen atom; B 1 represents an atomic group for forming a 5- or 6-membered heterocyclic ring together with Z 2 and the carbon atom; (X—Y) represents a monoanionic bidentate ligand; and n E1 represents an integer of from 1 to 3.

9. The organic electroluminescent element according to claim 8 , wherein the iridium complex represented by the general formula (E-1) is represented by the following general formula (E-2):

wherein: A E1 to A E8 each independently represent a nitrogen atom or C—R E ; R E represents a hydrogen atom or a substituent; (X—Y) represents a monoanionic bidentate ligand; and n E2 represents an integer of from 1 to 3.

10. The organic electroluminescent element according to claim 1 , wherein the iridium complex represented by the general formula (E-1) is the following compound:

11. The organic electroluminescent element according to claim 1 , wherein the compound represented by the general formula (1) has a molecular weight of not more than 800.

12. The organic electroluminescent element according to claim 1 , wherein the light emitting layer is funned by a vacuum deposition process.

13. The organic electroluminescent element according to claim 1 , wherein the light emitting layer is formed by a wet process.

14. A charge transporting material for an organic electroluminescent element represented by the following general formula (1):

wherein: R 1 , R 2 , and R 19 each independently represent a hydrogen atom, a phenyl group, a monovalent oligoaryl group having the number of rings of from 2 to 10, or a monovalent fused polycyclic aromatic hydrocarbon group having the number of rings of from 2 to 6, provided that at least one of R 1 , R 2 , and R 19 represents a monovalent oligoaryl group having the number of rings of from 2 to 10 or a monovalent fused polycyclic aromatic hydrocarbon group having the number of rings of from 2 to 6;

and that the phenyl group, the monovalent oligoaryl group having the number of rings of from 2 to 10, and the monovalent fused polycyclic aromatic hydrocarbon group having the number of rings of from 2 to 6 do not have an amino group as a substituent; R 11 to R 18 each independently represent a hydrogen atom or a substituent;

and A 1 to A 4 each independently represent a nitrogen atom or a carbon atom, provided that when A 1 to A 4 are a nitrogen atom, R 1 and R 11 to R 13 connecting to the nitrogen atom do not exist

wherein when only one of R 1 and R 2 is a p-phenylene, then the p-phenylene is p-phenylene-R 40 , wherein R 40 is an oligoaryl group having the number of rings of from 1 to 4, or a monovalent fused polycyclic aromatic hydrocarbon group having the number of rings of from 1 to 4; and

with the proviso that when R 1 and R 2 are H, R 19 cannot be an oligoaryl group having 3 or more rings.

15. The charge transporting material for an organic electro luminescent element according to claim 14 , wherein the compound represented by the general formula (1) is a compound represented by the following general formula (2):

wherein: R 1 and R 2 each independently represent a hydrogen atom, a phenyl group, a monovalent oligoaryl group having the number of rings of from 2 to 10, or a monovalent fused polycyclic aromatic hydrocarbon group having the number of rings of from 2 to 6, provided that at least one of R 1 and R 2 represents a monovalent oligoaryl group having the number of rings of from 2 to 10 or a monovalent fused polycyclic aromatic hydrocarbon group having the number of rings of from 2 to 6, and that the phenyl group, the monovalent oligoaryl group having the number of rings of from 2 to 10, and the monovalent fused polycyclic aromatic hydrocarbon group having the number of rings of from 2 to 6 do not have an amino group as a substituent; and R 11 to R 18 each independently represent a hydrogen atom or a substituent.

16. The charge transporting material for an organic electroluminescent element according to claim 14 , wherein the compound represented by the general formula (1) is a compound represented by the following general formula (3):

wherein: R 2 represents a hydrogen atom, a phenyl group, a monovalent oligoaryl group having the number of rings of from 2 to 10, or a monovalent fused polycyclic aromatic hydrocarbon group having the number of rings of from 2 to 6, and the phenyl group, the monovalent oligoaryl group having the number of rings of from 2 to 10, and the monovalent fused polycyclic aromatic hydrocarbon group having the number of rings of from 2 to 6 do not have an amino group as a substituent; and R 11 to R 18 , R 21 to R 25 , and R 31 to R 35 each independently represent a hydrogen atom or a substituent, provided that R 2 represents a monovalent oligoaryl group having the number of rings of from 2 to 10 or a monovalent fused polycyclic aromatic hydrocarbon group having the number of rings of from 2 to 6, at least one of R 21 to R 25 and R 31 to R 35 represents an aryl group, or two or more of R 21 to R 25 or two or more of R 31 to R 35 are bound to each other to form a fused polycyclic aromatic hydrocarbon ring having the number of rings of from 2 to 6.

17. The charge transporting material for an organic electroluminescent element according to claim 14 , wherein the compound represented by the general formula (1) is a compound represented by the following general formula (4):

wherein: R 1 , R 2 , and R 19 each independently represent a hydrogen atom, a phenyl group, a monovalent oligoaryl group having the number of rings of from 2 to 10, or a monovalent fused polycyclic aromatic hydrocarbon group having the number of rings of from 2 to 6, provided that at least one of R 1 , R 2 , and R 19 represents a group selected from the following general formulae (CH-1) to (CH-11), and that the phenyl group, the monovalent oligoaryl group having the number of rings of from 2 to 10, and the monovalent fused polycyclic aromatic hydrocarbon group having the number of rings of from 2 to 6 do not have an amino group as a substituent;

with the proviso that when R 1 and R 2 are H, R 19 cannot be an oligoaryl group having 3 or more rings;

and R 11 to R 18 each independently represent a hydrogen atom or a substituent;

wherein: * represents a binding site.

18. The charge transporting material for an organic electroluminescent element according to claim 14 , wherein, in the general formula (1), the group represented by R 1 or R 2 is a group containing only one p-phenylene-R 40 group, wherein R 40 represents an oligoaryl group having the number of rings of from 1 to 4, or a monovalent fused polycyclic aromatic hydrocarbon group having the number of rings of from 1 to 4.

19. The charge transporting material for an organic electroluminescent element according to claim 14 , wherein the compound represented by the general formula (1) has a molecular weight of not more than 800.

20. A light emitting device using the organic electroluminescent element of claim 1 .

21. A display device using the organic electroluminescent element of claim 1 .

22. An illumination device using the organic electroluminescent element of claim 1 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 9, 2014
From: TAKADA, SAKI; YAMAMOTO, YOSUKE; WATANABE, KOUSUKE; ITAI, YUICHIRO
To: UDC IRELAND LIMITED
Reel/Frame 032178/0244 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 6, 2013
From: FUJIFILM CORPORATION
To: UDC IRELAND LIMITED
Reel/Frame 029760/0235 →
Priority Claims (2)
JP 2012-011349 · Jan 23, 2012 · national
JP 2012-118492 · May 24, 2012 · national
Continuity (1)
Related Publication 20140034914A1 · Feb 6, 2014