IP Library Granted Patent US 10,243,153
Granted Patent B2
US 10,243,153 · App. 15/060,725 · Granted Mar 26, 2019

Material for organic electroluminescence device and organic electroluminescence device

Inventor: Toshihiro Ise (Kanagawa, JP)
Assignee: UDC IRELAND LIMITED
H01L51/0085C07D209/86C07F15/0033C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1044C09K2211/185H01L51/0072H01L51/5016H01L51/5024H01L51/5056H01L51/5072H01L51/5088H01L51/5092H01L51/5096H01L51/5268H01L51/56
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Quick Facts
Patent No.
US 10,243,153
App. No.
15/060,725
Granted
Mar 26, 2019
Kind
B2
Abstract

A material for an organic electroluminescence device, includes: an organic material that is to be provided for a film formation of any of at least one organic layer included in the organic electroluminescence device, the organic material having a water content before the film formation, as measured by the Karl Fischer method, of 100 ppm or more and not more than 1,000 ppm.

Claims (45)

1. A material in a solid state, said material being for an organic electroluminescence device, comprising:

an organometallic compound that is to be provided for a dry film formation process of any of at least one layer included in the electroluminescence device, wherein the material has a water content before the dry film formation process, as measured by the Karl Fischer method, of 100 ppm or more and not more than 1,000 ppm,

wherein the organometallic compound is an iridium complex represented by the following formula (E-3):

in the formula (E-3), each of A 9 to A 11 and A 13 to A 16 independently represents C—R, N or N—R′;

A 12 represents a carbon atom or a nitrogen atom;

R represents a hydrogen atom, an alkyl group, an aryl group, an aromatic heterocyclic group, a cyano group, a silyl group, an amino group or a fluorine atom;

R′ represents a hydrogen atom, an alkyl group or an aryl group;

n represents an integer of from 1 to 3; and

X—Y represents a monoanionic bidentate ligand represented by the following formula (I-1), (I-2) or (I-3):

in the formula (I-1), each of Rx and Rz independently represents an alkyl group, a perfluoroalkyl group or an aryl group; and

Ry represents a hydrogen atom, an alkyl group, a perfluoroalkyl group or an aryl group,

in the formula (I-2), each of Ri 1 to Ri 4 independently represents a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, an alkoxy group, an aryloxy group, a dialkylamino group, a diarylamino group, a cyano group, a fluorine atom, a trialkylsilyl group, a triarylsilyl group, an alkyldiarylsilyl group, a dialkylarylsilyl group, a heterocyclic group or a heterocyclic oxy group; and

adjacent substituents among Ri 1 to Ri 4 may be connected to each other, and

in the formula (I-3), each of Ri 5 to Ri 12 independently represents a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, an alkoxy group, an aryloxy group, a dialkylamino group, a diarylamino group, a cyano group, a fluorine atom, a trialkylsilyl group, a triarylsilyl group, an alkyldiarylsilyl group, a dialkylarylsilyl group, a heterocyclic group or a heterocyclic oxy group; and

adjacent substituents among Ri 5 to Ri 8 , adjacent substituents among Ri 9 to Ri 12 , and Ri 8 and Ri 9 may be each connected to each other.

2. The material for an organic electroluminescence device according to claim 1 ,

wherein the iridium complex represented by the formula (E-3) is represented by the following formula (E-4):

in the formula (E-4), each of R 1a to R 1i independently represents a hydrogen atom, an alkyl group, an aryl group, an aromatic heterocyclic group, a cyano group, a silyl group, an amino group or a fluorine atom;

X—Y is synonymous with X—Y in the formula (E-3); and

n represents an integer of from 1 to 3.

3. The material for an organic electroluminescence device according to claim 2 ,

wherein in the formula (E-4), n is 3.

4. A material in a solid state, said material being for an organic electroluminescence device, comprising:

an organometallic compound that is to be provided for a dry film formation process of any of at least one organic layer included in the electroluminescence device, wherein the material has a water content before the dry film formation process, as measured by the Karl Fischer method, of 100 ppm or more and not more than 1,000 ppm,

wherein the organometallic compound is an iridium complex represented by the following formula (PQ-1):

in the formula (PQ-1), each of R 1 to R 10 independently represents a hydrogen atom, an alkyl group, an aryl group, an aromatic heterocyclic group, a cyano group, a silyl group, an amino group or a fluorine atom;

R 1 to R 10 may be bonded to each other to form a ring, if possible;

n is 2; and

X P —Y P is a monoanionic bidentate ligand represented by the following formula L:

in the formula L, each of R L1 and R L2 independently represents an alkyl group having from 1 to 5 carbon atoms or a phenyl group which may have a substituent selected from the substituent group T2 consisting of an alkyl group having from 1 to 6 carbon atoms, an alkenyl group having from 2 to 6 carbon atoms, a phenyl group, and aromatic heterocyclic group having from 5 to 10 carbon atoms, an alkoxy group having from 1 to 4 carbon atoms, a phenoxy group, a fluorine atom, a silyl group, an amino group, a cyano group and a group composed of a combination of these groups; and

plural substituents selected from the substituent group T2 may be joined or fused to each other to form a ring.

5. A composition in a solid state that is to be provided for a dry film formation process, comprising:

the material for an organic electroluminescence device according to claim 1 .

6. The composition according to claim 5 , further comprising:

a compound represented by the following formula (4-1) or (4-2):

in the formulae (4-1) and (4-2), each of d and e independently represents an integer of from 0 to 3, and at least one of d and e is 1 or more;

f represents an integer of from 1 to 4;

R′ 8 represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a cyano group, an alkoxy group, an aryloxy group, an amino group or a silyl group, and when plural R′ 8 s are present, each R′ 8 may be the same as or different from every other R′ 8 ; and

at least one of R′ 8 s represents a group represented by the following formula (5):

in the formula (5), each of R′ 9 s independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a cyano group, an alkoxy group, an aryloxy group, an amino group or a silyl group; and

g represents an integer of from 0 to 8.

7. A method for manufacturing an organic electroluminescence device, comprising: forming a layer comprising the material for an organic electroluminescence device according to claim 1 .

8. A method for reducing a rate of occurrence of short-circuit device, comprising: forming a layer comprising the material for an organic electroluminescence device according to claim 1 .

9. A composition in a solid state that is to be provided for a dry film formation process, comprising:

the material for an organic electroluminescence device according to claim 4 .

Priority Claims (3)
JP 2009-201159 · Aug 31, 2009 · national
JP 2009-223453 · Sep 28, 2009 · national
JP 2010-100396 · Apr 23, 2010 · national
Continuity (2)
Continuation 12872775 · Aug 31, 2010
Related Publication 20160254462A1 · Sep 1, 2016
Cited By (3)
US 12,239,009 US 12,275,742 US 12,630,560