IP Library Granted Patent US 8,334,059
Granted Patent B2
US 8,334,059 · App. 12/324,229 · Granted Dec 18, 2012

Organic electroluminescence device

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Quick Facts
Patent No.
US 8,334,059
App. No.
12/324,229
Granted
Dec 18, 2012
Kind
B2
Abstract

An organic electroluminescence device includes an anode; a cathode; and at least one organic layer, which includes a light-emitting layer being provided between the anode and the cathode and containing at least one light-emitting material, and which contains at least one compound represented by formula (I): wherein each of A 11 , A 12 , A 13 , A 14 and A 15 represents an N atom or C—R 11 , and the number of N atoms represented by A 11 to A 15 is 1 or 2; R 11 represents a hydrogen atom or a substituent, and at least one of R 11 represents an aryl group or an aromatic heterocyclic group; Q 11 represents a monocyclic aryl group or an aromatic heterocyclic group; R 12 represents an alkyl group; and each of n, m and l represents an integer of from 0 to 4, provided that n is 1 or more, n+m is 2 or more, and n+m+l is 4.

Claims (53)

1. An organic electroluminescence device comprising:

an anode;

a cathode; and

at least one organic layer,

wherein

the at least one organic layer comprises a light-emitting layer being provided between the anode and the cathode and containing at least one light-emitting material, and

the at least one organic layer contains at least one compound represented by formula (I):

wherein

each of A 11 , A 12 , A 13 , A 14 and A 15 represents an N atom or C—R 11 , and the number of N atoms represented by A 11 to A 15 is an integer of 1 or 2;

R 11 represents a hydrogen atom or a substituent, and at least one of R 11 represents an aryl group or an aromatic heterocyclic group;

when a plurality of partial structures represented by the following formula (I-a) are present, each partial structure (I-a) may be the same with or different from every other (I-a); Q 11 represents a monocyclic aryl group or an aromatic heterocyclic group, and each Q 11 may be the same with or different from every other Q 11 , wherein when the aromatic heterocyclic group represented by Q 11 is substituted with a substituent, the substituent for the aromatic heterocyclic group represented by Q 11 is selected from the group consisting of an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an amino group an alkoxy group, an aryloxy group, a heterocyclic oxy group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, an arylthio group, a heterocyclic thio group, a sulfonyl group, a sulfinyl group, a ureido group, a phosphoric acid amido group, a hydroxyl group, a mercapto group, a halogen atom, a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydroxamic acid group, a sulfino group, a hydrazino group, an imino group, a silyl group, a silyloxy group, and a phosphoryl group, wherein the substituent for the aromatic heterocyclic group represented by Q 11 may further be substituted;

R 12 represents an alkyl group, and each R 12 may be the same with or different from every other R 12 ; and

each of m and l represents an integer of from 0 to 4, and n represents an integer of 1, 2 or 3, provided that n+m is an integer of 2 or more, and n+m+l is 4:

2. The organic electroluminescence device as claimed in claim 1 , wherein the compound represented by formula (I) is a compound represented by formula (II):

wherein

each of A 21 , A 22 , A 23 , A 24 and A 25 represents an N atom or C—R 21 , and the number of N atom represented by A 21 to A 25 is 1;

R 21 represents a hydrogen atom or a substituent, and at least one of R 21 represents an aryl group or an aromatic heterocyclic group;

when a plurality of partial structures represented by the following formula (II-a) are present, each partial structure (II-a) may be the same with or different from every other (II-a);

Q 21 represents a monocyclic aryl group or an aromatic heterocyclic group, and each Q 21 may be the same with or different from every other Q 21 , wherein when the aromatic heterocyclic group represented by Q 21 is substituted with a substituent, the substituent for the aromatic heterocyclic group represented by Q 21 is selected from the group consisting of an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a heterocyclic oxy group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, an arylthio group, a heterocyclic thio group, a sulfonyl group, a sulfinyl group, a ureido group, a phosphoric acid amido group, a hydroxyl group, a mercapto group, a halogen atom, a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydroxamic acid group, a sulfino group, a hydrazino group, an imino group, a silyl group, a silyloxy group, and a phosphoryl group, wherein the substituent for the aromatic heterocyclic group represented by Q 21 may further be substituted;

R 22 represents an alkyl group, and each R 22 may be the same with or different from every other R 22 ; and

each of m and l represents an integer of from 0 to 4, and n represents an integer of 1, 2 or 3 provided that n+m is an integer of 2 or more, and n+m+l is 4:

3. The organic electroluminescence device as claimed in claim 2 , wherein the compound represented by formula (II) is a compound represented by formula (III):

wherein

R 31 represents a hydrogen atom or a substituent, and at least one of R 31 represents an aryl group or an aromatic heterocyclic group;

when a plurality of partial structures represented by the following formula (III-a) are present, each partial structure (III-a) may be the same with or different from every other (III-a);

Q 31 represents a monocyclic aryl group or an aromatic heterocyclic group, and each Q 31 may be the same with or different from every other Q 31 , wherein when the aromatic heterocyclic group represented by Q 31 is substituted with a substituent, the substituent for the aromatic heterocyclic group represented by Q 31 is selected from the group consisting of an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a heterocyclic oxy group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, an arylthio group, a heterocyclic thio group, a sulfonyl group, a sulfonyl group, a ureido group, a phosphoric acid amido group, a hydroxyl group, a mercapto group, a halogen atom, a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydroxamic acid group, a sulfino group, a hydrazino group, an imino group, a silyl group, a silyloxy group, and a phosphoryl group, wherein the substituent for the aromatic heterocyclic group represented by Q 31 may further be substituted;

R 32 represents an alkyl group, and each R 32 may be the same with or different from every other R 32 ; and

each of m and l represents an integer of from 0 to 4, and n represents an integer of 1, 2 or 3, provided that n+m is an integer of 2 or more, and n+m+l is 4:

4. The organic electroluminescence device as claimed in claim 2 , wherein the compound represented by formula (II) is a compound represented by formula (IV):

wherein

R 41 represents a hydrogen atom or a substituent, and at least one of R 41 represents an aryl group or an aromatic heterocyclic group;

when a plurality of partial structures represented by the following formula (IV-a) are present, each partial structure (IV-a) may be the same with or different from every other (IV-a);

Q 41 represents a monocyclic aryl group or an aromatic heterocyclic group, and each Q 41 may be the same with or different from every other Q 41 , wherein when the aromatic heterocyclic group represented by Q 41 is substituted with a substituent, the substituent for the aromatic heterocyclic group represented by Q 41 is selected from the group consisting of an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a heterocyclic oxy group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, an arylthio group, a heterocyclic thio group, a sulfonyl group, a sulfinyl group, a ureido group, a phosphoric acid amido group, a hydroxyl group, a mercapto group, a halogen atom, a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydroxamic acid group, a sulfino group, a hydrazino group, an imino group, a silyl group, a silyloxy group, and a phosphoryl group, wherein the substituent for the aromatic heterocyclic group represented by Q 41 may further be substituted;

R 42 represents an alkyl group, and each R 42 may be the same with or different from every other R 42 ; and

each of m and 1 represents an integer of from 0 to 4, and n represents an integer of 1, 2 or 3, provided that n+m is an integer of 2 or more, and n+m+l is 4:

5. The organic electroluminescence device as claimed in claim 2 , wherein the compound represented by formula (II) is a compound represented by formula (V):

wherein

R 51 represents a hydrogen atom or a substituent, and at least one of R 51 represents an aryl group or an aromatic heterocyclic group;

when a plurality of partial structures represented by the following formula (V-a) are present, each partial structure (V-a) may be the same with or different from every other (V-a);

Q 51 represents a monocyclic aryl group or an aromatic heterocyclic group, and each Q 51 may be the same with or different from every other Q 51 , wherein when the aromatic heterocyclic group represented by Q 51 is substituted with a substituent, the substituent for the aromatic heterocyclic group represented by Q 51 is selected from the group consisting of an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a heterocyclic oxy group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, an arylthio group, a heterocyclic thio group, a sulfonyl group, a sulfinyl group, a ureido group, a phosphoric acid amido group, a hydroxyl group, a mercapto group, a halogen atom, a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydroxamic acid group, a sulfino group, a hydrazino group, an imino group, a silyl group, a silyloxy group, and a phosphoryl group, wherein the substituent for the aromatic heterocyclic group represented by Q 51 may further be substituted;

R 52 represents an alkyl group, and each R 52 may be the same with or different from every other R 52 ; and

each of m and l represents an integer of from 0 to 4, and n represents an integer of 1, 2 or 3, provided that n+m is an integer of 2 or more, and n+m+l is 4:

6. The organic electroluminescence device as claimed in claim 1 , wherein the compound represented by formula (I) has a glass transition temperature of 130° C. or more and 450° C. or less.

7. The organic electroluminescence device as claimed in claim 1 , wherein the compound represented by formula (I) has a lowest excitation triplet energy level of 65 kcal/mol (272.35 kJ/mol) or more and 95 kcal/mol (398.05 kJ/mol) or less.

8. The organic electroluminescence device as claimed in claim 1 , wherein the at least one light-emitting material comprises a phosphorescent material.

9. The organic electroluminescence device as claimed in claim 8 , wherein the phosphorescent material is an iridium complex or a platinum complex.

10. The organic electroluminescence device as claimed in claim 9 , wherein the platinum complex is a platinum complex represented by formula (C-1):

wherein

each of Q 1 , Q 2 , Q 3 and Q 4 independently represents a ligand to coordinate to Pt; and

each of L 1 , L 2 and L 3 independently represents a single bond or a divalent linking group.

11. The organic electroluminescence device as claimed in claim 1 , wherein the light-emitting layer contains the compound represented by formula (I).

12. The organic electroluminescence device as claimed in claim 1 , wherein the at least one organic layer further comprises at least one electron transporting layer being provided between the light-emitting layer and the cathode, and

the at least one electron transporting layer contains the compound represented by formula (I).

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 1, 2012
From: FUJIFILM CORPORATION
To: UDC IRELAND LIMITED
Reel/Frame 028889/0636 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 26, 2008
From: FUKUZAKI, EIJI
To: FUJIFILM CORPORATION
Reel/Frame 021896/0687 →