Material for organic electroluminescence device and organic electroluminescence device

Patent metadata

Field	Value
Publication number	US-9530969-B2
Application number	US-201313760928-A
Country	US
Kind code	B2
Filing date	Feb 6, 2013
Priority date	Dec 5, 2011
Publication date	Dec 27, 2016
Grant date	Dec 27, 2016

Abstract

An organic electroluminescence device employing a specific biscarbazole derivative having a cyano group as a first host and a compound having both a carbazole structure and a nitrogen-containing aromatic heteroring as a second host. The organic electroluminescence device has a prolonged lifetime.

First claim

What is claimed is:

1. An organic electroluminescence device which comprises a light emitting layer which is disposed between a cathode and an anode and comprises a first host material, a second host material and a light emitting material,
wherein the first host material is represented by formula (A):

wherein
each of A 1 and A 2 independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted residue selected from the group consisting of a pyrrole ring, an isoindole ring, a benzofuran ring, an isobenzofuran ring, a dibenzothiophene ring, an indole ring, a pyrrolidine ring, a dioxane ring, a piperidine ring, a morpholine ring, a piperazine ring, a carbazole ring, a furan ring, a thiophene ring, an oxazole ring, an oxadiazole ring, a benzoxazole ring, a thiazole ring, a thiadiazole ring, a benzothiazole ring, a triazole ring, an imidazole ring, a benzimidazole ring, a pyran ring, a dibenzofuran ring, and a benzo[c]dibenzofuran ring;
A 3 represents a divalent monocyclic heterocyclic group having 5 ring atoms;
A 3 may be independently substituted with at least one group selected from the group consisting of a cyano group, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a haloalkoxyl group having 1 to 20 carbon atoms, an alkyl silyl group having 1 to 10 carbon atoms, an aryloxy group having 6 to 30 ring carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an aralkyl group having 6 to 30 carbon atoms, and a heteroaryl group having 5 to 30 ring atoms, a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a phenanthryl group, a spirobifluorenyl group, a triphenylenyl group, a fluorenyl group, a spirobifluorenyl group, and a fluoranthenyl group,
m represents an integer of 0 to 3;
each of X 1 to X 8 and Y 1 to Y 8 independently represents N or CR a ;
each of R a independently represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted silyl group, a halogen atom, or a cyano group, provided that when two or more R a groups exist, the R a groups may be the same or different and one of X 5 to X 8 and one of Y 1 to Y 4 are bonded to each other via A 3 ; and
the formula (A) satisfies at least one of the following requirements (i) to (v):
(i) at least one of A 1 and A 2 represents a cyano-substituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a cyano-substituted group selected from the group consisting of a pyrrole ring, an isoindole ring, a benzofuran ring, an isobenzofuran ring, a dibenzothiophene ring, an indole ring, a pyrrolidine ring, a dioxane ring, a piperidine ring, a morpholine ring, a piperazine ring, a carbazole ring, a furan ring, a thiophene ring, an oxazole ring, an oxadiazole ring, a benzoxazole ring, a thiazole ring, a thiadiazole ring, a benzothiazole ring, a triazole ring, an imidazole ring, a benzimidazole ring, a pyran ring, a dibenzofuran ring, and a benzo[c]dibenzofuran ring;
(ii) at least one of X 1 to X 4 and Y 5 to Y 8 represents CR a , and at least one of R a in X 1 to X 4 and Y 5 to Y 8 represents a cyano-substituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a cyano-substituted heterocyclic group having 5 to 30 ring atoms;
(iii) m represents an integer of 1 to 3 and at least one of A 3 represents a cyano-substituted divalent heterocyclic group having 5 ring atoms;
(iv) at least one of X 5 to X 8 and Y 1 to Y 4 represents CR a , and at least one of R a in X 5 to X 8 and Y 1 to Y 8 represents a cyano-substituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a cyano-substituted heterocyclic group having 5 to 30 ring atoms; and
(v) at least one of X 1 to X 8 and Y 1 to Y 8 represents C—CN; and
the second host material is represented by formula (1):

wherein
Z 1 represents a ring structure fused to a side a and represented by formula (1-1) or (1-2), and Z 2 represents a ring structure fused to a side b and represented by formula (1-1) or (1-2), provided that at least one of Z 1 and Z 2 is represented by formula (1-1):

in formula (1-1),
a side c is fused to the side a or b of formula (1);

in formula (1-2),
any one of sides d, e and f is fused to the side a or b of formula (1);

in formulae (1-1) and (1-2),
X 11 represents a sulfur atom, an oxygen atom, N—R 19 , or C(R 20 )(R 21 );
each of R 11 to R 21 independently represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, provided that adjacent groups of R 11 to R 21 may be bonded to each other to form a a ring;
M 1 represent a substituted or unsubstituted nitrogen-containing aromatic heteroring having 5 to 30 ring atoms;
L 1 represents a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, a cycloalkylene group having 5 to 30 ring atoms, or a group in which the preceding groups are directly linked to each other; and
k represents 1 or 2.

2. The organic electroluminescence device according to claim 1 , wherein the first host material satisfies at least one of the requirements (i) and (ii).

3. The organic electroluminescence device according to claim 1 , wherein the second host material is represented by formula (2):

wherein
Z 1 represents a ring structure fused to the side a and represented by formula (1-1) or (1-2), and Z 2 represents a ring structure fused to the side b and represented by formula (1-1) or (1-2), provided that at least one of Z 1 and Z 2 is represented by formula (1-1);
L 1 is as defined in formula (1);
each of X 12 to X 14 independently represents a nitrogen atom, CH, or a carbon atom bonded to R 31 or L 1 , provided that at least one of X 12 to X 14 represents a nitrogen atom;
each of Y 11 to Y 13 independently represents CH or a carbon atom bonded to R 31 or L 1 ;
each of R 31 independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbo

Assignees

• Idemitsu Kosan Co

Inventors

• Mizuki Yumiko
• Ito Mitsunori
• Inoue Tetsuya
• Hibino Kumiko
• Nishimura Kazuki

Classifications

• H01L51/5024

  Electricity · mapped topic

• H01L51/0085

  Electricity · mapped topic

• C07D403/10 Primary

  linked by a carbon chain containing aromatic rings · CPC title

• C07D487/04

  Ortho-condensed systems · CPC title

• C07D403/14

  containing three or more hetero rings · CPC title