Compound, material for organic electroluminescence device, and organic electroluminescence device

Patent metadata

Field	Value
Publication number	US-9537111-B2
Application number	US-201214116896-A
Country	US
Kind code	B2
Filing date	May 9, 2012
Priority date	May 11, 2011
Publication date	Jan 3, 2017
Grant date	Jan 3, 2017

Abstract

A specific material for organic electroluminescence device having m-phenylene skeleton in its molecule realizes a highly heat-resistant and long lifetime organic electroluminescence device capable of driving at low voltage with high efficiency.

First claim

What is claimed is:

1. An organic electroluminescence device, comprising:
a cathode;
an anode; and
at least one organic thin film layer between the cathode and the anode;
wherein
the at least one organic thin film layer comprises a light emitting layer,
an electron transporting layer between the light emitting layer and the cathode, and
a hole blocking layer between the light emitting layer and the electron transporting layer, and
wherein
the hole blocking layer comprises;
a compound of formula (1-1) or formula (1-2):

wherein in formula (1-1):
X 1 represents an oxygen atom, a sulfur atom, or —N(R A )—;
X 2 represents an oxygen atom, a sulfur atom, or —N(R B )—;
each of A 1 to A 8 independently represents ═C(R A )— or ═N—;
each of A 9 to A 16 independently represents ═C(R B )— or ═N—;
each of B 1 to B 8 independently represents ═C(R)— or ═N—;
each of m and n independently represents an integer of 1 to 3;
L represents an oxygen atom, a sulfur atom, —N(R)—, —Si(R 1 )(R 2 )— or a linker represented by any one of formulae (2-1), (3-1), (4-1), (5-1), and (6-1):

wherein in formulae (2-1), (3-1), (4-1), (5-1), and (6-1):
each of C 1 to C 4 and C 29 to C 33 independently represents ═C(R)—;
each of C 5 to C 8 , C 13 to C 16 , C 21 to C 24 , and C 34 to C 37 independently represents ═C(R)—;
each of C 9 to C 12 , C 17 to C 20 , C 25 to C 28 and C 38 to C 41 independently represents ═C(R A )—;
provided that when m=n=1 and both of X 1 and X 2 represent oxygen atoms, L does not represent the formula (2-1);
when m=n=1 and both of X 1 and X 2 represent sulfur atoms, L does not represent the formula (2-1); and
when m=n=1 or m=n=2, X 1 and X 2 are not both nitrogen atoms;
R represents a hydrogen atom, a deuterium atom, or R C ;
each of R 1 and R 2 independently represents a hydrogen atom, a deuterium atom or R C , or R 1 and R 2 are bonded to each other to represent a divalent group represented by —(CR 3 R 4 ) p —;
R A represents a hydrogen atom, a deuterium atom, R C , or a single bond bonded to ring A;
R B represents a hydrogen atom, a deuterium atom, R C , or a single bond bonded to ring B;
R C independently represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atom, a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a silyl group substituted with a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and/or an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted silyl group, a cyano group, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a hydroxyl group, a nitro group, an amino group substituted with a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and/or an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted amino group, a carboxyl group, or —P(═O)R 3 R 4 ;
each of R 3 and R 4 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms; and
p represents an integer of 5 to 8;

wherein in formula (1-2):
X 1 represents an oxygen atom, a sulfur atom, or —N(R A )—;
X 2 represents an oxygen atom, a sulfur atom, or —N(R B )—;
each of A 1 to A 8 independently represents ═C(R A )— or ═N—;
each of A 9 to A 16 independently represents ═C(R B )— or ═N—;
at least one of A 1 to A 16 represents ═N—;
each of B 1 to B 8 independently represents ═C(R)— or ═N—;
each of m and n independently represents an integer of 1 to 3;
L represents an oxygen atom, a sulfur atom, —N(R)—, —Si(R 1 )(R 2 )—, or a linker represented by any one of formulae (2-2), (3-2), (4-2), (5-2), and (6-2):

wherein in formulae (2-2), (3-2), (4-2), (5-2), and (6-2):
each of C 1 to C 4 and C 29 to C 33 independently represents ═C(R)— or ═N—;
each of C 5 to C 8 , C 13 to C 16 , C 21 to C 24 and C 34 to C 37 independently represents ═C(R B )— or ═N—; and
each of C 9 to C 12 , C 17 to C 20 , C 25 to C 28 , and C 38 to C 41 independently represents ═C(R A )— or ═N—;
R represents a hydrogen atom, a deuterium atom, or R C ;
each of R 1 and R 2 independently represents a hydrogen atom, a deuterium atom or R C , or R 1 and R 2 are bonded to each other to represent a divalent group represented by —(CR 3 R 4 ) p —;
R A represents a hydrogen atom, a deuterium atom, R C , or a single bond bonded to ring A;
R B represents a hydrogen atom, a deuterium atom, R C , or a single bond bonded to ring B;
R C independently represents, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a silyl group substituted with a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and/or an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted silyl group, a cyano group, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a hydroxyl group, a nitro group, an amino group substituted with a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and/or an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted amino group, a carboxyl group, or —P(═O)R 3 R 4 ;
each of R 3 and R 4 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms; and
p represents an integer of 5 to 8.

2. An organic electroluminescence device, comprising:
a cathode;
an anode; and
at least one organic thin film layer between the cathode and the anode;
wherein
the at least one organic thin film layer comprises:
a light emitting layer,
a hole transporting layer between the light emitting layer and the anode, and
an electron blocking layer between the light emitting layer and the hole transporting layer, and wherein
the electron blocking layer comprises;
a compound of formula (1-1) or formula (1-2):

wherein in formula (1-1):
X 1 represents an oxygen atom, a sulfur atom, or —N(R A )—;
X 2 represents an oxyge

Assignees

• Nakano Yuki
• Numata Masaki
• Nagashima Hideaki
• Idemitsu Kosan Co

Inventors

• Nakano Yuki
• Numata Masaki
• Nagashima Hideaki

Classifications

• H10K50/181

  Electron blocking layers · CPC title

• H10K50/171

  Electron injection layers · CPC title

• H10K50/00

  Organic light-emitting devices (integrated devices or assemblies of multiple devices H10K59/00, H10K65/00; organic semiconductor lasers H01S5/36) · CPC title

• C07D209/86 Primary

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title