Organic electroluminescent element and electronic device

Patent metadata

Field	Value
Publication number	US-10396288-B2
Application number	US-201414909783-A
Country	US
Kind code	B2
Filing date	Sep 19, 2014
Priority date	Sep 20, 2013
Publication date	Aug 27, 2019
Grant date	Aug 27, 2019

Abstract

An organic EL device with high emission efficiency, an electronic equipment including the organic EL device, and a compound providing the organic EL device are provided. The compound is represented by formula (1):

wherein Ar 1 represents a substituted or unsubstituted naphthalene ring; the substituent on the naphthalene ring is at least one selected from a fluorine atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, a group represented by —Si(R 101 )(R 102 )(R 103 ), and a group represented by —Z—R a ; R 1 and R 2 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, a group represented by —Si(R 101 )(R 102 )(R 103 ), an aryl group, or a heteroaryl group; R 11 to R 18 each independently represent a hydrogen atom, a fluorine atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, a group represented by —Si(R 101 )(R 102 )(R 103 ), or a group represented by —Z—R a ; each Z represents a single bond, an arylene group, a heteroarylene group, or a divalent linking group in which 2 to 4 groups selected from the above groups are linked together; R a represents a group represented by —N(R 104 )(R 105 ), an aryl group, or a heteroaryl group; and R 101 to R 105 each represent a hydrogen atom, an alkyl group, a cycloalkyl group, aryl group, or a heteroaryl group; provided that at least one selected from the substituent on the naphthalene ring and R 11 to R 18 represents a group represented by —Z—R a .

First claim

What is claimed is:

1. A compound is represented by any of formulae (3) and (4-2):

wherein:
R 1 and R 2 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a group represented by —Si(R 101 )(R 102 )(R 103 ), a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms; and
R 11 to R 18 , and R 25 to R 36 each independently represents a hydrogen atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a group represented by —Si(R 101 )(R 102 )(R 103 ), a group represented by —N(R 104 )(R 105 ), 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, or a group represented by —Z—R a ;
R 101 to R 105 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms;
L 1 and L 2 each independently represent a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms, or a divalent linking group in which 2 to 4 groups selected from the arylene group and the heteroarylene group are linked together;
Ar 2 and Ar 1 each independently represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms
the group represented by —Z—R a is represented by formula (b):
—Z 2 —HAr  (b);

—HAr in formula (b) is a group selected from the following groups:

Z 1 and Z 2 each independently represent a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms, or a divalent linking group in which 2 to 4 groups selected from the arylene group and the heteroarylene group are linked together;
each R c independently represents a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms which has an aryl group having 6 to 30 ring carbon atoms, an amino group, a mono- or dialkylamino group having an alkyl group having 1 to 20 carbon atoms, a mono- or diarylamino group having an aryl group having 6 to 30 ring carbon atoms, 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 alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a mono-, di- or tri-substituted silyl group having a substituent selected from an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a halogen atom, a cyano group, or a nitro group;
when more than one R c occurs in each group, groups R c may be the same or different;
R d represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms; and
each p1 independently represents an integer of 0 to 4, each p2 independently represents an integer of 0 to 3, p3 represents an integer of 0 to 2, p4 represents an integer of 0 to 7, and p5 represents an integer of 0 to 5,
provided that one to four selected from R 11 to R 18 and R 25 to R 30 of formula (3) each represent a group represented by —Z—R a .

2. The compound according to claim 1 , wherein only one or two selected from R 11 to R 18 and R 25 to R 30 in formula (3), and only one or two selected from R 11 to R 12 and R 14 to R 18 and R 31 to R 33 and R 35 to R 36 in formula (4-2) are represented by formula (b).

3. The compound according to claim 1 , wherein R 28 in formula (3) is represented by formula (b).

4. The compound according to claim 1 , wherein Z 1 is a single bond.

5. The compound according to claim 1 , wherein Ar 2 and Ar 3 each represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

6. The compound according to claim 1 , wherein L 1 and L 2 are both single bonds, and Ar 2 and Ar 3 each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

7. A material for organic electroluminescence devices, the material comprising the compound according to claim 1 .

8. An organic electroluminescence device, comprising:
an organic thin film layer between a cathode and an anode,
wherein:
the organic thin film layer comprises one or more layers comprising a light emitting layer; and
at least one layer of the organic thin film layer comprises the compound represented by formula (3) or (4-2) according to claim 1 .

9. The organic electroluminescence device according to claim 8 , wherein the light emitting layer comprises the compound represented by formula (3) or (4-2).

10. The organic electroluminescence device according to claim 8 , wherein the at least one layer of the organic thin film layer comprises the compound represented by formula (3) or (4-2) and an anthracene derivative represented by formula (5):

wherein:
Ar 11 and Ar 12 each independently represent a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms or a substituted or unsubstituted fused ring group having 8 to 50 ring atoms; and
R 101 to R 108 are each independently selected from a hydrogen atom, a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted fused ring group having 8 to 50 ring atoms, a group comprising a combination of the monocyclic group and the fused ring group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsub

Assignees

• Idemitsu Kosan Co

Inventors

• Ito Hirokatsu
• Kawamura Masahiro
• Mizuki Yumiko
• Haketa Tasuku
• HAYAMA Tomoharu

Classifications

• C07D333/76

  Dibenzothiophenes · CPC title

• C07D307/77

  ortho- or peri-condensed with carbocyclic rings or ring systems · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• C07D209/86

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

• C07C211/61 Primary

  with at least one of the condensed ring systems formed by three or more rings · CPC title