Carbazole derivative, material for organic electroluminescent element which comprises same, and organic electroluminescent element and electronic device each manufactured using same

Patent metadata

Field	Value
Publication number	US-9963429-B2
Application number	US-201414911352-A
Country	US
Kind code	B2
Filing date	Sep 1, 2014
Priority date	Sep 4, 2013
Publication date	May 8, 2018
Grant date	May 8, 2018

Abstract

A novel carbazole derivative represented by formula (1) in which two or more groups each having a specific structure, such as a carbazolyl group, are bonded to two or more of 2-, 3- and 4-positions of the carbazole derivative is useful as a material for organic electroluminescence devices. A material for organic electroluminescence devices including the carbazole derivative, an organic electroluminescence device employing the carbazole derivative, and an electronic equipment are described.

wherein at least two selected from B 1 to B 3 are represented by formula (2) and A, X 1 to X 4 , L, n, Y, and R 1 to R 8 are as defined in claim 1.

First claim

What is claimed is:

1. A carbazole derivative represented by formula (1):

wherein:
A represents a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms;
X 1 represents N or CH;
X 2 to X 4 each represent N or CR;
R and B 3 each independently represent a hydrogen atom or a substituent, wherein adjacent substituents may be bonded to each other to form a saturated or unsaturated ring structure and when more than one R occurs, groups R may be the same or different; and
at least B 1 and B 2 are represented by formula (2):

wherein
* represents a bonding site of B 1 and B 2 to the carbon atom shown in formula (1);
n is an integer of 0 to 4;
L represents a substituted or unsubstituted arylene group having 6 to 60 ring carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 60 ring atoms, or a substituted or unsubstituted alkylene group having 1 to 50 carbon atoms;
Y represents NZ;
R 2 to R 7 and Z each independently represent a single bond, a hydrogen atom or a substituent, wherein adjacent substituents may be bonded to each other to form a saturated or unsaturated ring structure;
R 1 and R 8 are hydrogen atoms; and
one selected from R 1 to R 8 , Z, R′, and R″ represents a single bond which bonds to L, wherein when n is 0, formula (2) bonds to formula (1) via a single bond, and when n is 2 or more, groups L may be the same or different and may be bonded to each other to form a saturated or unsaturated ring structure.

2. A carbazole derivative represented by formula (1):

wherein:
A represents a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms;
X 1 represents N or CH;
X 2 to X 4 each represent N or CR;
R and B 1 to B 3 each independently represent a hydrogen atom or a substituent, wherein adjacent substituents may be bonded to each other to form a saturated or unsaturated ring structure and when more than one R occurs, groups R may be the same or different; and
at least two selected from B 1 to B 3 are represented by formula (2-2):

wherein
* represents a bonding site of B 1 to B 3 to the carbon atom shown in formula (1);
n is an integer of 0 to 4;
L represents a substituted or unsubstituted arylene group having 6 to 60 ring carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 60 ring atoms, or a substituted or unsubstituted alkylene group having 1 to 50 carbon atoms;
R 2 to R 7 and Z each independently represent a single bond, a hydrogen atom or a substituent, wherein adjacent substituents may be bonded to each other to form a saturated or unsaturated ring structure;
R 1 and R 8 are hydrogen atoms; and
one selected from R 2 to R 7 and Z represents a single bond which bonds to L, wherein when n is 0, formula (2) bonds to formula (1) via a single bond, and when n is 2 or more, groups L may be the same or different and may be bonded to each other to form a saturated or unsaturated ring structure.

3. The carbazole derivative according to claim 1 , wherein formula (2) is represented by formula (2-3):

4. The carbazole derivative according to claim 1 , wherein the carbazole derivative is represented by formula (3):

wherein R 11 to R 18 are the same as R 1 to R 8 , respectively.

5. The carbazole derivative according to claim 1 , wherein the carbazole derivative is represented by formula (5):

wherein:
X 11 to X 13 each independently represent CR 51 or N, provided that at least one selected from X 11 to X 13 represents N; and
R 11 to R 18 are the same as defined above with respect to R 1 to R 8 , and R 19 to R 20 and R 51 each independently represent a hydrogen atom or a substituent.

6. The carbazole derivative according to claim 1 , wherein the substituent represented by R, B 3 , R 2 to R 7 and Z is selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms; a substituted or unsubstituted aralkyl group having 7 to 61 carbon atoms; an amino group; a mono- or disubstituted amino group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms; a substituted or unsubstituted aryloxy group having 6 to 60 ring carbon atoms; a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms; a substituted or unsubstituted arylthio group having 6 to 60 ring carbon atoms; a mono-, di-, or trisubstituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 60 ring carbon atom; a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms; a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms; a halogen atom; a cyano group; a nitro group; a sulfonyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms; a disubstituted phosphoryl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms; an alkylsulfonyloxy group; an arylsulfonyloxy group; an alkylcarbonyloxy group; an arylcarbonyloxy group; a boron-containing group; a zinc-containing group; a tin-containing group; a silicon-containing group; a magnesium-containing group; a lithium-containing group; a hydroxyl group; an alkyl- or aryl-substituted carbonyl group; a carboxyl group; a vinyl group; a (meth)acryloyl group; an epoxy group; and an oxetanyl group.

7. The carbazole derivative according to claim 1 , wherein the substituent represented by R, B 1 to B 3 , R 1 to R 8 , Z, R′, and R″ is selected from the group consisting of a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenylyl group; a substituted or unsubstituted terphenylyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthryl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted 9,9′-spirobifluorenyl group; a substituted or unsubstituted chrysenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted 9,9-dimethylfluorenyl group; a substituted or unsubstituted 9,9-diphenylfluorenyl group; a substituted or unsubstituted pyridyl group; a substitute

Assignees

• Idemitsu Kosan Co

Inventors

• Mizuki Yumiko
• Ito Hirokatsu
• Haketa Tasuku
• HAYAMA Tomoharu
• Nishimura Kazuki
• Kawamura Masahiro
• Shibata Mitsuru

Classifications

• C07D403/14

  containing three or more hetero rings · CPC title

• C09K11/06

  containing organic luminescent materials · 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

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title