Aromatic amine compound, and organic electroluminescent elements including the compound

Patent metadata

Field	Value
Publication number	US-10243148-B2
Application number	US-201615502572-A
Country	US
Kind code	B2
Filing date	Jun 7, 2016
Priority date	Jun 8, 2015
Publication date	Mar 26, 2019
Grant date	Mar 26, 2019

Abstract

A compound represented by formula (1):

wherein R 1 to R 4 , a to d, L 0 to L 2 , and Ar are as defined in the description, is a material providing an organic electroluminescence device which can be operated at a low driving voltage and has a long lifetime.

First claim

The invention claimed is:

1. A compound represented by formula (1):

wherein:
each of R 1 to R 4 is independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms, a halogen atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 10 ring carbon atoms, or a cyano group;
a is an integer of 0 to 3 and each of b, c, and d is independently an integer of 0 to 4, wherein each of (R 1 ) 0 , (R 2 ) 0 , (R 3 ) 0 , and (R 4 ) 0 means that R 1 , R 2 , R 3 , or R 4 does not exist, and when a, b, c, or d is an integer of 2 or more, two or three R 1 's, two to four R 2 's, two to four R 3 's, and two to four R 4 's may be respectively the same or different, and adjacent two R 1 's, adjacent two R 2 's, adjacent two R 3 's, and adjacent two R 4 's may be bonded to each other to form a ring structure, respectively;
each of L 0 to L 2 is independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 50 ring atoms;
Ar is 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; and
an optional substituent referred to by “substituted or unsubstituted” is at least one group selected from the group consisting of an alkyl group having 1 to 20 carbon atoms; a cycloalkyl group having 3 to 50 ring carbon atoms; an aryl group having 6 to 10 ring carbon atoms; an aralkyl group having 7 to 30 carbon atoms which comprises an aryl group having 6 to 10 ring carbon atoms; an alkoxy group having 1 to 20 carbon atoms; an aryloxy group having 6 to 10 ring carbon atoms; a mono-, di-, or tri-substituted silyl group, wherein the substituent is selected from an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 10 ring carbon atoms; a haloalkyl group having 1 to 20 carbon atoms; a haloalkoxy group having 1 to 20 carbon atoms; a halogen atom; a cyano group; and a nitro group.

2. The compound according to claim 1 , wherein the compound is represented by formula (1-1),

wherein R 1 to R 4 , a to d, L 0 to L 2 , and Ar are as defined in formula (1).

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

wherein R 1 to R 4 , a to d, L 0 to L 2 , and Ar are as defined in formula (1).

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

wherein R 1 to R 4 , a to d, L 0 to L 2 , and Ar are as defined in formula (1).

5. The compound according to claim 1 , wherein the compound is represented by formula (1-4):

wherein R 1 to R 4 , a to d, L 0 to L 2 , and Ar are as defined in formula (1).

6. The compound according to claim 2 , wherein the compound is represented by formula (1-1a) or (1-1b):

wherein R 1 to R 4 , a to d, L 0 to L 2 , and Ar are as defined in formula (1).

7. The compound according to claim 3 , wherein the compound is represented by formula (1-2a) or (1-2b):

wherein R 1 to R 4 , a to d, L 0 to L 2 , and Ar are as defined in formula (1).

8. The compound according to claim 4 , wherein the compound is represented by formula (1-3a) or (1-3b),

wherein R 1 to R 4 , a to d, L 0 to L 2 , and Ar are as defined in formula (1).

9. The compound according to claim 5 , wherein the compound is represented by formula (1-4a) or (1-4b):

wherein R 1 to R 4 , a to d, L 0 to L 2 , and Ar are as defined in formula (1).

10. The compound according to claim 1 , wherein the aryl group in the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms for Ar is selected from the group consisting of a phenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, an acenaphthylenyl group, an anthryl group, a benzanthryl group, an aceanthryl group, a benzophenanthryl group, a triphenylenyl group, a phenalenyl group, a fluorenyl group, a pentacenyl group, a picenyl group, a pentaphenyl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, a s-indanyl group, an as-indanyl group, a fluoranthenyl group, and a perylenyl group.

11. The compound according to claim 1 , wherein the heteroaryl group in the substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms for Ar is selected from the group consisting of a pyrrolyl group, a furyl group, a thienyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a pyrazolyl group, an isoxazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, an isobenzofuranyl group, a benzothiophenyl group, an indolizinyl group, a quinolizinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, an indazolyl group, a benzisoxazolyl group, a benzisothiazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, a N-carbazolyl group, a benzo-N-carbazolyl group, a C-carbazolyl group, a benzo-C-carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a phenothiazinyl group, a phenoxazinyl group, and a xanthenyl group.

12. The compound according to claim 1 , wherein Ar is represented by any of formulae (a) to (n):

in formulae (a) to (n):
each R is independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms which comprises a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 10 ring carbon atoms, a mono-, di-, or tri-su

Assignees

• Idemitsu Kosan Co

Inventors

• Kato Tomoki
• Kawamura Masahiro
• Funahashi Masakazu

Classifications

• H01L51/0073

  Electricity · mapped topic

• C07D307/91

  Dibenzofurans; Hydrogenated dibenzofurans · CPC title

• H01L51/0058

  Electricity · mapped topic

• H01L51/5056

  Electricity · mapped topic

• C07D333/18

  by sulfur atoms · CPC title