Aromatic amine derivative and organic electroluminescent device using the same

Patent metadata

Field	Value
Publication number	US-2016285012-A1
Application number	US-201615174191-A
Country	US
Kind code	A1
Filing date	Jun 6, 2016
Priority date	Dec 28, 2007
Publication date	Sep 29, 2016
Grant date	—

Abstract

Provided are: an aromatic amine derivative in which a terminal substituent such as a dibenzofuran ring or a dibenzothiophene ring is bonded to a nitrogen atom directly or through an arylene group or the like; an organic electroluminescence device including an organic thin film layer formed of one or more layers including a light emitting layer and interposed between a cathode and an anode in which a layer of the organic thin film layer contains the aromatic amine derivative by itself or as a component of a mixture, and the device has a long lifetime and high luminous efficiency; and an aromatic amine derivative for realizing the device.

First claim

1 . An aromatic amine derivative represented by the following general formula (1):

where Ar 0 represents a substituted or unsubstituted, divalent fused aromatic hydrocarbon group having 10 to 50 ring-forming carbon atoms, and Ar 1 to Ar 4 each independently represent a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, provided that one or more of Ar 1 to Ar 4 each represent a group represented by the following general formula (2) or (3):

where n represents an integer of 0 to 3, m represents an integer of 0 to 5, 1 represents an integer of 0 to 7, X represents oxygen (O), sulfur (S), or selenium (Se), Ar represents a substituted or unsubstituted arylene group having 6 to 60 ring-forming carbon atoms, R represents a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, an amino group, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring-forming atoms, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a silyl group, or a carboxyl group, when n, m, or 1 represents 2 or more, multiple Ar's or multiple R's may be identical to or different from each other, and when multiple R's are present, the multiple R's may be bonded to each other to form a saturated or unsaturated, five- or six-membered cyclic structure that may be substituted, provided that:
when n=0, a five-membered ring portion including X in the general formula (2) is free from being directly bonded to N bonded to Ar 0 ; and
in the general formula (3), a case where (R) 1 and (Ar) n are bonded to a five-membered ring portion including X is excluded.

2 . The aromatic amine derivative according to claim 1 , wherein Ar 0 in the general formula (1) represents a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted chrysenylene group, a substituted or unsubstituted pyrenylene group, or a substituted or unsubstituted benzoanthracenylene group.

3 . The aromatic amine derivative according to claim 1 , wherein —NAr 1 Ar 2 and —NAr 3 Ar 4 are bonded to 2- and 6-positions of the naphthylene group, respectively, —NAr 1 Ar 2 and —NAr 3 Ar 4 are bonded to 9- and 10-positions of the anthracenylene group, respectively, —NAr 1 Ar 2 and —NAr 3 Ar 4 are bonded to 2-, and 6-positions of the anthracenylene group, respectively, —NAr 1 Ar 2 and —NAr 3 Ar 4 are bonded to 2- and 7-positions of the phenanthrylene group, respectively, —NAr 1 Ar 2 and —NAr 3 Ar 4 are bonded to 6- and 12-positions of the chrysenylene group, respectively, —NAr 1 Ar 2 and —NAr 3 Ar 4 are bonded to 1- and 6-positions of the pyrenylene group, respectively, —NAr 1 Ar 2 and —NAr 3 Ar 4 are bonded to 2- and 7-positions of the pyrenylene group, respectively, or —NAr 1 Ar 2 and —NAr 3 Ar 4 are bonded to 7- and 12-positions of the benzoanthracenylene group, respectively.

4 . The aromatic amine derivative according to claim 1 , wherein Ar 1 and Ar a in the general formula (1) each represent a group represented by the general formula (2) or (3).

5 . The aromatic amine derivative according to claim 1 , wherein all of Ar 1 to Ar 4 in the general formula (1) represent a group represented by the general formula (2) or (3).

6 . The aromatic amine derivative according to claim 1 , wherein one or more of Ar 1 to Ar 4 in the general formula (1) represent a group represented by the general formula (3).

7 . The aromatic amine derivative according to claim 1 , wherein n in each of the general formulae (2) and (3) represents 0.

8 . The aromatic amine derivative according to claim 1 , wherein m and 1 in each of the general formulae (2) and (3) represent 0.

9 . The aromatic amine derivative according to claim 1 , wherein x in each of the general formulae (2) and (3) represents an oxygen atom.

10 . The aromatic amine derivative according to claim 1 , wherein, when n in the general formula (3) represents 0, X represents an oxygen atom, and a bonding position is present at a 2-position of a fused ring including X.

11 . The aromatic amine derivative according to claim 1 , wherein X in each of the general formulae (2) and (3) represents a sulfur atom.

12 . The aromatic amine derivative according to claim 1 , wherein, when n in the general formula (3) represents 0, X represents a sulfur atom, and a bonding position is present at a 2-position of a fused ring including X.

13 . The aromatic amine derivative according to claim 1 , wherein R in each of the general formulae (2) and (3) represents a silyl group.

14 . The aromatic amine derivative according to claim 1 , wherein the aromatic amine derivative comprises a light emitting material for an organic electroluminescence device.

15 . The aromatic amine derivative according to claim 1 , wherein the aromatic amine derivative comprises a blue light emitting material for an organic electroluminescence device.

16 . The aromatic amine derivative according to claim 1 , wherein the aromatic amine derivative comprises a green light emitting material for an organic electroluminescence device.

17 . The aromatic amine derivative according to claim 1 , wherein the aromatic amine derivative comprises a doping material for an organic electroluminescence device.

18 . An organic electroluminescence device, comprising an organic thin film layer formed of one or more layers including a light emitting layer and interposed between a cathode and an anode, wherein a layer of the organic thin film layer contains the aromatic amine derivative according to claim 1 by itself or as a component of a mixture.

19 . The organic electroluminescence device according to claim 18 , wherein the light emitting layer contains the aromatic amine derivative.

20 . The organic electroluminescence device according to claim 18 , wherein the light emitting layer contains the aromatic amine derivative as a doping material and contains an anthracene derivative represented by the following general formula (i) as a host material:

where A 1 and A 2 each independently represent a group derived from a substituted or unsubstituted aromatic ring having 6 to 20 ring-forming carbon atoms, R 1 to R 8 each independently represent a group selected from a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 4 to 50 ring-forming atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycl

Assignees

• Idemitsu Kosan Co

Inventors

• Mizuki Yumiko
• Funahashi Masakazu
• Ito Mitsunori
• Kawamura Masahiro

Classifications

• H01L51/0052

  Electricity · mapped topic

• H01L51/0054

  Electricity · mapped topic

• H01L51/0058

  Electricity · mapped topic

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title