Organic electroluminescent element

Patent metadata

Field	Value
Publication number	US-10340460-B2
Application number	US-201314389003-A
Country	US
Kind code	B2
Filing date	Mar 25, 2013
Priority date	Mar 30, 2012
Publication date	Jul 2, 2019
Grant date	Jul 2, 2019

Abstract

Provided is a practically useful organic electroluminescent device (organic EL device) having high efficiency and high driving stability while being capable of being driven at a low voltage. The organic electroluminescent device includes a light-emitting layer between an anode and a cathode opposite to each other. The light-emitting layer contains two host materials and at least one light-emitting dopant. One of the two host materials is a host material selected from an indolocarbazole compound having one indolocarbazole ring and an indolocarbazole compound having two indolocarbazole rings, and the other thereof is a host material selected from carbazole compounds.

First claim

The invention claimed is:

1. An organic electroluminescent device, comprising one or more light-emitting layers between an anode and a cathode opposite to each other, wherein:
at least one of the light-emitting layers contains two host materials and at least one light-emitting dopant; and
one of the two host materials comprises a host material selected from compounds each represented by any one of the following general formulae (1) to (2), and another of the two host materials comprises a host material selected from compounds each represented by the following general formula (3):

wherein a ring a represents an aromatic ring or heterocycle represented by the formula (a1) condensed at arbitrary positions of two adjacent rings, X1 represents C—R, a ring b represents a heterocycle represented by the formula (b1) condensed at arbitrary positions of two adjacent rings, Ar1 and Ar2 each represent an aromatic hydrocarbon group having 6 to 22 carbon atoms or a monocyclic aromatic heterocyclic group having 3 to 6 carbon atoms, and at least one of Ar1 and Ar2 represents a substituted or unsubstituted monocyclic aromatic heterocyclic group having 3 to 6 carbon atoms, L1 represents an aromatic hydrocarbon group having 6 to 22 carbon atoms, an aromatic heterocyclic group having 3 to 16 carbon atoms, or a group obtained by linking 2 to 10 of the groups, the aromatic hydrocarbon groups or aromatic heterocyclic groups in Ar1, Ar2, and L1 may each have a substituent, p represents an integer of from 0 to 7 and when p represents 2 or more, L1s may be identical to or different from each other, and R and R1 to R3 each independently represent hydrogen, an alkyl group having 1 to 20 carbon atoms, an aralkyl group having 7 to 38 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a dialkylamino group having 2 to 40 carbon atoms, a diarylamino group having 12 to 44 carbon atoms, a diaralkylamino group having 14 to 76 carbon atoms, an acyl group having 2 to 20 carbon atoms, an acyloxy group having 2 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an alkoxycarbonyloxy group having 2 to 20 carbon atoms, an alkylsulfonyl group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 22 carbon atoms, or an aromatic heterocyclic group having 3 to 16 carbon atoms, and may each have a substituent;

wherein a ring c and a ring c′ each represent an aromatic ring or heterocycle represented by the formula (c1) condensed at an arbitrary position of an adjacent ring, a ring d and a ring d′ each represent a heterocycle represented by the formula (d1) condensed at an arbitrary position of an adjacent ring, and the ring c and the ring c′, or the ring d and the ring d′ may be identical to or different from each other, X2 represents C—R′ or N, Z represents an aromatic hydrocarbon group having 6 to 22 carbon atoms, an aromatic heterocyclic group having 3 to 16 carbon atoms, or a divalent linking group obtained by linking 2 to 10 of the groups, but a group linked to N comprises an aromatic hydrocarbon group having 6 to 22 carbon atoms or a monocyclic aromatic heterocyclic group having 3 to 6 carbon atoms, Ar3 represents an aromatic hydrocarbon group having 6 to 22 carbon atoms or a monocyclic aromatic heterocyclic group having 3 to 6 carbon atoms, L2 represents an aromatic hydrocarbon group having 6 to 22 carbon atoms, an aromatic heterocyclic group having 3 to 16 carbon atoms, or a group obtained by linking 2 to 10 of the groups, the aromatic hydrocarbon groups or aromatic heterocyclic groups in Z, Ar3, and L2 may each have a substituent, q represents an integer of from 0 to 7, and when q represents 2 or more, L2s may be identical to or different from each other, and R′ and R4 to R8 each independently represent hydrogen, an alkyl group having 1 to 20 carbon atoms, an aralkyl group having 7 to 38 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a dialkylamino group having 2 to 40 carbon atoms, a diarylamino group having 12 to 44 carbon atoms, a diaralkylamino group having 14 to 76 carbon atoms, an acyl group having 2 to 20 carbon atoms, an acyloxy group having 2 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an alkoxycarbonyloxy group having 2 to 20 carbon atoms, an alkylsulfonyl group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 22 carbon atoms, or an aromatic heterocyclic group having 3 to 16 carbon atoms, and may each have a substituent;

wherein R9 to R12 each independently represent hydrogen, an alkyl group having 1 to 20 carbon atoms, an acyl group having 2 to 20 carbon atoms, or an alkoxy group having 2 to 20 carbon atoms, 1 and m each represent an integer of 1 or 2, n represents 5 or 6, R13 and R14 each independently represent hydrogen or an alkyl group having 1 to 20 carbon atoms, and X3to X5 each independently represent C—H or N, and when n represents 2 or more, R13s, R14s, and X3s to X5s may be identical to or different from each other.

2. An organic electroluminescent device, comprising one or more light-emitting layers between an anode and a cathode opposite to each other, wherein:
at least one of the light-emitting layers contains two host materials and at least one light-emitting dopant; and one of the two host materials comprises a host material selected from compounds each represented by the following general formula (2), and another of the two host materials comprises a host material selected from compounds each represented by the following general formula (3)

wherein a ring c and a ring c′ each represent an aromatic ring or heterocycle represented by the formula (c1) condensed at an arbitrary position of an adjacent ring, a ring d and a ring d′ each represent a heterocycle represented by the formula (d1) condensed at an arbitrary position of an adjacent ring, and the ring c and the ring c′, or the ring d and the ring d′ may be identical to or different from each other, X2 represents C—R′ or N, Z represents an aromatic hydrocarbon group having 6 to 22 carbon atoms, an aromatic heterocyclic group having 3 to 16 carbon atoms, or a divalent linking group obtained by linking 2 to 10 of the groups, but a group linked to N comprises an aromatic hydrocarbon group having 6 to 22 carbon atoms or a monocyclic aromatic heterocyclic group having 3 to 6 carbon atoms, Ar3 represents an aromatic hydrocarbon group having 6 to 22 carbon atoms or a monocyclic aromatic heterocyclic group having 3 to 6 carbon atoms, L2 represents an aromatic hydrocarbon group having 6 to 22 carbon atoms, an aromatic heterocyclic group having 3 to 16 carbon atoms, or a group obtained by linking 2 to 10 of the groups, the aromatic hydrocarbon groups or aromatic heterocyclic groups in Z, Ar3, and L2 may each have a substituent, q represents an integer of from 0 to 7, and when q represents 2 or more, L2s may be identical to or different from each other, and R′ and R4 to R8 each independently represent hydrogen, an alkyl group having 1 to 20 carbon atoms, an aralkyl group having 7 to 38 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a dialkylamino group having 2 to 40 carbon atoms, a diarylamino group having 12 to 44 carbon atoms, a diaralkylamino group having 14 to 76 carbon atoms, an acyl gr

Assignees

• Nippon Steel & Sumikin Chem Co
• Pioneer Corp
• Pioneer Tohoku Corp
• Nippon Steel Chemical & Mat Co Ltd

Inventors

• Fukumatsu Takayuki
• Noguchi Katsuhide
• Tada Masashi
• Sakai Mitsuru
• Asari Tohru
• Shiraishi Kazuto
• Kai Takahiro
• Takahashi Yasuhiro
• Terao Yuhki
• Tsuji Taishi
• Nakajima Yusuke
• Yuki Toshinao

Classifications

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C07D487/04

  Ortho-condensed systems · CPC title

• H05B33/14

  characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} · CPC title

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title