IP Library Patent Application 15559695
Patent Application
App. No. 15/559,695

ORGANIC ELECTROLUMINESCENT ELEMENT

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Quick Facts
Patent No.
US None
App. No.
15/559,695
Abstract

Provided is an organic electroluminescent device having high efficiency and high driving stability while being driven at a low voltage. The organic electroluminescent device is an organic electroluminescent device including a light-emitting layer between an anode and a cathode opposite to each other, in which: the light-emitting layer contains two kinds of host materials and a light-emitting dopant; and a first host material (H1) out of the two kinds of host materials is an indolocarbazole-based compound having one or two indolocarbazole rings, and a second host material (H2) out of the materials is a host material selected from carbazole-based compounds each represented by the general formula (3), the compounds each having a structure in which two carbazole rings are bonded through a six-membered aromatic ring.

Claims (28)

1 - 12 . (canceled)

13 . 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 at least two kinds of host materials and at least one kind of light-emitting dopant; and at least one kind of the host materials comprises a host material (H1) selected from compounds each represented by any one of the following general formulae (1) and (2), and at least one kind of the host materials comprises a host material (H2) selected from compounds each represented by the following general formula (3):

wherein:

a ring a represents an aromatic ring or a heterocycle represented by the formula (a1) that is fused at arbitrary positions of two adjacent rings, X 1 represents C—R or N, a ring b represents a heterocycle represented by the formula (b1) that is fused at arbitrary positions of two adjacent rings, Ar 1 and Ar 2 each independently represent an aromatic hydrocarbon group having 6 to 24 carbon atoms, or an aromatic heterocyclic group having 3 to 16 carbon atoms, L 1 represents an aromatic hydrocarbon group having 6 to 24 carbon atoms, an aromatic heterocyclic group having 3 to 16 carbon atoms, or a linked aromatic group obtained by linking 2 to 10 aromatic rings of the groups, and the aromatic hydrocarbon group, the aromatic heterocyclic group, or the linked aromatic group in Ar 1 , Ar 2 , and L 1 may have a substituent;

p represents an integer of from 0 to 7, provided that when p represents 2 or more, L 1 's may be identical to or different from each other; and

R and R 1 to R 3 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 24 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 a heterocycle represented by the formula (c1) that is fused at arbitrary positions of adjacent rings, a ring d and a ring d′ each represent a heterocycle represented by the formula (d1) that is fused at arbitrary positions of adjacent rings, 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;

X 2 represents C—R′ or N, Z represents an aromatic hydrocarbon group having 6 to 24 carbon atoms, an aromatic heterocyclic group having 3 to 16 carbon atoms, or a divalent linked aromatic group obtained by linking 2 to 10 aromatic rings of the groups, Ar 3 represents an aromatic hydrocarbon group having 6 to 24 carbon atoms, or a monocyclic aromatic heterocyclic group having 3 to 6 carbon atoms, L 2 represents an aromatic hydrocarbon group having 6 to 24 carbon atoms, an aromatic heterocyclic group having 3 to 18 carbon atoms, or a linked aromatic group obtained by linking 2 to 10 aromatic rings of the groups, and the aromatic hydrocarbon group, the aromatic heterocyclic group, or the linked aromatic group in Z, Ar 3 , and L 2 may have a substituent;

q represents an integer of from 0 to 7, provided that when q represents 2 or more, L 2 's may be identical to or different from each other; and

R′ and R 4 to R 8 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 24 carbon atoms, or an aromatic heterocyclic group having 3 to 16 carbon atoms, and may each have a substituent;

wherein:

R 9 to R 12 each independently represent an aromatic hydrocarbon group having 6 to 18 carbon atoms or an aromatic heterocyclic group having 3 to 9 carbon atoms, and may each have a substituent;

Ar 4 's each independently represent hydrogen or an aromatic hydrocarbon group having 6 to 24 carbon atoms, and the aromatic hydrocarbon group may have a substituent, j represents an integer of from 1 to 6, and at least one Ar 4 does not represent hydrogen;

X 3 to X 5 each independently represent N, C—R″, or C—, and R″'s each independently represent hydrogen, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or a diarylamino group having 12 to 44 carbon atoms; and

k, l, m, and n represent integers satisfying 0≤k+1+m+n≤16,

provided that the following formula (III-7) is excluded from the general formula (3).

14 . An organic electroluminescent device according to claim 13 , wherein one of the two host materials comprises a host material selected from the compounds each represented by any one of the general formulae (1) and (2), another one of the two host materials comprises a host material selected from the compounds each represented by the general formula (3), and a difference in electron affinity (ΔEA) between the two host materials is more than 0.1 eV.

15 . An organic electroluminescent device according to claim 13 , wherein in the general formula (1), X 1 represents C—R.

16 . An organic electroluminescent device according to claim 13 , wherein in the general formula (2), X 2 represents C—R′.

17 . An organic electroluminescent device according to claim 13 , wherein in the general formula (1), at least one of Ar 1 or Ar 2 represents a substituted or unsubstituted aromatic heterocyclic group having 3 to 9 carbon atoms.

18 . An organic electroluminescent device according to claim 13 , wherein in the general formula (3), j represents an integer of 1.

19 . An organic electroluminescent device according to claim 13 , wherein in the general formula (3), X 3 to X 5 each represent C—H, N, or C—.

20 . An organic electroluminescent device according to claim 13 , wherein the organic electroluminescent device comprises a light-emitting layer produced by preliminarily mixing the host material (H1) and the host material (H2), and vapor-depositing the mixture from one vapor deposition source.

21 . An organic electroluminescent device according to claim 20 , wherein a presence ratio of each of the host material (H1) and the host material (H2) in the light-emitting layer changes by an amount within 5% relative to a preliminary mixing ratio of each of the host materials before the vapor deposition.

22 . An organic electroluminescent device according to claim 13 , wherein a difference in vaporization temperature between the host material (H1) and the host material (H2) is within 30° C.

23 . An organic electroluminescent device according to claim 22 , wherein the difference in vaporization temperature is within 10° C.

24 . An organic electroluminescent device according to claim 13 , wherein the light-emitting dopant comprises a phosphorescent light-emitting dopant comprising an organometallic complex containing at least one metal selected from ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum, and gold.

Assignments (3)
CHANGE OF ADDRESS Recorded Nov 13, 2019
From: NIPPON STEEL CHEMICAL & MATERIAL CO., LTD.
To: NIPPON STEEL CHEMICAL & MATERIAL CO., LTD.
Reel/Frame 050998/0200 →
CHANGE OF NAME Recorded Dec 18, 2018
From: NIPPON STEEL & SUMIKIN CHEMICAL CO., LTD.
To: NIPPON STEEL CHEMICAL & MATERIAL CO., LTD.
Reel/Frame 047805/0595 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 20, 2017
From: IKENAGA, YUJI; KAI, TAKAHIRO; HOTTA, MASANORI; OGAWA, JUNYA; SAKAI, MITSURU; TADA, MASASHI; UEDA, TOKIKO; NOGUCHI, KATSUHIDE
To: NIPPON STEEL & SUMIKIN CHEMICAL CO., LTD.
Reel/Frame 043635/0083 →