IP Library Granted Patent US 11,600,786
Granted Patent B2
US 11,600,786 · App. 15/558,898 · Granted Mar 7, 2023

Organic electroluminescent element

Inventors: Junya Ogawa (Kitakyushu, JP); Takahiro Kai (Kitakyushu, JP); Masanori Hotta (Kitakyushu, JP); Yuji Ikenaga (Kitakyushu, JP); Mitsuru Sakai (Kitakyushu, JP); Masashi Tada (Kitakyushu, JP); Tokiko Ueda (Kitakyushu, JP); Katsuhide Noguchi (Kitakyushu, JP)
Assignee: NIPPON STEEL CHEMICAL & MATERIAL CO., LTD.
H01L51/0072C07D209/88C07D405/14C07D487/04C09K11/025C09K11/06H01L51/0067H01L51/0073H01L51/0074H01L51/0085H01L51/50C09K2211/1029C09K2211/185H01L51/5016H01L2251/5384
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Quick Facts
Patent No.
US 11,600,786
App. No.
15/558,898
Granted
Mar 7, 2023
Kind
B2
Abstract

Provided is an organic EL device having high efficiency and high driving stability while being driven at a low voltage. The organic electroluminescent device includes one or more light-emitting layers between an anode and a cathode opposite to each other. At least one of the light-emitting layers contains a host material and a light-emitting dopant, and (i) a first host formed of an indolocarbazole compound having one or two indolocarbazole rings, and (ii) a second host formed of a carbazole compound having a plurality of carbazole rings and having a bond structure represented by the following general formula (3) are used as the host material.

Claims (30)

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 a host material and a light-emitting dopant; and

the host material contains (i) a compound represented by the following general formula (1) or (2) and (ii) a compound represented by the following general formula (3):

in the general formula (1) or (2):

a ring a, a ring c; and a ring c′ each independently represent an aromatic ring represented by the formula (a1) that is fused to two adjacent rings at arbitrary positions, and X 1 represents C—R 8 ;

a ring b, a ring d, and a ring d′ each independently represent a heterocycle represented by the formula (b1) that is fused to two adjacent rings at arbitrary positions;

Ar 1 's each independently represent a (p+1)-valent unsubstituted aromatic hydrocarbon group having 6 carbon atoms, or a (p+1)-valent unsubstituted aromatic heterocyclic group having 3 to 12 carbon atoms;

Z represents a divalent unsubstituted aromatic hydrocarbon group having 6 carbon atoms; or a divalent unsubstituted aromatic heterocyclic group having 3 carbon atoms, or a divalent substituted or unsubstituted linked aromatic group obtained by linking 2 aromatic rings of the groups;

L 1 's each independently represent an unsubstituted aromatic hydrocarbon group having 6 carbon atoms, an unsubstituted aromatic heterocyclic group having 3 to 12 carbon atoms, or an unsubstituted linked aromatic group obtained by linking 2 aromatic rings of the groups;

p's each independently represent a substitution number and each independently represent an integer of from 0 to 2;

R 1 and R 2 each independently represent a hydrogen atom, or a diarylamino group having 12 carbon atoms and R 3 to R 8 each independently represent a hydrogen atom;

in the general formula (3):

L represents an m-valent substituted or unsubstituted aromatic hydrocarbon group having 6 to 13 carbon atoms, an m-valent unsubstituted aromatic heterocyclic group having 12 carbon atoms, or an m-valent substituted or unsubstituted linked aromatic group obtained by linking 2 to 3 aromatic rings of the groups, provided that L does not represent a group containing a carbazole ring;

R's each independently represent a hydrogen atom;

m represents a substitution number and represents an integer of from 1 to 2; and

n's each represent a number of repetitions and each independently represent an integer of from 1 to 4, provided that at least one n represents an integer of from 2 to 4, and at least one bond structure represented by the formula (c1) is present in the general formula (3):

where R's each have the same meaning as that in the general formula (3).

2. An organic electroluminescent device according to claim 1 , wherein all bond structures between n carbazole rings in the general formula (3) comprise bond structures represented by the formula (c1) or by the formula (c1) and the following formula (d1):

where R's each have the same meaning as that in the general formula (3).

3. An organic electroluminescent device according to claim 1 , wherein in the general formula (3), L represents an m-valent group produced by removing m hydrogen atoms from an aromatic compound represented by any one of the formulae (4) to (7):

in the formulae (4) to (7), R's each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 11 carbon atoms, X 2 represents an oxygen atom or a sulfur atom, and q represents an integer of from 0 to 2.

4. An organic electroluminescent device according to claim 3 , wherein in the general formula (3), L represents an m-valent group produced from an aromatic compound represented by any one of the formula (4), (5), or (6).

5. An organic electroluminescent device according to claim 1 , wherein in the general formula (3), a product (n×m) of n and m comprises an integer of from 2 to 6.

6. An organic electroluminescent device according to claim 1 , wherein the host material contains (i) the compound represented by the general formula (I) and (ii) the compound represented by the general formula (3).

7. An organic electroluminescent device according to claim 1 , wherein:

the device comprises a light-emitting layer formed by preliminarily mixing the host material containing the compound represented by the general formula (1) or (2) and the compound represented by the general formula (3), and vapor-depositing the resultant from one evaporation source; and

a mixing ratio between the compound represented by the general formula (1) or (2) and the compound represented by the general formula (3) in the light-emitting layer changes by an amount within 5% relative to a preliminary mixing ratio therebetween before the vapor deposition.

8. An organic electroluminescent device according to claim 1 , wherein the light-emitting dopant comprises an organometallic complex containing at least one metal selected from the group consisting of ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum, and gold.

9. An organic electroluminescent device according to claim 1 , wherein the weight ratio between (i) the compound represented by general formula (1) or (2) and (ii) the compound represented by general formula (3) is within the range of from 10:90 to 90:10.

10. An organic electroluminescent device according to claim 1 , wherein the weight ratio between (i) the compound represented by general formula (1) or (2) and (ii) the compound represented by general formula (3) is within the range of from 20:80 to 80:20.

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 15, 2017
From: OGAWA, JUNYA; KAI, TAKAHIRO; HOTTA, MASANORI; IKENAGA, YUJI; SAKAI, MITSURU; TADA, MASASHI; UEDA, TOKIKO; NOGUCHI, KATSUHIDE
To: NIPPON STEEL & SUMIKIN CHEMICAL CO., LTD.
Reel/Frame 043605/0298 →
Priority Claims (1)
JP 2015-070126 · Mar 30, 2015 · national
Continuity (1)
Related Publication 20180083201A1 · Mar 22, 2018