IP Library › Granted Patent US 10,950,797
Granted Patent B2
US 10,950,797 · App. 15/762,360 · Granted Mar 16, 2021

Organic electroluminescent device

Inventors: Shuichi Hayashi (Tokyo, JP); Naoaki Kabasawa (Tokyo, JP); Keigo Naito (Tokyo, JP)
Assignee: HODOGAYA CHEMICAL CO., LTD.
H01L51/0059C07C211/54C07C211/61C07D401/10C09K11/06H01L51/006H01L51/0052H01L51/0067H01L51/50H01L51/5064C07C2603/18C07C2603/42C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1018H01L51/001H01L51/0054H01L51/0058H01L51/5012H01L51/5072H01L51/56H01L2251/558
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Quick Facts
Patent No.
US 10,950,797
App. No.
15/762,360
Granted
Mar 16, 2021
Kind
B2
Abstract

The present invention provides an organic EL device having at least an anode, a first hole transport layer, a second hole transport layer, a luminous layer, an electron transport layer, and a cathode in this order, wherein the second hole transport layer contains an arylamine compound represented by the following general formula (1), and the electron transport layer contains a pyrimidine derivative represented by the following general formula (2). The organic EL device of the present invention has a high efficiency, and is driven at a low driving voltage. Further, it has a particularly long lifetime.

Claims (38)

1. An organic electroluminescent device having at least an anode, a first hole transport layer, a second hole transport layer, a luminous layer, an electron transport layer, and a cathode in this order, wherein

the second hole transport layer contains an arylamine compound represented by the following general formula (1), and

the electron transport layer contains a pyrimidine derivative represented by the following general formula (2):

where

Ar 1 to Ar 4 may be identical or different, and each represents an aromatic hydrocarbon group, an aromatic heterocyclic group, or a condensed polycyclic aromatic group, and

n1 denotes an integer of 1 to 4;

where

Ar 5 and Ar 6 may be identical or different, and each represents an aromatic hydrocarbon group, an aromatic heterocyclic group, or a condensed polycyclic aromatic group, and Ar 7 represents a hydrogen atom, an aromatic hydrocarbon group, an aromatic heterocyclic group, or a condensed polycyclic aromatic group,

wherein the aromatic hydrocarbon group, the aromatic heterocyclic group, or the condensed polycyclic aromatic group represented by Ar 5 to Ar 7 may be unsubstituted or may have a substituent selected from the group consisting of

a deuterium atom, a cyano group, a nitro group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a straight-chain or branched alkyl group having 1 to 6 carbon atoms, a straight-chain or branched alkyloxy group having 1 to 6 carbon atoms, a straight-chain or branched alkenyl group, an aryloxy group, an arylalkyloxy group, a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a fluorenyl group, an indenyl group, a pyrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a spirobifluorenyl group, an acenaphthenyl group, a pyridyl group, a thienyl group, a furyl group, a pyrrolyl group, a quinolyl group, an isoquinolyl group, a benzofuranyl group, a benzothienyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a benzimidazolyl group, a pyrazolyl group, a dibenzofuranyl group, a dibenzothienyl group, an azafluorenyl group, a diazafluorenyl group, a carbolinyl group, an azaspirobifluorenyl group, a diazaspirobifluorenyl group, an arylvinyl group, and an acyl group;

A 1 and A 2 may be identical or different, and each represents a divalent group formed by removing two hydrogen atoms from benzene or naphthalene,

A 3 represents a single bond, and

B represents an aromatic heterocyclic group, which is at least one substituted or unsubstituted group selected from the group consisting of a triazinyl group, a pyridyl group, a pyrimidinyl group, a furyl group, a pyrrolyl group, a thienyl group, a quinolyl group, an isoquinolyl group, a benzofuranyl group, a benzothienyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a benzimidazolyl group, a pyrazolyl group, a dibenzofuranyl group, a dibenzothienyl group, an azafluorenyl group, a diazafluorenyl group, a naphthyridinyl group, a phenanthrolinyl group, an acridinyl group, a carbolinyl group, an azaspirobifluorenyl group, a diazaspirobifluorenyl group, a bipyridyl group, a terpyridyl group, a pyrazinyl group, an imidazolyl group, a quinazolinyl group, a benzotriazolyl group, a benzothiadiazolyl group, a pyridopyrrolyl group, a pyridoimidazolyl group, a pyridotriazolyl group, a phenazinyl group, a phenoxazinyl group, and a phenothiazinyl group.

2. The organic electroluminescent device according to claim 1 , wherein the first hole transport layer contains a hole transporting arylamine compound.

3. The organic electroluminescent device according to claim 2 , wherein the first hole transport layer contains a triarylamine compound having 2 triarylamine structures in a molecule thereof, the triarylamine structures being linked together by a single bond or a heteroatom-free divalent group.

4. The organic electroluminescent device according to claim 3 , wherein the triarylamine compound having 2 triarylamine structures in the molecule is represented by the following general formula (4):

where

r 13 , r 14 , r 17 and r 18 each denotes an integer of 0 to 5, while r 15 and r 16 each denotes an integer of 0 to 4,

R 13 to R 18 may be identical or different, and each represents a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, a cycloalkyloxy group having 5 to 10 carbon atoms, an aromatic hydrocarbon group, an aromatic heterocyclic group, a condensed polycyclic aromatic group, or an aryloxyl group and, if a plurality of these groups are bound to the same aromatic ring, the plurality of groups bound may be identical or different, and may bind to each other via a single bond, a methylene group, an oxygen atom, or a sulfur atom to form a ring, and

L 4 represents a divalent group represented by any of the following structural formulas (C) to (G), or a single bond;

5. The organic electroluminescent device according to claim 2 , wherein the first hole transport layer contains a triarylamine compound having 3 to 6 triarylamine structures in a molecule thereof, the triarylamine structures being linked together by a single bond or a heteroatom-free divalent group.

6. The organic electroluminescent device according to claim 5 , wherein the triarylamine compound having 3 to 6 triarylamine structures in the molecule is a triarylamine compound having 4 triarylamine structures in a molecule thereof, the triarylamine compound being represented by the following general formula (3):

where

r 1 , r 2 , r 5 , r 8 , r 11 and r 12 each denotes an integer of 0 to 5,

r 3 , r 4 , r 6 , r 7 , r 9 and r 10 each denotes an integer of 0 to 4,

R 1 to R 12 may be identical or different, and each represents a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, a cycloalkyloxy group having 5 to 10 carbon atoms, an aromatic hydrocarbon group, an aromatic heterocyclic group, a condensed polycyclic aromatic group, or an aryloxyl group and, if a plurality of these groups are bound to the same aromatic ring, the bound groups may be identical or different, and may bind to each other via a single bond, a methylene group, an oxygen atom, or a sulfur atom to form a ring, and

L 1 to L 3 may be identical or different, and each represents a divalent group represented by any of the following structural formulas (B) to (G), or a single bond;

where n2 denotes an integer of 1 to 3.

7. The organic electroluminescent device according to claim 1 , wherein the pyrimidine derivative is represented by the following general formula (2a):

where

Ar 5 to Ar 7 , A 1 to A 3 , and B are as defined in the general formula (2).

8. The organic electroluminescent device according to claim 1 , wherein the pyrimidine derivative is represented by the following general formula (2b):

where

Ar 5 to Ar 7 , A 1 to A 3 , and B are as defined in the general formula (2).

9. The organic electroluminescent device according to claim 1 , wherein the luminous layer contains a blue light emitting dopant.

10. The organic electroluminescent device according to claim 9 , wherein the blue light emitting dopant is a pyrene derivative.

11. The organic electroluminescent device according to claim 1 , wherein the luminous layer contains an anthracene derivative.

12. The organic electroluminescent device according to claim 11 , wherein the luminous layer contains the anthracene derivative as a host material.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 22, 2018
From: HAYASHI, SHUICHI; KABASAWA, NAOAKI; NAITO, KEIGO
To: HODOGAYA CHEMICAL CO., LTD.
Reel/Frame 045319/0592 →
Priority Claims (1)
JP JP2015-187600 · Sep 25, 2015 · national
Continuity (1)
Related Publication 20180294416A1 · Oct 11, 2018
Cited By (1)
US 12,509,415