IP Library Granted Patent US 10,276,800
Granted Patent B2
US 10,276,800 · App. 15/522,471 · Granted Apr 30, 2019

Organic electroluminescence device having at least an a node, a hole injection layer, a first hole transport layer. A second hole transport layer a luminous layer, an electron transport layer, and a cathode

Inventors: Shuichi Hayashi (Tokyo, JP); Daizo Kanda (Tokyo, JP); Kazunori Togashi (Tokyo, JP)
Assignee: HODOGAYA CHEMICAL CO., LTD.
H01L51/0059C07B59/00C07B59/001C07C211/54C07C211/58C07C211/61C07D307/91C09K11/06H01L51/006H01L51/0052H01L51/0061H01L51/0067H01L51/0072H01L51/0077H01L51/5064C07B2200/05C07C2603/18C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1018C09K2211/1029H01L51/0054H01L51/0073H01L51/5012H01L51/5016H01L51/5056H01L51/5072
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Quick Facts
Patent No.
US 10,276,800
App. No.
15/522,471
Granted
Apr 30, 2019
Kind
B2
Abstract

The present invention provides an organic EL device having at least an anode, a hole injection layer, a first hole transport layer, a second hole transport layer, a luminous layer, an electron transport layer, and a cathode in order of description. The second hole transport layer includes an arylamine compound having a specific structure, and the electron transport layer includes a pyrimidine derivative having a specific structure. The organic EL device of the present invention has a high efficiency, a low driving voltage, and a longer life.

Claims (32)

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

the second hole transport layer includes an arylamine compound represented by the following formula (1):

and

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

wherein

Ar 1 and Ar 3 each represents an aromatic hydrocarbon group, and Ar 2 and Ar 4 each represents an aromatic hydrocarbon group or an aromatic heterocyclic group; and

n represents an integer of 2 or 3,

Ar 5 represents an aromatic hydrocarbon group;

Ar 6 represents a phenyl group substituted with a condensed polycyclic aromatic group, and Ar 7 represents a hydrogen atom; and

A represents a monovalent group represented by the following structural formula (3b):

wherein

Ar 8 represents an aromatic heterocyclic group; and

R 1 to R 4 each represents a hydrogen atom.

2. The organic electroluminescence device according to claim 1 , wherein the first hole transport layer includes a triarylamine compound having 3 to 6 triarylamine structures in a molecule, the triarylamine structures being linked to each other via a single bond or a divalent group having no heteroatom.

3. The organic electroluminescence device according to claim 2 , wherein the triarylamine compound having 3 to 6 triarylamine structures is a triarylamine compound which has 4 triarylamine structures in a molecule and is represented by the following formula (4):

wherein

r 5 , r 6 , r 9 , r 12 , r 15 , and r 16 each represents an integer of 0 to 5;

r 7 , r 8 , r 10 , r 11 , r 13 , and r 14 each represents an integer of 0 to 4;

R 5 to R 16 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 aryloxy group; when a plurality of these groups is present in the same benzene ring, the plurality of groups may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring; and

L 1 to L 3 each represents a single bond or a divalent group represented by any of the following structural formulas (B) to (G):

wherein n1 represents an integer of 1 to 3,

4. The organic electroluminescence device according to claim 1 , wherein the first hole transport layer includes a triarylamine compound having 2 triarylamine structures in a molecule, the triarylamine structures being linked to each other via a single bond or a divalent group having no heteroatom.

5. The organic electroluminescence device according to claim 4 , wherein the triarylamine compound having 2 triarylamine structures is represented by the following formula (5):

wherein

r 17 , r 18 , r 21 , and r 22 each represents an integer of 0 to 5;

r 19 and r 20 each represents an integer of 0 to 4;

R 17 to R 22 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 aryloxy group; when a plurality of these groups is bonded to the same benzene ring, the plurality of bonded groups may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring; and

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

6. The organic electroluminescence device according to claim 1 , wherein the luminous layer includes a blue luminous dopant.

7. The organic electroluminescence device according to claim 6 , wherein the blue luminous dopant is a pyrene derivative.

8. The organic electroluminescence device according to claim 1 , wherein the luminous layer includes an anthracene derivative.

9. The organic electroluminescence device according to claim 8 , wherein the luminous layer includes the anthracene derivative as a host material.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 27, 2017
From: HAYASHI, SHUICHI; KANDA, DAIZO; TOGASHI, KAZUNORI
To: HODOGAYA CHEMICAL CO., LTD.
Reel/Frame 042164/0293 →
Priority Claims (1)
JP 2014-231515 · Nov 14, 2014 · national
Continuity (1)
Related Publication 20170317291A1 · Nov 2, 2017
Cited By (1)
US 12,545,656