IP Library › Granted Patent US 11,672,169
Granted Patent B2
US 11,672,169 · App. 16/480,913 · Granted Jun 6, 2023

Organic electroluminescent element

Inventors: Shunji Mochizuki (Tokyo, JP); Takeshi Yamamoto (Tokyo, JP); Naoaki Kabasawa (Tokyo, JP)
Assignee: HODOGAYA CHEMICAL CO., LTD.
H01L51/0059C09K11/06H01L51/0067H01L51/0072H01L51/0073H01L51/0074H01L51/0052H01L51/5064H01L51/5072
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Quick Facts
Patent No.
US 11,672,169
App. No.
16/480,913
Granted
Jun 6, 2023
Kind
B2
Abstract

An object of the present invention is to provide an organic EL element that has (1) high light emission efficiency and high power efficiency, (2) a low light-emission start voltage, (3) a low actual driving voltage, and (4) an especially long lifespan. According to the present invention, provided is an organic electroluminescent element, or organic EL element, having at least an anode, a hole injection layer, a first hole transport layer, a second hole transport layer, a light emitting layer, an electron transport layer, and a cathode, in this order, wherein the second hole transport layer contains an arylamine compound represented by the general formula (1) below, and the electron transport layer contains a pyrimidine derivative represented by the general formula (2) below. Note that A in the general formula (2) represents a monovalent group represented by the structural formula (3) below.

Claims (23)

1. An organic electroluminescent element having at least an anode, a hole injection layer, a first hole transport layer, a second hole transport layer, a light emitting layer, an electron transport layer, and a cathode, in this order,

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

the electron transport layer contains a pyrimidine derivative represented by formula (2-125) below:

where Ar 1 to Ar 4 may be the same or different, and represent an aromatic hydrocarbon group, an aromatic heterocyclic group, or a condensed polycyclic aromatic group; and

2. The organic electroluminescent element according to claim 1 ,

wherein the first hole transport layer contains a triarylamine compound having three to six triarylamine structures in a molecule, the triarylamine structures being linked via a divalent group having no heteroatom or a single bond.

3. The organic electroluminescent element according to claim 2 ,

wherein the triarylamine compound represented by the following general formula (4), is a triarylamine compound that has four triarylamine structures in a molecule:

where R 5 to R 16 may be the same or different, and represent a heavy hydrogen 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,

r 5 , r 6 , r 9 , r 12 , r 15 , and r 16 may be the same or different, and represent an integer of 0 to 5,

r 7 , r 8 , r 10 , r 11 , r 13 , and r 14 may be the same or different, and represent an integer of 0 to 4,

when r 5 , r 6 , r 9 , r 12 , r 15 , or r 16 is an integer of 2 to 5, or when r 7 , r 8 , r 10 , r 11 , r 13 , or r 14 is an integer of 2 to 4, the plurality of atoms or groups represented by the corresponding one of R 5 to R 16 which are bonded to the same benzene ring, may be the same or different, and may be bonded to each other to form a ring via a single bond, a methylene group, an oxygen atom, or a sulfur atom, and

L 1 to L 3 may be the same or different, and represent a divalent group represented by any of the following structural formulae (B) to (G) or a single bond:

where n1 represents an integer of 1 to 3.

4. The organic electroluminescent element according to claim 1 ,

wherein the first hole transport layer contains a triarylamine compound having two triarylamine structures in a molecule, the triarylamine structures being linked via a divalent group having no heteroatom or a single bond.

5. The organic electroluminescent element according to claim 4 ,

wherein the triarylamine compound is represented by the following general formula (5):

where R 17 to R 22 may be the same or different, and represent a heavy hydrogen 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,

r 17 , r 18 , r 21 , and r 22 may be the same or different, and represent an integer of 0 to 5,

r 19 and r 20 may be the same or different, and represent an integer of 0 to 4,

when r 17 , r 18 , r 21 , or r 22 is an integer of 2 to 5, or when r 19 or r 20 is an integer of 2 to 4, the plurality of atoms or groups represented by the corresponding one of R 17 to R 22 which are bonded to the same benzene ring, may be the same or different, and may be bonded to each other to form a ring via a single bond, a methylene group, an oxygen atom, or a sulfur atom, and

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

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 25, 2019
From: MOCHIZUKI, SHUNJI; YAMAMOTO, TAKESHI; KABASAWA, NAOAKI
To: HODOGAYA CHEMICAL CO., LTD.
Reel/Frame 049863/0439 →
Priority Claims (1)
JP JP2017-049617 · Mar 15, 2017 · national
Continuity (1)
Related Publication 20210135116A1 · May 6, 2021