Organic electroluminescent element, display device, lighting device, π-conjugated compound, and light-emitting thin film

Patent metadata

Field	Value
Publication number	US-11329234-B2
Application number	US-201916582774-A
Country	US
Kind code	B2
Filing date	Sep 25, 2019
Priority date	Jul 31, 2014
Publication date	May 10, 2022
Grant date	May 10, 2022

Abstract

An object of the present invention is to provide an organic electroluminescent element containing an organic layer interposed between an anode and a cathode, the organic layer containing at least one light emitting layer, wherein the at least one light emitting layer contains a π-conjugated compound having an electron donor portion and an electron acceptor portion in the molecule; the π-conjugated compound has a direction vector from an atom having a HOMO orbital in the electron donor portion to an electron cloud of the HOMO orbital, and a direction vector from an atom having a LUMO orbital in the electron acceptor portion to an electron cloud of the LUMO orbital, and the two direction vectors form an angle θ in the range of 90 to 180 degrees; and the π-conjugated compound has a plurality of the electron donor portions or a plurality of the electron acceptor portions.

First claim

The invention claimed is:

1. An organic electroluminescent element comprising an organic layer interposed between an anode and a cathode, the organic layer containing at least one light emitting layer,
wherein the at least one light emitting layer contains a π-conjugated compound having an electron donor portion and an electron acceptor portion in the molecule;
the π-conjugated compound has a direction vector from an atom having a HOMO orbital in the electron donor portion to an electron cloud of the HOMO orbital, and a direction vector from an atom having a LUMO orbital in the electron acceptor portion to an electron cloud of the LUMO orbital, and the two direction vectors form an angle θ in the range of 90 to 180 degrees; and the π-conjugated compound has a plurality of the electron donor portions or a plurality of the electron acceptor portions, and the π-conjugated compound is represented by any one of Formulas (1) and (4):

wherein, X 1 , X 4 , Y 1 to Y 4 , and Y 10 to Y 13 each respectively represent the electron donor portion or the electron acceptor portion; when X 1 and X 4 each respectively represent the electron donor portion, Y 1 to Y 4 and Y 10 to Y 13 each respectively represent the electron acceptor portion; when X 1 and X 4 each respectively represent the electron acceptor portion, Y 1 to Y 4 and Y 10 to Y 13 each respectively represent the electron donor portion; L 1 to L 4 and represent a linking group, L 1 to L 4 each respectively represent an aryl group which may have a substituent or a heteroaryl group which may have a substituent, L 1 binds X 1 and Y 1 through adjacent carbon atoms, L 2 binds X 1 and Y 2 through adjacent carbon atoms, L 3 binds X 1 and Y 3 through adjacent carbon atoms, and L 4 binds X 1 and Y 4 through adjacent carbon atoms.

2. The organic electroluminescent element described in claim 1 ,
wherein the angle θ is in the range of 135 to 180 degrees.

3. The organic electroluminescent element described in claim 1 ,
wherein one of the electron acceptor portions is bonded to two or more electron donor portions through the linking group, or one of the electron donor portions is bonded to two or more electron acceptor portions through the linking group.

4. The organic electroluminescent element described in claim 1 ,
wherein one of the electron acceptor portions is directly bonded to two or more electron donor portions, or one of the electron donor portions is directly bonded to two or more electron acceptor portions.

5. The organic electroluminescent element described in claim 1 ,
wherein the electron donor portion and the electron acceptor portion represented by X 1 , X 4 , Y 1 to Y 4 , and Y 10 to Y 13 in Formulas (1) and (4) each respectively are one selected from the group consisting of an aryl group which may have a substituent, a heteroaryl group which may have a substituent, an alkyl group which may have a substituent, a carbonyl group which may have a substituent, a nitrogen atom which may have a substituent, a sulfur atom which may have a substituent, a boron atom which may have a substituent, a phosphor atom which may have a substituent, an oxygen atom which may have a substituent, and a silicon atom which may have a substituent.

6. The organic electroluminescent element described in claim 1 ,
wherein L 1 to L 4 in Formula (1) each are a benzene ring.

7. The organic electroluminescent element described in claim 1 ,
wherein an absolute value of a difference between a lowest excited singlet energy level and a lowest triplet energy level (ΔE ST ) is 0.5 eV or less.

8. The organic electroluminescent element described in claim 1 ,
wherein the at least one light emitting layer contains:

the π-conjugated compound; and at least one of a fluorescent compound and a phosphorescent compound.

9. The organic electroluminescent element described in claim 1 ,
wherein the at least one light emitting layer contains:

the π-conjugated compound; at least one of a fluorescent compound and a phosphorescent compound; and a host compound.

10. A display device provided with the organic electroluminescent element described in claim 1 .

11. A lighting device provided with the organic electroluminescent element described in claim 1 .

12. A π-conjugated compound having an electron donor portion and an electron acceptor portion in the molecule,
wherein the π-conjugated compound has a direction vector from an atom having a HOMO orbital in the electron donor portion to an electron cloud of the HOMO orbital, and a direction vector from an atom having a LUMO orbital in the electron acceptor portion to an electron cloud of the LUMO orbital, and the two direction vectors form an angle θ in the range of 90 to 180 degrees; and the π-conjugated compound has a plurality of the electron donor portions or a plurality of the electron acceptor portions, and the π-conjugated compound is represented by any one of Formulas (1) and (4):

wherein, X 1 , X 4 , Y 1 to Y 4 , and Y 10 to Y 13 each respectively represent the electron donor portion or the electron acceptor portion; when X 1 and X 4 each respectively represent the electron donor portion, Y 1 to Y 4 and Y 10 to Y 13 each respectively represent the electron acceptor portion; when X 1 and X 4 each respectively represent the electron acceptor portion, Y 1 to Y 4 and Y 10 to Y 13 each respectively represent the electron donor portion; L 1 to L 4 represent a linking group, L 1 to L 4 each respectively represent an aryl group which may have a substituent or a heteroaryl group which may have a substituent, L 1 binds X 1 and Y 1 through adjacent carbon atoms, L 2 binds X 1 and Y 2 through adjacent carbon atoms, L 3 binds X 1 and Y 3 through adjacent carbon atoms, and L 4 binds X 1 and Y 4 through adjacent carbon atoms.

13. A light-emitting thin film containing the π-conjugated compound described in claim 12 .

Assignees

• Konica Minolta Inc
• Merck Patent Gmbh

Inventors

• Miyata Yasuo
• Namikawa Taketo
• Kita Hiroshi

Classifications

• H10K85/658 Primary

  Organoboranes · CPC title

• H10K2101/20

  Delayed fluorescence emission · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• C07D413/14 Primary

  containing three or more hetero rings · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title