Organic electroluminescent element, light-emitting material therefor, light emitting device, display device, and illumination device

Patent metadata

Field	Value
Publication number	US-11744144-B2
Application number	US-201916403800-A
Country	US
Kind code	B2
Filing date	May 6, 2019
Priority date	Oct 7, 2011
Publication date	Aug 29, 2023
Grant date	Aug 29, 2023

Abstract

An organic electroluminescent element including a luminescent compound represented by the following formula (in which R 1 to R 14 each independently represent a hydrogen atom, a deuterium atom, an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a cyano group, an amino group, an alkoxy group, an aryloxy group, a thio group, or a silyl group, and 8 to 13 groups out of R 1 to R 14 each represent a hydrogen atom or a deuterium atom) in a light emitting layer has high durability and excellent chromaticity.

First claim

The invention claimed is:

1. An organic electroluminescent element comprising:
a substrate;
a pair of electrodes including an anode and a cathode, disposed on the substrate; and
at least one organic layer including a light emitting layer, disposed between the electrodes,
wherein the light emitting layer contains a luminescent compound represented by the following general formula (1):

wherein R 1 to R 14 each independently represents a hydrogen atom, a deuterium atom, an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a cyano group, an amino group, an alkoxy group, an aryloxy group, a thio group, or a silyl group, and these may be bonded to each other to form a ring;
wherein at least one of R 1 to R 14 is an amino group, wherein the amino group is represented by NR 15 R 16 ,
wherein R 15 and R 16 each independently represent an alkyl group, an aryl group, a heteroaryl group, or a hydrogen atom; and
wherein one of R 15 and R 16 is bonded to an adjacent R 1 to R 14 to form a ring which may be further substituted.

2. The organic electroluminescent element according to claim 1 , wherein the ring formed by the amino group and the adjacent substituent forms a pyrrole skeleton which may be further substituted.

3. The organic electroluminescent element according to claim 1 , wherein the luminescent compound represented by the general formula (1) is a luminescent compound represented by the following general formula (2):

wherein R 15 and R 16 each independently represent an alkyl group, an aryl group, a heteroaryl group, or a hydrogen atom; wherein one of R 15 and R 16 is bonded to R 2 or R 14 to form a ring which may be further substituted.

4. The organic electroluminescent element according to claim 1 , wherein the luminescent compound represented by the general formula (1) is a luminescent compound represented by the following general formula (3);

wherein R 31 , R 32 and R 33 each independently represent an alkyl group, an aryl group, a heteroaryl group, or a hydrogen atom and at least two of R 31 , R 32 and R 33 optionally combine to form an aryl group which may be further substituted.

5. The organic electroluminescent element according to claim 1 , wherein the luminescent compound represented by the general formula (1) is a luminescent compound represented by the following general formula (7):

wherein R 25 , R 26 , R 27 , and R 28 each independently represent an alkyl group, an aryl group, a heteroaryl group, or a hydrogen atom; and
R 25 is bonded to R 2 or R 14 to form a ring which may be further substituted; or
R 27 is bonded to R 2 or R 4 to form a ring which may be further substituted.

6. The organic electroluminescent element according to claim 1 , wherein the light emitting layer contains an anthracene-based host material.

7. The organic electroluminescent element according to claim 1 , wherein the light emitting layer is formed by a vacuum deposition process.

8. The organic electroluminescent element according to claim 1 , wherein the light emitting layer is formed by a wet process.

9. A light emitting device using the organic electroluminescent element according to claim 1 .

10. A display device using the organic electroluminescent element according to claim 1 .

11. An illumination device using the organic electroluminescent element according to claim 1 .

12. A light emitting material for an organic electroluminescent element, represented by the following general formula (1):

wherein R 1 to R 14 each independently represents a hydrogen atom, a deuterium atom, an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a cyano group, an amino group, an alkoxy group, an aryloxy group, a thio group, or a silyl group, and these may be bonded to each other to form a ring;
wherein 8 to 12 groups out of R 1 to R 14 each represents a hydrogen atom or a deuterium atom; and
wherein at least one of R 1 to R 14 is an amino group, wherein the amino group is represented by NR 15 R 16 ,
wherein R 15 and R 16 each independently represent an alkyl group, an aryl group, a heteroaryl group, or a hydrogen atom; and
wherein one of R 15 and R 16 is bonded to an adjacent R 1 to R 14 to form a ring which may be further substituted.

13. The organic electroluminescent element according to claim 1 , wherein the ring formed by the amino group and the adjacent substituent forms a carbazole skeleton which may be further substituted.

14. The organic electroluminescent element according to claim 1 , wherein the luminescent compound represented by the general formula (1) is a luminescent compound represented by the following general formula (4):

wherein R 31 to R 36 each independently represents an alkyl group, an aryl group, a heteroaryl group, or a hydrogen atom; and
at least two of R 31 , R 32 and R 33 optionally combine to form an aryl group which may be further substituted; and
at least two of R 34 , R 35 and R 36 optionally combine to form an aryl group which may be further substituted.

15. The organic electroluminescent element according to claim 1 , wherein the luminescent compound represented by the general formula (1) is a luminescent compound represented by the following general formula (5):

wherein R 17 to R 20 each independently represents an alkyl group, an aryl group, a heteroaryl group, or a hydrogen atom; and
R 17 is bonded to R 2 or R 14 to form a ring which may be further substituted; or
R 19 is bonded to R 7 or R 9 to form a ring which may be further substituted.

16. The organic electroluminescent element according to claim 1 , wherein the luminescent compound represented by the general formula (1) is a luminescent compound represented by the following general formula (6):

wherein R 21 to R 24 each independently represents an alkyl group, an aryl group, a heteroaryl group, or a hydrogen atom; and
R 21 is bonded to R 2 or R 14 to form a ring which may be further substituted; or
R 23 is bonded to R 9 or R 11 to form a ring which may be further substituted.

Assignees

• Udc Ireland Ltd

Inventors

• Watanabe Toru
• Hirai Yuki
• OUYANG Tianhua
• Takaku Koji
• Sotoyama Wataru
• Kitamura Tetsu
• Yonekuta Yasunori

Classifications

• H10K59/877

  comprising scattering means · CPC title

• H10K85/624 Primary

  containing six or more rings · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C09B3/78

  Other dyes in which the anthracene nucleus is condensed with one or more carbocyclic rings · CPC title

• C09B57/001

  Pyrene dyes · CPC title