Electroluminescent element, and light emitting device, display device and lighting device each using organic electroluminescent element

Patent metadata

Field	Value
Publication number	US-11844229-B2
Application number	US-202016790316-A
Country	US
Kind code	B2
Filing date	Feb 13, 2020
Priority date	Jun 16, 2011
Publication date	Dec 12, 2023
Grant date	Dec 12, 2023

Abstract

An organic electroluminescent element which has a substrate, a pair of electrodes disposed on this substrate and composed of an anode and a cathode, and at least one organic layer disposed between these electrodes and including a light-emitting layer, and in which a compound expressed by General Formula 1-1 is contained in at least one layer of the aforementioned light-emitting layer(s) exhibits high luminous efficiency, excellent blue color purity, and little change in chromaticity accompanying drive deterioration. (R 1 to R 10 [each] represent a hydrogen atom or a substituent, and at least one of R 1 to R 10 is a substituent expressed by General Formula 1-2; however, a pyrene skeleton is never contained in R 1 to R 10 ; the asterisk indicates the bonding position with a pyrene ring; X 1 to X 5 [each] represent a carbon atom or a nitrogen atom, and at least one of X 1 to X 5 is a nitrogen atom; R 11 to R 15 [each] represent a hydrogen atom or a substituent, and at least one of R 11 to R 15 is an alkyl group or a silyl group; however, if X 1 to X 5 represent nitrogen atoms, there is no R 11 to R 15 bonded on these nitrogen atoms.)

First claim

The invention claimed is:

1. A material for an organic electroluminescent element composed of a compound expressed by General Formula 1-1 below:

R 1 to R 10 each independently represents a hydrogen atom or a substituent, wherein R to R 10 in General Formula 1-1 do not jointly form a ring; wherein exactly two of R 1 to R 10 are a substituent expressed by General Formula 1-2 below; however, a pyrene skeleton is never contained in R to R 10 ;

wherein the asterisk indicates a bonding position with a pyrene ring; X 1 to X 5 each independently represents a carbon atom or a nitrogen atom, and at least three of X 1 to X 5 is a nitrogen atom;
R 11 to R 15 each independently represents a hydrogen atom or a substituent, wherein exactly one of R 11 to R 15 in each substituent expressed by General Formula 1-2 represents a silyl group; however, if X 1 to X 5 represent nitrogen atoms, there is no R 11 to R 15 bonded on these nitrogen atoms.

2. The material for an organic electroluminescent element according to claim 1 , wherein the compound expressed by General Formula 1-1 is expressed by General Formula 2 below;

R 2 to R 10 each independently represents a hydrogen atom or a substituent; provided that exactly one of R 2 to R 10 is a substituent expressed by General Formula 1-2; X 1 , X 3 , and X 5 each independently represents a nitrogen atom; R 12 and R 14 each independently represents a hydrogen atom or a substituent, exactly one of R 12 and R 14 in each substituent expressed by General Formula 1-2 represents a silyl group; R 11 , R 13 , and R 15 are not present; however, a pyrene skeleton is never contained in R 2 to R 10 .

3. The material for an organic electroluminescent element according to claim 1 , wherein each R 12 in General Formula 1-1 is a silyl group.

4. The material for an organic electroluminescent element according to claim 1 , wherein the compound expressed by General Formula 1-1 is expressed by any of General Formulas 3-1 to 3-3 below;

R 2 to R 10 each independently represents a hydrogen atom or a substituent; wherein none of R 2 to R 10 represents a group of General Formula 1-2; X 1 , X 3 , X 5 , X 6 , X 7 , and X each represents a nitrogen atom; R 12 , R 14 , R 17 , and R 19 each independently represents a hydrogen atom or a substituent, and exactly one of R 12 and R 14 and exactly one of R 17 and R 18 represents a silyl group; R 11 , R 13 , R 15 , R 16 , R 18 , and R 20 are not present; however, a pyrene skeleton is never contained in R 2 to R 10 .

5. The material for an organic electroluminescent element according to claim 4 , wherein R 12 , R 14 , R 17 , and R 18 in General Formulas 3-1 to 3-3 each independently represents a hydrogen atom, an alkyl group, or a silyl group.

6. The material for an organic electroluminescent element according to claim 1 , wherein at least one of R 2 , R 3 , R 4 , R 5 , R 7 , R 9 , and R 10 in General Formula 1-1 is a substituent.

7. The material for an organic electroluminescent element according to claim 1 , wherein at least one of R 2 , R 3 , R 4 , R 5 , R 7 , R 9 , and R 10 in General Formula 1-1 is a substituent selected from the group consisting of an alkyl group, a silyl group, an amino group, and a fluorine group.

8. The material for an organic electroluminescent element according to claim 1 , wherein at least one of R 2 to R 10 in General Formula 1-1 is an ortho-alkyl-substituted phenyl group.

9. The material for an organic electroluminescent element according to claim 8 , wherein said ortho-alkyl-substituted phenyl group is an o-tolyl group, a 2,6-xylyl group, or a mesityl group.

10. The material for an organic electroluminescent element according to claim 1 , wherein R 2 , R 3 , R 4 , R 5 , R 7 , R 9 , and R 10 in General Formula 1-1 are each an alkyl group, a silyl group, an amino group, a fluorine atom, a phenyl group or pyridyl group, wherein the pyridyl group has been substituted with at least one alkyl group, silyl group, amino group, fluorine atom, or phenyl group, or a hydrogen atom.

11. The material for an organic electroluminescent element according to claim 1 , wherein the molecular weight of the compound expressed by General Formula 1-1 is no greater than 1000.

12. The material for an organic electroluminescent element according to claim 1 , wherein the compound expressed by General Formula 1-1 is a light-emitting material.

13. An organic electroluminescent element having
a substrate,
a pair of electrodes disposed on this substrate and composed of an anode and a cathode, and
at least one organic layer disposed between these electrodes and including a light-emitting layer, wherein
a compound expressed by General Formula 1-1 below is contained in at least one layer of said light-emitting layer:

R 1 to R 10 each independently represents a hydrogen atom or a substituent, wherein R 1 to R 10 in General Formula 1-1 do not jointly form a ring; wherein exactly two of R 1 to R 10 are a substituent expressed by General Formula 1-2 below; however, a pyrene skeleton is never contained in R 1 to R 10 ;

wherein the asterisk indicates a bonding position with a pyrene ring; X 1 to X 5 each independently represents a carbon atom or a nitrogen atom, and at least three of X 1 to X 5 is a nitrogen atom;
R 11 to R 15 each independently represents a hydrogen atom or a substituent, wherein exactly one of R 11 to R 15 in each substituent expressed by General Formula 1-2 represents a silyl group; however, if X 1 to X 5 represent nitrogen atoms, there is no R 11 to R 15 bonded on these nitrogen atoms.

14. The organic electroluminescent element according to claim 13 , wherein said light-emitting layer includes an anthracene-based host material.

15. A light-emitting device, display device, or lighting device comprising the organic electroluminescent element according to claim 13 .

16. The material for an organic electroluminescent element according to claim 1 , wherein at least one of R 1 to R 10 represents a silyl group.

Assignees

• Udc Ireland Ltd

Inventors

• Kitamura Tetsu
• Takaku Koji
• Sotoyama Wataru
• Yonekuta Yasunori
• Ise Toshihiro
• Takada Saki
• Watanabe Toru

Classifications

• H10K50/00 Primary

  Organic light-emitting devices (integrated devices or assemblies of multiple devices H10K59/00, H10K65/00; organic semiconductor lasers H01S5/36) · CPC title

• C07D251/14 Primary

  with hydrogen or carbon atoms directly attached to at least one ring carbon atom · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• H05B33/10

  Apparatus or processes specially adapted to the manufacture of electroluminescent light sources · CPC title

• H10K85/40

  Organosilicon compounds, e.g. TIPS pentacene · CPC title