IP Library Granted Patent US 9,287,510
Granted Patent B2
US 9,287,510 · App. 13/773,033 · Granted Mar 15, 2016

Thiadiazole, compound for light-emitting elements, light-emitting element, light-emitting apparatus, authentication apparatus, and electronic device

Inventors: Hidetoshi Yamamoto (Suwa, JP); Tetsuji Fujita (Chino, JP)
Assignee: SEIKO EPSON CORPORATION
H01L51/0071C07D513/04C09K11/06H01L51/0058H01L51/0061H01L51/5012
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,287,510
App. No.
13/773,033
Granted
Mar 15, 2016
Kind
B2
Abstract

The thiadiazole represented by formula (1), when used as a light-emitting material in a light-emitting element, allows the light-emitting element to emit near-infrared light: wherein, in formula (1), each A independently represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl amino group, or a substituted or unsubstituted triarylamine.

Claims (55)

1. A mixture comprising a thiadiazole represented by formula (1):

where each A independently represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl amino group, or a substituted or unsubstituted triarylamine; and

a compound represented by formula IRH-1:

where n represents a natural number of 1 to 12 and R represents a substituent or a functional group, and each R is independently a hydrogen atom, an alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aryl amino group.

2. The mixture according to claim 1 , wherein the thiadiazole represented by formula (1) is a compound represented by any of formulae (2) to (4):

where each R independently represents a hydrogen atom, an alkyl group, or a substituted or unsubstituted aryl group, and there may be a ring formed by a carbon linkage between two adjacent R's.

3. A composition for light-emitting elements comprising the mixture according to claim 1 .

4. A light-emitting material comprising the composition for light-emitting elements according to claim 3 .

5. A light-emitting element comprising:

an anode;

a cathode; and

a light-emitting layer that is disposed between the anode and the cathode and, when electric current flows between the anode and the cathode, emits light,

wherein the light-emitting layer contains a compound represented by formula (1) as a light-emitting material and a compound represented by formula IRH-1 as a host material;

where each A independently represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl amino group, or a substituted or unsubstituted triarylamine;

where n represents a natural number of 1 to 12 and R represents a substituent or a functional group, and each R is independently a hydrogen atom, an alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aryl amino group.

6. The light-emitting element according to claim 5 , wherein the compound represented by formula (1) is a compound represented by any of formulae (2) to (4), and

at least one of the compounds represented by formulae (2) to (4) is selected as the light-emitting material;

where each R independently represents a hydrogen atom, an alkyl group, or a substituted or unsubstituted aryl group, and there may be a ring formed by a carbon linkage between two adjacent R's.

7. The light-emitting element according to claim 5 , wherein the compound represented by formula IRH-1 is a compound represented by formula IRH-2 or IRH-3, and

at least one of the compounds represented by formulae IRH-2 and IRH-3 is selected as the host material;

where each of R 1 to R 4 independently represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aryl amino group, with some or all of R 1 to R 4 the same or all of R 1 to R 4 different.

8. The light-emitting element according to claim 5 , further comprising an electron transport layer, which is a layer having the capability of transporting electrons, provided between the cathode and the light-emitting layer so as to be in contact with the light-emitting layer,

wherein the electron transport layer contains a compound having an azaindolizine skeleton and an anthracene skeleton in the molecule as an electron transport material.

9. A light-emitting element comprising:

an anode;

a cathode; and

a light-emitting layer that is disposed between the anode and the cathode and, when electric current flows between the anode and the cathode, emits light,

wherein the light-emitting layer contains a compound represented by formula (1) as a light-emitting material and a compound represented by formula IRH-4 as a host material;

where each A independently represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl amino group, or a substituted or unsubstituted triarylamine;

where n represents a natural number of 1 to 10 and R represents a substituent or a functional group, and each R is independently a hydrogen atom, an alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aryl amino group.

10. The light-emitting element according to claim 9 , wherein the compound represented by formula (1) is a compound represented by any of formulae (2) to (4), and

at least one of the compounds represented by formulae (2) to (4) is selected as the light-emitting material;

where each R independently represents a hydrogen atom, an alkyl group, or a substituted or unsubstituted aryl group, and there may be a ring formed by a carbon linkage between two adjacent R's.

11. The light-emitting element according to claim 9 , wherein the compound represented by formula IRH-4 is a compound represented by formula IRH-5, IRH-7, or IRH-8, and

at least one of the compounds represented by formulae IRH-5, IRH-7, and IRH-8 is selected as the host material;

where each of R 1 and R 2 independently represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aryl amino group, with R 1 and R 2 the same or different.

12. The light-emitting element according to claim 9 , further comprising an electron transport layer, which is a layer having the capability of transporting electrons, provided between the cathode and the light-e ng layer so as to be in contact with the light-emitting layer,

wherein the electron transport layer contains a compound having an azaindolizine skeleton and an anthracene skeleton in the molecule as an electron transport material.

13. A light-emitting element comprising:

an anode;

a cathode;

a light-emitting layer that is disposed between the anode and the cathode and, when electric current flows between the anode and the cathode, emits light; and

an electron transport layer, which is a layer having the capability of transporting electrons, provided between the cathode and the light-emitting layer so as to be in contact with the light-emitting layer;

wherein the light-emitting layer contains a compound represented by formula (1) as a light-emitting material, and

the electron transport layer contains a compound having an azaindolizine skeleton and an anthracene skeleton in the molecule as an electron transport material;

where each A independently represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl amino group, or a substituted or unsubstituted triarylamine.

14. A light-emitting apparatus comprising the light-emitting element according to claim 5 .

15. A light-emitting apparatus comprising the light-emitting element according to claim 9 .

16. A light-emitting apparatus comprising the light-emitting element according to claim 13 .

17. An authentication apparatus comprising the light-emitting element according to claim 5 .

18. An authentication apparatus comprising the light-emitting element according to claim 9 .

19. An authentication apparatus comprising the light-emitting element according to claim 13 .

20. An electronic device comprising the light-emitting element according to claim 5 .

21. An electronic device comprising the light-emitting element according to claim 9 .

22. An electronic device comprising the light-emitting element according to claim 13 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 2, 2026
From: SEIKO EPSON CORPORATION
To: SHIHENG CREATION LIMITED
Reel/Frame 074264/0489 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 21, 2013
From: YAMAMOTO, HIDETOSHI; FUJITA, TETSUJI
To: SEIKO EPSON CORPORATION
Reel/Frame 029848/0575 →
Priority Claims (3)
JP 2012-041223 · Feb 28, 2012 · national
JP 2012-041224 · Feb 28, 2012 · national
JP 2012-230597 · Oct 18, 2012 · national
Continuity (1)
Related Publication 20130221334A1 · Aug 29, 2013