IP Library Granted Patent US 9,067,952
Granted Patent B2
US 9,067,952 · App. 13/564,376 · Granted Jun 30, 2015

Thiadiazole, light-emitting element, light-emitting apparatus, authentication apparatus, and electronic device

Inventors: Hidetoshi Yamamoto (Suwa, JP); Tetsuji Fujita (Chino, JP)
Assignee: SEIKO EPSON CORPORATION
C07D513/04C07D487/04H01L51/0058H01L51/0059H01L51/0069H01L51/5012C09K11/06H05B33/14C09K2211/1014C09K2211/1044C09K2211/1051
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 9,067,952
App. No.
13/564,376
Granted
Jun 30, 2015
Kind
B2
Abstract

The thiadiazole represented by formula (2) or (4), when used as a light-emitting material in a light-emitting element, allows the light-emitting element to emit near-infrared light: in formulae (2) and (4), each R independently represents a hydrogen atom, an alkyl group, or a substituted or unsubstituted aryl group. There may be a ring formed by a carbon linkage between two adjacent R's.

Claims (56)

1. A thiadiazole represented by formula D-1 or (4):

wherein each R independently represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aryl group, or a ring group, wherein the ring group includes two adjacent carbon atoms that bond to each other.

2. 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 the thiadiazole according to claim 1 .

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

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 for the light-emitting 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 is independently a hydrogen atom, an alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aryl amino group.

4. The light-emitting element according to claim 3 , wherein the compound 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, a substituted or unsubstituted aryl group, or a ring group, wherein the ring group includes two adjacent carbon atoms that bond to each other.

5. The light-emitting element according to claim 3 , wherein the compound represented by formula IRH-1, the host material, is a compound represented by formula IRH-2;

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.

6. The light-emitting element according to claim 3 , wherein the compound represented by formula IRH-1, the host material, is a compound represented by formula IRH-3;

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.

7. 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.

8. The light-emitting element according to claim 7 , wherein the compound 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, a substituted or unsubstituted aryl group, or a ring group, wherein the ring group includes two adjacent carbon atoms that bond to each other.

9. The light-emitting element according to claim 7 , wherein the light-emitting layer contains a compound represented by formula IRH-4 as a host material for the light-emitting material;

where n represents a natural number of 1 to 10 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. 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 electron transport layer contains a compound having an azaindolizine skeleton and an anthracene skeleton in the molecule as an electron transport material, and

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 for the light-emitting 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 each R is independently a hydrogen atom, an alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aryl amino group.

11. The light-emitting element according to claim 10 , wherein the compound 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, a substituted or unsubstituted aryl group, or a ring group, wherein the ring group includes two adjacent carbon atoms that bond to each other.

12. The light-emitting element according to claim 10 , wherein the compound represented by formula IRH-4, the host material, is a compound represented by formula IRH-5;

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.

13. The light-emitting element according to claim 10 , wherein the compound represented by formula IRH-4, the host material, is a compound represented by formula IRH-7;

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.

14. The light-emitting element according to claim 10 , wherein the compound represented by formula IRH-4, the host material, is a compound represented by formula IRH-8;

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.

15. A light-emitting apparatus comprising the light-emitting element according to claim 3 .

16. An authentication apparatus comprising the light-emitting element according to claim 3 .

17. An authentication apparatus comprising the light-emitting element according to claim 7 .

18. An authentication apparatus comprising the light-emitting element according to claim 10 .

19. An electronic device comprising the light-emitting element according to claim 3 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 2, 2026
From: SEIKO EPSON CORPORATION
To: SHIHENG CREATION LIMITED
Reel/Frame 074264/0478 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 1, 2012
From: YAMAMOTO, HIDETOSHI; FUJITA, TETSUJI
To: SEIKO EPSON CORPORATION
Reel/Frame 028710/0641 →
Priority Claims (3)
JP 2011-173660 · Aug 9, 2011 · national
JP 2011-173661 · Aug 9, 2011 · national
JP 2011-173662 · Aug 9, 2011 · national
Continuity (1)
Related Publication 20130037784A1 · Feb 14, 2013