IP Library Granted Patent US 9,905,782
Granted Patent B2
US 9,905,782 · App. 14/224,641 · Granted Feb 27, 2018

Light-emitting element, compound, organic compound, display module, lighting module, light-emitting device, display device, lighting device, and electronic device

Inventors: Hideko Inoue (Kanagawa, JP); Miki Kanamoto (Kanagawa, JP); Hiromi Seo (Kanagawa, JP); Satoshi Seo (Kanagawa, JP); Tatsuyoshi Takahashi (Kanagawa, JP); Tomoka Nakagawa (Kanagawa, JP)
Assignee: Semiconductor Energy Laboratory Co., Ltd.
H01L51/0074C07D491/048H01L51/0052H01L51/0071H01L51/0072H01L51/0073H01L51/0059H01L51/0085H01L51/5016H01L2251/5384
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Quick Facts
Patent No.
US 9,905,782
App. No.
14/224,641
Granted
Feb 27, 2018
Kind
B2
Abstract

A light-emitting element having high emission efficiency is provided. A light-emitting element having a low driving voltage is provided. A novel compound which can be used for a transport layer or as a host material or a light-emitting material of a light-emitting element is provided. A novel compound with a benzofuropyrimidine skeleton is provided. Also provided is a light-emitting element which includes the compound with the benzofuropyrimidine skeleton between a pair of electrodes.

Claims (68)

1. A compound represented by formula (G1),

wherein:

A 1 represents a group comprising at least one of a phenyl group, a fluorenyl group, a phenanthryl group, a triphenylenyl group, a dibenzothiophenyl group, a dibenzofuranyl group, a carbazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzthiazolyl group, and a triphenyl amine skeleton which are substituted or unsubstituted; and

R 1 to R 5 separately represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

2. The compound according to claim 1 ,

wherein:

the compound is represented by formula (G2):

α represents a substituted or unsubstituted phenylene group;

n is an integer from 0 to 4; and

Ht uni represents a hole-transport skeleton.

3. The compound according to claim 2 , wherein Ht uni represents any one of a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted carbazolyl group.

4. The compound according to claim 3 ,

wherein:

Ht uni represents any one of groups represented by formulae (Ht-1) to (Ht-6):

R 6 to R 15 separately represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group; and

R 16 represents any one of an alkyl group having 1 to 6 carbon atoms and a substituted or unsubstituted phenyl group.

5. The compound according to claim 2 , wherein n is 2.

6. The compound according to claim 5 ,

wherein:

the compound is represented by formula (G3):

7. The compound according to claim 1 , wherein the compound is represented by any one of formulae (100), (115), (200), and (300):

8. A light-emitting device comprising:

a first layer and a second layer between a pair of electrodes,

wherein at least one of the first layer and the second layer comprises a compound represented by formula (G1),

wherein:

A 1 represents a group comprising at least one of a phenyl group, a fluorenyl group, a phenanthryl group, a triphenylenyl group, a dibenzothiophenyl group, a dibenzofuranyl group, a carbazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzthiazolyl group, and a triphenyl amine skeleton which are substituted or unsubstituted; and

R 1 to R 5 separately represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

9. The light-emitting device according to claim 8 ,

wherein:

the compound is represented by formula (G2):

α represents a substituted or unsubstituted phenylene group;

n is an integer from 0 to 4; and

Ht uni represents a hole-transport skeleton.

10. The light-emitting device according to claim 9 , wherein Ht uni represents any one of a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted carbazolyl group.

11. The light-emitting device according to claim 10 ,

wherein:

Ht uni represents any one of groups represented by formulae (Ht-1) to (Ht-6):

R 6 to R 15 separately represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group; and

R 16 represents any one of an alkyl group having 1 to 6 carbon atoms and a substituted or unsubstituted phenyl group.

12. The light-emitting device according to claim 9 , wherein n is 2.

13. The light-emitting device according to claim 12 ,

wherein:

the compound is represented by formula (G3):

14. The light-emitting device according to claim 8 , wherein the compound is represented by any one of formulae (100), (115), (200), and (300):

15. The light-emitting device according to claim 8 ,

wherein the first layer is a light-emitting layer comprising a light-emitting substance and the compound, and

wherein the second layer is an electron-transport layer.

16. An electronic device comprising the light-emitting device according to claim 8 .

17. A lighting device comprising the light-emitting device according to claim 8 .

18. The light-emitting device according to claim 8 ,

wherein the first layer is a light-emitting layer comprising a light-emitting substance, and

wherein the second layer is an electron-transport layer including the compound.

19. The light-emitting device according to claim 8 ,

wherein the first layer is a light-emitting layer comprising a light-emitting substance including the compound, and

wherein the second layer is an electron-transport layer.

20. A light-emitting device comprising:

a first layer, a second layer over the first layer and a third layer over the second layer between a pair of electrodes;

wherein the first layer comprises a compound having hole-transport property,

wherein at least one of the second layer and the third layer comprises a compound represented by formula (G1),

wherein:

A 1 represents a group comprising at least one of a phenyl group, a fluorenyl group, a phenanthryl group, a triphenylenyl group, a dibenzothiophenyl group, a dibenzofuranyl group, a carbazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzthiazolyl group, and a triphenyl amine skeleton which are substituted or unsubstituted; and

R 1 to R 5 separately represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

21. The light-emitting device according to claim 20 ,

wherein the second layer is a light-emitting layer comprising a light-emitting substance, and

wherein the third layer is an electron-transport layer including the compound.

22. The light-emitting device according to claim 20 ,

wherein the second layer is a light-emitting layer comprising a light-emitting substance including the compound, and

wherein the third layer is an electron-transport layer.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 25, 2014
From: INOUE, HIDEKO; KANAMOTO, MIKI; SEO, HIROMI; SEO, SATOSHI; TAKAHASHI, TATSUYOSHI; NAKAGAWA, TOMOKA
To: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Reel/Frame 032519/0862 →
Priority Claims (1)
JP 2013-064261 · Mar 26, 2013 · national
Continuity (1)
Related Publication 20140291645A1 · Oct 2, 2014