IP Library Granted Patent US 10,700,291
Granted Patent B2
US 10,700,291 · App. 16/255,312 · Granted Jun 30, 2020

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 10,700,291
App. No.
16/255,312
Granted
Jun 30, 2020
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 (90)

1. A light-emitting device comprising:

a first electrode;

a light-emitting layer over the first electrode; and

a second electrode,

wherein the light-emitting layer comprises a first compound and a second compound and a light-emitting substance,

wherein the first compound is represented by formula (G1):

wherein A 1 represents a substituted or unsubstituted group having 6 to 100 carbon atoms, the 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; and

wherein 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 light-emitting device according to claim 1 ,

wherein:

the first 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 light-emitting device according to claim 1 ,

wherein:

the first compound is represented by formula (G3):

4. The light-emitting device according to claim 1 , wherein the first compound is represented by any one of formulae (100), (115), (200), and (300):

5. A light-emitting device comprising:

a first electrode;

a light-emitting layer over the first electrode;

an electron-transport layer over the light-emitting layer; and

a second electrode,

wherein the light-emitting layer comprises a first compound and a second compound and a light-emitting substance,

wherein the electron-transport layer comprises a fourth compound,

wherein at least one of the first compound and the fourth compound is represented by formula (G1):

wherein A 1 represents a substituted or unsubstituted group having 6 to 100 carbon atoms, the 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; and

wherein 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.

6. The light-emitting device according to claim 5 ,

wherein the first compound is represented by the formula (G1), and

wherein the fourth compound is represented by the formula (G1).

7. The light-emitting device according to claim 5 ,

wherein:

at least one of the first compound and the fourth 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.

8. The light-emitting device according to claim 5 ,

wherein:

at least one of the first compound and the fourth compound is represented by formula (G3):

9. The light-emitting device according to claim 5 , wherein at least one of the first compound and the fourth compound is represented by any one of formulae (100), (115), (200), and (300):

10. The light-emitting device according to claim 1 , wherein the light-emitting substance comprises a phosphorescent substance.

11. The light-emitting device according to claim 5 , wherein the light-emitting substance comprises a phosphorescent substance.

12. The light-emitting device according to claim 1 ,

wherein the first compound has an electron-transport property, and

wherein the second compound has an hole-transport property.

13. The light-emitting device according to claim 5 ,

wherein the first compound has an electron-transport property, and

wherein the second compound has an hole-transport property.

14. The light-emitting device according to claim 1 , wherein the first compound and the second compound form an exciplex.

15. The light-emitting device according to claim 5 , wherein the first compound and the second compound form an exciplex.

16. The light-emitting device according to claim 14 , wherein an emission spectrum of the exciplex overlaps with an absorption band of the light-emitting substance on a longest wavelength wide in an absorption spectrum.

17. The light-emitting device according to claim 15 , wherein an emission spectrum of the exciplex overlaps with an absorption band of the light-emitting substance on a longest wavelength wide in an absorption spectrum.

18. The light-emitting device 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.

19. The light-emitting device according to claim 7 , 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.

20. The light-emitting device according to claim 2 ,

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.

21. The light-emitting device according to claim 7 ,

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.

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

23. The light-emitting device according to claim 7 , wherein n is 2.

24. A light-emitting device comprising:

a first electrode;

a light-emitting layer over the first electrode; and

a second electrode,

wherein the light-emitting layer comprises a compound and a light-emitting substance,

wherein the compound is represented by formula (G1):

wherein A l represents a substituted or unsubstituted group having 6 to 100 carbon atoms, the 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; and

wherein 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.

25. The light-emitting device according to claim 24 , wherein the compound is included in a host material of the light-emitting layer.

26. The light-emitting device according to claim 24 , 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.

27. The light-emitting device according to claim 24 , wherein:

the compound is represented by formula (G3):

28. The light-emitting device according to claim 24 , wherein the compound is represented by any one of formulae (100), (115), (200), and (300):

29. The light-emitting device according to claim 24 , wherein the light-emitting substance comprises a phosphorescent substance.

30. The light-emitting device according to claim 26 , 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.

31. The light-emitting device according to claim 26 , wherein n is 2.

Priority Claims (1)
JP 2013-064261 · Mar 26, 2013 · national
Continuity (3)
Continuation 15890899 · Feb 7, 2018
Continuation 14224641 · Mar 25, 2014
Related Publication 20190173024A1 · Jun 6, 2019
Cited By (6)
US 12,219,873 US 12,252,496 US 12,382,779 US 12,534,434 US 12,624,046 US 12,648,355