IP Library › Granted Patent US 11,404,656
Granted Patent B2
US 11,404,656 · App. 16/954,692 · Granted Aug 2, 2022

Light-emitting device, light-emitting apparatus, electronic device, and lighting device

Inventors: Nobuharu Ohsawa (Kanagawa, JP); Satoshi Seo (Kanagawa, JP); Hiroshi Kadoma (Kanagawa, JP)
H01L51/5004H01L27/322H01L51/0072H01L51/0084H01L51/5206H01L51/5221
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Quick Facts
Patent No.
US 11,404,656
App. No.
16/954,692
Granted
Aug 2, 2022
Kind
B2
Abstract

A light-emitting device with low driving voltage and favorable reliability is provided. The light-emitting device includes an electron-injection layer between a cathode and a light-emitting layer. The electron-injection layer is a mixed film of a metal and an organic compound having a function of interacting with the metal as a tridentate or tetradentate ligand, and the metal atom and the organic compound form SOMO.

Claims (75)

1. A light-emitting device comprising:

a light-emitting layer between an anode and a cathode; and

a first layer between the light-emitting layer and the cathode,

wherein the first layer comprises a first organic compound and a metal,

wherein the metal belongs to any of Group 3 to Group 13 of a periodic table,

wherein the first organic compound comprises a substituted or unsubstituted heteroaromatic ring having 1 to 30 carbon atoms,

wherein the first organic compound has a three or four coordination positions,

wherein each of the three or four coordination positions is included in a heteroaromatic ring comprising nitrogen,

wherein the first organic compound is capable of interacting with the metal by the three or four coordination positions, and

wherein the first organic compound and the metal form SOMO.

2. The light-emitting device according to claim 1 , further comprising:

a first light-emitting unit and a second light-emitting unit between the anode and the cathode,

wherein the first light-emitting unit comprises the light-emitting layer and the first layer.

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

wherein the first organic compound is represented by formula (G0):

and

wherein each of A 1 , A 2 and A 3 independently represents a substituted or unsubstituted heteroaromatic ring having 1 to 30 carbon atoms.

4. The light-emitting device according to claim 3 ,

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

and

wherein:

each of X 1 to X 6 independently represents carbon or nitrogen;

the carbon bonds to any one of hydrogen, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroaromatic hydrocarbon group having 3 to 30 carbon atoms;

each of R 1 to R 4 independently represents any one of hydrogen, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroaromatic hydrocarbon group having 3 to 30 carbon atom; and

Ar represents any one of hydrogen, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms, and a substituted or unsubstituted heteroaromatic hydrocarbon group having 2 to 60 carbon atoms.

5. The light-emitting device according to claim 3 ,

wherein the first organic compound is represented by formula (G2):

and

wherein:

each of X 1 and X 2 independently represent carbon (C) or nitrogen (N); the carbon comprises any one of hydrogen, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroaromatic hydrocarbon group having 3 to 30 carbon atoms;

each of R 1 to R 8 independently represents any one of hydrogen, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroaromatic hydrocarbon group having 3 to 30 carbon atoms; and

Ar represents any one of hydrogen, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms, and a substituted or unsubstituted heteroaromatic hydrocarbon group having 2 to 60 carbon atoms.

6. The light-emitting device according to claim 3 ,

wherein the first organic compound is represented by any one of formulae (G3-1) to (G3-3):

and

wherein:

each of R 1 to R 8 independently represents any one of hydrogen, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroaromatic hydrocarbon group having 3 to 30 carbon atoms, and

Ar represents any one of hydrogen, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms, and a substituted or unsubstituted heteroaromatic hydrocarbon group having 2 to 60 carbon atoms.

7. The light-emitting device according to claim 3 ,

wherein the first organic compound is represented by any one of formulae (G4-1) to (G4-3):

and

wherein Ar represents any one of hydrogen, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 2 to 60 carbon atoms, and a substituted or unsubstituted heteroaromatic hydrocarbon group having 2 to 60 carbon atoms.

8. The light-emitting device according to claim 3 ,

wherein the first organic compound is represented by any one of formulae (100) to (103):

9. The light-emitting device according to claim 1 , wherein a work function of the metal is higher than or equal to 4.0 eV and lower than or equal to 5.3 eV.

10. The light-emitting device according to claim 1 , wherein the metal is a transition metal.

11. The light-emitting device according to claim 1 , wherein the metal belongs to any of Group 5, Group 7, Group 9, and Group 11 of the periodic table.

12. The light-emitting device according to claim 1 , wherein the metal belongs to Group 11 of the periodic table.

13. The light-emitting device according to claim 1 , wherein the metal is Ag or Cu.

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

wherein the heteroaromatic ring comprises an electron deficient heteroaromatic ring.

15. The light-emitting device according to claim 14 , wherein the electron deficient heteroaromatic ring is any one of a pyridine ring, a diazine ring and a triazine ring.

16. The light-emitting device according to claim 1 , wherein a LUMO level of the first organic compound is higher than or equal to 3.6 eV and lower than or equal to 2.3 eV.

17. The light-emitting device according to claim 1 , further comprising:

a second layer between the cathode and the first layer,

wherein the second layer comprises a second organic compound comprising an electron deficient heteroaromatic ring.

18. The light-emitting device according to claim 17 , wherein a LUMO level of the second organic compound is lower than an energy level of the SOMO.

19. The light-emitting device according to claim 1 , wherein the first layer comprises neither an alkali metal nor an alkaline earth metal.

20. The light-emitting device according to claim 1 , wherein a molar ratio of the metal to the first organic compound in the first layer is higher than or equal to 0.2 and lower than or equal to 0.8.

21. The light-emitting device according to claim 1 , wherein the cathode comprises the metal.

22. The light-emitting device according to claim 1 , wherein the cathode and the first layer are in contact with each other.

23. The light-emitting device according to claim 1 , wherein a work function of the metal is higher than or equal to a work function of a metal included in the cathode.

24. A light-emitting apparatus comprising:

the light-emitting device according to of claim 1 ; and

at least one of a color filter and a transistor.

25. An electronic device comprising:

the light-emitting apparatus according to claim 24 ; and

at least one of a housing and a display portion.

26. A lighting device comprising:

the light-emitting device according to claim 1 ; and

a housing.

27. An organic compound represented by any one of formulae (200) to (203):

28. A light-emitting device comprising any one of the organic compound according to claim 27 ,

wherein the light-emitting device optionally further comprises one or more compounds represented by formulae (200) to (203) other than the organic compound according to claim 27 .

29. The light-emitting device according to claim 3 , wherein R 1 , R 2 and R 3 form one condensed ring.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 17, 2020
From: OHSAWA, NOBUHARU; SEO, SATOSHI; KADOMA, HIROSHI
To: SEMICONDUCTOR ENERY LABORATORY CO., LTD.
Reel/Frame 052962/0728 →
Priority Claims (1)
JP JP2017-246022 · Dec 22, 2017 · national
Continuity (1)
Related Publication 20200388779A1 · Dec 10, 2020
Cited By (2)
US 12,527,190 US 12,581,796