Light emitting element, light emitting device, and electronic device

• US 9,397,308 B2
• Filed: 11/28/2007
• Issued: 07/19/2016
• Est. Priority Date: 12/04/2006
• Status: Active Grant

• Current Assignee: Semiconductor Energy Laboratory Co., Ltd.
• Original Assignee: Semiconductor Energy Laboratory Co., Ltd.
• Inventors: Seo, Satoshi, Ohsawa, Nobuharu
• Primary Examiner(s): Yang, J. L.
• Application Number:
  US11/946,484
• Publication Number:
  US 20080261075A1
• Time in Patent Office: 3,156 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: H10K 2101/40 Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers
• CPC Class Codes: H10K 30/865 Intermediate layers comprising a mixture of materials of the adjoining active layers
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/125 specially adapted for multicolour light emission, e.g. for emitting white light
• CPC Class Codes: H10K 50/155 comprising dopants
• CPC Class Codes: H10K 50/165 comprising dopants
• CPC Class Codes: H10K 85/111 comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
• CPC Class Codes: H10K 85/114 Poly-phenylenevinylene; Derivatives thereof
• CPC Class Codes: H10K 85/115 Polyfluorene; Derivatives thereof
• CPC Class Codes: H10K 85/146 poly N-vinylcarbazol; Derivatives thereof
• CPC Class Codes: H10K 85/151 Copolymers

Abstract

The present invention provides a light emitting element which includes an electron transporting layer and a hole transporting layer between an anode and a cathode, and a first layer and a second layer between the electron transporting layer and the hole transporting layer, wherein the first layer includes a first organic compound and an organic compound having a hole transporting property, the second layer includes a second organic compound and an organic compound having an electron transporting property, the first layer is formed in contact with the anode side of the second layer, the first organic compound and the second organic compound are the same compound, and at least one of either the organic compound having a hole transporting property and the organic compound having an electron transporting property is a high molecular compound.

Claims

1. A light emitting device comprising:

an anode;

a light emitting layer over the anode, the light emitting layer comprising;

a first layer; and

a second layer over the first layer; and

a cathode over the second layer,

wherein the first layer includes a first organic compound and a polymer having a hole transporting property,

wherein the second layer includes a second organic compound and an organic compound having an electron transporting property,

wherein the first organic compound and the second organic compound are the same as each other and are selected from 4-(9H-carbazol-9-yl)-4′

-(10-phenyl-9-anthryl)triphenylamine,4,4′

-(2-tert-butylanthracen-9,10-diyl)bis{N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylaniline}, N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine,N,N″

-(2-tert-butylanthracene-9,10-diyldi-4,1-phenylene)bis[N,N′

,N′

-triphenyl-1,4-phenylenediamine],N,N′

-bis[4-(9H-carbazol-9-yl)phenyl]-N,N′

-diphenylstilbene-4,4′

-diamine, N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylstilbene-4-amine, and N,N′

-diphenyl-N,N′

-bis(9-phenylcarbazol-3-yl)stilbene-4,4′

-diamine.

2. A light emitting device according to claim 1 further comprising:

a hole transporting layer between the anode and the first layer and an electron-transporting layer between the cathode and the second layer.

3. A light emitting device according to claim 1, wherein the polymer is selected from poly(N-vinylcarbazole), poly(4-vinyltriphenylamine), poly[N-(4-{N′

-[4-(4-diphenylamino)phenyl]phenyl-N′

-phenylamino}phenyl)methacrylamide], and poly[N,N′

-bis(4-butylphenyl)-N,N-′

bis(phenyl)benzidine.

4. A light emitting device according to claim 1, wherein the organic compound having the electron transporting property is selected from 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole,3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole,9,10-bis(3,5-diphenylphenyl)anthracene,9,10-di(2-naphthyl)anthracene,2-tert-butyl-9,10-di(2-naphthyl)anthracene,9,9′

-bianthryl,9,9′

-(stilben-3,3′

-diyl)diphenanthrene,9,9′

-(stilben-4,4′

-diyl)diphenanthrene, and 3,3′

,3″

-(benzene-1,3,5-tripyrene.

5. A light emitting device according to claim 1 further comprising:

a controller for controlling light emission of the light emitting device.

6. A light emitting device according to claim 1, wherein the light emitting device is a display portion.

7. A light emitting device comprising:

an anode;

a light emitting layer over the anode, the light emitting layer comprising;

a first layer; and

a second layer over the first layer; and

a cathode over the second layer,

wherein the first layer includes a first organic compound and a polymer having a hole transporting property,

wherein a highest occupied molecular orbital level of the polymer is greater than or equal to −

6.0 eV and less than or equal to −

5.0 eV, and a lowest unoccupied molecular orbital level of the polymer is greater than or equal to −

3.0 eV and less than or equal to −

2.0 eV,

wherein the second layer includes a second organic compound and an organic compound having an electron transporting property,

wherein a highest occupied molecular orbital level of the organic compound having the electron transporting property is greater than or equal to −

6.0 eV and less than or equal to −

5.0 eV, and a lowest unoccupied molecular orbital level of the organic compound having the electron transporting property is greater than or equal to −

3.0 eV and less than or equal to −

2.0 eV,

wherein the first organic compound and the second organic compound are the same as each other and are selected from 4-(9H-carbazol-9-yl)-4′

-(10-phenyl-9-anthryl)triphenylamine,4,4′

(2-tert-butylanthracen-9,10-diyl)bis{N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylaniline},N,9-diphenyl-N-[4-(10-phenyl-9anthryl)phenyl]-9H-carbazol-3-amine,N,N″

-(2-tert-butylanthracene-9,10-diyldi-4,1-phenylene)bis[N,N′

,N′

-triphenyl-1,4-phenylenediamine],N,N′

-bis[4-(9H-carbazol-9-yl)phenyl]-N,N′

-diphenylstilbene-4,4′

-diamine,N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylstilbene-4-amine, and N,N′

-diphenyl-N,N′

-bis(9-phenylcarbazol-3-yl)stilbene-4,4′

-diamine.

8. A light emitting device according to claim 7 further comprising:

a hole transporting layer between the anode and the first layer and an electron-transporting layer between the cathode and the second layer.

9. A light emitting device according to claim 7, wherein the polymer is selected from poly(N-vinylcarbazole), poly(4-vinyltriphenylamine), poly[N-(4-{N′

-[4-(4-diphenylamino)phenyl]phenyl-N′

-phenylamino}phenyl)methacrylamide], and poly[N,N′

-bis(4-butylphenyl)-N,N′

-bis(phenyl)benzidine.

10. A light emitting device according to claim 7, wherein the organic compound having the electron transporting property included in the second layer is selected from 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole,3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole,9,10-bis(3,5-diphenylphenyl)anthracene,9,10-di(2-naphthyl)anthracene,2-tert-butyl-9,10-di(2-naphthyl)anthracene,9,9′

-bianthryl,9,9′

-(stilben-3,3′

-diyl)diphenanthrene,9,9′

-(stilben-4,4′

-diyl)diphenanthrene, and 3,3′

,3″

-(benzene-1,3,5-triyl)tripyrene.

11. A light emitting device according to claim 7 further comprising:

a controller for controlling light emission of the light emitting device.

12. A light emitting device according to claim 7, wherein the light emitting device is a display portion.

13. A light emitting device comprising:

an anode;

a light emitting layer over the anode, the light emitting layer comprising;

a first layer ; and

a second layer over the first layer; and

a cathode over the second layer,

wherein the first layer includes a first organic compound and a polymer having a hole transporting property,

wherein the second layer includes a second organic compound and an organic compound having an electron transporting property,

wherein a difference between a highest occupied molecular orbital level of the polymer and a highest occupied molecular orbital level of the organic compound having the electron transporting property is 0.3 eV or less,

wherein a difference between a lowest unoccupied molecular orbital level of the polymer and a lowest unoccupied molecular orbital level of the organic compound having the electron transporting property is 0.3 eV or less,

wherein the first organic compound and the second organic compound are the same as each other and are selected from 4-(9H-carbazol-9-yl)-4′

-(10-phenyl-9-anthryl)triphenylamine,4,4′

-(2-tert-butylanthracen-9,10-diyl)bis{N[4-(9H-carbazol-9-yl)phenyl]-N-phenylaniline},N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine,N,N″

-(2-tert-butylanthracene-9,10-diyldi-4,1-phenylene)bis[N,N′

,N′

-triphenyl-1,4-pylenediamine],N,N′

-bis[4-(9H-carbazol-9-yl)phenyl]-N,N′

-diphenyltilbene-4,4′

-diamine,N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylstilbene-4-amine, and N,N′

-diphenyl-N,N′

-bis(9-phenylcarbazol-3-yl)stilbene-4,4′

-diamine.

14. A light emitting device according to claim 13 further comprising:

a hole transporting layer between the anode and the first layer and an electron-transporting layer between the cathode and the second layer.

15. A fight emitting device according to claim 13, wherein the polymer is selected from poly(N-vinylcarbazole), poly(-vinyltriphenylamine), poly[N-(4-{N′

-[4-(4-diphenylamino)phenyl]phenyl-N′

-phenylamino}phenyl)methacrylamide], and poly[N,N′

-bis(4-butylphenyl)-N,N′

-bis(phenyl)benzidine.

16. A light emitting device according to claim 13, wherein the organic compound having the electron transporting property included in the second layer is selected from 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole,3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole,9,10-bis(3,5-diphenylphenyl)anthracene,9,10-di(2-naphthyl)anthracene,2-tert-butyl-9,10-di(2-naphthyl)anthracene,9,9′

-bianthryl,9,9′

-(stilben-3,3′

-diyl)diphenanthrene,9,9′

-(stilben-4,4′

-diyl)diphenanthrene, and 3,3′

,3″

-(benzene-1,3,5-triyl)tripyrene.

17. A light emitting device according to claim 13 further comprising:

a controller for controlling light emission of the light emitting device.

18. A light emitting device according to claim 13, wherein the light emitting device is a display portion.

19. A light emitting device comprising:

an anode;

a first light emitting unit over the anode;

a charge generation layer over the first light emitting unit;

a second light emitting unit over the charge generation layer; and

a cathode over the second light emitting unit;

wherein each of the first light emitting unit and the second light emitting unit comprises;

a first layer including a first organic compound and a polymer having a hole transporting property; and

a second layer over and in contact with the first layer, the second layer including a second organic compound and an organic compound having an electron transporting property,

wherein in each of the first and second light emitting units, the first layer is located between the anode and the second layer,

wherein the first organic compound and the second organic compound are the same as each other and are selected from 4-(9H-carbazol-9-yl)-4′

-(10-phenyl-9-anthryl)triphenylamine,4,4′

-(2-tert-butylanthracen-9,10-diyl)bis{N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylaniline},N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine,N,N″

-(2-tert-butylanthracene-9,10-diyldi-4,1-phenylene)bis[N,N′

,N′

-triphenyl-1,4-phenylenediamine],N,N′

-bis[4-(9H-carbazol-9-yl)phenyl]-N,N′

-diphenylstilbene-4,4′

-diamine,N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylstilbene-4-amine, and N,N′

-diphenyl-N,N′

-bis(9-phenylcarbazol-3-yl)stilbene-4,4′

-diamine.

20. A light emitting device according to claim 19, wherein at least one of the first and second light emitting units further comprises a hole transporting layer between the anode and the first layer and an electron transporting layer between the cathode and the second layer.

21. A light emitting device according to claim 19, wherein the polymer is selected from poly(N-vinylcarbazole), poly(4-vinyltriphenylamine), poly[N-(4-{N′

-[4-(4-diphenylamino)phenyl]phenyl-N′

-phenylamino}phenyl)methacrylamide], and poly[N,N′

-bis(4-butylphenyl)-N,N′

-bis(phenyl)benzidine.

22. A light emitting device according to claim 19, wherein the organic compound having the electron transporting property included in the second layer is selected from 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole,3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole,9,10-bis(3,5-diphenylphenyl)anthracene,9,10-di(2-naphthyl)anthracene,2-tert-butyl-9,10-di(2-naphthyl)anthracene,9,9′

-bianthryl,9,9′

-(stilben-3,3′

-diyl)diphenanthrene,9,9′

-(stilben-4,4′

-diyl)diphenanthrene, and 3,3′

,3″

-(benzene-1,3,5-triyl)tripyrene.

23. A light emitting device according to claim 19, wherein the charge generation layer includes a composite material of an organic compound and a metal oxide.

24. A light emitting device according to claim 19 further comprising:

a controller for controlling light emission of the light emitting device.

25. A light emitting device according to claim 19, wherein the light emitting device is a display portion.