IP Library Granted Patent US 8,614,334
Granted Patent B2
US 8,614,334 · App. 13/241,313 · Granted Dec 24, 2013

Organic compound, light-emitting element, light-emitting device, electronic device, and lighting device

Inventors: Harue Osaka (Kanagawa, JP); Takako Takasu (Kanagawa, JP); Hiroshi Kadoma (Kanagawa, JP); Yuko Kawata (Kanagawa, JP); Satoko Shitagaki (Kanagawa, JP); Hiromi Nowatari (Kanagawa, JP); Tsunenori Suzuki (Kanagawa, JP); Nobuharu Ohsawa (Kanagawa, JP); Satoshi Seo (Kanagawa, JP)
Assignee: Semiconductor Energy Laboratory Co., Ltd.
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Quick Facts
Patent No.
US 8,614,334
App. No.
13/241,313
Granted
Dec 24, 2013
Kind
B2
Abstract

A novel substance with which an increase in life and emission efficiency of a light-emitting element can be achieved is provided. A carbazole compound having a structure represented by General Formula (G1) is provided. Note that a substituent which makes the HOMO level and the LUMO level of a compound in which a bond of the substituent is substituted with hydrogen deep and shallow, respectively is used as each of substituents in General Formula (G1) (R 1 , R 2 , Ar 3 , and α 3 ). Further, a substituent which makes the band gap (Bg) and the T1 level of a compound in which a bond of the substituent is substituted with hydrogen wide and high is used as each of the substituents in General Formula (G1) (R 1 , R 2 , Ar 3 , and α 3 ).

Claims (39)

1. A carbazole compound represented by General Formula (G1):

wherein R 1 represents an alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrylgroup, a substituted or unsubstituted triphenylenyl group, or a substituent represented by General Formula (G1-1);

wherein R 2 represents hydrogen, an alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituent represented by General Formula (G1-2);

wherein α 3 represents either a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenyldiyl group,

wherein Ar 3 represents a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted triphenylenyl group,

wherein Ar 1 represents an alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted triphenylenyl group,

wherein α 1 represents either a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenyldiyl group,

wherein n represents 0 or 1,

wherein Ar 2 represents an alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenylgroup, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted triphenylenyl group,

wherein α 2 represents either a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenyldiyl group,

wherein in the case where R 1 , R 2 , and Ar 3 have substituents, the subtituents are separately an alkyl group having 1 to 12 carbon atoms, an unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthryl group, or an unsubstituted triphenyl group, and

wherein in the case where α 3 has a substituent, the substituent of α 3 is an alkyl group having 1 to 12 carbon atoms.

2. The carbazole compound according to claim 1 , wherein R 1 in General Formula (G1) represents structures represented by Structural Formula (S-1), Structural Formula (S-2), Structural Formula (S-3), Structural Formula (S-4) or Structural Formula (S-5):

3. The carbazole compound according to claim 1 , wherein R 2 in General Formula (G1) represents structures represented by Structural Formula (S-11), Structural Formula (S-12), Structural Formula (S-13), Structural Formula (S-14), Structural Formula (S-15) or Structural Formula (S-16):

4. The carbazole compound according to claim 1 , wherein α 3 in General Formula (G1), α 1 in General Formula (G1-1), and α 2 in General Formula (G1-2) are separately structures represented by Structural Formula (α-1), Structural Formula (α-2), Structural Formula (α-3), Structural Formula (α-4), Structural Formula (α-5), Structural Formula (α-6)or Structural Formula (α-7):

5. The carbazole compound according to claim 1 , wherein Ar 1 in General Formula (G1-1) and Ar 2 in General Formula (G1-2) are separately structures represented by Structural Formula (Ar-1), Structural Formula (Ar-2), Structural Formula (Ar-3), Structural Formula (Ar-4), Structural Formula (Ar-5) Structural Formula (Ar-6Structural Formula (Ar-7), Structural Formula (Ar-8), Structural Formula (Ar-9) or Structural Formula (Ar-10):

6. The carbazole compound according to claim 1 , wherein Ar 3 in General Formula (G1) represents structures represented by Structural Formula (Ar-11), Structural Formula (Ar-12),Structural Formula (Ar-13), Structural Formula (Ar-14), Structural Formula (Ar-15):

7. A light-emitting element comprising the carbazole compound according to claim 1 .

8. A light-emitting device comprising the light-emitting element according to claim 7 .

9. A lighting device comprising the light-emitting element according to claim 7 .

10. An electronic device comprising the light-emitting element according to claim 7 .

11. A carbazole compound represented by General Formula (G1):

wherein R 1 represents a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group;

wherein R 2 represents hydrogen or a substituent represented by General Formula (G1-2);

wherein α 3 represents a substituted or unsubstituted phenylene group,

wherein Ar 3 represents a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted triphenylenyl group,

wherein Ar 2 represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted triphenylenyl group,

wherein α 2 represents either a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenyldiyl group,

wherein in the case where R 1 , R 2 , and Ar 3 have substituents, the subtituents are separately an alkyl group having 1 to 12 carbon atoms, an unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthryl group, or an unsubstituted triphenyl group, and

wherein in the case where α 3 has a substituent, the substituent of α 3 is an alkyl group having 1 to 12 carbon atoms.

12. A light-emitting element comprising the carbazole compound according to claim 11 .

13. A light-emitting device comprising the light-emitting element according to claim 12 .

14. A lighting device comprising the light-emitting element according to claim 12 .

15. An electronic device comprising the light-emitting element according to claim 12 .

16. A carbazole compound represented by General Formula (I2):

wherein X represents chlorine, bromine, or iodine.

17. The carbazole compound according to claim 1 , wherein the carbazole compound is represented by Structural Formula (102) or Structural formula (105):

18. The carbazole compound according to claim 1 , wherein the carbazloe compound is represented by Structural Formula (100), Structural Formula (108), Structural Formula (111), or Structural Formula (120):

19. The carbazole compound according to claim 1 , the wherein carbazloe compound is represented by Structural Formula (112):

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 23, 2011
From: OSAKA, HARUE; TAKASU, TAKAKO; KADOMA, HIROSHI; KAWATA, YUKO; SHITAGAKI, SATOKO; NOWATARI, HIROMI; SUZUKI, TSUNENORI; OHSAWA, NOBUHARU; SEO, SATOSHI
To: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Reel/Frame 026953/0994 →
Priority Claims (1)
JP 2010-215856 · Sep 27, 2010 · national
Continuity (1)
Related Publication 20120077987A1 · Mar 29, 2012