IP Library Granted Patent US 8,993,127
Granted Patent B2
US 8,993,127 · App. 13/227,022 · Granted Mar 31, 2015

Fluorene compound, light-emitting element, light-emitting device, electronic device, lighting device, and organic compound

Inventors: Harue Osaka (Kanagawa, JP); Takako Takasu (Kanagawa, JP); Hiromi Nowatari (Kanagawa, JP); Satoko Shitagaki (Kanagawa, JP); Nobuharu Ohsawa (Kanagawa, JP); Satoshi Seo (Kanagawa, JP); Kyoko Takeda (Kanagawa, JP); Sachiko Kawakami (Kanagawa, JP); Tsunenori Suzuki (Kanagawa, JP)
Assignee: Semiconductor Energy Laboratory Co., Ltd.
C07D307/91C07C25/02C07C25/22C07C33/50C07C49/80C07D333/76C07D409/10C09K11/06H01L51/0073H01L51/0074H05B33/10C09K2211/1007C09K2211/1011C09K2211/1088C09K2211/1092H01L51/0054H01L51/006H01L51/0072H01L51/0081H01L51/0085H01L51/5056Y10S428/917
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Quick Facts
Patent No.
US 8,993,127
App. No.
13/227,022
Granted
Mar 31, 2015
Kind
B2
Abstract

A substance having a hole-transport property and a wide band gap is provided. A fluorene compound represented by a general formula (G1) is provided. In the general formula (G1), α 1 and α 2 separately represent a substituted or unsubstituted arylene group having 6 to 13 carbon atoms; Ar 1 represents a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted 4-dibenzothiophenyl group, or a substituted or unsubstituted 4-dibenzofuranyl group; n and k separately represent 0 or 1; Q 1 represents sulfur or oxygen; and R 1 to R 15 separately represent hydrogen, an alkyl group having 1 to 12 carbon atoms, or an aryl group having 6 to 14 carbon atoms.

Claims (54)

1. A fluorene compound represented by a general formula (G1),

wherein α 1 represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms,

wherein α 2 represents an unsubstituted arylene group having 6 to 13 carbon atoms or a substituted arylene group having 6 to 13 carbon atoms which is substituted by an unsubstituted alkyl group having 1 to 12 carbon atoms,

wherein Ar 1 represents a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted 4-dibenzothiophenyl group, or a substituted or unsubstituted 4-dibenzofuranyl group,

wherein n represents 0 or 1,

wherein k represents 1,

wherein Q 1 represents sulfur or oxygen, and

wherein R 1 to R 15 separately represent hydrogen, an unsubstituted alkyl group having 1 to 12 carbon atoms, or an unsubstituted aryl group having 6 to 14 carbon atoms.

2. The fluorene compound according to claim 1 , wherein the R 1 to R 15 are separately represented by any one of structural formulae (R-1) to (R-14),

3. The fluorene compound according to claim 1 , wherein the α 1 and α 2 are separately represented by any one of structural formulae (α-1) to (α-7),

4. The fluorene compound according to claim 1 ,

wherein the α 1 has a substituent selected from an alkyl group having 1 to 12 carbon atoms and an aryl group having 6 to 14 carbon atoms.

5. The fluorene compound according to claim 1 ,

wherein the Ar 1 is represented by any one of structural formulae (Ar 1 -1) to (Ar 1 -21), and

wherein Q 2 represents sulfur or oxygen.

6. The fluorene compound according to claim 1 ,

wherein the Ar 1 represents an aryl group having 6 to 18 carbon atoms and having one or more substituents, a 4-dibenzothiophenyl group having one or more substituents, or a 4-dibenzofuranyl group having one or more substituents, and

wherein the one or more substituents are separately an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 14 carbon atoms.

7. The fluorene compound according to claim 1 , wherein the α 2 represents an unsubstituted arylene group having 6 carbon atoms or a substituted arylene group having 6 carbon atoms which is substituted by an unsubstituted alkyl group having 1 to 12 carbon atoms.

8. A light-emitting element comprising:

an anode;

a cathode; and

a layer comprising a fluorene compound between the anode and the cathode,

wherein the fluorene compound is represented by a general formula (G1),

wherein α 1 represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms,

wherein α 2 represents an unsubstituted arylene group having 6 to 13 carbon atoms or a substituted arylene group having 6 to 13 carbon atoms which is substituted by an unsubstituted alkyl group having 1 to 12 carbon atoms,

wherein Ar 1 represents a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted 4-dibenzothiophenyl group, or a substituted or unsubstituted 4-dibenzofuranyl group,

wherein n represents 0 or 1,

wherein k represents 1,

wherein Q 1 represents sulfur or oxygen, and

wherein R 1 to R 15 separately represent hydrogen, an unsubstituted alkyl group having 1 to 12 carbon atoms, or an unsubstituted aryl group having 6 to 14 carbon atoms.

9. The light-emitting element according to claim 8 , wherein the layer comprising the fluorene compound is in contact with the anode.

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

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

12. A lighting device comprising the light-emitting device according to claim 10 .

13. The light-emitting element according to claim 8 , wherein the α 2 represents an unsubstituted arylene group having 6 carbon atoms or a substituted arylene group having 6 carbon atoms which is substituted by an unsubstituted alkyl group having 1 to 12 carbon atoms.

14. A fluorene compound represented by a general formula (G1),

wherein α 1 represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms,

wherein α 2 represents an unsubstituted arylene group having 6 to 13 carbon atoms,

wherein Ar 1 represents a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted 4-dibenzothiophenyl group, or a substituted or unsubstituted 4-dibenzofuranyl group,

wherein n represents 0 or 1,

wherein k represents 1,

wherein Q 1 represents sulfur or oxygen, and

wherein R 1 to R 15 separately represent hydrogen, an unsubstituted alkyl group having 1 to 12 carbon atoms, or an unsubstituted aryl group having 6 to 14 carbon atoms.

15. The fluorene compound according to claim 14 , wherein the fluorene compound is represented by any one of structural formulae (103), (106), (111), (141), and (231),

16. A light-emitting element comprising the fluorene compound according to claim 14 , the light-emitting element comprising:

an anode;

a cathode; and

a layer comprising the fluorene compound between the anode and the cathode.

17. The light-emitting element according to claim 16 , wherein the layer comprising the fluorene compound is in contact with the anode.

18. A light-emitting device comprising the light-emitting element according to claim 16 .

19. An electronic device comprising the light-emitting device according to claim 18 .

20. A lighting device comprising the light-emitting device according to claim 18 .

21. The fluorene compound according to claim 14 , wherein the α 2 represents an unsubstituted arylene group having 6 carbon atoms.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 18, 2011
From: OSAKA, HARUE; TAKASU, TAKAKO; NOWATARI, HIROMI; SHITAGAKI, SATOKO; OHSAWA, NOBUHARU; SEO, SATOSHI; TAKEDA, KYOKO; KAWAKAMI, SACHIKO; SUZUKI, TSUNENORI
To: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Reel/Frame 027264/0437 →
Priority Claims (2)
JP 2010-200522 · Sep 8, 2010 · national
JP 2011-122811 · May 31, 2011 · national
Continuity (1)
Related Publication 20120061714A1 · Mar 15, 2012