IP Library › Granted Patent US 9,553,273
Granted Patent B2
US 9,553,273 · App. 14/161,847 · Granted Jan 24, 2017

Fluorene derivative, light-emitting element, light-emitting device, electronic device, and lighting device

Inventors: Kaori Ogita (Kanagawa, JP); Tsunenori Suzuki (Kanagawa, JP); Harue Osaka (Kanagawa, JP); Satoshi Seo (Kanagawa, JP)
Assignee: Semiconductor Energy Laboratory Co., Ltd.
H01L51/006C07C211/61C09K11/06H01L51/0058H01L51/5012H05B33/10C09K2211/1007C09K2211/1011C09K2211/1014H01L51/0054
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Quick Facts
Patent No.
US 9,553,273
App. No.
14/161,847
Granted
Jan 24, 2017
Kind
B2
Abstract

An object is to provide a new fluorene derivative as a good light-emitting material for organic EL elements. A fluorene derivative represented by General Formula (G1) is provided. In the formula, R 1 to R 8 separately represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group. Further, α 1 to α 4 separately represent a substituted or unsubstituted phenylene group. Ar 1 represents a substituted or unsubstituted condensed aromatic hydrocarbon having 14 to 18 carbon atoms forming a ring. Ar 2 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. Ar 3 represents an alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms. Further, j, m, and n separately represent 0 or 1, and p represents 1 or 2.

Claims (53)

1. A compound represented by Formula (G1),

wherein R 1 to R 8 separately represent any one of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an unsubstituted phenyl group; an unsubstituted biphenyl group; a phenyl group substituted by a methyl group, an ethyl group, a propyl group, a pentyl group, a hexyl group, or a biphenyl group; and a biphenyl group substituted by a methyl group, an ethyl group, a propyl group, a pentyl group, a hexyl group, or a biphenyl group,

wherein α 1 to α 4 separately represent an unsubstituted phenylene group or a phenylene group substituted by a methyl group, an ethyl group, a propyl group, a pentyl group, a hexyl group, a phenyl group, or a biphenyl group,

wherein Ar 1 represents an unsubstituted condensed aromatic hydrocarbon having 14 to 18 carbon atoms forming a ring or a condensed aromatic hydrocarbon having 14 to 18 carbon atoms forming a ring substituted by a methyl group, an ethyl group, a propyl group, a pentyl group, a hexyl group, a phenyl group, or a biphenyl group,

wherein Ar 2 is represented by any one of Formulas (Ar2-1) to (Ar2-4)

wherein Ar 3 is represented by any one of Formulas (Ar3-1) to (Ar3-8)

wherein j, m, and n separately represent 0 or 1, and

wherein p represents 1 or 2.

2. The compound according to claim 1 , wherein Ar 1 is any one of an unsubstituted phenanthryl group; an unsubstituted pyrenyl group; an unsubstituted triphenylenyl group; an unsubstituted chrysenyl group; an unsubstituted anthryl group; an unsubstituted tetracenyl group; a phenanthryl group substituted by a methyl group, an ethyl group, a propyl group, a pentyl group, a hexyl group, a phenyl group, or a biphenyl group; a pyrenyl group substituted by a methyl group, an ethyl group, a propyl group, a pentyl group, a hexyl group, a phenyl group, or a biphenyl group; a triphenylenyl group substituted by a methyl group, an ethyl group, a propyl group, a pentyl group, a hexyl group, a phenyl group, or a biphenyl group; a chrysenyl group substituted by a methyl group, an ethyl group, a propyl group, a pentyl group, a hexyl group, a phenyl group, or a biphenyl group; an anthryl group substituted by a methyl group, an ethyl group, a propyl group, a pentyl group, a hexyl group, a phenyl group, or a biphenyl group; and a tetracenyl group substituted by a methyl group, an ethyl group, a propyl group, a pentyl group, a hexyl group, a phenyl group, or a biphenyl group.

3. The compound according to claim 1 ,

wherein Ar 1 is represented by any one of Formulas (Ar1-1) to (Ar1-4)

wherein R 11 to R 17 and R 21 to R 23 separately represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and

wherein p is 1 when Ar 1 is represented by Formula (Ar1-1) or (Ar1-3), and p is 2 when Ar 1 is represented by Formula (Ar1-2) or (Ar1-4).

4. The compound according to claim 1 , wherein α 1 to α 4 are separately represented by any one of Formulas (α-1) to (α-3)

5. The compound according to claim 1 , wherein R 1 to R 8 are separately represented by any one of Formulas (R-1) to (R-9)

6. A light-emitting element comprising:

a pair of electrodes; and

a light-emitting layer including the compound according to claim 1 between the pair of electrodes.

7. A light-emitting device comprising the light-emitting element according to claim 6 .

8. A compound represented by Formula (G2),

wherein R 1 to R 8 separately represent any one of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an unsubstituted phenyl group; an unsubstituted biphenyl group; a phenyl group substituted by a methyl group, an ethyl group, a propyl group, a pentyl group, a hexyl group, or a biphenyl group; and a biphenyl group substituted by a methyl group, an ethyl group, a propyl group, a pentyl group, a hexyl group, or a biphenyl group,

wherein R 21 and R 23 separately represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,

wherein α 2 to α 4 separately represent an unsubstituted phenylene group or a phenylene group substituted by a methyl group, an ethyl group, a propyl group, a pentyl group, a hexyl group, a phenyl group, or a biphenyl group,

wherein Ar 2 represents an unsubstituted aryl group having 6 to 13 carbon atoms forming a ring or an aryl group having 6 to 13 carbon atoms forming a ring substituted by a methyl group, an ethyl group, a propyl group, a pentyl group, a hexyl group, a phenyl group, or a biphenyl group,

wherein Ar 3 represents an alkyl group having 1 to 6 carbon atoms or an unsubstituted aryl group having 6 to 12 carbon atoms, and

wherein j and n separately represent 0 or 1.

9. The compound according to claim 8 , wherein α 2 to α 4 are separately represented by any one of Formulas (α-1) to (α-3)

10. The compound according to claim 8 , wherein Ar 2 is represented by any one of Formulas (Ar2-1) to (Ar2-6)

11. The compound according to claim 8 , wherein Ar 3 is represented by any one of Formulas (Ar3-1) to (Ar3-8)

12. The compound according to claim 8 , wherein R 1 to R 8 are separately represented by any one of Formulas (R-1) to (R-9)

13. A light-emitting element comprising:

a pair of electrodes; and

a light-emitting layer including the compound according to claim 8 between the pair of electrodes.

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

15. An electronic device comprising the light-emitting device according to claim 14 .

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

17. A light-emitting element comprising:

a first electrode;

a first light-emitting unit over the first electrode, the first light-emitting unit comprising a first light-emitting layer;

a second light-emitting unit over the first light-emitting unit, the second light-emitting unit comprising a second light-emitting layer;

a charge-generation layer between the first light-emitting unit and the second light-emitting unit; and

a second electrode over the second light-emitting unit,

wherein at least one of the first light-emitting layer and the second light-emitting layer comprises the compound according to claim 9 between the first electrode and the second electrode.

18. The light-emitting element according to claim 17 , wherein the charge-generation layer is configured to inject electrons into one of the first light-emitting layer and the second light-emitting layer and to inject holes into the other of the first light-emitting layer and the second light-emitting layer.

19. The light-emitting element according to claim 17 ,

wherein the charge-generation layer comprises a first layer injecting holes and a second layer injecting electrons,

wherein the first layer comprises an acceptor substance and a substance having a hole-transport property, and

wherein the second layer comprises a donor substance and a substance having an electron-transport property.

20. The light-emitting element according to claim 19 ,

wherein the acceptor substance is any one of vanadium oxide, molybdenum oxide, and tungsten oxide,

wherein the substance having the hole-transport property is any one of an aromatic amine compound, a carbazole derivative, an aromatic hydrocarbon, an oligomer, a dendrimer, and a polymer,

wherein the donor substance is any one of an oxide of an alkali metal, an alkaline earth metal, a rare-earth metal, and a metal that belongs to Group 13, and

wherein the substance having the electron-transport property is a metal complex or a heterocyclic compound.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 26, 2014
From: OGITA, KAORI; SUZUKI, TSUNENORI; OSAKA, HARUE; SEO, SATOSHI
To: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Reel/Frame 032525/0809 →
Priority Claims (3)
JP 2009-243646 · Oct 22, 2009 · national
JP 2009-264300 · Nov 19, 2009 · national
JP 2010-167352 · Jul 26, 2010 · national
Continuity (2)
Continuation 12907699 · Oct 19, 2010
Related Publication 20140131697A1 · May 15, 2014