IP Library Granted Patent US 8,735,878
Granted Patent B2
US 8,735,878 · App. 13/518,239 · Granted May 27, 2014

Charge transporting material and organic electroluminescence device

Inventors: Tetsu Kitamura (Kanagawa, JP); Toru Watanabe (Kanagawa, JP); Toshihiro Ise (Kanagawa, JP)
Assignee: UDC Ireland Limited
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Quick Facts
Patent No.
US 8,735,878
App. No.
13/518,239
Granted
May 27, 2014
Kind
B2
Abstract

In order to provide an organic electroluminescence device with high luminous efficiency and good durability, the present invention provides a charge transporting material including a compound represented by Formula (Cz-1) wherein the content of a particular halogen-containing impurity in the charge transporting material is from 0.000% to 0.10% when the content is calculated as a proportion of the absorption intensity area of the impurity with respect to the total absorption intensity area of the charge transporting material, as measured by high-performance liquid chromatography at a measurement wavelength of 254 nm, and an organic electroluminescence device wherein the charge transporting material is included in an organic layer: wherein in Formula (Cz-1), each of R 1 to R 5 independently represents a particular atom or group; and each of n1 to n5 independently represents a particular integer.

Claims (44)

1. A charge transporting material, comprising:

a compound represented by Formula (Cz-1),

wherein a content of an impurity represented by Formula (I-1) in the charge transporting material is from 0.000% to 0.10% when the content is calculated as a proportion of an absorption intensity area of the impurity represented by Formula (I-1) with respect to a total absorption intensity area of the charge transporting material, as measured by high-performance liquid chromatography at a measurement wavelength of 254 nm:

wherein in Formula (Cz-1), each of R 1 to R 4 independently represents a fluorine atom, an alkyl group, an aryl group, a silyl group or a cyano group, provided that when R 1 to R 4 respectively exist in plurality, a plurality of R 1 's to a plurality of R 4 's may be the same or different respectively;

R 5 represents an alkyl group, an aryl group or a silyl group, provided that R 5 does not represent a carbazolyl group or a perfluoroalkyl group, and when R 5 exists in plurality, a plurality of R 5 's may be the same or different or a plurality of R 5 's may be bonded together to form an aryl ring;

each of n1 to n4 independently represents an integer from 0 to 4; and

n5 represents an integer from 0 to 5:

wherein in Formula (I-1), R 1 to R 4 are the same atoms or groups as defined for R 1 to R 4 in Formula (Cz-1) respectively; and

n1 to n4 are the same integers as defined for n1 to n4 in Formula (Cz-1) respectively.

2. The charge transporting material according to claim 1 ,

wherein a proportion of a sum of absorption intensity areas of the compound represented by Formula (Cz-1), the impurity represented by Formula (I-1), an impurity represented by Formula (II-1) and 1,3,5-tribromobenzene with respect to the total absorption intensity area of the charge transporting material, as measured by high-performance liquid chromatography at a measurement wavelength of 254 nm, is 100%:

wherein in Formula (II-1), R 5 is the same group as defined for R 5 in Formula (Cz-1); and

n5 is the same integer as defined for n5 in Formula (Cz-1).

3. The charge transporting material according to claim 1 ,

wherein the compound represented by Formula (Cz-1) is represented by Formula (Cz-2) and the impurity represented by Formula (I-1) is represented by Formula (I-2):

wherein in Formula (Cz-2), each of R 8 to R 11 independently represents a hydrogen atom, a fluorine atom, an alkyl group, an aryl group, a silyl group or a cyano group;

each of R 6 and R 7 independently represents an alkyl group, an aryl group, a cyano group or a fluorine atom, provided that when R 6 and R 7 respectively exist in plurality, a plurality of R 6 's and a plurality of R 7 's may be the same or different respectively or a plurality of R 6 's and a plurality of R 7 's may be bonded together to form an aryl ring that may have an alkyl group respectively; and

each of n6 and n7 independently represents an integer from 0 to 5:

wherein in Formula (I-2), R 8 to R 11 are the same atoms or groups as defined for R 8 to R 11 in Formula (Cz-2) respectively.

4. The charge transporting material according to claim 3 ,

wherein a proportion of a sum of absorption intensity areas of the compound represented by Formula (Cz-2), the impurity represented by Formula (I-2), an impurity represented by Formula (II-2) and 1,3,5-tribromobenzene with respect to the total absorption intensity area of the charge transporting material, as measured by high-performance liquid chromatography at a measurement wavelength of 254 nm, is 100%:

wherein in Formula (II-2), R 6 and R 7 are the same atoms or groups as defined for R 6 and R 7 in Formula (Cz-2) respectively; and

n6 and n7 are the same integers as defined for n6 and n7 in Formula (Cz-2) respectively.

5. The charge transporting material according to claim 3 ,

wherein in Formula (Cz-2), R 6 and R 7 represent phenyl groups and each of n6 and n7 independently represents 0 or 1, and in Formulae (Cz-2) and (I-2), each of R 8 to R 11 independently represents a hydrogen atom, a t-butyl group, a phenyl group, a trimethylsilyl group or a triphenylsilyl group.

6. A composition, comprising:

the charge transporting material according to claim 1 .

7. A thin film, comprising:

the charge transporting material according to claim 1 .

8. An organic electroluminescence device, comprising on a substrate:

a pair of electrodes; and

at least one layer of an organic layer including a light emitting layer between the electrodes,

wherein any layer of the at least one layer of an organic layer contains the charge transporting material according to claim 1 .

9. The organic electroluminescence device according to claim 8 ,

wherein the light emitting layer contains the charge transporting material.

10. The organic electroluminescence device according to claim 8 ,

wherein at least one layer of the organic layer between the pair of electrodes is formed by a solution Coating method.

11. A light emission apparatus using the organic electroluminescence device according to claim 8 .

12. A display apparatus using the organic electroluminescence device according to claim 8 .

13. An illumination apparatus using the organic electroluminescence device according to claim 8 .

14. The charge transporting material according to claim 1 ,

wherein the content of the impurity represented by Formula (I-1) in the charge transporting material is from greater than 0.000% to 0.10%.

15. The charge transporting material according to claim 14 ,

wherein the content of the impurity represented by Formula (I-1) in the charge transporting material is from 0.001% to 0.10%.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 31, 2013
From: FUJIFILM CORPORATION
To: UDC IRELAND LIMITED
Reel/Frame 029731/0363 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 21, 2012
From: KITAMURA, TETSU; WATANABE, TORU; ISE, TOSHIHIRO
To: FUJIFILM CORPORATION
Reel/Frame 028420/0926 →
Priority Claims (3)
JP 2010-007535 · Jan 15, 2010 · national
JP 2010-116666 · May 20, 2010 · national
JP 2010-247908 · Nov 4, 2010 · national
Continuity (1)
Related Publication 20120256173A1 · Oct 11, 2012