ANILINE DERIVATIVE AND USE THEREOF

20210061825

16/981142

March 13, 2019

An aniline derivative represented by formula (1) is provided. [chemical expression included] [In formula (1), R1 to R5 are each independently a hydrogen atom or a group represented by formula (2) or (3) [chemical expression included] (wherein Ar1 and Ar2 each independently represent a C6-20 aryl group and Ar3 represents a C6-20 arylene group, any two of Ar1 to Ar3 may be bonded to each other to form a ring in cooperation with the nitrogen atom, R6 to R8 each independently represent a C1-20 alkyl or C6-20 aryl group optionally substituted by W1, and W1 represents a halogen atom, a nitro group, a C1-20 alkoxy group, or a cyano group), at least one of R1 to R5 being a group represented by formula (3).]

NISSAN CHEMICAL CORPORATION (Tokyo, JP)

1. An aniline derivative of formula (1): [chemical expression included] wherein R1 to R5 are each independently a hydrogen atom, or a group of formula (2) or formula (3) [chemical expression included] (wherein Ar1 and Ar2 are each independently an aryl group of 6 to 20 carbon atoms, Ar3 is an arylene group of 6 to 20 carbon atoms, and any two of Ar1 to Ar3 may be bonded to each other to form a ring with a nitrogen atom, R6 to R8 are each independently an alkyl group of 1 to 20 carbon atoms or aryl group of 6 to 20 carbon atoms which may be substituted with W1, and W1 is a halogen atom, a nitro group, an alkoxy group of 1 to 20 carbon atoms, or a cyano group) and at least one of R1 to R5 is a group of formula (3).

2. The aniline derivative of claim 1, wherein R1 to R5 are all groups of formula (3).

3. The aniline derivative of claim 1, wherein R6 to R8 are alkyl groups of 1 to 10 carbon atoms or aryl groups of 6 to 10 carbon atoms.

4. The aniline derivative of claim 3, wherein two of R6 to R8 are methyl groups and the remaining one is a t-butyl group.

5. A charge-transporting substance comprising the aniline derivative of claim 1.

6. A charge-transporting material comprising the charge-transporting substance of claim 5.

7. A charge-transporting varnish comprising the charge-transporting substance of claim 5 and an organic solvent.

8. The charge-transporting varnish according to claim 7, further comprising a dopant.

9. The charge-transporting varnish of claim 8, wherein the dopant is at least one selected from aryl sulfonic acids and aryl sulfonates.

10. A charge-transporting thin film produced using the charge-transporting varnish of claim 7.

11. An electronic device comprising the charge-transporting thin film of claim 10.

12. An organic electroluminescent device comprising the charge-transporting thin film of claim 10.

13. The organic electroluminescent device of claim 12, wherein the charge-transporting thin film is a hole-injecting layer or a hole-transporting layer.

14. A method for producing an aniline derivative of formula (1): [chemical expression included] wherein R1 to R5 are each independently a hydrogen atom, or a group of formula (2) or formula (3): [chemical expression included] (wherein Ar1 to Ar3 and R6 to R8 have the same meaning as below) and at least one of R1 to R5 is a group of formula (3), the method comprising causing a coupling reaction of an amine compound of formula (1′): [chemical expression included] wherein R1′ to R5′ are each independently a hydrogen atom or a group of formula (2): [chemical expression included] (wherein Ar1 and Ar2 are each independently an aryl group of 6 to 20 carbon atoms, Ar3 is an arylene group of 6 to 20 carbon atoms, and any two of Ar1 to Ar3 may be bonded to each other to form a ring with a nitrogen atom) and at least one of R1′ to R5′ is a hydrogen atom; with a carbazole compound of formula (3′): [chemical expression included] wherein X is a halogen atom or a pseudohalogen atom, R6 to R8 are each independently an alkyl group of 1 to 20 carbon atoms or aryl group of 6 to 20 carbon atoms which may be substituted with W1, and W1 is an alkoxy group of 1 to 20 carbon atoms, a halogen atom, a nitro group, or a cyano group, in the presence of a catalyst and a base.

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edspap.20210061825