Aromatic amine derivatives and preparation method, uses and organic electroluminescent devices thereof

Patent metadata

Field	Value
Publication number	US-9515268-B2
Application number	US-201414436960-A
Country	US
Kind code	B2
Filing date	Sep 3, 2014
Priority date	Apr 24, 2014
Publication date	Dec 6, 2016
Grant date	Dec 6, 2016

Abstract

The present invention relates to the field of organic electroluminescent technology, particularly relates to an aromatic amine derivative, its preparation method, uses and organic electroluminescent devices. The technical aim of the present invention is to improve the film forming ability and the redox repeatability. The aromatic amine derivative has the structure of formula I, wherein, R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen, a substituted or unsubstituted C 1 -C 40 alkyl, a substituted or unsubstituted C 1 -C 40 alkoxy, a substituted or unsubstituted C 3 -C 40 cycloalkyl, a substituted or unsubstituted C 6 -C 50 aryl group, a substituted or unsubstituted C 3 -C 50 heteroaryl containing one or two heteroatoms selected from N, O and S, or a substituted or unsubstituted C 10 -C 40 fused aryl group formed together with the phenyl group linked therewith; wherein, m, n, p and q each independently represent 0, 1, 2, 3, 4 or 5; the substituents are one or more groups selected from the group consisting of a halogen, a C 1 -C 10 alkyl, a C 1 -C 10 alkoxy, a C 3 -C 20 cycloalkyl, a C 6 -C 20 aryl group or a C 4 -C 20 heteroaryl group. The present invention may be applied in organic electroluminescent devices.

First claim

The invention claimed is:

1. An aromatic amine derivative, having a structure of the following general formula I:

in which, R 1 , R 2 , R 3 and R 4 each independently represent a substituted or unsubstituted C 1 -C 40 alkyl, a substituted or unsubstituted C 1 -C 40 alkoxy, a substituted or unsubstituted C 3 -C 40 cycloalkyl, a substituted or unsubstituted C 6 -C 50 aryl group, a substituted or unsubstituted C 3 -C 50 heteroaryl containing one or two heteroatoms selected from N, O and S, or a substituted or unsubstituted C 10 -C 40 fused aryl grou formed together with the phenyl group linked therewith;
wherein, m, n, p and q each independently represent 0, 1, 2, 3, 4 or 5; and
the substituents are one or more groups selected from the group consisting of a halogen, a C 1 -C 10 alkyl, a C 1 -C 10 alkoxy, a C 3 -C 20 cycloalkyl, a C 6 -C 20 aryl group or a C 4 -C 20 heteroaryl group.

2. The aromatic amine derivative according to claim 1 , wherein,
R 1 , R 2 , R 3 and R 4 each independently represent a substituted or unsubstituted C 1 -C 6 alkyl, a substituted or unsubstituted C 1 -C 6 alkoxy, a substituted or unsubstituted C 3 -C 6 cycloalkyl, a substituted or unsubstituted C 6 -C 18 aryl group, a substituted or unsubstituted C 4 -C 10 heteroaryl containing one or two heteroatoms selected from N, O and S, or a substituted or unsubstituted C 10 -C 18 fused aryl grou formed together with the phenyl group linked therewith;
m, n, p and q each independently represent 0, 1, 2 or 3; and
the substituents are one or more groups selected from the group consisting of a C 1 -C 6 alkyl, a C 1 -C 6 alkoxy or a C 6 -C 18 aryl group.

3. The aromatic amine derivative according to claim 1 , wherein,
[R 1 ] m and [R 2 ] n are identical to [R 3 ] p and [R 4 ] q , respectively; and the substitution positions of [R 1 ] m and [R 2 ] n on the phenyls are identical to those of [R 3 ] p and [R 4 ] q , respectively.

4. The aromatic amine derivative according to claim 1 , wherein, [R 1 ] m ,[R 2 ] n , [R 3 ] p and [R 4 ] q are the same, and the substitution positions of [R 1 ] m , [R 2 ] n , [R 3 ] p and [R 4 ] q on the phenyls are the same.

5. A preparation method of the aromatic amine derivative according to claim 1 , comprising:
adding 5,11-disubstituted thieno[3′,2′:5,6] indolo [3,2-b]thieno [3,2-f] indole (formula II), triarylamine of the formula III and/or IV, a catalyst, a base and a solvent into a reaction vessel and mixing them; and

refluxing the obtained mixture under stirring to produce the aromatic amine derivative of the formula I, wherein,
X and Y independently represent a halogen; and
R 1 , R 2 , R 3 , R 4 , m, n, p and q are defined as in claim 1 .

6. The preparation method according to claim 5 , wherein,
the triarylamine of formula III is identical to the triarylamine of formula IV.

7. The preparation method according to claim 6 , wherein, the molar ratio of 5,11-disubstituted thieno[3′,2′:5,6] indolo [3,2-b]thieno [3,2-f] indole (formula II) to the triarylamine is from 1:2 to 1:4.

8. The preparation method according to claim 5 , wherein the method comprises the following steps when the triarylamine of formula III is different from the triarylamine of formula IV:
adding 5,11-disubstituted thieno[3′,2′:5,6] indolo [3,2-b]thieno [3,2-f] indole (formula II), triarylamine of the formula III or IV, a catalyst, a base and a solvent into a reaction vessel and mixing them;
refluxing the obtained mixture under stirring to produce a one-side substituted intermediate product (formula V);

adding the one-side substituted intermediate product (formula V), triarylamine of the formula IV or III, a catalyst, a base and a solvent into a reaction vessel and mixing them; and
refluxing the obtained mixture under stirring to produce the aromatic amine derivative of the formula I.

9. The preparation method according to claim 8 , wherein,
the molar ratio of 5,11-disubstituted thieno[3′,2′:5,6] indolo [3,2-b]thieno [3,2-f] indole (formula II) to the triarylamine of formula III or IV is from 1:1 to 1:2; and the molar ratio of the one-side substituted intermediate product (formula V) to the triarylamine of formula IV or III is from 1:1 to 1:2.

10. The preparation method according to claim 5 , wherein, the catalyst comprises a phase transfer catalyst.

11. An organic electroluminescent device comprising a cathode, at least one light emitting unit and an anode, wherein said light emitting unit comprises a hole transporting layer comprising the aromatic amine derivative according to claim 1 .

12. The aromatic amine derivative according to claim 2 , wherein,
[R 1 ] m and [R 2 ] n are identical to [R 3 ] p and [R 4 ] q , respectively; and the substitution positions of [R 1 ] m and [R 2 ] n on the phenyls are identical to those of [R 3 ] p and [R 4 ] q , respectively.

13. The aromatic amine derivative according to claim 2 , wherein,
[R 1 ] m , [R 2 ] n , [R 3 ] p and [R 4 ] q are the same, and the substitution positions of [R 1 ] m , [R 2 ] n , [R 3 ] p and [R 4 ] q on the phenyls are the same.

14. The organic electroluminescent device according to claim 11 , wherein in the general formula I,
R 1 , R 2 , R 3 and R 4 each independently represent a substituted or unsubstituted C 1 -C 6 alkyl, a substituted or unsubstituted C 1 -C 6 alkoxy, a substituted or unsubstituted C 3 -C 6 cycloalkyl, a substituted or unsubstituted C 6 -C 18 aryl group, a substituted or unsubstituted C 4 -C 10 heteroaryl containing one or two heteroatoms selected from N, O and S, or a substituted or unsubstituted C 10 -C 18 fused aryl group formed together with the phenyl group linked therewith;
m, n, p and q each independently represent 0, 1, 2 or 3; and
the substituents are one or more groups selected from the group consisting of a C 1 -C 6 alkyl, a C 1 -C 6 alkoxy or a C 6 -C 18 aryl group.

15. The organic electroluminescent device according to claim 11 , wherein in the general formula I,
[R 1 ] m and [R 2 ] n are identical to [R 3 ] p and [R 4 ] q , respectively; and the substitution positions of [R 1 ] m and [R 2 ] n on the phenyls are identical to those of [R 3 ] p and [R 4 ] q , respectively.

16. The organic electroluminescent device according to claim 11 , wherein in the general formula I,
[R 1 ] m , [R 2 ] n , [R 3 ] p and [R 4 ] q are the same, and the substitution positions of [R 1 ] m , [R 2 ] n , [R 3 ] p and [R 4 ] q on the phenyls are the same.

Assignees

• Boe Technology Group Co Ltd

Inventors

• Liu Fei
• Xu Xiaoguang
• Gao Xue

Classifications

• H01L51/0071

  Electricity · mapped topic

• H01L51/0061 Primary

  Electricity · mapped topic

• C07D519/00

  Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00 · CPC title

• H01L51/0072

  Electricity · mapped topic

• H01L51/0054

  Electricity · mapped topic