Dichroic dye, composition thereof, and liquid crystal composition and liquid crystal display element containing the same

• US 6,861,106 B2
• Filed: 05/23/2003
• Issued: 03/01/2005
• Est. Priority Date: 12/27/2002
• Status: Active Grant

• Current Assignee: Industrial Technology Research Institute
• Original Assignee: Industrial Technology Research Institute
• Inventors: Cheng, Kung-Lung, Ma, Jie-Hwa, Lai, Long-Li, Lin, Yang-Chu, Liu, Shih-Hsien, Tzeng, Woan-Shiow
• Primary Examiner(s): WU, SHEAN CHIU
• Application Number:
  US10/443,808
• Publication Number:
  US 20040135117A1
• Time in Patent Office: 648 Days
• Field of Search: 428/1.1, 252/299.1, 252/299.68, 534/688, 534/689, 544/392, 544/402, 548/128, 548/129, 548/130, 552/243
• US Class Current: 428/1.1
• CPC Class Codes: C07D 285/135 Nitrogen atoms
• CPC Class Codes: C07D 295/185 from aliphatic carboxylic acids
• CPC Class Codes: C09B 1/503 unsubstituted amino-hydroxy anthraquinone
• CPC Class Codes: C09B 29/083 having -N< (in a ring)
• CPC Class Codes: C09B 31/043 Amino-benzenes
• CPC Class Codes: C09B 43/006 by introduction of hydrocarbon radicals on C-atom of azo dye
• CPC Class Codes: C09K 19/601 Azoic
• CPC Class Codes: C09K 19/603 Anthroquinonic
• CPC Class Codes: C09K 2323/00 Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition

Abstract

Dichroic dyes, dichroic dye compositions, and liquid crystal composition and liquid crystal display element containing the dichroic dyes. The dichroic dye has increased solubility and stability.

Claims

1. A compound having formula (I):

wherein

A is

B is —

CHC(CN)COOR⁴ and X and Y are both hydrogen when A is

wherein R¹, and R⁴ are each independently a C_1-10 alkyl group which may be substituted by one or more fluorine atoms; and

B is —

NR⁶R⁷ and X and Y are different and X is a C_1-4 alkyl group, and Y is Cl, Br, I, a C_1-4 alkyl group, —

OCH₃, or —

OC₂H₅ or X and Y, being the same, are H, Cl, Br, I, a C_1-4 alkyl group, —

OCH₃, or —

OC₂H₅ when A is

wherein R⁵ is —

CH₃ or —

C₂H₅, and R⁶ and R⁷ are each independently a C_1-10 alkyl group, —

CH₂CH₂(CF₂)_mF,

wherein m is an integer of 1 to 10 and R³ is an C_1-4 alkyl group.

17. A dichroic dye liquid crystal composition, which includes liquid crystal compounds and the compound as claimed in claim 1 or 12.

18. The dichroic dye liquid crystal composition as claimed in claim 17, wherein the liquid crystal is selected from the group consisting of nematic liquid crystal, smetic liquid crystal, and cholesteric liquid crystal.

19. A liquid crystal display element, which includes the compound as claimed in claim 1 or 12.

20. The liquid crystal display element as claimed in claim 19, wherein the driver module used in the liquid crystal display element is active.

21. The liquid crystal display element as claimed in claim 19, wherein the drive module used in the liquid crystal display element is passive.

22. The liquid crystal display element as claimed in claim 19, wherein the liquid crystal display element is transmissive.

23. The liquid crystal display element as claimed in claim 19, wherein the liquid crystal display element is trans-flective.

24. The liquid crystal display element as claimed in claim 19, wherein the liquid crystal display element is reflective.

2. A compound having formula (III):

wherein R¹ and R⁴ are each independently a C_1-10 alkyl group which may be substituted by one or more fluorine atoms.

3. The compound as claimed in claim 2, wherein R¹ is a C_2-8 alkyl group which may be substituted by one or more fluorine atoms.

4. The compound as claimed in claim 2, wherein R⁴ is a C_2-8 alkyl group which may be substituted by one or more fluorine atoms.

5. The compound as claimed in claim 2, wherein R¹ is —

C₅H₁₁ and R⁴ is —

C₄H₉.

6. A compound having formula (IV):

wherein

X and Y are different and X is a C_1-4 alkyl group, and Y is Cl, Br, I, a C_1-4 alkyl group, —

OCH₃, or —

OC₂H₅, or X and Y, being the same, are Cl, Br, I, a C_1-4 alkyl group, —

OCH₃, or —

OC₂H₅;

R⁵ is —

CH₃ or —

C₂H₅; and

R⁶ and R⁷ are each independently a C_1-10 alkyl group, —

CH₂CH₂(CF₂)_mF,

wherein m is an integer of 1 to 10 and R³ is a C_1-4 alkyl group.

7. The compound as claimed in claim 6, wherein X is a C_1-4 alkyl group.

8. The compound as claimed in claim 6, wherein Y is a C_1-4 alkyl group.

9. The compound as claimed in claim 6, wherein R⁶ is a C_1-2 alkyl group.

10. The compound as claimed in claim 6, wherein R⁷ is a C_1-10 alkyl group.

11. The compound as claimed in claim 6, wherein X is methyl, Y is methyl, R⁶ is methyl, and R⁷ is —

C₈H₁₇.

12. A compound having formula (V):

wherein OR⁹ is OC₄H₈F,

or

wherein n is an integer of 1 to 10.

13. The compound as claimed in claim 12, wherein OR⁹ is OC₄H₈F or

wherein n is an integer of 1 to 6.

14. The compound as claimed in claim 13, wherein OR⁹ is OC₄H₈F.

15. A composition of dichroic dyes, which includes a compound selected from the group consisting of a compound having formula (I):

wherein

A is

B is —

CHC(CN)COOR⁴ and X and Y are both hydrogen when A is

wherein R¹, and R⁴ are each independently a C_1-10 alkyl group which may be substituted by one or more fluoride atoms; and

B is —

NR⁶R⁷ and X and Y are different and X is a C_1-4 alkyl group, and Y is Cl, Br, I, a C_1-4 alkyl group, —

OCH₃, or —

OC₂H₅ or X and Y, being the same, are H, Cl, Br, I, a C_1-4 alkyl group, —

OCH₃, or —

OC₂H₅ when A is

wherein R⁵ is —

CH₃ or —

C₂H₅, and R⁶ and R⁷ are each independently a C_1-10 alkyl group, —

CH₂CH₂(CF₂)_mF,

wherein m is an integer of 1 to 10 and R³ is an C_1-4 alkyl group;

and a compound having formula (V);

wherein OR⁹ is OC₄H₈F,

or

wherein n is an integer of 1 to 10.

16. The composition as claimed in claim 15, which is a black dichroic composition.