Polymerizable liquid crystal composition and polymer thereof

1. A polymerizable liquid crystal composition comprising at least one compound selected from the group of compounds represented by the formula (1-1) and the formula (1-2) as a first ingredient, at least one compound selected from the group of compounds represented by the formula (2-1) and the formula (2-2) as a second ingredient, and at least one compound selected from the group of compounds represented by the formula (3-1) as a third ingredient,

in which Y 1 and Y 2 each represents independently a single bond, —(CH 2 ) 2 — or —CH═CH—, W 1 and W 2 each represents independently hydrogen or fluorine, m 1 , m 2 , n 1 , and n 2 each represents independently an integer of from 2 to 15 in the formula (1-1) and the formula (1-2); W 3 represents hydrogen or fluorine, W 4 and W 5 each represents independently hydrogen or methyl, W 6 represents hydrogen or methyl, X 1 is a group represented by —O— or the following formula (X 1 -2),

and m 3 , m 4 , n 3 , and n 4 each represents independently an integer of from 2 to 15 in the formula (2-1) and the formula (2-2); and R 1 represents cyano, trifluoromethoxy, alkyl of 1 to 10 carbon atoms, or alkoxy of 1 to 10 carbon atoms, W 7 represents hydrogen or fluorine, X 2 represents a single bond, —COO—, or —OCO—, and m 5 represents an integer of from 2 to 15 in the formula (3-1).

2. The polymerizable liquid crystal composition according to claim 1 , wherein the second ingredient is at least one compound selected from the group of compounds represented by the formula (2-1), the ratio of the first ingredient is within a range from approximately 1% to approximately 25% by weight, the ratio of the second ingredient is within a range from approximately 50% to approximately 98% by weight, and the ratio of the third ingredient is within a range from approximately 1% to approximately 25% by weight based on the polymerizable liquid crystal composition; Y 1 and Y 2 each represents independently a single bond or —(CH 2 ) 2 —, W 1 and W 2 each represents independently hydrogen or fluoride, and m 1 , m 2 , n 1 , and n 2 each represents independently an integer of from 2 to 10 in the formula (1-1) and the formula (1-2); W 3 represents hydrogen, W 4 represents hydrogen, W 5 represents methyl, and m 3 and n 3 each represents independently an integer of from 2 to 10 in the general formula (2-1); and X 2 represents a single bond, —COO—, or —OCO—, W 7 represents hydrogen, m 5 represents an integer of from 2 to 10, and R 1 represents cyano, alkyl of 2 to 8 carbon atoms, or alkoxy of 2 to 8 carbon atoms in the formula (3-1).

3. The polymerizable liquid crystal composition according to claim 2 , wherein the ratio of the first ingredient is within a range from approximately 7% to approximately 22% by weight, the ratio of the second ingredient is within a range from approximately 56% to approximately 86% by weight, and the ratio of the third ingredient is within the range from approximately 7% to approximately 22% by weight based on the polymerizable liquid crystal composition; Y 1 and Y 2 each represents independently a single bond or —(CH 2 ) 2 —, W 1 and W 2 each represents hydrogen, and m 1 , m 2 , n 1 , and n 2 each represents independently an integer of from 4 to 6 in the formula (1-1) and the formula (1-2); W 3 represents hydrogen, W 4 represents hydrogen, W 5 represents methyl, and m 3 and n 3 each represents independently an integer of from 4 to 6 in the general formula (2-1); and X 2 represents a single bond, W 7 represents hydrogen, m 5 represents an integer of from 4 to 6, and R 1 represents cyano in the formula (3-1).

4. The polymerizable liquid crystal composition according to claim 1 , wherein the second ingredient is at least one compound selected from the group of compounds represented by the formula (2-2), the ratio ofthe first ingredient is within a range from approximately 1% to approximately 25% by weight, the ratio of the second ingredient is within a range from approximately 50% to approximately 98% by weight, and the ratio of the third ingredient is within a range from approximately 1% to approximately 25% by weight based on the polymerizable liquid crystal composition; Y 1 and Y 2 each represents independently a single bond or —(CH 2 ) 2 —, W 1 and W 2 each represents independently hydrogen or fluoride, and m 1 , m 2 , n 1 , and n 2 each represents independently an integer of from 2 to 10 in the formula (1-1) and the formula (1-2); X 1 is a group represented by —O— or the following formula (X 1 -2),

W 6 represents hydrogen or methyl, m 4 and n 4 each represents independently an integer of from 2 to 10 in the formula (2-2); and X 2 represents a single bond, —COO—, or —OCO—, W 7 represents hydrogen, m 5 represents an integer of from 2 to 10, and R 1 represents cyano, alkyl of 2 to 8 carbon atoms, or alkoxy of 2 to 8 carbon atoms in the formula (3-1).

5. The polymerizable liquid crystal composition according to claim 4 , wherein the ratio of the first ingredient is within a range from approximately 7% to approximately 22% by weight, the ratio of the second ingredient is within a range from approximately 56% to approximately 86% by weight, and the ratio of the third ingredient is within the range from approximately 7% to approximately 22% by weight based on the polymerizable liquid crystal composition; Y 1 and Y 2 each represents independently a single bond or —(CH 2 ) 2 —, W 1 and W 2 each represents hydrogen, and m 1 , m 2 , n 1 , and n 2 each represents independently an integer of from 4 to 6 in the formula (1-1) and the formula (1-2); W 6 represents methyl, X 1 represents —O—, and m 4 and n 4 each represents independently an integer of from 4 to 6 in the general formula (2-2); and X 2 represents a single bond, W 7 represents hydrogen, m 5 represents an integer of from 4 to 6, and R 1 represents cyano in the formula (3-1).

6. The polymerizable liquid crystal composition according to claim 1 , further comprising a silane coupling agent represented by the following formula (4),

wherein the ratio of the polymerizable liquid crystal composition to the silane coupling agent is within a range from approximately 100:1 to approximately 100:10 by weight ratio in which R 4 represents methyl or ethyl, and n 8 represents an integer of from 1 to 5 in the formula (4).

7. The polymerizable liquid crystal composition according to claim 2 , further comprising a silane coupling agent represented by the following formula (4),

wherein the ratio of the polymerizable liquid crystal composition to the silane coupling agent is within a range from approximately 100:1 to approximately 100:10 by weight ratio in which R 4 represents methyl or ethyl, and n 8 represents an integer of from 1 to 5 in the formula (4).

8. The polymerizable liquid crystal composition according to claim 3 , further comprising a silane coupling agent represented by the following formula (4),

wherein the ratio of the polymerizable liquid crystal composition to the silane coupling agent is within a range from approximately 100:1 to approximately 100:10 by weight ratio in which R 4 represents methyl or ethyl, and n 8 represents an integer of from 1 to 5 in the formula (4).

9. The polymerizable liquid crystal composition according to claim 4 , further comprising a silane coupling agent represented by the following formula (4),

wherein the ratio of the polymerizable liquid crystal composition to the silane coupling agent is within a range from approximately 100:1 to approximately 100:10 by weight ratio in which R 4 represents methyl or ethyl, and n 8 represents an integer of from 1 to 5 in the formula (4).

10. The polymerizable liquid crystal composition according to claim 5 , further comprising a silane coupling agent represented by the following formula (4),

wherein the ratio of the polymerizable liquid crystal composition to the silane coupling agent is within a range from approximately 100:1 to approximately 100:10 by weight ratio in which R 4 represents methyl or ethyl, and n 8 represents an integer of from 1 to 5 in the formula (4).

11. A polymerizable liquid crystal composition comprising at least one compound selected from the group of compounds represented by the formula (5-1) and the formula (5-2) as a first ingredient, at least one compound selected from the group of compounds represented by the formula (6-1) and the formula (6-2) as a second ingredient, and at least one compound selected from the group of compounds represented by the formula (7-1) as a third ingredient, in which R 2 and R 3 each represents independently methyl or ethyl, Y 3 and Y 4 each represents independently a single bond, —(CH 2 ) 2 — or —CH═CH—, W 8 and W 9 each represents independently hydrogen or fluorine, Q 1 and Q 2 each represents a single bond, —O—(CH 2 ) r 1 —, or —(CH 2 ) r 1 —O—, r 1 represents an integer of from 1 to 15 in the formula (5-1) and the formula (5-2); W 10 and W 11 each represents independently hydrogen or methyl, m 6 , m 7 , n 6 , and n 7 each represents independently an integer of from 2 to 15 in the formula (6-1) and the formula (6-2); X 3 represents a single bond, —COO—, or —OCO—, R 5 represents cyano, alkyl of 2 to 8 carbon atoms, or alkoxy of 2 to 8 carbon atoms, and m 8 represents an integer of from 2 to 15 in the formula (7-1).

12. The polymerizable liquid crystal composition according to claim 11 , wherein the first ingredient is at least one compound selected from the group of compounds represented by the general formula (5-1), and the second ingredient is at least one compound selected from the group of compounds represented by the general formula (6-1), the ratio of the first ingredient is within a range from approximately 1% to approximately 20% by weight, the ratio of the second ingredient is within a range from approximately 60% to approximately 98% by weight, and the ratio of the third ingredient is within a range from approximately 1% to approximately 20% by weight based on the polymerizable liquid crystal composition; R 2 represents methyl or ethyl, Y 3 represents a single bond or —(CH 2 ) 2 —, W 8 represents hydrogen or fluorine, Q 1 represents a single bond, —O—(CH 2 )r 1 -, or —(CH 2 )r 1 -O—, r 1 represents an integer of from 1 to 10 in the formula (5-1); W 10 and W 11 each represents independently hydrogen or methyl, m 6 , and n 6 each represents independently an integer of from 2 to 10 in the formula (6-1); and X 3 represents a single bond, R 5 represents cyano, and m 8 is an integer of from 2 to 10 in the formula (7-1).

13. The polymerizable liquid crystal composition according to claim 12 , wherein the ratio of the first ingredient is within a range from approximately 7% to approximately 20% by weight, the ratio of the second ingredient is within a range from approximately 60% to approximately 86% by weight, and the ratio of the third ingredient is within a range from approximately 7% to approximately 20% by weight based on the polymerizable liquid crystal composition; R 2 represents ethyl, Y 3 represents a single bond, W 8 represents hydrogen, and Q 1 represents a single bond in the formula (5-1); W 10 and W 11 each represents independently hydrogen or methyl, m 6 and n 6 each represents independently an integer of from 4 to 6 in the formula (6-1); and X 3 represents a single bond, R 5 represents cyano, and m 8 represents an integer of from 2 to 4 in the formula (7-1).

14. A polymer obtained by polymerizing the polymerizable liquid crystal composition according to claim 1 .

15. A polymer obtained by polymerizing the polymerizable liquid crystal composition according to claim 11 .

16. The polymer of claim 14 , wherein said polymer is a polymer film.

17. The polymer of claim 15 , wherein said polymer is a polymer film.

18. A phase difference plate comprising the polymer film of claim 16 .

19. A phase difference plate comprising the polymer film of claim 17 .

20. A liquid crystal display device comprising the polymer film of claim 16 .

21. A liquid crystal display device comprising the polymer film of claim 17 .

22. A compound represented by the formula (7):

in which Y 5 represents —CH 2 CH 2 — (—CH 2) 2 — , or —CH═CH—, and m 8 and n 8 each represents independently an integer of from 2 to 15 in the formula (7).

23. A compound represented by the formula (8):

in which m 9 and n 9 each represents independently an integer of from 2 to 15 in the formula (8).

24. A compound represented by the formula (9):

in which Y 6 represents —CH 2 CH 2 —, or —CH═CH—, and m 10 and n 10 each represents independently an integer of from 2 to 15 in the formula (9).

25. A compound represented by the formula (10):

in which R 7 represents hydrogen, methyl, or ethyl, A 4 represents 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, naphthalene-2,6-diyl or pyridine-2,5-diyl, Y 7 represents a single bond, —CH 2 CH 2 — (—CH 2) 2 — , or —CH═CH—, Q 3 represents a single bond, —O—(CH 2 )r 2 - or —(CH 2 )r 2 -O—, and r 2 represents an integer of from 1 to 15 in the formula (10).

26. The compound according to claim 25 , wherein R 7 represents methyl or ethyl, A 4 represents 1,4-phenylene, Y 7 represents a single bond, and Q 3 represents a single bond in the formula (10).

27. A compound represented by the formula (11):

in which R 8 represents hydrogen, methyl, or ethyl, A 5 represents 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, naphthalene-2,6-diyl or pyridine-2,5-diyl, Y 8 represents a single bond, —CH 2 CH 2 — (—CH 2) 2 — , or —CH═CH—, Q 4 represents a single bond, —O—(CH 2 )r 3 - or —(CH 2 )r 3 -O—, and r 3 represents an integer of from 1 to 15 in the formula (11).

28. The compound according to claim 27 , wherein R 8 represents ethyl, A 5 represents 1,4-phenylene, Y 8 represents a single bond, and Q 4 represents a single bond in the formula (11).

29. The compound according to claim 27 , wherein R 8 represents methyl, or ethyl, A 5 represents 1,4-phenylene, Y 8 represents a single bond, Q 4 represents —O—(CH 2 )r 3 - or —(CH 2 )r 3 -O—, and r 3 represents an integer of from 1 to 10 in the formula (11).

30. A compound represented by the formula ( 8 ):

in which W 1 represents independently hydrogen or fluorine, m 9 and n 9 each represents independently an integer of from 2 to 15 in the formula ( 8 ).

31. A compound represented by the formula ( 9 ):

in which Y 6 represents a single bond, — (CH 2 ) 2 —, or —CH═CH—, W 2 represents independently hydrogen or fluorine, and m 10 and n 10 each represents independently an integer of from 2 to 15 , in the case where W 2 is hydrogen, Y 6 represents independently — ( CH 2 ) 2 — or —CH═CH— in the formula ( 9 ).EP

32. A compound represented by the formula ( 1 - 1 ):

in which Y 1 represents independently a single bond, — (CH 2 ) 2 —, or —CH═CH—, W 1 represents independently hydrogen or fluorine, m 1 and n 1 each represents independently an integer of from 2 to 15 in the formula ( 1 - 1 ).