Trifunctional compound, composition and polymer thereof

• US 20080081133A1
• Filed: 09/21/2007
• Published: 04/03/2008
• Est. Priority Date: 09/21/2006
• Status: Active Grant

• Current Assignee: JNC Petrochemical Corporation (Chisso Corporation)
• Original Assignee: Chisso Corporation, Chisso Petrochemical Corporation
• Inventors: Kato, Takashi
• Granted Patent: US 7,927,671 B2
• Time in Patent Office: Days
• US Class Current: 428/1.1
• CPC Class Codes: C08F 222/1035 of aromatic trialcohols
• CPC Class Codes: C08F 26/06 by a heterocyclic ring containing nitrogen
• CPC Class Codes: C08G 59/3218 Carbocyclic compounds
• CPC Class Codes: C08G 59/38 together with di-epoxy compounds
• CPC Class Codes: C08L 63/00 Compositions of epoxy resins; Compositions of derivatives of epoxy resins
• CPC Class Codes: C09K 19/2007 the chain containing -COO- or -OCO- groups
• CPC Class Codes: C09K 19/32 containing condensed ring systems, i.e. fused, bridged or spiro ring systems
• CPC Class Codes: C09K 19/3411 the heterocyclic ring being a three-membered ring
• CPC Class Codes: C09K 19/3483 the heterocyclic ring being a non-aromatic ring
• CPC Class Codes: C09K 2019/0448 the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
• CPC Class Codes: C09K 2019/0481 Phenylene substituted in meta position
• CPC Class Codes: C09K 2019/0485 Phenylene substituted in ortho position
• CPC Class Codes: C09K 2019/3416 the heterocyclic ring being a four-membered ring, e.g. oxetane
• CPC Class Codes: C09K 2323/00 Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition

Abstract

The invention includes compounds represented by Formula (1):
wherein R^a is a polymerizable group such as (meth)acryloyloxy, an oxirane ring, an oxetane ring or the like; A is 1,4-cyclohexylene, 1,4-phenylene or the like; Z is a single bond, alkylene having 1 to 20 carbon atoms or the like; Y is a single bond, alkylene having 1 to 20 carbon atoms or the like; and m and n are an integer of 0 to 5.

Claims

1. A compound represented by Formula (1):

2. The compound of claim 1, wherein in Formula (1), m+n is an integer of 1, 2 or 3.

3. The compound of claim 1, wherein in Formula (1), m+n is 2.

4. The compound of claim 1, wherein in Formula (1), R^a is independently a group represented by Formula (2-4), (2-5) or (2-6).

5. The compound of claim 1, wherein in Formula (1), A is independently 1,4-cyclohexylene, 1,4-phenylene, pyridine-2,5-diyl, pyridazine-3,6-diyl or pyrimidine-2,5-diyl, and optional hydrogens in these rings may be replaced by Cl, F, alkyl having 1 to 3 carbon atoms or fluoroalkyl having 1 to 3 carbon atoms.

6. The compound of claim 1, wherein in Formula (1), Z is independently a single bond, —

CH₂O—

, —

OCH₂—

, —

COO—

, —

OCO—

, —

CH═

CH—

, —

(CH₂)₂COO—

, —

OCO(CH₂)₂—

, —

CH═

CH—

COO—

, —

OCO—

CH═

CH—

or —

C≡

C—

.

7. The compound of claim 1, wherein in Formula (1), Y is independently alkylene having 1 to 10 carbon atoms, and optional —

CH₂—

in the alkylene may be replaced by —

O—

, —

COO—

, —

OCO—

or —

OCOO—

.

16. A composition comprising at least one compound as described in claim 1.

18. A composition comprising at least one compound of claim 1 and at least one compound selected from the group of compounds represented by Formulas (M1), (M2), (M3) and (M4):

19. The composition of claim 18, wherein in Formula (1), R^a is independently a group represented by Formula (2-4), (2-5) or (2-6);

A is independently 1,4-cyclohexylene, 1,4-phenylene, pyridine-2,5-diyl, pyridazine-3,6-diyl or pyrimidine-2,5-diyl, and optional hydrogens in these rings may be replaced by Cl, F;

alkyl having 1 to 3 carbon atoms or fluoroalkyl having 1 to 3 carbon atoms;

Z is independently a single bond, —

CH₂O—

, —

OCH₂—

, —

COO—

, —

OCO—

, —

CH═

CH—

, —

(CH₂)₂COO—

, —

OCO(CH₂)₂—

, —

CH═

CH—

COO—

, —

OCO—

CH═

CH—

or —

C≡

C—

;

Y is independently a single bond or alkylene having 1 to 10 carbon atoms, and optional —

CH₂—

in the alkylene may be replaced by —

O—

, —

COO—

, —

OCO—

or —

OCOO—

;

m=n=1;

in Formulas (M1), (M2), (M3) and (M4), R¹ is independently a group represented by Formula (2-4), (2-5) or (2-6);

R² is alkyl having 1 to 5 carbon atoms, alkoxy having 1 to 5 carbon atoms, Cl, F, CN, CF₃ or OCF₃;

A¹ is independently 1,4-cyclohexylene, 1,4-phenylene, monofluoro-1,4-phenylene or difluoro-1,4-phenylene;

Z¹ is independently a single bond, —

CH₂O—

, —

OCH₂—

, —

COO—

, —

OCO—

, —

C≡

C—

, —

CH═

CHCOO—

, —

CH═

CHOCO—

, —

(CH₂)₂COO—

or —

(CH₂)₂OCO—

;

Y¹ is independently a single bond or alkylene having 1 to 10 carbon atoms, and in the alkylene, optional —

CH₂—

may be replaced by —

O—

, —

COO—

, —

OCO—

or —

OCOO—

;

L¹ is independently H, F or CH₃;

L² is independently H, Cl, F, CH₃ or CF₃;

p is an integer of 1 or 2;

the proportion of the compound represented by Formula (1) is approximately 5% to approximately 80% by weight, and the proportion of the compounds represented by Formulas (M1), (M2), (M3) and (M4) is approximately 20% to approximately 95% by weight each based on the total amount of the compound represented by Formula (1) and the compounds represented by Formulas (M1), (M2), (M3) and (M4).

20. The composition of claim 18, wherein in Formula (1), R^a is independently a group represented by Formula (2-4), (2-5) or (2-6);

A is independently 1,4-cyclohexylene or 1,4-phenylene, and optional hydrogens in these rings may be replaced by Cl, F, CH₃ or CF₃;

Z is independently a single bond, —

COO—

or —

OCO—

;

Y is independently alkylene having 1 to 10 carbon atoms, and in the alkylene, —

CH₂-adjacent to the ring may be replaced by —

O—

, —

COO—

, —

OCO—

or —

OCOO—

;

m=n=1;

in Formulas (M1), (M2), (M3) and (M4), R¹ is independently a group represented by Formula (2-4), (2-5) or (2-6);

R² is alkyl having 1 to 5 carbon atoms, alkoxy having 1 to 5 carbon atoms, CN, F or OCF₃;

A¹ is independently 1,4-cyclohexylene, 1,4-phenylene, monofluoro-1,4-phenylene or difluoro-1,4-phenylene;

Z¹ is independently a single bond, —

COO—

, —

OCO—

, —

CH═

CHCOO—

, —

CH═

CHOCO—

, —

(CH₂)₂COO—

or —

(CH₂)₂OCO—

;

Y¹ is independently a single bond or alkylene having 1 to 10 carbon atoms, and in the alkylene, —

CH₂—

adjacent to the ring may be replaced by —

O—

, —

COO—

, —

OCO—

or —

OCOO—

;

L¹ is independently H or CH₃;

L² is independently H, F, CH₃ or CF₃;

p is 2;

the proportion of the compound represented by Formula (1) is approximately 5% to approximately 60% by weight, and the proportion of the compounds represented by Formulas (M1), (M2), (M3) and (M4) is approximately 40% to approximately 95% by weight each based on the total amount of the compound represented by Formula (1) and the compounds represented by Formulas (M1), (M2), (M3) and (M4).

21. The composition of claim 16, further comprising at least one additional polymerizable compound.

23. The composition of claim 21, wherein the at least one additional polymerizable compound is actively active.

25. The composition of claim 16, further comprising at least one non-polymerizable liquid crystalline compound.

27. The composition of claim 16, further comprising at least one non-polymerizable optically active compound.

29. A polymer comprising a constitutional unit derived from a compound of claim 1.

31. A polymer obtained by polymerizing the composition of claim 16.

34. The polymer of claim 31, wherein said polymer is optically active.

35. A film comprising the polymer of claims 29.

37. A molded article having an optical anisotropy, comprising the polymer of claim 29.

39. A liquid crystal display element comprising the film of claim 35.

41. A liquid crystal display element comprising the molded article having an optical anisotropy of claim 37.

43. A liquid crystal display element comprising the composition of claim 16.

8. A compound represented by Formula (I) or (II):

9. The compound of claim 8, wherein in Formulas (I) and (II), R^a, R^a1 and R^a2 are each independently a group represented by Formula (2-4), (2-5) or (2-6).

10. The compound of claim 8, wherein in Formulas (I) and (II), A is independently 1,4-cyclohexylene, 1,4-phenylene, pyridine-2,5-diyl, pyridazine-3,6-diyl or pyrimidine-2,5-diyl, and optional hydrogens in these rings may be replaced by Cl, F, alkyl having 1 to 3 carbon atoms or fluoroalkyl having 1 to 3 carbon atoms.

11. The compound of claim 8, wherein in Formulas (I) and (II), Z is independently a single bond, —

CH₂O—

, —

OCH₂—

, —

COO—

, —

OCO—

, —

CH═

CH—

, —

(CH₂)₂COO—

, —

OCO(CH₂)₂—

, —

CH═

CH—

COO—

, —

OCO—

CH═

CH—

or —

C≡

C—

.

12. The compound of claim 8, wherein in Formulas (I) and (II), Y is independently a single bond or alkylene having 1 to 10 carbon atoms, and optional —

CH₂—

in the alkylene may be replaced by —

O—

, —

COO—

, —

OCO—

or —

OCOO—

.

13. The compound of claim 8, wherein in Formulas (I) and (II), A is independently 1,4-cyclo hexylene or 1,4-phenylene, and optional hydrogens in these rings may be replaced by Cl, F, CH₃ or CF₃.

14. The compound of claim 8, wherein in Formulas (I) and (II), Z is independently a single bond, —

COO—

or —

OCO—

.

15. The compound of claim 8, wherein in Formulas (I) and (II), Y is independently alkylene having 1 to 10 carbon atoms, and —

CH₂—

adjacent to the ring in the alkylene may be replaced by —

O—

, —

COO—

, —

OCO—

or —

OCOO—

.

17. A composition comprising at least one compound as described in claim 8.

22. The composition of claim 17, further comprising at least one additional polymerizable compound.

24. The composition of claim 22, wherein the at least one additional polymerizable compound is actively active.

26. The composition of claim 17, further comprising at least one non-polymerizable liquid crystalline compound.

28. The composition of claim 17, further comprising at least one non-polymerizable optically active compound.

30. A polymer comprising a constitutional unit derived from a compound of claim 8.

32. A polymer obtained by polymerizing the composition of claim 17.

33. The polymer of claim 30, wherein said polymer is optically active.

36. A film comprising the polymer of claims 30.

38. A molded article having an optical anisotropy, comprising the polymer of claim 30.

40. A liquid crystal display element comprising the film of claim 36.

42. A liquid crystal display element comprising the molded article having an optical anisotropy of claim 38.

44. A liquid crystal display element comprising the composition of claim 17.