Liquid crystal composition and liquid crystal element
View Patent ↗The invention provides an optically isotropic liquid crystal composition having: a liquid crystal component comprising a liquid crystal component A consisting of one or more compounds selected from the group consisting of compounds having difluoroalkenyl and compounds having alkenyl; and chiral dopants, wherein in the liquid crystal component, the content of compounds having 3 or more ring structures is approximately 15 wt % or more.
1. An optically isotropic liquid crystal composition having a liquid crystal component comprising a liquid crystal component A consisting of one or more compounds represented by general formula (1-1) or (1-2) and chiral dopants, wherein in the liquid crystal component, the content of compounds having 3 to 5 ring structures is approximately 15 wt % or more,
and wherein in formulae (1-1) and (1-2):
R 1 is alkenyl having 2 to 20 carbon atoms, wherein any —CH 2 — in the alkenyl can be replaced by —O—, —S—, —COO—, —OCO—, —CH═CH— or —C≡C—; and any hydrogen in the alkenyl can be replaced by halogen;
Ring A 1 , Ring A 2 , Ring A 3 and Ring A 4 are each independently a benzene ring, a naphthalene ring, a cyclohexene ring, a bicyclooctane ring or a cyclohexane ring, wherein any hydrogen in these rings can be replaced by halogen; any —CH 2 — in the rings can be replaced by —O— or —S—; and any —CH═ in the rings can be replaced by —N═;
Z 0 is a single bond or alkylene having 1 to 20 carbon atoms, wherein any —CH 2 — in the alkylene can be replaced by —O—, —S—, —COO—, —OCO—, —CSO—, —OCS—, —CH═CH—, —CF═CF— or —C≡C—; and any hydrogen can be replaced by halogen;
Z 1 , Z 2 , Z 3 and Z 4 are each independently a single bond or alkylene having 1 to 4 carbon atoms, wherein any —CH 2 — in the alkylene can be replaced by —O—, —S—, —COO—, —OCO—, —CSO—, —OCS—, —CH═CH—, —CF═CF— or —C≡C—; and any hydrogen can be replaced by halogen;
L 1 and L 2 are each independently hydrogen or halogen;
X 1 is halogen, —C≡N, —N═C═S, —C≡C—C≡N, —SF 5 , —CHF 2 , —CF 3 , —CF 2 CH 2 F, —CF 2 CHF 2 , —CF 2 CF 3 , —(CF 2 ) 3 —F, —CF 2 CHFCF 3 , —CHFCF 2 CF 3 , —(CF 2 ) 4 —F, —(CF 2 ) 5 —F, —OCHF 2 , —OCF 3 , —OCF 2 CH 2 F, —OCF 2 CHF 2 , —OCH 2 CF 3 , —OCF 2 CF 3 , —O—(CF 2 ) 3 —F, —OCF 2 CHFCF 3 , —OCHFCF 2 CF 3 , —O—(CF 2 ) 4 —F, —O—(CF 2 ) 5 —F, —CH═CF 2 , —CH═CHCF 3 or —CH═CHCF 2 CF 3 ; and
l, m, n and o are each independently 0 or 1; and
l+m+n+o≧1;
wherein the liquid crystal component does not contain a liquid crystal component D consisting of at least one compound selected from the group consisting of compounds represented by general formulae (7) to (9),
and wherein in the formulae:
R 4 and R 5 are each independently alkyl having 1 to 10 carbon atoms or alkenyl having 2 to 10 carbon atoms, wherein any —CH 2 — in the alkyl and the alkenyl can be replaced by —O—;
Ring D 1 , Ring D 2 and Ring D 3 are each independently 1,4-cyclohexylene, pyrimidine-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene or 2,5-difluoro-1,4-phenylene;
Z 9 and Z 10 are each independently —C≡C—, —COO—, —(CH 2 ) 2 —, —CH═CH— or a single bond; and
wherein the liquid crystal component has a value of Δn×Δε≧3.39, when there is no chiral dopant.
2. An optically isotropic liquid crystal composition having a liquid crystal component comprising a liquid crystal component A consisting of one or more compounds represented by general formula (1-1) or (1-2) and chiral dopants, wherein in the liquid crystal component, the content of the liquid crystal component A is approximately 15 wt % or more in the liquid crystal component,
and wherein in formulae (1-1) and (1-2):
R 1 is alkenyl having 2 to 20 carbon atoms, wherein any —CH 2 — in the alkenyl can be replaced by —O—, —S—, —COO—, —OCO—, —CH═CH— or —C≡C—; and any hydrogen in the alkenyl can be replaced by halogen;
Ring A 1 , Ring A 2 , Ring A 3 and Ring A 4 are each independently a benzene ring, a naphthalene ring, a cyclohexene ring, a bicyclooctane ring or a cyclohexane ring, wherein any hydrogen in these rings can be replaced by halogen; any —CH 2 — in the rings can be replaced by —O— or —S—; and any —CH═ in the rings can be replaced by —N═;
Z 0 is a single bond or alkylene having 1 to 20 carbon atoms, wherein any —CH 2 — in the alkylene can be replaced by —O—, —S—, —COO—, —OCO—, —CSO—, —OCS—, —CH═CH—, —CF═CF— or —C≡C—; and any hydrogen can be replaced by halogen;
Z 1 , Z 2 , Z 3 and Z 4 are each independently a single bond or alkylene having 1 to 4 carbon atoms, wherein any —CH 2 — in the alkylene can be replaced by —O—, —S—, —COO—, —OCO—, —CSO—, —OCS—, —CH═CH—, —CF═CF— or —C≡C—; and any hydrogen can be replaced by halogen;
L 1 and L 2 are each independently hydrogen or halogen;
X 1 is halogen, —C≡N, —N═C═S, —C≡C—C≡N, —SF 5 , —CHF 2 , —CF 3 , —CF 2 CH 2 F, —CF 2 CHF 2 , —CF 2 CF 3 , —(CF 2 ) 3 —F, —CF 2 CHFCF 3 , —CHFCF 2 CF 3 , —(CF 2 ) 4 —F, —(CF 2 ) 5 —F, —OCHF 2 , —OCF 3 , —OCF 2 CH 2 F, —OCF 2 CHF 2 , —OCH 2 CF 3 , —OCF 2 CF 3 , —O—(CF 2 ) 3 —F, —OCF 2 CHFCF 3 , —OCHFCF 2 CF 3 , —O—(CF 2 ) 4 —F, —O—(CF 2 ) 5 —F, —CH═CF 2 , —CH═CHCF 3 or —CH═CHCF 2 CF 3 ;
l, m, n and o are each independently 0 or 1; and
l+m+n+o≧2,
wherein the liquid crystal component does not contain a liquid crystal component D consisting of at least one compound selected from the group consisting of compounds represented by general formulae (7) to (9),
and wherein in the formulae:
R 4 and R 5 are each independently alkyl having 1 to 10 carbon atoms or alkenyl having 2 to 10 carbon atoms, wherein any —CH 2 — in the alkyl and the alkenyl can be replaced by —O—;
Ring D 1 , Ring D 2 and Ring D 3 are each independently 1,4-cyclohexylene, pyrimidine-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene or 2,5-difluoro-1,4-phenylene;
Z 9 and Z 10 are each independently —C≡C—, —COO—, —(CH 2 ) 2 —, —CH═CH— or a single bond; and
wherein the liquid crystal component has a value of Δn×Δε≧3.39, when there is no chiral dopant.
3. An optically isotropic liquid crystal composition having a liquid crystal component comprising a liquid crystal component A consisting of one or more compounds represented by general formula (1-1) or (1-2) and chiral dopants, wherein in the liquid crystal component, the content of compounds represented by l+m+n+o≧2 in formula (1-1) or (1-2) is approximately 15 wt % or more, and the content of compounds represented by l+m+n+o=1 is approximately 0.1 to approximately 85 wt %,
and wherein in formulae (1-1) and (1-2):
R 1 is alkenyl having 2 to 20 carbon atoms, wherein any —CH 2 — in the alkenyl can be replaced by —O—, —S—, —COO—, —OCO—, —CH═CH— or —C≡C—; and any hydrogen in the alkenyl can be replaced by halogen;
Ring A 1 , Ring A 2 , Ring A 3 and Ring A 4 are each independently a benzene ring, a naphthalene ring, a cyclohexene ring, a bicyclooctane ring or a cyclohexane ring, wherein any hydrogen in these rings can be replaced by halogen; any —CH 2 — in the rings can be replaced by —O— or —S—; and any —CH═ in the rings can be replaced by —N═;
Z 0 is a single bond or alkylene having 1 to 20 carbon atoms, wherein any —CH 2 — in the alkylene can be replaced by —O—, —S—, —COO—, —OCO—, —CSO—, —OCS—, —CH═CH—, —CF═CF— or —C≡C—; and any hydrogen can be replaced by halogen;
Z 1 , Z 2 , Z 3 and Z 4 are each independently a single bond or alkylene having 1 to 4 carbon atoms, wherein any —CH 2 — in the alkylene can be replaced by —O—, —S—, —COO—, —OCO—, —CSO—, —OCS—, —CH═CH—, —CF═CF— or —C≡C—; and any hydrogen can be replaced by halogen;
L 1 and L 2 are each independently hydrogen or halogen;
X 1 is halogen, —C≡N, —N═C═S, —C≡C—C≡N, —SF 5 , —CHF 2 , —CF 3 , —CF 2 CH 2 F, —CF 2 CHF 2 , —CF 2 CF 3 , —(CF 2 ) 3 —F, —CF 2 CHFCF 3 , —CHFCF 2 CF 3 , —(CF 2 ) 4 —F, —(CF 2 ) 5 —F, —OCHF 2 , —OCF 3 , —OCF 2 CH 2 F, —OCF 2 CHF 2 , —OCH 2 CF 3 , —OCF 2 CF 3 , —O—(CF 2 ) 3 —F, —OCF 2 CHFCF 3 , —OCHFCF 2 CF 3 , —O—(CF 2 ) 4 —F, —O—(CF 2 ) 5 —F, —CH═CF 2 , —CH═CHCF 3 or —CH═CHCF 2 CF 3 ; and
l, m, n and o are each independently 0 or 1,
wherein the liquid crystal component does not contain a liquid crystal component D consisting of at least one compound selected from the group consisting of compounds represented by general formulae (7) to (9),
and wherein in the formulae:
R 4 and R 5 are each independently alkyl having 1 to 10 carbon atoms or alkenyl having 2 to 10 carbon atoms, wherein any —CH 2 — in the alkyl and the alkenyl can be replaced by —O—;
Ring D 1 , Ring D 2 and Ring D 3 are each independently 1,4-cyclohexylene, pyrimidine-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene or 2,5-difluoro-1,4-phenylene;
Z 9 and Z 10 are each independently —C≡C—, —COO—, —(CH 2 ) 2 —, —CH═CH— or a single bond; and
wherein the liquid crystal component has a value of Δn×Δε≧3.39, when there is no chiral dopant.
4. An optically isotropic liquid crystal composition having a liquid crystal component comprising a liquid crystal component A consisting of one or more compounds represented by general formula (1-1) or (1-2) and a liquid crystal component B consisting of one or more compounds represented by general formula (1-3) and chiral dopants, wherein in the liquid crystal component, the content of the liquid crystal component B is approximately 15 to approximately 99.5 wt % or more,
and wherein in formulae (1-1) and (1-2):
R 1 is alkenyl having 2 to 20 carbon atoms, wherein any —CH 2 — in the alkenyl can be replaced by —O—, —S—, —COO—, —OCO—, —CH═CH— or —C≡C—; and any hydrogen in the alkenyl can be replaced by halogen;
Ring A 1 , Ring A 2 , Ring A 3 and Ring A 4 are each independently a benzene ring, a naphthalene ring, a cyclohexene ring, a bicyclooctane ring or a cyclohexane ring, wherein any hydrogen in these rings can be replaced by halogen; any —CH 2 — in the rings can be replaced by —O— or —S—; and any —CH═ in the rings can be replaced by —N═;
Z 0 is a single bond or alkylene having 1 to 20 carbon atoms, wherein any —CH 2 — in the alkylene can be replaced by —O—, —S—, —COO—, —OCO—, —CSO—, —OCS—, —CH═CH—, —CF═CF— or —C≡C—; and any hydrogen can be replaced by halogen;
Z 1 , Z 2 , Z 3 and Z 4 are each independently a single bond or alkylene having 1 to 4 carbon atoms, wherein any —CH 2 — in the alkylene can be replaced by —O—, —S—, —COO—, —OCO—, —CSO—, —OCS—, —CH═CH—, —CF═CF— or —C≡C—; and any hydrogen can be replaced by halogen;
L 1 and L 2 are each independently hydrogen or halogen;
X 1 is halogen, —C≡N, —N═C═S, —C≡C—C≡N, —SF 5 , —CHF 2 , —CF 3 , —CF 2 CH 2 F, —CF 2 CHF 2 , —CF 2 CF 3 , —(CF 2 ) 3 —F, —CF 2 CHFCF 3 , —CHFCF 2 CF 3 , —(CF 2 ) 4 —F, —(CF 2 ) 5 —F, —OCHF 2 , —OCF 3 , —OCF 2 CH 2 F, —OCF 2 CHF 2 , —OCH 2 CF 3 , —OCF 2 CF 3 , —O—(CF 2 ) 3 —F, —OCF 2 CHFCF 3 , —OCHFCF 2 CF 3 , —O—(CF 2 ) 4 —F, —O—(CF 2 ) 5 —F, —CH═CF 2 , —CH═CHCF 3 or —CH═CHCF 2 CF 3 ; and
l, m, n and o are each independently 0 or 1,
and wherein in general formula (1-3):
R 2 is hydrogen or alkyl having 1 to 20 carbon atoms, wherein any —CH 2 — in the alkyl can be replaced by —O—, —S—, —COO—, —OCO— or —C≡C—; and any hydrogen in the alkyl can be replaced by halogen;
Ring A 1 , Ring A 2 , Ring A 3 and Ring A 4 are each independently a benzene ring, a naphthalene ring, a cyclohexene ring, a bicyclooctane ring or a cyclohexane ring, wherein any hydrogen in these rings can be replaced by halogen; any —CH 2 — in the rings can be replaced by —O— or —S—; and any —CH═ in the rings can be replaced by —N═;
Z 1 , Z 2 , Z 3 and Z 4 are each independently a single bond or alkylene having 1 to 4 carbon atoms, wherein any —CH 2 — in the alkylene can be replaced by —O—, —S—, —COO—, —OCO—, —CSO—, —OCS—, —CH═CH—, —CF═CF— or —C≡C—; and any hydrogen in the alkylene can be replaced by halogen;
L 1 and L 2 are each independently hydrogen or halogen;
X 1 is halogen, —C≡N, —N═C═S, —C≡C—C≡N, —SF 5 , —CHF 2 , —CF 3 , —CF 2 CH 2 F, —CF 2 CHF 2 , —CF 2 CF 3 , —(CF 2 ) 3 —F, —CF 2 CHFCF 3 , —CHFCF 2 CF 3 , —(CF 2 ) 4 —F, —(CF 2 ) 5 —F, —OCHF 2 , —OCF 3 , —OCF 2 CH 2 F, —OCF 2 CHF 2 , —OCH 2 CF 3 , —OCF 2 CF 3 , —O—(CF 2 ) 3 —F, —OCF 2 CHFCF 3 , —OCHFCF 2 CF 3 , —O—(CF 2 ) 4 —F, —O—(CF 2 ) 5 —F, —CH═CF 2 , —CH═CHCF 3 or —CH═CHCF 2 CF 3 ; and
l and m are each independently 0 or 1; and
l+m≧1;
wherein the liquid crystal component does not contain a liquid crystal component D consisting of at least one compound selected from the group consisting of compounds represented by general formulae (7) to (9),
and wherein in the formulae:
R 4 and R 5 are each independently alkyl having 1 to 10 carbon atoms or alkenyl having 2 to 10 carbon atoms, wherein any —CH 2 — in the alkyl and the alkenyl can be replaced by —O—;
Ring D 1 , Ring D 2 and Ring D 3 are each independently 1,4-cyclohexylene, pyrimidine-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene or 2,5-difluoro-1,4-phenylene;
Z 9 and Z 10 are each independently —C≡C—, —COO—, —(CH 2 ) 2 —, —CH═CH— or a single bond; and
wherein the liquid crystal component has a value of Δn×Δε≧3.39, when there is no chiral dopant.
5. The optically isotropic liquid crystal composition according to claim 1 , wherein in the liquid crystal component A, the content of the compounds represented by general formula (1-1) is approximately 5 to approximately 85 wt %.
6. The optically isotropic liquid crystal composition according to claim 1 , wherein in the liquid crystal component, the content of the liquid crystal component A is approximately 40 to approximately 85 wt %.
7. The optically isotropic liquid crystal composition according to claim 1 , wherein in the liquid crystal component, the content of the liquid crystal component A is approximately 70 to approximately 85 wt %.
8. The optically isotropic liquid crystal composition according to claim 1 , wherein in the optically isotropic liquid crystal composition, the content of the liquid crystal component A is approximately 70 to approximately 84 wt %.
9. The optically isotropic liquid crystal composition according to claim 1 , wherein R 1 in general formula (1-2) is represented by any one of the formulae selected from the group consisting of the following formulae (CHN-1) to (CHN-12),
and wherein in formulae (CHN-1) to (CHN-12), each R 1a is independently hydrogen or alkyl having 1 to 10 carbon atoms.
10. The optically isotropic liquid crystal composition according to claim 1 , wherein in the liquid crystal component, the difference between the upper limit and the lower limit of a temperature allowing coexistence of a nematic phase and a non-liquid crystalline isotropic phase is approximately 3° C. to approximately 150° C.
11. The optically isotropic liquid crystal composition according to claim 1 , comprising the chiral dopants in an amount of 1 to approximately 40 wt % of the total weight of the liquid crystal composition.
12. The optically isotropic liquid crystal composition according to claim 1 , comprising the chiral dopants in an amount of approximately 5 to approximately 15 wt % of the total weight of the liquid crystal composition.
13. The optically isotropic liquid crystal composition according to claim 1 , wherein the chiral dopants comprise one or more compounds represented by any one of the following formulae (K1) to (K5),
and wherein in formulae (K1) to (K5):
each R K is independently hydrogen, halogen, —C≡N, —N═C═O, —N═C═S or alkyl having 1 to 20 carbon atoms, wherein any —CH 2 — in the alkyl can be replaced by —O—, —S—, —COO—, —OCO—, —CH═CH—, —CF═CF— or —C≡C—; and any hydrogen in the alkyl can be replaced by halogen;
each A is independently an aromatic or nonaromatic 3- to 8-membered ring or a condensed ring having 9 or more carbon atoms, wherein any hydrogen in these rings can be replaced by halogen, alkyl having 1 to 3 carbon atoms or haloalkyl; —CH 2 — in the rings can be replaced by —O—, —S— or —NH—; and CH═ in the rings can be replaced by —N═;
each Z is independently a single bond or alkylene having 1 to 8 carbon atoms, wherein any —CH 2 — in the alkylene can be replaced by —O—, —S—, —COO—, —OCO—, —CSO—, —OCS—, —N═N—, —CH═N—, —N═CH—, —N(O)═N—, —N═N(O)—, —CH═CH—, —CF═CF— or —C≡C—; and any hydrogen in the alkylene can be replaced by halogen;
each X is independently a single bond, —COO—, —CH 2 O—, —CF 2 O—, —OCO—, —OCH 2 —, —OCF 2 — or —CH 2 CH 2 —; and
each mK is independently an integer from 1 to 4.
14. The optically isotropic liquid crystal composition according to claim 1 , wherein the chiral dopants comprise one or more compounds represented by any one of the following formulae (K2-1) to (K2-8) and (K5-1) to (K5-3),
and wherein in formulae (K2-1) to (K2-8) and (K5-1) to (K5-3):
each R K is independently alkyl having 1 to 10 carbon atoms, wherein —CH 2 — adjacent to the ring in the alkyl can be replaced by —O—; and any —CH 2 — in the alkyl can be replaced by —CH═CH—.
15. The optically isotropic liquid crystal composition according to claim 1 , further comprising one or more agents selected from the group consisting of antioxidants and ultraviolet absorbers.
16. The optically isotropic liquid crystal composition according to claim 1 , wherein an optically isotropic liquid crystal phase does not show diffracted light with two or more colors.
17. The optically isotropic liquid crystal composition according to claim 1 , wherein an optically isotropic liquid crystal phase shows diffracted light with two or more colors.
18. The optically isotropic liquid crystal composition according to claim 1 , which exhibits a chiral nematic phase at approximately −20° C. to approximately 70° C., and wherein in at least a part of the temperature range, the spiral pitch is approximately 700 nm or less.
19. A mixture comprising the optically isotropic liquid crystal composition according to claim 1 and a polymerizable monomer.
20. The mixture according to claim 19 , wherein the polymerizable monomer is a photopolymerizable monomer or a thermopolymerizable monomer.
21. A polymer/liquid crystal composite for use in an element driven in a state of an optically isotropic liquid crystal phase, which can be obtained by polymerizing the mixture according to claim 19 .
22. A polymer/liquid crystal composite for use in an element driven in a state of an optically isotropic liquid crystal phase, which can be obtained by polymerizing the mixture according to claim 19 in a state of a non-liquid crystalline isotropic phase or the optically isotropic liquid crystal phase.
23. The polymer/liquid crystal composite according to claim 21 , wherein a polymer included in the polymer/liquid crystal composite has a mesogenic moiety.
24. The polymer/liquid crystal composite according to claim 21 , wherein the polymer included in the polymer/liquid crystal composite has a cross-linked structure.
25. The polymer/liquid crystal composite according to claim 21 , comprising the liquid crystal composition in an amount of approximately 60 to approximately 99 wt % and the polymer in an amount of 1 to 40 wt %.