IP Library Granted Patent US 10,385,269
Granted Patent B2
US 10,385,269 · App. 15/368,676 · Granted Aug 20, 2019

Liquid crystal composition and liquid crystal display device

Inventor: Masayuki Saito (Chiba, JP)
Assignees: JNC CORPORATION; JNC PETROCHEMICAL CORPORATION
C09K19/3001C09K19/20C09K19/3066C09K19/3068C09K19/3402C09K2019/0466C09K2019/123C09K2019/3004C09K2019/3009C09K2019/3015C09K2019/3016C09K2019/3021C09K2019/3025C09K2019/3071C09K2019/3077C09K2019/3078C09K2019/3083C09K2019/3422
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Quick Facts
Patent No.
US 10,385,269
App. No.
15/368,676
Granted
Aug 20, 2019
Kind
B2
Abstract

The subject is to show a liquid crystal composition in which the homeotropic alignment of liquid crystal molecules can be achieved by the action of a polymer, and a liquid crystal display device including this composition. The means concerns a nematic liquid crystal composition that has positive dielectric anisotropy and that includes a specific liquid crystal compound having a large positive dielectric anisotropy as a first component and a polar compound having a polymerizable group as a first additive, and the composition may include a specific liquid crystal compound having a high maximum temperature or a small viscosity as a second component, a specific liquid crystal compound having a positive dielectric anisotropy as a third component, a specific liquid crystal compound having negative dielectric anisotropy as a fourth component, and a polymerizable compound as a second additive, and concerns a liquid crystal display device including the composition.

Claims (37)

1. A liquid crystal composition having positive dielectric anisotropy and including at least one compound selected from the group consisting of compounds represented by formula (1) as a first component and at least one polar compound selected from the group consisting of compounds represented by formula (5) and formula (6) as a first additive:

in formula (1), R 1 is alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons or alkenyl having 2 to 12 carbons; ring A and ring B are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, pyrimidine-2,5-diyl, 1,3-dioxane-2,5-diyl or tetrahydropyran-2,5-diyl; Z 1 and Z 2 are independently a single bond, —CH 2 CH 2 —, —CH═CH—, —CH 2 O—, —OCH 2 —, —COO—, —OCO—, —CF 2 O— or —OCF 2 —; X 1 and X 2 are independently hydrogen or fluorine; Y 1 is fluorine, chlorine, alkyl having 1 to 12 carbons in which at least one hydrogen has been replaced by fluorine or chlorine, alkoxy having 1 to 12 carbons in which at least one hydrogen has been replaced by fluorine or chlorine, or alkenyloxy having 2 to 12 carbons in which at least one hydrogen has been replaced by fluorine or chlorine; and a is 1, 2, 3 or 4; b is 0, 1, 2 or 3, and the sum of a and b is 4 or less;

in formula (5), R 7 is hydrogen, fluorine, chlorine or alkyl having 1 to 25 carbons, and in the alkyl at least one —CH 2 — may be replaced by —NR 0 —, —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O— or cycloalkylene having 3 to 8 carbons, and at least one tertiary carbon (>CH—) may be replaced by nitrogen (>N—), and in these groups at least one hydrogen may be replaced by fluorine or chlorine, where R 0 is hydrogen or alkyl having 1 to 12 carbons; R 8 is a polar group having at least one of an oxygen atom of a OH moiety, a sulfur atom of an SH moiety and a nitrogen atom of primary, secondary or tertiary amine moiety; ring J, ring K and ring L are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, naphthalene-2,7-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl, and in these rings at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons or alkyl having 1 to 12 carbons in which at least one hydrogen has been replaced by fluorine or chlorine; Z 7 and Z 8 are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene at least one —CH 2 — may be replaced by —O—, —CO—, —COO— or —OCO—, and at least one —CH 2 CH 2 — may be replaced by —CH═CH—, —C(CH 3 )═CH—, —CH═C(CH 3 )— or —C(CH 3 )═C(CH 3 )—, and in these groups at least one hydrogen may be replaced by fluorine or chlorine; P 1 , P 2 and P 3 is a polymerizable group; Sp 1 , Sp 2 and Sp 3 are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene at least one —CH 2 — may be replaced by —O—, —COO—, —OCO— or —OCOO—, and at least one —CH 2 CH 2 — may be replaced by —CH═CH— or —C≡C—, and in these groups at least one hydrogen may be replaced by fluorine or chlorine; g and h are independently 0, 1, 2, 3 or 4, and the sum of g and h is 0, 1, 2, 3 or 4; k and p are independently 0, 1, 2, 3 or 4, o is 1, 2, 3 or 4; and

in formula (6), R 9 is hydrogen, fluorine, chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkyl having 1 to 12 carbons in which at least one hydrogen has been replaced by fluorine or chlorine, or alkenyl having 2 to 12 carbons in which at least one hydrogen has been replaced by fluorine or chlorine; R 10 is a group represented by —OH, —OR 0 , —NH 2 , —NHR 0 or —N(R 0 ) 2 , where R 0 is hydrogen or alkyl having 1 to 12 carbons; ring M and ring N are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, naphthalene-2,7-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl or anthracene-2,6-diyl, and in these rings at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons or alkyl having 1 to 12 carbons in which at least one hydrogen has been replaced by fluorine or chlorine; Z 9 is a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 — or —CF═CF—; Sp 4 and Sp 5 are independently a single bond or alkylene having 1 to 7 carbons, and in the alkylene at least one —CH 2 — may be replaced by —O—, —COO— or —OCO—, at least one —CH 2 CH 2 — may be replaced by —CH═CH—, and in these groups at least one hydrogen may be replaced by fluorine; and i is 0, 1, 2, 3 or 4.

2. The liquid crystal composition according to claim 1 , including at least one compound selected from the group consisting of compounds represented by formula (1-1) to formula (1-14) as the first component:

in formula (1-1) to formula (1-14), R 1 is alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons or alkenyl having 2 to 12 carbons; X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 0 , X 11 , X 12 , X 13 and X 14 are independently hydrogen or fluorine; and Y 1 is fluorine, chlorine, alkyl having 1 to 12 carbons in which at least one hydrogen has been replaced by fluorine or chlorine, alkoxy having 1 to 12 carbons in which at least one hydrogen has been replaced by fluorine or chlorine, or alkenyloxy having 2 to 12 carbons in which at least one hydrogen has been replaced by fluorine or chlorine.

3. The liquid crystal composition according to claim 1 , wherein the proportion of the first component is in the range of 5% by weight to 55% by weight based on the weight of the liquid crystal composition.

4. The liquid crystal composition according to claim 1 , including at least one compound selected from the group consisting of compounds represented by formula (2) as a second component:

in formula (2), R 2 and R 3 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons or alkenyl having 2 to 12 carbons in which at least one hydrogen has been replaced by fluorine or chlorine; ring C and ring D are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene or 2,5-difluoro-1,4-phenylene; Z 3 is a single bond, —CH 2 CH 2 —, —CH 2 O—, —OCH 2 —, —COO— or —OCO—; and c is 1, 2 or 3.

5. The liquid crystal composition according to claim 4 , including at least one compound selected from the group consisting of compounds represented by formula (2-1) to formula (2-13) as the second component:

in formula (2-1) to formula (2-13), R 2 and R 3 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkyl having 1 to 12 carbons in which at least one hydrogen has been replaced by fluorine or chlorine, or alkenyl having 2 to 12 carbons in which at least one hydrogen has been replaced by fluorine or chlorine.

6. The liquid crystal composition according to claim 4 , wherein the proportion of the second component is in the range of 10% by weight to 70% by weight based on the weight of the liquid crystal composition.

7. The liquid crystal composition according to claim 4 , including at least one compound selected from the group consisting of compounds represented by formula (3) as a third component:

in formula (3), R 4 is alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons or alkenyl having 2 to 12 carbons; ring E is 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, pyrimidine-2,5-diyl, 1,3-dioxane-2,5-diyl or tetrahydropyran-2,5-diyl; Z 4 is a single bond, —CH 2 CH 2 —, —COO— or —OCO—; X 15 and X 16 are independently hydrogen or fluorine; Y 2 is fluorine, chlorine, alkyl having 1 to 12 carbons in which at least one hydrogen has been replaced by fluorine or chlorine, alkoxy having 1 to 12 carbons in which at least one hydrogen has been replaced by fluorine or chlorine, or alkenyloxy having 2 to 12 carbons in which at least one hydrogen has been replaced by fluorine or chlorine; and d is 1, 2, 3 or 4.

8. The liquid crystal composition according to claim 7 , including at least one compound selected from the group consisting of compounds represented by formula (3-1) to formula (3-16) as the third component:

in formula (3-1) to formula (3-16), R 4 is alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons or alkenyl having 2 to 12 carbons.

9. The liquid crystal composition according to claim 4 , including at least one compound selected from the group consisting of compounds represented by formula (4) as a fourth component:

in formula (4), R 5 and R 6 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons or alkenyloxy having 2 to 12 carbons; ring F and ring I are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen has been replaced by fluorine or chlorine, or tetrahydropyran-2,5-diyl; ring G is 2,3-difluoro-1,4-phenylene, 2-chloro-3-fluoro-1,4-phenylene, 2,3-difluoro-5-methyl-1,4-phenylene, 3,4,5-trifluoronaphthalene-2,6-diyl or 7,8-difluorochromane-2,6-diyl; Z 5 and Z 6 are independently a single bond, —CH 2 CH 2 —, —CH 2 O—, —OCH 2 —, —COO— or —OCO—; and e is 1, 2 or 3, f is 0 or 1, and the sum of e and f is 3 or less.

10. The liquid crystal composition according to claim 9 , including at least one compound selected from the group consisting of compounds represented by formula (4-1) to formula (4-22) as the fourth component:

in formula (4-1) to formula (4-22), R 5 and R 6 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons or alkenyloxy having 2 to 12 carbons.

11. The liquid crystal composition according to claim 1 , wherein in formula (5), R 8 is a group represented by any one of formula (A1) to formula (A4):

in formula (A1) to formula (A4), Sp 6 , Sp 8 and Sp 9 are independently a single bond or alkylene having 1 to 12 carbons, and in the alkylene at least one —CH 2 — may be replaced by —O—, —S—, —NH—, —N(R 0 )—, —CO—, —CO—O—, —O—CO, —O—CO—O—, —S—CO—, —CO—S—, —N(R 0 )—CO—O—, —O—CO—N(R 0 )—, —N(R 0 )—CO—N(R 0 )—, —CH═CH— or —C≡C—, and in these groups at least one hydrogen may be replaced by fluorine or chlorine, where R 0 is hydrogen or alkyl having 1 to 12 carbons; Sp 7 is >CH—, >CR 0 —, >N— or >C<, where R 0 is hydrogen or alkyl having 1 to 12 carbons; X 17 is —OH, —OR 0 , —COOH, —NH 2 , —NHR 0 , —N(R 0 ) 2 , —SH, —SR 0 ,

where R 0 is hydrogen or alkyl having 1 to 12 carbons; X 18 is —O—, —CO—, —NH—, —NR 0 —, —S— or a single bond, where R 0 is hydrogen or alkyl having 1 to 12 carbons; Z 10 is a single bond or alkylene having 1 to 15 carbons, and in the alkylene at least one —CH 2 — may be replaced by —C≡C—, —CH═CH—, —COO—, —OCO—, —CO— or —O—, and in these groups at least one hydrogen may be replaced by fluorine or chlorine; Ring P is aryl having 6 to 25 carbons, and in the aryl one to three hydrogens may be replaced by —OH, —(CH 2 ) q —OH, fluorine, chlorine, alkyl having 1 to 5 carbons or alkyl having 1 to 5 carbons in which at least one hydrogen has been replaced by fluorine or chlorine, where q is 1, 2, 3 or 4; n is 0, 1, 2 or 3; and m is 1, 2, 3, 4 or 5.

12. The liquid crystal composition according to claim 1 , wherein in formula (5), P 1 , P 2 and P 3 are independently a polymerizable group selected from the group consisting of groups represented by formula (P-1) to formula (P-5):

in formula (P-1) to formula (P-5), M 1 , M 2 and M 3 are independently hydrogen, fluorine, alkyl having 1 to 5 carbons or alkyl having 1 to 5 carbons in which at least one hydrogen has been replaced by fluorine or chlorine.

13. The liquid crystal composition according to claim 1 , wherein the first additive is at least one polar compound selected from the group consisting of compounds represented by formula (5-1) to formula (5-15):

in formula (5-1) to formula (5-15), R 7 is hydrogen, fluorine, chlorine or alkyl having 1 to 25 carbons, and in the alkyl at least one —CH 2 — may be replaced by —NR 0 —, —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O— or cycloalkylene having 3 to 8 carbons, at least one tertiary carbon (>CH—) may be replaced by nitrogen (>N—), and in these groups at least one hydrogen may be replaced by fluorine or chlorine, where R 0 is hydrogen or alkyl having 1 to 12 carbons; Sp 2 is a single bond or alkylene having 1 to 10 carbons, and in the alkylene at least one —CH 2 — may be replaced by —O—, —COO—, —OCO— or —OCOO—, and at least one —CH 2 CH 2 — may be replaced by —CH═CH— or —C≡C—, and in these groups at least one hydrogen may be replaced by fluorine or chlorine; Sp 10 is a single bond or alkylene having 1 to 10 carbons, and in the alkylene at least one —CH 2 — may be replaced by —O—, —COO—, —OCO— or —OCOO—, and at least one —CH 2 CH 2 — may be replaced by —CH═CH— or —C≡C—, and in these groups at least one hydrogen may be replaced by fluorine or chlorine; L 1 , L 2 , L 3 and L 4 are independently hydrogen, fluorine, methyl or ethyl; and R 11 and R 12 are independently hydrogen or methyl.

14. The liquid crystal composition according to claim 1 , wherein the first additive is at least one polar compound selected from the group consisting of compounds represented by formula (6-1) to formula (6-9):

in formula (6-1) to formula (6-9), R 9 is hydrogen, fluorine, chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkyl having 1 to 12 carbons in which at least one hydrogen has been replaced by fluorine or chlorine, or alkenyl having 2 to 12 carbons in which at least one hydrogen has been replaced by fluorine or chlorine; Z 9 is a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 — or —CF═CF—; Sp 4 and Sp 5 are independently a single bond or alkylene having 1 to 7 carbons, and in the alkylene at least one —CH 2 — may be replaced by —O—, —COO— or —OCO—, at least one —CH 2 CH 2 — may be replaced by —CH═CH—, and in these groups at least one hydrogen may be replaced by fluorine; and L 5 , L 6 , L 7 , L 8 , L 9 , L 10 , L 11 , L 12 , L 13 , L 14 , L 15 and L 16 are independently hydrogen, fluorine, methyl or ethyl.

15. The liquid crystal composition according to claim 1 , wherein the proportion of the first additive is in the range of 0.05% by weight to 10% by weight based on the weight of the liquid crystal composition.

16. The liquid crystal composition according to claim 1 , including at least one polymerizable compound selected from the group consisting of compounds represented by formula (7) as a second additive:

in formula (7), ring T and ring V are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxane-2-yl, pyrimidine-2-yl or pyridine-2-yl, and in these rings at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons or alkyl having 1 to 12 carbons in which at least one hydrogen has been replaced by fluorine or chlorine; ring U is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, naphthalene-2,7-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl, and in these rings at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons or alkyl having 1 to 12 carbons in which at least one hydrogen has been replaced by fluorine or chlorine; Z 11 and Z 12 are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene at least one —CH 2 — may be replaced by —O—, —CO—, —COO— or —OCO—, and at least one —CH 2 CH 2 — may be replaced by —CH═CH—, —C(CH 3 )═CH—, —CH═C(CH 3 )— or —C(CH 3 )═C(CH 3 )—, and in these groups at least one hydrogen may be replaced by fluorine or chlorine; P 4 , P 5 and P 6 is a polymerizable group; S p10 , Sp 11 and Sp 12 are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene at least one —CH 2 — may be replaced by —O—, —COO—, —OCO— or —OCOO—, and at least one —CH 2 CH 2 — may be replaced by —CH═CH— or —C≡C—, and in these groups at least one hydrogen may be replaced by fluorine or chlorine; t is 0, 1 or 2; and u, v and w are independently 0, 1, 2, 3 or 4, and the sum u, v and w is 1 or more.

17. The liquid crystal composition according to claim 16 , including at least one polymerizable compound selected from the group consisting of compounds represented by formula (7-1) to formula (7-28) as the second additive:

in formula (7-1) to formula (7-28), P 4 , P 5 and P 6 are independently a polymerizable group selected from the group consisting of groups represented by formula (P-1) to formula (P-3):

where M 1 , M 2 and M 3 are independently hydrogen, fluorine, alkyl having 1 to 5 carbons or alkyl having 1 to 5 carbons in which at least one hydrogen has been replaced by fluorine or chlorine; and Sp 10 , Sp 11 and Sp 12 are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene at least one —CH 2 — may be replaced by —O—, —COO—, —OCO— or —OCOO—, and at least one —CH 2 CH 2 — may be replaced by —CH═CH— or —C≡C—, and in these groups at least one hydrogen may be replaced by fluorine or chlorine.

18. The liquid crystal composition according to claim 16 , wherein the proportion of the second additive is in the range of 0.03% by weight to 10% by weight based on the weight of the liquid crystal composition.

19. A liquid crystal display device without alignment films and including the liquid crystal composition according of claim 1 , where the polymerizable compound in the liquid crystal composition has been polymerized.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 18, 2025
From: JNC CORPORATION; JNC PETROCHEMICAL CORPORATION
To: JIANGSU HECHENG DISPLAY TECHNOLOGY CO., LTD.
Reel/Frame 072472/0384 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 11, 2016
From: SAITO, MASAYUKI
To: JNC CORPORATION; JNC PETROCHEMICAL CORPORATION
Reel/Frame 040704/0591 →
Priority Claims (2)
JP 2015-248229 · Dec 21, 2015 · national
JP 2016-172397 · Sep 5, 2016 · national
Continuity (1)
Related Publication 20170174993A1 · Jun 22, 2017