Liquid crystal composition and liquid crystal display device

Patent metadata

Field	Value
Publication number	US-9714210-B2
Application number	US-201414889440-A
Country	US
Kind code	B2
Filing date	Apr 17, 2014
Priority date	May 28, 2013
Publication date	Jul 25, 2017
Grant date	Jul 25, 2017

Abstract

A liquid crystal composition satisfies at least one of characteristics such as a high maximum temperature, a low minimum temperature, small viscosity, suitable optical anisotropy, large negative dielectric anisotropy, large specific resistance, high stability to ultraviolet light, to heat or the like, or has a suitable balance regarding at least two of the characteristics; and an AM device has characteristics such as a short response time, a large voltage holding ratio, a low threshold voltage, a large contrast ratio and a long service life. The liquid crystal composition contains a specific compound having at least two polymerizable groups, and the liquid crystal display device includes the composition. The composition contains a specific compound having large negative dielectric anisotropy as a first component, and may contain a specific compound having the high maximum temperature or the small viscosity as a second component.

First claim

What is claimed is:

1. A liquid crystal composition that has a negative dielectric anisotropy, and contains a polymerizable compound that is at least one compound selected from the group of compounds represented by formula (1):

wherein, in formula (1), ring A 1 or ring C 1 is 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 the rings, at least one of hydrogen may be replaced by halogen, alkyl having 1 to 12 carbons, or alkyl having 1 to 12 carbons in which at least one of hydrogen is replaced by halogen; ring B 1 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 the rings, at least one of hydrogen may be replaced by halogen, alkyl having 1 to 12 carbons, or alkyl having 1 to 12 carbons in which at least one of hydrogen may be replaced by halogen; Z 1 or Z 2 is independently a single bond or alkylene having 1 to 10 carbons, in the alkylene, at least one of —CH 2 — may be replaced by —O—, —CO—, —COO— or —OCO—, at least one of —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 the groups, at least one of hydrogen may be replaced by fluorine or chlorine; at least one of P 1 , P 2 and P 3 is acryloyloxy or methacryloyloxy, and at least one remainder is 2-butenoyloxy, 2-methyl-2-butenoyloxy, 2-methylenebutanoyloxy, 2-methyl-1-propenyloxy, 2,2-difluorovinyloxy, 2-butenyloxy, 2-methyl-2-butenyloxy or 2-methyl-2-propenyloxy; Sp 1 , Sp 2 or Sp 3 is independently a single bond or alkylene having carbons 1-10, in the alkylene, at least one of —CH 2 — may be replaced by —O—, —COO—, —OCO— or —OCOO—, at least one of —CH 2 —CH 2 — may be replaced by —CH═CH— or —C≡C—, and in the groups, at least one of hydrogen may be replaced by fluorine or chlorine; a is 0, 1 or 2; and b, c or d is independently an integer from 0 to 4, and a sum of b, c, and d is 2 or more.

2. The liquid crystal composition according to claim 1 , wherein the polymerizable compound is at least one compound selected from the group of compounds represented by formula (1-1):

wherein, in formula (1-1), ring A 2 , ring B 2 or ring C 2 is independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl or naphthalene-2,6-diyl, and in the rings, at least one of hydrogen may be replaced by halogen, alkyl having 1 to 12 carbons, or alkyl having 1 to 12 carbons in which at least one of hydrogen is replaced by halogen; Z 1 or Z 2 is independently a single bond or alkylene having 1 to 10 carbons, in the alkylene, at least one of —CH 2 — may be replaced by —O—, —CO—, —COO— or —OCO—, at least one of —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 the groups, at least one of hydrogen may be replaced by fluorine or chlorine; at least one of P 1 , P 2 and P 3 is acryloyloxy or methacryloyloxy, and at least one remainder is 2-butenoyloxy, 2-methyl-2-butenoyloxy, 2-methylenebutanoyloxy, 2-methyl-1-propenyloxy, 2,2-difluorovinyloxy, 2-butenyloxy, 2-methyl-2-butenyloxy or 2-methyl-2-propenyloxy; Sp 1 , Sp 2 or Sp 3 is independently a single bond or alkylene having 1 to 10 carbons, in the alkylene, at least one of —CH 2 — may be replaced by —O—, —COO—, —OCO— or —OCOO—, at least one of —CH 2 —CH 2 — may be replaced by —CH═CH— or —C≡C—, and in the groups, at least one of hydrogen may be replaced by fluorine or chlorine; a is 0, 1 or 2; and c is an integer from 0 to 4, f, g, h and i each are 0 or 1, and a sum of c, f, g, h and i is 1 or more.

3. The liquid crystal composition according to claim 1 , wherein the polymerizable compound is at least one compound selected from the group of compounds represented by formula (1-1-1):

wherein, in formula (1-1-1), ring A 3 , ring B 3 or ring C 3 is independently 1,4-phenylene in which at least one of hydrogen may be replaced by halogen, alkyl having 1 to 12 carbons, or alkyl having 1 to 12 carbons in which at least one of hydrogen is replaced by halogen; Z 1 or Z 2 is independently a single bond, —COO—, —CH═CH—, —CH═CH—COO—, —C(CH 3 )═CH—COO—, —CH═C(CH 3 )—COO—, —C(CH 3 )═C(CH 3 )—COO—, —COCH═CH—, —C(CH 3 )═C(CH 3 )—, —CH═CH—CH 2 O—, —CH═CH—OCH 2 — or —CO—; at least one of P 1 , P 2 and P 3 is acryloyloxy or methacryloyloxy, and at least one remainder is 2-butenoyloxy, 2-methyl-2-butenoyloxy, 2-methylenebutanoyloxy, 2-methyl-1-propenyloxy, 2,2-difluorovinyloxy, 2-butenyloxy, 2-methyl-2-butenyloxy, or 2-methyl-2-propenyloxy; Sp 1 , Sp 2 or Sp 3 is independently a single bond or alkylene having 1 to 10 carbons, in the alkylene, at least one of —CH 2 — may be replaced by —O—, —COO—, —OCO— or —OCOO—, at least one of —CH 2 —CH 2 — may be replaced by —CH═CH— or —C≡C—, and in the groups, at least one of hydrogen may be replaced by fluorine or chlorine; a is 0, 1 or 2; and c is an integer from 0 to 4.

4. The liquid crystal composition according to claim 1 , wherein the polymerizable compound is at least one compound selected from the group of compounds represented by formula (1-1-1-1) to formula (1-1-1-12):

wherein, in formula (1-1-1-1) to formula (1-1-1-12), P 4 or P 5 is independently acryloyloxy or methacryloyloxy; and Sp 1 or Sp 3 is independently a single bond or alkylene having 1 to 10 carbons, in the alkylene, at least one of —CH 2 — may be replaced by —O—, —COO—, —OCO— or —OCOO—, at least one of —CH 2 —CH 2 — may be replaced by —CH═CH— or —C≡C—, and in the groups, at least one of hydrogen may be replaced by fluorine or chlorine.

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

wherein, in formula (2), R 9 or R 10 is 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 D or ring F is independently 1,4-cyclohexylene, 1,4-phenylene, 1,4-phenylene in which at least one of hydrogen is replaced by fluorine or chlorine or tetrahydropyran-2,5-diyl; ring E 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-difluorochroman-2,6-diyl; Z 3 or Z 4 is independently a single bond, —CH 2 CH 2 —, —CH 2 O—, —OCH 2 —, —COO— or —OCO—; and j is 1, 2 or 3, k is 0 or 1, and a sum of j and k is 3 or less.

6. The liquid crystal composition according to claim 5 , containing at least one compound selected from the group of compounds represented by formula (2-1) to formula (2-19) as the first component:

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Furusato Yoshimasa
• Saito Masayuki

Classifications

• C07C69/54 Primary

  Acrylic acid esters; Methacrylic acid esters · CPC title

• C09K2019/3422

  the heterocyclic ring being a six-membered ring · CPC title

• C08F20/30 Primary

  containing aromatic rings in the alcohol moiety · CPC title

• C09K2019/0448

  the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate · CPC title

• C09K19/12

  at least two benzene rings directly linked, e.g. biphenyls · CPC title