Polymerizable compound, polymerizable composition and liquid crystal display device

Patent metadata

Field	Value
Publication number	US-10611964-B2
Application number	US-201414786555-A
Country	US
Kind code	B2
Filing date	Mar 13, 2014
Priority date	Apr 25, 2013
Publication date	Apr 7, 2020
Grant date	Apr 7, 2020

Abstract

A polymerizable compound has a high polymerizability, a high conversion ratio and a high solubility in a liquid crystal composition. A polymerizable composition contains the compound. A liquid crystal composite is prepared from the composition. A liquid crystal display device includes the liquid crystal composite. The polymerizable compound is formed in which the polymerizable compound has at least two polymerizable groups in which at least one polymerizable group is acryloyloxy or methacryloyloxy, and at least one remaining polymerizable group is a polymerizable group selected from the group of groups represented by formulas (P-1), (P-2) and (P-3).

In formulas (P-1) to (P-3), R 1 to R 8 are independently hydrogen, fluorine, methyl, ethyl or trifluoromethyl.

First claim

What is claimed is:

1. A polymerizable compound represented by formula (1):

wherein, in formula (1),
at least one of P 1 , P 2 , P 3 and P 4 is acryloyloxy or methacryloyloxy, and at least one remainder is a polymerizable group selected from the group of groups represented by formulas (P-1), (P-2) and (P-3);

wherein, in formulas (P-1) to (P-3), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are independently hydrogen, fluorine, alkyl having 1 to 3 carbons, or alkyl having 1 to 3 carbons in which at least one of hydrogen is replaced by halogen;
in formula (P-1), when R 1 is hydrogen or methyl, at least one of R 2 and R 3 is fluorine, alkyl having 1 to 3 carbons, or alkyl having 1 to 3 carbons in which at least one of hydrogen is replaced by halogen;
in formula (P-2), at least one of R 4 and R 5 is fluorine, alkyl having 1 to 3 carbons, or alkyl having 1 to 3 carbons in which at least one of hydrogen is replaced by halogen; and
in formula (P-3), at least one of R 6 , R 7 and R 8 is fluorine, alkyl having 1 to 3 carbons, or alkyl having 1 to 3 carbons in which at least one of hydrogen is replaced by halogen;
in formula (1),
S 1 , S 2 , S 3 and S 4 are independently a single bond or alkylene having 1 to 10 carbons, and 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 at least one of hydrogen may be replaced by fluorine or chlorine;
a1, a2, a3 and a4 are independently 0, 1, 2, 3 or 4, and a sum of a1, a2, a3 and a4 is an integer from 2 to 10;
ring A 1 and ring A 4 are independently phenyl, pyrimidyl, pyridyl, naphthyl, cyclohexyl, cyclohexenyl, tetrahydropyranyl or 1,3-dioxanyl, 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 A 2 and ring A 3 are independently 1,4-phenylene, pyrimidine-2,5-diyl, pyridine-2,5-diyl, 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, 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl or 1,3-dioxane-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 , Z 2 and Z 3 are independently a single bond, alkylene having 1 to 5 carbons, —CH═CH—, —CH═CH—COO—, —OCO—CH═CH—, —C(CH 3 )═CH—COO—, —OCO—CH═C(CH 3 )—, —CH═C(CH 3 )—COO—, —OCO—(CH 3 )C═CH—, —C(CH 3 )═C(CH 3 )—COO—, —OCO—C(CH 3 )═C(CH 3 )—, —CH═CH—CH 2 O—, —OCH 2 —CH═CH—, —CH═CH—OCH 2 — or —CH 2 O—CH═CH—; and
b1, b2 and b3 are independently 0 or 1, and at least one of b1, b2, and b3 is 1.

2. The polymerizable compound according to claim 1 , wherein, in formula (1) described in claim 1 ,
at least one of P 1 , P 2 , P 3 and P 4 is acryloyloxy or methacryloyloxy, and at least one remainder is 2-butenoyloxy, 2-methyl-2-butenoyloxy, 2-methylenebutanoyloxy, 2-methyl-1-ropenyloxy, 2,2-difluorovinyloxy, 2-butenyloxy or 2-methyl-2-propenyloxy;
S 1 , S 2 , S 3 and S 4 are independently a single bond or alkylene having 1 to 10 carbons, and 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 at least one of hydrogen may be replaced by fluorine or chlorine;
a1, a2, a3 and a4 are independently 0, 1, 2 or 3, and a sum of a1, a2, a3 and a4 is an integer from 2 to 6;
ring A 1 and ring A 4 are independently phenyl, pyrimidyl, pyridyl or naphthyl, 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 A 2 and ring A 3 are independently 1,4-phenylene, pyrimidine-2,5-diyl, pyridine-2,5-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-2,6-diyl, 1,4-cyclohexylene, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl, and in the rings, at least one of hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 5 carbons, alkoxy having 1 to 5 carbons, or alkyl having 1 to 5 carbons or alkoxy having 1 to 5 carbons in which at least one of hydrogen is replaced by halogen;
Z 1 , Z 2 and Z 3 are independently a single bond, alkylene having 1 to 5 carbons, —CH═CH—, —CH═CH—COO—, —OCO—CH═CH—, —C(CH 3 )═CH—COO—, —OCO—CH═C(CH 3 )—, —CH═C(CH 3 )—COO—, —OCO—(CH 3 )C═CH—, —C(CH 3 )═C(CH 3 )—COO—, —OCO—C(CH 3 )═C(CH 3 )—, —CH═CH—CH 2 O—, —OCH 2 —CH═CH—, —CH═CH—OCH 2 — or —CH 2 O—CH═CH—; and
b1, b2 and b3 are independently 0 or 1, and at least one of b1, b2, and b3 is 1.

3. The polymerizable compound according to claim 1 , represented by formula (1-1):

wherein, in formula (1-1), at least one of P 5 , P 6 , P 7 , P 8 , P 9 and P 10 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 or 2-methyl-2-propenyloxy;
S 5 , S 6 , S 7 , S 8 , S 9 and S 10 are independently a single bond or alkylene having 1 to 5 carbons, and in the alkylene, at least one of —CH 2 — may be replaced by —O—, —COO— or —OCO—, and at least one of —CH 2 —CH 2 — may be replaced by —CH═CH—;
c1, c2, c3 and c4 are independently 0, 1 or 2, and a sum of c1, c2, c3 and c4 is an integer from 0 to 5;
ring A 5 , ring A 6 , ring A 7 and ring A 8 are independently 1,4-phenylene, pyrimidine-2,5-diyl, pyridine-2,5-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-2,6-diyl, 1,4-cyclohexylene, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl, and in the rings, at least one of hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 5 carbons, alkoxy having 1 to 5 carbons, or alkyl having 1 to 5 carbons or alkoxy having 1 to 5 carbons in which at least one of hydrogen is replaced by halogen;
Z 4 , Z 5 and Z 6 are independently a single bond, alkylene having 1 to 5 carbons, —CH═CH—, —CH═CH—COO—, —OCO—CH═CH—, —C(CH 3 )═CH—COO—, —OCO—CH═C(CH 3 )—, —CH═C(CH 3 )—COO—, —OCO—(CH 3 )C═CH—, —C(CH 3 )═C(CH 3 )—COO—, —OCO—C(CH 3 )═C(CH 3 )—, —CH═CH—CH 2 O—, —OCH 2 —CH═CH—, —CH═CH—OCH 2 — or —CH 2 O—CH═CH—; and
d1, d2 and d3 are independently 0 or 1, and at least one of d1, d2, and d3 is 1.

4. The polymerizable compound according to claim 3 , wherein, in formula (1-1) described in claim 3 , P 5 and P 0 are independently acryloyloxy or methacryloyloxy, at least one of P 6 , P 7 , P 8 and P 9 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 or 2-methyl-2-propenyloxy: S 5 , S 6 , S 7 , S 8 , S 9 and S 10 are a single bond; c1, c2, c3 and c4 are independently 0 or 1, and a sum of c1, c2, c3 and c4 is 1, 2 or 3; ring A 5 , ring A 6 , ring A 7 and ring A 8 are independently 1,4-phenylene, and at least one of hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 5 carbons, alkoxy having 1 to 5 carbons, or alkyl having 1 to 5 carbons or alkoxy having 1 to 5 carbons in which at least one of hydrogen is replaced b

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Kobayashi Masahide
• Gotoh Yasuyuki
• Goto Mayumi

Classifications

• C08K5/0008

  Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59 · CPC title

• C07C69/73

  of unsaturated acids · CPC title

• C07C69/65

  of unsaturated acids · CPC title

• C09K2019/546

  creating a polymeric network · CPC title

• C08F20/30

  containing aromatic rings in the alcohol moiety · CPC title