Polymerizable compound, polymerizable composition and liquid crystal display device

Patent metadata

Field	Value
Publication number	US-10077401-B2
Application number	US-201414903594-A
Country	US
Kind code	B2
Filing date	Mar 13, 2014
Priority date	Jul 10, 2013
Publication date	Sep 18, 2018
Grant date	Sep 18, 2018

Abstract

A polymerizable compound having high polymerization reactivity, a high conversion ratio and high solubility in a liquid crystal composition, a polymerizable composition containing the compound, a liquid crystal composite prepared from the composition and a liquid crystal display device having the composite are shown. The polymerizable compound has three or four rings in a serial arrangement and not being mutually condensed, and has three or more polymerizable groups among which at least one is bonded with a ring which is not an either terminal of the three or four rings. The polymerizable composition contains the above polymerizable compound and a liquid crystal composition. The liquid crystal composite is prepared from the above polymerizable composition, and the liquid crystal display device has the liquid crystal composite.

First claim

The invention claimed is:

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

wherein in formula (1),
P 1 , P 2 , P 3 and P 4 are a polymerizable group;
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 —CH 2 — may be replaced by —O—, —COO—, —OCO— or —OCOO—, at least one —CH 2 —CH 2 — may be replaced by —CH═CH— or —C≡C—, and at least one hydrogen may be replaced by fluorine or chlorine;
a1, a3, and a4 are independently 0, 1, 2, 3 or 4, a2 is 1, 2, 3 or 4, and a sum of a1, a2, a3 and a4 is 3 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 hydrogen may be replaced by halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by halogen, or alkoxy having 1 to 12 carbons in which at least one 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 hydrogen may be replaced by halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by halogen, or alkoxy having 1 to 12 carbons in which at least one hydrogen is replaced by halogen;
Z 1 , Z 2 and Z 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—, —CO—, —COO— or —OCO—, with a proviso that a total number of —COO— and —OCO— in Z 1 , Z 2 and Z 3 is 0 or 1, 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 at least one hydrogen may be replaced by fluorine or chlorine; and
b1 is 0 or 1.

2. The polymerizable compound of claim 1 , wherein, in formula (1),
P 1 , P 2 , P 3 and P 4 are acryloyloxy or methacryloyloxy;
S 1 , S 2 , S 3 and S4 are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, one of —CH 2 — may be replaced by —O—, —COO—, —OCO— or —OCOO—one of —CH 2 —CH 2 — may be replaced by —CH═CH— or —C≡C—,and at least one hydrogen may be replaced by fluorine or chlorine;
a1, a3 and a4 are independently 0, 1, 2, 3 or 4, a2 is 1, 2, 3 or 4, and a sum of a1, a2, a3 and a4 is 3 to 10;
ring A 1 and ring A 4 are independently phenyl, pyrimidyl, pyridyl or naphthyl, and in the rings, at least one hydrogen may be replaced by halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by halogen, or alkoxy having 1 to 12 carbons in which at least one 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 hydrogen may be replaced by halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by halogen, or alkoxy having 1 to 12 carbons in which at least one hydrogen is replaced by halogen;
Z 1 , Z 2 and Z 3 are independently a single bond, alkylene having 1 to 5 carbons, —CO—, —COO—, —OCO—, —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 )—, —CO—CH═CH—, —CH═CH—CO—, —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—, with a proviso that a total number of —COO— and —OCO— in Z 1 , Z 2 and Z 3 is 0 or 1; and
b1 is 0 or 1.

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

wherein, in formula (1-1),
P 5 , P 6 , P 7 and P 8 are independently acryloyloxy or methacryloyloxy;
S 5 , S 6 , S 7 and S 8 are independently a single bond or alkylene having 1 to 5 carbons, and in the alkylene, one of —CH 2 —may be replaced by —O—, —COO— or —OCO—, and one of —CH 2 —CH 2 —may be replaced by —CH═CH—;
c1, c3 and c4 are independently 0, 1 or 2, c2 is 1 or 2, and a sum of c1, c2, c3 and c4 is 3 to 6;
ring A 5 and ring A 8 are independently phenyl in which at least one hydrogen may be replaced by halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by halogen, or alkoxy having 1 to 12 carbons in which at least one hydrogen is replaced by halogen;
ring A 6 and ring A 7 are independently 1,4-phenylene in which at least one hydrogen may be replaced by halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by halogen, or alkoxy having 1 to 12 carbons in which at least one hydrogen is replaced by halogen;
Z 4 , Z 5 and Z 6 are independently a single bond, alkylene having 1 to 5 carbons, —CO—, —COO—,—OCO—, —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 )—, —CO—CH═CH—, —CH═CH—CO—, —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—, with a proviso that a total number of —COO—and —OCO—in Z 4 , Z 5 and Z 6 is 0 or 1; and
d1is 0 or 1.

4. The polymerizable compound of claim 1 , represented by any one of formula (1-1-1) or (1-1-2):

wherein, in formulas (1-1-1) and (1-1-2),
P 9 , P 10 , P 11 , P 12 , P 13 and P 14 are independently acryloyloxy or methacryloyloxy;
S 11 , S 12 , S 13 , S 14 , S 15 and S 16 are independently a single bond or alkylene having 1 to 5 carbons, and in the alkylene, one of —CH 2 — may be replaced by —O—, —COO—or —OCO—, and one of —CH 2 —CH 2 — may be replaced by —CH═CH—;
e1, e3 and e4 are independently 0, 1 or 2, e2 is 1 or 2, and a sum of e1, e2, e3 and e4 is 1 to 4;
Z 7 , Z 8 and Z 9 are independently a single bond, alkylene having 1 to 5 carbons, —CO—, —COO—, —OCO—, —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 )—, —CO—CH═CH—, —CH═CH—CO—,—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—, with a proviso that a total number of —COO— and —OCO— in Z 7 , Z 8 and Z 9 in formula (1-1-1) or in Z 7 and Z 8 in formula (1-1-2) is 0 or 1;
g1 is 0, 1 or 2; and
Y 1 is halogen, alkyl having 1 to 5 carbons, alkoxy having 1 to 5 carbons, alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by halogen, or alkoxy having 1 to 5 carbons in which at least one hydrogen is replaced by halogen.

5. The polymerizable compound of claim 1 , represented by formula (1-2) or (1-3):

wherein, in formulas (1-2) and (1-3),
P 9 , P 10 ,P 11 , P 12 , P 13 and P 14 are independently acryloyloxy or methacryloyloxy;
S 9 , S 10 , S 11 , S 12 ,

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Kobayashi Masahide
• Gotoh Yasuyuki
• Kobayashi Takahiro

Classifications

• C07C69/653

  Acrylic acid esters; Methacrylic acid esters; Haloacrylic acid esters; Halomethacrylic acid esters · CPC title

• C08F222/1006

  of polyhydric alcohols or polyhydric phenols · CPC title

• C09K19/20

  linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters {or ethers} · CPC title

• C09K2019/123

  Ph-Ph-Ph · CPC title

• C07C69/017

  Esters of hydroxy compounds having the esterified hydroxy group bound to a carbon atom of a six-membered aromatic ring · CPC title