Compound, haze-lowering agent, liquid crystal composition, polymer material, and film

Patent metadata

Field	Value
Publication number	US-9481829-B2
Application number	US-201414163901-A
Country	US
Kind code	B2
Filing date	Jan 24, 2014
Priority date	Jul 27, 2011
Publication date	Nov 1, 2016
Grant date	Nov 1, 2016

Abstract

A compound represented by the following formula (1) has sufficient solubility, a wide usable concentration range, and excellent haze-lowering performance. In the formula, L 1 to L 6 represent a single bond, —O—, —CO—, —COO—, etc; Sp 1 to Sp 4 represent a single bond or alkylene of 1 to 10 carbon atoms; A 1 and A 2 represent trivalent or tetravalent aromatic hydrocarbon or heterocyclic; T represents the following formulae, etc; Hb represent perfluoroalkyl of 2 to 30 carbon atoms; m and n are 2 or 3; and o and p are an integer of 0 or more.

First claim

What is claimed is:

1. A compound represented by the following formula (I):
(Hb-Sp 1 -L 1 -Sp 2 -L 2 ) m -A 1 -L 3 -T-L 4 -A 2 -(L 5 -Sp 3 -L 6 -Sp 4 -Hb) n   Formula (I)

wherein L 1 , L 2 , L 5 , and L 6 each independently represent a single bond, —O—, —S—, —CO—, —COO—, —OCO—, —COS—, —SCO—, —NRCO—, or —CONR—, L 3 is —COO— or —CONR—, L 4 is —OCO—, and T is

 R in the formula (I) each independently represent a hydrogen atom or an alkyl group of 1 to 6 carbon atoms, Sp 1 , Sp 2 , Sp 3 , and Sp 4 each independently represent a single bond or an alkylene group of 1 to 10 carbon atoms in which each of the hydrogen atoms of the alkylene group may be substituted with a fluorine atom, A 1 and A 2 represent a trivalent or tetravalent aromatic hydrocarbon group, wherein X represents an alkyl group of 1 to 8 carbon atoms, an alkoxy group, a halogen atom, a cyano group, or —COOR 0 in which R 0 represents a hydrogen atom, an alkyl or fluoroalkyl group in which each of the linking CH 2 may be substituted with O or S, or -Sp 5 -P in which Sp 5 represents a single bond or an alkylene group of 1 to 10 carbon atoms in which each of the hydrogen atoms of the alkylene group may be substituted with a fluorine atom, and P represents a polymerizable group, Ya, Yb, Yc, and Yd each independently represent a hydrogen atom or an alkyl group of 1 to 4 carbon atoms,

Hb's each independently represent a perfluoroalkyl or fluoroalkyl group of 2 to 30 carbon atoms, m and n are each independently 2 or 3, and the structures in a plurality of parentheses may be the same or different, o is an integer of 0 or more, and a plurality of X when o is 2 or more may be the same or different.

2. The compound according to claim 1 , wherein, in the formula (I), L 3 is —COO—, L 4 is —OCO—, and A 1 and A 2 are each independently any one of the following:

and
L 2 and L 5 are —O—.

3. The compound according to claim 1 , wherein Hb's in the formula (I) are independently a perfluoroalkyl group of 2 to 30 carbon atoms.

4. A haze-lowering agent that comprises a compound represented by the following formula (I):
(Hb-Sp 1 -L 1 -Sp 2 -L 2 ) m -A 1 -L 3 -T-L 4 -A 2 -(L 5 -Sp 3 -L 6 -Sp 4 -Hb) n   Formula (I)

wherein L 1 , L 2 , L 5 , and L 6 each independently represent a single bond, —O—, —S—, —CO—, —COO—, —OCO—, —COS—, —SCO—, —NRCO—, or —CONR—, L 3 is —COO— or —CONR—, L 4 is —OCO—, and T is

 R in the formula (I) each independently represent a hydrogen atom or an alkyl group of 1 to 6 carbon atoms, Sp 1 , Sp 2 , Sp 3 , and Sp 4 each independently represent a single bond or an alkylene group of 1 to 10 carbon atoms in which each of the hydrogen atoms of the alkylene group may be substituted with a fluorine atom, A 1 and A 2 represent a trivalent or tetravalent aromatic hydrocarbon group, wherein X represents an alkyl group of 1 to 8 carbon atoms, an alkoxy group, a halogen atom, a cyano group, or —COOR 0 in which R 0 represents a hydrogen atom, an alkyl or fluoroalkyl group in which each of the linking CH 2 may be substituted with O or S, or -Sp 5 -P in which Sp 5 represents a single bond or an alkylene group of 1 to 10 carbon atoms in which each of the hydrogen atoms of the alkylene group may be substituted with a fluorine atom, and P represents a polymerizable group, Ya, Yb, Yc, and Yd each independently represent a hydrogen atom or an alkyl group of 1 to 4 carbon atoms,

Hb's each independently represent a perfluoroalkyl or fluoroalkyl group of 2 to 30 carbon atoms, m and n are each independently 2 or 3, and the structures in a plurality of parentheses may be the same or different, o is an integer of 0 or more, and a plurality of X when o is 2 or more may be the same or different.

5. A liquid crystal composition that comprises a polymerizable liquid crystal molecule, and a compound represented by the following formula (I):
(Hb-Sp 1 -L 1 -Sp 2 -L 2 ) m -A 1 -L 3 -T-L 4 -A 2 -(L 5 -Sp 3 -L 6 -Sp 4 -Hb) n   Formula (I)

wherein L 1 , L 2 , L 5 , and L 6 each independently represent a single bond, —O—, —S—, —CO—, —COO—, —OCO—, —COS—, —SCO—, —NRCO—, or —CONR—, L 3 is —COO— or —CONR—, L 4 is —OCO—, and T is

R in the formula (I) each independently represent a hydrogen atom or an alkyl group of 1 to 6 carbon atoms, Sp 1 , Sp 2 , Sp 3 , and Sp 4 each independently represent a single bond or an alkylene group of 1 to 10 carbon atoms in which each of the hydrogen atoms of the alkylene group may be substituted with a fluorine atom, A 1 and A 2 represent a trivalent or tetravalent aromatic hydrocarbon group, wherein X represents an alkyl group of 1 to 8 carbon atoms, an alkoxy group, a halogen atom, a cyano group, or —COOR 0 in which R 0 represents a hydrogen atom, an alkyl or fluoroalkyl group in which each of the linking CH 2 may be substituted with O or S, or -Sp 5 -P in which Sp 5 represents a single bond or an alkylene group of 1 to 10 carbon atoms in which each of the hydrogen atoms of the alkylene group may be substituted with a fluorine atom, and P represents a polymerizable group, Ya, Yb, Yc, and Yd each independently represent a hydrogen atom or an alkyl group of 1 to 4 carbon atoms,
Hb's each independently represent a perfluoroalkyl or fluoroalkyl group of 2 to 30 carbon atoms, m and n are each independently 2 or 3, and the structures in a plurality of parentheses may be the same or different, o is an integer of 0 or more, and a plurality of X when o is 2 or more may be the same or different.

6. The liquid crystal composition according to claim 5 , wherein the polymerizable liquid crystal molecule is a rod-like liquid crystal molecule.

7. The liquid crystal composition according to claim 5 , wherein said composition further contains at least one chiral compound.

8. A polymer material produced by polymerizing a liquid crystal composition, wherein the liquid crystal composition comprises a polymerizable liquid crystal molecule, and a compound represented by the following formula (I):
(Hb-Sp 1 -L 1 -Sp 2 -L 2 ) m -A 1 -L 3 -T-L 4 -A 2 -(L 5 -Sp 3 -L 6 -Sp 4 -Hb) n   Formula (I)

wherein L 1 , L 2 , L 5 , and L 6 each independently represent a single bond, —O—, —S—, —CO—, —COO—, —OCO—, —COS—, —SCO—, —NRCO—, or —CONR—, L 3 is —COO— or —CONR—, L 4 is —OCO—, and T is

R in the formula (I) each independently represent a hydrogen atom or an alkyl group of 1 to 6 carbon atoms, Sp 1 , Sp 2 , Sp 3 , and Sp 4 each independently represent a single bond or an alkylene group of 1 to 10 carbon atoms in which each of the hydrogen atoms of the alkylene group may be substituted with a fluorine atom, A 1 and A 2 represent a trivalent or tetravalent aromatic hydrocarbon group, wherein X represents an alkyl group of 1 to 8 carbon atoms, an alkoxy group, a halogen atom, a cyano group, or —COOR 0 in which R 0 represents a hydrogen atom, an alkyl or fluoroalkyl group in which each of the linking CH 2 may be substituted with O or S, or -Sp 5 -P in which Sp 5 represents a single bond or an alkylene group of 1 to 10 carbon atoms in which each of the hydrogen atoms of the alkylene group may be substituted with a fluorine atom, and P represents a polymerizable group, Ya, Yb, Yc, and Yd each independently represent

Assignees

• Fujifilm Corp

Inventors

• Mizumura Masatoshi
• Katoh Shunya
• Uemura Minoru
• Ishiwata Yasuhiro
• Yoshikawa Masaru
• Matsuyama Hiroshi

Classifications

• C09K2019/2078

  Ph-COO-Ph-COO-Ph · CPC title

• C09K19/588

  Heterocyclic compounds · CPC title

• C09K19/3475

  the heterocyclic ring being a six-membered aromatic ring containing at least three nitrogen atoms · CPC title

• C09K2019/0429

  the specific unit being a carbocyclic or heterocyclic discotic unit · CPC title

• C09K19/2007

  the chain containing -COO- or -OCO- groups · CPC title