Compound having four polymerizable groups, liquid crystal composition and liquid crystal display device

Patent metadata

Field	Value
Publication number	US-9617477-B2
Application number	US-201514820567-A
Country	US
Kind code	B2
Filing date	Aug 7, 2015
Priority date	Apr 24, 2012
Publication date	Apr 11, 2017
Grant date	Apr 11, 2017

Abstract

A compound represented by formula (1), a liquid crystal composition, a liquid crystal display device are described.

In formula (1), for example, the ring A 1 and the ring A 4 are phenylene or cyclohexylene; Z 1 , Z 2 , Z 3 and Z 4 are a single bond or alkylene having 1 to 6 carbons; L 1 is a single bond; s and t are 0; and P 1 , P 2 , P 3 and P 4 are a polymerizable group.

First claim

What is claimed is:

1. A compound represented by formula (1):

wherein ring A 1 , ring A 2 , ring A 3 and ring A 4 are independently phenylene or cyclohexylene, and in these groups at least one hydrogen may be replaced by alkyl having 1 to 10 carbons, fluorine, —CF 2 H or —CF 3 ;
Z 1 , Z 2 , Z 3 and Z 4 are independently a single bond, —COO—, —CH 2 O— or —CH═CHO—;
L 1 , L 2 and L 3 are independently a single bond, —CH═CH—, —CH═CH—COO—, —C(CH 3 )═CH—COO—, —CH═C(CH 3 )—COO—, —C(CH 3 )═C(CH 3 )—COO—, —C≡C—, —COCH═CH—, —C(CH 3 )═C(CH 3 )—, —CH═CH—CH 2 O—, —CH═CH—OCH 2 — or —CO—, and at least one of L 1 , L 2 and L 3 is —CH═CH—, —CH═CH—COO—, —C(CH 3 )═CH—COO—, —CH═C(CH 3 )—COO—, —C(CH 3 )═C(CH 3 )—COO—, —C≡C—, —COCH═CH—, —C(CH 3 )═C(CH 3 )—, —CH═CH—CH 2 O—, —CH═CH—OCH 2 — or —CO—;
s and t are independently 0 or 1, and the sum of s and t is 0, 1 or 2;
P 1 , P 2 , P 3 and P 4 are the group (P-1):

wherein M is hydrogen, fluorine, -CH 3 or -CF 3 .

2. The compound according to claim 1 , wherein the compound is represented by any one of formulas (1-1) to (1-6):

wherein Z 1 , Z 2 , Z 3 and Z 4 are independently a single bond, —COO—, —CH 2 O— or—CH═CHO—; L 1 and L 2 are independently a single bond, —CH═CH—, —CH═CH—COO—, —C(CH 3 )═CH—COO—, —CH ═C(CH 3 )—COO—, —C(CH 3 )═C(CH 3 )—COO—, —C≡C—, —COCH═CH—, —C(CH 3 )═C(CH 3 )—,—CH═CH—CH 2 O—, —CH═CH—OCH 2 — or —CO—, and at least one of L 1 and L 2 is —CH═CH—, —CH═CH—COO—, —C(CH 3 )═CH—COO—, —CH═C(CH 3 )—COO—, —C(CH 3 )═C(CH 3 )—COO—, —C≡C—, —COCH═CH—, —C(CH 3 )═C(CH 3 )—, —CH═CH—CH 2 O—, —CH═CH—OCH 2 — or —CO—; X 11 , X 12 , X 13 , X 14 , X 15 , X 16 , X 17 , X 18 , X 19 , X 20 , X 21 , X 22 , X 23 and X 24 are independently hydrogen, alkyl having 1 to 10 carbons, fluorine, —CF 2 H or —CF 3 ; s is 0 or 1; and P 1 , P 2 , P 3 and P 4 are the group (P-1):

wherein M is hydrogen, fluorine, —CH 3 or —CF 3 .

3. The compound according to claim 2 , wherein in formulas (1-1) to (1-6), s is 0.

4. The compound according to claim 2 , wherein in formulas (1-1) to (1-6), Z 1 , Z 2 , Z 3 and Z 4 are independently a single bond; s is 0 or 1; and P is CH 2 ═CH—COO— 5 or CH 2 ═C(CH 3 )—COO—.

5. The compound according to claim 2 , wherein in formulas (1-1) to (1-6), Z 1 , Z 2 , Z 3 and Z 4 are independently —COO—, —CH 2 O— or —CH═CHO—; s is 0 or 1; and P is CH 2 ═CH—COO— or CH 2 ═C(CH 3 )—COO—.

6. The compound according to claim 2 , wherein in formulas (1-1) to (1-3), Z 1 , Z 2 , Z 3 and Z 4 are independently a single bond; s is 0 or 1; L 1 and L 2 are independently a single bond, —CH═CH— or —CH═CHCOO—; and P is CH 2 ═CH—COO— or CH 2 ═C(CH 3 )—COO—.

7. The compound according to claim 2 , wherein in formulas (1-1) to (1-3), Z 1 , Z 2 , Z 3 and Z 4 are —CH═CHO—; s is 0 or 1; L 1 and L 2 are independently a single bond, —CH═CH— or —CH═CHCOO—; and P is CH 2 ═CH—COO— or CH 2 ═C(CH 3 )—COO—.

8. A polymer obtained from the compound according to claim 1 .

9. A liquid crystal composition including the compound according to claim 1 .

10. The liquid crystal composition according to claim 9 , further including at least one compound selected from the group consisting of compounds represented by formulas (2), (3) and (4):

wherein R 3 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in these groups at least one hydrogen may be replaced by fluorine and at least one —CH 2 —may be replaced —O—;
X 1 is independently fluorine, chlorine, —OCF 3 , —OCHF 2 , —CF 3 , —CHF 2 , —CH 2 F, —OCF 2 CHF 2 or —OCF 2 CHFCF 3 ;
ring B 1 , ring B 2 and ring B 3 are independently 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, tetrahydropyran-2,5-diyl, or 1,4-phenylene in which at least one hydrogen may be replaced by fluorine;
Y 1 and Y 2 are independently —(CH 2 ) 2 —, —(CH 2 ) 4 —, —COO—, —CF 2 O—, —OCF 2 —, —CH═CH—, —C≡C—, —CH 2 O— or a single bond; and
Q 1 and Q 2 are independently hydrogen or fluorine.

11. The liquid crystal composition according to claim 9 , further including at least one compound selected from the group consisting of compounds represented by formula (5):

wherein R 4 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in these groups at least one hydrogen may be replaced by fluorine and at least one —CH 2 —may be replaced by —O—;
X 2 is —CN or —C≡C—CN;
ring C 1 , ring C 2 and ring C 3 are independently 1,4-cyclohexylene, 1,4-phenylene in which at least one hydrogen may be replaced by fluorine, 1,3-dioxane-2,5-diyl, tetrahydropyran-2,5-diyl or pyrimidine-2,5-diyl;
Y 3 is —(CH 2 ) 2 —, —COO—, —CF 2 O—, —OCF 2 —, —C≡C—, —CH 2 O— or a single bond;
Q 3 and Q 4 are independently hydrogen or fluorine; and
q is 0, 1 or 2, and r is 0 or 1.

12. The liquid crystal composition according to claim 9 , further including at least one compound selected from the group consisting of compounds represented by formulas (6), (7), (8), (9), (10) and (11):

wherein R 5 and R 6 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in these groups at least one hydrogen may be replaced by fluorine and at least one —CH 2 — may be replaced by —O—;
ring D 1 , ring D 2 , ring D 3 and ring D 4 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene in which at least one hydrogen may be replaced by fluorine, tetrahydropyran-2,5-diyl or decahydro-2,6-naphthalene;
Y 4 , Y 5 , Y 6 and Y 7 are independently —(CH 2 ) 2 —, —COO—, —CH 2 O—, —OCF 2 —, —OCF 2 (CH 2 ) 2 — or a single bond;
Q 5 and Q 6 are independently fluorine or chlorine; and
j, k, l, m, n and p are independently 0 or 1, and the sum of k, l, m and n is 1 or 2.

13. The liquid crystal composition according to claim 9 , further including at least one compound selected from the group consisting of compounds represented by formulas (12), (13) and (14):

wherein R 7 and R 8 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in these groups at least one hydrogen may be replaced by fluorine and at least one —CH 2 — may be replaced by —O—;
ring E 1 , ring E 2 and ring E 3 are independently 1,4-cyclohexylene, pyrimidine-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene or 2,5-difluoro-1,4-phenylene; and
Y 8 and Y 9 are independently —C≡C—, —COO—, —(CH 2 ) 2 —, —CH═CH— or a single bond.

14. The liquid crystal composition according to claim 10 , further including at least one compound selected from the group consisting of compounds represented by formulas (12), (13) and (14):

wherein R 7 and R 8 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in these groups at least one hydrogen may

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Goto Yasuyuki
• MATSUKUMA Maiko
• Yamashita Junichi

Classifications

• C09K2019/0448

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

• C07C69/80

  Phthalic acid esters · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• C09K19/2007

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

• C09K19/3003

  Compounds containing at least two rings in which the different rings are directly linked (covalent bond) · CPC title