IP Library Granted Patent US 10,011,771
Granted Patent B2
US 10,011,771 · App. 14/238,153 · Granted Jul 3, 2018

Liquid crystal composition containing polymerizable compound and liquid crystal display element using same

Inventors: Kazuki Kurisawa (Saitama, JP); Takeshi Kuriyama (Saitama, JP); Shotaro Kawakami (Saitama, JP)
Assignee: DIC CORPORATION (TOKYO)
C09K19/542C09K19/10C09K19/12C09K19/20C09K19/3003C09K19/3028C09K19/3066C09K19/322C09K19/3402C09K19/3483C09K19/56G02F1/1341G02F1/133365G02F1/133528G02F1/133703G02F1/133723G02F1/133788C09K19/3411C09K2019/0448C09K2019/121C09K2019/122C09K2019/123C09K2019/301C09K2019/3004C09K2019/3009C09K2019/3016C09K2019/3036C09K2019/3037C09K2019/325C09K2019/3416C09K2019/3425C09K2019/548G02F1/133753G02F2001/133397G02F2001/133742G02F2001/133746G02F2001/133749G02F2202/022
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Quick Facts
Patent No.
US 10,011,771
App. No.
14/238,153
Granted
Jul 3, 2018
Kind
B2
Abstract

A liquid crystal composition containing a polymerizable compound of the present invention has excellent characteristics of being able to prepare a PSA type liquid crystal display element with no problem of depositing in a wide temperature range, having high polymerization speed, high liquid crystal alignment regulation force after polymerization, excellent display qualities with no display unevenness, and excellent display characteristics with no defects in display characteristics such as image sticking and is appropriate as a liquid crystal composition in a practical use. Further, the liquid crystal display element with the above-described liquid crystal composition can be appropriately used for a PSA type liquid crystal display element.

Claims (28)

1. A polymerizable-compound-containing liquid crystal composition, comprising:

a first component consisting of, one or two or more kinds of polymerizable compounds represented by general formula (I):

wherein R 1 and R 2 are the same and represent any one of the following formulae (R-1) to (R-15), S 1 and S 2 each independently represent an alkylene group having 1 to 12 carbon atoms or a single bond, a methylene group in the alkylene group may be substituted with an oxygen atom, a sulfur atom, —CO—, —COO—, —OCO—, —OCOO— or —CH═CH— as long as oxygen atoms are not directly bonded to each other, provided that at least one of S 1 and S 2 is not a single bond, and X 1 to X 12 each independently represent a hydrogen atom, a trifluoromethyl group, a trifluoromethoxy group, or a methyl group

as a second component, one or two or more kinds of compounds represented by general formula (II):

R 21 -M 21 -L 21 -M 22 -(L 22 -M 23 ) o -R 22   (II)

wherein R 21 and R 22 each independently represent an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, one methylene group or two or more non-adjacent methylene groups present in these groups may be substituted with —O— or —S—, and one or two or more hydrogen atoms present in these groups may be substituted with a fluorine atom or a chlorine atom,

M 21 , M 22 , and M 23 each independently represent a group selected from the group consisting of (a) a trans-1,4-cyclohexylene group (one methylene group or two or more non-adjacent methylene groups present in the group may be substituted with —O— or —S—), (b) a 1,4-phenylene group (one —CH═ or two or more non-adjacent (—CH═)'s present in the group may be substituted with a nitrogen atom), a 3-fluoro-1,4-phenylene group, a 3,5-difluoro-1,4-phenylene group, and (c) a 1,4-cyclohexenylene group, a 1,4-bicyclo[2,2,2]octylene group, a piperidine-2,5-diyl group, a naphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, and a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group,

o represents 0, 1, or 2, and

L 21 and L 22 each independently represent a single bond, —CH 2 CH 2 —, —(CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —OCF 2 —, —CF 2 O—, —CH═CH—, —CH═N—N═CH—, or —C≡C—, and when a plurality of L 22 's and/or M 23 's are present, they may be the same as or different from each other, and

as a third component, at least one compound selected from the group consisting of the compounds represented by general formulae (IVa-2c) and (IVa-3d):

wherein R 47 and R 48 each independently represent and alkyl group having 1 to 8 carbon atoms, and alkoxyl group having 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms), and optionally a compound selected from the group consisting of compounds represented by general formulae (IVa), (IVb), and (IVc):

wherein R 41 , R 42 , R 43 , R 44 , R 45 , and R 46 each independently represent an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and one methylene group or two or more non-adjacent methylene groups present in these groups may be substituted with —O— or —S—, and one or two or more of hydrogen atoms present in these groups may be substituted with a fluorine atom or a chloride atom,

M 41 , M 42 , M 43 , M 44 , M 45 , M 46 , M 47 , M 48 , and M 49 each independently represent a group selected from the group consisting of (d) a trans-1,4-cyclohexylene group (one methylene group or two or more non-adjacent methylene groups present in the group may be substituted with —O— or —S—), (e) a 1,4-phenylene group (one —CH═ or two or more non-adjacent (—CH═)'s present in the group may be substituted with a nitrogen atom), and (f) a 1,4-cyclohexenylene group, a 1,4-bicyclo[2,2,2]octylene group, a piperidine-2,5-diyl group, a naphthalene-2,6-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and a decahydronaphthalene-2,6-diyl group, and a hydrogen atom contained in the groups (d), (e), and (f) may be substituted with a cyano group, a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group, or a chlorine atom,

L 41 , L 42 , L 43 , L 44 , L 45 , L 46 , L 47 , L 48 and L 49 each independently represent a single bond, —COO—, —OCO—, —CH 2 CH 2 —, —(CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —OCF 2 —, —CF 2 O—, or —C≡C→, and when a plurality of M 42 , M 43 , M 45 , M 46 , M 48 , M 49 , L 41 , L 43 , L 44 , L 46 , L 47 , and/or L 49 are present, they may be the same as or different from each other,

X 41 , X 42 , X 43 , X 44 , X 45 , X 46 , X 47 , and X 48 each independently represent a hydrogen atom, a trifluoromethyl group, a trifluoromethoxy group, or a fluorine atom, any one of X 41 and X 42 represents a fluorine atom, any one of X 43 , X 44 , and X 45 represents a fluorine atom, any one of X 46 , X 47 , and X 48 represents a fluorine atom, provided that X 46 and X 47 do not represent a fluorine atom and X 46 and X 48 do not represent a fluorine atom at the same time,

G represents a methylene group or —O—, and

u, v, w, x, y, and z each independently represent 0, 1, or 2, and u+v, w+x, and y+z are each 2 or less;

wherein the liquid crystal composition contains the first component in the range of 0.01% by mass to 2% by mass, the second component in the range of 5% by mass to 70% by mass and the third component in the range of 5% by mass to 70% by mass.

2. The polymerizable-compound-containing liquid crystal composition according to claim 1 , wherein the liquid crystal composition contains as the first component, one or two or more kinds of compounds in which at least one of X 1 to X 12 in general formula (I) is a trifluoromethyl group, a trifluoromethoxy group, or a methyl group.

3. The polymerizable-compound-containing liquid crystal composition according to claim 1 , wherein the liquid crystal composition contains as the first component, one or two or more kinds of compounds in which at least one of X 1 to X 12 in general formula (I) is a methyl group.

4. The polymerizable-compound-containing liquid crystal composition according to claim 1 , wherein the liquid crystal composition contains as the first component, one or two or more kinds of compounds in which X 1 , X 6 , X 7 , and X 12 in general formula (I) are hydrogen atoms.

5. The polymerizable-compound-containing liquid crystal composition according to claim 1 , wherein the liquid crystal composition contains as the first component, one or two or more kinds of polymerizable compounds selected from polymerizable compounds represented by general formula (I-2), (I-3), (I-21), (I-26), and (I-36):

wherein S 1 and S 2 each independently represent an alkylene group having 1 to 12 carbon atoms or a single bond, a methylene group in the alkylene group may be substituted with an oxygen atom, a sulfur atom, —CO—, —COO—, —OCO—, —OCOO—OCOO— or —CH═CH— as long as oxygen atoms are not directly bonded to each other, provided that at least one of S 1 and S 2 is not a single bond, R 1 represents the same definition as R 1 according to claim 1 , and R 2 represents the same definition as R 2 according to claim 1 .

6. The polymerizable-compound-containing liquid crystal composition according to claim 1 , wherein a dielectric anisotropy of the polymerizable-compound-containing liquid crystal composition is negative.

7. The polymerizable-compound-containing liquid crystal composition according to claim 1 , wherein the liquid crystal composition is used for a liquid crystal display element that has a pair of substrates, a liquid crystal interposed between the substrates, a transparent electrode, and a polarizer, in which a liquid crystal alignment capability is provided by polymerizing a polymerizable compound contained in the liquid crystal composition.

8. A liquid crystal display element using the polymerizable-compound-containing liquid crystal composition according to claim 1 and comprising a pair of substrates, a liquid crystal interposed between the substrates, a transparent electrode, and a polarizer, wherein a liquid crystal alignment capability is provided by polymerizing a polymerizable compound contained in the liquid crystal composition.

9. The polymerizable-compound-containing liquid crystal composition according to claim 1 , wherein at least one of X 1 to X 12 is from the group consisting of a trifluoromethyl group, a trifluoromethoxy group or a methyl group.

10. The polymerizable-compound-containing liquid crystal composition according to claim 1 , wherein R 47 and R 48 each independently represent and alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 24, 2024
From: DIC CORPORATION
To: SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIAL CO., LTD.
Reel/Frame 067528/0688 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 12, 2014
From: KURISAWA, KAZUKI; KURIYAMA, TAKESHI; KAWAKAMI, SHOTARO
To: DIC CORPORATION
Reel/Frame 033092/0177 →
Priority Claims (1)
JP 2011-175909 · Aug 11, 2011 · national
Continuity (1)
Related Publication 20140293213A1 · Oct 2, 2014