Polymerizable compound-containing liquid crystal composition and liquid crystal display element using same

Patent metadata

Field	Value
Publication number	US-9725651-B2
Application number	US-201414778775-A
Country	US
Kind code	B2
Filing date	Mar 18, 2014
Priority date	Mar 21, 2013
Publication date	Aug 8, 2017
Grant date	Aug 8, 2017

Abstract

There is provided a polymerizable compound-containing liquid crystal composition having strong alignment regulating force of a liquid crystal compound. The polymerizable compound-containing liquid crystal composition includes: a polymerizable compound; and a liquid crystal compound, in which the polymerizable compound includes at least one polymerizable compound represented by General Formula (I), and in which the liquid crystal compound includes at least one component selected from the group consisting of at least one compound represented by General Formula (II) as a second component, at least one compound represented by General Formulae (IIIa), (IIIb), and (IIIc) as a third component, and at least one compound represented by General Formulae (IVa), (IVb), and (IVc) as a fourth component.

First claim

The invention claimed is:

1. A polymerizable compound-containing liquid crystal composition, comprising:
0.01 mass % to 2 mass % of at least one kind of compound represented by General Formula (I):
(R 11 l M 11 L 11 -M 12 m L 12 -M 13 Z) n   (1)

(in the general formula (I), Z represents —S 1 —R 12 , S 1 is at least one linking group selected from the group consisting of an alkylene group having 1 to 5 carbon atoms and a single bond, and one —CH 2 — or non-adjacent two or more —CH 2 — in the alkylene group may be substituted with —O—, —COO—, —OCO—, or —OCOO—,
R 11 and R 12 each independently represent any one of the following formulae (R-I) and (R-III) to (R-IX):

in the formulae (R-I) and (R-III) to (R-IX), R 21 , R 31 , R 41 , R 51 and R 61 each independently are a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms, W is a single bond, —O— or a methylene group, T is a single bond or —COO—, and p, t, and q each independently are 0, 1, or 2,
L 11 s a single bond, —OCH 2 —, —CH 2 O—, —C 2 H 4 —, —COO—, —OCO—, —OCOOCH 2 —, —CH 2 OCOO—, —OCH 2 CH 2 O—, —CH═CR a —COO—, —CH═CR a —OCO—, —COO—CR a ═CH—, —OCO—CR a ═CH—, —COO—CR a ═CH—COO—, —COO—CR a ═CH—OCO—, —OCO—CR a ═CH—COO—, —OCO—CR a ═CH—OCO—, —(CH 2 ) z —C(═O)—O—, —(CH 2 ) z —O—(C═O)—, —O—(C═O)—(CH 2 ) z —, —(C═O)—O—(CH 2 ) z —, —CH═CH—, —CF═CF—, —CF═CH—, —CH═CF—, —CF 2 O—, —OCF 2 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —CF 2 CF 2 —, or —C≡C— (in the formulae, R a s each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and z represents an integer of 2 or 4),
L 12 is —OCH 2 —, —CH 2 O—, —C 2 H 4 —, —COO—, —OCO—, —OCOOCH 2 —, —CH 2 OCOO—, —OCH 2 CH 2 O—, —CH═CR a —COO—, —CH═CR a —OCO—, —COO—CR a ═CH—, —OCO—CR a ═CH—, —COO—CR a ═CH—COO—,—COO—CR a ═CH—OCO—, —OCO—CR a ═CH—COO—, —OCO—CR a ═CH—OCO—, —(CH 2 ) z —C(═O)—O—, —(CH 2 ) z —O—(C═O)—, —O—(C═O)—(CH 2 ) z —, —(C═O)—O—(CH 2 ) z —, —CH═CH—, —CF═CF—, —CF═CH—, —CH═CF—, —CF 2 O—, —OCF 2 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —CF 2 CF 2 —, or —C≡C— (in the formulae, R a s each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and z represents an integer of 2 or 4),
M 12 represents a 1,4-phenylene group, a naphthalene-2,6-diyl group, or an indan-2,5-diyl group, but M 12 each independently may be unsubstituted or may be substituted with an alkyl group having 1 to 12 carbon atoms, a halogenated alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a halogenated alkoxy group having 1 to 12 carbon atoms, a halogen, a cyano group, or a nitro group,
M 13 is each independently any one of the following formulae (i) to (ix):

l is 1 or 2, m represents an integer of 1 to 3, n represents an integer of 1 to 3, when m represents 2 and 3, two or three L 11 and M 12 may be the same as or different from each other, provided that, at least one L 11 represents a single bond,
further, in the case of l=1, M 11 represents a 1,4-phenylene group, or an indan-2,5-diyl group, but M 11 each independently may be unsubstituted or may be substituted with an alkyl group having 1 to 12 carbon atoms, a halogenated alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a halogenated alkoxy group having 1 to 12 carbon atoms, a halogen, a cyano group, or a nitro group, and
in the case of l=2, M 11 is any one of the above formulae (iv) to (vi));
5 mass % to 80 mass % of at least one kind of compound represented by General Formula (II):
R 21 -M 21 -L 21 -M 22 -(L 22 -M 23 ) o -R 22   (II)

(in the general formula (II), 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 —CH 2 — or two or more non-adjacent —CH 2 — present in these groups may be substituted with —O— or —S—, at least one hydrogen atom 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 —CH 2 — or two or more non-adjacent —CH 2 —present in this group may be substituted with —O— or —S—),
(b) a 1,4-phenylene group (one —CH═ or two or more non-adjacent —CH═ present in this group may be substituted with —N═), a 2-fluoro-1,4-phenylene group, a 3-fluoro-1,4-phenylene group, and 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—, when a plurality of L 22 exist, they may be the same as or different from each other, and when a plurality of M 23 exist, they may be the same as or different from each other); and
5 mass % to 80 mass % of at least one compound selected from the group consisting of compounds represented by General formulae (IIIa), (IIIb), (IIIc), (IVa), (IVb), and (IVc):

(in the general formulae (IIIa), (IIIb), and (IIIc), R 31 , R 32 , and R 33 each independently represent an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, one —CH 2 — or two or more non-adjacent —CH 2 — present in these groups may be substituted with —O— or —S—, at least one kind of hydrogen atom present in these groups may be substituted with a fluorine atom or a chlorine atom,
M 31 , M 32 , M 33 , M 34 , M 35 , M 36 , M 37 , and M 38 each independently represent a group selected from the group consisting of:
(d) a trans-1,4-cyclohexylene group (one —CH 2 — or two or more non-adjacent —CH 2 —present in this group may be substituted with —O— or —S—),
(e) a 1,4-phenylene group (one —CH═ or two or more non-adjacent —CH═ present in this group may be substituted with —N═), a 3-fluoro-1,4-phenylene group, and a 3,5-difluoro-1,4-phenylene group, 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 each hydrogen atom included in the group (d), the group (e), or the group (f) may be substituted with a cyano group, a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group, or a chlorine atom,
L 31 , L 32 , L 33 , L 34 , L 35 , L 36 , L 37 , and L 38 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 32 , M 34 , M 35 , M 37 , M 38 , L 31 , L 33 , L 35 , L 36 , and/or L 38 are present, they may be the same as or different from each other,
X 31 , X 32 , X 33 , X 34 , X 35 , X 36 , and X 37 each independently represent a hydrogen atom or a fluorine atom,
Y 31 , Y 32 , and Y 33 each independently represent a fluorine atom, a chlorine atom, a cyano group, a thiocyanate group, a trifluoromethoxy group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, or a difluoromethoxy group, and
p, q, r, s, and t each independently represent 0, 1, or 2, provided that each of q+r and s+t is 2 or less); and

Assignees

• Dainippon Ink & Chemicals

Inventors

• Hirata Shinichi
• Kawakami Shotaro

Classifications

• C09K19/2014 Primary

  containing additionally a linking group other than -COO- or -OCO-, e.g. -CH2-CH2-, -CH=CH-, -C=C-; containing at least one additional carbon atom in the chain containing -COO- or -OCO- groups, e.g. -(CH2)m-COO-(CH2)n- · CPC title

• C09K2019/0466

  the linking chain being a -CF2O- chain · CPC title

• C09K2019/0448

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

• C09K2019/2078

  Ph-COO-Ph-COO-Ph · CPC title

• C09K19/322

  Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring · CPC title