Nematic liquid crystal composition and liquid crystal display element including the same

Patent metadata

Field	Value
Publication number	US-2016319192-A1
Application number	US-201415108859-A
Country	US
Kind code	A1
Filing date	Dec 17, 2014
Priority date	Jan 6, 2014
Publication date	Nov 3, 2016
Grant date	—

Abstract

There is provided a liquid crystal composition whose refractive index anisotropy (Δn) and nematic phase-isotropic liquid phase transition temperature (T ni ) are sufficiently high, whose viscosity (η) is sufficiently low, whose rotational viscosity (γ 1 ) is sufficiently low, whose elastic constant (K 33 ) is high, whose dielectric anisotropy (Δ∈) is high or whose Δ∈ is negative with a large absolute value, and whose decrease in reliability after UV irradiation is small, and also provide a liquid crystal display element including the same, which has the excellent display quality and the high response speed. It has been found that the above object can be achieved by forming a polymerizable compound containing liquid crystal composition, which includes a polymerizable compound with a particular chemical structure and a non-polymerizable liquid crystal compound, the polymerizable compound with a particular chemical structure being contained at a particular ratio, and a liquid crystal display element including the same.

First claim

1 . A polymerizable compound containing liquid crystal composition comprising a polymerizable compound and a liquid crystal compound, the polymerizable compound being contained by 0.41 mass % or more and 10.0 mass % or less in total, wherein
as the polymerizable compound, one kind or two or more kinds of compounds represented by a general formula (1) are contained:

(in the general formula (1), Z 11 represents a fluorine atom, a cyano group, a hydrogen atom, an alkyl group with 1 to 15 carbon atoms whose hydrogen atom may be substituted with a halogen atom, an alkoxy group with 1 to 15 carbon atoms whose hydrogen atom may be substituted with a halogen atom, an alkenyl group with 1 to 15 carbon atoms whose hydrogen atom may be substituted with a halogen atom, an alkenyloxy group with 1 to 15 carbon atoms whose hydrogen atom may be substituted with a halogen atom, or -Sp 12 -R 1 ,
R 11 and R 12 independently represent any of the following formulae (R-1) to (R-15):

Sp 11 and Sp 12 represent a spacer group,
L 11 and L 12 independently represent a single bond, —O—, —S—, —CH 2 —, —OCH 2 —, —CH 2 O—, —CO—, —C 2 H 4 —, —COO—, —OCO—, —OCOOCH 2 —, —CH 2 OCOO—, —OCH 2 CH 2 O—, —CO—NR a —, —NR a —CO—, —SCH 2 —, —CH 2 S—, —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 —, —CF 2 O—, —OCF 2 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —CF 2 CF 2 —, or —C≡C— (in the formula, R a independently represents a hydrogen atom or an alkyl group with 1 to 4 carbon atoms, and in the formula, z represents an integer of 1 to 4),
M 12 represents a 1,4-phenylene group, a 1,4-cyclohexylene group, an anthracene-2,6-diyl group, a phenanthrene-2,7-diyl group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, an indane-2,5-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, and M 12 may be non-substituted or be substituted with an alkyl group with 1 to 12 carbon atoms, a halogenated alkyl group with 1 to 12 carbon atoms, an alkoxy group with 1 to 12 carbon atoms, a halogenated alkoxy group with 1 to 12 carbon atoms, a halogen atom, a cyano group, a nitro group, or —R 11 ,
M 11 represents any of the following formulae (i-11) to (ix-11):

(in the formula, the compound is bonded to Sp 11 at ★, and to L 11 or L 12 at ★ ★),
M 13 represents any of the following formulae (i-13) to (ix-13):

(in the formula, the compound is bonded to Z 11 at ★ and to L 12 at ★ ★),
m 12 represents 0, 1, 2, or 3, m 11 and m 13 independently represent 1, 2, or 3, and when there is a plurality of Z 11 , the plurality of Z 11 is either the same or different, when there is a plurality of R 11 , the plurality of R 11 is either the same or different, when there is a plurality of R 12 , the plurality of R 12 is either the same or different, when there is a plurality of Sp 11 , the plurality of Sp 11 is either the same or different, when there is a plurality of Sp 12 , the plurality of Sp 12 is either the same or different, when there is a plurality of L 11 , the plurality of L 11 is either the same or different, and when there is a plurality of M 12 , the plurality of M 12 is either the same or different); and
as the liquid crystal compound, one kind or two or more kinds of compounds represented by a general formula (LC) are contained:

(in the general formula (LC), R LC represents an alkyl group with 1 to 15 carbon atoms, one or two or more CH 2 groups in the alkyl group may be substituted with —O—, —CH═CH—, —CO—, —OCO—, —COO—, or —C≡C— so that the oxygen atom is not adjacent directly, and one or two or more hydrogen atoms in the alkyl group may be substituted with a halogen atom arbitrarily,
A LC1 and A LC2 independently represent a group selected from:

(a) a trans-1,4-cyclohexylene group (one CH 2 group or two or more non-adjacent CH 2 groups in this trans-1,4-cyclohexylene group may be substituted with an oxygen atom or a sulfur atom);
(b) a 1,4-phenylene group (one CH group or two or more non-adjacent CH groups in this 1,4-phenylene group may be substituted with a nitrogen atom); and
(c) a 1,4-bicyclo(2.2.2)octylene group, a naphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and a chroman-2,6-diyl group, and one or two or more hydrogen atoms included in the group (a), the group (b), and the group (c) may be substituted with F, Cl, CF 3 , or OCF 3 ,
Z LC represents a single bond, —CH═CH—, —CF═CF—, —C≡C—, —CH 2 CH 2 —, —(CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —OCF 2 —, —CF 2 O—, —COO—, or —OCO—,
Y LC represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, or an alkyl group with 1 to 15 carbon atoms, and one or two or more CH 2 groups in the alkyl group may be substituted with —O—, —CH═CH—, —CO—, —OCO—, —COO—, —C≡C—, —CF 2 O—, or —OCF 2 — so that an oxygen atom is not directly adjacent, and one or two or more hydrogen atoms in the alkyl group may be substituted with a halogen atom arbitrarily, and
“a” represents an integer of 1 to 4, and when “a” represents 2, 3, or 4 and there is a plurality of A LC1 , the plurality of A LC1 is either the same or different, and when there is a plurality of Z LC , the plurality of Z LC is either the same or different).

2 . The polymerizable compound containing liquid crystal composition according to claim 1 , wherein as the compound represented by the general formula (LC), one kind or two or more kinds of compounds selected from the compounds represented by the following general formulae (LC1) and (LC2) are further contained:

(in the formula, R LC11 and R LC21 independently represent an alkyl group with 1 to 15 carbon atoms, and one or two or more CH 2 groups in the alkyl group may be substituted with —O—, —CH═CH—, —CO—, —OCO—, —COO—, or —C≡C—, so that an oxygen atom is not directly adjacent, and one or two or more hydrogen atoms in the alkyl group may be substituted with a halogen atom arbitrarily, and A LC11 and A LC21 independently represent any of the following structures:

(in the structure, one or two or more CH 2 groups in the cyclohexylene group may be substituted with an oxygen atom, one or two or more CH groups in the 1,4-phenylene group may be substituted with a nitrogen atom, and one or two or more hydrogen atoms in the structure may be substituted with F, Cl, CF 3 , or OCF 3 ), X LC11 , X LC12 , and X LC21 to X LC23 independently represent a hydrogen atom, F, Cl, CF 3 , or OCF 3 , Y LC11 and Y LC21 independently represent a hydrogen atom, Cl, F, CN, CF 3 , OCH 2 F, OCHF 2 , or OCF 3 , Z LC11 and Z LC12 independently represent a single bond, —CH═CH—, —CF═CF—, —C≡C—, —CH 2 CH 2 —, —(CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —OCF 2 —, —CF 2 O—, —COO—, or —OCO—, m LC11 and m LC21 indepe

Assignees

• Dainippon Ink & Chemicals

Inventors

• Hirata Shinichi
• Hara Tomoaki
• Hatano Naomi
• Umezu Yasuo

Classifications

• C09K2019/0448

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

• C09K19/3809

  Polyesters; Polyester derivatives, e.g. polyamides · CPC title

• C09K2019/3016

  Cy-Ph-Ph · CPC title

• C09K2019/3009

  Cy-Ph · CPC title

• C09K19/322 Primary

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