IP Library Granted Patent US 9,688,787
Granted Patent B2
US 9,688,787 · App. 14/826,630 · Granted Jun 27, 2017

Polymerizable compound having lateral substituent in terminal ring structure

Inventors: Tetsuo Kusumoto (Kita-adachi-gun, JP); Masahiro Horiguchi (Kita-adachi-gun, JP); Takashi Matsumoto (Kita-adachi-gun, JP); Yoshio Aoki (Kitaadachi-gun, JP); Masanao Hayashi (Kita-adachi-gun, JP); Masayuki Iwakubo (Kitaadachi-gun, JP)
Assignee: DIC CORPORATION
C08F22/20C07C69/78C07C69/92C07C69/94C09K19/2007C09K19/321C09K19/322C09K19/3814C09K19/3411C09K2019/0448C09K2019/325C09K2019/326C09K2019/3413C09K2019/3416
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Quick Facts
Patent No.
US 9,688,787
App. No.
14/826,630
Granted
Jun 27, 2017
Kind
B2
Abstract

An object of the invention is to provide a polymerizable compound having small refractive index anisotropy and having high storage stability and high alignment properties when constituting a polymerizable liquid crystal composition, and provide a polymerizable liquid crystal composition containing the polymerizable compound. Further, the object is to provide a polymer produced by polymerizing the polymerizable liquid crystal composition and an optically anisotropic body including the polymer. The present invention provides a polymerizable compound represented by general formula (I), a polymerizable liquid crystal composition containing the compound as a constituent component, and further provides a polymer produced by polymerizing the polymerizable liquid crystal composition and an optically anisotropic body including the polymer.

Claims (11)

1. A polymerizable compound represented by general formula (I),

wherein P represents a substituent selected from polymerizable groups represented by formulae (P-1) to (P-15) below,

S 1 represents an alkylene group having 1 to 20 carbon atoms, in which one —CH 2 — or unadjacent two or more —CH 2 — may be each independently substituted by —O—, or a single bond, and when a plurality of S 1 is present, S 1 may be the same or different; X 1 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH 2 CH 2 —, —CH 2 CF 2 —, —CF 2 CH 2 —, —CF 2 CF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CY 1 ═CY 2 —, —C≡C—, or a single bond, wherein Y 1 and Y 2 each independently represent a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a fluorine atom, a chlorine atom, or a cyano group, and when a plurality of X 1 is present, X 1 may be the same or different; n represents 0, 1, 2, 3, or 4; A 1 and A 2 each independently represent a 1,4-phenylene group, a naphthalene-2,6-diyl group, a 1,4-cyclohexylene group, a 1,4-cyclohexenylene group, a 1,4-bicyclo[2.2.2]octylene group, a decahydronaphthalene-2,6-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a pyridine-2,6-diyl group, a pyrimidine-2,5-diyl group, or a 1,3-dioxane-2,5-diyl group, which may be unsubstituted or substituted by a fluorine atom, a chlorine atom, a cyano group, a nitro group, an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, or an alkanoyl group having 1 to 7 carbon atoms; at least one hydrogen atom of the alkyl group, the alkoxy group, or the alkanoyl group may be substituted by a fluorine atom or chlorine atom, and when a plurality of A 1 is present, A 1 may be the same or different; A 3 represents a group selected from groups represented by formula (A 3 -1) to formula (A 3 -8) below,

wherein L 1 represents an alkyl group having 1 to 7 carbon atoms, in which at least one hydrogen atom may be substituted by a fluorine atom or a chlorine atom, one —CH═ or unadjacent two —CH═ in a group represented by the formula (A 3 -1) may be substituted by —N═, one —CH 2 — or unadjacent two —CH 2 — in groups represented by the formula (A 3 -2) and formula (A 3 -3) may be substituted by —O— or —S—, groups represented by the formula (A 3 -1) to the formula (A 3 -8) may be further substituted by a fluorine atom, a chlorine atom, a cyano group, a nitro group, or an alkyl group, alkoxy group, or alkanoyl group having 1 to 7 carbon atoms, in which at least one hydrogen atom may be substituted by a fluorine atom or chlorine atom; Z 1 and Z 2 each independently represent —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CO—S—, —S—CO—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH 2 CH 2 —, —CH 2 CF 2 —, —CF 2 CH 2 —, —CF 2 CF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —COO—CH 2 —, —CH 2 —COO—, CH 2 —OCO—, —CY 3 ═CY 4 —, or a single bond wherein Y 3 and Y 4 each independently represent a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a fluorine atom, a chlorine atom, or a cyano group, and when a plurality of Z 1 is present, Z 1 may be the same or different; R 1 represents a fluorine atom, a chlorine atom, a cyano group, or an alkyl group having 1 to 12 carbon atoms, at least one hydrogen atom in the alkyl group may be substituted by a fluorine atom, a chlorine atom, or a cyano group; and m represents 0, 1, 2, 3, or 4,

wherein a polymer obtained by polymerizing the polymerizable compound has a haze value of 1.1 to 1.5.

2. The polymerizable compound according to claim 1 , wherein in the general formula (1), A 3 is represented by the formula (A 3 -1) or the formula (A 3 -5) in which L 1 represents a fluorine atom, a chlorine atom, or an alkyl group or alkoxy having 1 to 4 carbon atoms, and a hydrogen atom on a benzene ring or naphthalene ring may be substituted by a fluorine atom, a chlorine atom, or an alkyl group or alkoxy group having 1 to 4 carbon atoms.

3. The polymerizable compound according to claim 1 , wherein in the general formula (1), A 3 is represented by the formula (A 3 -1) or the formula (A 3 -5) in which L 1 represents a fluorine atom, a chlorine atom, a CH 3 group, or a CH 3 O group, and a hydrogen atom on a benzene ring or naphthalene ring may be substituted by a fluorine atom, a chlorine atom, a CH 3 group, or a CH 3 O group.

4. The polymerizable compound according to claim 1 , wherein in the general formula (1), Z 1 and Z 2 each independently represent —COO—, —OCO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, or —CH 2 —OCO—.

5. A polymerizable liquid crystal composition containing the polymerizable compound according to claim 1 .

6. A polymer produced by polymerizing the polymerizable liquid crystal composition according to claim 5 .

7. The optically anisotropic body comprising the polymer according to claim 6 .

Assignments (3)
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 Apr 18, 2017
From: KUSUMOTO, TETSUO; HORIGUCHI, MASAHIRO; MATSUMOTO, TAKASHI; AOKI, YOSHIO; HAYASHI, MASANAO; IWAKUBO, MASAYUKI
To: DIC CORPORATION
Reel/Frame 042042/0363 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 2, 2015
From: KUSUMOTO, TETUO; HORIGUCHI, MASAHIRO; MATSUMOTO, TAKASHI; AOKI, YOSHIO; HAYASHI, MASANAO; IWAKUBO, MASAYUKI
To: DIC CORPORATION
Reel/Frame 036477/0725 →
Priority Claims (1)
JP 2011-092027 · Apr 18, 2011 · national
Continuity (2)
Continuation 14007242
Related Publication 20150361190A1 · Dec 17, 2015