IP Library Granted Patent US 10,655,066
Granted Patent B2
US 10,655,066 · App. 15/668,235 · Granted May 19, 2020

Optical isomer

Inventors: Masahiro Horiguchi (Saitama, JP); Sayaka Nose (Saitama, JP); Yasuhiro Kuwana (Saitama, JP); Kouichi Endo (Saitama, JP)
Assignee: DIC Corporation
C09K19/3857C08J5/18C09K19/3804C09K19/3852C09K19/54C08J2335/02C09K2019/0444C09K2019/0448C09K2219/03Y10T428/10Y10T428/105Y10T428/1036
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Quick Facts
Patent No.
US 10,655,066
App. No.
15/668,235
Granted
May 19, 2020
Kind
B2
Abstract

The problem that the present invention is to solve is to provide an optical film that has less alignment defects and is less liable to cause variation in the optical characteristics when placed in a high temperature state. The present invention provides an optical film containing a structural unit derived from a specific compound, that is, an optical film containing a structural unit derived from a compound represented by the general formula (I), which has less alignment defects and is less liable to cause variation in the optical characteristics when placed in a high temperature state, and also provides a display device including the optical film.

Claims (23)

1. An optical film,

which comprises a structural unit derived from a compound represented by the following general formula (I-A-111), a structural unit derived from a compound represented by the following general formula (I-A-221), a structural unit derived from a compound represented by the following general formula (I-A-121), and a structural unit derived from a compound represented by the following general formula (I-A-211):

wherein P 1 and P 2 respectively represent a group selected from the formulae (P-1) to (P-3):

and A 11 , A 12 , and A 21 each independently represent a 1,4-phenylene group or a 1,4-cyclohexylene group, wherein the group may be unsubstituted or substituted with one or more substituents L's, and L represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms in which one —CH 2 — group or two or more —CH 2 — groups that are not adjacent to each other each may be independently substituted by —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted by a fluorine atom, or L represents a group represented by the following formula (I-RL):

wherein, P L represents a group selected from the above formulae (P-1) to (P-3), R SL represents a linear or branched alkyl group having 1 to 20 carbon atoms in which one —CH 2 — group or two or more —CH 2 — groups that are not adjacent to each other each may be independently substituted by —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted by a fluorine atom or a chlorine atom, Sp L represents an alkylene group having 1 to 20 carbon atoms, wherein plural Sp L groups, if present, may be the same or different, X L 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═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—, —CH═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, wherein plural X L groups, if present, may be the same or different, kL represents an integer of 0 to 10, and nL1 and nL2 each independently represent an integer of 0 to 8), wherein plural L groups, if present in the compound, may be the same or different, and Z 11 and Z 12 each independently represent —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —COO—, —OCO—, —CO—NH—, —NH—CO—, —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—, or a single bond;

wherein P 1 and P 2 respectively represent the same meanings as in P 1 and P 2 in the general formula (I-A-111), and A 11 , A 12 , A 21 , Z 11 , and Z 12 respectively represent the same meanings as in A 11 , A 12 , Z 11 , and Z 12 in the general formula (I-A-111);

wherein P 1 and P 2 respectively represent the same meanings as in P 1 and P 2 the general formula (I-A-111), and A 11 , A 12 and Z 12 respectively represent the same meanings as in A 11 , A 12 , A 21 , Z 11 , and Z 12 in the general formula (I-A-111); and

wherein P 1 and P 2 respectively represent the same meanings as in P 1 and P 2 in the general formula (I-A-111), and A 11 , A 12 , A 21 , Z 11 , and Z 12 respectively represent the same meanings as in A 11 , A 12 , A 21 , Z 11 , and Z 12 in the general formula (I-A-111).

2. The optical film according to claim 1 , which further comprises a structural unit derived from a compound represented by the following general formula (II):

P 3 Sp 3 -X 3 k3 A 3 -Z 2 m2 A 4 X 4 -Sp 4 k4 P 4   (II)

wherein P 3 and P 4 each independently represent a group which undergoes polymerization by radical polymerization, cation polymerization, or anion polymerization,

Sp 3 and Sp 4 each independently represent a spacer group, wherein plural Sp 3 groups, if present, may be the same or different, and plural Sp 4 groups, if present, may be the same or different,

X 3 and X 4 each independently represent —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═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—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, wherein plural X 3 groups, if present, may be the same or different, and plural X 4 groups, if present, may be the same or different,

k3 and k4 each independently represent an integer of 0 to 10,

A 3 and A 4 each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a bicyclo[2.2.2]octane-1,4-diyl group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, which may be unsubstituted or substituted with one or more substituents Us, wherein plural A 3 groups, if present, may be the same or different,

Z 2 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 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—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, wherein plural Z 2 groups, if present, may be the same or different, and

m2 represents an integer of 0 to 5.

3. The optical film according to claim 1 , which further comprises a structural unit derived from a chiral compound.

4. The optical film according to claim 1 , which has a cholesteric structure.

5. A compound, which is represented by the general formula (I-A-111), the general formula (I-A-221), the general formula (I-A-121), or the general formula (I-A-211) as set forth in claim 1 .

6. A laminate film, comprising the optical film as set forth in claim 1 .

7. A display device, comprising the optical film as set forth in claim 1 .

8. A display device, comprising the laminate film as set forth in claim 6 .

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 Aug 3, 2017
From: HORIGUCHI, MASAHIRO; NOSE, SAYAKA; KUWANA, YASUHIRO; ENDO, KOUICHI
To: DIC CORPORATION
Reel/Frame 043189/0506 →
Priority Claims (2)
JP 2016-152889 · Aug 3, 2016 · national
JP 2017-113403 · Jun 8, 2017 · national
Continuity (1)
Related Publication 20180037819A1 · Feb 8, 2018