IP Library Granted Patent US 11,697,695
Granted Patent B2
US 11,697,695 · App. 15/543,430 · Granted Jul 11, 2023

Polymerizable composition and optically anisotropic body using same

Inventors: Kouichi Endo (Kita-adachi-gun, JP); Toru Ishii (Kita-adachi-gun, JP); Yasuhiro Kuwana (Kita-adachi-gun, JP); Kazuaki Hatsusaka (Kita-adachi-gun, JP); Mika Yamamoto (Kita-adachi-gun, JP)
Assignee: DIC CORPORATION
C08F2/42C08F2/48C08F2/50C08F20/38C09K19/2007C09K19/322C09K19/3497C09K19/38C09K19/54G02B5/30G02F1/13363C08F220/303C08F220/365C08F220/387C08F222/1025C08F222/1035C09K2019/0448
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Quick Facts
Patent No.
US 11,697,695
App. No.
15/543,430
Granted
Jul 11, 2023
Kind
B2
Abstract

A polymerizable composition containing: a) a polymerizable compound having one or two or more polymerizable groups and satisfying formula (I): Re(450 nm)/Re(550 nm)<1.0 (I); b) at least one photopolymerization initiator selected from the group consisting of alkylphenone-based compounds, acylphosphine oxide-based compounds, and oxime ester-based compounds; and c) a polymerization inhibitor. An optically anisotropic body, a retardation film, an antireflective film, and a liquid crystal display device that are produced using the polymerizable liquid crystal composition. The polymerizable composition is excellent in solubility and has high storage stability, so that no precipitation of crystals etc. occurs. When a film-shaped polymer is produced by polymerizing the above composition, the unevenness of the surface of the coating film is small while the alignment of the liquid crystal is maintained, and high durability is obtained. Therefore, the polymerizable composition is useful.

Claims (41)

1. A polymerizable composition comprising:

a) a polymerizable compound having one or more polymerizable groups and satisfying formula (I):

Re(450 nm)/Re(550 nm)<1.0  (I)

wherein Re(450 nm) is an in-plane retardation at a wavelength of 450 nm when the polymerizable compound having one or more polymerizable groups is aligned on a substrate such that the direction of long axes of molecules of the polymerizable compound is substantially horizontal to the substrate, and Re(550 nm) is an in-plane retardation at a wavelength of 550 nm when the polymerizable compound having one or more polymerizable groups is aligned on the substrate such that the direction of the long axes of the molecules of the polymerizable compound is substantially horizontal to the substrate;

b) at least one photopolymerization initiator represented by formula (b-1):

wherein R 1 s each independently represent a group selected from formula (R 1 -1) to (R 1 -4) and formula (R 1 -6) below:

R 2 represents a group selected from a single bond, —O—, —C(CH 3 ) 2 , —C(OCH 3 ) 2 , and —C(CH 2 CH 3 )—N(CH 3 )2; and R 3 represents a group selected from formula (R 3 -1) to formula (R 3 -8) below:

 and

c) a phenol-based polymerization inhibitor selected from the group consisting of a hydroquinone, methoxyphenol, methylhydroquinone, tert-butylhydroquinone, or tert-butylcatechol,

wherein the polymerizable compound having one or more polymerizable groups and satisfying formula (I) comprises at least one selected from liquid crystalline compounds represented by general formula (1) and at least one selected from liquid crystalline compound represented by general formula (2):

wherein P 11 to P 22 each represent any of general formulas (P-1) to (P-3):

S 11 to S 22 each represent an alkylene group which has 1 to 20 carbon atoms and in which one —CH 2 — group or two or more nonadjacent —CH 2 — groups may be each independently replaced by —O—, —COO—, —OCO—, —OCO—O—, —CO—NH—, —NH—CO—, —CH═CH—, —C≡C—, or formula (S-1) below:

when a plurality of S 11 s to S 22 s are present, they may be the same or different;

X 11 to X 22 each 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 provided that each P—(S—X)— bond contains no —O—O—; when a plurality of X 11 s to X 22 s are present, they may be the same or different;

MG 11 to MG 21 each independently represent formula (a):

wherein A 11 and A 12 each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene 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, each of which may be unsubstituted or substituted by at least one L 1 ; when a plurality of A 11 s and/or A 12 s are present, they may be the same or different;

Z 11 and Z 12 each independently represent —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—, —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; when a plurality of Z 11 s and/or Z 12 s are present, they may be the same or different;

M represents a group selected from formula (M-1) to formula (M-2) below:

the groups represented by formula (M-1) to formula (M-2) may be unsubstituted or substituted by at least one L 1 ;

G is formula (G-1) below:

wherein R 3 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, the alkyl group being linear or branched, wherein the branched alkyl has 3 to 20 carbon atoms, any hydrogen atom in the alkyl group being optionally replaced by a fluorine atom, one —CH 2 — group or more nonadjacent —CH 2 — groups in the alkyl group being each independently optionally replaced by —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, or —C≡C—;

W 81 represents formula (W-a-5):

wherein s represents an integer from 0 to 4;

W 82 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, the alkyl group being linear or branched, wherein the branched alkyl has 3 to 20 carbon atoms, any hydrogen atom in the alkyl group being optionally replaced by a fluorine atom, one —CH 2 — group or more nonadjacent —CH 2 — groups in the alkyl group being each independently optionally replaced by —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, or —C≡C—; the meaning of W 82 may be the same as the meaning of W 81 ;

L 1 represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro 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 an alkyl group having 1 to 20 carbon atoms, the alkyl group being linear or branched, wherein the branched alkyl has 3 to 20 carbon atoms, any hydrogen atom in the alkyl group being optionally replaced by a fluorine atom, one —CH 2 — group or more nonadjacent —CH 2 — groups in the alkyl group being each independently optionally replaced by a group selected from —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—, and —C≡C—; when a plurality of L 1 s are present in the compound, they may be the same or different;

j11 represents an integer from 1 to 5; and j12 represents an integer of 1 to 5 while j11+j12 is an integer from 2 to 5;

R 11 each represent a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a cyano group, a nitro group, an isocyano group, a thioisocyano group, or an alkyl group having 1 to 20 carbon atoms, the alkyl group being linear or branched, wherein the branched alkyl has 3 to 20 carbon atoms, any hydrogen atom in the alkyl group being optionally replaced by a fluorine atom, one —CH 2 — group or more nonadjacent —CH 2 — groups in the alkyl group being each independently optionally replaced by —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, or —C≡C—; m11 represents an integer of 0 to 8; and m2 and m3 each independently represent an integer from 0 to 5.

2. The polymerizable composition according to claim 1 , further comprising a dichroic pigment.

3. The polymerizable composition according to claim 1 , further comprising a cinnamate derivative.

4. A polymer of the polymerizable composition according to claim 1 .

5. An optically anisotropic body comprising the polymer according to claim 4 .

6. A retardation film comprising the polymer according to claim 4 .

7. A polarizing film comprising the polymer according to claim 4 .

8. A lens sheet comprising the polymer according to claim 4 .

9. A light-emitting diode lighting device comprising the polymer according to claim 4 .

10. A display device comprising the optically anisotropic body according to claim 5 .

11. A light-emitting device comprising the optically anisotropic body according to claim 5 .

12. An antireflective film comprising the retardation film according to claim 6 .

13. A display device comprising the retardation film according to claim 6 .

14. A light-emitting device comprising the retardation film according to claim 6 .

15. The polymerizable composition according to claim 1 , wherein W 82 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, the alkyl group being linear or branched, wherein the branched alkyl has 3 to 20 carbon atoms, one —CH 2 — group or more nonadjacent —CH 2 — groups in the alkyl group being each independently optionally replaced by —O—.

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 Jul 13, 2017
From: ENDO, KOUICHI; ISHII, TORU; KUWANA, YASUHIRO; HATSUSAKA, KAZUAKI; YAMAMOTO, MIKA
To: DIC CORPORATION
Reel/Frame 043001/0410 →
Priority Claims (1)
JP 2015-006299 · Jan 16, 2015 · national
Continuity (1)
Related Publication 20180002460A1 · Jan 4, 2018
Cited By (2)
US 12,570,901 US 12,662,632