Search

KR-102962783-B1 - Polymer composition and single-layer phase difference material

KR102962783B1KR 102962783 B1KR102962783 B1KR 102962783B1KR-102962783-B1

Abstract

(A) a side chain polymer having a side chain having a photoreactive site represented by the following formula (a) and a side chain having a site represented by the following formula (b), and (B) a polymer composition comprising an organic solvent.

Inventors

  • 네기 다카유키

Assignees

  • 닛산 가가쿠 가부시키가이샤

Dates

Publication Date
20260508
Application Date
20200326
Priority Date
20190329

Claims (7)

  1. (A) A side chain polymer having a side chain having a photoresponsive site represented by the following formula (a) and a side chain having a site represented by the following formula (b), and (B) Organic solvent A monolayer phase difference material obtained from a polymer composition comprising, A single-layer phase difference material with a film thickness of 0.5 to 3 μm. (In the formula, R1 is an alkylene group having 1 to 30 carbon atoms, and one or more hydrogen atoms of the alkylene group may be substituted with a fluorine atom or an organic group. Also, -CH2CH2- in R1 may be substituted with -CH =CH-, and -CH2- in R1 may be substituted with a group selected from the group consisting of -O-, -NH-C(=O)-, -C(=O)-NH-, -C(=O)-O-, -OC(=O)-, -NH-, -NH-C(=O)-NH-, and -C(=O)-. Provided, however, that adjacent -CH2- are not simultaneously substituted with these groups. Also, -CH2- may be the terminal -CH2- in R1 . R₂ is a divalent aromatic group, a divalent alicyclic group, a divalent complex cyclic group, or a divalent condensed cyclic group. R3 is a single bond, -O-, -C(=O)-O-, -OC(=O)-, or -CH=CH-C(=O)-O-. R 4 is a 1,4-phenylene group or a trans-1,4-cyclohexylene group. R is an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, a cyano group, or a nitro group, and when c ≥ 2, each R may be the same or different from each other. The benzene ring in formula (b) may be substituted with a substituent selected from a C1- to C6 alkyl group, a C1- to C6 haloalkyl group, a C1- to C6 alkoxy group, a C1- to C6 haloalkoxy group, a cyano group, and a nitro group. a is 0, 1, or 2. b is 0 or 1. c is an integer satisfying 0 ≤ c ≤ 2b + 4. The dashed line is a connecting hand.)
  2. In Article 1, A monolayer phase difference material having a side chain having the above-mentioned photoreactive site, represented by the following formula (a1). (In the formula, R1 , R2 and a are the same as above. R 3A is a single bond, -O-, -C(=O)-O- or -OC(=O)-. The benzene ring in formula (a1) may be substituted with a substituent selected from a carbon-1 to 6 alkyl group, a carbon-1 to 6 haloalkyl group, a carbon-1 to 6 alkoxy group, a carbon-1 to 6 haloalkoxy group, a cyano group, and a nitro group. The dashed line is a connecting hand.)
  3. In Article 1 or Article 2, (A) A single-layer phase difference material having a side chain polymer, additionally, a side chain that exhibits only liquid crystallization.
  4. In Paragraph 3, A single-layer phase difference material in which the side chains exhibiting only the liquid crystal properties are liquid crystal side chains represented by any of the following formulas (1) to (12). (In the formula, A1 and A2 are each independently a single bond, -O-, -CH2- , -C(=O)-O-, -OC(=O)-, -C(=O)-NH-, -NH-C(=O)-, -CH=CH-C(=O)-O- or -OC(=O)-CH=CH-. R 11 is -NO 2 , -CN, a halogen atom, a phenyl group, a naphthyl group, a biphenylal group, a furanyl group, a monovalent nitrogen-containing heterocyclic ring, a monovalent alicyclic hydrocarbon group having 5 to 8 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or an alkyloxy group having 1 to 12 carbon atoms. R 12 is a group selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a furanyl group, a monovalent nitrogen-containing heterocyclic group, a monovalent alicyclic hydrocarbon group having 5 to 8 carbon atoms, and a group obtained by combining these, and the hydrogen atoms bonded to these may be substituted with -NO 2 , -CN, a halogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkoxy group having 1 to 5 carbon atoms. R 13 is a hydrogen atom, -NO 2 , -CN, -CH=C(CN) 2 , -CH=CH-CN, a halogen atom, a phenyl group, a naphthyl group, a biphenyl group, a furanyl group, a monovalent nitrogen-containing heterocyclic ring, a monovalent alicyclic hydrocarbon group having 5 to 8 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. E is -C(=O)-O- or -OC(=O)-. d is an integer from 1 to 12. k1 to k5 are each independently integers from 0 to 2, but the sum of k1 to k5 is 2 or greater. k6 and k7 are each independently integers from 0 to 2, but the sum of k6 and k7 is 1 or greater. m1, m2, and m3 are each independently integers from 1 to 3. n is 0 or 1. Z1 and Z2 are, independently, single bonds, -C(=O)-, -CH2O- , -CH=N-, or -CF2- . The dashed line is a connecting hand.)
  5. In Article 4, A single-layer phase difference material in which the side chains exhibiting only liquid crystal properties are liquid crystal side chains represented by any of formulas (1) to (11).
  6. A method for manufacturing a single-layer phase difference material as described in claim 1, (I) A process of forming a coating film by applying a polymer composition comprising (A) a side chain having a photoreactive site represented by formula (a) and a side chain having a site represented by formula (b), and (B) an organic solvent onto a substrate. (II) A process of irradiating the above coating film with polarized ultraviolet light, and (III) A method for manufacturing a single-layer phase difference material, comprising a process of heating the coating film irradiated with ultraviolet light to obtain a phase difference material.
  7. delete

Description

Polymer composition and single-layer phase difference material The present invention relates to a composition comprising a polymer and a single-layer phase difference material. More specifically, the invention relates to a liquid crystal polymer that can be preferably used as an optical compensation film, such as a polarizer and a phase difference plate for a liquid crystal display, a material having optical properties desirable for applications such as display devices or recording materials, in particular, a composition comprising said polymer, and a single-layer phase difference material obtained from said composition. Due to demands for improved display quality and reduced weight of liquid crystal display devices, there is a growing demand for polymer films with controlled internal molecular orientation structures to serve as optical compensation films, such as polarizers and phase difference plates. To meet this demand, films utilizing the optical anisotropy of polymerizable liquid crystal compounds are being developed. The polymerizable liquid crystal compounds used here are generally liquid crystal compounds having polymerizable groups and liquid crystal structural regions (structural regions having spacer and mesogen groups), and acrylic groups are widely used as these polymerizable groups. Such polymerizable liquid crystal compounds are generally polymerized (films) by polymerizing them through irradiation with radiation such as ultraviolet rays. For example, a method of obtaining a polymer by supporting a specific polymerizable liquid crystal compound having an acrylic group between supports and irradiating it with radiation while maintaining the compound in a liquid crystal state (Patent Document 1), or a method of obtaining a polymer by adding a photopolymerization initiator to a mixture of two types of polymerizable liquid crystal compounds having an acrylic group or a composition in which a chiral liquid crystal is mixed with the mixture, and irradiating it with ultraviolet rays (Patent Document 2). In addition, various single-layer coating type alignment films have been reported, such as alignment films using polymerizable liquid crystal compounds or polymers that do not require a liquid crystal alignment layer (Patent Documents 3, 4) and alignment films using polymers containing photocrosslinking sites (Patent Documents 5, 6). However, the above film manufacturing process is difficult, and there are problems such as the low solubility of the polymer, such as the need to use solvents with excellent solubility such as NMP, chloroform, and chlorobenzene as solvents for the polymers used, and materials that solve these problems have not been discovered until now. As a result of conducting the aforementioned research, the inventor obtained the following findings and came to complete the present invention. The polymer composition of the present invention has a photosensitive side-chain polymer capable of exhibiting liquid crystal properties (hereinafter simply referred to as a side-chain polymer), and the film obtained using the polymer composition is a film having a photosensitive side-chain polymer capable of exhibiting liquid crystal properties. This film is not subjected to rubbing treatment, but is subjected to orientation treatment by polarized light irradiation. Then, after polarized light irradiation, the side-chain polymer film undergoes a heating process to become a film with imparted optical anisotropy (hereinafter also referred to as a single-layer phase difference material). At this time, the minute anisotropy imparted by polarized light irradiation becomes a driving force, and the liquid crystal side-chain polymer itself is efficiently re-oriented by self-organization. As a result, high-efficiency orientation treatment is realized as a single-layer phase difference material, and a single-layer phase difference material with high optical anisotropy can be obtained. Furthermore, in the polymer composition of the present invention, the side-chain type polymer, which is component (A), includes a side chain represented by formula (b) together with a side chain having a photo-oriented site represented by formula (a), thereby suppressing the aggregation of the polymer. As a result, the phase difference material obtained from the polymer composition of the present invention exhibits high retardation even in a thin film. Additionally, these include the inventor's views regarding the mechanism of the present invention and do not limit the present invention. Hereinafter, embodiments of the present invention will be described in detail. [Polymer Composition] The polymer composition of the present invention is characterized by comprising (A) a photosensitive side-chain polymer that exhibits liquid crystal properties within a predetermined temperature range and (B) an organic solvent. [(A) Side-chain polymer] (A) The component is a photosensitive side-chain polymer that exhibits liquid crystal prop