Liquid crystal aligning agent, liquid crystal alignment film and liquid crystal display element

Abstract

Provided are: a liquid crystal alignment film which is able to be suppressed in separation of the film or occurrence of foreign substances caused by a physical impact, while enhancing transmittance characteristics of an element and having excellent afterimage characteristics by alternating-current driving; and a liquid crystal aligning agent. A liquid crystal aligning agent which contains a component (A) and a component (B) described below as well as a solvent that dissolves these components. Component (A): a compound represented by formula (1) (In the formula, P has at least one group wherein a carbon atom is substituted by at least two nitrogen atoms, and at least one of the nitrogen atoms is substituted by a monovalent thermally cleavable group having 1-24 carbon atoms, said monovalent thermally cleavable group being substituted by a hydrogen atom by means of heat; X represents a single bond or the like; and Q represents a benzene ring or the like.) Component (B): at least one polymer that is selected from the group consisting of polyimide precursors and polyimides

Description

technical field

[0001] The present invention relates to a liquid crystal aligning agent used in a liquid crystal display element driven by applying a parallel electric field to a substrate, a liquid crystal aligning film, and a liquid crystal display element using the same. Background technique

[0002] Polyimide is a polymer material with excellent heat resistance, mechanical strength, electrical properties, and solvent resistance. It is widely used in the field of electronic materials in the form of polyimide films such as insulating films, protective films, and liquid crystal alignment films. . When attempting to obtain these polyimide films industrially, a common method is to prepare a coating liquid in which polyimide or a polyimide precursor is dissolved in a solvent, apply it, and bake it.

[0003] As a polyimide precursor, polyamic acid, polyamic acid ester, etc. can be used. They have higher solubility in solvents than polyimides, so in the case of the method of o...

Examples

preparation example Construction

[0186] The preparation method of the liquid-crystal aligning agent of this invention is not specifically limited. For example, the following methods are mentioned: a method of mixing component (A) at a specific ratio in a solution of component (B) dissolved in a solvent to prepare a homogeneous solution; or, in an appropriate stage of the production method, as needed A method of further adding and mixing the above-mentioned crosslinkable compound, a compound for improving the film thickness uniformity and surface smoothness of the resin film or liquid crystal aligning film, a compound for accelerating decharge, a dielectric substance, and a conductive substance.

[0187] In preparation of the liquid-crystal aligning agent of this invention, the solution of the polymer which is (B) component obtained by the polymerization reaction in a solvent can be used as it is. In this case, for example, (A) component etc. are injected|thrown-in to the solution of (B) component similarly to...

Embodiment

[0206] Hereinafter, although an Example is given and this invention is demonstrated in more detail, it is not limited to these.

[0207] It should be noted, 1 The measurement apparatus and measurement conditions of H-NMR are as follows.

[0208] Device: Fourier transform superconducting nuclear magnetic resonance device (FT-NMR) INOVA-400 (manufactured by Varian Corporation) 400MHz

[0209] Solvent: deuterated chloroform (CDCl 3 )

[0210] Standard substance: Tetramethylsilane (TMS)

[0211] Cumulative times: 8

Synthetic example 1X-1

[0212] [Synthesis Example 1] Synthesis of X-1

[0213]

[0214] Put 73.2 g of dichloromethane, 4.00 g (13.8 mmol) of N,N'-bis(tert-butoxycarbonyl)-S-methylisothiourea, and 1.77 g of benzylamine into a 200 mL four-neck flask equipped with a magnetic stirrer (1.2eq) and triethylamine (Et 3 N) 2.83g (2.0eq), after nitrogen substitution, N-iodosuccinimide (NIS) 3.10g (1.0eq) was added, and it stirred at room temperature. After 3 hours, add benzylamine 2.22g (1.5eq), N-iodosuccinimide (NIS) 1.54g (1.0eq) and triethylamine (Et 3 N) 1.39g (1.0eq), further reacted for 40 hours. After the reaction, the dichloromethane layer was washed twice with 1.0M aqueous sodium thiosulfate (50 ml) and twice with 0.5M aqueous hydrochloric acid (50 ml). Thereafter, water washing was performed twice with pure water (100 ml), and the dichloromethane layer was collected. Yellow crystals were recovered by concentrating the recovered dichloromethane layer under reduced pressure, and dissolved in 28...

technical field

[0001] The present invention relates to a liquid crystal aligning agent used in a liquid crystal display element driven by applying a parallel electric field to a substrate, a liquid crystal aligning film, and a liquid crystal display element using the same. Background technique

[0002] Polyimide is a polymer material with excellent heat resistance, mechanical strength, electrical properties, and solvent resistance. It is widely used in the field of electronic materials in the form of polyimide films such as insulating films, protective films, and liquid crystal alignment films. . When attempting to obtain these polyimide films industrially, a common method is to prepare a coating liquid in which polyimide or a polyimide precursor is dissolved in a solvent, apply it, and bake it.

[0003] As a polyimide precursor, polyamic acid, polyamic acid ester, etc. can be used. They have higher solubility in solvents than polyimides, so in the case of the method of o...

Examples

preparation example Construction

[0186] The preparation method of the liquid-crystal aligning agent of this invention is not specifically limited. For example, the following methods are mentioned: a method of mixing component (A) at a specific ratio in a solution of component (B) dissolved in a solvent to prepare a homogeneous solution; or, in an appropriate stage of the production method, as needed A method of further adding and mixing the above-mentioned crosslinkable compound, a compound for improving the film thickness uniformity and surface smoothness of the resin film or liquid crystal aligning film, a compound for accelerating decharge, a dielectric substance, and a conductive substance.

[0187] In preparation of the liquid-crystal aligning agent of this invention, the solution of the polymer which is (B) component obtained by the polymerization reaction in a solvent can be used as it is. In this case, for example, (A) component etc. are injected|thrown-in to the solution of (B) component similarly to...

Embodiment

[0206] Hereinafter, although an Example is given and this invention is demonstrated in more detail, it is not limited to these.

[0207] It should be noted, 1 The measurement apparatus and measurement conditions of H-NMR are as follows.

[0208] Device: Fourier transform superconducting nuclear magnetic resonance device (FT-NMR) INOVA-400 (manufactured by Varian Corporation) 400MHz

[0209] Solvent: deuterated chloroform (CDCl 3 )

[0210] Standard substance: Tetramethylsilane (TMS)

[0211] Cumulative times: 8

Synthetic example 1X-1

[0212] [Synthesis Example 1] Synthesis of X-1

[0213]

[0214] Put 73.2 g of dichloromethane, 4.00 g (13.8 mmol) of N,N'-bis(tert-butoxycarbonyl)-S-methylisothiourea, and 1.77 g of benzylamine into a 200 mL four-neck flask equipped with a magnetic stirrer (1.2eq) and triethylamine (Et 3 N) 2.83g (2.0eq), after nitrogen substitution, N-iodosuccinimide (NIS) 3.10g (1.0eq) was added, and it stirred at room temperature. After 3 hours, add benzylamine 2.22g (1.5eq), N-iodosuccinimide (NIS) 1.54g (1.0eq) and triethylamine (Et 3 N) 1.39g (1.0eq), further reacted for 40 hours. After the reaction, the dichloromethane layer was washed twice with 1.0M aqueous sodium thiosulfate (50 ml) and twice with 0.5M aqueous hydrochloric acid (50 ml). Thereafter, water washing was performed twice with pure water (100 ml), and the dichloromethane layer was collected. Yellow crystals were recovered by concentrating the recovered dichloromethane layer under reduced pressure, and dissolved in 28...

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