CN-121991005-A - Polymerizable compound containing chromophoric group for phase difference film and liquid crystal composition

Abstract

The invention discloses a polymerizable compound containing a chromophoric group for a reverse wavelength dispersion phase difference film and a liquid crystal composition thereof. The compound takes benzothiazole as a color nucleus, introduces a strong electron-withdrawing trifluoromethyl at a specific position and is connected with a side chain through a thioether bond, so that high reverse wavelength dispersibility, extremely high solubility and excellent compatibility with a conventional forward dispersion monomer are synchronously realized. After the liquid crystal composition containing the compound is subjected to orientation coating and photopolymerization, a high-transparency reverse wavelength dispersion phase difference film with extremely low haze, uniform orientation and small shrinkage stress can be prepared, the contradiction between the optical performance and the stability of a film forming process of the existing material is thoroughly solved, and the liquid crystal composition is suitable for high-end OLED and Mini/Micro-LED wide color gamut displays.

Inventors

• Ma dingfu
• HAN YU
• ZHANG WENQI
• DU SHIMING

Assignees

• 南京三江新材料研发有限公司

Dates

Publication Date

20260508

Application Date

20260109

Claims (8)

1. 1. A polymerizable compound represented by the following formula I: ; Q 1 、Q 2 each independently represents an alkyl/alkenyl group having 2 to 12 carbon atoms in which one or more non-adjacent-CH 2 -groups are replaced by O/S; P 1 、P 2 、Z 1 、Z 2 each independently represents-C (=o) -O-, -O-C (=o) -, -O-; Z 3 represents an alkyl/alkenyl group having 1 to 6 carbon atoms; r 1 、R 2 、R 3 、R 4 each independently represents a hydrogen atom, halogen, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, thioether, amino, cyano, nitro; R 5 represents an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, a cycloalkane, arene or aromatic heterocycle having 3 to 20 carbon atoms, and wherein one or more-CH 2 -which are not adjacent are substituted with O or C=O.
2. 2. The polymerizable compound of claim 1 wherein the polymerizable compound of formula I comprises the following: I-1; I-2; I-3; I-4; I-5; I-6; I-7; I-8; I-9; I-10; I-11; I-12; I-13; I-14; I-15; I-16; I-17; I-18; I-19; I-20; I-21; I-22; I-23; I-24; I-25; I-26; I-27。
3. 3. a process for the preparation of a polymerizable compound according to claim 1, comprising the following:
4. 4. a liquid crystal composition comprising at least one polymerizable compound according to claim 1 or 2, and at least one polymerizable liquid crystal compound.
5. 5. The liquid crystal composition according to claim 4, wherein the liquid crystal composition comprises 5 to 70 parts by weight of the liquid crystal compound and 5 to 50 parts by weight of the polymerizable liquid crystal compound.
6. 6. The liquid crystal composition of claim 4, wherein the polymerizable liquid crystal compound comprises the structure: R-1; R-2; R-3; R-4; R-5; R-6; R-7; R-8。
7. 7. A retardation film comprising the liquid crystal composition according to any one of claims 4 to 6.
8. 8. The retardation film of claim 7, which is used for a display, a liquid crystal panel, a projection apparatus, an optical compensation film or a polarizing optical element.

Description

Polymerizable compound containing chromophoric group for phase difference film and liquid crystal composition Technical Field The invention relates to the technical field of liquid crystal compounds, in particular to a polymerizable compound containing a chromophoric group and used for a phase difference film and a liquid crystal composition. Background The inverse wavelength dispersive retardation film depends on the wavelength-sensitive birefringence behavior of the liquid crystal polymer, and its optical mechanism is based on the electron transition characteristics of the chromophoric group. When the chromophoric group in the material has a rigid skeleton composed of a larger pi conjugated system, a stronger electron-withdrawing capability and multiple aromatic rings or heteroaromatic rings, the molecular polarization rate tensor can generate a significant difference along with the wavelength, so that the birefringence in the short wave direction is reduced, and the birefringence in the long wave direction is improved, thereby forming inverse wavelength dispersion. Therefore, the existing inverse dispersion liquid crystal polymer often adopts large conjugated chromophores such as benzothiazole, triazine, naphthalene ring and the like, and combines electron-withdrawing substituents such as cyano, trifluoromethyl and the like to enhance the wavelength response of pi-pi and n-pi transition centers and promote the inverse dispersion slope, which is the core structural mechanism basis of the inverse wavelength dispersion material. However, the above molecular structure capable of generating inverse dispersion brings about serious problems that are in conflict with practical use of materials. First, the large area pi conjugated surface results in relatively high intermolecular pi-pi stacking energy, so that intermolecular forces are significantly enhanced, and the solubility in environmentally friendly solvents (PMA or fluoroether HFE-458) which are industrially allowable is generally low, which is far from meeting the solid content of not less than 20 wt% required for roll-to-roll coating. And secondly, the polar parameter of the strong electron-withdrawing chromophoric group is seriously mismatched with the main stream positive dispersion acrylic ester liquid crystal monomer, so that microphase separation occurs when the polar parameter and the main stream positive dispersion acrylic ester liquid crystal monomer are mixed, nonuniform domains are formed in the coating and photo-curing stages, and finally obvious stripes, particles, haze rise and local refractive index discontinuity appear on the phase difference film. In addition, the strong conjugated structure seriously interferes with free radical transfer efficiency, so that the photopolymerization rate is locally unbalanced, shrinkage stress is concentrated, and the orientation order degree and the stability of a wavelength dispersion curve are further damaged. Therefore, the existing inverse dispersion material requires 'large conjugation and strong electron withdrawing' on the optical mechanism, but the existing inverse dispersion material is forced to require 'high solubility in PMA/fluoroether + high compatibility with positive dispersion monomer + mild polymerization behavior' on the industrial processing, and the two materials have irreconcilable structural contradiction essentially, which is the fundamental technical problem that the existing inverse dispersion phase difference film material is difficult to simultaneously combine excellent optical performance and mass production film stability. Disclosure of Invention In order to achieve the above object, the embodiment of the present specification adopts the following technical solutions: in a first aspect, the present application provides a polymerizable compound represented by the following formula I: Q 1、Q2 each independently represents an alkyl/alkenyl group having 2 to 12 carbon atoms in which one or more non-adjacent-CH 2 -groups are replaced by O/S; P 1、P2、Z1、Z2 each independently represents-C (=o) -O-, -O-C (=o) -, -O-; Z 3 represents an alkyl/alkenyl group having 1 to 6 carbon atoms; r 1、R2、R3、R4 each independently represents a hydrogen atom, halogen, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, thioether, amino, cyano, nitro; R 5 represents an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, a cycloalkane, arene or aromatic heterocycle having 3 to 20 carbon atoms, and wherein one or more-CH 2 -which are not adjacent are substituted with O or C=O. As a preferable technical scheme of the polymerizable compound, the polymerizable compound shown in the formula I comprises the following components: The polymerizable compound of claim 1 wherein the polymerizable compound of formula I comprises the following: I-1; I-2; I-3; I-4; I-5; I-6; I-7; I-8; I-9; I-10; I-11; I-12; I-13; I-14; I-15; I-16; I-17; I-18; I-19; I-20; I-21; I-22; I-23; I-24; I-25; I