A polymeric compound, a polymeric composition, and an optically anisotropic film
By using new polymerizable compounds to prepare optical anisotropic films, the problem of insufficient performance of polymerizable compounds in the prior art is solved, high contrast, uniform polarization conversion and good display effects are achieved, and the quality of the liquid crystal display is significantly improved.
Patent Information
- Application Number
- CN202310385161.6
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2023-04-12
- Publication Date
- 2025-06-10
- Estimated Expiration
- 2043-04-12
AI Technical Summary
The polymeric compounds used in the existing optical anisotropic films have problems such as insufficient inverse wavelength dispersion, poor UV stability, low solubility, high cost, and uneven brightness, reduced contrast and unnatural tone in the display.
A novel polymerizable compound is provided, with a general formula of a specific compound structure, which has high optical stability, low synthesis cost and excellent solubility. This compound is used to prepare an optically anisotropic film. The film has good alignment quality, has reverse wavelength dispersion, and can uniformly polarize conversion in a wide wavelength region.
It significantly improves the quality of the LCD display, enhances contrast and compensates tone when viewed from the front or oblique direction, and prevents contrast drops or image reflection glare caused by external light reflection.
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Abstract
Description
Technical Field
[0001] The present invention relates to the technical field of optical thin films. More specifically, it relates to a polymerizable compound, a polymerizable composition, and an optically anisotropic film. Background Art
[0002] With the continuous development of display technology, liquid crystal displays (LCDs) and organic light emitting diodes (OLEDs) are widely used in various devices, such as televisions, computer monitors, electronic shelf labels, e-books, digital signage, indoor signage, and display cabinets. Such electronic display elements can appropriately recognize the narrow viewing angle of the image. However, when observing the liquid crystal display from an inclined direction, or when there is reflection of external light or image input, its brightness or contrast will decrease, or its brightness will reverse in halftone. In order to eliminate the viewing angle dependence of display color and contrast changes caused by the viewing angle, or to prevent the contrast reduction caused by the reflection of external light or image input, and improve the display characteristics, a large number of optical films, especially optically anisotropic films, are required in the display. The optically anisotropic film can improve the contrast and compensate for the color tone when viewing the display from the front or obliquely, and can also prevent the contrast reduction or image reflection glare caused by the reflection of external light on the display surface.
[0003] An optically anisotropic film can be prepared by coating a composition containing a polymerizable compound on a substrate. In order to improve the viewing angle of the display, it is required that the wavelength dispersion of the birefringence of the optically anisotropic film is low, or it has inverse wavelength dispersion. However, the polymerizable compounds used in the optically anisotropic film with inverse wavelength dispersion still have many deficiencies in performance. For example: insufficient inverse wavelength dispersion; poor ultraviolet stability; low solubility in solvents commonly used in industrial production, limited solvents used in the production of optically anisotropic films, and low versatility; expensive raw material reagents, complex synthesis steps, and high costs; when used in displays, there are problems such as uneven picture brightness, reduced contrast, unnatural color tone, or inability to obtain the target optical properties, which greatly reduces the quality of display products.
[0004] Therefore, there is an urgent need to develop a new polymerizable compound with low wavelength dispersion or inverse wavelength dispersion to improve the quality of display products. Summary of the Invention
[0005] In view of this, the present invention provides a polymerizable compound, a polymerizable composition, and an optically anisotropic film. The polymerizable compound has high optical stability, low synthesis cost, and excellent solubility in common solvents. When the polymerizable compound or polymerizable composition provided by the present invention is prepared into an optically anisotropic film, the alignment quality of the optically anisotropic film is good, it has reverse wavelength dispersion, can uniformly perform polarization conversion in a wide wavelength region, can also prevent a decrease in contrast or reflection glare of an image caused by external light reflection on a display surface, and thus can improve the quality of display products, overcoming the defects of the prior art.
[0006] To achieve the above object of the invention, the following technical solutions are adopted:
[0007] In the first aspect of the present invention, a polymerizable compound is provided, and the general structural formula of the compound is shown as Formula I:
[0008]
[0009] X represents O or S;
[0010] R 11 represents hydrogen or a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms, and one -CH 2 - or two or more non-adjacent -CH 2 - can each 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 any one hydrogen in the alkyl group can be substituted by fluorine;
[0011] R 12 , R 31 each independently represents hydrogen or a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms;
[0012] R 21 is the same as or different from R 22 , and each independently selects a group represented by Formula R-1 or Formula R-2, and at least one of R 21 and R 22 is selected from the group represented by Formula R-1,
[0013]
[0014] P 0 -Ar 11 -Ar 21 -Q 21-*R-2
[0015] Among them, the P 1 represents a polymerizable group;
[0016] The P 0 represents a linear or branched alkyl group having 1 to 20 carbon atoms;
[0017] The E represents a single bond or an alkylene group having 1 to 8 carbon atoms;
[0018] The G is selected from -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, in any optional number combination of any one or more of them;
[0019] The n is selected from integers from 0 to 8;
[0020] The Ar 11 is a substituted or unsubstituted 1,4-cyclohexylene group or a substituted or unsubstituted 1,4-phenylene group;
[0021] When the Ar 11 has a substituent, the substituent of the Ar 11 can be one or more, and each is independently selected from fluorine, chlorine, or a linear or branched alkyl group having 1 to 20 carbon atoms, and one -CH in the alkyl group2 - or two or more non-adjacent -CH 2 - may each independently be substituted by -O-, -CO-, -COO- or -OCO-, and any one hydrogen in the alkyl may be substituted by fluorine;
[0022] Said Ar 21 represents a single bond or 1,4-cyclohexylene;
[0023] Said Q 11 is selected from a single bond, -OCH 2 -, -CH 2 O-, -COO- or -OCO-, or any combination of any one or more of them;
[0024] Said Q 21 is selected from -OCH 2 -, -CH 2 O-, -COO-CH 2 CH 2 -, -CH 2 CH 2 -OCO-, -COO- or -OCO-, or any combination of any one or more of them.
[0025] In the above formulas R-1 and R-2, the * part represents the connecting part.
[0026] Combined with the first aspect, said R 11 represents hydrogen or a straight-chain alkyl group having 1 to 12 carbon atoms, and one -CH 2 - or two or more non-adjacent -CH 2 - may each independently be 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 any one hydrogen in the alkyl may be substituted by fluorine.
[0027] Combined with the first aspect, said R 12 and R 31 represent hydrogen or a straight-chain alkyl group having 1 to 5 carbon atoms.
[0028] Combined with the first aspect, the compound represented by Formula I is selected from the structures represented by Formula I-1 or Formula I-2:
[0029]
[0030] Combined with the first aspect, said P 1 is selected from Any one of them. It should be noted that the * part represents the connecting part, and Me represents methyl.
[0031] In combination with the first aspect, the compound represented by Formula I is selected from any one of the structures represented by Formula I-11 to Formula I-18:
[0032]
[0033] In combination with the first aspect, the group represented by Formula R-1 is selected from any one of the groups represented by Formula R-11 to Formula R-15:
[0034]
[0035]
[0036] In the above Formulas R-11 to R-15, the * part represents the connecting part.
[0037] In combination with the first aspect, the group represented by Formula R-2 is selected from any one of the groups represented by Formula R-21 to Formula R-24:
[0038]
[0039] In the above Formulas R-21 to R-24, the * part represents the connecting part.
[0040] The second aspect of the present invention provides a polymerizable composition, comprising the above-mentioned polymerizable compound.
[0041] The third aspect of the present invention provides an optically anisotropic film obtained by polymerizing the above-mentioned polymerizable composition.
[0042] The beneficial effects of the present invention are as follows:
[0043] The polymerizable compound provided by the present invention has good liquid crystallinity, high optical stability, low synthesis cost, excellent solubility in common solvents, and high storage stability in solution state. When the polymerizable compound or polymerizable composition provided by the present invention is prepared into an optically anisotropic film, the alignment quality of the liquid crystal in the optically anisotropic film is good, having excellent inverse wavelength dispersion, capable of uniformly performing polarization conversion in a wide wavelength region, improving the contrast and compensating the color tone when viewing a liquid crystal display from the front or obliquely, and thus can significantly improve the quality of liquid crystal display products, overcoming the defects of the prior art. Detailed Embodiments
[0044] Those skilled in the art should understand that the content specifically described below is illustrative rather than restrictive, and should not be used to limit the protection scope of the present invention. The examples and comparative examples in this specification are provided to more completely illustrate this specification to those skilled in the art. According to the examples and comparative examples in this specification, various different forms can be deformed, and the protection scope of the present invention should not be limited only to the examples and comparative examples detailed below.
[0045] Example 1
[0046] This example provides a polymeric compound RM-1, and the synthesis route of this compound is as follows:
[0047] Step (1)
[0048]
[0049] Add lithium bis(trimethylsilyl)amide (0.44 mol) to a 250 ml three-necked flask, protect with nitrogen, cool down to -78 °C. Dissolve 2,5-dihydroxyacetophenone (20 g, 0.13 mol) in 50 ml of tetrahydrofuran to obtain a 2,5-dihydroxyacetophenone tetrahydrofuran solution. Add the 2,5-dihydroxyacetophenone tetrahydrofuran solution to the above lithium bis(trimethylsilyl)amide, stir at -78 °C for 1 hour, warm up to room temperature and stir for 20 minutes to obtain a first reaction solution. Dissolve lauroyl chloride (31 g, 0.14 mol) in 20 ml of tetrahydrofuran, and drop it into the above first reaction solution. Stir in an ice bath for 3 to 4 hours, warm up to room temperature and stir. After the reaction is completed, pour the first reaction system into ice water, adjust the pH to 6 - 7 with dilute hydrochloric acid, extract with dichloromethane, wash with saturated brine twice, dry over anhydrous sodium sulfate, and rotary evaporate the solvent to obtain a crude product. Purify the crude product through a separation column to obtain a solid compound 1-a (28 g, yield 63.6%);
[0050] Step (2)
[0051]
[0052] Add compound 1-a (28 g, 83.8 mmol), 200 ml of dichloromethane and imidazole (12 g, 209 mmol) to a 250 ml three-necked flask, stir in an ice-water bath to obtain a second reaction solution; dissolve tert-butyldimethylchlorosilane (28 g, 184 mmol) in 100 ml of tetrahydrofuran and then drop it into the above second reaction solution, stir for 2 hours, filter, wash the filtrate with water, dry and rotary evaporate to obtain 40 g of a crude oil-like compound 1-b;
[0053] Step (3)
[0054]
[0055] Add 200 ml of ethanol, crude product of compound 1-b (40 g), 2-hydrazinobenzothiazole (12 g, 72.7 mmol), and p-toluenesulfonic acid (2 g, 10 mmol) to a 500 ml three-necked flask. Heat the mixture to 50 °C and keep the temperature for 2 hours. After the reaction is completed, obtain the third reaction solution. Pour the third reaction solution into water, extract with ethyl acetate, dry, and purify by column chromatography to obtain compound 1-c (35 g, yield 70%);
[0056] Step (4)
[0057]
[0058] Add compound 1-c (35 g, 50.6 mmol) and 200 ml of tetrahydrofuran to a 500 ml three-necked flask. Then add tetrabutylammonium fluoride trihydrate (40 g, 126 mmol) in batches. Stir at room temperature for 12 hours to obtain the fourth reaction solution. Pour the fourth reaction solution into water, stir, extract with ethyl acetate, dry, evaporate to dryness, and then stir with petroleum ether to obtain solid compound 1-d (20 g, yield 85.4%);
[0059] Step (5)
[0060]
[0061] Add 150 ml of dimethylformamide, potassium carbonate (8 g, 58 mmol), compound 1-d (20 g, 43 mmol), and compound A (22.4 g, 95 mmol) to a 250 ml three-necked flask. Stir and heat to 80 °C, and keep the temperature for 3 hours. After the reaction is completed, obtain the fifth reaction solution. Pour the fifth reaction solution into ice water, stir, filter, and air-dry to obtain solid compound 1-e (21 g, yield 65.6%);
[0062] Step (6)
[0063]
[0064] Add compound 1-e (21 g, 28 mmol), 4-acryloyloxyhexyloxyphenol (16.4 g, 62 mmol), 4-dimethylaminopyridine (0.2 g, 1.6 mmol), 1,3-dicyclohexylcarbodiimide (12.6 g, 61.6 mmol), and 150 ml of dichloromethane to a 500 ml three-necked flask. Stir at room temperature for 4 hours under nitrogen protection, filter to obtain the filtrate. Evaporate the filtrate to dryness and recrystallize with ethanol and toluene to obtain the polymeric compound RM-1 (18.2 g, yield 52.1%), MS (m / z) (M+): 1237.
[0065] Example 2
[0066] This embodiment provides a polymeric compound RM-6, and the synthesis route of this compound is as follows:
[0067] Step (1)
[0068]
[0069] Add lithium bis(trimethylsilyl)amide (0.44 mol) to a 250 ml three-necked flask, protect it with nitrogen, cool it down to -78 °C. Dissolve 2,5-dihydroxyacetophenone (20 g, 0.13 mol) in 50 ml of tetrahydrofuran to obtain a 2,5-dihydroxyacetophenone tetrahydrofuran solution. Add the 2,5-dihydroxyacetophenone tetrahydrofuran solution to the above lithium bis(trimethylsilyl)amide, stir at -78 °C for 1 hour, then warm it up to room temperature and stir for 20 minutes to obtain the first reaction solution. Dissolve diethyl carbonate (18 g, 0.16 mol) in 20 ml of tetrahydrofuran, and drop it into the above-obtained first reaction solution. Stir in an ice bath for 3 to 4 hours, then warm it up to room temperature and stir. After the reaction is completed, pour the first reaction system into ice water, adjust the pH to 6 - 7 with dilute hydrochloric acid, extract with dichloromethane, wash with saturated brine twice, dry over anhydrous sodium sulfate, and rotary evaporate the solvent to obtain a crude product. Purify the crude product through a separation column to obtain a solid compound 2-a (15 g, yield 51%);
[0070] Step (2)
[0071]
[0072] Add compound 2-a (15 g, 0.067 mol), 150 ml of dichloromethane and imidazole (12 g, 0.17 mol) to a 250 ml three-necked flask, stir in an ice water bath to obtain a second reaction solution; dissolve tert-butyldimethylchlorosilane (22 g, 0.15 mol) in 100 ml of tetrahydrofuran and then drop it into the above second reaction solution, stir for 2 hours, filter, wash the filtrate with water, dry and rotary evaporate to obtain 31 g of a crude product of oily compound 2-b;
[0073] Step (3)
[0074]
[0075] Add 200 ml of ethanol, the crude product of compound 2-b (31 g), 2-hydrazinobenzothiazole (11 g, 67 mmol) and p-toluenesulfonic acid (1.3 g, 6.7 mmol) to a 500 ml three-necked flask, warm it up to 50 °C, keep the temperature for reaction for 2 hours. After the reaction is completed, obtain the third reaction solution. Pour the third reaction solution into water, extract with ethyl acetate, dry, and purify through a column to obtain compound 2-c (28 g, yield 75%);
[0076] Step (4)
[0077]
[0078] Add compound 2-c (28 g, 0.05 mol), potassium carbonate (9.6 g, 0.07 mol) and diethylene glycol monoether sulfonate (12 g, 0.06 mol) to a 500 ml three-necked flask, heat to 80 °C and stir for 2 hours to obtain the fourth reaction solution. Pour the fourth reaction solution into ice water, stir, filter by suction to obtain solid compound 2-d (20 g, yield 60.6%);
[0079] Step (5)
[0080]
[0081] Add compound 2-d (20 g, 0.03 mol) and 200 ml of tetrahydrofuran to a 500 ml three-necked flask, and then add tetrabutylammonium fluoride trihydrate (23.6 g, 0.075 mol) in batches. Stir at room temperature for 12 hours to obtain the fifth reaction solution. Pour the fifth reaction solution into water, stir, extract with ethyl acetate, dry, evaporate to dryness, and then stir with petroleum ether to obtain solid compound 2-e (10 g, yield 76.9%);
[0082] Step (6)
[0083]
[0084] Add 150 ml of dimethylformamide, potassium carbonate (8 g, 58 mmol), compound 2-e (10 g, 23 mmol) and compound A (11.8 g, 50 mmol) to a 250 ml three-necked flask, stir and heat to 80 °C, keep the temperature for reaction for 3 hours. After the reaction is completed, obtain the fifth reaction solution. Pour the fifth reaction solution into ice water, stir, filter, and dry in air to obtain solid 2-f (11 g, yield 66.7%);
[0085] Step (7)
[0086]
[0087] Add compound 2-f (11 g, 15.5 mmol), 4-acryloyloxyhexyloxyphenol (8.6 g, 33 mmol), 4-dimethylaminopyridine (0.2 g, 1.6 mmol), 1,3-dicyclohexylcarbodiimide (7.2 g, 35 mmol) and 150 ml of dichloromethane to a 500 ml three-necked flask. Stir at room temperature for 4 hours under nitrogen protection, filter to obtain the filtrate. Evaporate the filtrate to dryness and recrystallize with ethanol and toluene to obtain the polymeric compound RM-6 (13.4 g, yield 72%), MS (m / z) (M+): 1201.
[0088] Example 3
[0089] This example provides a polymeric compound RM-30, and the synthesis route of this compound is as follows:
[0090] Step (1)
[0091]
[0092] Add the compound 2-e (5 g, 11.7 mmol) obtained in step (5) of Example 2, trans-4-methylcyclohexanecarboxylic acid (2 g, 14 mmol), 4-dimethylaminopyridine (0.2 g, 1.6 mmol), dicyclohexylcarbodiimide (3.5 g, 17 mmol) and 100 ml of dichloromethane into a 250 ml three-necked flask. Stir at room temperature for 4 hours under nitrogen protection. After the reaction is completed, filter to obtain a filtrate. Rotate the filtrate to dryness and recrystallize with ethanol and toluene to obtain the compound 3-a (5.2 g, 80.6%);
[0093] Step (2)
[0094]
[0095] Add the compound 3-a (5.2 g, 9.4 mmol), 4-acryloyloxyhexyloxyphenol (3.3 g, 11.3 mmol), -dimethylaminopyridine (0.1 g, 0.8 mmol), dicyclohexylcarbodiimide (3.5 g, 17 mmol) and 100 ml of dichloromethane into a 250 ml three-necked flask. Stir at room temperature for 4 hours under nitrogen protection, filter to obtain a filtrate. Rotate the filtrate to dryness and recrystallize with ethanol and toluene to obtain the polymeric compound RM-30 (5.5 g, 0.6%), MS (m / z) (M+): 826.
[0096] Example 4
[0097] This example provides a polymeric compound RM-32, and the synthesis route of this compound is as follows:
[0098] Step (1)
[0099]
[0100] Add the compound 2-e (5 g, 11.7 mmol) obtained in step (5) of Example 2, trans-4'-propylbicyclohexanecarboxylic acid (3.5 g, 14 mmol), 4-dimethylaminopyridine (0.2 g, 1.6 mmol), dicyclohexylcarbodiimide (3.5 g, 17 mmol) and 100 ml of dichloromethane into a 250 ml three-necked flask. Stir at room temperature for 4 hours under nitrogen protection. After the reaction is completed, filter to obtain a filtrate. Rotate the filtrate to dryness and recrystallize with ethanol and toluene to obtain the compound 4-a (4.8 g, 62.3%);
[0101] Step (2)
[0102]
[0103] Add compound 4-a (4.8 g, 7.2 mmol), 4-acryloyloxyhexyloxyphenol (3.3 g, 8.7 mmol), 4-dimethylaminopyridine (0.1 g, 0.8 mmol), dicyclohexylcarbodiimide (2.7 g, 13 mmol) and 100 ml of dichloromethane to a 250 ml three-necked flask. Stir at room temperature for 4 hours under nitrogen protection, filter to obtain a filtrate. Rotate the filtrate to dryness and recrystallize with ethanol and toluene to obtain the polymerizable compound RM-32 (5.1 g, 76.1%), MS (m / z) (M+): 937.
[0104] Example 5
[0105] This example provides a polymerizable compound RM-5, and the synthetic route of this compound is as follows:
[0106]
[0107] Add the compound 1-d (5 g, 10.7 mmol) obtained in step (4) of Example 1, compound B (9.02 g, 23.7 mmol), 4-dimethylaminopyridine (0.2 g, 2 mmol), dicyclohexylcarbodiimide (5.6 g, 26.9 mmol) and 100 ml of dichloromethane to a 250 ml three-necked flask. Stir at room temperature for 4 hours under nitrogen protection, filter to obtain a filtrate. Rotate the filtrate to dryness and recrystallize with ethanol and toluene to obtain the polymerizable compound RM-5 (8.5 g, 66.4%), MS (m / z) (M+): 1189.
[0108] Example 6
[0109] This example provides a polymerizable compound RM-9, and the synthetic route of this compound is as follows:
[0110]
[0111] Add the compound 2-e (5 g, 11.7 mmol) obtained in step (5) of Example 2, compound B (9.79 g, 25.7 mmol), 4-dimethylaminopyridine (0.2 g, 2 mmol), dicyclohexylcarbodiimide (6.03 g, 29.3 mmol) and 100 ml of dichloromethane to a 250 ml three-necked flask. Stir at room temperature for 4 hours under nitrogen protection, filter to obtain a filtrate. Rotate the filtrate to dryness and recrystallize with ethanol and toluene to obtain the polymerizable compound RM-9 (6.2 g, 46%), MS (m / z) (M+): 1153.
[0112] Example 7
[0113] This example provides a composition comprising the following components in mass percentage:
[0114] The polymerizable compound RM-1 provided in Example 1 with a mass percentage of 14.693%, LC242 with a percentage of 10%, the inhibitor 2,6-di-tert-butyl-4-methylphenol with a mass percentage of 0.075%, the photoinitiator Irgacure 369 (manufactured by BASF) with a mass percentage of 0.15%, the light stabilizer Tinuvin 123 with a mass percentage of 0.150%, and the balance being toluene.
[0115] (The chemical formula of LC242 is as follows:
[0116]
[0117] Example 8
[0118] This example provides a composition comprising the following components in mass percentage:
[0119] The polymerizable compound RM-6 provided in Example 2 with a mass percentage of 14.693%, LC242 with a percentage of 10%, the inhibitor 2,6-di-tert-butyl-4-methylphenol with a mass percentage of 0.075%, the photoinitiator Irgacure 369 (manufactured by BASF) with a mass percentage of 0.15%, the light stabilizer Tinuvin 123 with a mass percentage of 0.150%, and the balance being toluene.
[0120] Example 9
[0121] This example provides a composition comprising the following components in mass percentage:
[0122] The polymerizable compound RM-30 provided in Example 3 with a mass percentage of 14.693%, LC242 with a percentage of 10%, the inhibitor 2,6-di-tert-butyl-4-methylphenol with a mass percentage of 0.075%, the photoinitiator Irgacure 369 (manufactured by BASF) with a mass percentage of 0.15%, the light stabilizer Tinuvin 123 with a mass percentage of 0.150%, and the balance being toluene.
[0123] Example 10
[0124] This example provides a composition comprising the following components in mass percentage:
[0125] The polymerizable compound RM-32 provided in Example 4 with a mass percentage content of 14.693%, LC242 with a percentage content of 10%, the inhibitor 2,6-di-tert-butyl-4-methylphenol with a mass percentage content of 0.075%, the photoinitiator Irgacure 369 (manufactured by BASF) with a mass percentage content of 0.15%, the light stabilizer Tinuvin 123 with a mass percentage content of 0.150%, and the balance being toluene.
[0126] Example 11
[0127] This example provides a composition comprising components with the following mass percentage contents:
[0128] The polymerizable compound RM-5 provided in Example 5 with a mass percentage content of 14.693%, LC242 with a percentage content of 10%, the inhibitor 2,6-di-tert-butyl-4-methylphenol with a mass percentage content of 0.075%, the photoinitiator Irgacure 369 (manufactured by BASF) with a mass percentage content of 0.15%, the light stabilizer Tinuvin 123 with a mass percentage content of 0.150%, and the balance being toluene.
[0129] Example 12
[0130] This example provides a composition comprising components with the following mass percentage contents:
[0131] The polymerizable compound RM-9 provided in Example 6 with a mass percentage content of 14.693%, LC242 with a percentage content of 10%, the inhibitor 2,6-di-tert-butyl-4-methylphenol with a mass percentage content of 0.075%, the photoinitiator Irgacure 369 (manufactured by BASF) with a mass percentage content of 0.15%, the light stabilizer Tinuvin 123 with a mass percentage content of 0.150%, and the balance being toluene.
[0132] Example 13
[0133] This example provides a composition comprising components with the following mass percentage contents:
[0134] The polymerizable compound RM-1 provided in Example 1 with a mass percentage content of 14.693%, LC242 with a percentage content of 10%, the inhibitor 2,6-di-tert-butyl-4-methylphenol with a mass percentage content of 0.075%, the photoinitiator Irgacure 369 (manufactured by BASF) with a mass percentage content of 0.15%, the light stabilizer Tinuvin 123 with a mass percentage content of 0.150%, and the balance being cyclohexanone.
[0135] Example 14
[0136] This example provides a composition, comprising components with the following mass percentages:
[0137] The polymerizable compound RM-6 provided in Example 2 with a mass percentage of 14.693%, LC242 with a percentage of 10%, the inhibitor 2,6-di-tert-butyl-4-methylphenol with a mass percentage of 0.075%, the photoinitiator Irgacure 369 (manufactured by BASF) with a mass percentage of 0.15%, the light stabilizer Tinuvin 123 with a mass percentage of 0.150%, and the balance being cyclopentanone.
[0138] Example 15
[0139] This example provides a composition, comprising components with the following mass percentages:
[0140] The polymerizable compound RM-30 provided in Example 3 with a mass percentage of 14.693%, LC242 with a percentage of 10%, the inhibitor 2,6-di-tert-butyl-4-methylphenol with a mass percentage of 0.075%, the photoinitiator Irgacure 369 (manufactured by BASF) with a mass percentage of 0.15%, the light stabilizer Tinuvin 123 with a mass percentage of 0.150%, and the balance being cyclohexanone.
[0141] Example 16
[0142] This example provides a composition, comprising components with the following mass percentages:
[0143] The polymerizable compound RM-32 provided in Example 4 with a mass percentage of 14.693%, LC242 with a percentage of 10%, the inhibitor 2,6-di-tert-butyl-4-methylphenol with a mass percentage of 0.075%, the photoinitiator Irgacure 369 (manufactured by BASF) with a mass percentage of 0.15%, the light stabilizer Tinuvin 123 with a mass percentage of 0.150%, and the balance being cyclopentanone.
[0144] Example 17
[0145] This example provides a composition, comprising components with the following mass percentages:
[0146] The polymerizable compound RM-9 provided in Example 5 with a mass percentage of 14.693%, LC242 with a percentage of 10%, the inhibitor 2,6-di-tert-butyl-4-methylphenol with a mass percentage of 0.075%, the photoinitiator Irgacure 369 (manufactured by BASF) with a mass percentage of 0.15%, the light stabilizer Tinuvin 123 with a mass percentage of 0.150%, and the balance being cyclohexanone.
[0147] Example 18
[0148] This example provides a composition comprising the following components in mass percentages:
[0149] The polymerizable compound RM-9 provided in Example 6 with a mass percentage of 14.693%, LC242 with a percentage of 10%, the inhibitor 2,6-di-tert-butyl-4-methylphenol with a mass percentage of 0.075%, the photoinitiator Irgacure 369 (manufactured by BASF) with a mass percentage of 0.15%, the light stabilizer Tinuvin 123 with a mass percentage of 0.150%, and the balance being cyclopentanone.
[0150] Example 19
[0151] This example provides an optically anisotropic film, which is prepared at least through the following steps:
[0152] Mix the composition provided in Example 7 evenly and stir until the solid is completely dissolved at room temperature to obtain a coating liquid. Spin-coat the coating liquid onto a TAC with an alignment layer to form a liquid crystal film. Dry the liquid crystal film at 140 °C for 2 min, cool it to room temperature, and irradiate it with UV light from a mercury lamp for about 2 min at room temperature and in a nitrogen atmosphere for photopolymerization to obtain the optically anisotropic film.
[0153] Example 20
[0154] This example provides an optically anisotropic film, which is prepared at least through the following steps:
[0155] Mix the composition provided in Example 8 evenly and stir until the solid is completely dissolved at room temperature to obtain a coating liquid. Spin-coat the coating liquid onto a TAC with an alignment layer to form a liquid crystal film. Dry the liquid crystal film at 140 °C for 2 min, cool it to room temperature, and irradiate it with UV light from a mercury lamp for about 2 min at room temperature and in a nitrogen atmosphere for photopolymerization to obtain the optically anisotropic film.
[0156] Example 21
[0157] This example provides an optically anisotropic film, which is prepared at least through the following steps:
[0158] Mix the composition provided in Example 9 evenly and stir until the solid is completely dissolved at room temperature to obtain a coating liquid. Spin-coat the coating liquid onto a TAC with an alignment layer to form a liquid crystal film. Dry the liquid crystal film at 140 °C for 2 min, cool it to room temperature, and irradiate it with UV light from a mercury lamp for about 2 min at room temperature and in a nitrogen atmosphere for photopolymerization to obtain the optically anisotropic film.
[0159] Example 22
[0160] This example provides an optically anisotropic film, which is prepared at least through the following steps:
[0161] Mix the composition provided in Example 10 evenly, stir until the solid is completely dissolved at room temperature to obtain a coating liquid. Spin-coat the coating liquid onto a TAC with an alignment layer to form a liquid crystal film. Dry the liquid crystal film at 140 °C for 2 min, cool it to room temperature, and irradiate it with UV light using a mercury lamp for about 2 min at room temperature and in a nitrogen atmosphere for photopolymerization to obtain an optically anisotropic film.
[0162] Example 23
[0163] This example provides an optically anisotropic film, which is prepared at least through the following steps:
[0164] Mix the composition provided in Example 11 evenly, stir until the solid is completely dissolved at room temperature to obtain a coating liquid. Spin-coat the coating liquid onto a TAC with an alignment layer to form a liquid crystal film. Dry the liquid crystal film at 140 °C for 2 min, cool it to room temperature, and irradiate it with UV light using a mercury lamp for about 2 min at room temperature and in a nitrogen atmosphere for photopolymerization to obtain an optically anisotropic film.
[0165] Example 24
[0166] This example provides an optically anisotropic film, which is prepared at least through the following steps:
[0167] Mix the composition provided in Example 12 evenly, stir until the solid is completely dissolved at room temperature to obtain a coating liquid. Spin-coat the coating liquid onto a TAC with an alignment layer to form a liquid crystal film. Dry the liquid crystal film at 140 °C for 2 min, cool it to room temperature, and irradiate it with UV light using a mercury lamp for about 2 min at room temperature and in a nitrogen atmosphere for photopolymerization to obtain an optically anisotropic film.
[0168] Example 25
[0169] This example provides an optically anisotropic film, which is prepared at least through the following steps:
[0170] Mix the composition provided in Example 13 evenly, stir until the solid is completely dissolved at room temperature to obtain a coating liquid. Spin-coat the coating liquid onto a TAC with an alignment layer to form a liquid crystal film. Dry the liquid crystal film at 140 °C for 2 min, cool it to room temperature, and irradiate it with UV light using a mercury lamp for about 2 min at room temperature and in a nitrogen atmosphere for photopolymerization to obtain an optically anisotropic film.
[0171] Example 26
[0172] This embodiment provides an optically anisotropic film, which is prepared at least through the following steps:
[0173] Mix the composition provided in Example 14 evenly, stir until the solid is completely dissolved at room temperature to obtain a coating liquid. Spin-coat the coating liquid onto a TAC with an alignment layer to form a liquid crystal film. Dry the liquid crystal film at 140 °C for 2 min, cool it to room temperature, and irradiate it with UV light using a mercury lamp for about 2 min under room temperature and nitrogen atmosphere for photopolymerization to obtain the optically anisotropic film.
[0174] Example 27
[0175] This embodiment provides an optically anisotropic film, which is prepared at least through the following steps:
[0176] Mix the composition provided in Example 15 evenly, stir until the solid is completely dissolved at room temperature to obtain a coating liquid. Spin-coat the coating liquid onto a TAC with an alignment layer to form a liquid crystal film. Dry the liquid crystal film at 140 °C for 2 min, cool it to room temperature, and irradiate it with UV light using a mercury lamp for about 2 min under room temperature and nitrogen atmosphere for photopolymerization to obtain the optically anisotropic film.
[0177] Example 28
[0178] This embodiment provides an optically anisotropic film, which is prepared at least through the following steps:
[0179] Mix the composition provided in Example 16 evenly, stir until the solid is completely dissolved at room temperature to obtain a coating liquid. Spin-coat the coating liquid onto a TAC with an alignment layer to form a liquid crystal film. Dry the liquid crystal film at 140 °C for 2 min, cool it to room temperature, and irradiate it with UV light using a mercury lamp for about 2 min under room temperature and nitrogen atmosphere for photopolymerization to obtain the optically anisotropic film.
[0180] Example 29
[0181] This embodiment provides an optically anisotropic film, which is prepared at least through the following steps:
[0182] Mix the composition provided in Example 17 evenly, stir until the solid is completely dissolved at room temperature to obtain a coating liquid. Spin-coat the coating liquid onto a TAC with an alignment layer to form a liquid crystal film. Dry the liquid crystal film at 140 °C for 2 min, cool it to room temperature, and irradiate it with UV light using a mercury lamp for about 2 min under room temperature and nitrogen atmosphere for photopolymerization to obtain the optically anisotropic film.
[0183] Example 30
[0184] This embodiment provides an optically anisotropic film, which is prepared at least through the following steps:
[0185] Mix the composition provided in Example 18 evenly, stir until the solid is completely dissolved at room temperature to obtain a coating liquid. Spin-coat the coating liquid onto a TAC with an alignment layer to form a liquid crystal film. Dry the liquid crystal film at 140 °C for 2 min, cool it to room temperature, and irradiate it with UV light from a mercury lamp for about 2 min under room temperature and a nitrogen atmosphere for photopolymerization to obtain the optically anisotropic film.
[0186] Comparative Example 1
[0187] This comparative example provides a polymerizable compound DRM-1, and its synthesis route is used to synthesize the polymerizable compound DRM-1 according to the synthesis route in Example 1 of Patent CN114026078A, [2-[(1,3-benzothiazol-2-ylhydrazono)methyl]-4-(4-methylcyclohexanecarbonyl)oxy-phenyl] 4-(6-prop-2-enoyloxyhexyloxy)benzoate.
[0188] Comparative Example 2
[0189] This comparative example provides a polymerizable compound DRM-2, and its synthesis route is used to synthesize the polymerizable compound DRM-2 according to the synthesis route in Example 7 of Patent CN114026078A, [2-[(1,3-benzothiazol-2-yl(hexyl)hydrazono)methyl]-4-(4-heptylcyclohexanecarbonyl)oxy-phenyl] 4-(6-prop-2-enoyloxyhexyloxy)benzoate.
[0190] Comparative Example 3
[0191] This comparative example provides a composition, including components with the following mass percentages:
[0192] The polymerizable compound DRM-1 provided in Comparative Example 1 with a mass percentage of 14.693%, LC242 with a percentage of 10%, the inhibitor 2,6-di-tert-butyl-4-methylphenol with a mass percentage of 0.075%, the photoinitiator Irgacure369 (manufactured by BASF) with a mass percentage of 0.15%, the light stabilizer Tinuvin 123 with a mass percentage of 0.150%, and the balance being cyclohexanone.
[0193] Comparative Example 4
[0194] This comparative example provides a composition, including components with the following mass percentages:
[0195] The polymeric compound DRM-1 provided in Comparative Example 1 with a mass percentage content of 14.693%, LC242 with a percentage content of 10%, the inhibitor 2,6-di-tert-butyl-4-methylphenol with a mass percentage content of 0.075%, the photoinitiator Irgacure 369 (manufactured by BASF) with a mass percentage content of 0.15%, the light stabilizer Tinuvin 123 with a mass percentage content of 0.150%, and the balance being toluene.
[0196] Comparative Example 5
[0197] This comparative example provides a composition, including components with the following mass percentage contents:
[0198] The polymeric compound DRM-2 provided in Comparative Example 2 with a mass percentage content of 14.693%, LC242 with a percentage content of 10%, the inhibitor 2,6-di-tert-butyl-4-methylphenol with a mass percentage content of 0.075%, the photoinitiator Irgacure 369 (manufactured by BASF) with a mass percentage content of 0.15%, the light stabilizer Tinuvin 123 with a mass percentage content of 0.150%, and the balance being cyclohexanone.
[0199] Comparative Example 6
[0200] This comparative example provides a composition, including components with the following mass percentage contents:
[0201] The polymeric compound DRM-2 provided in Comparative Example 2 with a mass percentage content of 14.693%, LC242 with a percentage content of 10%, the inhibitor 2,6-di-tert-butyl-4-methylphenol with a mass percentage content of 0.075%, the photoinitiator Irgacure 369 (manufactured by BASF) with a mass percentage content of 0.15%, the light stabilizer Tinuvin 123 with a mass percentage content of 0.150%, and the balance being toluene.
[0202] Comparative Example 7
[0203] This comparative example provides an optically anisotropic film, which is prepared at least through the following steps:
[0204] Mix the composition provided in Comparative Example 3 evenly and stir until the solid is completely dissolved at room temperature to obtain a coating liquid. Spin-coat the coating liquid onto a TAC with an alignment layer to form a liquid crystal film. Dry the liquid crystal film at 140°C for 2 min, cool it to room temperature, and irradiate it with UV light using a mercury lamp for about 2 min at room temperature and in a nitrogen atmosphere for photopolymerization to obtain an optically anisotropic film.
[0205] Comparative Example 8
[0206] This comparative example provides an optically anisotropic film, which is prepared at least through the following steps:
[0207] Mix the composition provided in Comparative Example 4 evenly, stir until the solid is completely dissolved at room temperature to obtain a coating liquid. Spin-coat the coating liquid onto a TAC with an alignment layer to form a liquid crystal film. Dry the liquid crystal film at 140 °C for 2 min, cool it to room temperature, and irradiate it with UV light using a mercury lamp for about 2 min under room temperature and a nitrogen atmosphere for photopolymerization to obtain an optically anisotropic film.
[0208] Comparative Example 9
[0209] This comparative example provides an optically anisotropic film, which is prepared at least through the following steps:
[0210] Mix the composition provided in Comparative Example 5 evenly, stir until the solid is completely dissolved at room temperature to obtain a coating liquid. Spin-coat the coating liquid onto a TAC with an alignment layer to form a liquid crystal film. Dry the liquid crystal film at 140 °C for 2 min, cool it to room temperature, and irradiate it with UV light using a mercury lamp for about 2 min under room temperature and a nitrogen atmosphere for photopolymerization to obtain an optically anisotropic film.
[0211] Comparative Example 10
[0212] This comparative example provides an optically anisotropic film, which is prepared at least through the following steps:
[0213] Mix the composition provided in Comparative Example 6 evenly, stir until the solid is completely dissolved at room temperature to obtain a coating liquid. Spin-coat the coating liquid onto a TAC with an alignment layer to form a liquid crystal film. Dry the liquid crystal film at 140 °C for 2 min, cool it to room temperature, and irradiate it with UV light using a mercury lamp for about 2 min under room temperature and a nitrogen atmosphere for photopolymerization to obtain an optically anisotropic film.
[0214] Compound Effect Example 1
[0215] Compound Solubility Experiment: To illustrate the solubility of the polymeric compounds provided by the present invention, the maximum solubility of the compounds was evaluated through the following experimental procedure, which is briefly described as follows: The polymeric compounds RM-1, RM-6, RM-30, RM-32, RM-5, RM-9, DRM-1, and DRM-2 provided in Examples 1 to 6 and Comparative Examples 1 and 2 were respectively placed in the industrial common solvent cyclohexanone and LC242 was added, where the mass percentage content of LC242 was 10%. The polymeric compounds RM-1, RM-6, RM-30, RM-32, RM-5, RM-9, DRM-1, and DRM-2 were respectively formulated into solutions with mass percentage contents of 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, and 45%. The above solutions were placed in an environment of 20°C ± 3°C for 30 days. The specific experimental results are shown in Table 1:
[0216] Table 1
[0217]
[0218] As can be seen from the data in Table 1, compared with the polymeric compounds provided in the comparative examples, the maximum solubility of the polymeric compounds provided by the present invention in cyclohexanone can reach 45%, while in Comparative Example 1 and Comparative Example 2, the solubility can only reach 25% - 30% under the same conditions, indicating that the polymeric compounds provided by the present invention have high solubility in the industrial common solvent - cyclohexanone.
[0219] Compound Effect Example 2
[0220] To illustrate that the polymeric compounds provided by the present invention can be dissolved in industrial common solvents and have high storage stability in solution state, the solubility and stability of the polymeric compounds were evaluated through the following experimental procedure, which is briefly described as follows: The polymeric compounds RM-1, RM-6, RM-30, RM-32, RM-5, RM-9, DRM-1, and DRM-2 provided in Examples 1 to 6 and Comparative Examples 1 and 2 were respectively placed in the industrial common solvents cyclohexanone, cyclopentanone, and toluene and LC242 was added, where the mass percentage content of LC242 was 10% and the mass percentage content of the polymeric compound was 15%. The above polymeric compound solutions were respectively placed in an environment of 20°C ± 3°C for 30 days, 60 days, and 90 days. The specific experimental results are shown in Table 2:
[0221] Table 2
[0222]
[0223]
[0224] As can be seen from the data in Table 2, compared with the polymeric compounds provided in the comparative examples, the polymeric compounds provided in the present invention can be well dissolved in industrially common solvents such as cyclohexanone, cyclopentanone, and toluene, and the above solutions still have high stability after being placed in an environment of 20°C ± 3°C for 30 days, 60 days, and 90 days respectively. However, in the case of Comparative Example 1, precipitation occurred after being placed in cyclopentanone for 30 days in an environment of 20°C ± 3°C, and the solubility of the polymeric compounds provided in Comparative Example 1 and Comparative Example 2 gradually decreased with the increase of the storage time, indicating that compared with the polymeric compounds provided in the comparative examples, the polymeric compounds provided in the present invention can be well dissolved in industrially common solvents such as cyclohexanone, cyclopentanone, and toluene, and have higher storage stability in the solution state.
[0225] Optical anisotropic film Effect Example 1
[0226] Method for evaluating the alignment quality of liquid crystal in an optical anisotropic film: The alignment quality of the liquid crystal in the film is checked by placing the optical anisotropic film between two crossed polarizers, and it is adjusted to obtain a dark state. If the dark state does not show defects and the liquid crystal is well aligned, the alignment quality is defined as very good. If the dark state has slight leakage due to uneven alignment of the liquid crystal, the alignment quality is defined as good. If the dark state has slight leakage in some regions with crystallization, the alignment quality is defined as medium. If the liquid crystal is not aligned and there is no dark state, the alignment quality is defined as poor.
[0227] The optical anisotropic films provided in Examples 19 to 30 of the present invention and the optical anisotropic films provided in Comparative Examples 7 to 10 were placed between two crossed polarizers to check the alignment quality of the liquid crystal in the optical anisotropic films. The specific evaluation results are shown in Table 2:
[0228] Table 3
[0229] Film Alignment quality Example 19 Very good Example 20 Very good Example 21 Very good Example 22 Very good Example 23 Very good Example 24 Very good Example 25 Very good Example 26 Very good Example 27 Very good Example 28 Very good Example 29 Very good Example 30 Very good Comparative Example 7 Very good Comparative Example 8 Very good Comparative Example 9 Good Comparative Example 10 Good
[0230] As can be seen from the evaluation results in Table 3, compared with the optical anisotropic films provided in Comparative Examples 7 to 10, the optical anisotropic films provided in Examples 19 to 30 of the present invention have better alignment quality.
[0231] Optical anisotropic film Effect Example 2
[0232] If the optical anisotropic film can satisfy the following formulas (1) and (2), then the optical anisotropic film has an inverse wavelength dispersion property that the in-plane retardation at a short wavelength is greater than the in-plane retardation at a long wavelength.
[0233] Re(450) / Re(550) ≤ 1.0 (1)
[0234] 1.0 ≤ Re(650) / Re(550) (2)
[0235] In the formula, Re(λ) represents the phase difference of the wavelength at wavelength λ, Re(λ) = (ne(λ) - no(λ)) × d, d represents the thickness of the optically anisotropic film, the direction of ne is parallel to the plane of the optically anisotropic film, and the direction of no is perpendicular to the plane of the optically anisotropic film.
[0236] The phase differences of the optically anisotropic films provided in Examples 19 to 30 and Comparative Examples 7 to 10 of the present invention were measured using an ellipsometer. Re450 represents the phase difference of the optically anisotropic film at a wavelength of 450 nm, Re550 represents the phase difference of the optically anisotropic film at a wavelength of 550 nm, and Re650 represents the phase difference of the optically anisotropic film at a wavelength of 650 nm. Re450 / Re550 and Re650 / Re550 were calculated from the measurement data, and the specific calculation results are shown in Table 3:
[0237] Table 4
[0238] Example Re450 / Re550 Re650 / Re550 Example 19 0.72 1.07 Example 20 0.74 1.08 Example 21 0.77 1.08 Example 22 0.75 1.07 Example 23 0.73 1.06 Example 24 0.72 1.07 Example 25 0.73 1.06 Example 26 0.76 1.07 Example 27 0.77 1.08 Example 28 0.76 1.07 Example 29 0.74 1.08 Example 30 0.73 1.07 Comparative Example 7 0.87 1.02 Comparative Example 8 0.91 0.98 Comparative Example 9 0.82 1.04 Comparative Example 10 0.89 0.99
[0239] When using the optically anisotropic film as a retarder plate or the like, in order to improve the non-uniform color and viewing angle characteristics, 0.7 < Re450 / Re550 < 0.9 is preferred, and the closer the Re450 / Re550 value is to 0.7, the better; in order to improve the color
[0240] 1.00 < Re650 / Re550 < 1.2 is preferred, and the closer the Re450 / Re550 value is to 1.2, the better. From the calculation results in Table 4, it can be seen that the Re450 / Re550 values of the optically anisotropic films provided in Examples 19 to 30 of the present invention are lower than the Re450 / Re550 values of the optically anisotropic films provided in Comparative Examples 7 to 10, and all the Re450 / Re550 values of the optically anisotropic films provided in Examples 19 to 30 of the present invention are < 0.77. It can also be found from Table 4 that the Re650 / Re550 values of the optically anisotropic films provided in Examples 19 to 30 of the present invention are significantly greater than the Re650 / Re550 values of the optically anisotropic films provided in Comparative Examples 7 to 10, and all the Re650 / Re550 values of the optically anisotropic films provided in Examples 19 to 30 of the present invention are ≥ 1.06. Therefore, the optically anisotropic film provided by the present invention has excellent inverse wavelength dispersion, is a retarder with excellent performance, can improve the contrast and compensate for the hue when viewing a liquid crystal display from the front or obliquely, and can also prevent the contrast from decreasing or the image from being reflected and glare caused by the reflection of external light on the display surface.
[0241] Obviously, the above embodiments of the present invention are merely examples for clearly illustrating the present invention, rather than limitations on the implementation manners of the present invention. For those of ordinary skill in the art, other different forms of changes or modifications can be made based on the above description. It is impossible to list all the implementation manners here. Any obvious changes or modifications derived from the technical solutions of the present invention still fall within the protection scope of the present invention.
Claims
1. A polymeric compound, characterized in that, the general structural formula of the compound is shown in Formula I: wherein X represents O or S; Said R 11 represents hydrogen or a straight-chain or branched alkyl group having 1 to 20 carbon atoms, and one -CH 2 - or two or more non-adjacent -CH 2 - may each independently be 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 any one hydrogen in the alkyl group may be substituted by fluorine; Said R 12 , R 31 each independently represents hydrogen or a linear or branched alkyl group having 1 to 20 carbon atoms; The R 21 is the same as or different from R 22 and each independently selected from the group represented by formula R-1 or formula R-2, and the R 21 and R 22 at least one of which is selected from the group represented by formula R-1, P 0 -Ar 11 -Ar 21 -Q 21 - * R-2 Among them, the P 1 represents a polymerizable group The P 0 represents a linear or branched alkyl group having 1 to 20 carbon atoms; E represents a single bond or an alkylene group having 1 to 8 carbon atoms; G is selected from -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, in any optional quantity combination of any one or any several of them; n is selected from integers from 0 to 8; The Ar 11 represents a substituted 1,4-cyclohexylene group, an unsubstituted 1,4-cyclohexylene group, a substituted 1,4-phenylene group or an unsubstituted 1,4-phenylene group; When the Ar 11 has a substituent, the substituent of the Ar 11 can be one or more, and each independently selected from fluorine, chlorine or a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms, and one -CH 2 - or two or more non-adjacent -CH 2 - can each independently be substituted by -O-, -CO-, -COO- or -OCO-, and any one hydrogen in the alkyl group can be substituted by fluorine; Said Ar 21 represents a single bond or 1,4-cyclohexylene; Said Q 11 selected from any one or any combination of a single bond, -OCH 2 -, -CH 2 O-, -COO- or -OCO-; The said Q 21 Selected from -OCH 2 -, -CH 2 O-, -COO-CH 2 CH 2 -, -CH 2 CH 2 -OCO-, -COO- or -OCO-, or any combination of any several of them.
2. The polymeric compound according to claim 1, characterized in that, The R 11 represents hydrogen or a straight-chain alkyl group having 1 to 12 carbon atoms, and one -CH 2 - in the alkyl group or two or more non-adjacent -CH 2 - may each independently be 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 any one hydrogen in the alkyl group may be substituted by fluorine.
3. The polymeric compound according to claim 1, characterized in that, Said R 12 and R 31 represent hydrogen or a straight-chain alkyl group having 1 to 5 carbon atoms.
4. The polymeric compound according to claim 1, characterized in that, the compound shown in Formula I is selected from the structures shown in Formula I-1 or Formula I-2:
5. The polymeric compound according to claim 1, characterized in that, the compound shown in Formula I is selected from any one of the structures shown in Formula I-11 to Formula I-18:
6. The polymeric compound according to claim 1, characterized in that, the group shown in Formula R-1 is selected from any one of the groups shown in Formula R-11, R-12, R-13, R-15:
7. The polymeric compound according to claim 1, characterized in that, the group shown in Formula R-2 is selected from any one of the groups shown in Formula R-21 to Formula R-24:
8. A polymeric composition, characterized in that, it comprises the polymeric compound according to any one of claims 1 to 7.
9. An optically anisotropic film, characterized in that, it is obtained by polymerizing the polymeric composition according to claim 8.
Citation Information
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