Deuterated negative dispersion compound and synthetic method and application thereof

Abstract

The invention discloses a deuterated negative dispersion compound and a synthesis method and application thereof, and belongs to the technical field of optical materials, the deuterated negative dispersion compound is selected from a compound shown in a general formula (1), the deuterated negative dispersion compound effectively prolongs the service life of a diaphragm due to the existence of deuterated hydrogen, and the service life of the diaphragm is prolonged. The deuterated negative dispersion compound can be applied to a negative dispersion optical film material.

Description

Technical Field

[0001] The invention relates to a deuterated negative dispersion compound and a synthesis method and application thereof, belonging to the technical field of optical materials. Background Art

[0002] A polymerizable compound (RM) is a raw material for preparing various optically anisotropic bodies. Usually, an RM solution is coated on a substrate to align it. After curing, an optically anisotropic polymer film with uniform orientation is formed, which is an optically anisotropic body. The orientation of the film can be planar (the liquid crystal molecules are basically parallel to the layer orientation), homeotropic (rectangular or perpendicular to the layer) or inclined, or it can be cholesteric oriented. Therefore, polymerizable compound materials have received widespread attention.

[0003] Depending on the application field, optical anisotropic bodies include, but are not limited to, birefringent films, optical retardation films (phase difference films), negative dispersion optical films, optical compensation films, vision expansion films, reflective films, selective reflective films, anti-reflective films, brightness enhancement films, liquid crystal orientation films, polarizing films (deflecting plates), polarizing elements, circular polarizing elements, elliptically polarizing elements, and various other optical elements.

[0004] The polymerizable compound material controls optical anisotropy by optically compensating for the dispersion caused by different wavelengths when light propagates in a medium, thereby improving optical efficiency and increasing the viewing angle. However, the life of the film made of the existing polymerizable compound material is still unsatisfactory.

[0005] Therefore, it is required to develop the following deuterated negative dispersion compounds and their synthesis methods and applications, so as to solve the above technical problems. Summary of the invention

[0006] In order to at least solve one problem existing in the above-mentioned prior art, the present invention provides a deuterated negative dispersion compound and a synthesis method thereof. The negative dispersion compound effectively improves the life of the film due to deuteration. The deuterated negative dispersion compound can be applied to negative dispersion optical film materials.

[0007] In order to achieve the above object, the present invention adopts the following technical solution: a polymerizable compound, wherein the polymerizable compound is a deuterated negative dispersion compound.

[0008] The deuterated negative dispersion compound is selected from the compounds represented by the general formula (1), (1) R represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, a haloalkoxy group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a haloalkenyl group having 2 to 30 carbon atoms, an alkenyloxy group having 2 to 30 carbon atoms, a haloalkenyloxy group having 2 to 30 carbon atoms, an alkoxycarbonyl group having 1 to 30 carbon atoms, a haloalkoxycarbonyl group having 1 to 30 carbon atoms, an alkylcarbonyl group having 1 to 30 carbon atoms, alkyl, a halogenated alkylcarbonyl group having 1 to 30 carbon atoms, an alkylacyloxy group having 1 to 30 carbon atoms, a halogenated alkylacyloxy group having 1 to 30 carbon atoms, an alkylaryl group having 6 to 30 carbon atoms, an arylalkyl group having 6 to 30 carbon atoms, an alkylaryloxy group having 6 to 30 carbon atoms, an arylalkyloxy group having 6 to 30 carbon atoms, an arylcarbonyl group having 6 to 30 carbon atoms, an aryloxycarbonyl group having 6 to 30 carbon atoms, an arylcarbonyloxy group having 6 to 30 carbon atoms, and a 30; one or more -CH2- in the alkyl, alkoxy, alkenyl and alkenyloxy groups may be substituted by -O-, -S-, -NH-, -CO-, -OCO-, -COO-, -SCO-, -COS-; optionally, one or more H atoms in the alkyl, alkoxy, alkenyl and alkenyloxy groups may be substituted by halogen, halogen, cyano, hydroxyl, nitro, carboxyl, carbamoyloxy, amino, sulfamoyl, methylamino, dimethylamino, diethylamino, diisopropylamino, trimethylsilyl, dimethylsilyl, thioisocyanato, an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, a haloalkoxy group having 1 to 30 carbon atoms, an alkylacyloxy group having 1 to 30 carbon atoms, a haloalkylacyloxy group having 1 to 30 carbon atoms, or a polymerizable group.

[0009] Preferably, the general formula (1) of the deuterated negative dispersion compound is selected from the general formula P~1, the general formula P~2 or the general formula P~3, and the general formula P~1, the general formula P~2 and the general formula P~3 are as follows: , , .

[0010] In addition, the present invention also provides a polymerizable compound composition, comprising a polymerizable compound of the above general formula (1) and at least one additional polymerizable compound.

[0011] Preferably, the additional polymerizable compound is selected from one or more compounds of formula M-1, formula M-2 or formula M-3; formula M-1, formula M-2 or formula M-3 is as follows: ; ; .

[0012] Preferably, in the polymerizable compound composition, the additional polymerizable compound comprises compounds of Formula M-1, Formula M-2 and Formula M-3.

[0013] Preferably, the additional polymerizable compound comprises, by weight percentage, 50% of the compound of the general formula M-1, 30% of the compound of the general formula M-2 and 20% of the compound of the general formula M-3.

[0014] Preferably, in the polymerizable compound composition, the added content of the polymerizable compound of the general formula (1) is 40 wt % of the additional polymerizable compound.

[0015] Preferably, the polymerizable compound composition further includes additives.

[0016] Preferably, the additives include a polymerization initiator and a polymerization inhibitor.

[0017] Preferably, the polymerization initiator is added to the polymerizable composition in an amount of 1 wt %.

[0018] Preferably, the content of the polymerization inhibitor added to the polymerizable composition is preferably 0.1 wt %.

[0019] Preferably, the deuterated negative dispersion compound is used in a negative dispersion optical film material.

[0020] Preferably, after the polymerizable compound composition solution is coated on the negative dispersion optical film material, it is dried.

[0021] Preferably, the polymerizable compound composition solution comprises the polymerizable compound composition described above and below and an organic solvent; the organic solvent is preferably chloroform.

[0022] When the polymerizable compound composition of the present invention is solution polymerized, it is desirable that the polymerization proceeds rapidly, and therefore it is preferably polymerized by irradiation with ultraviolet-visible active energy rays.

[0023] The polymerizable compound provided by the present invention is a deuterated negative dispersion compound with good orientation. At the same time, due to the presence of deuterated hydrogen, the negative dispersion compound can inhibit yellowing and delay decay, thereby effectively extending the life of the film. The deuterated negative dispersion compound can be applied to negative dispersion optical film materials. DETAILED DESCRIPTION

[0024] The following is a clear and complete description of the technical solutions in the implementation of the present invention. The described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention. If the specific conditions are not specified in the embodiments, they are carried out according to conventional conditions or the conditions recommended by the manufacturer.

[0025] The polymerizable compound provided by the present invention is a deuterated negative dispersion compound; the deuterated negative dispersion compound is selected from the compounds represented by the general formula (1).

[0026] (1) R represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, a haloalkoxy group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a haloalkenyl group having 2 to 30 carbon atoms, an alkenyloxy group having 2 to 30 carbon atoms, a haloalkenyloxy group having 2 to 30 carbon atoms, an alkoxycarbonyl group having 1 to 30 carbon atoms, a haloalkoxycarbonyl group having 1 to 30 carbon atoms, an alkylcarbonyl group having 1 to 30 carbon atoms, alkyl, a halogenated alkylcarbonyl group having 1 to 30 carbon atoms, an alkylacyloxy group having 1 to 30 carbon atoms, a halogenated alkylacyloxy group having 1 to 30 carbon atoms, an alkylaryl group having 6 to 30 carbon atoms, an arylalkyl group having 6 to 30 carbon atoms, an alkylaryloxy group having 6 to 30 carbon atoms, an arylalkyloxy group having 6 to 30 carbon atoms, an arylcarbonyl group having 6 to 30 carbon atoms, an aryloxycarbonyl group having 6 to 30 carbon atoms, an arylcarbonyloxy group having 6 to 30 carbon atoms, and a 30; one or more -CH2- in the alkyl, alkoxy, alkenyl and alkenyloxy groups may be substituted by -O-, -S-, -NH-, -CO-, -OCO-, -COO-, -SCO-, -COS-; optionally, one or more H atoms in the alkyl, alkoxy, alkenyl and alkenyloxy groups may be substituted by halogen, halogen, cyano, hydroxyl, nitro, carboxyl, carbamoyloxy, amino, sulfamoyl, methylamino, dimethylamino, diethylamino, diisopropylamino, trimethylsilyl, dimethylsilyl, thioisocyanato, an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, a haloalkoxy group having 1 to 30 carbon atoms, an alkylacyloxy group having 1 to 30 carbon atoms, a haloalkylacyloxy group having 1 to 30 carbon atoms, or a polymerizable group.

[0027] Hereinafter, the present invention is further explained by listing synthesis examples, comparative examples and application examples, but the present invention is not limited to these examples. Unless otherwise specified, the percentages in raw materials and compositions are percentages by weight.

[0028] Example 1 Synthesis of P-1 The synthesis steps of P-1 are as follows: Step 1, synthesis of intermediate S-2: Weigh 100g of S-1 and add it to a 500ml three-necked flask, add 300g of deuterated heavy water, heat and reflux for 24h to synthesize S-2, then cool, filter and dry to obtain 91.2g of S-2 product with a yield of 89%; the reaction equation of step 1 is as follows: ; Step 2, synthesis of intermediate S-4: add 25g of S-2 to a 500ml reaction bottle, add 245ml of DMF, lower the temperature to below 10°C, protect with nitrogen, add 25g of potassium tert-butoxide in batches, continue stirring for 1h, then add 30.5g of S-3 dropwise, after the addition is complete, heat to 25°C and react for 5h to synthesize S-4; the reaction equation of step 2 is as follows: ; Post-treatment, lower the temperature, then add 350g of dichloromethane, add 400g of water, separate and extract, wash once with 400g of saturated brine, wash once with 300g, 10% brine, add sodium sulfate to dry, add 70g of alumina and stir for 1h. Then pass through a 140g alumina chromatography column, elute with 150g of DCM, desolventize with the eluent, obtain 45g of green oil, stir and crystallize with 40g of dichloromethane and 40g of petroleum ether at low temperature, and filter to obtain 32g of green solid, with a yield of 70%; Step 3, synthesis of intermediate S-6: add 25g of S-5 to a 500ml reaction bottle, add 250ml of dichloromethane, add 10g of S-4, add 1g of camphorsulfonic acid, protect with nitrogen, heat to 50°C for 5h to synthesize S-6, and directly use it as the raw material for the next step without purification; due to impurity, the yield of this step is converted to 100%; the reaction equation of step 3 is as follows: ; Step 4, synthesis of product P-1: add 14 g of DIPEA to the reaction solution of S-6, protect with nitrogen, lower the temperature to 0°C, add 10 g of acryloyl chloride dropwise thereto, after the addition is complete, raise the temperature to 25°C, react for 3 hours, and synthesize P-1; the reaction equation of step 4 is as follows: ; After treatment, the reaction solution was directly passed through a silica gel chromatography column and then concentrated. The oil was dissolved with 40 g of dichloromethane, 400 g of methanol was added dropwise, stirred for crystallization, and filtered and dried to obtain 31 g of P-1 product with a yield of 87%.

[0029] H NMR (CDC13) of the product P-1 in this example: 1.21-1.28 (m, 4H), 1.40-1.81 (m, 22H), 1.90 (m, 2H), 2.07 (m, 4H), 2.23 (m, 4H), 2.52 (m, 2H), 3.61 (m, 3H), 3.66 (m, 2H), 3.83-3.90 (m, 5H), 3.93 (t, 4H), 4.14-4.18 (m, 6H), 4 .52(t,2H),5.75(d,1H),5.81(d,2H),6.07(d,1H),6.11(d,2H),6.36(d.1H),6.41(d,2H),6 .83-6.90 (m, 6H), 6.94~6.97 (m, 2H), 7.13 (t, 1H), 7.38 (d, 1H), 7.51 (s, 1H), 8.43 (s, 1H) ppm. The general formula of the product T-1 in this example is as follows: .

[0030] Example 2 Synthesis of P-2 The synthesis steps of P-2 are as follows: Step 1, synthesis of intermediate S-2: The synthesis of intermediate S-2 is similar to the synthesis of S-2 in Example 1; Step 2, synthesis of intermediate S-8: Add 25g of S-2 to a 500ml reaction bottle, add 245ml of DMF, lower the temperature to below 10°C, protect with nitrogen, add 25.7g of potassium tert-butoxide in batches, continue stirring for 1h, then add 30.5g of S-7 dropwise, after the addition is complete, heat to 25°C and react for 5h to synthesize S-8; the reaction equation of step 2 is as follows: ; Post-treatment, lower the temperature, then add 350g of dichloromethane, add 400g of water, separate and extract, wash once with 400g of saturated brine, wash once with 300g, 10% brine, add sodium sulfate to dry, add 70g of alumina and stir for 1h, then pass through a 100g alumina chromatography column, elute with 150g of DCM, desolventize with the eluent, and obtain 45g of a yellow oily substance, stir and crystallize with 40g of dichloromethane and 40g of petroleum ether at low temperature, and filter to obtain 28.5g of a yellow solid, with a yield of 71%; Step 3, synthesis of product P-2: add 30g of S-5 to a 500ml reaction bottle, add 250ml of dichloromethane, add 10.8g of S-8, add 1g of camphorsulfonic acid, protect with nitrogen, heat to 50°C for 5h to synthesize P-2; the reaction equation of step 3 is as follows: ; After treatment, the reaction solution was directly passed through a silica gel chromatography column and then concentrated. The oil was dissolved with 40 g of dichloromethane, 400 g of methanol was added dropwise thereto, stirred for crystallization, filtered and dried to obtain 36 g of P-2 product with a yield of 90%.

[0031] HNMR (CDC13) of the product P-2 of this example: 1.22-1.28 (m, 4H), 1.45-1.48 (m, 8H), 1.61-1.83 (m, 12H), 1.90 (m, 2H), 2.06 (t, 4H), 2.23 (d, 4H), 2.52 (m, 2H), 3.31 (s, 3H), 3.51 (t, 2H), 3.67 (t, 2H), 3.86-3 .89(m,6H),3.94(t,4H),4.16(t,4H),4.54(t,2H),5.83(d,2H),6.14(q,2H),6.41(d,2H),6 .82-6.91 (m, 6H), 6.95~6.98 (m, 2H), 7.14 (t, 1H), 7.39 (d, 1H), 7.51 (s, 1H), 8.44 (s, 1H) ppm.

[0032] The general formula of the product P-2 of this embodiment is as follows: .

[0033] Example 3 Synthesis of P-3 The synthesis steps of P-3 are as follows: Step 1, synthesis of intermediate S-2: The synthesis of intermediate S-2 is similar to the synthesis of S-2 in Example 1; Step 2, synthesis of intermediate S-10: Add 25g of S-2 to a 500ml reaction bottle, add 245ml of DMF, lower the temperature to below 10°C, protect with nitrogen, add 25.7g of potassium tert-butoxide in batches, continue stirring for 1h, then add 30.5g of S-9 dropwise, after the addition is complete, heat to 25°C and react for 5h to synthesize S-10; the reaction equation for step 2 is as follows: ; Post-treatment, lower the temperature, then add 350g of dichloromethane, add 400g of water, separate and extract, wash once with 400g of saturated brine, wash once with 300g, 10% brine, add sodium sulfate to dry, add 70g of alumina and stir for 1h, then pass through a 100g alumina chromatography column, elute with 150g of DCM, desolventize with the eluent, and obtain 45g of a yellow oily substance, stir and crystallize with 40g of dichloromethane and 40g of petroleum ether at low temperature, and filter to obtain 28.5g of a yellow solid, with a yield of 71%; Step 3, synthesis of product P-3: Add 30g of S-5 to a 500ml reaction bottle, add 250ml of dichloromethane, add 10.6g of S-10, and add 1g of camphorsulfonic acid. Protect with nitrogen, heat to 50℃ and react for 5h; synthesize P-3; the reaction equation of step 3 is as follows: ; After treatment, the reaction solution was directly passed through a silica gel chromatography column and then concentrated. The oil was dissolved with 40 g of dichloromethane, 400 g of methanol was added dropwise, stirred for crystallization, and filtered and dried to obtain 32.64 g of P-3 product with a yield of 89%.

[0034] HNMR (CDC13) of the product P-3 of this example: 0.89 (t, 3H), 1.20-1.35 (m, 10H), 1.61-1.69 (m, 6H), 1.78 (m, 2H), 1.90 (m, 2H), 2.07 (t, 4H), 2.23 (d, 4H), 2.50 (m, 2H), 3.69-3.76 (m, 10H), 3.83-3.87 (m, 8H), 4.1 1(t,4H),4.32(t,6H),5.82(d,2H),6.15(q,2H),6.42(d,2H),6.82~6.91(m,6 H), 6,95-6.98 (m, 2H), 7.14 (t, 1H), 7.39 (d, 1H), 7.51 (s, 1H), 8.44 (s, 1H) ppm.

[0035] The general formula of the product P-3 in this embodiment is as follows: .

[0036] In order to evaluate its good anti-aging performance, we will compare it with the following three products: Compound B-1, B-2, and B-3 as comparative examples: Comparative Example 1 Taking compound B-1 as a comparison, the general formula of compound B-1 is as follows: .

[0037] Comparative Example 2 Taking compound B-2 as a comparison, the general formula of compound B-2 is as follows: .

[0038] Comparative Example 3 Taking compound B-3 as a comparison, the general formula of compound B-3 is as follows: .

[0039] application Furthermore, a liquid crystal composition is provided as a mother liquid crystal (M), the liquid crystal composition comprising 50% of a compound (M-1) described in JP-A-2005-015473, 30% of a compound (M-2) described in JP-A-10-87565, and 20% of a compound (M-3) described in JP-T-2002-537280.

[0040] The general formula of compound M-1 is as follows: ; The general formula of compound M-2 is as follows: ; The general formula of compound M-3 is as follows: .

[0041] The oriented film was coated with a polyimide solution on a glass substrate with a thickness of 0.7 mm, dried at 100° C. for 10 minutes, and then sintered at 200° C. for 60 minutes to obtain a coating film. The obtained coating film was rubbed using a commercially available rubbing device to obtain a rubbed glass substrate.

[0042] In the mother liquid crystal M, the product compounds of Examples 1 to 3 and Comparative Examples 1 to 3 shown in Table 1 are added in an amount of 40% by weight of the mother liquid crystal M as the compounds to be evaluated, and a polymerizable compound composition is prepared, and 1% of a photopolymerization initiator Irgacure 907 (manufactured by BASF), 0.1% of a polymerization inhibitor 4-methoxyphenol and 80% of chloroform are added to prepare a coating liquid; the coating liquid is applied to a rubbed glass substrate by spin coating; after drying at 80°C for 1 min, it is further dried at 120°C for 1 min, and then a high-pressure mercury lamp is used to irradiate ultraviolet rays at an intensity of 40 mW / cm² for 25 seconds, thereby preparing a film to be evaluated. The film to be evaluated is as shown in Application Examples 1 to 6 in Table 1.

[0043] For the obtained polymer, the degree of unevenness was evaluated by polarizing microscope observation. Ten films were prepared to which the compound to be evaluated was added, and the number of unevenness was counted. The results are shown in Table 1. The number of unevenness observed in the 10 films was totaled, and if the number of unevenness was 0, it was recorded as excellent, if the number of unevenness was 1, it was recorded as good, if the number of unevenness was 1 to 10, it was recorded as medium, and if the number of unevenness was more than 10, it was recorded as poor.

[0044] A xenon irradiation tester (Suntest XLS, manufactured by ATLAS) was used at 60 mW / cm 2Each of the produced films was subjected to a sunlight test under the conditions of 26°C and 120J. The discoloration and poor orientation of the obtained films were evaluated. The yellowness index (YI) of each film was measured. The difference (△YI) between the YI value before the sunlight test and the YI value after the sunlight test was calculated. The yellowness index (YI) was measured using a JASCOUV / VIS spectrophotometer V-560 and calculated using the accompanying color diagnosis program. The results are shown in Table 1. The calculation formula is: YI=100×(1.28X-1.06Z) / Y (JIS K7373) (X, Y, Z represent the tristimulus values ​​in the XYZ color system). The smaller the △YI value, the less discoloration.

[0045] Table 1

[0046] As can be seen from the table, the three compounds of the embodiment, compared with the compounds of the comparative example, have good orientation when subjected to high-intensity ultraviolet irradiation. The functions of the deuterated compounds and the non-deuterated compounds are both qualified. We found in the test of their yellowing degree that the three compounds of the embodiment, due to the presence of deuterated hydrogen, have the effect of inhibiting yellowing and delaying decay, which can effectively extend the life of the film.

[0047] It will be apparent to those skilled in the art that the present invention is not limited to the details of the exemplary embodiments described above, and that the present invention can be implemented in other specific forms without departing from the spirit and essential features of the present invention. Therefore, the embodiments should be considered exemplary and non-restrictive in all respects, and the scope of the present invention is defined by the appended claims rather than the above description, and it is intended that all changes falling within the meaning and scope of the equivalent elements of the claims be included in the present invention.

[0048] In addition, it should be understood that although the present specification is described according to implementation modes, not every implementation mode contains only one independent technical solution. This description of the specification is only for the sake of clarity. Those skilled in the art should regard the specification as a whole. The technical solutions in each embodiment may also be appropriately combined to form other implementation modes that can be understood by those skilled in the art.

Claims

1. A polymerizable compound, characterized in that The polymerizable compound is a deuterated negative dispersion compound.

2. A polymerizable compound according to claim 1, characterized in that: The deuterated negative dispersion compound is selected from the compounds represented by the general formula (1), （1） R represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, a haloalkoxy group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a haloalkenyl group having 2 to 30 carbon atoms, an alkenyloxy group having 2 to 30 carbon atoms, a haloalkenyloxy group having 2 to 30 carbon atoms, an alkoxycarbonyl group having 1 to 30 carbon atoms, a haloalkoxycarbonyl group having 1 to 30 carbon atoms, an alkylcarbonyl group having 1 to 30 carbon atoms, alkyl, a halogenated alkylcarbonyl group having 1 to 30 carbon atoms, an alkylacyloxy group having 1 to 30 carbon atoms, a halogenated alkylacyloxy group having 1 to 30 carbon atoms, an alkylaryl group having 6 to 30 carbon atoms, an arylalkyl group having 6 to 30 carbon atoms, an alkylaryloxy group having 6 to 30 carbon atoms, an arylalkyloxy group having 6 to 30 carbon atoms, an arylcarbonyl group having 6 to 30 carbon atoms, an aryloxycarbonyl group having 6 to 30 carbon atoms, an arylcarbonyloxy group having 6 to 30 carbon atoms, and a 30; one or more -CH2- in the alkyl, alkoxy, alkenyl and alkenyloxy groups may be substituted by -O-, -S-, -NH-, -CO-, -OCO-, -COO-, -SCO-, -COS-; optionally, one or more H atoms in the alkyl, alkoxy, alkenyl and alkenyloxy groups may be substituted by halogen, halogen, cyano, hydroxyl, nitro, carboxyl, carbamoyloxy, amino, sulfamoyl, methylamino, dimethylamino, diethylamino, diisopropylamino, trimethylsilyl, dimethylsilyl, thioisocyanato, an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, a haloalkoxy group having 1 to 30 carbon atoms, an alkylacyloxy group having 1 to 30 carbon atoms, a haloalkylacyloxy group having 1 to 30 carbon atoms, or a polymerizable group.

3. A polymerizable compound according to claim 2, characterized in that The general formula (1) of the deuterated negative dispersion compound is selected from the general formula (P~1), the general formula (P~2) or the general formula (P~3), and the general formulas P~1, P~2 and P~3 are as follows: ， ， 。 4. A polymerizable compound composition, characterized in that The polymerizable compound composition comprises the polymerizable compound of any one of claims 1 to 3 and at least one additional polymerizable compound.

5. The polymerizable compound composition according to claim 4, characterized in that The additional polymerizable compound is selected from one or more compounds represented by the general formula M-1, the general formula M-2 or the general formula M-3; the general formula M-1, the general formula M-2 or the general formula M-3 is as follows: ； ； 。 6. A polymerizable compound composition according to claim 5, characterized in that: The additional polymerizable compound comprises, by weight percentage, 50% of the compound of the general formula M-1, 30% of the compound of the general formula M-2 and 20% of the compound of the general formula M-3.

7. A polymerizable compound composition according to claim 4, characterized in that: In the polymerizable compound composition, the added content of the polymerizable compound of the general formula (1) is 40 wt % of the additional polymerizable compound.

8. The polymerizable compound composition according to claim 5, characterized in that: The polymerizable compound composition further includes additives.

9. A polymerizable compound composition according to claim 8, characterized in that: The additives include a photopolymerization initiator and a polymerization inhibitor.

10. An application of a polymerizable compound, characterized in that: The deuterated negative dispersion compound described in any one of claims 1 to 3 is used in negative dispersion optical film materials.

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