CN110655465A - Novel diamine compound and preparation method and application thereof - Google Patents
Novel diamine compound and preparation method and application thereof Download PDFInfo
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- CN110655465A CN110655465A CN201810689534.8A CN201810689534A CN110655465A CN 110655465 A CN110655465 A CN 110655465A CN 201810689534 A CN201810689534 A CN 201810689534A CN 110655465 A CN110655465 A CN 110655465A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/39—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton
- C07C211/41—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- C—CHEMISTRY; METALLURGY
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/38—Polymers
- C09K19/3804—Polymers with mesogenic groups in the main chain
- C09K19/3809—Polyesters; Polyester derivatives, e.g. polyamides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/90—Ring systems containing bridged rings containing more than four rings
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Abstract
The invention relates to a novel diamine compound, a preparation method and application thereof. The diamine compound has the effect of enhancing the efficiency of the liquid crystal display element, and the polyamic acid, the polyimide and the liquid crystal alignment agent prepared by using the diamine compound have the properties of good chemical stability, thermal stability and the like, so that the formed liquid crystal alignment film has a higher pretilt angle.
Description
Technical Field
The invention relates to the field of liquid crystal materials. In particular to a novel diamine compound and a preparation method and application thereof.
Background
Among the liquid crystal displays, typical is a Twisted Nematic (TN) electric field effect type liquid crystal display using a nematic liquid crystal having positive dielectric anisotropy. Generally, liquid crystal molecules are interposed between a pair of substrates having electrodes, and the alignment directions of the two substrates are perpendicular to each other, and the arrangement of the liquid crystal molecules can be controlled by controlling an electric field. In this type of liquid crystal display, it is important to align the long axis direction of the liquid crystal molecules with the substrate surface with a uniform tilt angle. Such a material for aligning liquid crystal molecules in a uniform pretilt angle alignment is generally referred to as an alignment film.
Currently, there are two typical methods for preparing alignment films in the industry. The first method is to form an inorganic film from an inorganic substance by vapor deposition. For example, silicon dioxide is obliquely deposited on a substrate to form a thin film, and liquid crystal molecules are aligned in the deposition direction. However, the above method can obtain uniform alignment, but has no industrial benefit. The second method is to coat an organic film on the surface of the substrate and then rub the organic film with a soft cloth of cotton, nylon or polyester to orient the liquid crystal molecules in the rubbing direction. This method is generally used on an industrial scale because it is simple and relatively easy to obtain uniform alignment. In this method, a polymer such as polyvinyl alcohol (PVA), polyethylene oxide (PEO), Polyamide (PA) or polyimide, which has chemical stability and thermal stability, may be used as an alignment film material.
In the prior art, when a voltage is applied to the liquid crystal display, the generated ionic charges are absorbed by the liquid crystal alignment film, and even after the applied voltage is released, the ionic charges are difficult to be separated from the liquid crystal alignment film, thereby causing the problem of generating image retention on the screen. Therefore, the development of alignment film materials is primarily aimed at improving the image retention.
Disclosure of Invention
The first purpose of the invention is to provide a novel diamine compound, wherein the liquid crystal compound has a structure shown in a formula I:
the compound has the advantages that the effect of the liquid crystal display element is improved, and the polyamic acid, the polyimide and the liquid crystal alignment agent which are prepared by using the diamine compound have good chemical stability, thermal stability and other properties, so that the formed liquid crystal alignment film has a higher pretilt angle.
The second purpose of the invention is to provide a preparation method of the compound, and in order to achieve the second purpose, the invention adopts the following technical scheme:
the synthetic route of the compound shown in the formula I is as follows:
the preparation method of the compound shown in the formula I comprises the following steps:
1) dicyclopentadiene is taken as a raw material, and gas-phase depolymerization is carried out to obtain cyclopentadiene;
2) performing addition reaction on cyclopentadiene and cyclohexanedione to obtain a compound I-a;
3) and carrying out reduction reaction on the compound I-a and ammonium formate to obtain a compound I.
In the step 1), the depolymerization temperature is 280-380 ℃ and the retention time is 1-5 s; the preferable temperature is 320-340 ℃, and the time is 2-4 s;
in the step 2), the feeding molar ratio of the cyclohexanedione to the cyclopentadiene is 1.0: (1.9-3.0); the reaction temperature can be-20 to 30 ℃, preferably-5 to 0 ℃ or-10 to-5 ℃.
In the step 3), the feeding molar ratio of the compound I-a to ammonium formate is 1: (2.0-4.0); the reaction temperature can be 50-80 ℃; preferably 70-75 deg.C.
As one of the preferable embodiments of the invention, the preparation method of the compound shown in the formula I comprises the following steps:
1) depolymerizing dicyclopentadiene at 320-340 ℃ to generate cyclopentadiene;
in order to prevent the cyclopentadiene from being polymerized again, a compound polymerization inhibitor is added in the rectification process; the compound polymerization inhibitor is obtained by compounding hydroquinone, snorkeling and cuprous oxide in a weight ratio of 1:1: 0.5; or 4-tert-butyl catechol, snorkel and cuprous iodide are compounded in a weight ratio of 1:1:0.5 to obtain the compound.
2) Reacting the obtained cyclopentadiene with cyclohexanedione at the temperature of-5-0 ℃ or-10 to-5 ℃ to generate a compound I-a;
3) and under the action of a catalyst, further reacting the obtained compound I-a with ammonium formate to obtain a compound I. The catalyst is one or more of iridium catalyst (Ir-3), palladium catalyst, ruthenium catalyst and the like.
Further, it is to be noted that, in the production method of the present invention, the solvent used in each step and the amount thereof, the separation and purification of the product, the dropping rate of the reactant, and the like, which are not particularly limited in part, are understood and grasped by those skilled in the art. In the present invention, the solvent is used in an amount of 5 to 15 times the amount of the reaction substance, unless otherwise specified, and the specific amount can be suitably adjusted depending on the amount of the reaction substrate and the size of the reaction flask selected; the dropping rate of the reactants is generally controlled in combination with a specific reaction rate. Based on the disclosure of the present invention, those skilled in the art can select any available technical solutions to implement the present invention according to practical situations.
The preparation method can stably and efficiently obtain the compound.
The third purpose of the invention is to provide an application of the diamine compound in the field of liquid crystal display, and the application specifically comprises the following steps:
a polyimide which is produced from a raw material comprising the above diamine compound.
A polyamic acid is prepared from a raw material including the diamine compound.
A liquid crystal aligning agent contains polyimide or polyamic acid prepared from the raw material including the diamine compound.
Wherein, in terms of mole percentage, the content of the diamine compound in the polyimide, the polyamic acid or the liquid crystal aligning agent is at least 1%, preferably at least 10%, and more preferably at least 50%.
Experiments prove that the diamine compound is added in the preparation process of the liquid crystal alignment agent, so that the obtained liquid crystal alignment agent has good properties such as chemical stability, thermal stability and the like, and a liquid crystal alignment film formed by the liquid crystal alignment agent has a higher pretilt angle.
Alternatively, the application is a liquid crystal protective agent prepared from raw materials including the diamine compound.
Alternatively, the application is specifically a liquid crystal display element, and a liquid crystal alignment film contained in the liquid crystal display element is prepared from a raw material including the diamine compound. The liquid crystal display element has lower residual direct current charge and thus has higher efficiency.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
The starting materials are commercially available from the open literature unless otherwise specified.
According to the conventional detection method in the field, various performance parameters of the compound are obtained through linear fitting, wherein the specific meanings of the performance parameters are as follows:
Δ n represents optical anisotropy (25 ℃);
Δ ε represents the dielectric anisotropy (25 ℃, 1000 Hz);
ε | represents the dielectric constant (25 ℃, 1000Hz) in the direction parallel to the molecular axis;
cp represents a clearing point;
k represents the elastic constant (25 ℃).
Example 1
The method comprises the following specific steps:
(1)
synthesis of (2)
Adding pure heat conducting oil and a compound polymerization inhibitor in a weight ratio of 1:0.005 into a thermal decomposer and a rectification reboiler, introducing nitrogen to replace system air, heating the heat conducting oil to 320 ℃, adding crude dicyclopentadiene (83.5 mass percent) into the thermal decomposer from the bottom of the thermal decomposer through a metering pump, contacting with high-temperature heat conducting oil, controlling the feeding speed to enable the dicyclopentadiene to stay in the thermal decomposer for 2.0 seconds, controlling the internal temperature of the thermal decomposer to be 320 ℃, gasifying the dicyclopentadiene, feeding depolymerized cyclopentadiene into a rectification column for rectification, separating high-purity cyclopentadiene from the top of the column, feeding the cyclopentadiene into a collector through a condenser (low-temperature storage), heating a small amount of uncracked dicyclopentadiene and byproducts in the bottom reboiler, and then rectifying again.
The composite polymerization inhibitor is a complex of hydroquinone, veronica and cuprous oxide, and the weight ratio of the hydroquinone, the veronica and the cuprous oxide is 1:1:0.5
Continuously and stably operating for more than 48 hours, and analyzing the purity of the cyclopentadiene by gas chromatography to be 98.12 percent and the yield to be 95.7 percent.
(2)
Synthesis of (2)
Under the protection of nitrogen, adding 80ml of ethanol and 16.5g of cyclopentadiene into a reaction bottle, controlling the temperature to be between-10 and-5 ℃, dropwise adding a solution consisting of 11.2g of 1, 4-cyclohexanedione and 30ml of ethanol, controlling the temperature to be between-5 and 0 ℃ after dropwise adding, reacting for 1 hour, stopping the reaction by using an alkali liquor, carrying out conventional post-treatment, recrystallizing petroleum ether to obtain 22.8g of light yellow solid (compound I-a), wherein the HPLC (high performance liquid chromatography) ratio is 99.5%, and the yield is as follows: 95.0 percent.
(3)
Synthesis of (2)
Under the protection of nitrogen, 18.0g of ammonium formate, 200ml of methanol, 22.8g of compound I-a, 10ml of acetic acid and 0.001g of iridium catalyst (Ir-3) are added into a reaction bottle, the mixture is refluxed for 8 hours at the temperature of 75 ℃, cooled to room temperature, quenched by adding saturated aqueous sodium hydroxide solution, and then subjected to conventional post-treatment operation, dissolved and separated by dichloromethane, and chromatographically purified, and a mixed solution of n-heptane and toluene in a volume ratio of 3:1 is recrystallized to obtain 18.9g of white solid (compound I), HPLC: 99.8% and yield: 82.3%.
The white solid obtained, Compound I, was analyzed by GC-MS and the M/z of the product was 242.1(M +).
1H-NMR(300MHz,CDCl3):1.45-1.85(m,8H),1.95-2.65(m,6H),4.95-5.85(m,4H)。
Example 2
(1)
Synthesis of (2)
Adding pure heat conducting oil and a compound polymerization inhibitor in a weight ratio of 1:0.01 into a thermal decomposer and a rectification reboiler, introducing nitrogen to replace system air, heating the heat conducting oil to 340 ℃, adding crude dicyclopentadiene (92.7% by mass) into the thermal decomposer from the bottom of the thermal decomposer through a metering pump, contacting with high-temperature heat conducting oil, controlling the feeding speed to enable the dicyclopentadiene to stay in the thermal decomposer for 1.5 seconds, controlling the temperature in the thermal decomposer to be 340 ℃, gasifying the dicyclopentadiene, rectifying the depolymerized cyclopentadiene in a rectifying column, separating high-purity cyclopentadiene from the top of the tower, feeding the cyclopentadiene into a collector through a condenser (low-temperature storage), and rectifying a small amount of uncracked dicyclopentadiene and byproducts again after being heated in the reboiler at the bottom of the tower. The composite polymerization inhibitor is a complex ligand of 4-tert-butyl catechol, veronica and cuprous iodide, and the weight ratio of the three is 1:1: 0.5.
Continuously and stably operating for more than 48 hours, and analyzing the purity of the cyclopentadiene by gas chromatography to be 98.17 percent and the yield to be 96.4 percent.
(2)
Synthesis of (2)
Under the protection of nitrogen, adding 120ml of ethanol and 27.7g of cyclopentadiene into a reaction bottle, controlling the temperature to be between-10 and-5 ℃, dropwise adding a solution consisting of 16.8g of 1, 4-cyclohexanedione and 30ml of ethanol, controlling the temperature to be between-5 and 0 ℃ after dropwise adding, reacting for 1 hour, stopping the reaction by using an alkali liquor, carrying out conventional post-treatment, recrystallizing petroleum ether to obtain 34.8g of light yellow solid (compound I-a), wherein the HPLC (high performance liquid chromatography) ratio is 99.6%, and the yield is as follows: 96.8 percent.
(3)
Synthesis of (2)
Under the protection of nitrogen, 27.4g of ammonium formate, 300ml of methanol, 34.8g of compound I-a, 12ml of acetic acid and 0.001g of iridium catalyst (Ir-3) are added into a reaction bottle, the mixture is refluxed for 8 hours at the temperature of 70 ℃, cooled to room temperature, quenched by adding saturated aqueous sodium hydroxide solution, and then subjected to conventional post-treatment operation, dissolved and separated by dichloromethane, and chromatographically purified, and a mixed solution of n-heptane and toluene in a volume ratio of 3:1 is recrystallized to obtain 28.2g of white solid (compound I), HPLC: 99.7% and yield: 80.5%.
Effect verification
The materials used in the following experiments were:
as comparative examples: 4,4 'diaminodiphenylmethane (4,4' -methylenedianiline), abbreviated MDA.
As reactants: 1,2,3, 4-cyclobutanetetracarboxylic dianhydride (cyclobutane-1,2,3, 4-tetracarboxylic dianhydride), abbreviated as CBDA. And the performance of the proprietary product and the comparative product after mixed polymerization.
Experimental example 1
12.1 g (0.05 mol) of Compound I, 9.8 g (0.05 mol) of CBDA were dissolved in 92.8 g of NMP (N-methylpyrrolidone), reacted at room temperature for 12 hours, and then 348 g of NMP was added thereto for dilution to obtain a polyamic acid solution (specific viscosity: 0.57 dl/g).
Then, this polyamic acid solution was spin-coated at 3000rpm on a glass substrate having a transparent electrode.
Then, it was heated at 200 ℃ for 30 minutes to form a polyimide film, and it was assembled into a liquid crystal cell assembled in a parallel direction using a spacer of 40 μm. After filling liquid crystal (model: BYLC-1007, manufactured by billions of space-time liquid crystal technologies ltd.), the liquid crystal cell was rotated between crossed nicols and was in a dark state, and the pretilt angle value obtained by the pretilt angle measuring machine was 90 °.
Experimental example 2
2.42 g (0.01 mol) of Compound I, 14.8 g (0.04 mol) of MDA and 9.8 g (0.05 mol) of CBDA were dissolved in 110.2 g of NMP, reacted at room temperature for 12 hours, and further 413.4 g of NMP was added for dilution to obtain a polyamic acid solution (specific viscosity of 0.72 dl/g).
Then, this polyamic acid solution was spin-coated at 3000rpm on a glass substrate having a transparent electrode.
Subsequently, the mixture was heated at 200 ℃ for 30 minutes to form a polyimide film.
After cooling the polyimide film, it was rubbed with bristles and assembled into a liquid crystal cell assembled in parallel directions using a spacer of 40 microns. After filling liquid crystal (model: BYLC-1007, manufactured by the eight billion space-time liquid Crystal technology Co., Ltd.), the pretilt angle value obtained by the pretilt angle measuring machine was 5.5 °.
Comparative example
9.7 g (0.05 mol) of MDA and 9.8 g (0.05 mol) of CBDA were dissolved in 78 g of NMP, reacted at room temperature for 12 hours, and then 292.5 g of NMP was added to dilute them, to obtain a polyamic acid solution (specific viscosity: 0.81 dl/g).
This polyamic acid solution was then spin coated at 3000rpm on a glass substrate with a transparent electrode.
Subsequently, the mixture was heated at 200 ℃ for 30 minutes to form a polyimide film.
After cooling the polyimide film, it was rubbed with bristles and assembled into a liquid crystal cell assembled in parallel directions using a spacer of 40 microns. After filling liquid crystal (model: BYLC-1007, manufactured by the eight billion space-time liquid Crystal technology Co., Ltd.), the pretilt angle value obtained by the pretilt angle measuring machine was 2.1 °.
TABLE 1 pretilt Angle comparison of Experimental examples and comparative examples
As can be seen from table 1, when the diamine compound of the present invention was added to prepare a liquid crystal alignment agent, the pretilt angle of the formed liquid crystal alignment film was significantly improved.
TABLE 2 comparison of residual DC charges of the experimental examples and comparative examples
As can be seen from Table 2, when the diamine compound of the present invention was added to prepare a liquid crystal aligning agent, the resulting liquid crystal display device had a low residual DC charge.
In summary, the liquid crystal alignment agent contains polyimide or polyamic acid obtained by polymerization reaction of the diamine compound and the tetracarboxylic acid or the dianhydride compound thereof, so that the liquid crystal alignment film formed by the liquid crystal alignment agent has a higher pretilt angle, and the obtained liquid crystal display element has lower residual direct current charges, thereby enhancing the performance of the liquid crystal display element.
Although the present invention has been described with reference to the above embodiments, it should be understood that the scope of the present invention is defined by the appended claims.
Claims (10)
1. A diamine compound having a structure according to formula I:
2. a process for producing the diamine compound according to claim 1, which comprises:
1) dicyclopentadiene is taken as a raw material, and gas-phase depolymerization is carried out to obtain cyclopentadiene;
2) performing addition reaction on cyclopentadiene and cyclohexanedione to obtain a compound I-a;
3) and carrying out reduction reaction on the compound I-a and ammonium formate to obtain a compound I.
3. The method according to claim 2, wherein the depolymerization temperature in step 1) is 280-380 ℃, preferably 320-340 ℃.
4. The method according to claim 2 or 3, wherein the reaction temperature in step 2) is-20 to 30 ℃, preferably-5 to 0 ℃ or-10 to-5 ℃.
5. The method according to any one of claims 2 to 4, wherein the reaction temperature in step 3) is 50 ℃ to 80 ℃; preferably 70-75 deg.C.
6. The method of claim 2, comprising:
1) depolymerizing dicyclopentadiene at 320-340 ℃ to generate cyclopentadiene;
2) reacting the obtained cyclopentadiene with cyclohexanedione at the temperature of-5-0 ℃ or-10 to-5 ℃ to generate a compound I-a;
3) under the action of a catalyst, further reacting the obtained compound I-a with ammonium formate to obtain a compound I; the catalyst is one or more of iridium catalyst, palladium catalyst and ruthenium catalyst.
7. Use of the diamine compound according to claim 1 in the field of liquid crystal displays.
8. The application according to claim 7, characterized in that it is specifically:
a polyimide produced from a raw material comprising the diamine compound according to claim 1;
or, a polyamic acid prepared from a raw material comprising the diamine compound according to claim 1;
or, a liquid crystal aligning agent comprising a polyimide or polyamic acid prepared from a raw material comprising the diamine compound according to claim 1;
wherein, in terms of mole percentage, the content of the diamine compound in the polyimide, polyamic acid, or liquid crystal aligning agent is at least 1%, preferably at least 10%, and more preferably at least 50%.
9. Use according to claim 7, in particular a liquid crystal protectant, prepared from a starting material comprising a diamine compound according to claim 1.
10. The use according to claim 7, wherein the use is, in particular, a liquid crystal display element comprising a liquid crystal alignment film prepared from a raw material comprising the diamine compound according to claim 1.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113388109A (en) * | 2021-07-10 | 2021-09-14 | 南昌大学 | Polyimide with main chain containing benzonorbornene structure and preparation method thereof |
| CN113698761A (en) * | 2021-08-23 | 2021-11-26 | Tcl华星光电技术有限公司 | High-thermal-conductivity polyimide composite material, liquid crystal display panel and preparation method |
| CN117964897A (en) * | 2024-01-10 | 2024-05-03 | 上海八亿时空先进材料有限公司 | Alkali-soluble resin and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113388109A (en) * | 2021-07-10 | 2021-09-14 | 南昌大学 | Polyimide with main chain containing benzonorbornene structure and preparation method thereof |
| CN113698761A (en) * | 2021-08-23 | 2021-11-26 | Tcl华星光电技术有限公司 | High-thermal-conductivity polyimide composite material, liquid crystal display panel and preparation method |
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| CN117964897A (en) * | 2024-01-10 | 2024-05-03 | 上海八亿时空先进材料有限公司 | Alkali-soluble resin and application thereof |
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