CN111303166A - Green color resistance material, liquid crystal display panel and preparation method - Google Patents
Green color resistance material, liquid crystal display panel and preparation method Download PDFInfo
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- CN111303166A CN111303166A CN201911182787.7A CN201911182787A CN111303166A CN 111303166 A CN111303166 A CN 111303166A CN 201911182787 A CN201911182787 A CN 201911182787A CN 111303166 A CN111303166 A CN 111303166A
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133509—Filters, e.g. light shielding masks
- G02F1/133514—Colour filters
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Abstract
The invention provides a green color resistance material, a liquid crystal display panel and a preparation method thereof. By forming the dendritic compound substituent group, enough steric hindrance is generated between adjacent phthalocyanine molecules to hinder aggregation between the molecules, so that the green color-resisting material is in a monomolecular state, the scattering effect of the green color-resisting material is reduced, and the light penetration is improved.
Description
Technical Field
The invention relates to the field of display, in particular to a green color resistance material, a liquid crystal display panel and a preparation method.
Background
In the conventional liquid crystal display panel, in order to improve the optical penetration of the color resist layer, the color resist material is usually solubilized to reduce the particle state to the molecular state, and the solubilized color resist material is dispersed in a color resist solution solvent in the molecular state, so that the scattering effect of the color resist material on light is reduced, and the penetration and the contrast are improved. However, the green color resists in the color resist layer are easy to generate molecular aggregation in a solvent, are difficult to form a monomolecular state, have obvious scattering effect and cannot meet the requirement of high penetrating power.
Therefore, the technical problem of low green color resistance penetration of the existing liquid crystal display panel needs to be solved.
Disclosure of Invention
The invention provides a green color resistance material, a liquid crystal display panel and a preparation method thereof, which are used for relieving the technical problem of low green color resistance penetrating power of the existing liquid crystal display panel.
In order to solve the above problems, the technical scheme provided by the invention is as follows:
the invention provides a green color-resisting material, which comprises phthalocyanine molecules, wherein at least one group of the phthalocyanine molecules is a dendritic compound substituent group.
In the green color-resisting material, the main body of the dendritic compound substituent group is an alkyl chain.
In the green color resist material of the invention, the structural formula of the phthalocyanine molecule is shown in the specification
In the green color-resisting material, the structural formula of the dendritic compound substituent group is shown in the specification
In the green color resist material of the invention, the structural formula of R in the phthalocyanine molecule is shown in the specification
One kind of (1).
In the green color resist material of the invention, X in the phthalocyanine molecule is at least one of bromine or chlorine.
The invention also provides a liquid crystal display panel, which comprises a color resistance layer, wherein the color resistance layer comprises the green color resistance material.
The invention also provides a preparation method of the green color resistance material, which comprises the following steps:
preparing a phthalocyanine molecule precursor, wherein at least one group in the phthalocyanine molecule precursor is a dendritic compound substituent group;
synthesizing the phthalocyanine molecule precursor into phthalocyanine molecules to prepare the green color-resisting material.
In the method for preparing the green color-resisting material, the step of preparing the phthalocyanine molecule precursor, in which at least one group is a dendrimer substituent group, comprises the following steps:
in N2Dissolving a precursor compound and a dendritic compound in dimethyl formamide according to a molar ratio of 1:1 to form a 0.1M reaction solution under the environment;
adding K to the reaction solution2CO3And heating and refluxing for 12 hours, cooling to stop the reaction, and carrying out column purification treatment to enable the dendritic compound to replace at least one group in the precursor compound to form the phthalocyanine molecule precursor.
In the preparation method of the green color resistance material, the phthalocyanine molecule precursor is synthesized into the phthalocyanine molecule, and the step of preparing the green color resistance material comprises the following steps:
in N2Under the environment, dissolving the phthalocyanine molecule precursor, the intermediate compound and the acetate of the metal in an alcohol solvent;
heating and refluxing the alcohol solvent for 5 days, taking 1, 8-diazabicyclo [5,4,0] deca-7-ene as a catalyst, and purifying by a column after the reaction is completed to obtain the phthalocyanine molecule.
The invention has the beneficial effects that: the invention provides a green color resistance material, a liquid crystal display panel and a preparation method thereof. By forming the dendritic compound substituent group, enough steric hindrance is generated between adjacent phthalocyanine molecules to hinder aggregation between the molecules, so that the green color-resisting material is in a monomolecular state, the scattering effect of the green color-resisting material is reduced, and the light penetration is improved.
Drawings
The technical solution and other advantages of the present application will become apparent from the detailed description of the embodiments of the present application with reference to the accompanying drawings.
Fig. 1 is a schematic structural diagram of a liquid crystal display panel according to an embodiment of the invention.
Fig. 2 is a flowchart of a method for preparing a green color resist material according to an embodiment of the present invention.
Detailed Description
The technical solutions in the embodiments of the present application will be clearly and completely described below with reference to the drawings in the embodiments of the present application. It is to be understood that the embodiments described are only a few embodiments of the present application and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present application.
In the description of the present application, it is to be understood that the terms "center," "longitudinal," "lateral," "length," "width," "thickness," "upper," "lower," "front," "rear," "left," "right," "vertical," "horizontal," "top," "bottom," "inner," "outer," "clockwise," "counterclockwise," and the like are used in the orientations and positional relationships indicated in the drawings for convenience in describing the present application and for simplicity in description, and are not intended to indicate or imply that the referenced devices or elements must have a particular orientation, be constructed in a particular orientation, and be operated in a particular manner, and are not to be construed as limiting the present application. Furthermore, the terms "first", "second" and "first" are used for descriptive purposes only and are not to be construed as indicating or implying relative importance or implicitly indicating the number of technical features indicated. Thus, features defined as "first", "second", may explicitly or implicitly include one or more of the described features. In the description of the present application, "a plurality" means two or more unless specifically limited otherwise.
In the description of the present application, it is to be noted that, unless otherwise explicitly specified or limited, the terms "mounted," "connected," and "connected" are to be construed broadly, e.g., as meaning either a fixed connection, a removable connection, or an integral connection; may be mechanically connected, may be electrically connected or may be in communication with each other; either directly or indirectly through intervening media, either internally or in any other relationship. The specific meaning of the above terms in the present application can be understood by those of ordinary skill in the art as appropriate.
In this application, unless expressly stated or limited otherwise, the first feature "on" or "under" the second feature may comprise direct contact of the first and second features, or may comprise contact of the first and second features not directly but through another feature in between. Also, the first feature being "on," "above" and "over" the second feature includes the first feature being directly on and obliquely above the second feature, or merely indicating that the first feature is at a higher level than the second feature. A first feature being "under," "below," and "beneath" a second feature includes the first feature being directly under and obliquely below the second feature, or simply meaning that the first feature is at a lesser elevation than the second feature.
The following disclosure provides many different embodiments or examples for implementing different features of the application. In order to simplify the disclosure of the present application, specific example components and arrangements are described below. Of course, they are merely examples and are not intended to limit the present application. Moreover, the present application may repeat reference numerals and/or letters in the various examples, such repetition is for the purpose of simplicity and clarity and does not in itself dictate a relationship between the various embodiments and/or configurations discussed. In addition, examples of various specific processes and materials are provided herein, but one of ordinary skill in the art may recognize applications of other processes and/or use of other materials.
The invention provides a green color resistance material, a liquid crystal display panel and a preparation method thereof, which are used for relieving the technical problem of low green color resistance penetrating power of the existing liquid crystal display panel.
The green color-resisting material provided by the invention comprises phthalocyanine molecules, wherein at least one group of the phthalocyanine molecules is a dendritic compound substituent group.
The green color resistance material consists of phthalocyanine molecules and other components, wherein the phthalocyanine molecules are main color development components of the green color resistance material.
The liquid crystal display panel comprises a color resistance layer, wherein the color resistance layer comprises a red color resistance, a green color resistance and a blue color resistance, the red color resistance is made of a red color resistance material, the green color resistance is made of a green color resistance material, and the blue color resistance is made of a blue color resistance material.
The various color resistance materials used at the present stage are pigment particles, the particle size is about 50 nanometers, the particle size is large, when the liquid crystal display panel displays, when light rays emitted by the backlight module pass through the color resistance layer, the overlarge pigment particles can have a certain scattering effect on the light rays, so that the penetrating power and the contrast of the liquid crystal display panel are influenced, and the display effect of the liquid crystal display panel is influenced.
The current solution is to solubilize the color resist material to disperse it in the resist solution solvent in a molecular state, to minimize light scattering, and to improve the penetration and contrast.
At present, a great deal of development work is carried out on red color resistance materials and blue color resistance materials to achieve the effect of reducing scattering, and the green color resistance materials have strong pi-pi interaction force among molecules due to the fact that most of color development components of the green color resistance materials are phthalocyanine molecules, the phthalocyanine is a compound of a macrocyclic conjugated aromatic system with 18 electrons, and the conjugated planar structure of the phthalocyanine molecules enables the molecules to easily form molecular aggregation, so that a monomolecular state is difficult to form, the scattering effect is obvious, and the requirement of high penetrating power cannot be met.
The invention adopts the dendritic compound as the phthalocyanine peripheral substituent group, utilizes the dendritic compound to generate enough steric hindrance and hinders aggregation among molecules, thereby leading phthalocyanine molecules in the green color-resisting material to be in a monomolecular state and have higher solubility in a solvent, reducing the scattering effect of the green color-resisting material and improving the light penetrating power. The finally prepared novel phthalocyanine green light resistance material with high solubility and high penetration is used for manufacturing a color resistance layer for liquid crystal display, and the penetration rate and the contrast ratio of the material are greatly improved.
In one embodiment, the dendrimer substituent group is predominantly alkyl chain. The phthalocyanine molecule is mixed with a solvent to prepare the green color resistance material after the preparation of the phthalocyanine molecule is finished, the solvent usually adopted is propylene glycol methyl ether acetate PGMEA, and the intermiscibility of an alkyl chain and the propylene glycol methyl ether acetate is good, so that the solubilization effect of the phthalocyanine molecule is obvious, and the green light resistance material with high solubility and high penetrating power can be obtained more easily.
In one embodiment, the phthalocyanine molecule has the formula
Wherein L-is a dendritic compound substituent group, and the structural formula of the dendritic compound substituent group is
In one embodiment, R in the phthalocyanine molecule has the formula
One kind of (1).
In the present invention, there are various structures of the dendrimer substituent group, and the thermal stability, leveling property and developability can be adjusted by adjusting the composition of the dendrimer substituent group.
In the invention, the number of the peripheral dendritic compound substituent groups can be one or more, and the dispersion degree of the phthalocyanine molecules can be adjusted by regulating and controlling the number of the peripheral dendritic compound substituent groups.
In one embodiment, X in the phthalocyanine molecule is at least one of a halogen, bromine or chlorine, the halogen being used to adjust the chromaticity of the phthalocyanine molecule.
In one embodiment, M in the phthalocyanine molecule is a metal, which may be copper or zinc.
In addition, an embodiment of the present invention further provides a liquid crystal display panel, as shown in fig. 1, the liquid crystal display panel 10 includes an array substrate 100 and a color filter substrate 200 which are arranged in a box-to-box manner, and a liquid crystal 300 filled between the array substrate 100 and the color filter substrate 200; the color filter substrate 200 includes a substrate 210, a black matrix 220, a color resistance layer 230, a planarization layer 240, a common electrode layer 250, and a support pillar 260, which are sequentially disposed from top to bottom, where the color resistance layer 230 includes a red color resistance 231, a green color resistance 232, and a blue color resistance 233, where the green color resistance 232 includes a green color resistance material, and the green color resistance material is the green color resistance material described in any of the embodiments above.
The invention adopts the dendritic compound as the phthalocyanine peripheral substituent group, utilizes the dendritic compound to generate enough steric hindrance and hinders aggregation among molecules, thereby leading phthalocyanine molecules in the green color-resisting material to be in a monomolecular state and have higher solubility in a solvent, reducing the scattering effect of the green color-resisting material and improving the light penetrating power.
The finally prepared novel phthalocyanine green light resistance material with high solubility and high penetration is used for preparing the green color resistance 232 in the color resistance layer 230, and the green color resistance 232 is used in the liquid crystal display panel, so that the penetration and the contrast of the display panel are improved, the display effect of the display panel is enhanced, and the market competitiveness is improved.
Meanwhile, the invention also provides a preparation method of the green color resistance material, as shown in fig. 2, the method comprises the following steps:
s1: preparing a phthalocyanine molecule precursor, wherein at least one group in the phthalocyanine molecule precursor is a dendritic compound substituent group;
s2: synthesizing a phthalocyanine molecule precursor into phthalocyanine molecules to prepare a green color resistance material;
the steps are specifically described below.
In S1, a phthalocyanine molecule precursor is prepared, at least one group of which is a dendrimer substituent group. The steps may specifically include:
s11: precursor compounds and dendrimers are provided.
Precursor combinationThe structural formula of the compound is
Wherein X is at least one of bromine or chlorine.
The structural formula of the dendritic compound is
S12: and reacting the precursor compound with the dendritic compound, wherein the dendritic compound substitutes at least one group in the precursor compound to form the phthalocyanine molecule precursor. The steps may specifically include:
s121: the precursor compound and the dendrimer compound were dissolved in dimethylformamide at a molar ratio of 1:1 under N2 to form a 0.1M reaction solution.
S122: adding K to the reaction solution2CO3And heating and refluxing for 12 hours, cooling to stop the reaction, and carrying out column purification treatment to enable the dendritic compound to replace at least one group in the precursor compound to form a phthalocyanine molecule precursor.
The synthesis process in S12 is as follows:
wherein the content of the first and second substances,
is a precursor compound, 0TsL is a dendrimer compound,
is a phthalocyanine molecule precursor.
Group L-in dendrimer 0TsL, substituted precursor Compound
Group H-in (1) to form a phthalocyanine molecule precursor
The structural formula of L-is
One kind of (1).
And X is one or more of halogen Br or Cl.
The phthalocyanine molecule precursor is prepared through the processes.
In S2, the phthalocyanine molecule precursor is synthesized into phthalocyanine molecules to obtain the green color resist material. The method comprises the following steps:
s21: in N2Under the environment, dissolving a phthalocyanine molecule precursor, an intermediate compound and metal acetate in an alcohol solvent;
s22: heating and refluxing the alcohol solvent for 5 days, taking 1, 8-diazabicyclo [5,4,0] deca-7-ene as a catalyst, and purifying by a column after the reaction is completed to obtain the phthalocyanine molecule.
The reaction process in S2 is:
wherein the content of the first and second substances,
is a precursor of phthalocyanine molecules,
is an intermediate compound, M (CH)3COO)2Is an acetate salt of a metal, and is,
is a phthalocyanine molecule.
The metal in the metal acetate can adopt copper or zinc, and the alcohol solvent is a high-boiling-point alcohol solvent.
The structural formula of R in phthalocyanine molecule is
One kind of (1).
The green color resistance material is prepared through the steps.
After the preparation of the green color resistance material is finished, the green color resistance material is mixed with a solvent, a photoinitiator, a polymer and a monomer to form a green color resistance liquid, the light resistance liquid is coated on a glass substrate in a coating mode, then pre-baking is carried out to remove the solvent, exposure and development are carried out to manufacture a pattern, post-baking is carried out to cure to form a color resistance sheet, and the prepared color resistance sheet is used in a liquid crystal display panel as a color resistance layer.
In one example, the solvent is propylene glycol methyl ether acetate PGMEA.
In the prior art, most of the color development components of the green color resists are phthalocyanine molecules, the phthalocyanine is a compound of a macrocyclic conjugated aromatic system with 18 electrons, and the conjugated planar structure of the compound enables the molecules to have strong pi-pi interaction force, so that the compound is easy to form molecular aggregation, is difficult to form a monomolecular state, has obvious scattering effect, and cannot meet the requirement of high penetrating power.
The invention adopts the dendritic compound as the phthalocyanine peripheral substituent group, utilizes the dendritic compound to generate enough steric hindrance and hinders aggregation among molecules, thereby leading phthalocyanine molecules in the green color-resisting material to be in a monomolecular state and have higher solubility in a solvent, reducing the scattering effect of the green color-resisting material and improving the light penetrating power. The finally prepared novel phthalocyanine green light resistance material with high solubility and high penetration is used for manufacturing a color resistance layer for liquid crystal display, and the penetration rate and the contrast ratio of the material are greatly improved.
In one embodiment, the dendrimer substituent group is predominantly alkyl chain. The intermiscibility of the alkyl chain and propylene glycol methyl ether acetate is good, so that the solubilization effect of phthalocyanine molecules is obvious, and a green photoresist material with high solubility and high penetrating power is easier to obtain.
In the present invention, there are various structures of the dendrimer substituent group, and the thermal stability, leveling property and developability can be adjusted by adjusting the composition of the dendrimer substituent group.
In the invention, the number of the peripheral dendritic compound substituent groups can be one or more, and the dispersion degree of the phthalocyanine molecules can be adjusted by regulating and controlling the number of the peripheral dendritic compound substituent groups.
In one embodiment, X in the phthalocyanine molecule is at least one of a halogen, bromine or chlorine, the halogen being used to adjust the chromaticity of the phthalocyanine molecule.
The chroma can be adjusted by adjusting the type and the number of the phthalocyanine molecular halogen, and the length balance dissolving capacity and the thermal stability of the branched chain can be adjusted by adjusting the number of the dendritic compound substituent groups or adjusting the length of the branched chain.
The invention provides a green color resistance material, a liquid crystal display panel and a preparation method thereof. By forming the dendritic compound substituent group, enough steric hindrance is generated between adjacent phthalocyanine molecules to hinder aggregation between the molecules, so that the green color-resisting material is in a monomolecular state, the scattering effect of the green color-resisting material is reduced, and the light penetration is improved.
In the foregoing embodiments, the descriptions of the respective embodiments have respective emphasis, and for parts that are not described in detail in a certain embodiment, reference may be made to related descriptions of other embodiments.
The green color resistance material, the liquid crystal display panel and the preparation method provided by the embodiment of the application are introduced in detail, a specific example is applied in the description to explain the principle and the implementation mode of the application, and the description of the embodiment is only used for helping to understand the technical scheme and the core idea of the application; those of ordinary skill in the art will understand that: the technical solutions described in the foregoing embodiments may still be modified, or some technical features may be equivalently replaced; such modifications or substitutions do not depart from the spirit and scope of the present disclosure as defined by the appended claims.
Claims (10)
1. A green color resist material, which is characterized by comprising phthalocyanine molecules, wherein at least one group of the phthalocyanine molecules is a dendritic compound substituent group.
2. A green color-resist material according to claim 1, wherein the main body of the substituent group of the dendrimer is an alkyl chain.
3. The green color resist material of claim 2, wherein the phthalocyanine molecule has a formula of
Wherein L-is the dendrimer substituent group.
4. The green color-resist material according to claim 3, wherein the structural formula of the substituent group of the dendrimer is
One kind of (1).
5. A green color resist according to claim 3, wherein R in the phthalocyanine molecule has the formula
One kind of (1).
6. A green color resist according to claim 3, wherein X in the phthalocyanine molecule is at least one of bromine or chlorine.
7. A liquid crystal display panel comprising a color resist layer comprising the green color resist material according to any one of claims 1 to 6.
8. A preparation method of a green color resistance material is characterized by comprising the following steps:
preparing a phthalocyanine molecule precursor, wherein at least one group in the phthalocyanine molecule precursor is a dendritic compound substituent group;
synthesizing the phthalocyanine molecule precursor into phthalocyanine molecules to prepare the green color-resisting material.
9. The method for preparing a green color resist material according to claim 8, wherein the step of preparing a phthalocyanine molecule precursor in which at least one group is a dendrimer substituent group comprises:
in N2Dissolving a precursor compound and a dendritic compound in dimethyl formamide according to a molar ratio of 1:1 to form a 0.1M reaction solution under the environment;
adding K to the reaction solution2CO3And heating and refluxing for 12 hours, cooling to stop the reaction, and carrying out column purification treatment to enable the dendritic compound to replace at least one group in the precursor compound to form the phthalocyanine molecule precursor.
10. The method for preparing a green color resist material according to claim 8, wherein the step of synthesizing the phthalocyanine molecule precursor into a phthalocyanine molecule to prepare the green color resist material comprises:
in N2Under the environment, willDissolving the phthalocyanine molecule precursor, the intermediate compound and the metal acetate in an alcohol solvent;
heating and refluxing the alcohol solvent for 5 days, taking 1, 8-diazabicyclo [5,4,0] deca-7-ene as a catalyst, and purifying by a column after the reaction is completed to obtain the phthalocyanine molecule.
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Application publication date: 20200619 |
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