CN110964208B - Green photoresist material, LCD display panel and preparation method - Google Patents
Green photoresist material, LCD display panel and preparation method Download PDFInfo
- Publication number
- CN110964208B CN110964208B CN201911198196.9A CN201911198196A CN110964208B CN 110964208 B CN110964208 B CN 110964208B CN 201911198196 A CN201911198196 A CN 201911198196A CN 110964208 B CN110964208 B CN 110964208B
- Authority
- CN
- China
- Prior art keywords
- substituent group
- phthalocyanine
- display panel
- dendrimer
- dendritic compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000000463 material Substances 0.000 title claims abstract description 49
- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title abstract description 11
- 239000000412 dendrimer Substances 0.000 claims abstract description 116
- 125000001424 substituent group Chemical group 0.000 claims abstract description 90
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims abstract description 86
- 229920000736 dendritic polymer Polymers 0.000 claims description 47
- 239000002243 precursor Substances 0.000 claims description 27
- 239000000126 substance Substances 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 239000004698 Polyethylene Substances 0.000 claims description 12
- 239000002202 Polyethylene glycol Substances 0.000 claims description 12
- -1 polyethylene Polymers 0.000 claims description 12
- 229920000573 polyethylene Polymers 0.000 claims description 12
- 229920001223 polyethylene glycol Polymers 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 7
- 230000002194 synthesizing effect Effects 0.000 claims description 7
- 125000004427 diamine group Chemical group 0.000 claims description 6
- 150000004985 diamines Chemical class 0.000 claims description 6
- 230000035515 penetration Effects 0.000 abstract description 16
- 238000000149 argon plasma sintering Methods 0.000 abstract description 6
- 238000006243 chemical reaction Methods 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 229910000104 sodium hydride Inorganic materials 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- 238000010791 quenching Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- 125000003282 alkyl amino group Chemical group 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 230000004438 eyesight Effects 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- SNHOURMNEXCAJV-UHFFFAOYSA-N sulfuryl dichloride;toluene Chemical compound ClS(Cl)(=O)=O.CC1=CC=CC=C1 SNHOURMNEXCAJV-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/002—Dendritic macromolecules
- C08G83/003—Dendrimers
- C08G83/004—After treatment of dendrimers
-
- 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
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Nonlinear Science (AREA)
- Optics & Photonics (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Mathematical Physics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
Abstract
The application provides a green light resistance material, an LCD display panel and a preparation method, wherein the green light resistance material is phthalocyanine molecules, and one substituent group of the phthalocyanine molecules is a dendritic compound; on one hand, the dendritic compound has large steric hindrance of a substituent group, and can prevent phthalocyanine molecules from accumulating and gathering due to strong pi-pi acting force; on the other hand, the dendritic compound substituent group has amphipathy, so that the solubility of phthalocyanine molecules is improved, and the problem that a photoresist material is easy to remain in development is solved; the phthalocyanine molecule with monomolecular state and high solubility can avoid stray light caused by light scattering problem and greatly improve the penetration and contrast of color resistance; therefore the green photoresist material that this application provided has possessed high solubility, high penetration simultaneously, the thermal stability is good, the characteristic of self-development, is applied to LCD display panel, will promote display panel's luminance, contrast, has alleviated current LCD display panel and has had luminance, the not enough problem of contrast.
Description
Technical Field
The application relates to the field of display, in particular to a green light resistance material, an LCD display panel and a preparation method.
Background
The Liquid Crystal Display (LCD) technology is a passive light emitting mode, and its color reduction capability is mainly reproduced by a backlight through a color filter, and the demand for developing color chips is increasing under the current demands of high brightness, wide color gamut and high contrast. The influence of the green light resistance is the largest, and because the eye sight function shows that the vision is most sensitive to the green, the green light is slightly improved, and the integral improvement assistance to the LCD penetration is large.
However, the conventional pigment particles have a large size and a significant scattering effect, so that the backlight utilization rate is low, the brightness and the contrast are reduced, and the requirements of high definition, large size and high resolution are not met.
Therefore, the conventional LCD display panel has insufficient brightness and contrast, and needs to be solved.
Disclosure of Invention
The application provides a green photoresist material, a green photoresist sheet and a preparation method thereof, which are used for solving the problems of insufficient brightness and contrast of the existing LCD display panel.
The application provides a green light-resistant material, the green light-resistant material is phthalocyanine molecule, and a substituent group of the phthalocyanine molecule is dendritic compound.
In some embodiments, the main constituent of the dendrimer substituent group is an alkoxy chain.
In some embodiments, the phthalocyanine molecule has the general chemical formula
Wherein LO-is the dendrimer substituent group.
In some embodiments, the dendrimer substituent group comprises a primary dendrimer substituent group
Substituent group of second generation dendritic compound
Substituent group of third generation dendritic compound
In some embodiments, the
The above-mentioned
And said
R in the formula (I) is a polyethylene glycol or polyethylene diamine structure with different chain lengths.
In some embodiments, the polyethylene glycol has the general chemical formula
In some embodiments, the polyethylene diamine has the formula
In some embodiments, the
And said
Wherein n is 1 to 4.
The present application provides an LCD display panel comprising a green photoresist layer comprising a green photoresist material as described above.
Meanwhile, the application also provides a preparation method of the green photoresist material, which comprises the following steps:
preparing a dendrimer substituent;
an HO-group protecting a dendrimer substituent;
synthesizing a phthalocyanine molecule precursor;
synthesizing the phthalocyanine molecule by using the phthalocyanine molecule precursor.
The application provides a green light resistance material, an LCD display panel and a preparation method, wherein the green light resistance material is phthalocyanine molecules, and one substituent group of the phthalocyanine molecules is a dendritic compound taking an alkoxy chain as a main body; on one hand, the dendritic compound has large steric hindrance of a substituent group, can prevent phthalocyanine molecules from accumulating and gathering due to strong pi-pi acting force, and ensures the monomolecular state of the phthalocyanine molecules; on the other hand, the main body of the dendritic compound substituent group is an alkoxy chain and has amphipathy, so that phthalocyanine molecules and common solvents of the color-resisting material have similar compatibility, the solubility of the phthalocyanine molecules is further improved, meanwhile, the phthalocyanine molecules also have certain water-soluble capacity, can be partially dissolved in an alkaline developing solution, and the problem that the developing of the light-resisting material is easy to remain is solved; the phthalocyanine molecule with monomolecular state and high solubility can avoid the stray light caused by light scattering problem and greatly improve the penetration rate and contrast ratio of color resistance. Therefore, the green photoresist material provided by the application has the characteristics of high solubility, high penetration, good thermal stability and self-development, is prepared into a green photoresist sheet, greatly improves the penetration rate of the green photoresist sheet, is applied to an LCD display panel, greatly improves the brightness and contrast of the LCD display panel, and alleviates the problem that the brightness and contrast of the existing LCD display panel are not enough.
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 flowchart illustrating a process of preparing a green photoresist according to an embodiment of the present disclosure.
Fig. 2 is a schematic structural diagram of an LCD display panel according to an embodiment of the present disclosure.
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.
To there being the not enough problem of luminance, contrast in current LCD display panel, this application provides a green photoresist material can alleviate this problem.
In one embodiment, the present application provides a green photoresist material that is a phthalocyanine molecule whose LO-substituent is a dendrimer.
The embodiment of the application provides a green photoresist material, which is phthalocyanine molecules, wherein one substituent group of the phthalocyanine molecules is a dendritic compound. On one hand, the dendritic compound has large steric hindrance of a substituent group, can prevent phthalocyanine molecules from accumulating and gathering due to strong pi-pi acting force, and ensures the monomolecular state of the phthalocyanine molecules; on the other hand, the dendritic compound substituent group has amphipathy, so that phthalocyanine molecules and common solvents of the color-resisting materials have similar compatibility, the solubility of the phthalocyanine molecules is further improved, meanwhile, the phthalocyanine molecules also have certain water-soluble capacity, can be partially dissolved in an alkaline developing solution, and the problem that the developing of the light-resisting materials is easy to remain is solved; the phthalocyanine molecule with monomolecular state and high solubility can avoid the stray light caused by light scattering problem and greatly improve the penetration rate and contrast ratio of color resistance. Therefore, the green photoresist material provided by the application has the characteristics of high solubility, high penetration, good thermal stability and self-development, is prepared into a green photoresist sheet, greatly improves the penetration rate of the green photoresist sheet, is applied to an LCD display panel, greatly improves the brightness and contrast of the LCD display panel, and alleviates the problem that the brightness and contrast of the existing LCD display panel are not enough.
In one embodiment, the phthalocyanine molecule has the general chemical formula
Wherein LO-is a dendritic compound substituent group, and the main body of the dendritic compound substituent group is an alkoxy chain.
In one embodiment, the dendrimer substituent group LO-is a one-generation dendrimer substituent group
In the chemical formula, R is polyethylene glycol or polyethylene diamine structure with different chain lengths; the chemical general formula of the polyethylene glycol is
The chemical general formula of the polyethylene diamine is
Wherein n is 1 to 4.
In another embodiment, the dendrimer substituent LO-is a second generation dendrimer substituent
In the chemical formula, R is polyethylene glycol or polyethylene diamine structure with different chain lengths; the chemical general formula of the polyethylene glycol is
The chemical general formula of the polyethylene diamine is
Wherein n is 1 to 4.
In another embodiment, the dendrimer substituent LO-is a tri-generation dendrimer substituent
In the chemical formula, R is polyethylene glycol or polyethylene diamine structure with different chain lengths, and the chemical general formula of the polyethylene glycol is
The chemical general formula of the polyethylene diamine is
Wherein n is 1 to 4.
In the embodiment of the application, the phthalocyanine molecule has a certain developing capability, and the water solubility of the ligand can be adjusted by adjusting the substituent groups of the dendritic compounds with different generations or adjusting the length of the alkoxy chain, so as to control the developing capability of the phthalocyanine molecule. For the same alkoxy chain length, the larger the generation number of the substituent group of the dendritic compound, the larger the steric hindrance of the substituent group of the dendritic compound, the better the amphipathy, and the better the developing effect of the phthalocyanine molecule as a green light resistance material; for the same generation of dendritic compound substituent groups, the longer the length of an alkoxy chain, the larger the steric hindrance of the dendritic compound substituent group, the better the amphipathy, and the better the developing effect of the phthalocyanine molecule as a green photoresist material.
In another embodiment, in the phthalocyanine molecule provided by the present application, the main body of the dendritic compound substituent group is an alkylamino chain, and the working principle thereof is similar to that of the above embodiment in which the dendritic compound substituent group is an alkoxy chain.
Meanwhile, the embodiment of the present application provides a method for preparing a green photoresist material, the preparation method implants a substituent group of a dendrimer into a phthalocyanine molecule, as shown in fig. 1, and the specific preparation steps include:
s1, preparing a dendritic compound substituent;
s2, an HO-group protecting a dendrimer substituent;
s3, synthesizing a phthalocyanine molecule precursor;
and S4, synthesizing phthalocyanine molecules by using the phthalocyanine molecule precursor.
The embodiment of the application provides a preparation method of a green photoresist material, wherein a substituent group of a dendritic compound is implanted into a phthalocyanine molecule; on one hand, the dendritic compound has large steric hindrance of a substituent group, can prevent phthalocyanine molecules from accumulating and gathering due to strong pi-pi acting force, and ensures the monomolecular state of the phthalocyanine molecules; on the other hand, the dendritic compound substituent group has amphipathy, so that phthalocyanine molecules and common solvents of the color-resisting materials have similar compatibility, the solubility of the phthalocyanine molecules is further improved, meanwhile, the phthalocyanine molecules also have certain water-soluble capacity, can be partially dissolved in an alkaline developing solution, and the problem that the developing of the light-resisting materials is easy to remain is solved; the phthalocyanine molecule with monomolecular state and high solubility can avoid stray light caused by light scattering problem, and greatly improve the penetration rate and contrast ratio of color resistance; therefore, the green photoresist material provided by the application has the characteristics of high solubility, high penetration, good thermal stability and self-development, is prepared into a green photoresist sheet, greatly improves the penetration rate of the green photoresist sheet, is applied to an LCD display panel, greatly improves the brightness and contrast of the LCD display panel, and alleviates the problem that the brightness and contrast of the existing LCD display panel are not enough.
In one embodiment, the specific steps for preparing the dendrimer substituent include:
s11, preparing a dendritic compound precursor;
s12, preparing a dendritic compound substituent by using the dendritic compound precursor.
In one embodiment, the dendrimer substituent group of the phthalocyanine molecule provided in the examples herein is a first generation dendrimer substituent group
The dendritic compound substituent is a generation of dendritic compound substituent
The specific steps for preparing the first generation dendrimer precursor comprise:
s1111, dissolving alcohol in 100mL THF (Tetrahydrofuran) to form 0.1mol/L reaction bottom liquid;
s1112, slowly adding NaH (sodium hydride) at room temperature, and stirring for 5min to fully dissolve the NaH;
s1113, adding dihydroxy chloride in batches to ensure that the molar ratio of alcohol to dihydroxy chloride is 2.5:1, and then heating and refluxing overnight;
s1114, cooling after the reaction is completed, and adding water to quench the reaction;
s1115, filtering, spin-drying, and purifying by column chromatography to obtain the target generation dendritic compound precursor.
In this example, the synthetic route of the first generation dendrimer precursor is:
the specific steps for preparing the first generation dendrimer substituent by using the first generation dendrimer precursor comprise:
s1211, dissolving the first generation dendritic compound precursor in 100mL THF to form 0.1mol/L reaction bottom liquid;
s1212, adding BH dropwise at 0 DEG C3(borohydrido) and stirred overnight at 0 ℃;
s1213, after the reaction is completed, adding NaOH (sodium hydroxide) aqueous solution in batches to quench the reaction;
s1214, spin-drying, and purifying by column walking to obtain a first generation dendritic compound substituent.
In this example, the synthetic route for one generation of dendrimer substituents is:
in another embodiment, the dendrimer substituent group of the phthalocyanine molecule provided in the examples herein is a second generation dendrimer substituent group
The dendritic compound substituent is a second generation dendritic compound substituent
The specific steps for preparing the second generation dendritic compound precursor comprise:
s1121, dissolving a first generation dendritic compound substituent in 100mL THF to form 0.1mol/L reaction base solution;
s1122, slowly adding NaH at room temperature, and stirring for 5min to fully dissolve the NaH;
s1123, adding the dihydroxy chloride in batches to ensure that the molar ratio of the alcohol to the dihydroxy chloride is 2.5:1, and then heating and refluxing for overnight;
s1124, cooling after the reaction is completed, and adding water to quench the reaction;
s1125, filtering, spin-drying, and purifying by a column to obtain the target second-generation dendritic compound precursor.
In this embodiment, the synthetic route of the second generation dendrimer precursor is as follows:
the specific steps of preparing the substituent of the second generation dendritic compound by utilizing the second generation dendritic compound precursor comprise:
s1221, dissolving the second generation dendritic compound precursor in 100mL THF to form 0.1mol/L reaction base solution;
s1222 dropwise addition of BH at 0 deg.C3Keeping the temperature at 0 ℃ and stirring overnight;
s1223, after the reaction is completed, adding NaOH aqueous solution in batches to quench the reaction;
s1224, spin-drying, and purifying by column chromatography to obtain the second generation dendrimer substituent.
In this example, the synthetic route for the substituent of the second generation dendrimer is:
in yet another embodiment, the dendrimer substituent group of the phthalocyanine molecule provided in the examples herein is a tertiary dendrimer substituent group
The dendritic compound substituent is a second generation dendritic compound substituent
The specific steps for preparing the third generation dendritic compound precursor comprise:
s1131, dissolving the substituent of the second generation dendritic compound in 100mL THF to form 0.1mol/L reaction base solution;
s1132, slowly adding NaH at room temperature, and stirring for 5min to fully dissolve the NaH;
s1133, adding the dihydroxy chloride in batches to ensure that the molar ratio of the alcohol to the dihydroxy chloride is 2.5:1, and then heating and refluxing for overnight;
s1134, cooling after the reaction is completed, and adding water to quench the reaction;
s1135, filtering, spin-drying and purifying by column chromatography to obtain the target third-generation dendritic compound precursor.
In this embodiment, the synthetic route of the third generation dendrimer precursor is as follows:
the specific steps for preparing the substituent of the third-generation dendritic compound by utilizing the third-generation dendritic compound precursor comprise:
s1231, dissolving the third generation dendritic compound precursor in 100mL THF to form 0.1mol/L reaction base solution;
s1232, dropwise adding BH at 0 DEG C3Keeping the temperature at 0 ℃ and stirring overnight;
s1233, after the reaction is completed, adding NaOH aqueous solution in batches to quench the reaction;
and S1234, spin-drying, and purifying by column chromatography to obtain the third generation dendritic compound substituent.
In this example, the synthetic route of the substituent of the third generation dendrimer is:
in one embodiment, the specific steps of protecting the HO-groups of the dendrimer substituent include:
s21, dissolving a dendritic compound substituent in THF to form 0.1mol/L reaction base solution;
s22, slowly adding NaH at room temperature, and stirring for 5min to fully dissolve the NaH;
s23, adding p-TsCl (methyl benzene sulfonyl chloride) under strong stirring to ensure that the molar ratio of Ts to the dendritic compound substituent is 1.5: 1;
s24, stirring for 3 hours at room temperature, and adding deionized water to quench the reaction;
s25, filtering, spin-drying and purifying by column chromatography to obtain the product protected by Ts.
In this embodiment, the dendrimer substituent includes L1
The corresponding Ts-protected products are TsOL1, TsOL2 and TsOL3, respectively.
In one embodiment, the phthalocyanine molecule precursor is synthesized by the specific steps of:
s31 at N2Under (nitrogen) environment, the compound is mixed
Adding DMF (dimethylformamide) into the product TsOL (wherein L comprises L1, L2 and L3) after Ts protection in a molar ratio of 1:1
X in the (B) is one or more of halogen Br or Cl;
s32, adding K2CO3Heating and refluxing for 6 h;
s33, cooling to stop reaction, and purifying by column chromatography to obtain the phthalocyanine precursor compound
In this example, the synthesis route of the phthalocyanine molecule precursor is:
in one embodiment, the specific steps of synthesizing the phthalocyanine molecule by using the phthalocyanine molecule precursor include:
s41 at N2Under the environment, the compound
Compound (I)
Heating and refluxing the mixture with metal acetate in a high boiling alcohol solvent for 5 days by using 1, 8-diazabicyclo [5,4, 0%]Deca-7-ene (DBU) as catalyst, the metal is copper or zinc
R' in the formula (I) is one or more of Br, Cl or tert-butyl benzene;
and S42, performing column purification after the reaction is completed to obtain the target phthalocyanine molecule.
In this example, the synthesis route of the phthalocyanine molecule is:
in addition, an LCD display panel is further provided in the embodiment of the present application, as shown in fig. 2, the LCD display panel 10 includes an array substrate 100 and a color filter substrate 200 that are oppositely disposed, 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 photoresist 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 photoresist layer 230 includes a red photoresist layer 231, a green photoresist layer 232, and a blue photoresist layer 233, where the material of the green photoresist layer 232 includes a green photoresist material, the green photoresist material is a phthalocyanine molecule, and one substituent group of the phthalocyanine molecule is a dendrimer.
The embodiment of the application provides an LCD display panel, which comprises a green light resistance layer, wherein the green light resistance layer comprises a green light resistance material, the green light resistance material is phthalocyanine molecules, and one substituent group of the phthalocyanine molecules is a dendritic compound. On one hand, the dendritic compound has large steric hindrance of a substituent group, can prevent phthalocyanine molecules from accumulating and gathering due to strong pi-pi acting force, and ensures the monomolecular state of the phthalocyanine molecules; on the other hand, the dendritic compound substituent group has amphipathy, so that phthalocyanine molecules and common solvents of the color-resisting materials have similar compatibility, the solubility of the phthalocyanine molecules is further improved, meanwhile, the phthalocyanine molecules also have certain water-soluble capacity, can be partially dissolved in an alkaline developing solution, and the problem that the developing of the light-resisting materials is easy to remain is solved; the phthalocyanine molecule with monomolecular state and high solubility can avoid the stray light caused by light scattering problem and greatly improve the penetration rate and contrast ratio of color resistance. Therefore, the green photoresist material provided by the application has the characteristics of high solubility, high penetration, good thermal stability and self-development, is applied to the LCD display panel, greatly improves the brightness and contrast of the LCD display panel, and alleviates the problem that the brightness and contrast of the existing LCD display panel are not enough.
In one embodiment, the main constituent of the dendrimer substituent group is an alkoxy chain.
In another embodiment, the dendrimer substituent group is predominantly an alkylamino chain.
In one embodiment, the phthalocyanine molecule has the chemical formula
Wherein LO-is a dendrimer substituent group.
In one embodiment, the dendrimer substituent group includes a one-generation dendrimer substituent group
Substituent group of second generation dendritic compound
Substituent group of third generation dendritic compound
In one embodiment of the present invention, the substrate is,
r in the formula (I) is a polyethylene glycol or polyethylene diamine structure with different chain lengths.
In one embodiment, the polyethylene glycol has the general chemical formula
In one embodiment, the polyethylene diamine has the formula
In one embodiment of the present invention, the substrate is,
wherein n is 1 to 4.
In one embodiment, green resist layer 232 may be obtained by conventional fabrication methods: mixing the phthalocyanine molecule provided by the embodiment of the application with a solvent PGMEA (propylene glycol methyl ether acetate), a photoinitiator, a polymer and a monomer in a pre-prepared proportion to prepare a green photoresist liquid; after the red photoresist layer 131 is prepared, the green photoresist liquid is coated on the color film substrate 200 in a coating mode; followed by a pre-bake to remove the solvent PGMEA; then carrying out exposure and development, and patterning to obtain a green photoresist pattern; and finally, carrying out post-baking curing.
In the developing process, the phthalocyanine molecule has certain developing capacity, and the alkoxy chain and the alkyl amino chain have amphipathy and can be partially dissolved in an alkaline developing solution, so that the problem that the photoresist is easy to remain in the developing process is solved, and the developing capacity of the phthalocyanine molecule can be controlled by adjusting dendritic compound substituent groups with different generations or adjusting the lengths of the alkoxy chain and the alkyl amino chain. In the dendritic compound substituent groups with the same main body, the greater the algebraic number of the dendritic compound substituent groups with the same chain length, the greater the steric hindrance of the dendritic compound substituent groups, the better the amphipathy, and the better the developing effect of the phthalocyanine molecules as green photoresist materials; for the dendritic compound substituent group with the same generation number, the longer the chain length is, the larger the steric hindrance of the dendritic compound substituent group is, the better the amphipathy is, and the better the developing effect of the phthalocyanine molecule as a green photoresist material is.
According to the above embodiments:
the embodiment of the application provides a green light resistance material, an LCD display panel and a preparation method, wherein the green light resistance material is phthalocyanine molecules, one substituent group of the phthalocyanine molecules is a dendritic compound, and the main body of the substituent group of the dendritic compound is an alkoxy chain or an alkylamino chain. On one hand, the dendritic compound has large steric hindrance of a substituent group, can prevent phthalocyanine molecules from accumulating and gathering due to strong pi-pi acting force, and ensures the monomolecular state of the phthalocyanine molecules; on the other hand, the main body of the dendritic compound substituent group is an alkoxy chain or an alkylamino chain, and the main body has amphipathy, so that phthalocyanine molecules and common solvents of the color-resisting material have similar compatibility, the solubility of the phthalocyanine molecules is further improved, and meanwhile, the phthalocyanine molecules also have certain water-soluble capacity, can be partially dissolved in an alkaline developing solution, and the problem that the development of the light-resisting material is easy to remain is solved; the phthalocyanine molecule with monomolecular state and high solubility can avoid the stray light caused by light scattering problem and greatly improve the penetration rate and contrast ratio of color resistance. Therefore, the green photoresist material provided by the application has the characteristics of high solubility, high penetration, good thermal stability and self-development, is applied to the LCD display panel, greatly improves the brightness and contrast of the display panel, and alleviates the problem that the brightness and contrast of the existing LCD display panel are not enough.
In summary, although the present application has been described with reference to the preferred embodiments, the above-described preferred embodiments are not intended to limit the present application, and those skilled in the art can make various changes and modifications without departing from the spirit and scope of the present application, so that the scope of the present application shall be determined by the appended claims.
Claims (5)
1. A green light resistance material is characterized in that the green light resistance material is phthalocyanine molecules, one substituent group of the phthalocyanine molecules is a dendrimer, and the dendrimer substituent group comprises a first generation dendrimer substituent group
Substituent group of second generation dendritic compound
Substituent group of third generation dendritic compound
The above-mentioned
The above-mentioned
And said
Wherein R is polyethylene glycol and polyethylene diamine structure with different chain lengths,
wherein the chemical general formula of the phthalocyanine molecule is
The chemical general formula of the polyethylene glycol is
The chemical general formula of the polyethylene diamine is
The above-mentioned
And said
Wherein n is 1 to 4.
2. The green photoresist material of claim 1, wherein the main body of the substituent group of the dendrimer is an alkoxy chain.
3. The green resist according to claim 2, wherein LO "in the chemical formula of the phthalocyanine molecule is the substituent group of the dendrimer.
4. An LCD display panel comprising a green photoresist layer comprising the green photoresist material of any one of claims 1 to 3.
5. A method for preparing a green photoresist, which is used for preparing the green photoresist of claim 1, the method comprising:
preparing a dendrimer substituent;
an HO-group protecting a dendrimer substituent;
synthesizing a phthalocyanine molecule precursor;
synthesizing the phthalocyanine molecule by using the phthalocyanine molecule precursor.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911198196.9A CN110964208B (en) | 2019-11-29 | 2019-11-29 | Green photoresist material, LCD display panel and preparation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911198196.9A CN110964208B (en) | 2019-11-29 | 2019-11-29 | Green photoresist material, LCD display panel and preparation method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN110964208A CN110964208A (en) | 2020-04-07 |
| CN110964208B true CN110964208B (en) | 2021-12-28 |
Family
ID=70032163
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911198196.9A Active CN110964208B (en) | 2019-11-29 | 2019-11-29 | Green photoresist material, LCD display panel and preparation method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110964208B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111978757B (en) * | 2020-08-11 | 2021-09-03 | Tcl华星光电技术有限公司 | Three-dimensional dye, preparation method of three-dimensional dye and photoresist mixture |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11281813A (en) * | 1998-03-30 | 1999-10-15 | Sony Corp | Manufacture of color filter for solid image pickup element |
| CN106597722A (en) * | 2016-12-13 | 2017-04-26 | 深圳市华星光电技术有限公司 | Liquid crystal lens, manufacturing method thereof and liquid crystal display |
| CN106700528B (en) * | 2016-12-29 | 2019-12-17 | 淮阴师范学院 | Supermolecule assembly and preparation and shape regulation and control method thereof |
-
2019
- 2019-11-29 CN CN201911198196.9A patent/CN110964208B/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN110964208A (en) | 2020-04-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6097247B2 (en) | Near-infrared absorbing composition, near-infrared cut filter using the same, and method for manufacturing the same, and camera module and method for manufacturing the same | |
| CN105189431A (en) | Vinyl-group-containing fluorene compound | |
| CN103357346B (en) | Pigment dispersing agent, pigment dispersion liquid, colorized photoresist, and preparation and application thereof | |
| JP6617703B2 (en) | Photosensitive resin composition, cured product, black matrix, and image display device | |
| CN103025831B (en) | Dye composition, colored solidification constituent, colored filter and manufacture method thereof, solid-state image sensors and liquid crystal display device | |
| TWI742166B (en) | Photosensitive color resin composition for color filter, color filter and display device | |
| JP2017201003A (en) | Coloring composition, colored cured film, color filter, display element and solid state image sensor | |
| CN110964208B (en) | Green photoresist material, LCD display panel and preparation method | |
| CN103154052A (en) | Diene-based carboxylate anion and salt thereof, and polymerizable or curable composition thereof | |
| TW201202403A (en) | Composition used for hard coating, hard coating film and display device | |
| JP5659761B2 (en) | Red pigment dispersion for color filter, red photosensitive resin composition for color filter, color filter, and liquid crystal display device | |
| CN106471398A (en) | Connection carbazole compound, Photocurable composition, its solidfied material, the solidification compound for plastic lens and plastic lens | |
| TW201235365A (en) | Colored resin composition | |
| CN105622788B (en) | Three arm ATRP initiators and its preparation and application with planar conjugate structure | |
| CN105801477B (en) | Azo compound and polymer including it | |
| CN108181785B (en) | Nano silver wire photoresist and application thereof in manufacturing of touch screen device | |
| CN105467640A (en) | Manufacturing method for display panel substrate, display panel substrate, and touch panel display device | |
| JP6322226B2 (en) | Method for preparing diblock copolymer containing amino group | |
| CN112088192B (en) | Color material dispersion liquid, composition, film, optical filter, and display device | |
| CN111303166A (en) | Green color resistance material, liquid crystal display panel and preparation method | |
| KR20090022692A (en) | Cyanine dyestuff and optical filter for plasma display device | |
| CN113480681A (en) | Compound of electrochromic material and preparation method thereof | |
| CN110709477A (en) | Colorant compound and coloring composition comprising the same | |
| KR20140106832A (en) | Colored photosensitive resin composition | |
| JP2018173461A (en) | Photosensitive coloring resin composition, cured product, color filter, and display device |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |