CN111303167A - Color development material, optical filter and preparation method thereof - Google Patents
Color development material, optical filter and preparation method thereof Download PDFInfo
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- CN111303167A CN111303167A CN202010234854.1A CN202010234854A CN111303167A CN 111303167 A CN111303167 A CN 111303167A CN 202010234854 A CN202010234854 A CN 202010234854A CN 111303167 A CN111303167 A CN 111303167A
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- 238000002360 preparation method Methods 0.000 title claims abstract description 9
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- 239000002184 metal Substances 0.000 claims description 17
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- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 10
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- 238000001816 cooling Methods 0.000 claims description 9
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- 125000000732 arylene group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910001507 metal halide Inorganic materials 0.000 claims description 6
- 150000005309 metal halides Chemical class 0.000 claims description 6
- 125000004419 alkynylene group Chemical group 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- 125000004957 naphthylene group Chemical group 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 10
- 239000001007 phthalocyanine dye Substances 0.000 abstract description 6
- 238000004220 aggregation Methods 0.000 abstract description 3
- 230000002776 aggregation Effects 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
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- 238000003786 synthesis reaction Methods 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000007809 chemical reaction catalyst Substances 0.000 description 7
- GVRWIAHBVAYKIZ-UHFFFAOYSA-N dec-3-ene Chemical compound CCCCCCC=CCC GVRWIAHBVAYKIZ-UHFFFAOYSA-N 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- 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 description 7
- 239000003086 colorant Substances 0.000 description 6
- 229920002120 photoresistant polymer Polymers 0.000 description 6
- -1 methylene, ethylene, propylene Chemical group 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 239000010409 thin film Substances 0.000 description 4
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- ZTHNOZQGTXKVNZ-UHFFFAOYSA-L dichloroaluminum Chemical compound Cl[Al]Cl ZTHNOZQGTXKVNZ-UHFFFAOYSA-L 0.000 description 2
- BUMGIEFFCMBQDG-UHFFFAOYSA-N dichlorosilicon Chemical compound Cl[Si]Cl BUMGIEFFCMBQDG-UHFFFAOYSA-N 0.000 description 2
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- 239000003112 inhibitor Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical class N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
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- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/067—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
- C09B47/0671—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile having halogen atoms linked directly to the Pc skeleton
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/067—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
- C09B47/0675—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile having oxygen or sulfur linked directly to the skeleton
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
-
- 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
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Nonlinear Science (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Optical Filters (AREA)
Abstract
The application discloses a color developing material, an optical filter and a preparation method thereof, wherein an amphiphilic group is introduced to a molecular structure of a phthalocyanine dye, so that the developing capability of the phthalocyanine dye is improved, and the problem of residue of the phthalocyanine dye in the process of preparing the color optical filter is solved; meanwhile, a substituent with large steric hindrance is introduced to prevent aggregation among molecules, so that the color developing material keeps good solubility and heat resistance, and the optical filter prepared from the color developing material has excellent optical performance and highly fine patterns, and improves the display quality of display products such as LCDs, OLEDs and the like.
Description
Technical Field
The application relates to the field of display, in particular to a color developing material, an optical filter and a preparation method thereof.
Background
With the widespread use of Display products such as Liquid Crystal Displays (LCDs), Organic Light Emitting Diodes (OLEDs), and the like, the requirements for color Display of displays are increasing. The color filter is an important material for realizing colorized display of flat panel display products such as LCD panels, OLEDs and the like. The developability of current color developing materials is a key factor affecting the performance of color photoresists. A commonly used color developing material in a color photoresist is a green phthalocyanine, and because the solubility of the phthalocyanine is good, a dispersant is not required to be additionally added for stabilization, and a polymer is not required to be coated on the periphery of a dye molecule to promote the intermiscibility with an organic system, the developing capability of the phthalocyanine is insufficient, and the residual problem is easy to occur in the process of preparing a color filter by using the phthalocyanine, so that the optical performance of the color filter is seriously influenced.
Disclosure of Invention
In order to solve the problems in the prior art, the application provides a developing material which is strong in developing capability and not easy to remain, an optical filter and a preparation method thereof.
The present application provides a color developing material, the structure of which is represented by formula (1),
wherein R is1To R16At least one of which is selected from-O-Y-R, Y being an alkylene group and R being an amphiphilic group; r1To R16The other groups in (a) are independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, and M is a metal or a metal halide.
In some embodiments, the amphiphilic group is selected from hydroxyl, carboxyl, amino, pyridine, ammonium ion.
In some embodiments, Y is an alkylene group, an alkenylene group, an alkynylene group, or an arylene group having 3 to 20 carbon atoms, or 6 to 48 carbon atoms.
In some embodiments, the arylene group is a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group.
In some embodiments, R1To R16At least one of which is selected from the group consisting of substituents represented by the formula (2), the formula (3) and the formula (4),
wherein Z is alkenylene.
In some embodiments, the formula (1) is asymmetric.
In some embodiments, R1To R16Wherein at least one of the other groups is selected from the group consisting of C3-20 substituted or unsubstituted alkoxy, C6-E24 substituted or unsubstituted aryloxy group, and the remainder being halogen atoms.
In some embodiments, the structure of the chromogenic material is represented by formula (5),
wherein, R is2Or R3Is selected from-O-Y-R, R6Or R7Selected from substituted or unsubstituted aryloxy, R1To R16The other group in (1) is a halogen atom.
The application also provides an optical filter which comprises at least one color development material.
The application also provides a preparation method of the color developing material, which comprises the following steps: dissolving a first reactant represented by a formula (6), a second reactant represented by a formula (7), a third reactant represented by a formula (8), a fourth reactant represented by a formula (9), metal acetate and a catalyst in a solvent under an inert gas atmosphere, heating, refluxing, cooling, eluting and purifying to obtain a chromogenic material; the color developing material comprises a structure shown as a general formula (1),
wherein R is1To R16At least one-O-Y-R in (1), Y is alkylene, and R is an amphiphilic group; r1To R16The other group(s) in (b) is independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, and M is a metal or a metal halide.
Compared with the prior art, the method has the following beneficial effects and advantages:
the application provides a color developing material, which improves the developing capability of phthalocyanine through introducing an amphiphilic group into the molecular structure of the phthalocyanine, and solves the residual problem of the phthalocyanine in the process of preparing a color filter; meanwhile, a substituent with large steric hindrance is introduced to prevent aggregation among molecules, so that the color developing material keeps good solubility and heat resistance, and the optical filter prepared from the color developing material has excellent optical performance and highly fine patterns, and improves the display quality of display products such as LCDs, OLEDs and the like.
Drawings
To more clearly illustrate the exemplary embodiments of the present application or the prior art, the drawings that are needed to be used in the exemplary embodiments are briefly described below. The drawings in the following description are only some embodiments of the present application, and it will be obvious to those skilled in the art that other drawings can be obtained from the drawings without inventive effort.
Fig. 1 is a schematic structural view of a liquid crystal display according to an exemplary embodiment of the present application.
Detailed Description
Detailed description of the inventiondefinitions and explanations of terms are first set forth, followed by exemplary embodiments of the present application to enable those skilled in the art to understand and practice the present application. This application, however, may be embodied in many different forms and should not be construed as limited to the embodiments set forth herein.
The present application provides a color developing material, the structure of which is represented by formula (1),
wherein R is1To R16At least one of which is selected from-O-Y-R, Y being an alkylene group and R being an amphiphilic group; r1To R16The other groups in (a) are independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted aryloxy group.
M is a metal or metal halide, and may be Zn2+、Cu2+、Ni2+、Co2+、Fe2+、AlCl2+Or SiCl2 2+。
The amphiphilic group is selected from hydroxyl, carboxyl, amino, pyridine and ammonium salt. The amphiphilic group refers to a group having both hydrophilic and lipophilic properties. The introduction of the amphiphilic group can improve the coloring capability of the phthalocyanine dye and effectively solve the residue problem of the phthalocyanine dye in the process of preparing the color filter.
Y is an alkylene group having 3 to 20 carbon atoms, an alkenylene group, an alkynylene group, or an arylene group having 6 to 48 carbon atoms. The alkylene group having 3 to 20 carbon atoms may be a linear, branched or cyclic alkylene group having 3 to 20 carbon atoms, such as methylene, ethylene, propylene, etc. The C3-20 alkenylene group may be a C3-20 linear, branched or cyclic alkenylene group, such as vinylene, propenylene, butenylene, and the like. The alkynylene group having 3 to 20 carbon atoms may be a substituted or unsubstituted alkynylene group, such as propynyl or butynyl. The arylene group having 6 to 48 carbon atoms may be a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group. In addition, if the heat resistance of the color developing material is considered to be improved, Y can be phenylene with 6-48 carbon atoms, and in a specific embodiment, -O-Y-R can be a group with a structural formula represented by a formula (2), a formula (3) or a formula (4),
wherein Z is alkenylene.
In addition, the structure of the color developing material may be asymmetric, which means that groups connected to symmetric sites on the molecular structure of the phthalocyanine dye are not all the same. The term "not all of the same means not all of the same or partially the same, specifically, R1、R8、R9、R16Is a first symmetric group, R2、R7、R10And R15Is a second symmetric group, R3、R6、R11And R14Is a third symmetrical group, R4、R5、R12And R13A fourth symmetric group. At least one symmetric group exists in the first symmetric group to the fourth symmetric group, groups connected with any two symmetric sites in the symmetric group are not independent and identical with other symmetric groups, and the independent identity means that any two symmetric sites in one symmetric group are both connected with a group A, and any two symmetric sites in the other symmetric group are both connected with a group B. The asymmetric structure is more favorable for improving the solubility of the chromogenic material. R1To R16At least one of the other groups in (1) is selected from a substituted or unsubstituted alkoxy group having 3 to 20 carbon atoms and a substituted or unsubstituted aryloxy group having 6 to 24 carbon atoms. The aryloxy group may be phenoxy, naphthoxy or biphenyloxy. If the solubility of the chromogenic material is considered, in some embodiments, R1To R16Wherein at least one C6-24 substituted or unsubstituted aryloxy group of the other group can prevent aggregation of color developing material molecules due to steric hindrance of the substituent group. In one embodiment, R1To R16Wherein 1 to 3 of the other functional groups in the group (A) are selected from substituted or unsubstituted phenoxy groups having 6 to 24 carbon atoms, and the substituted or unsubstituted phenoxy groups may be substituents represented by the formula (10),
the structure of the color developing material can also be represented by the general formula (5),
wherein, R is2Or R3Is selected from-O-Y-R, R6Or R7Selected from substituted or unsubstituted aryloxy groups, the remainder being halogen atoms.
There is also provided in another exemplary embodiment of the present application a method of preparing a color developing material, including the steps of: dissolving a first reactant represented by a formula (6), a second reactant represented by a formula (7), a third reactant represented by a formula (8), a fourth reactant represented by a formula (9), metal acetate and a catalyst in a solvent under an inert gas atmosphere, heating for reflux reaction for 7 days at the heating temperature of 140-150 ℃, cooling to room temperature, eluting and purifying to obtain a chromogenic material; the color developing material comprises a structure shown as a general formula (1),
wherein R is1To R16At least one-O-Y-R in (1), Y is alkylene, and R is an amphiphilic group; r1To R16Wherein M is a metal or metal halide, and may be Zn, is independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group2+、Cu2+、Ni2+、Co2+、Fe2+、AlCl2+Or SiCl2 2+。
In the above reaction, the first reactant to the fourth reactant are added according to the structure of the color developing material represented by formula (1), but in other embodiments, 1 to 3 of the first reactant to the fourth reactant may be selected according to the structure of the target color developing material. In the first to fourth reactants represented by the formulae (6) to (9), R is1～R16The structure of the target color developing material is defined. In this reaction, the ratio of the sum of the amounts of the substances of the first to fourth reactants to the amount of the substance of the metal acetate is 4: (0.5-2). In the above production method, the phthalonitrile compounds represented by the formulae (6) to (9) as starting materials may be commercially available or synthesized by a known method. For example, a halogenated phthalonitrile is used to react with the precursor containing the amphiphilic group represented by formula (11).
The following examples are given by way of illustration, but the scope of the present application is not limited to the following examples.
Synthesis example 1, the first reactant is represented by formula (12),
the second reactant is represented by formula (13),
the third reactant is represented by formula (14),
the fourth reactant is represented by formula (15),
dissolving the first reactant, the second reactant, the third reactant and the fourth reactant with the molar weight of 1mol and 0.5mol of metal acetate in 100ml of high boiling point alcohol solvent under nitrogen environment, heating and refluxing for 7 days by using 1, 8-diazabicyclo [5,4,0] dec-7-ene (DBU) as a reaction catalyst, cooling to room temperature after the reaction is finished, passing through a column by using n-hexane/dichloromethane as eluent for purification to obtain the chromogenic material shown in formula (16),
synthesis example 2, the first reactant is represented by formula (12), the second reactant is represented by formula (13), and the third reactant is represented by formula (17),
dissolving 1mol of a first reactant represented by formula (12), 1mol of a second reactant represented by formula (13), 2mol of a third reactant represented by formula (17) and 1mol of a metal acetate in 100ml of a high-boiling-point alcohol solvent under a nitrogen atmosphere, heating and refluxing for 7 days by using 1, 8-diazabicyclo [5,4,0] dec-7-ene (DBU) as a reaction catalyst, cooling to room temperature after the reaction is finished, passing the mixture through a column by using n-hexane/dichloromethane as an eluent, and purifying to obtain a color-developing material represented by formula (18),
synthesis example 3, the first reactant is represented by the formula (14), the second reactant is represented by the formula (19),
the third reactant is represented by formula (20),
dissolving 1mol of the first reactant represented by the formula (14), 1mol of the second reactant represented by the formula (19), 2mol of the third reactant represented by the formula (20) and 1mol of a metal acetate in 100ml of a high-boiling-point alcohol solvent under a nitrogen atmosphere, heating and refluxing the mixture for 7 days by using 1, 8-diazabicyclo [5,4,0] dec-7-ene (DBU) as a reaction catalyst, cooling the mixture to room temperature after the reaction is finished, and purifying the mixture by using n-hexane/dichloromethane as an eluent through a column to obtain the color-developing material represented by the formula (21),
synthesis example 4, the first reactant is represented by the formula (14), the second reactant is represented by the formula (22),
dissolving 2mol of the first reactant represented by the formula (14), 2mol of the second reactant represented by the formula (22) and 0.8mol of metal acetate in 100ml of a high-boiling-point alcohol solvent under a nitrogen atmosphere, heating and refluxing for 7 days by using 1, 8-diazabicyclo [5,4,0] dec-7-ene (DBU) as a reaction catalyst, cooling to room temperature after the reaction is finished, and purifying by column using n-hexane/dichloromethane as an eluent to obtain the color developing material represented by the formula (23),
synthesis example 5, the first reactant is represented by the formula (13),
the second reactant is represented by formula (22),
dissolving 2mol of the first reactant represented by the formula (13), 2mol of the second reactant represented by the formula (22) and 0.8mol of metal acetate in 100ml of a high-boiling-point alcohol solvent under a nitrogen atmosphere, heating and refluxing for 7 days by using 1, 8-diazabicyclo [5,4,0] dec-7-ene (DBU) as a reaction catalyst, cooling to room temperature after the reaction is finished, and purifying by using n-hexane/dichloromethane as an eluent through a column to obtain the color developing material represented by the formula (24),
in Synthesis example 6, the first reactant is represented by the formula (25), the second reactant is represented by the formula (22),
dissolving 2mol of the first reactant represented by the formula (25), 2mol of the second reactant represented by the formula (22) and 0.5mol of metal acetate in 100ml of a high-boiling-point alcohol solvent under a nitrogen atmosphere, heating and refluxing for 7 days by using 1, 8-diazabicyclo [5,4,0] dec-7-ene (DBU) as a reaction catalyst, cooling to room temperature after the reaction is finished, and purifying by column using n-hexane/dichloromethane as an eluent to obtain the color developing material represented by the formula (26),
as another practical mode, the proportion of the number of-O-Y-R in the color developing material can be adjusted by adjusting the ratio of the amount of the added reactant, and the developability, solubility and heat resistance of the color developing material can be adjusted. For example, in synthesis examples 2 and 3, the first reactant is added in a range of 1 to 2 moles and the second reactant is added in a range of 1 to 2 moles with respect to 1 mole of the third reactant; the molar ratio of the first reactant to the second reactant in synthesis examples 4 to 6 may be 1: 3-3: 1, or any ratio therebetween.
Synthesis example 7, the molar ratio of the first reactant represented by formula (14) to the second reactant represented by formula (22) was 3: 1, the coloring material represented by the formula (27) was prepared according to the preparation procedure of Synthesis example 4, in which the amount of the first reactant represented by the formula (14) added was 3mol and the amount of the second reactant represented by the formula (22) added was 1mol,
synthesis example 8, the molar ratio of the first reactant represented by formula (14) to the second reactant represented by formula (22) was 1: 3, the coloring material represented by the formula (28) was prepared according to the preparation procedure in Synthesis example 4, in comparison with the case where the amount of the first reactant represented by the formula (14) was 1mol and the amount of the second reactant represented by the formula (22) was 3mol,
synthesis example 9, 1mol of the first reactant represented by the formula (14), 2mol of the second reactant represented by the formula (19), 1mol of the third reactant represented by the formula (20) and 2mol of a metal acetate were dissolved in 100ml of a high boiling point alcohol solvent, 1, 8-diazabicyclo [5,4,0] dec-7-ene (DBU) was used as a reaction catalyst, and the mixture was heated under reflux for 7 days, cooled to room temperature after the completion of the reaction, and purified by column chromatography using n-hexane/dichloromethane as an eluent to obtain a coloring material represented by the formula (29) or the formula (30),
another exemplary embodiment of the present disclosure also provides an optical filter, in which the color developing material, the binder resin, the photoinitiator, the polymerizable monomer, and the thermal polymerization inhibitor, the foam inhibitor, the leveling agent, and the solvent are mixed to prepare a photoresist solution, the solvent may be Propylene Glycol Methyl Ether Acetate (PGMEA), the binder resin may be an acrylic resin, the photoinitiator may be a benzophenone compound, the polymerizable monomer may be an acrylate of a polyhydric alcohol, and the dispersant is polystyrene-polyacrylic acid diblock copolymer (PS-PAA).
And (3) coating, prebaking, exposing, developing, postbaking, patterning and the like on the prepared photoresist liquid to obtain the color filter. The color filter may have a target pattern depending on the number and arrangement of three colors of red (R), green (G), and blue (B). After the photoresist liquid is irradiated by ultraviolet light, the part which is not irradiated by light is removed during development, and the part which is irradiated by light is reserved, so that the required pattern is formed. In the developing process, the photoresist solution containing the color developing material disclosed by the application and the developing solution react completely and quickly, no residue is generated, and the formed square pattern is high in fineness.
The obtained color filter has a remarkably fine square pattern, and can be applied to the display field of Liquid Crystal Display (LCD) and the like. FIG. 1 is a schematic structural diagram of a Thin Film Transistor-Liquid Crystal Display (TFT-LCD) including the color filter. The liquid crystal display 10 includes a color filter substrate 11 and a thin film transistor array substrate 12 which are oppositely arranged, a pixel electrode 131 and a common electrode 132 are arranged on the opposite inner sides of the two substrates, an alignment film 14 is pasted on one side of the pixel electrode 131 and the common electrode 132, which is far away from the substrates, a liquid crystal layer 15 is further arranged between the color filter substrate 11 and the thin film transistor array substrate 12, the liquid crystal display 10 further includes a backlight module 16, the orientation of liquid crystal molecules of the liquid crystal layer 15 is controlled by applying a driving voltage on the color filter substrate 11 and the thin film transistor array substrate 12, the polarization state of light is changed, and the penetration and blocking of a light path are realized through a polarizing plate (not shown), so that the purpose of display is realized. The color filter includes a black matrix 111 and a color resistance material layer 112 of three colors of red (R), green (G), and blue (B), the arrangement of the three colors of red (R), green (G), and blue (B) is not limited herein, and the arrangement in fig. 1 is only an example. The transmitted light 17 passes through the color resist layer 112 of three colors of red (R), green (G), and blue (B) to show the light of three colors of red (R), green (G), and blue (B), and then the driving voltage is applied to the two substrates to control the orientation of the liquid crystal molecules of the liquid crystal layer 15, so as to control the intensity of the light passing through the liquid crystal molecules, and the liquid crystal display 10 shows a pattern of six colors according to the three-line color principle of light. The color filter substrate 11 of the present application has a fine pattern, and thus the resolution of the LCD is significantly improved.
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 (10)
1. A color developing material characterized in that the structure of the color developing material is represented by formula (1),
wherein R is1To R16At least one of them being selected from the group consisting of-O-Y-R, Y being an alkylene group, RIs an amphiphilic group; r1To R16The other groups in (a) are independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, and M is a metal or a metal halide.
2. The coloring material according to claim 1, wherein the amphiphilic group is selected from the group consisting of hydroxyl group, carboxyl group, amino group, pyridine, ammonium ion.
3. The coloring material according to claim 1, wherein Y is an alkylene group having 3 to 20 carbon atoms, an alkenylene group, an alkynylene group, or an arylene group having 6 to 48 carbon atoms.
4. The coloring material according to claim 3, wherein the arylene group is a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group.
5. The coloring material according to claim 1, wherein R is1To R16At least one of which is selected from the group consisting of substituents represented by the formula (2), the formula (3) and the formula (4),
wherein Z is alkenylene.
6. The coloring material according to claim 1, wherein the formula (1) is asymmetric.
7. The coloring material according to claim 6, wherein R is1To R16Wherein at least one of the other groups is selected from a substituted or unsubstituted alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 24 carbon atoms, and the balance is a halogen atom.
8. The coloring material according to claim 1, wherein the structure of the coloring material is represented by the general formula (5),
wherein, R is2Or R3Is selected from-O-Y-R, R6Or R7Selected from substituted or unsubstituted aryloxy, R1To R16The other group in (1) is a halogen atom.
9. An optical filter comprising at least one color-developing material according to any one of claims 1 to 8.
10. The preparation method of the color developing material is characterized by comprising the following steps of: dissolving a first reactant represented by a formula (6), a second reactant represented by a formula (7), a third reactant represented by a formula (8), a fourth reactant represented by a formula (9), metal acetate and a catalyst in a solvent under an inert gas atmosphere, heating, refluxing, cooling, eluting and purifying to obtain a chromogenic material; the color developing material comprises a structure shown as a general formula (1),
wherein R is1To R16At least one-O-Y-R in (1), Y is alkylene, and R is an amphiphilic group; r1To R16The other group(s) in (b) is independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, and M is a metal or a metal halide.
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