CN111334065A - Phthalocyanine dye, optical filter and preparation method thereof - Google Patents

Phthalocyanine dye, optical filter and preparation method thereof Download PDF

Info

Publication number
CN111334065A
CN111334065A CN202010234379.8A CN202010234379A CN111334065A CN 111334065 A CN111334065 A CN 111334065A CN 202010234379 A CN202010234379 A CN 202010234379A CN 111334065 A CN111334065 A CN 111334065A
Authority
CN
China
Prior art keywords
group
phthalocyanine dye
formula
represented
integer
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.)
Pending
Application number
CN202010234379.8A
Other languages
Chinese (zh)
Inventor
艾琳
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
TCL China Star Optoelectronics Technology Co Ltd
TCL Huaxing Photoelectric Technology Co Ltd
Original Assignee
TCL Huaxing Photoelectric Technology Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by TCL Huaxing Photoelectric Technology Co Ltd filed Critical TCL Huaxing Photoelectric Technology Co Ltd
Priority to CN202010234379.8A priority Critical patent/CN111334065A/en
Publication of CN111334065A publication Critical patent/CN111334065A/en
Pending legal-status Critical Current

Links

Images

Classifications

    • 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
    • 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
    • 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
    • G02F1/133516—Methods for their manufacture, e.g. printing, electro-deposition or photolithography

Landscapes

  • Physics & Mathematics (AREA)
  • Nonlinear Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Mathematical Physics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Optical Filters (AREA)

Abstract

The phthalocyanine dye has an asymmetric structure, the aggregation of molecules is prevented by the asymmetric structure, the phthalocyanine dye can be stably dispersed in a photoresist liquid, the saturation of the phthalocyanine dye in a green light area is high, the penetrating performance is good, substituent groups on the asymmetric structure are selected from a group consisting of aryloxy and arylester groups, the heat resistance of the phthalocyanine dye is excellent, the chemical stability of the phthalocyanine dye is high, the requirements of an optical filter manufacturing process are met, the optical performance of a color filter prepared from the phthalocyanine dye is excellent, and the display quality of an LCD is improved.

Description

Phthalocyanine dye, optical filter and preparation method thereof
Technical Field
The application relates to the field of dyes, in particular to a phthalocyanine dye, an optical filter and a preparation method thereof.
Background
Most of traditional photoresist green color developing materials are halogenated phthalocyanine derivatives, but due to the symmetrical structure of the halogenated phthalocyanine derivatives, phthalocyanine derivative molecules are easy to aggregate, so when the halogenated phthalocyanine derivatives are dispersed in a photoresist liquid, the halogenated phthalocyanine derivatives often exist in the form of large-particle aggregates, and the optical performance of a filter prepared from the halogenated phthalocyanine derivatives is seriously influenced due to the heterogeneity of particles.
Disclosure of Invention
In order to solve the problems in the prior art, the present application provides a phthalocyanine dye with an asymmetric structure, an optical filter and a preparation method thereof.
The present application provides a phthalocyanine dye, the structure of which is represented by formula (1),
Figure BDA0002430485780000011
wherein R is1To R16At least one of which is selected from the group consisting of(2) A first group consisting of a first group represented by the formula (I) and a second group represented by the formula (3), and R1To R16Is selected from a second group consisting of a third group represented by formula (4) and a fourth group represented by formula (5), R1To R16The other group(s) in (b) is a halogen atom or a hydrogen atom;
Figure BDA0002430485780000021
wherein m is1Is an integer of 0 to 4, n1Is an integer of 1 to 5, m1+n1＜6；m2Is an integer of 0 to 3, n2Is an integer of 1 to 4, m2+n2＜8；p1And p2Is an integer of 0 to 3; r17、R18、R19、R20Is alkyl, X is oxygen atom or sulfur atom; m is a metal or metal halide.
In some embodiments, the phthalocyanine dye has an odd number of groups selected from the first group and an odd number of groups selected from the second group.
In some embodiments, the phthalocyanine dye comprises a molar ratio of groups of the first group to groups of the second group of 1: 3-3: 1.
in some embodiments, R1To R4One of (1), R5To R8One of (1), R9To R12Is selected from the first group; r13To R16One of them is selected from the second group, and the others are halogen atoms or hydrogen atoms.
In some embodiments, R1To R4One of (1), R5To R8Is selected from the first group, R9To R12One of (1), R13To R16One of them is selected from the second group, and the others are halogen atoms or hydrogen atoms.
In some embodiments, R1To R4Is selected from the first group, R5To R8One of (1), R9To R12One of (1), R13To R16One of them is selected from the second group, and the others are halogen atoms or hydrogen atoms.
In some embodiments, R17、R18、R19、R20Is an alkyl group having 1 to 8 carbon atoms.
In some embodiments, m is1And m2Is 2, n1And n2Is 1, p1And p2Is 1.
The application also provides an optical filter for an LCD display, which comprises at least one phthalocyanine dye.
The application also provides a preparation method of the phthalocyanine dye, which comprises the following steps: dissolving a first compound represented by a formula (10), a second compound represented by a formula (11), a third compound represented by a formula (12), a fourth compound represented by a formula (13) and metal acetate in an alcohol solvent under an inert atmosphere, adding a catalyst, reacting, cooling to room temperature, and purifying to obtain a phthalocyanine dye represented by a formula (1);
wherein R is1To R16Is selected from a first group consisting of a first group represented by formula (2) and a second group represented by formula (3), and R1To R16Is selected from a second group consisting of a third group represented by formula (4) and a fourth group represented by formula (5), R1To R16The other group(s) in (b) is a halogen atom or a hydrogen atom;
Figure BDA0002430485780000031
Figure BDA0002430485780000041
wherein m is1Is an integer of 0 to 4, n1Is an integer of 1 to 5, m1+n1＜6；m2Is an integer of 0 to 3, n2Is an integer of 1 to 4, m2+n2＜8；p1And p2Is an integer of 0 to 3; r17、R18、R19、R20Is alkyl, X is oxygen atom or sulfur atom; m is a metal or metal halide.
Compared with the prior art, the method has the following beneficial effects and advantages:
according to the phthalocyanine dye provided by the application, different large steric hindrance functional groups are introduced to phthalocyanine molecules to construct an asymmetric structure, so that the phthalocyanine dye can be stably dispersed in a photoresist liquid, and the phthalocyanine dye has high saturation in a green light region and good penetrating performance; the functional group with large steric hindrance is selected from a group consisting of aryloxy and arylester, the phthalocyanine dye has good heat resistance and high chemical stability, meets the requirements of the optical filter in the manufacturing process, and the color optical filter prepared by the phthalocyanine dye has excellent optical performance and improves the display quality of an LCD.
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 phthalocyanine dye, the structure of which is represented by formula (1),
Figure BDA0002430485780000051
wherein R is1To R16Is selected from a first group consisting of a first group represented by formula (2) and a second group represented by formula (3), and R1To R16Is selected from a second group consisting of a third group represented by formula (4) and a fourth group represented by formula (5), R1To R16The other group(s) in (b) is a halogen atom;
Figure BDA0002430485780000052
wherein m is1Is an integer of 0 to 4, n1Is an integer of 1 to 5, m1+n1＜6；m2Is an integer of 0 to 3, n2Is an integer of 1 to 4, m2+n2＜8；p1And p2Is an integer of 0 to 3; r17、R18、R19、R20Is alkyl, X is oxygen atom or sulfur atom; m is a metal or metal halide, and may be Zn2+、Cu2+、Ni2+、Co2+、Fe2+、AlCl2+Or SiCl2 2+。
The structure of the phthalocyanine dye simultaneously has the group selected from the first group and the group selected from the second group, so that the molecular structure of the phthalocyanine dye is more three-dimensional, and the dispersibility of the phthalocyanine dye in the photoresist liquid is improved. The combination of the aryloxy group and the arylate group enables the phthalocyanine dye to have more excellent heat resistance and high chemical stability.
In some embodiments, m is1Can be 0, 1 or 2, n1Can be 1 or 2; m is2Can be 0, 1 or 2, n2Can be 1 or 2; p is a radical of1And p2And may be 0 or 1. In a specific embodiment, m1And m2Is 2, n1And n2Is 1, p1And p2Is 1. In a specific embodiment, the structure of the first group may be represented by formula (6), the second group may be represented by formula (7), the third group may be represented by formula (8), and the fourth group may be represented by formula (9),
Figure BDA0002430485780000061
in some embodiments, R17、R18、R19、R20The alkyl group having 1 to 8 carbon atoms is not particularly limited, and examples thereof include: a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms. If solubility of the phthalocyanine dye is considered, R in some embodiments17、R18、R19、R20Is a linear or branched alkyl group having 1 to 5 carbon atoms. In a specific embodiment, the first group may be represented by formula (14), the second group may be represented by formula (15), the third group may be represented by formula (16), and the fourth group may be represented by formula (17),
Figure BDA0002430485780000071
in some embodiments, the phthalocyanine dye has an odd number of groups selected from the first group and an odd number of groups selected from the second group, and the phthalocyanine dye has a higher asymmetry of the molecular structure, can prevent aggregation between molecules of the phthalocyanine dye, and can be stably and uniformly dispersed in the resist liquid.
In some embodiments, the phthalocyanine dye comprises a ratio of groups of the first group to groups of the second group of 1: 3-3: 1, for example, may be 1: 3. 1: 1 or 3: 1.
in some embodiments, R1To R4One of (1), R5To R8One of (1), R9To R12Is selected from the first group; r13To R16One of which is selected from the second group and the remainder being halogen atoms. For example, R may be2Or R3、R6Or R7、R10Or R11Selected from the first group, R14Or R15Is selected from the group consisting ofA second group, the remainder being halogen atoms or hydrogen atoms. As a specific example, the phthalocyanine dye may be,
Figure BDA0002430485780000072
in some embodiments, R1To R4One of (1), R5To R8Is selected from the first group, R9To R12One of (1), R13To R16One of which is selected from the second group and the remainder being halogen atoms. For example, R may be2Or R3、R6Or R7Selected from the first group, R10Or R11、R14Or R15Selected from the second group, and the remainder being halogen atoms or hydrogen atoms. As a specific example, the phthalocyanine dye may be,
Figure BDA0002430485780000081
in some embodiments, R1To R4Is selected from the first group, R5To R8One of (1), R9To R12One of (1), R13To R16One of which is selected from the second group and the remainder being halogen atoms. For example, R may be2Or R3Selected from the first group, R6Or R7、R10Or R11、R14Or R15Selected from the second group, the remainder being halogen atoms or hydrogen atoms. As a specific example, the phthalocyanine dye may be,
Figure BDA0002430485780000082
the halogen atom may be a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
Another exemplary embodiment of the present application also provides a method for preparing the phthalocyanine dye, the method comprising the steps of: dissolving a first compound represented by formula (10), a second compound represented by formula (11), a third compound represented by formula (12), a fourth compound represented by formula (13) and metal acetate in an alcohol solvent with a high boiling point, adding a catalyst 1, 8-diazabicyclo [5,4,0] dec-7-ene (DBU), heating and refluxing for 7 days at the heating temperature of 140-150 ℃, cooling to room temperature after the reaction is finished, and purifying by column chromatography using n-hexane/dichloromethane as an eluent to obtain the phthalocyanine dye represented by formula (1).
Wherein R is1To R16Is selected from a first group consisting of a first group represented by formula (2) and a second group represented by formula (3), and R1To R16Is selected from a second group consisting of a third group represented by formula (4) and a fourth group represented by formula (5), R1To R16The other group in (1) is a halogen atom or a hydrogen atom.
Figure BDA0002430485780000091
Figure BDA0002430485780000101
Wherein m is1Is an integer of 0 to 4, n1Is an integer of 1 to 5, m1+n1＜6；m2Is an integer of 0 to 3, n2Is an integer of 1 to 4, m2+n2＜8；p1And p2Is an integer of 0 to 3; r17、R18、R19、R20Is an alkyl group, and X is an oxygen atom or a sulfur atom. M metal or metal halide, specifically Zn2+、Cu2+、Ni2+、Co2+、Fe2+、AlCl2+Or SiCl2 2+。
In the above reaction, the first to fourth compounds are added according to the structure of the phthalocyanine dye represented by formula (1), but according to the structure of the phthalocyanine dye to be targeted, in other embodimentsIn the formula, 1 to 3 kinds of the first to fourth compounds may be selected. In addition, in the first to fourth compounds represented by formulas (10) to (13), R1～R16The specification is made in accordance with the structure of the phthalocyanine dye to be targeted. In this reaction, the ratio of the sum of the amounts of the substances of the first to fourth compounds 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 (10) to (13) as starting materials may be commercially available or synthesized by a known method. For example by reacting a halogenated phthalonitrile with a precursor comprising a group selected from said first and second groups, which is not described in detail herein.
In a specific embodiment, the first compound may be,
Figure BDA0002430485780000111
the second compound may be a compound of formula (i),
Figure BDA0002430485780000112
the third compound may be a compound of formula (i),
Figure BDA0002430485780000113
the fourth compound may be a compound of formula (i),
Figure BDA0002430485780000114
dissolving 1mol of the first compound, 1mol of the second compound, 1mol of the third compound, 1mol of the fourth compound and 0.5mol of metal acetate in 100ml of high-boiling-point alcohol solvent, adding a catalyst 1, 8-diazabicyclo [5,4,0] dec-7-ene (DBU), heating and refluxing for 7 days, heating to 145 ℃, finishing the reaction, cooling to room temperature, and purifying by using n-hexane/dichloromethane as eluent to obtain phthalocyanine dye,
Figure BDA0002430485780000122
。
in some embodiments, R2、R6、R10、R14Selected from the first group and the second group, the phthalocyanine dye having a structure represented by the formula (18),
Figure BDA0002430485780000121
the preparation method of the phthalocyanine dye represented by the formula (18) comprises the following steps of mixing a first reactant represented by the formula (19) and a second reactant represented by the formula (20) in a molar ratio of 3: 1-1: dissolving 3, 0.5mol of metal acetate in 100ml of high-boiling-point alcohol solvent, adding a catalyst 1, 8-diazabicyclo [5,4,0] dec-7-ene (DBU), heating and refluxing for 7 days at the heating temperature of 140-150 ℃, finishing the reaction, cooling to room temperature, and purifying by using n-hexane/dichloromethane as eluent to obtain the phthalocyanine dye represented by the formula (18).
Figure BDA0002430485780000131
Wherein Q1 is selected from the first group and Q2 is selected from the second group.
In a specific example, the first reactant is added in an amount of 3mol, the second reactant is added in an amount of 1mol, and the phthalocyanine dye prepared has a structural formula represented by formula (21),
Figure BDA0002430485780000132
the equation of the reaction is that,
Figure BDA0002430485780000133
for example, the first reactant may be,
Figure BDA0002430485780000141
the second reactant is a mixture of a first reactant,
Figure BDA0002430485780000142
the phthalocyanine dye prepared is then a dye of,
Figure BDA0002430485780000143
in one embodiment, the first reactant is added in an amount of 2mol, the second reactant is added in an amount of 2mol, the phthalocyanine dye is prepared by the formula (22),
Figure BDA0002430485780000151
for example, the first reactant may be,
Figure BDA0002430485780000152
the second reactant is a mixture of a first reactant,
Figure BDA0002430485780000153
the phthalocyanine dye prepared is then a dye of,
Figure BDA0002430485780000161
in a specific example, the first reactant is added in an amount of 1mol, the second reactant is added in an amount of 3mol, and the phthalocyanine dye prepared has a structural formula represented by formula (23),
Figure BDA0002430485780000162
for example, the first reactant may be,
Figure BDA0002430485780000171
the second reactant is a mixture of a first reactant,
Figure BDA0002430485780000172
the phthalocyanine dye prepared is then a dye of,
Figure BDA0002430485780000173
another exemplary embodiment of the present application also provides an optical filter, wherein the above phthalocyanine dye, 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 the photoresist solution, the solvent may be Propylene Glycol Methyl Ether Acetate (PGMEA), the binder resin is 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. Of course, this is only an example, and the method for manufacturing the color filter is not limited herein, and please refer to the prior art for further detailed description, which is not described herein.
The obtained optical filter has high penetration property and good optical property, and can be used in the field of LCD (Liquid Crystal Display). Fig. 1 is a schematic structural view 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 attached to one side of the pixel electrode 131 and one side of the common electrode 132, which are 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, and the backlight module 16 provides a surface light source to the direction of the liquid crystal layer 15. The liquid crystal molecules of the liquid crystal layer 15 are controlled by applying a driving voltage to the color filter substrate 11 and the thin film transistor array substrate 12 to change the polarization state of light, and the transmission and blocking of light paths are realized by a polarizing plate (not shown), thereby achieving the purpose of display. 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 is because of having higher penetrating nature, for the color filter substrate among the prior art, sees through light 17 and obtains very big reinforcing to the luminousness that makes light increases, thereby promotes the holistic luminance of LCD.
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 phthalocyanine dye characterized in that the structure of the phthalocyanine dye is represented by the formula (1),
Figure FDA0002430485770000011
wherein R is1To R16Is selected from a first group consisting of a first group represented by formula (2) and a second group represented by formula (3), and R1To R16Is selected from a second group consisting of a third group represented by formula (4) and a fourth group represented by formula (5), R1To R16The other group(s) in (b) is a halogen atom or a hydrogen atom;
Figure FDA0002430485770000012
wherein m is1Is an integer of 0 to 4, n1Is an integer of 1 to 5, m1+n1＜6；m2Is an integer of 0 to 3, n2Is an integer of 1 to 4, m2+n2＜8；p1And p2Is an integer of 0 to 3; r17、R18、R19、R20Is alkyl, X is oxygen atom or sulfur atom; m is a metal or metal halide.
2. The phthalocyanine dye according to claim 1, wherein the phthalocyanine dye has an odd number of groups selected from the first group and an odd number of groups selected from the second group.
3. The phthalocyanine dye according to claim 1, wherein the phthalocyanine dye comprises a molar ratio of the groups of the first group to the groups of the second group of from 1: 3 to 3: 1.
4. The phthalocyanine dye according to claim 3, wherein R is1To R4One of (1), R5To R8One of (1), R9To R12Is selected from the first group; r13To R16One of them is selected from the second group, and the others are halogen atoms or hydrogen atoms.
5. The phthalocyanine dye according to claim 3, wherein R is1To R4One of (1), R5To R8Is selected from the first group, R9To R12One of (1), R13To R16One of them is selected from the second group, and the others are halogen atoms or hydrogen atoms.
6. The phthalocyanine dye according to claim 3, wherein R is1To R4Is selected from the first group, R5To R8One of (1), R9To R12One of (1), R13To R16One of them is selected from the second group, and the others are halogen atoms or hydrogen atoms.
7. The phthalocyanine dye according to claim 1, wherein R is17、R18、R19、R20Is an alkyl group having 1 to 8 carbon atoms.
8. The phthalocyanine dye according to claim 1, wherein m is1And m2Is 2, n1And n2Is 1, p1And p2Is 1.
9. An optical filter for LCD displays, comprising at least one phthalocyanine dye according to any one of claims 1 to 8.
10. A method for preparing a phthalocyanine dye, comprising the steps of: dissolving a first compound represented by a formula (10), a second compound represented by a formula (11), a third compound represented by a formula (12), a fourth compound represented by a formula (13) and metal acetate in a solvent under an inert atmosphere, adding a catalyst, reacting, cooling to room temperature, and purifying to obtain a phthalocyanine dye represented by a formula (1);
wherein R is1To R16At least one selected from the group consisting of a first group represented by formula (2) and a table of formula (3)A first group consisting of the second groups shown, and R1To R16Is selected from a second group consisting of a third group represented by formula (4) and a fourth group represented by formula (5), R1To R16The other group(s) in (b) is a halogen atom or a hydrogen atom;
Figure FDA0002430485770000031
wherein m is1Is an integer of 0 to 4, n1Is an integer of 1 to 5, m1+n1＜6；m2Is an integer of 0 to 3, n2Is an integer of 1 to 4, m2+n2＜8；p1And p2Is an integer of 0 to 3; r17、R18、R19、R20Is alkyl, X is oxygen atom or sulfur atom; m is a metal or metal halide.
CN202010234379.8A 2020-03-30 2020-03-30 Phthalocyanine dye, optical filter and preparation method thereof Pending CN111334065A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202010234379.8A CN111334065A (en) 2020-03-30 2020-03-30 Phthalocyanine dye, optical filter and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202010234379.8A CN111334065A (en) 2020-03-30 2020-03-30 Phthalocyanine dye, optical filter and preparation method thereof

Publications (1)

Publication Number Publication Date
CN111334065A true CN111334065A (en) 2020-06-26

Family

ID=71180417

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202010234379.8A Pending CN111334065A (en) 2020-03-30 2020-03-30 Phthalocyanine dye, optical filter and preparation method thereof

Country Status (1)

Country Link
CN (1) CN111334065A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022032757A1 (en) * 2020-08-11 2022-02-17 Tcl华星光电技术有限公司 Three-dimensional dye, method for preparing three-dimensional dye, and photoresist mixture
WO2022141152A1 (en) * 2020-12-28 2022-07-07 Tcl华星光电技术有限公司 Bundled-type dye, preparation method for bundled-type dye, and photoresist mixture

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1356329A (en) * 2001-08-16 2002-07-03 天津青迈信息材料有限公司 Unsymmetric phthalocyanine derivative and its application in optical record medium
CN101083299A (en) * 2007-05-24 2007-12-05 同济大学 Unsymmetrical Unsymmetrical phthalocyanine material and method for making same
CN101373329A (en) * 2007-08-24 2009-02-25 住友化学株式会社 Colored cured composition
CN104861039A (en) * 2015-05-14 2015-08-26 山东大学 Phthalocyanine compound, preparation method and application as single/two-photon fluorescent probe in cancer targeting and mitochondria labeling
CN105017504A (en) * 2015-07-08 2015-11-04 江西理工大学 Phthalocyanine polymer, optical limiting device and preparation method therefor
CN109021606A (en) * 2017-06-12 2018-12-18 三星显示有限公司 Dye composition, the polarizer using the dye composition and the display device using the dye composition
CN110294945A (en) * 2019-05-31 2019-10-01 周峰 Preparation method of blue pigment with nano particle size, photosensitive resin and color filter

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1356329A (en) * 2001-08-16 2002-07-03 天津青迈信息材料有限公司 Unsymmetric phthalocyanine derivative and its application in optical record medium
CN101083299A (en) * 2007-05-24 2007-12-05 同济大学 Unsymmetrical Unsymmetrical phthalocyanine material and method for making same
CN101373329A (en) * 2007-08-24 2009-02-25 住友化学株式会社 Colored cured composition
CN104861039A (en) * 2015-05-14 2015-08-26 山东大学 Phthalocyanine compound, preparation method and application as single/two-photon fluorescent probe in cancer targeting and mitochondria labeling
CN105017504A (en) * 2015-07-08 2015-11-04 江西理工大学 Phthalocyanine polymer, optical limiting device and preparation method therefor
CN109021606A (en) * 2017-06-12 2018-12-18 三星显示有限公司 Dye composition, the polarizer using the dye composition and the display device using the dye composition
CN110294945A (en) * 2019-05-31 2019-10-01 周峰 Preparation method of blue pigment with nano particle size, photosensitive resin and color filter

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022032757A1 (en) * 2020-08-11 2022-02-17 Tcl华星光电技术有限公司 Three-dimensional dye, method for preparing three-dimensional dye, and photoresist mixture
WO2022141152A1 (en) * 2020-12-28 2022-07-07 Tcl华星光电技术有限公司 Bundled-type dye, preparation method for bundled-type dye, and photoresist mixture

Similar Documents

Publication Publication Date Title
JP4465293B2 (en) Color filter and liquid crystal display device including the same
CN111334065A (en) Phthalocyanine dye, optical filter and preparation method thereof
KR101991699B1 (en) Photosensitive resin composition, black pixel defining layer using the same and display device
TWI275832B (en) Colored composition for color filter and a display using the color filters
KR20180094651A (en) Photosensitive resin composition, black pixel defining layer using the same and display device
WO2020228191A1 (en) Preparation method for dye and optical film
TWI399585B (en) Liquid crystal display panel and color filter substrate
TWI766152B (en) Colored curable resin composition, color filter, and display device
JP6728765B2 (en) Resin composition, color filter substrate and display device
JP6260276B2 (en) Color filter and display device
KR102131993B1 (en) Coloring agent compound and coloring composition comprising the same
WO2021184510A1 (en) Preparation method for oligomer organic dye, color film photoresist, and color film optical filter
CN103665919B (en) Highly transmissive yellow dye and synthetic method thereof for liquid crystal display
KR20110070032A (en) Composition of pigment dispersed liquid, colored resin composition, color filter and display device having the same
KR101788088B1 (en) Liquid crystal display
CN111303166A (en) Green color resistance material, liquid crystal display panel and preparation method
CN111303167A (en) Color development material, optical filter and preparation method thereof
KR102422792B1 (en) Compound, photosensitive resin composition including the same, photosensitive resin layer, color filter and display device
KR20180069563A (en) Color filter and liquid crystal display comprising the same
JP6844146B2 (en) Colorants, coloring compositions, colored cured films, display devices, solid-state image sensors, compounds and polymers
KR101623402B1 (en) Yellow color resin composition for color filter and yellow color filter using same
KR102603294B1 (en) Photosensitive resin composition, photosensitive resin layer using the same, color filter and display device
WO2024116819A1 (en) Color filter, and display device
WO2021114409A1 (en) Black photoresist and preparation method therefor, and display panel
TW200931077A (en) Colored composition for color filter

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
RJ01 Rejection of invention patent application after publication

Application publication date: 20200626

RJ01 Rejection of invention patent application after publication