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WO2020228191A1 - Procédé de préparation de colorant et de film optique - Google Patents

Procédé de préparation de colorant et de film optique Download PDF

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Publication number
WO2020228191A1
WO2020228191A1 PCT/CN2019/104468 CN2019104468W WO2020228191A1 WO 2020228191 A1 WO2020228191 A1 WO 2020228191A1 CN 2019104468 W CN2019104468 W CN 2019104468W WO 2020228191 A1 WO2020228191 A1 WO 2020228191A1
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WO
WIPO (PCT)
Prior art keywords
dye
reactant
rhodamine
ranges
alkoxy
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.)
Ceased
Application number
PCT/CN2019/104468
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English (en)
Chinese (zh)
Inventor
查宝
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
Original Assignee
Shenzhen China Star Optoelectronics 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.)
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Publication date
Application filed by Shenzhen China Star Optoelectronics Technology Co Ltd filed Critical Shenzhen China Star Optoelectronics Technology Co Ltd
Publication of WO2020228191A1 publication Critical patent/WO2020228191A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C09B69/109—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing other specific dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics

Definitions

  • the present invention relates to the field of display technology, in particular to a dye preparation method and an optical film.
  • the high color gamut means that the display can display more colorful colors and has a stronger color display ability, thereby effectively avoiding distortion and color blocks in the display process.
  • the color switching of the screen in the display can be more natural, making the level of the screen more distinct, showing more details and closer to the real effect.
  • the improvement of the color gamut is mainly achieved by color film filters of the three primary colors (red, green, and blue); in addition, the color gamut can also be adjusted by adjusting the backlight
  • color film filters of the three primary colors red, green, and blue
  • the color gamut can also be adjusted by adjusting the backlight
  • QD quantum dot
  • the red, green, and blue primary colors are not purified in the process of increasing the color gamut, that is, there are cyan light and yellow-orange light
  • the above two color gamut enhancement methods make the final red, green and blue light not Pure.
  • the color gamut increases, light penetration also decreases, making it difficult to achieve an increase in brightness while increasing the color gamut.
  • rhodamine-based dyes Although the stray light other than RGB is currently absorbed by rhodamine-based materials, rhodamine-based dyes have a shoulder on the left side of the maximum absorption peak, which absorbs part of the blue and green light. Rhodamine-based dyes are easy to produce Agglomeration causes the absorption of the shoulder peak to increase, and the green part directly affects the transmittance, resulting in a decrease in the transmittance.
  • the purpose of the present invention is to provide a dye preparation method and an optical film, which can improve the brightness of the three primary colors while improving the purity of the three primary colors.
  • the present invention provides a dye preparation method, which includes:
  • the second reactant is washed with dichloromethane and methanol, and separated by a chromatographic column to obtain the dye monomer; the volume ratio of the dichloromethane to the methanol is 1:2;
  • the rhodamine dye includes the following chemical structural formula:
  • X - include, but are not limited to, F -, Cl -, Br - , CF 3 SO 3 -, CF 2 HSO 3 - and CFH 2 SO 3 -; wherein 1 ⁇ R 5 and the structure of R 7 ⁇ R 11, R comprises Straight chain alkanes, branched alkanes, alkoxy straight and branched alkanes, chains containing ester groups, F substituted alkane derivatives, conjugated structures connected by alkoxy groups and ester groups, and At least one of the compounds containing a heterocyclic ring; the carbon chain length in the F-substituted alkane derivative group ranges from 1 to 30;
  • R 7 can also include, but is not limited to, -F, -Cl, -Br, -I, and -CN substituent groups;
  • the present invention also provides a method for preparing the dye, which includes:
  • the second reactant is washed with dichloromethane and methanol, and separated by a chromatographic column to obtain the dye monomer.
  • the present invention also provides an optical film, the optical film layer, the material of which includes dye monomers, resins, and photoinitiators; the dye monomers include:
  • the structure of R 6 includes linear alkanes, branched alkanes, linear alkoxy, branched alkanes, chains containing ester groups, F substituted alkane derivatives, through alkoxy and ester groups. At least one of the connected conjugated structure and the compound containing a heterocyclic ring; the carbon chain length in the F-substituted alkane derivative group is in the range of 1-30.
  • the rhodamine dye is added to thionyl chloride to react to obtain a first reaction solution, and the thionyl chloride in the first reaction solution is removed,
  • a first reactant add the first reactant and 4-hydroxy R acrylate to anhydrous tetrahydrofuran to react to obtain a second reaction solution, and remove the anhydrous tetrahydrofuran in the second reaction solution,
  • a second reactant is obtained; the second reactant is washed with dichloromethane and methanol, and separated by a chromatography column to obtain a dye monomer.
  • the stability of the rhodamine dyes after monomerization is stronger, so as to avoid polymerization reaction, reduce the energy of blue absorption and filter light, and improve the purity of the three primary colors. , Improve the brightness.
  • Fig. 1 is a schematic diagram of the structure of the optical film of the present invention.
  • the preparation method of the dye of the present invention includes:
  • the rhodamine dye is added to the thionyl chloride SOCl 2 solvent, and the two are allowed to react for a period of time at a preset temperature to obtain the first reaction solution.
  • the thionyl chloride solvent in the first reaction solution is removed by vacuum distillation to obtain the first reactant. It is understandable that the method of removing the thionyl chloride solvent may be other methods, and is not limited to the vacuum distillation method.
  • the molar amount of the rhodamine dye ranges from 15 mmol to 30 mmol.
  • the capacity range of the thionyl chloride is 20ml-60ml.
  • the molar amount of the 4-hydroxy R acrylate is in the range of 10 mmol-40 mmol.
  • the capacity range of the anhydrous tetrahydrofuran is 50ml-150ml.
  • the reaction temperature of the rhodamine dye and the thionyl chloride ranges from 80°C to 100°C, preferably 90°C.
  • the rhodamine dye includes at least one of rhodamine B, rhodamine 6G, rhodamine 19, rhodamine 101, and rhodamine 110 derivatives, and the chemical structural formula of the rhodamine 6G derivatives is as follows:
  • X- includes but not limited to F-, Cl-, Br-, CF 3 SO 3 -, CF 2 HSO 3 -and CFH 2 SO 3 -; wherein the structures of R 1 ⁇ R 5 and R 7 ⁇ R 11 include Straight chain alkanes, branched alkanes, alkoxy straight and branched alkanes, chains containing ester groups, F substituted alkane derivatives, conjugated structures connected by alkoxy groups and ester groups, and At least one of the compounds containing a heterocyclic ring; the carbon chain length in the F-substituted alkane derivative group ranges from 1 to 30;
  • R 7 may also include, but is not limited to, F, Cl, Br, I and CN substituent groups
  • R 1 to R 5 and R 7 to R 11 can be non-conjugated structures (straight-chain alkanes, or branched alkanes, alkoxy-based straight or branched alkanes, and ester-containing chains. F-substituted alkane derivatives, the carbon chain length can range from 1 to 30, etc.), R 1 to R 5 can also be conjugated structures connected by alkoxy and ester groups or contain hetero Ring compound.
  • the heterocyclic compound may be five- and six-membered heterocyclic, benzoheterocyclic compounds and the like.
  • Five-membered heterocyclic compounds include but are not limited to furan, thiophene, pyrrole, thiazole, imidazole, etc.; six-membered heterocyclic compounds include but are not limited to pyridine, pyrazine, pyrimidine, pyridazine, etc. and condensed ring heterocyclic compounds: indole, quine Phrin, pteridine, acridine, etc.
  • the second reaction liquid is washed with saturated brine, and the second reaction liquid is washed with saturated sodium bicarbonate solution to remove the anhydrous tetrahydrofuran to obtain the second reactant.
  • the structure of R 6 includes linear alkanes, branched alkanes, linear alkoxy, branched alkanes, chains containing ester groups, F substituted alkane derivatives, through alkoxy and ester groups. At least one of the connected conjugated structure and the compound containing a heterocyclic ring; the carbon chain length in the F-substituted alkane derivative group is in the range of 1-30.
  • the second reactant is washed with a detergent of dichloromethane DCM: methanol MeOH and separated by a chromatographic column to obtain a dye monomer, and the dye monomer is a rhodamine dye monomer.
  • the dye monomer includes:
  • the structure of R 6 includes linear alkanes, branched alkanes, linear alkoxy, branched alkanes, chains containing ester groups, F substituted alkane derivatives, through alkoxy and ester groups. At least one of the connected conjugated structure and the compound containing a heterocyclic ring; the carbon chain length in the F-substituted alkane derivative group is in the range of 1-30.
  • the volume ratio of the dichloromethane to the methanol is 1:2.
  • the preparation method of the above dye specifically includes:
  • Rhodamine B Add Rhodamine B to the SOCl 2 solvent of thionyl chloride, and allow the two to react at 90° C. for 6 hours to obtain a first reaction solution; then, the second reaction solution in the first reaction solution is distilled under reduced pressure. The thionyl chloride solvent is removed to obtain the first reactant.
  • the chemical structure of Rhodamine B is as follows:
  • the second reactant is washed with dichloromethane DCM: methanol MeOH detergent, and separated by a chromatographic column to obtain rhodamine B dye monomer.
  • the present invention also provides an optical film, which includes an optical film layer, the material of which includes the above-mentioned dye monomer, resin and photoinitiator; in addition, it also includes a solvent and additives.
  • the manufacturing method of the optical film includes the following steps:
  • the resin mainly uses transparent acrylic resin, which includes dimethylaminoethyl methacrylate, butyl methacrylate, hydroxyethyl methacrylate, cyclohexyl methacrylate, and isooctyl methacrylate. One or more.
  • the photoinitiator can be an acetophenone derivative: ⁇ , ⁇ -diethoxyacetophenone, 2-methyl-2-morpholino-1-(4-methylphenylthio)propane-1-one And one or more of HMPP.
  • the solvent may be one or a mixture of PGMEA (propylene glycol methyl ether acetate), PGME propylene glycol monomethyl ether, and MEA ethanolamine.
  • PGMEA propylene glycol methyl ether acetate
  • PGME propylene glycol monomethyl ether propylene glycol monomethyl ether
  • MEA ethanolamine MEA ethanolamine
  • the additives may be silane coupling agents and the like.
  • the above-mentioned optical film material is coated on the substrate 21, and then exposed to it with an exposure mask (Mask) to cause the above-mentioned optical film material to undergo a crosslinking reaction, and then it is thermally baked After baking, the optical film layer 22 containing rhodamine dye monomers is obtained.
  • the substrate 21 may be one of a polarizer, an overcoat (OC), an organic flat layer (the material is perfluoroalkoxy resin, PFA), and a color film resist.
  • the color gamut is improved, that is, the purity of the three primary colors is improved, and the transmittance is improved.
  • the dye of the present invention is obtained by monomerizing the structure of rhodamine dye, the stability of the rhodamine dye after monomerization is relatively strong, so as to avoid the agglomeration of rhodamine molecules to increase the shoulder peak. Reduce the absorption intensity of blue and green light due to shoulder peaks. While improving the purity of the three primary colors, it can avoid the excessive loss of brightness of the display. Reduce the energy of blue and filter absorption, that is, while improving the purity of the three primary colors. , Improve the brightness.
  • the dye of the present invention is obtained by monomerizing the rhodamine dye structure, it is then mixed with a transparent resin and a photoinitiator, and exposed to crosslinking reaction, thereby making the rhodamine dye monomer Polymerization, this can make the rhodamine dye monomers form a monodisperse structure, avoid the agglomeration of rhodamine molecules to increase the shoulder peak, reduce the absorption intensity of blue and green light due to the shoulder peak, and improve the purity of the three primary colors at the same time, Can avoid excessive loss of brightness of the display.
  • the use of rhodamine dye monomer polymerization can improve the thermal stability of the dye.
  • the rhodamine dye is added to thionyl chloride to react to obtain a first reaction solution, and the thionyl chloride in the first reaction solution is removed,
  • a first reactant add the first reactant and 4-hydroxy R acrylate to anhydrous tetrahydrofuran to react to obtain a second reaction solution, and remove the anhydrous tetrahydrofuran in the second reaction solution,
  • a second reactant is obtained; the second reactant is washed with dichloromethane and methanol, and separated by a chromatography column to obtain a dye monomer.
  • the stability of rhodamine dyes after monomerization is relatively strong, thereby avoiding polymerization reaction, reducing the energy of blue absorption and filtering, and improving the purity of the three primary colors. Improved brightness.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne un procédé de préparation d'un colorant et d'un film optique. Le procédé consiste à : ajouter un colorant à base de rhodamine à du chlorure de thionyle pour une réaction et à éliminer le chlorure de thionyle dans une solution de réaction ; puis à ajouter le réactif et de l'ester R 4-hydroxy d'acide propénoïque à du tétrahydrofuranne anhydre pour une réaction pour obtenir une deuxième solution de réaction ; à éliminer le tétrahydrofuranne anhydre dans la deuxième solution de réaction ; et à laver le réactif avec du dichlorométhane et du méthanol et à réaliser une séparation à l'aide d'une colonne de chromatographie pour obtenir un monomère colorant.
PCT/CN2019/104468 2019-05-14 2019-09-05 Procédé de préparation de colorant et de film optique Ceased WO2020228191A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201910405059.1 2019-05-14
CN201910405059.1A CN110194901A (zh) 2019-05-14 2019-05-14 一种染料的制备方法及光学膜片

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WO2020228191A1 true WO2020228191A1 (fr) 2020-11-19

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Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110194901A (zh) * 2019-05-14 2019-09-03 深圳市华星光电技术有限公司 一种染料的制备方法及光学膜片
CN110407970A (zh) * 2019-07-19 2019-11-05 深圳市华星光电技术有限公司 罗丹明类染料单体低聚合物的制备方法、纯色材料及液晶显示装置
CN110927851A (zh) * 2019-11-13 2020-03-27 Tcl华星光电技术有限公司 纯色膜片及其制备方法、显示装置
CN111077698A (zh) * 2019-12-17 2020-04-28 Tcl华星光电技术有限公司 一种背光模组及液晶显示装置

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WO2001007430A1 (fr) * 1999-07-22 2001-02-01 Nalco Chemical Compant Polymeres fluorescents solubles dans l'eau
CN105073801A (zh) * 2013-02-15 2015-11-18 和光纯药工业株式会社 着色组合物
US20170137628A1 (en) * 2015-11-16 2017-05-18 StoreDot Ltd. Color conversion in lcd displays
CN109116625A (zh) * 2018-09-03 2019-01-01 深圳市华星光电技术有限公司 背光模组及其光学膜片
CN110194901A (zh) * 2019-05-14 2019-09-03 深圳市华星光电技术有限公司 一种染料的制备方法及光学膜片

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CN1226627C (zh) * 2003-11-27 2005-11-09 上海交通大学 一种以罗丹明为母体的荧光探针及制备方法
CN102070734B (zh) * 2009-11-24 2014-04-30 中国科学院化学研究所 一种单个荧光分子标记的聚苯乙烯磺酸盐及其制备方法
CN101921587B (zh) * 2010-07-19 2014-07-02 西安交通大学 一种具有肿瘤细胞增殖抑制活性的荧光探针及其制备方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001007430A1 (fr) * 1999-07-22 2001-02-01 Nalco Chemical Compant Polymeres fluorescents solubles dans l'eau
CN105073801A (zh) * 2013-02-15 2015-11-18 和光纯药工业株式会社 着色组合物
US20170137628A1 (en) * 2015-11-16 2017-05-18 StoreDot Ltd. Color conversion in lcd displays
CN109116625A (zh) * 2018-09-03 2019-01-01 深圳市华星光电技术有限公司 背光模组及其光学膜片
CN110194901A (zh) * 2019-05-14 2019-09-03 深圳市华星光电技术有限公司 一种染料的制备方法及光学膜片

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