WO2018032967A1 - Photosensibilisateur macromoléculaire de 9-phénylacridine, son procédé de préparation et son utilisation - Google Patents

Photosensibilisateur macromoléculaire de 9-phénylacridine, son procédé de préparation et son utilisation Download PDF

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Publication number
WO2018032967A1
WO2018032967A1 PCT/CN2017/095373 CN2017095373W WO2018032967A1 WO 2018032967 A1 WO2018032967 A1 WO 2018032967A1 CN 2017095373 W CN2017095373 W CN 2017095373W WO 2018032967 A1 WO2018032967 A1 WO 2018032967A1
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integer
phenyl acridine
photosensitizer
group
linear
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PCT/CN2017/095373
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English (en)
Chinese (zh)
Inventor
钱晓春
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常州强力电子新材料股份有限公司
常州强力先端电子材料有限公司
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Priority to KR1020197001977A priority Critical patent/KR102179484B1/ko
Priority to JP2019503540A priority patent/JP6697125B2/ja
Publication of WO2018032967A1 publication Critical patent/WO2018032967A1/fr

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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
    • C08G65/33379—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing nitro group
    • C08G65/33393—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing nitro group heterocyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
    • C08G65/33303—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group
    • C08G65/33317—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group heterocyclic
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light

Definitions

  • the invention belongs to the field of organic chemistry, and particularly relates to a 9-phenyl acridine macromolecular photosensitizer and a preparation method thereof, and the application of the photosensitizer in the field of photocuring.
  • the acridine compound is a macrocyclic conjugated system with a rigid planar structure and excellent fluorescence performance. It is a good fluorescent reagent and can be used as a photoinitiator in a photopolymerization system. It can also be used as a sensitizer to initiate photoinitiation.
  • the agent is photopolymerized.
  • 9-phenyl acridine is a derivative of acridine which belongs to the biphenyl type structure and can emit a photocurable material mainly composed of an unsaturated resin and a monomer material thereof under ultraviolet light, X-ray or light (photocurable coating, Cross-linking curing of inks and photoresists, etc., and stable properties, and good photosensitivity in photocurable materials composed of unsaturated resins and their monomer materials, and thus are widely used in the field of photocuring.
  • a photocurable material mainly composed of an unsaturated resin and a monomer material thereof under ultraviolet light, X-ray or light (photocurable coating, Cross-linking curing of inks and photoresists, etc., and stable properties, and good photosensitivity in photocurable materials composed of unsaturated resins and their monomer materials, and thus are widely used in the field of photocuring.
  • acridine compounds as photosensitizers is known, as disclosed in Chinese Patent Application Nos. CN101525392A, CN102675203A, etc., which disclose the use of different acridine compounds in photosensitive resins.
  • the conventional acridine compounds have disadvantages such as unsatisfactory solubility and poor sensitivity improvement effect when used as a photosensitizer.
  • 9-phenyl acridine is one of the most widely used products in the existing acridine photosensitizers. As a small molecule photosensitizer, it often appears to be difficult to separate from the reactants during use, difficult to recover or not compatible with the system.
  • 9-phenyl acridine has extremely low water solubility, which seriously affects its use as a photosensitizer in the field of photocuring, especially dry film photoresist.
  • the unexposed portion is usually washed away with an alkaline aqueous solution, and 9-phenyl acridine is precipitated and adsorbed on the surface of the circuit board due to its extremely low water solubility, thus not only affecting the use of the dry film, It also reduces the precision of the product, so it is necessary to increase the surface cleaning process of the board, which leads to cumbersome process and greatly increased cost.
  • the present invention is directed to a 9-phenyl acridine macromolecular photosensitizer.
  • the photosensitizer of the invention has good compatibility when applied to a photocuring system, has good effect on sensitivity improvement, and has excellent resolution and adhesion, and high water solubility (easy to be used). Washed off).
  • the 9-phenyl acridine macromolecular photosensitizer of the present invention comprises at least one of the compounds having a structure represented by the formula (I):
  • R 1 represents a C 1 -C 60 linear or branched m+n valent alkyl group, wherein -CH 2 - may be optionally substituted with oxygen, sulfur or 1,4-phenylene;
  • A each independently represents -[(CHR 4 ) x -O] y -, wherein R 4 each independently represents hydrogen, methyl or ethyl, x is an integer from 1 to 10, and y is an integer from 1 to 20;
  • R 2 represents a C 1 -C 20 linear or branched alkylene group, wherein -CH 2 - may be optionally substituted by oxygen, sulfur or phenylene;
  • R 3 represents hydrogen or a substituent
  • n represents an integer of 1-20.
  • R 1 represents a C 1 -C 20 linear or branched m+n valent alkyl group, wherein -CH 2 - may be optionally substituted by oxygen or 1,4-phenylene, with the conditions It is not directly connected between the two oxygen.
  • R 1 is selected from the group consisting of the following groups:
  • A represents -[(CHR 4 ) x -O] y - wherein R 4 each independently represents hydrogen, methyl or ethyl, x is an integer from 1 to 10, and y is an integer from 1 to 20. -[(CHR 4 ) x -O] The terminal oxygen atom of the y - group is bonded to R 1 .
  • A is selected from the group consisting of:
  • R 2 represents a C 1 -C 8 linear or branched alkylene group, wherein -CH 2 - may be optionally substituted by oxygen or 1,4-phenylene, provided that two oxygens Not directly connected.
  • R 2 is selected from the group consisting of:
  • R 3 is selected from H, CH 3 , NO 2 , or a halogen (such as F, Cl, Br).
  • n represents an integer from 1 to 8
  • the sum of m and n is an integer from 2 to 8.
  • the present invention also relates to a method for preparing the above-mentioned 9-phenyl acridine macromolecular photosensitizer, comprising the following steps:
  • intermediate a and starting material c are reacted in a solvent containing an acid binding agent to obtain intermediate b;
  • intermediate b and starting material d undergo transesterification under the action of a catalyst to obtain a product
  • R 5 represents a C 1 -C 8 linear or branched alkyl group.
  • the photosensitizer of the present invention is an improvement and optimization of the structure of existing compounds.
  • the synthesis involved in the preparation method involves acridine structure construction, esterification, transesterification, etc., all of which are conventional processes in the field of organic chemistry.
  • specific process parameters are readily ascertainable to those skilled in the art. For example, reference is made to the content described in the Chinese patent CN101525392A, which is incorporated herein in its entirety by reference.
  • the catalyst is a composite catalyst of zinc chloride and 85% phosphoric acid.
  • the reaction temperature varies slightly depending on the type of the raw material, and is usually 150-220 ° C, and the reaction time is 4-8 h.
  • R 5 in the structure of the starting material c represents a C 1 -C 4 linear or branched alkyl group, particularly CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 .
  • the type of the solvent to be used is not particularly limited as long as it can dissolve the reaction raw material and has no adverse effect on the reaction, and examples thereof include acetone, acetonitrile, methanol, ethanol, and N,N-dimethylformamide.
  • the acid binding agent may be sodium carbonate, sodium hydroxide, potassium carbonate, sodium methoxide, pyridine, triethylamine or the like.
  • the reaction temperature is 40-100 ° C, and the reaction time is usually 4-18 h.
  • the transesterification reaction is carried out in a solvent.
  • the type of the solvent is not particularly limited as long as it can dissolve the reaction raw material and has no adverse effect on the reaction, for example, toluene, xylene, benzene, cyclohexane or the like.
  • the catalyst may be one of sodium hydroxide, lithium hydroxide, potassium hydroxide, sodium methoxide, methanesulfonic acid, p-toluenesulfonic acid, sulfuric acid, hypophosphorous acid or a combination of two or more thereof.
  • the amount of the catalyst used is preferably from 5 ⁇ to 15 ⁇ based on the total mass of the reaction raw materials.
  • the reaction temperature is usually from 70 to 130 °C.
  • the reaction time is usually from 1 to 8 hours.
  • the 9-phenyl acridine macromolecular photosensitizer of the invention has excellent water-solubility and is particularly suitable for use as a photosensitizer in a photocuring system, and has excellent effect on sensitivity improvement, and the prepared film has good resolution. And adhesion. Accordingly, the present invention also relates to the use of the 9-phenyl acridine macromolecular photosensitizer in a photocurable composition, the photoinitiator used in the photocurable composition preferably being photogenerated by photoacid generator, photoproduction Alkaline agent and free radical photoinitiator.
  • the macromolecularization of the photosensitive group limits the migration of the photosensitive group, thereby preventing the yellowing and aging of the coating;
  • the methanol produced by the reaction is added, and toluene is added in a timely manner until no methanol is distilled off, and the filtrate is filtered while being vacuumed, and the obtained filtrate is distilled under reduced pressure until the residue of toluene is less than 5000 ppm, and 304.4 g of a pale yellow viscous substance is obtained, that is, product 1 .
  • the product 3-9 having the following structure was synthesized by the method of Example 1 or 2.
  • the application properties of the photosensitizer of the present invention were evaluated by formulating an exemplary photocurable composition (i.e., a photosensitive resin composition).
  • the photosensitive resin composition having the composition shown in Table 1 and propylene glycol monoethyl ether acetate were thoroughly stirred and mixed, and coated on the surface of a 19 ⁇ m-thick polyethylene terephthalate film as a support using a rod.
  • the film was uniformly coated, and then dried in a dryer at 95 ° C for 4 minutes to form a photosensitive resin layer having a thickness of 40 ⁇ m.
  • a 23 ⁇ m-thick polyethylene film which is a protective layer is bonded to the surface of the photosensitive resin layer on which the polyethylene terephthalate film is not laminated, to obtain a photosensitive resin laminate.
  • a ketone laminate processed by a jet washing and polishing machine at a spray pressure of 0.20 MPa was used as a substrate for sensitivity and resolution evaluation.
  • the surface was flattened, and the laminate was laminated to a ketone laminate preheated to 60 ° C by a hot roll laminator at a roll temperature of 105 ° C.
  • the pressure was 0.35 MPa and the lamination speed was 1.5 m/min.
  • the exposure was performed by an exposure amount of a stepwise exposure level of 8 which was evaluated by the following sensitivity using a hray type direct drawing exposure apparatus (Digital Light Processing).
  • the photosensitive resin composition having the composition shown in Table 1 was sufficiently stirred and mixed, and uniformly applied onto the surface of a 19 ⁇ m-thick polyethylene terephthalate film as a support using a bar coater. It was dried in a dryer at 95 ° C for 4 minutes to form a photosensitive resin layer. Thereafter, the coated surface was visually observed and classified as follows:
  • the laminated substrate was exposed to light for 15 min using a 21-stage stage exposure meter manufactured by Stouffer, which has a 21 degree brightness change from transparent to black, to evaluate its sensitivity. After the exposure, the development was performed twice as long as the minimum development time, and the exposure was performed according to the exposure amount of the staged exposure level of 8 which was completely left by the resist film, and was classified as follows:
  • the exposure amount is 20 mJ/cm 2 or less
  • the exposure amount is 20 mJ/cm 2 -50 mJ/cm 2 (excluding the end value);
  • the exposure amount is 50 mJ/cm 2 or more.
  • the laminated substrate was exposed for 15 minutes by a line pattern mask having a ratio of the exposed portion and the unexposed portion having a width of 1:1, and then developed with twice the minimum development time to form a cured resist line normally.
  • the minimum mask line width is used as the resolution value. Perform the following classification:
  • the resolution value is 30 ⁇ m or less
  • the resolution value is 30 ⁇ m-50 ⁇ m (excluding the end value);
  • the resolution value is 50 ⁇ m or more.
  • the laminated substrate was exposed for 15 minutes by a line pattern mask having a ratio of the exposed portion and the unexposed portion having a width of 1:100, and then developed with twice the minimum development time to form a cured resist line normally.
  • the minimum mask line width is used as the adhesion value. Perform the following classification:
  • the adhesion value is 30 ⁇ m or less
  • ⁇ : adhesion value is 30 ⁇ m-50 ⁇ m (excluding end value);
  • the adhesion value is 50 ⁇ m or more.
  • the composition using the 9-phenyl acridine type photosensitizer of the present invention has good compatibility with the other components being the same.
  • the sensitivity is high and exhibits good resolution and adhesion, and the water solubility is good, which is superior to Comparative Example 1-2 using the existing photosensitizer.
  • Comparative Example 3 the compatibility, sensitivity, resolution, adhesion and water solubility of the composition were far lower than those of the 9-phenyl group using the present invention in the case of containing only the TPS photoacid generator.
  • a composition of an acridine photosensitizer (Schemes 1-5). Comparative Example 4 shows that the composition does not cure at all in the absence of TPS and the photosensitizer.
  • a photosensitive resin composition as formulated in Table 4 was prepared.
  • the sensitivity was evaluated by referring to the above evaluation method, and the evaluation results are shown in Table 6.
  • the photosensitizer of the present invention exhibits excellent application performance in the field of photocuring and has broad application prospects.
  • the photosensitizer of the present invention is not limited to the application fields indicated by the above formula, and all the photosensitizers of the present invention are used in all of the photocurable coatings, inks, and photoresists, and are all within the scope of this patent.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Materials For Photolithography (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne un photosensibilisateur macromoléculaire de 9-phénylacridine, son procédé de préparation et son utilisation. Le photosensibilisateur macromoléculaire de 9-phénylacridine comprend au moins l'un des composés ayant une structure telle que représentée dans la formule (I), dans laquelle R 1 est un groupe alkyle C 1 -C 60 linéaire ou ramifié ayant une valence de m + n, dans laquelle a-CH 2 - de celui-ci peut être éventuellement substitué par de l'oxygène, du soufre ou du 1,4-phénylène; chaque A représente indépendamment -[(CHR 4 ) x -O] y -, où chaque R 4 représentant indépendamment l'hydrogène, un groupe méthyle, ou un groupe éthyle, x est un nombre entier de 1 à 10, et y est un nombre entier de 1 à 20; R 2 représente un groupe alkylène linéaire ou ramifié en C 1 -C 20 , dans laquelle a-CH 2 de celui-ci peut être éventuellement substitué par de l'oxygène, le soufre ou un phénylène; R 3 représente l'hydrogène ou un groupe substituant; m représente un nombre entier de 0 à 20, et n représente un nombre entier de 1 à 20. Lorsqu'il est utilisé dans un système de photopolymérisation, le photosensibilisateur présente une bonne compatibilité et un bon effet d'amélioration de photosensibilité, et un film préparé à partir de celui-ci présente une excellente résolution, une excellente adhérence et une solubilité élevée dans l'eau.
PCT/CN2017/095373 2016-08-16 2017-08-01 Photosensibilisateur macromoléculaire de 9-phénylacridine, son procédé de préparation et son utilisation WO2018032967A1 (fr)

Priority Applications (2)

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KR1020197001977A KR102179484B1 (ko) 2016-08-16 2017-08-01 9-페닐아크리딘 고분자 감광제 및 이의 제조 방법과 용도
JP2019503540A JP6697125B2 (ja) 2016-08-16 2017-08-01 ９−フェニルアクリジン大分子類光増感剤及びその製造方法、ならびに使用

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CN201610673715.2 2016-08-16
CN201610673715.2A CN107765510B (zh) 2016-08-16 2016-08-16 一种9-苯基吖啶大分子类光敏剂及其制备方法和应用

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CN112835261B (zh) 2019-11-25 2022-06-07 常州强力电子新材料股份有限公司 一种eo/po改性9-苯基吖啶类光敏剂及其应用

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