WO2018062652A1 - Composition de résine photosensible, film durci formé de là, et dispositif électronique ayant le film durci - Google Patents

Composition de résine photosensible, film durci formé de là, et dispositif électronique ayant le film durci Download PDF

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Publication number
WO2018062652A1
WO2018062652A1 PCT/KR2017/003499 KR2017003499W WO2018062652A1 WO 2018062652 A1 WO2018062652 A1 WO 2018062652A1 KR 2017003499 W KR2017003499 W KR 2017003499W WO 2018062652 A1 WO2018062652 A1 WO 2018062652A1
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Prior art keywords
group
substituted
unsubstituted
resin composition
photosensitive resin
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PCT/KR2017/003499
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English (en)
Korean (ko)
Inventor
백택진
김태수
박종희
신동주
안치원
유홍정
Original Assignee
삼성에스디아이 주식회사
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Priority to CN201780059584.1A priority Critical patent/CN109791360B/zh
Priority to JP2019516137A priority patent/JP6826193B2/ja
Publication of WO2018062652A1 publication Critical patent/WO2018062652A1/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
    • 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
    • G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents
    • 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
    • G03F7/022—Quinonediazides
    • 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
    • G03F7/075—Silicon-containing compounds
    • 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
    • G03F7/16—Coating processes; Apparatus therefor
    • 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
    • G03F7/16—Coating processes; Apparatus therefor
    • G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking
    • 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
    • G03F7/20—Exposure; Apparatus therefor
    • 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
    • G03F7/70—Microphotolithographic exposure; Apparatus therefor
    • G03F7/708—Construction of apparatus, e.g. environment aspects, hygiene aspects or materials
    • G03F7/7095—Materials, e.g. materials for housing, stage or other support having particular properties, e.g. weight, strength, conductivity, thermal expansion coefficient
    • G03F7/70958—Optical materials or coatings, e.g. with particular transmittance, reflectance or anti-reflection properties

Definitions

  • An electronic device having a photosensitive resin composition, a cured film formed therefrom, and the cured film
  • the present substrate relates to a photosensitive resin composition, a cured film formed therefrom, and an electronic device including the cured film.
  • the aperture ratio of the display device In order to achieve more accurate and higher resolution in liquid crystal displays and organic EL displays, the aperture ratio of the display device must be increased. To this end, a transparent flattening film is provided as a protective film on the TFT substrate to overlap the C data line and the pixel electrode, thereby increasing the high aperture ratio. There is a way to make this possible.
  • a material for forming the organic insulating film for the TFT substrate As a material for forming the organic insulating film for the TFT substrate, a material having high heat resistance, high transparency, high temperature crack resistance, low dielectric constant, chemical resistance, and the like is required, and to secure the conduction between the TFT substrate electrode and the IT0 electrode. It is necessary to form a hole pattern on the order of 50 to several mils.
  • the material which combined phenolic resin and a numone diazide compound, or the photosensitive resin composition which combined an acryl-type resin and a numone diazide compound has been mainly used.
  • these materials are not rapidly deteriorated at a high temperature of 2 (xrc or higher, but are gradually decomposed at 230 ° C or higher, and a problem of deterioration in film thickness or cracking occurs, or transparent treatment due to high temperature treatment of the substrate.
  • the membrane is colored and the transmittance is lowered.
  • an organic EL element cracks and decomposition products generated from the above materials are not optimal materials for use because they adversely affect the luminous efficiency and lifetime of the organic EL element.
  • the acrylic material imparted heat resistance may cause a crack phenomenon at 300 ° C or more, otherwise the dielectric constant is generally high. Therefore, the parasitic capacitance caused by the insulating film is increased due to the high dielectric constant, which causes a problem in the quality of the image quality due to the increased power consumption or the delay of the liquid crystal element drive signal.
  • the capacity can be reduced by increasing the film thickness, but it is generally difficult to form a uniform thick film, and the amount of material used is not preferable.
  • silsesquioxane is known as a high heat resistant and high transparency material.
  • the photosensitive composition which consists of an acryl-type copolymer and the quinonediazide compound which copolymerized the silsesquioxane compound which provided the acryl group to specific silsesquioxane, the unsaturated compound containing unsaturated carboxylic acid and an epoxy group, and an olefinic unsaturated compound. And the like have been proposed.
  • these compounds also have a high thermal content of organic compounds and decompose after high temperature curing at 250 ° C.
  • the system which combined the quinonediazide compound in order to give positive photosensitive property to a siloxane polymer The material which combined the siloxane polymer and quinonediazide compound which have a phenolic hydroxyl group at the terminal, and the phenolic hydroxyl group by cyclic heat addition reaction, Materials in which a siloxane polymer to which a carboxyl group or the like is added and a quinonediazide compound are combined are known.
  • these materials contain large amounts of quinonediazide compounds, or because phenolic hydroxyl groups are present in the siloxane polymer, This coating film tends to occur whitening or coloring during heat curing, in the above 300 ° C acrid high temperatures can cause the cracking and thus can not be utilized permeability 'and due to the decrease as a transparent material according to.
  • these materials have a problem of low sensitivity at the time of pattern formation because of their low transparency.
  • thermosetting When the photosensitive composition material which consists only of polysiloxane and a quinone diazide compound is thermoset, crosslinking and high molecular weight generate
  • the film is melted by the low viscosity of the film by high temperature, and the patterns such as holes and lines obtained after development flow. As a result, a crack does not occur, but a "pattern" deterioration occurs in which the resolution decreases, which must be prevented.
  • insoluble polysiloxane a combination of the insoluble polysiloxane, the soluble polysiloxane system, and the quinone diazide compound is combined with the developer, and during heat curing, a pattern such as a hole or a line obtained after development collapses, resulting in a "pattern sagging" that results in a decrease in resolution.
  • a photosensitive composition which prevents is proposed.
  • insoluble polysiloxane when used in the developing solution, it melts after development, but causes a development pattern defect to occur due to re-adhesion of residues or difficult-to-melt materials that start to melt.
  • the photosensitive material is low in sensitivity and high reaction energy is required.
  • the residual film ratio is also not divided, resulting in a large loss of material.
  • cracks margin is improved to provide a photosensitive resin composition which is easy to adjust the thickness.
  • Another embodiment is to provide a cured film obtained by curing the photosensitive resin composition.
  • Another embodiment is to provide an electronic device including the cured film.
  • TMAH tetramethylammonium hydroxide
  • X 1 is a C1 to C6 alkoxy group, a hydroxy group, a halogen, a carboxyl group, or any combination thereof 0 igo,
  • a 0 ⁇ a ⁇ 4
  • R 1 is hydrogen, C1 to C10 alkyl group, C2 to C10 alkenyl group, C6 to C16 aryl group, or a combination thereof
  • X 1 is C1 to C6 alkoxy group, hydroxy group, halogen, or a combination thereof May be a combination.
  • R 1 is a methyl group or a phenyl group, a may be 1.
  • the polysiloxane polymer (A) is a silane compound represented by the following formula (2) It may be further included hydrolyzed and condensation.
  • Y 1 is a single bond, oxygen, substituted or unsubstituted C1 to C20 alkylene group, substituted or unsubstituted C3 to C30 cycloalkalene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C2 to A C30 heteroarylene group, a substituted or unsubstituted C2 to C30 alkenylene group, a substituted or unsubstituted C2 to C20 alkynylene group, or a combination thereof,
  • X 2 and X 3 are each independently a C1 to C6 alkoxy group, a hydroxy group, a halogen, a carboxyl group, or a combination thereof.
  • Y 1 may be a C1 to C10 alkylene group, a C3 to C10 cycloalkylene group, a C6 to C12 arylene group, or a combination thereof, and X 2 and X 3 may be a C1 to C6 alkoxy group.
  • the film after prebaking of the photosensitive resin composition may be insoluble in a 2.38 wt% TMAH aqueous solution and the dissolution rate in the 5 wt% TMAH aqueous solution may be 50 A / sec or less.
  • the polysiloxane polymer (A) is prepared by hydrolyzing and condensing the silane compound represented by Formula 1 to 80 mol% to 97 mol3 ⁇ 4> and 3 to 20 mol% of the silane compound represented by Formula 2 together. can do.
  • At least 70% of the total silicon atoms of the polysiloxane polymer (A) may be substituted by phenyl groups.
  • the photosensitive resin composition may further include (C) an additive capable of generating an acid or a base with heat or light, (D) a quinonediazide compound, or a combination thereof.
  • the refractive index of the photosensitive resin composition may be at least 1.50.
  • Another embodiment provides a cured film prepared by curing the photosensitive resin composition.
  • the cured film may have a light transmittance of 98% or more at a 400 nm wavelength.
  • Another embodiment provides an electronic device including the cured film.
  • the photosensitive resin composition according to an embodiment may have excellent chemical resistance, have high light transmittance and crack resistance after high silver curing, and may provide a cured film having an improved crack margin.
  • the cured film may be usefully used for manufacturing a planarization film for a thin film transistor (TF) substrate, an interlayer insulating film of a semiconductor device, and the like.
  • TF thin film transistor
  • 'substituted' means that a hydrogen atom in a compound is a halogen atom (F, Br, C1, or 1), a hydroxyl group, an alkoxy group, a nitro group, a cyano group, an amino group, an azido group, an amino group Dino group, hydrazino group, hydrazono group, carbonyl group, carbamyl group, thiol group, ester group, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, C1 to C20 alkyl group, C2 to C20 alkenyl group, C2 C20 to C20 alkynyl group, C6 to C30 aryl group, C7 to C30 arylalkyl group, C1 to C30 alkoxy group, C1 to C20 heteroalkyl group, C3 to C20 heteroarylalkyl group, C3 to C30 cycloalkyl group, C
  • hetero means containing at least one hetero atom selected from N, 0, S and P.
  • 'combination' means a combination or copolymerization.
  • the photosensitive resin composition according to one embodiment is formed by (A) hydrolyzing and condensing at least one silane compound represented by Formula 1 below, and a polysiloxane polymer in which at least 65% of all silicon atoms are substituted by phenyl groups And (B) a solvent, wherein the membrane after prebaking is insoluble in a 2.38 wt% tetramethylammonium hydroxide (TMAH) water ' solution and the dissolution rate in a 5 wt% TMAH aqueous solution is 100 A / sec or less:
  • TMAH tetramethylammonium hydroxide
  • X 1 is a C1 to C6 alkoxy group, a hydroxy group, a halogen, a carboxyl group, or a combination thereof,
  • n 0 ⁇ n ⁇ 4.
  • the photosensitive resin composition according to the embodiment includes a polysiloxane polymer prepared by hydrolyzing and condensing at least one silane compound represented by Chemical Formula 1, thereby having excellent chemical resistance, and having a high tangerine index having a refractive index of 1.5 or more. It provides a resin composition. Accordingly, the photosensitive resin composition according to the embodiment has a high light transmittance at high temperature curing, the crack margin is improved to exhibit an easy thickness control of the insulating film.
  • R 1 of Formula 1 may be hydrogen, C1 to C10 alkyl group, C2 to C10 alkenyl group, C6 to C16 aryl group, or a combination thereof, X 1 is C1 to C6 alkoxy group, hydroxy group, halogen , Or a combination thereof, and n in Formula 1 may be 0 or 1.
  • R 1 is a methyl group or a phenyl group
  • a may be 1.
  • the polysiloxane polymer (A) according to the embodiment may further be hydrolyzed and condensation-polymerized further comprising a silane compound represented by the following formula (2):
  • Y 1 is a single bond, oxygen, substituted or unsubstituted C1 to C20 alkylene group, substituted or unsubstituted C3 to C30 cycloalkylene group substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C2 to C30 hetero
  • X 2 and X 3 are each independently a C1 to C6 alkoxy group, a hydroxy group, a halogen, a carboxyl group, or a combination thereof.
  • Y 1 may be C1 to C10 alkylene group, C3 to C10 cycloalkylene group, C6 to C12 arylene group, or a combination thereof
  • X 2 and X 3 may be C1 to C6 alkoxy. It may be a flag.
  • the photosensitive resin composition is hydrolyzed and condensed at least one type represented by the formula (1) and 80 mol% to 97 mol% of the silane compound, and 3 mol% to 20 mol% of the silane compound represented by Chemical Formula 2 It can be prepared by reaction.
  • the photosensitive resin composition has a refractive index of 1.50 or more, for example, 1.51 or more, for example, 1.52 or more, 1.53 or more, for example, 1.54 or more, for example, 1.55 or more.
  • the photosensitive resin composition according to the embodiment has a high refractive index of 1.50 or more, crack margin is improved to control the thickness of the insulating film. It shows an easy effect.
  • the molecular weight of the polysiloxane polymer (A) formed by hydrolysis and polycondensation has a weight average molecular weight of 1,000 to 500,000 in terms of polystyrene standard measured by Gel Permeation Chromatography (GPC), for example 1,000 To 100,000, for example, 1,000 to 50,000, for example, 1,000 to 30,000, for example, 1,000 to 20,000, for example, 1,000 to 15,000, for example, 1,000 to 10,000, for example 1,000 to 8,000, for example, 1,000 to 6,000, for example, 1,000 to 5,000, for example, 2,000 to 5,000.
  • GPC Gel Permeation Chromatography
  • the weight average molecular weight of the compound is ⁇ , ⁇ or more, it is possible to implement the desired thickness of the cured film without causing cracks on the surface during curing.
  • the weight average molecular weight is 500,000 or less, it is possible to improve the surface planarity while maintaining the viscosity required for coating.
  • the polysiloxane polymer (A) is a compound in which the membrane after prebaking is insoluble in an aqueous 2.38 wt% TMAH solution and has a dissolution rate of 100 A / sec or less in a 5 wt% TMAH aqueous solution.
  • the polysiloxane polymer (A) is a compound in which the film after prebaking is insoluble in a 2.38 wt% TMAH aqueous solution and has a dissolution rate of 50 A / sec or less in a 5 wt% aqueous TMAH solution.
  • the cured film obtained by curing the composition has a crack free thickness margin of 3.0 or more, for example, 3.2 m or more.
  • the cured film obtained by hardening the said photosensitive resin composition is very high crack resistance in silver.
  • Thickness change rate (w (film thickness after chemical resistance evaluation-film thickness before chemical resistance evaluation) / film thickness before chemical resistance evaluation x ioo
  • the content of phenyl groups substituted for all silicon atoms in the polysiloxane copolymer, or the membrane prepared from the composition comprising the copolymer does not meet the above dissolution rate range for TMAH.
  • the cured film cured from such a composition does not have the above crack resistance and chemical resistance.
  • the content of a phenyl group substituted in the polysiloxane polymer (A) is at least 65%, for example at least 70%, based on the number of all Si atoms.
  • the photosensitive resin composition comprising the polysiloxane polymer substituted with the phenyl group of the above content can significantly reduce the crack incidence upon curing at high temperature. If the content of phenyl groups in the polysiloxane polymer (A) is less than 65%, for example less than 60%, for example less than 55%, based on the number of all Si atoms, the photosensitive resin composition prepared therefrom is cured at high temperatures. The incidence of stacks may increase.
  • the curable film may be used as a protective film or an insulating film of a display display device.
  • the conventional positive photosensitive resin composition is low in refractive index, and it became a cause which lowered the efficiency and thermal stability of an electronic device, for example, a 0LED light emitting element.
  • the photosensitive resin composition includes a polysiloxane polymer formed by hydrolysis and polycondensation of a silane compound represented by Chemical Formula 1 and / or Chemical Formula 2 to form a surface protective film and an interlayer insulating film of a display device by increasing the refractive index. It can be usefully used.
  • the photosensitive resin composition according to one embodiment contains a solvent (B).
  • the solvent which can be used Preferably the compound which has an alcoholic hydroxyl group, and / or the cyclic compound which has a carbonyl group is used.
  • the silane compound is uniformly dissolved to form a film after application of the composition. High transparency can be achieved without whitening of the temporal membrane.
  • the compound having an alcoholic hydroxyl group can be preferably used for a boiling point of 110 ° C to 250 ° C under atmospheric pressure compound. If the boiling point is higher than 25CTC, the amount of remaining solvent in the film increases, and the film shrinks during curing, thereby making it impossible to obtain good flatness. If the boiling point is lower than 110 ° C, the coating film becomes too dry and the film surface becomes rough, resulting in poor coating properties.
  • the compound having an alcoholic hydroxyl group examples include ace, 3-hydroxy-3-methyl-2-butanone, 4-hydroxy-3-methyl-2—butanone and 5-hydroxy-2-pentanone. , 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), ethyl lactate, butyl lactate, propylene glycol mono methyl ether, propylene glycol mono ethyl ether, propylene glycol mono n-propyl ether, propylene glycol mono n-butyl ether, propylene glycol mono t-butyl ether, 3-methoxy-1-butanol, 3-methyl-3- methoxy-1-butanol, and the like.
  • diacetone alcohol is particularly preferably used.
  • a cyclic compound having a carbonyl group preferably may be under atmospheric pressure boiling point of the phosphorus compound to 150 ° C 25CTC. If the boiling point is higher than 250 ° C., the amount of residual solvent in the film increases, the film shrinkage during curing increases, and good elasticity cannot be obtained. If the boiling point is lower than 15 CTC, the coating film properties become poor due to too fast drying during coating.
  • cyclic compound having a carbonyl group examples include ⁇ -butyrolactone, ⁇ -valerlactone, ⁇ -valerolactone, propylene carbonate, ⁇ -methyl pyridone, cyclonucleanone, cycloheptanone, and the like. .
  • ⁇ -butyrolactone may be preferably used.
  • the compound having an alcoholic hydroxyl group and the cyclic compound having a carbonyl group may be used alone or in combination with each other. When used in combination, although there is no restriction
  • the compound having an alcoholic hydroxyl group is more than 99% by weight (the cyclic compound having a carbonyl group is less than 1% by weight)
  • the compatibility of the silane compound of Formula 1 may be deteriorated, the cured film may be whitened, and transparency may be decreased.
  • the condensation reaction of unreacted silanol groups in the silane compound of Formula 1 may easily occur, leading to poor storage stability. have.
  • the photosensitive resin composition according to the above embodiment may further include other solvents in a range that does not impair the effects of the present invention.
  • Other solvents include ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, propylene glycol mono methyl ether acetate, 3-methoxy-1-butyl acetate, 3-methyl-3-medium when 1-ester such as butyl acetate, methyl isobutyl ketone, diisopropyl ketone, diisobutyl ketone, ketones such as acetyl acetone, diethyl ether, diisopropyl ether, di-n - butyl ether, diphenyl ether Ethers such as : c.
  • a solvent Preferably it can be used in the range of 100-1, 000 weight% with respect to 100 weight% of said silane compounds of the said Formula (1).
  • the solvent may be included so that the solid content is 10 to 50 wt% based on the total weight of the photosensitive resin composition.
  • the said solid content means the composition component except a solvent in the resin composition of this invention.
  • the photosensitive resin composition according to the embodiment may contain an additive capable of generating an acid or a base with (C) heat or light.
  • an additive capable of generating an acid or a base with (C) heat or light.
  • it may be a thermal acid generator, a photoacid generator, a thermal base generator or a photoacid generator, for example, may be a thermal acid generator.
  • Such (C) additive can improve the resolution by strengthening the shape of the pattern during the manufacture of the cured film, or by increasing the contrast of development,
  • Photosensitive resin composition according to an embodiment is the (A) polysiloxane polymer 100
  • the (C) additive may include 0.001 to 10.0 parts by weight, for example, 0.01 to 5.0 parts by weight.
  • thermal acid generator examples include various aliphatic sulfonic acids and salts thereof, various aliphatic carboxylic acids such as citric acid, acetic acid and maleic acid, salts thereof, various aromatic carboxylic acids such as benzoic acid and phthalic acid, salts thereof, aromatic sulfonic acids and ammonium salts, and various amines. Salts, aromatic diazonium salts, phosphonic acids, and salts thereof; salts and esters for generating organic acids;
  • the thermal acid generator in one embodiment may be a salt consisting of an organic acid and an organic base, or a salt consisting of a sulfonic acid and an organic base, but is not limited thereto.
  • a thermal acid generator containing sulfonic acid may be P-luenesulfonic acid, benzenesulfonic acid, P-dodecylbenzenesulfonic acid, 1,4-naphthalenedisulfonic acid, methanesulfonic acid ⁇ , or a combination thereof.
  • P-luenesulfonic acid benzenesulfonic acid
  • P-dodecylbenzenesulfonic acid 1,4-naphthalenedisulfonic acid
  • methanesulfonic acid ⁇ or a combination thereof.
  • photoacid generator examples include diazomethane compounds, diphenyl iodonium salts, triphenylsulfonium salts, sulfonium salts, ammonium salts, phosphonium salts, sulfonimide compounds and the like.
  • the structure of these photo-acid generators can be represented by General formula (3).
  • R + is hydrogen, substituted or unsubstituted alkyl group, aryl group, alkenyl group, acyl group, alkoxyl group, etc.
  • X— is, BF 4 " , PIV, Sbl, SCN-, (CF 3 S0 2 ) 2 N 1, carboxylic acid ions, sulfonium ions and the like.
  • Examples of the photobase generator may include a polysubstituted amide compound having an amide group, a lactam, an imide compound, and the like.
  • Examples of the thermal base generator include N- (2-nitrobenzyloxycarbonyl) imidazole, N -(3-nitrobenzyloxycarbonyl) imidazole, N- (4-nitrobenzyloxycarbonyl) imidazole, N- (5-methyl-2-nitrobenzyloxycarbonyl) imidazole, N- (4- Imidazole derivatives such as chloro-2-nitrobenzyloxycarbonyl) imidazole, 1,8- Diazabicyclo (5, 4, 0) undecene-7, tertiary amines, quaternary ammonium salts, or combinations thereof.
  • the photosensitive resin composition according to the embodiment may include (D) a quinonediazide compound.
  • (D) The photosensitive resin composition containing a mundone diazide compound forms the positive type by which an exposure part is removed with a developing solution.
  • the quinonediazide compound which can be used is not particularly limited, but for example, a compound obtained by ester bonding of naphthozinone diazide sulfonic acid to a compound having a phenolic hydroxyl group can be used, and the ortho position of the phenolic hydroxyl group of the compound; and Each of the para positions may independently be hydrogen, or a compound having any one of substituents represented by the following general formula (5):
  • R 12 , R 13 , and R 14 each independently represent any of C1 to C10 alkyl, carboxyl, phenyl and substituted phenyl groups, and R 12 , R 13 , and R 14 together form a ring. You may.
  • the alkyl group may be any of unsubstituted or substituted.
  • the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, n-nuclear group, cyclonuclear group, n-heptyl group and n-octyl group And trifluoromethyl group and 2-carboxyethyl group.
  • the substituted phenyl group includes a phenyl group substituted with a hydroxy group.
  • R 12 , R 13 , and R 14 may form a ring together, and specific examples thereof include a cyclopentane ring, a cyclonucleic acid ring, an adamantane ring, and a fluorene ring.
  • Ortho position of a phenolic hydroxyl group, and a para position the group of that excepting the above, for example
  • oxidative decomposition occurs by thermosetting, and the conjugated compound represented by a quinoid structure is formed, a cured film is colored and colorless transparency falls.
  • These quinonediazide compounds can be synthesized by a known esterification reaction of a compound having a phenolic hydroxyl group with naphthoquinone diazide sulfonic acid chloride.
  • a specific example of a compound which has a phenolic hydroxyl group the following compounds are mentioned (all are the products of Unshu Chemical Co., Ltd.).
  • 4-naphthoquinone diazide sulfonic acid or 5-naphthoquinone diazide sulfonic acid can be used as a naphthoquinone diazide sulfonic acid.
  • the 4-naphthoquinone diazide sulfone acid ester compound is suitable for i-ray exposure because it has absorption in the i-ray (wavelength 365 nm) region.
  • the 5-naphthoquinone diazide sulfonic acid ester compound is suitable for exposure at a wide range of wavelengths because absorption occurs in a wide range of wavelengths.
  • 4-naphthozinone diazide sulfonic acid ester compound or 5-naphthoquinone diazide sulfonic acid ester compound can be selected.
  • the 4-naphthoquinone diazide sulfonic acid ester compound and the 5-naphthoquinone diazide sulfonic acid ester compound can also be used in combination.
  • 0.1-15 weight part for example, 1-10 weight part can be used with respect to 100 weight part of said siloxane compounds of the said Formula (1).
  • 0.1 weight part of addition amount of a quinonediazide compound When less, the melt
  • 1 weight part or more is preferable in order to acquire more favorable melt contrast.
  • the amount of the quinone diazide compound is more than 15 parts by weight, the compatibility between the siloxane compound and the quinone diazide compound is deteriorated, so that whitening of the coating film occurs or coloring due to decomposition of the quinone diazide compound occurs during thermal curing. Since it becomes, the colorless transparency of a cured film falls. Moreover, in order to obtain a more transparent film, it is preferable to use a quinonediazide compound at 10 weight part or less.
  • the photosensitive resin composition according to the above embodiment may further include additional components conventionally used in the photosensitive resin composition, for example, a silane coupling agent, a surfactant, and the like, as necessary.
  • a silane coupling agent is added in order to improve the adhesiveness of the cured film formed and a board
  • the functional silane compound which has a semi-aromatic substituent can be used.
  • the semi-aromatic substituent include carboxyl group, methacryloyl group, isocyanate group, epoxy group and the like.
  • silane coupling agent examples include trimethoxysilylbenzoic acid, Y-methacryloxypropyltrimethoxysilane, vinyltriacexoxysilane, vinyltrimethoxysilane, Y-isocyanatopropyltriethoxysilane, Y One or more selected from -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropyltriethoxysilane, and ⁇ - (3,4-epoxycyclonucleosil) ethyltrimethoxysilane can be used, preferably Glycidoxypropyltriethoxysilane and / or glycidoxypropyltrimethoxysilane having an epoxy group may be used in view of the residual film ratio and the adhesion between the substrate, but the present invention is not limited thereto.
  • the silane coupling agent may be included in the range of 0.01 to 10 parts by weight, for example, 0.01 to 5 parts by weight, based on 100 parts by weight (based on the solid content) of the compound represented by Formula 1 in the photosensitive composition.
  • the content of the silane coupling agent is 0.01 parts by weight or more, the adhesion to the substrate is improved, when the content is less than 10 parts by weight, the thermal stability is improved at high temperatures, and staining after development can be prevented. have.
  • the photosensitive resin composition according to the present invention may further include a surfactant to improve coating performance.
  • surfactants include fluorine-based surfactants, silicone-based surfactants, nonionic surfactants, and other surfactants.
  • the surfactant for example, FZ2122 Dow Corning Toray Corporation), BM-1000, BM-
  • the surfactant may be used in the range of 0.05 to 10 parts by weight, for example, 0.01 to 5 parts by weight, based on 100 parts by weight of the compound represented by Formula 1 (based on the solid content).
  • content of the surfactant is 0.05 parts by weight or more, the applicability is improved and cracks do not occur on the coated surface, and when it is 10 parts by weight or less, it is advantageous in terms of price.
  • the photosensitive resin composition according to one embodiment in addition to the components, is typically in the thermosetting resin composition and / or photosensitive resin composition, if necessary It may further comprise additional ingredients used.
  • the photosensitive resin composition according to the above embodiment may contain additives such as a dissolution accelerator, a dissolution inhibitor, a surfactant, a stabilizer, and an antifoaming agent, as necessary.
  • the photosensitive resin composition according to the above embodiment is applied onto the base substrate by a known method such as spinner, dipping, slit or the like, and prebaked with a heating device such as a hot plate or an oven.
  • Prebaking is carried out in the range of 50 ° C to 150 ° C for 30 seconds to 30 minutes, the film thickness after prebaking can be 0.1 [M to 15.
  • ultraviolet light exposure devices such as stepper, mirror projection mask aligner (MPA) and paratel light mask aligner (PLA) are used to detect 10 mJ / cin in the wavelength range of 2Q0 nm to 450 nm .
  • the exposure may be performed at an exposure amount of from 500 mJ / cin 2 .
  • the exposed portion is dissolved by development, and a positive pattern can be obtained.
  • the developing method it is preferably immersed in the developing solution for 5 seconds to 10 minutes by a method such as showering, dipping, paddle or the like.
  • a well-known alkali developing solution can be used as a developing solution. Specific examples include inorganic alkalis such as hydroxides, carbonates, phosphates, silicates and borates of alkali metals, amines such as 2-diethylamino ethanol, monoethanol amines and diethan amines, tetramethylammonium hydroxide and choline.
  • the aqueous solution containing 1 type, or 2 or more types of ammonium salts is mentioned.
  • a drying bake may be performed in a range of 50 ° C. to 150 ° C. with a heating device such as a hot plate or an oven.
  • soft bake in a range of 50 ° C to 150 ° C with a heating apparatus such as a hot plate or an oven, and then in a range of 150 ° C to 450 ° C with a heating apparatus such as a hot plate, an oven, for example, 10
  • the desired cured film can be prepared by post-baking for minutes to 5 hours.
  • the cured film has high crack resistance and chemical resistance and is excellent in light transmittance. Therefore, the cured film is a thin film transistor (TFT) substrate It can be effectively used for planarization film, interlayer insulation film of semiconductor element and the like.
  • TFT thin film transistor
  • the cured film according to the embodiment manufactured as described above in the case of a cured film of 2 urn thickness, high light of 903 ⁇ 4> or more, for example, 95% or more, for example, 983 ⁇ 4> or more in the 400 nm wavelength range Has transmittance.
  • Conventional acrylic insulating film has a problem that yellowing at 250 ° C or more due to the low heat resistance characteristics, the transmittance is reduced and the polymer is decomposed to reduce the chemical resistance, silsesquioxane containing acrylic group or epoxy group is more heat resistant than acrylic insulating film This improved but the transmittance was still low at high temperatures and there was a problem of low residual film after development.
  • the photosensitive resin composition comprising a polysiloxane copolymer synthesized by hydrolyzing and condensing the silane compound represented by 2, and a solvent may be used as a cross l inker of a carbosilane structural unit in the siloxane compound to form a cured film prepared therefrom.
  • the hardness can be easily adjusted to form a high hardness coating film, thereby improving the high temperature crack resistance.
  • the organic solvent and the like can be effectively prevented from penetrating through the cured film.
  • the cured film prepared by curing the composition solves the problem of the residual film rate, in which the film thickness is reduced after development, thereby failing to form a flat film, and also does not have a pattern collapse phenomenon due to excellent chemical resistance after curing.
  • the conventional acrylic copolymer or silsesquioxane copolymerized with the organic compound has a high heat resistance, it does not discolor at a curing temperature of 300 ° C or more.
  • the cured film may be a planarization film for a thin film transistor (TFT) substrate such as a liquid crystal display device or an organic EL display device, a protective or insulating film such as a touch panel sensor element, an interlayer insulation film for a semiconductor device, a planarization film for a solid-state imaging device, and a microlens array. It can be used as a core or clad material of an optical waveguide such as a pattern or an optical semiconductor element.
  • TFT thin film transistor
  • an electronic device including the cured film is provided.
  • the device is a liquid crystal comprising the cured film as a flattening film of a TFT substrate. It can be a display element, an organic EL element, a semiconductor device, a solid-state image sensor, etc., It is not limited to these.
  • phenyltrimethoxysilane and methyltrimethoxysilane which are silane compounds represented by Chemical Formula 1
  • 1,2-bistriethoxysilylethane represented by Chemical Formula 2
  • the refractive index exhibits a high refractive index of 1.50 or more.
  • the polysiloxane copolymer prepared in Synthesis Example 7 in which only 50% of the total silicon atoms in the polysiloxane copolymer were substituted with phenyl groups was insoluble in 2.38% aqueous TMAH solution and had a dissolution rate of 45 A / sec for 5.0% TMAH aqueous solution. Even, the refractive index was lower than 1.50.
  • the refractive index was lower than 1.50.
  • the MultiSpec-1500 (trade name, manufactured by SHIMADZU Corporation), first, the light transmittance of only the glass substrate was measured, and this ultraviolet visible absorption spectrum was used as a reference. Subsequently, a cured film of the photosensitive resin composition was formed (the pattern exposure was not performed) on the glass substrate, the sample was measured by a single beam, and a light transmittance having a wavelength of 400 nm per 1 was obtained to determine the difference from the reference. It was set as transmittance
  • Example 1 Preparation and Evaluation of Cured Film 3 parts by weight of the thermal acid generator are added to 100 parts by weight of the polysiloxane copolymer obtained in Synthesis Example 1. After adding the solvent which mixed PGMEA and GBL to this, it mixed and stirred to make a homogeneous solution, and it filtered with the filter of 0.2 Pa, and prepared the resin composition. The composition was spin-coated with a spin coater (Mikasa Corporat ion) in a 10 ⁇ 10 class and then prebaked at 140 ° C. for 120 seconds using a hot plate (SCW-636 from Dainippon Screen Mfg. Co., Ltd.). To adjust the film thickness to 2.7.
  • a spin coater Moikasa Corporat ion
  • Example 2 Preparation and Evaluation of Cured Film A resin composition was prepared in the same manner as in Example 1, except that 100 parts by weight of the polysiloxane copolymer obtained in Synthesis Example 2 was used, and a cured film was prepared in the same manner. As a result of hardening, an insulating film with high temperature crack resistance and chemical resistance maintained at a transmittance of 98% and a crack-free thickness margin of 3.2 zm was obtained.
  • Example 3 Preparation and Evaluation of Cured Film
  • a resin composition was prepared in the same manner as in Example 1, except that 100 parts by weight of the polysiloxane copolymer obtained in Synthesis Example 3 was used, and a cured film was prepared in the same manner.
  • an insulating film having high transmittance of 98% and a crack-free thickness margin of 3.5 kPa having high temperature crack resistance and chemical resistance was obtained.
  • Example 4 Preparation of cured film prepared and evaluated, except that with the polysiloxane 100 parts by weight of copolymer obtained in Synthesis Example 4 and Example 1 to produce the resin composition in the same manner, and using this, was' prepared cured film in the same manner .
  • Example 5 Preparation and Evaluation of Cured Film A resin composition was prepared in the same manner as in Example 1, except that 100 parts by weight of the polysiloxane copolymer obtained in Synthesis Example 5 was used, and a cured film was prepared in the same manner. As a result of curing, an insulating film having a high permeability and chemical resistance of 98% in transmittance and no crack generation thickness margin of 4.0 was obtained.
  • Example 6 Preparation and Evaluation of Cured Film A resin composition was prepared in the same manner as in Example 1, except that 100 weight% of the polysiloxane copolymer obtained in Synthesis Example 6 was used, and a cured film was prepared in the same manner. . As a result of curing, an insulating film having a high permeability and chemical resistance of 98% having a transmittance and no crack generation thickness margin of 4.5 was obtained. Comparative Example 1: Preparation and Evaluation of Cured Film A resin composition was prepared in the same manner as in Example 1, except that 100 parts by weight of the polysiloxane copolymer obtained in Synthesis Example 7 was used, and a cured film was prepared in the same manner.
  • Comparative Example 2 Preparation and Evaluation of Cured Film A resin composition was prepared in the same manner as in Example 1, except that 100 parts by weight of the polysiloxane copolymer obtained in Synthesis Example 8 was used, and a cured film was prepared in the same manner. As a result of curing, an insulating film having a transmittance of 97% and a crack-free thickness margin of 2.5 was obtained.
  • the cured film manufactured from the photosensitive resin composition which is insoluble in a 38 weight% TMAH aqueous solution and has a dissolution rate of 100 A / sec or less for a 5.0 weight% -TMAH aqueous solution has a thickness of 2. There is no cracking at 3 and no crack-free thickness margin that maintains a light transmittance of 98% for 400 nm wavelength. It can be seen that it has excellent anti-tacktack and a high light transmittance of 2 i or more. Moreover, the rate of change of the thickness of the cured film with respect to the chemical resistance evaluation solvent is 5% or less, and the chemical resistance is also very excellent.
  • the photosensitive resin composition according to Comparative Example 1 and Comparative Example 2 comprising the polysiloxane co-polymer prepared in Synthesis Example 7 and Synthesis Example 8, in which only 50% of all silicon atoms in the polysiloxane copolymer were substituted with phenyl groups, had a thickness after curing. Both cracks occurred, and the crack-free thickness margin maintaining 97% light transmittance for the 400 nm wavelength was 2. 5 j ⁇ , it can be seen that it is significantly lower than the crack resistance of the cured film according to Examples 1 to 6.
  • the photosensitive resin composition according to the embodiment has excellent crack resistance and chemical resistance after curing of the cured film prepared therefrom, maintains high light transmittance, and can increase the crack margin to easily control the thickness of the cured film. It can be seen that.

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Abstract

L'invention concerne une composition de résine photosensible, un film durci produit par durcissement de la composition de résine photosensible, et un dispositif électronique comprenant le film durci, la composition de résine photosensible comprenant (A) un polymère de polysiloxane et (B) un solvant, le polymère de polysiloxane (A) étant formé par soumission d'au moins un type d'un composé de silane, représenté par la formule chimique (1) ci-dessous, à l'hydrolyse et une réaction de condensation, un film précuit étant insoluble dans une solution aqueuse à 2,38 % en poids d'hydroxyde de tétraméthylammonium (TMAH) et a un taux de dissolution de 100Å/sec ou moins dans une solution aqueuse de TMAH à 5 % en poids : [formule chimique 1] (R1) aSiX1 4-a, où R1, X1 et a sont tels que définis dans la description.
PCT/KR2017/003499 2016-09-28 2017-03-30 Composition de résine photosensible, film durci formé de là, et dispositif électronique ayant le film durci WO2018062652A1 (fr)

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