KR101852458B1

KR101852458B1 - Photo-sensitive Composition, Cured Film Prepared Therefrom, and Device Incoporating the Cured Film

Info

Publication number: KR101852458B1
Application number: KR1020150152577A
Authority: KR
Inventors: 박종희; 김우한; 백윤희; 백택진; 심수연; 유홍정; 이승은; 이지호
Original assignee: 삼성에스디아이 주식회사
Priority date: 2015-10-30
Filing date: 2015-10-30
Publication date: 2018-04-26
Also published as: KR20170050704A

Abstract

(A) a siloxane compound represented by the following formula (1); (B) a quinone diazide compound, and (C) a solvent.
[Chemical Formula 1]
^{(R 1 R 2 R 3 SiO} 1/2) M (R 4 R 5 SiO 2/2) D (R 6 SiO 3/2) T1 (O 3/2 Si-Y-SiO 3/2) T2 (SiO _4/2 ) _Q
In Formula 1,
The definitions of R ¹ to R ⁶ , Y, M, D, T 1, T 2, and Q are as described in the description of the invention.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a photosensitive resin composition, a cured film formed therefrom, and a device having a cured film (Photo-sensitive Composition, Cured Film Prepared Therefrom, and Device Incorporating the Cured Film)

A photosensitive resin composition, a cured film formed therefrom, and a device having the cured film.

In order to realize more precise and high resolution in a liquid crystal display, an organic EL display, etc., the aperture ratio of the display device must be raised. This is because a transparent planarization film is provided as a protective film on the TFT substrate to overlap the data line and the pixel electrode, .

As a material for forming the organic insulating film for a TFT substrate, a material having high heat resistance, high transparency, crack resistance at high temperature, low dielectric constant, and chemical resistance is required. In order to secure the conduction between the TFT substrate electrode and the ITO electrode It is necessary to form hole patterns of about 50 mu m to several mu m.

Conventionally, a light-sensitive resin composition comprising a combination of a phenolic resin and a quinone diazide compound or a combination of an acrylic resin and a quinone diazide compound has been mainly used. However, these materials do not rapidly deteriorate in material properties at a high temperature of 200 DEG C or more, but decomposition starts slowly at 230 DEG C or higher, and the film thickness or the cracking phenomenon occurs, or the transparent film is colored And the transmittance is lowered.

In recent years, in order to improve the transparency and the functionality of the touch panel, a transparent electrode member made of ITO having high transparency and high conductivity has been used for a liquid crystal display or the like. However, . Along with this, the protective film or insulating film of the transparent electrode member is required to have heat resistance to high temperature treatment. However, since the acrylic resin is insufficient in heat resistance and chemical resistance, the cured film is colored due to the high temperature treatment of the substrate, the high-temperature film formation such as a transparent electrode or various kinds of etching solution treatment, There is a problem that the conductivity of the electrode is lowered. Therefore, it can not be used in a process of forming a film at a high temperature by using a device such as PE-CVD on the transparent film material.

Also in the organic EL device, cracks and decomposition products generated from the above materials have no adverse effect on the luminous efficiency and lifetime of the organic EL device, and therefore, they are not suitable for use. In addition, the acrylic material imparted with heat resistance may also crack at 300 DEG C or higher, otherwise the dielectric constant generally increases. As a result, the parasitic capacitance due to the insulating film becomes large due to the high dielectric constant, which causes power consumption to increase and a problem of image quality due to delay of the liquid crystal element driving signal. Even in the case of an insulating material having a high dielectric constant, for example, it is possible to reduce the capacitance by increasing the film thickness, but it is generally not preferable to form a uniform thick film and the amount of material used is also increased.

On the other hand, silsesquioxane is known as a material having high heat resistance and high transparency. In particular, a photosensitive composition comprising a silsesquioxane compound having an acrylic group added to a specific silsesquioxane, an unsaturated compound containing an unsaturated carboxylic acid and an epoxy group, and an acrylic copolymer obtained by copolymerizing an olefinically unsaturated compound and a quinone diazide compound Have been proposed. However, since these compounds also have a high content of organic compounds, they have a problem of heat resistance which is colored and yellow after being cured after being cured at a high temperature of 250 ° C. or higher and have a low permeability. Since the residual film ratio after development is low, a flat film is not formed or NMP the chemical resistance to a solvent such as pyrrolidone, tetramethylammonium hydroxide (TMAH) solution and 10% NaOH is also reduced.

As a system in which a quinone diazide compound is combined with a siloxane polymer in order to impart positive photosensitivity to the siloxane polymer, a material obtained by combining a siloxane polymer having a phenolic hydroxyl group at the terminal thereof with a quinone diazide compound, A material obtained by combining a siloxane polymer having a carboxyl group added thereto and a quinone diazide compound is known. However, since these materials contain a large amount of quinone diazide compound, or phenolic hydroxyl groups are present in the siloxane polymer, coloring of the coating film tends to occur during whitening or thermal curing, and cracking occurs at a high temperature of 300 ° C or higher And can not be used as a material with high transparency due to a decrease in transmittance. Further, since these materials have low transparency, there is also a problem that the sensitivity is low during pattern formation.

When a photosensitive composition made solely of a polysiloxane and a quinone diazide compound is thermally cured, crosslinking and high molecular weight are caused by dehydration condensation of a silanol group in the polysiloxane. In this thermosetting process, before the thermal curing of the pattern sufficiently progresses, it is melted by the low viscosity of the film due to the high temperature, and patterns such as holes and lines obtained after the development flow. As a result, cracks do not occur, but degradation of the pattern, which degrades the resolution, occurs and must be prevented.

In addition, when a quinone diazide compound is combined with a polysiloxane-insoluble polysiloxane and a polysiloxane compound which is insoluble in a developer, patterns of holes and lines obtained after development are collapsed upon heating and curing, resulting in "pattern sagging" A photosensitive composition is proposed. However, if a polysiloxane insoluble in a developing solution is used, it will dissolve after development, but re-adherence of residues or unstable water starting to melt may cause development pattern defects. In order to prevent pattern deterioration, it is necessary to sufficiently increase the molecular weight of the siloxane. As a result, the photosensitive material has low sensitivity and high reaction energy is required. Further, there is a drawback that the residual film ratio is not sufficient and the loss of the material is large.

One embodiment provides a positive photosensitive resin composition having high heat resistance, high transparency, high hardness, and low dielectric constant properties.

Another embodiment provides a cured film obtained by curing the composition.

Another embodiment provides an element comprising the cured film.

(A) a siloxane compound represented by the following formula (1); (B) a quinone diazide compound, and (C) a solvent.

[Chemical Formula 1]

^{(R 1 R 2 R 3 SiO} 1/2) M (R 4 R 5 SiO 2/2) D (R 6 SiO 3/2) T1 (O 3/2 Si-Y-SiO 3/2) T2 (SiO _4/2 ) _Q

In Formula 1,

R ¹ to R ⁶ are each independently selected from the group consisting of hydrogen, hydroxy, halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, A substituted or unsubstituted C1 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C2 A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C1 to C30 alkoxy group, R (C = O) - Or an unsubstituted or substituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C7 to C30 arylalkyl group), or a combination thereof, wherein R ¹ to R ⁶ Combined Based on the content of silicon atoms, at least 40 mol% of R ¹ to R ⁶ are substituted or unsubstituted C6 to C30 aryl groups,

Y is a single bond, oxygen, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 hetero A substituted or unsubstituted C2 to C30 alkenylene group, a substituted or unsubstituted C2 to C20 alkynylene group, or a combination thereof,

0 < 0.4, 0 < D < 0.4, 0.6 &

M + D + T1 + T2 + Q = 1,

The structural units represented by M, D, T1, T2, and Q may each include one or more different structural units.

In the formula (1), M and Q are each 0, and 0? D? 0.2, 0.65? T1 <1, and 0 <T2 <0.2.

In the formula (1), M and Q are all 0, and 0? D? 0.2, 0.7? T1 <1, and 0 <T2?

In formula (1), R ¹ to R ⁶ are a substituted or unsubstituted C6 to C30 aryl group, based on the content of Si atoms to which they are bonded, at least 40 mol%, and at least 30 mol% C30 < / RTI > alkyl group.

And R ¹ to R ⁶ wherein the substituted or unsubstituted C6 to C30 aryl group is a phenyl ring of the substituted or unsubstituted C1 to C30 alkyl ring may be a C1 to C4 alkyl group.

In Formula (1), Y may be a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, or a substituted or unsubstituted C6 to C30 arylene group.

In another embodiment, there is provided a cured film obtained by curing the photosensitive resin composition according to the above embodiment.

The cured film may be used as a flattening film for a thin film transistor (TFT) substrate of a liquid crystal display element or an organic EL display element, a protective film or insulating film of a touch panel sensor element, an interlayer insulating film of a semiconductor element, a flattening film for a solid- Or a core or a clad material of an optical waveguide of an optical semiconductor device .

The cured film exhibits a hole characteristic of less than 7 mu m at a temperature of 200 DEG C or higher and a light transmittance of 95% or more at a wavelength of 400 nm at a thickness of 2.5 mu m.

The cured film has a residual film ratio of 87% or more, which is defined as " (film thickness of unexposed area after development / film thickness after pre-baking) x 100 ".

According to another embodiment, there is provided an element comprising the cured film.

The photosensitive resin composition according to one embodiment has a high heat resistance, a high transparency, a high hardness, and a low dielectric constant, which do not generate scum after pattern collapse at high temperature, and exhibit excellent resistance to cracking at high temperatures and a positive photosensitive A cured film prepared by curing the resin composition can be usefully used for the production of a planarizing film for a thin film transistor (TFT) substrate, an interlayer insulating film for a semiconductor device, and the like.

Hereinafter, exemplary embodiments of the present invention will be described in detail so that those skilled in the art can easily carry out the present invention. The present invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein.

Unless otherwise defined herein, "substituted" means that the hydrogen atom in the compound is a halogen atom (F, Br, Cl, or I), a hydroxy group, an alkoxy group, a nitro group, a cyano group, an amino group, A thio group, an ester group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof, a C1 to C20 alkyl group, a C2 to C20 alkenyl group, a C2 to C20 alkenyl group, a C2 to C20 alkenyl group, A C 1 to C 30 arylalkyl group, a C 7 to C 30 arylalkyl group, a C 1 to C 30 alkoxy group, a C 1 to C 20 heteroalkyl group, a C 3 to C 20 heteroarylalkyl group, a C 3 to C 30 cycloalkyl group, a C 3 to C 15 cycloalkenyl group, C6 to C15 cycloalkynyl groups, C3 to C30 heterocycloalkyl groups, and combinations thereof.

Also, unless otherwise defined herein, 'hetero' means containing at least one heteroatom selected from N, O, S, and P.

Unless otherwise specified herein, 'combination' means mixing or copolymerization.

Hereinafter, the photosensitive resin composition according to one embodiment will be described.

The photosensitive resin composition according to one embodiment comprises (A) a siloxane compound represented by the following formula (1); (B) a quinone diazide compound, and (C) a solvent.

[Chemical Formula 1]

In Formula 1,

R ¹ to R ⁶ are each independently selected from the group consisting of hydrogen, hydroxy, halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, A substituted or unsubstituted C1 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C2 A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C1 to C30 alkoxy group, R (C = O) - Or an unsubstituted or substituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C7 to C30 arylalkyl group), or a combination thereof, wherein R ¹ to R ⁶ Combined Is at least 40 mol% based on the content of Si atoms, R ¹ to R ⁶ are substituted or unsubstituted C6 to C30 aryl groups,

0 < 0.4, 0 < D < 0.4, 0.6 &

M + D + T1 + T2 + Q = 1,

As shown by the above formula (1), the siloxane compound comprises at least 0.6 the structural unit represented by (R ⁶ SiO _3/2) in the compounds in a molar fraction, and _{(O 3/2 Si-Y} -SiO 3 / ₂ ) is less than 0.2.

_{(O 3/2 Si-Y} -SiO 3/2) when including a structural unit represented by the above-described range, the photosensitive resin composition comprising a compound of the formula (1) is a dense structure with a sufficient cross-linking upon curing , It has high mechanical strength, chemical resistance, and high retention rate.

Further, by including the appropriate adjustment in the _{(O 3/2 Si-Y} -SiO 3/2) structural unit represented by the and the cross-linking agent acts in the compound represented by general formula (1), therefore, the range of the structural unit , The hardness of the coating film can be easily controlled and the hardness of the coating film can be improved. The resulting coating film having a high hardness has a high crack resistance at a high temperature and at the same time effectively prevents penetration of the organic solvent. It is possible to solve the problem of residual film ratio which can not be formed and to realize an organic insulating film excellent in chemical resistance after curing, crack resistance at high temperature, etch resistance and the like.

, A siloxane compound represented by the formula (1) R ¹ to R ⁶ are combined based on the content of the Si atoms at least 40 mol% R ¹ to R ⁶ is a substituted or unsubstituted C6 to C30 aryl group, for example as described above, For example, a phenyl group.

When at least 40 mol% of the R ¹ to R ⁶ in the compound represented by the formula (1) is a substituted or unsubstituted C6 to C30 aryl group, for example, a phenyl group, based on the content of Si atoms to which they are bonded, The photosensitive resin composition comprising It is possible to remarkably reduce the cracking rate at the time of curing at a high temperature. In the case where the compound represented by the general formula (1) comprises a substituted or unsubstituted C6 to C30 aryl group of less than 40 mol% based on the content of Si atoms bonded to R ¹ to R ⁶ , the photosensitive resin composition prepared therefrom has a high Cracking rate increases during curing.

In one embodiment, T1 among the constituent units constituting the compound represented by Formula 1 is 0.6? T1 <1, for example, 0.65? T1 <1, for example, 0.7? T1 <1, Lt; T1 < 1.

When the structural unit represented by T1 in the compound represented by the formula (1), that is, (R ⁶ SiO _3/2 ) is present within the above-described range within the above-mentioned compound, the photosensitive resin composition comprising the compound has storage stability High transparency after curing, high hardness, high retention rate, high resolution, and excellent sensitivity to light.

Further, of the structural units constituting the compound represented by general formula (1) structural unit represented by T2, _{i.e., (O 3/2 Si-} Y-SiO 3/2) is 0 <T2 <0.2, for example, 0 < For example, 0 < T2 < 0.10, for example 0 < For example, 0 < T2 < 0.05, for example 0 < T2? 0.03.

When the structural unit represented by T2 among the compounds represented by Formula 1 is included in the above range, the photosensitive resin composition containing the compound has high surface hardness, residual film ratio, and crack resistance after curing.

Further, the structural unit represented by D in the structural units constituting the compound represented by general formula (1), ^{_{i.e., (R 4 R 5 SiO 2}} /2) is, 0≤D <0.4, for example, 0≤D≤0.3 , For example, 0 D? 0.2, e.g., 0 D? 0.15.

In one embodiment, M and Q in formula (1) may each be 0, 0 < D < 0.2, 0.65 <

In one embodiment, M and Q in formula (1) are all 0, 0? D? 0.2, 0.7? T1 <1, and 0 <T2?

The compound represented by the formula (1) is, for example, R ¹ R ² R ³ SiZ ¹ , A monomer represented by R ⁴ R ⁵ SiZ ² Z ³ and a monomer represented by R ⁶ SiZ ⁴ Z ⁵ Z ⁶ , A monomer represented by Z ⁷ Z ⁸ Z ⁹ Si-Y-SiZ ¹⁰ Z ¹¹ Z ¹² , and a monomer represented by SiZ ¹³ Z ¹⁴ Z ¹⁵ Z ¹⁶ by hydrolysis and condensation polymerization. Wherein the definitions of R ¹ to R ⁶ are as defined above, and Z ¹ to Z ¹⁶ are each independently a C ¹ to C 6 alkoxy group, a hydroxy group, a halogen, a carboxyl group, or a combination thereof.

The hydrolysis and polycondensation reaction for preparing the compound represented by the formula (1) can be carried out by a general method well known to those skilled in the art. For example, adding a solvent, water and, if necessary, a catalyst to the above mixture of monomers and stirring at a temperature of 50 ° C to 150 ° C, for example, 90 ° C to 130 ° C for 0.5 hours to 100 hours do. During the stirring, the hydrolysis by-products (alcohol such as methanol) and condensation by-products can be distilled and removed by distillation, if necessary.

The reaction solvent is not particularly limited, but usually the same solvent as the solvent contained in the photosensitive resin composition according to the embodiment can be used.

The amount of the solvent to be added may be 10 to 1000 parts by weight based on 100 parts by weight of the total weight of the monomers. The amount of water to be used for the hydrolysis reaction may be in the range of 0.5 to 3 mol per 1 mol of the hydrolyzable group.

The catalyst to be added is not particularly limited, but an acid catalyst, a base catalyst and the like can be used. The amount of the catalyst to be added may be in the range of 0.01 to 10 parts by weight based on 100 parts by weight of the total weight of the monomers.

The compound represented by the formula (1) may be used alone or in combination of two or more.

The molecular weight of the compound of Formula 1 may be about 1,000 to 500,000, for example, about 1,000 to 100,000, for example, in terms of a polystyrene standard sample measured by Gel Permeation Chromatography (GPC) For example, from about 3,000 to about 20,000, such as from about 3,000 to about 15,000, such as from about 3,000 to about 10,000, such as from about 3,000 to about 8,000, such as from about 3,000 to about 10,000, To 6,000, for example, from 3,000 to 5,000.

When the weight average molecular weight of the compound is 1,000 or more, cracks do not occur on the surface during curing, and a preferable thickness of the cured film can be realized. When the weight average molecular weight is 500,000 or less, the surface flatness can be improved by maintaining the viscosity required for coating.

The photosensitive resin composition according to this embodiment includes (B) a quinone diazide compound. A photosensitive resin composition comprising a quinone diazide compound forms a positive type in which an exposed portion is removed by a developer. No particular limitation is imposed on the quinone diazide compound that can be used. For example, a compound in which a naphthoquinone diazide sulfonic acid is ester-bonded to a compound having a phenolic hydroxyl group can be used. The ortho position of the phenolic hydroxyl group of the compound, And para position are each independently selected from the group consisting of hydrogen and a substituent represented by the following formula (2):

(2)

In Formula 2,

R ¹² , R ¹³ and R ¹⁴ each independently represents a C1 to C10 alkyl group, a carboxyl group, a phenyl group or a substituted phenyl group, and R ¹² , R ¹³ and R ¹⁴ together form a ring You may.

In R ¹² , R ¹³ and R ¹⁴ of the group represented by the general formula (2), the alkyl group may be unsubstituted or substituted. Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, a n-hexyl group, a cyclohexyl group, , A trifluoromethyl group, and a 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 cyclohexane ring, an adamantane ring, and a fluorene ring.

When the ortho position and the para position of the phenolic hydroxyl group are other than the above groups, for example, a methyl group, oxidative decomposition occurs due to thermal curing to form a conjugated system represented by a quinoid structure, The transparency deteriorates. These quinone diazide compounds can be synthesized by a known esterification reaction between a compound having a phenolic hydroxyl group and naphthoquinone diazidesulfonic acid chloride. Specific examples of the compound having a phenolic hydroxyl group include the following compounds (all available from Honshu Chemical Industry Co., Ltd.).

As naphthoquinonediazidesulfonic acid, 4-naphthoquinonediazidesulfonic acid or 5-naphthoquinonediazidesulfonic acid can be used. The 4-naphthoquinonediazide sulfonic acid ester compound is suitable for i-line exposure because it has absorption in the i-line (wavelength 365 nm) region. Further, the 5-naphthoquinone diazidesulfonic acid ester compound is suitable for exposure at a wide wavelength because absorption occurs in a wide wavelength range. Depending on the exposure wavelength, a 4-naphthoquinonediazide sulfonic acid ester compound or a 5-naphthoquinone diazide sulfonic acid ester compound can be selected. A 4-naphthoquinone diazidesulfonic acid ester compound and a 5-naphthoquinone diazidesulfonic acid ester compound may be mixed and used.

The amount of the quinone diazide compound to be added is not particularly limited. For example, 0.1 to 15 parts by weight, for example, 1 to 10 parts by weight, based on 100 parts by weight of the siloxane compound of Formula 1 may be used. When the addition amount of the quinone diazide compound is less than 0.1 part by weight, the dissolution contrast between the exposed portion and the unexposed portion is too low to be practically photosensitive. Further, 1 part by weight or more is preferable in order to obtain better dissolution contrast. When the addition amount of the quinone diazide compound is more than 15 parts by weight, the compatibility of the siloxane compound and the quinone diazide compound is deteriorated, resulting in whitening of the coating film, or coloration due to decomposition of the quinone diazide compound The colorless transparency of the cured film deteriorates. In order to obtain a film having a higher transparency, it is preferable that the quinone diazide compound is used in an amount of 10 parts by weight or less.

Further, the photosensitive resin composition according to this embodiment contains (C) a solvent.

The usable solvent is not particularly limited, but preferably a compound having an alcoholic hydroxyl group and / or a cyclic compound having a carbonyl group is used. When these solvents are used, the siloxane compound and the quinone diazide compound dissolve uniformly, so that the film is not whitened at the time of coating after application, and high transparency can be achieved.

The compound having an alcoholic hydroxyl group is not particularly limited, but preferably a compound having a boiling point of 110 to 250 DEG C at atmospheric pressure can be used. If the boiling point is higher than 250 deg. C, the amount of the residual solvent in the film increases, and the film shrinkage ratio during curing becomes large, and good flatness can not be obtained. If the boiling point is lower than 110 ° C, the film becomes too dry during coating, resulting in roughness of the film surface.

Specific examples of the compound having an alcoholic hydroxyl group include acetol, 3-hydroxy-3-methyl-2-butanone, 4-hydroxy- Propylene glycol monomethyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono n-butyl ether, propylene glycol monomethyl ether, Butyl ether, propylene glycol mono t-butyl ether, 3-methoxy-1-butanol and 3-methyl-3-methoxy-1-butanol. Of these, compounds having a carbonyl group are particularly preferable, and diacetone alcohol is particularly preferably used. These compounds having an alcoholic hydroxyl group may be used alone or in combination of two or more.

The cyclic compound having a carbonyl group is not particularly limited, but preferably a compound having a boiling point of 150 ° C to 250 ° C at atmospheric pressure can be used. When the boiling point is higher than 250 占 폚, the amount of the residual solvent in the film becomes large, and the film shrinkage increases during curing and good elasticity can not be obtained. If the boiling point is lower than 150 ° C, the film becomes too dry during the coating, resulting in a rough film surface and poor coatability.

Specific examples of the cyclic compound having a carbonyl group include? -Butylolactone,? -Valerolactone,? -Valerolactone, propylene carbonate, N-methylpyrrolidone, cyclohexanone and cycloheptanone . Of these, especially? -Butyrolactone can be preferably used. These cyclic compounds having a carbonyl group may be used singly or in combination of two or more kinds.

The compound having an alcoholic hydroxyl group and the cyclic compound having a carbonyl group may be used alone or in combination. The weight ratio of the compound having an alcoholic hydroxyl group to the cyclic compound having a carbonyl group is preferably about 99 to 50: 1 to 50, or, for example, 97 to 60: 3 / RTI > When the amount of 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 siloxane compound and the quinone diazide compound of the formula (1) becomes poor and the cured film becomes white can do. When the amount of the compound having an alcoholic hydroxyl group is less than 50% by weight (more than 50% by weight of the cyclic compound having a carbonyl group), the condensation reaction of unreacted silanol groups in the siloxane compound of the formula (1) tends to occur and storage stability may deteriorate .

The photosensitive resin composition according to the above embodiments may further contain other solvents insofar as the effect of the present invention is not impaired. Other examples of the solvent include ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, propylene glycol monomethyl ether acetate, 3-methoxy- Butyl acetate, and the like; ketones such as methyl isobutyl ketone, diisopropyl ketone, diisobutyl ketone and acetyl acetone; ketones such as diethyl ether, diisopropyl ether, di-n-butyl ether, diphenyl ether And the like.

The amount of the solvent to be added is not particularly limited, but is preferably in the range of 100 to 1,000 parts by weight based on 100 parts by weight of the siloxane compound of the formula (1). Alternatively, the solvent may be contained so that the solids content is 10 to 50% by weight based on the total weight of the photosensitive resin composition. The solid content means a composition component excluding the solvent in the resin composition of the present invention.

The photosensitive resin composition according to the above embodiments may further contain additional components commonly used in the photosensitive resin composition, for example, a silane coupling agent, a surfactant, and the like, if necessary.

The silane coupling agent is added in order to improve the adhesion between the cured film to be formed and the substrate. As the known silane coupling agent, a functional silane compound having a reactive substituent can be used. Examples of the reactive substituent include a carboxyl group, a methacryloyl group, an isocyanate group, and an epoxy group.

Specific examples of the silane-based coupling agent include trimethoxysilylbenzoic acid,? -Methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane,? -Isocyanatopropyltriethoxysilane,? -Glycidoxypropyltrimethoxysilane,? -Glycidoxypropyltriethoxysilane, and? - (3,4-epoxycyclohexyl) ethyltrimethoxysilane, and preferably at least one selected from the group consisting of Gamma -glycidoxypropyltriethoxysilane and / or gamma -glycidoxypropyltrimethoxysilane having an epoxy group can be used in view of adhesion between the residual film ratio and the substrate, but the present invention is not limited thereto Do not.

The silane coupling agent may be contained in the photosensitive composition in the range of 0.01 to 10 parts by weight, for example, 0.1 to 5 parts by weight based on 100 parts by weight (based on the solid content) of the compound represented by the formula (1). When the content of the silane coupling agent is 0.01 parts by weight or more, the adhesion to the substrate is improved. When the amount is 10 parts by weight or less, the thermal stability is improved at a high temperature, and the occurrence of unevenness after development can be prevented.

The photosensitive resin composition according to the present invention may further include a surfactant to improve the coating performance. Examples of such surfactants include fluorine surfactants, silicone surfactants, nonionic surfactants, and other surfactants.

Examples of the surfactant include FZ2122 (Dow Corning Toray Corporation), BM-1000, BM-1100 (manufactured by BM CHEMIE), Megafac F142D, Copper F172, Copper F173, Copper F183 S-113, S-131 (manufactured by Sumitomo 3M Limited), Florad FC-135, FC-170C, FC-430 and FC-431 , S-141, S-145, S-382, SC-101, SC-102, SC-103, SC-104, SC-105 and SC-106 (Asahi Garasu Co., SH-193, SZ-6032, SF-8428, DC-57, DC (available from Shin-Aichi Kasei Kogyo Co., Ltd.) -190 (manufactured by Toray Silicone Co., Ltd.); Polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether and polyoxyethylene oleyl ether, polyoxyethylene aryl ethers such as polyoxyethylene octylphenyl ether and polyoxyethylene nonylphenyl ether , Polyoxyethylene dialkyl esters such as polyoxyethylene dilaurate and polyoxyethylene distearate, and other nonionic surfactants; (Manufactured by Shin-Etsu Chemical Co., Ltd.) or (meth) acrylic acid-based copolymer polyflow No. 57,95 (manufactured by Kyoeisha Chemical Co., Ltd.) And can be used in parallel.

The surfactant may be used in an amount of 0.05 to 10 parts by weight, for example, 0.1 to 5 parts by weight based on 100 parts by weight (based on the solid content) of the compound represented by Formula 1. When the content of the surfactant is 0.05 parts by weight or more, the coatability is improved and cracks are not generated on the coated surface, and when the content is 10 parts by weight or less, it is advantageous in terms of cost.

In addition to the above components, the photosensitive resin composition according to one embodiment may further include additional components that are conventionally used in the thermosetting resin composition and / or the photosensitive resin composition, if necessary. For example, the photosensitive resin composition according to the above embodiment may contain additives such as a dissolution accelerator, a dissolution inhibitor, a surface active agent, a stabilizer, and an antifoaming agent, if necessary.

In particular, the dissolution enhancer can improve the sensitivity. As the solubility promoting agent, a compound having a phenolic hydroxyl group or an N-hydroxydicarboximide compound is preferably used. As a specific example, a compound having a phenolic hydroxyl group used in a quinone diazide compound can be mentioned.

Hereinafter, a method of forming a cured film using the photosensitive resin composition according to the above embodiment will be described.

The photosensitive resin composition according to this embodiment is coated on a base substrate by a known method such as spinner, dipping, or slit, and is prebaked by a heating device such as a hot plate or oven. The prebaking may be performed at a temperature in the range of 50 DEG C to 150 DEG C for 30 seconds to 30 minutes, and the film thickness after prebaking may be 0.1 mu m to 15 mu m.

After pre-baking, an ultraviolet visible light exposure apparatus such as a stepper, a mirror projection mask aligner (MPA), and a parallel light mask aligner (PLA) was used to measure the exposure amount at a wavelength band of 200 nm to 450 nm at 10 mJ / cm 2 to 500 mJ / As shown in FIG.

After exposure, the exposed portion is dissolved by development to obtain a positive pattern. As the developing method, it is preferable to immerse the developing solution for 5 seconds to 10 minutes by a method such as shower, dipping, paddle, or the like. As the developer, a known alkali developer can be used. Specific examples thereof include inorganic alkalis such as hydroxides, carbonates, phosphates, silicates and borates of alkali metals, amines such as 2-diethylaminoethanol, monoethanolamine and diethanolamine, quaternary ammonium salts such as tetramethylammonium hydroxide and choline Or an aqueous solution containing one or more of these.

After development, it is preferable to rinse with water. If necessary, drying baking may be performed in a range of 50 ° C to 150 ° C by a heating apparatus such as a hot plate or an oven.

Then, it is preferable to perform the bleaching exposure. By carrying out the bleaching exposure, the unreacted quinonediazide compound remaining in the film is photodegraded, so that the optical transparency of the film can be further improved. As a bleaching exposure method, an entire surface is exposed to an exposure dose of about 100 J / m ² to about 20,000 J / m ² (equivalent to a wavelength of 365 nm in terms of exposure dose) using an ultraviolet exposure apparatus such as PLA.

If necessary, the film subjected to the bleaching exposure may be subjected to a soft bake in a range of 50 ° C to 150 ° C by a heating apparatus such as a hot plate or an oven, and then heated at 150 ° C to 450 ° C by a heating apparatus such as a hot plate, For example, post-bake for 10 minutes to 5 hours to prepare a desired cured film.

As described above, the cured film has high heat resistance, high transparency, high hardness, and low dielectric constant characteristics, and has a high pattern resolution. Therefore, the cured film can be effectively used for a display element, a semiconductor element, or an optical waveguide material.

For example, the cured film according to one embodiment may have a light transmittance of 95% or more at a wavelength of 400 nm and a retention rate of 87% or more in the case of a cured film having a thickness of 2.5 탆.

The residual film ratio is defined as " (film thickness after development / film thickness after prebaking) x 100 ", and when the residual film ratio is 87% or more, crack resistance is very high at high temperature.

Further, the cured film may exhibit a hole characteristic of less than 7 mu m at 200 DEG C or more. When the hole characteristic is less than 7 탆, it can be considered to have a high resolution.

The conventional acrylic insulating film has a problem that the transmittance decreases due to yellowing at 250 DEG C or higher due to the low heat resistance property and the decomposition of the polymer degrades the chemical resistance due to yellowing. Silsesquioxane containing acrylic group or epoxy group has heat resistance But the transmittance was still lowered at a high temperature and the residual film ratio after the development was low.

Siloxane compounds represented by the general formula (1) according to one embodiment the quinone diazide compound, and a photosensitive resin composition containing the solvent is a siloxane compound in _{(O 3/2 Si-Y} -SiO 3/2) a structural unit represented by, That is, through the role of a crosslinker of the carbosilane structural unit, it is easy to control the hardness of the cured film produced therefrom, and it is possible to form a coating film having high hardness and effectively prevent the organic solvent and the like from penetrating through the cured film . Also, the photosensitive resin composition is characterized in that R ¹ to R ⁶ in the compound represented by the general formula (1) is a substituted or unsubstituted C6 to C30 aryl group based on the content of silicon atoms to which they are bonded, For example, a cured film prepared by curing the composition may have increased crack resistance at high temperatures, since it contains a phenyl group.

Therefore, the cured film can be used as a protective film or an insulating film such as a planarizing film for a thin film transistor (TFT) substrate such as a liquid crystal display element or an organic EL display element, a touch panel sensor element, an interlayer insulating film of a semiconductor element, a planarizing film for a solid- A lens array pattern, or a core or clad material of an optical waveguide such as an optical semiconductor device.

The element may be a liquid crystal display element, an organic EL element, a semiconductor device, a solid-state image pickup element, or the like that includes the cured film as a flattening film of a TFT substrate, but is not limited thereto.

Hereinafter, embodiments of the present invention will be described in detail with reference to examples. The following examples are for illustrative purposes only and are not intended to limit the scope of the invention.

( Example )

Synthetic example 1 to 4: Siloxane Preparation of Copolymer

Synthetic example One: Siloxane Preparation of Copolymer 1

A 500 ml three-necked flask was charged with 42.45 g (0.411 mol) of phenyltrimethoxysilane, 36.99 g (0.514 mol) of methyltrimethoxysilane, 14.05 g (0.075 mol) of 1,2-bistriethoxysilylethane, and 177.34 g, and an aqueous paratoluene sulfonic acid solution in which 3.22 g of para toluenesulfonic acid was dissolved in 30.85 g of water was added over 10 minutes while stirring at room temperature. Thereafter, the flask was immersed in an oil bath at 30 DEG C, stirred for 240 minutes, and then the water layer was removed to prepare a polymer solution dissolved in toluene. The obtained polymer solution was washed with water to remove the residual catalyst, and a further neutral polymer solution was distilled under reduced pressure to obtain a siloxane copolymer solution 1 in which PGMEA (Propylene glycol methyl ether acetate) was finally used as a solvent. The solid content concentration of the obtained siloxane copolymer solution 1 was 30% by weight. The molecular weight of the obtained siloxane copolymer 1 was measured by gel permeation chromatography (GPC). As a result, the weight average molecular weight of the obtained siloxane copolymer 1 was 2,000 g / mol in terms of polystyrene standards.

Synthetic example 2: Siloxane Preparation of Copolymer 2

Siloxane copolymer solution 2 was obtained in the same manner as in Synthesis Example 1, except that the monomers were mixed in the molar ratio shown in Table 1 below. The molecular weight was measured in the same manner as in Synthesis Example 1 and found to be 2,400 g / mol.

Synthetic example 3: Siloxane Preparation of Copolymer 3

Siloxane copolymer solution 3 was obtained in the same manner as in Synthesis Example 1, except that the monomers were mixed in the molar ratio shown in Table 1 below. The molecular weight was measured in the same manner as in Synthesis Example 1 and found to be 2,900 g / mol.

Synthetic example 4: Siloxane Preparation of Copolymer 4

Siloxane copolymer solution 4 was obtained in the same manner as in Synthesis Example 1, except that the monomers were mixed in the molar ratio shown in Table 1 below. The molecular weight was measured in the same manner as in Synthesis Example 1 and found to be 3,700 g / mol.

Synthetic example 5: Siloxane Preparation of Copolymer 5

Siloxane copolymer solution 5 was obtained in the same manner as in Synthesis Example 1, except that the monomers were mixed in the molar ratio shown in Table 1 below. The molecular weight was measured in the same manner as in Synthesis Example 1 and found to be 4,000 g / mol.

Synthesis Example 1 Synthesis Example 2 Synthesis Example 3 Synthesis Example 4 Synthesis Example 5 Phenyltrimethoxysilane 41.1 41.1 41.1 41.1 35.0 Methyltrimethoxysilane 51.4 41.4 31.4 11.4 57.5 Dimethyldimethoxysilane - 10 20 40 - 1,2-bistriethoxysilylethane 7.5 7.5 7.5 7.5 7.5

(In Table 1, the content of each component is mol%)

Example 1 to 3 and Comparative Example 1 and 2: Preparation and evaluation of photosensitive resin composition

Example 1: Preparation and evaluation of composition 1

2 wt% of naphthoquinone diazide compound (MIPHOTO TPA517: Miwon Commercial Co., Ltd.) was added to the siloxane copolymer solution 1 obtained in Synthesis Example 1. PGMEA and GBL were mixed as a solvent under a yellow or the like and stirred to prepare a homogeneous solution, which was then filtered through a 0.20 mu m filter to prepare Composition 1.

The composition 1 was spin-coated on a 10 x 10 glass plate using a spin coater (Mikasa Corporation), pre-baked at 110 占 폚 for 90 seconds using a hot plate (SCW-636, manufactured by Dainippon Screen Mfg. Co., And adjusted to have a film thickness of 3 mu m. After pre-baking, exposure was performed at 100 mJ / cm 2 using an i, g, and h line exposing machine (UX-1200SM-AKS03 available from Ushio), development was performed with a 2.38% TMAH aqueous solution and rinsing with pure water was performed. As a result, it was confirmed that the contact hole (C / H) pattern of 5 占 퐉 was removed without residue. After performing the entire exposure at 1000 mJ / cm < 2 > and baking at 350 [deg.] C, a good shape was maintained with a degree of roundness of 98% and a pattern of 5 [mu] m was maintained.

In Table 2, the remaining film ratios, sensitivity to light, resolution, light transmittance, and pencil hardness of the cured films prepared from the above-prepared compositions were measured by the following methods, respectively, and are shown in Table 2 below:

(1) Remaining film ratio:

It is calculated according to the following formula:

(%) = (Film thickness of non-visible portion after development / film thickness after pre-baking) x 100

(2) Sensitivity to photosensitivity

After development, the amount of exposure (hereinafter referred to as optimal exposure amount) in which a hole pattern of 5 mu m is formed with a width of 1: 1 is defined as a photosensitive sensitivity.

(3) Resolution

The minimum post-development pattern size at the optimum exposure amount is set as the post-development resolution, and the minimum post-curing pattern size is set as the resolution after curing.

(4) Light transmittance

First, only the glass substrate is measured using MultiSpec-1500 (trade name, product of SHIMADZU Corporation), and the ultraviolet visible absorption spectrum thereof is used as a reference. Subsequently, a cured film of the composition was formed on the glass substrate (pattern exposure was not performed), and this sample was measured with a single beam to determine the light transmittance at a wavelength of 400 nm per 1 mu m to determine the difference from the reference as the light transmittance .

(5) Pencil hardness

Using a HEIDON (Type: 14FW) equipment, a cured film of the composition is formed on a glass substrate, the sample is scratched, and the surface is scratched at a rate of 0.1 cm / s while the pencil (hardness 6B to 6H) . The maximum pencil hardness at which the surface of the cured composition is not scratched is set as the hardness of the cured film by increasing the hardness of the pencil in one step.

Example 2: Preparation and evaluation of Composition 2

A naphthoquinone diazide compound (MIPHOTO TPA517: Miwon Commercial Co., Ltd.) was added in an amount of 2% by weight based on the weight of the siloxane copolymer solution 2 obtained in Synthesis Example 2. PGMEA and GBL as a solvent were mixed in a yellow color or the like and stirred to prepare a homogeneous solution, which was then filtered through a 0.20 mu m filter to prepare Composition 2.

Composition 2 was spin-coated on a 10 x 10 glass plate using a spin coater (Mikasa Corporation), pre-baked at 110 占 폚 for 90 seconds using a hot plate (SCW-636, manufactured by Dainippon Screen Mfg. Co., Mu] m. After pre-baking, exposure was performed at 110 mJ / cm 2 using an i, g, and h line exposing machine (UX-1200SM-AKS03 available from Ushio), development was performed with a 2.38% TMAH aqueous solution and rinsing with pure water was performed. As a result, it was confirmed that the contact hole (C / H) pattern of 5 mu m was removed without residue. Further, after the entire exposure was performed at 1000 mJ / cm 2 and the plasticity was cured at 350 ° C, a good shape was maintained at a degree of rounding of the corners at a transmittance of 98%, and a pattern of 5 μm was maintained.

The residual film ratio, sensitivity to light, resolution, light transmittance, and pencil hardness of the cured film prepared from the prepared composition 2 were measured according to the method described in Example 1, and the results are shown in Table 2 below.

Example 3: Preparation and evaluation of Composition 3

A naphthoquinone diazide compound (MIPHOTO TPA517: Miwon Commercial Co., Ltd.) was added in an amount of 2% by weight based on the weight of the siloxane copolymer solution 3 obtained in Synthesis Example 3. PGMEA and GBL were mixed and stirred under a yellow color as a solvent to prepare a homogeneous solution, which was then filtered through a 0.20 탆 filter to prepare Composition 3.

Composition 3 was spin-coated on a 10 x 10 glass substrate using a spin coater (Mikasa Corporation), pre-baked at 110 占 폚 for 90 seconds using a hot plate (SCW-636 manufactured by Dainippon Screen Mfg. Co., Ltd.) Mu] m. After pre-baking, exposure was performed at 110 mJ / cm 2 using an i, g, and h line exposing machine (UX-1200SM-AKS03 available from Ushio), development was performed with a 2.38% TMAH aqueous solution and rinsing with pure water was performed. As a result, it was confirmed that the contact hole (C / H) pattern of 7 mu m was removed without residue. After the entire exposure was performed at 1000 mJ / cm 2, the resin was cured at 350 ° C, and then a good shape was maintained at a degree of roundness at a transmittance of 97%, and a pattern of 7 μm was maintained.

The residual film ratio, sensitivity to light, resolution, light transmittance, and pencil hardness of the cured film prepared from the prepared composition 3 were measured according to the method described in Example 1, and the results are shown in Table 2 below.

Comparative Example 1: Preparation and evaluation of Composition 4

2 wt% of naphthoquinone diazide compound (MIPHOTO TPA517: Miwon Commercial Co., Ltd.) was added to the weight of the siloxane copolymer solution 4 obtained in Synthesis Example 4. PGMEA and GBL were mixed as a solvent under yellow light and stirred to prepare a homogeneous solution, which was then filtered through a 0.20 占 퐉 filter to prepare Composition 4.

Composition 4 was spin-coated on a 10 x 10 glass plate using a spin coater (Mikasa Corporation), prebaked at 120 占 폚 for 90 seconds using a hot plate (SCW-636, manufactured by Dainippon Screen Mfg. Co., Ltd.) Mu] m. After pre-baking, exposure was performed at 110 mJ / cm 2 using an i, g, and h line exposing machine (UX-1200SM-AKS03 available from Ushio), development was performed with a 2.38% TMAH aqueous solution and rinsing with pure water was performed. As a result, it was confirmed that the contact hole (C / H) pattern of 7 mu m was removed without residue. After the entire exposure was performed at 1000 mJ / cm 2, the resin was cured at 350 ° C, and a good shape was maintained with a degree of roundness of 97% at a transmittance of 97%, and a pattern of 7 μm was maintained.

The residual film ratio, sensitivity to light, resolution, light transmittance, and pencil hardness of the cured film prepared from the prepared composition 4 were measured according to the method described in Example 1, and the results are shown in Table 2 below.

Comparative Example 2: Preparation and evaluation of Composition 5

A naphthoquinone diazide compound (MIPHOTO TPA517: Miwon Commercial Co., Ltd.) was added in an amount of 2% by weight based on the weight of the siloxane copolymer solution 5 obtained in Synthesis Example 5. PGMEA and GBL were mixed and stirred under a yellow color as a solvent to prepare a homogeneous solution, which was then filtered through a 0.20 mu m filter to prepare Composition 5.

Composition 5 was spin-coated on a 10 x 10 glass plate using a spin coater (Mikasa Corporation), prebaked at 120 占 폚 for 90 seconds using a hot plate (SCW-636, manufactured by Dainippon Screen Mfg. Co., Ltd.) Mu] m. After pre-baking, exposure was performed at 110 mJ / cm 2 using an i, g, and h line exposing machine (UX-1200SM-AKS03 available from Ushio), development was performed with a 2.38% TMAH aqueous solution and rinsing with pure water was performed. As a result, it was confirmed that the contact hole (C / H) pattern of 5 mu m was developed without residue or the like. In addition, when plastic curing was performed at 350 占 폚 after the entire exposure at 1000 mJ / cm2, cracking occurred and measurement of physical properties after curing was impossible.

The residual film ratio, sensitivity to light, resolution, light transmittance, and pencil hardness of the cured film prepared from the prepared composition 5 were measured according to the method described in Example 1, and the results are shown in Table 2 below.

Siloxane
Copolymer solution After pre-baking
Film thickness
(탆) After development
Film thickness
(탆) Residual film ratio
(%) Sensitivity to light
(mJ / cm 2) After curing
resolution
(탆) ore
Transmittance
(%) After curing
Pencil hardness Example 1 Synthesis Example 1 3.01 2.72 90.36 100 5 98 4H Example 2 Synthesis Example 2 3.05 2.70 88.92 110 5 98 3H Example 3 Synthesis Example 3 3.03 2.69 88.78 110 7 97 2H Comparative Example 1 Synthesis Example 4 3.12 2.70 86.54 120 7 96 3B Comparative Example 2 Synthesis Example 5 3.07 2.67 86.97 110 Not measurable Not measurable Not measurable

As can be seen from the above Table 2, the photosensitive resin composition according to one embodiment, that is, the siloxane compound represented by the general formula (1), has a structure in which R ¹ to R ⁶ in the general formula (1) Examples comprising a compound containing a substituted or unsubstituted C6 to C30 aryl group of at least mol% and having a structural unit represented by T1 in an amount of 60 mol% or more and a structural unit represented by T2 in an amount of less than 20 mol% The cured film prepared by curing the photosensitive resin composition of Examples 1 to 3 has a residual film ratio of 85% or more at a thickness of 2 占 퐉 after drying, a resolution after curing of less than 7 占 퐉, and a light transmittance of 95 %, A pencil hardness of 2H or more It can be seen that a hard hardened film can be produced. It is also understood that the photosensitive resin compositions of Examples 1 to 3 can be patterned at a low exposure dose of 110 mJ / cm 2.

On the other hand, in the case of the photosensitive resin composition according to Comparative Example 1 in which the content of the structural unit represented by T1 in the formula (1) does not become 50 mol% or the D structure exceeds 40 mol%, the photosensitivity It can be seen that the resin composition has a lower residual film ratio, a higher energy is required for pattern formation, a lower resolution after curing, a lower light transmittance, and a markedly lower hardness than anything else. On the other hand, when the photosensitive resin of Comparative Example 2 having a phenyl group content of less than 40 mol% was used, cracks occurred after curing.

As a result, it can be seen that the photosensitive resin composition according to one embodiment has high resolution and residual film ratio after curing, high light transmittance, high hardness, and pattern formation with low energy.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, but, on the contrary, And falls within the scope of the present invention.

Claims

(A) a siloxane compound represented by the following formula (1); (B) a quinone diazide compound, and (C) a solvent.
[Chemical Formula 1]
^{(R 1 R 2 R 3 SiO} 1/2) M (R 4 R 5 SiO 2/2) D (R 6 SiO 3/2) T1 (O 3/2 Si-Y-SiO 3/2) T2 (SiO _4/2 ) _Q
In Formula 1,
R ¹ to R ⁶ are each independently hydrogen, halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, A substituted or unsubstituted C1 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C2 to C30 alkane group, a substituted or unsubstituted C2 to C30 alkynyl group, or being a combination thereof, wherein R ¹ to R of more than 40 mol%, based on the amount of silicon atoms to which the ^hexavalent coupling R ¹ to R ⁶ is substituted or unsubstituted C 6 -C 30 aryl group,
Y is a single bond, oxygen, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 hetero A substituted or unsubstituted C2 to C30 alkenylene group, a substituted or unsubstituted C2 to C20 alkynylene group, or a combination thereof,
0 < 0.4, 0 < D < 0.4, 0.6 &
M + D + T1 + T2 + Q = 1,
The structural units represented by M, D, T1, T2, and Q may each include one or more different structural units.

The positive photosensitive resin composition according to claim 1, wherein M and Q are 0, 0? D? 0.2, 0.65? T1 <1, and 0 <T2 <0.2.

The positive photosensitive resin composition according to claim 1, wherein M and Q are all 0, 0? D? 0.2, 0.7? T1 <1, and 0 <T2?

The positive photosensitive resin composition according to claim ¹ , wherein R ¹ to R ⁶ are a substituted or unsubstituted C6 to C30 aryl group in an amount of not less than 40 mol% based on the content of Si atoms to which they are bonded.

The positive photosensitive resin composition according to claim 1, wherein the substituted or unsubstituted C6 to C30 aryl group is a phenyl group, and the substituted or unsubstituted C1 to C30 alkyl group is a C1 to C4 alkyl group.

The positive photosensitive resin composition according to claim 1, wherein Y is a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, or a substituted or unsubstituted C6 to C30 arylene group.

A cured film obtained by curing the photosensitive resin composition according to any one of claims 1 to 6.

The method of claim 7, wherein the cured film is a planarizing film for a thin film transistor (TFT) substrate of a liquid crystal display element or an organic EL display element, a protective film or insulating film of a touch panel sensor element, an interlayer insulating film of a semiconductor element, A micro lens array pattern, or a cured film which is a core or clad material of an optical waveguide of an optical semiconductor element.

The cured film according to claim 7, wherein the cured film exhibits a hole characteristic of less than 7 占 퐉 at a temperature of 200 占 폚 or more and a light transmittance of 95% or more at a wavelength of 400 nm at a thickness of 2.5 占 퐉.

The cured film according to claim 7, wherein the cured film has a residual film ratio of 87% or more, which is defined as (film thickness of unexposed area after development / film thickness after pre-baking) x 100.

An electronic device comprising the cured film according to claim 7.