KR20170050705A - Photo-sensitive Composition, Cured Film Prepared Therefrom, and Device Incoporating the Cured Film - Google Patents

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

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KR20170050705A
KR20170050705A KR1020150152578A KR20150152578A KR20170050705A KR 20170050705 A KR20170050705 A KR 20170050705A KR 1020150152578 A KR1020150152578 A KR 1020150152578A KR 20150152578 A KR20150152578 A KR 20150152578A KR 20170050705 A KR20170050705 A KR 20170050705A
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substituted
unsubstituted
group
weight
film
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KR1020150152578A
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KR101862710B1 (en
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백택진
김우한
김태수
김하늘
박종희
백윤희
송규석
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삼성에스디아이 주식회사
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Priority to KR1020150152578A priority Critical patent/KR101862710B1/en
Priority to PCT/KR2016/011429 priority patent/WO2017073935A1/en
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/022—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
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • 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
    • G03F7/004—Photosensitive materials
    • G03F7/075—Silicon-containing compounds
    • G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Materials For Photolithography (AREA)
  • Silicon Polymers (AREA)

Abstract

(A) a siloxane compound represented by the following formula (1); Wherein the siloxane compound represented by the formula (1) is at least one compound selected from the group consisting of (i) a siloxane compound represented by the following formula (i) and (ii) Of a siloxane compound represented by the following formula (1): < EMI ID =
(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
(Wherein R 1 to R 6 , Y, M, D, T 1, T 2 and Q are as defined in the description of the invention).
(i) a polystyrene standard sample-converted weight average molecular weight of 3,000 g / mole or less measured by gel permeation chromatography (GPC) and a dissolution rate of the prebaked film in a 2.38% by weight aqueous TMAH solution of 1,500 Å / Siloxane compounds; (ii) a polystyrene standard sample-converted weight average molecular weight of not less than 3,000 g / mole and not more than 6,000 g / mole measured by gel permeation chromatography and having a dissolution rate in a 2.38% by weight aqueous solution of TMAH in a prebaked film of not less than 200 Å / A / sec or less; And (iii) a polystyrene standard sample-converted weight average molecular weight measured by gel permeation chromatography of 6,000 g / mole or more and a dissolution rate in a 5.0 wt% TMAH aqueous solution of the prebaked membrane of 200 to 3,000 Å / Siloxane compound.

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 photosensitive resin composition having high heat resistance, crack resistance at high temperature, high permeability, high resolution, and high residual film ratio without causing pattern flow at high temperature and scum after development.

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); Wherein the siloxane compound represented by the formula (1) is at least one of the siloxane compounds (i) and (ii), (iii) the siloxane compound represented by the formula (1) Of a siloxane compound represented by the following general formula

[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 the 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 C 2 to C 30 alkynyl group, a substituted or unsubstituted C 2 to C 30 alkynyl group, a substituted or unsubstituted C 2 to C 30 alkynyl group, a substituted or unsubstituted C 2 to C 30 alkynyl group, A substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C7 to C30 arylalkyl group), or a combination thereof,

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 < 0.5 < 0.5, 0.5 <

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.

(i) a polystyrene standard sample-converted weight average molecular weight of 3,000 g / mole or less measured by gel permeation chromatography (GPC) and a dissolution rate of the prebaked film in a 2.38% by weight aqueous TMAH solution of 1,500 Å / Siloxane compounds;

(ii) a polystyrene standard sample-converted weight average molecular weight of not less than 3,000 g / mole and not more than 6,000 g / mole measured by gel permeation chromatography and having a dissolution rate in a 2.38% by weight aqueous solution of TMAH in a prebaked film of not less than 200 Å / A / sec or less; And

(iii) a siloxane having a weight average molecular weight of 6,000 g / mole or more in terms of polystyrene standard sample measured by gel permeation chromatography and having a dissolution rate in a 5.0 wt% TMAH aqueous solution of the prebaked film of 200 Å / sec or more and 3,000 Å / compound.

In the formula (1), M, D and Q are all 0, and 0.8 < T1 < 1, and 0 <

In the formula (1), M, D and Q are all 0, 0.85? T1 <1, and 0 <T2? 0.15.

In Formula (1), at least one of R 1 to R 6 includes a substituted or unsubstituted C6 to C30 aryl group, and at least one of R 1 to R 6 may include a substituted or unsubstituted C1 to C30 alkyl group have.

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.

The siloxane compound (i) may be contained in an amount of 20 to 80% by weight based on the total weight of the siloxane compound represented by the formula (1).

The siloxane compound (ii) may be contained in an amount of 20 to 80% by weight based on the total weight of the siloxane compound represented by the formula (1).

The siloxane compound (iii) may be contained in an amount of 10% by weight to 70% by weight based on the total weight of the siloxane compound represented by the formula (1).

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 占 퐉 at a temperature of 200 占 폚 or more and a light transmittance of 90% or more at a wavelength of 400 nm at a thickness of 2.5 占 퐉.

The cured film has a residual film ratio of 85% or more, which is defined as &quot; (film thickness after development / non-exposed portion thickness / pre-baked film thickness) x 100 &quot;.

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

The photosensitive resin composition according to one embodiment is a positive photosensitive resin composition having high heat resistance, crack resistance at high temperature, high permeability, and high resolution, which does not generate scum after pattern collapse or development at high temperature, The film can be usefully used for manufacturing 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, wherein the siloxane compound represented by the formula (1) comprises at least one siloxane compound of the following (i) and (ii) Mixtures include:

[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 the 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 C 2 to C 30 alkynyl group, a substituted or unsubstituted C 2 to C 30 alkynyl group, a substituted or unsubstituted C 2 to C 30 alkynyl group, a substituted or unsubstituted C 2 to C 30 alkynyl group, A substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C7 to C30 arylalkyl group), or a combination thereof,

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 < 0.5 < 0.5, 0.5 <

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.

(i) a polystyrene standard sample-converted weight average molecular weight of 3,000 g / mole or less measured by gel permeation chromatography (GPC) and a dissolution rate of the prebaked film in a 2.38% by weight aqueous TMAH solution of 1,500 Å / Siloxane compounds;

(ii) a polystyrene standard sample-converted weight average molecular weight of not less than 3,000 g / mole and not more than 6,000 g / mole measured by gel permeation chromatography and having a dissolution rate in a 2.38% by weight aqueous solution of TMAH in a prebaked film of not less than 200 Å / A / sec or less; And

(iii) a siloxane having a weight average molecular weight of 6,000 g / mole or more in terms of polystyrene standard sample measured by gel permeation chromatography and having a dissolution rate in a 5.0 wt% TMAH aqueous solution of the prebaked film of 200 Å / sec or more and 3,000 Å / compound.

As shown by the above formula (1), the siloxane compound comprises at least 0.5 mole fraction of the structural unit as represented by (R 6 SiO 3/2) in the compounds, and (O 3/2 Si-Y -SiO 3 / 2 ) may be contained in an amount of 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.

As described above, the siloxane compound represented by the above formula (1) has (i) a weight average molecular weight in terms of polystyrene standard sample of 3,000 g / mole or less measured by gel permeation chromatography and a 2.38% by weight aqueous solution of TMAH (Ii) a weight average molecular weight of not less than 3,000 g / mole and not more than 6,000 g / mole in terms of a polystyrene standard sample measured by gel permeation chromatography, and a 2.38% by weight aqueous solution of TMAH in a prebaked film And a siloxane compound having a dissolution rate of not less than 200 Å / s and not more than 1,500 Å / s; And (iii) a polystyrene standard sample-converted weight average molecular weight measured by gel permeation chromatography of 6,000 g / mole or more and a dissolution rate in a 5.0 wt% TMAH aqueous solution of the prebaked membrane of 200 to 3,000 Å / Is used as a mixture containing a siloxane compound.

The cured film obtained by curing the photosensitive resin composition by using the siloxane compound represented by the formula (1) as a combination of the siloxane compounds having the specific molecular weight range and the specific dissolution rate for the TMAH aqueous solution of the prebaked film at the above specified range, A residual film ratio of 85% or more, which is defined as &quot; (film thickness after development / film thickness after pre-baking) x 100 &quot;, and a cured film thickness of 2.5 m and a wavelength of 400 nm High heat resistance, high transmittance, and high resolution of a photosensitive resin composition having a light transmittance of 90% or more can be provided.

When the hole property is less than 7 占 퐉, it can be considered that the cured film obtained from the composition has sufficiently high resolution.

Further, when the residual film ratio obtained by multiplying the value obtained by dividing the film thickness after pre-baking by 100 in the film thickness of the unexposed portion after development by 85% or more, it can be considered to have a residual film ratio sufficient to be used as the photosensitive resin composition.

On the other hand, as can be seen from the comparative examples to be described later, the compound represented by the above formula (1) includes a combination of the above-mentioned molecular weight ranges and / or compounds in which the dissolution rate range for the TMAH film prepared therefrom does not satisfy the above range , The cured film that is cured from the composition does not exhibit the above-mentioned hole property and residual film ratio.

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, 0.75? T1 <1, for example, 0.8? T1 <1.

In the case where the structural unit represented by T1 among the compounds represented by the above-mentioned general formula (1), that is, (R 6 SiO 3/2 ) is present within the above-mentioned range within the above-mentioned compound, the polystyrene standard sample conversion measured by gel permeation chromatography It is possible to easily produce a siloxane compound having a weight average molecular weight of 3,000 g / mole to 6,000 g / mole, and at the same time dissolving rate of the prebake film to aqueous solution of 2.38% by weight TMAH of 200 Å / second to 1,500 Å / second.

In addition, in one embodiment, the structural unit represented by the T2 of the structural units constituting the compound of the formula (1), i.e., (O 3/2 Si- Y-SiO 3/2) is 0 <T2 <0.2, For example, 0 <T2? 0.17, for example 0 <T2? 0.15, for example 0 <T2? 0.13, for example 0 <T2? 0.12.

When the structural unit represented by the formula (1) is contained in the above range, the photosensitive resin composition comprising the compound has an effect of improving the surface hardness, residual film ratio and chemical resistance after curing.

In one embodiment, M, D and Q of formula (1) are all 0, 0.8 < T1 < 1, and 0 <

In another embodiment, M, D, and Q in Formula 1 are all 0, 0.85 < T1 < 1, and 0 &lt;

The siloxane compound (i) may be contained in an amount of 20 to 80% by weight based on the total weight of the siloxane compound represented by the formula (1).

Within this range, the siloxane compound (i) may be present in an amount of, for example, 25 wt% to 75 wt%, for example, 25 wt% to 70 wt%, based on the total weight of the siloxane compound represented by Formula By weight, for example, from 30% by weight to 65% by weight.

The siloxane compound (ii) may be contained in an amount of 20 to 80% by weight based on the total weight of the siloxane compound represented by the formula (1).

Within this range, the siloxane compound of (ii) may include, for example, from 30 wt% to 75 wt%, for example, from 35 wt% to 70 wt%, based on the total weight of the siloxane compound represented by Formula The siloxane compound (iii) may be contained in an amount of 10 to 70% by weight, based on the total weight of the siloxane compound represented by the formula (1) .

Within this range, the siloxane compound of (iii) may be present in an amount of, for example, from 15 wt% to 65 wt%, for example, from 15 wt% to 60 wt%, based on the total weight of the siloxane compound represented by Formula By weight, for example, from 20% by weight to 60% by weight.

In Formula (1), at least one of R 1 to R 6 includes a substituted or unsubstituted C6 to C30 aryl group, and at least one of R 1 to R 6 may include a substituted or unsubstituted C1 to C30 alkyl group have.

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.

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 0.001 to 10 parts by weight, for example, 0.1 to 8 parts by weight based on 100 parts by weight of the total weight of the monomers.

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)

Figure pat00001

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.).

Figure pat00002

Figure pat00003

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 non-exposed portion is too low to have practically no photosensitivity. 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 &gt; 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 whitened, 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 ° C to 150 ° C for 30 seconds to 30 minutes, and the film thickness after prebaking may be 0.1 to 15 μm.

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 (corresponding to a wavelength of 365 nm in terms of an exposure dose) using an ultraviolet ray 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, transparency, crack resistance, dielectric constant and solvent resistance, and 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 of the present invention may have a light transmittance of 90% or more, for example, 92% or more, for example, 95% or more at a wavelength of 400 nm for a 2 탆 thick cured film And has a residual film ratio of 70% or more, for example, 75% or more, for example, 80% or more.

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, so that a coating film having a high hardness can be formed, thereby improving crack resistance at high temperature, It is possible to effectively prevent penetration of organic solvents and the like. Thus, the cured film prepared by curing the composition has a problem that the film thickness after development is reduced to prevent a residual film ratio problem that can not form a flat film, and there is no pattern collapse due to excellent chemical resistance after curing. In addition, it has higher heat resistance than silsesquioxane copolymerized with an existing acrylic copolymer or organic compound, so that it does not discolor even at a curing temperature of 350 ° C or higher.

The cured film may be a protective film or an insulating film such as a flattening 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 flattening film for a solid- Pattern or a core or clad material of an optical waveguide such as an optical semiconductor device.

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

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  One: Polysiloxane  Produce

In a 500 ml three-necked flask, 66.75 g (0.49 mol) of methyltrimethoxysilane, 89.24 g (0.45 mol) of phenyltrimethoxysilane, 21.28 g (0.06 mol) of 1,2-bistriethoxysilylethane, 177.27 g of PGMEA was added, and an aqueous nitric acid solution containing 0.315 g (50 ppm) of nitric acid dissolved in 21.62 g of water was added over 10 minutes while stirring at room temperature. Thereafter, the flask was immersed in an oil bath at 25 DEG C and stirred for 60 minutes, and then the oil bath was heated to 110 DEG C over 60 minutes. The resulting mixture was heated and stirred for 2 hours (internal temperature: 100 to 110 ° C) to obtain a polysiloxane solution. During the reaction, a total of 67.3 g of the by-product methanol and water were spilled out. The solid content concentration of the obtained polysiloxane solution was 40% by weight. The molecular weight (in terms of polystyrene) of the obtained polysiloxane was a weight average molecular weight (Mw) = 1,970. The obtained resin solution was coated on a silicon wafer so that the film thickness after pre-baking was 2 占 퐉, and the dissolution rate in a 2.38% TMAH aqueous solution was measured at room temperature to be 1750 占 sec.

The composition and molecular weight of the polysiloxane thus prepared, and the dissolution rate in aqueous TMAH solution after prebaking are shown in Table 1 below.

Synthetic example  2: Polysiloxane  Produce

In a 500 ml three-necked flask, 66.75 g (0.46 mol) of methyltrimethoxysilane, 89.24 g (0.45 mol) of phenyltrimethoxysilane, 31.91 g (0.09 mol) of 1,2-bistriethoxysilylethane, 187.9 g of PGMEA was added, and an aqueous nitric acid solution containing 0.315 g (50 ppm) of nitric acid dissolved in 21.62 g of water was added over 10 minutes while stirring at room temperature. Thereafter, the flask was immersed in an oil bath at 25 DEG C and stirred for 60 minutes, and then the oil bath was heated to 110 DEG C over 60 minutes. Thereafter, the mixture was heated and stirred for 4 hours (internal temperature: 100 to 110 ° C) to obtain a polysiloxane solution. During the reaction, 73.75 g of methanol and water as a by-product were spilled out. The solid content concentration of the obtained polysiloxane solution was 40% by weight. The molecular weight (in terms of polystyrene) of the obtained polysiloxane had a weight average molecular weight (Mw) = 4,750. The obtained resin solution was coated on a silicon wafer so that the film thickness after pre-baking was 2 占 퐉 and the dissolution rate in a 2.38% TMAH aqueous solution was measured and found to be 820 占 sec.

The composition and molecular weight of the polysiloxane thus prepared, and the dissolution rate in aqueous TMAH solution after prebaking are shown in Table 1 below.

Synthetic example  3: Polysiloxane  Produce

58.57 g (0.43 mol) of methyltrimethoxysilane, 89.24 g (0.45 mol) of phenyltrimethoxysilane and 42.55 g (0.12 mol) of 1,2-bistriethoxysilylethane were added to a 500-ml three- 190.36 g of PGMEA was added, and an aqueous nitric acid solution containing 0.315 g (50 ppm) of nitric acid dissolved in 21.62 g of water was added over 10 minutes while stirring at room temperature. Thereafter, the flask was immersed in an oil bath at 25 DEG C and stirred for 60 minutes, and then the oil bath was heated to 110 DEG C over 60 minutes. Thereafter, the mixture was heated and stirred for 5 hours (internal temperature: 100 to 110 ° C) to obtain a polysiloxane solution. During the reaction, a total of 97.25 g of the by-product methanol and water were spilled out. The solid content concentration of the obtained polysiloxane solution was 40% by weight. The molecular weight (in terms of polystyrene) of the obtained polysiloxane had a weight average molecular weight (Mw) = 6,920. The obtained resin solution was coated on a silicon wafer so that the film thickness after prebaking was 2 占 퐉, and the dissolution rate in a 5% TMAH aqueous solution was measured and found to be 350 占 sec.

The composition and molecular weight of the polysiloxane thus prepared, and the dissolution rate in aqueous TMAH solution after prebaking are shown in Table 1 below.

Synthetic example  4: Polysiloxane  Produce

In a 500 ml three-necked flask, 68.11 g (0.50 mol) of methyltrimethoxysilane, 89.24 g (0.45 mol) of phenyltrimethoxysilane, 17.73 g (0.05 mol) of 1,2-bistriethoxysilylethane, 175.08 g of PGMEA was added, and an aqueous nitric acid solution containing 0.315 g (50 ppm) of nitric acid dissolved in 21.62 g of water was added over 10 minutes while stirring at room temperature. Thereafter, the flask was immersed in an oil bath at 25 DEG C and stirred for 60 minutes, and then the oil bath was heated to 110 DEG C over 60 minutes. Thereafter, the mixture was heated and stirred for 1 hour (internal temperature of 100 to 110 ° C) to obtain a solution of polysiloxane D. During the reaction, a total of 59.36 g of the by-product methanol and water were spilled out. The solid content concentration of the obtained polysiloxane solution was 40% by weight. The molecular weight (in terms of polystyrene) of the obtained polysiloxane was a weight average molecular weight (Mw) = 1,765. The obtained resin solution was coated on a silicon wafer so that the film thickness after pre-baking was 2 占 퐉, and the dissolution rate in a 2.38% TMAH aqueous solution was measured. As a result, it was 6000 占 sec.

The composition and molecular weight of the polysiloxane thus prepared, and the dissolution rate in aqueous TMAH solution after prebaking are shown in Table 1 below.

Synthetic example  5: Polysiloxane  Produce

74.92 g (0.55 mol) of methyltrimethoxysilane, 89.24 g (0.45 mol) of phenyltrimethoxysilane and 164.16 g of PGMEA were added to a 500 ml three-necked flask, and while stirring at room temperature, 21.62 g of TMAH 0.456 g (50 ppm) dissolved in TMAH was added over 10 minutes. Thereafter, the flask was immersed in an oil bath at 25 DEG C and stirred for 60 minutes, and then the oil bath was heated to 110 DEG C over 60 minutes. Thereafter, the mixture was heated and stirred for 3 hours (internal temperature was 100 to 110 ° C) to obtain a polysiloxane solution. During the reaction, a total of 59.36 g of the by-product methanol and water were spilled out. The solid content concentration of the obtained polysiloxane solution was 40% by weight. The molecular weight (in terms of polystyrene) of the obtained polysiloxane had a weight average molecular weight (Mw) = 3,130. The obtained resin solution was coated on a silicon wafer so that the film thickness after pre-baking was 2 占 퐉, and the dissolution rate in a 2.38% TMAH aqueous solution was measured and found to be 160 占 sec.

The composition and molecular weight of the polysiloxane thus prepared, and the dissolution rate in aqueous TMAH solution after prebaking are shown in Table 1 below.

Synthetic example  6: Polysiloxane  Produce

In a 500 ml three-necked flask, 68.11 g (0.50 mol) of methyltrimethoxysilane, 89.24 g (0.45 mol) of phenyltrimethoxysilane, 17.73 g (0.05 mol) of 1,2-bistriethoxysilylethane, 175.08 g of PGMEA was added, and an aqueous solution of TMAH in which 0.456 g (50 ppm) of TMAH was dissolved in 21.62 g of water was added over 10 minutes while stirring at room temperature. Thereafter, the flask was immersed in an oil bath at 25 DEG C and stirred for 60 minutes, and then the oil bath was heated to 110 DEG C over 60 minutes. Thereafter, the mixture was heated and stirred for 3 hours (internal temperature was 100 to 110 ° C) to obtain a polysiloxane solution. During the reaction, a total of 59.36 g of the by-product methanol and water were spilled out. The solid content concentration of the obtained polysiloxane solution was 40% by weight. The molecular weight (in terms of polystyrene) of the obtained polysiloxane was a weight average molecular weight (Mw) = 1,765. The obtained resin solution was coated on a silicon wafer so that the film thickness after pre-baking was 2 占 퐉, and the dissolution rate in a 2.38% TMAH aqueous solution was measured. As a result, it was 6000 占 sec.

The composition and molecular weight of the polysiloxane thus prepared, and the dissolution rate in aqueous TMAH solution after prebaking are shown in Table 1 below.

MeSiO 3/2
(mole%) PheSiO 3/2
(mole%) O 3/2 Si-CH 2 CH 2 -SiO 3/2 (% mol) catalyst Molecular Weight
(g / mole) Dissolution rate 2.38% TMAH
(Å / sec) 5% TMAH
(Å / sec) Synthesis Example 1 49 45 6 mountain 1970 1750 - Synthesis Example 2 46 45 9 mountain 4750 820 - Synthesis Example 3 43 45 12 mountain 6920 - 350 Synthesis Example 4 50 45 5 mountain 1765 6000 - Synthesis Example 5 55 45 0 alkali 3130 160 - Synthesis Example 6 50 45 5 alkali 4260 - 200

Example  And evaluation: Photosensitive resin composition and Cured film  Manufacturing and Evaluation

The photosensitive resin compositions according to the following examples and comparative examples were prepared by mixing the polysiloxane and the naphthoquinone diazide compound prepared in the above Synthesis Example and a solvent, and the compositions prepared in each of the Examples and Comparative Examples were coated Baked, exposed, developed, and rinsed with pure water. Then, the diameter of the contact hole is measured and the residual film ratio is calculated. Further, after the entire surface is exposed, the plasticity is cured at 350 DEG C, and then the transmittance is measured and the shape of the film is observed. Each of the measurements was carried out in the following manner and the results are shown in Table 2 below:

(1) Calculation of the residual film ratio

The residual film ratio was calculated according to the following formula.

Remaining film ratio (%) = (film thickness after development / film thickness after prebaking) x 100

(2) Calculation of photosensitivity

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

(3) Resolution

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

(4) Measurement of light transmittance

First, only the glass substrate was measured using MultiSpec-1500 (trade name, product of SHIMADZU Corporation), and the ultraviolet visible absorption spectrum thereof was taken as a reference. Subsequently, a cured film of a photosensitive resin 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 m, And the light transmittance was determined.

Example  1: Photosensitive resin composition and Cured film  Manufacturing and Evaluation

50% by weight of the polysiloxane obtained in Synthesis Example 1 and 50% by weight of the polysiloxane obtained in Synthesis Example 3 were mixed, and a naphthoquinone diazide compound (MIPHOTO TPA517: Miwon Commercial Co., Ltd.) 2% by weight as a standard. A solvent mixed with PGMEA and GBL was added thereto, and the mixture was mixed under yellow light and stirred to obtain a homogeneous solution, which was then filtered through a 0.2 탆 filter to prepare a photosensitive resin composition.

The composition was spin-coated on a 10 x 10 layer using a spin coater (Mikasa Corporation), pre-baked at 110 DEG C for 90 seconds using a hot plate (SCW-636, manufactured by Dainippon Screen Mfg. Co., Ltd.) Mu] m. After prebaking, exposure was performed at 120 mJ / cm 2 using an i, g, and h line exposing machine (UX-1200SM-AKS03 available from Ushio), developed with 2.38% aqueous TMAH solution and rinsed with pure water. As a result, it was confirmed that the contact hole (C / H) pattern of 5 탆 was removed without residue. Further, after the entire exposure was performed at 1,000 mJ / cm 2 and plastic curing was carried out at 350 ° C, a good shape was maintained with a degree of roundness at a transmittance of 97%, and a pattern of 5 μm was maintained.

Example  2: Photosensitive resin composition and Cured film  Manufacturing and Evaluation

A photosensitive resin composition was prepared in the same manner as in Example 1 except that 50% by weight of the polysiloxane obtained in Synthesis Example 2 and 50% by weight of the polysiloxane obtained in Synthesis Example 3 were used, and a cured film was prepared by the same method .

The cured film was subjected to development and cleaning under the same conditions as in Example 1. As a result, it was confirmed that a contact hole (C / H) pattern of 3.5 μm was removed without residue. Further, the entire surface was exposed at 1,000 mJ / cm 2 and subjected to firing and curing at 350 ° C. As a result, a good shape was maintained with a degree of roundness at a transmittance of 97%, and a pattern of 3.5 μm was maintained.

Example  3: Photosensitive resin composition and Cured film  Manufacturing and Evaluation

A photosensitive resin composition was prepared in the same manner as in Example 1, except that 30% by weight of the polysiloxane obtained in Synthesis Example 1, 50% by weight of the polysiloxane obtained in Synthesis Example 2 and 20% by weight of the polysiloxane obtained in Synthesis Example 3 were used And a cured film was prepared therefrom in the same manner.

The cured film was developed and cleaned under the same conditions as in Example 1, and as a result, it was confirmed that a contact hole (C / H) pattern of 5 탆 was removed without residue. Further, the entire surface was exposed at 1,000 mJ / cm 2 and subjected to firing and curing at 350 ° C. As a result, a good shape was maintained with a degree of rounding at 98%, and a pattern of 5 μm was maintained.

Example  4: Photosensitive resin composition and Cured film  Manufacturing and Evaluation

A mixed solution was prepared in the same manner as in Example 1, except that 30% by weight of the polysiloxane obtained in Synthesis Example 1, 40% by weight of the polysiloxane obtained in Synthesis Example 2, and 30% by weight of the polysiloxane obtained in Synthesis Example 3 were used And a cured film was prepared therefrom in the same manner.

The cured film was developed and cleaned under the same conditions as in Example 1, and as a result, it was confirmed that a contact hole (C / H) pattern of 4 탆 was removed without residue. Further, the entire surface was exposed at 1,000 mJ / cm 2 and subjected to firing and curing at 350 ° C. As a result, a good shape was maintained with a degree of roundness of 98%, and a pattern of 4 μm was maintained.

Example  5: Photosensitive resin composition and Cured film  Manufacturing and Evaluation

A mixed solution was prepared in the same manner as in Example 1 except that 40% by weight of the polysiloxane obtained in Synthesis Example 1, 40% by weight of the polysiloxane obtained in Synthesis Example 2, and 20% by weight of the polysiloxane obtained in Synthesis Example 3 were used And a cured film was prepared therefrom in the same manner.

The cured film was developed and cleaned under the same conditions as in Example 1, and as a result, it was confirmed that a contact hole (C / H) pattern of 4 탆 was removed without residue. Further, the entire surface was exposed at 1,000 mJ / cm 2 and subjected to firing and curing at 350 ° C. As a result, a good shape was maintained with a degree of roundness of 98%, and a pattern of 4 μm was maintained.

Example  6: Photosensitive resin composition and Cured film  Manufacturing and Evaluation

A mixed solution was prepared in the same manner as in Example 1 except that 35% by weight of the polysiloxane obtained in Synthesis Example 1, 45% by weight of the polysiloxane obtained in Synthesis Example 2, and 20% by weight of the polysiloxane obtained in Synthesis Example 3 were used And a cured film was prepared therefrom in the same manner.

The cured film was developed and cleaned under the same conditions as in Example 1, and as a result, it was confirmed that a contact hole (C / H) pattern of 5 mu m was removed without residue. Further, the entire surface was exposed at 1,000 mJ / cm 2 and subjected to firing and curing at 350 ° C. As a result, a good shape was maintained with a degree of rounding at 98%, and a pattern of 5 μm was maintained.

Comparative Example  1: Photosensitive resin composition and Cured film  Manufacturing and Evaluation

A mixed solution was prepared in the same manner as in Example 1 except that 50% by weight of the polysiloxane obtained in Synthesis Example 4 and 50% by weight of the polysiloxane obtained in Synthesis Example 6 were used, and a cured film was prepared from the same manner .

The cured film was developed and cleaned under the same conditions as in Example 1, and as a result, it was confirmed that a contact hole (C / H) pattern of 15 mu m was removed without residue. Further, the entire surface was exposed at 1,000 mJ / cm 2 and subjected to firing and curing at 350 ° C. As a result, a good shape was maintained with a degree of roundness at a transmittance of 97%, and a pattern of 15 μm was maintained.

Comparative Example  2:: Photosensitive resin composition and Cured film  Manufacturing and Evaluation

A mixed solution was prepared in the same manner as in Example 1 except that 50% by weight of the polysiloxane obtained in Synthesis Example 4 and 50% by weight of the polysiloxane obtained in Synthesis Example 5 were used, and a cured film was prepared from the same manner .

The cured film was developed and cleaned under the same conditions as in Example 1. As a result, it was confirmed that a contact hole (C / H) pattern of 10 mu m was removed without residue. Further, the entire surface was exposed at 1,000 mJ / cm 2 and subjected to firing and curing at 350 ° C. As a result, a good shape was maintained with a degree of roundness at a transmittance of 97%, and a pattern of 10 μm was maintained.

Comparative Example  3: Photosensitive resin composition and Cured film  Manufacturing and Evaluation

A mixed solution was prepared in the same manner as in Example 1 except that 50% by weight of the polysiloxane obtained in Synthesis Example 5 and 50% by weight of the polysiloxane obtained in Synthesis Example 6 were used, and a cured film was prepared from the same manner .

The cured film was developed and cleaned under the same conditions as in Example 1, and as a result, it was confirmed that a contact hole (C / H) pattern of 20 mu m was removed without residue. Further, the entire surface was exposed at 1,000 mJ / cm 2 and subjected to firing and curing at 350 ° C. As a result, a good shape was maintained with a degree of roundness at a transmittance of 97%, and a pattern of 20 μm was maintained.

Comparative Example  4: Photosensitive resin composition and Cured film  Manufacturing and Evaluation

A mixed solution was prepared in the same manner as in Example 1 except that 35% by weight of the polysiloxane obtained in Synthesis Example 4, 45% by weight of the polysiloxane obtained in Synthesis Example 5, and 20% by weight of the polysiloxane obtained in Synthesis Example 6 were used And a cured film was prepared therefrom in the same manner.

The cured film was subjected to development and cleaning under the same conditions as in Example 1, and as a result, it was confirmed that a contact hole (C / H) pattern of 7 탆 was removed without residue. Further, the entire surface was exposed at 1,000 mJ / cm &lt; 2 &gt; and subjected to firing and curing at 350 DEG C, and as a result, a good shape was maintained with a degree of roundness at a transmittance of 97% and a pattern of 7 mu m was maintained.

Siloxane
Copolymer After pre-baking
Film thickness
(탆) After development
Film thickness
(탆) Residual film ratio
(%) Sensitivity to light
(mJ / cm 2) After curing
resolution
(탆) Light transmittance
(%) Example 1 Synthesis Example 1 + 3 3.01 2.71 90.03 120 5 97 Example 2 Synthesis Example 2 + 3 3.10 2.72 89.45 100 3.5 97 Example 3 Synthesis Example 1 + 2 + 3 3.03 2.70 89.11 50 5 98 Example 4 Synthesis Example 1 + 2 + 3 3.12 2.70 86.54 100 4 98 Example 5 Synthesis Example 1 + 2 + 3 3.11 2.73 87.78 70 4 98 Example 6 Synthesis Example 1 + 2 + 3 2.98 2.73 91.61 50 5 97 Comparative Example 1 Synthesis Example 4 + 6 3.33 2.70 82 120 15 97 Comparative Example 2 Synthesis Example 4 + 5 3.34 2.70 82 100 10 97 Comparative Example 3 Synthesis Example 5 + 6 3.36 2.72 82 200 20 97 Comparative Example 4 Synthesis Example 4 + 5 + 6 3.23 2.71 84.37 120 7 97

As can be seen from Table 2 above, the siloxane compound represented by the formula (1) according to one embodiment has (i) a polystyrene reduced weight average molecular weight measured by gel permeation chromatography of 3,000 g / mole or less and a 2.38 weight (Ii) a compound having a weight average molecular weight of 3,000 g / mole or more and 6,000 g / mole or less in terms of a polystyrene standard sample measured by gel permeation chromatography and having a dissolution rate of not less than 1,500 Å / A siloxane compound having a dissolution rate of not less than 200 Å / sec and not more than 1,500 Å / s in a 2.38 wt% TMAH aqueous solution; And (iii) a polystyrene standard sample-converted weight average molecular weight measured by gel permeation chromatography of 6,000 g / mole or more and a dissolution rate in a 5.0 wt% TMAH aqueous solution of the prebaked membrane of 200 to 3,000 Å / The cured film prepared by curing the photosensitive resin composition contained as a mixture containing the siloxane compound has a residual film ratio of 85% or more, a resolution after curing of less than 7 占 퐉, and a high light transmittance.

However, the siloxane compound according to Synthesis Example 4, in which the weight average molecular weight of the siloxane compound was 1,765 g / mole and the dissolution rate of the membrane in the 2.38% by weight aqueous solution of TMAH was 6,000 Å / sec, had a weight average molecular weight of 3,130 g / A siloxane compound according to Synthesis Example 5 having a solubility of 160 Å / sec in an aqueous solution of TMAH in weight% and / or a siloxane compound having a weight average molecular weight of 4,260 g / mole and having a dissolution rate of 200 Å / sec in a 5.0 wt% TMAH aqueous solution 6, the cured photosensitive resin compositions (Comparative Examples 1, 2 and 4) containing these mixtures had a resolution of 7 탆 or more and a residual film ratio of less than 85% As shown in Fig.

In particular, when the siloxane compound according to Synthesis Example 4, which has a weight average molecular weight of 1,765 g / mole and a dissolution rate of 6,000 Å / sec in the 2.38% by weight aqueous solution of the membrane, is not included in the siloxane compound and has a weight average molecular weight of 3,130 g / mole And a solubility of the membrane in a 2.38% by weight aqueous solution of TMAH of 160 A / sec and a siloxane compound according to Synthesis Example 5 having a weight average molecular weight of 4,260 g / mole and a dissolution rate of the membrane in a 5.0 wt% TMAH aqueous solution of 200 A / It can be seen that the resolution after curing of the photosensitive resin composition of Comparative Example 3 using the siloxane compound according to Example 6 is 20 占 퐉 and the residual film ratio is also lower than 82%.

As a result, it can be seen that the photosensitive resin composition according to one embodiment can increase the resolution and the residual film ratio after curing of the cured film prepared from the photosensitive resin composition and maintain high light transmittance.

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 (13)

(A) a siloxane compound represented by the following formula (1);
(B) a quinone diazide compound, and
(C) a solvent,
Wherein the siloxane compound represented by the formula (1) comprises a mixture of at least one of the siloxane compounds of the following (i) and (ii) and the siloxane compound of the following (iii):
[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 the 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 C 2 to C 30 alkynyl group, a substituted or unsubstituted C 2 to C 30 alkynyl group, a substituted or unsubstituted C 2 to C 30 alkynyl group, a substituted or unsubstituted C 2 to C 30 alkynyl group, A substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C7 to C30 arylalkyl group), or a combination thereof,
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 < 0.5 < 0.5, 0.5 <
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.
(i) a polystyrene standard sample-converted weight average molecular weight of 3,000 g / mole or less measured by gel permeation chromatography (GPC) and a dissolution rate of the prebaked film in a 2.38% by weight aqueous solution of TMAH of 1,500 Å / Siloxane compounds;
(ii) a polystyrene standard sample-converted weight average molecular weight of not less than 3,000 g / mole and not more than 6,000 g / mole measured by gel permeation chromatography and having a dissolution rate in a 2.38% by weight aqueous solution of TMAH in a prebaked film of not less than 200 Å / A / sec or less; And
(iii) a siloxane having a weight average molecular weight of 6,000 g / mole or more in terms of polystyrene standard sample measured by gel permeation chromatography and having a dissolution rate in a 5.0 wt% TMAH aqueous solution of the prebaked film of 200 Å / sec or more and 3,000 Å / compound. 2. The photosensitive resin composition according to claim 1, wherein M, D and Q in formula (1) are all 0, and 0.8 < T1 < 1 and 0 < The photosensitive resin composition according to claim 1, wherein M, D and Q are all 0 in the formula (1), 0.85? T1 <1, and 0 <T2? 0.15. Wherein at least one of R 1 to R 6 in Formula (1) includes a substituted or unsubstituted C6 to C30 aryl group, at least one of R 1 to R 6 is a substituted or unsubstituted C1 to C30 alkyl group . The photosensitive resin composition according to claim 1, wherein Y in the formula (1) 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. The photosensitive resin composition according to claim 1, wherein the siloxane compound (i) is contained in an amount of 20% by weight to 80% by weight, based on the total weight of the siloxane compound represented by the formula (1). The photosensitive resin composition according to claim 1, wherein the siloxane compound (ii) is contained in an amount of 20% by weight to 80% by weight, based on the total weight of the siloxane compound represented by the formula (1). The photosensitive resin composition according to claim 1, wherein the siloxane compound (iii) is contained in an amount of 10% by weight to 70% by weight, based on the total weight of the siloxane compound represented by the formula (1). A cured film obtained by curing the photosensitive resin composition according to claim 1. The method according to claim 9, 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 9, wherein the cured film exhibits a hole characteristic of less than 7 占 퐉 at a temperature of 200 占 폚 or more, and has a light transmittance of 90% or more at a wavelength of 2.5 占 퐉 and a wavelength of 400 nm. 10. The cured film according to claim 9, wherein the cured film has a residual film ratio of 85% or more, which is defined as &quot; (film thickness after development / film thickness after pre-baking) x 100 &quot;. An electronic device comprising the cured film according to claim 9.
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