KR102106398B1 - Photo-sensitive Composition, Cured Film Prepared Therefrom, and Electronic Device Incorporating the Cured Film - Google Patents

Abstract

[화학식 2]

[화학식 3]

상기 화학식 1 내지 화학식 3의 각 치환기에 대한 정의는 명세서에서 정의한 바와 같다. A photosensitive resin composition comprising a copolymer unit, a photosensitive diazoquinone compound and a solvent comprising a structural unit represented by Formula 1, a structural unit represented by Formula 2, and a structural unit represented by Formula 3 below, A cured film obtained by curing and an electronic device comprising the cured film are provided:
[Formula 1]

[Formula 2]

[Formula 3]

Definitions for each substituent in Chemical Formulas 1 to 3 are as defined in the specification.

Description

Photosensitive composition, cured film prepared therefrom, and electronic device incorporating the cured film

It relates to a photosensitive resin composition, a cured film formed therefrom, and an electronic device having a cured film.

In general, an electronic component such as a thin film transistor type liquid crystal display element or a solid-state imaging element is provided with an insulating film to insulate wiring or the like arranged in a layer form. As a material for forming the insulating film, a positive photosensitive composition having a small number of steps for obtaining an insulating film having a required pattern shape has been widely used.

The positive photosensitive composition needs to have a wide process margin in the process of forming an insulating film, and after forming the insulating film, a solvent, an acid, in a post process such as wet etching of an ITO (Indium Tin Oxide) transparent electrode, or an alignment film, etc. Since it may be contacted by immersion in an alkali solution or the like and heat-treated, it is necessary to have resistance to these.

In the positive photosensitive material, the portion that receives light through UV exposure causes a chemical change and is developed in an alkali solution. It is then cured to harden the membrane. In this case, if the adhesion between the cured film and the lower substrate is poor, reliability is deteriorated. Particularly, a high temperature process of 200 or more and a curing time of 30 minutes or more during the process of manufacturing an insulating film may cause a decrease in adhesive strength between a lower substrate and an upper substrate in the display device due to continuous exposure at a high temperature. In the past, a silane coupling agent was used to improve the problem of lowering adhesion. Although the adhesive strength with the substrate could be improved by using a silane coupling agent, there was a problem in that the resolution and sensitivity, which are the main characteristics in the photosensitive material, were deteriorated by crosslinking easily even at low temperatures. Accordingly, there is an increasing need for developing new positive photosensitive materials that can increase adhesion without negatively affecting resolution and sensitivity.

One embodiment provides a photosensitive resin composition having excellent elongation while not having a pattern collapse after curing and having excellent elongation.

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

Another embodiment provides an electronic device including the cured film.

One embodiment (A) a structural unit represented by the formula (1), a structural unit represented by the formula (2), and a copolymer resin comprising a structural unit represented by the formula (3); (B) photosensitive diazoquinone compound; And (C) provides a photosensitive resin composition comprising a solvent.

[Formula 1]

In Formula 1,

R ¹ is a hydroxy group, a carboxyl group, a cyano group, a nitro group, a halogen, a C1 to C30 alkoxy group, 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, substituted or unsubstituted C7 to C30 arylalkyl group, substituted or unsubstituted C2 to C30 heterocycloalkyl group, substituted or unsubstituted C1 to C30 heteroaryl group, substituted or unsubstituted C2 to C30 alkenyl group , Substituted or unsubstituted C2 to C30 alkynyl group, or a combination thereof,

a is an integer from 0 to 3,

[Formula 2]

In Formula 2,

L ¹ to L ⁶ are each independently a single bond, a substituted or unsubstituted C1 to C30 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 heterocycloalkylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,

 [Formula 3]

In Formula 3,

Y ¹ and Y ² are each independently -S-, -O-, or -NH-,

R ² , R ³ , R ¹⁰ , and R ¹¹ are each independently a substituted or unsubstituted C1 to C30 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 heteroarylene group, or a combination thereof,

R ⁴ to R ⁹ are each independently, 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 C7 to C30 Arylalkyl group, substituted or unsubstituted C1 to C30 heteroalkyl group, substituted or unsubstituted C2 to C30 heterocycloalkyl group, substituted or unsubstituted C1 to C30 heteroaryl group, substituted or unsubstituted C2 to C30 alkenyl group, substituted Or an unsubstituted C2 to C30 alkynyl group, or a combination thereof,

b and c are each independently an integer from 0 to 5,

n is 0 to 350.

The structural unit represented by Chemical Formula 2 and the structural unit represented by Chemical Formula 3 may be included in the copolymer resin in a weight ratio of 9.9: 0.1 to 8: 2.

The structural unit represented by Chemical Formula 1 may include 50% to 70% by weight based on the total weight of the copolymer resin.

The weight average molecular weight of the copolymer resin may be 1,000 g / mol to 30,000 g / mol.

R ¹ of Formula 1 may be a hydroxy group.

L ¹ to L ⁶ of Formula 2 may be each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C1 to C20 alkylene group, or a combination thereof.

Formula 2 of L ¹ and L ² are, each independently, a substituted or unsubstituted C6 to C12 arylene group, L ³ to L ⁶ may each independently, a date alkylene substituted or unsubstituted C1 to C10 alkyl.

R ² and R ³ in Chemical Formula 3 may be each independently a substituted or unsubstituted C6 to C12 arylene group, a substituted or unsubstituted C1 to C10 alkylene group, or a combination thereof.

R ⁴ to R ⁹ in Chemical Formula 3 are each independently 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, or a combination thereof You can.

The photosensitive resin composition may include 5 to 100 parts by weight of the (B) photosensitive diazoquinone compound, and 200 to 2,000 parts by weight of the solvent (C) relative to 100 parts by weight of the (A) copolymer resin.

The photosensitive resin composition may further include 1 to 30 parts by weight of the crosslinking agent (D), based on 100 parts by weight of the (A) copolymer resin.

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

Another embodiment provides an electronic device including the cured film.

The photosensitive resin composition according to one embodiment not only has excellent elongation, but also enables low temperature curing, and the pattern does not crumble after curing, thereby obtaining a cured film having excellent resolution and adhesion to metal and an electronic device comprising the same You can.

Hereinafter, embodiments of the present invention will be described in detail so that those skilled in the art to which the present invention pertains can easily practice. However, the present invention can be implemented in many different forms and is not limited to the embodiments described herein.

Unless otherwise defined in the present specification, 'substituted' means that a hydrogen atom in a compound is a halogen atom (F, Br, Cl, or I), a hydroxyl group, a C1 to C30 alkoxy group, a nitro group, a cyano group, or an amino group. , Azide group, amidino group, hydrazino group, hydrazono group, carbonyl group, carbamyl group, thiol group, ester group, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, C1 to C20 alkyl group, C2 To C20 alkenyl group, C2 to C20 alkynyl group, C6 to C30 aryl group, C7 to C30 arylalkyl group, C1 to C20 heteroalkyl group, C3 to C20 heteroarylalkyl group, C3 to C30 cycloalkyl group, C3 to C15 cycloalkenyl group, It means substituted with a substituent selected from C6 to C15 cycloalkynyl group, C3 to C30 heterocycloalkyl group and combinations thereof.

In addition, unless otherwise defined herein, 'hetero' means that at least one hetero atom selected from N, O, S and P is included.

Unless otherwise specified in this specification, 'combination' means mixing or copolymerization.

Also, unless otherwise specified in this specification, "*" means a portion connected to the same or different atom or chemical formula.

Hereinafter, a photosensitive resin composition according to an embodiment will be described.

The photosensitive resin composition according to an embodiment includes (A) a copolymer unit comprising a structural unit represented by Chemical Formula 1, a structural unit represented by Chemical Formula 2, and a structural unit represented by Chemical Formula 3; (B) photosensitive diazoquinone compound; And (C) a solvent.

[Formula 1]

In Formula 1,

R ¹ is a hydroxy group, a carboxyl group, a cyano group, a nitro group, a halogen, a C1 to C30 alkoxy group, 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, substituted or unsubstituted C7 to C30 arylalkyl group, substituted or unsubstituted C2 to C30 heterocycloalkyl group, substituted or unsubstituted C1 to C30 heteroaryl group, substituted or unsubstituted C2 to C30 alkenyl group , Substituted or unsubstituted C2 to C30 alkynyl group, or a combination thereof,

a is an integer from 0 to 3,

[Formula 2]

In Formula 2,

L ¹ to L ⁶ are each independently a single bond, a substituted or unsubstituted C1 to C30 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 heterocycloalkylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,

[Formula 3]

In Formula 3,

Y ¹ and Y ² are each independently -S-, -O-, or -NH-,

R ² , R ³ , R ¹⁰ , and R ¹¹ are each independently a substituted or unsubstituted C1 to C30 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 heteroarylene group, or a combination thereof,

R ⁴ to R ⁹ are each independently, 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 C7 to C30 Arylalkyl group, substituted or unsubstituted C1 to C30 heteroalkyl group, substituted or unsubstituted C2 to C30 heterocycloalkyl group, substituted or unsubstituted C1 to C30 heteroaryl group, substituted or unsubstituted C2 to C30 alkenyl group, substituted Or an unsubstituted C2 to C30 alkynyl group, or a combination thereof,

b and c are each independently an integer from 0 to 5,

n is 0 to 350.

In recent years, in order to improve the processing capability of the semiconductor manufacturing process, a package material having low heat resistance is often used, and a reduction in the thermal curing temperature is required for the protective film or the interlayer insulating film forming material. Accordingly, after curing at a temperature of 250 ° C. or less, there is a need for a material having excellent pattern elongation and high elongation, which is considered important in reliability testing, without reflow, which is a phenomenon of pattern collapse as well as pattern characteristics.

Copolymers included in the photosensitive resin composition according to one embodiment may improve the reflow phenomenon after curing by including the structural units represented by Chemical Formula 1 and Chemical Formula 2, and further add structural units represented by Chemical Formula 3 By including, it is possible to improve the stretching force and the adhesion to the metal.

Hereinafter, each component of the photosensitive resin composition according to an embodiment will be described in detail.

(A) Copolymer resin

The copolymer resin according to an embodiment includes a structural unit represented by Chemical Formula 1, a structural unit represented by Chemical Formula 2, and a structural unit represented by Chemical Formula 3.

The photosensitive resin composition according to an embodiment includes the polydimethylsiloxane (Polydimethylsiloxane, PDMS) having a modified terminal as a linker in a copolymerization resin as a linker, and thus stretching properties of the film prepared by curing the resin composition. This is greatly improved. In addition, when synthesizing the PDMS linker, the polymerization degree is adjusted to properly adjust the molecular weight of the PDMS to control the crosslinking length in the copolymer resin, thereby not only excellent stretching properties, but also metal materials during low temperature curing at 250 ° C. or less. In particular, a cured film excellent in adhesion to titanium, aluminum, and copper can be obtained.

On the other hand, as a linker in the copolymer resin, not only the structural unit of Chemical Formula 3 but also a structural unit represented by Chemical Formula 2, that is, a structural unit having a large linear property including a -O- group, exhibits excellent stretching properties. In addition, the non-covalent electron pair possessed by the -O- group can provide a cured film that is more excellent in adhesion to metal materials, particularly titanium, aluminum, and copper even at low temperature curing of 250 or less.

In one example, in Formula 1, R ¹ Is a hydroxyl group, a may be an integer of 1 to 3.

In one example, L ¹ to L ⁶ of Formula 2 may be each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C1 to C20 alkylene group, or a combination thereof. .

In one example, L ¹ and L ² of Formula 2 may be each independently, a substituted or unsubstituted C6 to C12 arylene group. For example, L ¹ and L ² in Formula 2 may be a phenylene group.

In one example, L ³ to L ⁶ of Formula 2 may be each independently, a substituted or unsubstituted C1 to C10 alkylene group. For example, L ³ to L ⁶ in Formula 2 may each independently be a methylene group, an ethylene group, a propylene group, or a butylene group.

In one example, Y ¹ and Y ² in Chemical Formula 3 are each independently, -S-, -O-, or -NH-, and may be, for example, -S-.

In one example, R ² and R ³ of Formula 3 are each independently, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroaryl Rengi, or a combination thereof. For example, R ² and R ³ in Formula 3 may each independently be a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C6 to C12 arylene group, or a combination thereof.

In one example, R ⁴ to R ⁹ of Formula 3 may be each independently, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or a combination thereof. For example, R ⁴ to R ⁹ in Formula 3 may be each independently a substituted or unsubstituted C1 to C10 alkyl group, for example, a methyl group, an ethyl group, a propyl group, or a butyl group.

In one example, R ¹⁰ and R ¹¹ of Formula 3, each independently, a single bond, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, or a combination thereof You can. For example, R ¹⁰ and R ¹¹ in Formula 3 may be each independently a single bond, a substituted or unsubstituted C1 to C10 alkylene group, or a combination thereof, such as a single bond, a methylene group, Or it may be an ethylene group.

In one example, b and c in Chemical Formula 3 are each independently an integer of 1 to 5, for example, an integer of 1 to 3, for example, 2.

In one example, n in Formula 3 may be an integer from 0 to 350. When the n-value in the structural unit represented by Chemical Formula 3 satisfies the above range, the resolution of the film prepared from the copolymer resin containing it is excellent and the pattern collapse phenomenon can be improved.

In one example, the structural unit represented by Formula 2 and the structural unit represented by Formula 3 are 9.9: 0.1 to 8: 2 in a molar ratio, such as 9.9: 0.1 to 9: 1, such as 9.7: 0.3 to 9: 1 , For example, it may be included in the copolymer resin in a weight ratio of 9.5: 0.5, to 9: 1, for example, 9.3: 0.3 to 9: 1. When the structural unit represented by Chemical Formula 2 and the structural unit represented by Chemical Formula 3 are included in the copolymer resin in the mixing ratio, the elongation can be greatly improved.

The content of the structural unit represented by Formula 1 may be included in the range of 50% to 70% by weight, for example, 55% to 65% by weight relative to the total structural unit of the copolymer resin.

The weight average molecular weight of the copolymer resin may be 1,000 g / mol to 30,000 g / mol. For example, the weight average molecular weight of the copolymer resin is 1,000 g / mol to 20,000 g / mol, for example 2,000 g / mol to 20,000 g / mol, for example 3,000 g / mol to 20,000 g / mol, for example For example 3,000 g / mol to 15,000 g / mol, for example 4,000 g / mol to 15,000 g / mol. When having a weight average molecular weight in the above range, while having excellent stretching properties, as well as excellent adhesion to the metal, it has an effect that does not occur pattern collapse phenomenon.

(B) Photosensitive diazoquinone compound

The photosensitive diazoquinone compound according to an embodiment may be a compound having a 1,2-benzoquinonediazide structure or a 1,2-phthoquinonediazide structure.

For example, the photosensitive diazoquinone compound may be a compound represented by any one of the following Chemical Formulas 4 to 7, but is not limited thereto.

[Formula 4]

In Chemical Formula 4,

R31 to R33 may each independently be a hydrogen atom or a substituted or unsubstituted alkyl group, for example, may be CH ₃ , D1 to D3 may each independently be -OQ, and Q is a hydrogen atom, the following Chemical Formula 4 It may be a functional group represented by -a, or a functional group represented by the following formula 4-b, wherein Q may not be a hydrogen atom at the same time, and n31 to n33 may be independently 1 to 5, respectively.

[Formula 4-a]

[Formula 4-b]

[Formula 5]

In Formula 5,

R ³⁴ may be a hydrogen atom or a substituted or unsubstituted alkyl group,

D ⁴ to D ⁶ may each independently be OQ, wherein Q is the same as defined in Chemical Formula 4,

Each of n34 to n36 may be 1 to 5 independently.

[Formula 6]

In Formula 6,

A ₃ may be CO or CR ⁵⁰⁰ R ⁵⁰¹ , wherein R ⁵⁰⁰ and R ⁵⁰¹ may each independently be a substituted or unsubstituted alkyl group,

D ⁷ to D ¹⁰ may be each independently a hydrogen atom, a substituted or unsubstituted alkyl group, OQ, or NHQ, wherein Q is the same as defined in Chemical Formula 4,

n37, n38, n39 and n40 may each independently be an integer from 1 to 4,

n37 + n38 and n39 + n40 may each independently be an integer of 5 or less,

However, at least one of D ⁷ to D ¹⁰ is OQ, and one to three OQs may be included in one aromatic ring, and one to four OQs may be included in the other aromatic ring.

[Formula 7]

In Formula 7,

R ³⁵ to R ⁴² may be each independently a hydrogen atom or a substituted or unsubstituted alkyl group,

n41 and n42 may be each independently 1 to 5, specifically 2 to 4,

Q is the same as defined in Formula 4 above.

The photosensitive diazoquinone compound may be included in an amount of 5 parts by weight to 100 parts by weight, for example, 10 parts by weight to 50 parts by weight, for example, 10 parts by weight to 30 parts by weight based on 100 parts by weight of the copolymer resin. When the content of the photosensitive diazoquinone compound is within the above range, the pattern is well formed without residue by exposure, and there is no film thickness loss during development, and a good pattern can be obtained.

(C) menstruum

The photosensitive resin composition according to an embodiment may include a solvent that can easily dissolve each component of the copolymer resin and the photosensitive diazoquinone.

For example, the solvent uses an organic solvent, specifically N-methyl-2-pyrrolidone, gamma-butyrolactone, N, N-dimethylacetamide, dimethyl sulfoxide, diethylene glycol dimethyl ether, di Ethylene glycol diethyl ether, diethylene glycol dibutyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, methyl lactate (methyl lactate), ethyl lactate (ethyl lactate), lactic acid Butyl (butyl lactate), methyl-1,3-butylene glycol acetate, 1,3-butylene glycol-3-monomethyl ether, methyl pyruvate (methylpyruvate), ethyl pyruvate (ethyl pyruvate), methyl- 3-methoxy propionate or a combination thereof may be used, but is not limited thereto.

The solvent may be appropriately selected and used according to a process of forming a photosensitive resin film such as spin coating or slit die coating.

The solvent may be used in 200 parts by weight to 2,000 parts by weight with respect to 100 parts by weight of the alkali-soluble resin, for example, 200 parts by weight to 1,000 parts by weight. When the content of the solvent is within the above range, a film having a sufficient thickness can be coated, and solubility and coating properties are excellent.

(D) Crosslinker

The photosensitive resin composition according to an embodiment may further include a crosslinking agent. For example, the crosslinking agent may be a compound represented by any one of the following Chemical Formulas 8 to 10.

[Formula 8]

[Formula 9]

[Formula 10]

In Formulas 8 to 10,

R ¹¹ to R ¹³ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C1 to C10 alkoxy group,

R ¹⁴ and R ¹⁵ are each independently a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,

R ¹⁶ to R ²⁵ are each independently a hydrogen atom, a hydroxyl group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C1 to C10 alkoxy group.

The crosslinking agent serves to prevent the taper angle from lowering after curing of the photosensitive resin composition according to one embodiment. Further, in the photosensitive resin composition, when firing after pattern formation, a crosslinking agent reacts with the copolymer resin to form a crosslinked structure, and by including the above-described photosensitive diazoquinone compound together, the photosensitive diazoquinone compound is used as a photosensitive agent. , Catalyzing the formation of a crosslinked structure of the crosslinking agent. Therefore, in one embodiment, curing of the photosensitive resin composition is possible even at a low temperature of 250 or less, crosslinking occurs more actively, there is no reflow phenomenon in which the pattern collapses after curing, and mechanical properties such as elongation and strength also increase. .

The crosslinking agent may be included in 1 to 30 parts by weight based on 100 parts by weight of the copolymer resin. For example, the crosslinking agent may be included in 1 to 20 parts by weight, for example, 5 to 20 parts by weight based on 100 parts by weight of the copolymer resin.

(E) Other additives

The photosensitive resin composition according to an embodiment may further include other additives.

The photosensitive resin composition is a malonic acid or 3-amino-1,2-propanediol, a leveling agent, a fluorine-based surfactant, a radical to prevent stains or spots when coating, or to prevent generation of residues due to undeveloped properties Polymerization initiators or combinations thereof, and the like. The amount of these additives can be easily adjusted according to the desired physical properties.

In addition, the photosensitive resin composition may further use a silane coupling agent as an additive as an adhesion promoter to improve adhesion to a substrate. The silane coupling agent is, for example, vinyl trimethoxysilane, vinyl triethoxysilane, vinyl trichlorosilane, vinyl tris (? -Methoxyethoxy) silane; Or 3-methacryloxypropyltrimethoxysilane, 3-acryloxypropyltrimethoxysilane, p-styryl trimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropylmethyldi Ethoxysilane; Carbon-carbon unsaturated bond-containing silane compounds such as trimethoxy [3- (phenylamino) propyl] silane may be used, but the present invention is not limited thereto.

The photosensitive resin composition may be a positive photosensitive resin composition.

The process of forming a pattern using the photosensitive resin composition may include applying a photosensitive resin composition on a support substrate by spin coating, slit coating, inkjet printing, or the like; Drying the applied photosensitive resin composition to form a film; A step of exposing the film; Developing the exposed film with an aqueous alkali solution to produce an insulating film; And heating the insulating film. The process conditions for forming a pattern are widely known in the art, and thus detailed descriptions thereof will be omitted.

According to another embodiment, the photosensitive resin composition, for example, a positive type photosensitive resin composition is cured to provide a cured film prepared.

The cured film may be a thin film transistor type liquid crystal display device, a solid-state imaging device, an insulating film such as an organic light emitting diode (OLED), but is not limited thereto.

According to another embodiment, an electronic device including the cured film is provided. The electronic device may be a liquid crystal display, a light emitting diode, a plasma display, or a display device such as an organic light emitting device (eg OLED).

The photosensitive resin composition may be useful for forming an insulating film, a passivation layer, or a buffer coating layer in an electronic device. That is, the photosensitive resin composition has excellent adhesion to a metal and can be usefully used to form an insulating film between electrodes or wiring layers.

The embodiments of the present invention described above will be described in more detail through the following examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.

(Example)

Synthesis Examples 1 to 6: Synthesis of PDMS linker

Synthesis Example 1

Propyleneglycol methyl ether acetate (PGMEA) was added as a solvent to a 500 ml three-necked flask, and the reactant 4-methoxymethyl benzenethiol, 4-MMBT; molecular weight 154.23 g / mol) and DMS-V00 (gelest; molecular weight 186 g / mol) were dissolved by adding the solvent: reactant in a weight ratio of 3: 7. At this time, the reactants 4-methoxymethyl benzenethiol (4-MMBT) and DMS-V00 is a mixture of 60.3 parts by weight of DMS-VOO per 100 parts by weight of 4-MMBT. Thereafter, 2,2-dimethoxy-2-phenylacetophenone (2,2-Dimethoxy-2-phenylacetophenone, DMPA) as a photoinitiator is added by 1 wt% based on the total weight of the reactants. The reactor was mounted in an oil bath while maintaining 40 ° C. in an N ₂ atmosphere, and irradiated with UV at 365 nm for 6 hours under 0.6 mW / cm ² conditions. The solvent is then removed to obtain PDMS linker (A-1).

Synthesis Example 2

Propyleneglycol methyl ether acetate PGMEA was added as a solvent to a 500 ml three-necked flask, and the reactant 4-methoxymethylbenzenethiol, 4-MMBT; molecular weight 154.23 g / mol) and DMS-V03 (gelest company; molecular weight 500 g / mol) are dissolved by adding the solvent: reactant in a weight ratio of 3: 7. At this time, the reactants 4-methoxymethyl benzenethiol (4-MMBT) and DMS-V03 is a mixture of 162.1 parts by weight of DMS-VO3 per 100 parts by weight of 4-MMBT. Thereafter, 2,2-dimethoxy-2-phenylacetophenone (2,2-Dimethoxy-2-phenylacetophenone, DMPA) as a photoinitiator is added by 1 wt% based on the total weight of the reactants. While maintaining the reactor at 40 ° C. in an N ₂ atmosphere, the reactor was mounted in an oil bath and irradiated with 365 nm UV for 6 hours under 0.6 mW / cm ² conditions. The solvent is then removed to obtain a PDMS linker (A-2).

Synthesis Example 3

Propyleneglycol methyl ether acetate PGMEA was added as a solvent to a 500 ml three-necked flask, and the reactant 4-methoxymethylbenzenethiol, 4-MMBT; molecular weight 154.23 g / mol) and DMS-V05 (gelest; molecular weight 800 g / mol) are dissolved by adding the solvent: reactant in a weight ratio of 3: 7. At this time, the reactants 4-methoxymethyl benzenethiol (4-MMBT) and DMS-V05 is a mixture of 259.3 parts by weight of DMS-VO5 per 100 parts by weight of 4-MMBT. Then, 2,2-dimethoxy-2-phenylacetophenone (2,2-Dimethoxy-2-phenylacetophenone, DMPA) is added as a photoinitiator by 1 wt% based on the total weight of the reactants. The reactor was mounted in an oil bath while maintaining 40 ° C. in an N ₂ atmosphere, and 365 nm UV was 0.6 mW / cm ² Investigate for 6 hours by case. The solvent is then removed to obtain PDMS linker (A-3).

Synthesis Example 4

Propyleneglycol methyl ether acetate PGMEA was added as a solvent to a 500 ml three-necked flask, and the reactant 4-methoxymethylbenzenethiol, 4-MMBT; molecular weight 154.23 g / mol) and DMS-V21 (gelest company; molecular weight 6,000 g / mol) are dissolved by adding the solvent: reactant in a weight ratio of 3: 7. At this time, the reactants 4-methoxymethyl benzenethiol (4-MMBT) and DMS-V21 is a mixture of 1,945 parts by weight of DMS-V21 per 100 parts by weight of 4-MMBT. Then, 2,2-dimethoxy-2-phenylacetophenone (2,2-Dimethoxy-2-phenylacetophenone, DMPA) as a photoinitiator was added 1 wt% based on the total weight of the reactants. It is mounted in an oil bath to maintain 40 ° C in an N ₂ air atmosphere, and irradiated with 365 nm UV at 0.6 mW / cm ^{2 for} 6 hours. Thereafter, the solvent is removed to obtain a PDMS linker (A-4).

Synthesis Example 5

Propyleneglycol methyl ether acetate PGMEA was added as a solvent to a 500 ml three-necked flask, and the reactant 4-methoxymethylbenzenethiol, 4-MMBT; molecular weight 154.23 g / mol) and DMS-V25 (gelest; molecular weight 17,200 g / mol) are dissolved in the solvent: reactant such that the weight ratio is 3: 7. At this time, the reactants 4-methoxymethyl benzenethiol (4-MMBT) and DMS-V25 is a mixture of 5,576 parts by weight of DMS-V25 per 100 parts by weight of 4-MMBT. Then, 2,2-dimethoxy-2-phenylacetophenone (2,2-Dimethoxy-2-phenylacetophenone, DMPA) as a photoinitiator was added 1 wt% based on the total weight of the reactants. The reactor is mounted in an oil bath while maintaining 40 ° C. in an N ₂ atmosphere, and irradiated with 365 nm UV for 6 hours under 0.6 mW / cm ² conditions. Thereafter, the solvent is removed to obtain a PMDS linker (A-5).

Synthesis Example 6

Propyleneglycol methyl ether acetate PGMEA was added as a solvent to a 500 ml three-necked flask, and the reactant 4-methoxymethylbenzenethiol, 4-MMBT; molecular weight 154.23 g / mol) and DMS-V31 (gelest; molecular weight 28,000 g / mol) are dissolved by adding the solvent: reactant in a weight ratio of 3: 7. At this time, the reactants 4-methoxymethyl benzenethiol (4-MMBT) and DMS-V31 is a mixture of 9,077 parts by weight of DMS-V31 per 100 parts by weight of 4-MMBT. Thereafter, 2,2-dimethoxy-2-phenylacetophenone (2,2-Dimethoxy-2-phenylacetophenone, DMPA) as a photoinitiator is added by 1 wt% based on the total weight of the reactants. The reactor is mounted in an oil bath while maintaining 40 ° C. in an N ₂ atmosphere, and irradiated with 365 nm UV for 6 hours under 0.6 mW / cm ² conditions. After this, the solvent is removed to obtain a PDMS linker (A-6).

Synthesis Examples 7 to 12 and Comparative Synthesis Example 1: Synthesis of copolymer resin

Synthesis Example 7

Resorcinol was added to a nitrogen-substituted three-necked flask, and a solvent diethylene glycol dimethyl ether (DGDME) was added. Here, 4,4-bismethoxymethyldiphenyl ether (4,4'-BIS (Methoxymethyl) diphenyl ether, OMB) to be used as a linker and the linker (linker) prepared in Synthesis Example 1 (A-1) The mixture was added at a weight ratio of 9: 1, and the catalyst paratoluenesulfonic acid was added at 2% by weight based on the total weight of the copolymer resin to be prepared and stirred at 70 ° C. The ratio of the resorcinol and the linkers is added in a ratio of 1.5: 1 by weight, and the reactants are in a ratio of 60% by weight in the solvent. When it is confirmed that the reactants are dissolved to some extent, it is heated to 120 ° C. After confirming that it has completely melted, it is reacted by heating for another 6 hours. After the reaction was completed, the mixture was cooled to room temperature, and the prepared copolymer resin was dissolved in tetrahydrofuran (THF), and a mixture of deionized water and methanol (DIW / MeOH) was slowly added dropwise to precipitate. This process was repeated 5 times to remove the catalyst and unreacted monomers, and then dried in a vacuum oven to obtain a copolymer resin (B-1) (weight average molecular weight 9,000 g / mol).

Synthesis Example 8

Resorcinol was added to a nitrogen-substituted three-necked flask, and a solvent diethylene glycol dimethyl ether (DGDME) was added. Here, 4,4-bismethoxymethyldiphenyl ether (4,4'-BIS (Methoxymethyl) diphenyl ether, OMB) to be used as a linker and the linker (A-2) prepared in Synthesis Example 2 9: 1 The mixture was added in a weight ratio, and the catalyst paratoluenesulfonic acid was added at 2C by weight based on the total weight of the copolymer resin to be prepared and stirred at 70 ° C. The ratio of the resorcinol and the linkers is added in a ratio of 1.5: 1 by weight, and the reactants are in a ratio of 60% by weight in the solvent. When the reactants are confirmed to be somewhat dissolved, they are heated to 120 ° C. After confirming that it is completely melted, it is reacted by heating for another 6 hours. After the reaction was completed, the mixture was cooled to room temperature, and the prepared copolymer resin was dissolved in tetrahydrofuran (THF), and a mixture of deionized water and methanol (DIW / MeOH) was slowly added dropwise to precipitate. This process was repeated 5 times to remove the catalyst and unreacted monomers, and then dried in a vacuum oven to obtain a copolymer resin (B-2) (weight average molecular weight 11,000 g / mol).

Synthesis Example 9

Resorcinol was added to a nitrogen-substituted three-necked flask, and a solvent diethylene glycol dimethyl ether (DGDME) was added. Here, 4,4-bismethoxymethyldiphenyl ether (4,4'-BIS (Methoxymethyl) diphenyl ether, OMB) to be used as a linker and the linker (A-3) prepared in Synthesis Example 3 are 9: 1. The mixture was added in a weight ratio, and the catalyst paratoluenesulfonic acid was added at 2C by weight based on the total weight of the copolymer resin to be prepared and stirred at 70 ° C. The ratio of the resorcinol and the linkers is added in a ratio of 1.5: 1 by weight, and the reactants are in a ratio of 60% by weight in the solvent. When the reactants are confirmed to be somewhat dissolved, they are heated to 120 ° C. After confirming that it is completely melted, it is reacted by heating for another 6 hours. After the reaction was completed, the mixture was cooled to room temperature, and the prepared copolymer resin was dissolved in tetrahydrofuran (THF), and a mixture of deionized water and methanol (DIW / MeOH) was slowly added dropwise to precipitate. This process is repeated 5 times to remove the catalyst and unreacted monomer, and then dried in a vacuum oven to obtain a copolymer resin (B-3) (weight average molecular weight 15,000 g / mol).

Synthesis Example 10

Resorcinol was added to a nitrogen-substituted three-necked flask, and a solvent diethylene glycol dimethyl ether (DGDME) was added. Here, 4,4-bismethoxymethyldiphenyl ether (4,4'-BIS (Methoxymethyl) diphenyl ether, OMB) to be used as a linker and the linker (A-4) prepared in Synthesis Example 4 are 9: 1. The mixture was added in a weight ratio, and the catalyst paratoluenesulfonic acid was added at 2C by weight based on the total weight of the copolymer resin to be prepared and stirred at 70 ° C. The ratio of the resorcinol and the linkers is added in a ratio of 1.5: 1 by weight, and the reactants are in a ratio of 60% by weight in the solvent. When the reactants are confirmed to be somewhat dissolved, they are heated to 120 ° C. After confirming that it is completely melted, it is reacted by heating for another 6 hours. After the reaction was completed, the mixture was cooled to room temperature, and the prepared copolymer resin was dissolved in tetrahydrofuran (THF), and a mixture of deionized water and methanol (DIW / MeOH) was slowly added dropwise to precipitate. This process was repeated 5 times to remove the catalyst and unreacted monomers, and then dried in a vacuum oven to obtain a copolymer resin (B-4) (weight average molecular weight 10,000 g / mol).

Synthesis Example 11

Resorcinol was added to a nitrogen-substituted three-necked flask, and a solvent diethylene glycol dimethyl ether (DGDME) was added. Here, 4,4-bismethoxymethyldiphenyl ether (4,4'-BIS (Methoxymethyl) diphenyl ether, OMB) to be used as a linker and the linker (A-5) prepared in Synthesis Example 5 are 9: 1. The mixture was added in a weight ratio, and the catalyst paratoluenesulfonic acid was added at 2C by weight based on the total weight of the copolymer resin to be prepared and stirred at 70 ° C. The ratio of the resorcinol and the linkers is added in a ratio of 1.5: 1 by weight, and the reactants are in a ratio of 60% by weight in the solvent. When the reactants are confirmed to be somewhat dissolved, they are heated to 120 ° C. After confirming that it is completely melted, it is reacted by heating for another 6 hours. After the reaction was completed, the mixture was cooled to room temperature, and the prepared copolymer resin was dissolved in tetrahydrofuran (THF), and a mixture of deionized water and methanol (DIW / MeOH) was slowly added dropwise to precipitate. This process is repeated 5 times to remove the catalyst and unreacted monomer, and then dried in a vacuum oven to obtain a copolymer resin (B-5) (weight average molecular weight 12,000 g / mol).

Synthesis Example 12

Resorcinol was added to a nitrogen-substituted three-necked flask, and a solvent diethylene glycol dimethyl ether (DGDME) was added. Here, 4,4-bismethoxymethyldiphenyl ether (4,4'-BIS (Methoxymethyl) diphenyl ether, OMB) to be used as a linker and the linker (A-6) prepared in Synthesis Example 6 are 9: 1. The mixture was added in a weight ratio, and the catalyst paratoluenesulfonic acid was added at 2C by weight based on the total weight of the copolymer resin to be prepared and stirred at 70 ° C. The ratio of the resorcinol and the linkers is added in a ratio of 1.5: 1 by weight, and the reactants are in a ratio of 60% by weight in the solvent. When the reactants are confirmed to be somewhat dissolved, they are heated to 120 ° C. After confirming that it is completely melted, it is reacted by heating for another 6 hours. After the reaction was completed, the mixture was cooled to room temperature, and the prepared copolymer resin was dissolved in tetrahydrofuran (THF), and a mixture of deionized water and methanol (DIW / MeOH) was slowly added dropwise to precipitate. This process is repeated 5 times to remove the catalyst and unreacted monomers, and then dried in a vacuum oven to obtain a copolymer resin (B-6) (weight average molecular weight 11,000 g / mol).

Comparative Synthesis Example 1

Resorcinol is added to a nitrogen-substituted three-necked flask, and a solvent diethylene glycol dimethyl ether (DGDME) is added. Here, 4,4-bismethoxymethyldiphenyl ether (4,4'-BIS (Methoxymethyl) diphenyl ether, OMB) to be used as a linker is added, and a copolymerization resin to be prepared as a catalyst paratoluenesulfonic acid 2% by weight based on the total weight of and stirred at 70 ℃. The ratio of the resorcinol and the linker is added in a ratio of 1.5: 1 by weight, and the reactants are in a ratio of 60% by weight in the solvent. When the reactants are confirmed to be somewhat dissolved, they are heated to 120 ° C. After confirming that it was completely dissolved, the reaction was further performed by heating for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, and the prepared copolymer resin was dissolved in tetrahydrofuran (THF), and a mixture of deionized water and methanol (DIW / MeOH) was slowly added dropwise to precipitate. This process was repeated 5 times to remove the catalyst and unreacted monomer, and then dried in a vacuum oven to obtain a copolymer resin (B-0) (weight average molecular weight 13,000 g / mol).

Examples and Comparative Examples: Preparation of photosensitive resin composition

Each of the copolymer resins obtained in Synthesis Examples 7 to 12 and Comparative Synthesis Example 1, a photosensitive diazonaptoquinone compound (TPD425, Miwon Corporation), and 1,3,4,6-tetrakis (methoxymethyl) as a crosslinking agent Glycuryl (Sanwa Chemical Co., Ltd.) was mixed at the contents shown in Table 1 below to prepare photosensitive resin compositions according to Examples 1 to 5 and Comparative Examples 1 and 2, respectively.

In addition, in place of the copolymer resins obtained in Synthesis Examples 7 to 12 and Comparative Synthesis Example 1, novolak resin 1 (MEH-7500, MEIWA) or novolak resin 2 (MEH-7851, MEIWA) is listed in Table 1 below. By mixing with the composition, to prepare a photosensitive resin composition according to Comparative Example 3 and Comparative Example 4.

Copolymer resin
(40% dissolved in PGMEA) Photosensitivity
Diazonaptoquinone Crosslinker Example 1 B-1 75 15 10 Example 2 B-2 75 15 10 Example 3 B-3 75 15 10 Example 4 B-4 75 15 10 Example 5 B-5 75 15 10 Comparative Example 1 B-0 75 15 10 Comparative Example 2 B-6 75 15 10 Comparative Example 3 Novolak 1 75 15 10 Comparative Example 4 Novolak 2 75 15 10

(Unit:% by weight)

Preparation of cured film and evaluation

(1) Developability evaluation

After spin-coating the photosensitive resin compositions prepared in Examples 1 to 5 and Comparative Examples 1 to 4 on the glass, prebaking them at 120 ° C. for 120 seconds on a hot plate to obtain a film thickness of 10 μm. A coating film is formed. The exposure wavelength of the I line (365 nm) was irradiated to the coating film at an exposure amount of 600 mJ / cm ² , and then a pattern was formed using a 23 ° C., 2.38% tetramethylammonium hydroxide (TMAH) aqueous solution AZ-300 as a developer. Rinse with pure deionized water (DIW). After rinsing, check the state of the 10 um pattern formed using an optical microscope.

The case where the residual film remains is "defect" and the case patterned cleanly without the residual film is indicated as "amount", and the results are shown in Table 2 below.

(2) Reflow phenomenon evaluation

After spin-coating the photosensitive resin compositions prepared in Examples 1 to 5 and Comparative Examples 1 to 4 on glass, prebaking them at 120 ° C. for 120 seconds on a hot plate to obtain a coating film having a thickness of 10 um. To form. The exposure wavelength of I line (365 nm) was irradiated to the coating film at an exposure amount of 600 mJ / cm ² . Thereafter, a pattern was formed using a 23 ° C., 2.38% tetramethylammonium hydroxide aqueous solution AZ-300 with a developer, and then rinsed with pure deionized water to confirm the state of the 10 um pattern formed using an optical microscope. Thereafter, the pattern is obtained by heating and curing at 220 ° C. for 1 hour in a nitrogen atmosphere.

The obtained cured pattern was observed with an optical microscope to confirm that the 10 um pattern maintained its shape. According to the degree of shape retention, Δ and X are indicated, and the results are shown in Table 2 below.

(3) Evaluation of tensile elongation

The photosensitive resin compositions prepared in Examples 1 to 5 and Comparative Examples 1 to 4 were spin-coated on an 8-inch wafer substrate on which aluminum was deposited so that the film thickness after curing was about 10 um, followed by hot Pre-baked on the plate at 120 ° C for 120 seconds to form a coating film. A cured film having a thickness of 7 to 10 um is obtained by heating and curing the coating film at 220 ° C. for 1 hour in a nitrogen atmosphere. The obtained cured film was cut to a width of 1 cm with a diamond knife, and then immersed in an aqueous hydrofluoric acid solution having a concentration of 1 mass% for 4 to 5 hours to peel off the wafer, thereby obtaining five film samples. After the samples were dried in a drying oven for 10 hours or more, tensile elongation was measured using a UTM facility, and the results are shown in Table 2 below.

Initial sample length: 50 mm, test speed: 40 mm / min, load cell rating: 100 N

(4) Adhesion evaluation

First, copper, aluminum, and titanium are sputtered on a silicon wafer to prepare substrates (copper sputtering substrate, aluminum sputtering substrate, and titanium sputtering substrate) each having a metal material layer formed to a thickness of 200 to 500 nm. After spin coating on the substrate using the photosensitive resin compositions prepared in Examples 1 to 5, and Comparative Examples 1 to 4, pre-baking at 120 ° C. for 120 seconds on a hot plate to form a coating film.

A cured film having a thickness of 7 to 10 um is obtained by heating and curing the coating film at 220 ° C. for 1 hour in a nitrogen atmosphere. After curing for each substrate, cut to 2x2 cm using a diamond cutter, and fix the epoxy-embedded pin at a right angle to cure at 160 ° C for 30 minutes. Each cured sample was applied vertically using a stud pull device to measure the force when the pin fell, confirming the adhesion, and the results are shown in Table 2 below.

Developability Reflow Tensile elongation (%) Adhesion (Mpa) Ti Al Cu Example 1 amount ○ 8 19 21 25 Example 2 amount ○ 11 21 25 31 Example 3 amount ○ 18 26 31 34 Example 4 amount ○ 22 25 36 45 Example 5 amount △ 28 29 41 50 Comparative Example 1 amount ○ 5 18 18 21 Comparative Example 2 Bad X 32 32 46 54 Comparative Example 3 amount ○ 3 17 16 18 Comparative Example 4 amount ○ 2 18 21 20

Referring to Table 2, in the case of Examples 1 to 5 including all of the structural units of Chemical Formulas 1 to 3 according to one embodiment, developability is good and pattern reflow does not occur and the pattern shape is It was maintained as it is, and it can be seen that both the tensile elongation and the adhesion to the metal are excellent.

On the other hand, Comparative Example 1, which did not include the structural unit represented by Chemical Formula 3, had no significant difference in tensile elongation from Comparative Examples 3 and 4 containing the conventional novolac resin, and the structures represented by Chemical Formulas 1 to 3 Even if all of the units are included, it can be confirmed that the structural unit represented by Chemical Formula 3, that is, Comparative Example 2 in which the molecular weight of the PDMS linker exceeds 27,000 g / mol, has poor developability and a pattern collapse phenomenon. .

The preferred embodiments of the present invention have been described in detail above, but the present invention is not limited to the above embodiments, and may be manufactured in various different forms, and those skilled in the art to which the present invention pertains have technical aspects of the present invention. It will be understood that it may be implemented in other specific forms without changing the idea or essential features. Therefore, it should be understood that the embodiments described above are illustrative in all respects and not restrictive.

Claims (13)

(A) a copolymer unit comprising a structural unit represented by the following formula (1), a structural unit represented by the following formula (2), and a structural unit represented by the following formula (3);
(B) photosensitive diazoquinone compound; And
(C) Photosensitive resin composition comprising a solvent:
[Formula 1]

In Formula 1,
R ¹ is a hydroxy group, a carboxyl group, a cyano group, a nitro group, a halogen, a C1 to C30 alkoxy group, 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, substituted or unsubstituted C7 to C30 arylalkyl group, substituted or unsubstituted C2 to C30 heterocycloalkyl group, substituted or unsubstituted C1 to C30 heteroaryl group, substituted or unsubstituted C2 to C30 alkenyl group , Substituted or unsubstituted C2 to C30 alkynyl group, or a combination thereof,
a is an integer from 0 to 3,
[Formula 2]

In Formula 2,
L ¹ to L ⁶ are each independently a single bond, a substituted or unsubstituted C1 to C30 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 heterocycloalkylene group, a substituted or unsubstituted C1 to C30 heteroarylene group, or a combination thereof,
[Formula 3]

In Formula 3,
Y ¹ and Y ² are each independently -S, -O, or -NH,
R ² , R ³ , R ¹⁰ , and R ¹¹ are each independently a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C2 to C30 arylene group , Substituted or unsubstituted C1 to C30 heteroarylene group, or a combination thereof,
R ⁴ to R ⁹ are each independently, 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 C7 to C30 Arylalkyl group, substituted or unsubstituted C1 to C30 heteroalkyl group, substituted or unsubstituted C2 to C30 heterocycloalkyl group, substituted or unsubstituted C1 to C30 heteroaryl group, substituted or unsubstituted C2 to C30 alkenyl group, substituted Or an unsubstituted C2 to C30 alkynyl group, or a combination thereof,
b and c are each independently an integer from 0 to 5,
n is 0 to 350. The photosensitive resin composition of claim 1, wherein the structural unit represented by Chemical Formula 2 and the structural unit represented by Chemical Formula 3 are included in the copolymer resin in a weight ratio of 9.9: 0.1 to 8: 2. The photosensitive resin composition of claim 1, wherein the content of the structural unit represented by Chemical Formula 1 is included in an amount of 50% to 70% by weight relative to the total structural unit of the copolymer resin. The photosensitive resin composition of claim 1, wherein the weight average molecular weight of the copolymer resin is 1,000 g / mol to 30,000 g / mol. The photosensitive resin composition of claim 1, wherein R ¹ in Formula ¹ is a hydroxy group. In claim 1, L ¹ to L ⁶ of Formula 2 are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C1 to C20 alkylene group, or a combination thereof photosensitive Resin composition. In claim 1, L ¹ and L ² of Formula 2 are each independently, a substituted or unsubstituted C6 to C12 arylene group, L ³ to L ⁶ are each independently, a substituted or unsubstituted C1 to C10 alkyl. Lengiin photosensitive resin composition. In claim 1, R ² and R ³ of the formula (3) are each independently, a substituted or unsubstituted C6 to C12 arylene group, a substituted or unsubstituted C1 to C10 alkylene group, or a combination of these photosensitive resin composition. In claim 1, R ⁴ to R ⁹ of Formula 3 are each independently, 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. Or a combination of these photosensitive resin composition. The photosensitive resin composition of claim 1, wherein the (A) 100 parts by weight of the copolymer resin, (B) 5 to 100 parts by weight of the photosensitive diazoquinone compound, and (C) 200 to 2,000 parts by weight of the solvent Photosensitive resin composition containing. The photosensitive resin composition of claim 1, wherein the photosensitive resin composition further comprises (D) 1 to 30 parts by weight of a crosslinking agent (A) with respect to 100 parts by weight of the copolymer resin.  A cured film obtained by curing the photosensitive resin composition of any one of claims 1 to 11. An electronic device comprising the cured film according to claim 12.