JP4556616B2 - Positive photosensitive resin composition, semiconductor device and display element using the positive photosensitive resin composition, and method for manufacturing semiconductor device and display element - Google Patents

Description

  The present invention relates to a positive photosensitive resin composition, a semiconductor device and a display element using the positive photosensitive resin composition, and a method for manufacturing the semiconductor device and the display element.

Conventionally, polybenzoxazole resins and polyimide resins having excellent heat resistance and excellent electrical characteristics, mechanical characteristics, and the like have been used for surface protection films and interlayer insulating films of semiconductor elements. On the other hand, in order to simplify the process, a positive photosensitive resin in which the polybenzoxazole resin or polyimide resin is combined with a diazoquinone compound as a photosensitive material is also used (for example, see Patent Document 1). The development mechanism of this positive photosensitive resin composition is hardly soluble in an alkaline aqueous solution in the unexposed area due to the effect of inhibiting dissolution of the diazoquinone compound into a resin such as polybenzoxazole resin or polyimide resin. On the other hand, in the exposed area, the diazoquinone compound undergoes a chemical change and becomes soluble in an alkaline aqueous solution. By utilizing the difference in solubility between the exposed portion and the unexposed portion to dissolve and remove the exposed portion, a coating film pattern of only the unexposed portion can be created. When these photosensitive resin compositions are used, the sensitivity of the photosensitive resin composition is particularly important. If the sensitivity is low, the exposure time becomes long and the throughput decreases. Therefore, in an attempt to improve the sensitivity of the photosensitive resin composition, for example, when the molecular weight of the base resin is reduced, the film thickness of the unexposed area is increased during development, so that the required film thickness cannot be obtained, There arises a problem that the pattern shape collapses. Conversely, if the diazoquinone compound, which is a photosensitive material, is increased in order to increase the dissolution inhibition of the unexposed area, a development residue called scum may occur at the bottom of the pattern after development. In addition, these photosensitive resins are patterned on a silicon wafer, but in recent years, as the diameter of the wafer has been increased, the uniformity of film thickness is also regarded as important. Regarding the film thickness uniformity, it is a matter of course that the film thickness after development is important. As described above, development of a positive photosensitive resin composition having high sensitivity, no scum, and excellent film thickness uniformity is strongly desired.
Japanese Examined Patent Publication No. 1-46862

  The present invention provides a positive photosensitive resin composition, a semiconductor device, and a display element that have high sensitivity, can be patterned without scum, and have excellent film thickness uniformity.

Such an object is achieved by the present invention described in the following [1] to [14].
[1] A positive photosensitive composition comprising an alkali-soluble resin (A), a diazoquinone compound (B), and two or more mixed solvents (C), wherein the mixed solvent (C) is γ-butyrolactone and propylene A positive photosensitive resin composition comprising a glycol monoalkyl ether, wherein the total amount of γ-butyrolactone and propylene glycol monoalkyl ether is 70% by weight or more of the total amount of the solvent.
[2] The positive photosensitive resin composition according to item [1], wherein the mixed solvent (C) further contains a solvent having a dipole moment of 3.5 debye or more.
[3] Item [1] or [2], wherein the propylene glycol monoalkyl ether is selected from the group consisting of propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, and propylene glycol monobutyl ether. The positive photosensitive resin composition as described.
[4] The positive photosensitive resin according to item [2] or [3], wherein the solvent having a dipole moment of 3.5 debye or more is selected from the group consisting of N-methylpyrrolidone, dimethyl sulfoxide and sulfolane. Composition.
[5] The alkali-soluble resin (A) has one or more structures selected from the group consisting of a polybenzoxazole structure, a polybenzoxazole precursor structure, a polyimide structure, a polyimide precursor structure, and a polyamic acid ester structure. A positive photosensitive resin composition as described in item [1], [2], [3] or [4].
[6] The positive photosensitive property according to item [1], [2], [3], [4] or [5], wherein the alkali-soluble resin (A) has a structure represented by the following general formula (1). Resin composition.

[7] The positive photosensitive resin composition according to the item [6], wherein X in the polyamide resin including the structure represented by the general formula (1) is selected from the group of the following structures.

[8] The positive photosensitive resin composition according to any one of [6] and [7], wherein Y in the polyamide resin having the structure represented by the general formula (1) is selected from the group of the following structures: .

[9] A polyamide resin having a structure represented by the general formula (1) is end-capped with a compound containing an aliphatic group or a cyclic compound group having at least one alkenyl group or alkynyl group [6], The positive photosensitive resin composition according to any one of [7] or [8].
[10] A step of coating the positive photosensitive resin composition according to any one of [1] to [9] on a substrate to form a composition layer, and an active energy ray on the approximate composition layer. A method for producing a patterned resin film, comprising: a step of forming a pattern by irradiation and contact with a developer; and a step of heating an approximate composition.
[11] A semiconductor device manufactured using the positive photosensitive resin composition according to any one of [1] to [9].
[12] A display element manufactured using the positive photosensitive resin composition according to any one of [1] to [9].
[13] The positive photosensitive resin composition according to any one of [1] to [9] is patterned on a semiconductor element so that the film thickness after heating is 0.1 to 30 μm. A method for manufacturing a semiconductor device, which is obtained.
[14] Pattern processing on the display element substrate so that the film thickness after heating the positive photosensitive resin composition according to any one of [1] to [9] is 0.1 to 30 μm. A method for manufacturing a display element, characterized by being obtained in the above manner.

  According to the present invention, it is possible to obtain a positive photosensitive resin composition with high sensitivity, no scum, and excellent film thickness uniformity, and a semiconductor device and a display element using the same.

  Examples of the alkali-soluble resin used in the present invention include a polybenzoxazole structure, a polybenzoxazole precursor structure, a polyimide structure, a polyimide precursor structure, or a polyamic acid ester structure, and a hydroxyl group, a carboxyl group, or a main chain or a side chain. Examples of the resin having a sulfonic acid group include a cresol type novolac resin, polyhydroxystyrene, and a polyamide resin having a structure represented by the general formula (1). The general formula (1) is used from the viewpoint of heat resistance after the final heating. ) Is preferred.

X of the polyamide resin having the structure represented by the general formula (1) represents a divalent to tetravalent organic group, R ₁ is a hydroxyl group or O—R ₃ , and m is an integer of 0 to 2. . Each R ₁ may be the same or different. Y in the general formula (1) represents a divalent to hexavalent organic group, R ₂ is a hydroxyl group, a carboxyl group, O—R ₃ or COO—R ₃ , and n is an integer of 0 to 4. Each R ₂ may be the same or different. Here, R ₃ is an organic group having 1 to 15 carbon atoms. However, when R ₁ has no hydroxyl group, at least one R ₂ must be a carboxyl group. When R ₂ has no carboxyl group, at least one R ₁ must be a hydroxyl group.

  The polyamide resin having the structure represented by the general formula (1) is, for example, a compound selected from diamine having an X structure or bis (aminophenol), 2,4-diaminophenol, and the like, and a tetracarboxylic acid having a Y structure. It is obtained by reacting with a compound selected from anhydride, trimellitic anhydride, dicarboxylic acid or dicarboxylic acid dichloride, dicarboxylic acid derivative, hydroxydicarboxylic acid, hydroxydicarboxylic acid derivative and the like. In the case of dicarboxylic acid, an active ester type dicarboxylic acid derivative obtained by reacting 1-hydroxy-1,2,3-benzotriazole or the like in advance may be used in order to increase the reaction yield or the like.

In the polyamide resin containing the structure represented by the general formula _{(1), O-R 3} , COO-R 3 as a substituent of O-R _3, Y as a substituent of X is a hydroxyl group, an alkaline aqueous solution of the carboxyl group Is a group protected by R ₃ which is an organic group having 1 to 15 carbon atoms, and if necessary, a hydroxyl group or a carboxyl group may be protected. Examples of R ₃ include formyl group, methyl group, ethyl group, propyl group, isopropyl group, tertiary butyl group, tertiary butoxycarbonyl group, phenyl group, benzyl group, tetrahydrofuranyl group, tetrahydropyranyl group and the like. It is done.

  When this polyamide resin is heated at about 250 to 400 ° C., it is dehydrated and closed, and a heat-resistant resin is obtained in the form of polyimide resin, polybenzoxazole resin, or copolymerization of both.

As X in the general formula (1), for example,
However, it is not limited to these.

Among these, particularly preferred are:
Two or more types may be used.

Moreover, as Y of general formula (1), for example,

However, it is not limited to these.

Among these, particularly preferred are:

Two or more types may be used.

  In the present invention, it is desirable to seal the end from the viewpoint of storage stability. For sealing, a derivative having an aliphatic group or a cyclic compound group having at least one alkenyl group or alkynyl group can be introduced as an acid derivative or an amine derivative at the end of the polyamide represented by the general formula (1). Specifically, for example, a compound selected from diamine or bis (aminophenol) having a structure of X, 2,4-diaminophenol, and the like, and a tetracarboxylic acid anhydride, trimellitic acid anhydride, dicarboxylic acid having a structure of Y After synthesizing a polyamide resin having a structure represented by the general formula (1) obtained by reacting with a compound selected from acid or dicarboxylic acid dichloride, dicarboxylic acid derivative, hydroxydicarboxylic acid, hydroxydicarboxylic acid derivative, etc. It is preferable to cap the terminal amino group contained in the polyamide resin as an amide using an acid anhydride or acid derivative containing an aliphatic group or cyclic compound group having at least one alkenyl group or alkynyl group. Examples of the group derived from an acid anhydride or acid derivative containing an aliphatic group or cyclic compound group having at least one alkenyl group or alkynyl group that reacts with an amino group include:

However, it is not limited to these.

Among these, particularly preferred are:

Two or more types may be used. The method is not limited to this method, and the terminal acid contained in the polyamide resin is capped as an amide using an amine derivative containing an aliphatic group or a cyclic compound group having at least one alkenyl group or alkynyl group. You can also

  The diazoquinone compound (B) used in the present invention is a compound having a 1,2-benzoquinonediazide or 1,2-naphthoquinonediazide structure, and is a substance known from U.S. Pat. It is. For example, the following are mentioned.

  Among these, an ester of a phenol compound and 1,2-naphthoquinone-2-diazide-5-sulfonic acid or 1,2-naphthoquinone-2-diazide-4-sulfonic acid is particularly preferable. Examples of these include, but are not limited to, the following. Two or more of these may be used.

  The preferable addition amount of the diazoquinone compound (B) used in the present invention is 1 to 50 parts by weight with respect to 100 parts by weight of the polyamide resin. If the amount is less than 1 part by weight, a good pattern cannot be obtained, and if it exceeds 50 parts by weight, the sensitivity is greatly reduced.

  The solvent used in the present invention is two or more kinds of mixed solvents (C), and the mixed solvent (C) contains γ-butyrolactone and propylene glycol monoalkyl ether, and γ-butyrolactone and propylene glycol monoalkyl ether. A solvent whose total amount is 70% by weight or more of the total amount of the solvent is used. γ-Butyrolactone is a good solvent for alkali-soluble resins and photosensitive diazoquinones, and is an essential component in the present invention. The propylene glycol monoalkyl ether used in the present invention acts to improve coating uniformity and reduce scum. As propylene glycol monoalkyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether can be used. Of these, propylene glycol monomethyl ether is preferred. Propylene glycol monoalkyl ether is preferably 80% by weight or less of the total solvent used. If it exceeds 80% by weight, the film thickness uniformity after coating is adversely decreased, and the photosensitive diazoquinone reprecipitates from the composition.

  In the present invention, it is more preferable to achieve high sensitivity by using a solvent composed of γ-butyrolactone, propylene glycol monoalkyl ether and a solvent having a dipole moment of 3.5 debye or more as the mixed solvent (C). Solvents with a dipole moment of 3.5 debye or more include N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, N, N-dimethylformamide, N, N-dimethylacetamide, ε-caprolactam, acetonitrile, acrylonitrile, benzonitrile , Butanenitrile, crotonaldehyde, ethylene carbonate, formamide, isobutylnitrile, methacrylonitrile, N-methylacetamide, 4-methylbutanenitrile, N-methylformamide, pentanenitrile, pentaneacetonitrile, propanenitrile, propiononitrile, 2-pyrrolidinone 1,3-dimethyl-2-imidazole can be used, but can be used without being limited thereto. Among these, N-methyl-2-pyrrolidone, dimethyl sulfoxide, and sulfolane are preferable. The solvent having a dipole moment of 3.5 debye or more is preferably 30% by weight or less of the total solvent used. If it exceeds 30% by weight, scum tends to occur. Further, one kind or two or more kinds of solvents having a dipole moment of 3.5 debye or more may be used.

  In the present invention, a compound having a phenolic hydroxyl group may be used in combination for higher sensitivity. As for the compounding quantity of the compound which has a phenolic hydroxyl group, 1-30 weight part is preferable with respect to 100 weight part of polyamide resins. Examples of the compound having a phenolic hydroxyl group include the following compounds, but are not limited thereto.

Of these, preferably

It is chosen from.

  In the method of using the positive photosensitive resin composition of the present invention, first, the composition is applied to a suitable support such as a silicon wafer, a ceramic substrate, an aluminum substrate and the like. In the case of a semiconductor device, the coating amount is applied so that the final film thickness after curing is 0.1 to 30 μm. If the film thickness is below the lower limit value, it will be difficult to fully function as a protective surface film of the semiconductor element. If the film thickness exceeds the upper limit value, it will be difficult to obtain a fine processing pattern. Takes a long time to reduce throughput. Examples of the coating method include spin coating using a spinner, spray coating using a spray coater, dipping, printing, roll coating, and the like. Next, after prebaking at 60 to 130 ° C. to dry the coating film, actinic radiation is applied to the desired pattern shape. As the actinic radiation, X-rays, electron beams, ultraviolet rays, visible rays and the like can be used, but those having a wavelength of 200 to 500 nm are preferable.

  Next, a relief pattern is obtained by dissolving and removing the irradiated portion with a developer. As the developer, inorganic alkalis such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, and aqueous ammonia, primary amines such as ethylamine and n-propylamine, diethylamine, di-n Secondary amines such as propylamine, tertiary amines such as triethylamine and methyldiethylamine, alcohol amines such as dimethylethanolamine and triethanolamine, quaternary ammonium such as tetramethylammonium hydroxide and tetraethylammonium hydroxide An aqueous solution of an alkali such as a salt and an aqueous solution to which an appropriate amount of a water-soluble organic solvent such as methanol or ethanol or a surfactant is added can be preferably used. As a developing method, methods such as spraying, paddle, dipping, and ultrasonic waves are possible.

  Next, the relief pattern formed by development is rinsed. Distilled water is used as the rinse liquid. Next, heat treatment is performed to form an oxazole ring and / or an imide ring, thereby obtaining a final pattern rich in heat resistance.

  The photosensitive resin composition according to the present invention is useful not only for semiconductor applications but also as interlayer insulation for multilayer circuits, cover coats for flexible copper-clad plates, solder resist films and liquid crystal alignment films, interlayer insulation films for elements in display elements, etc. It is.

  Examples of specific uses for semiconductors include a passivation film obtained by forming the above-described photosensitive resin composition film on a semiconductor element, and a photosensitive resin composition described above on a passivation film formed on a semiconductor element. Examples thereof include a buffer coat film formed by forming a physical film, and an interlayer insulating film formed by forming the above-described photosensitive resin composition film on a circuit formed on a semiconductor element.

  Among them, as one application example in which the photosensitive resin composition of the present invention is used in a semiconductor device, application to a semiconductor device having bumps will be described with reference to the drawings. FIG. 1 is an enlarged cross-sectional view of a pad portion of a semiconductor device having a bump according to the present invention. As shown in FIG. 1, a passivation film 3 is formed on an input / output Al pad 2 in a silicon wafer 1, and a via hole is formed in the passivation film 3. Further, a positive photosensitive resin (buffer coating film) 4 is formed thereon, and a metal (Cr, Ti, etc.) film 5 is formed so as to be connected to the Al pad 2, and the metal film 5 is formed of solder bumps. The periphery of 10 is etched to insulate between the pads. Barrier metal 8 and solder bumps 9 are formed on the insulated pads.

  Examples of display device applications include TFT interlayer insulating films, TFT element flattening films, color filter flattening films, protrusions for MVA liquid crystal display devices, and cathode partitions for organic EL elements. The usage method is based on forming the photosensitive resin composition layer patterned on the board | substrate which formed the display body element and the color filter by said method according to a semiconductor use. High transparency is required for display device applications, especially interlayer insulation films and planarization films, but by introducing a post-exposure process before curing the photosensitive resin composition layer, it is excellent in transparency. A resin layer can be obtained, which is more preferable in practical use.

Example 1
[Synthesis of polyamide resin]
Dicarboxylic acid obtained by reacting 4.13 g (0.016 mol) of diphenyl ether-4,4′-dicarboxylic acid with 4.32 g (0.032 mol) of 1-hydroxy-1,2,3-benzotriazole A mixture of acid derivatives (0.016 mol) and 7.33 g (0.020 mol) of hexafluoro-2,2-bis (3-amino-4-hydroxyphenyl) propane were thermometer, stirrer, raw material inlet, Into a four-necked separable flask equipped with a dry nitrogen gas inlet tube, 57.0 g of N-methyl-2-pyrrolidone was added and dissolved. Thereafter, the mixture was reacted at 75 ° C. for 12 hours using an oil bath. Next, 1.31 g (0.008 mol) of 5-norbornene-2,3-dicarboxylic anhydride dissolved in 7 g of N-methyl-2-pyrrolidone was added, and the mixture was further stirred for 12 hours to complete the reaction. After filtering the reaction mixture, the reaction mixture was poured into a solution of water / methanol = 3/1 (volume ratio), the precipitate was collected by filtration, washed thoroughly with water, dried under vacuum, and the desired polyamide resin ( A-1) was obtained.

[Preparation of resin composition]
10 g of synthesized polyamide resin (A-1), 2 g of photosensitive diazoquinone (B-1) having the following structure, γ-butyrolactone / propylene glycol methyl ether / N-methyl-2-pyrrolidone = 5/2/3 (weight ratio) ), And then filtered through a 0.2 μm fluororesin filter to obtain a positive photosensitive resin composition.

[Developability evaluation]
This positive photosensitive resin composition was applied to an 8-inch silicon wafer using a spin coater and then dried on a hot plate at 120 ° C. for 4 minutes to obtain a coating film having a thickness of about 10 μm. The film thickness of the obtained coating film was measured at 9 points in the plane of an 8-inch wafer (see FIG. 2), and the film thickness range (maximum value-minimum value) was 0.06 μm, which was good. It was. Through this coating film, a mask made by Toppan Printing Co., Ltd. (test chart No. 1: remaining pattern and blank pattern with a width of 0.88 to 50 μm are drawn), Nikon Corporation i-line stepper NSR-4425i The exposure was performed by increasing the exposure amount in steps of 100 mJ / cm ² to 10 mJ / cm ² . Next, the development time was adjusted in a 2.38% tetramethylammonium hydroxide aqueous solution so that the film slip during development was 1.5 μm, and the exposed portion was dissolved and removed, followed by rinsing with pure water for 30 seconds. When the pattern was observed, it was confirmed that the pattern was satisfactorily opened with no scum at an exposure amount of 290 mJ / cm ² . Next, when the film thickness of the unexposed part was measured, the film thickness range was as good as 0.11 μm.

<< Examples 2 to 10 >>
Using the polyamide resin (A-1) synthesized in Example 1, γ-butyrolactone / propylene glycol methyl ether / N-methyl-2-pyrrolidone used in [Preparation of resin composition] in Example 1 = 5 / Evaluation was performed in the same manner as in Example 1 using the solvents described in Table 1 instead of 2/3.

Example 11
[Synthesis of polyamide resin]
Thermometer containing 17.06 g (0.055 mol) of 4,4′-oxydiphthalic anhydride, 8.15 g (0.110 mol) of 2-methyl-2-propanol and 10.9 g (0.138 mol) of pyridine Into a four-necked separable flask equipped with a stirrer, a raw material inlet, and a dry nitrogen gas inlet tube, 150 g of N-methyl-2-pyrrolidone was added and dissolved. 14.9 g (0.110 mol) of 1-hydroxy-1,2,3-benzotriazole was added dropwise to this reaction solution together with 30 g of N-methyl-2-pyrrolidone, and then 22.7 g (0.110 mol) of dicyclohexylcarbodiimide. Was added dropwise together with 50 g of N-methyl-2-pyrrolidone and allowed to react overnight at room temperature. Thereafter, 27.1 g of a dicarboxylic acid derivative (active ester) obtained by reacting 1 mol of diphenyl ether-4,4′-dicarboxylic acid and 2 mol of 1-hydroxy-1,2,3-benzotriazole with this reaction solution. (0.055 mol) and 44.7 g (0.122 mol) of hexafluoro-2,2-bis (3-amino-4-hydroxyphenyl) propane together with 70 g of N-methyl-2-pyrrolidone are added at room temperature. Stir for 2 hours. Thereafter, the mixture was reacted at 75 ° C. for 12 hours using an oil bath.
Next, 3.94 g (0.024 mol) of 5-norbornene-2,3-dicarboxylic anhydride dissolved in 20 g of N-methyl-2-pyrrolidone was added, and the mixture was further stirred for 12 hours to complete the reaction. In the same manner as in Example 1, reprecipitation and purification were performed to synthesize the target polyamide resin (A-2).

[Production of resin composition, evaluation of developability]
10 g of synthesized polyamide resin (A-2), 2 g of photosensitive diazoquinone (B-2) having the following structure, mixed solution of γ-butyrolactone / propylene glycol methyl ether / N-methyl-2-pyrrolidone = 50/20/30 After dissolving in 20 g, the mixture was filtered through a 0.2 μm fluororesin filter to obtain a positive photosensitive resin composition. This positive photosensitive resin composition was evaluated in the same manner as in Example 1. The range of film thickness after coating was 0.08 μm. When exposure and development were performed, it was confirmed that the pattern was satisfactorily opened without scum at an exposure amount of 300 mJ / cm ² . Furthermore, when the film thickness of the unexposed part was measured, the film thickness range was as good as 0.12 μm.

<< Comparative Examples 1-4 >>
The polyamide resin (A-1) used in Example 1 was used in the solvents described in Table 1 and evaluated in the same manner as in Example 1.

  INDUSTRIAL APPLICABILITY The present invention provides a photosensitive resin composition that is highly sensitive, can be patterned without scum, and has excellent film thickness uniformity, and can be suitably used for a surface protective film, an interlayer insulating film, etc. of semiconductor elements and display elements it can.

The expanded sectional view of the pad part of an example of the semiconductor device which has a bump of the present invention is shown. Diagram of film thickness measurement points on 8-inch wafer

Explanation of symbols

1 Silicon wafer 2 Al pad 3 Passivation film 4 Buffer coat film 5 Metal (Cr, Ti, etc.) film 6 Wiring (Al, Cu, etc.)
7 Insulating film 8 Barrier metal 9 Solder bump 11 8 inch wafer 12 Measurement location (9 locations)
13 notches

Claims (9)

A positive photosensitive composition comprising an alkali-soluble resin (A), a diazoquinone compound (B), and a mixed solvent (C),
The alkali-soluble resin (A) includes one or more structures selected from the group consisting of a polybenzoxazole structure, a polybenzoxazole precursor structure, a polyimide structure, a polyimide precursor structure, and a polyamic acid ester structure. Yes,
The mixed solvent (C) is γ- butyrolactone, propylene glycol monoalkyl ether and 70% by weight of γ- butyrolactone and total amount solvent amount of propylene glycol monoalkyl ether with a dipole moment includes a 3.5 Debye or more solvents The positive photosensitive resin composition characterized by the above. The propylene glycol monoalkyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, positive photosensitive resin composition according to claim 1, wherein those selected from the group consisting of propylene glycol monopropyl ether and propylene glycol monobutyl ether object. The positive photosensitive resin composition according to claim 1 or 2, wherein the solvent having a dipole moment of 3.5 debye or more is selected from the group consisting of N-methylpyrrolidone, dimethyl sulfoxide and sulfolane. The positive photosensitive resin composition according to any one of claims 1 to 3, wherein the alkali-soluble resin (A) has a structure represented by the following general formula (1).
Formula X is in (1), the positive photosensitive resin composition according to claim 4, wherein is made is selected from the group of the following structure.


Y which definitive said general formula (1) The positive photosensitive resin composition according to claim 4 or 5 is made is selected from the group of the following structure.





Formula alkali-soluble resin containing a structure represented by (1), an alkenyl group or of claims 4 to 6 comprising end-capped by a compound containing an aliphatic group or a cyclic compound group having at least one alkynyl group The positive photosensitive resin composition according to any one of the above. Forming a composition layer of the positive photosensitive resin composition was coated on a substrate according to any one of claims 1 to 7, a developer by irradiation with active energy rays to the composition layer A method for producing a patterned resin film, comprising: a step of forming a pattern by contacting with a substrate ; and a step of heating the composition. A step of coating the positive photosensitive resin composition according to any one of claims 1 to 7 on a substrate to form a composition layer, and irradiating the composition layer with active energy rays to develop a developer A method for manufacturing a semiconductor device, comprising: a step of forming a pattern by contacting with a substrate; and a step of heating the composition.