JP4345441B2 - Positive photosensitive resin composition and semiconductor device - Google Patents

Description

  The present invention relates to a positive photosensitive resin composition and a semiconductor device.

Conventionally, polyimide resin having excellent heat resistance and excellent electrical characteristics, mechanical characteristics, etc. has been used for the surface protection film and interlayer insulation film of semiconductor elements. Due to the thinning and downsizing of semiconductor devices and the shift to surface mounting by solder reflow, there is a need for significant improvements in characteristics such as heat cycle resistance and heat shock resistance, and higher performance resins are required. I came.
On the other hand, a technique for imparting photosensitivity to the polyimide resin itself has attracted attention, and examples thereof include a photosensitive polyimide resin represented by the following formula (5).

If this is used, a part of the pattern creation process can be simplified, and there is an effect of shortening the process and improving the yield. However, since a solvent such as N-methyl-2-pyrrolidone is required for development, safety and handling There is a problem with sex.
Therefore, a positive photosensitive resin composition that can be developed with an alkaline aqueous solution has recently been developed. For example, Patent Document 1 discloses a positive photosensitive resin composition composed of a polybenzoxazole precursor as a base resin and a diazoquinone compound as a photosensitive material. This has high heat resistance, excellent electrical properties, and fine processability, and has the potential as a resin composition for interlayer insulation as well as for wafer coating. The development mechanism of this positive photosensitive resin composition is as follows. The unexposed portion of the diazoquinone compound is insoluble in the aqueous alkali solution and has resistance against this by interacting with the base resin. On the other hand, upon exposure, the diazoquinone compound undergoes a chemical change, becomes soluble in an alkaline aqueous solution, and dissolves the base resin. 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 actually 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 order 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, or the pattern There arises a problem that the shape collapses. Recently, the trend of reducing the size of semiconductor elements has been accelerated, and it has become important to be able to form higher resolution patterns. As described above, when priority is given to the sensitivity, the pattern shape of the unexposed portion is destroyed, so that a pattern with a narrow width cannot be formed, resulting in low resolution. Conversely, if the molecular weight of the base resin is increased or the amount of the photosensitive diazoquinone compound, which is a photosensitive material, is increased so that the unexposed area does not collapse, the exposed area becomes difficult to dissolve in an alkaline aqueous solution. Or the remaining of the photosensitive resin composition (scum) occurs at the bottom of the pattern after development. Thus, in general, sensitivity and resolution are in a trade-off relationship, and development of a photosensitive resin composition that satisfies the characteristics of both has recently been strongly desired. Further, techniques for adding a phenol compound to a positive resist composition are disclosed in, for example, Patent Documents 2 to 9. However, the phenol compounds as shown in these documents have been problematic because the effect of improving the sensitivity is small when used in a positive photosensitive resin composition having a polyamide resin as a base resin.

Japanese Examined Patent Publication No. 1-46862 JP-A-3-200251 JP-A-3-2000025 JP-A-3-200263 Japanese Patent Laid-Open No. 3-200244 JP-A-4-1650 JP-A-4-11260 JP-A-4-12356 Japanese Patent Laid-Open No. 4-12357

  The present invention provides a positive photosensitive resin composition and a semiconductor device that have high sensitivity and high resolution.

Such an object is achieved by the present invention described in the following [1] to [9].
[ 1 ] Positive containing 100 parts by weight of an alkali-soluble resin (A), 1 to 50 parts by weight of a photosensitive diazoquinone compound (B) and 1 to 30 parts by weight of a phenol compound (C) having a structure represented by the general formula (1) Type photosensitive resin composition, wherein the alkali-soluble resin (A) is a resin having a polybenzoxazole structure, a polybenzoxazole precursor structure, a polyimide structure, a polyimide precursor structure, or a polyamic acid ester structure alone or 2 A positive photosensitive resin composition characterized by comprising more than one type,

[2] The positive photosensitive resin composition according to [ 1 ], wherein the alkali-soluble resin (A) is a polyamide resin having a structure represented by the general formula (2),

[ 3 ] The positive photosensitive resin composition according to [ 2 ], wherein X in the polyamide resin having a structure represented by the general formula (2) is selected from the group of the formula (3),

[ 4 ] The positive photosensitive resin composition according to [ 2 ] or [ 3 ], wherein Y in the polyamide resin having the structure represented by the general formula (2) is selected from the group of the formula (4),

[5] A polyamide resin having a structure represented by the general formula (2) is end-capped with a derivative containing an aliphatic group or a cyclic compound group having at least one alkenyl group or alkynyl group [2] ] The positive photosensitive resin composition in any one of-[4],
[6] The photosensitive diazoquinone compound (B) is an ester compound of a phenol compound and 1,2-naphthoquinone-2-diazide-5-sulfonic acid or 1,2-naphthoquinone-2-diazide-4-sulfonic acid. The positive photosensitive resin composition according to any one of [1] to [5],
[7] A semiconductor device comprising a surface protective film and an interlayer insulating film made of the positive photosensitive resin composition according to any one of [1] to [6],
[8] The positive photosensitive resin composition described in [2] is applied onto a semiconductor element, prebaked, exposed, developed, and heated, and the film thickness after heat dehydration and ring closure is 0.1 to 30 μm. A method of manufacturing a semiconductor device, characterized in that
It is.

  The positive-type photosensitive resin composition of the present invention has high sensitivity and high resolution with the characteristics that there is little film loss, the pattern shape does not collapse, and there is no remaining (scum) of the photosensitive resin composition in the exposed area. It has an excellent feature.

  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 novolak resin, polyhydroxystyrene, and a polyamide resin having a structure represented by the general formula (2). From the viewpoint of heat resistance after the final heating, the general formula (2 ) Is preferred.

X in the polyamide resin having the structure represented by the general formula (2) represents a divalent to tetravalent organic group, R ₇ is a hydroxyl group, O—R ₉ , m is an integer of 0 to 2, and these are It may be the same or different. Y represents a divalent to hexavalent organic group, R ₈ represents a hydroxyl group, a carboxyl group, O—R ₉ or COO—R ₉ , and n represents an integer of 0 to 4, which may be the same or different. Here, R ₉ is an organic group having 1 to 15 carbon atoms. However, when R ₇ has no hydroxyl group, at least one R ₈ must be a carboxyl group. When R ₈ has no carboxyl group, at least one R ₇ must be a hydroxyl group.

  The polyamide resin having the structure represented by the general formula (2) is, for example, a compound selected from diamine or bis (aminophenol) having a structure of X, 2,4-diaminophenol, etc., and a structure of Z blended as necessary. And a compound selected from tetracarboxylic anhydride, trimellitic anhydride, dicarboxylic acid or dicarboxylic acid dichloride, dicarboxylic acid derivative, hydroxydicarboxylic acid, hydroxydicarboxylic acid derivative having the structure of Y. Is obtained. 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 having the structure represented by the general formula _{(2), O-R 9} , COO-R 9 as a substituent of O-R _9, Y as a substituent of X is a hydroxyl group, an alkaline aqueous solution of the carboxyl group Is a group protected with an organic group having 1 to 15 carbon atoms for the purpose of adjusting the solubility in the solvent, and a hydroxyl group and a carboxyl group may be protected as necessary. Examples of R ₉ 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 300 to 400 ° C., dehydration ring closure occurs, and a heat resistant resin is obtained in the form of polyimide, polybenzoxazole, or copolymerization of both.

等であるがこれらに限定されるものではない。 X of the polyamide resin having the structure represented by the general formula (2) of the present invention is, for example,

However, it is not limited to these.

より選ばれるものであり、又２種以上用いても良い。 Among these, as particularly preferred,

Two or more kinds may be used.

等であるがこれらに限定されるものではない。 Y of the polyamide resin having the structure represented by the general formula (2) is, for example,

However, it is not limited to these.

より選ばれるものであり、又２種以上用いても良い。 Among these, particularly preferred are:

Two or more kinds 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 (2). Specifically, a diamine having a structure of X or a compound selected from bis (aminophenol) and 2,4-diaminophenol, a silicone diamine having a structure of Z and a tetracarboxylic having a structure of Y, which are blended as necessary. It is represented by the general formula (2) obtained by reacting with a compound selected from acid anhydride, trimellitic anhydride, dicarboxylic acid or dicarboxylic acid dichloride, dicarboxylic acid derivative, hydroxydicarboxylic acid, hydroxydicarboxylic acid derivative and the like. After synthesizing a polyamide resin having a structure, an acid anhydride or acid derivative containing an aliphatic group or cyclic compound group having at least one alkenyl group or alkynyl group as the terminal amino group contained in the polyamide resin is used. And capping as an amide. 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 after reacting with an amino group include:

等が挙げられるが、これらに限定されるものではない。

However, it is not limited to these.

より選ばれるものであり、これらは２種以上用いても良い。またこの方法に限定される事はなく、該ポリアミド樹脂中に含まれる末端の酸をアルケニル基又はアルキニル基を少なくとも１個有する脂肪族基又は環式化合物基を含むアミン誘導体を用いてアミドとしてキャップすることもできる。 Among these, particularly preferred are:

Two or more of these 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 cyclic compound group having at least one alkenyl group or alkynyl group. You can also

Furthermore, Z of the polyamide resin having the structure represented by the general formula (2) used as necessary is, for example,

However, the present invention is not limited to these, and two or more kinds may be used.

  Z of the polyamide resin having the structure represented by the general formula (2) is used, for example, when particularly excellent adhesion to a substrate such as a silicon wafer is required. Up to%. If it exceeds 40 mol%, the solubility of the resin in the exposed area will be extremely lowered, developing residue (scum) will occur, and pattern processing will not be possible, which is not preferred.

  The photosensitive diazoquinone compound (B) used in the present invention is a compound having a 1,2-benzoquinonediazide or 1,2-naphthoquinonediazide structure, and is known from US Pat. Nos. 2,729,975, 2,797,213 and 3,669,658. It is a substance. For example, the following are mentioned.

  Among these, an ester compound 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 the phenol compound include, but are not limited to, the following. Two or more of these may be used.

  The addition amount of the photosensitive diazoquinone compound (B) used by this invention is 1-50 weight part with respect to 100 weight part of alkali-soluble resin. If the amount is less than 1 part by weight, the patterning property of the polyamide resin becomes poor, and if it exceeds 50 parts by weight, the sensitivity is greatly reduced.

  In the positive photosensitive resin composition of the present invention, it is important to contain a phenol compound having a structure represented by the general formula (1).

  When the phenol compound having the structure represented by the general formula (1) is used, the dissolution rate of the exposed portion in the developing solution is increased and the sensitivity is improved, and the occurrence of scum is suppressed as compared with the conventional case. In addition, the film loss at the unexposed area as seen when the sensitivity is improved by reducing the molecular weight is very small. The phenol compound represented by the general formula (1) of the present invention is, for example,

However, it is not limited to these.

  The positive photosensitive resin composition of the present invention may contain other phenolic compounds as necessary for the purpose of improving sensitivity. Examples include the following, but are not limited thereto.

  The addition amount of the phenol compound (C) represented by the general formula (1) is 1 to 30 parts by weight with respect to 100 parts by weight of the alkali-soluble resin. If the amount is less than 1 part by weight, the sensitivity at the time of development decreases, and if it exceeds 30 parts by weight, the unexposed part is significantly reduced in film thickness during development, or precipitation occurs during freezing storage, resulting in lack of practicality.

  The positive photosensitive resin composition of the present invention may contain a dihydropyridine derivative in order to enhance the photosensitive characteristics as necessary. Examples of the dihydropyridine derivative include 2,6-dimethyl-3,5-diacetyl-4- (2′-nitrophenyl) -1,4-dihydropyridine, 4- (2′-nitrophenyl) -2,6-dimethyl. -3,5-dicarboethoxy-1,4-dihydropyridine, 4- (2 ', 4'-dinitrophenyl) -2,6-dimethyl-3,5-dicarbomethoxy-1,4-dihydropyridine, etc. be able to.

The positive photosensitive resin composition in the present invention may contain additives such as a leveling agent and a silane coupling agent as necessary.
In the present invention, these components are dissolved in a solvent and used in the form of a varnish. Solvents include N-methyl-2-pyrrolidone, γ-butyrolactone, N, N-dimethylacetamide, dimethyl sulfoxide, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dibutyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, propylene glycol Monomethyl ether acetate, methyl lactate, ethyl lactate, butyl lactate, methyl-1,3-butylene glycol acetate, 1,3-butylene glycol-3-monomethyl ether, methyl pyruvate, ethyl pyruvate, methyl-3-methoxypropio And the like, and may be used alone or in combination.

  In the method of using the positive photosensitive resin composition of the present invention, first, the resin 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. When the film thickness is less than 0.1 μm, it is difficult to sufficiently exert the function as a protective surface film of the semiconductor element, and when it exceeds 30 μm, it is difficult to obtain a fine processed pattern. Application methods 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. Developers include 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, and 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 a polyimide ring, an oxazole ring, or both a polyimide ring and an oxazole ring, thereby obtaining a final pattern rich in heat resistance.
The positive 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, liquid crystal alignment films, and the like.

Hereinafter, the present invention will be described specifically by way of examples.
<Example 1>
A thermometer containing 17.1 g (0.055 mol) of 4,4′-oxydiphthalic anhydride, 12.4 g (0.105 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 44.8 g (0.122 mol) of hexafluoro-2,2-bis (3-amino-4-hydroxyphenyl) propane with 70 g of N-methyl-2-pyrrolidone are added at room temperature. Stir for 2 hours. Thereafter, the reaction was terminated by stirring for 12 hours at 75 ° C. using an oil bath. After filtering the reaction mixture, the reaction mixture was put into a solution of water / methanol = 3/1 (volume ratio), the precipitate was collected by filtration, washed thoroughly with water, and dried under vacuum to obtain the general formula (2) And X is the following formula X-1, Y is the following formulas Y-1 and Y-2, and a polyamide resin (A-1) having a = 100 and b = 0 was synthesized.

Production of positive photosensitive resin composition 100 g of synthesized polyamide resin (A-1), 16 g of photosensitive diazoquinone compound having the structure of the following formula (Q-1), phenolic compound having the structure of the following formula (C-1) 10 g was dissolved in 150 g of γ-butyrolactone and then filtered through a 0.2 μm Teflon (R) filter to obtain a positive photosensitive resin composition.

Characteristic Evaluation This positive photosensitive resin composition was applied onto a silicon wafer using a spin coater and then pre-baked on a hot plate at 120 ° C. for 4 minutes to obtain a coating film having a thickness of about 13 μm. Through this coating film, a mask made by Toppan Printing Co., Ltd. (test chart No. 1: a remaining pattern and a blanking pattern with a width of 0.88 to 50 μm are drawn), and an i-line stepper (Nikon Corporation 4425i) ) And changed the exposure amount.
Next, the exposed portion was dissolved and removed by immersing in a 2.38% tetramethylammonium hydroxide aqueous solution for 110 seconds, and then rinsed with pure water for 10 seconds. As a result, it was confirmed that a pattern was formed from a portion irradiated with an exposure amount of 340 mJ / cm ² . (Sensitivity is 340 mJ / cm ² ). The resolution was as high as 3 μm.

<Example 2>
Evaluation similar to Example 1 was performed except having changed the addition amount of the phenolic compound (C-1) in Example 1 into the quantity shown in Table 1.

<Example 3>
The same evaluation as in Example 1 was performed except that the addition amount of the photosensitive material (Q-1) in Example 1 was changed to the amount shown in Table 1.

<Example 4>
Evaluation similar to Example 1 was performed except having changed the addition amount of the phenolic compound (C-1) in Example 1 into the quantity shown in Table 1.

<Example 5>
Synthesis of polyamide resin 360.4 g of dicarboxylic acid derivative (active ester) obtained by reacting 0.9 mol of terephthalic acid, 0.1 mol of isophthalic acid and 2 mol of 1-hydroxy-1,2,3-benzotriazole (0.9 mol) and 366.3 g (1 mol) of hexafluoro-2,2-bis (3-amino-4-hydroxyphenyl) propane were added to a thermometer, a stirrer, a raw material inlet, and a dry nitrogen gas inlet tube. It was put into a four-necked separable flask, and 3000 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, 32.8 g (0.2 mol) of 5-norbornene-2,3-dicarboxylic anhydride dissolved in 500 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 put into a solution of water / methanol = 3/1 (volume ratio), the precipitate was collected by filtration, washed thoroughly with water, and then dried under vacuum to obtain the general formula (2) Where X is a mixture of the following formula X-1, Y is a mixture of the following formulas Y-3 and Y-4, and the target polyamide resin (A-2) having a = 100 and b = 0 was obtained.

Production of positive photosensitive resin composition 100 g of synthesized polyamide resin (A-2), 16 g of photosensitive diazoquinone compound having the structure of the following formula (Q-1), phenol compound having the structure of the following formula (C-1) 10 g was dissolved in 150 g of γ-butyrolactone and then filtered through a 0.2 μm Teflon (R) filter to obtain a positive photosensitive resin composition. Otherwise, the same evaluation as in Example 1 was performed.

<Example 6>
In the synthesis of the polyamide resin in Example 3, hexafluoro-2,2-bis (3-amino-4-hydroxyphenyl) propane was reduced to 348.0 g (0.95 mol), and 1,3-bis ( 3-aminopropyl) -1,1,3,3-tetramethyldisiloxane (12.4 g, 0.05 mol) is added, and is represented by the general formula (2). A mixture of formulas Y-3 and Y-4, Z was the following formula Z-1, and a polyamide resin (A-3) comprising a = 95 and b = 5 was synthesized. A positive photosensitive resin composition was prepared in the same manner as in Example 3 except that (A-2) was changed to (A-3), and the same evaluation as in Example 1 was performed.

<Example 7>
Evaluation similar to Example 1 was performed except having changed the phenol compound (C-1) in Example 1 into (C-2).

<Example 8>
Evaluation similar to Example 1 was performed except having changed the phenol compound (C-1) in Example 1 into (C-3).

<Example 9>
Evaluation similar to Example 1 was performed except having changed the phenol compound (C-1) in Example 1 into (C-4).

<Comparative Example 1>
Evaluation similar to Example 1 was performed except having changed the phenol compound (C-1) in Example 1 into (C-5).

<Comparative example 2>
The same evaluation as in Example 1 was performed except that the phenol compound (C-1) in Example 3 was not added.

It is to be noted that Comparative Example 1 corresponds to Examples 1 to 4 and 6 to 9, and Comparative Example 2 corresponds to Example 5.
Below, X-1 of Examples 1-9 and Comparative Examples 1-2, Y-1 to Y-4, Z-1, Q-1,
The structure of C-1 to C-5 is shown.

The high-sensitivity and high-resolution positive photosensitive resin composition of the present invention has the characteristics that there is little film loss, there is no collapse of the pattern shape, and there is no remaining (scum) of the photosensitive resin composition in the exposed area. And is suitably used for a surface protection film, an interlayer insulating film, and the like of a semiconductor element.

Claims (8)

Positive photosensitive resin containing 100 parts by weight of alkali-soluble resin (A), 1 to 50 parts by weight of photosensitive diazoquinone compound (B) and 1 to 30 parts by weight of phenol compound (C) having the structure represented by formula (1) A resin composition comprising:
The alkali-soluble resin (A) comprises a resin having a polybenzoxazole structure, a polybenzoxazole precursor structure, a polyimide structure, a polyimide precursor structure, or a polyamic acid ester structure, alone or in combination. Positive photosensitive resin composition.

The positive photosensitive resin composition according to claim 1, wherein the alkali-soluble resin (A) is a polyamide resin having a structure represented by the general formula (2).

The positive photosensitive resin composition according to claim 2, wherein X in the polyamide resin having a structure represented by the general formula (2) is selected from the group of the formula (3).

The positive photosensitive resin composition according to claim 2 or 3, wherein Y in the polyamide resin having a structure represented by the general formula (2) is selected from the group of the formula (4).

  The polyamide resin having the structure represented by the general formula (2) is end-capped with a derivative containing an aliphatic group or a cyclic compound group having at least one alkenyl group or alkynyl group. The positive photosensitive resin composition according to any one of the above. The photosensitive diazoquinone compound (B) is an ester compound of a phenol compound and 1,2-naphthoquinone-2-diazide-5-sulfonic acid or 1,2-naphthoquinone-2-diazide-4-sulfonic acid. The positive photosensitive resin composition in any one of -5. A semiconductor device comprising a surface protective film and an interlayer insulating film made of the positive photosensitive resin composition according to claim 1.   The positive photosensitive resin composition according to claim 2 is applied onto a semiconductor element, prebaked, exposed, developed and heated so that the film thickness after heat dehydration and ring closure is 0.1 to 30 μm. A method of manufacturing a semiconductor device.