JPH02149849A - Photosensitive resin composition - Google Patents

Abstract

PURPOSE:To improve a resistance to oxygen plasma and image resolution of a photosensitive resin compsn. by incorporating a base resin consisting of a specified polysilsesquioxane deriv. having unsatd. groups and a photosensitizing agent consisting of a haloalkyl aromatic compd. having an absorption in far ultraviolet region into a photosensitive resin compsn. CONSTITUTION:The subject photosensitive resin compsn. contains a base resin consisting of a polysilsesquioxane deriv. expressed by the formula I having unsatd. groups, a photosensitizing agent consisting of a haloalkyl aromatic compd. having an absorption in far ultraviolet region, and a solvent. In the formula I, R<1> is a vinyl group, aryl group, an alkenyl group selected from isopropenyl group and 2-butenyl group; k is a positive integer. When the polysilsesquioxane deriv. is used in the photosensitive resin compsn., preferred weight average mol.wt. of the deriv. is 1,000-100,000. Thus, the resistance to oxygen plasma and image resolution of the photosensitive resin compsn. are improved.

Description

DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a photosensitive resin composition used, for example, in the manufacture of semiconductor devices, etc.
The present invention relates to a negative photosensitive resin composition that is sensitive to deep ultraviolet rays of 0.00 (nm) and has excellent etching resistance.

(Prior Art) Photolithography technology is widely used as a microfabrication technology for semiconductor devices (hereinafter sometimes simply referred to as snowmaking) such as integrated circuits (ICs). This photolithography technique is performed through the following process, for example, to form a metal wiring pattern constituting a device.

First, a metal film for forming wiring is deposited on the entire surface of the base to obtain a substrate to be processed. Subsequently, a photosensitive resin composition (hereinafter sometimes simply referred to as a composition) is applied to the surface of the substrate to form a resist layer. Thereafter, this resist layer is exposed to light to form a resist pattern with a predetermined shape according to the design. Subsequently, using this resist pattern as a mask, the aforementioned metal film for wiring formation is etched, and the resist pattern is further removed to obtain a metal wiring pattern.

On the other hand, in recent years, with the demand for higher integration and higher speed of semiconductor devices, the constituent components of snow making are rapidly becoming smaller and more multi-layered.

Among these, the miniaturization of the metal wiring pattern is achieved by reducing the backbone width, so that the wiring resistance increases under the condition that the thickness of the metal film for forming the wiring is constant as described above. Therefore, in order to avoid an increase in wiring resistance, it is necessary to increase the aspect ratio of the metal wiring pattern, and the etching depth during pattern formation tends to increase. Therefore, it is necessary to increase the aspect ratio of the resist pattern so that it can sufficiently withstand the etching process. In addition, due to the multilayered metal wiring pattern, the surface shape of the base described above has complex irregularities.

Thus, in the photolithography technique, it is required to expose a resist layer deposited on the above-mentioned unevenness to form a resist pattern with a small pattern width and a high aspect ratio.

Further, as is well known, a reduction projection exposure apparatus is generally used in the exposure process. Here, if the numerical aperture of the reduction projection lens provided for the exposure drawing is NA and the wavelength of the light used for exposure is λ, the resolution line width corresponding to the pattern width is determined by R = λ/NA. be done. Therefore, in order to reduce the resolution line width, it is necessary to use a lens with a large numerical aperture NA, but such a lens usually has a shallow depth of focus and is used to form fine resist patterns with a high aspect ratio. The drawback was that it was difficult to do so.

As a conventional technique that can eliminate the above-mentioned drawbacks, for example, there is a literature: Journal of Electroche.
micalSociety: S Kano 10-5 TATE 5
CIENCE AND TEC: HNOLOGY (Journal of Electrochemical Society: Solid-State Science and Technology)
” (Vol. I32. No. 5.

1178-1182, May 1985) is known. This conventional technique uses a positive photosensitive resin composition that is sensitive in the deep ultraviolet region (200 to 300 (nm)) in addition to a resist pattern forming technique called a two-layer resist method. .

First, to briefly explain the two-layer resist method, a base is obtained by depositing a thick thermosetting resin on the surface of a substrate to be processed. This thermosetting resin can be used by heating and curing the photosensitive resin composition so that the photosensitivity disappears.In addition, in this process, the unevenness formed on the surface of the substrate to be processed is eliminated by the thermosetting resin. It can be used as a flat base.

Subsequently, a thin resist layer is formed on the surface of the base described above. Thereafter, the resist layer is exposed to light using a mask, and a resist pattern is formed through a predetermined development process and the like.

Next, using the above-mentioned resist pattern as an etching mask, the thermosetting resin formed on the lower layer side is etched to obtain a two-layer resist pattern consisting of the above-mentioned resist pattern and thermosetting resin.

Using the two-layer resist pattern thus obtained as an etching mask, etching is carried out in accordance with the material composition of the substrate to be processed, thereby completing patterning of the substrate to be processed.

According to this two-layer resist method, even when a resist pattern is formed using an exposure bag with a shallow depth of focus that is advantageous for the resolution line width, a thin resist pattern obtained by exposure and a pattern formed by etching are used. A high aspect ratio two-layer resist pattern can be formed by using a thick thermosetting resin.

In forming the above-mentioned two-layer resist pattern,
An etching process that can remove only the thermosetting resin by etching without damaging the substrate to be processed is preferable, and usually,
A dry etching process using oxygen (02) plasma is used.

Therefore, among the above-mentioned two-layer resist patterns, the resist patterned by exposure needs to have higher oxygen plasma resistance than the thermosetting resin.

According to this document, for example, a copolymer of trimethylsilylmethyl methacrylate and 3-oximino-2-butanone methacrylate (hereinafter referred to as Simply P (Sl
-OM). ) has been used as a photosensitive resin composition. In this composition, the molecule represented by the structural formula (2) itself functions as a base resin and a photosensitizer.

To explain in detail, 3-oximino-2-
The butanone methacrylate moiety becomes a radical, and the main chain constituting the copolymer is cut, forming a positive resist pattern.

According to this document, when dry etching treatment using oxygen plasma (under the condition of 20 W power) is performed, photosensitive P(Sl-OM) 1-lymethylsilyl methacrylate: 3-oximino -2-butanone methacrylate = 62: 38 (mol ratio)
(Si content is 9.6 (wt%)) the etching rate is 15 (nm/m1n).

Moreover, P (Sl-OM) could achieve line and space of 0=7 (um).

(Problem to be Solved by the Invention) However, the above-mentioned conventional technology has the problem that the oxygen plasma resistance of photosensitive P (Sl-OM) and the resolution when forming it as a resist pattern are insufficient. There was.

In view of the above-mentioned conventional problems, an object of the present invention is to provide a novel photosensitive resin composition that has excellent oxygen plasma resistance and resolution.

(Means for Solving the Problems) In order to achieve this object, the photosensitive resin composition of the present invention uses a base resin made of a polysilsesquioxane derivative having an unsaturated group and a photosensitizer made of a halogenated alkyl aromatic compound having absorption;
It is characterized by containing a solvent.

In carrying out this invention, the above-mentioned polysilsesquioxane derivative is a compound represented by the following general formula (I) (wherein R1 represents an alkenyl group and k represents a positive integer). is preferable.

As the polysilsesquioxane derivative represented by this formula (I), the vinyl group (CH2=C
H-), an alkenyl group selected from a 1-nor group (CH2=CHCH2-), an isopropenyl group (CH2・C-CH5), and a 2-butenyl group (CH2・CH-CH2-CH2-) It's good.

Such a polysilsesquioxane derivative is a compound proposed by the inventors of this application in JP-A-61-127638, and has a weight average molecular weight of 1.
00,000 does not gel during the synthesis stage and can be easily obtained. Moreover, the weight average molecular weight of this polysilsesquioxane derivative is 1
.

Therefore, when using a polysilsesquioxane derivative as a photosensitive resin composition, its weight average molecular weight is 1,
It is preferable to use a value within the range of 000 or more and 100,000 or less.

Next, the halogenated alkyl aromatic compound contained in the photosensitive resin composition according to the present invention has a wavelength of 200 to 3
It is preferable to use a material that generates halogen radicals when irradiated with deep ultraviolet rays of 0.00 (nm).

There are various halogenated alkyl aromatic compounds having such properties, but they mainly have the following general formulas (H) to (■) Ar 1 + CH 3-1, ... (II
)Ar'-0-CH3-IX, -(In)A
r'-X,, -CH2-n-CH2-,, x, -Ar'
-(IV)Ar' CH=CH2-nXn
”...(V)Ar1CUP R2Jr
+++++ (Vl) Ar'a-, -CX,
+++++ (VII) (However, in the formula, Ar' is a phenyl group, a 7-medoxycoumaryl group, a 7-acetoxycoumaryl group, a carbosylphenyl group, a human Ooxyphenyl group,
represents an aryl group such as a halophenyl group, a 9-fluorenyl group, a 4-phthaloimidyl group, a ]-naphthyl group, a nitrophenyl group, a cyanophenyl group, a 2-quinaldyl group, or a 9-anthracenyl group; X is fluorine; Represents the same or different halogens, either chlorine, bromine or iodine.

Furthermore, β, m, n, p, q, and r each represent the following integer.

β=1.2.3, m≧1, n=1.21)+Q+
r=3, and q and r=1.2) are preferred. All of these halogenated alkyl aromatic compounds represented by the formula have an aryl group in the molecule, and have a structure in which the hydrogen bonded to the α-position carbon is replaced with a halogen atom. This is because aromatic rings have large absorption in the deep ultraviolet region, and when there is an aromatic substituent group adjacent to a carbon-halogen bond, the bond becomes activated and easily cleaved, resulting in highly efficient radical formation. It acts as a generator.

In addition, among these halogenated alkyl aromatic compounds, the following general formula (■) or -Fukudai (XI) Ar2-GO-CH3-nXn '''' (■)A
r2-day3-CO-CH3-,,X,-...(XI)(
However, Ar2 is a phenyl group, a halophenyl group, an alkylphenyl group, a methoxyphenyl group, a nitrophenyl group,
It represents any aryl group of naphthyl group, halonaphthyl group, and biphenylyl group, and R3 is a methyl group (-C
H3), ethyl group (C2H5-), propyl group (C3
H7-), X represents any one of fluorine, chlorine, bromine or iodine,
Represents the same or different types of halogen, and n is 1≦n≦
The compound represented by ), which represents an integer of 3, is one in which the α-position carbon having a halogen atom is bonded to an aryl group via a carbonyl group,
Alternatively, an α-position carbon having a halogen atom is bonded to an alkyl group connected to an aryl group via a carbonyl group. This is because - Clothes cost (VIII) or OG
) is a halogenated alkyl aromatic compound represented by α
The bond between the carbon at the position and the halogen atom is easily activated, making it suitable as a compound with high generation efficiency of halogen radicals.

As described above, there are many types of halogenated alkyl aromatic compounds that can be used as the photosensitive resin composition of the present invention.
Although readily available, any material with suitable properties for use as a photosensitive resin composition may be used, such as those that are solid at the baking temperature when drying as a resist film, or those that have low sublimation or self-decomposition properties. You can choose .

Next, in carrying out this invention, the content of the halogenated alkyl aromatic compound as a photosensitizer with respect to the polysilsesquioxane derivative used as the base resin (mol number of photosensitizer/(number of lTlOI of photosensitizer) mol number of base resin) x 100)! 1 (mol%) or more 30 (mol%)
1%) is preferably within the following range. The lower limit of this content, 1 (mol%), is the amount necessary to maintain the sensitivity of the photosensitive composition, and the upper limit of this content, 30 (mol%), is the amount necessary to maintain the sensitivity of the photosensitive composition. ff1W
These conditions are necessary to maintain the properties of the resist and prevent the photosensitive agent from depositing on the surface of the resist.

(Function) According to the photosensitive resin composition of the present invention, at least the polysilsesquioxane derivative represented by the above-mentioned general formula (I) and the halogen represented by the above-mentioned general formulas (II) to (IX) are combined. The structure includes an alkyl aromatic compound. The mechanism of forming a resist pattern using such a composition is thought to be as follows.

First, a halogenated alkyl aromatic compound that serves as a photosensitizer generates halogen radicals when irradiated with deep ultraviolet rays.

This halogen radical acts on the unsaturated group (alkenyl group shown as 81 in -fukushiro (I)) contained in the polysilsesquioxane derivative to generate a polymer radical. Subsequently, these polymer radicals crosslink with each other to form a polymer, making it difficult to dissolve in a developer such as an organic solvent or an alkaline aqueous solution, and a negative resist pattern is obtained.

Since resist pattern formation is achieved using such halogen radicals, the content of the photosensitizer required for pattern formation can be reduced. Therefore, it is possible to use a base resin with a large Si content, such as a polysilsesquioxane derivative, and to reduce the content of the photosensitizer, thereby increasing the Si content of the photosensitive resin composition as a whole. (average about 10 to 28 (wt%)).

Therefore, it is considered that oxygen plasma resistance is improved by increasing the Si-containing tV.

(Example) Hereinafter, an example of the present invention will be described in detail. In addition, in the following examples, specific conditions will be illustrated and explained in order to facilitate understanding of this invention, but it should be understood that this invention is not limited only to these examples. Further, among the chemicals used in the following examples, although the sources may be omitted, all were chemically sufficiently pure and easily available.

Sensitivity and resolution of resist pattern formation> First, some of the photosensitive resin compositions according to the present invention will be exemplified, and the measurement results of sensitivity and resolution when actually forming resist patterns will be explained. do.

First, regarding the preparation of Compositions 1 to 7 used in this measurement, the composition and content of the base resin and photosensitizer were mainly measured. As mentioned above, the polysilsesquioxane derivative used as the base resin is disclosed in Japanese Patent Application Laid-open No. 6K127638.
After obtaining polysilsesquioxane according to the synthesis method disclosed in the publication, the hydroxyl group present at the terminal was replaced with a trimethylsilyl group. In addition, in this measurement, in order to facilitate comparison of measurement results, the weight average molecular weight was
o, ooo polyallylsilsesquioxane (in the above general formula (I), 1 is an allyl group)
was used as the base resin, only the type of the halogenated alkyl aromatic compound that became the photosensitizer was changed, and the content of the photosensitizer was 3.
(mol%).

"Cosmetic products" Polyallylsilsesquioxane 97 (mmol) (equivalent to 9,0 (9)) with a weight average molecular weight of 100,000
and 2,4-dichloropencitrichloride 3, which is classified into the general formula (II) described above and is represented by the following structural formula (■).
(mmol Composition 1 was obtained by filtering the solution.

HBr2 HBr2 α, α, α″, α°-tetrabromo=p-
3 (mmol) of xylene (corresponding to 1,3(9)) is mixed and dissolved in xylene 90 (mβ) as a solvent. Thereafter, Composition 2 was obtained by filtration in the same manner as in Composition].

In this composition 3, the above-mentioned boria-1-norsilsesquioxane 97 (mmol) is classified into the above-mentioned general formula (II), and the composition 2 is classified into the above-mentioned general formula (II). and α,α,α-tribromoquinaldine 3 (
mmol) (equivalent to 1,+(9)) and dissolved in the solvent xylene 90 (mβ). After that, Composition 3 was obtained by filtration in the same manner as Composition 1.

Coarse Dust Group J 1 This composition 4 contains the above-mentioned polyallylsilsesquioxane 97 (mmol) and p-nitrobenzyl bromide, which is classified into the above-mentioned general formula (I!) and is represented by the following structural formula (1). 3 (mm
ol) (corresponding to 0.65(9)) and dissolved in the solvent xylene 90 (mρ). After that, Composition 4 was obtained by filtration in the same manner as Composition 1.

Incorporation ■1 In this composition 5, the above-mentioned polyallylsilsesquioxane 97 (mmol) and 2-bromoacetylnaphthalene, which is classified into the above-mentioned general formula (■) and is classified into the following structural formula 〇, are used. 3 (mm
olMO,75(9)) and dissolved in xylene 90 (mβ), which is a solvent. After that, Composition 5 was obtained by filtration in the same manner as Composition 1.

In this composition 6, the above-mentioned polyallylsilsesquioxane 97 (mmol) and m-methoxyphena, which is classified into the above-mentioned general formula (■) and is classified into the following structural formula ■ r Sylbromide 3 (
mmol) (equivalent to 0.69(9)) and dissolved in the solvent xylene 90 (mβ). Thereafter, Composition 6 was obtained by filtration in the same manner as in Composition].

Group Au1ヱThis composition 7 contains the above-mentioned polyallylsilsesquioxane 97 (mmol), and p-bu and romofena, which are classified into the above-mentioned general formula (■) and are classified into the following structural formula 〇0CHJr. Sylbromide 3 (
mmo180.83 (equivalent to 9)) and dissolved in xylene 90 (mβ), which is a solvent. Thereafter, Composition 7 was obtained by filtration in the same manner as Composition 1.

Next, a procedure for actually forming a resist pattern using the above-mentioned composition 1 to 7% will be explained.

First, r MP2400J (manufactured by Silapray Co., Ltd., trade name) is spin-coated on the surface of a silicon substrate, and then heated and cured to form a thermosetting resin that has lost its photosensitivity. The film thickness of the thermosetting resin at this time was unified to 1.5 (μm).

Subsequently, a small amount of each of the above-mentioned compositions 1 to 7 was spin-coated onto the base obtained in this manner, and the mixture was coated using a hot plate at a temperature of 60 ('C) for 1 minute. It was baked to form a resist layer having a thickness of 0.2 (um).

Next, a Xe-Hg lamp (a Canon PLA501 aligner equipped with a CM250 cold mirror) was applied to this resist layer, and the wavelength was 220 to 300.
(equivalent to (nm)) and a quartz mask to carry out contact exposure.

After that, development was carried out for 30 seconds using a mixture of methyl isobutyl ketone (CMIB) and isopropyl alcohol (IPA) as a developer, and then roughly
Rinsing was performed for 20 seconds using the above-mentioned IPA to prepare measurement samples for each composition.

In addition, in the above-mentioned contact exposure, in order to compare the sensitivity of each composition, 50 (%) (0) of the initial film thickness of the resist layer was used.
, 1 (um)) remains as a resist pattern (hereinafter, the dose amount in this exposure is
,.・Abbreviated as 5. ). In addition, 1. By changing the lines and spaces of the quartz mask used during exposure and observing the pattern shape with an electron microscope, we found that the minimum pattern width (
Hereinafter, this will be referred to as the minimum resolution dimension. ) was observed.

Hereinafter, the measurement results of the sensitivity using the dose 1i (D,,'·5) as an index and the minimum resolution dimension obtained using each of the above-mentioned compositions 1 to 7 will be described in Example 1. ~Example 7 is shown in Attached Table 1.

As can be understood from this Attached Table 1, the minimum resolution dimension was 0.5 (um) for any of the compositions according to each of Examples 1 to 7.

In addition, D, 0.5 had various values shown in Attached Table 1 depending on the type of photosensitizer, but among these, for the composition according to Example 1, it was 180 (mJ/cm2), and for the composition according to Example 7
It is 220 (mJ/cm2) for the composition related to
This example showed better results than the other examples listed in the table.

Next, as a light source when forming a resist pattern,
Instead of the Xe-89 lamp, use an rF excimer laser (
Examples 8 and 9 will be described in which exposure was performed using an oscillation wavelength of approximately 250 (nm). In this example, a laser oscillator manufactured by Lambda Physics was used, and the irradiation amount per pulse was 4.8 (mJ/c).
Example 1 to Example 7 described above, except that m2)
A measurement sample was prepared using the same procedure and conditions as described above. In addition, in Example 8, the above-mentioned composition was used as a measurement sample,
In Example 9, the composition 7 described above was used as a measurement sample.

Below, referring to Attached Table 2, the measurement results obtained in Example 8 or Example 9 will be explained. The minimum resolution size of these two Examples is 0.5 (mm). , high resolution was obtained in the case of using an excimer laser and in the case of using an Xe-H (l lamp (corresponding to Example 1 or Example 7, respectively). In addition, DoO.5 In the case of Example 8, it is 210 (mJ/cm2), and in Example 9
In this case, it was 260 (mJ/cm2).

As can be understood from this result, the photosensitive resin composition according to the present invention exhibits excellent resolution even when exposed using an excimer laser.

Oxygen plasma resistance> Next, oxygen plasma resistance will be explained. In measuring this oxygen plasma resistance, the aforementioned composition 7v!
After coating the surface of a silicon substrate, a dry film of 0.2 (um) was obtained without exposure or development to obtain a sample according to Example 10.

This measurement was performed using a parallel plate dry etching device rDEM.
451'' (manufactured by Nikkei Anelva). In detail, oxygen gas pressure @ 1.0 (Pa), gas flow j
l is 20 (SCCM), and the day F power density is 0.12
(W/cm2) (75 (W) converted to RF power)
), 10 for the sample according to Example 10 described above.
Oxygen plasma etching was performed for 20 minutes or 20 minutes, and the thickness of the film remaining after etching was measured for each sample using "Talystep" (manufactured by Taylor Hoven, trade name).

As a result, among the samples according to Example 10, the sample subjected to oxygen plasma etching for 10 minutes had an etching rate of 5.2
The resist film was reduced at an etching rate of (nm/m1n). On the other hand, the film thickness remaining after etching was the same between the sample subjected to oxygen plasma etching for 20 minutes and the sample subjected to oxygen plasma etching for 10 minutes.

In addition, a plurality of samples according to Comparative Example were prepared using the same composition as Composition 7, except that it did not contain a photosensitizer, and the same procedure as in Example 10. Oxygen plasma etching was performed for 20 minutes, and the remaining film thickness was measured. As a result, among the samples according to Comparative Example 1, in the sample subjected to oxygen plasma etching for 10 minutes, film thinning occurred at an etching rate of 4.5 (nm/m1n). In addition, the sample subjected to oxygen plasma etching for 20 minutes and the sample
A comparison of the film thickness remaining after etching with a sample subjected to oxygen plasma etching for 0 minutes revealed that the film thickness was the same as in Example 10.

From the results of Example 10 and Comparative Example], it can be understood that the presence or absence of a photosensitizer does not substantially affect the oxygen plasma resistance of the resist pattern.

Formation of a two-layer resist pattern> Next, Example 11 in which the photosensitive resin composition of the present invention was used in a two-layer resist method will be described.

The procedure of this Example 11 was as follows: First, the above-mentioned r MP2400J was spin-coated on the surface of a silicon substrate and cured by heating to obtain a thermosetting resin having a film thickness of 2 (um).

Thereafter, the composition 7 described above is applied by spin coating and baked under the same conditions as described above to obtain a film thickness of 0.2 (um).

Next, using the aforementioned Xe-89 lamp and a quartz mask with a line and space of 0.5 (um),
Contact exposure was performed at a dose of (mJ/cm2). Thereafter, development processing and rinsing were performed under the same conditions as in Examples 1 to 7 described above.

Oxygen plasma etching was performed for 35 minutes under roughly the same etching conditions as in Example 10.
A two-layer resist pattern was obtained.

When this two-layer resist pattern was observed with an electron microscope, it was found that the pattern had a line and space of 0.5 (um) and an aspect ratio of 4 and had a rectangular cross-sectional shape.

As a result, it was confirmed that since the photosensitive resin composition according to the present invention has high oxygen plasma resistance, it can realize a high aspect ratio when used in a two-layer resist method.

Although the embodiments of the present invention have been described above, it is clear that the present invention is not limited only to the above-described embodiments.

For example, in the above example, when preparing the composition, xylene was used as a solvent in order to avoid phase separation between the base resin and the photosensitizer and form a good resist pattern. explained. However, the same effect can be obtained even when isoamyl acetate, ethyl cellosolve acetate, or methyl isobutyl ketone is used instead of xylene, or when a mixture of these solvents is used.

It is clear that any suitable design changes and modifications may be made to these materials, numerical conditions, N'M ratios, and other conditions within the scope of the invention.

(Effects of the Invention) As is clear from the above description, the photosensitive resin composition of the present invention contains at least a polysilsesquioxane derivative having an unsaturated group and halogen radicals by irradiation with deep ultraviolet rays. The structure includes the generated halogenated alkyl aromatic compound. Therefore, by using a highly sensitive photosensitizer, it is possible to form a resist pattern with high resolution, and by using a polysilsesquioxane derivative, the Si content of the entire photosensitive resin composition can be increased. Therefore, it is possible to improve oxygen plasma resistance.

Therefore, by applying the present invention, it is possible to provide a photosensitive resin composition that has excellent oxygen plasma resistance and can achieve high resolution.

Claims (7)

[Claims] (1) A photosensitive resin comprising a base resin made of a polysilsesquioxane derivative having an unsaturated group and a photosensitizer made of a halogenated alkyl aromatic compound having absorption in the deep ultraviolet region Composition. (2) The polysilsesquioxane derivative according to claim 1 has the following general formula (I) ▲ Numerical formula, chemical formula, table, etc.▼・・・(I) (However, R^1 represents an alkenyl group. where k is a positive integer). (3) R^1 of the polysilsesquioxane derivative represented by general formula (I) in claim 2 is a vinyl group (CH_2=
CH-), allyl group (CH_2=CHCH_2-), isopropenyl group (▲There are mathematical formulas, chemical formulas, tables, etc.▼)
, 2-butenyl group (CH_2=CH-CH_2-CH_2-). (4) A photosensitive resin composition, wherein the polysilsesquioxane derivative according to claim 1 has a weight average molecular weight of 1,000 or more and 100,000 or less. (5) The halogenated alkyl aromatic compound according to claim 1 has the following general formulas (II) to (VII) ▲There are numerical formulas, chemical formulas, tables, etc.▼...(II) Ar^1-O -CH_3_-_lX_l...(III
)Ar^1-X_n-CH_2_-_n-CH_2_-
_nXn-Ar^1...(IV) Ar^1-CH=C
H_2_-_nX_n...(V)Ar^1-CH_
pR^2_qX_r・・・(VI)Ar^1_4_-_
l-CX_l...(VII) (wherein Ar^1 is a phenyl group, 7-methoxycoumaryl group, 7-acetoxycoumaryl group, carbosylphenyl group, hydroxyphenyl group, halophenyl group, 9- Represents any aryl group of fluorenyl group, 4-phthaloimidyl group, 1-naphthyl group, nitrophenyl group, cyanophenyl group, 2-quinaldyl group or 9-anthracenyl group, and X is fluorine, chlorine, bromine or iodine. any of the
Represents the same or different halogens. Furthermore, l, m, n, p, q, and r each represent the following integer. 1, 2, 3, m≧1, n=1, 2, p+q+r=3, and q and r=1, 2). resin composition. (6) The halogenated alkyl aromatic compound according to claim 1 has the following general formula (VIII) Ar^2-CO-CH_3_-_nX_n... (V
III) or the following general formula (X I ) Ar^2-R^3-CO-CH_3_-_nX_n...
...(X I ) (However, Ar^2 is a phenyl group, a halophenyl group, an alkylphenyl group, a methoxyphenyl group,
R represents any aryl group of a nitrophenyl group, a naphthyl group, a halonaphthyl group, and a biphenylyl group;
^3 is a methyl group (-CH_3), an ethyl group (C_2H_
5-), propyl group (C_3H_7-), X represents the same or different halogen of fluorine, chlorine, bromine or iodine, and n is 1≦ Indicates an integer of n≦3. ) A photosensitive resin composition characterized by being one or more kinds of compounds represented by the following. (7) Photosensitivity according to claim 1, characterized in that the content of the halogenated alkyl aromatic compound with respect to the polysilsesquioxane derivative is within the range of 1 (mol%) to 30 (mol%). resin composition.