KR19990069076A - Siloxane polyimide precursor composition - Google Patents

Abstract

The present invention is to prepare a polyamic acid by reacting an organic solvent with an aromatic siloxane dianhydride of the formula (1), an aromatic tetracarboxylic dianhydride of the formula (2) and an aromatic diamine of the formula (3), to a photosensitive agent and a crosslinking aid to the polyamic acid The present invention relates to a siloxane polyimide precursor composition produced by adding and a method for producing the same.

H ₂ NR ₁ -NH ₂

Wherein R ₁ is an aromatic or aliphatic cyclic group, and X is a photosensitive compound having a saturated aliphatic or unsaturated aliphatic group.

A photoinitiator, a sensitizer, a polymerization inhibitor and / or a colloidal inorganic additive may be further added to the polyimide composition to improve photosensitivity, thermal stability, and hardness of the film.

Description

Siloxane polyimide precursor composition

The present invention relates to siloxane polyimide precursor compositions. More specifically, the present invention relates to an improved siloxane polyimide precursor composition having improved heat resistance and adhesion, comprising an aromatic siloxane dianhydride, an aromatic tetracarboxylic dianhydride and an aromatic diamine.

Recently, in the semiconductor device field mainly on semiconductors and liquid crystal display devices, as the movement of high integration, high density, high reliability, and high speed of electronic devices are rapidly spreading, there is an attempt to use the advantages of organic materials that are easy to process and high purity. Research is ongoing. However, in order for the organic polymer to be used in these fields, it must be thermally stable in a process requiring 200 ° C. or more during device fabrication. In addition to the excellent electrical properties such as high heat resistance, excellent mechanical strength, low dielectric constant and high insulation, the polyimide resin has good planarization characteristics of the coating surface, very low content of impurities which degrades the reliability of the device, and can easily form fine shapes. There is a resin most suitable for the above purpose. A general method for synthesizing polyimide is a two-stage condensation polymerization, in which a diamine component and an acid dianhydride are polymerized in a polar organic solvent such as NMP (N-methyl-2-pyrrolidone), DMAc (demethylacetamide) or DMF (dimethylformamide) to form a polyimide precursor. A solution is obtained, which is coated on a silicon wafer or glass and then cured by heat treatment to obtain a polyimide film. Polyimide products for commercialized electronic materials are supplied in the form of polyimide precursor solutions or polyimide films, and are mainly supplied in the polyimide precursor solution state in the semiconductor device field. In resin-encapsulated LSIs, cracks in the passivation film of chips or damage to metal wiring may occur due to the thermal shrinkage of the resin after encapsulation and the thermal stress caused by the difference between the chip and the thermal expansion coefficient of the resin. . This problem is solved by using a polyimide between the chip and the encapsulant as a buffer layer, and a polyimide film thickness of 10 μm or more plays a buffer role. As the thickness of the coating film becomes thicker, the buffer effect is improved to improve the yield of semiconductor products. Can be. Polyimides require the formation of micro holes (via holes) such as inter-electrode connections and wire bonding pads. In order to form a fine pattern of polyimide, a method of coating a photoresist on an existing polyimide and etching is widely used. However, recently, application of a photosensitive polyimide having a photosensitive function to the polyimide has been attempted.

Conventional non-photosensitive polyimide requires an etching process to process holes using a separate photoresist for wire-bonding and metal wiring, but the use of photosensitive polyimide If it is possible to omit some of the processes can greatly increase the productivity. Practical photosensitive polyimide was developed by Rubner et al. Of Siemen (US-A-3957512). This is a form in which the photosensitive group is bonded to the polyamic acid as a polyimide precursor through an ester bond. When the photosensitive polyimide precursor solution is coated on a substrate to form a film and exposed to ultraviolet light, photopolymerization occurs in the exposed portion to form a crosslinked structure. In this state, the unexposed portion is removed during development with the organic solvent, and the final heat treatment causes the ester-bonded photosensitive component to be decomposed and removed at the same time as the imidization reaction to obtain a desired pattern of polyimide. However, the patterning of the thick polyimide precursor film has a disadvantage of poor resolution. Meanwhile, Toray Corp., Japan, has developed a photosensitive polyimide in which a compound having a photosensitive group and an amino component in a polyamic acid is ion-bonded (US-A-4243743). Such photosensitive polyimide has advantages in that it is easy to manufacture and generates less harmful by-products than conventional photosensitive polyimide. In the production of the photosensitive polyimide in the above examples, the provision of adhesion between polyimide, lead on chip (LOC) tape, polyimide and passivation film is one of the important factors in securing the reliability of semiconductor. . When the adhesion of the polyimide is poor, impurities such as moisture penetrate and cause defects such as cracks. To impart adhesion to polyimides, siloxane-based diamines having the following structure are generally used, as shown in US Pat. No. 3,740,305.

Wherein x is an integer from 1 to 20.

However, when the aliphatic siloxane-based diamine is used, the thermal decomposition temperature of the polyimide is greatly decreased, and furthermore, when applied to the photosensitive polyimide, the film characteristics of the finally obtained polyimide film are denatured and decomposed easily by decomposition decomposition products of the photosensitive compound having low heat resistance. There is a disadvantage that is greatly reduced. When the film characteristics of the polyimide film are deteriorated, problems such as the occurrence of cracks increase in later processes, such as a LOC tape bonding process and an epoxy encapsulation material molding process, lower the reliability of semiconductor products.

The present inventors intend to manufacture a polyimide precursor composition having improved heat resistance and adhesion by introducing an aromatic siloxane dianhydride as an adhesion aid and a semiconductor device using the same.

The technical problem to be achieved by the present invention is to provide a polyimide precursor composition having improved adhesion by using an aromatic siloxane dianhydride as an adhesion aid.

Another object of the present invention is to provide a polyimide precursor composition having improved heat resistance and mechanical properties by using an aromatic siloxane dianhydride as an adhesion aid.

The above and other technical problems of the present invention can be achieved by the present invention described below.

The present invention relates to a siloxane polyimide precursor composition consisting of an aromatic siloxane dianhydride of formula (1), an aromatic tetracarboxylic dianhydride of formula (2), and an aromatic diamine of formula (3) in an organic solvent, and a semiconductor device using the same.

Formula 1

Formula 2

Formula 3

H ₂ NR ₁ -NH ₂

Wherein R ₁ is an aromatic or aliphatic cyclic group, and X is a photosensitive compound having a saturated aliphatic or unsaturated aliphatic group.

The present invention may further include a photopolymerization initiator, a sensitizer and a thermal polymerization inhibitor according to the purpose.

The organic solvent may be a pretreatment of the aromatic tetracarboxylic dianhydride of the formula (4) with an alcohol, in which case a part of the aromatic tetracarboxylic dianhydride of the formula (2) is changed to a compound of the formula (4).

Wherein R ₂ is an aromatic or aliphatic cyclic group and X is a photosensitive compound having a saturated aliphatic or unsaturated aliphatic group.

The polyimide acid solution according to the siloxane polyimide precursor composition of the present invention can maintain the solution viscosity as low as 2,000 to 15,000 centipoise even at 20% by weight of solid content, and the coating film thickness may be 10 to 50 μm depending on the rotation speed by a spin coater or the like. A thick film exceeding the range can be easily formed. The polyamic acid resin is also produced by the reaction of tetracarboxylic dianhydride as an acid component and diamine as an amine component in an organic solvent.

Each of these components is described in detail below.

Tetracarboxylic dianhydride is largely classified into aromatic tetracarboxylic dianhydride, alicyclic dianhydride and aliphatic tetra dianhydride. The aromatic acid dianhydride includes butanetetracarboxylic dianhydride, butanetetracarboxylic dianhydride, hexanetetracarboxylic dianhydride, cyclopentanetetracarboxylic dianhydride ( cyclopentanetetracarboxylic dianhydride, bicyclopentanetetracarboxylic dianhydride, cyclopropanetetracarboxylic dianhydride, methylcyclohexanetetracarboxylic dianhydride, 3,3 ', 4,4'-benzophenonetetracarboxylic dianhydride (3,3 ', 4,4'-benzophenonetetracarboxylic dianhydride), pyromellitic acid dianhydride, 3,4,9,10-perylenetetra Carboxylic dianhydrides (3,4,9,10-perylenetetracaboxylic dianhydride), 4,4-sulfonyldiphthalic dianhydride (4,4-sulfonyld) iphthalic dianhydride), 3,3'4,4'-biphenyl tetracarboxylic dianhydride (3,3'4,4'-biphenyltetracarboxylic dianhydride), 1,2,5,6-naphthalenetetracarboxylic dianhydride (1,2,5,6-naphthalenetetracaboxylic dianhydride), 2,3,6,7-naphthalenetetracarboxylic dianhydride (2,3,6,7-naphthalenetetracaboxylic dianhydride), 1,4,5,8-naphthalene Tetracarboxylic dianhydride (1,4,5,8-naphthalenetetracaboxylic dianhydride), 2,3,5,6-pyridinetetracarboxylic dianhydride (2,3,5,6-pyridinetetracaboxylic dianhydride), m-ter Phenyl-3,3 ', 4,4', tetracarboxylic dianhydride (m-terphenyl-3,3 ', 4,4', tetracaboxylic dianhydride), p-terphenyl-3,3 ', 4 , 4 ',-tetracarboxylic dianhydride (p-terphenyl-3,3', 4,4 ',-tetracaboxylic dianhydride), 4,4-oxydiphthalic dianhydride, 1 , 1,1,3,3,3, -hexafluoro-2,2-bis (2,3 or 3,4-dicarboxyphenoxy) phenylpropane dianhydride (1,1,1,3,3, 3, -hexafluoro-2,2-bis (2,3 or 3,4- dicarboxyphenoxy) phenylpropane dianhydride), 2,2-bis [4- (2,3 or 3,4-dicarboxyphenoxy) phenyl] propane dianhydride (2,2-bis [4- (2,3 or 3,4) -dicarboxyphenoxy) phenyl] propane dianhydride), and 1,1,1,3,3,3, -hexafluoro-2,2-bis [4- (2,3 or 3,4-dicarboxyphenoxy) phenol ] Propane dianhydride (1,1,1,3,3,3, -hexafluoro-2,2-bis [4- (2,3 or 3,4-dicarboxyphenoxy) phenyl] propane dianhydride).

Aromatic diamines that can be used in the present invention include m-phenylene diamine, p-phenylenediamine, m-xylylenediamine, 1,5-diamino Naphthalene (1,5-diaminonaphthalene), 3,3'-dimethylbenzidine, 4,4- (or 3,4'-, 3,3'-, 2,4'- or 2 , 2 '-) diaminodiphenylmethane (4,4- (or 3,4'-, 3,3'-2,4'- or 2,2'-) diaminodiphenylmethane), 4,4- (or 3 , 4'-, 3,3'-, 2,4'- or 2,2 '-) diaminodiphenylether (4,4- (or 3,4'-, 3,3'-, 2,4 '-or 2,2'-) diaminodiphenylether), 4,4- (or 3,4'-, 3,3'-, 2,4'- or 2,2 '-) diaminodiphenylsulfide (4 , 4- (or 3,4 '-, 3,3'-2,4' or-2,2 '-) diaminodiphenylsulfide), 4,4- (or 3,4'-, 3,3'-, 2 , 4'- or 2,2 '-) diaminodiphenylsulfone (4,4- (or 3,4'-, 3,3'-2,4 'or-2,2'-) diaminodiphenylsulfide), 1 , 1,1,3,3,3, -hexafluoro-2,2-bis (4-aminophenyl) propane ((1,1,1,3,3,3, -hexafluoro-2,2-bis (4-aminophenyl) propane), 2,2-bis (4- (4-aminophenoxy) phene Yl) propane (2,2-bis (4- (4-aminophenoxy) phenyl) propane), 4,4-benzophenonediamine, 4,4'-di- (4-aminophenoxy ) Phenyl sulfone (4,4'-di- (4-aminophenoxy) phenylsulfone), 3,3-dimethyl-4,4-diaminodiphenylmethane, 4,4 4'-di- (3-aminophenoxy) phenylsulfone (4,4'-di- (3-aminophenoxy) phenylsulfone), 2,4-diaminotoluene, 2,5-dia Minotoluene (2,5-diaminotoluene), 2,6-diaminotoluene, benzidine, o-tolidine, 4,4'-diaminoterphenyl ( 4,4'-diaminoterphenyl), 2,5-diaminopyridine, 4,4'-bis (p-aminophenoxy) biphenyl (4,4'-bis (p-aminophenoxy) biphenyl), and hexahydro-4,7-methanoindanylene dimethylene diamine.

In the present invention, the siloxane dianhydride is used in an amount of 1 to 30 mol%, preferably 2 to 5 mol%, based on the total dianhydride. If the amount of the siloxane-based diamine is less than 1 mol%, the adhesive strength is lowered, and using more than 30 mol% does not need to use too much amount because of the high manufacturing cost.

Alcohol compounds used for R ₂ OH in the present invention include methyl alcohol, ethyl alcohol, isopropyl alcohol, isobutyl alcohol and allyl alcohol, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacryl. There are alcohols having a photoreceptor such as a rate.

Organic solvents used in the preparation of the polyamic acid include N-methyl-2-pyrrolidone, N, N-dimethylformamide, dimethyl sulfoxide, tetramethylurea, hexamethylphosphoric triamide, gamma-butyrolactone And general organic solvents. Examples of the compound having a photoreactive carbon-carbon unsaturated group added to the polyamic acid include N-methylacrylamide, N-methylmethacrylamide, N-ethylmethacrylamide, N, N-dimethylacrylamide, N, N-diethyl acrylamide, N-acryl oil morpholine, N-vinylpyrrolidone, etc. are mentioned. There is no restriction on the compound including the carbon-carbon unsaturated group used in the present invention. However, when the unsaturated group is bonded to an amino group, the carboxyl group of the polyamic acid is preferably bonded in the form of a salt, and the photoreactivity is superior to that of the photoreactive compound containing no amino group. Examples of the compound including both the carbon-carbon unsaturated group and the amino group having photoreactivity include N, N-dimethylaminoethyl acrylate, N, N-diethylaminoethyl acrylate, N, N-dimethylaminopropyl acrylate, N, N-diethylaminopropyl acrylate, N, N-dimethylaminobutyl acrylate, and the like, and instead of acrylate, 2-vinylpyridine, 4-vinylpyridine, arylamine, 2-methylarylamine, diarylamine, and the like. .

Photopolymerization initiators that can be used in the present invention include 2,6-di- (p-azidobenzal) -4-methylcyclohexanone (2,6-di- (p-azidobenzal) -4-methylcyclohexanone), and Bisazide compounds such as 2,6-di- (p-azidobenzal) -cyclohexanone, benzophenone, methyl o-benzoylbenzoate, 4,4'-bis (dimethylaminobenzophenone), 4,4-bis (diethylaminobenzophenone), 4,4-dichlorobenzophenone, 4-benzoyl-4'-methyldiphenylketone, dibenzylketone, florenone, 2,2'diethoxyacetophenone , 1-phenyl-1,2-butanedione-2- (o-ethoxycarbonyl) oxime (1-phenyl-butandione-2- (o-ethoxycarbonyl) oxime), 1,3-diphenyl-propanedione- 2- (o-ethoxycarbonyl) oxime (1,3-diphenyl-propandione-2- (o-ethoxycarbonyl) oxime, 1-phenyl-3-ethoxy-propanedione-2- (o-benzyl) oxime ( 1-phenyl-3-ethoxy-propandione-2- (o-benzyl) oxime), miharazketone, N-phenylglycidine, 3-phenyl-5-isoxazolone, 1-hydroxycyclohexylphenylketone, 2-methyl- (4- (methylthio) Phenyl) -2-morpholino-1-propanone, naphthalenesulfonylchloride, quinolinesulfonyl chloride, N-phenylthioacridone, 4,4'-azobisisobutyronitrile, diphenyldisulfide, Benzthiazole disulfide, triphenylpolspin, campolquinone, carbon tetrabromide, tribrophenylsulfone, benzoyl peroxide, etc. The photopolymerization initiator may be used alone or in combination of two or more.

The quantity of the photoinitiator contained in the siloxane polyimide precursor of this invention is 0.1-30 weight% based on a polyamic acid resin, and 2-15 weight% is preferable. If the amount of the photopolymerization initiator is 0.1% by weight or less, the photosensitivity of the composition is lowered, and if it is 30% by weight or more, the film thickness is decreased during the final curing of the film.

In the present invention, a sensitizer may be used to improve photosensitivity. Such sensitizers include 2,5-bis (4'-diethylaminobenzal) cyclopentanone, 2,6-bis (4'-dimethylaminobenzal) cyclohexanone, miharazketone, 4,4'-bis ( Diethylamino) benzophenone, 4,4'-bis (dimethylamino) chalcone, 4,4'-bis (diethylamino) chalcone, p-dimethylaminobenzylidene indanone, 2- (p-dimethylaminophenylvinyl Ene) -isonnaphthothiazole, 2- (p-dimethylaminophenylvinylene) benzothiazole, 1,3-bis (4'-dimethylaminobenzal) acetone, 1,3-bis (4'-diethylamino Benzal) acetone, 3,3'-carbonyl-bis- (7-diethylaminocumalin), N-phenyldiethanoldiamine, N-tolyldiethanolamine, N-phenylethanoldiamine, dimethylaminobenzoic acid isoamyl, 3-phenyl-5-isoxazolone, 1-phenyl-5-benzoylthio-tetrazole, 1-5-ethoxycarbonylthio-tetrazole and the like. One or more sensitizers may be used, and 0.1 to 30% by weight based on the polyamic acid is preferably 0.5 to 15% by weight. If the added amount of the sensitizer is 30% by weight or more, the thickness of the film decreases and the mechanical properties deteriorate during curing of the film. If the amount is less than 0.1% by weight, the photosensitivity of the composition is lowered.

When preserving the siloxane polyimide precursor of the present invention, a thermal polymerization inhibitor may be added to improve thermal stability. As the thermal polymerization inhibitor, a thermal polymerization inhibitor may also be added to improve thermal stability upon storage of the siloxane polyimide precursor. Examples of thermal polymerization inhibitors include hydroquinone, N-nitrosodiphenylamine, phenoxyazine, pt-butylcatechol, N-phenylnaphthylamine, 2,6-di-t-butyl-p-methylphenol, charonanyl And pyrogallol.

In order to improve the hardness of the formed polyimide film, colloidal inorganic fine particles may be added. The inorganic fine particles include silica sol, titania sol, zirconia sol and the like. The amount of the colloidal inorganic fine particles used is 1 to 50% by weight based on the polyamic acid, preferably 2 to 30% by weight.

When mixing all the components constituting the siloxane polyimide precursor composition or when dissolving the additive in the composition, it can be prepared as a coating solution by adding colloidal inorganic fine particles and the like. Most of these photosensitive compounds added to the polyimide precursor solution are pyrolyzed and removed at a final curing temperature of 350 ° C. or higher, leaving only the fully cured polyimide. Conventional aliphatic siloxane-based diamine compounds tend to deteriorate the film properties of the final film due to easily damaged aliphatic groups in the photosensitive compound that is thermally decomposed and to reduce heat resistance, but polyimide using siloxane dianhydride according to the present invention has a poor heat resistance. By reducing the length of the group it is possible to obtain excellent heat resistance and mechanical properties.

The present invention will be further illustrated by the following examples, which are only described for the purpose of illustrating the present invention and are not intended to limit the protection scope of the present invention.

Example

Example 1

Synthesis of polyamic acid by siloxane dianhydride, 3,3 ', 4,4'-biphenyl tetracarboxylic dianhydride and oxydianiline

147.1 g (0.5 mol) of 3,3 ', 4,4'-biphenyl tetracarboxylic dianhydride, 95 g (0.475 mol) of oxydianiline, 15.45 g (0.025 mol) of tetramethylsiloxane dianhydride of formula (I), 1030 g of N-methyl-2-pyrrolidone was placed in a polymerization tank and stirred for 5 hours at 60 ° C. under a nitrogen stream to obtain a polyamic acid solution as a polymer having a viscosity of 6,000 centipoise at room temperature. To 20 g of the polyamic acid prepared above, 3.2 g of dimethylaminoethyl methacrylate and 0.01 g of 2,6-di- (p-azidobenzal) -4-methylcyclohexanone and 1-phenyl-1,2-butadione 0.05 g of 2- (o-methoxycarbonyl) oxime was mixed and stirred for 30 minutes to obtain a siloxane polyimide precursor composition having a viscosity of 6,500 centipoise. The viscosity was measured using a Brookfield Viscometer No. 40 spindle. The obtained siloxane polyimide composition was coated on a silicon wafer for 30 seconds at a rotational speed of 1500 rpm and then cured at 95 ° C. for 4 minutes to form a film of polyimide precursor having a coating having a thickness of 18 μm. A photomask was put thereon to show a resolution of 8 μm or more when developed by N-methylpyrrolidone solution after ultraviolet irradiation. Then, after curing at 200 ° C. for 30 minutes and 350 ° C. for 30 minutes in a nitrogen gas atmosphere, the film thickness of the polyimide was 10 μm, thereby forming a very thick coating film. The adhesion characteristics of the polyimide were evaluated by scotch tape after preliminary storage of the polyimide film on the wafer for 100 hours under PCT (Pressure Cooking Test). The heat resistance of the obtained polyimide film was evaluated under a nitrogen atmosphere using TGA, and the 5% weight reduction temperature was 550 ° C., indicating very good heat resistance characteristics. The mechanical strength of the film was measured by Instron, and good values of tensile strength of 130 MPa and elongation of 80% or more were obtained.

Comparative Example 1

Preparation of polyimide precursor composition by siloxane dianhydride, 3,3 ', 4,4'-biphenyl tetracarboxylic dianhydride and oxydianiline

147.1 g (0.5 mol) of 3,3 ', 4,4'-biphenyl tetracarboxylic dianhydride, 95 g (0.475 mol) of oxydianiline, 6.2 g (0.025 mol) of bisgammaaminopropyl tetramethylsiloxane, N 993 g of -methyl-2-pyrrolidone was put into a polymerization tank and stirred for 5 hours at 60 DEG C under a nitrogen stream to obtain a polyamic acid solution as a polymer having a viscosity of 5,500 centipoise at room temperature. To 20 g of the polyamic acid prepared above, 3.2 g of dimethylaminoethyl methacrylate and 0.01 g of 2,6-di- (p-azidobenzal) -4-methylcyclohexanone and 1-phenyl-1,2-butadione 0.05 g of 2- (o-methoxycarbonyl) oxime was mixed and stirred for 30 minutes to obtain a siloxane polyimide precursor composition having a viscosity of 6,000 centipoise. The viscosity was measured using a Brookfield Viscometer No. 40 spindle. The obtained siloxane polyimide composition was coated on a silicon wafer for 30 seconds at a rotational speed of 1400 rpm and then cured at 95 ° C. for 4 minutes to form a film of polyimide precursor having a coating having a thickness of 18 μm. A photomask was put thereon to show a resolution of 8 μm or more when developed by N-methylpyrrolidone solution after ultraviolet irradiation. Then, after curing at 200 ° C. for 30 minutes and 350 ° C. for 30 minutes in a nitrogen gas atmosphere, the film thickness of the polyimide was 10 μm, thereby forming a very thick coating film. The adhesion properties of the polyimide were measured in the same manner as in the above example, and showed good adhesion properties without any release parts. The heat resistance of the obtained polyimide film showed a very good heat resistance property with a 5% weight reduction temperature of 515 ° C., but was significantly reduced compared to the above examples. The mechanical strength of the film was somewhat insufficient as the tensile strength of 120 MPa, elongation 30%.

The effect of the present invention is that the thermal decomposition temperature is improved by using an aliphatic siloxane diamine as an adhesion aid.

Another effect of the present invention is to improve the physical properties of the film after final curing by using an aliphatic siloxane diamine as an adhesion aid.

Another effect of the present invention is that the adhesion is improved by using an aliphatic siloxane diamine as an adhesion aid.

Simple modifications or changes of the present invention can be easily carried out by those skilled in the art, and all such modifications or changes can be seen to be included in the scope of the present invention.

Claims (4)

A siloxane polyimide precursor composition produced by reacting an organic solvent with an aromatic siloxane dianhydride of Formula 1, an aromatic tetracarboxylic dianhydride of Formula 2, and an aromatic diamine of Formula 3: Formula 1 Formula 2 Formula 3 H ₂ NR ₁ -NH ₂ Wherein R ₁ is an aromatic or aliphatic cyclic group, X is a photosensitive compound having a saturated aliphatic or unsaturated aliphatic group. The siloxane polyimide precursor composition according to claim 1, wherein a part of the tetracarboxylic dianhydride is converted into a compound represented by the following Chemical Formula 4 by pretreating the aromatic tetracarboxylic dianhydride of Formula 2 to the organic solvent. : Formula 4 Wherein R ₁ is an aromatic or aliphatic cyclic group, X is a photosensitive compound having a saturated aliphatic or unsaturated aliphatic group. 3. The alcohol according to claim 2, wherein the alcohol is selected from the group consisting of methyl alcohol, ethyl alcohol, isopropyl alcohol, isobutyl alcohol and allyl alcohol, 2-hydroxy ethyl acrylate, 2-hydroxy ethyl methacrylate. A siloxane polyimide precursor composition, characterized in that it is selected. A semiconductor device made from the siloxane polyimide precursor composition according to claim 1.