Radiation imagery chemistry: process – composition – or product th – Imaging affecting physical property of radiation sensitive... – Radiation sensitive composition or product or process of making
Reexamination Certificate
1994-04-28
2001-03-06
Chapman, Mark (Department: 1753)
Radiation imagery chemistry: process, composition, or product th
Imaging affecting physical property of radiation sensitive...
Radiation sensitive composition or product or process of making
C430S283100, C430S284100, C430S326000, C430S919000, C522S065000
Reexamination Certificate
active
06197475
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to a photosensitive resin composition, more specifically to a photosensitive resin composition having an excellent film property, heat-resistance, adhesivity and image-formability which does not require complex steps for preparation and does not cause contamination with chlorides.
2. Prior Art
In the semiconductor industries, inorganic materials have conventionally been used for interlaminar insulation. Recently, organic materials having an excellent heat-resistance such as a polyimide resin have been put to use as materials for interlaminar insulation because of properties thereof.
A process for forming a pattern in a semiconductor integrated circuit or forming a pattern of a circuit of a print substrate comprises complex and various steps such as formation of a resist material film on the substrate surface; exposure of required portion to light; removal of unnecessary portion by etching or so; and washing of the base surface. Therefore, development of heat-resistant photosensitive materials have been desired, which enables the required portion of the resist material to be used as insulating materials even after the pattern is formed by exposure to light and development.
As such a material, heat-resistant photosensitive materials comprising, for example, a photosensitive polyimide or a cyclized polybutadiene as a base polymer have been proposed. The photosensitive polyimide has attracted attentions since it has an excellent heat-resistance and impurities can easily be removed.
As such a photosensitive polyimide, for example, a photosensitive polyimide precursor (a polyamic acid ester) in which a photosensitive group is introduced into the polyimide precursor by an ester bond is proposed in Japanese Patent Publication No. 30207/1980. This material which requires the use of an acid chloride group in synthesis of the photosensitive polyimide precursor has a disadvantage that a finally obtained photosensitive resin composition is easily contaminated with the chloride. Also, thermal cure of the polyamic acid ester to obtain the objective polyimide requires a high temperature, and therefore, the polyamic acid ester cannot be used when an element which cannot be heated at a high temperature is used.
As another example, a photosensitive resin composition which mainly comprises a mixture of a polyamic acid, an amine having a photoactive functional group and an azide compound as a photosensitizer is proposed in Japanese Provisional Patent Publication No. 168942/1982.
However, the photosensitive resin composition has a disadvantage that a thick film thereof cannot be formed.
Japanese Provisional Patent Publication No. 95697/1979 proposes a photosensitive resin composition which mainly comprises a mixture of a polyamic acid and a polymerizable unsaturated compound having a photoactive functional group. This photosensitive resin composition, however, has a disadvantage that it has a lower resolution as compared with a photosensitive resin composition which uses a photosensitive group-containing polyamic acid in which the photosensitive group is directly bound with the polyamic acid.
SUMMARY OF THE INVENTION
The present invention is to overcome the above described problems of the prior arts, and it is an object of the present invention to provide a photosensitive resin composition having an excellent film property, heat-resistance, adhesions and image-formability which does not require complex steps for preparation and does not cause contamination with chlorides.
The present invention relates to a positive type photo-sensitive resin composition which comprises an alkali-soluble polymer (A) having a carboxyl group and/or a phenolic hydroxyl group, and a compound (B) which forms an amine compound with irradiation of light.
DESCRIPTION OF THE PREFERRED EMBODIMENT
In the following, the present invention is explained in detail.
The alkali-soluble polymer (A) of the present invention is a polymer having an acidic group such as a carboxyl group, a sulfonic acid group and/or a phenolic hydroxyl group capable of forming a salt with a basic compound mentioned below and is not particularly limited, and may include, for example, a polyamic acid resin, a solvent-soluble polyimide resin having at least one of a carboxy group and a phenolic hydroxy group, and a phenol novolak resin. Among them, the polyamic acid resin is preferred, and the polyamic acid resin having recurring units represented by the formula:
wherein R
1
represents a tetravalent group may have one or more substituents, R
2
represents a divalent group which may have one or more substituents; R
3
and R
4
are in the ortho-position of one of two carbonyl groups, respectively, and each independently represent a hydrogen atom or a carboxyl group, provided that at least one of which is a carboxyl group, is more preferred.
In the formula (I), the tetravalent group of R
1
may include, for example, the following groups:
and the hydrogenated groups thereof, wherein A represents
sulfur atom or a direct linkage, each A is the same or different, R
7
and R
8
may be the same or different from each other and each represents an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an aryl group having 6 to 14 carbon atoms or an aralkyl group having 7 to 17 carbon atoms, and s represents 0 or an integer of 1 or more, and the divalent group of R
2
may include, for example, the following groups:
and the hydrogenated groups thereof, wherein B has the same meaning as A, each B is the same or different, R
9
and R
10
may be the same or different from each other and each represents an alkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 3 to 8 carbon atoms, an arylene group having 6 to 14 carbon atoms or an aralkylene group having 7 to 17 carbon atoms, R
11
and R
12
may be the same or different from each other and each represents an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an aryl group having 6 to 14 carbon atoms or an aralkyl group having 7 to 17 carbon atoms, and t represents an integer of 1 or more.
The aromatic rings of the above tetravalent groups may have one or more substituents such as alkyl groups having 1 to 6 carbon atoms and alkoxy groups having 1 to 6 carbon atoms.
The aromatic rings of the above divalent groups may have one or more substituents such as alkyl groups having 1 to 6 carbon atoms, alkoxy groups having 1 to 6 carbon atoms and hydroxyl groups.
R
3
and R
4
exist at the ortho-position relative to one of the carbonyl groups bonded to R
1
, and at least one of which is a carboxyl group and the other is a hydrogen atom or a carboxyl group.
The polyamic acid resin preferably has a number average molecular weight of 3,000 to 200,000, more preferably 5,000 to 100,000, most preferably 7,000 to 50,000.
If the number average molecular weight is too low, the mechanical property is lowered. If the number average molecular weight is too high, the resolution is lowered.
The polyamic acid resin having the recurring units represented by the formula (I) can be prepared by reacting, for example, a tetracarboxylic dianhydride as an acidic component and a diamine as an amine component in an organic solvent.
In such a case, the group represented by R
1
and R
2
in the formula (I) represents an acidic component residue as for R
1
and an amine component residue as for R
2
.
As the above tetracarboxylic dianhydride, for example, pyrromellitic dianhydride, 3,3′,4,4′-benzophenonetetracarboxylic dianhydride, 3,3′,4,4′-biphenyltetracarboxylic dianhydride, 1,2,5,6-naphthalenetetracarboxylic dianhydride, 2,3,6,7-naphthalenetetracarboxylic dianhydride, 2,3,5,6-pyridinetetracarboxylic dianhydride, 1,4,5,8-naphthalenetetracarboxylic dianhydride, 3,4,9,10-perylene tetracarboxylic dianhydride, 4,4′-sulfonyldiphthalic dianhydride, m-terphenyl-3,3″,4,4″-tetracarboxylic dianhydride, p-terphenyl-3,3″,4,4″-tetracarboxylic dianhydr
Hagiwara Hideo
Kaji Makoto
Kojima Yasunori
Antonelli, Terry Stout & Kraus, LLP.
Chapman Mark
Hitachi Chemical Co. Ltd.
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