Radiation imagery chemistry: process – composition – or product th – Imaged product – Including resin or synthetic polymer
Reexamination Certificate
2001-11-01
2003-07-15
Chu, John S. (Department: 1752)
Radiation imagery chemistry: process, composition, or product th
Imaged product
Including resin or synthetic polymer
C430S020000, C430S028000, C430S165000, C430S191000, C430S192000, C430S193000
Reexamination Certificate
active
06593043
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a composition of a positive photosensitive polyimide precursor, which is suitable as a surface protective layer and interlayer dielectric of a semiconductor device and an insulating layer of an organic electroluminescent device. In the resulting positive photosensitive polyimide precursor, exposed portions irradiated with ultraviolet rays are dissolved in an alkaline aqueous solution.
2. Description of the Related Art
Known compositions of positive heat-resistant resin precursors, in which exposed portions are dissolved by alkali-development, include a composition containing a polyamic acid with a naphthoquinonediazide, a composition containing a soluble polyimide having a hydroxyl group with a naphthoquinonediazide, and a composition containing a polyamide having a hydroxyl group with a naphthoquinonediazide.
However, such a composition containing a conventional polyamic acid with a naphthoquinonediazide cannot yield a desired pattern in most cases, since high solubility of the carboxyl group of the polyamic acid overcomes dissolution-inhibitory effect of the naphthoquinonediazide to an alkaline developer. In order to control the alkaline solubility of a polyamic acid, a polyamic acid derivative in which the carboxyl group of the polyamic acid is protected with an ester group has been developed.
However, a composition containing the above polyamic acid derivative with a naphthoquinonediazide exhibits very high dissolution-inhibitory effect to an alkaline developer due to the naphthoquinonediazide, therefore cannot be developed in a short time (hereinafter referred to as “low sensitivity”) and cannot yield a fine pattern with a high resolution (hereinafter referred to as “low resolution”) in most cases, whereas it can yield a desired pattern.
SUMMARY OF THE INVENTION
Specifically, the present invention provides, in an aspect, a composition of a positive photosensitive resin precursor (hereinafter briefly referred to as “resin composition” or “precursor composition”), including (a) a polyamic acid ester and/or a polyamic acid each having at least one of a carboxyl group, a phenolic hydroxyl group, a sulfonic acid group, a thiol group and combinations thereof at the end of a principal chain of the polymer, (b) a compound having a phenolic hydroxyl group and (c) a quinonediazide sulfonate.
In another aspect, the present invention provides a display device including a substrate, a first electrode formed on the substrate, an insulating layer formed on the first electrode in such a manner that part of the first electrode is exposed, and a second electrode facing the first electrode, in which the insulating layer includes the aforementioned resin composition.
The resin composition of the present invention can be developed in an alkaline aqueous solution, exhibits excellent resolution, sensitivity and film residual rate and can specifically advantageously used as an insulating layer of a display.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The present inventors have found that a resin composition containing a compound having a phenolic hydroxyl group and a naphthoquinonediazide compound in addition to a polyimide precursor is dissolved little in an alkali developer before exposure and is readily dissolved in the alkali developer after exposure, which polyimide precursor is synthetically obtained by using an endcapping agent having an alkali-soluble group. This resin composition exhibits less reduction in film thickness due to development, can be developed in a short time (hereinafter referred to as “high sensitivity”) and can yield a fine pattern (hereinafter referred to as “high resolution”). The present invention has been accomplished based on these findings.
Polyamic acid esters for use in the present invention can become polymers each having an imide ring structure by heat or by catalysis of an appropriate catalyst. The resulting polymers each have an imide ring structure and have significantly improved heat resistance and solvent resistance.
In Formulae (1), (2), (3) and (4), R
1
is an organic group having a valency of 4; R
2
is an organic group having a valency of from 2 to 4; R
3
is a hydrogen atom and/or an organic group having from 1 to 20 carbon atoms; R
4
is an organic group having a valency of 2; X is an organic group having at least one of a carboxyl group, a phenolic hydroxyl group, a sulfonic acid group and a thiol group and having a valency of from 2 to 8; n is an integer from 10 to 100000; and m is an integer from 0 to 10.
The component R
1
in Formulae (1), (2), (3) and (4) represents a structural component of a dianhydride. The dianhydride is preferably a tetravalent organic group having an aromatic ring or an aliphatic ring and having a valency of from 4, of which an organic group having from 5 to 40 carbon atoms is typically preferred.
Such dianhydrides include, but are not limited to, pyromellitic dianhydride, 3,3′,4,4′-biphenyltetracarboxylic dianhydride, 2,3,3′,4′-biphenyltetracarboxylic dianhydride, 2,2′,3,3′-biphenyltetracarboxylic dianhydride, 3,3′,4,4′-benzophenonetetracarboxylic dianhydride, 2,2′,3,3′-benzophenonetetracarboxylic dianhydride, 2,2-bis(3,4-dicarboxyphenyl)propane dianhydride, 2,2-bis(2,3-dicarboxyphenyl)propane dianhydride, 1,1-bis(3,4-dicarboxyphenyl)ethane dianhydride, 1,1-bis(2,3-dicarboxyphenyl)ethane dianhydride, bis(3,4-dicarboxyphenyl)methane dianhydride, bis(2,3-dicarboxyphenyl)methane dianhydride, bis(3,4-dicarboxyphenyl) sulfone dianhydride, bis(3,4-dicarboxyphenyl) ether dianhydride, 1,2,5,6-naphthalenetetracarboxylic dianhydride, 2,3,6,7-naphthalenetetracarboxylic dianhydride, 2,3,5,6-pyridinetetracarboxylic dianhydride, 3,4,9,10-perylenetetracarboxylic dianhydride, 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride, and other aromatic tetracarboxylic dianhydrides; and butanetetracarboxylic dianhydride, 1,2,3,4-cyclopentanetetracarboxylic dianhydride, and other aliphatic tetracarboxylic dianhydrides. Among them, 3,3′,4,4′-biphenyltetracarboxylic dianhydride, 2,3,3′,4′-biphenyltetracarboxylic dianhydride, 2,2′,3,3′-biphenyltetracarboxylic dianhydride, 3,3′,4,4′-benzophenonetetracarboxylic dianhydride, 2,2′,3,3′-benzophenonetetracarboxylic dianhydride, 2,2-bis(3,4-dicarboxyphenyl)propane dianhydride, 2,2-bis(2,3-dicarboxyphenyl)propane dianhydride, 1,1-bis(3,4-dicarboxyphenyl)ethane dianhydride, 1,1-bis(2,3-dicarboxyphenyl)ethane dianhydride, bis(3,4-dicarboxyphenyl)methane dianhydride, bis(2,3-dicarboxyphenyl)methane dianhydride, bis(3,4-dicarboxyphenyl) sulfone dianhydride, bis(3,4-dicarboxyphenyl) ether dianhydride, and 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride are preferred. Each of these components can be used alone or in combination.
The component R
2
in Formulae (1), (2), (3) and (4) represents a structural component of a diamine. Such diamines are preferably organic groups each having an aromatic ring or an aliphatic ring and having a valency of from 2 to 4, of which organic groups each having from 5 to 40 carbon atoms are typically preferred.
Such diamines include, but are not limited to, 3,4′-diaminodiphenyl ether, 4,4′-diaminodiphenyl ether, 3,4′-diaminodiphenylmethane, 4,4′-diaminodiphenylmethane, 3,4′-diaminodiphenyl sulfone, 4,4′-diaminodiphenyl sulfone, 3,4′-diaminodiphenyl sulfide, 4,4′-diaminodiphenyl sulfide, 1,4-bis(4-aminophenoxy)benzene, benzidine, m-phenylenediamine, p-phenylenediamine, 1,5-naphthalenediamine, 2,6-naphthalenediamine, bis(4-aminophenoxyphenyl) sulfone, bis(3-aminophenoxyphenyl) sulfone, bis(4-aminophenoxy)biphenyl, bis{4-(4-aminophenoxy)phenyl}ether, 2,2′-dimethyl-4,4′-diaminobiphenyl, 2,2′-diethyl-4,4′-diaminobiphenyl, 3,3′-dimethyl-4,4′-diaminobiphenyl, 3,3′-diethyl-4,4′-diaminobiphenyl, 2,2′,3,3′-tetramethyl-4,4′-diaminobiphenyl, 3,3′,
Miyoshi Kazuto
Suwa Mitsuhito
Tomikawa Masao
Chu John S.
Kubovcik & Kubovcik
Toray Industries Inc.
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