Radiation sensitive composition

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

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Details

C430S283100, C430S905000, C430S913000, C430S918000, C430S920000

Reexamination Certificate

active

06255034

ABSTRACT:

DETAILED DESCRIPTION OF THE INVENTION
The present invention relates to a radiation sensitive composition comprising a colorant. More specifically, it relates to a radiation sensitive composition which is advantageously used for the production of a color filter for use in color liquid crystal display devices, color image pick-up elements and the like.
A radiation sensitive composition is used to form a color filter for use in color liquid crystal display devices, color image pick-up elements and the like. Since high sensitivity, adhesion to a substrate, chemical resistance and the like are required for the composition, a negative radiation sensitive composition is generally used.
In general, to form a color filter using such a negative radiation sensitive composition, a light screening layer pattern is formed on a transparent substrate, a negative radiation sensitive composition resin having a colorant dispersed therein is applied to the substrate, exposed to radiation through a photomask (to be referred to as “exposure” hereinafter) to be developed, and unexposed portions are dissolved with a developer to form a pixel pattern. Red, green and blue colorants are used as the colorant.
As the negative radiation sensitive composition having the colorant dispersed therein has been conventionally used a negative radiation sensitive composition comprising a resin containing an acidic functional group such as (meth)acrylic acid, a polyfunctional monomer such as pentaerythritol tri(meth)acrylate, and a photopolymerization initiator such as 1-hydroxycyclohexyl phenyl ketone.
However, when a color filter is to be formed from such a negative radiation sensitive composition, a pixel portion which has been cured by exposure may be swollen with an alkali developer at the time of development using the alkali developer, the resolution of the obtained pixel pattern may lower and the pixel pattern may deform. Particularly when a negative radiation sensitive composition having a colorant dispersed therein is used for electronically engineering application in which it is used to form a fine pixel array on a silicon wafer as in the case of an image pick-up element, scum may be produced on the obtained pixel pattern, the surface of the pixel pattern may be roughened, or part of the pixel array may fall off at the time of development with an alkali developer, thereby making it difficult to produce a high-resolution pixel array at a high yield. Further, the adhesion strength of the pixel pattern is lowered by development, whereby the pixel pattern detaches from the substrate when an alignment layer or transparent conductive film is formed after the formation of the pixel array.
As a solution to the above problems, there is proposed, for example, a chemically amplified negative radiation sensitive composition which comprises a red pigment, polyvinyl phenol, methylol melamine and an optical acid generating agent such as 1,1-bis(p-chlorophenyl)-2,2,2-trichloroethane. A color filter obtained by using this composition has a fine pixel pattern having sufficient adhesion strength.
However, when a fine pixel array is to be formed using this chemically amplified negative radiation sensitive composition, an undissolved product (residue) of the composition may remain in unexposed portions (non-pixel portions) or scum may be produced on pixels at the time of development with an alkali developer.
Therefore, the development of a negative radiation sensitive composition for a color filter which is free from an undissolved product (residue) of the composition remaining in an unexposed portions and scum produced on pixels even when a fine pixel array is formed and can form a pixel array having high resolution and excellent adhesion strength to a substrate has been desired.
It is an object of the present invention to provide a novel radiation sensitive composition.
It is another object of the present invention to provide a radiation sensitive composition which is free from undissolved product (residue) of the composition remaining in an unexposed portions and scum produced pixels even when a fine pixel array is formed and can form a pixel array having excellent adhesion strength to a substrate and an excellent pattern shape at a high yield.
It is still another object of the present invention to provide a radiation sensitive composition which is suitable for the production of a color filter.
The other objects and advantages of the present invention will become apparent from the following description.
According to the present invention, firstly, the above objects and advantages of the present invention can be attained by a radiation sensitive composition (may be referred to as “the first composition of the present invention” hereinafter) which comprises:
(A) a colorant;
(B) a binder polymer;
(C) a polyfunctional monomer;
(D1) at least one carboxyl group-containing monofunctional monomer selected from the group consisting of &ohgr;-carboxy-polycaprolactone mono(meth)acrylate, (meth)acrylic acid dimers and mono(2-(meth)acryloyloxyethyl)ester of dicarboxylic acid; and
(E) a photopolymerization initiator.
According to the present invention, secondly, the above objects and advantages of the present invention can be attained by a radiation sensitive composition (may be referred to as “the second composition of the present invention” hereinafter) which comprises;
(A) a colorant;
(B) a binder polymer;
(C) a polyfunctional monomer;
(D2) an amide group-containing monoethylenically unsaturated monomer; and
(E) a photopolymerization initiator.
Thirdly, the above objects and advantages of the present invention can be attained by a radiation sensitive composition (may be referred to as “the third composition of the present invention” hereinafter) which comprises:
(A) a colorant;
(B) a binder polymer;
(C) a polyfunctional monomer;
(D3) a monoethylenically unsaturated monomer having a cyclic amide group or cyclic imide group; and
(E) a photopolymerization initiator.
Fourthly, the above objects and advantages of the present invention can be attained by a radiation sensitive composition (may be referred to as “the fourth composition of the present invention” hereinafter) which comprises:
(A) a colorant;
(B) a binder polymer;
(C) a polyfunctional monomer;
(D4) at least one phenyl group-containing (meth)acrylate selected from the group consisting of compounds represented by the following formula (2):
 wherein R
1
, R
2
and R
3
are independently a hydrogen atom, alkyl group having 1 to 10 carbon atoms, phenyl group, group represented by —COOR
6
, group represented by
 group represented by
 group represented by
 group represented by —R
7
—H, group represented by —R
8
, group represented by
 or group represented by
 or group represented by
R
4
is a hydrogen atom or methyl group, and R
5
is a group represented by
 group represented by
 group represented by
 or group represented by
R
6
is a hydrogen atom or methyl group, R
7
is a group selected from the same groups as those represented by R
5
, and R
8
is a group represented by
R
9
is a hydrogen atom, hydroxyl group or methyl group,
R
10
is a hydrogen atom or methyl group and R
11
is a group selected from the same groups as those represented by R
5
,
and p is an integer of 1 to 10, and compounds represented by the following formula (3):
 wherein R
1
, R R
3
and R
4
are the same as defined in the above formula (2), R
12
and R
13
are independently a group represented by
 or a group selected from the same groups as those represented by R
1
to R
3
in the above formula (2), and q and r are independently an integer of 0 or 1 to 10; and
(E) a photopolymerization initiator.
The present invention will be described in detail below.
The colorant (A), the binder polymer (B) and the polyfunctional monomer (C) will be described first. It should be understood that these descriptions are common to the first, second, third and fourth compositions of the present invention.
(A) Colorant
The colorant in the present invention is not

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