Radiation imagery chemistry: process – composition – or product th – Transfer procedure between image and image layer – image... – Imagewise heating – element or image receiving layers...
Reexamination Certificate
1999-12-10
2001-01-30
Baxter, Janet (Department: 1752)
Radiation imagery chemistry: process, composition, or product th
Transfer procedure between image and image layer, image...
Imagewise heating, element or image receiving layers...
C430S208000, C430S292000, C430S334000, C430S336000, C430S363000, C430S374000, C347S212000, C427S532000, C427S554000, C427S557000, C427S596000, C427S256000
Reexamination Certificate
active
06180315
ABSTRACT:
The present invention relates to novel compositions for making structured color images and applications thereof.
As methods for forming polymer pattern or image layers, there are known various techniques like photolithography, impact printing, such as screen printing, gravure printing, flexo printing and offset printing, non-impact printing, such as ink-jet printing, thermal dye diffusion transfer, laser marking, electrodeposition, etc. In all such imaging and recording methods, the actual coloring material comprises pigments and dyestuffs combined with appropriate resins, binders, polymers and additives.
Such colors are applied, thus, for example, as recording elements of optical memories as disclosed in JP Kokai 05050757 A, as recording elements of thermal recording memories as disclosed in EP-A535788, and as coloring materials for color filters of LCDs (liquid crystal displays) as described in H. Aruga, J. Photopolym. Sci. Technol., 3(1)9-16(1990), EP-A380223, K. Mizuno et al., Jpn. J. Appl. Phys., Part 1, 30 3313-17(1991) and K. Kobayashi, Solid State Technology, 11(1992)15-18. Polymeric pattern layers may be coloured after crosslinking, for example through thermal dye diffusion transfer with well-known dyes as mentioned in EP-008828.
According to the above literature, pigments and dyestuffs are used in the form of compositions containing pigments or dyestuffs, polymers or prepolymers and optionally other additives, which are subject to image formation in order to achieve recording or form colored patterns. The process usually comprises the polymerization of a prepolymer or the depolymerization of a structurable polymer by applying heat or electromagnetic radiation or the combination thereof, and the subsequent development using appropriate developers; alternatively, pigments or dyestuffs may be applied directly in a selective pattern, for example through non-impact printing.
While dyes in general are deficient in terms of light, heat, solvent and chemical resistance, pigments in such applications show problems related to dispersion and dispersion stability, transparency, profile sharpness of absorption or transmission spectra and/or lack of solubility or diffusibility. Many properties desirable for the dye's or pigment's nice incorporation into critical systems such as colour LCD's are contradictory with such required for high quality applications. Unsatisfactory compromises have thus to be complied with, like in JP Kokai 60180889 where stability is obtained at the cost of low optical reflection density and poor color gamut, and many pigment classes cannot be used at all. The present invention overcomes this problem.
Recent development in imaging and recording technology requires, however, compositions for producing patterns or images with:
higher transparency (i.e. high light transmittance), especially for color filter of LCDs,
higher contrast ratio,
higher color purity and strength,
higher pattern resolution and precision of image,
no (dye) color mixing,
no clogging of sieves during purification of color/polymer mixtures,
smoothness of image surface,
pinhole free and noncontaminated image layer,
higher registration accuracy,
higher sharpness of image edges,
higher thermal, chemical and light stability, and
ultra thin film characteristics.
It has now been found, surprisingly, that special soluble pigment precursors may be effected by chemical, thermal, photolytical means, by laser and other means of irradiation to undergo in situ generation of insoluble nano-sized pigment particles, and that the compositions containing the above special pigment precursors for structured color patterns and image formation satisfy the aforementioned requirements.
The present invention relates, accordingly, to novel compositions for forming structured color images containing soluble pigment precursors, in which the precursors regenerate insoluble nano-sized pigment particles by the effect of chemical, thermal, photolytical means or by laser and other means, and application thereof to recording and imaging technology, especially to the fabrication of color filters for LCDs.
In one aspect of the present invention, therefore, there are provided novel compositions for making structured color images comprising:
(a) a soluble pigment precursor which can be transformed to an insoluble pigment by means of chemical-, thermal-, photolytic- or radiation-induced method or a combination thereof; and
(b) a positive or negative resist-type resin, polymer or prepolymer which can be structured by polarity changes, crosslinking, polymerization or depolymerization by applying heat or electromagnetic irradiation such as UV-, visible-, electron-, neutron-, laser- or X-ray irradiation or a combination thereof.
The soluble pigment precursor (a) according to the present invention is represented by formula I
A(B)
x
(I),
wherein x is a number from 1 to 4,
A is the residue of a colorant of the quinacridone-, anthraquinone-, perylene-, indigo-, quinophthalone-, isoindolinone-, isoindoline-, dioxazine-, diketopyrrolopyrrole- or azo series, which is linked to x groups B via N atoms, which nitrogens are part of A and preferably adjacent to or conjugated with a carbonyl group;
B is a group bound to A, represented by formulae
and wherein in formulae II, III and IV m, n and p are each independently of the other 0 or 1,
X is C
1
-C
14
-alkylene or C
2
-C
8
-alkenylene,
Y is a group —V—(CH
2
)
q
—,
Z is a group —V—(CH
2
)
r
—,
V is C
3
-C
6
-cycloalkylen,
q is a number between 1 and 6,
r is a number between 0 and 6,
R
1
and R
2
are each independently of the other hydrogen, C
1
-C
6
-alkyl, C
1
-C
4
-alkoxy, halogen, CN, NO
2
, phenyl or phenoxy which are unsubstituted or substituted by C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy or halogen,
Q is hydrogen, CN, Si(R
1
)
3
, a group C(R
5
)(R
6
)(R
7
), wherein R
5
, R
6
and R
7
are each independently of the other hydrogen or halogen and at least one of the residues R
5
, R
6
and R
7
is halogen, a group
wherein R
1
and R
2
have the same meaning as given above,
a group SO
2
R
8
or SR
8
, wherein R
8
is C
1
-C
4
-alkyl,
a group CH(R
9
)
2
, wherein R
9
is phenyl which is unsubstituted or substituted by C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy or halogen, or
a group of formula
and R
3
and R
4
are each independently of the other hydrogen; C
1
-C
18
-alkyl
or a group
wherein X, Y, R
1
, R
2
, m and n have the above given meaning, or R
3
and R
4
together with the nitrogen, on which they are bound, form a pyrrolidinyl-, piperidinyl- or morpholinyl residue,
and wherein A(B)
x
may contain additional
═N—, —NH— or —NH
2
groups.
It is not necessary, and in many cases not indicated, that all the N atoms are linked to groups B; on the other hand, more than one group B may be linked to a single N atom.
A means a residue of well-known nitrogen containing chromophores, for example,
as well as all the known derivatives of such chromophores, respectively.
If X is C
1
-C
4
-alkylene, then, it is a straight-chain or branched alkylene, such as methylene, dimethylene, trimethylene, 1-methyl-methylene, 1,1-dimethyl-methylene, 1,1-dimethyl-dimethylene, 1,1-dimethyl-trimethylene, 1-ethyl-dimethylene, 1-ethyl-1-methyl-dimethylene, tetramethylene, 1,1-dimethyl-tetramethylene, 2,2-dimethyl-trimethylene, hexamethylene decamethylene, 1,1-dimethyl-decamethylene, 1,1-diethyl-decamethylene or tetradecamethylene.
X as C
2
-C
8
-alkenylene means straightchain or branched alkylene, such as vinylene, allylene, methallylene, 1-methyl-2-butenylene, 1,1-dimethyl-3-butenylene, 2-butenylene, 2-hexenylene, 3-hexenylene or 2-octenylene.
C
3
-C
6
-cycloalkylene means, for example, cyclopropylene, cyclopentylene and, especially, cyclohexylene.
If the substituents are halogen, then, they are, for example, iodo, fluoro, especially bromo, or preferably chloro.
If the substituents are C
1
-C
6
-alkyl, then, they are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-amyl, tert-amyl or hexyl, and if the substituents are C
1
Dubas Henri
Hao Zhimin
Iqbal Abul
Sch{umlaut over (a)}deli Ulrich
Zambounis John S.
Baxter Janet
Ciba Specialty Chemcials Corporation
Clarke Yvette M
Crichton David R.
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