EP0476086A1 - Orange filter dye and filter element for color filter arrays - Google Patents

Orange filter dye and filter element for color filter arrays

Info

Publication number
EP0476086A1
EP0476086A1 EP19910905969 EP91905969A EP0476086A1 EP 0476086 A1 EP0476086 A1 EP 0476086A1 EP 19910905969 EP19910905969 EP 19910905969 EP 91905969 A EP91905969 A EP 91905969A EP 0476086 A1 EP0476086 A1 EP 0476086A1
Authority
EP
European Patent Office
Prior art keywords
dye
filter
color filter
orange
color
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP19910905969
Other languages
German (de)
French (fr)
Inventor
Derek D. Chapman
James K. Elwood
Laurel J. Pace
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eastman Kodak Co
Original Assignee
Eastman Kodak Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Publication of EP0476086A1 publication Critical patent/EP0476086A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
    • G03C1/83—Organic dyestuffs therefor
    • G03C1/831—Azo dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
    • C09B29/0007—Monoazo dyes prepared by diazotising and coupling from diazotized anilines containing acid groups, e.g. CO2H, SO3H, PO3H2, OSO3H, OPO2H2; Salts thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
    • C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
    • C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
    • C09B29/363—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O) from diazotized amino carbocyclic rings
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices

Definitions

  • This invention relates to color solid-state imagers and, more specifically, to an orange azo dye for organic color filter arrays that are used on these imagers and a color filter element containing such orange dye.
  • Background Art Solid-state imagers can be made to discriminate colors by fabrication of color filter arrays (CFAs) over the light-sensitive areas of the device. Typically, CFAs are produced by imbibing organic dyes into a layer that has been patterned in the appropriate filter pattern.
  • CFAs color filter arrays
  • CMFs color matching functions
  • the curves corresponding to y and " z CMFs can generally be approximated by green and blue color filters, respectively.
  • a typical red color filter is a poor match to the x CMF, which would be better approximated by a dye having an orange hue.
  • the x CMF curve can be produced by placing an appropriate infrared cut-off filter in front of the sensor, the hypsochromic edge must be defined by the filter dye in the CFA. Consequently, the spectral requirements for the dye are defined by the characteristics of its absorption edge: for a dye that transmits less than 57 ⁇ of the light at 500 nm (optical density or
  • the dye must be compatible with the matrix used to bind the dye in the color filter.
  • Commercially available CFAs often are made using a photopatternable composition containing a cationic mordant. In order to bind well to this mordant, the filter dye must be anionic.
  • the dye should be soluble in a solvent or aqueous solution of an appropriate p ⁇ (between 3 and 10) that does not attack the rest of the CFA. 3.
  • the dye should be attainable by a straightforward and high-yield synthetic route.
  • the dye should have good light stability.
  • good light stability is defined as a less than 10% decrease in the dye's peak absorbance after exposure to 150 klux—hours of light.
  • Light stability can be enhanced by the use of overcoats, additives, or device packaging procedures that prevent oxygen from reaching the dye.
  • the dye must have good thermal stability. It has been found that various steps used in packaging solid-state imagers require that the dye withstand temperatures of at least 150 ⁇ C for at least 1 hour. Summary of the Invention
  • R'.,—R' are selected from the group consisting of hydrogen, alkyl from 1—8 carbons and halogens and wherein the dye is metallized by a metal such as nickel.
  • the dyes included in this invention are soluble in aqueous solution, are good spectral matches to the x CMF (FIG. 2) and show acceptable stability characteristics. In some cases (specific dye in a particular dye-binding matrix), sufficient light stability can be obtained without the need to exclude oxygen from the layer. In other cases, oxygen exclusion is required in order to attain acceptable light stability.
  • a layer containing one of the dyes may be used in combination (i.e., on top of or under) a layer containing a different dye (e.g., yellow).
  • FIG. 1 is a conventional representation of color matching functions plotted as relative intensity vs. wavelength; and FIG. 2 is a graph of transmission vs. wavelength comprising representative dyes in accordance with this invention with the color matching function x.
  • a metallizable azo dye in accordance with this invention includes: a 3-pyridinol moiety substituted in the 2—position with a methyl group; and an aryl ring connected to the 6-position of the pyridinol moiety through an azo linkage and substituted in an ortho position relative to such connection with a carboxyl group.
  • R, and R 2 which may be the same or different, represents an aryl, an arylalkyl or an alkaryl group having from 6 to less than about 20 carbon atoms or an alkyl group having from 1 to about 10 carbon atoms;
  • R 3 is alkyl containing from 1 to about 3 carbon atoms ; n is 0 , 1 or 2 ;
  • R, and 5 are either both hydrogen or, together with the carbon atom to which they are attached, form a saturated, unsaturated or aromatic ring system containing from 5 to 10 carbon atoms such as cyclohexyl, cyclopentyl, phenyl and naphthyl; X is an acid anion.
  • R ⁇ and R 2 are lower alkyl groups
  • R is a divalent linking group
  • R, , R 5 and R 6 are hydrocarbon groups containing from 1 to 16 carbon atoms
  • X is a photocrosslinking group
  • the diazonium salt B was prepared by dissolving NaOH (4 g; 0.1 mole) in 100 ml of water and then adding anthranilic acid (13.71 g; 0.1 mole). Sodium nitrite (6.9 g; 0.1 mole) was added with stirring until dissolved. This solution was then added with stirring to a beaker containing 200 g of crushed ice and 30 ml of concentrated HC1.
  • the solution of B was added dropwise to a cold stirring solution made up of compound A (10.9 g; 0.1 mole) and Na 2 C0 3 .H 2 0 (95 g; 0.766 moles) dissolved in 500 ml of cold ( ⁇ 5°C) water.
  • the dye solution was stirred for an hour, and the dye (Compound 1) was then separated by carefully adding concentrated HC1 (120 ml; 1.44 mole) with manual stirring. This mixture was stirred for an hour, after which it was filtered. The dye was washed with water and allowed to dry. The reaction yielded 24.0 g (93.3%) of the yellow-orange solid. 2.
  • a dye solution was prepared by adding 2 grams of compound 1 to 1 liter of a standard pH 10 borate buffer.
  • the layer was exposed to UV light for 22 seconds using a Canon PLA501F aligner and developed for 30 seconds with a mixture of 20% methanol and 80% iso-butanol.
  • the dried coating was immersed in the dye solution for 1 minute, rinsed, dried, immersed in a 2% by weight aqueous solution of nickelous acetate for 30 seconds, rinsed, and dried.
  • the final dyed coating had the following transmission characteristics: 500 nm: 1.4% T, 570 nm: 63% T, 600 nm: 87% T.
  • the resulting dye in the filter layer is believed to have the following structure:
  • the dyes which are suitable for color filter arrays included in this invention are soluble in aqueous solution, are good spectral matches to the x CMF (FIG. 2) and show acceptable stability characteristics. In some cases (specific dye in a particular dye-binding matrix), sufficient light stability can be obtained without the need to exclude oxygen from the layer. In other cases, oxygen exclusion is required in order to attain acceptable light stability.

Abstract

Une teinture orangée azoïque et métallisable pour réseaux de filtres-couleur est décrite. Cette teinture est composée de: une partie de 3-pyridinol substituée en position 2 avec un groupe méthyle et un composé cyclique aryle connecté en position 6 de la partie de pyridinol à travers une liaison azoïque et substitué dans une position ortho relative à une telle connection avec un groupe carbonyle. Une couche contenant cette teinture métallisée peut être utilisée pour former un élément de filtrage en couleur.An azo and metallizable orange dye for color filter networks is described. This dye is composed of: a part of 3-pyridinol substituted in position 2 with a methyl group and an aryl cyclic compound connected in position 6 of the part of pyridinol through an azo bond and substituted in an ortho position relative to such a connection with a carbonyl group. A layer containing this metallic dye can be used to form a color filter element.

Description

ORANGE FILTER DYE AND FILTER ELEMENT FOR COLOR FILTER ARRAYS Field of the Invention
This invention relates to color solid-state imagers and, more specifically, to an orange azo dye for organic color filter arrays that are used on these imagers and a color filter element containing such orange dye. Background Art Solid-state imagers can be made to discriminate colors by fabrication of color filter arrays (CFAs) over the light-sensitive areas of the device. Typically, CFAs are produced by imbibing organic dyes into a layer that has been patterned in the appropriate filter pattern.
For some solid-state imaging applications, it is sometimes desirable that the devices have a spectral sensitivity that approximates color matching functions (CMFs). While typical red, green and blue color filters provide sufficient color information for most imagers, CMFs are preferred for some applications requiring higher quality color repoduction because they allow for a more accurate reconstruction of -perceived color. (For more information on CMFs, see "The Theory of the Photographic Process," T.H. James, Ed., 4th Edition, Macmillan Publishing Company, Inc., 1977). Shown in FIG. 1 are the 1931 CIE Color-
Matching Functions x, y and z, plotted as relative intensity vs. wavelength; these CMFs are the internationally adopted standard. The curves corresponding to y and "z CMFs can generally be approximated by green and blue color filters, respectively. A typical red color filter, however, is a poor match to the x CMF, which would be better approximated by a dye having an orange hue. In order to produce a filter to approximate the x CMF, it is necessary to have a CFA dye with the appropriate spectral curve shape, structure, and stability characteristics. The following criteria are considered to be sufficient and reference should be made to FIG. 2. Shown in FIG. 2 is the x CMF curve compared with the transmittance vs. wavelength curve of a coating that contains a dye that meets the specifications set forth in this patent application.
1. While the bathochromic absorption edge of the
x CMF curve can be produced by placing an appropriate infrared cut-off filter in front of the sensor, the hypsochromic edge must be defined by the filter dye in the CFA. Consequently, the spectral requirements for the dye are defined by the characteristics of its absorption edge: for a dye that transmits less than 57β of the light at 500 nm (optical density or
0D>1.3), it should transmit at least 50% (OD<0.3) by 570 nm and at least 80% (0D<0.1) by 600 nm. The hue of this dye is best described as orange, but it should be understood by those skilled in the art that the hue may vary between orange and pink depending on the concentration of the dye.
2. The dye must be compatible with the matrix used to bind the dye in the color filter. Commercially available CFAs often are made using a photopatternable composition containing a cationic mordant. In order to bind well to this mordant, the filter dye must be anionic. Also, to be compatible with the rest of the CFA process, the dye should be soluble in a solvent or aqueous solution of an appropriate pΞ (between 3 and 10) that does not attack the rest of the CFA. 3. The dye should be attainable by a straightforward and high-yield synthetic route.
4. The dye should have good light stability. For the purposes of this invention, good light stability is defined as a less than 10% decrease in the dye's peak absorbance after exposure to 150 klux—hours of light. Light stability can be enhanced by the use of overcoats, additives, or device packaging procedures that prevent oxygen from reaching the dye.
5. The dye must have good thermal stability. It has been found that various steps used in packaging solid-state imagers require that the dye withstand temperatures of at least 150βC for at least 1 hour. Summary of the Invention
The following dye class was found to be particularly well suited to meet all of the criteria set forth above:
wherein R'.,—R', are selected from the group consisting of hydrogen, alkyl from 1—8 carbons and halogens and wherein the dye is metallized by a metal such as nickel.
The dyes included in this invention are soluble in aqueous solution, are good spectral matches to the x CMF (FIG. 2) and show acceptable stability characteristics. In some cases (specific dye in a particular dye-binding matrix), sufficient light stability can be obtained without the need to exclude oxygen from the layer. In other cases, oxygen exclusion is required in order to attain acceptable light stability.
In addition to using these dyes by themselves in a single layer, a layer containing one of the dyes may be used in combination (i.e., on top of or under) a layer containing a different dye (e.g., yellow). Brief Description of the Drawings
FIG. 1 is a conventional representation of color matching functions plotted as relative intensity vs. wavelength; and FIG. 2 is a graph of transmission vs. wavelength comprising representative dyes in accordance with this invention with the color matching function x.
Modes of Carrying Out the Invention
A metallizable azo dye in accordance with this invention includes: a 3-pyridinol moiety substituted in the 2—position with a methyl group; and an aryl ring connected to the 6-position of the pyridinol moiety through an azo linkage and substituted in an ortho position relative to such connection with a carboxyl group.
Specifically, three dyes with the following substituents have been evaluated and found to be acceptable:
Compound 1) H Ξ H H H H
Compound 2) H H H Cl H H
Compound 3) H H. H n-Bu H H Dyes were evaluated in two photopatternable mordant systems, one of which is a mixture of a photosensitive diazo resin (Formula I) and a cationic mordant (Formula II) like that described in McGuckin and Cohen, U.S. Patent No. 4,247,615, and one of which is a polymer containing both a photocrosslinkable cinnamate group and a cationic mordant (Formula III) like that described in Snow et al., U.S. Pat. No. 4,808,510.
FORMULA I
fCH-,-CH7
R - N - R4
FORMULA II wherein:
R, and R2, which may be the same or different, represents an aryl, an arylalkyl or an alkaryl group having from 6 to less than about 20 carbon atoms or an alkyl group having from 1 to about 10 carbon atoms;
R3 is alkyl containing from 1 to about 3 carbon atoms ; n is 0 , 1 or 2 ;
R, and 5 are either both hydrogen or, together with the carbon atom to which they are attached, form a saturated, unsaturated or aromatic ring system containing from 5 to 10 carbon atoms such as cyclohexyl, cyclopentyl, phenyl and naphthyl; X is an acid anion.
FORMULA III wherein:
R^ and R2 are lower alkyl groups;
R is a divalent linking group;
R, , R5 and R6 are hydrocarbon groups containing from 1 to 16 carbon atoms;
X is a photocrosslinking group; and
Z is a charge—balancing counter ion. Examples: 1. Synthetic procedure for preparation of Compound 1:
Compound 1
The diazonium salt B was prepared by dissolving NaOH (4 g; 0.1 mole) in 100 ml of water and then adding anthranilic acid (13.71 g; 0.1 mole). Sodium nitrite (6.9 g; 0.1 mole) was added with stirring until dissolved. This solution was then added with stirring to a beaker containing 200 g of crushed ice and 30 ml of concentrated HC1.
The solution of B was added dropwise to a cold stirring solution made up of compound A (10.9 g; 0.1 mole) and Na2C03.H20 (95 g; 0.766 moles) dissolved in 500 ml of cold (<5°C) water. The dye solution was stirred for an hour, and the dye (Compound 1) was then separated by carefully adding concentrated HC1 (120 ml; 1.44 mole) with manual stirring. This mixture was stirred for an hour, after which it was filtered. The dye was washed with water and allowed to dry. The reaction yielded 24.0 g (93.3%) of the yellow-orange solid. 2. Preparation of filter element containing Compound 1: A dye solution was prepared by adding 2 grams of compound 1 to 1 liter of a standard pH 10 borate buffer. A layer was prepared by spin—coating onto a glass wafer at 3000 rpm an 8.0% solids aqueous solution containing a polymer of Formula III where y = R2 = R4 = R5 = CH3, R3 = -CΞ2CH2-, R& = CH2CH2CH20H and X = -CH2CH20-C0-CH=CH-C6H5 and a sensitizer 3-(7—methoxy-3—coumarinoyl)—1—methylpyridinium p-toluenesulfonate. The ratio of polymer to sensitizer was 12 to 1.
The layer was exposed to UV light for 22 seconds using a Canon PLA501F aligner and developed for 30 seconds with a mixture of 20% methanol and 80% iso-butanol. The dried coating was immersed in the dye solution for 1 minute, rinsed, dried, immersed in a 2% by weight aqueous solution of nickelous acetate for 30 seconds, rinsed, and dried. The final dyed coating had the following transmission characteristics: 500 nm: 1.4% T, 570 nm: 63% T, 600 nm: 87% T. The resulting dye in the filter layer is believed to have the following structure:
Industrial Applicability
The dyes which are suitable for color filter arrays included in this invention are soluble in aqueous solution, are good spectral matches to the x CMF (FIG. 2) and show acceptable stability characteristics. In some cases (specific dye in a particular dye-binding matrix), sufficient light stability can be obtained without the need to exclude oxygen from the layer. In other cases, oxygen exclusion is required in order to attain acceptable light stability.

Claims

Claims :
1. A metallizable azo dye for a color filter array characterized by the following structure:
wherein R1,—R1, are selected from the group consisting of hydrogen, alkyl from 1—8 carbons and halogens and wherein the dye is metallized by a metal such as nickel.
2. The dye of claim 1 wherein R! = R» 2 = R« = Ri = R« = H and R'4 is selected from the group consisting of Cl, n-Bu and H.
3. A color filter element for an image sensor or the like characterized by: a support, and on said support a layer having a photosensitive diazo resin and a cationic mordant and the dye according to claim 1.
4. A color filter element for an image sensor or the like, characterized by: a support, and on said support a layer having polymer with a photocrosslinkable cinnamate group and a cationic mordant and the orange dye according to claim 1.
EP19910905969 1990-03-05 1991-02-27 Orange filter dye and filter element for color filter arrays Withdrawn EP0476086A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US48856590A 1990-03-05 1990-03-05
US488565 1990-03-05

Publications (1)

Publication Number Publication Date
EP0476086A1 true EP0476086A1 (en) 1992-03-25

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP19910905969 Withdrawn EP0476086A1 (en) 1990-03-05 1991-02-27 Orange filter dye and filter element for color filter arrays

Country Status (3)

Country Link
EP (1) EP0476086A1 (en)
JP (1) JPH04505635A (en)
WO (1) WO1991013942A1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6646248B2 (en) 2001-04-24 2003-11-11 Xerox Corporation Photosensitive imaging apparatus sensitive to orange light
JP4408380B2 (en) * 2003-08-20 2010-02-03 富士フイルム株式会社 Negative curable composition, negative color filter and method for producing the same
JP7350280B2 (en) * 2018-09-27 2023-09-26 東海光学株式会社 plastic eyeglass lenses and glasses

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3316887A1 (en) * 1983-05-07 1984-11-08 Agfa-Gevaert Ag, 5090 Leverkusen PHOTOGRAPHIC RECORDING MATERIAL AND NEW AZO DYES
CA1293879C (en) * 1986-06-20 1992-01-07 Laurel Jean Pace Color filter arrays

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9113942A1 *

Also Published As

Publication number Publication date
WO1991013942A1 (en) 1991-09-19
JPH04505635A (en) 1992-10-01

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