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WO2002014435A1 - Chromophores a base de dibenzoanthraquinone - Google Patents

Chromophores a base de dibenzoanthraquinone Download PDF

Info

Publication number
WO2002014435A1
WO2002014435A1 PCT/AU2001/001001 AU0101001W WO0214435A1 WO 2002014435 A1 WO2002014435 A1 WO 2002014435A1 AU 0101001 W AU0101001 W AU 0101001W WO 0214435 A1 WO0214435 A1 WO 0214435A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituents
substituted
fused
infrared
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.)
Ceased
Application number
PCT/AU2001/001001
Other languages
English (en)
Inventor
Lachlan Everett Hall
Kia Silverbrook
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.)
Silverbrook Research Pty Ltd
Original Assignee
Silverbrook Research Pty Ltd
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
Priority claimed from AUPQ9376A external-priority patent/AUPQ937600A0/en
Priority claimed from AUPQ9412A external-priority patent/AUPQ941200A0/en
Priority claimed from AUPQ9509A external-priority patent/AUPQ950900A0/en
Priority claimed from AUPQ9561A external-priority patent/AUPQ956100A0/en
Priority claimed from AUPQ9571A external-priority patent/AUPQ957100A0/en
Application filed by Silverbrook Research Pty Ltd filed Critical Silverbrook Research Pty Ltd
Priority to AU2001279502A priority Critical patent/AU2001279502A1/en
Publication of WO2002014435A1 publication Critical patent/WO2002014435A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/50—Sympathetic, colour changing or similar inks
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
    • B41J3/00—Typewriters or selective printing or marking mechanisms characterised by the purpose for which they are constructed
    • B41J3/44—Typewriters or selective printing mechanisms having dual functions or combined with, or coupled to, apparatus performing other functions
    • B41J3/50—Mechanisms producing characters by printing and also producing a record by other means, e.g. printer combined with RFID writer
    • B41J3/51—Mechanisms producing characters by printing and also producing a record by other means, e.g. printer combined with RFID writer the printed and recorded information being identical; using type elements with code-generating means
    • 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
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/007—Squaraine dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes

Definitions

  • the present invention relates to compounds that consist of molecules that are suitable for use as dyes.
  • the present invention relates to compounds that are suitable for use as infrared dyes, to compositions containing these compounds, including color light-sensitive material, and to processes for their use as infrared absorbers.
  • the present invention has particular application to infrared printing inks.
  • GaAlAs gallium aluminium arsenide
  • InP indium phosphide
  • Infrared dyes have applications in many areas. For example, infrared dyes are important in the optical data storage field, particular in the DRAW (Direct Reading After Writing) and WORM (Write Once, Read Many) disk, which is used for recording.
  • DRAW Direct Reading After Writing
  • WORM Write Once, Read Many
  • indolinocyanine dyes, triphenylmethane dyes, naphthalocyanine dyes and indonanaphthalo-metal complex dyes are commercially available for use as organic colorants in DRAW disks. Cyanine dyes can only be used if additives improve the lightfastness.
  • infrared dyes are in thermal writing displays. In this application, heat is provided by a laser beam or heat impulse current.
  • the most common type of infrared dyes used in this application are the cyanine dyes, which are known as laser dyes for infrared lasing. Infrared dyes are also used as photoreceptors in laser printing. Some infrared-absorbing dyes are used in laser filters. They, also find application in infrared photography and even have application in medicine, for example, in photodynamic therapy.
  • U.S. Pat. No. 5,093,147 describes a method exploiting the process of fluorescence in which a dye is excited by ultra-violet (UV), visible or near-IR radiation and fluorescent light emitted by the dye material is detected.
  • UV ultra-violet
  • This reference describes a jet printing process used to apply a compatible liquid or viscous substance containing an organic laser dye that is poorly absorptive of radiation in the visible wavelength range of about 400 nm to about 700 nm, and is highly absorptive of radiation in the near-IR wavelength range of about 750 nm to about 900 nm.
  • the dye fluoresces at longer wavelengths in the TR in response to radiation excitation in the near-IR range.
  • a first embodiment of the invention is a molecule 1
  • m and n are the number of fused 6-membered aromatic rings connected to each side of the central moiety such that the first 6-membered aromatic ring, if present, is connected as shown in 1;
  • Qi and Q 2 are one of the same or different fused rings shown as 2 whereby one ring shown
  • 1 2 as 2 is connected at any of the two adjoining positions to C 4 at any orientation and another ring shown as 2 is connected to any of the two adjoining positions C 5 to Cg at any orientation of the outer aromatic rings shown in 1 which may also include one or many substituents individually selected from the group consisting of Ri, a fused 5-membered ring or a 6-membered aromatic ring optionally substituted with 1 to 4 substituents individually selected from R 2 , and fused polyaromatic rings optionally substituted with one or more substituents selected from R 3 where R l5 R 2 and R 3 are individually selected from the group R; and where X is selected from the group consisting of CO, 0, S, SO, S0 2 , Se, SeO, Se0 2 , Te, TeO, Te0 2 , CR Rs , NR 4 , SiR 4 R 5 ⁇ GeRjRs , PR, where R, and R 5 , which may be the same or different, are selected from the group R; and where Y is individually selected from the group
  • Te, TeO, Te0 2 , CR ⁇ Rv , NR 6 , SiR ⁇ Rv, GeRe ? , PR 6 and Z is selected from CR 8 or N where R 6 , R 7 and R 8 which may be the same or different, are selected from the group R; and where Z is individually selected from the group consisting of CO, O, S, SO, S0 2 , Se, SeO, Se0 2 ,
  • Te, TeO, Te0 2 , CR 9 R 10, NR 9 , SiR 9 R, 0 , GeR 9 R ⁇ 0 , PR 9 and Y is selected from CRscene or N where R 9 , R ⁇ 0 and
  • R ⁇ which may be the same or different, are selected from the group R;
  • Q and Q may be 0, 1 or more than 1 substituents that are individually selected from the group consisting of Rj 2 , a fused 5-memebered ring or a 6-membered aromatic ring optionally substituted with 1 to 4 substituents individually selected from R1 3 , and fused polyaromatic rings optionally substituted with one or more substituents selected from R 14 where R 12 , R 13 and R 14 are individually selected from the group
  • R is the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a halide atom, a hydroxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thioalkyl group; where the infrared dye absorbs strongly in the near infrared region of the spectrum but poorly in the visible region of the spectrum.
  • a preferred form of the invention is an infrared dye composition comprising a molecule as described herein.
  • a further preferred form of the invention is an infrared absorbing dye composition
  • an infrared absorbing dye composition comprising a molecule as disclosed herein where bulky substituents are utilized.
  • a further preferred form of the invention is an infrared absorbing compound comprising a molecule as disclosed herein where one or more polar group substituents such as -S0 3 H, -NH 2 and -CN are utilized.
  • a further preferred form of the invention is a solvent-based ink composition comprising a molecule as disclosed herein.
  • a further preferred form of the invention is a solvent-based ink jet printer ink composition comprising a molecule as disclosed herein.
  • Figure 1 shows a calculated absorption spectrum for dye molecule 3
  • Figure 2 shows a calculated absorption spectrum for dye molecule 4
  • Figure 3 shows a calculated absorption spectrum for dye molecule 5;
  • Figure 4 shows a calculated absorption spectrum for dye molecule 6
  • Figure 5 shows a calculated absorption spectrum for dye molecule 7
  • Figure 6 shows a calculated absorption spectrum for dye molecule 8.
  • Figure 7 shows a calculated absorption spectrum for dye molecule 9
  • Figure 8 shows a calculated absorption spectrum for dye molecule 10
  • croconium and squarylium dyes have absorption peaks in the near infrared part of the spectrum, typically from 700 to 900 nanometers.
  • the croconate dyes of Simard et al (supra) actually extend up to 1081 nanometers.
  • the ratio of near infrared absorption, that is absorption from 700 to less than about 2000 nm in wavelength, to visible absorption ( ⁇ ratio ) for the squarylium or croconate dyes is not sufficient when deposited onto a surface. We have found that an improvement of this ratio can be achieved by using a molecule that is shown as 1.
  • m and n are the number of fused 6-membered aromatic rings connected to each side of the central moiety such that the first 6-membered aromatic ring, if present, is connected as shown in 1; and wherein Qi and Q 2 are one of the same or different fused rings shown as 2 whereby one ring shown as 2 is connected at any of the two adjoining positions C, to C 4 at any orientation and another ring shown as 2 is connected to any of the two adjoining positions C 5 to C 8 at any orientation of the outer aromatic rings shown in 1 which may also include one or many substituents individually selected from the group consisting of Ri, a fused 5-membered ring or a 6-membered aromatic ring optionally substituted with 1 to 4 substituents individually selected from R 2 , and fused polyaromatic rings optionally substituted with one or more substituents selected from R 3 wherein R l5 R 2 and R 3 are individually selected from the group R; and wherein X is selected from the group consisting of CO, O, S, SO, S0 2
  • Se0 2 , Te, TeO, Te0 2 , CR ⁇ Ry, NR 6 , SiR ⁇ R ⁇ , GeReR ? , PR 6 and Z is selected from CR 8 or N where R 5 , R 7 and R 8 which may be the same or different, are selected from the group R; and wherein Z is individually selected from the group consisting of CO, O, S, SO, S0 2 , Se, SeO, Se0 2 , Te, TeO, Te0 2 , CR 9 R I0 , NR 9 , SiR 9 R 10 , GeR 9 R, 0, PR 9 and Y is selected from CRn or N where R 9 , R 10 and R ⁇ which may be the same or different, are selected from the group R; and
  • Q 3 and Q 4 may be 0, 1 or more than 1 substituents that are individually selected from the group consisting of R t2 , a fused 5-memebered ring or a 6-membered aromatic ring optionally substituted with 1 to 4 substituents individually selected from R 13 , and fused polyaromatic rings optionally substituted with one or more substituents selected from R 1 wherein R ⁇ 2 , R1 3 and R t are individually selected from the group R; and
  • R is the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a halide atom, a hydroxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thioalkyl group.
  • Bulky substituents are preferably used in an attempt to decrease the intermolecular interactions as these intermolecular interactions may increase the absorption of the compound in the visible part of the spectrum.
  • the present invention provides an infrared dye, characterized in that the dye comprises of a molecule shown in 1.
  • the present invention provides indicia for a substrate.
  • the substrate may be paper, polymer, and the like.
  • the indicia may be printed characters, shapes or the like that any machine readable instrument may detect or any visual markings that may be detected.
  • Examples of infrared dyes in accordance with the present invention comprise of the molecules 3 to 10 given below.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Accessory Devices And Overall Control Thereof (AREA)
  • Record Information Processing For Printing (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Photometry And Measurement Of Optical Pulse Characteristics (AREA)
  • Optical Filters (AREA)

Abstract

L'invention concerne des colorants infrarouge à forte capacité d'absorption dans la région proche de l'infrarouge, mais à faible capacité d'absorption dans la région visible, représentés par les formules (1) et (2). Dans ces formules, m et n sont le nombre de chaînes aromatiques fusionnées à 6 éléments, reliées à chacun des côtés de la fraction centrale de sorte que la première chaîne aromatique à 6 éléments, lorsqu'elle est présente, soit reliée comme indiqué sur la formule (1). Q1 et Q2 sont des chaînes fusionnées identiques ou différentes comme indiqué sur la formule (2); une chaîne, telle que représentée en (2), est reliée en l'une quelconque des deux positions adjacentes C1 à C4, selon une orientation quelconque, et une autre chaîne, telle que représentée en (2), est reliée en l'une quelconque des deux positions adjacentes C5 à C8, selon une orientation quelconque des chaînes aromatiques externes représentées en (1). Q3, X, Y, Z sont tels que décrits dans l'invention. L'invention concerne également des compositions renfermant les composés considérés, et leur utilisation comme éléments absorbant l'infrarouge, particulièrement en liaison avec les encres d'imprimerie à infrarouge.
PCT/AU2001/001001 2000-08-14 2001-08-14 Chromophores a base de dibenzoanthraquinone Ceased WO2002014435A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001279502A AU2001279502A1 (en) 2000-08-14 2001-08-14 Dibenzoanthraquinone based chromophores

Applications Claiming Priority (10)

Application Number Priority Date Filing Date Title
AUPQ9376 2000-08-14
AUPQ9412 2000-08-14
AUPQ9376A AUPQ937600A0 (en) 2000-08-14 2000-08-14 Infrared ink composition (ink02)
AUPQ9412A AUPQ941200A0 (en) 2000-08-14 2000-08-14 Infrared ink composition (ink01)
AUPQ9509A AUPQ950900A0 (en) 2000-08-18 2000-08-18 Infrared ink composition (INK03)
AUPQ9509 2000-08-18
AUPQ9561A AUPQ956100A0 (en) 2000-08-21 2000-08-21 Infrared ink composition (INK04)
AUPQ9561 2000-08-21
AUPQ9571A AUPQ957100A0 (en) 2000-08-21 2000-08-21 Infrared ink composition (INK03A)
AUPQ9571 2000-08-21

Publications (1)

Publication Number Publication Date
WO2002014435A1 true WO2002014435A1 (fr) 2002-02-21

Family

ID=27507491

Family Applications (5)

Application Number Title Priority Date Filing Date
PCT/AU2001/001000 Ceased WO2002014434A1 (fr) 2000-08-14 2001-08-14 Chromophores a base de dibenzofluorenone
PCT/AU2001/001002 Ceased WO2002014437A1 (fr) 2000-08-14 2001-08-14 Chromophores du type a diarylpolymethine ponte
PCT/AU2001/000996 Ceased WO2002014075A1 (fr) 2000-08-14 2001-08-14 Imprimante a encre sympathique imprimant une interface sur une surface
PCT/AU2001/001001 Ceased WO2002014435A1 (fr) 2000-08-14 2001-08-14 Chromophores a base de dibenzoanthraquinone
PCT/AU2001/000999 Ceased WO2002014438A1 (fr) 2000-08-14 2001-08-14 Chromophores infrarouges

Family Applications Before (3)

Application Number Title Priority Date Filing Date
PCT/AU2001/001000 Ceased WO2002014434A1 (fr) 2000-08-14 2001-08-14 Chromophores a base de dibenzofluorenone
PCT/AU2001/001002 Ceased WO2002014437A1 (fr) 2000-08-14 2001-08-14 Chromophores du type a diarylpolymethine ponte
PCT/AU2001/000996 Ceased WO2002014075A1 (fr) 2000-08-14 2001-08-14 Imprimante a encre sympathique imprimant une interface sur une surface

Family Applications After (1)

Application Number Title Priority Date Filing Date
PCT/AU2001/000999 Ceased WO2002014438A1 (fr) 2000-08-14 2001-08-14 Chromophores infrarouges

Country Status (2)

Country Link
EP (1) EP1311396A4 (fr)
WO (5) WO2002014434A1 (fr)

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Publication number Priority date Publication date Assignee Title
AU2002952483A0 (en) 2002-11-05 2002-11-21 Silverbrook Research Pty Ltd Methods and Systems (NPW009)
WO2014123102A1 (fr) 2013-02-08 2014-08-14 三菱瓦斯化学株式会社 Composé, matériau de formation de film de sous-couche pour lithographie, film de sous-couche pour lithographie et procédé de formation de motif
EP2955577B1 (fr) * 2013-02-08 2018-01-31 Mitsubishi Gas Chemical Company, Inc. Composé, substance formatrice de sous-couche pour lithographie, sous-couche pour lithographie ainsi que procédé de formation de motif
WO2014123032A1 (fr) 2013-02-08 2014-08-14 三菱瓦斯化学株式会社 Composition de réserve, procédé de formation de motif de réserve, et dérivé de polyphénol mis en œuvre dans ce procédé
KR20170099908A (ko) 2014-12-25 2017-09-01 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 화합물, 수지, 리소그래피용 하층막 형성 재료, 리소그래피용 하층막, 패턴 형성방법 및 정제방법
JP6766803B2 (ja) 2015-03-31 2020-10-14 三菱瓦斯化学株式会社 レジスト組成物、レジストパターン形成方法、及びそれに用いるポリフェノール化合物
KR102548109B1 (ko) 2015-03-31 2023-06-27 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 화합물, 레지스트 조성물 및 이것을 이용하는 레지스트패턴 형성방법
EP3346335A4 (fr) 2015-08-31 2019-06-26 Mitsubishi Gas Chemical Company, Inc. Matériau destiné à former des films de sous-couche pour lithographie, composition destinée à former des films de sous-couche pour lithographie, film de sous-couche pour lithographie et procédé de fabrication associé, procédé de formation de motif, résine, et procédé de purification
WO2017038643A1 (fr) 2015-08-31 2017-03-09 三菱瓦斯化学株式会社 Matériau permettant de former des films de sous-couche pour lithographie, composition pour former des films de sous-couche pour lithographie, film de sous-couche pour lithographie et son procédé de production, et procédé de formation de motif de réserve
KR102687507B1 (ko) 2015-09-10 2024-07-24 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 화합물, 수지, 레지스트 조성물 또는 감방사선성 조성물, 레지스트 패턴 형성방법, 아몰퍼스막의 제조방법, 리소그래피용 하층막 형성재료, 리소그래피용 하층막 형성용 조성물, 회로패턴의 형성방법 및 정제방법
JP7222517B2 (ja) * 2018-08-31 2023-02-15 国立研究開発法人理化学研究所 新規化合物及びその製造方法

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Also Published As

Publication number Publication date
WO2002014438A1 (fr) 2002-02-21
WO2002014437A8 (fr) 2002-04-18
WO2002014434A1 (fr) 2002-02-21
EP1311396A4 (fr) 2005-06-08
WO2002014437A1 (fr) 2002-02-21
EP1311396A1 (fr) 2003-05-21
WO2002014075A1 (fr) 2002-02-21

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