WO2009123056A1 - 赤外線吸収性化合物および該化合物からなる微粒子 - Google Patents
赤外線吸収性化合物および該化合物からなる微粒子 Download PDFInfo
- Publication number
- WO2009123056A1 WO2009123056A1 PCT/JP2009/056300 JP2009056300W WO2009123056A1 WO 2009123056 A1 WO2009123056 A1 WO 2009123056A1 JP 2009056300 W JP2009056300 W JP 2009056300W WO 2009123056 A1 WO2009123056 A1 WO 2009123056A1
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- WIPO (PCT)
- Prior art keywords
- carbon atoms
- group
- ring
- alkyl
- heteroaryl
- Prior art date
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- 239000011859 microparticle Substances 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 77
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 70
- 125000003118 aryl group Chemical group 0.000 claims abstract description 62
- 125000001424 substituent group Chemical group 0.000 claims abstract description 37
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 27
- 229910052796 boron Inorganic materials 0.000 claims abstract description 19
- 150000001638 boron Chemical group 0.000 claims abstract description 16
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- 239000002184 metal Chemical group 0.000 claims abstract description 13
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- 125000002252 acyl group Chemical group 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 14
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- 229910052717 sulfur Inorganic materials 0.000 claims description 8
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- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- YRZZLAGRKZIJJI-UHFFFAOYSA-N oxyvanadium phthalocyanine Chemical compound [V+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 YRZZLAGRKZIJJI-UHFFFAOYSA-N 0.000 description 1
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- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoric acid amide group Chemical group P(N)(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 1
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- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 125000005554 pyridyloxy group Chemical group 0.000 description 1
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- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
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- 239000004332 silver Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
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- 125000000213 sulfino group Chemical group [H]OS(*)=O 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229930192474 thiophene Chemical group 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
-
- 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
- C09B23/005—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a COOH and/or a functional derivative thereof
- C09B23/0058—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a COOH and/or a functional derivative thereof the substituent being CN
-
- 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0075—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of an heterocyclic ring
-
- 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
-
- 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
- C09B57/10—Metal complexes of organic compounds not being dyes in uncomplexed form
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/30—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing heterocyclic ring with at least one nitrogen atom as ring member
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
Definitions
- the present invention relates to an infrared-absorbing compound having absorption in the near-infrared region and having no absorption in the visible region, and fine particles comprising the compound.
- Near-infrared absorbing dyes are used for plasma display panels (PDP), infrared cut films for CCDs and optical filters as heat-shielding films, write-once optical discs (CD-R), and photothermal conversion materials as flash fusion fixing materials It is used as an information display material as security ink and invisible barcode ink. It is invisible in addition to having strong absorption in the near-infrared region, especially as a characteristic feature of near-infrared pigments. There is a high demand for invisibility. At the same time, high fastness is required as a performance required for all dyes.
- Examples of dyes with excellent invisibility that have almost no absorption in the region of 400 nm to 700 nm include cyanine methine dyes and J-aggregates thereof, but long methine conjugated chains are flexible and have absorption forms accompanying isomerization. It is easy to decompose due to changes in heat and reaction with heat, oxygen, and nucleophiles, and has low robustness.
- Highly robust near-infrared absorbing dyes with a rigid skeleton include vanadyl naphthalocyanine dyes marketed by Nippon Shokubai Co., Ltd. and quartertalylene dyes marketed by BASF Corporation, but vanadyl phthalocyanine is invisible. Insufficient sex.
- quarterrylene has good invisibility in a molecular dispersion state such as a solution
- concentration when the concentration is increased, absorption occurs in the visible region due to association, the invisibility is lost, and the use form is limited.
- diimonium dyes marketed by Nippon Kayaku Co., Ltd., etc., but they are easy to be reduced, their fastness is insufficient, and their usage is limited. Will be.
- no near-infrared dye that achieves both invisibility and fastness has been put on the market, and development of a near-infrared dye that achieves both of these performances is desired.
- Non-Patent Document 1 describes the results of studies aimed at infrared fluorescent dyes, and describes that a high fluorescence quantum yield is achieved by forming a boron complex and increasing molecular rigidity.
- Patent Documents 1 to 3 As an example of applying a fluorescent dye characteristic of this skeleton group, application to an organic electroluminescence element is known (see, for example, Patent Documents 1 to 3).
- a fluorescent dye is used in a dilute state that does not cause concentration quenching, and a host material is co-deposited and used in a molecular dispersion state.
- Such fluorescent dyes are generally known to have low light resistance.
- An object of the present invention is to provide a highly robust near-infrared absorbing dye and dye fine particles having absorption in the near-infrared region and excellent in invisibility without absorption in the 400-700 nm region. It is an object of the present invention to provide a composition and a filter using the above. Moreover, in order to achieve it with a pyrrolopyrrole pigment
- Fine particles comprising a compound represented by the following general formula (1).
- R 1a and R 1b may be the same or different and each independently represents an alkyl group, an aryl group or a heteroaryl group.
- R 2 and R 3 each independently represents a hydrogen atom or a substituent. And at least one is an electron-withdrawing group, and R 2 and R 3 may combine to form a ring, and R 4 represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, a substituted boron, or a metal atom.
- R 1a , R 1b and / or R 3 may be covalently bonded or coordinated.
- ⁇ 3> The fine particles according to ⁇ 1> or ⁇ 2>, wherein the fine particles absorb infrared rays having a wavelength of 700 nm to 1000 nm.
- ⁇ 4> A composition comprising the fine particles according to any one of ⁇ 1> to ⁇ 3>.
- ⁇ 5> A coated product containing the fine particles according to any one of ⁇ 1> to ⁇ 3>.
- ⁇ 6> An infrared absorbing compound represented by the following general formula (2).
- Z 1a and Z 1b each independently represent an atomic group forming an aryl ring or a heteroaryl ring.
- R 5a and R 5b each independently represents an aryl group having 6 to 20 carbon atoms, or 4 to 20 carbon atoms.
- R 5a or R 5b and Z 1a or Z 1b may combine to form a condensed ring, each of R 22 and R 23 being independently a cyano group, Represents an acyl group having 6 carbon atoms, an alkoxycarbonyl group having 1 to 6 carbon atoms, an alkyl or arylsulfinyl group having 1 to 10 carbon atoms, or a nitrogen-containing heteroaryl group having 3 to 20 carbon atoms, or R 22 and R 23 are bonded Cyclic acid .
- R 4 representing the nuclei of hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 1 to 20 carbon atoms, a carboxyl group, a carbamoyl group having 1 to 20 carbon atoms, a halogen atom, or cyano
- R 5a or R 5b and Z 1a or Z 1b may combine to form a
- R 31a and R 31b each independently represents an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.
- R 32 represents a cyano group or a carbon atom.
- R 6 and R 7 Each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a heteroaryl group having 4 to 10 carbon atoms, and R 6 and R 7 are bonded to form a ring.
- the ring to be formed is an alicyclic ring having 5 to 10 carbon atoms, an aryl ring having 6 to 10 carbon atoms, or a heteroaryl ring having 3 to 10 carbon atoms, wherein R 8 and R 9 are each independently carbon.
- An alkyl group having 1 to 10 carbon atoms and 1 to 10 carbon atoms Represents an alkoxy group, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 10 carbon atoms
- X represents an oxygen atom, a sulfur atom, —NR—, —CRR′—
- R and R ′ represent hydrogen Represents an atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms.
- R 41a and R 41b represent different groups from each other, and represent an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.
- R 42 represents cyano.
- Z 2 Represents an atomic group that forms a nitrogen-containing hetero 5 or 6-membered ring with —C ⁇ N—, and the nitrogen-containing hetero ring includes a pyrazole ring, a thiazole ring, an oxazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, and a triazole.
- alkyl group having 1 to 20 carbon atoms aryl group having 6 to 20 carbon atoms, heteroaryl group having 4 to 20 carbon atoms, metal atom, or halogen atom as a substituent
- alkyl group having 1 to 10 carbon atoms carbon It represents a substituted boron having an aryl group of 6 to 20 or a heteroaryl group of 4 to 20 carbon atoms, and may have a covalent bond or a coordinate bond with the nitrogen-containing heterocycle formed by Z 2 .
- the compound may further have a substituent.
- the fine particles comprising the compound represented by the general formula (1) of the present invention have performances that satisfy all of excellent infrared absorption characteristics, invisibility and fastness.
- fine particles in which R 3 in the general formula (1) is a heterocyclic ring exhibit good performance.
- the fine particles can selectively absorb infrared rays of 700 nm or more and 1000 nm or less.
- the composition and the coated product (ink or filter) containing the fine particles of the present invention have excellent infrared absorptivity and achieve both excellent invisibility and excellent durability.
- the infrared absorbing compound represented by the general formula (2) of the present invention is a novel compound and has particularly excellent invisibility.
- the infrared absorbing compound represented by the general formula (3) of the present invention is also a novel compound, and achieves both high fastness and high invisibility.
- the infrared absorbing compound represented by the general formula (4) of the present invention is also a novel compound, and exhibits high fastness, high invisibility, excellent dispersibility, and high organic solvent solubility.
- FIG. 1 shows a solution spectrum of exemplary compound (D-17) and exemplary compound (D-9) in chloroform.
- FIG. 2 shows the absorption spectrum of the gelatin dispersion film of the exemplified compound (D-10) and the absorption spectrum in a chloroform solution.
- FIG. 3 shows the absorption spectrum of the gelatin dispersion film of the exemplified compound (D-28) and the absorption spectrum in a chloroform solution.
- FIG. 4 shows the results of light resistance evaluation of each dispersion film obtained in Examples and Comparative Examples.
- the fine particles of the present invention are composed of a compound represented by the following general formula (1).
- the fine particles of the present invention have performances that satisfy all of excellent infrared absorption characteristics, invisibility and fastness.
- R 1a and R 1b may be the same or different and each independently represents an alkyl group, an aryl group or a heteroaryl group.
- R 2 and R 3 each independently represents a hydrogen atom or a substituent. And at least one is an electron-withdrawing group, and R 2 and R 3 may combine to form a ring, and R 4 represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, a substituted boron, or a metal atom.
- R 1a , R 1b and / or R 3 may be covalently bonded or coordinated.
- the alkyl group represented by R 1a or R 1b preferably has 1 to 30 carbon atoms (in the present invention, “A to B” means “A or more and B or less”). ), More preferably an alkyl group having 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl. , Cyclopropyl, cyclopentyl, cyclohexyl and the like.
- the aryl group represented by R 1a or R 1b is preferably an aryl group having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms. o-Methylphenyl, p-methylphenyl, biphenyl, naphthyl, anthranyl, phenanthryl and the like.
- the heteroaryl group represented by R 1a or R 1b is preferably a heteroaryl group having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms. Examples of the hetero atom include a nitrogen atom, an oxygen atom, and a sulfur atom.
- heteroaryl group examples include imidazolyl, pyridyl, quinolyl, furyl, thienyl, benzoxazolyl, benzimidazolyl, benzthiazolyl, naphthothiazolyl, benzoxazolyl, m-carbazolyl, azepinyl and the like.
- R 1a and R 1b in the general formula (1) may be the same as or different from each other.
- R 2 and R 3 each independently represent a hydrogen atom or a substituent, at least one of which is an electron-withdrawing group, and R 2 and R 3 may combine to form a ring.
- the substituent include an alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, iso-propyl, tert-butyl, and n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), alkenyl groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably carbon numbers).
- alkynyl group preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably carbon number
- alkynyl group preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably carbon number
- an aryl group preferably having 6 carbon atoms
- amino group preferably carbon Number 0 to 30, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 10 carbon atoms, including alkylamino group, arylamino group and heterocyclic amino group, such as amino, methylamino, dimethylamino, diethylamino , Dibenzylamino, diphenylamino, di
- An acyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as acetyl, benzoyl, formyl, pivaloyl, etc.), an alkoxycarbonyl group ( Preferably it has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, and examples thereof include methoxycarbonyl, ethoxycarbonyl, etc.), an aryloxycarbonyl group (preferably having a carbon number) 7-30, more preferably 7-20 carbon atoms, particularly preferably 7-12 carbon atoms, such as phenyloxycarbonyl), acyloxy groups (preferably 2-30 carbon atoms, more preferably carbon atoms) 2 to 20, particularly preferably 2 to 10 carbon atoms.
- acylamino group preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and examples thereof include acetylamino and benzoylamino).
- An alkoxycarbonylamino group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonylamino), an aryloxycarbonylamino group (Preferably having 7 to 30 carbon atoms, more preferably having 7 to 20 carbon atoms, particularly preferably having 7 to 12 carbon atoms, such as phenyloxycarbonylamino), a sulfonylamino group (preferably having 1 carbon atom) Having 30 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms.
- carbamoyl methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl, etc.
- alkylthio group preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, Methylthio, ethylthio, etc.
- An thio group preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms, such as phenylthio).
- Aromatic heterocyclic thio group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as pyridylthio, 2-benzimidazolylthio, 2-benzoxazolyl Luthio, 2-benzthiazolylthio, etc.), sulfonyl groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms such as mesyl, tosyl) ), Sulfinyl groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfinyl, benzenesulfinyl, etc.).
- a ureido group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, Ureido, methylureido, phenylureido and the like), phosphoric acid amide groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms.
- Acid amide, phenylphosphoric acid amide, etc. hydroxy group, mercapto group, halogen atom (eg fluorine atom, chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, carboxyl group, nitro group, hydroxam
- halogen atom eg fluorine atom, chlorine atom, bromine atom, iodine atom
- cyano group eg fluorine atom, chlorine atom, bromine atom, iodine atom
- sulfo group carboxyl group, nitro group
- hydroxam An acid group, a sulfino group, a hydrazino group, an imino group, a heterocyclic group (preferably having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms.
- hetero atom examples include a nitrogen atom, an oxygen atom, a sulfur atom, Specifically, for example, imidazolyl, pyridyl, quinolyl, furyl, thienyl, piperidyl, morpholino, ben Oxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl group, azepinyl group, etc.), silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, Examples thereof include trimethylsilyl and triphenylsilyl). These substituents may be further substituted.
- the electron-withdrawing group represented by R 2 or R 3 preferably represents an electron-withdrawing group having a Hammett ⁇ p value (sigma para value) of 0.2 or more.
- Hammett's substituent constant ⁇ value will be described.
- Hammett's rule is a method described in 1935 by L. E. in order to quantitatively discuss the effect of substituents on the reaction or equilibrium of benzene derivatives.
- P. A rule of thumb proposed by Hammett which is widely accepted today.
- Substituent constants determined by Hammett's rule include ⁇ p value and ⁇ m value, and these values can be found in many general books. For example, J. et al. A. Dean ed., “Lange's Handbook of Chemistry”, 12th edition, 1979 (Mc Graw-Hill) and “Chemicals” special edition, No. 122, pages 96-103, 1979 (Nankodo), Chem. Rev.
- the substituent having Hammett's substituent constant ⁇ p value of 0.2 or more in the present invention is an electron-attracting group.
- the ⁇ p value is preferably 0.25 or more, more preferably 0.3 or more, and particularly preferably 0.35 or more.
- cyano group 0.66)
- carboxyl group —COOH: 0.45
- alkoxycarbonyl group —COOMe: 0.45
- aryloxycarbonyl group —COOPh: 0.44
- carbamoyl group —CONH 2 : 0.36
- An alkylcarbonyl group (—COMe: 0.50), an arylcarbonyl group (—COPh: 0.43), an alkylsulfonyl group (—SO 2 Me: 0.72), an arylsulfonyl group (—SO 2 Ph: 0.68), and the like.
- Me represents a methyl group
- Ph represents a phenyl group.
- the values in parentheses are the ⁇ p values of typical substituents in Chem. Rev. 1991, Vol. 91, pp. 165-195.
- a 5- to 7-membered ring (preferably a 5- to 6-membered ring) is formed, and the formed ring is usually a merocyanine dye and an acidic nucleus.
- a merocyanine dye and an acidic nucleus are preferably used, and specific examples thereof include the following.
- (B) pyrazolinone nucleus for example 1-phenyl-2-pyrazolin-5-one, 3-methyl-1-phenyl-2-pyrazolin-5-one, 1- (2-benzothiazoyl) -3-methyl-2 -Pyrazolin-5-one and the like.
- (D) Oxindole nucleus for example, 1-alkyl-2,3-dihydro-2-oxindole.
- (E) 2,4,6-triketohexahydropyrimidine nucleus for example, barbituric acid or 2-thiobarbituric acid and its derivatives.
- the derivatives include 1-alkyl compounds such as 1-methyl and 1-ethyl, 1,3-dialkyl compounds such as 1,3-dimethyl, 1,3-diethyl and 1,3-dibutyl, 1,3-diphenyl, 1,3-diaryl compounds such as 1,3-di (p-chlorophenyl) and 1,3-di (p-ethoxycarbonylphenyl), 1-alkyl-1-aryl compounds such as 1-ethyl-3-phenyl, Examples include 1,3-di (2-pyridyl) 1,3-diheterocyclic substituents and the like.
- (F) 2-thio-2,4-thiazolidinedione nucleus for example, rhodanine and its derivatives.
- the derivatives include 3-alkylrhodanine such as 3-methylrhodanine, 3-ethylrhodanine and 3-allylrhodanine, 3-arylrhodanine such as 3-phenylrhodanine, and 3- (2-pyridyl) rhodanine. And the like.
- (J) 2,4-thiozolidinedione nucleus for example, 2,4-thiazolidinedione, 3-ethyl-2,4-thiazolidinedione, 3-phenyl-2,4-thiazolidinedione and the like.
- (K) Thiazolin-4-one nucleus for example, 4-thiazolinone, 2-ethyl-4-thiazolinone, etc.
- (L) 4-thiazolidinone nucleus for example, 2-ethylmercapto-5-thiazoline-4-one, 2-alkylphenylamino-5-thiazoline-4-one, etc.
- (M) 2,4-imidazolidinedione (hydantoin) nucleus for example, 2,4-imidazolidinedione, 3-ethyl-2,4-imidazolidinedione, etc.
- (N) 2-thio-2,4-imidazolidinedione (2-thiohydantoin) nucleus for example 2-thio-2,4-imidazolidinedione, 3-ethyl-2-thio-2,4-imidazolidinedione
- (O) imidazolin-5-one nucleus for example, 2-propylmercapto-2-imidazolin-5-one and the like.
- (P) 3,5-pyrazolidinedione nucleus for example, 1,2-diphenyl-3,5-pyrazolidinedione, 1,2-dimethyl-3,5-pyrazolidinedione, etc.
- the ⁇ p values of R 2 and R 3 in the case of forming a ring cannot be defined, but in the present invention, it is considered that R 2 and R 3 are each substituted with a partial structure of the ring. In this case, the ⁇ p value is defined. For example, when a 1,3-indandione ring is formed, it is considered that R 2 and R 3 are each substituted with a benzoyl group.
- the ring formed by combining R 2 and R 3 is preferably a 1,3-dicarbonyl nucleus, a pyrazolinone nucleus, a 2,4,6-triketohexahydropyrimidine nucleus (including a thioketone body), 2- Thio-2,4-thiazolidinedione nucleus, 2-thio-2,4-oxazolidinedione nucleus, 2-thio-2,5-thiazolidinedione nucleus, 2,4-thiazolidinedione nucleus, 2,4-imidazolidinedione nucleus 2-thio-2,4-imidazolidinedione nucleus, 2-imidazolin-5-one nucleus, 3,5-pyrazolidinedione nucleus, benzothiophen-3-one nucleus, or indanone nucleus, more preferably 1,3-dicarbonyl nucleus, 2,4,6-triketohexahydropyrimidine nucleus (
- R 3 is particularly preferably a heterocycle.
- Two R 2 in the general formula (1) may be the same or different from each other, and two R 3 may be the same or different from each other.
- the alkyl group, aryl group, and heteroaryl group represented by R 4 have the same meanings as the substituents described for R 1a and R 1b , and the preferred ranges are also the same.
- the substituent of the substituted boron represented by R 4 has the same meaning as the substituent described above for R 2 and R 3 , and is preferably an alkyl group, an aryl group, or a heteroaryl group.
- the metal atom represented by R 4 is preferably a transition metal, magnesium, aluminum, calcium, barium, zinc, or tin, and more preferably aluminum, zinc, tin, vanadium, iron, cobalt, nickel, copper Palladium, iridium, or platinum, particularly preferably aluminum, zinc, vanadium, iron, copper, palladium, iridium, or platinum.
- R 4 may be covalently bonded or coordinated to R 1a , R 1b and / or R 3 .
- Two R 4 in the general formula (1) may be the same as or different from each other.
- the compound represented by the general formula (1) is preferably an infrared absorbing compound represented by any one of the following general formulas (2), (3), or (4).
- Z 1a and Z 1b each independently represent an atomic group forming an aryl ring or a heteroaryl ring.
- R 5a and R 5b each independently represents an aryl group having 6 to 20 carbon atoms, or 4 to 20 carbon atoms.
- R 5a or R 5b and Z 1a or Z 1b may combine to form a condensed ring, each of R 22 and R 23 being independently a cyano group, Represents an acyl group having 6 carbon atoms, an alkoxycarbonyl group having 1 to 6 carbon atoms, an alkyl or arylsulfinyl group having 1 to 10 carbon atoms, or a nitrogen-containing heteroaryl group having 3 to 20 carbon atoms, or R 22 and R 23 are bonded Cyclic acid .
- R 4 representing the nuclei of hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 1 to 20 carbon atoms, a carboxyl group, a carbamoyl group having 1 to 20 carbon atoms, a halogen atom, or cyano
- R 5a or R 5b and Z 1a or Z 1b may combine to form a
- R 31a and R 31b each independently represents an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.
- R 32 represents a cyano group or a carbon atom.
- R 6 and R 7 Each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a heteroaryl group having 4 to 10 carbon atoms, and R 6 and R 7 are bonded to form a ring.
- the ring to be formed is an alicyclic ring having 5 to 10 carbon atoms, an aryl ring having 6 to 10 carbon atoms, or a heteroaryl ring having 3 to 10 carbon atoms, wherein R 8 and R 9 are each independently carbon.
- An alkyl group having 1 to 10 carbon atoms and 1 to 10 carbon atoms Represents an alkoxy group, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 10 carbon atoms
- X represents an oxygen atom, a sulfur atom, —NR—, —CRR′—
- R and R ′ represent hydrogen Represents an atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms.
- R 41a and R 41b represent different groups from each other, and represent an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.
- R 42 represents cyano.
- Z 2 Represents an atomic group that forms a nitrogen-containing hetero 5 or 6-membered ring with —C ⁇ N—, and the nitrogen-containing hetero ring includes a pyrazole ring, a thiazole ring, an oxazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, and a triazole.
- alkyl group having 1 to 20 carbon atoms aryl group having 6 to 20 carbon atoms, heteroaryl group having 4 to 20 carbon atoms, metal atom, or halogen atom as a substituent
- alkyl group having 1 to 10 carbon atoms carbon It represents a substituted boron having an aryl group of 6 to 20 or a heteroaryl group of 4 to 20 carbon atoms, and may have a covalent bond or a coordinate bond with the nitrogen-containing heterocycle formed by Z 2 .
- the compound may further have a substituent.
- Z 1a and Z 1b each independently represent an atomic group that forms an aryl ring or a heteroaryl ring.
- the aryl ring and heteroaryl ring formed are synonymous with the aryl group and heteroaryl group described as the substituents for R 2 and R 3 in the general formula (1), and the preferred ranges are also the same.
- Z 1a and Z 1b are preferably the same.
- R 5a and R 5b are each independently an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 4 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or 1 to It represents any one of 20 alkoxycarbonyl groups, carboxyl groups, carbamoyl groups having 1 to 20 carbon atoms, halogen atoms, and cyano groups. Specific examples are synonymous with the examples described for R 2 and R 3 in the general formula (1), and preferred ranges are also the same. R 5a and R 5b are preferably the same.
- R 5a or R 5b and Z 1a or Z 1b may combine to form a condensed ring, and examples of the condensed ring include a naphthyl ring and a quinoline ring.
- R 22 and R 23 are each independently a cyano group, an acyl group having 1 to 6 carbon atoms, an alkoxycarbonyl group having 1 to 6 carbon atoms, an alkyl or arylsulfinyl group having 1 to 10 carbon atoms, or a group having 3 to 20 carbon atoms It represents a nitrogen-containing heteroaryl group, or R 22 and R 23 are combined to represent a cyclic acidic nucleus. Specifically, it is synonymous with the example demonstrated by R ⁇ 2 > and R ⁇ 3 > in the said General formula (1), and its preferable range is also the same.
- R 4 has the same meaning as R 4 in the general formula (1), and the preferred range is also the same.
- R 4 may have a covalent bond or a coordinate bond with R 23 .
- the compound represented by the general formula (2) may further have a substituent, and the substituent is synonymous with the substituents of R 2 and R 3 , and the preferred range is also the same.
- Z 1a and Z 1b each independently form a benzene ring or a pyridine ring
- R 5a and R 5b each independently represent an alkyl group, an alkoxy group, a halogen atom, a cyano group
- R 22 and R 23 are each independently a heterocyclic group, a cyano group, an acyl group, an alkoxycarbonyl group, or a cyclic acidic nucleus in which R 22 and R 23 are bonded
- R 4 is a hydrogen atom, a substituted boron, This is the case of transition metal atoms, magnesium, aluminum, calcium, barium, zinc, and tin.
- Z 1a and Z 1b together form a benzene ring
- R 5a and R 5b are both an alkyl group, a halogen atom, or a cyano group
- R 22 and R 23 are each independently a nitrogen-containing heterocycle.
- R 31a and R 31b each independently represent an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. These are synonymous with the examples described for R 1a and R 1b in the general formula (1), and the preferred ranges are also the same. R 31a and R 31b are preferably the same.
- R 32 is a cyano group, an acyl group having 1 to 6 carbon atoms, an alkoxycarbonyl group having 1 to 6 carbon atoms, an alkyl or arylsulfinyl group having 1 to 10 carbon atoms, or a nitrogen-containing heteroaryl group having 3 to 10 carbon atoms. Specifically, it is synonymous with the example of R 2 in the general formula (1), and the preferred range is also the same.
- R 6 and R 7 are each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a heteroaryl group having 4 to 10 carbon atoms. (1) have the same meanings as examples of the substituents of R 2 and R 3 in the preferred range is also the same.
- R 6 and R 7 may combine to form a ring, and the formed ring includes an alicyclic ring having 5 to 10 carbon atoms, an aryl ring having 6 to 10 carbon atoms, and a heteroaryl ring having 3 to 10 carbon atoms.
- Preferred examples include a benzene ring, naphthalene ring, and pyridine ring.
- R 8 and R 9 are each independently an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 10 carbon atoms. to are the same as examples of the substituents R 2 and R 3 in the general formula (1), and preferred ranges are also the same.
- X represents an oxygen atom, a sulfur atom, —NR— or —CRR′—.
- R and R ′ each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms, preferably a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group.
- R 31a and R 31b are each independently an alkyl group having 1 to 10 carbon atoms, a benzene ring or a pyridine ring
- R 32 is a cyano group
- R 6 and R 7 are bonded to form a benzene ring, a pyridine ring, a pyrazine ring, or a pyrimidine ring
- R 8 and R 9 are each independently an alkyl group having 1 to 6 carbon atoms, a phenyl group, or a naphthyl group
- X is an oxygen atom, a sulfur atom, —NR— or —CRR′—
- R and R ′ are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group.
- R 31a and R 31b are both an alkyl group having 1 to 10 carbon atoms or a benzene ring
- R 32 is a cyano group
- R 6 and R 7 are bonded to form a benzene ring or a pyridine ring
- R 8 and R 9 are each independently an alkyl group having 1 to 6 carbon atoms, a phenyl group, or a naphthyl group
- X is oxygen or sulfur.
- R 41a and R 41b each represents an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. It is synonymous with the example demonstrated by R ⁇ 1a> and R ⁇ 1b> in Formula (1), and its preferable range is also the same. However, R 41a and R 41b represent different groups.
- R 42 is a cyano group, an acyl group having 1 to 6 carbon atoms, an alkoxycarbonyl group having 1 to 6 carbon atoms, an alkyl or arylsulfinyl group having 1 to 10 carbon atoms, or a nitrogen-containing heteroaryl group having 3 to 10 carbon atoms. Specifically, it is synonymous with the example of R 2 in the general formula (1), and the preferred range is also the same.
- Z 2 represents an atomic group that forms a nitrogen-containing hetero 5- or 6-membered ring with —C ⁇ N—
- the nitrogen-containing hetero ring includes a pyrazole ring, thiazole ring, oxazole ring, imidazole ring, oxadiazole ring, thiadiazole ring , A triazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a benzo condensed ring or a naphth condensed ring, or a complex of these condensed rings.
- R 44 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 4 to 20 carbon atoms, a metal atom or a halogen atom as a substituent, an alkyl having 1 to 10 carbon atoms Represents a substituted boron having a group, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 4 to 20 carbon atoms, and may have a covalent bond or a coordinate bond with the nitrogen-containing heterocycle formed by Z 2 .
- R 41a and R 41b are each independently an alkyl group having 1 to 10 carbon atoms, a benzene ring or a pyridine ring, R 42 is a cyano group and has 1 to 10 carbon atoms.
- An alkyl or arylsulfinyl group, an alkoxycarbonyl group, and Z 2 together with —C ⁇ N— is a thiazole ring, an oxazole ring, an imidazole ring, a thiadiazole ring, a triazole ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, or a benzo-condensation thereof.
- R 44 is a hydrogen atom, a substituted boron, a transition metal atom, magnesium, aluminum, calcium, barium, zinc, or tin.
- R 41a and R 41b each independently represents an alkyl group having 1 to 10 carbon atoms or a benzene ring
- R 42 represents a cyano group
- Z 2 together with —C ⁇ N— represents a thiazole ring, oxazole A ring, an imidazole ring, a triazole ring, a pyridine ring, a pyrimidine ring, or a benzo condensed ring or a naphth condensed ring thereof
- R 44 is a hydrogen atom, a substituted boron (the substituent is an alkyl group having 1 to 10 carbon atoms, A benzene ring, a pyridine ring, or a thiophene ring), aluminum, zinc, vanadium, iron, copper, palladium, iridium, or platinum.
- the compound represented by any one of the general formulas (1) to (4) can be obtained by condensing an active methylene compound with a corresponding diketopyrrolopyrrole compound and, in some cases, further reacting with boron or a metal. Can be synthesized.
- the diketopyrrolopyrrole compound can be synthesized by the method described in “High Performance Pigments”, Wiley-VCH, 2002, pages 160 to 163, and more specific examples include US Pat. No. 5,969. 154, and Japanese Patent Laid-Open No. 9-323993.
- condensation reaction between the diketopyrrolopyrrole compound and the active methylene compound and the subsequent boronation can be synthesized in accordance with the aforementioned Non-Patent Document 1.
- Boronating reagents are described in J. Med. Chem. It can be synthesized with reference to Volume 3, pages 356 to 360 (1976).
- bromocatechol borane can be purchased from Tokyo Chemical Industry Co., Ltd. and used.
- the compound represented by any one of the general formulas (1) to (4) is not particularly limited, but preferably has an absorption maximum at 700 to 1050 nm, more preferably 700 to 1000 nm.
- the compound represented by any one of the general formulas (1) to (4) preferably selectively absorbs infrared rays having a wavelength of 700 nm to 1000 nm.
- the compound represented by any one of the general formulas (1) to (4) has a molar extinction coefficient ⁇ that is not particularly limited, but is preferably 50,000 to 300,000, and more preferably 100,000. ⁇ 250,000.
- the compound represented by any one of the general formulas (1) to (4) can be preferably used as an IR dye. Since it is invisible, the color of the compound is preferably transparent, but may be slightly colored green or gray.
- the fine particles of the present invention comprise a compound represented by the general formula (1).
- the particle diameter of the fine particles of the present invention is preferably 1 to 1000 nm, more preferably 5 to 600 nm, and particularly preferably 20 to 200 nm.
- the particle size of the fine particles can be measured using a Nanotrac UPA particle size analyzer (UPA-EX150, trade name, manufactured by Nikkiso Co., Ltd.) using a dynamic light scattering method.
- UPA-EX150 Nanotrac UPA particle size analyzer
- a method for preparing fine particles using the compound represented by any one of the general formulas (1) to (4) will be described.
- the compound represented by any one of the general formulas (1) to (4) can be obtained as a crude crystal by the above-described compound synthesis method, but when used as the fine particles of the present invention, post-treatment is preferably performed.
- post-treatment methods include fine particle control processes such as solvent salt milling, salt milling, dry milling, solvent milling, and acid pasting, solvent heat treatment, resin, surfactant and dispersant, etc. The surface treatment process by.
- the compound represented by any one of the general formulas (1) to (4) may be subjected to a solvent heating treatment as a post-treatment.
- the solvent used in the solvent heat treatment include water, aromatic hydrocarbon solvents such as toluene and xylene, halogenated hydrocarbon solvents such as chlorobenzene and o-dichlorobenzene, and alcohols such as isopropanol and isobutanol.
- examples thereof include a solvent, polar aprotic organic solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, and N-methyl-2-pyrrolidone, glacial acetic acid, pyridine, and mixtures thereof.
- the average particle diameter of the pigment is preferably adjusted to 0.01 ⁇ m to 1 ⁇ m by these post-treatments.
- the composition containing the fine particles of the present invention may be aqueous or non-aqueous.
- aqueous liquid in which the fine particles are dispersed in the aqueous fine particle composition of the present invention a mixture containing water as a main component and optionally adding a hydrophilic organic solvent can be used.
- the hydrophilic organic solvent include alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, sec-butanol, t-butanol, pentanol, hexanol, cyclohexanol, benzyl alcohol, ethylene glycol, diethylene glycol, and the like.
- Alcohols such as triethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, butylene glycol, hexanediol, pentanediol, glycerin, hexanetriol, thiodiglycol, ethylene glycol monomethyl ether, ethylene glycol mono Ethyl ether, ethylene glycol butyl ether, diethylene glycol mono Chill ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monobutyl ether, dipropylene glycol monomethyl ether, triethylene glycol monomethyl ether, ethylene glycol diacetate, ethylene glycol monomethyl ether acetate triethylene glycol monoethyl ether, ethylene glycol monophenyl ether Glycol derivatives such as ethanolamine, diethanolamine, triethanolamine, N-methyldiethanolamine, N-ethyldiethanolamine, ethylene
- the aqueous fine particle composition of the present invention may contain an aqueous resin.
- the aqueous resin include a water-soluble resin that dissolves in water, a water-dispersible resin that disperses in water, a colloidal dispersion resin, or a mixture thereof.
- Specific examples of the aqueous resin include acrylic, styrene-acrylic, polyester, polyamide, polyurethane, and fluorine resins.
- the water-dispersible resin used in the present invention is a dispersion in which a hydrophobic synthetic resin is dispersed in a dispersion medium whose main component is water (sometimes referred to as a solvent in this specification).
- the content of water contained in the solvent is preferably 30% to 100%, more preferably 50% to 100%.
- a solvent having solubility in water such as alcohols such as methanol, ethanol and isopropyl alcohol, ketones such as acetone and methyl ethyl ketone, tetrahydrofuran and butyl cellosolve is preferably used.
- the synthetic resin polymer
- various polymers such as acrylic resin, styrene-acrylic resin, vinyl resin, polyurethane resin, polyester resin, polyamide resin, and fluorine resin can be used.
- the water-soluble resin include gelatin, polyvinyl alcohol, and carboxymethyl cellulose.
- Acrylic resins include acrylic acid esters such as acrylic acid and alkyl acrylate, acrylamide, acrylonitrile, methacrylic acid esters such as methacrylic acid and alkyl methacrylate, and homopolymers of any monomer of methacrylamide and methacrylonitrile. Or the copolymer obtained by superposition
- the acrylic resin has the above composition as a main component and, for example, partially uses a monomer having any group of a methylol group, a hydroxyl group, a carboxyl group, and an amino group so that a crosslinking reaction with a carbodiimide compound is possible.
- the resulting polymer has the above composition as a main component and, for example, partially uses a monomer having any group of a methylol group, a hydroxyl group, a carboxyl group, and an amino group so that a crosslinking reaction with a carbodiimide compound is possible.
- vinyl resin examples include polyvinyl alcohol, acid-modified polyvinyl alcohol, polyvinyl formal, polyvinyl butyral, polyvinyl methyl ether, polyolefin, ethylene / butadiene copolymer, polyvinyl acetate, vinyl chloride / vinyl acetate copolymer, vinyl chloride / ( A meth) acrylic acid ester copolymer and an ethylene / vinyl acetate copolymer (preferably ethylene / vinyl acetate / (meth) acrylic acid ester copolymer) can be mentioned.
- the vinyl resin can be crosslinked with a carbodiimide compound so that, for example, polyvinyl alcohol, acid-modified polyvinyl alcohol, polyvinyl formal, polyvinyl butyral, polyvinyl methyl ether, and polyvinyl acetate leave a vinyl alcohol unit in the polymer.
- the polymer having a hydroxyl group is used, and the other polymer is, for example, a crosslinkable polymer by partially using a monomer having any of a methylol group, a hydroxyl group, a carboxyl group, and an amino group.
- polyurethane resin examples include polyhydroxy compounds (eg, ethylene glycol, propylene glycol, glycerin, trimethylolpropane), aliphatic polyester polyols obtained by reaction of polyhydroxy compounds and polybasic acids, polyether polyols (eg, Polyurethanes derived from poly (oxypropylene ether) polyols, poly (oxyethylene-propylene ether) polyols), polycarbonate-based polyols, and polyethylene terephthalate polyols, or mixtures thereof and polyisocyanates can be mentioned.
- polyurethane resin for example, the hydroxyl group remaining unreacted after the reaction between polyol and polyisocyanate can be used as a functional group capable of crosslinking reaction with a carbodiimide compound.
- the polyester resin generally used is a polymer obtained by reacting a polyhydroxy compound (eg, ethylene glycol, propylene glycol, glycerin, trimethylolpropane) with a polybasic acid.
- a polyhydroxy compound eg, ethylene glycol, propylene glycol, glycerin, trimethylolpropane
- the polyester resin for example, after the reaction between the polyol and the polybasic acid is completed, the hydroxyl group and carboxyl group remaining unreacted can be used as a functional group capable of crosslinking reaction with the carbodiimide compound.
- a third component having a functional group such as a hydroxyl group may be added.
- the dispersion state of the aqueous dispersion of the polymer may be one in which the polymer is emulsified in a dispersion medium, emulsion polymerized, micelle-dispersed, or partially hydrophilic in the polymer molecule. Any of them may be used.
- the average particle size is preferably in the range of about 1 to 50000 nm, more preferably about 5 to 1000 nm
- the particle size distribution of the dispersed particles is not particularly limited, and even those having a wide particle size distribution have a monodispersed particle size distribution. It may be a thing.
- the following commercially available polymers may be used (all are trade names).
- Superflex 830, 460, 870, 420, 420NS Polyurethane made by Daiichi Kogyo Seiyaku), Bondick 1370NS, 1320NS, Hydran Hw140SF, WLS201, WLS202, WLS213 (Polyurethane made by Dainippon Ink & Chemicals), Olester UD350, UD500, UD600 (Mitsui Chemicals Polyurethane), Neoletz R972, R966, R9660 (Enomoto Kasei Polyurethane), Finetex Es650, Es2200 (Dainippon Ink Chemicals Polyester), Vironal MD1100, MD1400, MD1480 (Toyobo Polyester), Julimer ET325 ET410, AT-613, SEK301 (Nippon Pure Chemicals Acrylic), Boncoat AN117, AN226 (Dainippon Ink Industrial acrylic), Luckstar DS616,
- the polymer used as the binder of the composition of the present invention may be used alone or as a mixture of two or more if necessary.
- the molecular weight of the polymer used as the binder of the near infrared absorbing layer is not particularly limited, but usually a weight average molecular weight of about 3000 to 1000000 is preferred. When the weight average molecular weight is too small, the strength of the coating layer may be insufficient, and when it is too large, the coated surface may be poor.
- a surfactant and a dispersant may be used in order to improve fine particle dispersion and image quality.
- the surfactant include anionic, nonionic, cationic, and amphoteric surfactants. Any surfactant may be used, but an anionic or nonionic surfactant is used. Is preferred.
- the anionic surfactant include fatty acid salts, alkyl sulfate esters, alkylbenzene sulfonates, alkyl naphthalene sulfonates, dialkyl sulfosuccinates, alkyl diaryl ether disulfonates, alkyl phosphates, and polyoxyethylene alkyls.
- Examples thereof include ether sulfate, polyoxyethylene alkylaryl ether sulfate, naphthalene sulfonic acid formalin condensate, polyoxyethylene alkyl phosphate ester salt, glycerol borate fatty acid ester, polyoxyethylene glycerol fatty acid ester and the like.
- Nonionic surfactants include, for example, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene oxypropylene block copolymer, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbitol fatty acid ester, glycerin Examples include fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene alkylamines, fluorine-based resins, and silicon-based materials.
- the non-aqueous fine particle composition is obtained by dispersing a compound represented by any one of the general formulas (1) to (4) in a non-aqueous vehicle.
- Resins used in non-aqueous vehicles are, for example, petroleum resins, casein, shellac, rosin modified maleic resin, rosin modified phenolic resin, nitrocellulose, cellulose acetate butyrate, cyclized rubber, chlorinated rubber, oxidized rubber, hydrochloric acid rubber , Phenolic resin, alkyd resin, polyester resin, unsaturated polyester resin, amino resin, epoxy resin, vinyl resin, vinyl chloride, vinyl chloride-vinyl acetate copolymer, acrylic resin, methacrylic resin, polyurethane resin, silicone resin, fluorine resin , Drying oil, synthetic drying oil, styrene / maleic resin, styrene / acrylic resin, polyamide resin, polyimide resin, polyester resin, benzoguanamine resin, melamine resin, urea resin
- Examples of the solvent used in the non-aqueous vehicle include aromatic solvents such as toluene, xylene, and methoxybenzene, and acetates such as ethyl acetate, butyl acetate, propylene glycol monomethyl ether acetate, and propylene glycol monoethyl ether acetate.
- aromatic solvents such as toluene, xylene, and methoxybenzene
- acetates such as ethyl acetate, butyl acetate, propylene glycol monomethyl ether acetate, and propylene glycol monoethyl ether acetate.
- Solvents propionate solvents such as ethoxyethyl propionate, alcohol solvents such as methanol and ethanol, ether solvents such as butyl cellosolve, propylene glycol monomethyl ether, diethylene glycol ethyl ether, diethylene glycol dimethyl ether, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.
- Ketone solvents aliphatic hydrocarbon solvents such as hexane, N, N-dimethylformamide, ⁇ -butyrolactam, - methyl-2-pyrrolidone, aniline, nitrogen compound-based solvent such as pyridine, a lactone-based solvents such as ⁇ - butyrolactone, carbamic acid esters such as a mixture of 48:52 of methyl carbamate and ethyl carbamate acid.
- the composition of the present invention can be obtained by dispersing the compound represented by any one of the general formulas (1) to (4) and an aqueous or non-aqueous medium using a dispersing device.
- a dispersing device examples include a ball mill, a sand mill, a bead mill, a roll mill, a jet mill, a paint shaker, an attritor, an ultrasonic disperser, and a disper.
- the volume average particle diameter of the fine particles is preferably 10 nm or more and 250 nm or less.
- the volume average particle diameter of the fine particles refers to the particle diameter of the fine particles themselves or, in the case where an additive such as a dispersant is attached to the fine particles, the particle diameter to which the additive is attached.
- a nanotrac UPA particle size analyzer UPA-EX150, trade name, manufactured by Nikkiso Co., Ltd.
- UPA-EX150 nanotrac UPA particle size analyzer
- the measurement is performed according to a predetermined measurement method by placing 3 ml of the fine particle dispersion in a measurement cell.
- ink viscosity is used for viscosity
- fine particle density is used for the density of dispersed particles.
- More preferable volume average particle diameter is 20 nm or more and 250 nm or less, and further preferably 30 nm or more and 230 nm or less.
- the concentration of fine particles contained in the composition of the present invention is preferably in the range of 1 to 35% by mass, more preferably in the range of 2 to 25% by mass. If the concentration is too low, sufficient color concentration may not be obtained when the fine particle composition is used alone. If the concentration is too high, the dispersion stability may decrease.
- inventions include image recording materials for forming images, particularly invisible images, and specifically, ink-jet recording materials, heat-sensitive recording materials, pressure-sensitive recording materials, electrophotography.
- image recording materials for forming images, particularly invisible images, and specifically, ink-jet recording materials, heat-sensitive recording materials, pressure-sensitive recording materials, electrophotography.
- recording materials using a method transfer-type silver halide photosensitive materials, printing inks, recording pens, etc., preferably ink jet recording materials, thermal recording materials, and recording materials using an electrophotographic method.
- the present invention can also be applied to an infrared cut filter used in a solid-state imaging device such as a CCD or a display such as a PDP, and a staining solution for dyeing various fibers.
- a solid-state imaging device such as a CCD or a display such as a PDP
- a staining solution for dyeing various fibers e.g., a staining solution for dyeing various fibers.
- Example 1 (Preparation of exemplary compound (D-1)) Exemplified compound (D-1) was prepared according to the following scheme.
- a diketopyrrolopyrrole compound (DPP) was synthesized according to the method described in US Pat. No. 5,969,154 using 4- (2-ethylhexyloxy) benzonitrile as a raw material.
- Example 2 (Preparation of exemplary compound (D-25)) Exemplified compound (D-25) was prepared according to the above scheme. 0.75 g (1 equivalent) of Exemplified Compound (D-1) and 0.5 g (2.5 equivalent) of chlorodiphenyl boron were heated to reflux in 20 mL of orthodichlorobenzene for 3 hours. After cooling to room temperature and adding 10 mL of water, the organic layer was taken out by a liquid separation operation, washed with an aqueous sodium bicarbonate solution, and then the solvent was distilled off under reduced pressure.
- Example 3 (Preparation of exemplary compound (D-30)) Exemplified compound (D-30) was prepared according to the above scheme. 1 gram (1 equivalent) of the exemplified compound (D-1) and 0.5 gram (2.5 equivalent) of boron trifluoride diethyl ether complex were heated to reflux in 20 mL of orthodichlorobenzene for 1 hour, and then diisopropylmethyl. 0.75 grams (5 equivalents) of amine was added and the mixture was further heated to reflux for 1 hour. After cooling to room temperature and adding 10 mL of water, the organic layer was taken out by a liquid separation operation, and the solvent was distilled off under reduced pressure.
- Example 4 The following exemplary compounds were prepared in the same manner as in Example 1 except that the raw materials in Example 1 were changed. 1 H-NMR whose structure has been identified is shown.
- Example 5 (Preparation of exemplary compound (D-101)) Exemplified compound (D-101) was prepared according to the following scheme.
- a diketopyrrolopyrrole compound (DPP) was synthesized according to the method described in “Tetrahedron”, 58, (2002), p.5547-5565.
- Example 6 (Preparation of exemplary compound (D-102)) Exemplified compound (D-102) was prepared according to the above scheme.
- Example compound (D-101) 0.18 g (1 equivalent), 2-aminoethyl diphenylborate 0.125 g (2.2 equivalent) and titanium tetrachloride 0.19 g were heated in 4 mL of toluene for 1 hour. Refluxed. After cooling to room temperature and adding 5 mL of methyl alcohol, the mixture was filtered to obtain crystals. The obtained crude product was purified by silica gel column chromatography (chloroform solvent) to obtain 0.2 g of the target compound (D-102) in a yield of 77%. ⁇ max was 780 nm in chloroform.
- Example 7 (Preparation of exemplary compound (D-106)
- Exemplified compound (D-105) was prepared in the same manner as in Example 1, except that the raw materials in Example 1 were changed.
- Example 8 (Preparation of exemplary compound (D-107)) Exemplified compound (D-107) was prepared in the same manner as in Example 1, except that the raw materials in Example 1 were changed. ⁇ max was 727 nm in chloroform. The molar absorption coefficient was 8.14 ⁇ 10 4 dm 3 / mol ⁇ cm in chloroform.
- Example 9 (Preparation of exemplary compound (D-108))
- Example compound (D-107) 0.71 g (1 equivalent), 2-aminoethyl diphenylborate 0.48 g (2.2 equivalents) and titanium tetrachloride 0.72 g were heated in 10 mL of toluene for 1 hour. Refluxed. After cooling to room temperature and adding 10 mL of methyl alcohol, the mixture was filtered to obtain crystals. The resulting crude product was purified by silica gel column chromatography (chloroform solvent) to obtain 0.7 g of the target compound (D-108) in a yield of 70%. ⁇ max was 779 nm in chloroform.
- Example 10 (Preparation of exemplary compound (D-131)) 2.6 g (1 equivalent) of exemplary compound (D-17) and 2.4 g (4 equivalent) of bromocatechol borane (manufactured by Tokyo Chemical Industry Co., Ltd.) were heated to reflux in 20 mL of toluene for 3 hours. After cooling to room temperature, 20 mL of methanol was added, and the precipitated crystals were filtered. The resulting crude product was purified by silica gel column chromatography (solvent chloroform) and recrystallized using chloroform / methanol solvent to obtain 2.3 g of the target compound (D-131) in a yield of 70%. It was.
- Example 11 (Preparation of exemplary compound (D-138)) Exemplified compound (D-138) was prepared according to the following scheme.
- Compound (B1) was synthesized according to the method described in “Heterocycles”, 57, (2002), p. 1319-1326.
- Example 12 The following exemplary compounds were prepared in the same manner as in Example 11 except that the raw materials in Example 11 were changed. The yield, ⁇ max, molar absorption coefficient, and structure-identified 1 H-NMR are shown respectively. Exemplary compound (D-135) Yield 92%. ⁇ max was 779 nm in chloroform. The molar absorption coefficient was 2.16 ⁇ 10 5 dm 3 / mol ⁇ cm in chloroform.
- Exemplary compound (D-136) Yield 89%. ⁇ max was 779 nm in chloroform. The molar absorption coefficient was 1.77 ⁇ 10 5 dm 3 / mol ⁇ cm in chloroform.
- Exemplary compound (D-137) Yield 56%.
- ⁇ max was 802 nm in chloroform.
- the molar absorption coefficient was 1.97 ⁇ 10 5 dm 3 / mol ⁇ cm in chloroform.
- Exemplary compound (D-139) Yield 80%. ⁇ max was 782 nm in chloroform. The molar absorption coefficient was 1.96 ⁇ 10 5 dm 3 / mol ⁇ cm in chloroform.
- Example 13 [Invisibility evaluation by evaluation of solution absorption spectrum] The solution spectra of Example Compound (D-17) and Example Compound (D-9) in chloroform were normalized and compared, respectively. The results are shown in FIG. In FIG. 1, the horizontal axis represents wavelength and the vertical axis represents absorbance. As is clear from FIG. 1, it was found that Exemplified Compound (D-9) has a smaller absorption at 400 to 500 nm and is more invisible compared to Exemplified Compound (D-17).
- exemplary compound (D-1) and exemplary compound (D-4), exemplary compound (D-25) and exemplary compound (D-28), exemplary compound (D-10) and exemplary compound (D -31), the exemplary compounds (D-4), (D-28) and (D-31) represented by the general formula (2) all have small absorption at 400 to 500 nm. It was found that the invisibility was further improved.
- the exemplified compound (D-6), the exemplified compound (D-11), the exemplified compound (D-12), and other compounds represented by the general formula (2) of the present invention are all 400 to 500 nm. It was found that the absorption was small and the invisibility was even better.
- Example 14 Preparation of fine particles
- Water was added to 500 parts by adding 10 parts of exemplified compound (D-10) and 2 parts of dodecylbenzenesulfonic acid (DBS) as a dispersant.
- DBS dodecylbenzenesulfonic acid
- UPA-EX150 Ultratrac UPA particle size analyzer
- FIG. 2 shows together the absorption spectrum of the gelatin dispersion film of the exemplified compound (D-10) and the absorption spectrum of the exemplified compound (D-10) in a chloroform solution, normalized by ⁇ max.
- the horizontal axis indicates the wavelength
- the vertical axis indicates the absorbance.
- the wavelength was increased by 60 nm or more compared to the absorption in the solution, the absorption ⁇ max reached 843 nm, and good infrared light absorptivity was obtained.
- the absorption spectrum of the gelatin dispersion film had almost no absorption at 400 to 700 nm, and realized excellent invisibility.
- a gelatin dispersion film was prepared in the same manner as in the above example using an infrared absorbent e-color IR-10A (trade name, manufactured by Nippon Shokubai Co., Ltd.). The light resistance of the dispersion films obtained in the above examples and comparative examples was evaluated. Using a light resistance tester (super xenon weather meter, trade name, manufactured by Suga Test Instruments Co., Ltd .; irradiance 180 W / m 2 at 290 nm), Xe light (no UV filter) was irradiated. The results are shown in FIG. In FIG. 4, the horizontal axis represents time (hour), and the vertical axis represents the remaining rate (%). As is apparent from the results of FIG. 4, the dispersion film using the fine particles of the exemplified compound (D-10) or (D-28) has excellent light resistance equal to or better than that of the dispersion film of the comparative example. It was.
- a light resistance tester super xenon weather
- the fine particles of the compound of the present invention have excellent characteristics such as good infrared absorption and invisibility and high light resistance, such as markers such as filters and inks, industrial photothermal conversion materials, It can be applied as a medical material.
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Abstract
Description
剛直な骨格をもち高堅牢な近赤外吸収色素としては、日本触媒(株)から上市されているバナジルナフタロシアニン色素やBASF(株)から上市されているクオータリレン色素があるが、バナジルフタロシアニンは不可視性が不十分である。また、クオータリレンは溶液など分子分散状態では良好な不可視性を有するものの、濃度を上げると会合により可視域に吸収を生じ、不可視性が失われ、使用形態が限定される。
不可視性に優れ、赤外領域を広くカバーする色素としては、日本化薬(株)等から上市されているジインモニウム色素があるが、還元されやすく、堅牢性は不十分であり、使用形態が限定されてしまう。
このように、現在、不可視性と堅牢性を両立する近赤外色素は上市されておらず、これら性能を両立する近赤外色素の開発が望まれている。
一般に、強い蛍光を発するには、蛍光色素を濃度消光を起こさない希薄状態で用い、ホスト材料を共蒸着を行い分子分散状態で使用される。また、このような蛍光色素は、一般に耐光性が低いことが知られている。
<1>下記一般式(1)で表される化合物からなる微粒子。
<2>前記R3がヘテロ環である、<1>項に記載の微粒子。
<3><1>又は<2>項に記載の微粒子であって、波長700nm以上1000nm以下の赤外線を吸収する、赤外線吸収性微粒子。
<4><1>~<3>のいずれか1項に記載の微粒子を含む組成物。
<5><1>~<3>のいずれか1項に記載の微粒子を含む塗布物。
<6>下記一般式(2)で表される赤外線吸収性化合物。
<7>下記一般式(3)で表される赤外線吸収性化合物。
<8>下記一般式(4)で表される赤外線吸収性化合物。
また、本発明の微粒子を含む組成物および塗布物(インクやフィルタ)は、優れた赤外吸収能を有し、優れた不可視性と優れた耐久性とを両立する。
また、本発明の前記一般式(2)で表される赤外線吸収性化合物は、新規化合物であり、特に優れた不可視性を有する。また、本発明の前記一般式(3)で表される赤外線吸収性化合物も、新規化合物であり、高い堅牢性および高い不可視性を両立する。また、本発明の前記一般式(4)で表される赤外線吸収性化合物も、新規化合物であり、高い堅牢性、高い不可視性、優れた分散性、および高い有機溶媒溶解性を示す。
本発明の微粒子は、下記一般式(1)で表される化合物からなる。本発明の微粒子は、優れた赤外吸収特性、不可視性、堅牢性をすべて満足する性能を有する。
また、R1a又はR1bで表されるアリール基としては、好ましくは炭素数6~30、より好ましくは炭素数6~20、特に好ましくは炭素数6~12のアリール基であり、例えばフェニル、o-メチルフェニル、p-メチルフェニル、ビフェニル、ナフチル、アントラニル、フェナントリルなどが挙げられる。
R1a又はR1bで表されるヘテロアリール基としては、好ましくは炭素数1~30、より好ましくは炭素数1~12のヘテロアリール基である。ヘテロ原子としては、例えば窒素原子、酸素原子、硫黄原子が挙げられる。ヘテロアリール基としては、具体的には例えばイミダゾリル、ピリジル、キノリル、フリル、チエニル、ベンズオキサゾリル、ベンズイミダゾリル、ベンズチアゾリル、ナフトチアゾリル、ベンズオキサゾリル、m-カルバゾリル、アゼピニルなどが挙げられる。
一般式(1)中のR1a及びR1bは、互いに同一でも異なってもよい。
(a)1,3-ジカルボニル核:例えば1,3-インダンジオン核、1,3-シクロヘキサンジオン、5,5-ジメチル-1,3-シクロヘキサンジオン、1,3-ジオキサン-4,6-ジオンなど。
(b)ピラゾリノン核:例えば1-フェニル-2-ピラゾリン-5-オン、3-メチル-1-フェニル-2-ピラゾリン-5-オン、1-(2-ベンゾチアゾイル)-3-メチル-2-ピラゾリン-5-オンなど。
(c)イソオキサゾリノン核:例えば3-フェニル-2-イソオキサゾリン-5-オン、3-メチル-2-イソオキサゾリン-5-オンなど。
(d)オキシインドール核:例えば1-アルキル-2,3-ジヒドロ-2-オキシインドールなど。
(e)2,4,6-トリケトヘキサヒドロピリミジン核:例えばバルビツル酸または2-チオバルビツル酸およびその誘導体など。誘導体としては例えば1-メチル、1-エチル等の1-アルキル体、1,3-ジメチル、1,3-ジエチル、1,3-ジブチル等の1,3-ジアルキル体、1,3-ジフェニル、1,3-ジ(p-クロロフェニル)、1,3-ジ(p-エトキシカルボニルフェニル)等の1,3-ジアリール体、1-エチル-3-フェニル等の1-アルキル-1-アリール体、1,3-ジ(2-ピリジル)等の1,3位ジヘテロ環置換体等が挙げられる。
(f)2-チオ-2,4-チアゾリジンジオン核:例えばローダニンおよびその誘導体など。誘導体としては例えば3-メチルローダニン、3-エチルローダニン、3-アリルローダニン等の3-アルキルローダニン、3-フェニルローダニン等の3-アリールローダニン、3-(2-ピリジル)ローダニン等の3位ヘテロ環置換ローダニン等が挙げられる。
(g)2-チオ-2,4-オキサゾリジンジオン(2-チオ-2,4-(3H,5H)-オキサゾールジオン核:例えば3-エチル-2-チオ-2,4-オキサゾリジンジオンなど。
(h)チアナフテノン核:例えば3(2H)-チアナフテノン-1,1-ジオキサイドなど。
(i)2-チオ-2,5-チオゾリジンジオン核:例えば3-エチル-2-チオ-2,5-チアゾリジンジオンなど。
(j)2,4-チオゾリジンジオン核:例えば2,4-チアゾリジンジオン、3-エチル-2,4-チアゾリジンジオン、3-フェニル-2,4-チアゾリジンジオンなど。
(k)チアゾリン-4-オン核:例えば4-チアゾリノン、2-エチル-4-チアゾリノンなど。
(l)4-チアゾリジノン核:例えば2-エチルメルカプト-5-チアゾリン-4-オン、2-アルキルフェニルアミノ-5-チアゾリン-4-オンなど。
(m)2,4-イミダゾリジンジオン(ヒダントイン)核:例えば2,4-イミダゾリジンジオン、3-エチル-2,4-イミダゾリジンジオンなど。
(n)2-チオ-2,4-イミダゾリジンジオン(2-チオヒダントイン)核:例えば2-チオ-2,4-イミダゾリジンジオン、3-エチル-2-チオ-2,4-イミダゾリジンジオンなど。
(o)イミダゾリン-5-オン核:例えば2-プロピルメルカプト-2-イミダゾリン-5-オンなど。
(p)3,5-ピラゾリジンジオン核:例えば1,2-ジフェニル-3,5-ピラゾリジンジオン、1,2-ジメチル-3,5-ピラゾリジンジオンなど。
(q)ベンゾチオフェン-3-オン核:例えばベンゾチオフェン-3-オン、オキソベンゾチオフェンー3-オン、ジオキソベンゾチオフェンー3-オンなど。
(r)インダノン核:例えば1-インダノン、3-フェニル-1-インダノン、3-メチル-1-インダノン、3,3-ジフェニル-1-インダノン、3,3-ジメチル-1-インダノンなど。
一般式(1)中の2つのR2は、互いに同一でも異なってもよく、また、2つのR3は、互いに同一でも異なってもよい。
R4は、R1a、R1b及び/又はR3と共有結合もしくは配位結合しても良い。
一般式(1)中の2つのR4は、互いに同一でも異なってもよい。
前記一般式(2)中、Z1a及びZ1bは各々独立にアリール環もしくはヘテロアリール環を形成する原子団を表す。形成されるアリール環、ヘテロアリール環は、前記一般式(1)におけるR2及びR3の置換基として説明したアリール基、ヘテロアリール基と同義であり、好ましい範囲も同様である。Z1a及びZ1bは同一であることが好ましい。
R5a及びR5bは各々独立に炭素数6~20のアリール基、炭素数4~20のヘテロアリール基、炭素数1~20のアルキル基、炭素数1~20のアルコキシ基、炭素数1~20のアルコキシカルボニル基、カルボキシル基、炭素数1~20のカルバモイル基、ハロゲン原子、又はシアノ基のいずれか1つを表す。具体例には、前記一般式(1)におけるR2及びR3で説明した例と同義であり、好ましい範囲も同様である。R5a及びR5bは同一であることが好ましい。
R5a又はR5bとZ1a又はZ1bとが結合し縮合環を形成しても良く、該縮合環としてはナフチル環、キノリン環などが挙げられる。
Z1a又はZ1bが形成するアリール環もしくはヘテロアリール環にR5a又はR5bで表される基を導入することで、不可視性を大きく向上することができる。
一般式(3)中、R31a及びR31bは各々独立に炭素数1~20のアルキル基、炭素数6~20のアリール基または炭素数3~20のヘテロアリール基を表し、具体的には、前記一般式(1)におけるR1a及びR1bで説明した例と同義であり、好ましい範囲も同様である。R31a及びR31bは同一であることが好ましい。
R32はシアノ基、炭素数1~6のアシル基、炭素数1~6のアルコキシカルボニル基、炭素数1~10のアルキルもしくはアリールスルフィニル基、又は炭素数3~10の含窒素ヘテロアリール基であり、具体的には、前記一般式(1)におけるR2の例と同義であり、好ましい範囲も同様である。
R6及びR7が置換した5員含窒素ヘテロ環を導入し、更にホウ素錯体とすることで、高い堅牢性、高い不可視性を両立する赤外線吸収色素を実現することができる。
Xは酸素原子、イオウ原子、-NR-、-CRR’-を表す。R及びR’は各々独立に水素原子、炭素数1~10のアルキル基、又は炭素数6~10のアリール基を表し、好ましくは水素原子、炭素数1~6のアルキル基、フェニル基である。
一般式(4)中、R41a及びR41bは炭素数1~20のアルキル基、炭素数6~20のアリール基または炭素数3~20のヘテロアリール基を表し、具体的には、前記一般式(1)におけるR1a及びR1bで説明した例と同義であり、好ましい範囲も同様である。ただし、R41a及びR41bは互いに異なる基を表す。
R42はシアノ基、炭素数1~6のアシル基、炭素数1~6のアルコキシカルボニル基、炭素数1~10のアルキルもしくはアリールスルフィニル基、又は炭素数3~10の含窒素ヘテロアリール基であり、具体的には、前記一般式(1)におけるR2の例と同義であり、好ましい範囲も同様である。
Z2は-C=N-と共に含窒素ヘテロ5又は6員環を形成する原子団を表し、含窒素ヘテロ環としてはピラゾール環、チアゾール環、オキサゾール環、イミダゾール環、オキサジアゾール環、チアジアゾール環、トリアゾール環、ピリジン環、ピリダジン環、ピリミジン環、ピラジン環、これらのベンゾ縮環もしくはナフト縮環、又はこれら縮環の複合体を表す。
R44は水素原子、炭素数1~20のアルキル基、炭素数6~20のアリール基、炭素数4~20のヘテロアリール基、金属原子または置換基としてハロゲン原子、炭素数1~10のアルキル基、炭素数6~20のアリール基、もしくは炭素数4~20のヘテロアリール基を有する置換ホウ素を表し、Z2が形成する含窒素ヘテロ環と共有結合もしくは配位結合を有しても良い。
互いに異なるR41a及びR41bで表される基を導入し、Z2が-C=N-と共に形成する含窒素ヘテロ5又は6員環を導入することで、高い堅牢性、高い不可視性、優れた分散性、および高い有機溶媒溶解性を付与することができる。
前記一般式(1)~(4)のいずれかで表される化合物は、該当するジケトピロロピロール化合物に、活性メチレン化合物を縮合させ、場合によっては、さらに、ホウ素や金属を反応させることで合成することができる。ジケトピロロピロール化合物は、「ハイパフォーマンス・ピグメンツ(High Performance Pigments)」,Wiley-VCH,2002年,160~163ページに記載の方法で合成でき、より具体的な例としては米国特許第5,969,154号明細書や特開平9-323993号公報に記載の方法で合成できる。また、ジケトピロロピロール化合物と活性メチレン化合物との縮合反応やその後のホウ素化については、先述の非特許文献1に従って合成できる。ホウ素化試薬はJ.Med.Chem.第3巻356~360頁(1976年)を参考にして合成することができる。また、例えばブロモカテコールボランは東京化成工業社より購入して使用することができる。
また、前記一般式(1)~(4)のいずれかで表される化合物は、モル吸光係数εは特に限定されないが、好ましくは50,000~300,000であり、より好ましくは100,000~250,000である。
本発明の微粒子の粒径は、好ましくは1~1000nmであり、より好ましく5~600nmであり、特に好ましくは20~200nmである。微粒子の粒径は、動的光散乱法を用いたナノトラックUPA粒度分析計(UPA-EX150、商品名、日機装社製)などを用いて測定することができる。
以下に、前記一般式(1)~(4)のいずれかで表される化合物を用いた微粒子の調製方法について説明する。
上記した化合物の合成方法によって、前記一般式(1)~(4)のいずれかで表される化合物は粗結晶として得られるが、本発明の微粒子として用いる場合、後処理を行うことが好ましい。この後処理の方法としては、例えば、ソルベントソルトミリング、ソルトミリング、ドライミリング、ソルベントミリング、アシッドペースティング等の摩砕処理、溶媒加熱処理などによる微粒子制御工程、樹脂、界面活性剤および分散剤等による表面処理工程が挙げられる。
本発明の微粒子を含有する組成物は、水系であっても非水系であってもよい。本発明の水系微粒子組成物において微粒子を分散する水性の液体は、水を主成分とし、所望により親水性有機溶剤を添加した混合物を用いることができる。
前記親水性有機溶剤としては、例えば、メタノール、エタノール、プロパノール、イソプロパノール、ブタノール、イソブタノール、sec-ブタノール、t-ブタノール、ペンタノール、ヘキサノール、シクロヘキサノール、ベンジルアルコール等のアルコール類、エチレングリコール、ジエチレングリコール、トリエチレングリコール、ポリエチレングリコール、プロピレングリコール、ジプロピレングリコール、ポリプロピレングリコール、ブチレングリコール、ヘキサンジオール、ペンタンジオール、グリセリン、ヘキサントリオール、チオジグリコール等の他価アルコール類、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールものブチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノブチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノブチルエーテル、ジプロピレングリコールモノメチルエーテル、トリエチレングリコールモノメチルエーテル、エチレングリコールジアセテート、エチレングリコールモノメチルエーテルアセテートトリエチレングリコールモノエチルエーテル、エチレングリコールモノフェニルエーテル等のグリコール誘導体、エタノールアミン、ジエタノールアミン、トリエタノールアミン、N-メチルジエタノールアミン、N-エチルジエタノールアミン、モルホリン、N-エチルモルホリン、エチレンジアミン、ジエチレントリアミン、トリエチレンテトラミン、ポリエチレンイミン、テトラメチルプロピレンジアミン等のアミン、ホルムアミド、N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、ジメチルスルホキシド、スルホラン、2-ピロリドン、N-メチル-2-ピロリドン、N-ビニル-2-ピロリドン、2-オキサゾリドン、1,3-ジメチル-2-イミダゾリジノン、アセトニトリル、アセトン等が挙げられる。
本発明において用いられる水分散性の樹脂は、主成分が水である分散媒(本明細書では溶媒と呼ぶこともある)に疎水性の合成樹脂が分散された分散物である。
溶媒中に含まれる水の含量は、30%~100%が好ましく、50%~100%がより好ましい。水以外の溶媒としては、メタノールやエタノール、イソプロピルアルコールなどのアルコール類、アセトンやメチルエチルケトンなどのケトン類、テトラヒドロフランやブチルセロソルブなど、水に溶解性を有する溶剤が好ましく用いられる。
合成樹脂(ポリマー)としては、アクリル樹脂、スチレン-アクリル樹脂、ビニル樹脂、ポリウレタン樹脂、ポリエステル樹脂等、ポリアミド樹脂、フッ素系樹脂など種々のポリマーを使用することができる。また、水溶性の樹脂としてはゼラチン、ポリビニルアルコール、カルボキシメチルセルロースなどが挙げられる。
また、分子状態で扱い場合には、上記用途に加え、人体透過性に優れる近赤外領域に吸収をもつことから、診断用マーカーや、光線力学療法にも適応できる。
(例示化合物(D-1)の調製)
下記スキームに従って、例示化合物(D-1)を調製した。
1H-NMR(CDCl3):δ0.9-1.0(m,12H),1.3-1.6(m,16H),1.8(m,2H),3.95(d,4H),7.0(t,2H),7.1(d,4H),7.6(m,4H),7.7(d,4H),8.45(d,2H)
(例示化合物(D-25)の調製)
前記スキームに従い例示化合物(D-25)を調製した。
例示化合物(D-1)0.75グラム(1等量)とクロロジフェニルホウ素0.5グラム(2.5等量)とをオルトジクロロベンゼン20mL中で3時間加熱還流した。室温に冷却して水10mLを加えた後、分液操作により有機層を取り出し、炭酸水素ナトリウム水溶液で洗浄した後、溶媒を減圧留去した。得られた粗生成物をシリカゲルカラムクロマトグラフィー(クロロホルム溶媒)で精製し、さらにクロロホルム/メタノール溶媒を用いて再結晶し、目的化合物(D-25)を0.58グラム、収率53%で得た。
1H-NMR(CDCl3):δ0.9-1.0(m,12H),1.3-1.6(m,16H),1.8(m,2H),3.75(d,4H),6.35(d,4H),6.65(d,4H),6.7(t,2H),7.1-7.2(m,20H),7.35(d,2H),7.45(t,2H),7.8(d,2H)
(例示化合物(D-30)の調製)
前記スキームに従い例示化合物(D-30)を調製した。
例示化合物(D-1)1グラム(1等量)と三フッ化ホウ素ジエチルエーテル錯体0.5グラム(2.5等量)とをオルトジクロロベンゼン20mL中で1時間加熱還流した後、ジイソプロピルメチルアミン0.75グラム(5等量)を加えさらに一時間加熱還流した。室温に冷却して水10mLを加えた後、分液操作により有機層を取り出し、溶媒を減圧留去した。得られた粗生成物をシリカゲルカラムクロマトグラフィー(クロロホルム溶媒)で精製し、さらにクロロホルム/メタノール溶媒を用いて再結晶し、目的化合物(D-30)を0.8グラム、収率70%で得た。
1H-NMR(CDCl3):δ0.9-1.0(m,12H),1.3-1.6(m,16H),1.8(m,2H),3.95(d,4H),7.05(d,4H),7.6(d,4H),7.7(t,2H),7.85(t,2H),8.35(d,2H)
以下の例示化合物を、実施例1における原料を代えたこと以外は実施例1と同様にして調製した。構造同定した1H-NMRを示す。
1H-NMR(CDCl3):0.9(t,6H),1.25-1.45(m,16H),1.7(m,4H),2.75(t,4H),7.0(t,2H),7.4(d,4H),7.6(d,4H),7.65(m,4H),8.45(d,2H)
1H-NMR(CDCl3):0.9(t,6H),1.2-1.6(m,36H),1.7(m,4H),3.15(m,4H),7.0(t,2H),7.4-7.5(m,4H),7.55-7.7(m,4H),8.5(d,2H)
1H-NMR(CDCl3):2.5(s,6H),7.0(m,2H),7.35-7.45(m,4H),7.5(t,4H),7.5(m,4H),8.4(d,2H)
1H-NMR(CDCl3):2.5(s,6H),7.3(m,2H),7.4-7.5(m,6H),7.55(m,2H),7.65(d,2H),7.8(m,4H)
1H-NMR(CDCl3):δ0.9-1.0(m,12H),1.35-1.6(m,16H),1.8(m,2H),3.85(d,4H),6.45(s,8H),7.0(d,4H),7.15(m12H),7.2(m,2H),7.25(m,4H+4H),7.5(m,2H)
1H-NMR(CDCl3):δ0.9-1.1(m,12H),1.4-1.6(m,16H),1.85(m,2H),4.0(d,4H),7.15(d,4H),7.4(m4H),7.6(t,2H),7.75(d,4H),7.8-7.9(m,6H)
1H-NMR(CDCl3):δ0.9-1.0(m,12H),1.35-1.6(m,16H),1.8(m,2H),3.95(d,4H),7.1(d,4H),7.4-7.5(m,4H),7.7(d,4H),7.75(d,2H),8.0(d,2H)
1H-NMR(CDCl3):δ1.0(m,12H),1.4-1.55(m,16H),1.8(m,2H),3.85(d,4H),6.5(s,8H),7.1(d,2H),7.15(m,12H),7.3(m,4H+4H),7.4(d,4H),7.5(m,2H),7.7(t,4H)
1H-NMR(CDCl3):1.9(s,6H),6.65(d,2H),6.7-6.8(m,6H),6.95(m,8H),7.0-7.1(m,4H),7.25-7.35(m,12H),7.5(m,2H),7.85(d,2H)
1H-NMR(CDCl3):1.7(s,6H),6.45(t,2H),6.75-7.0(m,16H),7.0-7.15(m,4H),7.2-7.35(m,8H),7.5(m,4H),7.6(d,2H)
1H-NMR(CDCl3):δ0.9-1.0(m,12H),1.35-1.55(m,16H),1.8(m,2H),3.95(d,4H),7.1(d,4H),7.35-7.5(m,4H),7.7(d,4H),7.75(m,2H),8.0(m,2H)
1H-NMR(CDCl3):δ0.9-1.0(m,6H),1.3-1.6(m,8H),1.8(m,1H),3.85(d,2H),7.1(d,2H),7.3(m,2H),7.4(m,2H),7.6(m,3H),7.7-7.8(m,8H)
(例示化合物(D-102)の調製)
前記スキームに従い例示化合物(D-102)を調製した。
例示化合物(D-101)0.18グラム(1等量)、ジフェニルボリン酸2-アミノエチル0.125グラム(2.2等量)及び四塩化チタン0.19gをトルエン4mL中で1時間加熱還流した。室温に冷却してメチルアルコール5mLを加えた後ろ過し、結晶を得た。得られた粗生成物をシリカゲルカラムクロマトグラフィー(クロロホルム溶媒)で精製し、目的化合物(D-102)を0.2グラム、収率77%で得た。λmaxはクロロホルム中で780nmだった。モル吸収係数は、クロロホルム中、2.15×105dm3/mol・cmであった。
1H-NMR(CDCl3):δ0.9-1.0(m,6H),1.3-1.6(m,8H),1.8(m,1H),3.8(d,2H),6.4(s,4H),6.5(d,2H),7.0(m,6H),7.1-7.2(m,15H),7.3(m,8H),7.5(d,2H)
(例示化合物(D-106)の調製)
まず、実施例1における原料を代えたこと以外は実施例1と同様にして、例示化合物(D-105)を調製した。
次に、例示化合物(D-105)0.15グラム(1等量)、ジフェニルボリン酸2-アミノエチル0.11グラム(2.2等量)及び四塩化チタン0.17gをトルエン4mL中で1時間加熱還流した。室温に冷却してメチルアルコール5mLを加えた後ろ過し、結晶を得た。得られた粗生成物をシリカゲルカラムクロマトグラフィー(クロロホルム溶媒)で精製し、目的化合物(D-106)を0.1グラム、収率45%で得た。λmaxはクロロホルム中で779nmだった。モル吸収係数は、クロロホルム中、2.24×105dm3/mol・cmであった。
1H-NMR(CDCl3):δ1.3(s,9H),6.5(m,4H),6.9-7.0(m,8H),7.1-7.2(m,14H),7.2-7.3(m,9H),7.5(d,2H)
(例示化合物(D-107)の調製)
実施例1における原料を代えたこと以外は実施例1と同様にして、例示化合物(D-107)を調製した。λmaxはクロロホルム中で727nmだった。モル吸収係数は、クロロホルム中、8.14×104dm3/mol・cmであった。
(例示化合物(D-108)の調製)
例示化合物(D-107)0.71グラム(1等量)、ジフェニルボリン酸2-アミノエチル0.48グラム(2.2等量)及び四塩化チタン0.72gをトルエン10mL中で1時間加熱還流した。室温に冷却してメチルアルコール10mLを加えた後ろ過し、結晶を得た。得られた粗生成物をシリカゲルカラムクロマトグラフィー(クロロホルム溶媒)で精製し、目的化合物(D-108)を0.7グラム、収率70%で得た。λmaxはクロロホルム中で779nmだった。モル吸収係数は、クロロホルム中、1.94×105dm3/mol・cmであった。
1H-NMR(CDCl3):δ0.9-1.0(m,6H),1.3-1.6(m,8H),1.8(m,1H),3.8(s、3H),3.85(d,2H),6.5(s,8H),7.0(m,4H),7.1-7.2(m,14H),7.3(m,8H),7.5(d,2H)
(例示化合物(D-131)の調製)
例示化合物(D-17)2.6グラム(1等量)とブロモカテコールボラン(東京化成工業社製)2.4グラム(4等量)とをトルエン20mL中、3時間加熱還流した。室温に冷却してメタノールを20mL加え、析出した結晶をろ過した。得られた粗生成物をシリカゲルカラムクロマトグラフィー(溶媒クロロホルム)で精製し、さらにクロロホルム/メタノール溶媒を用いて再結晶し、目的化合物(D-131)を2.3グラム、収率70%で得た。
1H-NMR(CDCl3):δ0.95-1.05(m,12H),1.35-1.6(m,16H),1.7-1.8(m,2H),3.75(d,4H),6.4(m,4H),6.5-6.65(m,8H),7.1(d,2H),7.15-7.3(m,8H),7.45(t,2H),7.7(d,2H)
1H-NMR(CDCl3):δ0.9-1.0(m,12H),1.3-1.7(m,16H),1.8(m,2H),3.8(d,4H),6.5(m,8H),6.9(m,4H),7.0(m,4H),7.0-7.2(m,4H),7.4(d,4H),7.5(d,2H)7.6(d,2H)
以下の例示化合物を、実施例11における原料を代えたこと以外は実施例11と同様にして調製した。収率、λmax、モル吸収係数、構造同定した1H-NMRについてそれぞれ示す。
例示化合物(D-135)
収率92%。λmaxはクロロホルム中で779nmだった。モル吸収係数は、クロロホルム中、2.16×105dm3/mol・cmであった。
1H-NMR(CDCl3):δ0.9-1.0(m,12H),1.3-1.7(m,16H),1.8(m,2H),3.8(d,4H),6.5(m,8H),6.9(d,2H),7.0-7.2(m,20H),7.6(d,2H)
収率89%。λmaxはクロロホルム中で779nmだった。モル吸収係数は、クロロホルム中、1.77×105dm3/mol・cmであった。
1H-NMR(CDCl3):δ0.9-1.0(m,12H),1.2(s,36H),1.3-1.7(m,16H),1.8(m,2H),3.8(d,4H),6.5(m,8H),7.0-7.2(m,20H),7.5(d,2H),7.6(d,2H)
収率56%。λmaxはクロロホルム中で802nmだった。モル吸収係数は、クロロホルム中、1.97×105dm3/mol・cmであった。
1H-NMR(CDCl3):δ0.7(t,12H),0.9-1.0(m,12H),1.1-1.2(m,12H),1.3-1.4(m,12H),1.3-1.7(m,16H),1.8(m,2H),3.8(d,4H),6.9(d,4H),7.3-7.4(m,4H),7.5(d,4H),7.7(d,2H)7.9(d,2H)
収率80%。λmaxはクロロホルム中で782nmだった。モル吸収係数は、クロロホルム中、1.96×105dm3/mol・cmであった。
1H-NMR(CDCl3):δ0.9-1.0(m,12H),1.3-1.7(m,16H),1.8(m,2H),3.5(d,4H),6.1(m,4H),6.4(m,4H),6.9-7.2(m,4H),7.4-7.6(m,14H),7.6-7.8(m,16H)
[溶液吸収スペクトルの評価による不可視性評価]
例示化合物(D-17)及び例示化合物(D-9)のクロロホルム中での溶液スペクトルをそれぞれ規格化し、比較した。結果を図1に示す。図1中、横軸は波長を、縦軸は吸光度を示す。図1から明らかなように、例示化合物(D-9)は、例示化合物(D-17)に比較して400~500nmの吸収が小さく、不可視性が更に優れることがわかった。
また、例示化合物(D-6)、例示化合物(D-11)、例示化合物(D-12)や、その他の本発明の前記一般式(2)で表される化合物はいずれも400~500nmの吸収が小さく、不可視性が更に優れることがわかった。
(微粒子の調製)
例示化合物(D-10)を10部および分散剤としてドデシルベンゼンスルホン酸(DBS)2部に水を加え500部とした。これにさらに0.1mmφのジルコニアビーズを500部添加し、遊星型ボールミルにて300rpmで5時間処理を行い、微細粒子からなる水分散液を作製した。
その後、前記水分散物からビーズを濾過で分離し、ナノトラックUPA粒度分析計(UPA-EX150、商品名、日機装社製)を用い粒径を測定したところ、平均粒径は0.05μmであった。
得られた水分散物にゼラチン水溶液を添加し、ゼラチン下塗りしたポリエチレンテレフタレート(PET)板に塗布し、例示化合物(D-10)微粒子のゼラチン分散膜を作製した。得られたゼラチン膜の吸収スペクトルを測定し、例示化合物(D-10)の吸収のλmax光学濃度が1.5となるよう水分散物濃度を調節した。
図2に、例示化合物(D-10)のゼラチン分散膜の吸収スペクトルと例示化合物(D-10)のクロロホルム溶液中での吸収スペクトルとをλmaxで規格化して併せて示す。図2中、横軸は波長を、縦軸は吸光度を示す。図2から明らかなように、微粒子化することで、溶液中における吸収に比べて60nm以上長波長化し、吸収のλmaxは843nmに到達し、良好な赤外光吸収性が得られた。また、ゼラチン分散膜の吸収スペクトルは、400~700nmにほとんど吸収を有せず、優れた不可視性を実現した。
比較例として、赤外吸収剤イーエクスカラーIR-10A(商品名、日本触媒製)を用い、上記実施例と同様の方法でゼラチン分散膜を作製した。
上記実施例及び比較例で得られた分散膜の耐光性評価を行った。耐光性試験機(スーパーキセノンウエザーメーター、商品名、スガ試験機(株)社製; 放射照度180W/m2 at 290nm)を用い、Xe光(UVフィルタなし)を照射した。結果を図4に示す。図4中、横軸は時間(時間)を、縦軸は残存率(%)を示す。図4の結果から明らかなように、例示化合物(D-10)又は(D-28)の微粒子を用いた分散膜は、比較例の分散膜と同等以上の優れた耐光性を有することがわかった。
Claims (8)
- 前記R3がヘテロ環である、請求項1記載の微粒子。
- 請求項1又は2に記載の微粒子であって、波長700nm以上1000nm以下の赤外線を吸収する、赤外線吸収性微粒子。
- 請求項1~3のいずれか1項に記載の微粒子を含む組成物。
- 請求項1~3のいずれか1項に記載の微粒子を含む塗布物。
- 下記一般式(2)で表される赤外線吸収性化合物。
- 下記一般式(3)で表される赤外線吸収性化合物。
- 下記一般式(4)で表される赤外線吸収性化合物。
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Also Published As
Publication number | Publication date |
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EP2272849A4 (en) | 2011-08-10 |
KR20110008062A (ko) | 2011-01-25 |
US8303863B2 (en) | 2012-11-06 |
KR20160097387A (ko) | 2016-08-17 |
KR101687837B1 (ko) | 2016-12-19 |
EP2272849B1 (en) | 2016-11-23 |
JP5380019B2 (ja) | 2014-01-08 |
KR101697913B1 (ko) | 2017-01-18 |
US20110012075A1 (en) | 2011-01-20 |
CN101983200A (zh) | 2011-03-02 |
CN101983200B (zh) | 2013-07-24 |
EP2272849A1 (en) | 2011-01-12 |
JP2009263614A (ja) | 2009-11-12 |
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