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WO2019151121A1 - Composé, composition le contenant, corps moulé et dispositif électroluminescent l'utilisant - Google Patents

Composé, composition le contenant, corps moulé et dispositif électroluminescent l'utilisant Download PDF

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WO2019151121A1
WO2019151121A1 PCT/JP2019/002348 JP2019002348W WO2019151121A1 WO 2019151121 A1 WO2019151121 A1 WO 2019151121A1 JP 2019002348 W JP2019002348 W JP 2019002348W WO 2019151121 A1 WO2019151121 A1 WO 2019151121A1
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泰宜 市橋
畛于 権
富永　剛
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Toray Industries Inc
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Toray Industries Inc
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    • 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
    • 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
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces

Definitions

  • the present invention relates to a compound that emits light in the near-infrared region, a composition containing the compound, a molded body using the composition, and a light emitting device including the molded body.
  • Compounds having luminescence in the near infrared region are used in various industrial products such as home appliance remote control, optical communication such as wireless digital communication, and various measuring devices such as sugar content sensors. Recently, it has been used for medical applications such as bioimaging probes because it has little impact on the living body. Furthermore, with the further development of the digital society, biometric authentication technologies such as vein authentication and face authentication are also being used. It is also used.
  • inorganic compounds such as rare earth metals and semiconductor compounds are known. These have restrictions that a certain size and shape are required for the expression of characteristics, such as the necessity of using a uniform particle size and the need for a pn junction.
  • organic compounds since an organic compound has a light emitting function with a single molecule, it has high flexibility, and development aimed at application to medical use is being performed (for example, Patent Document 1).
  • organic compounds generally have a low quantum yield and do not have high reliability that is assumed to be mounted on mobile devices and digital home appliances.
  • an organic compound that efficiently absorbs light in the near-infrared region has been developed (for example, Patent Document 2), but high-efficiency and high-reliability light emission has not been confirmed.
  • the problem to be solved by the present invention is that a compound having light emission in the near infrared region (hereinafter, abbreviated as “near infrared light emission” as appropriate), for example, an organic compound having flexibility, is highly efficient near infrared. This is to achieve both light emission and highly reliable near-infrared light emission against oxidation by excitation light.
  • near infrared light emission for example, an organic compound having flexibility
  • the compound according to the present invention is a compound represented by the general formula (1).
  • Ar 1 and Ar 2 may be the same or different, and are a 5-membered aromatic ring, a 6-membered aromatic ring, or two or more 5-membered rings and / or A condensed aromatic ring in which a 6-membered ring is condensed, and these aromatic ring and condensed aromatic ring may have a substituent, and X a and X b are CR 7 or a nitrogen atom; 7 is an electron withdrawing group, and R 1 and R 2 may be the same or different and are a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, R 3 to R 6 are Cyano group, halogen, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted alkynyl group, substituted or unsubstituted aryl group, and substituted or unsubstituted Heter
  • the compound represented by the general formula (1) is a compound represented by the general formula (2), a compound represented by the general formula (3), A compound represented by formula (4), a compound represented by formula (5), a compound represented by formula (6), or a compound represented by formula (7), It is characterized by.
  • X a and X b are CR 7 or a nitrogen atom, and R 7 is an electron withdrawing group.
  • X 1 and X 2 may be the same or different.
  • a sulfur atom, an oxygen atom, a nitrogen atom or a phosphorus atom, X 3 and X 4 may be the same or different, and a nitrogen atom or a phosphorus atom, and R 101 and R 102 may be the same or different.
  • R 103 to R 106 may be the same or different, and may be a cyano group, a halogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted group; It is selected from the group consisting of a substituted alkoxy group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroaryl group.
  • At least one of R 103 to R 106 is a cyano group, and R 107 to R 118 may be the same or different, and may be a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cyclohexane.
  • alkyl group a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a hydroxyl group, a thiol group, a substituted or unsubstituted alkoxy group, Substituted or unsubstituted alkylthio group, substituted or unsubstituted aryl ether group, substituted or unsubstituted aryl thioether group, substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group, halogen, cyano group, aldehyde group , Substituted or unsubstituted carbonyl group, carboxyl group, substituted Or an unsubstituted oxycarbonyl group, a substituted or unsubstituted
  • the compound represented by the general formula (1) is a compound represented by the general formula (8), a compound represented by the general formula (9), It is either a compound represented by Formula (10) or a compound represented by General Formula (11).
  • X a and X b are CR 7 or a nitrogen atom, and R 7 is an electron withdrawing group.
  • X 5 and X 6 may be the same or different.
  • a sulfur atom, an oxygen atom, a nitrogen atom or a phosphorus atom, X 7 to X 10 may be the same or different, and a nitrogen atom or a phosphorus atom, and R 201 and R 202 may be the same or different.
  • a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, R 203 to R 206 which may be the same or different, are a cyano group, a halogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted group; Selected from the group consisting of a substituted alkoxy group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroaryl group And, .R 207 ⁇ R 216 at least one of them is a cyano group of R 203 ⁇ R 206 may be the same or different, a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl An alkyl group, a substituted or unsubstituted heterocyclic
  • At least one of R 209 to R 216 is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group. Or a ring structure formed between adjacent substituents.
  • the compound represented by the general formula (1) is a compound represented by the general formula (12), a compound represented by the general formula (13), A compound represented by formula (14), a compound represented by formula (15), a compound represented by formula (16), or a compound represented by formula (17), It is characterized by.
  • R 301 to R 304 may be the same or different, and are a cyano group, a halogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted group.
  • R 301 to R 304 is a cyano group
  • R 305 to R 316 may be the same or different and each represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, substituted or unsubstituted Unsubstituted cycloalkenyl group, substituted or unsubstituted alkynyl group, hydroxyl group, thiol group, substituted or Substituted alkoxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted aryl ether
  • At least one of R 309 to R 316 is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group. Or a ring structure formed between adjacent substituents.
  • the compound according to the present invention is characterized in that, in the above-mentioned invention, in the general formula (1), R 3 to R 6 are all cyano groups.
  • the compound according to the present invention is characterized in that, in the above invention, the compound represented by the general formula (1) has a maximum light emission in a wavelength range of 700 nm or more.
  • composition according to the present invention is characterized by including the compound according to any one of the above inventions and a bainter resin.
  • the molded body according to the present invention is a molded body molded using the composition described in the above invention.
  • the light-emitting device is a light-emitting device including a light source and a near-infrared light conversion unit, wherein the near-infrared light conversion unit includes the molded body described in the above invention. To do.
  • the present invention there is an effect that it is possible to provide a compound that emits light in the near infrared region while having high luminous efficiency and excellent reliability. Moreover, there exists an effect that the composition containing the said compound, the molded object using the same, and a light-emitting device can be provided.
  • FIG. 1 is a schematic cross-sectional view showing a configuration of a first example of a light emitting device according to an embodiment of the present invention.
  • FIG. 2 is a schematic cross-sectional view showing the configuration of the second example of the light emitting device according to the embodiment of the invention.
  • FIG. 3 is a schematic cross-sectional view showing the configuration of the third example of the light emitting device according to the embodiment of the invention.
  • FIG. 4 is a schematic cross-sectional view showing the configuration of the fourth example of the light emitting device according to the embodiment of the invention.
  • FIG. 5 is a schematic cross-sectional view showing the configuration of the fifth example of the light-emitting device according to the embodiment of the present invention.
  • the compound according to the embodiment of the present invention is a compound represented by the following general formula (1).
  • Ar 1 and Ar 2 may be the same or different, and are a 5-membered aromatic ring, a 6-membered aromatic ring, or two or more 5-membered rings and / or 6 It is a condensed aromatic ring in which member rings are condensed. These aromatic rings and condensed aromatic rings may have a substituent.
  • X a and X b are CR 7 or a nitrogen atom, and R 7 is an electron withdrawing group.
  • R 1 and R 2 may be the same or different and each represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
  • R 3 to R 6 may be the same or different, and are a cyano group, a halogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryl group And a group consisting of a substituted or unsubstituted heteroaryl group. At least one of R 3 to R 6 is a cyano group.
  • hydrogen may be deuterium.
  • a substituted or unsubstituted aryl group having 6 to 40 carbon atoms includes 6 to 40 carbon atoms including the number of carbon atoms contained in the substituent group substituted on the aryl group.
  • An aryl group The same applies to other substituents that define the number of carbon atoms.
  • the substituents in the case of substitution include alkyl groups, cycloalkyl groups, heterocyclic groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, hydroxyl groups, thiol groups, alkoxy groups, alkylthio groups.
  • Aryl ether group, aryl thioether group, aryl group, heteroaryl group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, oxycarbonyl group, carbamoyl group, amino group, nitro group, silyl group, siloxanyl group, boryl Group and a phosphine oxide group are preferable, and specific substituents that are preferable in the description of each substituent are preferable. Moreover, these substituents may be further substituted with the above-mentioned substituents.
  • substituted means that a hydrogen atom or a deuterium atom is substituted.
  • substituted or unsubstituted means that a hydrogen atom or a deuterium atom is substituted.
  • substituted or unsubstituted is the same as described above.
  • the alkyl group is, for example, a saturated aliphatic hydrocarbon such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, etc.
  • the additional substituent when it is substituted and examples thereof include an alkyl group, a halogen, an aryl group, a heteroaryl group, and the like, and this point is common to the following description.
  • the number of carbon atoms of the alkyl group is not particularly limited, but is preferably in the range of 1 to 20 and more preferably 1 to 8 from the viewpoint of availability and cost.
  • the cycloalkyl group refers to, for example, a saturated alicyclic hydrocarbon group such as a cyclopropyl group, a cyclohexyl group, a norbornyl group, an adamantyl group, which may or may not have a substituent.
  • carbon number of an alkyl group part is not specifically limited, Preferably it is the range of 3-20.
  • the heterocyclic group refers to, for example, an aliphatic ring having an atom other than carbon, such as a pyran ring, piperidine ring, or cyclic amide, in the ring, which may or may not have a substituent. Good. Although carbon number of a heterocyclic group is not specifically limited, Preferably it is the range of 2-20.
  • alkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond such as a vinyl group, an allyl group, or a butadienyl group, which may or may not have a substituent.
  • carbon number of an alkenyl group is not specifically limited, Preferably it is the range of 2-20.
  • the cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond such as a cyclopentenyl group, a cyclopentadienyl group, a cyclohexenyl group, and the like, which may have a substituent. It may not have.
  • the alkynyl group refers to, for example, an unsaturated aliphatic hydrocarbon group containing a triple bond such as an ethynyl group, which may or may not have a substituent.
  • carbon number of an alkynyl group is not specifically limited, Preferably it is the range of 2-20.
  • An alkoxy group refers to a functional group to which an aliphatic hydrocarbon group is bonded through an ether bond such as a methoxy group, an ethoxy group, or a propoxy group, and the aliphatic hydrocarbon group has a substituent. May not be included.
  • carbon number of an alkoxy group is not specifically limited, Preferably it is the range of 1-20.
  • the alkylthio group is a group in which an oxygen atom of an ether bond of an alkoxy group is substituted with a sulfur atom.
  • the hydrocarbon group of the alkylthio group may or may not have a substituent. Although carbon number of an alkylthio group is not specifically limited, Preferably it is the range of 1-20.
  • An aryl ether group refers to a functional group to which an aromatic hydrocarbon group is bonded via an ether bond, such as a phenoxy group, and the aromatic hydrocarbon group may or may not have a substituent. Also good. Although carbon number of an aryl ether group is not specifically limited, Preferably, it is the range of 6-40.
  • the aryl thioether group is a group in which an oxygen atom of an ether bond of an aryl ether group is substituted with a sulfur atom.
  • the aromatic hydrocarbon group in the aryl thioether group may or may not have a substituent.
  • the number of carbon atoms of the arylthioether group is not particularly limited, but is preferably in the range of 6 or more and 40 or less.
  • the aryl group is, for example, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthryl group, anthracenyl group, benzophenanthryl group, benzoanthracene group.
  • An aromatic hydrocarbon group such as a nyl group, a chrycenyl group, a pyrenyl group, a fluoranthenyl group, a triphenylenyl group, a benzofluoranthenyl group, a dibenzoanthracenyl group, a perylenyl group, or a helicenyl group.
  • a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, an anthracenyl group, a pyrenyl group, a fluoranthenyl group, and a triphenylenyl group are preferable.
  • the aryl group may or may not have a substituent. Although carbon number of an aryl group is not specifically limited, Preferably it is 6-40, More preferably, it is the range of 6-30.
  • the aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, or an anthracenyl group.
  • a phenyl group and a naphthyl group are more preferable. Particularly preferred is a phenyl group.
  • Heteroaryl group is, for example, pyridyl group, furanyl group, thienyl group, quinolinyl group, isoquinolinyl group, pyrazinyl group, pyrimidyl group, pyridazinyl group, triazinyl group, naphthyridinyl group, cinnolinyl group, phthalazinyl group, quinoxalinyl group, quinazolinyl group, Benzofuranyl group, benzothienyl group, indolyl group, dibenzofuranyl group, dibenzothienyl group, carbazolyl group, benzocarbazolyl group, carbolinyl group, indolocarbazolyl group, benzofurocarbazolyl group, benzothienocarbazolyl Group, dihydroindenocarbazolyl group, benzoquinolinyl group, acridinyl group, dibenzoacridinyl
  • the naphthyridinyl group is any of 1,5-naphthyridinyl group, 1,6-naphthyridinyl group, 1,7-naphthyridinyl group, 1,8-naphthyridinyl group, 2,6-naphthyridinyl group, and 2,7-naphthyridinyl group.
  • the heteroaryl group may or may not have a substituent. Although carbon number of a heteroaryl group is not specifically limited, Preferably it is 2-40, More preferably, it is the range of 2-30.
  • the heteroaryl group includes pyridyl, furanyl, thienyl, quinolinyl, pyrimidyl, triazinyl, benzofuranyl, benzothienyl, indolyl, dibenzo A furanyl group, a dibenzothienyl group, a carbazolyl group, a benzimidazolyl group, an imidazopyridyl group, a benzoxazolyl group, a benzothiazolyl group, and a phenanthrolinyl group are preferable, and a pyridyl group, a furanyl group, a thienyl group, and a quinolinyl group are more preferable. Particularly preferred is a pyridyl group.
  • Halogen refers to an atom selected from fluorine, chlorine, bromine and iodine.
  • the carbonyl group, carboxyl group, oxycarbonyl group, and carbamoyl group may or may not have a substituent.
  • substituents include an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group, and these substituents may be further substituted.
  • the ester group refers to a functional group having a substituent bonded thereto through an ester bond such as an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group, and this substituent may be further substituted.
  • carbon number of an ester group is not specifically limited, Preferably it is the range of 1-20. More specifically, examples of the ester group include a methyl ester group, an ethyl ester group, a propyl ester group, a butyl ester group, an isopropyl ester group, a hexyl ester group, and a phenyl ester group.
  • the amide group refers to a functional group in which a substituent such as an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group is bonded via an amide bond, and this substituent may be further substituted.
  • carbon number of an amide group is not specifically limited, Preferably it is the range of 1-20. More specifically, examples of the amide group include a methylamide group, an ethylamide group, a propylamide group, a butylamide group, an isopropylamide group, a hexylamide group, and a phenylamide group.
  • An amino group is a substituted or unsubstituted amino group.
  • the amino group may or may not have a substituent.
  • substituents in the case of substitution include an aryl group, a heteroaryl group, a linear alkyl group, and a branched alkyl group.
  • aryl group and heteroaryl group a phenyl group, a naphthyl group, a pyridyl group, and a quinolinyl group are preferable. These substituents may be further substituted.
  • carbon number of an amino group is not specifically limited, Preferably it is 2-50, More preferably, it is 6-40, Most preferably, it is the range of 6-30.
  • silyl groups include trimethylsilyl groups, triethylsilyl groups, tert-butyldimethylsilyl groups, propyldimethylsilyl groups, vinyldimethylsilyl groups, and other alkylsilyl groups, phenyldimethylsilyl groups, tert-butyldiphenylsilyl groups, An arylsilyl group such as a phenylsilyl group or a trinaphthylsilyl group is shown. Substituents on silicon may be further substituted. Although carbon number of a silyl group is not specifically limited, Preferably it is the range of 1-30.
  • the siloxanyl group refers to a silicon compound group via an ether bond such as a trimethylsiloxanyl group. Substituents on silicon may be further substituted.
  • the boryl group is a substituted or unsubstituted boryl group.
  • the boryl group may or may not have a substituent. Examples of the substituent in the case of substitution include an aryl group, a heteroaryl group, a linear alkyl group, a branched alkyl group, and an aryl ether group. , An alkoxy group, and a hydroxyl group. Of these, an aryl group and an aryl ether group are preferable.
  • the phosphine oxide group is a group represented by —P ( ⁇ O) R 8 R 9 .
  • R 8 and R 9 are selected from the above substituents in the same manner as R 1 to R 6 in the general formula (1).
  • Acyl group refers to a functional group in which substituents such as an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group are bonded via a carbonyl bond, and this substituent may be further substituted.
  • carbon number of an acyl group is not specifically limited, Preferably it is the range of 1-20. More specifically, examples of the acyl group include an acetyl group, a propionyl group, a benzoyl group, and an acrylyl group.
  • the sulfonyl group refers to a functional group in which a substituent such as an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group is bonded via a —S ( ⁇ O) 2 — bond. May be substituted.
  • the arylene group refers to a divalent or higher valent group derived from an aromatic hydrocarbon group such as benzene, naphthalene, biphenyl, fluorene, phenanthrene, etc., which may or may not have a substituent. .
  • a divalent or trivalent arylene group is preferable. Specifically as an arylene group, a phenylene group, a biphenylene group, a naphthylene group etc. are mentioned as an arylene group.
  • the heteroarylene group is a divalent or higher valent group derived from an aromatic group having one or more atoms other than carbon in the ring, such as pyridine, quinoline, pyrimidine, pyrazine, triazine, quinoxaline, quinazoline, dibenzofuran, dibenzothiophene. This may or may not have a substituent.
  • a divalent or trivalent heteroarylene group is preferable.
  • the number of carbon atoms in the heteroarylene group is not particularly limited, but is preferably in the range of 2-30.
  • heteroarylene group examples include 2,6-pyridylene group, 2,5-pyridylene group, 2,4-pyridylene group, 3,5-pyridylene group, 3,6-pyridylene group, 2,4, 6-pyridylene group, 2,4-pyrimidinylene group, 2,5-pyrimidinylene group, 4,6-pyrimidinylene group, 2,4,6-pyrimidinylene group, 2,4,6-triazinylene group, 4,6-dibenzofurani
  • Examples include a len group, a 2,6-dibenzofuranylene group, a 2,8-dibenzofuranylene group, and a 3,7-dibenzofuranylene group.
  • Ar 1 is a X a and boron atoms, is bonded to the pyrrolo-pyrrole skeleton.
  • Ar 2 is bonded to the pyrrolopyrrole skeleton through Xb and a boron atom. Therefore, since the compound represented by the general formula (1) is a strong and highly planar skeleton, it exhibits a high fluorescence quantum yield.
  • the compound represented by the general formula (1) since the intramolecular conjugation of the compound represented by the general formula (1) can be expanded using such a skeleton, the compound represented by the general formula (1) has a maximum emission wavelength. It becomes 700 nm or more and shows near-infrared emission characteristics.
  • Ar 1 and Ar 2 are condensed by condensing two or more 5-membered rings and / or 6-membered rings.
  • An aromatic ring is preferred.
  • a condensed aromatic ring a condensed aromatic ring in which two or more five-membered rings are condensed, a condensed aromatic ring in which two or more six-membered rings are condensed, and one or more five-membered rings
  • examples thereof include a condensed aromatic ring in which a ring and one or more 6-membered rings are condensed.
  • the condensed aromatic ring is more preferably a structure in which 2 to 3 5-membered or 6-membered rings are condensed.
  • a condensed aromatic ring having a suitable structure specifically, a condensed aromatic ring in which two 5-membered rings are condensed, a condensed aromatic ring in which two six-membered rings are condensed, one 5 A condensed aromatic ring in which a member ring and one 6-membered ring are condensed, a condensed aromatic ring in which three 5-membered rings are condensed, a condensed aromatic ring in which three 6-membered rings are condensed, one 5 Examples thereof include a condensed aromatic ring in which a member ring and two 6-membered rings are condensed, and a condensed aromatic ring in which two 5-membered rings and one 6-membered ring are condensed.
  • a structure in which two 5-membered rings or 6-membered rings are condensed is more preferable.
  • a condensed aromatic ring having a more preferable structure specifically, a condensed aromatic ring in which two 5-membered rings are condensed, a condensed aromatic ring in which two six-membered rings are condensed, A condensed aromatic ring obtained by condensing a 5-membered ring and one 6-membered ring is exemplified.
  • the condensed aromatic ring includes a condensed aromatic ring in which two 6-membered rings are condensed, a condensed aromatic ring in which one 5-membered ring and one 6-membered ring are condensed, and one 5 A condensed aromatic ring in which a member ring and two 6-membered rings are condensed, or a condensed aromatic ring in which two 5-membered rings and one 6-membered ring are condensed is particularly preferable.
  • aromatic ring structure examples include ring structures such as a pyrrole ring, an imidazole ring, a pyrazole ring, an oxazole ring, a thiazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, and a triazine ring.
  • the aromatic ring structure is not particularly limited as long as it is a skeleton having aromaticity.
  • the above aromatic ring may or may not have a substituent.
  • condensed aromatic ring structures include isoindole ring, indole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, indazole ring, purine ring, thienopyrrole ring, pyrrolothiazole ring, pyrrolooxazole ring, quinoline.
  • the ring structure include a ring, an isoquinoline ring, a quinoxaline ring, an imidazopyridine ring, a perimidine ring, and a phenanthridine ring.
  • the condensed aromatic ring structure is not particularly limited as long as it is a skeleton having aromaticity.
  • the above condensed aromatic ring may or may not have a substituent.
  • An electron-withdrawing group is also called an electron-accepting group, and is an atomic group that attracts electrons from a substituted atomic group by an induced effect or a resonance effect in organic electron theory.
  • Examples of the electron withdrawing group include those having a positive value as the Hammett's rule substituent constant ( ⁇ p (para)).
  • the Hammett's rule substituent constant ( ⁇ p (para)) can be cited from the Chemical Handbook, Basic Revision 5 (II-380).
  • a phenyl group also has the example which takes the said positive value, a phenyl group is not contained in the electron withdrawing group in this invention.
  • electron withdrawing groups include, for example, -F ( ⁇ p: +0.06), -Cl ( ⁇ p: +0.23), -Br ( ⁇ p: +0.23), -I ( ⁇ p: +0.18) , -CO 2 R 10 ( ⁇ p: when R 10 is an ethyl group +0.45), -CONH 2 ( ⁇ p: +0.38), -COR 10 ( ⁇ p: when R 10 is a methyl group +0.49), —CF 3 ( ⁇ p: +0.50), —CN ( ⁇ p: +0.66), —SO 2 R 10 ( ⁇ p: +0.69 when R 10 is a methyl group), —NO 2 ( ⁇ p: +0.81) ) And the like.
  • R 10 represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted carbon number, It represents an alkyl group having 1 to 30 or a substituted or unsubstituted cycloalkyl group having 1 to 30 carbon atoms. Specific examples of these groups include the same examples as described above.
  • Preferred electron withdrawing groups include fluorine, fluorine-containing aryl groups, fluorine-containing heteroaryl groups, fluorine-containing alkyl groups, substituted or unsubstituted acyl groups, substituted or unsubstituted ester groups, substituted or unsubstituted amide groups.
  • the fluorine-containing aryl group is an aryl group containing a fluorine atom.
  • the fluorine-containing heteroaryl group is a heteroaryl group containing fluorine.
  • the fluorine-containing alkyl group is an alkyl group containing fluorine.
  • More preferable electron withdrawing groups include a fluorine-containing alkyl group, a substituted or unsubstituted acyl group, a substituted or unsubstituted ester group, or a cyano group. This is because these groups prevent concentration quenching and lead to the effect of improving the emission quantum yield. Among these, a cyano group is particularly preferable as the electron withdrawing group.
  • R 10 contained in the electron withdrawing group include a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms. And a substituted or unsubstituted cycloalkyl group having 1 to 30 carbon atoms. More preferred substituents (R 10 ) include substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms from the viewpoint of solubility.
  • examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a hexyl group, an isopropyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group.
  • an ethyl group is preferably used as the alkyl group.
  • the nitrogen atom forms a multiple bond with an adjacent atom, and the nitrogen atom is a high electron. Since it has a negative degree, the multiple bond has an electron withdrawing property. In this case, Xa and Xb have electron withdrawing properties.
  • the compound represented by the general formula (1) can prevent concentration quenching due to aggregation because R 1 and R 2 are a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. As a result, the compound represented by the general formula (1) can obtain a high fluorescence quantum yield. From the viewpoint of obtaining a higher fluorescence quantum yield, R 1 and R 2 are preferably a substituted or unsubstituted aryl group. Among the aryl groups, a phenyl group and a naphthyl group are particularly preferable examples.
  • R 1 and R 2 are substituted aryl groups or substituted heteroaryl groups, and the substitution thereof
  • the group is preferably a substituted or unsubstituted alkyl group or a substituted or unsubstituted alkoxy group.
  • the substituent is more preferably an alkyl group having 1 to 20 carbon atoms or an alkoxy group. From the viewpoint of compatibility with the solvent, the substituent is particularly preferably a branched alkyl group or alkoxy group.
  • R 3 to R 6 since at least one of R 3 to R 6 is a cyano group, the electron density in the molecule can be lowered, so that the reliability can be improved. From the viewpoint of further improving the reliability of the compound represented by the general formula (1), it is preferable that all of R 3 to R 6 are cyano groups.
  • the compound represented by the general formula (1) includes a compound represented by the following general formula (2), a compound represented by the general formula (3), a compound represented by the general formula (4), It is preferably any one of a compound represented by the formula (5), a compound represented by the general formula (6), or a compound represented by the general formula (7).
  • X a and X b are CR 7 or a nitrogen atom, and R 7 is an electron withdrawing group.
  • X 1 and X 2 may be the same or different and are a sulfur atom, an oxygen atom, a nitrogen atom or a phosphorus atom.
  • X 3 and X 4 may be the same or different and are a nitrogen atom or a phosphorus atom.
  • R 101 and R 102 may be the same or different and are a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
  • R 103 to R 106 may be the same or different, and are a cyano group, a halogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryl group And selected from the group consisting of substituted or unsubstituted heteroaryl groups. At least one of R 103 to R 106 is a cyano group.
  • R 107 to R 118 may be the same or different and each represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl Group, substituted or unsubstituted cycloalkenyl group, substituted or unsubstituted alkynyl group, hydroxyl group, thiol group, substituted or unsubstituted alkoxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted aryl ether group, substituted Or an unsubstituted arylthioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen, a cyano group, an aldehyde group, a
  • the ring structure formed between adjacent substituents means R 107 and R 108 , R 109 and R 110 in the above general formula (2), or R 111 to R 114 in the general formulas (3) to (7). And any two substituents selected from R 115 to R 118 (for example, R 111 and R 112 ) are bonded to each other to form a conjugated or non-conjugated condensed ring.
  • These condensed rings may contain at least one nitrogen atom, oxygen atom or sulfur atom in the ring structure, or may be further condensed with another ring.
  • the compound represented by the general formula (1) is a compound represented by the following general formula (8), a compound represented by the general formula (9), a compound represented by the general formula (10), or More preferably, it is one of the compounds represented by the general formula (11).
  • X a and X b are CR 7 or a nitrogen atom, and R 7 is an electron withdrawing group.
  • X 5 and X 6 may be the same or different and are a sulfur atom, an oxygen atom, a nitrogen atom or a phosphorus atom.
  • X 7 to X 10 may be the same or different and are a nitrogen atom or a phosphorus atom.
  • R 201 and R 202 may be the same or different and each represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
  • R 203 to R 206 may be the same or different and are each a cyano group, a halogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryl group And selected from the group consisting of substituted or unsubstituted heteroaryl groups. At least one of R 203 to R 206 is a cyano group.
  • R 207 to R 216 may be the same or different and are each a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl Group, substituted or unsubstituted cycloalkenyl group, substituted or unsubstituted alkynyl group, hydroxyl group, thiol group, substituted or unsubstituted alkoxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted aryl ether group, substituted Or an unsubstituted arylthioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen, a cyano group, an aldehyde group, a
  • R 209 to R 216 may be the same or different, and are a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group.
  • At least one of R 209 to R 216 is more preferably a ring structure formed between a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or an adjacent substituent.
  • at least one of R 209 to R 212 and at least one of R 213 to R 216 are formed between a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or an adjacent substituent. More preferably, the ring structure is
  • the compound represented by the general formula (1) includes a compound represented by the following general formula (12), a compound represented by the general formula (13), a compound represented by the general formula (14), The compound represented by the formula (15), the compound represented by the general formula (16), or the compound represented by the general formula (17) is particularly preferable.
  • R 301 to R 304 may be the same or different, and are a cyano group, a halogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted group. Selected from the group consisting of a alkynyl group, a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroaryl group. At least one of R 301 to R 304 is a cyano group.
  • R 305 to R 316 may be the same or different and are each a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl Group, substituted or unsubstituted cycloalkenyl group, substituted or unsubstituted alkynyl group, hydroxyl group, thiol group, substituted or unsubstituted alkoxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted aryl ether group, substituted Or an unsubstituted arylthioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen, a cyano group, an aldehyde group, a
  • R 309 to R 316 may be the same or different, and represent a hydrogen atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and an adjacent substituent. It is preferably selected from ring structures formed therebetween. In particular, at least one of R 309 to R 316 is more preferably a ring structure formed between a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or an adjacent substituent. .
  • the compound represented by the general formula (1) among the compounds represented by the general formulas (12) to (17), a compound represented by the general formula (12), represented by the general formula (13) More preferably, the compound represented by the general formula (14), the compound represented by the general formula (16), and the compound represented by the general formula (17) are represented by the general formula (14).
  • the compound, the compound represented by the general formula (16), and the compound represented by the general formula (17) are particularly preferable.
  • the compound represented by the general formula (1) can be synthesized, for example, by the following method. That is, after condensing an active methylene compound to the corresponding intermediate having a diketopyrrolopyrrole skeleton, the target compound is obtained by reacting the metal salt in the presence of a base.
  • a method of generating a carbon-carbon bond by using a coupling reaction between a halogenated derivative and a boronic acid or a boronic acid esterified derivative can be mentioned.
  • the present invention is not limited to this.
  • introducing an amino group or a carbazolyl group for example, there is a method of generating a carbon-nitrogen bond by using a coupling reaction between a halogenated derivative and an amine or a carbazole derivative under a metal catalyst such as palladium.
  • the present invention is not limited to this.
  • the compound represented by the general formula (1) preferably has a maximum light emission in a wavelength range of 700 nm or more.
  • the compound represented by the general formula (1) can emit near infrared light by having maximum light emission in a wavelength range of 700 nm or more.
  • the compound represented by the general formula (1) can be used as a sensing function material in biometric authentication.
  • the composition according to the embodiment of the present invention preferably includes a compound represented by the general formula (1) and a binder resin.
  • the content of the compound represented by the general formula (1) in this composition is the molar extinction coefficient of the compound, the fluorescence quantum yield and the absorption intensity at the excitation wavelength, and the thickness of the molded product such as a film to be produced.
  • it depends on the transmittance, it is usually 1.0 ⁇ 10 ⁇ 4 to 30 parts by weight, and 1.0 ⁇ 10 ⁇ 3 to 10 parts by weight with respect to 100 parts by weight of the binder resin. More preferably, it is 1.0 ⁇ 10 ⁇ 2 to 5 parts by weight.
  • Binder resin forms a continuous phase and may be any material that is excellent in molding processability, transparency, heat resistance, and the like.
  • binder resins include photocurable resist materials having reactive vinyl groups such as acrylic acid, methacrylic acid, polyvinyl cinnamate, and ring rubber, epoxy resins, silicone resins (silicone rubber, silicone gel, etc.
  • Organopolysiloxane cured products including crosslinked products
  • urea resins fluororesins
  • polycarbonate resins acrylic resins, urethane resins, melamine resins
  • polyvinyl resins polyamide resins
  • phenol resins polyvinyl alcohol resins
  • cellulose resins aliphatics
  • ester resin aromatic ester resin
  • aliphatic polyolefin resin aromatic polyolefin resin
  • thermoplastic resin is preferable because the molding process is easy. Furthermore, from the viewpoint of transparency and heat resistance, an aromatic ester resin, an epoxy resin, a silicone resin, an acrylic resin, or a mixture thereof can be suitably used.
  • the composition according to the embodiment of the present invention includes, as an additive, a dispersant or a leveling agent for stabilizing a coating film, You may contain adhesion assistants, such as a silane coupling agent for modification, etc. Further, this composition may contain inorganic particles such as silica particles and silicone fine particles as a component for suppressing precipitation of the compound represented by the general formula (1). Furthermore, the composition may contain light-resistant stabilizers such as light stabilizers, antioxidants, processing and heat stabilizers, UV absorbers and the like.
  • Examples of the light stabilizer include tertiary amines, catechol derivatives, and nickel compounds, but are not particularly limited. These light stabilizers may be used alone or in combination.
  • antioxidants examples include phenolic antioxidants such as 2,6-di-tert-butyl-p-cresol and 2,6-di-tert-butyl-4-ethylphenol. It is not particularly limited. These antioxidants may be used alone or in combination.
  • processing and heat stabilizer examples include phosphorus stabilizers such as tributyl phosphite, tricyclohexyl phosphite, triethylphosphine, and diphenylbutylphosphine, but are not particularly limited. Moreover, these stabilizers may be used alone or in combination.
  • Examples of the light resistance stabilizer include 2- (5-methyl-2-hydroxyphenyl) benzotriazole, 2- [2-hydroxy-3,5-bis ( ⁇ , ⁇ -dimethylbenzyl) phenyl] -2H- Although benzotriazoles, such as benzotriazole, can be mentioned, it is not specifically limited. Moreover, these light resistance stabilizers may be used alone or in combination.
  • composition according to the embodiment of the present invention includes fine particles such as fumed silica, glass powder, and quartz powder, titanium oxide, zirconia oxide, and titanic acid as necessary, as long as the effects of the present invention are not impaired.
  • You may contain inorganic fillers, such as barium and a zinc oxide, a pigment, a flame retardant, a heat-resistant agent.
  • the content of these additives includes the molar extinction coefficient of the compound, the fluorescence quantum yield and the absorption intensity at the excitation wavelength, and the thickness and transmission of a molded article such as a film to be produced. Although it depends on the ratio, it is usually preferably 1.0 ⁇ 10 ⁇ 3 parts by weight or more and 30 parts by weight or less with respect to 100 parts by weight of the compound represented by the general formula (1).
  • the content of these additives is more preferably 1.0 ⁇ 10 ⁇ 2 parts by weight to 15 parts by weight with respect to 100 parts by weight of the compound represented by the general formula (1). It is particularly preferably 1.0 ⁇ 10 ⁇ 1 part by weight or more and 10 parts by weight or less.
  • the composition according to the embodiment of the present invention may contain a solvent.
  • the solvent is not particularly limited as long as it can adjust the viscosity of the composition in a fluid state and does not excessively affect the light emission and reliability of the luminescent material.
  • examples of such solvents include toluene, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, hexane, acetone, isopropanol, terpineol, texanol, methyl cellosolve, butyl carbitol, butyl carbitol acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate. , Dimethoxyethane, tetrahydrofuran, dioxane, ethyl acetate and the like. These solvents can be used alone, but it is preferable to use a mixture of two or more.
  • the boiling point of each solvent is preferably 150 ° C. or less, and the difference between the highest and lowest of the boiling points is preferably 50 ° C. or less.
  • the difference in boiling points is more preferably in the range from 20 ° C to 50 ° C. *
  • ⁇ Method for producing composition> an example of the manufacturing method of the composition which concerns on embodiment of this invention is demonstrated.
  • a predetermined amount of the compound represented by the general formula (1), a binder resin, a solvent, and the like is mixed.
  • the mixture is homogeneously mixed and dispersed with a homogenizer, a self-revolving stirrer, a three-roller, a ball mill, a planetary ball mill, a bead mill or the like.
  • a composition is obtained.
  • Defoaming is preferably carried out under vacuum or reduced pressure conditions after mixing or dispersing.
  • a specific component may be mixed in advance or a process such as aging may be performed. It is also possible to remove the solvent with an evaporator to obtain a desired solid content concentration.
  • the molded body according to the embodiment of the present invention is a molded body molded using the composition according to the present invention.
  • the molded body include a thin film, a film, a sheet, an injection molded product, an extrusion molded product, a vacuum / pressure air molded product, a blow molded product, and a composite with another material.
  • This molded body is preferably a thin film, a sheet, or a film from the viewpoint of easily absorbing excitation light.
  • the molded body according to the embodiment of the present invention may be formed by desolvation of the composition used in the composition, or the composition used in the composition may be cured by heating, light irradiation, or the like. It may be molded.
  • a light emitting device includes a light source and a near infrared light conversion unit.
  • the near-infrared light conversion unit includes the molded body according to the present invention.
  • Such a light-emitting device can be configured by combining a near-infrared light conversion unit including the molded body and a light source.
  • any light source can be used as long as it emits light in a wavelength region that can be absorbed by the compound represented by the general formula (1).
  • a light source include a fluorescent light source such as a hot cathode tube, a cold cathode tube, and an inorganic EL, an organic electroluminescence element light source, an LED, and an incandescent light source. Any of these light sources can be used in principle for the light emitting device of the present invention.
  • organic electroluminescence element light sources and LEDs can be cited as suitable light sources.
  • the light source may have one type of emission peak or may have two or more types of emission peaks. In the light emitting device of the present invention, a plurality of excitation light sources having different types of emission peaks can be used in any combination.
  • the near-infrared light conversion unit including the molded body according to the embodiment of the present invention may be subjected to pattern processing as necessary.
  • the pattern processing method include various printing methods such as photolithography, screen printing, and inkjet.
  • FIG. 1 is a schematic cross-sectional view showing a configuration of a first example of a light emitting device according to an embodiment of the present invention.
  • FIG. 2 is a schematic cross-sectional view showing the configuration of the second example of the light emitting device according to the embodiment of the invention.
  • FIG. 3 is a schematic cross-sectional view showing the configuration of the third example of the light emitting device according to the embodiment of the invention.
  • FIG. 4 is a schematic cross-sectional view showing the configuration of the fourth example of the light emitting device according to the embodiment of the invention.
  • FIGS. 5 is a schematic cross-sectional view showing the configuration of the fifth example of the light-emitting device according to the embodiment of the present invention.
  • the same components are denoted by the same reference numerals.
  • the light emitting device according to the embodiment of the present invention is not limited to the one having the structure illustrated in FIGS.
  • the light emitting device 15A of the first example includes a light source 10 and a near-infrared light conversion unit 11 including the molded body of the present invention.
  • a typical structural example of the light emitting device 15A as shown in FIG. 1, there is a structure of a laminated body in which a near infrared light conversion unit 11 is laminated on the light source 10.
  • the light emitting device 15 ⁇ / b> B of the second example includes the light source 10, the near infrared light conversion unit 11, and the base material 12 described above.
  • the light emitting device 15B As a typical structural example of the light emitting device 15B, as shown in FIG. 2, there is a structure of a laminated body in which a base material 12 and a near infrared light conversion unit 11 are laminated in this order on a light source 10.
  • the light emitting device 15 ⁇ / b> C of the third example includes the light source 10, the near infrared light conversion unit 11, and the base material 12 described above.
  • the light emitting device 15C As a typical structural example of the light emitting device 15C, as shown in FIG. 3, there is a structure of a laminated body in which a near-infrared light conversion unit 11 and a base material 12 are laminated in this order on a light source 10.
  • the light emitting device 15 ⁇ / b> D of the fourth example includes the light source 10 and the near infrared light conversion unit 11 described above, and a plurality of base materials 12.
  • the light emitting device 15D As a typical structural example of the light emitting device 15D, as shown in FIG. 4, there is a structure of a laminated body in which a near infrared light conversion unit 11 sandwiched between a plurality of base materials 12 is laminated on a light source 10. It is done.
  • the light emitting device 15E of the fifth example includes the light source 10, the near-infrared light conversion unit 11, the plurality of base materials 12, and the plurality of barrier films 13.
  • the barrier film 13 is for preventing deterioration of the compound (specifically, the compound represented by the general formula (1)) contained in the near-infrared light conversion unit 11 due to oxygen, moisture, or heat.
  • a near infrared light conversion unit 11 sandwiched between a plurality of barrier films 13 and a plurality of base materials 12 on a light source 10.
  • a known metal, film, glass, ceramic, paper, or the like can be used without particular limitation.
  • metal including aluminum alloy), zinc, copper, iron, and other metal plates and foils, cellulose acetate, polyethylene terephthalate (PET), polyethylene, polyester, polyamide, polyimide, polyphenylene sulfide, polystyrene , Polypropylene, polycarbonate, polyvinyl acetal, aramid, silicone, polyolefin, thermoplastic fluororesin, plastic film such as tetrafluoroethylene and ethylene copolymer (ETFE), ⁇ -polyolefin resin, polycaprolactone resin, acrylic resin, silicone Plastic film made of a resin and a copolymer resin of these with ethylene, paper laminated with the plastic, or coated with the plastic Paper was, said metal laminate
  • glass and resin films are preferably used because of the transmittance and the ease of molding of the near infrared light conversion part (for example, the near infrared light conversion part 11 shown in FIGS. 1 to 5). Moreover, a film with high strength is preferable so that there is no fear of breakage when handling a film-like substrate.
  • Resin films are preferred in terms of their required characteristics and economy, and among these, plastic films selected from the group consisting of PET, polyphenylene sulfide, polycarbonate, and polypropylene are preferred in terms of economy and handleability.
  • a polyimide film is preferable at a heat resistant surface.
  • the surface of the base material may be subjected to a release treatment in advance.
  • the thickness of the substrate is not particularly limited, but the lower limit is preferably 25 ⁇ m or more, and more preferably 38 ⁇ m or more. Moreover, as an upper limit, 5000 micrometers or less are preferable and 3000 micrometers or less are more preferable.
  • the barrier film (for example, the barrier film 13 shown in FIG. 5) applied to the light emitting device of the present invention is appropriately used in the case of improving the gas barrier property with respect to the near infrared light conversion part.
  • the barrier film include inorganic oxides such as silicon oxide, aluminum oxide, titanium oxide, tantalum oxide, zinc oxide, tin oxide, indium oxide, yttrium oxide, and magnesium oxide, silicon nitride, aluminum nitride, titanium nitride, Inorganic nitrides such as silicon carbonitride, or mixtures thereof, or metal oxide thin films and metal nitride thin films obtained by adding other elements to these, or polyvinylidene chloride, acrylic resins, silicon resins, melamine resins, Mention may be made of films made of various resins such as urethane resins, fluorine resins, polyvinyl alcohol resins such as saponified vinyl acetate.
  • Examples of the film having a barrier function against moisture include polyethylene, polypropylene, nylon, polyvinylidene chloride, a copolymer of vinylidene chloride and vinyl chloride, a copolymer of vinylidene chloride and acrylonitrile, and a fluorine resin. And membranes made of various resins such as polyvinyl alcohol resins such as saponified vinyl acetate.
  • the barrier film may be provided on both surfaces of the near-infrared light conversion unit 11 as in the barrier film 13 shown in FIG. 5, for example, or only on one surface of the near-infrared light conversion unit 11. It may be provided.
  • an auxiliary layer having a function, a visible light cut function, an ultraviolet ray cut function, a polarization function, and a toning function may be further provided.
  • reaction solution was concentrated and dried, and then the concentrate was extracted with toluene and washed with pure water. The organic layer was separated from the obtained solution, dried over magnesium sulfate, filtered, and the solvent was removed. Hexane (200 mL) was added to the resulting concentrate, stirred for 1 hour, dried, and purified by silica gel chromatography to give 4- (3,7-dimethyloctyloxy) benzonitrile (45 g). .
  • boron trifluoride diethyl etherate (0) was added to a mixture of the above compound 1a (1.0 g), trimethylsilyl cyanide (1.8 g), and dehydrated dichloromethane (60 mL) in a flask under a nitrogen stream. .3 g) was added and stirred at room temperature for 1 hour. Next, pure water (60 mL) was added to the reaction solution, stirred for 30 minutes, and then the solution was extracted with dichloromethane. The resulting solution was dried over magnesium sulfate and then concentrated to dryness. The obtained concentrate was purified by silica gel chromatography to obtain compound 1A (0.8 g).
  • Example 1 Evaluation of the optical characteristics of Example 1 in the present invention will be described.
  • 500 parts by weight of chlorobenzene and 0.5 part by weight of compound 1A as a light emitting material were mixed with 100 parts by weight of a polyester resin as a binder resin, and then stirred at 300 rpm for 3 hours. The thing was manufactured.
  • Example 1 which is an example of a molded body applied to the near-infrared light conversion part of the light-emitting device according to the present invention, the optical characteristics were evaluated using such a film.
  • Example 1 when the light emission characteristics of this film were evaluated using Quantaurus-QY manufactured by Hamamatsu Photonics, light emission in the near infrared region having a peak wavelength of 827 nm was obtained. The full width at half maximum of the emission spectrum at this peak wavelength was 110 nm. The emission intensity of Example 1 was 1.05, expressed by a relative value when the emission intensity in Conventional Comparative Example 2 described later was 1.00. In addition, when UV light having a wavelength of 365 nm was continuously irradiated at room temperature, the time until the light absorption characteristics of the film decreased by 5% (this is an index of “photoreliability”) was 600 hours. It was. The evaluation results of Example 1 are summarized in Table 1 described later.
  • Example 2 to 9 and Comparative Examples 1 to 3 Evaluation of optical characteristics of Examples 2 to 9 in the present invention and Comparative Examples 1 to 3 with respect to the present invention will be described.
  • films were prepared and optical characteristics were evaluated in the same manner as in Example 1 except that the compounds described in Table 1 were used as the light emitting materials.
  • Compound R1 as the light emitting material of Comparative Example 1 is a compound shown below.
  • the evaluation results of Examples 2 to 9 and Comparative Examples 1 to 3 are shown in Table 1.
  • each film of Examples 1 to 9 had higher optical reliability than Comparative Examples 1 to 3.
  • the peak wavelength of light emission is in the near-infrared light emission wavelength region (for example, a region of 700 nm or more) and the light emission intensity is relatively Higher ones, that is, higher ones that emit near-infrared light are preferred.
  • the peak wavelength of near-infrared light emission is preferably a longer wavelength. Therefore, each of the films of Examples 1 to 9 has a higher near-infrared emission efficiency than Comparative Examples 1 to 3. From the above, it was confirmed that the films of Examples 1 to 9 had both high emission efficiency of near-infrared light emission and high light reliability.
  • Example 2 is the best from the viewpoint that the peak wavelength of near-infrared emission can be made longer, and Example 6 is followed by Example 6. It is good.
  • Example 7, Example 8, Example 1, Example 5, Example 3, Example 9, and Example 4 are favorable in this order.
  • Examples 2, 7, and 8 are relatively good from the viewpoint of easily synthesizing a compound as a light emitting material.
  • Example 6, Example 1, Example 5, Example 3, Example 9, and Example 4 are favorable in this order.
  • Example 2 is the best from both the viewpoints of increasing the peak wavelength of near-infrared light emission and ease of synthesis of the light-emitting material.
  • Compound 2A used for the synthesis of the film of Example 2 is an example of a compound represented by General Formula (14).
  • the compound according to the present invention the composition containing the compound, the molded body using the compound, and the light-emitting device are suitable for achieving both high emission efficiency of near-infrared light emission and high reliability.

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Abstract

L'invention concerne un composé représenté par la formule générale (1). (dans la formule générale (1), Ar1 et Ar2 peuvent être identiques ou différents, et sont soit un cycle aromatique à 5 chaînons, un cycle aromatique à 6 chaînons, soit un cycle aromatique fusionné dans lequel deux ou plusieurs cycles à cinq chaînons et/ou des cycles à 6 chaînons ont été fusionnés, les cycles aromatiques et le cycle aromatique fusionné peuvent avoir un groupe substituant, Xa et Xb sont soit CR7 soit un atome d'azote, et R7 représente un groupe électro-attracteur, R1 et R2 peuvent être identiques ou différents, et sont soit un groupe aryle substitué ou non substitué, soit un groupe hétéroaryle substitué ou non substitué, R3-R6 peuvent être identiques ou différents, et sont choisis dans le groupe constitué par : des groupes cyano; des groupes alkyle substitués ou non substitués; des groupes alcoxy substitués ou non substitués; des groupes alcynyle substitués ou non substitués; des groupes aryle substitués ou non substitués; et des groupes hétéroaryle substitués ou non substitués, de plus, au moins l'un parmi R3-R6 représente un groupe cyano.)
PCT/JP2019/002348 2018-01-31 2019-01-24 Composé, composition le contenant, corps moulé et dispositif électroluminescent l'utilisant Ceased WO2019151121A1 (fr)

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Cited By (3)

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Publication number Priority date Publication date Assignee Title
CN111440208A (zh) * 2020-04-30 2020-07-24 上海天马有机发光显示技术有限公司 化合物、显示面板和显示装置
WO2022044589A1 (fr) * 2020-08-31 2022-03-03 東レ株式会社 Élément de réception/émission de lumière, et dispositif électronique et dispositif de détection biologique l'utilisant
JP2024500537A (ja) * 2020-12-28 2024-01-09 サントル ナシオナル ドゥ ラ ルシェルシェ サイアンティフィク ピロロピロールシアニンの新規誘導体及びその使用

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Publication number Priority date Publication date Assignee Title
CN111440208A (zh) * 2020-04-30 2020-07-24 上海天马有机发光显示技术有限公司 化合物、显示面板和显示装置
CN111440208B (zh) * 2020-04-30 2023-02-24 武汉天马微电子有限公司 化合物、显示面板和显示装置
WO2022044589A1 (fr) * 2020-08-31 2022-03-03 東レ株式会社 Élément de réception/émission de lumière, et dispositif électronique et dispositif de détection biologique l'utilisant
JPWO2022044589A1 (fr) * 2020-08-31 2022-03-03
JP7639687B2 (ja) 2020-08-31 2025-03-05 東レ株式会社 受発光素子、これを用いた電子デバイスおよび生体センシングデバイス
JP2024500537A (ja) * 2020-12-28 2024-01-09 サントル ナシオナル ドゥ ラ ルシェルシェ サイアンティフィク ピロロピロールシアニンの新規誘導体及びその使用
JP7765478B2 (ja) 2020-12-28 2025-11-06 サントル ナシオナル ドゥ ラ ルシェルシェ サイアンティフィク ピロロピロールシアニンの新規誘導体及びその使用

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