WO2019112369A1 - Nitrogen-containing compound, color conversion film comprising same, and backlight unit and display device each comprising same - Google Patents

Nitrogen-containing compound, color conversion film comprising same, and backlight unit and display device each comprising same Download PDF

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Publication number
WO2019112369A1
WO2019112369A1 PCT/KR2018/015522 KR2018015522W WO2019112369A1 WO 2019112369 A1 WO2019112369 A1 WO 2019112369A1 KR 2018015522 W KR2018015522 W KR 2018015522W WO 2019112369 A1 WO2019112369 A1 WO 2019112369A1
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Prior art keywords
group
substituted
unsubstituted
compound
same
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PCT/KR2018/015522
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French (fr)
Korean (ko)
Inventor
손선경
이미림
이호용
송철준
김지선
유형욱
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주식회사 엘지화학
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Priority claimed from KR1020180156173A external-priority patent/KR102141741B1/en
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to US16/603,168 priority Critical patent/US11498931B2/en
Priority to JP2019551526A priority patent/JP6896970B2/en
Priority to CN201880020163.2A priority patent/CN110520429B/en
Publication of WO2019112369A1 publication Critical patent/WO2019112369A1/en

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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/55Boron-containing compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00Compounds containing elements of Groups 3 or 13 of the Periodic System
    • C07F5/02Boron compounds
    • GPHYSICS
    • G02OPTICS
    • G02FOPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333Constructional arrangements; Manufacturing methods
    • G02F1/1335Structural association of cells with optical devices, e.g. polarisers or reflectors

Definitions

  • the present invention relates to a nitrogen-containing compound, a color conversion film comprising the same, a backlight unit, and a display device.
  • LEDs Conventional light emitting diodes
  • LEDs are obtained by mixing a green phosphor and a red phosphor in a blue light emitting diode or by mixing a yellow phosphor and a blue-green phosphor in a UV light emitting diode.
  • a method is difficult to control the color and thus has poor color rendering properties. Therefore, the color reproduction rate drops.
  • quantum dots have safety problems, and other quantum dots are less efficient than cadmium-based ones.
  • the quantum dots have a disadvantage that their stability against oxygen and water is poor and their performance remarkably decreases when they are aggregated.
  • the present specification provides a nitrogen-containing compound, a color conversion film containing the same, a backlight unit, and a display device.
  • L1 and L2 are the same or different and are each independently a substituted or unsubstituted arylene group
  • L10 to L13 are the same or different and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
  • R1 to R4 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted fluoroalkyl group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted allyloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted
  • At least one of R 1 to R 4 is represented by the following formula (2)
  • the groups not bonded to the formula (1) among R10 to R19 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted fluoroalkyl group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted allyloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group;
  • X1 and X2 are the same or different from each other, and each independently represents a halogen group; A nitrile group; -CO 2 R ""; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted hydrocarbon ring group, or X 1 and X 2 are bonded to each other to form a substituted or unsubstituted ring,
  • R "" is a substituted or unsubstituted alkyl group; A substituted or unsubstituted fluoroalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted hydrocarbon ring group.
  • a resin matrix a resin matrix; And a color conversion film containing the compound represented by the formula (1) dispersed in the resin matrix.
  • a backlight unit including the color conversion film.
  • a display device including the backlight unit.
  • FIG. 1 is a schematic diagram showing a color conversion film according to an embodiment of the present invention applied to a backlight;
  • a member when a member is located on another member, it includes not only the case where the member is in contact with the other member but also the case where another member exists between the two members.
  • substituted means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, , Two or more substituents may be the same as or different from each other.
  • substituted or unsubstituted A halogen group; A nitrile group; A nitro group; An amino group; Carbonyl group; Carboxy group (-COOH); Ether group; An ester group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted fluoroalkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted fluoroalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or that at least two of the substituents
  • a substituent to which at least two substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.
  • Quot refers to a moiety bonded to another substituent or bond.
  • the halogen group may be fluorine, chlorine, bromine or iodine.
  • the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 30 carbon atoms.
  • (C ( O) R 100 ) R 101 or a compound having the following structure: wherein R 100 and R 101 are the same or different from each other and each independently represents hydrogen, A substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group.
  • the amide group may be substituted with nitrogen of the amide group by hydrogen, a straight chain, branched chain or cyclic alkyl group of 1 to 30 carbon atoms or an aryl group of 6 to 30 carbon atoms.
  • -C ( O) NR 102 R 103 or Wherein R 102 and R 103 are the same or different from each other and each independently represents hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group
  • the present invention is not limited thereto, and the present invention is not limited thereto.
  • the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 30 carbon atoms.
  • R 104 is hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl
  • the present invention is not limited thereto.
  • the ether group is a straight chain, branched or cyclic alkyl group having 1 to 25 carbon atoms in which the ether is oxygen; Or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • the ester group means that the oxygen in the ester group is a straight, branched or cyclic alkyl group having 1 to 25 carbon atoms; An alkenyl group; A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a heterocyclic group having 2 to 30 carbon atoms.
  • R 105 and R 106 are the same or different from each other and each independently represents hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl
  • R 105 and R 106 are the same or different from each other and each independently represents hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl
  • the present invention is not limited thereto.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, Cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methyl
  • the cycloalkyl group is not particularly limited, but is preferably a group having 3 to 30 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, isobutyl, sec-butyl, It is not.
  • the fluoroalkyl group is not particularly limited, but preferably has 1 to 10 carbon atoms, and specifically includes, but is not limited to, a trifluoromethyl group, a perfluoroethyl group, and the like.
  • the alkylthio device is not particularly limited, but preferably has 1 to 10 carbon atoms, and specifically includes methylthio, ethylthio, and the like, but is not limited thereto.
  • the alkoxy group may be linear, branched or cyclic.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.
  • the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.
  • the alkynyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably from 2 to 30. Specific examples include, but are not limited to, alkynyl groups such as ethynyl, propynyl, 2-methyl-2-propynyl, 2-butynyl, 2-pentynyl and the like.
  • the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group,
  • the present invention is not limited thereto.
  • the boron group may be -BR 107 R 108 R 109 , wherein R 107 , R 108 and R 109 are the same or different and each independently hydrogen; heavy hydrogen; halogen; A nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • the phosphine oxide group specifically includes a diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like, but is not limited thereto.
  • the amine group is -NH 2 ; Monoalkylamine groups; A dialkylamine group; N-alkylarylamine groups; Monoarylamine groups; A diarylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, a monoheteroarylamine group, and a diheteroarylamine group.
  • the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • amine group examples include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; An N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; An N-biphenyl phenanthrenyl amine group; N-phenylfluorenylamine group; An N-biphenyl phenanthrenyl amine group; N-phenylfluorenylamine group; An N-phenyltriphenylamine group; N-phenanthrenyl fluorenyl
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group.
  • the arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.
  • the aryl group in the arylamine group may be selected from the examples of the aryl group described above.
  • the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
  • the aryl group is a monocyclic aryl group
  • the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms.
  • Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.
  • the aryl group is a polycyclic aryl group
  • the number of carbon atoms is not particularly limited. And preferably 10 to 30 carbon atoms.
  • Specific examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a triphenyl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.
  • the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
  • the aryl group of the aryloxy group is the same as that of the above-mentioned aryl group.
  • Specific examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6- trimethylphenoxy group, a p- Naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group and 9-phenanthryloxy group and the arylthioxy group and the arylthioxy group includes phenylthio group, 2- Methylphenylthio group, 4-tert-butylphenylthio group and the like, and examples of the arylsulfoxy group include a
  • the heterocyclic group includes at least one non-carbon atom or hetero atom, and specifically, the hetero atom may include at least one atom selected from the group consisting of O, N, Se and S, and the like.
  • the number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic.
  • heterocyclic group examples include a thiophene group, a furanyl group, a pyrrolyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, , A pyrazine group, a pyrazine group, a quinoline group, a quinazoline group, a quinoxaline group, a phthalazine group, a pyridopyrimidine group, a pyridopyrazine group, a pyrazinopyrazine group, an isoquinoline group, An oxazolyl group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofur
  • the heterocyclic group may be monocyclic or polycyclic, and may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and examples of the heterocyclic group may be selected.
  • the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from the examples of the cycloalkyl group or the aryl group except the univalent hydrocarbon ring, and the aromatic and aliphatic condensed rings
  • the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from the examples of the cycloalkyl group or the aryl group except the univalent hydrocarbon ring, and the aromatic and aliphatic condensed rings
  • a 1,2,3,4-tetrahydronaphthalene group ( ), 2,3-dihydro-1H-indene group ( ) But the present invention is not limited thereto.
  • an arylene group means a group having two bonding positions in an aryl group, that is, a divalent group.
  • the description of the aryl group described above can be applied except that each of these is 2 groups.
  • the heteroarylene group means that the heteroaryl group has two bonding positions, that is, divalent.
  • the description of the above-mentioned heteroaryl groups can be applied, except that they are each 2 groups.
  • adjacent means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom .
  • two substituents substituted in the benzene ring to the ortho position and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.
  • adjacent groups are bonded to each other to form a ring
  • substituent group means a substituted or unsubstituted hydrocarbon ring bonded to adjacent groups to form a ring; Or a substituted or unsubstituted heterocycle.
  • At least one of R 1 and R 2 and at least one of R 3 and R 4 is Formula 2.
  • R 1 and R 3 are the same as those in Formula 2, and R 2 and R 4 are the same or different and each independently hydrogen; A halogen group; A nitrile group; A nitro group; An ester group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted fluoroalkyl group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or a substituted or unsubstituted hydrocarbon ring group.
  • the R < 200 &gt to be.
  • the 'substituted or unsubstituted' in R 2 and R 4 is an aryl group; An alkyl group; An alkoxy group; A halogen group; Silyl group; Or substituted or unsubstituted with a nitrile group.
  • the 'substituted or unsubstituted' in R 2 and R 4 is a phenyl group; Methoxy group; Methyl group; An ethyl group; Butyl group; F; A trimethylsilyl group; Or substituted or unsubstituted with a nitrile group.
  • At least two of R 1 to R 4 are represented by the formula (2).
  • R 1 to R 4 are as defined in the above formula (2).
  • Formula 2 according to the present invention has a molecular structure with a high molar extinction coefficient.
  • the absorbance against blue light increases.
  • absorption at 450 nm is increased, so that when the number of molecules introduced into the molecule increases, absorption toward 450 nm increases, green fluorescence emitted in the molecule increases, The probability of color conversion is increased.
  • the efficiency of the color conversion film is increased.
  • R1 to R4 are all the above-described Formula 2, a compound having a high color conversion rate can be obtained, and the color conversion rate can be further increased according to the type of the substituent to be substituted in Formula 2 above.
  • L 1 and L 2 are the same or different and each independently represents a substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted anthracenylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted quaterphenylene group; Or a substituted or unsubstituted triphenylene group.
  • L 1 and L 2 are the same or different and each independently represents a substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.
  • L 1 and L 2 are the same or different and each independently represent a phenylene group substituted or unsubstituted with an alkyl group, an alkoxy group, or a halogen group; Or a biphenylene group substituted or unsubstituted with an alkyl group, an alkoxy group or a halogen group.
  • L 1 and L 2 are the same or different and each independently a substituted or unsubstituted phenylene group.
  • L 1 and L 2 are the same or different and each independently represent a phenylene group substituted or unsubstituted with an alkyl group, an alkoxy group, or a halogen group.
  • the groups not bonded to the formula (1) among R10 to R19 are the same or different and each independently hydrogen; A nitrile group; A nitro group; An ester group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted fluoroalkyl group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted hydrocarbon ring group.
  • the 'substituted or unsubstituted' fluoroalkyl group in the group not bonded to the formula (1) among R10 to R19 is a fluoroalkyl group; Silyl group; A halogen group; An aryl group; A heteroaryl group; An ester group; A nitrile group; An alkoxy group; A nitro group; An alkyl group; An aryloxy group; An arylamine group; A cycloalkyl group; And a substituent represented by the general formula (2).
  • the 'substituted or unsubstituted' group in the group not bonded to the formula (1) among R10 to R19 is a trifluoromethyl group; Triphenylsilyl groups; A trimethylsilyl group; Triethylsilyl group; F; A phenyl group; Naphthyl group; A fluorenyl group; Furan group; Thiophene group; A dibenzofurane group; A dibenzothiophene group; Carbazole group; A phenoxathine group; Benzoxazole group; Chromen group; -COOR201; A nitrile group; An alkoxy group; A nitro group; An alkyl group; Phenoxy group; Diphenylamine group; A cyclohexyl group; And a substituent represented by the general formula (2).
  • X1 and X2 are the same or different and each independently represents a halogen group; Nitrile equipment; -CO 2 R ""; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted C2-C20 alkynyl; A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms; A substituted or unsubstituted C1-C20 alkoxy group; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • X1 and X2 are the same or different and are each independently F; A nitrile group; -CO 2 R ""; Methyl group; Hexyl group; A phenoxy group substituted with a nitro group or a propyl group; Methoxy group; Ethoxy group; A phenyl group substituted or unsubstituted with F, an ethoxy group or a propyl group; A dimethylfluorenyl group; Thiophene group; or to be.
  • R "" represents a substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted trifluoromethyl group; A substituted or unsubstituted perfluoropropyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted methoxy group; A substituted or unsubstituted dihydrobenzoisoquinoline group; Or a substituted or unsubstituted chlorenone group.
  • X1 and X2 are the same or different and are each independently F; A nitrile group; -CO 2 R ""; Methyl group; Hexyl group; A phenoxy group substituted with a nitro group or a propyl group; Methoxy group; Ethoxy group; A phenyl group substituted or unsubstituted with F, an ethoxy group or a propyl group; A dimethylfluorenyl group; Thiophene group; or Quot; is a substituted or unsubstituted perfluoropropyl group; Or a substituted or unsubstituted chlorenone group.
  • X1 and X2 are the same or different and are each independently F; A nitrile group; -CO 2 R ""; Methyl group; Hexyl group; A phenoxy group substituted with a nitro group or a propyl group; Methoxy group; Ethoxy group; A phenyl group substituted or unsubstituted with F, an ethoxy group or a propyl group; A dimethylfluorenyl group; Thiophene group; or Quot; is a perfluoropropyl group; Or a chlorenone group substituted or unsubstituted with a ketone group.
  • X1 and X2 are the same or different and are F or a nitrile group.
  • X1 and X2 are F.
  • the formula (2) is represented by any one of the following formulas (2-1) to (2-3).
  • R20 to R22 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted fluoroalkyl group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted allyloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group;
  • a to c are an integer of 0 to 4, and when a to c are two or more, the substituents in parentheses are the same or different from each other.
  • the compound of Formula 1 is selected from the following structural formulas.
  • the compound according to one embodiment of the present application can be produced by a production method described below.
  • the compound of Formula 1 may be prepared as shown in Reaction Scheme 1 below.
  • Substituent groups may be attached by methods known in the art, and the type, position or number of substituent groups may be varied according to techniques known in the art.
  • bromophenylacetonitrile derivative of the above reaction scheme a derivative such as bromonaphthalenyl acetate nitrile, bromoanthraceneacetonitrile, or a derivative of bromo phenylacetonitrile, which is substituted with R200 to R204, Can be prepared, and the kind, position and number of substituent groups can be changed according to techniques known in the art.
  • the compound of the present invention can be obtained by substituting the compound obtained in Reaction Scheme 1 with an amine compound substituted with azabodipyr at the Br position, and the position of the bromine of bromophenylacetonitrile of Scheme 1, Can be used to prepare the compounds of the present invention.
  • a resin matrix comprising the compound represented by the general formula (1) dispersed in the resin matrix.
  • the content of the compound represented by the formula (1) in the color conversion film may be in the range of 0.001 to 10% by weight.
  • the color conversion film may contain one kind or two or more kinds of the compounds represented by the above formula (1).
  • the color conversion film may further include a fluorescent substance in addition to the compound represented by Formula 1.
  • the color conversion film preferably includes both a green light emitting fluorescent material and a red light emitting fluorescent material.
  • the color conversion film may include only a red light emitting fluorescent material.
  • the present invention is not limited thereto.
  • the color conversion film may include only a red light emitting compound.
  • the color conversion film may include only a green light-emitting compound.
  • the color conversion film comprises a resin matrix; And a further layer containing a light-emitting compound dispersed in the resin matrix and having a wavelength different from that of the compound represented by the general formula (1).
  • the compound emitting light having a wavelength different from that of the compound represented by the formula (1) may also be a compound represented by the formula (1) or a known fluorescent material.
  • the material of the resin matrix is preferably a thermoplastic polymer or a thermosetting polymer.
  • examples of the material of the resin matrix include poly (meth) acrylate, polycarbonate (PC), polystyrene (PS), polyarylene (PAR), polyurethane (TPU ), Styrene-acrylonitrile series (SAN), polyvinylidene fluoride series (PVDF), and modified polyvinylidene fluoride series (modified-PVDF).
  • the color conversion film according to the above-described embodiment further includes light diffusing particles.
  • the adhesion process can be omitted as compared with the use of a separate optical acid film, .
  • resin matrices and particles having a high refractive index can be used.
  • Polymer particles including polystyrene, polycarbonate, polymethylmethacrylate, acrylic, methylmethacrylate, styrene, melamine resin, formaldehyde resin, or melamine and formaldehyde resin, or any suitable combination thereof may be used .
  • the particle size of the light-diffusing particles may be in the range of 0.1 micrometer to 5 micrometers, for example, in the range of 0.3 micrometer to 1 micrometer.
  • the content of the light-diffusing particles may be determined as necessary, and may be, for example, within a range of about 1 to 30 parts by weight based on 100 parts by weight of the resin matrix.
  • the color conversion film according to the above-described embodiment may have a thickness of 2 micrometers to 200 micrometers.
  • the color conversion film can exhibit high luminance even at a thin thickness of 2 to 20 micrometers. This is because the content of the fluorescent substance molecules contained in the unit volume is higher than the quantum dots.
  • the color conversion film according to the above-described embodiments may have a substrate on one side thereof.
  • This substrate may serve as a support in the production of the color conversion film.
  • the kind of the substrate is not particularly limited and is not limited to the material and thickness as long as it is transparent and can function as the support.
  • transparent means that the visible light transmittance is 70% or more.
  • a PET film may be used as the substrate.
  • the above-mentioned color conversion film can be produced by coating a resin solution in which the compound represented by the formula (1) has been dissolved on a substrate and drying or extruding the compound represented by the formula (1) together with the resin to form a film.
  • the compound represented by the above-mentioned formula (1) is dissolved in the resin solution, the compound represented by the formula (1) is homogeneously distributed in the solution. This is different from the manufacturing process of a quantum dot film requiring a separate dispersion process.
  • the resin solution in which the compound represented by Formula 1 is dissolved is not particularly limited as long as the compound represented by Formula 1 is dissolved in the solution.
  • the resin solution in which the compound represented by Formula 1 is dissolved may be prepared by preparing a first solution by dissolving the compound represented by Formula 1 in a solvent, dissolving the resin in a solvent to prepare a second solution, And then mixing the solution and the second solution.
  • the present invention is not limited to this, and a method of dissolving the compound represented by Chemical Formula 1 and a resin simultaneously in a solvent to dissolve the compound represented by Chemical Formula 1 and dissolving the compound represented by Chemical Formula 1 in a solvent followed by dissolving the resin by dissolving the resin in a solvent, A method of dissolving a compound represented by the formula
  • the above-mentioned resin matrix material a monomer curable with the resin matrix resin, or a mixture thereof can be used.
  • the monomer curable with the resin matrix resin there is a (meth) acrylic monomer, which can be formed from a resin matrix material by UV curing.
  • an initiator necessary for curing may be further added if necessary.
  • the solvent is not particularly limited and is not particularly limited as long as it can be removed by drying without adversely affecting the coating process.
  • Nonlimiting examples of the solvent include toluene, xylene, acetone, chloroform, various alcohol solvents, MEK (methyl ethyl ketone), MIBK (methyl isobutyl ketone), EA (ethyl acetate), butyl acetate, DMF Dimethylformamide), DMAc (dimethylacetamide), DMSO (dimethylsulfoxide), NMP (N-methyl-pyrrolidone) and the like may be used alone or in admixture of two or more.
  • the solvent contained in each of these solutions may be the same or different. Even when different kinds of solvents are used for the first solution and the second solution, it is preferable that these solvents have compatibility so that they can be mixed with each other.
  • a roll-to-roll process can be used for the step of coating the resin solution on which the compound represented by the formula (1) is dissolved. For example, a step of dissolving a substrate from a roll on which a substrate is wound, coating a resin solution in which the compound represented by the formula (1) is dissolved on one surface of the substrate, drying, and then winding the same on a roll again.
  • a die coater may be used, and various bar coating methods such as a comma coater, a reverse comma coater, and the like may be used.
  • a drying process is performed.
  • the drying process can be carried out under the conditions necessary for removing the solvent.
  • the substrate is dried in an oven located adjacent to the coater in a direction in which the substrate proceeds in a coating process, under conditions that the solvent is sufficiently blown, and a color conversion including a fluorescent substance, A film can be obtained.
  • curing such as UV curing may be performed before or during the drying.
  • the compound represented by the formula (1) When the compound represented by the formula (1) is extruded together with the resin to form a film, extrusion methods known in the art can be used. For example, the compound represented by the formula (1) is reacted with a polycarbonate- ) Acrylic resin, and styrene-acrylonitrile (SAN) resin are simultaneously extruded to produce a color conversion film.
  • a polycarbonate- ) Acrylic resin and styrene-acrylonitrile (SAN) resin are simultaneously extruded to produce a color conversion film.
  • SAN styrene-acrylonitrile
  • the color conversion film may be provided on at least one side with a protective film or a barrier film.
  • a protective film or a barrier film those known in the art can be used.
  • FIG. 1 shows a schematic diagram of a backlight unit structure according to an example.
  • the backlight unit according to FIG. 1 includes a side-chain type light source 101, a reflection plate 102 surrounding the light source, a light guide plate 103 for directly emitting light from the light source or guiding light reflected from the reflection plate, And a color conversion film 105 provided on the opposite surface of the light guide plate opposite to the reflective layer.
  • the portion indicated by (106) is a light dispersion pattern of the light guide plate.
  • the light introduced into the light guide plate has a non-uniform light distribution due to repetition of optical processes such as reflection, total reflection, refraction, and transmission, and a two-dimensional light dispersion pattern can be used to induce uniform brightness.
  • the scope of the present invention is not limited to that shown in FIG. 1, and the light source may be a direct-type as well as a side-chain type, and the reflection plate or the reflective layer may be omitted or replaced with another structure if necessary, A light-diffusing film, a light-condensing film, a luminance improving film, and the like.
  • a display device including the backlight unit is not particularly limited as long as it is a display device including a backlight unit, and may be included in a TV, a computer monitor, a notebook computer, a mobile phone, and the like.
  • Compound 2 was prepared in the same manner as Compound 1 except that 2 g of Compound 35a was used instead of Compound 1c and Compound 8d was used instead of Compound 1d. At this time, 1.20 g (52%) of Compound 36 was obtained.
  • HR LC / MS / MS m / z Calcd C 138 H 86 B 2 F 10 N 10 O 2 (M +): 2127.6995; found: 2127.6997
  • Compound 2 was prepared in the same manner as Compound 1 except that 2 g of Compound 37a was used instead of Compound 1c and Compound 8d was used instead of Compound 1d. At this time, 1.75 g (76%) of Compound 37 was obtained.
  • HR LC / MS / MS m / z Calcd C 142 H 86 B 2 F 6 N 14 O 2 (M +): 2155.7182; found: 2155.7182
  • Compound 1 (maximum absorption wavelength in a toluene solution: 450 nm, maximum light emission wavelength: 621 nm) prepared in Preparation Example 1 was mixed with 33.9 parts by weight of an acrylic binder, 30 parts by weight of a polyfunctional monomer (pentaerythritol triacrylate, ), 59.3 parts by weight of an adhesion promoter and 2.3 parts by weight of a surfactant (KBM 503, shinetsu) and 3.0 parts by weight of a photoinitiator (Tinuvin 477, BASF) were dissolved in a solvent PGEMA (propylene glycol monomethyl ether acetate: glycol monomethyl ether acetate) to prepare a solution.
  • PGEMA propylene glycol monomethyl ether acetate: glycol monomethyl ether acetate
  • a thin film was coated on a glass substrate and dried to prepare a color conversion film.
  • the luminance spectrum of the prepared color conversion film was measured with a spectroradiometer (TOPCON SR series). Specifically, the prepared color conversion film was laminated on one side of a light guide plate of a backlight unit including LED blue backlight (maximum emission wavelength: 450 nm) and a light guide plate, and a prism sheet and a DBEF film were laminated on the color conversion film, The initial value was set so that the brightness of the blue LED light would be 600 nit.
  • Example 1 The procedure of Example 1 was repeated, except that Compound 2 (maximum absorption wavelength in toluene solution: 427 nm, 454 nm maximum emission wavelength: 630 nm) was used instead of Compound 1 in Example 1.
  • Compound 2 maximum absorption wavelength in toluene solution: 427 nm, 454 nm maximum emission wavelength: 630 nm
  • Example 1 The procedure of Example 1 was repeated, except that Compound 3 (maximum absorption wavelength in toluene solution: 428 nm, maximum emission wavelength: 454 nm, 635 nm) was used instead of Compound 1 in Example 1.
  • Compound 3 maximum absorption wavelength in toluene solution: 428 nm, maximum emission wavelength: 454 nm, 635 nm
  • Example 1 The procedure of Example 1 was repeated, except that Compound 8 (maximum absorption wavelength in toluene solution: 472 nm, 496 nm maximum emission wavelength: 652 nm) was used instead of Compound 1 in Example 1.
  • Compound 8 maximum absorption wavelength in toluene solution: 472 nm, 496 nm maximum emission wavelength: 652 nm
  • Example 1 The procedure of Example 1 was repeated, except that Compound 9 (maximum absorption wavelength in toluene solution: 492 nm, 506 nm maximum emission wavelength: 655 nm) was used instead of Compound 1 in Example 1.
  • Compound 9 maximum absorption wavelength in toluene solution: 492 nm, 506 nm maximum emission wavelength: 655 nm
  • Example 1 The procedure of Example 1 was repeated, except that Compound 12 (maximum absorption wavelength in a toluene solution: 468 nm, 495 nm maximum emission wavelength: 652 nm) was used instead of Compound 1 in Example 1.
  • Compound 12 maximum absorption wavelength in a toluene solution: 468 nm, 495 nm maximum emission wavelength: 652 nm
  • Example 1 The procedure of Example 1 was repeated, except that Compound 13 (maximum absorption wavelength in toluene solution: 473 nm, maximum emission wavelength: 500 nm, 655 nm) was used instead of Compound 1 in Example 1.
  • Compound 13 maximum absorption wavelength in toluene solution: 473 nm, maximum emission wavelength: 500 nm, 655 nm
  • Example 1 was carried out in the same manner as in Example 1, except that Compound 21 (maximum absorption wavelength in a toluene solution: 463 nm, 490 nm maximum emission wavelength: 640 nm) was used instead of Compound 1 in Example 1.
  • Example 1 The procedure of Example 1 was repeated, except that Compound 22 (maximum absorption wavelength in a toluene solution: 467 nm, 495 nm maximum emission wavelength: 650 nm) was used instead of Compound 1 in Example 1.
  • Example 1 The procedure of Example 1 was repeated, except that Compound 23 (maximum absorption wavelength in a toluene solution: 468 nm, 495 nm maximum emission wavelength: 652 nm) was used instead of Compound 1 in Example 1.
  • Example 1 The procedure of Example 1 was repeated, except that Compound 24 was used instead of Compound 1 in Example 1 (maximum absorption wavelength in toluene solution: 488 nm, 511 nm maximum emission wavelength: 667 nm).
  • Example 1 The procedure of Example 1 was repeated, except that Compound 25 (maximum absorption wavelength in toluene solution: 470 nm, 500 nm maximum emission wavelength: 650 nm) was used instead of Compound 1 in Example 1.
  • Compound 25 maximum absorption wavelength in toluene solution: 470 nm, 500 nm maximum emission wavelength: 650 nm
  • Example 1 The procedure of Example 1 was repeated, except that Compound 26 (maximum absorption wavelength in a toluene solution: 475 nm, maximum emission wavelength: 504 nm, 655 nm) was used instead of Compound 1 in Example 1.
  • Compound 26 maximum absorption wavelength in a toluene solution: 475 nm, maximum emission wavelength: 504 nm, 655 nm
  • Example 1 The procedure of Example 1 was repeated, except that Compound 27 (maximum absorption wavelength in toluene solution: 475 nm, 505 nm maximum emission wavelength: 652 nm) was used instead of Compound 1 in Example 1.
  • Compound 27 maximum absorption wavelength in toluene solution: 475 nm, 505 nm maximum emission wavelength: 652 nm
  • Example 1 The procedure of Example 1 was repeated, except that Compound 29 (maximum absorption wavelength in toluene solution: 492 nm, 524 nm maximum emission wavelength: 672 nm) was used instead of Compound 1 in Example 1.
  • Compound 29 maximum absorption wavelength in toluene solution: 492 nm, 524 nm maximum emission wavelength: 672 nm
  • Example 1 The procedure of Example 1 was repeated, except that Compound 30 was used instead of Compound 1 in Example 1 (maximum absorption wavelength in toluene solution: 460 nm, 488 nm maximum emission wavelength: 645 nm).
  • Example 1 was carried out in the same manner as in Example 1, except that Compound 31 (maximum absorption wavelength in a toluene solution: 467 nm, 498 nm maximum emission wavelength: 647 nm) was used instead of Compound 1 in Example 1.
  • Example 1 The procedure of Example 1 was repeated, except that Compound 32 (maximum absorption wavelength in a toluene solution: 468 nm, maximum emission wavelength: 500 nm, 643 nm) was used instead of Compound 1 in Example 1.
  • Compound 32 maximum absorption wavelength in a toluene solution: 468 nm, maximum emission wavelength: 500 nm, 643 nm
  • Example 1 The procedure of Example 1 was repeated, except that Compound 35 (maximum absorption wavelength in toluene solution: 482 nm, 510 nm maximum emission wavelength: 658 nm) was used instead of Compound 1 in Example 1.
  • Compound 35 maximum absorption wavelength in toluene solution: 482 nm, 510 nm maximum emission wavelength: 658 nm
  • Example 1 The procedure of Example 1 was repeated, except that Compound 36 (maximum absorption wavelength in toluene solution: 485 nm, 513 nm maximum emission wavelength: 650 nm) was used instead of Compound 1 in Example 1.
  • Example 1 The procedure of Example 1 was repeated, except that Compound 38 (maximum absorption wavelength in toluene solution: 483 nm, 514 nm maximum emission wavelength: 665 nm) was used instead of Compound 1 in Example 1.
  • Example 1 The procedure of Example 1 was repeated, except that Comparative Compound B5 (maximum absorption wavelength in a toluene solution: 494 nm, maximum emission wavelength: 687 nm) was used instead of Compound 1 in Example 1.
  • Comparative Compound B5 maximum absorption wavelength in a toluene solution: 494 nm, maximum emission wavelength: 687 nm
  • Each compound used in Examples 1 to 21 and Comparative Example 1 was made to have a concentration of 10 -5 M in a toluene solvent, and the solution properties were measured.
  • the maximum absorption wavelength ( ⁇ uv, MAX ) was measured using a UV-visible spectrometer (Mega-200) manufactured by Sinco and the absorbance at 450 nm
  • the maximum emission wavelength ( ⁇ PL , MAX ) was measured using a fluorescenc spectrometer (FS-2) manufactured by Sinco.
  • the maximum emission wavelength ( ⁇ PL , MAX ) of the thin films prepared in Examples 1 to 21 and Comparative Example 1 was measured using a fluorescence spectrometer (FS-2) manufactured by Hamamatsu Co., -QY (C11347-11) was used to measure the quantum efficiency of the thin film.

Abstract

The present specification relates to a nitrogen-containing compound, a color conversion film comprising the same, and a backlight unit and a display device each comprising same.

Description

함질소 화합물, 이를 포함하는 색변환 필름, 및 이를 포함하는 백라이트 유닛 및 디스플레이 장치Nitrogen compound, color conversion film containing the same, and backlight unit and display device including the same
본 명세서는 함질소 화합물, 이를 포함하는 색변환 필름, 백라이트 유닛 및 디스플레이 장치에 관한 것이다.TECHNICAL FIELD The present invention relates to a nitrogen-containing compound, a color conversion film comprising the same, a backlight unit, and a display device.
본 명세서는 2017년 12월 7일에 한국특허청에 제출된 한국특허출원 제10-2017-0167119호 및 2018년 12월 6일에 한국특허청에 제출된 한국특허출원 제10-2018-0156173호의 출원일의 이익을 주장하며, 그 내용은 전부 본 명세서에 포함된다. This specification is based on Korean Patent Application No. 10-2017-0167119 filed on December 7, 2017, and Korean Patent Application No. 10-2018-0156173 filed on December 6, 2018 All of which are incorporated herein by reference.
기존의 발광다이오드(LED)들은 청색광 발광 다이오드에 녹색 인광체 및 적색 인광체를 혼합하거나 UV광 방출 발광다이오드에 황색 인광체 및 청-녹색 인광체를 혼합하여 얻어진다. 하지만, 이와 같은 방식은 색상을 제어하기 어렵고 이에 따라 연색성이 좋지 않다. 따라서, 색재현율이 떨어진다. Conventional light emitting diodes (LEDs) are obtained by mixing a green phosphor and a red phosphor in a blue light emitting diode or by mixing a yellow phosphor and a blue-green phosphor in a UV light emitting diode. However, such a method is difficult to control the color and thus has poor color rendering properties. Therefore, the color reproduction rate drops.
이러한 색재현율 하락을 극복하고, 생산 비용을 줄이기 위하여 양자점을 필름화하여 청색 LED에 결합시키는 방식으로 녹색 및 적색을 구현하는 방식이 최근에 시도되고 있다. 하지만, 카드뮴 계열의 양자점은 안전성 문제가 있고, 그외 양자점은 카드뮴 계열에 비하여 효율이 크게 떨어진다. 또한, 양자점은 산소 및 물에 대한 안정도가 떨어지며 응집될 경우 그 성능이 현저하게 저하되는 단점이 있다. 또한, 양자점의 생산시 그 크기를 일정하게 유지하기 힘들어 생산 단가가 높다.Recently, attempts have been made to realize green and red colors by bonding quantum dots to a blue LED in order to overcome the decrease in the color reproducibility and reduce the production cost. However, cadmium-based quantum dots have safety problems, and other quantum dots are less efficient than cadmium-based ones. Further, the quantum dots have a disadvantage that their stability against oxygen and water is poor and their performance remarkably decreases when they are aggregated. Moreover, it is difficult to keep the size of the quantum dot constant during the production of the quantum dot, resulting in a high production cost.
본 명세서는 함질소 화합물, 이를 포함하는 색변환 필름, 백라이트 유닛 및 디스플레이 장치를 제공한다.The present specification provides a nitrogen-containing compound, a color conversion film containing the same, a backlight unit, and a display device.
본 명세서의 일 실시상태에 따르면, 하기 화학식 1로 표시되는 화합물을 제공한다.According to one embodiment of the present invention, there is provided a compound represented by the following formula (1).
[화학식 1][Chemical Formula 1]
Figure PCTKR2018015522-appb-I000001
Figure PCTKR2018015522-appb-I000001
상기 화학식 1에 있어서, In Formula 1,
L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴렌기이고, L1 and L2 are the same or different and are each independently a substituted or unsubstituted arylene group,
L10 내지 L13은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 2가의 헤테로고리기이며, L10 to L13 are the same or different and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
R1 내지 R4는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카르보닐기; 에스테르기; 이미드기; 아미드기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 플루오로알킬기; 치환 또는 비치환된 알킬티오기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 헤테로아릴기; 또는 치환 또는 비치환된 탄화수소고리기이고, R1 to R4 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted fluoroalkyl group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted allyloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or a substituted or unsubstituted hydrocarbon ring group,
R1 내지 R4중 적어도 하나는 하기 화학식 2로 표시되며, At least one of R 1 to R 4 is represented by the following formula (2)
[화학식 2](2)
Figure PCTKR2018015522-appb-I000002
Figure PCTKR2018015522-appb-I000002
상기 화학식 2에 있어서, In Formula 2,
R10 내지 R19 중 하나는 화학식 1과 결합하고, One of R10 to R19 is bonded to the formula (1)
R10 내지 R19 중 화학식 1과 결합하지 않는 기는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카르보닐기; 에스테르기; 이미드기; 아미드기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 플루오로알킬기; 치환 또는 비치환된 알킬티오기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 헤테로아릴기; 또는 치환 또는 비치환된 탄화수소고리기이거나, 서로 결합하여 치환 또는 비치환된 고리를 형성하며, The groups not bonded to the formula (1) among R10 to R19 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted fluoroalkyl group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted allyloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or a substituted or unsubstituted hydrocarbon ring group, or may be bonded to each other to form a substituted or unsubstituted ring,
X1 및 X2는 서로 같거나 상이하고, 각각 독립적으로 할로겐기; 니트릴기; -CO2R""; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 헤테로고리기; 또는 치환 또는 비치환된 탄화수소고리기이거나, 상기 X1 및 X2가 서로 결합하여 치환 또는 비치환된 고리를 형성하고, X1 and X2 are the same or different from each other, and each independently represents a halogen group; A nitrile group; -CO 2 R ""; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted hydrocarbon ring group, or X 1 and X 2 are bonded to each other to form a substituted or unsubstituted ring,
R""은 치환 또는 비치환된 알킬기; 치환 또는 비치환된 플루오로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 헤테로고리기; 또는 치환 또는 비치환된 탄화수소고리기이다. R "" is a substituted or unsubstituted alkyl group; A substituted or unsubstituted fluoroalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted hydrocarbon ring group.
본 명세서의 또 하나의 실시상태에 따르면, 수지 매트릭스; 및 상기 수지 매트릭스 내에 분산된 상기 화학식 1로 표시되는 화합물을 포함하는 색변환 필름을 제공한다. According to another embodiment of the present disclosure, a resin matrix; And a color conversion film containing the compound represented by the formula (1) dispersed in the resin matrix.
본 명세서의 또 하나의 실시상태에 따르면, 상기 색변환 필름을 포함하는 백라이트 유닛을 제공한다. According to another embodiment of the present disclosure, there is provided a backlight unit including the color conversion film.
본 명세서의 또 하나의 실시상태에 따르면, 상기 백라이트 유닛을 포함하는 디스플레이 장치를 제공한다.According to another embodiment of the present disclosure, there is provided a display device including the backlight unit.
종래의 아자보디피 구조(화학식 2)의 화합물은 녹색 및 주황색 영역의 형광물질로 사용하는 것을 특징으로 하나, 본 명세서의 일 실시상태에 따른 화합물은 CN=CN(fumaronitrile)구조를 도입하여, 청색광(blue backlight)에 대한 흡수도를 증가시키고, 적색 형광할 수 있다. 따라서, 종래의 아자보디피 화합물은 색변환을 위하여 녹색염료과 적색염료를 함께 사용하였으나, 본 명세서에 따른 화합물은 적색염료를 단독으로 사용할 수 있으며, 공정성이 우수하다. The compound according to one embodiment of the present invention introduces CN = CN (fumaronitrile) structure to form blue light (blue light) (blue backlight) and red fluorescence. Accordingly, the conventional azabodicar compound used a green dye and a red dye together for color conversion, but the compound according to the present invention can use a red dye alone, and is excellent in fairness.
도 1은 본 명세서의 일 실시상태에 따른 색변환 필름을 백라이트에 적용한 모식도이다.BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is a schematic diagram showing a color conversion film according to an embodiment of the present invention applied to a backlight; FIG.
[부호의 설명][Description of Symbols]
101: 측쇄형 광원101: a side-chain type light source
102: 반사판102: reflector
103: 도광판103: light guide plate
104: 반사층104: reflective layer
105: 색변환 필름105: color conversion film
106: 광분산 패턴106: light dispersion pattern
이하, 본 명세서에 대하여 더욱 상세하게 설명한다.Hereinafter, the present invention will be described in more detail.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1로 표시되는 화합물을 제공한다.According to one embodiment of the present invention, there is provided a compound represented by the above formula (1).
본 명세서에 있어서, 어떤 부분이 어떤 구성요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성 요소를 더 포함할 수 있는 것을 의미한다.In this specification, when a part is referred to as "including " an element, it is to be understood that it may include other elements as well, without departing from the other elements unless specifically stated otherwise.
본 명세서에 있어서, 어떤 부재가 다른 부재 "상에" 위치하고 있다고 할 때, 이는 어떤 부재가 다른 부재에 접해 있는 경우뿐 아니라 두 부재 사이에 또 다른 부재가 존재하는 경우도 포함한다.In this specification, when a member is located on another member, it includes not only the case where the member is in contact with the other member but also the case where another member exists between the two members.
본 명세서에 있어서 치환기의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다.Examples of substituents in the present specification are described below, but are not limited thereto.
상기 "치환"이라는 용어는 화합물의 탄소 원자에 결합된 수소 원자가 다른 치환기로 바뀌는 것을 의미하며, 치환되는 위치는 수소 원자가 치환되는 위치 즉, 치환기가 치환 가능한 위치라면 한정하지 않으며, 2 이상 치환되는 경우, 2 이상의 치환기는 서로 동일하거나 상이할 수 있다.The term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, , Two or more substituents may be the same as or different from each other.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 니트릴기; 니트로기; 아미노기; 카르보닐기; 카르복시기(-COOH); 에테르기; 에스테르기; 히드록시기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 플루오로알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 플루오로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되었거나 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 바이페닐기일 수 있다. 즉, 바이페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 있다. As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; An amino group; Carbonyl group; Carboxy group (-COOH); Ether group; An ester group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted fluoroalkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted fluoroalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or that at least two of the substituents exemplified above are substituted with a substituent to which they are linked, or have no substituent. For example, "a substituent to which at least two substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.
본 명세서에 있어서,
Figure PCTKR2018015522-appb-I000003
는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.
In the present specification,
Figure PCTKR2018015522-appb-I000003
Quot; refers to a moiety bonded to another substituent or bond.
본 명세서에 있어서, 할로겐기는 플루오르, 염소, 브롬 또는 요오드가 될 수 있다.In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.
본 명세서에 있어서, 이미드기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 30인 것이 바람직하다. 구체적으로 -C(=O)N(C(=O)R100)R101 또는 하기와 같은 구조의 화합물이 될 수 있으며, 상기 R100 및 R101은 서로 같거나 상이하며, 각각 독립적으로 수소, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 시클로알킬기, 또는 치환 또는 비치환된 아릴기이나, 이에 한정되는 것은 아니다.In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 30 carbon atoms. (C (= O) R 100 ) R 101 or a compound having the following structure: wherein R 100 and R 101 are the same or different from each other and each independently represents hydrogen, A substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group.
Figure PCTKR2018015522-appb-I000004
Figure PCTKR2018015522-appb-I000004
본 명세서에 있어서, 아미드기는 아미드기의 질소가 수소, 탄소수 1 내지 30의 직쇄, 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 30의 아릴기로 치환될 수 있다. 구체적으로, -C(=O)NR102R103 또는 하기 구조식의 화합물이 될 수 이며, 상기 R102 및 R103는 서로 같거나 상이하고, 각각 독립적으로 수소, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 시클로알킬기, 또는 치환 또는 비치환된 아릴기이나, 이에 한정되는 것은 아니다.이에 한정되는 것은 아니다.In the present specification, the amide group may be substituted with nitrogen of the amide group by hydrogen, a straight chain, branched chain or cyclic alkyl group of 1 to 30 carbon atoms or an aryl group of 6 to 30 carbon atoms. Specifically, -C (= O) NR 102 R 103 or Wherein R 102 and R 103 are the same or different from each other and each independently represents hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group However, the present invention is not limited thereto, and the present invention is not limited thereto.
Figure PCTKR2018015522-appb-I000005
Figure PCTKR2018015522-appb-I000005
본 명세서에서 카르보닐기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 30인 것이 바람직하다. 구체적으로 -C(=O)R104 또는 하기와 같은 구조의 화합물이 될 수 있으며, 상기 R104은 수소, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 시클로알킬기, 또는 치환 또는 비치환된 아릴기이나, 이에 한정되는 것은 아니다.In the present specification, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, -C (= O) R 104 or a compound having the following structure, and R 104 is hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl However, the present invention is not limited thereto.
Figure PCTKR2018015522-appb-I000006
Figure PCTKR2018015522-appb-I000006
본 명세서에 있어서, 에테르기는 에테르의 산소가 탄소수 1 내지 25의 직쇄, 분지쇄 또는 고리쇄 알킬기; 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환될 수 있다. In the present specification, the ether group is a straight chain, branched or cyclic alkyl group having 1 to 25 carbon atoms in which the ether is oxygen; Or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서에 있어서, 에스테르기는 에스테르기의 산소가 탄소수 1 내지 25의 직쇄, 분지쇄 또는 고리쇄 알킬기; 알케닐기; 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 탄소수 2 내지 30의 헤테고리기로 치환될 수 있다. 구체적으로, -C(=O)OR105, -OC(=O)R106 또는 하기 구조식의 화합물이 될 수 있으며, 상기 R105 및 R106는 서로 같거나 상이하고, 각각 독립적으로 수소, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 시클로알킬기, 또는 치환 또는 비치환된 아릴기이나, 이에 한정되는 것은 아니다.In the present specification, the ester group means that the oxygen in the ester group is a straight, branched or cyclic alkyl group having 1 to 25 carbon atoms; An alkenyl group; A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a heterocyclic group having 2 to 30 carbon atoms. Specifically, -C (= O) OR 105 , -OC (= O) R 106 Or a compound of the following structural formula, wherein R 105 and R 106 are the same or different from each other and each independently represents hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl However, the present invention is not limited thereto.
Figure PCTKR2018015522-appb-I000007
Figure PCTKR2018015522-appb-I000007
Figure PCTKR2018015522-appb-I000008
Figure PCTKR2018015522-appb-I000009
Figure PCTKR2018015522-appb-I000008
Figure PCTKR2018015522-appb-I000009
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 30인 것이 바람직하다. 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸-부틸, 1-에틸-부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 시클로펜틸메틸, 시클로헥실메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸-프로필, 1,1-디메틸-프로필, 이소헥실, 2-메틸펜틸, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, Cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.
본 명세서에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 30인 것이 바람직하며, 구체적으로 시클로프로필, 시클로부틸, 시클로펜틸, 3-메틸시클로펜틸, 2,3-디메틸시클로펜틸, 시클로헥실, 3-메틸시클로헥실, 4-메틸시클로헥실, 2,3-디메틸시클로헥실, 3,4,5-트리메틸시클로헥실, 4-tert-부틸시클로헥실, 시클로헵틸, 시클로옥틸 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the cycloalkyl group is not particularly limited, but is preferably a group having 3 to 30 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, isobutyl, sec-butyl, It is not.
본 명세서에 있어서, 플루오로알킬기는 특별히 한정되지 않으나, 탄소수 1 내지 10인 것이 바람직하며, 구체적으로 트리플루오로메틸기, 퍼플루오로에틸기 등이 있으나 이에 한정되는 것은 아니다. In the present specification, the fluoroalkyl group is not particularly limited, but preferably has 1 to 10 carbon atoms, and specifically includes, but is not limited to, a trifluoromethyl group, a perfluoroethyl group, and the like.
본 명세서에 있어서, 알킬티오기기는 특별히 한정되지 않으나, 탄소수 1 내지 10 인 것이 바람직하며, 구체적으로 메틸티오기, 에틸티오기 등이 있으나 이에 한정되는 것은 아니다.In the present specification, the alkylthio device is not particularly limited, but preferably has 1 to 10 carbon atoms, and specifically includes methylthio, ethylthio, and the like, but is not limited thereto.
본 명세서에 있어서, 상기 알콕시기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 30인 것이 바람직하다. 구체적으로, 메톡시, 에톡시, n-프로폭시, 이소프로폭시, i-프로필옥시, n-부톡시, 이소부톡시, tert-부톡시, sec-부톡시, n-펜틸옥시, 네오펜틸옥시, 이소펜틸옥시, n-헥실옥시, 3,3-디메틸부틸옥시, 2-에틸부틸옥시, n-옥틸옥시, n-노닐옥시, n-데실옥시, 벤질옥시, p-메틸벤질옥시 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 30인 것이 바람직하다. 구체적인 예로는 비닐, 1-프로페닐, 이소프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 1-펜테닐, 2-펜테닐, 3-펜테닐, 3-메틸-1-부테닐, 1,3-부타디에닐, 알릴, 1-페닐비닐-1-일, 2-페닐비닐-1-일, 2,2-디페닐비닐-1-일, 2-페닐-2-(나프틸-1-일)비닐-1-일, 2,2-비스(디페닐-1-일)비닐-1-일, 스틸베닐기, 스티레닐기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.
본 명세서에 있어서, 상기 알키닐기는 직쇄 또는 빈지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 30인 것이 바람직하다. 구체적인 예로는 에티닐, 프로피닐, 2-메틸-2프로피닐, 2-부티닐, 2-펜티닐 등의 알키닐기 등이 있으나, 이에 한정되지 않는다.In the present specification, the alkynyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably from 2 to 30. Specific examples include, but are not limited to, alkynyl groups such as ethynyl, propynyl, 2-methyl-2-propynyl, 2-butynyl, 2-pentynyl and the like.
본 명세서에 있어서, 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, However, the present invention is not limited thereto.
본 명세서에 있어서, 붕소기는 -BR107R108R109일 수 있으며, 상기 R107, R108 및 R109은 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐; 니트릴기; 치환 또는 비치환된 탄소수 3 내지 30의 단환 또는 다환의 시클로알킬기; 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 및 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기로 이루어진 군으로부터 선택될 수 있다.In the present specification, the boron group may be -BR 107 R 108 R 109 , wherein R 107 , R 108 and R 109 are the same or different and each independently hydrogen; heavy hydrogen; halogen; A nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
본 명세서에 있어서, 포스핀옥사이드기는 구체적으로 디페닐포스핀옥사이드기, 디나프틸포스핀옥사이드 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the phosphine oxide group specifically includes a diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like, but is not limited thereto.
본 명세서에 있어서, 아민기는 -NH2; 모노알킬아민기; 디알킬아민기; N-알킬아릴아민기; 모노아릴아민기; 디아릴아민기; N-아릴헤테로아릴아민기; N-알킬헤테로아릴아민기, 모노헤테로아릴아민기 및 디헤테로아릴아민기로 이루어진 군으로부터 선택될 수 있으며, 탄소수는 특별히 한정되지 않으나, 1 내지 30인 것이 바람직하다. 아민기의 구체적인 예로는 메틸아민기, 디메틸아민기, 에틸아민기, 디에틸아민기, 페닐아민기, 나프틸아민기, 바이페닐아민기, 안트라세닐아민기, 9-메틸-안트라세닐아민기, 디페닐아민기, 디톨릴아민기, N-페닐톨릴아민기, 트리페닐아민기, N-페닐바이페닐아민기; N-페닐나프틸아민기; N-바이페닐나프틸아민기; N-나프틸플루오레닐아민기; N-페닐페난트레닐아민기; N-바이페닐페난트레닐아민기; N-페닐플루오레닐아민기; N-페닐터페닐아민기; N-페난트레닐플루오레닐아민기; N-바이페닐플루오레닐아민기 등이 있으나, 이에 한정되는 것은 아니다.In this specification, the amine group is -NH 2 ; Monoalkylamine groups; A dialkylamine group; N-alkylarylamine groups; Monoarylamine groups; A diarylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, a monoheteroarylamine group, and a diheteroarylamine group. The number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; An N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; An N-biphenyl phenanthrenyl amine group; N-phenylfluorenylamine group; An N-phenyltriphenylamine group; N-phenanthrenyl fluorenylamine group; And an N-biphenylfluorenylamine group, but are not limited thereto.
본 명세서에 있어서, 아릴아민기의 예로는 치환 또는 비치환된 모노아릴아민기, 치환 또는 비치환된 디아릴아민기, 또는 치환 또는 비치환된 트리아릴아민기가 있다. 상기 아릴아민기 중의 아릴기는 단환식 아릴기일 수 있고, 다환식 아릴기일 수 있다. 상기 아릴기가 2 이상을 포함하는 아릴아민기는 단환식 아릴기, 다환식 아릴기, 또는 단환식 아릴기와 다환식 아릴기를 동시에 포함할 수 있다. 예컨대, 상기 아릴아민기 중의 아릴기는 전술한 아릴기의 예시 중에서 선택될 수 있다.In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나, 탄소수 6 내지 30인 것이 바람직하며, 상기 아릴기는 단환식 또는 다환식일 수 있다.In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
상기 아릴기가 단환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나, 탄소수 6 내지 30인 것이 바람직하다. 구체적으로 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms. Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.
상기 아릴기가 다환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나. 탄소수 10 내지 30인 것이 바람직하다. 구체적으로 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 트리페닐기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably 10 to 30 carbon atoms. Specific examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a triphenyl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.
본 명세서에 있어서, 상기 플루오레닐기는 치환될 수 있으며, 인접한 치환기들이 서로 결합하여 고리를 형성할 수 있다. In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
상기 플루오레닐기가 치환되는 경우,
Figure PCTKR2018015522-appb-I000010
,
Figure PCTKR2018015522-appb-I000011
,
Figure PCTKR2018015522-appb-I000012
Figure PCTKR2018015522-appb-I000013
등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.
When the fluorenyl group is substituted,
Figure PCTKR2018015522-appb-I000010
,
Figure PCTKR2018015522-appb-I000011
,
Figure PCTKR2018015522-appb-I000012
And
Figure PCTKR2018015522-appb-I000013
And the like. However, the present invention is not limited thereto.
본 명세서에 있어서, 아릴옥시기의 아릴기는 전술한 아릴기의 예시와 같다. 구체적으로 아릴옥시기로는 페녹시기, p-토릴옥시기, m-토릴옥시기, 3,5-디메틸-페녹시기, 2,4,6-트리메틸페녹시기, p-tert-부틸페녹시기, 3-바이페닐옥시기, 4-바이페닐옥시기, 1-나프틸옥시기, 2-나프틸옥시기, 4-메틸-1-나프틸옥시기, 5-메틸-2-나프틸옥시기, 1-안트릴옥시기, 2-안트릴옥시기, 9-안트릴옥시기, 1-페난트릴옥시기, 3-페난트릴옥시기, 9-페난트릴옥시기 등이 있고, 아릴티옥시기로는 페닐티옥시기, 2-메틸페닐티옥시기, 4-tert-부틸페닐티옥시기 등이 있으며, 아릴술폭시기로는 벤젠술폭시기, p-톨루엔술폭시기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the aryl group of the aryloxy group is the same as that of the above-mentioned aryl group. Specific examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6- trimethylphenoxy group, a p- Naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group and 9-phenanthryloxy group and the arylthioxy group includes phenylthio group, 2- Methylphenylthio group, 4-tert-butylphenylthio group and the like, and examples of the arylsulfoxy group include a benzene sulfoxide group and a p-toluenesulfoxy group. However, the present invention is not limited thereto.
본 명세서에 있어서, 헤테로고리기는 탄소가 아닌 원자, 이종원자를 1 이상 포함하는 것으로서, 구체적으로 상기 이종 원자는 O, N, Se 및 S 등으로 이루어진 군에서 선택되는 원자를 1 이상 포함할 수 있다. 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 30인 것이 바람직하며, 상기 헤테로아릴기는 단환식 또는 다환식일 수 있다. 헤테로고리기의 예로는 티오펜기, 퓨라닐기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 피리딘기, 바이피리딘기, 피리미딘기, 트리아진기, 트리아졸기, 아크리딘기, 피리다진기, 피라진기, 퀴놀린기, 퀴나졸린기, 퀴녹살린기, 프탈라진기, 피리도 피리미딘기, 피리도 피라진기, 피라지노 피라진기, 이소퀴놀린기, 인돌기, 카바졸기, 벤즈옥사졸기, 벤즈이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨란기, 페난쓰롤리닐기(phenanthroline), 이소옥사졸기, 티아디아졸기, 페노티아진기, 디벤조퓨란기, 디하이드로페노티아진기(
Figure PCTKR2018015522-appb-I000014
); 디하이드로벤조이소퀴놀린기(
Figure PCTKR2018015522-appb-I000015
)및 크로멘기(
Figure PCTKR2018015522-appb-I000016
) 등이 있으나, 이에 한정되는 것은 아니다.
In the present specification, the heterocyclic group includes at least one non-carbon atom or hetero atom, and specifically, the hetero atom may include at least one atom selected from the group consisting of O, N, Se and S, and the like. The number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include a thiophene group, a furanyl group, a pyrrolyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, , A pyrazine group, a pyrazine group, a quinoline group, a quinazoline group, a quinoxaline group, a phthalazine group, a pyridopyrimidine group, a pyridopyrazine group, a pyrazinopyrazine group, an isoquinoline group, An oxazolyl group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuran group, a phenanthroline group, an isoxazole group, a thiadiazole group, , A dibenzofurane group, a dihydrophenothiazine group (
Figure PCTKR2018015522-appb-I000014
); Dihydrobenzoisoquinoline group (
Figure PCTKR2018015522-appb-I000015
) And chromen group (
Figure PCTKR2018015522-appb-I000016
), But the present invention is not limited thereto.
본 명세서에 있어서, 헤테로고리기는 단환 또는 다환일 수 있으며, 방향족, 지방족 또는 방향족과 지방족의 축합고리일 수 있으며, 상기 헤테로고리기의 예시 중에서 선택될 수 있다.In the present specification, the heterocyclic group may be monocyclic or polycyclic, and may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and examples of the heterocyclic group may be selected.
본 명세서에 있어서, 탄화수소고리는 방향족, 지방족 또는 방향족과 지방족의 축합고리일 수 있으며, 상기 1가가 아닌 것을 제외하고 상기 시클로알킬기 또는 아릴기의 예시 중에서 선택될 수 있으며, 방향족과 지방족의 축합고리의 예로서 1,2,3,4-테트라하이드로나프탈렌기(
Figure PCTKR2018015522-appb-I000017
), 2,3-디하이드로-1H-인덴기(
Figure PCTKR2018015522-appb-I000018
) 등을 들 수 있지만 이에 한정되는 것은 아니다.
In the present specification, the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from the examples of the cycloalkyl group or the aryl group except the univalent hydrocarbon ring, and the aromatic and aliphatic condensed rings For example, a 1,2,3,4-tetrahydronaphthalene group (
Figure PCTKR2018015522-appb-I000017
), 2,3-dihydro-1H-indene group (
Figure PCTKR2018015522-appb-I000018
), But the present invention is not limited thereto.
본 명세서에 있어서, 아리렌기는 아릴기에 결합 위치가 두개 있는 것, 즉 2가기를 의미한다. 이들은 각각 2가기인 것을 제외하고는 전술한 아릴기의 설명이 적용될 수 있다. In the present specification, an arylene group means a group having two bonding positions in an aryl group, that is, a divalent group. The description of the aryl group described above can be applied except that each of these is 2 groups.
본 명세서에 있어서, 헤테로아릴렌기는 헤테로아릴기에 결합 위치가 두 개 있는 것 즉 2가기를 의미한다. 이들은 각각 2가기인 것을 제외하고는 전술한 헤테로아릴기의 설명이 적용될 수 있다. In the present specification, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, divalent. The description of the above-mentioned heteroaryl groups can be applied, except that they are each 2 groups.
본 명세서에 있어서, "인접한" 기는 해당 치환기가 치환된 원자와 직접 연결된 원자에 치환된 치환기, 해당 치환기와 입체구조적으로 가장 가깝게 위치한 치환기, 또는 해당 치환기가 치환된 원자에 치환된 다른 치환기를 의미할 수 있다. 예컨대, 벤젠고리에서 오르토(ortho)위치로 치환된 2개의 치환기 및 지방족 고리에서 동일 탄소에 치환된 2개의 치환기는 서로 "인접한" 기로 해석될 수 있다.As used herein, the term "adjacent" means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom . For example, two substituents substituted in the benzene ring to the ortho position and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.
본 명세서에 있어서, 치환기 중 "인접한 기는 서로 결합하여 고리를 형성한다"는 의미는 인접한 기와 서로 결합하여 치환 또는 비치환된 탄화수소고리; 또는 치환 또는 비치환된 헤테로고리를 형성하는 것을 의미한다.In the present specification, the term "adjacent groups are bonded to each other to form a ring" in the substituent group means a substituted or unsubstituted hydrocarbon ring bonded to adjacent groups to form a ring; Or a substituted or unsubstituted heterocycle.
본 명세서의 일 실시상태에 있어서, 상기 R1 및 R2중 적어도 하나와 R3 및 R4 중 적어도 하나는 상기 화학식 2이다.In one embodiment of the present disclosure, at least one of R 1 and R 2 and at least one of R 3 and R 4 is Formula 2.
본 명세서의 일 실시상태에 있어서, 상기 R1 및 R3은 상기 화학식 2이고,상기 R2 및 R4는 서로 같거나 상이하고, 각각 독립적으로 수소; 할로겐기; 니트릴기; 니트로기; 에스테르기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 플루오로알킬기; 치환 또는 비치환된 알킬티오기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 헤테로아릴기; 또는 치환 또는 비치환된 탄화수소고리기이다. In one embodiment of the present invention, R 1 and R 3 are the same as those in Formula 2, and R 2 and R 4 are the same or different and each independently hydrogen; A halogen group; A nitrile group; A nitro group; An ester group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted fluoroalkyl group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or a substituted or unsubstituted hydrocarbon ring group.
본 명세서의 일 실시상태에 있어서, 상기 R2 및 R4는 서로 같거나 상이하고, 각각 독립적으로 수소; F; 니트릴기; 니트로기; -C(=O))R200; 치환 또는 비치환된 메틸기; 치환 또는 비치환된 부틸기; 치환 또는 비치환된 시클로헥실기; 치환 또는 비치환된 메톡시기; 치환 또는 비치환된 트리플루오로메틸기; 치환 또는 비치환된 메틸티오기; 치환 또는 비치환된 트리페닐실릴기; 치환 또는 비치환된 트리메틸실릴기; 치환 또는 비치환된 디에틸아민기; 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 스피로비플루오레닐기; 치환 또는 비치환된 티오펜기; 치환 또는 비치환된 퓨란기; 치환 또는 비치환된 디벤조티오펜기; 치환 또는 비치환된 디벤조퓨란기; 치환 또는 비치환된 카바졸기; 치환 또는 비치환된 벤조카바졸기; 치환 또는 비치환된 티아졸기; 치환 또는 비치환된 페노티아진기; 치환 또는 비치환된 페녹사진기; 또는 치환 또는 비치환된 테트라하이드로나프탈렌기이다.In one embodiment of the present specification, R 2 and R 4 are the same or different from each other, and each independently hydrogen; F; A nitrile group; A nitro group; -C (= O) R 200 ; A substituted or unsubstituted methyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted cyclohexyl group; A substituted or unsubstituted methoxy group; A substituted or unsubstituted trifluoromethyl group; A substituted or unsubstituted methylthio group; A substituted or unsubstituted triphenylsilyl group; A substituted or unsubstituted trimethylsilyl group; A substituted or unsubstituted diethylamine group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted spirobifluorenyl group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted furan group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted thiazole group; A substituted or unsubstituted phenothiazine group; A substituted or unsubstituted phenoxy group; Or a substituted or unsubstituted tetrahydronaphthalene group.
본 명세서의 일 실시상태에 있어서, 상기 R200
Figure PCTKR2018015522-appb-I000019
이다.
In one embodiment of the present disclosure, the R < 200 >
Figure PCTKR2018015522-appb-I000019
to be.
본 명세서의 일 실시상태에 있어서, 상기 R2 및 R4에서 '치환 또는 비치환된'은 아릴기; 알킬기; 알콕시기; 할로겐기; 실릴기; 또는 니트릴기로 치환 또는 비치환되는 것을 의미한다. In one embodiment of the present specification, the 'substituted or unsubstituted' in R 2 and R 4 is an aryl group; An alkyl group; An alkoxy group; A halogen group; Silyl group; Or substituted or unsubstituted with a nitrile group.
본 명세서의 일 실시상태에 있어서, 상기 R2 및 R4에서 '치환 또는 비치환된'은 페닐기; 메톡시기; 메틸기; 에틸기; 부틸기; F; 트리메틸실릴기; 또는 니트릴기로 치환 또는 비치환되는 것을 의미한다. In one embodiment of the present specification, the 'substituted or unsubstituted' in R 2 and R 4 is a phenyl group; Methoxy group; Methyl group; An ethyl group; Butyl group; F; A trimethylsilyl group; Or substituted or unsubstituted with a nitrile group.
본 명세서의 일 실시상태에 있어서, 상기 R1 내지 R4 중 적어도 2는 상기 화학식 2로 표시된다. In one embodiment of the present invention, at least two of R 1 to R 4 are represented by the formula (2).
본 명세서의 일 실시상태에 있어서, 상기 R1 내지 R4은 상기 화학식 2이다.In one embodiment of the present invention, R 1 to R 4 are as defined in the above formula (2).
본 명세서에 따른 상기 화학식 2는 몰흡광계수가 높은 것을 특징으로 하는 분자구조이며, 한 분자 내에 도입되는 수가 증가할수록 청색광(blue light)에 대한 흡수도가 향상된다. 특히, 아자보디피의 경우, 450nm에 대한 흡수도가 존재하므로, 분자내에 도입되는 수가 증가되면 450nm 에 대한 흡수도 증가하여, 분자 내에서 내어 놓는 녹색 형광이 증가하고, 적색 영역으로 다시 재흡수 및 형광으로 색변환하는 확률을 증가시킨다. 따라서, 색변환필름의 효율을 증가시킨다. Formula 2 according to the present invention has a molecular structure with a high molar extinction coefficient. As the number of molecules introduced into one molecule increases, the absorbance against blue light increases. In particular, in the case of azabodipine, absorption at 450 nm is increased, so that when the number of molecules introduced into the molecule increases, absorption toward 450 nm increases, green fluorescence emitted in the molecule increases, The probability of color conversion is increased. Thus, the efficiency of the color conversion film is increased.
따라서, 상기 R1 내지 R4가 모두 상기 화학식 2인 경우, 높은 색변환률의 화합물을 얻을 수 있으며, 상기 화학식 2의 치환되는 치환기의 종류에 따라 색변환률을 보다 증가시킬 수 있다. Therefore, when R1 to R4 are all the above-described Formula 2, a compound having a high color conversion rate can be obtained, and the color conversion rate can be further increased according to the type of the substituent to be substituted in Formula 2 above.
본 명세서의 일 실시상태에 있어서, 상기 L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐렌기; 치환 또는 비치환된 바이페닐릴렌기; 치환 또는 비치환된 나프틸렌기; 치환 또는 비치환된 안트라세닐렌기; 치환 또는 비치환된 터페닐렌기; 치환 또는 비치환된 쿼터페닐렌기; 또는 치환 또는 비치환된 트리페닐릴렌기이다.In one embodiment of the present invention, L 1 and L 2 are the same or different and each independently represents a substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted anthracenylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted quaterphenylene group; Or a substituted or unsubstituted triphenylene group.
본 명세서의 일 실시상태에 있어서, 상기 L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐렌기; 또는 치환 또는 비치환된 바이페닐렌기이다.In one embodiment of the present invention, L 1 and L 2 are the same or different and each independently represents a substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.
본 명세서의 일 실시상태에 있어서, 상기 L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 알킬기, 알콕시기 또는 할로겐기로 치환 또는 비치환된 페닐렌기; 또는 알킬기, 알콕시기 또는 할로겐기로 치환 또는 비치환된 바이페닐릴렌기이다. In one embodiment of the present invention, L 1 and L 2 are the same or different and each independently represent a phenylene group substituted or unsubstituted with an alkyl group, an alkoxy group, or a halogen group; Or a biphenylene group substituted or unsubstituted with an alkyl group, an alkoxy group or a halogen group.
본 명세서의 일 실시상태에 있어서, 상기 L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐렌기이다. In one embodiment of the present invention, L 1 and L 2 are the same or different and each independently a substituted or unsubstituted phenylene group.
본 명세서의 일 실시상태에 있어서, 상기 L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 알킬기, 알콕시기 또는 할로겐기로 치환 또는 비치환된 페닐렌기이다. In one embodiment of the present invention, L 1 and L 2 are the same or different and each independently represent a phenylene group substituted or unsubstituted with an alkyl group, an alkoxy group, or a halogen group.
본 명세서의 일 실시상태에 있어서, 상기 R10 내지 R19 중 화학식 1과 결합하지 않는기는 서로 같거나 상이하고 각각 독립적으로 수소; 니트릴기; 니트로기; 에스테르기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 플루오로알킬기; 치환 또는 비치환된 알킬티오기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 헤테로고리기; 또는 치환 또는 비치환된 탄화수소고리기이다.In one embodiment of the present specification, the groups not bonded to the formula (1) among R10 to R19 are the same or different and each independently hydrogen; A nitrile group; A nitro group; An ester group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted fluoroalkyl group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted hydrocarbon ring group.
본 명세서의 일 실시상태에 있어서, 상기 R10 내지 R19 중 화학식 1과 결합하지 않는기에서 '치환 또는 비치환된'은 플루오로알킬기; 실릴기; 할로겐기; 아릴기; 헤테로아릴기; 에스테르기; 니트릴기; 알콕시기; 니트로기; 알킬기; 아릴옥시기; 아릴아민기; 시클로알킬기; 및 화학식 2로 표시되는 치환기로 이루어진 군에서 선택되는 1이상의 치환기로 치환 또는 비치환되는 것을 의미한다.In one embodiment of the present invention, the 'substituted or unsubstituted' fluoroalkyl group in the group not bonded to the formula (1) among R10 to R19 is a fluoroalkyl group; Silyl group; A halogen group; An aryl group; A heteroaryl group; An ester group; A nitrile group; An alkoxy group; A nitro group; An alkyl group; An aryloxy group; An arylamine group; A cycloalkyl group; And a substituent represented by the general formula (2).
본 명세서의 일 실시상태에 있어서, 상기 R10 내지 R19 중 화학식 1과 결합하지 않는기에서 '치환 또는 비치환된'은 트리플루오로메틸기; 트리페닐실릴기; 트리메틸실릴기; 트리에틸실릴기; F; 페닐기; 나프틸기; 플루오레닐기; 퓨란기; 티오펜기; 디벤조퓨란기; 디벤조티오펜기; 카바졸기; 페녹사틴기; 벤조옥사졸기; 크로멘기; -COOR201; 니트릴기; 알콕시기; 니트로기; 알킬기; 페녹시기; 디페닐아민기; 시클로헥실기; 및 화학식 2로 표시되는 치환기로 이루어진 군에서 선택되는 1이상의 치환기로 치환 또는 비치환되는 것을 의미한다.In one embodiment of the present specification, the 'substituted or unsubstituted' group in the group not bonded to the formula (1) among R10 to R19 is a trifluoromethyl group; Triphenylsilyl groups; A trimethylsilyl group; Triethylsilyl group; F; A phenyl group; Naphthyl group; A fluorenyl group; Furan group; Thiophene group; A dibenzofurane group; A dibenzothiophene group; Carbazole group; A phenoxathine group; Benzoxazole group; Chromen group; -COOR201; A nitrile group; An alkoxy group; A nitro group; An alkyl group; Phenoxy group; Diphenylamine group; A cyclohexyl group; And a substituent represented by the general formula (2).
본 명세서의 일 실시상태에 있어서, X1 및 X2는 서로 같거나 상이하고, 각각 독립적으로 할로겐기; 니트릴기기; -CO2R""; 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 치환 또는 비치환된 탄소수 2 내지 20의 알키닐기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기; 치환 또는 비치환된 탄소수 1 내지 20의 알콕시기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기이다.In one embodiment of the present specification, X1 and X2 are the same or different and each independently represents a halogen group; Nitrile equipment; -CO 2 R ""; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted C2-C20 alkynyl; A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms; A substituted or unsubstituted C1-C20 alkoxy group; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, X1 및 X2는 서로 같거나 상이하고, 각각 독립적으로 F; 니트릴기; -CO2R""; 메틸기; 헥실기; 니트로기 또는 프로필기로 치환된 페녹시기; 메톡시기; 에톡시기; F, 에톡시기 또는 프로필기로 치환 또는 비치환된 페닐기; 디메틸플루오레닐기; 티오펜기;
Figure PCTKR2018015522-appb-I000020
또는
Figure PCTKR2018015522-appb-I000021
이다.
In one embodiment of the present disclosure, X1 and X2 are the same or different and are each independently F; A nitrile group; -CO 2 R ""; Methyl group; Hexyl group; A phenoxy group substituted with a nitro group or a propyl group; Methoxy group; Ethoxy group; A phenyl group substituted or unsubstituted with F, an ethoxy group or a propyl group; A dimethylfluorenyl group; Thiophene group;
Figure PCTKR2018015522-appb-I000020
or
Figure PCTKR2018015522-appb-I000021
to be.
본 명세서의 일 실시상태에 있어서, 상기 R""은 치환 또는 비치환된 메틸기; 치환 또는 비치환된 에틸기; 치환 또는 비치환된 프로필기; 치환 또는 비치환된 부틸기; 치환 또는 비치환된 트리플루오로메틸기; 치환 또는 비치환된 퍼플루오로프로필기; 치환 또는 비치환된 페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 메톡시기; 치환 또는 비치환된 디하이드로벤조이소퀴놀린기; 또는 치환 또는 비치환된 크로메논기이다. In one embodiment of the present specification, R "" represents a substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted trifluoromethyl group; A substituted or unsubstituted perfluoropropyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted methoxy group; A substituted or unsubstituted dihydrobenzoisoquinoline group; Or a substituted or unsubstituted chlorenone group.
본 명세서의 일 실시상태에 있어서, X1 및 X2는 서로 같거나 상이하고, 각각 독립적으로 F; 니트릴기; -CO2R""; 메틸기; 헥실기; 니트로기 또는 프로필기로 치환된 페녹시기; 메톡시기; 에톡시기; F, 에톡시기 또는 프로필기로 치환 또는 비치환된 페닐기; 디메틸플루오레닐기; 티오펜기;
Figure PCTKR2018015522-appb-I000022
또는
Figure PCTKR2018015522-appb-I000023
이고, 상기 R""은 치환 또는 비치환된 퍼플루오로프로필기; 또는 치환 또는 비치환된 크로메논기이다.
In one embodiment of the present disclosure, X1 and X2 are the same or different and are each independently F; A nitrile group; -CO 2 R ""; Methyl group; Hexyl group; A phenoxy group substituted with a nitro group or a propyl group; Methoxy group; Ethoxy group; A phenyl group substituted or unsubstituted with F, an ethoxy group or a propyl group; A dimethylfluorenyl group; Thiophene group;
Figure PCTKR2018015522-appb-I000022
or
Figure PCTKR2018015522-appb-I000023
Quot; is a substituted or unsubstituted perfluoropropyl group; Or a substituted or unsubstituted chlorenone group.
본 명세서의 일 실시상태에 있어서, X1 및 X2는 서로 같거나 상이하고, 각각 독립적으로 F; 니트릴기; -CO2R""; 메틸기; 헥실기; 니트로기 또는 프로필기로 치환된 페녹시기; 메톡시기; 에톡시기; F, 에톡시기 또는 프로필기로 치환 또는 비치환된 페닐기; 디메틸플루오레닐기; 티오펜기;
Figure PCTKR2018015522-appb-I000024
또는
Figure PCTKR2018015522-appb-I000025
이고, 상기 R""은 퍼플루오로프로필기; 또는 케톤기로 치환 또는 비치환된 크로메논기이다.
In one embodiment of the present disclosure, X1 and X2 are the same or different and are each independently F; A nitrile group; -CO 2 R ""; Methyl group; Hexyl group; A phenoxy group substituted with a nitro group or a propyl group; Methoxy group; Ethoxy group; A phenyl group substituted or unsubstituted with F, an ethoxy group or a propyl group; A dimethylfluorenyl group; Thiophene group;
Figure PCTKR2018015522-appb-I000024
or
Figure PCTKR2018015522-appb-I000025
Quot; is a perfluoropropyl group; Or a chlorenone group substituted or unsubstituted with a ketone group.
본 명세서의 일 실시상태에 있어서, X1 및 X2는 서로 같거나 상이하고, F 또는 니트릴기이다. In one embodiment of the present specification, X1 and X2 are the same or different and are F or a nitrile group.
본 명세서의 일 실시상태에 있어서, X1 및 X2는 F이다. In one embodiment of the present disclosure, X1 and X2 are F.
본 명세서의 일 실시상태에 있어서, 상기 화학식 2는 하기 화학식 2-1 내지 2-3 중 어느하나로 표시된다.In one embodiment of the present invention, the formula (2) is represented by any one of the following formulas (2-1) to (2-3).
[화학식 2-1][Formula 2-1]
Figure PCTKR2018015522-appb-I000026
Figure PCTKR2018015522-appb-I000026
[화학식 2-2][Formula 2-2]
Figure PCTKR2018015522-appb-I000027
Figure PCTKR2018015522-appb-I000027
[화학식 2-3] [Formula 2-3]
Figure PCTKR2018015522-appb-I000028
Figure PCTKR2018015522-appb-I000028
상기 화학식 2-1 내지 2-3 에 있어서, In the general formulas (2-1) to (2-3)
상기 R10 내지 R19, X1 및 X2는 화학식 2에서의 정의와 같고, Wherein R10 to R19, X1 and X2 have the same definitions as in the formula (2)
R20 내지 R22는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카르보닐기; 에스테르기; 이미드기; 아미드기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 플루오로알킬기; 치환 또는 비치환된 알킬티오기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 헤테로아릴기; 또는 치환 또는 비치환된 탄화수소고리기이고, R20 to R22 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted fluoroalkyl group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted allyloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or a substituted or unsubstituted hydrocarbon ring group,
a 내지 c는 0 내지 4의 정수이고, a 내지 c가 2이상인 경우, 괄호안의 치환기는 서로 같거나 상이하다. a to c are an integer of 0 to 4, and when a to c are two or more, the substituents in parentheses are the same or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1의 화합물은 하기 구조식들 중에서 선택된다.In one embodiment of the present invention, the compound of Formula 1 is selected from the following structural formulas.
Figure PCTKR2018015522-appb-I000029
Figure PCTKR2018015522-appb-I000029
Figure PCTKR2018015522-appb-I000030
Figure PCTKR2018015522-appb-I000030
Figure PCTKR2018015522-appb-I000031
Figure PCTKR2018015522-appb-I000031
Figure PCTKR2018015522-appb-I000032
Figure PCTKR2018015522-appb-I000032
Figure PCTKR2018015522-appb-I000033
Figure PCTKR2018015522-appb-I000033
Figure PCTKR2018015522-appb-I000034
Figure PCTKR2018015522-appb-I000034
Figure PCTKR2018015522-appb-I000035
Figure PCTKR2018015522-appb-I000035
Figure PCTKR2018015522-appb-I000036
Figure PCTKR2018015522-appb-I000036
Figure PCTKR2018015522-appb-I000037
Figure PCTKR2018015522-appb-I000037
Figure PCTKR2018015522-appb-I000038
Figure PCTKR2018015522-appb-I000038
Figure PCTKR2018015522-appb-I000039
Figure PCTKR2018015522-appb-I000039
Figure PCTKR2018015522-appb-I000040
Figure PCTKR2018015522-appb-I000040
Figure PCTKR2018015522-appb-I000041
Figure PCTKR2018015522-appb-I000041
Figure PCTKR2018015522-appb-I000042
Figure PCTKR2018015522-appb-I000042
본 출원의 일 실시 상태에 따른 화합물은 후술하는 제조방법으로 제조될 수 있다.The compound according to one embodiment of the present application can be produced by a production method described below.
예컨대 상기 화학식 1의 화합물은 하기 반응식 1 과 같이 코어구조가 제조될수 있다. 치환기는 당기술분야에 알려져 있는 방법에 의하여 결합될 수 있으며, 치환기의 종류, 위치 또는 개수는 당기술분야에 알려져 있는 기술에 따라 변경될 수 있다.For example, the compound of Formula 1 may be prepared as shown in Reaction Scheme 1 below. Substituent groups may be attached by methods known in the art, and the type, position or number of substituent groups may be varied according to techniques known in the art.
[반응식 1] [Reaction Scheme 1]
Figure PCTKR2018015522-appb-I000043
Figure PCTKR2018015522-appb-I000043
브로모페닐아세토나이트릴 유도체 1당량에 아이오딘 1당량을 다이에틸에테르 용매에 희석하여, 영하 78℃에서 질소 하에 30분간 교반하여 주었다. 온도가 안정화된 후, 소튬메톡사이드 2 당량을 다이에틸에테르 용매에 희석하여, 위의 용액에 서서히 적가해준 후, 반응온도를 0℃로 올려 질소 하에서 5시간동안 교반해주었다. 반응 완료 후, 염산을 첨가하여 2시간 동안 추가로 교반해준 후 생성된 흰색 고체를 감압 여과를 통해 획득하여 주었다. 이 때 획득한 생성물은 메탄올을 이용하여 씻어주어 중화해주었다.1 equivalent of iodine to 1 equivalent of bromophenylacetonitrile derivative was diluted in a diethyl ether solvent, and the mixture was stirred at -78 占 폚 under nitrogen for 30 minutes. After the temperature was stabilized, 2 equivalents of sodium methoxide was diluted in a diethyl ether solvent, and the solution was slowly added dropwise to the above solution. The reaction temperature was raised to 0 캜 and stirred for 5 hours under nitrogen. After completion of the reaction, hydrochloric acid was added and the mixture was further stirred for 2 hours, and the resulting white solid was obtained by filtration under reduced pressure. At this time, the obtained product was neutralized by washing with methanol.
상기 반응식의 브로모페닐아세토나이트릴 유도체 대신,브로모나프탈레닐아세테이트나이트릴, 브로모안트라센일아세테이트니트릴과 같은 유도체를 사용하거나, 브로모페닐아세토나이트릴의 치환기인 R200 내지 R204를 치환하여 본원 발명의 화학식 1의 화합물을 제조할 수 있으며, 치환기의 종류, 위치, 개수는 당기술분야에 알려져 있는 기술에 따라 변경할 수 있다. Instead of the bromophenylacetonitrile derivative of the above reaction scheme, a derivative such as bromonaphthalenyl acetate nitrile, bromoanthraceneacetonitrile, or a derivative of bromo phenylacetonitrile, which is substituted with R200 to R204, Can be prepared, and the kind, position and number of substituent groups can be changed according to techniques known in the art.
구체적으로 상기 반응식 1로 얻어진 화합물에 Br 위치에, 아자보디피로 치환된 아민 화합물로 치환하여 본원 발명의 화합물 얻을 수 있으며, 반응식 1의 브로모페닐아세토나이트릴의 브롬의 위치나, 페닐 대신 다른 링커를 갖는 화합물을 사용하여 본원 발명의 화합물을 제조할 수 있다. Specifically, the compound of the present invention can be obtained by substituting the compound obtained in Reaction Scheme 1 with an amine compound substituted with azabodipyr at the Br position, and the position of the bromine of bromophenylacetonitrile of Scheme 1, Can be used to prepare the compounds of the present invention.
본 명세서의 일 실시상태에 따르면, 수지 매트릭스; 및 상기 수지 매트릭스 내에 분산된 화학식 1로 표시되는 화합물을 포함하는 색변환 필름을 제공한다. According to one embodiment of the present disclosure, a resin matrix; And a color conversion film comprising the compound represented by the general formula (1) dispersed in the resin matrix.
상기 색변환 필름 중의 상기 화학식 1로 표시되는 화합물의 함량은 0.001 내지 10 중량% 범위 내일 수 있다. The content of the compound represented by the formula (1) in the color conversion film may be in the range of 0.001 to 10% by weight.
상기 색변환 필름은 상기 화학식 1로 표시되는 화합물을 1종 포함할 수도 있고, 2 종 이상 포함할 수 있다. The color conversion film may contain one kind or two or more kinds of the compounds represented by the above formula (1).
상기 색변환 필름은 상기 화학식 1로 표시되는 화합물 이외에 추가의 형광물질을 더 포함할 수 있다. 청색 광을 발광하는 광원을 사용하는 경우에는 상기 색변환 필름은 녹색 발광 형광물질과 적색 발광 형광물질이 모두 포함되는 것이 바람직하다. 또한, 청색 광과 녹색 광을 발광하는 광원을 사용하는 경우에는 상기 색변환 필름은 적색 발광 형광물질만 포함할 수 있다. 다만, 이에 한정되는 것은 아니고, 청색 광을 발광하는 광원을 사용하는 경우에도, 녹색 발광 형광물질을 포함하는 별도의 필름을 적층하는 경우에는, 상기 색변환 필름은 적색 발광 화합물만을 포함할 수 있다. 반대로, 청색 광을 발광하는 광원을 사용하는 경우에도, 적색 발광 형광물질을 포함하는 별도의 필름을 적층하는 경우에는, 상기 색변환 필름은 녹색 발광 화합물만을 포함할 수 있다.The color conversion film may further include a fluorescent substance in addition to the compound represented by Formula 1. [ When a light source that emits blue light is used, the color conversion film preferably includes both a green light emitting fluorescent material and a red light emitting fluorescent material. When a light source that emits blue light and green light is used, the color conversion film may include only a red light emitting fluorescent material. However, the present invention is not limited thereto. In the case of using a light source that emits blue light, when a separate film containing a green light emitting fluorescent material is laminated, the color conversion film may include only a red light emitting compound. Conversely, even when a light source that emits blue light is used, in the case of laminating a separate film containing a red light-emitting fluorescent material, the color conversion film may include only a green light-emitting compound.
상기 색변환 필름은 수지 매트릭스; 및 상기 수지 매트릭스 내에 분산되고 상기 화학식 1로 표시되는 화합물과 상이한 파장의 빛을 발광하는 화합물을 포함하는 추가의 층을 더 포함할 수 있다. 상기 화학식 1로 표시되는 화합물과 상이한 파장의 빛을 발광하는 화합물도 역시 상기 화학식 1로 표현되는 화합물일 수도 있고, 공지된 다른 형광 물질일 수도 있다. Wherein the color conversion film comprises a resin matrix; And a further layer containing a light-emitting compound dispersed in the resin matrix and having a wavelength different from that of the compound represented by the general formula (1). The compound emitting light having a wavelength different from that of the compound represented by the formula (1) may also be a compound represented by the formula (1) or a known fluorescent material.
상기 수지 매트릭스의 재료는 열가소성 고분자 또는 열경화성 고분자인 것이 바람직하다. 구체적으로, 상기 수지 매트릭스의 재료로는 폴리메틸메타크릴레이트(PMMA)와 같은 폴리(메트)아크릴계, 폴리카보네이트계(PC), 폴리스티렌계(PS), 폴리아릴렌계(PAR), 폴리우레탄계(TPU), 스티렌-아크릴로니트릴계(SAN), 폴리비닐리덴플루오라이드계(PVDF), 개질된 폴리비닐리덴플루오라이드계(modified-PVDF) 등이 사용될 수 있다. The material of the resin matrix is preferably a thermoplastic polymer or a thermosetting polymer. Specifically, examples of the material of the resin matrix include poly (meth) acrylate, polycarbonate (PC), polystyrene (PS), polyarylene (PAR), polyurethane (TPU ), Styrene-acrylonitrile series (SAN), polyvinylidene fluoride series (PVDF), and modified polyvinylidene fluoride series (modified-PVDF).
본 명세서의 일 실시상태에 따르면, 전술한 실시상태에 따른 색변환 필름이 추가로 광확산 입자를 포함한다. 휘도를 향상시키기 위하여 종래에 사용되는 광확산 필름 대신 광확산 입자를 색변환 필름 내부에 분산시킴으로써, 별도의 광학산 필름을 사용하는 것에 비하여, 부착 공정을 생략할 수 있을 뿐만 아니라, 더 높은 휘도를 나타낼 수 있다.According to one embodiment of the present specification, the color conversion film according to the above-described embodiment further includes light diffusing particles. By dispersing the light diffusion particles in the color conversion film in place of the conventional light diffusion film in order to improve the brightness, the adhesion process can be omitted as compared with the use of a separate optical acid film, .
광확산 입자로는 수지 매트릭스와 굴절율이 높은 입자가 사용될 수 있으며, 예컨대 TiO2, 실리카, 보로실리케이트, 알루미나, 사파이어, 공기 또는 다른 가스, 공기- 또는 가스-충진된 중공 비드들 또는 입자들(예컨대, 공기/가스-충진된 유리 또는 폴리머); 폴리스티렌, 폴리카보네이트, 폴리메틸메타크릴레이트, 아크릴, 메틸 메타크릴레이트, 스티렌, 멜라민 수지, 포름알데히드 수지, 또는 멜라민 및 포름알데히드 수지를 비롯한 폴리머 입자들, 또는 이들의 임의의 적합한 조합이 사용될 수 있다.As the light-diffusing particles, resin matrices and particles having a high refractive index can be used. For example, TiO 2 , silica, borosilicate, alumina, sapphire, air or other gas, air- or gas- filled hollow beads or particles , Air / gas-filled glass or polymer); Polymer particles including polystyrene, polycarbonate, polymethylmethacrylate, acrylic, methylmethacrylate, styrene, melamine resin, formaldehyde resin, or melamine and formaldehyde resin, or any suitable combination thereof may be used .
상기 광확산 입자의 입경은 0.1 마이크로미터 내지 5 마이크로미터의 범위내, 예컨대 0.3 마이크로미터 내지 1 마이크로미터 범위내일 수 있다. 광확산 입자의 함량은 필요에 따라 정해질 수 있으며, 예컨대 수지 매트릭스 100 중량부를 기준으로 약 1 내지 30 중량부 범위내일 수 있다. The particle size of the light-diffusing particles may be in the range of 0.1 micrometer to 5 micrometers, for example, in the range of 0.3 micrometer to 1 micrometer. The content of the light-diffusing particles may be determined as necessary, and may be, for example, within a range of about 1 to 30 parts by weight based on 100 parts by weight of the resin matrix.
전술한 실시상태에 따른 색변환 필름은 두께가 2 마이크로미터 내지 200 마이크로미터일 수 있다. 특히, 상기 색변환 필름은 두께가 2 마이크로미터 내지 20 마이크로미터의 얇은 두께에서도 높은 휘도를 나타낼 수 있다. 이는 단위 부피 상에 포함되는 형광 물질 분자의 함량이 양자점에 비하여 높기 때문이다. The color conversion film according to the above-described embodiment may have a thickness of 2 micrometers to 200 micrometers. In particular, the color conversion film can exhibit high luminance even at a thin thickness of 2 to 20 micrometers. This is because the content of the fluorescent substance molecules contained in the unit volume is higher than the quantum dots.
전술한 실시상태에 따른 색변환 필름은 일면에 기재가 구비될 수 있다. 이 기재는 상기 색변환 필름의 제조시 지지체로서의 기능을 할 수 있다. 기재의 종류로는 특별히 한정되지 않으며, 투명하고, 상기 지지체로서의 기능을 할 수 있는 것이라면 그 재질이나 두께에 한정되지 않는다. 여기서 투명이란, 가시광선 투과율이 70% 이상인 것을 의미한다. 예컨대 상기 기재로는 PET 필름이 사용될 수 있다. The color conversion film according to the above-described embodiments may have a substrate on one side thereof. This substrate may serve as a support in the production of the color conversion film. The kind of the substrate is not particularly limited and is not limited to the material and thickness as long as it is transparent and can function as the support. Here, transparent means that the visible light transmittance is 70% or more. For example, a PET film may be used as the substrate.
전술한 색변환 필름은 전술한 화학식 1로 표시되는 화합물이 용해된 수지 용액을 기재 위에 코팅하고 건조하거나, 전술한 화학식 1로 표시되는 화합물을 수지와 함께 압출하여 필름화함으로써 제조될 수 있다. The above-mentioned color conversion film can be produced by coating a resin solution in which the compound represented by the formula (1) has been dissolved on a substrate and drying or extruding the compound represented by the formula (1) together with the resin to form a film.
상기 수지 용액 중에는 전술한 화학식 1로 표시되는 화합물이 용해되어 있기 때문에 화학식 1로 표시되는 화합물이 용액 중에 균질하게 분포하게 된다. 이는 별도의 분산공정을 필요로 하는 양자점 필름의 제조공정과는 상이하다. Since the compound represented by the above-mentioned formula (1) is dissolved in the resin solution, the compound represented by the formula (1) is homogeneously distributed in the solution. This is different from the manufacturing process of a quantum dot film requiring a separate dispersion process.
상기 화학식 1로 표시되는 화합물이 용해된 수지 용액은 용액 중에 전술한 화학식 1로 표시되는 화합물이 수지가 녹아있는 상태라면 그 제조방법은 특별히 한정되지 않는다. The resin solution in which the compound represented by Formula 1 is dissolved is not particularly limited as long as the compound represented by Formula 1 is dissolved in the solution.
일 예에 따르면, 상기 화학식 1로 표시되는 화합물이 용해된 수지 용액은 화학식 1로 표시되는 화합물을 용매에 녹여 제1 용액을 준비하고, 수지를 용매에 녹여 제2 용액을 준비하고, 상기 제1 용액과 제2 용액을 혼합하는 방법에 의하여 제조될 수 있다. 상기 제1 용액과 제2 용액을 혼합할 때, 균질하게 섞는 것이 바람직하다. 그러나, 이에 한정되지 않고, 용매에 화학식 1로 표시되는 화합물과 수지를 동시에 첨가하여 녹이는 방법, 용매에 화학식 1로 표시되는 화합물을 녹이고 이어서 수지를 첨가하여 녹이는 방법, 용매에 수지를 녹이고 이어서 화학식 1로 표시되는 화합물을 첨가하여 녹이는 방법 등이 사용될 수 있다. According to an example, the resin solution in which the compound represented by Formula 1 is dissolved may be prepared by preparing a first solution by dissolving the compound represented by Formula 1 in a solvent, dissolving the resin in a solvent to prepare a second solution, And then mixing the solution and the second solution. When the first solution and the second solution are mixed, it is preferable to mix them homogeneously. However, the present invention is not limited to this, and a method of dissolving the compound represented by Chemical Formula 1 and a resin simultaneously in a solvent to dissolve the compound represented by Chemical Formula 1 and dissolving the compound represented by Chemical Formula 1 in a solvent followed by dissolving the resin by dissolving the resin in a solvent, A method of dissolving a compound represented by the formula
상기 용액 중에 포함되어 있는 수지로는 전술한 수지 매트릭스 재료, 이 수지 매트릭스 수지로 경화가능한 모노머, 또는 이들의 혼합이 사용될 수 있다. 예컨대, 상기 수지 매트릭스 수지로 경화가능한 모노머로는 (메트)아크릴계 모노머가 있으며, 이는 UV 경화에 의하여 수지 매트릭스 재료로 형성될 수 있다. 이와 같이 경화가능한 모노머를 사용하는 경우, 필요에 따라 경화에 필요한 개시제가 더 첨가될 수 있다. As the resin contained in the solution, the above-mentioned resin matrix material, a monomer curable with the resin matrix resin, or a mixture thereof can be used. For example, as the monomer curable with the resin matrix resin, there is a (meth) acrylic monomer, which can be formed from a resin matrix material by UV curing. In the case of using such a curable monomer, an initiator necessary for curing may be further added if necessary.
상기 용매로는 특별히 한정되지 않으며, 상기 코팅 공정에 악영향을 미치지 않으면서 추후 건조에 의하여 제거될 수 있는 것이라면 특별히 한정되지 않는다. 상기 용매의 비제한적인 예로는 톨루엔, 자일렌, 아세톤, 클로로포름, 각종 알코올계 용매, MEK(메틸에틸케톤), MIBK(메틸이소부틸케톤), EA(에틸에세테이트), 부틸아세테이트, DMF(디메틸포름아미드), DMAc(디메틸아세트아미드), DMSO(디메틸술폭사이드), NMP(N-메틸-피롤리돈) 등이 사용될 수 있으며, 1 종 또는 2 종 이상이 혼합되어 사용될 수 있다. 상기 제1 용액과 제2 용액을 사용하는 경우, 이들 각각의 용액에 포함되는 용매는 동일할 수도 있고, 상이할 수도 있다. 상기 제1 용액과 상기 제2 용액에 서로 상이한 종류의 용매가 사용되는 경우에도, 이들 용매는 서로 혼합될 수 있도록 상용성을 갖는 것이 바람직하다. The solvent is not particularly limited and is not particularly limited as long as it can be removed by drying without adversely affecting the coating process. Nonlimiting examples of the solvent include toluene, xylene, acetone, chloroform, various alcohol solvents, MEK (methyl ethyl ketone), MIBK (methyl isobutyl ketone), EA (ethyl acetate), butyl acetate, DMF Dimethylformamide), DMAc (dimethylacetamide), DMSO (dimethylsulfoxide), NMP (N-methyl-pyrrolidone) and the like may be used alone or in admixture of two or more. When the first solution and the second solution are used, the solvent contained in each of these solutions may be the same or different. Even when different kinds of solvents are used for the first solution and the second solution, it is preferable that these solvents have compatibility so that they can be mixed with each other.
상기 화학식 1로 표시되는 화합물이 용해된 수지 용액을 기재 상에 코팅하는 공정은 롤투롤 공정을 이용할 수 있다. 예컨대, 기재가 권취된 롤로부터 기재를 푼 후, 상기 기재의 일면에 상기 화학식 1로 표시되는 화합물이 용해된 수지 용액을 코팅하고, 건조한 후, 이를 다시 롤에 권취하는 공정으로 수행될 수 있다. 롤투롤 공정을 이용하는 경우, 상기 수지 용액의 점도를 상기 공정이 가능한 범위로 결정하는 것이 바람직하며, 예컨대 200 내지 2,000 cps 범위 내에서 결정할 수 있다. A roll-to-roll process can be used for the step of coating the resin solution on which the compound represented by the formula (1) is dissolved. For example, a step of dissolving a substrate from a roll on which a substrate is wound, coating a resin solution in which the compound represented by the formula (1) is dissolved on one surface of the substrate, drying, and then winding the same on a roll again. In the case of using a roll-to-roll process, it is preferable to determine the viscosity of the resin solution within a range in which the process can be performed, and may be determined within a range of, for example, 200 to 2,000 cps.
상기 코팅 방법으로는 공지된 다양한 방식을 이용할 수 있으며, 예컨대 다이(die) 코터가 사용될 수도 있고, 콤마(comma) 코터, 역콤마(reverse comma) 코터 등 다양한 바 코팅 방식이 사용될 수도 있다. As the coating method, various known methods can be used, for example, a die coater may be used, and various bar coating methods such as a comma coater, a reverse comma coater, and the like may be used.
상기 코팅 이후에 건조 공정을 수행한다. 건조 공정은 용매를 제거하기에 필요한 조건으로 수행할 수 있다. 예컨대, 기재가 코팅 공정시 진행하는 방향으로, 코터에 인접하여 위치한 오븐에서 용매가 충분히 날아갈 조건으로 건조하여, 기재 위에 원하는 두께 및 농도의 화학식 1로 표시되는 화합물을 비롯한 형광 물질을 포함하는 색변환 필름을 얻을 수 있다. After the coating, a drying process is performed. The drying process can be carried out under the conditions necessary for removing the solvent. For example, the substrate is dried in an oven located adjacent to the coater in a direction in which the substrate proceeds in a coating process, under conditions that the solvent is sufficiently blown, and a color conversion including a fluorescent substance, A film can be obtained.
상기 용액 중에 포함되는 수지로서 상기 수지 매트릭스 수지로 경화가능한 모노머를 사용하는 경우, 상기 건조 전에 또는 건조와 동시에 경화, 예컨대 UV 경화를 수행할 수 있다. When a monomer curable with the resin matrix resin is used as the resin contained in the solution, curing such as UV curing may be performed before or during the drying.
상기 화학식 1로 표시되는 화합물을 수지와 함께 압출하여 필름화하는 경우에는 당기술분야에 알려져 있는 압출 방법을 이용할 수 있으며, 예컨대, 화학식 1로 표시되는 화합물을 폴리카보네이트계(PC), 폴리(메트)아크릴계, 스티렌-아크릴로니트릴계(SAN)와 같은 수지를 함께 압출함으로써 색변환 필름을 제조할 수 있다.When the compound represented by the formula (1) is extruded together with the resin to form a film, extrusion methods known in the art can be used. For example, the compound represented by the formula (1) is reacted with a polycarbonate- ) Acrylic resin, and styrene-acrylonitrile (SAN) resin are simultaneously extruded to produce a color conversion film.
본 명세서의 일 실시상태에 따르면, 상기 색변환 필름은 적어도 일면에 보호 필름 또는 배리어 필름이 구비될 수 있다. 보호 필름 및 배리어 필름으로는 당 기술분야에 알려져 있는 것이 사용될 수 있다. According to one embodiment of the present invention, the color conversion film may be provided on at least one side with a protective film or a barrier film. As the protective film and the barrier film, those known in the art can be used.
본 명세서의 일 실시상태에 따르면, 전술한 색변환 필름을 포함하는 백라이트 유닛을 제공한다. 상기 백라이트 유닛은 상기 색변환 필름을 포함하는 것을 제외하고는 당기술분야에 알려져 있는 백라이트 유닛 구성을 가질 수 있다. 도 1에 일 예에 따른 백라이트 유닛 구조의 모식도를 나타내었다. 도 1에 따른 백라이트 유닛은 측쇄형 광원(101), 광원을 둘러싸는 반사판(102), 상기 광원으로부터 직접 발광하거나, 상기 반사판에서 반사된 빛을 유도하는 도광판(103), 상기 도광판의 일면에 구비된 반사층(104), 및 상기 도광판의 상기 반사층에 대향하는 면의 반대면에 구비된 색변환 필름(105)을 포함한다. 도 1에서 (106)으로 표시된 부분은 도광판의 광분산 패턴이다. 도광판 내부로 유입된 광은 반사, 전반사, 굴절, 투과 등의 광학적 과정의 반복으로 불균일한 광분포를 가지는데, 이를 균일한 밝기로 유도하기 위하여 2차원 적인 광분산 패턴을 이용할 수 있다. 그러나, 본 발명의 범위가 도 1에 의하여 한정되는 것은 아니며, 광원은 측쇄형 뿐만 아니라 직하형이 사용될 수도 있으며, 반사판이나 반사층은 필요에 따라 생략되거나 다른 구성으로 대체될 수도 있으며, 필요에 따라 추가의 필름, 예컨대 광확산 필름, 집광 필름, 휘도 향상 필름 등이 더 추가로 구비될 수 있다. According to one embodiment of the present disclosure, there is provided a backlight unit including the above-mentioned color conversion film. The backlight unit may have a backlight unit configuration known in the art, except that it includes the color conversion film. FIG. 1 shows a schematic diagram of a backlight unit structure according to an example. The backlight unit according to FIG. 1 includes a side-chain type light source 101, a reflection plate 102 surrounding the light source, a light guide plate 103 for directly emitting light from the light source or guiding light reflected from the reflection plate, And a color conversion film 105 provided on the opposite surface of the light guide plate opposite to the reflective layer. In Fig. 1, the portion indicated by (106) is a light dispersion pattern of the light guide plate. The light introduced into the light guide plate has a non-uniform light distribution due to repetition of optical processes such as reflection, total reflection, refraction, and transmission, and a two-dimensional light dispersion pattern can be used to induce uniform brightness. However, the scope of the present invention is not limited to that shown in FIG. 1, and the light source may be a direct-type as well as a side-chain type, and the reflection plate or the reflective layer may be omitted or replaced with another structure if necessary, A light-diffusing film, a light-condensing film, a luminance improving film, and the like.
본 명세서의 일 실시상태에 따르면, 상기 백라이트 유닛을 포함하는 디스플레이 장치를 제공한다. 백라이트 유닛을 포함하는 디스플레이 장치라면 특별히 한정되지 않으며, TV, 컴퓨터의 모니터, 노트북, 휴대폰 등에 포함될 수 있다.According to an embodiment of the present disclosure, there is provided a display device including the backlight unit. And is not particularly limited as long as it is a display device including a backlight unit, and may be included in a TV, a computer monitor, a notebook computer, a mobile phone, and the like.
이하, 본 명세서를 구체적으로 설명하기 위해 실시예를 들어 상세하게 설명하기로 한다. 그러나, 본 명세서에 따른 실시예들은 여러 가지 다른 형태로 변형될 수 있으며, 본 출원의 범위가 아래에서 상술하는 실시예들에 한정되는 것으로 해석되지 않는다. 본 출원의 실시예들은 당업계에서 평균적인 지식을 가진 자에게 본 명세서를 보다 완전하게 설명하기 위해 제공되는 것이다.Hereinafter, the present invention will be described in detail by way of examples with reference to the drawings. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present application is not construed as being limited to the embodiments described below. The embodiments of the present application are provided to enable those skilled in the art to more fully understand the present invention.
<합성예 1>&Lt; Synthesis Example 1 &
Figure PCTKR2018015522-appb-I000044
Figure PCTKR2018015522-appb-I000044
1) 화합물 A1 합성1) Synthesis of Compound A1
4-브로모아닐린 1당량에 아자보디피(a) 1.5 당량을 테트라하이드로퓨란 용매에 용해한 후, 포타슘카보네이트 3당량을 물에 녹여 섞어준 후, 질소 하에서 80℃로 가열 교반해주었다. 온도가 안정화된 후, 촉매 Pd(PPh3)4 0.03 당량을 첨가하여 반응을 진행해주었다. 반응 종결 후, 반응물을 상온으로 내리고 물과 클로로포름을 이용하여 추출을 진행하고, 무수 마그네슘설패이트를 이용하여 수분을 제거해주었다. 수분이 제거된 반응물을 감압 증류를 통해 농축 후 클로로포름과 에탄올을 이용하여 화합물 A2를 획득하였다. 1.5 equivalents of azabodiphe (a) in 1 equivalent of 4-bromoaniline was dissolved in a tetrahydrofuran solvent, and 3 equivalents of potassium carbonate was dissolved in water and mixed. The mixture was stirred under heating at 80 占 폚 under nitrogen. After the temperature stabilized, the catalyst Pd (PPh 3) The reaction was proceeded by the addition of 4 equiv. 0.03. After completion of the reaction, the reaction mixture was cooled to room temperature, extracted with water and chloroform, and water was removed using anhydrous magnesium sulfate. The water-removed reaction product was concentrated by distillation under reduced pressure, and Compound A2 was obtained by using chloroform and ethanol.
2) 화합물 A2 합성2) Synthesis of Compound A2
합성된 A1 물질 1당량과 1-브로모-4-아이오도벤젠 1.5 당량을 톨루엔 용매에 희석한 후, 소듐뷰톡사이드 1.2 당량을 첨가하여, 질소 하에서 90℃로 가열하여주었다. 온도가 안정화된 후, Pd(dba)2 촉매를 0.01당량 첨가하여 반응을 진행해주었다. 반응 종결 후, 반응물을 상온으로 내리고 물과 클로로포름을 이용하여 추출을 진행하고, 무수 마그네슘설패이트를 이용하여 수분을 제거해주었다. 수분이 제거된 반응물을 감압 증류를 통해 농축 후 클로로포름과 에탄올을 이용하여 생성물을 획득하였다. 1 equivalent of the synthesized Al material and 1.5 equivalent of 1-bromo-4-iodobenzene were diluted in a toluene solvent, 1.2 equivalents of sodium butoxide was added, and the mixture was heated to 90 DEG C under nitrogen. After the temperature was stabilized, 0.01 equivalent of Pd (dba) 2 catalyst was added to proceed the reaction. After completion of the reaction, the reaction mixture was cooled to room temperature, extracted with water and chloroform, and water was removed using anhydrous magnesium sulfate. The water-removed reaction product was concentrated by distillation under reduced pressure, and the product was obtained by using chloroform and ethanol.
제조예Manufacturing example 1. 화합물  1. Compound 1 의1 of 합성 synthesis
Figure PCTKR2018015522-appb-I000045
Figure PCTKR2018015522-appb-I000045
1) 화합물 1c 의 합성1) Synthesis of Compound 1c
화합물 1a 2g 을 화합물 1b 2 당량과 함께 테트라하이드로퓨란(THF) 용매 100 mL 에서 희석한 후, 포타슘카보네이트 3당량을 물 50 mL 에 희석하여 첨가해주었다. 혼합된 용액을 질소 하에서 80℃로 가열 교반하여 반응을 진행하였다. 반응이 완료된 후, 클로로포름과 물을 이용하여 추출을 진행하였고, 추출된 유기층을 무수마그네슘설패이트를 이용하여 물을 제거해준 후, 감압 증류를 통해 농축 후 클로로포름과 에탄올을 이용하여 생성물을 획득해주었다. 이를 통해 화합물 1c을 1.78g (82%) 획득하였다. HR LC/MS/MS m/z calcd for C38H26BF2N4 (M+): 587.2219; found: 587.22182 g of Compound 1a was diluted with 100 mL of a tetrahydrofuran (THF) solvent together with 2 equivalents of Compound 1b, and then 3 equivalents of potassium carbonate was diluted to 50 mL of water. The mixed solution was heated and stirred at 80 DEG C under nitrogen to conduct the reaction. After completion of the reaction, the extraction was carried out using chloroform and water. The extracted organic layer was washed with water using anhydrous magnesium sulfate, concentrated by distillation under reduced pressure, and then the product was obtained using chloroform and ethanol gave. This gave 1.78 g (82%) of compound 1c . HR LC / MS / MS m / z calcd for C 38 H 26 BF 2 N 4 (M +): 587.2219; found: 587.2218
2) 화합물 1 의 합성2) Synthesis of Compound 1
합성된 화합물 1c 1 g을 화합물 1d 0.5 당량, 세슘카보네이트 3당량과 함께 톨루엔 30 mL 에 희석한 후, 질소 하에서 90℃로 가열 교반하여 주었다. 가열 온도 안정화 후, 촉매 Pd[P(t-Bu)3]2 를 0.01 당량 첨가하여 반응을 진행해주었다. 반응이 완료되면, 필터를 진행하여 염기를 제거해준 후, 획득한 유기층을 물을 이용하여 추출을 진행해주었다. 추출된 유기층은 무수 마그네슘설패이트를 이용하여 수분을 제거 후, 감압 증류를 통해 용매를 농축 후, 클로로포름과 에탄올을 이용하여 화합물 1을 0.90 g (76%)를 획득하였다. HR LC/MS/MS m/z calcd for C92H58B2F4N10 (M+): 1400.4968; found: 1400.49661 g of the synthesized Compound 1c was diluted with 0.5 equivalent of Compound 1d and 3 equivalents of cesium carbonate in 30 mL of toluene, and the mixture was heated and stirred at 90 占 폚 under nitrogen. After stabilizing the heating temperature, 0.01 equivalent of the catalyst Pd [P (t-Bu) 3 ] 2 was added to proceed the reaction. When the reaction was completed, the filter was allowed to proceed to remove the base, and the obtained organic layer was extracted with water. The extracted organic layer was dried over anhydrous magnesium sulfate, and the solvent was concentrated by distillation under reduced pressure. Then, 0.90 g (76%) of compound 1 was obtained using chloroform and ethanol. HR LC / MS / MS m / z calcd for C 92 H 58 B 2 F 4 N 10 (M +): 1400.4968; found: 1400.4966
제조예Manufacturing example 2. 화합물  2. Compound 2 의2 of 합성 synthesis
Figure PCTKR2018015522-appb-I000046
Figure PCTKR2018015522-appb-I000046
1) 화합물 2c 의 합성1) Synthesis of compound 2c
화합물 1b 대신 화합물 2b 를 2 당량을 이용한 것을 제외하고, 화합물 1c 와 합성법은 동일하다. 이 때 화합물 2c 는 1.50g (65%) 을 획득하였다. HR LC/MS/MS m/z calcd for C40H26BF2N4O (M+): 627.2168; found: 627.2169Compound 1c and the synthesis method are the same except that 2 equivalents of compound 2b is used instead of compound 1b. At this time, Compound 2c obtained 1.50 g (65%). HR LC / MS / MS m / z calcd for C 40 H 26 BF 2 N 4 O (M +): 627.2168; found: 627.2169
2) 화합물 2의 합성2) Synthesis of Compound 2
화합물 1c 대신 화합물 2c 1 g 을 이용하여, 반응을 진행한 것을 제외하고 화합물 1의 합성과 동일하게 진행하였다. 이를 통해 화합물 2를 0.80 g(68%) 획득하였다. HR LC/MS/MS m/z calcd for C96H58B2F4N10O2 (M+): 1481.4900; found: 1481.4901Compound 1c was used instead of Compound 1c, and the reaction was carried out in the same manner as the synthesis of Compound 1, except that the reaction was carried out. This gave 0.80 g (68%) of compound 2. HR LC / MS / MS m / z calcd for C 96 H 58 B 2 F 4 N 10 O 2 (M +): 1481.4900; found: 1481.4901
제조예Manufacturing example 3. 화합물  3. Compound 3 의3 of 합성 synthesis
Figure PCTKR2018015522-appb-I000047
Figure PCTKR2018015522-appb-I000047
1) 화합물 3c 의 합성1) Synthesis of Compound 3c
화합물 1b 대신 화합물 3b 를 2 당량을 이용한 것을 제외하고, 화합물 1c 와 합성법은 동일하다. 이 때 화합물 3c 는 1.56g (61%) 을 획득하였다. HR LC/MS/MS m/z calcd for C46H32BF2N4 (M+): 663.2532; found: 663.2533Compound 1c and the synthesis method are the same except that 2 equivalents of compound 3b are used instead of compound 1b. At this time, Compound 3c obtained 1.56 g (61%). HR LC / MS / MS m / z calcd for C 46 H 32 BF 2 N 4 (M +): 663.2532; found: 663.2533
2) 화합물 3의 합성2) Synthesis of Compound 3
화합물 1c 대신 화합물 3c 1 g 을 이용하여, 반응을 진행한 것을 제외하고 화합물 1의 합성방법과 동일하게 진행하였다. 이를 통해 화합물 3을 0.5 g(43%) 획득하였다. HR LC/MS/MS m/z calcd for C108H70B2F4N10 (M+): 1605.5941; found: 1605.5939Compound 1c was used instead of Compound 1c, and the reaction was carried out in the same manner as in the synthesis of Compound 1, except that 1 g of Compound 3c was used. 0.5 g (43%) of compound 3 was obtained. HR LC / MS / MS m / z calcd for C 108 H 70 B 2 F 4 N 10 (M +): 1605.5941; found: 1605.5939
제조예Manufacturing example 4. 화합물 4의 합성  4. Synthesis of Compound 4
Figure PCTKR2018015522-appb-I000048
Figure PCTKR2018015522-appb-I000048
1) 화합물 4c 의 합성1) Synthesis of compound 4c
화합물 1b 대신 화합물 4b 를 2 당량을 이용한 것을 제외하고, 화합물 1c 와 합성법은 동일하다. 이 때 화합물 4c 는 1.64g (78%) 을 획득하였다. HR LC/MS/MS m/z calcd for C35H26BF2N4O (M+): 567.2168; found: 567.2169Compound 1c and the synthesis method are the same except that 2 equivalents of compound 4b is used instead of compound 1b. At this time, Compound 4c obtained 1.64 g (78%). HR LC / MS / MS m / z calcd for C 35 H 26 BF 2 N 4 O (M +): 567.2168; found: 567.2169
2) 화합물 4의 합성2) Synthesis of Compound 4
화합물 1c 대신 화합물 4c 1 g 을 이용하여, 반응을 진행한 것을 제외하고 화합물 1의 합성방법과 동일하게 진행하였다. 이를 통해 화합물 4을 0.68 g(57%) 획득하였다. HR LC/MS/MS m/z calcd for C86H58B2F4N10O2 (M+): 1360.4866; found: 1360.4866The procedure of the synthesis of Compound 1 was repeated except that 1 g of Compound 4c was used instead of Compound 1c, and the reaction proceeded. 0.68 g (57%) of compound 4 was obtained. HR LC / MS / MS m / z calcd for C 86 H 58 B 2 F 4 N 10 O 2 (M +): 1360.4866; found: 1360.4866
제조예Manufacturing example 5. 화합물 5의 합성 5. Synthesis of Compound 5
Figure PCTKR2018015522-appb-I000049
Figure PCTKR2018015522-appb-I000049
1) 화합물 5c 의 합성1) Synthesis of compound 5c
화합물 1b 대신 화합물 5b 를 2 당량을 이용한 것을 제외하고, 화합물 1c 와 합성법은 동일하다. 이 때 화합물 5c 는 1.48g (72%) 을 획득하였다. HR LC/MS/MS m/z calcd for C34H23BF3N4 (M+): 555.1968; found: 555.1968Compound 1c was synthesized in the same manner as Compound 1c, except that 2 equivalents of Compound 5b was used instead of Compound 1b. At this time, Compound 5c obtained 1.48 g (72%). HR LC / MS / MS m / z calcd for C 34 H 23 BF 3 N 4 (M +): 555.1968; found: 555.1968
2) 화합물 5의 합성2) Synthesis of Compound 5
화합물 1c 대신 화합물 5c 1 g 을 이용하여, 반응을 진행한 것을 제외하고 화합물 1의 합성방법과 동일하게 진행하였다. 이를 통해 화합물 5을 0.82 g(68%) 획득하였다. HR LC/MS/MS m/z calcd for C84H52B2F6N10 (M+): 1336.4467; found: 1336.4466Compound 1c was used instead of Compound 1c, and the reaction was carried out in the same manner as in the synthesis of Compound 1, except that 1 g of Compound 5c was used. This gave 0.82 g (68%) of compound 5. HR LC / MS / MS m / z calcd for C 84 H 52 B 2 F 6 N 10 (M +): 1336.4467; found: 1336.4466
제조예Manufacturing example 6. 화합물 6의 합성 6. Synthesis of Compound 6
Figure PCTKR2018015522-appb-I000050
Figure PCTKR2018015522-appb-I000050
1) 화합물 6c 의 합성1) Synthesis of Compound 6c
화합물 1a 대신 화합물 6a 2g을 사용하고,화합물 1b 대신 화합물 6b 를 2 당량을 이용한 것을 제외하고, 화합물 1c 와 합성법은 동일하다. 이 때 화합물 6c 는 1.43g (58%) 을 획득하였다. HR LC/MS/MS m/z calcd for C53H34BF5N5 (M+): 846.2827; found: 846.2828Compound 1c and the synthesis method are the same except that 2 g of Compound 6a is used in place of Compound 1a and 2 equivalents of Compound 6b is used in place of Compound 1b. At this time, Compound 6c obtained 1.43 g (58%). HR LC / MS / MS m / z Calcd for C 53 H 34 BF 5 N 5 (M +): 846.2827; found: 846.2828
2) 화합물 6의 합성2) Synthesis of Compound 6
화합물 1c 대신 화합물 6c 1 g 을 이용하여, 반응을 진행한 것을 제외하고 화합물 1의 합성과 동일하게 진행하였다. 이를 통해 화합물 6을 0.72 g(63%) 획득하였다. HR LC/MS/MS m/z calcd for C122H74B2F10N12 (M+): 1919.6219; found: 1919.6217Compound 1c was used instead of Compound 1c, and the reaction was carried out in the same manner as the synthesis of Compound 1, except that 1 g of Compound 6c was used. This gave 0.72 g (63%) of compound 6. HR LC / MS / MS m / z calcd for C 122 H 74 B 2 F 10 N 12 (M +): 1919.6219; found: 1919.6217
제조예Manufacturing example 7. 화합물  7. Compound 7 의7's 합성 synthesis
Figure PCTKR2018015522-appb-I000051
Figure PCTKR2018015522-appb-I000051
1) 화합물 7c 의 합성1) Synthesis of Compound 7c
화합물 1a 대신 화합물 7a 2g을 사용하고, 화합물 1b 대신 화합물 7b 를 2 당량을 이용한 것을 제외하고, 화합물 1c 와 합성법은 동일하다. 이 때 화합물 7c 는 1.41g (58%) 을 획득하였다. HR LC/MS/MS m/z calcd for C85H56BF8N4Si (M+):1323.4240; found: 1323.4241Compound 1c and the synthesis method are the same except that 2 g of compound 7a is used in place of compound 1a and 2 equivalents of compound 7b is used in place of compound 1b. At this time, Compound (7c) obtained 1.41 g (58%). HR LC / MS / MS m / z calcd for C 85 H 56 BF 8 N 4 Si (M +): 1323.4240; found: 1323.4241
2) 화합물 7의 합성2) Synthesis of Compound 7
화합물 1c 대신 화합물 7c 1 g을 이용하여, 반응을 진행한 것을 제외하고 화합물 1의 합성과 동일하게 진행하였다. 이를 통해 화합물 7을 0.93 g(85%) 획득하였다. HR LC/MS/MS m/z calcd for C186H118B2F16N10Si2 (M+): 2873.9044; found: 2873.9044Compound 1c was used instead of Compound 1c, and the reaction was carried out in the same manner as in the synthesis of Compound 1, except that 1 g of Compound 7c was used. This gave 0.93 g (85%) of compound 7. HR LC / MS / MS m / z calcd for C 186 H 118 B 2 F 16 N 10 Si 2 (M +): 2873.9044; found: 2873.9044
제조예Manufacturing example 8. 화합물 8의 합성 8. Synthesis of Compound 8
Figure PCTKR2018015522-appb-I000052
Figure PCTKR2018015522-appb-I000052
1) 화합물 8c 의 합성1) Synthesis of Compound 8c
화합물 1a 대신 화합물 8a 2g을 사용하고, 화합물 1b 대신 화합물 8b 를 2 당량을 이용한 것을 제외하고, 화합물 1c 와 합성법은 동일하다. 이 때 화합물 8c 는 2.0g (76%) 을 획득하였다. HR LC/MS/MS m/z calcd C61H36BF8N4 (M+):987.2905; found: 987.2905Compound 1c and the synthesis method are the same except that 2 g of compound 8a is used instead of compound 1a and 2 equivalents of compound 8b is used in place of compound 1b. At this time, 2.0g (76%) of Compound 8c was obtained. HR LC / MS / MS m / z calcd C 61 H 36 BF 8 N 4 (M +): 987.2905; found: 987.2905
2) 화합물 8의 합성2) Synthesis of Compound 8
화합물 1c 대신 화합물 8c 1 g을 이용하여, 화합물 1d 대신 화합물 8d를 이용하여 반응을 진행한 것을 제외하고 화합물 1의 합성과 동일하게 진행하였다. 이를 통해 화합물 8을 0.92 g(81%) 획득하였다. HR LC/MS/MS m/z calcd for C140H82B2F16N10O2 (M+): 2261.6586; found: 2261.6586Compound 1c was used instead of Compound 1c, and the reaction was conducted in the same manner as Compound 1 except that Compound 8d was used instead of Compound 1d. This gave 0.92 g (81%) of compound 8. HR LC / MS / MS m / z calcd for C 140 H 82 B 2 F 16 N 10 O 2 (M +): 2261.6586; found: 2261.6586
제조예Manufacturing example 9. 화합물 9의 합성 9. Synthesis of Compound 9
Figure PCTKR2018015522-appb-I000053
Figure PCTKR2018015522-appb-I000053
1) 화합물 9c 의 합성1) Synthesis of Compound 9c
화합물 1a 대신 화합물 9a 2g을 사용하고,화합물 1b 대신 화합물 8b 를 2 당량을 이용한 것을 제외하고, 화합물 1c 와 합성법은 동일하다. 이 때 화합물 9c 는 2.12g (83%) 을 획득하였다. HR LC/MS/MS m/z calcd C78H48BF2N4 (M+):1089.3940; found: 1089.3941Compound 1c and the synthesis method are the same except that 2g of Compound 9a is used instead of Compound 1a and 2eq of Compound 8b is used instead of Compound 1b. At this time, 2.12 g (83%) of Compound 9c was obtained. HR LC / MS / MS m / z calcd C 78 H 48 BF 2 N 4 (M +): 1089.3940; found: 1089.3941
2) 화합물 9의 합성2) Synthesis of Compound 9
화합물 1c 대신 화합물 9c 1 g을 이용하여, 화합물 1d 대신 화합물 8d를 이용하여 반응을 진행한 것을 제외하고 화합물 1의 합성과 동일하게 진행하였다. 이를 통해 화합물 9를 0.81 g(72%) 획득하였다. HR LC/MS/MS m/z calcd for C174H106B2F4N10O2 (M+): 2465.8656; found: 2465.8655Compound 1c was prepared in the same manner as Compound 1 except that 1 g of Compound 9c was used instead of Compound 1c and Compound 8d was used instead of Compound 1d. This gave 0.81 g (72%) of compound 9. HR LC / MS / MS m / z calcd for C 174 H 106 B 2 F 4 N 10 O 2 (M +): 2465.8656; found: 2465.8655
제조예Manufacturing example 10. 화합물 10의 합성 10. Synthesis of Compound 10
Figure PCTKR2018015522-appb-I000054
Figure PCTKR2018015522-appb-I000054
화합물 1c 대신 화합물 10a 2g을 이용한 것을 제외하고, 화합물 1의 합성과 동일하게 진행하였다. 이 때 화합물 10을 2.00 g (85%) 획득하였다. HR LC/MS/MS m/z calcd C72H46B2F4N10 (M+):1148.4029; found: 1148.4028The procedure was the same as the synthesis of Compound 1, except that 2 g of Compound 10a was used instead of Compound 1c. At this time, 2.00 g (85%) of compound 10 was obtained. HR LC / MS / MS m / z Calcd C 72 H 46 B 2 F 4 N 10 (M +): 1148.4029; found: 1148.4028
제조예Manufacturing example 11. 화합물 11의 합성 11. Synthesis of Compound 11
Figure PCTKR2018015522-appb-I000055
Figure PCTKR2018015522-appb-I000055
화합물 1c 대신 화합물 11a 2g을 이용한 것을 제외하고, 화합물 1의 합성과 동일하게 진행하였다. 이 때 화합물 11을 1.66 g (73%) 획득하였다. HR LC/MS/MS m/z calcd C120H82B2F4N10Si2 (M+):1817.6418; found: 1817.6419The procedure was the same as the synthesis of Compound 1, except that 2g of Compound 11a was used instead of Compound 1c. At this time, 1.66 g (73%) of Compound 11 was obtained. HR LC / MS / MS m / z Calcd C 120 H 82 B 2 F 4 N 10 Si 2 (M +): 1817.6418; found: 1817.6419
제조예Manufacturing example 12. 화합물 12의 합성 12. Synthesis of Compound 12
Figure PCTKR2018015522-appb-I000056
Figure PCTKR2018015522-appb-I000056
화합물 1c 대신 화합물 12a 2g을 이용한 것을 제외하고, 화합물 1의 합성과 동일하게 진행하였다. 이 때 화합물 12를 1.66 g (73%) 획득하였다. HR LC/MS/MS m/z calcd C120H82B2F4N10Si2 (M+):1817.6418; found: 1817.6419The procedure was the same as the synthesis of Compound 1, except that 2g of Compound 12a was used instead of Compound 1c. At this time, 1.66 g (73%) of Compound 12 was obtained. HR LC / MS / MS m / z Calcd C 120 H 82 B 2 F 4 N 10 Si 2 (M +): 1817.6418; found: 1817.6419
제조예Manufacturing example 13. 화합물 13의 합성 13. Synthesis of Compound 13
Figure PCTKR2018015522-appb-I000057
Figure PCTKR2018015522-appb-I000057
화합물 1c 대신 화합물 13a 2g을 이용한 것을 제외하고, 화합물 1의 합성과 동일하게 진행하였다. 이 때 화합물 13을 1.50 g (68%) 획득하였다. HR LC/MS/MS m/z calcd C148H94B2F16N10Si2 (M+):2393.7166; found: 2393.7155The procedure was the same as the synthesis of Compound 1, except that 2 g of Compound 13a was used instead of Compound 1c. At this time, 1.50 g (68%) of Compound 13 was obtained. HR LC / MS / MS m / z calcd C 148 H 94 B 2 F 16 N 10 Si 2 (M +): 2393.7166; found: 2393.7155
제조예Manufacturing example 14. 화합물 14의 합성 14. Synthesis of Compound 14
Figure PCTKR2018015522-appb-I000058
Figure PCTKR2018015522-appb-I000058
화합물 1c 대신 화합물 14a 2g을 이용한 것을 제외하고, 화합물 1의 합성과 동일하게 진행하였다. 이 때 화합물 14를 1.58 g (72%) 획득하였다. HR LC/MS/MS m/z calcd C136H72B4F32N16 (M+):2581.6021; found: 2581.6022The procedure was the same as the synthesis of Compound 1, except that 2 g of Compound 14a was used instead of Compound 1c. At this time, 1.58 g (72%) of Compound 14 was obtained. HR LC / MS / MS m / z Calcd C 136 H 72 B 4 F 32 N 16 (M +): 2581.6021; found: 2581.6022
제조예Manufacturing example 15. 화합물 15의 합성 15. Synthesis of Compound 15
Figure PCTKR2018015522-appb-I000059
Figure PCTKR2018015522-appb-I000059
화합물 1c 대신 화합물 15a 2g을 이용한 것을 제외하고, 화합물 1의 합성과 동일하게 진행하였다. 이 때 화합물 15를 1.86 g (81%) 획득하였다. HR LC/MS/MS m/z calcd C100H54B2F16N12 (M+):1749.4559; found: 1749.4558The procedure was the same as the synthesis of Compound 1, except that 2g of Compound 15a was used instead of Compound 1c. At this time, 1.86 g (81%) of compound 15 was obtained. HR LC / MS / MS m / z Calcd C 100 H 54 B 2 F 16 N 12 (M +): 1749.4559; found: 1749.4558
제조예Manufacturing example 16. 화합물 16의 합성 16. Synthesis of Compound 16
Figure PCTKR2018015522-appb-I000060
Figure PCTKR2018015522-appb-I000060
화합물 1c 대신 화합물 16a 2g을 이용한 것을 제외하고, 화합물 1의 합성과 동일하게 진행하였다. 이 때 화합물 16를 1.61 g (74%) 획득하였다. HR LC/MS/MS m/z calcd C174H108B2F16N10Si2 (M+):2719.8216; found: 2719.8216The procedure was the same as the synthesis of Compound 1, except that 2g of Compound 16a was used instead of Compound 1c. At this time, 1.61 g (74%) of Compound 16 was obtained. HR LC / MS / MS m / z calcd C 174 H 108 B 2 F 16 N 10 Si 2 (M +): 2719.8216; found: 2719.8216
<합성예 2>&Lt; Synthesis Example 2 &
Figure PCTKR2018015522-appb-I000061
Figure PCTKR2018015522-appb-I000061
a. 화합물 A3 합성a. Compound A3 Synthesis
4-브로모아닐린 1당량에 아자보디피 (b) 1.5 당량을 사용하여, 화합물 A1 과 동일한 방법으로 합성을 진행하였다.The synthesis was carried out in the same manner as the compound A1 using 1.5 equivalents of azabodipine (b) in one equivalent of 4-bromoaniline.
b. 화합물 A4 합성.b. Compound A4 synthesis.
합성된 A3 화합물을 이용하여 화합물 A2 와 동일한 방법으로 합성을 진행하였다.Synthesis was conducted in the same manner as Compound A2 using the synthesized A3 compound.
제조예Manufacturing example 17. 화합물 17의 합성 17. Synthesis of Compound 17
Figure PCTKR2018015522-appb-I000062
Figure PCTKR2018015522-appb-I000062
1) 화합물 17c 의 합성1) Synthesis of Compound 17c
화합물 1a 대신 화합물 17a 2g 을 사용하고, 화합물 1b 대신 화합물 17b 를 2 당량을 이용한 것을 제외하고, 화합물 1c 와 합성법은 동일하다. 이 때 화합물 9c 는 2.12g (83%) 을 획득하였다. HR LC/MS/MS m/z calcd C48H27BF5N5O (M+):795.2229; found: 795.2228Compound 1c and the synthesis method are the same except that 2g of compound 17a is used in place of compound 1a and 2 equivalents of compound 17b is used in place of compound 1b. At this time, 2.12 g (83%) of Compound 9c was obtained. HR LC / MS / MS m / z calcd C 48 H 27 BF 5 N 5 O (M +): 795.2229; found: 795.2228
2) 화합물 17의 합성2) Synthesis of Compound 17
화합물 1c 대신 화합물 17c 1 g을 이용하여 반응을 진행한 것을 제외하고 화합물 1의 합성과 동일하게 진행하였다. 이를 통해 화합물 17을 0.81 g(72%) 획득하였다. HR LC/MS/MS m/z calcd for C112H60B2F10N12O2 (M+): 1817.5022; found: 1817.5022Compound 1 was prepared in the same manner as Compound 1 except that 1 g of Compound 17c was used instead of Compound 1c. This gave 0.81 g (72%) of compound 17. HR LC / MS / MS m / z calcd for C 112 H 60 B 2 F 10 N 12 O 2 (M +): 1817.5022; found: 1817.5022
제조예Manufacturing example 18. 화합물 18의 합성 18. Synthesis of Compound 18
Figure PCTKR2018015522-appb-I000063
Figure PCTKR2018015522-appb-I000063
화합물 1c 대신 화합물 18a 2g을 이용한 것을 제외하고, 화합물 1의 합성과 동일하게 진행하였다. 이 때 화합물 18를 2.06 g (85%) 획득하였다. HR LC/MS/MS m/z calcd C84H52B2F4N10 (M+):1298.4499; found: 1298.4499The procedure was the same as the synthesis of Compound 1, except that 2g of Compound 18a was used instead of Compound 1c. At this time, 2.06 g (85%) of compound 18 was obtained. HR LC / MS / MS m / z Calcd C 84 H 52 B 2 F 4 N 10 (M +): 1298.4499; found: 1298.4499
제조예Manufacturing example 19. 화합물 19의 합성 19. Synthesis of Compound 19
Figure PCTKR2018015522-appb-I000064
Figure PCTKR2018015522-appb-I000064
화합물 1c 대신 화합물 19a 2g을 이용한 것을 제외하고, 화합물 1의 합성과 동일하게 진행하였다. 이 때 화합물 19를 1.63 g (71%) 획득하였다. HR LC/MS/MS m/z calcd C102H54B2F16N12 (M+):1773.4559; found: 1773.4558The procedure was the same as the synthesis of Compound 1, except that 2g of Compound 19a was used instead of Compound 1c. At this time, 1.63 g (71%) of compound 19 was obtained. HR LC / MS / MS m / z Calcd C 102 H 54 B 2 F 16 N 12 (M +): 1773.4559; found: 1773.4558
제조예Manufacturing example 20. 화합물  20. Compound 20 의Twenty 합성 synthesis
Figure PCTKR2018015522-appb-I000065
Figure PCTKR2018015522-appb-I000065
화합물 1c 대신 화합물 20a 2g을 이용한 것을 제외하고, 화합물 1의 합성과 동일하게 진행하였다. 이 때 화합물 20을 1.53 g (67%) 획득하였다. HR LC/MS/MS m/z calcd C106H54B2F12N16 (M+):1801.4745; found: 1801.4745The procedure was the same as the synthesis of Compound 1, except that 2 g of Compound 20a was used instead of Compound 1c. At this time, 1.53 g (67%) of compound 20 was obtained. HR LC / MS / MS m / z Calcd C 106 H 54 B 2 F 12 N 16 (M +): 1801.4745; found: 1801.4745
<< 합성예Synthetic example 3> 3>
Figure PCTKR2018015522-appb-I000066
Figure PCTKR2018015522-appb-I000066
a. 화합물 A5 합성a. Compound A5 Synthesis
4-브로모아닐린 1당량에 아자보디피 (c) 1.5 당량을 사용하여, 화합물 A1 과 동일한 방법으로 합성을 진행하였다.The synthesis was carried out in the same manner as the compound A1 using 1.5 equivalents of azabodipine (c) in one equivalent of 4-bromoaniline.
b. 화합물 A6 합성.b. Compound A6 Synthesis.
합성된 A5 화합물을 이용하여 화합물 A2 와 동일한 방법으로 합성을 진행하였다.Synthesis was conducted in the same manner as Compound A2 using the synthesized A5 compound.
제조예Manufacturing example 21. 화합물 21의 합성 21. Synthesis of Compound 21
Figure PCTKR2018015522-appb-I000067
Figure PCTKR2018015522-appb-I000067
1) 화합물 21c 의 합성1) Synthesis of Compound 21c
화합물 1a 대신 화합물 21a 2g 과 화합물 1b 를 2 당량을 이용한 것을 제외하고, 화합물 1c 와 합성법은 동일하다. 이 때 화합물 21c 는 1.57g (72%) 을 획득하였다. HR LC/MS/MS m/z calcd C38H25BF2N4 (M+):586.2140; found: 586.2140Compound 1c and the synthesis method are the same except that 2g of Compound 21a and 2eq of Compound 1b are used instead of Compound 1a. At this time, compound 21c obtained 1.57 g (72%). HR LC / MS / MS m / z Calcd C 38 H 25 BF 2 N 4 (M +): 586.2140; found: 586.2140
2) 화합물 21의 합성2) Synthesis of Compound 21
화합물 1c 대신 화합물 21c 2 g을 이용한 것을 제외하고 화합물 1의 합성과 동일하게 진행하였다. 이를 통해 화합물 21를 1.72 g(72%) 획득하였다. HR LC/MS/MS m/z calcd for C92H56B2F4N10 (M+): 1398.4812; found: 1398.4813The procedure was the same as the synthesis of Compound 1 except that 2 g of Compound 21c was used instead of Compound 1c. This gave 1.72 g (72%) of compound 21. HR LC / MS / MS m / z calcd for C 92 H 56 B 2 F 4 N 10 (M +): 1398.4812; found: 1398.4813
제조예Manufacturing example 22. 화합물 22의 합성 22. Synthesis of Compound 22
Figure PCTKR2018015522-appb-I000068
Figure PCTKR2018015522-appb-I000068
1) 화합물 22c 의 합성1) Synthesis of Compound 22c
화합물 1a 대신 화합물 21a 2g을 사용하고, 화합물 1b 대신 화합물 2b 를 2 당량을 이용한 것을 제외하고, 화합물 1c 와 합성법은 동일하다. 이 때 화합물 22c 는 2.49g (64%) 을 획득하였다. HR LC/MS/MS m/z calcd C40H25BF2N4O (M+): 626.2089; found: 626.2088Compound 1c and the synthesis method are the same except that 2 g of compound 21a is used in place of compound 1a and 2 equivalents of compound 2b is used in place of compound 1b. At this time, Compound 22c obtained 2.49 g (64%). HR LC / MS / MS m / z Calcd C 40 H 25 BF 2 N 4 O (M +): 626.2089; found: 626.2088
2) 화합물 22의 합성2) Synthesis of Compound 22
화합물 1c 대신 화합물 22c 2 g을 이용한 것을 제외하고 화합물 1의 합성과 동일하게 진행하였다. 이를 통해 화합물 22를 1.37 g(58%) 획득하였다. HR LC/MS/MS m/z calcd for C96H56B2F4N10O2 (M+): 1479.4743; found: 1479.4742The procedure was the same as the synthesis of Compound 1 except that 2 g of Compound 22c was used instead of Compound 1c. This gave 1.37 g (58%) of compound 22. HR LC / MS / MS m / z calcd for C 96 H 56 B 2 F 4 N 10 O 2 (M +): 1479.4743; found: 1479.4742
제조예Manufacturing example 23. 화합물 23의 합성 23. Synthesis of Compound 23
Figure PCTKR2018015522-appb-I000069
Figure PCTKR2018015522-appb-I000069
1) 화합물 23c 의 합성1) Synthesis of Compound 23c
화합물 1a 대신 화합물 21a 2g을 사용하고, 화합물 1b 대신 화합물 3b 를 2 당량을 이용한 것을 제외하고, 화합물 1c 와 합성법은 동일하다. 이 때 화합물 23c 는 1.48 g (58%) 을 획득하였다. HR LC/MS/MS m/z calcd C46H31BF2N4 (M+): 688.2610; found: 688.2612Compound 1c and the synthesis method are the same except that 2 g of compound 21a is used instead of compound 1a and 2 equivalents of compound 3b is used in place of compound 1b. At this time, Compound 23c obtained 1.48 g (58%). HR LC / MS / MS m / z calcd C 46 H 31 BF 2 N 4 (M +): 688.2610; found: 688.2612
2) 화합물 23의 합성2) Synthesis of Compound 23
화합물 1c 대신 화합물 23c 2 g을 이용한 것을 제외하고 화합물 1의 합성과 동일하게 진행하였다. 이를 통해 화합물 23을 1.77 g (76%) 획득하였다. HR LC/MS/MS m/z calcd for C108H68B2F4N10 (M+): 1603.5784; found: 1603.5783The same procedure as in the synthesis of Compound 1 was conducted except that 2 g of Compound 23c was used instead of Compound 1c. This gave 1.77 g (76%) of compound 23. HR LC / MS / MS m / z calcd for C 108 H 68 B 2 F 4 N 10 (M +): 1603.5784; found: 1603.5783
제조예Manufacturing example 24. 화합물 24의 합성 24. Synthesis of Compound 24
Figure PCTKR2018015522-appb-I000070
Figure PCTKR2018015522-appb-I000070
화합물 1c 대신 화합물 24a 2g을 이용한 것을 제외하고, 화합물 1의 합성과 동일하게 진행하였다. 이 때 화합물 24를 1.57 g (65%) 획득하였다. HR LC/MS/MS m/z calcd C84H52B2F4N10 (M+): 1298.4499; found: 1298.4498The procedure was the same as the synthesis of Compound 1 except that 2 g of Compound 24a was used instead of Compound 1c. At this time, 1.57 g (65%) of Compound 24 was obtained. HR LC / MS / MS m / z Calcd C 84 H 52 B 2 F 4 N 10 (M +): 1298.4499; found: 1298.4498
제조예Manufacturing example 25. 화합물 25의 합성 25. Synthesis of Compound 25
Figure PCTKR2018015522-appb-I000071
Figure PCTKR2018015522-appb-I000071
1) 화합물 25c 의 합성1) Synthesis of compound 25c
화합물 1a 대신 화합물 25a 2g 을 이용한 것을 제외하고, 화합물 1c 와 합성법은 동일하다. 이 때 화합물 25c 는 1.52 g (72%) 을 획득하였다. HR LC/MS/MS m/z calcd C63H41BF2N4 (M+): 902.3392; found: 902.3393Compound 1c and the synthesis method are the same except that 2g of Compound 25a is used instead of Compound 1a. At this time, Compound 25c obtained 1.52 g (72%). HR LC / MS / MS m / z Calcd C 63 H 41 BF 2 N 4 (M +): 902.3392; found: 902.3393
2) 화합물 25의 합성2) Synthesis of Compound 25
화합물 1c 대신 화합물 25c 2 g을 이용한 것을 제외하고 화합물 1의 합성과 동일하게 진행하였다. 이를 통해 화합물 25를 1.51 g(67%) 획득하였다. HR LC/MS/MS m/z calcd for C142H88B2F4N10 (M+): 2031.7349; found: 2031.7349The procedure of synthesis of Compound 1 was repeated except that 2 g of Compound 25c was used instead of Compound 1c. This gave 1.51 g (67%) of compound 25. HR LC / MS / MS m / z calcd for C 142 H 88 B 2 F 4 N 10 (M +): 2031.7349; found: 2031.7349
제조예Manufacturing example 26. 화합물 26의 합성 26. Synthesis of Compound 26
Figure PCTKR2018015522-appb-I000072
Figure PCTKR2018015522-appb-I000072
1) 화합물 26c 의 합성1) Synthesis of Compound 26c
화합물 1a 대신 화합물 25a 2g 을 사용하고, 화합물 1b 대신 화합물 2b 를 2 당량을 이용한 것을 제외하고, 화합물 1c 와 합성법은 동일하다. 이 때 화합물 26c 는 1.23 g (56%) 을 획득하였다. HR LC/MS/MS m/z calcd C65H41BF2N4O (M+): 942.3341; found: 942.3340Compound 1c and the synthesis method are the same except that 2g of Compound 25a is used in place of Compound 1a and 2 equivalents of Compound 2b is used in place of Compound 1b. At this time, Compound 26c was obtained 1.23 g (56%). HR LC / MS / MS m / z calcd C 65 H 41 BF 2 N 4 O (M +): 942.3341; found: 942.3340
2) 화합물 26의 합성2) Synthesis of Compound 26
화합물 1c 대신 화합물 26c 2 g을 이용한 것을 제외하고 화합물 1의 합성과 동일하게 진행하였다. 이를 통해 화합물 26을 1.39 g (62%) 획득하였다. HR LC/MS/MS m/z calcd for C146H88B2F4N10O0 (M+): 2111.7248; found: 2111.7249The procedure was the same as the synthesis of Compound 1 except that 2 g of Compound 26c was used instead of Compound 1c. This gave 1.39 g (62%) of compound 26. HR LC / MS / MS m / z calcd for C 146 H 88 B 2 F 4 N 10 O 0 (M +): 2111.7248; found: 2111.7249
제조예Manufacturing example 27. 화합물 27의 합성 27. Synthesis of Compound 27
Figure PCTKR2018015522-appb-I000073
Figure PCTKR2018015522-appb-I000073
1) 화합물 27c 의 합성1) Synthesis of Compound 27c
화합물 1a 대신 화합물 25a 2g을 사용하고, 화합물 1b 대신 화합물 3b 를 2 당량을 이용한 것을 제외하고, 화합물 1c 와 합성법은 동일하다. 이 때 화합물 27c 는 1.81 g (77%) 을 획득하였다. HR LC/MS/MS m/z calcd C71H47BF2N4 (M+): 1004.3862; found: 1004.3862Compound 1c and the synthesis method are the same except that 2 g of Compound 25a is used instead of Compound 1a and 2 equivalents of Compound 3b is used in place of Compound 1b. At this time, Compound 27c was obtained 1.81 g (77%). HR LC / MS / MS m / z calcd C 71 H 47 BF 2 N 4 (M +): 1004.3862; found: 1004.3862
2) 화합물 27의 합성2) Synthesis of Compound 27
화합물 1c 대신 화합물 27c 2 g을 이용한 것을 제외하고 화합물 1의 합성과 동일하게 진행하였다. 이를 통해 화합물 27을 1.27 g (57%) 획득하였다. HR LC/MS/MS m/z calcd for C158H100B2F4N10 (M+): 2235.8288; found: 2235.8287The procedure was the same as the synthesis of Compound 1 except that 2 g of Compound 27c was used instead of Compound 1c. This gave 1.27 g (57%) of compound 27. HR LC / MS / MS m / z calcd for C 158 H 100 B 2 F 4 N 10 (M +): 2235.8288; found: 2235.8287
제조예Manufacturing example 28. 화합물 28의 합성 28. Synthesis of Compound 28
Figure PCTKR2018015522-appb-I000074
Figure PCTKR2018015522-appb-I000074
1) 화합물 28c 의 합성1) Synthesis of Compound 28c
화합물 1a 대신 화합물 25a 2g을 사용하고, 화합물 1b 대신 화합물 28b 를 2 당량을 이용한 것을 제외하고, 화합물 1c 와 합성법은 동일하다. 이 때 화합물 28c 는 1.27 g (60%) 을 획득하였다. HR LC/MS/MS m/z calcd C63H47BF2N4 (M+): 908.3862; found: 908.3864Compound 1c and the synthesis method are the same except that 2g of Compound 25a is used in place of Compound 1a and 2 equivalents of Compound 28b is used in place of Compound 1b. At this time, Compound 28c was obtained 1.27 g (60%). HR LC / MS / MS m / z Calcd C 63 H 47 BF 2 N 4 (M +): 908.3862; found: 908.3864
2) 화합물 28의 합성2) Synthesis of compound 28
화합물 1c 대신 화합물 28c 2 g을 이용한 것을 제외하고 화합물 1의 합성과 동일하게 진행하였다. 이를 통해 화합물 28을 1.30 g (58%) 획득하였다. HR LC/MS/MS m/z calcd for C142H100B2F4N10 (M+): 2043.8288; found: 2043.8287The same procedure as in the synthesis of Compound 1 was conducted except that 2 g of Compound 28c was used instead of Compound 1c. This gave 1.30 g (58%) of compound 28. HR LC / MS / MS m / z calcd for C 142 H 100 B 2 F 4 N 10 (M +): 2043.8288; found: 2043.8287
제조예Manufacturing example 29. 화합물 29의 합성 29. Synthesis of Compound 29
Figure PCTKR2018015522-appb-I000075
Figure PCTKR2018015522-appb-I000075
화합물 1c 대신 화합물 29a 2g을 이용한 것을 제외하고, 화합물 1의 합성과 동일하게 진행하였다. 이 때 화합물 29를 1.54 g (68%) 획득하였다. HR LC/MS/MS m/z calcd C134H84B2F4N10 (M+): 1931.7036; found: 1931.7037The procedure was the same as the synthesis of Compound 1, except that 2g of Compound 29a was used instead of Compound 1c. At this time, 1.54 g (68%) of Compound 29 was obtained. HR LC / MS / MS m / z Calcd C 134 H 84 B 2 F 4 N 10 (M +): 1931.7036; found: 1931.7037
제조예Manufacturing example 30. 화합물  30. Compound 30 의Thirty 합성 synthesis
Figure PCTKR2018015522-appb-I000076
Figure PCTKR2018015522-appb-I000076
1) 화합물 30c 의 합성1) Synthesis of Compound 30c
화합물 1a 대신 화합물 30a 2g 과 화합물 1b 2 당량을 이용한 것을 제외하고, 화합물 1c 와 합성법은 동일하다. 이 때 화합물 30c 는 1.41g (67%) 을 획득하였다. HR LC/MS/MS m/z calcd C64H40BF5N4 (M+): 970.3266; found: 970.3265Compound 1c and the synthesis method are the same except that 2g of compound 30a and 2eq of compound 1b are used instead of compound 1a. At this time, compound 30c obtained 1.41 g (67%). HR LC / MS / MS m / z Calcd C 64 H 40 BF 5 N 4 (M +): 970.3266; found: 970.3265
2) 화합물 30의 합성2) Synthesis of Compound 30
화합물 1c 대신 화합물 30c 2 g을 이용한 것을 제외하고 화합물 1의 합성과 동일하게 진행하였다. 이를 통해 화합물 30을 1.27 g (57%) 획득하였다. HR LC/MS/MS m/z calcd for C144H86B2F10N10 (M+): 2167.7097; found: 2167.7099The procedure was the same as the synthesis of Compound 1 except that 2 g of Compound 30c was used instead of Compound 1c. This gave 1.27 g (57%) of compound 30. HR LC / MS / MS m / z calcd for C 144 H 86 B 2 F 10 N 10 (M +): 2167.7097; found: 2167.7099
제조예Manufacturing example 31. 화합물 31의 합성 31. Synthesis of Compound 31
Figure PCTKR2018015522-appb-I000077
Figure PCTKR2018015522-appb-I000077
1) 화합물 31c 의 합성1) Synthesis of Compound 31c
화합물 1a 대신 화합물 30a 2g을 사용하고, 화합물 1b 대신 화합물 2b 를 2 당량을 이용한 것을 제외하고, 화합물 1c 와 합성법은 동일하다. 이 때 화합물 31c 는 1.60g (73%) 을 획득하였다. HR LC/MS/MS m/z calcd C66H40BF5N4O (M+): 1010.3215; found: 1010.3216Compound 1c and the synthesis method are the same except that 2g of Compound 30a is used in place of Compound 1a and 2 equivalents of Compound 2b is used in place of Compound 1b. At this time, Compound 31c obtained 1.60 g (73%). HR LC / MS / MS m / z calcd C 66 H 40 BF 5 N 4 O (M +): 1010.3215; found: 1010.3216
2) 화합물 31의 합성2) Synthesis of Compound 31
화합물 1c 대신 화합물 31c 2 g을 이용한 것을 제외하고 화합물 1의 합성과 동일하게 진행하였다. 이를 통해 화합물 31을 1.47 g (66%) 획득하였다. HR LC/MS/MS m/z calcd for C148H86B2F10N10O2 (M+): 2247.6995; found: 2247.6997The procedure was the same as the synthesis of Compound 1 except that 2 g of Compound 31c was used instead of Compound 1c. This gave 1.47 g (66%) of compound 31. HR LC / MS / MS m / z calcd for C 148 H 86 B 2 F 10 N 10 O 2 (M +): 2247.6995; found: 2247.6997
제조예Manufacturing example 32. 화합물  32. Compound 32 의32 합성 synthesis
Figure PCTKR2018015522-appb-I000078
Figure PCTKR2018015522-appb-I000078
1) 화합물 32c 의 합성1) Synthesis of Compound 32c
화합물 1a 대신 화합물 30a 2g 을 사용하고, 화합물 1b 대신 화합물 3b 를 2 당량을 이용한 것을 제외하고, 화합물 1c 와 합성법은 동일하다. 이 때 화합물 32c 는 1.32g (57%) 을 획득하였다. HR LC/MS/MS m/z calcd C72H46BF5N4 (M+): 1072.3736; found: 1072.3735Compound 1c and the synthesis method are the same except that 2g of Compound 30a is used in place of Compound 1a and 2 equivalents of Compound 3b is used in place of Compound 1b. At this time, Compound 32c obtained 1.32 g (57%). HR LC / MS / MS m / z calcd C 72 H 46 BF 5 N 4 (M +): 1072.3736; found: 1072.3735
2) 화합물 32의 합성2) Synthesis of Compound 32
화합물 1c 대신 화합물 32c 2 g을 이용한 것을 제외하고 화합물 1의 합성과 동일하게 진행하였다. 이를 통해 화합물 32를 1.66 g (75%) 획득하였다. HR LC/MS/MS m/z calcd for C160H98B2F10N10 (M+): 2371.8036; found: 2371.8035The procedure was the same as the synthesis of Compound 1 except that 2 g of Compound 32c was used instead of Compound 1c. This gave 1.66 g (75%) of compound 32. HR LC / MS / MS m / z calcd for C 160 H 98 B 2 F 10 N 10 (M +): 2371.8036; found: 2371.8035
제조예Manufacturing example 33. 화합물 33의 합성 33. Synthesis of Compound 33
Figure PCTKR2018015522-appb-I000079
Figure PCTKR2018015522-appb-I000079
1) 화합물 33c 의 합성1) Synthesis of Compound 33c
화합물 1a 대신 화합물 30a 2g 을 사용하고, 화합물 1b 대신 화합물 33b 를 2 당량을 이용한 것을 제외하고, 화합물 1c 와 합성법은 동일하다. 이 때 화합물 33c 는 1.63g (77%) 을 획득하였다. HR LC/MS/MS m/z calcd C64H46BF5N4 (M+): 976.3736; found: 976.3736Compound 1c and the synthesis method are the same except that 2g of Compound 30a is used in place of Compound 1a and 2 equivalents of Compound 33b is used in place of Compound 1b. At this time, Compound 33c obtained 1.63 g (77%). HR LC / MS / MS m / z Calcd for C 64 H 46 BF 5 N 4 (M +): 976.3736; found: 976.3736
2) 화합물 33의 합성2) Synthesis of Compound 33
화합물 1c 대신 화합물 33c 2 g을 이용한 것을 제외하고 화합물 1의 합성과 동일하게 진행하였다. 이를 통해 화합물 33을 1.81 g (81%) 획득하였다. HR LC/MS/MS m/z calcd for C144H98B2F10N10 (M+): 2179.8036; found: 2179.8035The procedure was the same as the synthesis of Compound 1 except that 2 g of Compound 33c was used instead of Compound 1c. 1.81 g (81%) of compound 33 was obtained. HR LC / MS / MS m / z calcd for C 144 H 98 B 2 F 10 N 10 (M +): 2179.8036; found: 2179.8035
제조예Manufacturing example 34. 화합물 34의 합성 34. Synthesis of Compound 34
Figure PCTKR2018015522-appb-I000080
Figure PCTKR2018015522-appb-I000080
1) 화합물 34c 의 합성1) Synthesis of Compound 34c
화합물 1a 대신 화합물 30a 2g 을 사용하고, 화합물 1b 대신 화합물 34b 를 2 당량을 이용한 것을 제외하고, 화합물 1c 와 합성법은 동일하다. 이 때 화합물 34c 는 1.37 g (67%) 을 획득하였다. HR LC/MS/MS m/z calcd C61H37BF5N5 (M+): 945.3062; found: 945.3061Compound 1c and the synthesis method are the same except that 2g of Compound 30a is used in place of Compound 1a and 2 equivalents of Compound 34b is used in place of Compound 1b. At this time, Compound 34c obtained 1.37 g (67%). HR LC / MS / MS m / z Calcd C 61 H 37 BF 5 N 5 (M +): 945.3062; found: 945.3061
2) 화합물 34의 합성2) Synthesis of Compound 34
화합물 1c 대신 화합물 34c 2 g을 이용한 것을 제외하고 화합물 1의 합성과 동일하게 진행하였다. 이를 통해 화합물 34를 1.21 g (54%) 획득하였다. HR LC/MS/MS m/z calcd for C138H80B2F10N12 (M+): 2117.6689; found: 2117.6689The procedure was the same as the synthesis of Compound 1 except that 2 g of Compound 34c was used instead of Compound 1c. This gave 1.21 g (54%) of compound 34. HR LC / MS / MS m / z calcd for C 138 H 80 B 2 F 10 N 12 (M +): 2117.6689; found: 2117.6689
제조예Manufacturing example 35. 화합물 35의 합성 35. Synthesis of Compound 35
Figure PCTKR2018015522-appb-I000081
Figure PCTKR2018015522-appb-I000081
화합물 1c 대신 화합물 35a 2g을 이용한 것을 제외하고, 화합물 1의 합성과 동일하게 진행하였다. 이 때 화합물 35를 1.48 g (66%) 획득하였다. HR LC/MS/MS m/z calcd C136H82B2F10N10 (M+): 2067.6784; found: 2067.6783The procedure was the same as the synthesis of Compound 1, except that 2g of Compound 35a was used instead of Compound 1c. At this time, 1.48 g (66%) of Compound 35 was obtained. HR LC / MS / MS m / z Calcd C 136 H 82 B 2 F 10 N 10 (M +): 2067.6784; found: 2067.6783
제조예Manufacturing example 36. 화합물 36의 합성 36. Synthesis of Compound 36
Figure PCTKR2018015522-appb-I000082
Figure PCTKR2018015522-appb-I000082
화합물 1c 대신 화합물 35a 2g을 이용하고, 화합물 1d 대신에 화합물 8d를 사용한 것을 제외하고, 화합물 1의 합성과 동일하게 진행하였다. 이 때 화합물 36을 1.20 g (52%) 획득하였다. HR LC/MS/MS m/z calcd C138H86B2F10N10O2 (M+): 2127.6995; found: 2127.6997Compound 2 was prepared in the same manner as Compound 1 except that 2 g of Compound 35a was used instead of Compound 1c and Compound 8d was used instead of Compound 1d. At this time, 1.20 g (52%) of Compound 36 was obtained. HR LC / MS / MS m / z Calcd C 138 H 86 B 2 F 10 N 10 O 2 (M +): 2127.6995; found: 2127.6997
제조예Manufacturing example 37. 화합물 37의 합성 37. Synthesis of Compound 37
Figure PCTKR2018015522-appb-I000083
Figure PCTKR2018015522-appb-I000083
화합물 1c 대신 화합물 37a 2g을 이용하고, 화합물 1d 대신에 화합물 8d를 사용한 것을 제외하고, 화합물 1의 합성과 동일하게 진행하였다. 이 때 화합물 37을 1.75 g (76%) 획득하였다. HR LC/MS/MS m/z calcd C142H86B2F6N14O2 (M+): 2155.7182; found: 2155.7182Compound 2 was prepared in the same manner as Compound 1 except that 2 g of Compound 37a was used instead of Compound 1c and Compound 8d was used instead of Compound 1d. At this time, 1.75 g (76%) of Compound 37 was obtained. HR LC / MS / MS m / z Calcd C 142 H 86 B 2 F 6 N 14 O 2 (M +): 2155.7182; found: 2155.7182
제조예Manufacturing example 38. 화합물 38의 합성 38. Synthesis of Compound 38
Figure PCTKR2018015522-appb-I000084
Figure PCTKR2018015522-appb-I000084
화합물 1c 대신 화합물 38a 2g을 이용한 것을 제외하고, 화합물 1의 합성과 동일하게 진행하였다. 이 때 화합물 38을 1.64 g (72%) 획득하였다. HR LC/MS/MS m/z calcd C108H60B2F16N10 (M+): 1823.4970; found: 1823.4969The procedure was the same as the synthesis of Compound 1, except that 2 g of Compound 38a was used instead of Compound 1c. At this time, 1.64 g (72%) of Compound 38 was obtained. HR LC / MS / MS m / z Calcd C108H60B2F6N10 (M +): 1823.4970; found: 1823.4969
제조예Manufacturing example 39. 비교화합물 B5의 합성 39. Synthesis of Comparative Compound B5
Figure PCTKR2018015522-appb-I000085
Figure PCTKR2018015522-appb-I000085
1) 비교화합물 B3 의 합성1) Synthesis of Comparative Compound B3
화합물 B1 5 g 과 화합물 B2 1당량, 아연(zinc) 4당량을 THF 50 mL 에 녹인 후, 영하 78℃로 온도를 내려 질소 하에서 교반을 진행해주었다. 온도가 안정화 되면, TiCl4 2당량을 서서히 첨가하고, 적가가 완료되면 상온으로 온도를 올려준 후, 30분간 교반을 진행하였다. 30분 교반 진행 후, 온도를 70℃로 올려 가열 교반을 진행하여 반응을 완결해주었다. 반응이 완결되면,10% 포타슘 카보네이트 용액을 첨가한 후, 생성된 고체 화합물을 필터해주었다. 필터 진행한 여액을 확보하여, 클로로포름과 물을 이용하여 추출을 진행하였다. 추출된 유기층을 무수마그네슘설패이트를 이용하여 물을 제거해준 후, 감압 증류를 통해 농축 후 클로로포름과 에탄올을 이용하여 생성물을 획득하였다. 이를 통해 화합물 B3를 7.95 g (75%) 획득하였다. HR LC/MS/MS m/z calcd for C34H37BrN2 (M+): 552.2140; found: 552.21395 g of Compound B1, 1 equivalent of Compound B2 and 4 equivalents of zinc were dissolved in 50 mL of THF, and the temperature was lowered to -78 &lt; 0 &gt; C under stirring in nitrogen. When the temperature stabilized, 2 equivalents of TiCl 4 was slowly added. After the dropwise addition was completed, the temperature was raised to room temperature, and stirring was continued for 30 minutes. After stirring for 30 minutes, the temperature was raised to 70 DEG C and the reaction was completed by heating and stirring. When the reaction was completed, 10% potassium carbonate solution was added, and the resulting solid compound was filtered. The filtered filtrate was obtained and extracted with chloroform and water. Water was removed from the extracted organic layer using anhydrous magnesium sulfate, concentrated by distillation under reduced pressure, and then the product was obtained using chloroform and ethanol. This gave 7.95 g (75%) of compound B3 . HR LC / MS / MS m / z calcd for C 34 H 37 BrN 2 (M +): 552.2140; found: 552.2139
2) 비교화합물 B4의 합성2) Synthesis of Comparative Compound B4
합성된 화합물 B3 5g 을 THF 100 mL 에 희석한 후, 반응온도를 영하 78℃로 안정화시켜 질소 하에서 교반해주었다. 안정화된 용액에 1.6 M n-BuLi 용액 1.2 당량을 주사기를 이용하여 서서히 적가해주었다. 후 30분간 교반을 유지해준 후, 보로네이트 에스터 2당량을 첨가하고 반응온도를 상온으로 올려 반응을 진행하였다. 반응이 완료된 후 클로로포름과 물을 이용하여 추출을 진행한다. 추출된 유기층을 무수마그네슘설패이트를 이용하여 물을 제거해준 후, 감압 증류를 통해 농축 후 클로로포름과 에탄올을 이용하여 생성물을 획득하였다. 이를 통해 화합물 B4를 2.88 g (63%) 획득하였다. HR LC/MS/MS m/z calcd for C40H49BN2O2 (M+): 600.3887; found: 600.38885 g of the synthesized compound B3 was diluted with 100 mL of THF, and then the reaction temperature was stabilized at -78 DEG C and stirred under nitrogen. To the stabilized solution, 1.2 equivalents of 1.6 M n-BuLi solution was gradually added using a syringe. After stirring for 30 minutes, 2 equivalents of boronate ester was added and the reaction was allowed to proceed to room temperature. After completion of the reaction, extraction is carried out using chloroform and water. Water was removed from the extracted organic layer using anhydrous magnesium sulfate, concentrated by distillation under reduced pressure, and then the product was obtained using chloroform and ethanol. This gave 2.88 g (63%) of compound B4 . HR LC / MS / MS m / z calcd for C 40 H 49 BN 2 O 2 (M +): 600.3887; found: 600.3888
3) 비교화합물 B5의 합성3) Synthesis of Comparative Compound B5
화합물 B4 2g을 이용한 것을 제외하고, 화합물 1의 합성과 동일하게 진행하였다. 이 때 비교 화합물 B5를 1.52 g (78%) 획득하였다. HR LC/MS/MS m/z calcd C84H82N6(M+): 1174.6601; found: 1174.6600The procedure was the same as the synthesis of the compound 1 except that 2 g of the compound B4 was used. At this time, 1.52 g (78%) of the comparative compound B5 was obtained. HR LC / MS / MS m / z Calcd C 84 H 82 N 6 (M +): 1174.6601; found: 1174.6600
실시예Example 1.  One.
제조예 1에서 제조한 화합물 1 (톨루엔 용액에서의 최대흡수파장 423 nm, 450 nm, 최대발광파장 621 nm) 1.5 중량부를 아크릴계 바인더 33.9 중량부, 다광능성 모노머 (펜타에리트리톨트리아크릴레이트, 일본 화약) 59.3 중량부, 접착 조제 및 계면활성제 (KBM 503, shinetsu) 2.3 중량부, 광개시제 (Tinuvin® 477, BASF) 3.0 중량부를 고형분 함량이 21 중량% 가 되도록 용매 PGEMA (프로필렌 글리콜 모노메틸 에테르 아세테이트:Propylene glycol monomethyl ether acetate) 에 녹여 용액을 제조하였다. 혼합된 용액을 충분히 교반 해준 후, 유리 기판 위에 박막을 코팅 후 건조하여 색변환 필름을 제조하였다. 제조된 색변환필름의 휘도 스펙트럼을 분광방사휘도계 (TOPCON 사 SR series) 로 측청하였다. 구체적으로, 제조된 색변환 필름을 LED 청색 백라이트 (최대 발광파장 450 nm) 와 도광판을 포함하는 백라이트 유닛의 도광판의 일 면에 적층하고, 색변환 필름 상에 프리즘 시트와 DBEF 필름을 적층한 후 필름 기준으로 청색 LED 광의 밝기가 600 nit 가 되도록 초기값을 설정하였다.1.5 parts by weight of Compound 1 (maximum absorption wavelength in a toluene solution: 450 nm, maximum light emission wavelength: 621 nm) prepared in Preparation Example 1 was mixed with 33.9 parts by weight of an acrylic binder, 30 parts by weight of a polyfunctional monomer (pentaerythritol triacrylate, ), 59.3 parts by weight of an adhesion promoter and 2.3 parts by weight of a surfactant (KBM 503, shinetsu) and 3.0 parts by weight of a photoinitiator (Tinuvin 477, BASF) were dissolved in a solvent PGEMA (propylene glycol monomethyl ether acetate: glycol monomethyl ether acetate) to prepare a solution. After the mixed solution was sufficiently stirred, a thin film was coated on a glass substrate and dried to prepare a color conversion film. The luminance spectrum of the prepared color conversion film was measured with a spectroradiometer (TOPCON SR series). Specifically, the prepared color conversion film was laminated on one side of a light guide plate of a backlight unit including LED blue backlight (maximum emission wavelength: 450 nm) and a light guide plate, and a prism sheet and a DBEF film were laminated on the color conversion film, The initial value was set so that the brightness of the blue LED light would be 600 nit.
실시예Example 2.  2.
실시예 1 에서 화합물 1 대신 화합물 2 (톨루엔 용액에서의 최대흡수파장 427 nm, 454 nm 최대발광파장 630 nm) 를 사용한 것을 제외하고는 실시예 1 과 동일하게 실시하였다.The procedure of Example 1 was repeated, except that Compound 2 (maximum absorption wavelength in toluene solution: 427 nm, 454 nm maximum emission wavelength: 630 nm) was used instead of Compound 1 in Example 1.
실시예Example 3.  3.
실시예 1 에서 화합물 1 대신 화합물 3 (톨루엔 용액에서의 최대흡수파장 428 nm, 454 nm 최대발광파장 635 nm) 를 사용한 것을 제외하고는 실시예 1 과 동일하게 실시하였다.The procedure of Example 1 was repeated, except that Compound 3 (maximum absorption wavelength in toluene solution: 428 nm, maximum emission wavelength: 454 nm, 635 nm) was used instead of Compound 1 in Example 1.
실시예Example 4.  4.
실시예 1 에서 화합물 1 대신 화합물 8 (톨루엔 용액에서의 최대흡수파장 472 nm, 496 nm 최대발광파장 652 nm) 를 사용한 것을 제외하고는 실시예 1 과 동일하게 실시하였다.The procedure of Example 1 was repeated, except that Compound 8 (maximum absorption wavelength in toluene solution: 472 nm, 496 nm maximum emission wavelength: 652 nm) was used instead of Compound 1 in Example 1.
실시예Example 5.  5.
실시예 1 에서 화합물 1 대신 화합물 9 (톨루엔 용액에서의 최대흡수파장 492 nm, 506 nm 최대발광파장 655 nm) 를 사용한 것을 제외하고는 실시예 1 과 동일하게 실시하였다.The procedure of Example 1 was repeated, except that Compound 9 (maximum absorption wavelength in toluene solution: 492 nm, 506 nm maximum emission wavelength: 655 nm) was used instead of Compound 1 in Example 1.
실시예Example 6.  6.
실시예 1 에서 화합물 1 대신 화합물 12 (톨루엔 용액에서의 최대흡수파장 468 nm, 495 nm 최대발광파장 652 nm) 를 사용한 것을 제외하고는 실시예 1 과 동일하게 실시하였다.The procedure of Example 1 was repeated, except that Compound 12 (maximum absorption wavelength in a toluene solution: 468 nm, 495 nm maximum emission wavelength: 652 nm) was used instead of Compound 1 in Example 1.
실시예Example 7.  7.
실시예 1 에서 화합물 1 대신 화합물 13 (톨루엔 용액에서의 최대흡수파장 473 nm, 500 nm 최대발광파장 655 nm) 를 사용한 것을 제외하고는 실시예 1 과 동일하게 실시하였다.The procedure of Example 1 was repeated, except that Compound 13 (maximum absorption wavelength in toluene solution: 473 nm, maximum emission wavelength: 500 nm, 655 nm) was used instead of Compound 1 in Example 1.
실시예Example 8.  8.
실시예 1 에서 화합물 1 대신 화합물 21 (톨루엔 용액에서의 최대흡수파장 463 nm, 490 nm 최대발광파장 640 nm) 를 사용한 것을 제외하고는 실시예 1 과 동일하게 실시하였다.Example 1 was carried out in the same manner as in Example 1, except that Compound 21 (maximum absorption wavelength in a toluene solution: 463 nm, 490 nm maximum emission wavelength: 640 nm) was used instead of Compound 1 in Example 1.
실시예Example 9.  9.
실시예 1 에서 화합물 1 대신 화합물 22 (톨루엔 용액에서의 최대흡수파장 467 nm, 495 nm 최대발광파장 650 nm) 를 사용한 것을 제외하고는 실시예 1 과 동일하게 실시하였다.The procedure of Example 1 was repeated, except that Compound 22 (maximum absorption wavelength in a toluene solution: 467 nm, 495 nm maximum emission wavelength: 650 nm) was used instead of Compound 1 in Example 1.
실시예Example 10.  10.
실시예 1 에서 화합물 1 대신 화합물 23 (톨루엔 용액에서의 최대흡수파장 468 nm, 495 nm 최대발광파장 652 nm) 를 사용한 것을 제외하고는 실시예 1 과 동일하게 실시하였다.The procedure of Example 1 was repeated, except that Compound 23 (maximum absorption wavelength in a toluene solution: 468 nm, 495 nm maximum emission wavelength: 652 nm) was used instead of Compound 1 in Example 1.
실시예Example 11.  11.
실시예 1 에서 화합물 1 대신 화합물 24 (톨루엔 용액에서의 최대흡수파장 488 nm, 511 nm 최대발광파장 667 nm) 를 사용한 것을 제외하고는 실시예 1 과 동일하게 실시하였다.The procedure of Example 1 was repeated, except that Compound 24 was used instead of Compound 1 in Example 1 (maximum absorption wavelength in toluene solution: 488 nm, 511 nm maximum emission wavelength: 667 nm).
실시예Example 12.  12.
실시예 1 에서 화합물 1 대신 화합물 25 (톨루엔 용액에서의 최대흡수파장 470 nm, 500 nm 최대발광파장 650 nm) 를 사용한 것을 제외하고는 실시예 1 과 동일하게 실시하였다.The procedure of Example 1 was repeated, except that Compound 25 (maximum absorption wavelength in toluene solution: 470 nm, 500 nm maximum emission wavelength: 650 nm) was used instead of Compound 1 in Example 1.
실시예Example 13.  13.
실시예 1 에서 화합물 1 대신 화합물 26 (톨루엔 용액에서의 최대흡수파장 475 nm, 504 nm 최대발광파장 655 nm) 를 사용한 것을 제외하고는 실시예 1 과 동일하게 실시하였다.The procedure of Example 1 was repeated, except that Compound 26 (maximum absorption wavelength in a toluene solution: 475 nm, maximum emission wavelength: 504 nm, 655 nm) was used instead of Compound 1 in Example 1.
실시예Example 14.  14.
실시예 1 에서 화합물 1 대신 화합물 27 (톨루엔 용액에서의 최대흡수파장 475 nm, 505 nm 최대발광파장 652 nm) 를 사용한 것을 제외하고는 실시예 1 과 동일하게 실시하였다.The procedure of Example 1 was repeated, except that Compound 27 (maximum absorption wavelength in toluene solution: 475 nm, 505 nm maximum emission wavelength: 652 nm) was used instead of Compound 1 in Example 1.
실시예Example 15.  15.
실시예 1 에서 화합물 1 대신 화합물 29 (톨루엔 용액에서의 최대흡수파장 492 nm, 524 nm 최대발광파장 672 nm) 를 사용한 것을 제외하고는 실시예 1 과 동일하게 실시하였다.The procedure of Example 1 was repeated, except that Compound 29 (maximum absorption wavelength in toluene solution: 492 nm, 524 nm maximum emission wavelength: 672 nm) was used instead of Compound 1 in Example 1.
실시예Example 16.  16.
실시예 1 에서 화합물 1 대신 화합물 30 (톨루엔 용액에서의 최대흡수파장 460 nm, 488 nm 최대발광파장 645 nm) 를 사용한 것을 제외하고는 실시예 1 과 동일하게 실시하였다.The procedure of Example 1 was repeated, except that Compound 30 was used instead of Compound 1 in Example 1 (maximum absorption wavelength in toluene solution: 460 nm, 488 nm maximum emission wavelength: 645 nm).
실시예Example 17.  17.
실시예 1 에서 화합물 1 대신 화합물 31 (톨루엔 용액에서의 최대흡수파장 467 nm, 498 nm 최대발광파장 647 nm) 를 사용한 것을 제외하고는 실시예 1 과 동일하게 실시하였다.Example 1 was carried out in the same manner as in Example 1, except that Compound 31 (maximum absorption wavelength in a toluene solution: 467 nm, 498 nm maximum emission wavelength: 647 nm) was used instead of Compound 1 in Example 1.
실시예Example 18.  18.
실시예 1 에서 화합물 1 대신 화합물 32 (톨루엔 용액에서의 최대흡수파장 468 nm, 500 nm 최대발광파장 643 nm) 를 사용한 것을 제외하고는 실시예 1 과 동일하게 실시하였다.The procedure of Example 1 was repeated, except that Compound 32 (maximum absorption wavelength in a toluene solution: 468 nm, maximum emission wavelength: 500 nm, 643 nm) was used instead of Compound 1 in Example 1.
실시예Example 19.  19.
실시예 1 에서 화합물 1 대신 화합물 35 (톨루엔 용액에서의 최대흡수파장 482 nm, 510 nm 최대발광파장 658 nm) 를 사용한 것을 제외하고는 실시예 1 과 동일하게 실시하였다.The procedure of Example 1 was repeated, except that Compound 35 (maximum absorption wavelength in toluene solution: 482 nm, 510 nm maximum emission wavelength: 658 nm) was used instead of Compound 1 in Example 1.
실시예Example 20.  20.
실시예 1 에서 화합물 1 대신 화합물 36 (톨루엔 용액에서의 최대흡수파장 485 nm, 513 nm 최대발광파장 650 nm) 를 사용한 것을 제외하고는 실시예 1 과 동일하게 실시하였다.The procedure of Example 1 was repeated, except that Compound 36 (maximum absorption wavelength in toluene solution: 485 nm, 513 nm maximum emission wavelength: 650 nm) was used instead of Compound 1 in Example 1.
실시예Example 21. 21.
실시예 1 에서 화합물 1 대신 화합물 38 (톨루엔 용액에서의 최대흡수파장 483 nm, 514 nm 최대발광파장 665 nm) 를 사용한 것을 제외하고는 실시예 1 과 동일하게 실시하였다.The procedure of Example 1 was repeated, except that Compound 38 (maximum absorption wavelength in toluene solution: 483 nm, 514 nm maximum emission wavelength: 665 nm) was used instead of Compound 1 in Example 1.
비교실시예Comparative Example 1.  One.
실시예 1 에서 화합물 1 대신 비교화합물 B5 (톨루엔 용액에서의 최대흡수파장 494 nm, 최대발광파장 687 nm) 를 사용한 것을 제외하고는 실시예 1 과 동일하게 실시하였다.The procedure of Example 1 was repeated, except that Comparative Compound B5 (maximum absorption wavelength in a toluene solution: 494 nm, maximum emission wavelength: 687 nm) was used instead of Compound 1 in Example 1.
실시예 1 내지 21 및 비교실시예 1에 사용된 각각의 화합물을 톨루엔 용매 하에서 10-5M 농도로 만든 후 용액물성을 측정하였다. 구체적으로 제조된 용액으로 신코(Sinco) 사의 UV-visible spectrometer (Mega-200)을 이용하여 최대흡수파장 (λuv, MAX)을 측정하였으며, 흡수영역 450nm 에서의 흡수도 (abs intensity @450nm)를 확인하였고, 신코(Sinco)사의 fluorescenc spectrometer (FS-2)를 이용하여 최대발광파장 (λPL , MAX)을 측정하였다. Each compound used in Examples 1 to 21 and Comparative Example 1 was made to have a concentration of 10 -5 M in a toluene solvent, and the solution properties were measured. The maximum absorption wavelength (λ uv, MAX ) was measured using a UV-visible spectrometer (Mega-200) manufactured by Sinco and the absorbance at 450 nm And the maximum emission wavelength (λ PL , MAX ) was measured using a fluorescenc spectrometer (FS-2) manufactured by Sinco.
또한, 실시예 1 내지 21 및 비교실시예 1에 의하여 제조된 박막에 대하여 사의 fluorescenc spectrometer (FS-2)를 이용하여 최대발광파장 (λPL , MAX)을 측정하였고, 하마마츠 (Hammatsu)사의 Quantarurs-QY(C11347-11)를 이용하여 박막의 양자효율을 측정하였다. The maximum emission wavelength (λ PL , MAX ) of the thin films prepared in Examples 1 to 21 and Comparative Example 1 was measured using a fluorescence spectrometer (FS-2) manufactured by Hamamatsu Co., -QY (C11347-11) was used to measure the quantum efficiency of the thin film.
실시예Example 제조예Manufacturing example 용액solution 박막pellicle
λuv , MAX (nm)λ uv , MAX (nm) λPL , MAX (nm)? PL , MAX (nm) abs intensity (@450 nm)abs intensity (@ 450 nm) λPL , MAX (nm)? PL , MAX (nm) 양자효율,PLQY (%)Quantum efficiency, PLQY (%)
1One 1One 423,450423,450 621621 0.850.85 626626 13.113.1
22 22 427,454427,454 630630 0.820.82 635635 17.717.7
33 33 428,454428,454 635635 0.790.79 640640 20.520.5
44 88 472,496472,496 652652 0.610.61 656656 27.827.8
55 99 492,506492,506 655655 0.550.55 660660 25.725.7
66 1212 468,495468,495 652652 0.680.68 657657 37.037.0
77 1313 473,500473,500 655655 0.630.63 660660 58.058.0
88 2121 463,490463,490 640640 0.720.72 645645 29.329.3
99 2222 467,495467,495 650650 0.680.68 651651 35.735.7
1010 2323 468,495468,495 652652 0.650.65 655655 55.855.8
1111 2424 488,511488,511 667667 0.570.57 678678 42.342.3
1212 2525 470,500470,500 650650 0.630.63 652652 48.548.5
1313 2626 475,504475,504 655655 0.610.61 660660 52.352.3
1414 2727 475,505475,505 652652 0.620.62 654654 57.657.6
1515 2929 492,524492,524 672672 0.570.57 675675 56.156.1
1616 3030 460,488460,488 645645 0.720.72 647647 38.938.9
1717 3131 467,498467,498 647647 0.690.69 653653 57.657.6
1818 3232 468,500468,500 643643 0.690.69 648648 62.162.1
1919 3535 482,510482,510 658658 0.600.60 663663 63.563.5
2020 3636 485,513485,513 650650 0.580.58 652652 20.120.1
2121 3838 483, 514483, 514 665665 0.620.62 670670 28.928.9
비교실시예 1Comparative Example 1 비교화합물 B5Comparative compound B5 494,687494,687 687687 0.150.15 688688 0.30.3

Claims (8)

  1. 하기 화학식 1로 표시되는 화합물:A compound represented by the following formula (1):
    [화학식 1][Chemical Formula 1]
    Figure PCTKR2018015522-appb-I000086
    Figure PCTKR2018015522-appb-I000086
    상기 화학식 1에 있어서, In Formula 1,
    L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴렌기이고, L1 and L2 are the same or different and are each independently a substituted or unsubstituted arylene group,
    L10 내지 L13은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 2가의 헤테로고리기이며, L10 to L13 are the same or different and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
    R1 내지 R4는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카르보닐기; 에스테르기; 이미드기; 아미드기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 플루오로알킬기; 치환 또는 비치환된 알킬티오기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 헤테로아릴기; 또는 치환 또는 비치환된 탄화수소고리기이고, R1 to R4 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted fluoroalkyl group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted allyloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or a substituted or unsubstituted hydrocarbon ring group,
    R1 내지 R4중 적어도 하나는 하기 화학식 2로 표시되며, At least one of R 1 to R 4 is represented by the following formula (2)
    [화학식 2](2)
    Figure PCTKR2018015522-appb-I000087
    Figure PCTKR2018015522-appb-I000087
    상기 화학식 2에 있어서, In Formula 2,
    R10 내지 R19 중 하나는 화학식 1과 결합하고, One of R10 to R19 is bonded to the formula (1)
    R10 내지 R19 중 화학식 1과 결합하지 않는 기는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카르보닐기; 에스테르기; 이미드기; 아미드기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 플루오로알킬기; 치환 또는 비치환된 알킬티오기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 헤테로아릴기; 또는 치환 또는 비치환된 탄화수소고리기이거나, 서로 결합하여 치환 또는 비치환된 고리를 형성하며, The groups not bonded to the formula (1) among R10 to R19 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted fluoroalkyl group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted allyloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or a substituted or unsubstituted hydrocarbon ring group, or may be bonded to each other to form a substituted or unsubstituted ring,
    X1 및 X2는 서로 같거나 상이하고, 각각 독립적으로 할로겐기; 니트릴기; -CO2R""; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 헤테로고리기; 또는 치환 또는 비치환된 탄화수소고리기이거나, 상기 X1 및 X2가 서로 결합하여 치환 또는 비치환된 고리를 형성하고, X1 and X2 are the same or different from each other, and each independently represents a halogen group; A nitrile group; -CO 2 R ""; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted hydrocarbon ring group, or X 1 and X 2 are bonded to each other to form a substituted or unsubstituted ring,
    R""은 치환 또는 비치환된 알킬기; 치환 또는 비치환된 플루오로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 헤테로고리기; 또는 치환 또는 비치환된 탄화수소고리기이다.R "" is a substituted or unsubstituted alkyl group; A substituted or unsubstituted fluoroalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted hydrocarbon ring group.
  2. 청구항 1에 있어서, 상기 R1 및 R2 중 적어도 하나와 R3 및 R4 중 적어도 하나는 상기 화학식 2로 표시되는 것인 화합물.The compound according to claim 1, wherein at least one of R 1 and R 2 and at least one of R 3 and R 4 is represented by the general formula (2).
  3. 청구항 1에 있어서, 상기 L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 알킬기, 알콕시기 또는 할로겐기로 치환 또는 비치환된 페닐렌기인 것인 화합물.The compound according to claim 1, wherein L 1 and L 2 are the same or different and are each independently a substituted or unsubstituted phenylene group with an alkyl group, an alkoxy group or a halogen group.
  4. 청구항 1에 있어서, 상기 화학식 2는 하기 화학식 2-1 내지 2-3 중 어느 하나로 표시되는 것인 화합물:The compound according to claim 1, wherein the formula (2) is represented by any one of the following formulas (2-1) to (2-3):
    [화학식 2-1][Formula 2-1]
    Figure PCTKR2018015522-appb-I000088
    Figure PCTKR2018015522-appb-I000088
    [화학식 2-2][Formula 2-2]
    Figure PCTKR2018015522-appb-I000089
    Figure PCTKR2018015522-appb-I000089
    [화학식 2-3][Formula 2-3]
    Figure PCTKR2018015522-appb-I000090
    Figure PCTKR2018015522-appb-I000090
    상기 화학식 2-1 내지 2-3 에 있어서, In the general formulas (2-1) to (2-3)
    상기 R10 내지 R19, X1 및 X2는 화학식 2에서의 정의와 같고, Wherein R10 to R19, X1 and X2 have the same definitions as in the formula (2)
    R20 내지 R22는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카르보닐기; 에스테르기; 이미드기; 아미드기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 플루오로알킬기; 치환 또는 비치환된 알킬티오기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 헤테로아릴기; 또는 치환 또는 비치환된 탄화수소고리기이고, R20 to R22 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted fluoroalkyl group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted allyloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or a substituted or unsubstituted hydrocarbon ring group,
    a 내지 c는 0 내지 4의 정수이고, a 내지 c가 2이상인 경우, 괄호안의 치환기는 서로 같거나 상이하다. a to c are an integer of 0 to 4, and when a to c are two or more, the substituents in parentheses are the same or different from each other.
  5. 청구항 1에 있어서, 상기 화학식 1의 화합물은 하기 구조식들 중에서 선택되는 것인 화합물:3. The compound of claim 1, wherein the compound of formula (1) is selected from the group consisting of:
    Figure PCTKR2018015522-appb-I000091
    Figure PCTKR2018015522-appb-I000091
    Figure PCTKR2018015522-appb-I000092
    Figure PCTKR2018015522-appb-I000092
    Figure PCTKR2018015522-appb-I000093
    Figure PCTKR2018015522-appb-I000093
    Figure PCTKR2018015522-appb-I000094
    Figure PCTKR2018015522-appb-I000094
    Figure PCTKR2018015522-appb-I000095
    Figure PCTKR2018015522-appb-I000095
    Figure PCTKR2018015522-appb-I000096
    Figure PCTKR2018015522-appb-I000096
    Figure PCTKR2018015522-appb-I000097
    Figure PCTKR2018015522-appb-I000097
    Figure PCTKR2018015522-appb-I000098
    Figure PCTKR2018015522-appb-I000098
    Figure PCTKR2018015522-appb-I000099
    Figure PCTKR2018015522-appb-I000099
    Figure PCTKR2018015522-appb-I000100
    Figure PCTKR2018015522-appb-I000100
    Figure PCTKR2018015522-appb-I000101
    Figure PCTKR2018015522-appb-I000101
    Figure PCTKR2018015522-appb-I000102
    Figure PCTKR2018015522-appb-I000102
    Figure PCTKR2018015522-appb-I000103
    Figure PCTKR2018015522-appb-I000103
    Figure PCTKR2018015522-appb-I000104
    Figure PCTKR2018015522-appb-I000104
  6. 수지 매트릭스; 및 상기 수지 매트릭스 내에 분산된 청구항 1 내지 5 중 어느 한 항에 따른 화합물을 포함하는 색변환 필름.Resin matrix; And a coloring film comprising a compound according to any one of claims 1 to 5 dispersed in the resin matrix.
  7. 청구항 6에 따른 색변환 필름을 포함하는 백라이트 유닛.A backlight unit comprising the color conversion film according to claim 6.
  8. 청구항 7에 따른 백라이트 유닛을 포함하는 디스플레이 장치.A display device comprising a backlight unit according to claim 7.
PCT/KR2018/015522 2017-12-07 2018-12-07 Nitrogen-containing compound, color conversion film comprising same, and backlight unit and display device each comprising same WO2019112369A1 (en)

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JP2019551526A JP6896970B2 (en) 2017-12-07 2018-12-07 Nitrogen-containing compounds, color conversion films containing them, and backlight units and display devices containing them.
CN201880020163.2A CN110520429B (en) 2017-12-07 2018-12-07 Nitrogen-containing compound, color conversion film comprising same, and backlight unit and display device comprising same

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Publication number Priority date Publication date Assignee Title
JP2007221087A (en) * 2006-01-18 2007-08-30 Fuji Xerox Co Ltd Organic electroluminescent device
KR20140029315A (en) * 2012-08-31 2014-03-10 캐논 가부시끼가이샤 Electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus
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Publication number Priority date Publication date Assignee Title
JP2007221087A (en) * 2006-01-18 2007-08-30 Fuji Xerox Co Ltd Organic electroluminescent device
KR20140029315A (en) * 2012-08-31 2014-03-10 캐논 가부시끼가이샤 Electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus
CN103865290A (en) * 2014-04-01 2014-06-18 安徽师范大学 Fluorine-boron fluorescent dye as well as preparation method and application thereof

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SHIMIZU, S. ET AL.: "Benzo[c,d]indole-Containing Aza-BODIPY Dyes: Asymmetrization-Induced Solid-State Emission and Aggregation-Induced Emission Enhancement as New Properties of a Well-Known Chromophore", CHEM. EUR. J., 2015, pages 12996 - 13003, XP055606897, DOI: doi:10.1002/chem.201501464 *

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