WO2019112369A1 - Composé contenant de l'azote, film de conversion de couleur le comprenant, unité de rétroéclairage et dispositif d'affichage comprenant chacun celui-ci - Google Patents

Composé contenant de l'azote, film de conversion de couleur le comprenant, unité de rétroéclairage et dispositif d'affichage comprenant chacun celui-ci Download PDF

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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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group
substituted
unsubstituted
compound
same
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PCT/KR2018/015522
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English (en)
Korean (ko)
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손선경
이미림
이호용
송철준
김지선
유형욱
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주식회사 엘지화학
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Priority claimed from KR1020180156173A external-priority patent/KR102141741B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201880020163.2A priority Critical patent/CN110520429B/zh
Priority to JP2019551526A priority patent/JP6896970B2/ja
Priority to US16/603,168 priority patent/US11498931B2/en
Publication of WO2019112369A1 publication Critical patent/WO2019112369A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/55—Boron-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL 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
    • G02F1/00—Devices 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
    • G02F1/01—Devices 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 
    • G02F1/13—Devices 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
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural 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.

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Abstract

La présente invention concerne un composé contenant de l'azote, un film de conversion de couleur comprenant ce composé, une unité de rétroéclairage et un dispositif d'affichage comprenant chacun celui-ci.
PCT/KR2018/015522 2017-12-07 2018-12-07 Composé contenant de l'azote, film de conversion de couleur le comprenant, unité de rétroéclairage et dispositif d'affichage comprenant chacun celui-ci WO2019112369A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN201880020163.2A CN110520429B (zh) 2017-12-07 2018-12-07 含氮化合物、包含其的色彩转换膜以及包含其的背光单元和显示装置
JP2019551526A JP6896970B2 (ja) 2017-12-07 2018-12-07 含窒素化合物、これを含む色変換フィルム、およびこれを含むバックライトユニットおよびディスプレイ装置
US16/603,168 US11498931B2 (en) 2017-12-07 2018-12-07 Nitrogen-containing compound, color conversion film comprising same, and backlight unit and display device each comprising same

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KR20170167119 2017-12-07
KR10-2017-0167119 2017-12-07
KR1020180156173A KR102141741B1 (ko) 2017-12-07 2018-12-06 함질소 화합물, 이를 포함하는 색변환 필름, 및 이를 포함하는 백라이트 유닛 및 디스플레이 장치
KR10-2018-0156173 2018-12-06

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JP2007221087A (ja) * 2006-01-18 2007-08-30 Fuji Xerox Co Ltd 有機電界発光素子
KR20140029315A (ko) * 2012-08-31 2014-03-10 캐논 가부시끼가이샤 전자 사진감광체, 프로세스 카트리지, 및 전자 사진장치
CN103865290A (zh) * 2014-04-01 2014-06-18 安徽师范大学 氟硼荧光染料及其制备方法和应用

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JP2007221087A (ja) * 2006-01-18 2007-08-30 Fuji Xerox Co Ltd 有機電界発光素子
KR20140029315A (ko) * 2012-08-31 2014-03-10 캐논 가부시끼가이샤 전자 사진감광체, 프로세스 카트리지, 및 전자 사진장치
CN103865290A (zh) * 2014-04-01 2014-06-18 安徽师范大学 氟硼荧光染料及其制备方法和应用

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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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