COMPOUND AND COLOR CONVERSION FILM COMPRISING SAME

Information

  • Patent Application
  • 20210347790
  • Publication Number
    20210347790
  • Date Filed
    October 15, 2019
    4 years ago
  • Date Published
    November 11, 2021
    2 years ago
Abstract
The present specification relates to a compound, and a color conversion film, a backlight unit and a display apparatus including the same.
Description
TECHNICAL FIELD

The present specification relates to a compound, and a color conversion film, a backlight unit and a display apparatus including the same.


BACKGROUND OF THE INVENTION

Existing light emitting diodes (LED) are obtained by mixing a green phosphorescent substance and a red phosphorescent substance to a blue light emitting diode, or mixing a yellow phosphorescent substance and a blue-green phosphorescent substance to a UV light emitting diode. However, with such a method, it is difficult to control colors, and therefore, color rendering is not favorable. Accordingly, color gamut declines.


In order to overcome such color gamut decline and reduce production costs, methods of obtaining green and red in a manner of filming quantum dots and binding the dots to a blue LED have been recently tried. However, cadmium series quantum dots have safety problems, and other quantum dots have significantly decreased efficiency compared to cadmium series quantum dots. In addition, quantum dots have reduced stability for oxygen and water, and have a disadvantage in that the performance is significantly degraded when aggregated. Furthermore, unit costs of production are high since, when producing quantum dots, maintaining the sizes is difficult.


BRIEF SUMMARY OF THE INVENTION

The present disclosure provides a compound, and a color conversion film, a backlight unit and a display apparatus including the same.


One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.




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In Chemical Formula 1,


X1 to X3 are the same as or different from each other, and each independently O or S,


X4 and X5 are the same as or different from each other, and each independently a halogen group; CN; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aryloxy group; or a substituted or unsubstituted heteroaryl group,


R1 and R6 are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; CN; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,


R2 and R5 are the same as or different from each other, and each independently a substituted or unsubstituted ester group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,


R3 and R4 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and


R7 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.


Another embodiment of the present specification provides a color conversion film including a resin matrix; and the compound represented by Chemical Formula 1 dispersed into the resin matrix.


Another embodiment of the present specification provides a backlight unit including the color conversion film.


Another embodiment of the present specification provides a display apparatus including the backlight unit.


ADVANTAGEOUS EFFECTS

A compound according to one embodiment of the present specification is, as well as having high fluorescence efficiency, stable for water or oxygen, and has lower unit costs of production compared to quantum dots. Accordingly, by using a compound represented by Chemical Formula 1 described in the present specification as a fluorescent substance of a color conversion film, a color conversion film having excellent luminance and color gamut, having a simple manufacturing process, and having low manufacturing costs can be provided.





BRIEF DESCRIPTION OF DRAWINGS


FIG. 1 is a mimetic diagram using a color conversion film according to one embodiment of the present specification in a backlight unit.



FIG. 2 is a mimetic diagram illustrating a structure of a display apparatus according to one embodiment of the present specification.





DETAILED DESCRIPTION OF THE INVENTION

Hereinafter, the present application will be described in more detail.


One embodiment of the present specification provides a compound represented by Chemical Formula 1.


In the present specification, a certain part “including” certain constituents means capable of further including other constituents, and does not exclude other constituents unless particularly stated on the contrary.


In the present specification, one member being placed “on” another member includes not only a case of the one member being in contact with the another member but a case of still another member being present between the two members.


Examples of substituents in the present specification are described below, however, the substituents are not limited thereto.


The term “substitution” means a hydrogen atom bonding to a carbon atom of a compound is changed to another substituent, and the position of substitution is not limited as long as it is a position at which the hydrogen atom is substituted, that is, a position at which a substituent can substitute, and when two or more substituents substitute, the two or more substituents may be the same as or different from each other.


The term “substituted or unsubstituted” in the present specification means being substituted with one, two or more substituents selected from the group consisting of hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a carbonyl group; an imide group; an amide group; an ester group; a hydroxyl group; an amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; and a substituted or unsubstituted heteroaryl group, or being substituted with a substituent linking two or more substituents among the substituents illustrated above, or having no substituents. For example, “a substituent linking two or more substituents” may include a biphenyl group. In other words, a biphenyl group may be an aryl group, or interpreted as a substituent linking two phenyl groups.


In the present specification,




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mean a site bonding to other substituents or bonding sites.


In the present specification, examples of the halogen group may include fluorine, chlorine, bromine or iodine.


In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably from 1 to 30.


In the present specification, in the amide group, nitrogen of the amide group may be substituted with hydrogen, a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms.


In the present specification, in the ester group, oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. Specifically, compound having a structure such as —C(═O)ORa or —O(C═O)Ra may be included, and in this case, Ra is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.


In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably from 1 to 30. Specifically, compounds having a structure such as —C(═O)Rb may be included, and in this case, Rb is hydrogen or an alkyl group, however, the carbonyl group is not limited thereto.


In the present specification, the alkyl group may be linear or branched, and although not particularly limited thereto, the number of carbon atoms is preferably from 1 to 30. Specific examples thereof may include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.


In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specific examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.


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 from 1 to 30. Specific examples thereof may include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like, but are not limited thereto.


In the present specification, the alkenyl group may be linear or branched, and although not particularly limited thereto, the number of carbon atoms is preferably from 2 to 30. Specific examples thereof may include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, a stilbenyl group, a styrenyl group and the like, but are not limited thereto.


In the present specification, the alkynyl group may be linear or branched, and although not particularly limited thereto, the number of carbon atoms is preferably from 2 to 30. Specific examples thereof may include an alkynyl group such as ethynyl, propynyl, 2-methyl-2-propynyl, 2-butynyl or 2-pentynyl, but are not limited thereto.


In the present specification, the amine group may be selected from the group consisting of —NH2; a monoalkylamine group; a dialkylamine group; an N-alkylarylamine group; a monoarylamine group; a diarylamine group; an N-arylheteroarylamine group; an N-alkylheteroarylamine group, a monoheteroarylamine group and a diheteroarylamine group, and although not particularly limited thereto, the number of carbon atoms is preferably from 1 to 30. Specific examples of the amine group may include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a ditolylamine group, an N-phenyltolylamine group, a triphenylamine group, an N-phenylbiphenylamine group; an N-phenylnaphthylamine group; an N-biphenylnaphthylamine group; an N-naphthylfluorenylamine group; an N-phenylphenanthrenylamine group; an N-biphenylphenanthrenylamine group; an N-phenylfluorenylamine group; an N-phenylterphenylamine group; an N-phenanthrenylfluorenylamine group; an N-biphenylfluorenylamine group and the like, but are not limited thereto.


In the present specification, the N-alkylarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and an aryl group.


In the present specification, the N-arylheteroarylamine group means an amine group in which N of the amine group is substituted with an aryl group and a heteroaryl group.


In the present specification, the N-alkylheteroarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and a heteroaryl group.


In the present specification, the alkyl group in the alkylamine group, the N-alkylarylamine group, the alkylthioxy group, the alkylsulfoxy group and the N-alkylheteroarylamine group is the same as the examples of the alkyl group described above. Specific examples of the alkylthioxy group may include a methylthioxy group, an ethylthioxy group, a tert-butylthioxy group, a hexylthioxy group, an octylthioxy group and the like, and specific examples of the alkylsulfoxy group may include mesyl, an ethylsulfoxy group, a propylsulfoxy group, a butylsulfoxy group and the like, however, the alkylthoixy group and the alkylsulfoxy group are not limited thereto.


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.


When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably from 6 to 30. Specific examples of the monocyclic aryl group may include a phenyl group, a biphenyl group, a terphenyl group and the like, but are not limited thereto.


When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably from 10 to 30. Specific examples of the polycyclic aryl group may include a naphthyl group, an anthracenyl group, a phenanthryl group, a triphenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group and the like, but are not limited thereto.


In the present specification, the fluorenyl group may be substituted, and adjacent substituents may bond to each other to form a ring.


When the fluorenyl group is substituted,




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and the like may be included. However, the structure is not limited thereto.


In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the N-alkylarylamine group and the N-arylheteroarylamine group is the same as the examples of the aryl group described above. Specific examples of the aryloxy group may include phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenom p-tert-butylphenoxy, 3-biphenyloxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthryloxy, 2-anthryloxy, 9-anthryloxy, 1-phenanthryloxy, 3-phenanthryloxy, 9-phenanthryloxy and the like, and specific examples of the arylthioxy group may include a phenylthioxy group, a 2-methylphenylthioxy group, a 4-tert-butylphenylthioxy group and the like, however, the aryloxy group and the arylthioxy group are not limited thereto.


In the present specification, the heteroaryl group is a group including one or more atoms that are not carbon, that is, heteroatoms, and specifically, the heteroatom may include one or more atoms selected from the group consisting of O, N, Se, S and the like. The number of carbon atoms is not particularly limited, but is preferably from 2 to 30, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heteroaryl group may include a thiophene group, a furanyl group, a pyrrole group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridine group, a bipyridine group, a pyrimidine group, a triazinyl group, a triazolyl group, an acridyl group, a pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolinyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a dibenzofuranyl group, a chromene group and the like, but are not limited thereto.


In the present specification, the heteroaryl group may be monocyclic or polycyclic, may be aromatic or a fused ring of aromatic and aliphatic, and may be selected from among the examples of the heterocyclic group.


In the present specification, an “adjacent” group may mean a substituent substituting an atom directly linked to an atom substituted by the corresponding substituent, a substituent sterically most closely positioned to the corresponding substituent, or another substituent substituting an atom substituted by the corresponding substituent. For example, two substituents substituting ortho positions in a benzene ring, and two substituents substituting the same carbon in an aliphatic ring may be interpreted as groups “adjacent” to each other.


In the present specification, the meaning of “adjacent groups bond to each other to form a ring” among substituents means adjacent groups bonding to each other to form a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heteroring.


One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.




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In Chemical Formula 1,


X1 to X3 are the same as or different from each other, and each independently O or S,


X4 and X5 are the same as or different from each other, and each independently a halogen group; CN; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aryloxy group; or a substituted or unsubstituted heteroaryl group,


R1 and R6 are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; CN; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,


R2 and R5 are the same as or different from each other, and each independently a substituted or unsubstituted ester group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,


R3 and R4 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and


R7 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.


According to one embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulae 1-1 to 1-4.




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In Chemical Formulae 1-1 to 1-4, R1 to R7, X4 and X5 have the same definitions as in Chemical Formula 1.


In one embodiment of the present specification, X1 to X3 are the same as or different from each other, and each independently O or S.


In one embodiment of the present specification, X1 to X3 are O.


In another embodiment, X1 is O, and X2 and X3 are S.


In another embodiment, X1 to X3 are S.


In another embodiment, X1 is S, and X2 and X3 are O.


In one embodiment of the present specification, X4 and X5 are the same as or different from each other, and each independently a halogen group; CN; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aryloxy group; or a substituted or unsubstituted heteroaryl group.


In one embodiment of the present specification, X4 and X5 are the same as or different from each other, and each independently a halogen group; CN; an alkoxy group unsubstituted or substituted with a halogen group; an alkynyl group unsubstituted or substituted with a substituted or unsubstituted aryl group; an aryl group unsubstituted or substituted with a nitro group; an aryloxy group; or a heteroaryl group.


In one embodiment of the present specification, X4 and X5 are the same as or different from each other, and each independently fluorine; CN; an n-butoxy group substituted with a halogen group; an ethynyl group substituted with a substituted or unsubstituted aryl group; a phenyl group unsubstituted or substituted with a nitro group; a substituted or unsubstituted phenoxy group; or a pyridine group.


In one embodiment of the present specification, X4 and X5 are the same as or different from each other, and each independently fluorine; CN; an n-butoxy group substituted with fluorine; an ethynyl group substituted with a phenyl group unsubstituted or substituted with an alkyl group; a phenyl group unsubstituted or substituted with NO2; a phenoxy group; or a pyridine group.


In one embodiment of the present specification, R1 and R6 are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; CN; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.


In one embodiment of the present specification, R1 and R6 are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; CN; an alkyl group; a cycloalkyl group unsubstituted or substituted with an alkyl group; an alkoxy group; an aryloxy group unsubstituted or substituted with a halogen group, CN, CF3 or an alkyl group; an aryl group unsubstituted or substituted with a halogen group, CN, CF3, an alkyl group or an alkoxy group; or a substituted or unsubstituted heteroaryl group.


In one embodiment of the present specification, R1 and R6 are the same as or different from each other, and each independently hydrogen; deuterium; chlorine; bromine; CN; a methyl group; a cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with an alkyl group; a methoxy group; an isopropoxy group; an aryloxy group having 6 to 30 carbon atoms unsubstituted or substituted with a halogen group, CN, CF3or an alkyl group; an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a halogen group, CN, CF3, an alkyl group or an alkoxy group; a pyrrole group; a pyridine group; or a thiophene group.


In one embodiment of the present specification, R1 and R6 are the same as or different from each other, and each independently hydrogen; deuterium; chlorine; bromine; CN; a methyl group; a cyclopropyl group; a cyclobutyl group; a cyclopentyl group; a cyclohexyl group unsubstituted or substituted with an alkyl group; an aryloxy group having 6 to 30 carbon atoms unsubstituted or substituted with fluorine, CN, CF3 or a methyl group; an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with fluorine, CN, CF3, a methyl group, a butyl group, a tert-butyl group or a methoxy group; a pyrrole group; a pyridine group; or a thiophene group.


In one embodiment of the present specification, R2 and R5 are the same as or different from each other, and each independently a substituted or unsubstituted ester group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.


In one embodiment of the present specification, R2 and R5 are the same as or different from each other, and each independently —C(═O)ORa; an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of a halogen group, CN, CF3, —C(═O)ORa, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; or a heteroaryl group having 6 to 30 carbon atoms unsubstituted or substituted with an aryl group, and Ra is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.


In one embodiment of the present specification, R2 and R5 are the same as or different from each other, and each independently —C(═O)ORa; an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of a halogen group, CN, CF3, —C(═O)ORa, an alkyl group unsubstituted or substituted with a halogen group, an alkoxy group, an amine group unsubstituted or substituted with an alkyl group, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 2 to 30 carbon atoms unsubstituted or substituted with an ester group and ═O; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophene group; a substituted or unsubstituted carbazole group; or a substituted or unsubstituted phenanthrolinyl group, and Ra is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms.


In one embodiment of the present specification, R2 and R5 are the same as or different from each other, and each independently —C(═O)ORa; an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of fluorine, chlorine, bromine, CN, CF3, —C(═O)ORa, a methyl group unsubstituted or substituted with a halogen group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a pentyl group, a hexyl group, a methoxy group, NH2, a dialkylamine group, a naphthyl group, an anthracenyl group, a carbazole group, a dibenzofuranyl group, a pyridine group, and a chromene group substituted with an ester group and ═O; a dibenzofuranyl group unsubstituted or substituted with a phenyl group; a dibenzothiophene group unsubstituted or substituted with a phenyl group; a carbazole group unsubstituted or substituted with a phenyl group; or a phenanthrolinyl group, and Ra is a methyl group, a phenyl group unsubstituted or substituted with CN, or a chromene group substituted with ═O.


In one embodiment of the present specification, R3 and R4 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.


In one embodiment of the present specification, R3 and R4 are the same as or different from each other, and each independently an alkyl group having 1 to 30 carbon atoms unsubstituted or substituted with CF3; a cycloalkyl group having 1 to 30 carbon atoms unsubstituted or substituted with an alkyl group; an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of a halogen group, CN, CF3, —C(═O)ORa, an amine group, an alkoxy group, an alkyl group having 1 to 30 carbon atoms and a heteroaryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms, and Ra is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.


In one embodiment of the present specification, R3 and R4 are the same as or different from each other, and each independently an alkyl group having 1 to 30 carbon atoms unsubstituted or substituted with CF3; a cyclohexyl group unsubstituted or substituted with an alkyl group; an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of a halogen group, CN, CF3, —C(═O)ORa, NH2, a dialkylamine group, a diphenylamine group, an alkoxy group, an alkyl group having 1 to 30 carbon atoms, a pyridine group, a dibenzofuranyl group and a carbazole group; a dibenzofuranyl group unsubstituted or substituted with an aryl group; a dibenzothiophene group unsubstituted or substituted with an aryl group; a carbazole group unsubstituted or substituted with an aryl group; or a chromene group unsubstituted or substituted with ═O, and Ra is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.


In one embodiment of the present specification, R3 and R4 are the same as or different from each other, and each independently an alkyl group having 1 to 30 carbon atoms unsubstituted or substituted with CF3; a cyclohexyl group unsubstituted or substituted with an alkyl group; an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of fluorine, chlorine, CN, CF3, —C(═O)ORa, NH2, a dialkylamine group, a diphenylamine group, a methoxy group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a pentyl group, a hexyl group, a pyridine group, a dibenzofuranyl group and a carbazole group; a dibenzofuranyl group unsubstituted or substituted with a phenyl group; a dibenzothiophene group; a carbazole group unsubstituted or substituted with a phenyl group; or a chromene group substituted with ═O, and Ra is a methyl group.


In one embodiment of the present specification, R3 and R4 are the same as each other, and an alkyl group having 1 to 30 carbon atoms unsubstituted or substituted with CF3; a cyclohexyl group unsubstituted or substituted with an alkyl group; an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of fluorine, chlorine, CN, CF3, —C(═O)ORa, NH2, a dialkylamine group, a diphenylamine group, a methoxy group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a pentyl group, a hexyl group, a pyridine group, a dibenzofuranyl group and a carbazole group; a dibenzofuranyl group unsubstituted or substituted with a phenyl group; a dibenzothiophene group; a carbazole group unsubstituted or substituted with a phenyl group; or a chromene group substituted with ═O, and Ra is a methyl group.


In one embodiment of the present specification, R7 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.


In one embodiment of the present specification, R7 is an aryl group unsubstituted or substituted with one or more selected from the group consisting of a halogen group, CN, CF3, an alkoxy group, an alkyl group unsubstituted or substituted with a halogen group, a substituted or unsubstituted aryl group, and a heteroaryl group; or a heteroaryl group unsubstituted or substituted with O═.


In one embodiment of the present specification, R7 is an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of fluorine, chlorine, CN, CF3, an alkoxy group, an alkyl group having 1 to 30 carbon atoms unsubstituted or substituted with a halogen group, an aryl group and a heteroaryl group; a pyridine group; a dibenzofuranyl group; a dibenzothiophene group; a carbazolyl group; or




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In one embodiment of the present specification, R7 is an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of fluorine, chlorine, CN, CF3, a methoxy group, an alkyl group having 1 to 30 carbon atoms unsubstituted or substituted with fluorine or chlorine, a naphthyl group, a dibenzofuranyl group and a pyridine group; a pyridine group; a dibenzofuranyl group; a dibenzothiophene group; a carbazolyl group; or




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In one embodiment of the present specification, X1 to X5 of Chemical Formula 1 may be selected from the following Tables 1-1 to 1-4, R1, R6 and R7 of Chemical Formula 1 may be selected from the following Tables 2-1 to 2-9, and R2 to R5 of Chemical Formula 1 may be selected from the following Tables 3-1 to 3-14.














TABLE 1-1






X4
X5
X1
X2
X3







A1
F
F
O
O
O


A2
F
CN
O
O
O


A3
CN
CN
O
O
O





A4


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O
O
O





A5


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O
O
O





A6


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O
O
O





A7


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O
O
O





A8


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O
O
O





A9


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O
O
O





A10


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O
O
O





















TABLE 1-2






X4
X5
X1
X2
X3







A11
F
F
O
S
S


A12
F
CN
O
S
S


A13
CN
CN
O
S
S





A14


embedded image




embedded image


O
S
S





A15


embedded image




embedded image


O
S
S





A16


embedded image




embedded image


O
S
S





A17


embedded image




embedded image


O
S
S





A18


embedded image




embedded image


O
S
S





A19


embedded image




embedded image


O
S
S





A20


embedded image




embedded image


S
S
S





















TABLE 1-3






X4
X5
X1
X2
X3







A21
F
F
S
O
O


A22
F
CN
S
O
O


A23
CN
CN
S
O
O





A24


embedded image




embedded image


S
O
O





A25


embedded image




embedded image


S
O
O





A26


embedded image




embedded image


S
O
O





A27


embedded image




embedded image


S
O
O





A28


embedded image




embedded image


S
O
O





A29


embedded image




embedded image


S
O
O





A30


embedded image




embedded image


S
O
O





















TABLE 1-4






X4
X5
X1
X2
X3







A31
F
F
S
S
S


A32
F
CN
S
S
S


A33
CN
CN
S
S
S





A34


embedded image




embedded image


S
S
S





A35


embedded image




embedded image


S
S
S





A36


embedded image




embedded image


S
S
S





A37


embedded image




embedded image


S
S
S





A38


embedded image




embedded image


S
S
S





A39


embedded image




embedded image


S
S
S





A40


embedded image




embedded image


S
S
S


















TABLE 2-1









R7












          R1
          R6
    embedded image


embedded image


embedded image
    embedded image





H
H
B1 
B2 
B3 
B4 


Cl
H
B5 
B6 
B7 
B8 


Cl
Cl
B9 
B10 
B11 
B12 


Br
Br
B13 
B14 
B15 
B16 


H
CN
B17 
B18 
B19 
B20 


H
*—
B21 
B22 
B23 
B24 


*—
*—
B25 
B26 
B27 
B28 





H


embedded image


B29 
B30 
B31 
B32 





H


embedded image


B33 
B34 
B35 
B36 





H


embedded image


B37 
B38 
B39 
B40 







embedded image




embedded image


B41 
B42 
B43 
B44 







embedded image




embedded image


B45 
B46 
B47 
B48 







embedded image




embedded image


B49 
B50 
B51 
B52 





H


embedded image


B53 
B54 
B55 
B56 





H


embedded image


B57 
B58 
B59 
B60 





H


embedded image


B61 
B62 
B63 
B64 





H


embedded image


B65 
B66 
B67 
B68 





H


embedded image


B69 
B70 
B71 
B72 





H


embedded image


B73 
B74 
B75 
B76 





H


embedded image


B77 
B78 
B79 
B80 







embedded image




embedded image


B81 
B82 
B83 
B84 







embedded image




embedded image


B85 
B86 
B87 
B88 







embedded image




embedded image


B89 
B90 
B91 
B92 







embedded image




embedded image


B93 
B94 
B95 
B96 







embedded image




embedded image


B97 
B98 
B99 
B100







embedded image




embedded image


B101
B102
B103
B104







embedded image




embedded image


B105
B106
B107
B108





H


embedded image


B109
B110
B111
B112





H


embedded image


B113
B114
B115
B116







embedded image




embedded image


B117
B118
B119
B120







embedded image




embedded image


B121
B122
B123
B124





H


embedded image


B125
B126
B127
B128





H


embedded image


B129
B130
B131
B132





H


embedded image


B133
B134
B135
B136





H


embedded image


B137
B138
B139
B140





H


embedded image


B141
B142
B143
B144





H


embedded image


B145
B146
B147
B148







embedded image




embedded image


B149
B150
B151
B152







embedded image




embedded image


B153
B154
B155
B156







embedded image




embedded image


B157
B158
B159
B160







embedded image




embedded image


B161
B162
B163
B164







embedded image




embedded image


B165
B166
B167
B168







embedded image




embedded image


B169
B170
B171
B172







embedded image




embedded image


B173
B174
B175
B176


















TABLE 2-2









R7












              R1
              R6
      embedded image


embedded image


    embedded image
        embedded image





H
H
B177
B178
B179
B180


Cl
H
B181
B182
B183
B184


Cl
Cl
B185
B186
B187
B188


Br
Br
B189
B190
B191
B192


H
CN
B193
B194
B195
B196


H
*—
B197
B198
B199
B200


*—
*—
B201
B202
B203
B204





H


embedded image


B205
B206
B207
B208





H


embedded image


B209
B210
B211
B212





H


embedded image


B213
B214
B215
B216







embedded image


H
B217
B218
B219
B220







embedded image




embedded image


B221
B222
B223
B224







embedded image




embedded image


B225
B226
B227
B228







embedded image




embedded image


B229
B230
B231
B232





H


embedded image


B233
B234
B235
B236





H


embedded image


B237
B238
B239
B240





H


embedded image


B241
B242
B243
B244





H


embedded image


B245
B246
B247
B248





H


embedded image


B249
B250
B251
B252





H


embedded image


B253
B254
B255
B256





H


embedded image


B257
B258
B259
B260







embedded image




embedded image


B261
B262
B263
B264







embedded image




embedded image


B265
B266
B267
B268







embedded image




embedded image


B269
B270
B271
B272







embedded image




embedded image


B273
B274
B275
B276







embedded image




embedded image


B277
B278
B279
B280







embedded image




embedded image


B281
B282
B283
B284







embedded image




embedded image


B285
B286
B287
B288





H


embedded image


B289
B290
B291
B292





H


embedded image


B293
B294
B295
B296







embedded image




embedded image


B297
B298
B299
B300







embedded image




embedded image


B301
B302
B303
B304





H


embedded image


B305
B306
B307
B308





H


embedded image


B309
B310
B311
B312





H


embedded image


B313
B314
B315
B316





H


embedded image


B317
B318
B319
B320





H


embedded image


B321
B322
B323
B324







embedded image


H
B325
B326
B327
B328







embedded image




embedded image


B329
B330
B331
B332







embedded image




embedded image


B333
B334
B335
B336







embedded image




embedded image


B337
B338
B339
B340







embedded image




embedded image


B341
B342
B343
B344







embedded image




embedded image


B345
B346
B347
B348







embedded image




embedded image


B349
B350
B351
B352


















TABLE 2-3









R7












              R1
              R6
      embedded image
embedded image
embedded image


embedded image







H
H
B353
B354
B355
B356


Cl
H
B357
B358
B359
B360


Cl
Cl
B361
B362
B363
B364


Br
Br
B365
B366
B367
B368


H
CN
B369
B370
B371
B372


H
*—
B373
B374
B375
B376


*—
*—
B377
B378
B379
B380





H


embedded image


B381
B382
B383
B384





H


embedded image


B385
B386
B387
B388





H


embedded image


B389
B390
B391
B392







embedded image




embedded image


B393
B394
B395
B396







embedded image




embedded image


B397
B398
B399
B400







embedded image




embedded image


B401
B402
B403
B404





H


embedded image


B405
B046
B407
B408





H


embedded image


B409
B410
B411
B412





H


embedded image


B413
B414
B415
B416





H


embedded image


B417
B418
B419
B420





H


embedded image


B421
B422
B423
B424





H


embedded image


B425
B426
B427
B428





H


embedded image


B429
B430
B431
B432







embedded image




embedded image


B433
B434
B435
B436







embedded image




embedded image


B437
B438
B439
B440







embedded image




embedded image


B441
B442
B443
B444







embedded image




embedded image


B445
B446
B447
B448







embedded image




embedded image


B449
B450
B451
B452







embedded image




embedded image


B453
B454
B455
B456







embedded image




embedded image


B457
B458
B459
B460





H


embedded image


B461
B462
B463
B464





H


embedded image


B465
B466
B467
B468







embedded image




embedded image


B469
B470
B471
B472







embedded image




embedded image


B473
B474
B475
B476





H


embedded image


B477
B478
B479
B480





H


embedded image


B481
B482
B483
B484





H


embedded image


B485
B486
B487
B488





H


embedded image


B489
B490
B491
B492





H


embedded image


B493
B494
B495
B496





H


embedded image


B497
B498
B499
B500







embedded image




embedded image


B501
B502
B503
B504







embedded image




embedded image


B505
B506
B507
B508







embedded image




embedded image


B509
B510
B511
B512







embedded image




embedded image


B513
B514
B515
B516







embedded image




embedded image


B517
B518
B519
B520







embedded image




embedded image


B521
B522
B523
B524


















TABLE 2-4









R7












              R1
              R6
embedded image


embedded image




embedded image


      embedded image





H
H
B525
B526
B527
B528


Cl
H
B529
B530
B531
B532


Cl
Cl
B533
B534
B535
B536


Br
Br
B537
B538
B539
B540


H
CN
B541
B542
B543
B544


H
*—
B545
B546
B547
B548


*—
*—
B549
B550
B551
B552





H


embedded image


B553
B554
B555
B556





H


embedded image


B557
B558
B559
B560





H


embedded image


B561
B562
B563
B564







embedded image




embedded image


B565
B566
B567
B568







embedded image




embedded image


B569
B570
B571
B572







embedded image




embedded image


B573
B574
B575
B576





H


embedded image


B577
B578
B579
B580







embedded image


H
B581
B582
B583
B584





H


embedded image


B585
B586
B587
B588





H


embedded image


B589
B590
B591
B592





H


embedded image


B593
B594
B595
B596





H


embedded image


B597
B598
B599
B600





H


embedded image


B601
B602
B603
B604





H


embedded image


B605
B606
B607
B608







embedded image




embedded image


B609
B610
B611
B612







embedded image




embedded image


B613
B614
B615
B616







embedded image




embedded image


B617
B618
B619
B620







embedded image




embedded image


B621
B622
B623
B624







embedded image




embedded image


B625
B626
B627
B628







embedded image




embedded image


B629
B630
B631
B632







embedded image




embedded image


B633
B634
B635
B636





H


embedded image


B637
B638
B639
B640





H


embedded image


B641
B642
B643
B644







embedded image




embedded image


B645
B646
B647
B648







embedded image




embedded image


B649
B650
B651
B652





H


embedded image


B653
B654
B655
B656





H


embedded image


B657
B658
B659
B660





H


embedded image


B661
B662
B663
B664





H


embedded image


B665
B666
B667
B668





H


embedded image


B669
B670
B671
B672





H


embedded image


B673
B674
B675
B676







embedded image




embedded image


B677
B678
B679
B680







embedded image




embedded image


B681
B682
B683
B684







embedded image




embedded image


B685
B686
B687
B688







embedded image




embedded image


B689
B690
B691
B692







embedded image




embedded image


B693
B694
B695
B696







embedded image




embedded image


B697
B698
B699
B700


















TABLE 2-5









R7












          R1
          R6
    embedded image
embedded image


embedded image


    embedded image





H
H
B701
B702
B703
B704


Cl
H
B705
B706
B707
B708


Cl
Cl
B709
B710
B711
B712


Br
Br
B713
B714
B715
B716


H
CN
B717
B718
B719
B720


H
*—
B721
B722
B723
B724


*—
*—
B725
B726
B727
B728





H


embedded image


B729
B730
B731
B732





H


embedded image


B733
B734
B735
B736





H


embedded image


B737
B738
B739
B740







embedded image




embedded image


B741
B742
B743
B744







embedded image




embedded image


B745
B746
B747
B748







embedded image




embedded image


B749
B750
B751
B752





H


embedded image


B753
B754
B755
B756





H


embedded image


B757
B758
B759
B760





H


embedded image


B761
B762
B763
B764





H


embedded image


B765
B766
B767
B768





H


embedded image


B769
B770
B771
B772





H


embedded image


B773
B774
B775
B776





H


embedded image


B777
B778
B779
B780







embedded image




embedded image


B781
B782
B783
B784







embedded image




embedded image


B785
B786
B787
B788







embedded image




embedded image


B789
B790
B791
B792







embedded image




embedded image


B793
B794
B795
B796







embedded image




embedded image


B797
B798
B799
B800







embedded image




embedded image


B801
B802
B803
B804







embedded image




embedded image


B805
B806
B807
B808





H


embedded image


B809
B810
B811
B812





H


embedded image


B813
B814
B815
B816







embedded image




embedded image


B817
B818
B819
B820







embedded image




embedded image


B821
B822
B823
B824





H


embedded image


B825
B826
B827
B828





H


embedded image


B829
B830
B831
B832





H


embedded image


B833
B834
B835
B836





H


embedded image


B837
B838
B839
B840





H


embedded image


B841
B842
B843
B844





H


embedded image


B845
B846
B847
B848







embedded image




embedded image


B849
B850
B851
B852







embedded image




embedded image


B853
B854
B855
B856







embedded image




embedded image


B857
B858
B859
B860







embedded image




embedded image


B861
B862
B863
B864







embedded image




embedded image


B865
B866
B867
B868







embedded image




embedded image


B869
B870
B871
B872







embedded image




embedded image


B873
B874
B875
B876


















TABLE 2-6









R7












                  R1
                  R6
            embedded image


embedded image


          embedded image
            embedded image





H
H
B877 
B878 
B879 
B880 


Cl
H
B881 
B882 
B883 
B884 


Cl
Cl
B885 
B886 
B887 
B888 


Br
Br
B889 
B890 
B891 
B892 


H
CN
B893 
B894 
B895 
B896 


H
*—
B897 
B898 
B899 
B900 


*—
*—
B901 
B902 
B903 
B904 





H


embedded image


B905 
B906 
B907 
B908 





H


embedded image


B909 
B910 
B911 
B912 







embedded image


H
B913 
B914 
B915 
B916 







embedded image




embedded image


B917 
B918 
B919 
B920 







embedded image




embedded image


B921 
B922 
B923 
B924 







embedded image




embedded image


B925 
B926 
B927 
B928 





H


embedded image


B929 
B930 
B931 
B932 





H


embedded image


B933 
B934 
B935 
B936 





H


embedded image


B937 
B938 
B939 
B940 





H


embedded image


B941 
B942 
B943 
B944 





H


embedded image


B945 
B946 
B947 
B948 





H


embedded image


B949 
B950 
B951 
B952 





H


embedded image


B953 
B954 
B955 
B956 







embedded image




embedded image


B957 
B958 
B959 
B960 







embedded image




embedded image


B961 
B962 
B963 
B964 







embedded image




embedded image


B965 
B966 
B967 
B968 







embedded image




embedded image


B969 
B970 
B971 
B972 







embedded image




embedded image


B973 
B974 
B975 
B976 







embedded image




embedded image


B977 
B978 
B979 
B980 







embedded image




embedded image


B981 
B982 
B983 
B983 





H


embedded image


B985 
B986 
B987 
B988 





H


embedded image


B989 
B990 
B991 
B992 







embedded image




embedded image


B993 
B994 
B995 
B996 







embedded image




embedded image


B997 
B998 
B999 
B1000





H


embedded image


B1001
B1002
B1003
B1004





H


embedded image


B1005
B1006
B1007
B1008





H


embedded image


B1009
B1010
B1011
B1012





H


embedded image


B1013
B1014
B1015
B1016





H


embedded image


B1017
B1018
B1019
B1020





H


embedded image


B1021
B1022
B1023
B1024







embedded image




embedded image


B1025
B1026
B1027
B1028







embedded image




embedded image


B1029
B1030
B1031
B1032







embedded image




embedded image


B1033
B1034
B0135
B1036







embedded image




embedded image


B1037
B1038
B1039
B1040







embedded image




embedded image


B1041
B1042
B1043
B1044







embedded image




embedded image


B1045
B1046
B1047
B1048







embedded image




embedded image


B1049
B1050
B1051
B1052


















TABLE 2-7









R7












R1
R6


embedded image




embedded image




embedded image




embedded image







H
H
B1053
B1054
B1055
B1056


Cl
H
B1057
B1058
B1059
B1060


Cl
Cl
B1061
B1062
B1063
B1064


Br
Br
B1065
B1066
B1067
B1068


H
CN
B1069
B1070
B1071
B1072


H
*—
B1073
B1074
B1075
B1076


*—
*—
B1077
B1078
B1079
B1080





H


embedded image


B1081
B1082
B1083
B1084





H


embedded image


B1085
B1086
B1087
B1088





H


embedded image


B1089
B1090
B1091
B1092







embedded image




embedded image


B1093
B1094
B1095
B1096







embedded image




embedded image


B1097
B1098
B1099
B1100







embedded image




embedded image


B1101
B1102
B1103
B1104





H


embedded image


B1105
B1106
B1107
B1108





H


embedded image


B1109
B1110
B1111
B1112





H


embedded image


B1113
B1114
B1115
B1116





H


embedded image


B1117
B1118
B1119
B1120





H


embedded image


B1121
B1122
B1123
B1123





H


embedded image


B1124
B1125
B1126
B1127





H


embedded image


B1128
B1129
B1130
B1131







embedded image




embedded image


B11132
B1133
B1134
B1135







embedded image




embedded image


B1136
B1137
B1138
B1139







embedded image




embedded image


B1140
B1141
B1142
B1143







embedded image




embedded image


B1144
B1145
B1146
B1147







embedded image




embedded image


B1148
B1149
B1150
B1151







embedded image




embedded image


B1152
B1153
B1154
B1155







embedded image




embedded image


B1156
B1157
B1158
B1169





H


embedded image


B1160
B1161
B1162
B1163





H


embedded image


B1164
B1165
B1166
B1167







embedded image




embedded image


B1168
B1169
B1170
B1171







embedded image




embedded image


B1172
B1173
B1174
B1175





H


embedded image


B1176
B1177
B1178
B1179





H


embedded image


B1180
B1181
B1182
B1183





H


embedded image


B1184
B1185
B1186
B1187





H


embedded image


B1188
B1189
B1190
B1191





H


embedded image


B1192
B1193
B1194
B1195





H


embedded image


B1196
B1197
B1198
B1199







embedded image




embedded image


B1200
B1201
B1202
B1203







embedded image




embedded image


B1204
B1205
B1206
B1207







embedded image




embedded image


B1208
B1209
B1210
B1211







embedded image




embedded image


B1212
B1213
B1214
81215







embedded image




embedded image


B1216
B1217
B1218
B1219







embedded image




embedded image


B1220
B1221
B1222
B1223







embedded image




embedded image


B1224
B1225
B1226
B1227







embedded image


H
B1228
B1229
B1230
B1231


















TABLE 2-8









R7












R1
R6


embedded image




embedded image




embedded image




embedded image







H
H
B1232
B1233
B1234
B1235


Cl
H
B1236
B1237
B1237
B1238


Cl
Cl
B1239
B1240
B1241
B1242


Br
Br
B1243
B1244
B1245
B1246


H
CN
B1247
B1248
B1249
B1250


H
*—
B1251
B1252
B1253
B1254


*—
*—
B1255
B1256
B1257
B1258





H


embedded image


B1259
B1260
B1261
B1262





H


embedded image


B1263
B1264
B1265
B1266





H


embedded image


B1267
B1268
B1269
B1270







embedded image


H
B1271
B1272
B1273
B1274







embedded image




embedded image


B1275
B1276
B1277
B1278







embedded image




embedded image


B1279
B1280
B1281
B1282







embedded image




embedded image


B1283
B1284
B1285
B1286





H


embedded image


B1287
B1288
B1289
B1290







embedded image


H
B1291
B1292
B1293
B1294





H


embedded image


B1295
B1296
B1297
B1298





H


embedded image


B1299
B1300
B1301
B1302





H


embedded image


B1303
B1304
B1035
B1306





H


embedded image


B1037
B1308
B1309
B1310





H


embedded image


B1311
B1312
B1313
B1314





H


embedded image


B1315
B1316
B1317
B1318







embedded image




embedded image


B1319
B1320
B1321
B1322







embedded image




embedded image


B1323
B1324
B1325
B1326







embedded image




embedded image


B1327
B1328
B1329
B1330







embedded image




embedded image


B1331
B1332
B1333
B1334







embedded image




embedded image


B1335
B1336
B1337
B1338







embedded image




embedded image


B1339
B1340
B1341
B1342







embedded image




embedded image


B1343
B1344
B1345
B1346





H


embedded image


B1347
B1348
B1349
B1350





H


embedded image


B1351
B1352
B1353
B1354







embedded image




embedded image


B1355
B1356
B1357
B1358







embedded image




embedded image


B1359
B1360
B1361
B1362





H


embedded image


B1363
B1364
B1365
B1366





H


embedded image


B1367
B1368
B1369
B1370





H


embedded image


B1371
B1372
B1373
B1374





H


embedded image


B1375
B1376
B1377
B1378





H


embedded image


B1379
B1380
B1381
B1382





H


embedded image


B1383
B1384
B1385
B1386







embedded image




embedded image


B1387
B1388
B1389
B1390







embedded image




embedded image


B1391
B1392
B1303
B1394







embedded image




embedded image


B1395
B1396
B1397
B1393







embedded image




embedded image


B1399
B1400
B1401
B1402







embedded image




embedded image


B1403
B1404
B1405
B1406







embedded image




embedded image


B1407
B1408
B1409
B1410







embedded image




embedded image


B1411
B1412
B1413
B1414







embedded image


H
B1415
B1416
B1417
B1413


















TABLE 2-9









R7











R1
R6


embedded image




embedded image




embedded image







H
H
B1419
B1420
B1421


Cl
H
B1422
B1423
B1424


Cl
Cl
B1425
B1426
B1427


Br
Br
B1428
B1429
B1430


H
CN
B1431
B1432
B1433


H
*—
B1434
B1435
B1436


*—
*—
B1437
B1438
B1430





H


embedded image


B1440
B1441
B1442





H


embedded image


B1443
B1444
B1445





H


embedded image


B1446
B1447
B1448







embedded image


H
B1449
B1450
B1451







embedded image




embedded image


B1452
B1453
B1454







embedded image




embedded image


B1455
B1456
B1457







embedded image




embedded image


B1458
B1459
B1460





H


embedded image


B1461
B1462
B1463







embedded image


H
B1464
B1465
B1466





H


embedded image


B1467
B1468
B1469





H


embedded image


B1470
B1471
B1472





H


embedded image


B1473
B1474
B1475





H


embedded image


B1476
B1477
B1478





H


embedded image


B1479
B1480
B1481





H


embedded image


B1482
B1483
B1484







embedded image




embedded image


B1485
B1486
B1487







embedded image




embedded image


B1488
B1489
B1490







embedded image




embedded image


B1491
B1492
B1493







embedded image




embedded image


B1494
B1495
B1496







embedded image




embedded image


B1497
B1498
B1499







embedded image




embedded image


B1500
B1501
B1502







embedded image




embedded image


B1503
B1504
B1505





H


embedded image


B1506
B1507
B1508





H


embedded image


B1509
B1510
B1511







embedded image




embedded image


B1512
B1513
B1514







embedded image




embedded image


B1515
B1516
B1517





H


embedded image


B1518
B1519
B1520







embedded image


H
B1521
B1522
B1523





H


embedded image


B1524
B1526
B1526





H


embedded image


B1527
B1528
B1529





H


embedded image


B1530
B1531
B1532





H


embedded image


B1533
B1534
B1535





H


embedded image


B1536
B1537
B1538







embedded image




embedded image


B1539
B1540
B1541







embedded image




embedded image


B1542
B1543
B1544







embedded image




embedded image


B1545
B1546
B1547







embedded image




embedded image


B1548
B1549
B1550







embedded image




embedded image


B1551
B1552
B1553







embedded image




embedded image


B1554
B1555
B1556







embedded image




embedded image


B1557
B1558
B1559







embedded image


H
B1560
B1561
B1562





H


embedded image


B1563
B1564
B1565







embedded image




embedded image


B1566
B1567
B1568







embedded image


H
B1569
B1570
B1571







embedded image




embedded image


B1572
B1573
B1574





H


embedded image


B1575
B1576
B1577


















TABLE 3-1









R3, R4













R2
R5


embedded image




embedded image




embedded image




embedded image




embedded image









embedded image




embedded image


C1
C2
C3
C4
C5







embedded image




embedded image


C6
C7
C8
C9
C10







embedded image




embedded image


C11
C12
C13
C14
C15







embedded image




embedded image


C16
C17
C18
C19
C20







embedded image




embedded image


C21
C22
C23
C24
C25







embedded image




embedded image


C26
C27
C28
C29
C30







embedded image




embedded image


C31
C32
C33
C34
C35







embedded image




embedded image


C36
C37
C38
C39
C40







embedded image




embedded image


C41
C42
C43
C44
C45







embedded image




embedded image


C46
C47
C48
C49
C50







embedded image




embedded image


C51
C52
C53
C54
C55







embedded image




embedded image


C56
C57
C58
C59
CC0







embedded image




embedded image


C61
C62
C63
C64
C65







embedded image




embedded image


C66
C67
C68
C69
C70







embedded image




embedded image


C71
C72
C73
C74
C75







embedded image




embedded image


C76
C77
C78
C79
C80







embedded image




embedded image


C81
C82
C83
C84
C85







embedded image




embedded image


C86
C87
C88
C89
C90







embedded image




embedded image


C91
C92
C93
C94
C95







embedded image




embedded image


C96
C97
C98
C99
C100







embedded image




embedded image


C101
C102
C103
C104
C105







embedded image




embedded image


C106
C107
C108
C109
C110







embedded image




embedded image


C111
C112
C113
C114
C115







embedded image




embedded image


C116
C117
C118
C119
C120







embedded image




embedded image


C121
C122
C123
C124
C125







embedded image




embedded image


C126
C127
C128
C129
C130







embedded image




embedded image


C131
C132
C133
C134
C135







embedded image




embedded image


C136
C137
C138
C139
C140


















TABLE 3-2









R3, R4












R2
R5


embedded image




embedded image




embedded image




embedded image









embedded image




embedded image


C141
C142
C143
C144







embedded image




embedded image


C145
C146
C147
C148







embedded image




embedded image


C149
C150
C151
C152







embedded image




embedded image


C153
C154
C155
C156







embedded image




embedded image


C157
C158
C159
C160







embedded image




embedded image


C161
C162
C163
C164







embedded image




embedded image


C165
C166
C167
C168







embedded image




embedded image


C169
C170
C171
C172







embedded image




embedded image


C173
C174
C176
C176







embedded image




embedded image


C177
C178
C179
C180







embedded image




embedded image


C181
C182
C183
C184







embedded image




embedded image


C185
C186
C187
C188







embedded image




embedded image


C189
C190
C191
C192







embedded image




embedded image


C193
C194
C195
C196







embedded image




embedded image


C197
C198
C199
C200







embedded image




embedded image


C201
C202
C203
C204







embedded image




embedded image


C205
C206
C207
C208







embedded image




embedded image


C209
C210
C211
C212







embedded image




embedded image


C213
C214
C215
C216







embedded image




embedded image


C217
C218
C219
C220







embedded image




embedded image


C221
C222
C223
C224







embedded image




embedded image


C225
C226
C227
C228







embedded image




embedded image


C229
C230
C231
C232







embedded image




embedded image


C233
C234
C235
C236







embedded image




embedded image


C237
C238
C239
C240







embedded image




embedded image


C241
C242
C243
C244







embedded image




embedded image


C245
C246
C247
C248


















TABLE 3-3









R3, R4











R2
R5


embedded image




embedded image




embedded image









embedded image




embedded image


C249
C260
C251







embedded image




embedded image


C252
C253
C254







embedded image




embedded image


C255
C256
C257







embedded image




embedded image


C258
C259
C260







embedded image




embedded image


C261
C262
C263







embedded image




embedded image


C264
C265
C266







embedded image




embedded image


C267
C268
C269







embedded image




embedded image


C270
C271
C272







embedded image




embedded image


C273
C274
C275







embedded image




embedded image


C276
C277
C278







embedded image




embedded image


C279
C280
C281







embedded image




embedded image


C282
C283
C284







embedded image




embedded image


C285
C286
C287







embedded image




embedded image


C288
C289
C290







embedded image




embedded image


C291
C292
C293







embedded image




embedded image


C294
C295
C296







embedded image




embedded image


C297
C298
C299







embedded image




embedded image


C300
C301
C302







embedded image




embedded image


C303
C304
C305







embedded image




embedded image


C306
C307
C308







embedded image




embedded image


C309
C310
C311







embedded image




embedded image


C312
C313
C314







embedded image




embedded image


C315
C316
C317







embedded image




embedded image


C318
C319
C320







embedded image




embedded image


C321
C322
C323







embedded image




embedded image


C324
C325
C326







embedded image




embedded image


C327
C328
C329


















TABLE 3-4









R3, R4












R2
R5


embedded image




embedded image




embedded image




embedded image









embedded image




embedded image


C330
C331
C332
C333







embedded image




embedded image


C334
C335
C336
C337







embedded image




embedded image


C338
C339
C340
C341







embedded image




embedded image


C342
C343
C344
C345







embedded image




embedded image


C346
C347
C348
C349







embedded image




embedded image


C350
C351
C352
C353







embedded image




embedded image


C354
C356
C356
C357







embedded image




embedded image


C358
C359
C360
C361







embedded image




embedded image


C362
C363
C364
C365







embedded image




embedded image


C366
C367
C368
C360







embedded image




embedded image


C370
C371
C372
C373







embedded image




embedded image


C374
C375
C376
C377







embedded image




embedded image


C378
C379
C380
C381







embedded image




embedded image


C382
C383
C384
C385







embedded image




embedded image


C386
C387
C388
C389







embedded image




embedded image


C390
C391
C392
C393







embedded image




embedded image


C394
C395
C396
C397







embedded image




embedded image


C398
C399
C400
C401







embedded image




embedded image


C402
C403
C404
C405







embedded image




embedded image


C406
C407
C408
C409







embedded image




embedded image


C410
C411
C412
C413







embedded image




embedded image


C414
C415
C416
C417







embedded image




embedded image


C418
C419
C420
C421







embedded image




embedded image


C422
C423
C424
C425







embedded image




embedded image


C426
C427
C428
C429

















TABLE 3-5








R3, R4











R2
R5


embedded image




embedded image




embedded image









embedded image




embedded image


C430
C431
C432







embedded image




embedded image


C433
C434
C435







embedded image




embedded image


C436
C437
C438







embedded image




embedded image


C439
C440
C441







embedded image




embedded image


C442
C443
C444







embedded image




embedded image


C445
C446
C447







embedded image




embedded image


C448
C449
C450







embedded image




embedded image


C451
C452
C453







embedded image




embedded image


C454
C455
C456







embedded image




embedded image


C457
C458
C459







embedded image




embedded image


C460
C461
C462







embedded image




embedded image


C463
C464
C465







embedded image




embedded image


C466
C467
C468







embedded image




embedded image


C469
C470
C471







embedded image




embedded image


C472
C473
C474







embedded image




embedded image


C475
C476
C477







embedded image




embedded image


C478
C479
C480







embedded image




embedded image


C481
C482
C483







embedded image




embedded image


C484
C485
C486







embedded image




embedded image


C487
C488
C489







embedded image




embedded image


C490
C491
C492







embedded image




embedded image


C493
C494
C495







embedded image




embedded image


C496
C497
C498







embedded image




embedded image


C499
C500
C501







embedded image




embedded image


C502
C503
C504

















TABLE 3-6








R3, R4











R2
R5


embedded image




embedded image




embedded image









embedded image




embedded image


C505
C506
C507







embedded image




embedded image


C508
C509
C510







embedded image




embedded image


C511
C512
C513







embedded image




embedded image


C514
C515
C516







embedded image




embedded image


C517
C518
C519







embedded image




embedded image


C520
C521
C522







embedded image




embedded image


C523
C524
C525







embedded image




embedded image


C526
C527
C528







embedded image




embedded image


C529
C530
C531







embedded image




embedded image


C532
C533
C534







embedded image




embedded image


C535
C536
C537







embedded image




embedded image


C538
C539
C540







embedded image




embedded image


C541
C542
C543







embedded image




embedded image


C544
C545
C546







embedded image




embedded image


C547
C548
C549







embedded image




embedded image


C550
C551
C552







embedded image




embedded image


C553
C554
C555







embedded image




embedded image


C556
C557
C558







embedded image




embedded image


C559
C560
C561







embedded image




embedded image


C562
C563
C564







embedded image




embedded image


C565
C566
C567







embedded image




embedded image


C568
C569
C570







embedded image




embedded image


C571
C572
C573







embedded image




embedded image


C574
C575
C576







embedded image




embedded image


C577
C578
C579







embedded image




embedded image


C580
C581
C582







embedded image




embedded image


C583
C584
C585

















TABLE 3-7








R3, R4











R2
R5


embedded image




embedded image




embedded image









embedded image




embedded image


C586
C587
C588







embedded image




embedded image


C589
C590
C591







embedded image




embedded image


C592
C593
C594







embedded image




embedded image


C595
C596
C597







embedded image




embedded image


C598
C599
C600







embedded image




embedded image


C601
C602
C603







embedded image




embedded image


C604
C605
C606







embedded image




embedded image


C607
C608
C609







embedded image




embedded image


C610
C611
C612







embedded image




embedded image


C613
C614
C615







embedded image




embedded image


C616
C617
C618







embedded image




embedded image


C619
C620
C621







embedded image




embedded image


C622
C623
C624







embedded image




embedded image


C625
C626
C627







embedded image




embedded image


C628
C629
C630







embedded image




embedded image


C631
C632
C633







embedded image




embedded image


C634
C635
C636







embedded image




embedded image


C637
C638
C639







embedded image




embedded image


C640
C641
C642







embedded image




embedded image


C643
C644
C645







embedded image




embedded image


C646
C647
C648







embedded image




embedded image


C649
C650
C651







embedded image




embedded image


C652
C653
C654







embedded image




embedded image


C655
C656
C657







embedded image




embedded image


C658
C659
C660

















TABLE 3-8








R3, R4











R2
R5


embedded image




embedded image




embedded image









embedded image




embedded image


C661
C662
C663







embedded image




embedded image


C664
C665
C666







embedded image




embedded image


C667
C668
C669







embedded image




embedded image


C670
C671
C672







embedded image




embedded image


C673
C674
C675







embedded image




embedded image


C676
C677
C678







embedded image




embedded image


C679
C680
C681







embedded image




embedded image


C682
C683
C684







embedded image




embedded image


C685
C686
C687







embedded image




embedded image


C688
C689
C690







embedded image




embedded image


C691
C692
C693







embedded image




embedded image


C694
C695
C696







embedded image




embedded image


C697
C698
C699







embedded image




embedded image


C700
C701
C702







embedded image




embedded image


C703
C704
C705







embedded image




embedded image


C706
C707
C708







embedded image




embedded image


C709
C710
C711







embedded image




embedded image


C712
C713
C714







embedded image




embedded image


C715
C716
C717







embedded image




embedded image


C718
C719
C720







embedded image




embedded image


C721
C722
C723







embedded image




embedded image


C724
C725
C726







embedded image




embedded image


C727
C728
C729







embedded image




embedded image


C730
C731
C732







embedded image




embedded image


C733
C734
C735







embedded image




embedded image


C736
C737
C738







embedded image




embedded image


C739
C740
C741







embedded image




embedded image


C742
C743
C744

















TABLE 3-9








R3, R4











R2
R5


embedded image




embedded image




embedded image









embedded image




embedded image


C745
C746
C747







embedded image




embedded image


C748
C749
C750







embedded image




embedded image


C751
C752
C753







embedded image




embedded image


C754
C755
C756







embedded image




embedded image


C757
C758
C759







embedded image




embedded image


C760
C761
C762







embedded image




embedded image


C763
C764
C765







embedded image




embedded image


C766
C767
C768







embedded image




embedded image


C769
C770
C771







embedded image




embedded image


C772
C773
C774







embedded image




embedded image


C775
C776
C777







embedded image




embedded image


C778
C779
C780







embedded image




embedded image


C781
C782
C783







embedded image




embedded image


C784
C785
C786







embedded image




embedded image


C787
C788
C789







embedded image




embedded image


C790
C791
C792







embedded image




embedded image


C793
C794
C795







embedded image




embedded image


C796
C797
C798







embedded image




embedded image


C799
C800
C801







embedded image




embedded image


C802
C803
C804







embedded image




embedded image


C805
C806
C807







embedded image




embedded image


C808
C809
C810







embedded image




embedded image


C811
C812
C813







embedded image




embedded image


C814
C815
C816







embedded image




embedded image


C817
C818
C819







embedded image




embedded image


C820
C821
C822







embedded image




embedded image


C823
C824
C825







embedded image




embedded image


C826
C827
C828







embedded image




embedded image


C829
C830
C831







embedded image




embedded image


C832
C833
C834







embedded image




embedded image


C835
C836
C837







embedded image




embedded image


C838
C839
C840

















TABLE 3-10








R3, R4











R2
R5


embedded image




embedded image




embedded image









embedded image




embedded image


C841
C842
C843







embedded image




embedded image


C844
C845
C846







embedded image




embedded image


C847
C848
C849







embedded image




embedded image


C850
C851
C852







embedded image




embedded image


C853
C854
C855







embedded image




embedded image


C856
C857
C858







embedded image




embedded image


C859
C860
C861







embedded image




embedded image


C862
C863
C864







embedded image




embedded image


C865
C866
C867







embedded image




embedded image


C868
C869
C870







embedded image




embedded image


C871
C872
C873







embedded image




embedded image


C874
C875
C876







embedded image




embedded image


C877
C878
C879







embedded image




embedded image


C880
C881
C882







embedded image




embedded image


C883
C884
C885







embedded image




embedded image


C886
C887
C888







embedded image




embedded image


C889
C890
C891







embedded image




embedded image


C892
C893
C894







embedded image




embedded image


C895
C896
C897







embedded image




embedded image


C898
C899
C900







embedded image




embedded image


C901
C902
C903







embedded image




embedded image


C904
C905
C906







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embedded image


C907
C908
C909







embedded image




embedded image


C910
C911
C912







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embedded image


C913
C914
C915


















TABLE 3-11









R3, R4












R2
R5


embedded image




embedded image




embedded image




embedded image









embedded image




embedded image


C916
C917
C918
C919







embedded image




embedded image


C920
C921
C922
C923







embedded image




embedded image


C924
C925
C926
C927







embedded image




embedded image


C928
C929
C930
C931







embedded image




embedded image


C932
C933
C934
C935







embedded image




embedded image


C936
C937
C938
C939







embedded image




embedded image


C940
C941
C942
C943







embedded image




embedded image


C944
C945
C946
C947







embedded image




embedded image


C948
C949
C950
C951







embedded image




embedded image


C952
C953
C954
C955







embedded image




embedded image


C956
C957
C958
C959







embedded image




embedded image


C960
C961
C962
C963







embedded image




embedded image


C964
C965
C966
C967







embedded image




embedded image


C968
C969
C970
C971







embedded image




embedded image


C972
C973
C974
C975







embedded image




embedded image


C976
C977
C978
C979







embedded image




embedded image


C980
C981
C982
C983







embedded image




embedded image


C984
C985
C986
C987







embedded image




embedded image


C988
C989
C990
C991







embedded image




embedded image


C992
C993
C994
C995







embedded image




embedded image


C996
C997
C998
C999







embedded image




embedded image


C1000
C1001
C1002
C1003







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embedded image


C1004
C1005
C1006
C1007







embedded image




embedded image


C1008
C1009
C1010
C1011







embedded image




embedded image


C1012
C1013
C1014
C1015







embedded image




embedded image


C1016
C1017
C1018
C1019


















TABLE 3-12









R3, R4












R2
R5


embedded image




embedded image




embedded image




embedded image









embedded image




embedded image


C1020
C1021
C1022
C1023







embedded image




embedded image


C1024
C1025
C1026
C1027







embedded image




embedded image


C1028
C1029
C1030
C1031







embedded image




embedded image


C1032
C1033
C1034
C1035







embedded image




embedded image


C1036
C1037
C1038
C1039







embedded image




embedded image


C1040
C1041
C1042
C1043







embedded image




embedded image


C1044
C1045
C1046
C1047







embedded image




embedded image


C1048
C1049
C1050
C1051







embedded image




embedded image


C1052
C1053
C1054
C1055







embedded image




embedded image


C1056
C1057
C1058
C1059







embedded image




embedded image


C1060
C1061
C1062
C1063







embedded image




embedded image


C1064
C1065
C1066
C1067







embedded image




embedded image


C1068
C1069
C1070
C1071







embedded image




embedded image


C1072
C1073
C1074
C1075







embedded image




embedded image


C1076
C1077
C1078
C1079







embedded image




embedded image


C1080
C1081
C1082
C1083







embedded image




embedded image


C1084
C1085
C1086
C1087







embedded image




embedded image


C1088
C1089
C1090
C1091







embedded image




embedded image


C1092
C1093
C1094
C1095







embedded image




embedded image


C1096
C1097
C1098
C1099







embedded image




embedded image


C1100
C1101
C1102
C1103







embedded image




embedded image


C1104
C1105
C1106
C1107







embedded image




embedded image


C1108
C1109
C1110
C1111







embedded image




embedded image


C1112
C1113
C1114
C1115







embedded image




embedded image


C1116
C1117
C1118
C1119







embedded image




embedded image


C1120
C1121
C1122
C1123







embedded image




embedded image


C1124
C1125
C1126
C1127







embedded image




embedded image


C1128
C1129
C1130
C1131







embedded image




embedded image


C1132
C1133
C1134
C1135







embedded image




embedded image


C1136
C1137
C1138
C1139







embedded image




embedded image


C1140
C1141
C1142
C1143







embedded image




embedded image


C1144
C1145
C1146
C1147







embedded image




embedded image


C1148
C1149
C1150
C1151







embedded image




embedded image


C1152
C1153
C1154
C1155







embedded image




embedded image


C1156
C1157
C1158
C1159







embedded image




embedded image


C1160
C1161
C1162
C1163







embedded image




embedded image


C1164
C1165
C1166
C1167


















TABLE 3-13









R3, R4












R2
R5


embedded image




embedded image




embedded image




embedded image









embedded image




embedded image


C1168
C1169
C1170
C1171







embedded image




embedded image


C1172
C1173
C1174
C1175







embedded image




embedded image


C1176
C1177
C1178
C1179







embedded image




embedded image


C1180
C1181
C1182
C1183







embedded image




embedded image


C1184
C1185
C1186
C1187







embedded image




embedded image


C1188
C1189
C1190
C1191







embedded image




embedded image


C1192
C1193
C1194
C1195







embedded image




embedded image


C1196
C1197
C1198
C1199







embedded image




embedded image


C1200
C1201
C1202
C1203







embedded image




embedded image


C1204
C1205
C1206
C1207







embedded image




embedded image


C1208
C1209
C1210
C1211







embedded image




embedded image


C1212
C1213
C1214
C1215







embedded image




embedded image


C1216
C1217
C1218
C1219







embedded image




embedded image


C1220
C1221
C1222
C1223







embedded image




embedded image


C1224
C1225
C1226
C1227







embedded image




embedded image


C1228
C1229
C1230
C1231







embedded image




embedded image


C1232
C1233
C1234
C1235







embedded image




embedded image


C1236
C1237
C1238
C1239







embedded image




embedded image


C1240
C1241
C1242
C1243







embedded image




embedded image


C1244
C1245
C1246
C1247







embedded image




embedded image


C1248
C1249
C1250
C1251







embedded image




embedded image


C1252
C1253
C1254
C1255







embedded image




embedded image


C1256
C1257
C1258
C1259







embedded image




embedded image


C1260
C1261
C1262
C1263







embedded image




embedded image


C1264
C1265
C1266
C1267







embedded image




embedded image


C1268
C1269
C1270
C1271







embedded image




embedded image


C1272
C1273
C1274
C1275







embedded image




embedded image


C1276
C1277
C1278
C1279







embedded image




embedded image


C1280
C1281
C1282
C1283







embedded image




embedded image


C1284
C1285
C1286
C1287







embedded image




embedded image


C1288
C1289
C1290
C1291







embedded image




embedded image


C1292
C1293
C1294
C1295







embedded image




embedded image


C1296
C1297
C1298
C1299







embedded image




embedded image


C1300
C1301
C1302
C1303







embedded image




embedded image


C1304
C1305
C1306
C1307







embedded image




embedded image


C1308
C1309
C1310
C1311







embedded image




embedded image


C1312
C1313
C1314
C1315







embedded image




embedded image


C1316
C1317
C1318
C1319







embedded image




embedded image


C1320
C1321
C1322
C1323







embedded image




embedded image


C1324
C1325
C1326
C1327







embedded image




embedded image


C1328
C1329
C1330
C1331







embedded image




embedded image


C1332
C1333
C1334
C1335







embedded image




embedded image


C1336
C1337
C1338
C1339







embedded image




embedded image


C1340
C1341
C1342
C1343







embedded image




embedded image


C1344
C1345
C1346
C1347


















TABLE 3-14









R3, R4










R2
R5


embedded image




embedded image









embedded image




embedded image


C1348
C1349







embedded image




embedded image


C1350
C1351







embedded image




embedded image


C1352
C1353







embedded image




embedded image


C1354
C1355







embedded image




embedded image


C1356
C1357







embedded image




embedded image


C1358
C1359







embedded image




embedded image


C1360
C1361







embedded image




embedded image


C1362
C1363







embedded image




embedded image


C1364
C1365







embedded image




embedded image


C1366
C1367







embedded image




embedded image


C1368
C1369







embedded image




embedded image


C1370
C1371







embedded image




embedded image


C1372
C1373







embedded image




embedded image


C1374
C1375







embedded image




embedded image


C1376
C1377







embedded image




embedded image


C1378
C1379







embedded image




embedded image


C1380
C1381







embedded image




embedded image


C1382
C1383







embedded image




embedded image


C1384
C1385







embedded image




embedded image


C1386
C1387







embedded image




embedded image


C1388
C1389







embedded image




embedded image


C1390
C1391







embedded image




embedded image


C1392
C1393







embedded image




embedded image


C1394
C1395







embedded image




embedded image


C1396
C1397







embedded image




embedded image


C1398
C1399







embedded image




embedded image


C1400
C1401







embedded image




embedded image


C1402
C1403







embedded image




embedded image


C1404
C1405







embedded image




embedded image


C1406
C1407







embedded image




embedded image


C1408
C1409







embedded image




embedded image


C1410
C1411







embedded image




embedded image


C1412
C1413







embedded image




embedded image


C1414
C1415







embedded image




embedded image


C1416
C1417







embedded image




embedded image


C1418
C1419







embedded image




embedded image


C1420
C1421







embedded image




embedded image


C1422
C1423







embedded image




embedded image


C1424
C1425







embedded image




embedded image


C1426
C1427







embedded image




embedded image


C1428
C1429







embedded image




embedded image


C1430
C1431







embedded image




embedded image


C1432
C1433







embedded image




embedded image


C1434
C1435









In Tables 1-1 to 1-4, 2-1 to 2-9, and 3-1 to 3-14 in one embodiment of the present specification, * means a position bonding to Chemical Formula 1.


In one embodiment of the present specification, the compounds represented by Chemical Formula 1 are referred to as [1-1 to 1-4]-[2-1 to 2-9]-[3-1 to 3-14] according to the above-described Tables 1-1 to 1-4, 2-1 to 2-9, and 3-1 to 3-14, and specifically, for example, the compound of A1-B328-C437 has a structure as the following Structure 1, and the compound of A21-B423-C628 has a structure as the following Structure 2.




embedded image


According to one embodiment of the present specification, the compound represented by Chemical Formula 1 has a maximum light emission peak present in 500 nm to 550 nm in a film state. Such a compound emits green light.


According to one embodiment of the present specification, the compound represented by Chemical Formula 1 has a maximum light emission peak present in 520 nm to 550 nm in a film state, and the light emission peak has a full width at half maximum of 50 nm or less. Having such a small full width at half maximum may further increase color gamut. Herein, it is the better that the light emission peak of the compound represented by Chemical Formula 1 has a smaller full width at half maximum.


According to one embodiment of the present specification, the compound represented by Chemical Formula 1 has a maximum light emission peak present in 580 nm to 680 nm in a film state. Such a compound emits red light.


According to one embodiment of the present specification, the compound represented by Chemical Formula 1 has a maximum light emission peak present in 580 nm to 680 nm in a film state, and the light emission peak has a full width at half maximum of 60 nm or less. Having such a small full width at half maximum may further increase color gamut. Herein, the light emission peak of the compound represented by Chemical Formula 1 may have a full width at half maximum of 5 nm or greater.


According to one embodiment of the present specification, the compound represented by Chemical Formula 1 has quantum efficiency of 0.8 or greater.


In the present specification, the “film state” means, instead of a solution state, a state prepared to a film form with the compound represented by Chemical Formula 1 alone or by mixing the compound represented by Chemical Formula 1 with other components that do not affect measurements of full width at half maximum and quantum efficiency.


In the present specification, the full width at half maximum means a width of a light emission peak at a half of the maximum height in a maximum light emission peak of the light emitting from the compound represented by Chemical Formula 1.


In the present specification, the quantum efficiency may be measured using methods known in the art, and for example, may be measured using an integrating sphere.


According to one embodiment of the present specification, the core of the compound represented by Chemical Formula 1 may be prepared using a general preparation method of a reaction formula as below, however, the preparation method is not limited thereto.




embedded image


In the reaction formula, substituents have the same definitions as above. For example, X4 and X5 of the reaction formula may each have the same definition as in Chemical Formula 1 described above, and may be fluorine.


One embodiment of the present specification provides a color conversion film including a resin matrix; and the compound represented by Chemical Formula 1 dispersed into the resin matrix.


The content of the compound represented by Chemical Formula 1 in the color conversion film may be in a range of 0.001% by weight to 10% by weight.


The color conversion film may include one type of the compound represented by Chemical Formula 1, or may include two or more types thereof. For example, the color conversion film may include one type of compound emitting green light among the compounds represented by Chemical Formula 1. As another example, the color conversion film may include one type of compound emitting red light among the compounds represented by Chemical Formula 1. As another example, the color conversion film may include one type of compound emitting green light and one type of compound emitting red light among the compounds represented by Chemical Formula 1.


The color conversion film may further include additional fluorescent substances in addition to the compound represented by Chemical Formula 1. When using a light source emitting blue light, the color conversion film preferably includes both a green light emitting fluorescent substance and a red light emitting fluorescent substance. In addition, when using a light source emitting blue light and green light, the color conversion film may only include a red light emitting fluorescent substance. However, the color conversion film is not limited thereto, and even when using a light source emitting blue light, the color conversion film may only include a red light emitting compound when a separate film including a green light emitting fluorescent substance is laminated. On the other hand, even when using a light source emitting blue light, the color conversion film may only include a green light emitting compound when a separate film including a red light emitting fluorescent substance is laminated.


The color conversion film may further include a resin matrix; and an additional layer including a compound dispersed into the resin matrix and emitting light in a wavelength different from the wavelength of the compound represented by Chemical Formula 1. The compound emitting light in a wavelength different from the wavelength of the compound represented by Chemical Formula 1 may also be the compound represented by Chemical Formula 1, or may be other known fluorescent substances.


The resin matrix material is preferably a thermoplastic polymer or a thermocurable polymer. Specifically, a poly(meth)acryl-based such as polymethyl methacrylate (PMMA), a polycarbonate (PC)-based, a polystyrene (PS)-based, a polyarylene (PAR)-based, a polyurethane (TPU)-based, a styrene-acrylonitrile (SAN)-based, a polyvinylidene fluoride (PVDF)-based, a modified polyvinylidene fluoride (modified-PVDF)-based and the like may be used as the resin matrix material.


According to one embodiment of the present specification, the color conversion film according to the embodiments described above additionally includes light diffusing particles. By dispersing light diffusing particles into the color conversion film instead of a light diffusing film used in the art for enhancing luminance, higher luminance may be exhibited compared to using a separate light diffusing film, and an adhering process may be skipped as well.


As the light diffusing particles, particles having a high refractive index with the resin matrix may be used, and examples thereof may include TiO2, silica, borosilicate, alumina, sapphire, air or other gases, air- or gas-filled hollow beads or particles (for example, air/gas-filled glass or polymers); polystyrene, polycarbonate, polymethyl methacrylate, acryl, methyl methacrylate, styrene, melamine resin, formaldehyde resin, or polymer particles including melamine and formaldehyde resins, or any suitable combination thereof.


The light diffusing particles may have particle diameters in a range of 0.1 μm to 5 μm, for example, in a range of 0.3 μm to 1 μm. The content of the light diffusing particles may be determined as necessary, and for example, may be in a range of approximately 1 part by weight to 30 parts by weight based on 100 parts by weight of the resin matrix.


The color conversion film according to the embodiments described above may have a thickness of 2 μm to 200 μm. Particularly, the color conversion film may exhibit high luminance even with a small thickness of 2 μm to 20 μm. This is due to the fact that the content of the fluorescent substance molecules included in the unit volume is higher compared to quantum dots.


The color conversion film according to the embodiments described above may have a substrate provided on one surface. This substrate may function as a support when preparing the color conversion film. Types of the substrate are not particularly limited, and the material or thickness is not limited as long as it is transparent and is capable of functioning as the support. Herein, being transparent means having visible light transmittance of 70% or higher. For example, a PET film may be used as the substrate.


The color conversion film described above may be prepared by coating a resin solution in which the compound represented by Chemical Formula 1 described above is dissolved on a substrate and drying the result, or by extruding and filming the compound represented by Chemical Formula 1 described above together with a resin.


The compound represented by Chemical Formula 1 is dissolved in the resin solution, and therefore, the compound represented by Chemical Formula 1 is uniformly distributed in the solution. This is different from a quantum dot film preparation process that requires a separate dispersion process.


As for the resin solution in which the compound represented by Chemical Formula 1 is dissolved, the preparation method is not particularly limited as long as the compound represented by Chemical Formula 1 and the resin described above are dissolved in the solution.


According to one example, the resin solution in which the compound represented by Chemical Formula 1 is dissolved may be prepared using a method of preparing a first solution by dissolving the compound represented by Chemical Formula 1 in a solvent, preparing a second solution by dissolving a resin in a solvent, and mixing the first solution and the second solution. When mixing the first solution and the second solution, it is preferable that these be uniformly mixed. However, the method is not limited thereto, and a method of simultaneously adding and dissolving the compound represented by Chemical Formula 1 and a resin in a solvent, a method of dissolving the compound represented by Chemical Formula 1 in a solvent and subsequently adding and dissolving a resin, a method of dissolving a resin in a solvent and then subsequently adding and dissolving the compound represented by Chemical Formula 1, and the like, may be used.


As the resin included in the solution, the resin matrix material described above, a monomer curable to this resin matrix resin, or a mixture thereof, may be used. For example, the monomer curable to the resin matrix resin includes a (meth)acryl-based monomer, and this may be formed to a resin matrix material by UV curing. When using such a curable monomer, an initiator required for curing may be further added as necessary.


The solvent is not particularly limited as long as it is capable of being removed by drying afterword while having no adverse effects on the coating process. Non-limiting examples of the solvent may include toluene, xylene, acetone, chloroform, various alcohol-based solvents, methylethyl ketone (MEK), methylisobutyl ketone (MIBK), ethyl acetate (EA), butyl acetate (BA), dimethylformamide (DMF), dimethylacetamide (DMAc), dimethyl sulfoxide (DMSO), N-methyl-pyrrolidone (NMP) and the like, and one type or a mixture of two or more types may be used. When the first solution and the second solution are used, solvents included in each of the solutions may be the same as or different from each other. Even when different types of solvents are used in the first solution and the second solution, these solvents preferably have compatibility so as to be mixed with each other.


The process of coating the resin solution in which the compound represented by Chemical Formula 1 is dissolved on a substrate may use a roll-to-roll process. For example, a process of unwinding a substrate from a substrate-wound roll, coating the resin solution in which the compound represented by Chemical Formula 1 is dissolved on one surface of the substrate, drying the result, and then winding the result again on the roll may be used. When a roll-to-roll process is used, viscosity of the resin solution is preferably determined in a range capable of conducting the process, and for example, may be determined in a range of 200 cps to 2,000 cps.


As the coating method, various known methods may be used, and for example, a die coater may be used, or various bar coating methods such as a comma coater and a reverse comma coater may be used.


After the coating, a drying process is conducted. The drying process may be conducted under a condition required to remove a solvent. For example, a color conversion film including a fluorescent substance including the compound represented by Chemical Formula 1 having target thickness and concentration may be obtained on a substrate by carrying out the drying in an oven located close to a coater under a condition to sufficiently evaporate a solvent, in a direction of the substrate progressing during the coating process.


When a monomer curable to the resin matrix resin is used as the resin included in the solution, curing, for example, UV curing, may be conducted prior to or at the same time as the drying.


When the compound represented by Chemical Formula 1 is filmed by being extruded with a resin, extrusion methods known in the art may be used, and for example, the color conversion film may be prepared by extruding the compound represented by Chemical Formula 1 with a resin such as a polycarbonate (PC)-based, a poly(meth)acryl-based and a styrene-acrylonitrile (SAN)-based.


According to one embodiment of the present specification, the color conversion film may have a protective film or a barrier film provided on at least one surface. As the protective film or the barrier film, those known in the art may be used.


Another embodiment of the present specification provides a backlight unit including the color conversion film described above. The backlight unit may have backlight unit constitutions known in the art except for including the color conversion film. For example, FIG. 1 illustrates one example. According to FIG. 1, the color conversion film according to the embodiments described above is provided on a surface opposite to a surface facing a reflecting plate of a light guide plate. FIG. 1 illustrates a constitution including a light source and a reflecting plate surrounding the light source, however, the constitution is not limited to such a structure, and may vary depending on the backlight unit structure known in the art. In addition, as the light source, a direct type as well as a side chain type may be used, and the reflecting plate or the reflective layer may not be included or may be replaced with other constituents as necessary, and when necessary, additional films such as a light diffusing film, a light concentrating film and a luminance enhancing film may be further provided. Preferably, a light concentrating film and a luminance enhancing film are further provided on the color conversion film.


In the constitution of the backlight unit as in FIG. 1, a scattering pattern may be provided as necessary on the upper surface or a lower surface of the light guide plate. Light introduced into the light guide plate has non-uniform light distribution due to repetition of optical processes such as reflection, total reflection, refraction or transmission, and the scattering pattern may be used to induce the non-uniform light distribution to uniform brightness.


Another embodiment of the present application uses a display apparatus including the backlight unit described above. This display apparatus is not particularly limited as long as it includes the above-described backlight unit as a constituent. For example, the display apparatus includes a display module and a backlight unit. FIG. 2 illustrates a structure of the display apparatus. However, the structure is not limited thereto, and between the display module and the backlight unit, additional films such as a light diffusing film, a light concentrating film and a luminance enhancing film may be further provided as necessary.


Hereinafter, the present specification will be described in detail with reference to examples. However, the examples according to the present specification may be modified to various other forms, and the scope of the present specification is not to be construed as being limited to the examples described below. Examples of the present specification are provided in order to more fully describe the present specification to those having average knowledge in the art.


PREPARATION EXAMPLE

The compound according to one embodiment of the present specification may be prepared using the following Synthesis Methods 1 to 14.


[Synthesis Method 1]




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Chloro BODIPY (1 equivalent), R—OH (1 equivalent) and potassium carbonate (1.2 equivalents) were introduced into an acetonitrile (ACN) solvent, and the result was stirred while heating. After the reaction was finished, the result was extracted using water and chloroform, and the organic layer was dried with anhydrous magnesium sulfate. The solvent was dried through a vacuum distillation apparatus, and produced solids were filtered using a methanol solvent to obtain a target material.


[Synthesis Method 2]


After dissolving a starting material (1 equivalent) in an acetonitrile solvent, N-bromosuccinimide (NBS) was slowly introduced thereto at room temperature. When connecting 5 Brs, N-bromosuccinimide was used in 6 equivalents, and for 6 Brs, 10 equivalents were used. The reaction was conducted through stirring while heating, and when the reaction was finished, the result was cooled to room temperature, and then sufficiently stirred after introducing a sodium thiosulfate solution thereto. The organic layer was separated and dried with anhydrous magnesium sulfate, and the solvent was dried using a vacuum distillation apparatus. After the drying, solids were filtered using a methanol solvent to obtain a target material.


[Synthesis Method 3]


After dissolving a starting material (1 equivalent) in a dichloromethane (DCM) solvent, the result was stirred at −78° C. under the nitrogen atmosphere. Bromine (4 equivalents) diluted to 10 times in an acetonitrile solvent was slowly added dropwise thereto. During the dropwise addition, the temperature was continuously maintained so that the temperature did not rise. After the stepwise addition, the reaction progress was checked, and when the reaction was finished, a sodium thiosulfate solution and a potassium carbonate solution were introduced thereto, and the result was stirred for a sufficient period of time. The organic layer was separated, washed once more with water, and dried using anhydrous magnesium sulfate. After the drying, produced solids were filtered using a methanol solvent to obtain a target material.


[Synthesis Method 4]


After dissolving a starting material (1 equivalent) in an acetonitrile solvent, aryl alcohol/alkyl alcohol (3 equivalents) and potassium carbonate (5 equivalents) to use in the reaction were added thereto, and the result was stirred while heating. When the reaction was finished, the result was cooled to room temperature, and then extracted using water and chloroform. The organic layer was dried using anhydrous magnesium sulfate, and then the solvent was dried through a vacuum distillation apparatus. Produced solids were filtered using methanol to obtain a target material.


[Synthesis Method 5]


A starting material (1 equivalent) having halogen and a material having boronic acid were introduced using toluene and ethanol, potassium carbonate was dissolved in water, and these were stirred together while heating. For one Suzuki coupling, the boronic acid was used in 1.1 equivalents, and for two Suzuki couplings, 3 equivalents were used. Tetrakistriphenylphosphine palladium (Pd(PPh3)4) was used in 0.01 equivalents to conduct the reaction. After the reaction was finished, the result was cooled to room temperature, and extracted using water and ethyl acetate. The organic layer was dried using anhydrous magnesium sulfate, and the solvent was dried through a vacuum distillation apparatus. Produced solids were filtered using a methanol solvent to obtain a target material.


[Synthesis Method 6]


After dissolving a starting material (1 equivalent) in an acetonitrile solvent, N-chlorosuccinimide (NCS) was slowly added dropwise thereto. To make 5 Cls, the N-chlorosuccinimide was used in 7 equivalents, and for 6 Cls, 10 equivalents were used. After the dropwise addition was completed, the reaction was progressed through stirring while heating, and after the reaction was finished, the result was cooled to room temperature, and sufficiently stirred using a sodium thiosulfate solution. The organic layer was separated, and then dried using anhydrous magnesium sulfate, and the solvent was dried through a vacuum distillation apparatus. Produced solids were filtered using a methanol solvent to obtain a target material.


[Synthesis Method 7]


After dissolving a starting material in a dichloromethane solvent, the result was stirred at 0° C. under the nitrogen atmosphere. Trimethylsilyl cyanide (TMS-CN) and boron trifluoride ethyl ether (BF3OEt2) were slowly added dropwise thereto. For one cyanide substitution, the trimethylsilyl cyanide was used in 5 equivalents and the boron trifluoride ethyl ether was used in 2 equivalents, and for two cyanide substitution, 15 equivalents and 5 equivalents were respectively used. When the reaction was finished, the result was extracted using water and chloroform, and the organic layer was dried using anhydrous magnesium sulfate. The solvent was dried through a vacuum distillation apparatus, and produced solids were filtered using a methanol solvent to obtain a target material.


[Synthesis Method 8]


After dissolving a starting material (1 equivalent) in a dimethylformamide (DMF) solvent, a cycloalkyl-boron trifluoride potassium salt was introduced thereto, and manganese triacetate dihydrate (Mn(OAc)32H2O) was introduced thereto. For one cycloalkyl, the corresponding cycloalkyl was used in 1.5 equivalents and the manganese was used in 3 equivalents, and for two cycloalkyls, the cycloalkyl was used in 3 equivalents and the manganese was used in 5 equivalents. When the reaction was finished, water was introduced thereto, and produced solids were filtered through filtration. The solids were dissolved again in chloroform, and the result was dried using anhydrous magnesium sulfate. Produced solids were filtered using a methanol solvent to obtain a target material.


[Synthesis Method 9]


After introducing a dichloroethane (DCE) solvent to a flask at 0° C. under the nitrogen atmosphere, phosphorous oxychloride (POCl3) and dimethylformamide were introduced thereto in 1:1, and the result was stirred for approximately 1 hour. After introducing a starting material (1 equivalent) to the flask, the reaction was progressed through stirring while heating. To make one aldehyde, the phosphorous oxychloride was used in 3 equivalents to prepare a solution, and to make two aldehydes, 10 equivalents were used to prepare a solution. When checking the reaction progress, a small amount was taken out, washed with a sodium bicarbonate solution, and then checked. After the reaction was finished, the flask was immersed in ice water, and then the result was neutralized by slowly adding a sodium bicarbonate solution thereto. After finishing the neutralization, the organic layer was separated, dried using anhydrous magnesium sulfate, and produced solids were filtered using a methanol solvent to obtain a target material.


[Synthesis Method 10]


After dissolving a starting material in a tetrahydrofuran (THF) solvent, sulfamic acid corresponding to 3 equivalents per 1 equivalent of aldehyde to oxidize was dissolved in water, and these were stirred together. The temperature was lowered to 0° C. after 30 minutes, and sodium chloride (1.2 equivalents) dissolved in water was slowly introduced thereto. After the reaction was completed, a sodium thiosulfate solution was introduced thereto, and after stirring the result, the organic layer was separated. The separated organic layer was dried using anhydrous magnesium sulfate, and the solvent was removed through a vacuum distillation apparatus. Produced solids were filtered using a methanol solvent to obtain a target material.


[Synthesis Method 11]


A starting material including an acid and a starting material including an alcohol were dissolved in chloroform with 1.05 equivalent of the alcohol for 1 equivalent of the acid. Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) and dimethylaminopyridine (DMAP) were introduced thereto in 1.1 equivalents each with respect to the acid, and the result was stirred while heating. After the reaction was finished, the result was extracted using water and chloroform, and the organic layer was dried using anhydrous magnesium sulfate. Produced solids were filtered using methanol to obtain a target material.


[Synthesis Method 12]


After stirring palladium acetate (Pd(OAc)2) and Xantphos (Sigma-Aldrich, CAS Number 161265-03-8/4,5-bis(diphenylphosphino)-9,9-dimethylxanthene) in a dimethylformamide solvent, the result was introduced to a starting material having halogen placed in a flask at room temperature under the nitrogen atmosphere. After approximately 5 minutes, the result was introduced to a flask in which an indium starting material and diisopropylethylamine (DIPEA) were stirred in a dimethylformamide solvent using a cannula (double ended needle), and the result was stirred while heating. After the reaction was finished, the result was extracted using a sodium bicarbonate solution and chloroform, and the organic layer was dried using anhydrous magnesium sulfate. Produced solids were filtered using methanol to obtain a target material.


[Synthesis Method 13]


After dissolving a starting material (1 equivalent) in dichloromethane, aluminum chloride (5 equivalents) was introduced thereto, and the result was stirred. Heptafluorobutanol (C3F7CH2OH) (3 equivalents) was introduced thereto, the result was stirred while heating, and when the reaction was finished, the result was extracted using water and chloroform. The organic layer was dried using anhydrous magnesium sulfate, and after removing the solvent through a vacuum distillation apparatus, produced solids were filtered using methanol to obtain a target material.


[Synthesis Method 14]


After dissolving a starting material (1 equivalent) and t-butyl ethynylbenzene (2.1 equivalents) in an anhydrous tetrahydrofuran solvent, the flask was maintained under the nitrogen atmosphere at −78° C. for approximately 1 hour. n-BuLi (2.05 equivalents) was slowly added dropwise thereto, and the temperature was raised to room temperature. When the reaction was finished, the result was extracted using water and chloroform, and the organic layer was dried using anhydrous magnesium sulfate. The solvent was removed through a vacuum distillation apparatus, and produced solids were filtered using methanol to obtain a target material.


Preparation Example 1
Compound 1



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(Synthesis of 1-1)


Synthesis was progressed according to Synthesis Method 1 using chloro BODIPY and 7-hydroxycoumarin. Compound 1-1 was obtained in 6.6 g (yield 85%).


(Synthesis of 1-2)


Synthesis was progressed according to Synthesis Method 2 using Compound 1-1 and N-bromosuccinimide. Compound 1-2 was obtained in 9.1 g (yield 72%).


(Synthesis of 1-3)


Synthesis was progressed according to Synthesis Method 4 using Compound 1-2 and tetrakistrifluoromethylbiphenyl-ol. Compound 1-3 was obtained in 14.3 g (yield 81%).


(Synthesis of 1-4)


Synthesis was progressed according to Synthesis Method 5 using Compound 1-3 and t-butylphenylboronic acid. Compound 1-4 was obtained in 11.4 g (yield 76%).


(Synthesis of Compound 1)


Synthesis was progressed according to Synthesis Method 4 using Compound 1-4 and biphenylol. Final Compound 1 was obtained in 9.7 g (yield 84%) through column chromatography.


HR LC/MS/MS m/z calculated for C82H51BF26N2O6 (M+): 1664.3425; found: 1664.3428


Preparation Example 2
Compound 2



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(Synthesis of 2-1)


Synthesis was progressed according to Synthesis Method 1 using chloro BODIPY and 2,6-diisopropylphenol. Compound 2-1 was obtained in 14.1 g (yield 87%).


(Synthesis of 2-2)


Synthesis was progressed according to Synthesis Method 3 using Compound 2-1 and bromine. Compound 2-2 was obtained in 23.1 g (yield 89%).


(Synthesis of 2-3)


Synthesis was progressed according to Synthesis Method 4 using Compound 2-2 and 4-cyano-2,6-diisopropylphenol. Compound 2-3 was obtained in 10.5 g (yield 77%).


(Synthesis of Compound 2)


Synthesis was progressed according to Synthesis Method 5 using Compound 2-3 and 2,4-ditrifluoromethylboronic acid. Compound 2 was obtained in 11.1 g (yield 86%).


HR LC/MS/MS m/z calculated for C63H57BF14N4O3 (M+): 1194.4300; found: 1194.4296


Preparation Example 3
Compound 3



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(Synthesis of 3-1)


Synthesis was progressed according to Synthesis Method 1 using chloro BODIPY and 4-cyano-2,6-diisopropylphenol. Compound 3-1 was obtained in 15.5 g (yield 89%).


(Synthesis of 3-2)


Synthesis was progressed according to Synthesis Method 6 using Compound 3-1. Compound 3-2 was obtained in 9.8 g (yield 68%).


(Synthesis of 3-3)


Synthesis was progressed according to Synthesis Method 4 using Compound 3-2 and 2,6-dichlorophenol. Compound 3-3 was obtained in 7.4 g (yield 59%).


(Synthesis of Compound 3)


Synthesis was progressed according to Synthesis Method 5 using Compound 3-3 and 2,4-ditrifluoromethylboronic acid. Compound 3 was obtained in 8.0 g (yield 76%).


HR LC/MS/MS m/z calculated for C50H29BCl5F14N3O3 (M+): 1171.0521; found: 1171.0525


Preparation Example 4
Compound 4



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(Synthesis of 4-1)


Synthesis was progressed according to Synthesis Method 1 using chloro BODIPY and phenol. Compound 4-1 was obtained in 5.6 g (yield 90%).


(Synthesis of 4-2)


Synthesis was progressed according to Synthesis Method 2 using Compound 4-1. Compound 4-2 was obtained in 9.7 g (yield 81%).


(Synthesis of 4-3)


Synthesis was progressed according to Synthesis Method 4 using Compound 4-2 and cyanobenzenethiol. Compound 4-3 was obtained in 9.4 g (yield 90%).


(Synthesis of 4-4)


Synthesis was progressed according to Synthesis Method 5 using Compound 4-3 and t-butylbenzeneboronic acid. Compound 4-4 was obtained in 8.4 g (yield 82%).


(Synthesis of Compound 4)


Synthesis was progressed according to Synthesis Method 5 using Compound 4-4 and benzeneboronic acid. Compound 4 was obtained in 6.3 g (yield 79%).


HR LC/MS/MS m/z calculated for C55H45BF2N4OS2 (M+): 890.3096; found: 890.3094


Preparation Example 5
Compound 5



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(Synthesis of 5-1)


Synthesis was progressed according to Synthesis Method 1 using chloro BODIPY and cyanophenol. Compound 5-1 was obtained in 6.2 g (yield 91%).


(Synthesis of 5-2)


Synthesis was progressed according to Synthesis Method 2 using Compound 5-1. Compound 5-2 was obtained in 13.1 g (yield 86%).


(Synthesis of 5-3)


Synthesis was progressed according to Synthesis Method 4 using Compound 5-2 and dibenzofuran-4-thiol. Compound 5-3 was obtained in 14.8 g (yield 87%).


(Synthesis of 5-4)


Synthesis was progressed according to Synthesis Method 5 using Compound 5-3 and t-butylbenzeneboronic acid. Compound 5-4 was obtained in 11.2 g (yield 76%).


(Synthesis of 5-5)


Synthesis was progressed according to Synthesis Method 5 using Compound 5-4 and benzeneboronic acid. Compound 5-5 was obtained in 7.9 g (yield 76%).


(Synthesis of Compound 5)


Synthesis was progressed according to Synthesis Method 4 using Compound 5-5 and cyanophenol. Compound 5 was obtained in 6.4 g (yield 86%).


HR LC/MS/MS m/z calculated for C70H44BF2N5O5S2 (M+): 1147.2845; found: 1147.2850


Preparation Example 6
Compound 6



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(Synthesis of 6-1)


Synthesis was progressed according to Synthesis Method 4 using Compound 2-2 and dichlorobenzenethiol. Compound 6-1 was obtained in 5.0 g (yield 78%).


(Synthesis of Compound 6)


Synthesis was progressed according to Synthesis Method 5 using Compound 6-1 and 4-methoxyphenylboronic acid. Compound 6 was obtained in 4.8 g (yield 90%).


HR LC/MS/MS m/z calculated for C47H39BCl4F2N2O3S2 (M+): 932.1217; found: 932.1215


Preparation Example 7
Compound 7



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(Synthesis of 7-1)


Synthesis was progressed according to Synthesis Method 1 using chloro BODIPY and 4-cyano-2,6-diisopropylbenzenethiol. Compound 7-1 was obtained in 5.8 g (yield 64%).


(Synthesis of 7-2)


Synthesis was progressed according to Synthesis Method 2 using Compound 7-1. Compound 7-2 was obtained in 7.2 g (yield 73%).


(Synthesis of 7-3)


Synthesis was progressed according to Synthesis Method 4 using Compound 7-2 and 5′-fluoro-2,2″-bis(trifluoromethyl)terphenyl-2′-ol. Compound 7-3 was obtained in 9.5 g (yield 76%).


(Synthesis of 7-4)


Synthesis was progressed according to Synthesis Method 5 using Compound 7-3 and dibenzothiopheneboronic acid. Compound 7-4 was obtained in 7.0 g (yield 68%).


(Synthesis of Compound 7)


Synthesis was progressed according to Synthesis Method 5 using Compound 7-4 and 4-trifluoromethylphenylboronic acid. Compound 7 was obtained in 5.3 g (yield 73%).


HR LC/MS/MS m/z calculated for C93H55BF19N3O2S3 (M+): 1713.3246; found: 1713.3242


Preparation Example 8
Compound 8



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(Synthesis of 8-1)


Synthesis was progressed according to Synthesis Method 1 using chloro BODIPY and dibenzofuran-4-thiol. Compound 8-1 was obtained in 6.8 g (yield 79%).


(Synthesis of 8-2)


Synthesis was progressed according to Synthesis Method 2 using Compound 8-1. Compound 8-2 was obtained in 11.2 g (yield 84%).


(Synthesis of 8-3)


Synthesis was progressed according to Synthesis Method 4 using Compound 8-2 and benzenethiol. Compound 8-3 was obtained in 8.6 g (yield 81%).


(Synthesis of 8-4)


Synthesis was progressed according to Synthesis Method 5 using Compound 8-3 and 2,4-difluorobenzeneboronic acid. Compound 8-4 was obtained in 6.5 g (yield 76%).


(Synthesis of Compound 8)


Synthesis was progressed according to Synthesis Method 5 using Compound 8-4 and 4-cyanobenzeneboronic acid. Compound 8 was obtained in 4.8 g (yield 77%).


HR LC/MS/MS m/z calculated for C59H31BF6N4OS3 (M+): 1032.1657; found: 1032.1653


Preparation Example 9
Compound 9



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(Synthesis of 9-1)


Synthesis was progressed according to Synthesis Method 1 using chloro BODIPY and 3,5-dimethoxyphenol. Compound 9-1 was obtained in 6.5 g (yield 86%).


(Synthesis of 9-2)


Synthesis was progressed according to Synthesis Method 6 using Compound 9-1. Compound 9-2 was obtained in 7.0 g (yield 73%).


(Synthesis of 9-3)


Synthesis was progressed according to Synthesis Method 4 using Compound 9-2 and 2,6-dimethylphenol. Compound 9-3 was obtained in 7.0 g (yield 76%).


(Synthesis of 9-4)


Synthesis was progressed according to Synthesis Method 5 using Compound 9-3 and 6-phenyl-dibenzofuranyl-4-boronic acid. Compound 9-4 was obtained in 6.1 g (yield 65%).


(Synthesis of Compound 9)


Synthesis was progressed according to Synthesis Method 7 using Compound 9-4. Compound 9 was obtained in 2.7 g (yield 45%).


HR LC/MS/MS m/z calculated for C70H49BCl2FN3O7 (M+): 1143.3025; found: 1143.3027


Preparation Example 10
Compound 10



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(Synthesis of 10-1)


Synthesis was progressed according to Synthesis Method 2 using Compound 4-1. Compound 10-1 was obtained in 11.5 g (yield 86%).


(Synthesis of 10-2)


Synthesis was progressed according to Synthesis Method 4 using Compound 10-1 and 2-(2′-trifluoromethylphenyl)-4,6-difluorobenzenethiol. Compound 10-2 was obtained in 13.5 g (yield 79%).


(Synthesis of 10-3)


Synthesis was progressed according to Synthesis Method 5 using Compound 10-2 and 4-cyanophenylboronic acid. Compound 10-3 was obtained in 10.8 g (yield 80%).


(Synthesis of 10-4)


Synthesis was progressed according to Synthesis Method 5 using Compound 10-3 and biphenyl-4-ol. Compound 10-4 was obtained in 8.3 g (yield 72%).


(Synthesis of Compound 10)


Synthesis was progressed according to Synthesis Method 7 using Compound 10-4. Compound 10 was obtained in 4.1 g (yield 51%).


HR LC/MS/MS m/z calculated for C80H43BF11N5O3S2 (M+): 1405.2725; found: 1405.2730


Preparation Example 11
Compound 11



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(Synthesis of 11-1)


Synthesis was progressed according to Synthesis Method 2 using Compound 7-1. Compound 11-1 was obtained in 9.1 g (yield 84%).


(Synthesis of 11-2)


Synthesis was progressed according to Synthesis Method 4 using Compound 11-1 and dibenzofuran-4-ol. Compound 11-2 was obtained in 8.7 g (yield 79%).


(Synthesis of 11-3)


Synthesis was progressed according to Synthesis Method 5 using Compound 11-2 and 2,4-di(trifluoromethyl)phenylboronic acid. Compound 11-3 was obtained in 7.2 g (yield 72%).


(Synthesis of 11-4)


Synthesis was progressed according to Synthesis Method 5 using Compound 11-3 and phenylboronic acid. Compound 11-4 was obtained in 4.7 g (yield 68%).


(Synthesis of Compound 11)


Synthesis was progressed according to Synthesis Method 7 using Compound 11-4. Compound 11 was obtained in 2.0 g (yield 49%).


HR LC/MS/MS m/z calculated for C75H46BF13N4O4S (M+): 1356.3125; found: 1356.3129


Preparation Example 12
Compound 12



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(Synthesis of 12-1)


Synthesis was progressed according to Synthesis Method 1 using chloro BODIPY and 5′-methoxy-terphenyl-2′-thiol. Compound 12-1 was obtained in 8.1 g (yield 76%).


(Synthesis of 12-2)


Synthesis was progressed according to Synthesis Method 6 using Compound 12-1. Compound 12-2 was obtained in 7.9 g (yield 69%).


(Synthesis of 12-3)


Synthesis was progressed according to Synthesis Method 4 using Compound 12-2 and 2,4-di(trifluoromethyl)benzenethiol. Compound 12-3 was obtained in 7.2 g (yield 64%).


(Synthesis of 12-4)


Synthesis was progressed according to Synthesis Method 5 using Compound 12-3 and 4-methoxyphenylboronic acid. Compound 12-4 was obtained in 6.8 g (yield 86%).


(Synthesis of Compound 12)


Synthesis was progressed according to Synthesis Method 7 using Compound 12-4. Compound 12 was obtained in 3.0 g (yield 49%).


HR LC/MS/MS m/z calculated for C59H35BCl2F13N3O3S3 (M+): 1257.1103; found: 1257.1106


Preparation Example 13
Compound 13



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(Synthesis of 13-1)


Synthesis was progressed according to Synthesis Method 3 using Compound 3-1. Compound 13-1 was obtained in 7.9 g (yield 88%).


(Synthesis of 13-2)


Synthesis was progressed according to Synthesis Method 4 using Compound 13-1 and 4-trifluoromethylphenol. Compound 13-2 was obtained in 7.3 g (yield 85%).


(Synthesis of 13-3)


Synthesis was progressed according to Synthesis Method 5 using Compound 13-2 and dibenzofuranyl-4-boronic acid. Compound 13-3 was obtained in 5.2 g (yield 68%).


(Synthesis of 13-4)


Synthesis was progressed according to Synthesis Method 5 using Compound 13-3 and phenylboronic acid. Compound 13-4 was obtained in 4.3 g (yield 86%).


(Synthesis of Compound 13)


Synthesis was progressed according to Synthesis Method 7 using Compound 13-4. Compound 13 was obtained in 1.8 g (yield 44%).


HR LC/MS/MS m/z calculated for C56H38BF6N5O4 (M+): 696.2921; found: 696.2918


Preparation Example 14
Compound 14



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(Synthesis of 14-1)


Synthesis was progressed according to Synthesis Method 4 using Compound 2-2 and 3,5-dimethoxyphenol. Compound 14-1 was obtained in 4.8 g (yield 79%).


(Synthesis of 14-2)


Synthesis was progressed according to Synthesis Method 5 using Compound 14-1 and 4-cyanophenylboronic acid. Compound 14-2 was obtained in 3.8 g (yield 89%).


(Synthesis of 14-3)


Synthesis was progressed according to Synthesis Method 8 using Compound 14-2 and cyclopentyl potassium trifluoroborate. Compound 14-3 was obtained in 2.1 g (yield 61%).


(Synthesis of Compound 14)


Synthesis was progressed according to Synthesis Method 7 using Compound 14-3. Compound 14 was obtained in 1.6 g (yield 78%).


HR LC/MS/MS m/z calculated for C63H61BN6O7 (M+): 1024.4695; found: 1024.4693


Preparation Example 15
Compound 15



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(Synthesis of 15-1)


Synthesis was progressed according to Synthesis Method 1 using chloro BODIPY and 5′-fluoro-terphenyl-2′-ol. Compound 15-1 was obtained in 7.2 g (yield 72%).


(Synthesis of 15-2)


Synthesis was progressed according to Synthesis Method 2 using Compound 15-1. Compound 15-2 was obtained in 12.2 g (yield 85%).


(Synthesis of 15-3)


Synthesis was progressed according to Synthesis Method 4 using Compound 15-2 and 7-hydroxycoumarin. Compound 15-3 was obtained in 11.6 g (yield 82%).


(Synthesis of 15-4)


Synthesis was progressed according to Synthesis Method 5 using Compound 15-3 and 2,6-dimethylphenylboronic acid. Compound 15-4 was obtained in 9.1 g (yield 79%).


(Synthesis of 15-5)


Synthesis was progressed according to Synthesis Method 5 using Compound 15-4 and 3-fluorophenylboronic acid. Compound 15-5 was obtained in 6.3 g (yield 68%).


(Synthesis of Compound 15)


Synthesis was progressed according to Synthesis Method 7 using Compound 15-5. Compound 15 was obtained in 4.4 g (yield 73%).


HR LC/MS/MS m/z calculated for C75H48BF3N4O7 (M+): 1184.3568; found: 1184.3571


Preparation Example 16
Compound 16



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(Synthesis of 16-1)


Synthesis was progressed according to Synthesis Method 9 using Compound 2-1. Compound 16-1 was obtained in 4.3 g (yield 80%).


(Synthesis of 16-2)


Synthesis was progressed according to Synthesis Method 3 using Compound 16-1. Compound 16-2 was obtained in 5.0 g (yield 79%).


(Synthesis of 16-3)


Synthesis was progressed according to Synthesis Method 4 using Compound 16-2 and benzenethiol. Compound 16-3 was obtained in 4.7 g (yield 86%).


(Synthesis of 16-4)


Synthesis was progressed according to Synthesis Method 5 using Compound 16-3 and benzeneboronic acid. Compound 16-4 was obtained in 3.2 g (yield 81%).


(Synthesis of 16-5)


Synthesis was progressed according to Synthesis Method 10 using Compound 16-4. Compound 16-5 was obtained in 2.2 g (yield 72%).


(Synthesis of 16-6)


Synthesis was progressed according to Synthesis Method 11 using Compound 16-5 and 7-hydroxycoumarin. Compound 16-6 was obtained in 2.2 g (yield 91%).


(Synthesis of 16-7)


Synthesis was progressed according to Synthesis Method 8 using Compound 16-6 and cyclohexyl potassium trifluoroborate. Compound 16-7 was obtained in 1.5 g (yield 68%).


(Synthesis of Compound 16)


Synthesis was progressed according to Synthesis Method 7 using Compound 16-7. Compound 16 was obtained in 1.4 g (yield 91%).


HR LC/MS/MS m/z calculated for C57H49BN4O5S2 (M+): 944.3237; found: 944.3235


Preparation Example 17
Compound 17



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(Synthesis of 17-1)


Synthesis was progressed according to Synthesis Method 1 using chloro BODIPY and 2,4,6-trimethylphenol. Compound 17-1 was obtained in 6.2 g (yield 86%).


(Synthesis of 17-2)


Synthesis was progressed according to Synthesis Method 2 using Compound 17-1. Compound 17-2 was obtained in 12.4 g (yield 84%).


(Synthesis of 17-3)


Synthesis was progressed according to Synthesis Method 12 using Compound 17-2 and indium hexafluoropropane-2-thiolate. Compound 17-3 was obtained in 6.3 g (yield 42%).


(Synthesis of 17-4)


Synthesis was progressed according to Synthesis Method 5 using Compound 17-3 and 2-methoxyphenylboronic acid. Compound 17-4 was obtained in 5.4 g (yield 86%).


(Synthesis of 17-5)


Synthesis was progressed according to Synthesis Method 5 using Compound 17-4 and phenylboronic acid. Compound 17-5 was obtained in 3.6 g (yield 72%).


(Synthesis of Compound 17)


Synthesis was progressed according to Synthesis Method 7 using Compound 17-5. Compound 17 was obtained in 2.3 g (yield 76%).


HR LC/MS/MS m/z calculated for C52H37BF12N4O3S2 (M+): 1068.2209; found: 1068.2213


Preparation Example 18
Compound 18



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(Synthesis of 18-1)


Synthesis was progressed according to Synthesis Method 1 using chloro BODIPY and 5′-methoxyterphenyl-2′-ol. Compound 18-1 was obtained in 8.9 g (yield 86%).


(Synthesis of 18-2)


Synthesis was progressed according to Synthesis Method 2 using Compound 18-1. Compound 18-2 was obtained in 13.1 g (yield 81%).


(Synthesis of 18-3)


Synthesis was progressed according to Synthesis Method 4 using Compound 18-2 and 5′-cyanoterphenyl-2′-thiol. Compound 18-3 was obtained in 14.2 g (yield 76%).


(Synthesis of 18-4)


Synthesis was progressed according to Synthesis Method 5 using Compound 18-3 and benzeneboronic acid. Compound 18-4 was obtained in 11.6 g (yield 83%).


(Synthesis of 18-5)


Synthesis was progressed according to Synthesis Method 4 using Compound 18-4 and 4-cyanophenol. Compound 18-5 was obtained in 8.7 g (yield 75%).


(Synthesis of Compound 18)


Synthesis was progressed according to Synthesis Method 7 using Compound 18-5. Compound 18 was obtained in 5.8 g (yield 72%).


HR LC/MS/MS m/z calculated for C94H57BN8O4S2 (M+): 1436.4037; found: 1436.4040


Preparation Example 19
Compound 19



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(Synthesis of 19-1)


Synthesis was progressed according to Synthesis Method 9 using Compound 8-1. Compound 19-1 was obtained in 4.8 g (yield 84%).


(Synthesis of 19-2)


Synthesis was progressed according to Synthesis Method 3 using Compound 19-1. Compound 19-2 was obtained in 5.9 g (yield 86%).


(Synthesis of 19-3)


Synthesis was progressed according to Synthesis Method 4 using Compound 19-2 and 2-methylcyclohexanol. Compound 19-3 was obtained in 3.5 g (yield 64%).


(Synthesis of 19-4)


Synthesis was progressed according to Synthesis Method 10 using Compound 19-3. Compound 19-4 was obtained in 2.5 g (yield 79%).


(Synthesis of 19-5)


Synthesis was progressed according to Synthesis Method 11 using Compound 19-4 and 7-hydroxycoumarin. Compound 19-5 was obtained in 2.4 g (yield 91%).


(Synthesis of 19-6)


Synthesis was progressed according to Synthesis Method 4 using Compound 19-5 and 2-methylphenol. Compound 19-6 was obtained in 2.0 g (yield 96%).


(Synthesis of Compound 19)


Synthesis was progressed according to Synthesis Method 7 using Compound 19-6. Compound 19 was obtained in 1.6 g (yield 86%).


HR LC/MS/MS m/z calculated for C71H57BN4O13S (M+): 1216.3736; found: 1216.3739


Preparation Example 20
Compound 20



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(Synthesis of 20-1)


Synthesis was progressed according to Synthesis Method 1 using chloro BODIPY and 4-mercaptobenzonitrile. Compound 20-1 was obtained in 6.2 g (yield 86%).


(Synthesis of 20-2)


Synthesis was progressed according to Synthesis Method 9 using Compound 20-1. Compound 20-2 was obtained in 5.3 g (yield 82%).


(Synthesis of 20-3)


Synthesis was progressed according to Synthesis Method 2 using Compound 20-2. Compound 20-3 was obtained in 7.8 g (yield 74%).


(Synthesis of 20-4)


Synthesis was progressed according to Synthesis Method 4 using Compound 20-3 and 4-cyano-2,6-diisopropylbenzenethiol. Compound 20-4 was obtained in 7.4 g (yield 77%).


(Synthesis of 20-5)


Synthesis was progressed according to Synthesis Method 5 using Compound 20-4 and benzeneboronic acid. Compound 20-5 was obtained in 5.0 g (yield 72%).


(Synthesis of 20-6)


Synthesis was progressed according to Synthesis Method 10 using Compound 20-5. Compound 20-6 was obtained in 3.5 g (yield 68%).


(Synthesis of 20-7)


Synthesis was progressed according to Synthesis Method 11 using Compound 20-6 and 7-hydroxycoumarin. Compound 20-7 was obtained in 3.1 g (yield 91%).


(Synthesis of Compound 20)


Synthesis was progressed according to Synthesis Method 7 using Compound 20-7. Compound 20 was obtained in 2.5 g (yield 84%).


HR LC/MS/MS m/z calculated for C60H46BBr2N7O4S3 (M+): 1193.1233; found: 1193.1230


Preparation Example 21
Compound 21



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(Synthesis of 21-1)


Synthesis was progressed according to Synthesis Method 4 using Compound 18-2 and 4-(9H-carbazol-9-yl)phenol. Compound 21-1 was obtained in 10.5 g (yield 76%).


(Synthesis of 21-2)


Synthesis was progressed according to Synthesis Method 5 using Compound 21-1 and benzeneboronic acid. Compound 21-2 was obtained in 6.8 g (yield 68%).


(Synthesis of 21-3)


Synthesis was progressed according to Synthesis Method 5 using Compound 21-2 and 4-trifluoromethylphenylboronic acid. Compound 21-3 was obtained in 4.7 g (yield 75%).


(Synthesis of 21-4)


Synthesis was progressed according to Synthesis Method 5 using Compound 21-3 and 2-methoxyphenylboronic acid. Compound 21-4 was obtained in 3.0 g (yield 81%).


(Synthesis of Compound 21)


Synthesis was progressed according to Synthesis Method 13 using Compound 21-4. Compound 21 was obtained in 1.3 g (yield 51%).


HR LC/MS/MS m/z calculated for C86H55BF18N4O7 (M+): 1608.3876; found: 1608.3872


Preparation Example 22
Compound 22



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(Synthesis of 22-1)


Synthesis was progressed according to Synthesis Method 1 using chloro BODIPY and 2-(pyridin-2-yl)phenol. Compound 22-1 was obtained in 5.0 g (yield 63%).


(Synthesis of 22-2)


Synthesis was progressed according to Synthesis Method 2 using Compound 22-1. Compound 22-2 was obtained in 7.6 g (yield 73%).


(Synthesis of 22-3)


Synthesis was progressed according to Synthesis Method 4 using Compound 22-2 and 5′-fluoroterphenyl-2′-thiol. Compound 22-3 was obtained in 8.6 g (yield 80%).


(Synthesis of 22-4)


Synthesis was progressed according to Synthesis Method 5 using Compound 22-3 and phenylboronic acid. Compound 22-4 was obtained in 6.2 g (yield 78%).


(Synthesis of Compound 22)


Synthesis was progressed according to Synthesis Method 13 using Compound 22-4. Compound 22 was obtained in 3.1 g (yield 39%).


HR LC/MS/MS m/z calculated for C82H52BF16N3O3S2 (M+): 1505.3288; found: 1505.3291


Preparation Example 23
Compound 23



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(Synthesis of 23-1)


Synthesis was progressed according to Synthesis Method 1 using chloro BODIPY and terphenyl-2′-thiol. Compound 23-1 was obtained in 6.5 g (yield 65%).


(Synthesis of 23-2)


Synthesis was progressed according to Synthesis Method 2 using Compound 23-1. Compound 23-2 was obtained in 10.7 g (yield 87%).


(Synthesis of 23-3)


Synthesis was progressed according to Synthesis Method 4 using Compound 23-2 and 5′-(t-butyl)-terphenyl-2′-ol. Compound 23-3 was obtained in 10.8 g (yield 73%).


(Synthesis of 23-4)


Synthesis was progressed according to Synthesis Method 5 using Compound 23-3 and phenylboronic acid. Compound 23-4 was obtained in 6.4 g (yield 64%).


(Synthesis of 23-5)


Synthesis was progressed according to Synthesis Method 5 using Compound 23-4 and 4-aminophenylboronic acid. Compound 23-5 was obtained in 4.4 g (yield 73%).


(Synthesis of 23-6)


Synthesis was progressed according to Synthesis Method 4 using Compound 23-5 and 2-trifluoromethylphenol. Compound 23-6 was obtained in 3.6 g (yield 81%).


(Synthesis of Compound 23)


Synthesis was progressed according to Synthesis Method 13 using Compound 23-6. Compound 23 was obtained in 1.6 g (yield 43%).


HR LC/MS/MS m/z calculated for C105H78BF20N3O6S (M+): 1899.5385; found: 1899.5382


Preparation Example 24
Compound 24



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(Synthesis of 24-1)


Synthesis was progressed according to Synthesis Method 1 using chloro BODIPY and 2,4,6-trimethylbenzenethiol. Compound 24-1 was obtained in 6.2 g (yield 82%).


(Synthesis of 24-2)


Synthesis was progressed according to Synthesis Method 3 using Compound 24-1. Compound 24-2 was obtained in 9.7 g (yield 84%).


(Synthesis of 24-3)


Synthesis was progressed according to Synthesis Method 4 using Compound 24-2 and 2,6-diisopropylbenzenethiol. Compound 24-3 was obtained in 9.8 g (yield 81%).


(Synthesis of 24-4)


Synthesis was progressed according to Synthesis Method 5 using Compound 24-3 and 2,4-difluorophenylboronic acid. Compound 24-4 was obtained in 8.6 g (yield 89%).


(Synthesis of Compound 24)


Synthesis was progressed according to Synthesis Method 13 using Compound 24-4. Compound 24 was obtained in 5.3 g (yield 48%).


HR LC/MS/MS m/z calculated for C62H57BF18N2O2S3 (M+): 1310.3388; found: 1310.3390


Preparation Example 25
Compound 25



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(Synthesis of 25-1)


Synthesis was progressed according to Synthesis Method 1 using chloro BODIPY and 4′-hydroxy-3′,5′-diisopropyl-biphenyl-4-carbonitrile. Compound 25-1 was obtained in 7.8 g (yield 75%).


(Synthesis of 25-2)


Synthesis was progressed according to Synthesis Method 2 using Compound 25-1. Compound 25-2 was obtained in 8.8 g (yield 68%).


(Synthesis of 25-3)


Synthesis was progressed according to Synthesis Method 4 using Compound 25-2 and 2,4-difluorophenol. Compound 25-3 was obtained in 7.1 g (yield 80%).


(Synthesis of 25-4)


Synthesis was progressed according to Synthesis Method 5 using Compound 25-3 and dibenzothiophenyl-4-boronic acid. Compound 25-4 was obtained in 4.6 g (yield 59%).


(Synthesis of 25-5)


Synthesis was progressed according to Synthesis Method 5 using Compound 25-4 and phenylboronic acid. Compound 25-5 was obtained in 2.5 g (yield 63%).


(Synthesis of 25-6)


Synthesis was progressed according to Synthesis Method 4 using Compound 25-5 and phenol. Compound 25-6 was obtained in 4.6 g (yield 78%).


(Synthesis of Compound 25)


Synthesis was progressed according to Synthesis Method 14 using Compound 25-6. Compound 25 was obtained in 0.8 g (yield 62%).


HR LC/MS/MS m/z calculated for C88H70BF4N3O4S (M+): 1351.5116; found: 1351.5118


Preparation Example 26
Compound 26



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(Synthesis of 26-1)


Synthesis was progressed according to Synthesis Method 1 using chloro BODIPY and terphenyl-2′-ol. Compound 26-1 was obtained in 8.3 g (yield 86%).


(Synthesis of 26-2)


Synthesis was progressed according to Synthesis Method 3 using Compound 26-1. Compound 26-2 was obtained in 11.2 g (yield 81%).


(Synthesis of 26-3)


Synthesis was progressed according to Synthesis Method 4 using Compound 26-2 and 2-(2-pyridinyl)-benzenethiol. Compound 26-3 was obtained in 10.2 g (yield 72%).


(Synthesis of 26-4)


Synthesis was progressed according to Synthesis Method 5 using Compound 26-3 and phenylboronic acid. Compound 26-4 was obtained in 7.7 g (yield 77%).


(Synthesis of 26-5)


Synthesis was progressed according to Synthesis Method 8 using Compound 26-4 and cyclopropyl potassium trifluoroborate. Compound 26-5 was obtained in 4.8 g (yield 63%).


(Synthesis of Compound 26)


Synthesis was progressed according to Synthesis Method 14 using Compound 26-5. Compound 26 was obtained in 2.8 g (yield 56%).


HR LC/MS/MS m/z calculated for C91H75BN4OS2 (M+): 1314.5475; found: 1314.5473


Preparation Example 27
Compound 27



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(Synthesis of 27-1)


Synthesis was progressed according to Synthesis Method 1 using chloro BODIPY and 2-trifluoromethylbenzenethiol. Compound 27-1 was obtained in 6.3 g (yield 78%).


(Synthesis of 27-2)


Synthesis was progressed according to Synthesis Method 3 using Compound 27-1. Compound 27-2 was obtained in 7.5 g (yield 85%).


(Synthesis of 27-3)


Synthesis was progressed according to Synthesis Method 4 using Compound 27-2 and 2′-hydroxy-2,2″-bistrifluoromethyl-terphenyl-5′-carbonitrile. Compound 27-3 was obtained in 12.8 g (yield 73%).


(Synthesis of 27-4)


Synthesis was progressed according to Synthesis Method 5 using Compound 27-3 and 4-(phenoxycarbonyl)phenylboronic acid. Compound 27-4 was obtained in 8.6 g (yield 61%).


(Synthesis of 27-5)


Synthesis was progressed according to Synthesis Method 8 using Compound 27-4 and cyclohexyl potassium trifluoroborate. Compound 27-5 was obtained in 5.0 g (yield 57%).


(Synthesis of Compound 27)


Synthesis was progressed according to Synthesis Method 14 using Compound 27-5. Compound 27 was obtained in 2.0 g (yield 34%).


HR LC/MS/MS m/z calculated for C120H90BF15N4O6S (M+): 2010.6435; found: 2010.6439


Preparation Example 28
Compound 28



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(Synthesis of 28-1)


Synthesis was progressed according to Synthesis Method 1 using chloro BODIPY and 7-mercapto-2H-chromen-2-one. Compound 28-1 was obtained in 11.9 g (yield 73%).


(Synthesis of 28-2)


Synthesis was progressed according to Synthesis Method 2 using Compound 28-1. Compound 28-2 was obtained in 21.1 g (yield 84%).


(Synthesis of 28-3)


Synthesis was progressed according to Synthesis Method 4 using Compound 28-2 and 4-aminobenzenethiol. Compound 28-3 was obtained in 15.8 g (yield 68%).


(Synthesis of 28-4)


Synthesis was progressed according to Synthesis Method 5 using Compound 28-3 and 4-aminobenzeneboronic acid. Compound 28-4 was obtained in 11.2 g (yield 73%).


(Synthesis of 28-5)


Synthesis was progressed according to Synthesis Method 12 using Compound 28-4 and indium(III)propan-2-olate. Compound 28-5 was obtained in 4.9 g (yield 47%).


(Synthesis of Compound 28)


Synthesis was progressed according to Synthesis Method 14 using Compound 28-5. Compound 28 was obtained in 2.7 g (yield 52%).


HR LC/MS/MS m/z calculated for C72H69BN6O4S3 (M+): 1188.4635; found: 1188.4639


EXAMPLE
Example 1

A first solution was prepared by dissolving Compound 1, an organic fluorescent substance, in a xylene solvent.


A second solution was prepared by dissolving a thermoplastic resin SAN (styrene-acrylonitrile-based) in a xylene solvent. The first solution and the second solution were mixed so that the amount of the organic fluorescent substance was 0.5 parts by weight based on 100 parts by weight of the SAN, and the result was homogeneously mixed. The solid content in the mixed solution was 20% by weight and viscosity was 200 cps. This solution was coated on a PET substrate, and the result was dried to prepare a color conversion film.


A luminance spectrum of the prepared color conversion film was measured using a spectroradiometer (SR series of TOPCON Corporation). Specifically, the prepared color conversion film was laminated on one surface of a light guide plate of a backlight unit including an LED blue backlight (maximum light emission wavelength 450 nm) and the light guide plate, and after laminating a prism sheet and a DBEF film on the color conversion film, a luminance spectrum of the film was measured. When measuring the luminance spectrum, an initial value was set so that the brightness of the blue LED light was 600 nit based on without the color conversion film.


Example 2

An experiment was performed in the same manner as in Example 1 except that Compound 2 was used instead of Compound 1.


Example 3

An experiment was performed in the same manner as in Example 1 except that Compound 4 was used instead of Compound 1.


Example 4

An experiment was performed in the same manner as in Example 1 except that Compound 6 was used instead of Compound 1.


Example 5

An experiment was performed in the same manner as in Example 1 except that Compound 11 was used instead of Compound 1.


Example 6

An experiment was performed in the same manner as in Example 1 except that Compound 12 was used instead of Compound 1.


Example 7

An experiment was performed in the same manner as in Example 1 except that Compound 18 was used instead of Compound 1.


Example 8

An experiment was performed in the same manner as in Example 1 except that Compound 20 was used instead of Compound 1.


Example 9

An experiment was performed in the same manner as in Example 1 except that Compound 21 was used instead of Compound 1.


Example 10

An experiment was performed in the same manner as in Example 1 except that Compound 23 was used instead of Compound 1.


Example 11

An experiment was performed in the same manner as in Example 1 except that Compound 27 was used instead of Compound 1.


Example 12

An experiment was performed in the same manner as in Example 1 except that Compound 28 was used instead of Compound 1.


Comparative Example 1

An experiment was performed in the same manner as in Example 1 except that diPh was used instead of Compound 1.


Comparative Example 2

An experiment was performed in the same manner as in Example 1 except that diPhO was used instead of Compound 1.


Comparative Example 3

An experiment was performed in the same manner as in Example 1 except that OdiPh was used instead of Compound 1.


Comparative Example 4

An experiment was performed in the same manner as in Example 1 except that diPhS was used instead of Compound 1.


Comparative Example 5

An experiment was performed in the same manner as in Example 1 except that SdiPh was used instead of Compound 1.




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Thin film light emission wavelength, PLQY (thin film quantum efficiency) and PL intensity (%) of each of the color conversion films according to Examples 1 to 12 and Comparative Examples 1 to 5 are as shown in the following Table 4.













TABLE 4







Thin Film





Light Emission

PL



Wavelength PLλmax
PLQY
Intensity



(nm)
(%)
(%)




















Example 1
Compound 1
520
97
93


Example 2
Compound 2
531
94
94


Example 3
Compound 4
620
96
82


Example 4
Compound 6
626
95
86


Example 5
Compound 11
624
96
91


Example 6
Compound 12
682
97
88


Example 7
Compound 18
613
95
92


Example 8
Compound 20
689
94
91


Example 9
Compound 21
555
94
86


Example 10
Compound 23
536
93
84


Example 11
Compound 27
629
94
95


Example 12
Compound 28
703
92
93


Comparative
diPh
622
90
54


Example 1


Comparative
diPhO
550
32
49


Example 2


Comparative
OdiPh
519
85
52


Example 3


Comparative
diPhS
616
56
53


Example 4


Comparative
SdiPh
622
78
48


Example 5









When a color conversion film has low stability, there is a problem in that a wavelength of light finally appearing after passing through a light source and a film continuously changes over time.


According to Table 4, it was identified that the color conversion films according to Examples 1 to 12 had small changes in the PL intensity compared to Comparative Examples 1 to 5 leading to small changes in the wavelength, and therefore, light emission efficiency was high and stability was excellent.


The thin film light emission wavelength (PL λmax(nm)) was measured using FS-2 equipment of SCINCO Co., Ltd., and the thin film quantum efficiency (PLQY) was measured using Quantaurus-QY equipment of HAMAMATSU Photonics K.K.


PL intensity (%) is a value obtained by, based on PL of a manufactured film, irradiating an LED light source for 1,000 hours on the corresponding film, measuring PL again, and calculating a difference in the intensity from the initial value.

Claims
  • 1. A compound represented by Chemical Formula 1:
  • 2. The compound of claim 1, wherein X4 and X5 are the same as or different from each other, and each independently a halogen group; CN; an alkoxy group unsubstituted or substituted with a halogen group; an alkynyl group unsubstituted or substituted with a substituted or unsubstituted aryl group; an aryl group unsubstituted or substituted with a nitro group; an aryloxy group; or a heteroaryl group.
  • 3. The compound of claim 1, wherein R1 and R6 are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; CN; an alkyl group; a cycloalkyl group unsubstituted or substituted with an alkyl group; an alkoxy group; an aryloxy group unsubstituted or substituted with a halogen group, CN, CF3 or an alkyl group; an aryl group unsubstituted or substituted with a halogen group, CN, CF3, an alkyl group or an alkoxy group; or a substituted or unsubstituted heteroaryl group.
  • 4. The compound of claim 1, wherein R2 and R5 are the same as or different from each other, and each independently —C(═O)ORa; an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of a halogen group, CN, CF3, —C(═O)ORa, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; or a heteroaryl group having 6 to 30 carbon atoms unsubstituted or substituted with an aryl group, and Ra is a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.
  • 5. The compound of claim 1, wherein R3 and R4 are the same as or different from each other, and each independently an alkyl group having 1 to 30 carbon atoms unsubstituted or substituted with CF3; a cycloalkyl group having 1 to 30 carbon atoms unsubstituted or substituted with an alkyl group; an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of a halogen group, CN, CF3, —C(═O)ORa, an amine group, an alkoxy group, an alkyl group having 1 to 30 carbon atoms and a heteroaryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms, and Ra is a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.
  • 6. The compound of claim 1, wherein R7 is an aryl group unsubstituted or substituted with one or more selected from the group consisting of a halogen group, CN, CF3, an alkoxy group, an alkyl group unsubstituted or substituted with a halogen group, a substituted or unsubstituted aryl group, and a heteroaryl group; or a heteroaryl group unsubstituted or substituted with O═.
  • 7. The compound of claim 1, wherein X1 to X5 are selected from the combinations consisting of A1 to A40 of the following Tables 1-1 to 1-4, R1, R6 and R7 are selected from the combinations consisting of B1 to B1577 of the following Tables 2-1 to 2-9, and R2 to R5 are selected from the combinations consisting of C1 to C1435 of the following Tables 3-1 to 3-14:
  • 8. A color conversion film comprising: a resin matrix; andthe compound of claim 1 dispersed in the resin matrix.
  • 9. A backlight unit comprising the color conversion film of claim 8.
  • 10. A display apparatus comprising the backlight unit of claim 9.
  • 11. The compound of claim 1, wherein the Chemical Formula 1 is represented by any one of the following Chemical Formulae 1-1 to 1-4:
  • 12. The color conversion film of claim 8, wherein a material for the resin matrix is a thermoplastic polymer or a thermocurable polymer.
  • 13. The color conversion film of claim 12, wherein the material is a resin selected from the group consisting of a poly(meth)acryl-based resin, a polycarbonate (PC)-based, a polystyrene (PS)-based, a polyarylene (PAR)-based, a polyurethane (TPU)-based, a styrene-acrylonitrile (SAN)-based, a polyvinylidene fluoride (PVDF)-based, and a modified polyvinylidene fluoride (modified-PVDF)-based resin.
Priority Claims (1)
Number Date Country Kind
10-2018-0122401 Oct 2018 KR national
Parent Case Info

This application is a 35 U.S.C. 371 National Phase Entry Application from PCT/KR2019/013487, filed on Oct. 15, 2019, designating the United States and claiming priority to and the benefits of Korean Patent Application No. 10-2018-0122401 filed with the Korean Intellectual Property Office on Oct. 15, 2018, the entire contents of which are incorporated herein by reference.

PCT Information
Filing Document Filing Date Country Kind
PCT/KR2019/013487 10/15/2019 WO 00