US20180002256A1 - Double-spiro type compound and organic light-emitting device containing same - Google Patents

Double-spiro type compound and organic light-emitting device containing same Download PDF

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US20180002256A1
US20180002256A1 US15/545,577 US201615545577A US2018002256A1 US 20180002256 A1 US20180002256 A1 US 20180002256A1 US 201615545577 A US201615545577 A US 201615545577A US 2018002256 A1 US2018002256 A1 US 2018002256A1
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Yongbum CHA
Jin Joo Kim
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LG Chem Ltd
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LG Chem Ltd
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Definitions

  • the present specification relates to a double spiro structure compound and an organic light emitting device comprising the same.
  • An organic light emission phenomenon generally refers to a phenomenon converting electrical energy to light energy using an organic material.
  • An organic light emitting device using an organic light emission phenomenon normally has a structure comprising an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often formed in a multilayer structure formed with different materials in order to increase efficiency and stability of the organic light emitting device, and for example, may be formed with a hole injection layer, a hole transfer layer, a light emitting layer, an electron transfer layer, an electron injection layer and the like.
  • the present specification provides a double spiro structure compound and an organic light emitting device comprising the same.
  • One embodiment of the present specification provides a double spiro structure compound represented by the following Chemical Formula 1.
  • R 1 is represented by any one of the following Chemical Formula A to Chemical Formula C.
  • X 1 to X 3 are the same as or different from each other, and each independently CH or N,
  • At least one of X 1 to X 3 is N,
  • X 4 is O, S or NAr 5 ,
  • L 1 to L 3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms,
  • Ar 1 to Ar 5 are the same as or different from each other, and each independently selected from the group consisting of a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and
  • Cy1 is a substituted or unsubstituted monocyclic or multicyclic hydrocarbon ring having 3 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or multicyclic heteroring having 2 to 30 carbon atoms.
  • Another embodiment of the present invention provides an organic light emitting device comprising an anode; a cathode provided opposite to the anode; and a light emitting layer and one or more organic material layers provided between the anode and the cathode, wherein the light emitting layer and one or more layers of the organic material layers comprise the double spiro structure compound represented by Chemical Formula 1.
  • Compounds according to one embodiment of the present invention can be used as a material of an organic material layer of an organic light emitting device, and by using the compounds, efficiency enhancement, a low driving voltage and/or lifespan property enhancement can be accomplished in the organic light emitting device.
  • FIG. 1 is a diagram showing an organic light emitting device ( 10 ) according to one embodiment of the present specification.
  • FIG. 2 is a diagram showing an organic light emitting device ( 11 ) according to another embodiment of the present specification.
  • the present specification provides a double spiro structure compound represented by Chemical Formula 1.
  • a description of one member being placed “on” another member includes not only a case of the one member adjoining the another member but a case of still another member being present between the two members.
  • an “adjacent” group may mean a substituent substituting an atom directly linking 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.
  • two substituents substituting ortho positions in a benzene ring, and two substituents substituting the same carbon in an aliphatic ring may be interpreted as “adjacent” groups.
  • 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.
  • substituted or unsubstituted in the present specification means being substituted with one, two or more substituents selected from the group consisting of deuterium; a halogen group; a nitrile group; a nitro group; an imide group; an amide group; a carbonyl group; an ester group; a hydroxyl 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 alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group;
  • the halogen group may include fluorine, chlorine, bromine or iodine.
  • the number of carbon atoms of the imide group is not particularly limited, but is preferably from 1 to 30. Specifically, compounds having structures such as below may be included, but the imide group is not limited thereto.
  • the nitrogen of the amide group may be substituted with a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms.
  • compounds having the following structural formulae may be included, but the amide group is not limited thereto.
  • the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably from 1 to 30. Specifically, compounds having structures such as below may be included, but the carbonyl group is not limited thereto.
  • the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 carbon atoms.
  • a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 carbon atoms may be included, but the ester group is not limited thereto.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 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
  • 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.
  • 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, benxyloxy, p-methylbenxyloxy and the like, but are not limited thereto.
  • the amine group may be selected from the group consisting of —NH 2 ; an alkylamine group; an N-alkylarylamine group; an arylamine group; an N-arylheteroarylamine group; an N-alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is, although not particularly limited thereto, preferably 1 to 30.
  • 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, an N-9-methyl-anthracenylamine group, a diphenylamine group, an N-phenylnaphthylamine group, a ditolylamine group, an N-phenyltolylamine group, a triphenylamine group, an N-biphenylfluorenylamine group, an N-phenylfluorenylamine group, an N-phenylspirobifluorenylamine group, an N-biphenylspirobifluorenylamine group, an N-biphenyldibenzofuranylamine group, an N-phenylphenanthrenylamine group, an N-biphenyl
  • 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.
  • 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.
  • the N-alkylheteroarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and a heteroarylamine group.
  • the alkyl group in the alkylamine group, the N-alkylarylamine group, the N-alkylheteroarylamine group, the alkylthioxy group and the alkylsulfoxy group is the same as the examples of the alkyl group described above.
  • the alkylthioxy group may include a methylthioxy group, an ethylthioxy group, a tert-butylthioxy group, a hexylthioxy group, an octylthioxy group and the like
  • the alkylsulfoxy group may include a mesyl group, an ethylsulfoxy group, a propylsulfoxy group, a butylsulfoxy group and the like, however, the examples are not limited thereto.
  • 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.
  • silyl group may include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group and the like, but are not limited thereto.
  • the boron group may be —BR 100 R 101 R 102 , and herein, R 100 , R 101 and R 102 are the same as or different from each other, and may be each independently selected from the group consisting of hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted monocyclic or multicyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or multicyclic heteroaryl group having 2 to 30 carbon atoms.
  • phosphine oxide group may include a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, a dimethylphosphine oxide group and the like, but are not limited thereto.
  • 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, a quaterphenyl group and the like, but are not limited thereto.
  • the number of carbon atoms is not particularly limited, but is preferably from 10 to 30.
  • Specific examples of the multicyclic aryl group may include a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a crycenyl group, a fluorenyl group, a fluoranthenyl group and the like, but are not limited thereto.
  • the fluorenyl group may be substituted, and adjacent substituents may bond to each to form a ring.
  • the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the N-alkylarylamine group, the N-arylheteroarylamine group and the arylphosphine group may be same as the examples of the aryl group described above.
  • aryloxy group may include phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, 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
  • specific examples of the arylthioxy group may include a phenylthioxy group, a 2-methylphenylthioxy group, a 4-tert-butylphenylthioxy group and the like
  • specific examples of the arylsulfoxy group may include a benzenesulfoxy group, a p-tolu
  • examples of the arylamine group may include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group or a multicyclic aryl group.
  • the arylamine group comprising two or more aryl groups may include monocyclic aryl groups, multicyclic aryl groups, or both a monocyclic aryl group and a multicyclic aryl group.
  • the aryl group in the arylamine group may be selected from the examples of the aryl group described above.
  • the heteroaryl group is a group comprising 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 favorably from 2 to 30, and the heteroaryl group may be monocyclic or multicyclic.
  • heteroaryl group may include a thiophene group, a furanyl group, a pyrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, triazinyl group, a triazolyl group, an acridyl group, a pyridazinyl group, a pyrazinyl group, a qinolinyl 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,
  • examples of the heteroarylamine group may include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group.
  • the heteroarylamine group comprising two or more heteroaryl groups may include monocyclic heteroaryl groups, multicyclic heteroaryl groups, or both a monocyclic heteroaryl group and a multicyclic heteroaryl group.
  • the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroring group described above.
  • heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as the examples of the heteroaryl group described above.
  • the heteroring group may be monocyclic or multicyclic, may be aromatic, aliphatic or a fused ring of aromatic and aliphatic, and may be selected from the examples of the heteroaryl group.
  • the arylene group means an aryl group having two bonding sites, that is, a divalent group. Descriptions on the aryl group made above may be applied except for those that are each a divalent group.
  • the heteroarylene group means a heteroaryl group having two bonding sites, that is, a divalent group. Descriptions on the heteroaryl group made above may be applied except for those that are each a divalent group.
  • the hydrocarbon ring may be aromatic, aliphatic or a fused ring of aromatic and aliphatic, and may be selected from the examples of the cycloalkyl group or the aryl group except for those are not monovalent.
  • the aromatic ring may be monocyclic or multicyclic, and may be selected from the examples of the aryl group except for those are not monovalent.
  • the heteroring is a group comprising 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 heteroring may be monocyclic or multicyclic, may be aromatic, aliphatic or a fused ring of aromatic and aliphatic, and may be selected from the examples of the heteroaryl group except for those are not monovalent.
  • the double spiro structure compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulae 2 to 4.
  • the double spiro structure compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulae 1-1 to 1-3.
  • the double spiro structure compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulae 2-1 to 2-3.
  • X 1 to X 3 are the same as or different from each other, and each independently CH or N, and at least one of X 1 to X 3 is N.
  • X 1 to X 3 are the same as or different from each other, and each independently CH or N, and at least two of X 1 to X 3 are N.
  • X 1 to X 3 are N.
  • the double spiro structure compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulae 3-1 to 3-4.
  • the double spiro structure compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulae 3-5 to 3-16.
  • Chemical Formula 1 may be represented by any one of the following Chemical Formula 4-1 to Chemical Formula 4-3.
  • Cy1 is a substituted or unsubstituted monocyclic or multicyclic hydrocarbon ring having 3 to 30 carbon atoms.
  • Cy1 is a substituted or unsubstituted monocyclic or multicyclic hydrocarbon ring having 3 to 20 carbon atoms.
  • Cy1 is a substituted or unsubstituted monocyclic or multicyclic hydrocarbon ring having 3 to 10 carbon atoms.
  • Cy1 is a substituted or unsubstituted benzene ring.
  • Cy1 is a benzene ring.
  • Chemical Formula 1 may be represented by the following Chemical Formula 4-4.
  • the double spiro structure compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulae 4-5 to 4-7.
  • L 1 to L 3 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 20 carbon atoms.
  • L 1 to L 3 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 15 carbon atoms.
  • L 1 to L 3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylylene group.
  • L 1 to L 3 are the same as or different from each other, and each independently a direct bond; a phenylene group; or a biphenylylene group.
  • Ar 1 to Ar 5 are the same as or different from each other, and each independently selected from the group consisting of a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 25 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms.
  • a substituted or unsubstituted arylamine group a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 25 carbon atoms
  • a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms.
  • Ar 1 to Ar 5 are the same as or different from each other, and each independently selected from the group consisting of a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenylyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted quaterphenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted terphenylenyl group; a substituted or unsubstituted dibenzothiophene group; and a substituted or unsubstituted dibenzofuran group.
  • Ar 1 to Ar 5 are the same as or different from each other, and each independently selected from the group consisting of a phenyl group; a biphenylyl group; a naphthyl group; a terphenyl group; a quaterphenyl group; a fluorenyl group; a phenanthrenyl group; a terphenylenyl group; a dibenzothiophene group; and a dibenzofuran group, and
  • Ar 1 to Ar 5 may be unsubstituted or substituted with one or more selected from the group consisting of deuterium; a fluorine group; a nitrile group; a methyl group; a phenyl group; a biphenyl group; a naphthyl group; a fluorenyl group; a phenanthrenyl group; a dibenzothiophene group; a dibenzofuran group; a carbazolyl group; a benzocarbazolyl group; a diphenylamine group; a dibiphenylamine group; an N-phenylbiphenylamine group; an N-phenylfluorenylamine group; and an N-biphenylfluorenylamine group.
  • Ar 1 to Ar 5 are the same as or different from each other, and may be each independently selected as any one among the following structural formulae.
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently selected from the group consisting of a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenylyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted quaterphenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted terphenylenyl group; a substituted or unsubstituted dibenzothiophene group; and a substituted or unsubstituted dibenzofuran group.
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently selected from the group consisting of a phenyl group; a biphenylyl group; a naphthyl group; a terphenyl group; a quaterphenyl group; a fluorenyl group; a phenanthrenyl group; a terphenylenyl group; a dibenzothiophene group; and a dibenzofuran group, and
  • Ar 1 and Ar 2 may be unsubstituted or substituted with one or more selected from the group consisting of deuterium; a fluorine group; a nitrile group; a methyl group; a phenyl group; a biphenyl group; a naphthyl group; a fluorenyl group; a dibenzothiophene group; a dibenzofuranyl group; a carbazolyl group; a benzocarbazolyl group; a diphenylamine group; a dibiphenylamine group; an N-phenylbiphenylamine group; an N-phenylfluorenylamine group; and an N-biphenylfluorenylamine group.
  • Ar 1 and Ar 2 are the same as or different from each other, and may be each independently selected as any one among the following structural formulae.
  • Ar 3 and Ar 4 are the same as or different from each other, and each independently selected from the group consisting of a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenylyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted fluorenyl group; and a substituted or unsubstituted phenanthrenyl group.
  • Ar 3 and Ar 4 are the same as or different from each other, and each independently selected from the group consisting of a phenyl group; a biphenylyl group; a naphthyl group; a terphenyl group; a fluorenyl group; and a phenanthrenyl group, and
  • Ar 3 and Ar 4 may be unsubstituted or substituted with one or more selected from the group consisting of a methyl group; a phenyl group; a biphenyl group; a naphthyl group; and a fluorenyl group.
  • Ar 3 and Ar 4 are the same as or different from each other, and may be each independently selected as any one among the following structural formulae.
  • Ar 5 is selected from the group consisting of a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenylyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted dibenzothiophene group; and a substituted or unsubstituted dibenzofuran group.
  • Ar 5 is selected from the group consisting of a phenyl group; a biphenylyl group; a naphthyl group; a terphenyl group; a fluorenyl group; a phenanthrenyl group; a dibenzothiophene group; and a dibenzofuran group, and
  • Ar 5 may be unsubstituted or substituted with one or more selected from the group consisting of a methyl group; a phenyl group; a biphenyl group; a naphthyl group; a phenanthrenyl group; and a fluorenyl group.
  • Ar 5 may be selected as any one among the following structural formulae.
  • the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 2, and in the following Chemical Formula 2, L 1 , Ar 1 and Ar 2 are any one selected from among 2-1-1 to 2-1-334 of the following Table 1.
  • the double spiro structure compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulae 2-1 to 2-3, and in the following Chemical Formulae 2-1 to 2-3, L 1 , Ar 1 and Ar 2 may be selected from Table 1.
  • L 1 when Ar 1 and Ar 2 correspond to 2-1-10 in Table 1, it may be expressed as Compound 2-1-10 (2-1), and when corresponding to 2-1-20, it may be expressed as Compound 2-1-20 (2-1).
  • the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-1, and in the following Chemical Formula 3-1, L 2 , Ar 3 and Ar 4 are any one selected from among 3-1-1 to 3-1-104 of the following Table 2.
  • the double spiro structure compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulae 3-5 to 3-7, and in the following Chemical Formulae 3-5 to 3-7, L 2 , Ar 3 and Ar 4 may be selected from Table 2.
  • L 2 , Ar 3 and Ar 4 may be selected from Table 2.
  • L 2 , Ar 3 and Ar 4 when L 2 , Ar 3 and Ar 4 correspond to 3-1-10 in Table 2, it may be expressed as Compound 3-1-10 (3-5), and when corresponding to 3-1-20, it may be expressed as Compound 3-1-20 (3-5).
  • the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-2, and in the following Chemical Formula 3-2, L 2 , Ar 3 and Ar 4 are any one selected from among 3-2-1 to 3-2-104 of the following Table 3.
  • the double spiro structure compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulae 3-8 to 3-10, and in the following Chemical Formulae 3-8 to 3-10, L 2 , Ar 3 and Ar 4 may be selected from Table 3.
  • L 2 , Ar 3 and Ar 4 may be selected from Table 3.
  • t when L 2 , Ar 3 and Ar 4 correspond to 3-2-10 in Table 3, t may be expressed as Compound 3-2-10 (3-8), and when corresponding to 3-2-20, it may be expressed as Compound 3-2-20 (3-8).
  • the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-3, and in the following Chemical Formula 3-3, L 2 , Ar 3 and Ar 4 are any one selected from among 3-3-1 to 3-3-104 of the following Table 4.
  • the double spiro structure compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulae 3-11 to 3-13, and in the following Chemical Formulae 3-11 to 3-13, L 2 , Ar 3 and Ar 4 may be selected from Table 4.
  • L 2 when Ar 3 and Ar 4 correspond to 3-3-10 in Table 4, it may be expressed as Compound 3-3-10 (3-11), and when corresponding to 3-3-20, it may be expressed as Compound 3-3-20 (3-11).
  • the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-4, and in the following Chemical Formula 3-4, L 2 , Ar 3 and Ar 4 are any one selected from among 3-4-1 to 3-4-104 of the following Table 5.
  • the double spiro structure compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulae 3-14 to 3-16, and in the following Chemical Formulae 3-14 to 3-16, L 2 , Ar 3 and Ar 4 may be selected from Table 5.
  • L 2 , Ar 3 and Ar 4 when L 2 , Ar 3 and Ar 4 correspond to 3-4-10 in Table 5, it may be expressed as Compound 3-4-10 (3-14), and when corresponding to 3-4-20, it may be expressed as Compound 3-4-20 (3-14).
  • the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 4-4, and in the following Chemical Formula 4-4, L 3 and X 4 are any one selected from among 4-4-1 to 4-4-22 of the following Table 6.
  • the double spiro structure compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulae 4-5 to 4-7, and in the following Chemical Formulae 4-5 to 4-7, L 3 and X 4 may be selected from Table 6.
  • L 3 and X 4 may be selected from Table 6.
  • L 3 and X 4 when L 3 and X 4 correspond to 4-4-10 in Table 6, it may be expressed as Compound 4-4-10 (4-5), and when corresponding to 4-4-20, it may be expressed as Compound 4-4-20 (4-5).
  • One embodiment of the present specification provides an organic light emitting device comprising an anode; a cathode provided opposite to the anode; and a light emitting layer and one or more organic material layers provided between the anode and the cathode, wherein the light emitting layer or one or more layers of the organic material layers comprise the double spiro structure compound represented by Chemical Formula 1.
  • the organic material layer of the organic light emitting device of the present specification may be formed in a single layer structure, but may be formed in a multilayer structure in which two or more organic material layers are laminated.
  • the organic light emitting device of the present invention may have a structure comprising a hole injection layer, a hole transfer layer, an electron blocking layer, a hole blocking layer, an electron transfer layer, an electron injection layer and the like as the organic material layer.
  • the structure of the organic light emitting device is not limited thereto, and may comprise less numbers of organic material layers.
  • the structure of the organic light emitting device of the present invention may be as shown in FIG. 1 and FIG. 2 , but is not limited thereto.
  • FIG. 1 illustrates a structure of an organic light emitting device ( 10 ) in which an anode ( 30 ), a light emitting layer ( 40 ) and a cathode ( 50 ) are consecutively laminated on a substrate ( 20 ).
  • FIG. 1 is an illustrative structure of the organic light emitting device according to one embodiment of the present specification, and other organic material layers may be further included therein.
  • FIG. 2 illustrates a structure of an organic light emitting device in which an anode ( 30 ), a hole injection layer ( 60 ), a hole transfer layer ( 70 ), a light emitting layer ( 40 ), an electron transfer layer ( 80 ), an electron injection layer ( 90 ) and a cathode ( 50 ) are consecutively laminated on a substrate ( 20 ).
  • FIG. 2 is an illustrative structure of the organic light emitting device according to one embodiment of the present specification, and other organic material layers may be further included therein.
  • the organic material layer comprises a hole injection layer or a hole transfer layer
  • the hole injection layer or the hole transfer layer comprises the double spiro structure compound represented by Chemical Formula 1.
  • the organic material layer comprises an electron blocking layer
  • the electron blocking layer comprises the double spiro structure compound represented by Chemical Formula 1.
  • the light emitting layer comprises the double spiro structure compound represented by Chemical Formula 1.
  • the organic material layer comprises an electron transfer layer or an electron injection layer, wherein the electron transfer layer or the electron injection layer comprises the double spiro structure compound represented by Chemical Formula 1.
  • the organic material layer comprises an electron transfer layer, an electron injection layer, or a layer carrying out electron transfer and electron injection at the same time
  • the electron transfer layer, the electron injection layer, or the layer carrying out electron transfer and electron injection at the same time comprises the double spiro structure compound represented by Chemical Formula 1.
  • the organic light emitting device comprises one or more organic material layers provided between the anode and the light emitting layer, wherein the organic material layer comprises a double spiro structure compound represented by the following Chemical Formula 2.
  • L 1 is a direct bond; a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, and
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • the double spiro structure compound represented by Chemical Formula 2 may be represented by any one of Chemical Formulae 2-1 to 2-3 described above.
  • the organic light emitting device comprises one or more organic material layers provided between the cathode and the light emitting layer, and the light emitting layer and one or more layers of the organic material layers comprise a double spiro structure compound represented by the following Chemical Formula 3.
  • X 1 to X 3 are the same as or different from each other, and each independently CH or N,
  • At least one of X 1 to X 3 is N,
  • L 2 is a direct bond; a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or multicyclic heteroarylene group having 2 to 30 carbon atoms, and
  • Ar 3 and Ar 4 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • the double spiro structure compound represented by Chemical Formula 3 may be represented by any one of Chemical Formulae 3-1 to 3-9 described above.
  • the organic light emitting device comprises one or more organic material layers provided between the cathode and the light emitting layer, wherein the organic material layer comprises a double spiro structure compound represented by the following Chemical Formula 4.
  • X 4 is O, S or NAr 5 ,
  • L 3 is a direct bond; a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or multicyclic heteroarylene group having 2 to 30 carbon atoms,
  • Ar 5 is selected from the group consisting of hydrogen; a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and
  • Cy1 is a substituted or unsubstituted monocyclic or multicyclic hydrocarbon ring having 3 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or multicyclic heteroring having 2 to 30 carbon atoms.
  • the double spiro structure compound represented by Chemical Formula 4 may be represented by any one of Chemical Formulae 4-1 to 4-3 described above.
  • the organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that one or more layers of organic material layers comprise the double spiro structure compound of the present specification, that is, the double spiro structure compound represented by Chemical Formula 1.
  • the organic material layers may be formed with the same material or with different materials.
  • the organic light emitting device of the present specification may be manufactured by consecutively laminating an anode, an organic material layer and a cathode on a substrate.
  • the organic light emitting device may be manufactured by forming the anode on the substrate by depositing a metal, a metal oxide having conductivity, or alloys thereof using a physical vapor deposition (PVD) method such as a sputtering method or an e-beam evaporation method, forming the organic material layer comprising a hole injection layer, a hole transfer layer, a light emitting layer and an electron transfer layer thereon, then depositing a material capable of being used as the cathode thereon.
  • PVD physical vapor deposition
  • the organic light emitting device may be manufactured by consecutively depositing a cathode material, an organic material layer, and an anode material.
  • the double Spiro structure compound represented by Chemical Formula 1 may be formed as the organic material layer using a solution coating method as well as a vacuum deposition method.
  • the solution coating method means spin coating, dip coating, doctor blading, ink jet printing, screen printing, a spray method, roll coating and the like, but is not limited thereto.
  • anode material a material having large work function is normally preferable so that hole injection to the organic material layer is smooth.
  • the anode material capable of being used in the present invention include metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylen-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode material a material having small work function is normally preferable so that electron injection to the organic material layer is smooth.
  • the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials such as LiF/Al, LiO 2 /Al or Mg/Ag, and the like, but are not limited thereto.
  • the hole injection layer is a layer that injects holes from an electrode
  • the hole injection material is preferably a compound that has an ability to transfer holes, therefore, has a hole injection effect in an anode, has an excellent hole injection effect for a light emitting layer or a light emitting material, prevents excitons generated in the light emitting layer from moving to an electron injection layer or an electron injection material, and in addition, has an excellent thin film forming ability.
  • the highest occupied molecular orbital (HOMO) of the hole injection material is preferably in between the work function of an anode material and the HOMO of surrounding organic material layers.
  • the hole injection material examples include a metal porphyrin, oligothiophene, an arylamine-based organic material, a hexanitrile hexazatriphenylene-based organic material, a quinacridone-based organic material, a perylene-based organic material, anthraquinone, and a polyaniline- and a polythiophene-based conductive polymer, and the like, but are not limited thereto.
  • the hole transfer layer is a layer that receives holes from a hole injection layer and transfers the holes to a light emitting layer
  • a hole transfer material a material capable of receiving holes from an anode or a hole injection layer, moving the holes to a light emitting layer, and having high mobility for the holes, is suitable.
  • Specific examples thereof include an arylamine-based organic material, a conductive polymer, a block copolymer having conjugated parts and non-conjugated parts together, and the like, but are not limited thereto.
  • a light emitting material of the light emitting layer is a material capable of emitting light in a visible light region by receiving holes and electrons from a hole transfer layer and an electron transfer layer, respectively, and binding the holes and the electrons, and is preferably a material having favorable quantum efficiency for fluorescence or phosphorescence.
  • Specific examples thereof include a 8-hydroxy-quinoline aluminum complex (Alq 3 ); a carbazole-based compound; a dimerized styryl compound; BAlq; a 10-hydroxybenzo quinoline-metal compound; a benzoxazole-, a benzthiazole- and a benzimidazole-based compound; a poly(p-phenylenevinylene) (PPV)-based polymer; a spiro compound; polyfluorene, rubrene, and the like, but are not limited thereto.
  • Alq 3 8-hydroxy-quinoline aluminum complex
  • a carbazole-based compound a dimerized styryl compound
  • BAlq a 10-hydroxybenzo quinoline-metal compound
  • a benzoxazole-, a benzthiazole- and a benzimidazole-based compound a poly(p-phenylenevinylene) (PPV)-based polymer
  • PPV poly(p-
  • the light emitting layer may comprise a host material and a dopant material.
  • the host material includes a fused aromatic ring derivative, a heteroring-containing compound or the like.
  • the fused aromatic ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound and the like
  • the heteroring-containing compound includes a carbazole derivative, a dibenzofuran derivative, a ladder-type furan compound, a pyrimidine derivative and the like, but the material is not limited thereto.
  • the dopant material includes an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, a metal complex and the like.
  • the aromatic amine derivative is a fused aromatic ring derivative having a substituted or unsubstituted arylamino group and includes arylamino group-including pyrene, anthracene, crycene, peryflanthene and the like
  • the styrylamine compound is a compound in which substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, and one, two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • styrylamine styryldiamine, styryltriamine, styryltetramine or the like is included, but the styrylamine compound is not limited thereto.
  • the metal complex includes an iridium complex, a platinum complex or the like, but is not limited thereto.
  • the electron transfer layer is a layer that receives electrons from an electron injection layer and transfers the electrons to a light emitting layer
  • a material capable of favorably receiving electrons from a cathode, moving the electrons to a light emitting layer, and having high mobility for the electrons is suitable.
  • Specific examples thereof include an Al complex of 8-hydroxyquinoline; a complex including Alq 3 ; an organic radical compound; a hydroxyflavon-metal complex and the like, but are not limited thereto.
  • the electron transfer layer may be used together with any desired cathode material as used according to existing technologies.
  • the suitable cathode material include common materials that have small work function, and in which an aluminum layer or a silver layer follows.
  • the cathode material includes cesium, barium, calcium, ytterbium and samarium, and in each case, an aluminum layer or a silver layer follows.
  • the electron injection layer is a layer that injects electrons from an electrode
  • the electron injection material is preferably a compound that has an ability to transfer electrons, has an electron injection effect from a cathode, has an excellent electron injection effect for a light emitting layer or a light emitting material, prevents excitons generated in the light emitting layer from moving to a hole injection layer, and in addition, has an excellent thin film forming ability.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone or the like, and derivatives thereof, a metal complex compound, a nitrogen-containing 5-membered ring derivative, and the like, but are not limited thereto.
  • the metal complex compound includes 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)berylium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium and the like, but is not limited thereto.
  • the organic light emitting device may be a top-emission type, a bottom-emission type or a dual-emission type depending on the materials used.
  • the double spiro structure compound represented by Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.
  • the double spiro structure compound represented by Chemical Formula 1 according to the present specification may be prepared through a multi-step chemical reaction.
  • the preparation of the compounds is described by the following synthesis examples and preparation examples.
  • the double spiro structure compound represented by Chemical Formula 1 may be prepared to compounds corresponding to Chemical Formula 2, Chemical Formula 3 and Chemical Formula 4 using methods and orders as in the following Reaction Formula 1-1, Reaction Formula 1-2 and Reaction Formula 1-3, respectively, and although not limited to such reactions, reaction formulae are simply described in order to illuminate the present invention.
  • compounds represented by Chemical Formulae 2 to 4 may be diversely prepared through varying L 1 to L 3 , Ar 1 to Ar 4 , Cy 1 , and X 1 to X 4 .
  • Compound 2-1-6 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that phenylfluoreneaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-7 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that biphenylfluoreneaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-10 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that 1,1′-biphenylphenylaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-15 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that bisbiphenylaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-20 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that terphenylphenylaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-25 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that orthobiphenylphenylaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-26 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that orthobiphenylfluoreneaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-40 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that 2-dibenzothiophenephenylaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-41 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that 2-dibenzothiophenebiphenylaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-42 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that 2-dibenzothiophenefluoreneaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-46 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that 2-dibenzofuranphenylaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-47 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that 2-dibenzofuranbiphenylaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-48 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that 2-dibenzofuranfluoreneaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-52 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that N-(4-(9H-carbazol-9-yl)phenyl)-9,9′-dimethyl-9H-fluoren-2-aminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-54 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that N-(9,9′-dimethyl-9H-fluoren-2-yl)-9-phenyl-9H-carbazol-3-1-Amino)phenyl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-64 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-(diphenylamino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-65 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-([1,1′-biphenyl]-4-yl(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-66 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-([1,1′:4′,1′′-terphenyl]-4-yl(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-67 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-(di([1,1′-biphenyl]-4-yl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-69 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-([1,1′-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-75 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-([1,1′-biphenyl]-2-yl([1,1′-biphenyl]-4-yl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-77 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-((9,9-dimethyl-9H-fluoren-2-yl)(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-81 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-([1,1′-biphenyl]-2-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-241 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-(dibenzo[b,d]thiophen-2-yl(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-242 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-(dibenzo[b,d]thiophen-4-yl(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-246 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-(dibenzo[b,d]furan-4-yl(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-315 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-((4′-(diphenylamino)-[1,1′-biphenyl]-4-yl)(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-316 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-((4-(diphenylamino)phenyl)(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-311 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-((4-([1,1′-biphenyl]-4-yl(phenyl)amino)phenyl)(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-318 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-((4-(di([1,1′-biphenyl]-4-yl)amino)phenyl)(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-320 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-((4-([1,1′-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)phenyl)(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 3-1-2 (3-5) was prepared in the same manner as in Preparation Example 2-1-1 preparing Compound 3-1-1 (3-5) except that (4-(4-([1,1′-biphenyl]-4-yl)-6-phenylpyridin-2-yl)phenyl)boronic acid was used instead of (4-(4,6-diphenylpyridin-2-yl)phenyl)boronic acid.
  • Compound 3-1-6 (3-5) was prepared in the same manner as in Preparation Example 2-1-1 preparing Compound 3-1-1 (3-5) except that (4-4-(9,9-dimethyl-9H-fluoren-2-yl)-6-phenylpyridin-2-yl)phenyl)boronic acid was used instead of (4-(4, 6-diphenylpyridin-2-yl)phenyl)boronic acid.
  • Compound 3-1-9 (3-5) was prepared in the same manner as in Preparation Example 2-1-1 preparing Compound 3-1-1 (3-5) except that (4-(4,6-di([1,1′-biphenyl]-4-yl)pyridin-2-yl)phenyl)boronic acid was used instead of (4-(4,6-diphenylpyridin-2-yl)phenyl)boronic acid.
  • Compound 3-1-15 (3-5) was prepared in the same manner as in Preparation Example 2-1-1 preparing Compound 3-1-1 (3-5) except that (4′-(4,6-diphenylpyridin-2-yl)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(4,6-diphenylpyridin-2-yl)phenyl)boronic acid.
  • Compound 3-1-16 (3-5) was prepared in the same manner as in Preparation Example 2-1-1 preparing Compound 3-1-1 (3-5) except that (4′-(6-([1,1′-biphenyl]-4-yl)-4-phenylpyridin-2-yl)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(4,6-diphenylpyridin-2-yl)phenyl)boronic acid.
  • Compound 3-1-18 (3-5) was prepared in the same manner as in Preparation Example 2-1-1 preparing Compound 3-1-1 (3-5) except that (4′-(4,6-di([1,1′-biphenyl]-4-yl)pyridin-2-yl)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(4,6-diphenylpyridin-2-yl)phenyl)boronic acid.
  • Compound 3-1-20 (3-5) was prepared in the same manner as in Preparation Example 2-1-1 preparing Compound 3-1-1 (3-5) except that (4′-(6-([1,1′-biphenyl]-4-yl)-4-(9,9-dimethyl-9H-fluoren-2-yl)pyridin-2-yl)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(4,6-diphenylpyridin-2-yl)phenyl)boronic acid.
  • Compound 4-4-1 (4-5) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that 4′-(benzo[d]oxazol-2-yl)biphenyl-4-ylboronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 4-4-2 (4-5) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that 4′-(benzo[d]thiazol-2-yl)biphenyl-4-ylboronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • a glass substrate on which indium tin oxide (ITO) was coated as a thin film to a thickness of 1,000 ⁇ was placed in detergent-dissolved distilled water and ultrasonic cleaned.
  • ITO indium tin oxide
  • a product of Fischer Co. was used as the detergent, and as the distilled water, distilled water filtered twice with a filter manufactured by Millipore Co. was used.
  • the substrate was ultrasonic cleaned with solvents of isopropyl alcohol, acetone and methanol, then dried, and then transferred to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using oxygen plasma, and then transferred to a vacuum depositor.
  • a hole injection layer was formed by thermal vacuum depositing hexanitrile hexaazatriphenylene (HAT) of the following chemical formula to a thickness of 500 ⁇ .
  • HAT hexanitrile hexaazatriphenylene
  • a hole transfer layer was formed on the hole injection layer by vacuum depositing the following compound 4-4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) (300 ⁇ ), a material transferring holes.
  • an electron blocking layer was formed on the hole transfer layer to a film thickness of 100 ⁇ by vacuum depositing the following compound N-([1,1′-bisphenyl]-4-yl)-N-(4-(11-([1,1′-biphenyl]-4-yl)-11H-benzo[a]carbazol-5-yl)phenyl)-[1,1′-biphenyl]-4-amine (EB1)(100 ⁇ ).
  • a light emitting layer was formed on the electron blocking layer to a film thickness of 300 ⁇ by vacuum depositing BH and BD shown below in a weight ratio of 25:1.
  • An electron injection and transfer layer was formed on the light emitting layer to a thickness of 300 ⁇ by vacuum depositing the compound ET1 and the compound lithium quinolate (LiQ) in a weight ratio of 1:1.
  • a cathode was formed on the electron injection and transfer layer by depositing lithium fluoride (LiF) to a thickness of 12 ⁇ and aluminum to a thickness of 2,000 ⁇ in consecutive order.
  • An organic light emitting device was manufactured by maintaining, in the above-mentioned processes, the deposition rates of the organic materials at 0.4 ⁇ /sec to 0.7 ⁇ /sec, the deposition rates of the lithium fluoride and the aluminum of the cathode at 0.3 ⁇ /sec and 2 ⁇ /sec, respectively, and the degree of vacuum during the deposition at 2 ⁇ 10 ⁇ 7 torr to 5 ⁇ 10 ⁇ 6 torr.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-1 (2-1) was used instead of EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-6 (2-1) was used instead of EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-7 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-10 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-15 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-25 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-26 (2-1) was used instead of EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-40 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-41 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-42 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-47 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-48 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-52 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-54 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-64 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-66 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-67 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-69 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-75 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-77 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-241 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-242 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-246 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-315 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-316 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-318 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-320 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that a compound of the following HT1 was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that a compound of the following HT3 was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that a compound of the following HT4 was used instead of Compound EB1.
  • the devices of Examples 1-1 to 1-32 using compounds having the double spiro structure compound represented by Chemical Formula 2 as the core had a lower driving voltage and enhanced efficiency compared to the devices of Comparative Example 1-1 to 1-4, and the device of Comparative Example 1 using a material of Compound EB1 as an electron blocking layer.
  • the double spiro structure compound according to the present specification had an excellent electron blocking ability and was capable of being used in an electron blocking layer of an organic light emitting device.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that the compounds of Examples 1-1 to 32 were used instead of NPB as the hole transfer layer.
  • the devices of Examples 2-1 to 2-32 using compounds having the double spiro structure represented by Chemical Formula 2 as the core had a lower driving voltage and enhanced efficiency compared to the devices of Comparative Examples 1-1 to 1-4, and the device of Comparative Example 1 using a material of NPB as the hole transfer layer.
  • the double spiro structure compound according to the present specification had an excellent hole transfer ability, and was capable of being used as a hole transfer layer in an organic light emitting device.
  • a glass substrate on which indium tin oxide (ITO) was coated as a thin film to a thickness of 1,000 ⁇ was placed in detergent-dissolved distilled water and ultrasonic cleaned.
  • ITO indium tin oxide
  • a product of Fischer Co. was used as the detergent, and as the distilled water, distilled water filtered twice with a filter manufactured by Millipore Co. was used.
  • the substrate was ultrasonic cleaned with solvents of isopropyl alcohol, acetone and methanol, then dried, and then transferred to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using oxygen plasma, and then transferred to a vacuum depositor.
  • a light emitting device was formed in order of m-MTDATA (60 nm)/TCTA (80 nm)/CBP+10% Ir(ppy) 3 (300 nm)/BCP (10 nm)/Alq 3 (30 nm)/LiF (1 nm)/Al (200 nm) using CBP as a host to manufacture an organic light emitting device.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-1-1 (3-5) was used instead of CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-1-2 (3-5) was used instead of CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-1-6 (3-5) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-1-9 (3-5) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-1-15 (3-5) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-1-16 (3-5) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-1-20 (3-5) was used instead of CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-2-1 (3-8) was used instead of CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-2-2 (3-8) was used instead of CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-2-6 (3-8) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-2-9 (3-8) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-2-16 (3-8) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-2-18 (3-8) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-2-20 (3-8) was used instead of CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-3-1 (3-11) was used instead of CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-3-2 (3-11) was used instead of CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-3-9 (3-11) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-3-15 (3-11) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-3-16 (3-11) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-3-18 (3-11) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-3-20 (3-11) was used instead of CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-4-2 (3-14) was used instead of CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-4-6 (3-14) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-4-9 (3-14) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-4-15 (3-14) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-4-16 (3-14) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-4-20 (3-14) was used instead of CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that a compound of the following GH1 was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that a compound of the following GH2 was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that a compound of the following GH3 was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that a compound of the following GH4 was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that a compound of the following GH6 was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that a compound of the following GH7 was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that a compound of the following GH8 was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that compounds of Examples 4-1 to 4-34 were used as in the following Table 10 instead of ET1 as the electron transfer layer.

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Abstract

The present specification relates to a double spiro structure compound, and an organic light emitting device comprising the same.

Description

    TECHNICAL FIELD
  • This application claims priority to and the benefits of Korean Patent Application No. 10-2015-0023506, filed with the Korean Intellectual Property Office on Feb. 16, 2015, the entire contents of which are incorporated herein by reference.
  • The present specification relates to a double spiro structure compound and an organic light emitting device comprising the same.
    • BACKGROUND ART
  • An organic light emission phenomenon generally refers to a phenomenon converting electrical energy to light energy using an organic material. An organic light emitting device using an organic light emission phenomenon normally has a structure comprising an anode, a cathode, and an organic material layer therebetween. Herein, the organic material layer is often formed in a multilayer structure formed with different materials in order to increase efficiency and stability of the organic light emitting device, and for example, may be formed with a hole injection layer, a hole transfer layer, a light emitting layer, an electron transfer layer, an electron injection layer and the like. When a voltage is applied between the two electrodes in such an organic light emitting device structure, holes and electrons are injected to the organic material layer from the anode and the cathode, respectively, and when the injected holes and electrons meet, excitons are formed, and light emits when these excitons fall back to the ground state.
  • Development of new materials for such an organic light emitting device has been continuously required.
    • PRIOR ART DOCUMENTS Patent Document
  • International Patent Application Laid-Open Publication No. 2003-012890.
    • DISCLOSURE Technical Problem
  • The present specification provides a double spiro structure compound and an organic light emitting device comprising the same.
    • Technical Solution
  • One embodiment of the present specification provides a double spiro structure compound represented by the following Chemical Formula 1.
  • Figure US20180002256A1-20180104-C00001
  • In Chemical Formula 1,
  • R1 is represented by any one of the following Chemical Formula A to Chemical Formula C.
  • Figure US20180002256A1-20180104-C00002
  • In Chemical Formula A to Chemical Formula C,
  • X1 to X3 are the same as or different from each other, and each independently CH or N,
  • at least one of X1 to X3 is N,
  • X4 is O, S or NAr5,
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms,
  • Ar1 to Ar5 are the same as or different from each other, and each independently selected from the group consisting of a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and
  • Cy1 is a substituted or unsubstituted monocyclic or multicyclic hydrocarbon ring having 3 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or multicyclic heteroring having 2 to 30 carbon atoms.
  • Another embodiment of the present invention provides an organic light emitting device comprising an anode; a cathode provided opposite to the anode; and a light emitting layer and one or more organic material layers provided between the anode and the cathode, wherein the light emitting layer and one or more layers of the organic material layers comprise the double spiro structure compound represented by Chemical Formula 1.
    • Advantageous Effects
  • Compounds according to one embodiment of the present invention can be used as a material of an organic material layer of an organic light emitting device, and by using the compounds, efficiency enhancement, a low driving voltage and/or lifespan property enhancement can be accomplished in the organic light emitting device.
    • DESCRIPTION OF DRAWINGS
  • FIG. 1 is a diagram showing an organic light emitting device (10) according to one embodiment of the present specification.
  • FIG. 2 is a diagram showing an organic light emitting device (11) according to another embodiment of the present specification.
    •  MODE FOR DISCLOSURE
  • Hereinafter, the present specification will be described in more detail.
  • The present specification provides a double spiro structure compound represented by Chemical Formula 1.
  • In the present specification, a description of a certain part “comprising” certain constituents means capable of further comprising other constituents, and does not exclude other constituents unless particularly stated on the contrary.
  • In the present specification, a description of one member being placed “on” another member includes not only a case of the one member adjoining the another member but a case of still another member being present between the two members.
  • In the present specification, an “adjacent” group may mean a substituent substituting an atom directly linking 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 “adjacent” groups.
  • Examples of the substituents 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 deuterium; a halogen group; a nitrile group; a nitro group; an imide group; an amide group; a carbonyl group; an ester group; a hydroxyl 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 alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; and a substituted or unsubstituted heteroring 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,
  • Figure US20180002256A1-20180104-C00003
  • means a site bonding to other substituents or bonding sites.
  • In the present specification, 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. Specifically, compounds having structures such as below may be included, but the imide group is not limited thereto.
  • Figure US20180002256A1-20180104-C00004
  • In the present specification, in the amide group, the nitrogen of the amide group may be substituted with a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, compounds having the following structural formulae may be included, but the amide group is not limited thereto.
  • Figure US20180002256A1-20180104-C00005
  • 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 structures such as below may be included, but the carbonyl group is not limited thereto.
  • Figure US20180002256A1-20180104-C00006
  • In the present specification, in the ester group, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, compounds having the following structural formulae may be included, but the ester group is not limited thereto.
  • Figure US20180002256A1-20180104-C00007
  • In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 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, benxyloxy, p-methylbenxyloxy and the like, but are not limited thereto.
  • In the present specification, the amine group may be selected from the group consisting of —NH2; an alkylamine group; an N-alkylarylamine group; an arylamine group; an N-arylheteroarylamine group; an N-alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is, although not particularly limited thereto, preferably 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, an N-9-methyl-anthracenylamine group, a diphenylamine group, an N-phenylnaphthylamine group, a ditolylamine group, an N-phenyltolylamine group, a triphenylamine group, an N-biphenylfluorenylamine group, an N-phenylfluorenylamine group, an N-phenylspirobifluorenylamine group, an N-biphenylspirobifluorenylamine group, an N-biphenyldibenzofuranylamine group, an N-phenylphenanthrenylamine group, an N-biphenylphenanthrenylamine group, an N-phenyldibenzofuranylamine group, an N-phenylbiphenylamine group, an N-phenylcarbazolylamine group, an N-biphenylcarbazolylamine group, an N-biphenyldibenzothiophenylamine group, an N-phenyldibenzothiophenylamine group, an N-biphenylnaphthylamine group, an N-biphenylterphenylamine group, an N-phenylterphenylamine group, an N-phenylnaphthylamine group, an N-quaterphenylfluorenylamine group, an N-terphenylfluorenylamine group, a difluorenylamine group, an N-phenylbenzocarbazolylamine group, an N-biphenylbenzocarbazolylamine group, an N-fluorenylcarbazolylamine 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 heteroarylamine group.
  • In the present specification, the alkyl group in the alkylamine group, the N-alkylarylamine group, the N-alkylheteroarylamine group, the alkylthioxy group and the alkylsulfoxy group is the same as the examples of the alkyl group described above. Specifically, 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 the alkylsulfoxy group may include a mesyl group, an ethylsulfoxy group, a propylsulfoxy group, a butylsulfoxy group and the like, however, the examples 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, specific examples of the silyl group may include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group and the like, but are not limited thereto.
  • In the present specification, the boron group may be —BR100R101R102, and herein, R100, R101 and R102 are the same as or different from each other, and may be each independently selected from the group consisting of hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted monocyclic or multicyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or multicyclic heteroaryl group having 2 to 30 carbon atoms.
  • In the present specification, specific examples of the phosphine oxide group may include a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, a dimethylphosphine oxide group and the like, but are not limited thereto.
  • 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, a quaterphenyl group and the like, but are not limited thereto.
  • When the aryl group is a multicyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably from 10 to 30. Specific examples of the multicyclic aryl group may include a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a crycenyl group, a fluorenyl group, a fluoranthenyl 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 to form a ring.
  • When the fluorenyl group is substituted,
  • Figure US20180002256A1-20180104-C00008
  • and the like may be included. However, the compound is not limited thereto.
  • In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the N-alkylarylamine group, the N-arylheteroarylamine group and the arylphosphine group may be 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-trimethylphenoxy, 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, and specific examples of the arylsulfoxy group may include a benzenesulfoxy group, a p-toluenesulfoxy group and the like, however, the examples are not limited thereto.
  • In the present specification, examples of the arylamine group may include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a multicyclic aryl group. The arylamine group comprising two or more aryl groups may include monocyclic aryl groups, multicyclic aryl groups, or both a monocyclic aryl group and a multicyclic aryl group. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.
  • In the present specification, the heteroaryl group is a group comprising 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 favorably from 2 to 30, and the heteroaryl group may be monocyclic or multicyclic. Examples of the heteroaryl group may include a thiophene group, a furanyl group, a pyrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, triazinyl group, a triazolyl group, an acridyl group, a pyridazinyl group, a pyrazinyl group, a qinolinyl 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 benxzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthrolinyl group, a thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, a benzoquinazolinyl group, an indolofluorenyl group, an indolocarbazolyl group, a dibenzocarbazolyl group, a benzoquinolinyl group, a benzonaphthofuranyl group, a benzonaphthothiophene group, a dibenzofuranyl group, a phenoxazinyl group and the like, but are not limited thereto.
  • In the present specification, examples of the heteroarylamine group may include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroarylamine group comprising two or more heteroaryl groups may include monocyclic heteroaryl groups, multicyclic heteroaryl groups, or both a monocyclic heteroaryl group and a multicyclic heteroaryl group. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroring group described above.
  • In the present specification, examples of the heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as the examples of the heteroaryl group described above.
  • In the present specification, the heteroring group may be monocyclic or multicyclic, may be aromatic, aliphatic or a fused ring of aromatic and aliphatic, and may be selected from the examples of the heteroaryl group.
  • In the present specification, the arylene group means an aryl group having two bonding sites, that is, a divalent group. Descriptions on the aryl group made above may be applied except for those that are each a divalent group.
  • In the present specification, the heteroarylene group means a heteroaryl group having two bonding sites, that is, a divalent group. Descriptions on the heteroaryl group made above may be applied except for those that are each a divalent group.
  • In the present specification, the hydrocarbon ring may be aromatic, aliphatic or a fused ring of aromatic and aliphatic, and may be selected from the examples of the cycloalkyl group or the aryl group except for those are not monovalent.
  • In the present specification, the aromatic ring may be monocyclic or multicyclic, and may be selected from the examples of the aryl group except for those are not monovalent.
  • In the present specification, the heteroring is a group comprising 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 heteroring may be monocyclic or multicyclic, may be aromatic, aliphatic or a fused ring of aromatic and aliphatic, and may be selected from the examples of the heteroaryl group except for those are not monovalent.
  • According to one embodiment of the present specification, the double spiro structure compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulae 2 to 4.
  • Figure US20180002256A1-20180104-C00009
  • In Chemical Formulae 2 to 4, definitions of X1 to X4, L1 to L3, Ar1 to Ar4 and Cy1 are the same as in Chemical Formula 1.
  • According to one embodiment of the present specification, the double spiro structure compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulae 1-1 to 1-3.
  • Figure US20180002256A1-20180104-C00010
  • In Chemical Formula 1-1 to Chemical Formula 1-3, a definition of R1 is the same as in Chemical Formula 1.
  • According to one embodiment of the present specification, the double spiro structure compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulae 2-1 to 2-3.
  • Figure US20180002256A1-20180104-C00011
  • In Chemical Formula 2-1 to Chemical Formula 2-3, definitions of L1, Ar1 and Ar2 are the same as in Chemical Formula 1.
  • According to one embodiment of the present specification, in Chemical Formula 1, X1 to X3 are the same as or different from each other, and each independently CH or N, and at least one of X1 to X3 is N.
  • According to another embodiment of the present specification, in Chemical Formula 1, X1 to X3 are the same as or different from each other, and each independently CH or N, and at least two of X1 to X3 are N.
  • According to another embodiment of the present specification, in Chemical Formula 1, X1 to X3 are N.
  • According to one embodiment of the present specification, the double spiro structure compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulae 3-1 to 3-4.
  • Figure US20180002256A1-20180104-C00012
  • In Chemical Formulae 3-1 to 3-4, definitions of L2, Ar3 and Ar4 are the same as in Chemical Formula 1.
  • According to one embodiment of the present specification, the double spiro structure compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulae 3-5 to 3-16.
  • Figure US20180002256A1-20180104-C00013
    Figure US20180002256A1-20180104-C00014
    Figure US20180002256A1-20180104-C00015
  • In Chemical Formulae 3-5 to 3-16, definitions of L2, Ar3 and Ar4 are the same as in Chemical Formula 1.
  • According to one embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following Chemical Formula 4-1 to Chemical Formula 4-3.
  • Figure US20180002256A1-20180104-C00016
  • In Chemical Formula 4-1 to Chemical Formula 4-3, definitions of X4, L3 and Cy1 are the same as in Chemical Formula 1.
  • According to one embodiment of the present specification, in Chemical Formula 1, Cy1 is a substituted or unsubstituted monocyclic or multicyclic hydrocarbon ring having 3 to 30 carbon atoms.
  • According to one embodiment of the present specification, Cy1 is a substituted or unsubstituted monocyclic or multicyclic hydrocarbon ring having 3 to 20 carbon atoms.
  • According to one embodiment of the present specification, Cy1 is a substituted or unsubstituted monocyclic or multicyclic hydrocarbon ring having 3 to 10 carbon atoms.
  • According to one embodiment of the present specification, Cy1 is a substituted or unsubstituted benzene ring.
  • According to one embodiment of the present specification, Cy1 is a benzene ring.
  • According to one embodiment of the present specification, Chemical Formula 1 may be represented by the following Chemical Formula 4-4.
  • Figure US20180002256A1-20180104-C00017
  • In Chemical Formula 4-4, definitions of X4 and L3 are the same as in Chemical Formula 1.
  • According to one embodiment of the present specification, the double spiro structure compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulae 4-5 to 4-7.
  • Figure US20180002256A1-20180104-C00018
  • In Chemical Formula 4-5 to Chemical Formula 4-7, definitions of X4 and L3 are the same as in Chemical Formula 1.
  • According to one embodiment of the present specification, in Chemical Formula 1, L1 to L3 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 20 carbon atoms.
  • According to one embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 15 carbon atoms.
  • According to one embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylylene group.
  • According to one embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; a phenylene group; or a biphenylylene group.
  • According to one embodiment of the present specification, in Chemical Formula 1, Ar1 to Ar5 are the same as or different from each other, and each independently selected from the group consisting of a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 25 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms. According to one embodiment of the present specification,
  • Ar1 to Ar5 are the same as or different from each other, and each independently selected from the group consisting of a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenylyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted quaterphenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted terphenylenyl group; a substituted or unsubstituted dibenzothiophene group; and a substituted or unsubstituted dibenzofuran group.
  • According to one embodiment of the present specification, Ar1 to Ar5 are the same as or different from each other, and each independently selected from the group consisting of a phenyl group; a biphenylyl group; a naphthyl group; a terphenyl group; a quaterphenyl group; a fluorenyl group; a phenanthrenyl group; a terphenylenyl group; a dibenzothiophene group; and a dibenzofuran group, and
  • Ar1 to Ar5 may be unsubstituted or substituted with one or more selected from the group consisting of deuterium; a fluorine group; a nitrile group; a methyl group; a phenyl group; a biphenyl group; a naphthyl group; a fluorenyl group; a phenanthrenyl group; a dibenzothiophene group; a dibenzofuran group; a carbazolyl group; a benzocarbazolyl group; a diphenylamine group; a dibiphenylamine group; an N-phenylbiphenylamine group; an N-phenylfluorenylamine group; and an N-biphenylfluorenylamine group.
  • According to one embodiment of the present specification, Ar1 to Ar5 are the same as or different from each other, and may be each independently selected as any one among the following structural formulae.
  • Figure US20180002256A1-20180104-C00019
    Figure US20180002256A1-20180104-C00020
    Figure US20180002256A1-20180104-C00021
    Figure US20180002256A1-20180104-C00022
    Figure US20180002256A1-20180104-C00023
    Figure US20180002256A1-20180104-C00024
    Figure US20180002256A1-20180104-C00025
  • According to one embodiment of the present specification,
    Figure US20180002256A1-20180104-P00001
    means a site linking to other substituents.
  • According to one embodiment of the present specification, in Chemical Formula 1, Ar1 and Ar2 are the same as or different from each other, and each independently selected from the group consisting of a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenylyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted quaterphenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted terphenylenyl group; a substituted or unsubstituted dibenzothiophene group; and a substituted or unsubstituted dibenzofuran group.
  • According to one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently selected from the group consisting of a phenyl group; a biphenylyl group; a naphthyl group; a terphenyl group; a quaterphenyl group; a fluorenyl group; a phenanthrenyl group; a terphenylenyl group; a dibenzothiophene group; and a dibenzofuran group, and
  • Ar1 and Ar2 may be unsubstituted or substituted with one or more selected from the group consisting of deuterium; a fluorine group; a nitrile group; a methyl group; a phenyl group; a biphenyl group; a naphthyl group; a fluorenyl group; a dibenzothiophene group; a dibenzofuranyl group; a carbazolyl group; a benzocarbazolyl group; a diphenylamine group; a dibiphenylamine group; an N-phenylbiphenylamine group; an N-phenylfluorenylamine group; and an N-biphenylfluorenylamine group.
  • According to one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and may be each independently selected as any one among the following structural formulae.
  • Figure US20180002256A1-20180104-C00026
    Figure US20180002256A1-20180104-C00027
    Figure US20180002256A1-20180104-C00028
    Figure US20180002256A1-20180104-C00029
    Figure US20180002256A1-20180104-C00030
    Figure US20180002256A1-20180104-C00031
    Figure US20180002256A1-20180104-C00032
  • According to one embodiment of the present specification, in Chemical Formula 1, Ar3 and Ar4 are the same as or different from each other, and each independently selected from the group consisting of a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenylyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted fluorenyl group; and a substituted or unsubstituted phenanthrenyl group.
  • According to one embodiment of the present specification, in Chemical Formula 1, Ar3 and Ar4 are the same as or different from each other, and each independently selected from the group consisting of a phenyl group; a biphenylyl group; a naphthyl group; a terphenyl group; a fluorenyl group; and a phenanthrenyl group, and
  • Ar3 and Ar4 may be unsubstituted or substituted with one or more selected from the group consisting of a methyl group; a phenyl group; a biphenyl group; a naphthyl group; and a fluorenyl group.
  • According to one embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and may be each independently selected as any one among the following structural formulae.
  • Figure US20180002256A1-20180104-C00033
    Figure US20180002256A1-20180104-C00034
  • According to one embodiment of the present specification, in Chemical Formula 1, Ar5 is selected from the group consisting of a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenylyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted dibenzothiophene group; and a substituted or unsubstituted dibenzofuran group.
  • According to one embodiment of the present specification, in Chemical Formula 1, Ar5 is selected from the group consisting of a phenyl group; a biphenylyl group; a naphthyl group; a terphenyl group; a fluorenyl group; a phenanthrenyl group; a dibenzothiophene group; and a dibenzofuran group, and
  • Ar5 may be unsubstituted or substituted with one or more selected from the group consisting of a methyl group; a phenyl group; a biphenyl group; a naphthyl group; a phenanthrenyl group; and a fluorenyl group.
  • According to one embodiment of the present specification, Ar5 may be selected as any one among the following structural formulae.
  • Figure US20180002256A1-20180104-C00035
    Figure US20180002256A1-20180104-C00036
  • According to one embodiment of the present specification, the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 2, and in the following Chemical Formula 2, L1, Ar1 and Ar2 are any one selected from among 2-1-1 to 2-1-334 of the following Table 1.
  • Figure US20180002256A1-20180104-C00037
  • TABLE 1
    Figure US20180002256A1-20180104-C00038
    Figure US20180002256A1-20180104-C00039
    Figure US20180002256A1-20180104-C00040
    2-1- 1 Direct bond
    Figure US20180002256A1-20180104-C00041
    Figure US20180002256A1-20180104-C00042
    2-1- 2 Direct bond
    Figure US20180002256A1-20180104-C00043
    Figure US20180002256A1-20180104-C00044
    2-1- 3 Direct bond
    Figure US20180002256A1-20180104-C00045
    Figure US20180002256A1-20180104-C00046
    2-1- 4 Direct bond
    Figure US20180002256A1-20180104-C00047
    Figure US20180002256A1-20180104-C00048
    2-1- 5 Direct bond
    Figure US20180002256A1-20180104-C00049
    Figure US20180002256A1-20180104-C00050
    2-1- 6 Direct bond
    Figure US20180002256A1-20180104-C00051
    Figure US20180002256A1-20180104-C00052
    2-1- 7 Direct bond
    Figure US20180002256A1-20180104-C00053
    Figure US20180002256A1-20180104-C00054
    2-1- 8 Direct bond
    Figure US20180002256A1-20180104-C00055
    Figure US20180002256A1-20180104-C00056
    2-1- 9 Direct bond
    Figure US20180002256A1-20180104-C00057
    Figure US20180002256A1-20180104-C00058
    2-1- 10 Direct bond
    Figure US20180002256A1-20180104-C00059
    Figure US20180002256A1-20180104-C00060
    2-1- 11 Direct bond
    Figure US20180002256A1-20180104-C00061
    Figure US20180002256A1-20180104-C00062
    2-1- 12 Direct bond
    Figure US20180002256A1-20180104-C00063
    Figure US20180002256A1-20180104-C00064
    2-1- 13 Direct bond
    Figure US20180002256A1-20180104-C00065
    Figure US20180002256A1-20180104-C00066
    2-1- 14 Direct bond
    Figure US20180002256A1-20180104-C00067
    Figure US20180002256A1-20180104-C00068
    2-1- 15 Direct bond
    Figure US20180002256A1-20180104-C00069
    Figure US20180002256A1-20180104-C00070
    2-1- 16 Direct bond
    Figure US20180002256A1-20180104-C00071
    Figure US20180002256A1-20180104-C00072
    2-1- 17 Direct bond
    Figure US20180002256A1-20180104-C00073
    Figure US20180002256A1-20180104-C00074
    2-1- 18 Direct bond
    Figure US20180002256A1-20180104-C00075
    Figure US20180002256A1-20180104-C00076
    2-1- 19 Direct bond
    Figure US20180002256A1-20180104-C00077
    Figure US20180002256A1-20180104-C00078
    2-1- 20 Direct bond
    Figure US20180002256A1-20180104-C00079
    Figure US20180002256A1-20180104-C00080
    2-1- 21 Direct bond
    Figure US20180002256A1-20180104-C00081
    Figure US20180002256A1-20180104-C00082
    2-1- 22 Direct bond
    Figure US20180002256A1-20180104-C00083
    Figure US20180002256A1-20180104-C00084
    2-1- 23 Direct bond
    Figure US20180002256A1-20180104-C00085
    Figure US20180002256A1-20180104-C00086
    2-1- 24 Direct bond
    Figure US20180002256A1-20180104-C00087
    Figure US20180002256A1-20180104-C00088
    2-1- 25 Direct bond
    Figure US20180002256A1-20180104-C00089
    Figure US20180002256A1-20180104-C00090
    2-1- 26 Direct bond
    Figure US20180002256A1-20180104-C00091
    Figure US20180002256A1-20180104-C00092
    2-1- 27 Direct bond
    Figure US20180002256A1-20180104-C00093
    Figure US20180002256A1-20180104-C00094
    2-1- 28 Direct bond
    Figure US20180002256A1-20180104-C00095
    Figure US20180002256A1-20180104-C00096
    2-1- 29 Direct bond
    Figure US20180002256A1-20180104-C00097
    Figure US20180002256A1-20180104-C00098
    2-1- 30 Direct bond
    Figure US20180002256A1-20180104-C00099
    Figure US20180002256A1-20180104-C00100
    2-1- 31 Direct bond
    Figure US20180002256A1-20180104-C00101
    Figure US20180002256A1-20180104-C00102
    2-1- 32 Direct bond
    Figure US20180002256A1-20180104-C00103
    Figure US20180002256A1-20180104-C00104
    2-1- 33 Direct bond
    Figure US20180002256A1-20180104-C00105
    Figure US20180002256A1-20180104-C00106
    2-1- 34 Direct bond
    Figure US20180002256A1-20180104-C00107
    Figure US20180002256A1-20180104-C00108
    2-1- 35 Direct bond
    Figure US20180002256A1-20180104-C00109
    Figure US20180002256A1-20180104-C00110
    2-1- 36 Direct bond
    Figure US20180002256A1-20180104-C00111
    Figure US20180002256A1-20180104-C00112
    2-1- 37 Direct bond
    Figure US20180002256A1-20180104-C00113
    Figure US20180002256A1-20180104-C00114
    2-1- 38 Direct bond
    Figure US20180002256A1-20180104-C00115
    Figure US20180002256A1-20180104-C00116
    2-1- 39 Direct bond
    Figure US20180002256A1-20180104-C00117
    Figure US20180002256A1-20180104-C00118
    2-1- 40 Direct bond
    Figure US20180002256A1-20180104-C00119
    Figure US20180002256A1-20180104-C00120
    2-1- 41 Direct bond
    Figure US20180002256A1-20180104-C00121
    Figure US20180002256A1-20180104-C00122
    2-1- 42 Direct bond
    Figure US20180002256A1-20180104-C00123
    Figure US20180002256A1-20180104-C00124
    2-1- 43 Direct bond
    Figure US20180002256A1-20180104-C00125
    Figure US20180002256A1-20180104-C00126
    2-1- 44 Direct bond
    Figure US20180002256A1-20180104-C00127
    Figure US20180002256A1-20180104-C00128
    2-1- 45 Direct bond
    Figure US20180002256A1-20180104-C00129
    Figure US20180002256A1-20180104-C00130
    2-1- 46 Direct bond
    Figure US20180002256A1-20180104-C00131
    Figure US20180002256A1-20180104-C00132
    2-1- 47 Direct bond
    Figure US20180002256A1-20180104-C00133
    Figure US20180002256A1-20180104-C00134
    2-1- 48 Direct bond
    Figure US20180002256A1-20180104-C00135
    Figure US20180002256A1-20180104-C00136
    2-1- 49 Direct bond
    Figure US20180002256A1-20180104-C00137
    Figure US20180002256A1-20180104-C00138
    2-1- 50 Direct bond
    Figure US20180002256A1-20180104-C00139
    Figure US20180002256A1-20180104-C00140
    2-1- 51 Direct bond
    Figure US20180002256A1-20180104-C00141
    Figure US20180002256A1-20180104-C00142
    2-1- 52 Direct bond
    Figure US20180002256A1-20180104-C00143
    Figure US20180002256A1-20180104-C00144
    2-1- 53 Direct bond
    Figure US20180002256A1-20180104-C00145
    Figure US20180002256A1-20180104-C00146
    2-1- 54 Direct bond
    Figure US20180002256A1-20180104-C00147
    Figure US20180002256A1-20180104-C00148
    2-1- 55 Direct bond
    Figure US20180002256A1-20180104-C00149
    Figure US20180002256A1-20180104-C00150
    2-1- 56 Direct bond
    Figure US20180002256A1-20180104-C00151
    Figure US20180002256A1-20180104-C00152
    2-1- 57 Direct bond
    Figure US20180002256A1-20180104-C00153
    Figure US20180002256A1-20180104-C00154
    2-1- 58 Direct bond
    Figure US20180002256A1-20180104-C00155
    Figure US20180002256A1-20180104-C00156
    2-1- 59 Direct bond
    Figure US20180002256A1-20180104-C00157
    Figure US20180002256A1-20180104-C00158
    2-1- 60 Direct bond
    Figure US20180002256A1-20180104-C00159
    Figure US20180002256A1-20180104-C00160
    2-1- 61 Direct bond
    Figure US20180002256A1-20180104-C00161
    Figure US20180002256A1-20180104-C00162
    2-1- 62 Direct bond
    Figure US20180002256A1-20180104-C00163
    Figure US20180002256A1-20180104-C00164
    2-1- 63 Direct bond
    Figure US20180002256A1-20180104-C00165
    Figure US20180002256A1-20180104-C00166
    2-1- 64
    Figure US20180002256A1-20180104-C00167
    Figure US20180002256A1-20180104-C00168
    Figure US20180002256A1-20180104-C00169
    2-1- 65
    Figure US20180002256A1-20180104-C00170
    Figure US20180002256A1-20180104-C00171
    Figure US20180002256A1-20180104-C00172
    2-1- 66
    Figure US20180002256A1-20180104-C00173
    Figure US20180002256A1-20180104-C00174
    Figure US20180002256A1-20180104-C00175
    2-1- 67
    Figure US20180002256A1-20180104-C00176
    Figure US20180002256A1-20180104-C00177
    Figure US20180002256A1-20180104-C00178
    2-1- 68
    Figure US20180002256A1-20180104-C00179
    Figure US20180002256A1-20180104-C00180
    Figure US20180002256A1-20180104-C00181
    2-1- 69
    Figure US20180002256A1-20180104-C00182
    Figure US20180002256A1-20180104-C00183
    Figure US20180002256A1-20180104-C00184
    2-1- 70
    Figure US20180002256A1-20180104-C00185
    Figure US20180002256A1-20180104-C00186
    Figure US20180002256A1-20180104-C00187
    2-1- 71
    Figure US20180002256A1-20180104-C00188
    Figure US20180002256A1-20180104-C00189
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    Figure US20180002256A1-20180104-C00979
  • According to one embodiment of the present specification, the double spiro structure compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulae 2-1 to 2-3, and in the following Chemical Formulae 2-1 to 2-3, L1, Ar1 and Ar2 may be selected from Table 1. For example, in the following Chemical Formula 2-1, L1, when Ar1 and Ar2 correspond to 2-1-10 in Table 1, it may be expressed as Compound 2-1-10 (2-1), and when corresponding to 2-1-20, it may be expressed as Compound 2-1-20 (2-1).
  • In addition, in the following Chemical Formula 2-2, when L1, Ar1 and Ar2 correspond to 2-1-10 in Table 1, it may be expressed as Compound 2-1-10 (2-2), and when corresponding to 2-1-20, it may be expressed as Compound 2-1-20 (2-2).
  • Furthermore, in the following Chemical Formula 2-3, when L1, Ar1 and Ar2 correspond to 2-1-10 in Table 1, it may be expressed as Compound 2-1-10 (2-3), and when corresponding to 2-1-20, it may be expressed as Compound 2-1-20 (2-3).
  • Figure US20180002256A1-20180104-C00980
  • According to one embodiment of the present specification, the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-1, and in the following Chemical Formula 3-1, L2, Ar3 and Ar4 are any one selected from among 3-1-1 to 3-1-104 of the following Table 2.
  • Figure US20180002256A1-20180104-C00981
  • TABLE 2
    Figure US20180002256A1-20180104-C00982
    Figure US20180002256A1-20180104-C00983
    Figure US20180002256A1-20180104-C00984
    3-1-1 Direct bond
    Figure US20180002256A1-20180104-C00985
    Figure US20180002256A1-20180104-C00986
    3-1-2 Direct bond
    Figure US20180002256A1-20180104-C00987
    Figure US20180002256A1-20180104-C00988
    3-1-3 Direct bond
    Figure US20180002256A1-20180104-C00989
    Figure US20180002256A1-20180104-C00990
    3-1-4 Direct bond
    Figure US20180002256A1-20180104-C00991
    Figure US20180002256A1-20180104-C00992
    3-1-5 Direct bond
    Figure US20180002256A1-20180104-C00993
    Figure US20180002256A1-20180104-C00994
    3-1-6 Direct bond
    Figure US20180002256A1-20180104-C00995
    Figure US20180002256A1-20180104-C00996
    3-1-7 Direct bond
    Figure US20180002256A1-20180104-C00997
    Figure US20180002256A1-20180104-C00998
    3-1-8 Direct bond
    Figure US20180002256A1-20180104-C00999
    Figure US20180002256A1-20180104-C01000
    3-1-9 Direct bond
    Figure US20180002256A1-20180104-C01001
    Figure US20180002256A1-20180104-C01002
    3-1-10 Direct bond
    Figure US20180002256A1-20180104-C01003
    Figure US20180002256A1-20180104-C01004
    3-1-11 Direct bond
    Figure US20180002256A1-20180104-C01005
    Figure US20180002256A1-20180104-C01006
    3-1-12
    Figure US20180002256A1-20180104-C01007
    Figure US20180002256A1-20180104-C01008
    Figure US20180002256A1-20180104-C01009
    3-1-13
    Figure US20180002256A1-20180104-C01010
    Figure US20180002256A1-20180104-C01011
    Figure US20180002256A1-20180104-C01012
    3-1-14
    Figure US20180002256A1-20180104-C01013
    Figure US20180002256A1-20180104-C01014
    Figure US20180002256A1-20180104-C01015
    3-1-15
    Figure US20180002256A1-20180104-C01016
    Figure US20180002256A1-20180104-C01017
    Figure US20180002256A1-20180104-C01018
    3-1-16
    Figure US20180002256A1-20180104-C01019
    Figure US20180002256A1-20180104-C01020
    Figure US20180002256A1-20180104-C01021
    3-1-17
    Figure US20180002256A1-20180104-C01022
    Figure US20180002256A1-20180104-C01023
    Figure US20180002256A1-20180104-C01024
    3-1-18
    Figure US20180002256A1-20180104-C01025
    Figure US20180002256A1-20180104-C01026
    Figure US20180002256A1-20180104-C01027
    3-1-19
    Figure US20180002256A1-20180104-C01028
    Figure US20180002256A1-20180104-C01029
    Figure US20180002256A1-20180104-C01030
    3-1-20
    Figure US20180002256A1-20180104-C01031
    Figure US20180002256A1-20180104-C01032
    Figure US20180002256A1-20180104-C01033
    3-1-21
    Figure US20180002256A1-20180104-C01034
    Figure US20180002256A1-20180104-C01035
    Figure US20180002256A1-20180104-C01036
    3-1-22
    Figure US20180002256A1-20180104-C01037
    Figure US20180002256A1-20180104-C01038
    Figure US20180002256A1-20180104-C01039
    3-1-23
    Figure US20180002256A1-20180104-C01040
    Figure US20180002256A1-20180104-C01041
    Figure US20180002256A1-20180104-C01042
    3-1-24
    Figure US20180002256A1-20180104-C01043
    Figure US20180002256A1-20180104-C01044
    Figure US20180002256A1-20180104-C01045
    3-1-25
    Figure US20180002256A1-20180104-C01046
    Figure US20180002256A1-20180104-C01047
    Figure US20180002256A1-20180104-C01048
    3-1-26
    Figure US20180002256A1-20180104-C01049
    Figure US20180002256A1-20180104-C01050
    Figure US20180002256A1-20180104-C01051
    3-1-27
    Figure US20180002256A1-20180104-C01052
    Figure US20180002256A1-20180104-C01053
    Figure US20180002256A1-20180104-C01054
    3-1-28
    Figure US20180002256A1-20180104-C01055
    Figure US20180002256A1-20180104-C01056
    Figure US20180002256A1-20180104-C01057
    3-1-29
    Figure US20180002256A1-20180104-C01058
    Figure US20180002256A1-20180104-C01059
    Figure US20180002256A1-20180104-C01060
    3-1-30
    Figure US20180002256A1-20180104-C01061
    Figure US20180002256A1-20180104-C01062
    Figure US20180002256A1-20180104-C01063
    3-1-31
    Figure US20180002256A1-20180104-C01064
    Figure US20180002256A1-20180104-C01065
    Figure US20180002256A1-20180104-C01066
    3-1-32
    Figure US20180002256A1-20180104-C01067
    Figure US20180002256A1-20180104-C01068
    Figure US20180002256A1-20180104-C01069
    3-1-33
    Figure US20180002256A1-20180104-C01070
    Figure US20180002256A1-20180104-C01071
    Figure US20180002256A1-20180104-C01072
    3-1-34
    Figure US20180002256A1-20180104-C01073
    Figure US20180002256A1-20180104-C01074
    Figure US20180002256A1-20180104-C01075
    3-1-35
    Figure US20180002256A1-20180104-C01076
    Figure US20180002256A1-20180104-C01077
    Figure US20180002256A1-20180104-C01078
    3-1-36
    Figure US20180002256A1-20180104-C01079
    Figure US20180002256A1-20180104-C01080
    Figure US20180002256A1-20180104-C01081
    3-1-37
    Figure US20180002256A1-20180104-C01082
    Figure US20180002256A1-20180104-C01083
    Figure US20180002256A1-20180104-C01084
    3-1-38
    Figure US20180002256A1-20180104-C01085
    Figure US20180002256A1-20180104-C01086
    Figure US20180002256A1-20180104-C01087
    3-1-39
    Figure US20180002256A1-20180104-C01088
    Figure US20180002256A1-20180104-C01089
    Figure US20180002256A1-20180104-C01090
    3-1-40
    Figure US20180002256A1-20180104-C01091
    Figure US20180002256A1-20180104-C01092
    Figure US20180002256A1-20180104-C01093
    3-1-41
    Figure US20180002256A1-20180104-C01094
    Figure US20180002256A1-20180104-C01095
    Figure US20180002256A1-20180104-C01096
    3-1-42
    Figure US20180002256A1-20180104-C01097
    Figure US20180002256A1-20180104-C01098
    Figure US20180002256A1-20180104-C01099
    3-1-43
    Figure US20180002256A1-20180104-C01100
    Figure US20180002256A1-20180104-C01101
    Figure US20180002256A1-20180104-C01102
    3-1-44
    Figure US20180002256A1-20180104-C01103
    Figure US20180002256A1-20180104-C01104
    Figure US20180002256A1-20180104-C01105
    3-1-45
    Figure US20180002256A1-20180104-C01106
    Figure US20180002256A1-20180104-C01107
    Figure US20180002256A1-20180104-C01108
    3-1-46
    Figure US20180002256A1-20180104-C01109
    Figure US20180002256A1-20180104-C01110
    Figure US20180002256A1-20180104-C01111
    3-1-47
    Figure US20180002256A1-20180104-C01112
    Figure US20180002256A1-20180104-C01113
    Figure US20180002256A1-20180104-C01114
    3-1-48
    Figure US20180002256A1-20180104-C01115
    Figure US20180002256A1-20180104-C01116
    Figure US20180002256A1-20180104-C01117
    3-1-49
    Figure US20180002256A1-20180104-C01118
    Figure US20180002256A1-20180104-C01119
    Figure US20180002256A1-20180104-C01120
    3-1-50
    Figure US20180002256A1-20180104-C01121
    Figure US20180002256A1-20180104-C01122
    Figure US20180002256A1-20180104-C01123
    3-1-51
    Figure US20180002256A1-20180104-C01124
    Figure US20180002256A1-20180104-C01125
    Figure US20180002256A1-20180104-C01126
    3-1-52
    Figure US20180002256A1-20180104-C01127
    Figure US20180002256A1-20180104-C01128
    Figure US20180002256A1-20180104-C01129
    3-1-53
    Figure US20180002256A1-20180104-C01130
    Figure US20180002256A1-20180104-C01131
    Figure US20180002256A1-20180104-C01132
    3-1-54
    Figure US20180002256A1-20180104-C01133
    Figure US20180002256A1-20180104-C01134
    Figure US20180002256A1-20180104-C01135
    3-1-55
    Figure US20180002256A1-20180104-C01136
    Figure US20180002256A1-20180104-C01137
    Figure US20180002256A1-20180104-C01138
    3-1-56
    Figure US20180002256A1-20180104-C01139
    Figure US20180002256A1-20180104-C01140
    Figure US20180002256A1-20180104-C01141
    3-1-57
    Figure US20180002256A1-20180104-C01142
    Figure US20180002256A1-20180104-C01143
    Figure US20180002256A1-20180104-C01144
    3-1-58
    Figure US20180002256A1-20180104-C01145
    Figure US20180002256A1-20180104-C01146
    Figure US20180002256A1-20180104-C01147
    3-1-59
    Figure US20180002256A1-20180104-C01148
    Figure US20180002256A1-20180104-C01149
    Figure US20180002256A1-20180104-C01150
    3-1-60
    Figure US20180002256A1-20180104-C01151
    Figure US20180002256A1-20180104-C01152
    Figure US20180002256A1-20180104-C01153
    3-1-61
    Figure US20180002256A1-20180104-C01154
    Figure US20180002256A1-20180104-C01155
    Figure US20180002256A1-20180104-C01156
    3-1-62
    Figure US20180002256A1-20180104-C01157
    Figure US20180002256A1-20180104-C01158
    Figure US20180002256A1-20180104-C01159
    3-1-63
    Figure US20180002256A1-20180104-C01160
    Figure US20180002256A1-20180104-C01161
    Figure US20180002256A1-20180104-C01162
    3-1-64
    Figure US20180002256A1-20180104-C01163
    Figure US20180002256A1-20180104-C01164
    Figure US20180002256A1-20180104-C01165
    3-1-65
    Figure US20180002256A1-20180104-C01166
    Figure US20180002256A1-20180104-C01167
    Figure US20180002256A1-20180104-C01168
    3-1-66
    Figure US20180002256A1-20180104-C01169
    Figure US20180002256A1-20180104-C01170
    Figure US20180002256A1-20180104-C01171
    3-1-67
    Figure US20180002256A1-20180104-C01172
    Figure US20180002256A1-20180104-C01173
    Figure US20180002256A1-20180104-C01174
    3-1-68
    Figure US20180002256A1-20180104-C01175
    Figure US20180002256A1-20180104-C01176
    Figure US20180002256A1-20180104-C01177
    3-1-69
    Figure US20180002256A1-20180104-C01178
    Figure US20180002256A1-20180104-C01179
    Figure US20180002256A1-20180104-C01180
    3-1-70
    Figure US20180002256A1-20180104-C01181
    Figure US20180002256A1-20180104-C01182
    Figure US20180002256A1-20180104-C01183
    3-1-71
    Figure US20180002256A1-20180104-C01184
    Figure US20180002256A1-20180104-C01185
    Figure US20180002256A1-20180104-C01186
    3-1-72
    Figure US20180002256A1-20180104-C01187
    Figure US20180002256A1-20180104-C01188
    Figure US20180002256A1-20180104-C01189
    3-1-73
    Figure US20180002256A1-20180104-C01190
    Figure US20180002256A1-20180104-C01191
    Figure US20180002256A1-20180104-C01192
    3-1-74
    Figure US20180002256A1-20180104-C01193
    Figure US20180002256A1-20180104-C01194
    Figure US20180002256A1-20180104-C01195
    3-1-75
    Figure US20180002256A1-20180104-C01196
    Figure US20180002256A1-20180104-C01197
    Figure US20180002256A1-20180104-C01198
    3-1-76
    Figure US20180002256A1-20180104-C01199
    Figure US20180002256A1-20180104-C01200
    Figure US20180002256A1-20180104-C01201
    3-1-77
    Figure US20180002256A1-20180104-C01202
    Figure US20180002256A1-20180104-C01203
    Figure US20180002256A1-20180104-C01204
    3-1-78
    Figure US20180002256A1-20180104-C01205
    Figure US20180002256A1-20180104-C01206
    Figure US20180002256A1-20180104-C01207
    3-1-79
    Figure US20180002256A1-20180104-C01208
    Figure US20180002256A1-20180104-C01209
    Figure US20180002256A1-20180104-C01210
    3-1-80
    Figure US20180002256A1-20180104-C01211
    Figure US20180002256A1-20180104-C01212
    Figure US20180002256A1-20180104-C01213
    3-1-81
    Figure US20180002256A1-20180104-C01214
    Figure US20180002256A1-20180104-C01215
    Figure US20180002256A1-20180104-C01216
    3-1-82
    Figure US20180002256A1-20180104-C01217
    Figure US20180002256A1-20180104-C01218
    Figure US20180002256A1-20180104-C01219
    3-1-83
    Figure US20180002256A1-20180104-C01220
    Figure US20180002256A1-20180104-C01221
    Figure US20180002256A1-20180104-C01222
    3-1-84
    Figure US20180002256A1-20180104-C01223
    Figure US20180002256A1-20180104-C01224
    Figure US20180002256A1-20180104-C01225
    3-1-85
    Figure US20180002256A1-20180104-C01226
    Figure US20180002256A1-20180104-C01227
    Figure US20180002256A1-20180104-C01228
    3-1-86
    Figure US20180002256A1-20180104-C01229
    Figure US20180002256A1-20180104-C01230
    Figure US20180002256A1-20180104-C01231
    3-1-87
    Figure US20180002256A1-20180104-C01232
    Figure US20180002256A1-20180104-C01233
    Figure US20180002256A1-20180104-C01234
    3-1-88
    Figure US20180002256A1-20180104-C01235
    Figure US20180002256A1-20180104-C01236
    Figure US20180002256A1-20180104-C01237
    3-1-89
    Figure US20180002256A1-20180104-C01238
    Figure US20180002256A1-20180104-C01239
    Figure US20180002256A1-20180104-C01240
    3-1-90
    Figure US20180002256A1-20180104-C01241
    Figure US20180002256A1-20180104-C01242
    Figure US20180002256A1-20180104-C01243
    3-1-91
    Figure US20180002256A1-20180104-C01244
    Figure US20180002256A1-20180104-C01245
    Figure US20180002256A1-20180104-C01246
    3-1-92
    Figure US20180002256A1-20180104-C01247
    Figure US20180002256A1-20180104-C01248
    Figure US20180002256A1-20180104-C01249
    3-1-93
    Figure US20180002256A1-20180104-C01250
    Figure US20180002256A1-20180104-C01251
    Figure US20180002256A1-20180104-C01252
    3-1-94
    Figure US20180002256A1-20180104-C01253
    Figure US20180002256A1-20180104-C01254
    Figure US20180002256A1-20180104-C01255
    3-1-95
    Figure US20180002256A1-20180104-C01256
    Figure US20180002256A1-20180104-C01257
    Figure US20180002256A1-20180104-C01258
    3-1-96
    Figure US20180002256A1-20180104-C01259
    Figure US20180002256A1-20180104-C01260
    Figure US20180002256A1-20180104-C01261
    3-1-97
    Figure US20180002256A1-20180104-C01262
    Figure US20180002256A1-20180104-C01263
    Figure US20180002256A1-20180104-C01264
    3-1-98
    Figure US20180002256A1-20180104-C01265
    Figure US20180002256A1-20180104-C01266
    Figure US20180002256A1-20180104-C01267
    3-1-99
    Figure US20180002256A1-20180104-C01268
    Figure US20180002256A1-20180104-C01269
    Figure US20180002256A1-20180104-C01270
    3-1-100
    Figure US20180002256A1-20180104-C01271
    Figure US20180002256A1-20180104-C01272
    Figure US20180002256A1-20180104-C01273
    3-1-101
    Figure US20180002256A1-20180104-C01274
    Figure US20180002256A1-20180104-C01275
    Figure US20180002256A1-20180104-C01276
    3-1-102
    Figure US20180002256A1-20180104-C01277
    Figure US20180002256A1-20180104-C01278
    Figure US20180002256A1-20180104-C01279
    3-1-103
    Figure US20180002256A1-20180104-C01280
    Figure US20180002256A1-20180104-C01281
    Figure US20180002256A1-20180104-C01282
    3-1-104
    Figure US20180002256A1-20180104-C01283
    Figure US20180002256A1-20180104-C01284
    Figure US20180002256A1-20180104-C01285
  • According to one embodiment of the present specification, the double spiro structure compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulae 3-5 to 3-7, and in the following Chemical Formulae 3-5 to 3-7, L2, Ar3 and Ar4 may be selected from Table 2. For example, in the following Chemical Formula 3-5, when L2, Ar3 and Ar4 correspond to 3-1-10 in Table 2, it may be expressed as Compound 3-1-10 (3-5), and when corresponding to 3-1-20, it may be expressed as Compound 3-1-20 (3-5).
  • In addition, in the following Chemical Formula 3-6, when L2, Ar3 and Ar4 correspond to 3-1-10 in Table 2, it may be expressed as Compound 3-1-10 (3-6), and when corresponding to 3-1-20, it may be expressed as Compound 3-1-20 (3-6).
  • Furthermore, in the following Chemical Formula 3-7, when L2, Ar3 and Ar4 correspond to 3-1-10 in Table 2, it may be expressed as Compound 3-1-10 (3-7), and when corresponding to 3-1-20, it may be expressed as Compound 3-1-20 (3-7).
  • Figure US20180002256A1-20180104-C01286
  • According to one embodiment of the present specification, the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-2, and in the following Chemical Formula 3-2, L2, Ar3 and Ar4 are any one selected from among 3-2-1 to 3-2-104 of the following Table 3.
  • Figure US20180002256A1-20180104-C01287
  • TABLE 3
    Figure US20180002256A1-20180104-C01288
    Figure US20180002256A1-20180104-C01289
    Figure US20180002256A1-20180104-C01290
    3-2-1 Direct bond
    Figure US20180002256A1-20180104-C01291
    Figure US20180002256A1-20180104-C01292
    3-2-2 Direct bond
    Figure US20180002256A1-20180104-C01293
    Figure US20180002256A1-20180104-C01294
    3-2-3 Direct bond
    Figure US20180002256A1-20180104-C01295
    Figure US20180002256A1-20180104-C01296
    3-2-4 Direct bond
    Figure US20180002256A1-20180104-C01297
    Figure US20180002256A1-20180104-C01298
    3-2-5 Direct bond
    Figure US20180002256A1-20180104-C01299
    Figure US20180002256A1-20180104-C01300
    3-2-6 Direct bond
    Figure US20180002256A1-20180104-C01301
    Figure US20180002256A1-20180104-C01302
    3-2-7 Direct bond
    Figure US20180002256A1-20180104-C01303
    Figure US20180002256A1-20180104-C01304
    3-2-8 Direct bond
    Figure US20180002256A1-20180104-C01305
    Figure US20180002256A1-20180104-C01306
    3-2-9 Direct bond
    Figure US20180002256A1-20180104-C01307
    Figure US20180002256A1-20180104-C01308
    3-2-10 Direct bond
    Figure US20180002256A1-20180104-C01309
    Figure US20180002256A1-20180104-C01310
    3-2-11 Direct bond
    Figure US20180002256A1-20180104-C01311
    Figure US20180002256A1-20180104-C01312
    3-2-12
    Figure US20180002256A1-20180104-C01313
    Figure US20180002256A1-20180104-C01314
    Figure US20180002256A1-20180104-C01315
    3-2-13
    Figure US20180002256A1-20180104-C01316
    Figure US20180002256A1-20180104-C01317
    Figure US20180002256A1-20180104-C01318
    3-2-14
    Figure US20180002256A1-20180104-C01319
    Figure US20180002256A1-20180104-C01320
    Figure US20180002256A1-20180104-C01321
    3-2-15
    Figure US20180002256A1-20180104-C01322
    Figure US20180002256A1-20180104-C01323
    Figure US20180002256A1-20180104-C01324
    3-2-16
    Figure US20180002256A1-20180104-C01325
    Figure US20180002256A1-20180104-C01326
    Figure US20180002256A1-20180104-C01327
    3-2-17
    Figure US20180002256A1-20180104-C01328
    Figure US20180002256A1-20180104-C01329
    Figure US20180002256A1-20180104-C01330
    3-2-18
    Figure US20180002256A1-20180104-C01331
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    Figure US20180002256A1-20180104-C01573
    3-2-99
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    Figure US20180002256A1-20180104-C01575
    Figure US20180002256A1-20180104-C01576
    3-2-100
    Figure US20180002256A1-20180104-C01577
    Figure US20180002256A1-20180104-C01578
    Figure US20180002256A1-20180104-C01579
    3-2-101
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    Figure US20180002256A1-20180104-C01581
    Figure US20180002256A1-20180104-C01582
    3-2-102
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    Figure US20180002256A1-20180104-C01584
    Figure US20180002256A1-20180104-C01585
    3-2-103
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    Figure US20180002256A1-20180104-C01587
    Figure US20180002256A1-20180104-C01588
    3-2-104
    Figure US20180002256A1-20180104-C01589
    Figure US20180002256A1-20180104-C01590
    Figure US20180002256A1-20180104-C01591
  • According to one embodiment of the present specification, the double spiro structure compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulae 3-8 to 3-10, and in the following Chemical Formulae 3-8 to 3-10, L2, Ar3 and Ar4 may be selected from Table 3. For example, in the following Chemical Formula 3-8, when L2, Ar3 and Ar4 correspond to 3-2-10 in Table 3, t may be expressed as Compound 3-2-10 (3-8), and when corresponding to 3-2-20, it may be expressed as Compound 3-2-20 (3-8).
  • In addition, in the following Chemical Formula 3-9, when L2, Ar3 and Ar4 correspond to 3-2-10 in Table 3, it may be expressed as Compound 3-2-10 (3-9), and when corresponding to 3-2-20, it may be expressed as Compound 3-2-20 (3-9).
  • Furthermore, in the following Chemical Formula 3-10, when L2, Ar3 and Ar4 correspond to 3-2-10 in Table 3, it may be expressed as Compound 3-2-10 (3-10), and when corresponding to 3-2-20, it may be expressed as Compound 3-2-20 (3-10).
  • Figure US20180002256A1-20180104-C01592
  • According to one embodiment of the present specification, the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-3, and in the following Chemical Formula 3-3, L2, Ar3 and Ar4 are any one selected from among 3-3-1 to 3-3-104 of the following Table 4.
  • Figure US20180002256A1-20180104-C01593
  • TABLE 4
    Figure US20180002256A1-20180104-C01594
    Figure US20180002256A1-20180104-C01595
    Figure US20180002256A1-20180104-C01596
    3-3-1 Direct bond
    Figure US20180002256A1-20180104-C01597
    Figure US20180002256A1-20180104-C01598
    3-3-2 Direct bond
    Figure US20180002256A1-20180104-C01599
    Figure US20180002256A1-20180104-C01600
    3-3-3 Direct bond
    Figure US20180002256A1-20180104-C01601
    Figure US20180002256A1-20180104-C01602
    3-3-4 Direct bond
    Figure US20180002256A1-20180104-C01603
    Figure US20180002256A1-20180104-C01604
    3-3-5 Direct bond
    Figure US20180002256A1-20180104-C01605
    Figure US20180002256A1-20180104-C01606
    3-3-6 Direct bond
    Figure US20180002256A1-20180104-C01607
    Figure US20180002256A1-20180104-C01608
    3-3-7 Direct bond
    Figure US20180002256A1-20180104-C01609
    Figure US20180002256A1-20180104-C01610
    3-3-8 Direct bond
    Figure US20180002256A1-20180104-C01611
    Figure US20180002256A1-20180104-C01612
    3-3-9 Direct bond
    Figure US20180002256A1-20180104-C01613
    Figure US20180002256A1-20180104-C01614
    3-3-10 Direct bond
    Figure US20180002256A1-20180104-C01615
    Figure US20180002256A1-20180104-C01616
    3-3-11 Direct bond
    Figure US20180002256A1-20180104-C01617
    Figure US20180002256A1-20180104-C01618
    3-3-12
    Figure US20180002256A1-20180104-C01619
    Figure US20180002256A1-20180104-C01620
    Figure US20180002256A1-20180104-C01621
    3-3-13
    Figure US20180002256A1-20180104-C01622
    Figure US20180002256A1-20180104-C01623
    Figure US20180002256A1-20180104-C01624
    3-3-14
    Figure US20180002256A1-20180104-C01625
    Figure US20180002256A1-20180104-C01626
    Figure US20180002256A1-20180104-C01627
    3-3-15
    Figure US20180002256A1-20180104-C01628
    Figure US20180002256A1-20180104-C01629
    Figure US20180002256A1-20180104-C01630
    3-3-16
    Figure US20180002256A1-20180104-C01631
    Figure US20180002256A1-20180104-C01632
    Figure US20180002256A1-20180104-C01633
    3-3-17
    Figure US20180002256A1-20180104-C01634
    Figure US20180002256A1-20180104-C01635
    Figure US20180002256A1-20180104-C01636
    3-3-18
    Figure US20180002256A1-20180104-C01637
    Figure US20180002256A1-20180104-C01638
    Figure US20180002256A1-20180104-C01639
    3-3-19
    Figure US20180002256A1-20180104-C01640
    Figure US20180002256A1-20180104-C01641
    Figure US20180002256A1-20180104-C01642
    3-3-20
    Figure US20180002256A1-20180104-C01643
    Figure US20180002256A1-20180104-C01644
    Figure US20180002256A1-20180104-C01645
    3-3-21
    Figure US20180002256A1-20180104-C01646
    Figure US20180002256A1-20180104-C01647
    Figure US20180002256A1-20180104-C01648
    3-3-22
    Figure US20180002256A1-20180104-C01649
    Figure US20180002256A1-20180104-C01650
    Figure US20180002256A1-20180104-C01651
    3-3-23
    Figure US20180002256A1-20180104-C01652
    Figure US20180002256A1-20180104-C01653
    Figure US20180002256A1-20180104-C01654
    3-3-24
    Figure US20180002256A1-20180104-C01655
    Figure US20180002256A1-20180104-C01656
    Figure US20180002256A1-20180104-C01657
    3-3-25
    Figure US20180002256A1-20180104-C01658
    Figure US20180002256A1-20180104-C01659
    Figure US20180002256A1-20180104-C01660
    3-3-26
    Figure US20180002256A1-20180104-C01661
    Figure US20180002256A1-20180104-C01662
    Figure US20180002256A1-20180104-C01663
    3-3-27
    Figure US20180002256A1-20180104-C01664
    Figure US20180002256A1-20180104-C01665
    Figure US20180002256A1-20180104-C01666
    3-3-28
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    Figure US20180002256A1-20180104-C01668
    Figure US20180002256A1-20180104-C01669
    3-3-29
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    Figure US20180002256A1-20180104-C01671
    Figure US20180002256A1-20180104-C01672
    3-3-30
    Figure US20180002256A1-20180104-C01673
    Figure US20180002256A1-20180104-C01674
    Figure US20180002256A1-20180104-C01675
    3-3-31
    Figure US20180002256A1-20180104-C01676
    Figure US20180002256A1-20180104-C01677
    Figure US20180002256A1-20180104-C01678
    3-3-32
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    Figure US20180002256A1-20180104-C01680
    Figure US20180002256A1-20180104-C01681
    3-3-33
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    Figure US20180002256A1-20180104-C01683
    Figure US20180002256A1-20180104-C01684
    3-3-34
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    Figure US20180002256A1-20180104-C01686
    Figure US20180002256A1-20180104-C01687
    3-3-35
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    Figure US20180002256A1-20180104-C01689
    Figure US20180002256A1-20180104-C01690
    3-3-36
    Figure US20180002256A1-20180104-C01691
    Figure US20180002256A1-20180104-C01692
    Figure US20180002256A1-20180104-C01693
    3-3-37
    Figure US20180002256A1-20180104-C01694
    Figure US20180002256A1-20180104-C01695
    Figure US20180002256A1-20180104-C01696
    3-3-38
    Figure US20180002256A1-20180104-C01697
    Figure US20180002256A1-20180104-C01698
    Figure US20180002256A1-20180104-C01699
    3-3-39
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    Figure US20180002256A1-20180104-C01701
    Figure US20180002256A1-20180104-C01702
    3-3-40
    Figure US20180002256A1-20180104-C01703
    Figure US20180002256A1-20180104-C01704
    Figure US20180002256A1-20180104-C01705
    3-3-41
    Figure US20180002256A1-20180104-C01706
    Figure US20180002256A1-20180104-C01707
    Figure US20180002256A1-20180104-C01708
    3-3-42
    Figure US20180002256A1-20180104-C01709
    Figure US20180002256A1-20180104-C01710
    Figure US20180002256A1-20180104-C01711
    3-3-43
    Figure US20180002256A1-20180104-C01712
    Figure US20180002256A1-20180104-C01713
    Figure US20180002256A1-20180104-C01714
    3-3-44
    Figure US20180002256A1-20180104-C01715
    Figure US20180002256A1-20180104-C01716
    Figure US20180002256A1-20180104-C01717
    3-3-45
    Figure US20180002256A1-20180104-C01718
    Figure US20180002256A1-20180104-C01719
    Figure US20180002256A1-20180104-C01720
    3-3-46
    Figure US20180002256A1-20180104-C01721
    Figure US20180002256A1-20180104-C01722
    Figure US20180002256A1-20180104-C01723
    3-3-47
    Figure US20180002256A1-20180104-C01724
    Figure US20180002256A1-20180104-C01725
    Figure US20180002256A1-20180104-C01726
    3-3-48
    Figure US20180002256A1-20180104-C01727
    Figure US20180002256A1-20180104-C01728
    Figure US20180002256A1-20180104-C01729
    3-3-49
    Figure US20180002256A1-20180104-C01730
    Figure US20180002256A1-20180104-C01731
    Figure US20180002256A1-20180104-C01732
    3-3-50
    Figure US20180002256A1-20180104-C01733
    Figure US20180002256A1-20180104-C01734
    Figure US20180002256A1-20180104-C01735
    3-3-51
    Figure US20180002256A1-20180104-C01736
    Figure US20180002256A1-20180104-C01737
    Figure US20180002256A1-20180104-C01738
    3-3-52
    Figure US20180002256A1-20180104-C01739
    Figure US20180002256A1-20180104-C01740
    Figure US20180002256A1-20180104-C01741
    3-3-53
    Figure US20180002256A1-20180104-C01742
    Figure US20180002256A1-20180104-C01743
    Figure US20180002256A1-20180104-C01744
    3-3-54
    Figure US20180002256A1-20180104-C01745
    Figure US20180002256A1-20180104-C01746
    Figure US20180002256A1-20180104-C01747
    3-3-55
    Figure US20180002256A1-20180104-C01748
    Figure US20180002256A1-20180104-C01749
    Figure US20180002256A1-20180104-C01750
    3-3-56
    Figure US20180002256A1-20180104-C01751
    Figure US20180002256A1-20180104-C01752
    Figure US20180002256A1-20180104-C01753
    3-3-57
    Figure US20180002256A1-20180104-C01754
    Figure US20180002256A1-20180104-C01755
    Figure US20180002256A1-20180104-C01756
    3-3-58
    Figure US20180002256A1-20180104-C01757
    Figure US20180002256A1-20180104-C01758
    Figure US20180002256A1-20180104-C01759
    3-3-59
    Figure US20180002256A1-20180104-C01760
    Figure US20180002256A1-20180104-C01761
    Figure US20180002256A1-20180104-C01762
    3-3-60
    Figure US20180002256A1-20180104-C01763
    Figure US20180002256A1-20180104-C01764
    Figure US20180002256A1-20180104-C01765
    3-3-61
    Figure US20180002256A1-20180104-C01766
    Figure US20180002256A1-20180104-C01767
    Figure US20180002256A1-20180104-C01768
    3-3-62
    Figure US20180002256A1-20180104-C01769
    Figure US20180002256A1-20180104-C01770
    Figure US20180002256A1-20180104-C01771
    3-3-63
    Figure US20180002256A1-20180104-C01772
    Figure US20180002256A1-20180104-C01773
    Figure US20180002256A1-20180104-C01774
    3-3-64
    Figure US20180002256A1-20180104-C01775
    Figure US20180002256A1-20180104-C01776
    Figure US20180002256A1-20180104-C01777
    3-3-65
    Figure US20180002256A1-20180104-C01778
    Figure US20180002256A1-20180104-C01779
    Figure US20180002256A1-20180104-C01780
    3-3-66
    Figure US20180002256A1-20180104-C01781
    Figure US20180002256A1-20180104-C01782
    Figure US20180002256A1-20180104-C01783
    3-3-67
    Figure US20180002256A1-20180104-C01784
    Figure US20180002256A1-20180104-C01785
    Figure US20180002256A1-20180104-C01786
    3-3-68
    Figure US20180002256A1-20180104-C01787
    Figure US20180002256A1-20180104-C01788
    Figure US20180002256A1-20180104-C01789
    3-3-69
    Figure US20180002256A1-20180104-C01790
    Figure US20180002256A1-20180104-C01791
    Figure US20180002256A1-20180104-C01792
    3-3-70
    Figure US20180002256A1-20180104-C01793
    Figure US20180002256A1-20180104-C01794
    Figure US20180002256A1-20180104-C01795
    3-3-71
    Figure US20180002256A1-20180104-C01796
    Figure US20180002256A1-20180104-C01797
    Figure US20180002256A1-20180104-C01798
    3-3-72
    Figure US20180002256A1-20180104-C01799
    Figure US20180002256A1-20180104-C01800
    Figure US20180002256A1-20180104-C01801
    3-3-73
    Figure US20180002256A1-20180104-C01802
    Figure US20180002256A1-20180104-C01803
    Figure US20180002256A1-20180104-C01804
    3-3-74
    Figure US20180002256A1-20180104-C01805
    Figure US20180002256A1-20180104-C01806
    Figure US20180002256A1-20180104-C01807
    3-3-75
    Figure US20180002256A1-20180104-C01808
    Figure US20180002256A1-20180104-C01809
    Figure US20180002256A1-20180104-C01810
    3-3-76
    Figure US20180002256A1-20180104-C01811
    Figure US20180002256A1-20180104-C01812
    Figure US20180002256A1-20180104-C01813
    3-3-77
    Figure US20180002256A1-20180104-C01814
    Figure US20180002256A1-20180104-C01815
    Figure US20180002256A1-20180104-C01816
    3-3-78
    Figure US20180002256A1-20180104-C01817
    Figure US20180002256A1-20180104-C01818
    Figure US20180002256A1-20180104-C01819
    3-3-79
    Figure US20180002256A1-20180104-C01820
    Figure US20180002256A1-20180104-C01821
    Figure US20180002256A1-20180104-C01822
    3-3-80
    Figure US20180002256A1-20180104-C01823
    Figure US20180002256A1-20180104-C01824
    Figure US20180002256A1-20180104-C01825
    3-3-81
    Figure US20180002256A1-20180104-C01826
    Figure US20180002256A1-20180104-C01827
    Figure US20180002256A1-20180104-C01828
    3-3-82
    Figure US20180002256A1-20180104-C01829
    Figure US20180002256A1-20180104-C01830
    Figure US20180002256A1-20180104-C01831
    3-3-83
    Figure US20180002256A1-20180104-C01832
    Figure US20180002256A1-20180104-C01833
    Figure US20180002256A1-20180104-C01834
    3-3-84
    Figure US20180002256A1-20180104-C01835
    Figure US20180002256A1-20180104-C01836
    Figure US20180002256A1-20180104-C01837
    3-3-85
    Figure US20180002256A1-20180104-C01838
    Figure US20180002256A1-20180104-C01839
    Figure US20180002256A1-20180104-C01840
    3-3-86
    Figure US20180002256A1-20180104-C01841
    Figure US20180002256A1-20180104-C01842
    Figure US20180002256A1-20180104-C01843
    3-3-87
    Figure US20180002256A1-20180104-C01844
    Figure US20180002256A1-20180104-C01845
    Figure US20180002256A1-20180104-C01846
    3-3-88
    Figure US20180002256A1-20180104-C01847
    Figure US20180002256A1-20180104-C01848
    Figure US20180002256A1-20180104-C01849
    3-3-89
    Figure US20180002256A1-20180104-C01850
    Figure US20180002256A1-20180104-C01851
    Figure US20180002256A1-20180104-C01852
    3-3-90
    Figure US20180002256A1-20180104-C01853
    Figure US20180002256A1-20180104-C01854
    Figure US20180002256A1-20180104-C01855
    3-3-91
    Figure US20180002256A1-20180104-C01856
    Figure US20180002256A1-20180104-C01857
    Figure US20180002256A1-20180104-C01858
    3-3-92
    Figure US20180002256A1-20180104-C01859
    Figure US20180002256A1-20180104-C01860
    Figure US20180002256A1-20180104-C01861
    3-3-93
    Figure US20180002256A1-20180104-C01862
    Figure US20180002256A1-20180104-C01863
    Figure US20180002256A1-20180104-C01864
    3-3-94
    Figure US20180002256A1-20180104-C01865
    Figure US20180002256A1-20180104-C01866
    Figure US20180002256A1-20180104-C01867
    3-3-95
    Figure US20180002256A1-20180104-C01868
    Figure US20180002256A1-20180104-C01869
    Figure US20180002256A1-20180104-C01870
    3-3-96
    Figure US20180002256A1-20180104-C01871
    Figure US20180002256A1-20180104-C01872
    Figure US20180002256A1-20180104-C01873
    3-3-97
    Figure US20180002256A1-20180104-C01874
    Figure US20180002256A1-20180104-C01875
    Figure US20180002256A1-20180104-C01876
    3-3-98
    Figure US20180002256A1-20180104-C01877
    Figure US20180002256A1-20180104-C01878
    Figure US20180002256A1-20180104-C01879
    3-3-99
    Figure US20180002256A1-20180104-C01880
    Figure US20180002256A1-20180104-C01881
    Figure US20180002256A1-20180104-C01882
    3-3-100
    Figure US20180002256A1-20180104-C01883
    Figure US20180002256A1-20180104-C01884
    Figure US20180002256A1-20180104-C01885
    3-3-101
    Figure US20180002256A1-20180104-C01886
    Figure US20180002256A1-20180104-C01887
    Figure US20180002256A1-20180104-C01888
    3-2-102
    Figure US20180002256A1-20180104-C01889
    Figure US20180002256A1-20180104-C01890
    Figure US20180002256A1-20180104-C01891
    3-3-103
    Figure US20180002256A1-20180104-C01892
    Figure US20180002256A1-20180104-C01893
    Figure US20180002256A1-20180104-C01894
    3-3-104
    Figure US20180002256A1-20180104-C01895
    Figure US20180002256A1-20180104-C01896
    Figure US20180002256A1-20180104-C01897
  • According to one embodiment of the present specification, the double spiro structure compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulae 3-11 to 3-13, and in the following Chemical Formulae 3-11 to 3-13, L2, Ar3 and Ar4 may be selected from Table 4. For example, in the following Chemical Formula 3-11, L2, when Ar3 and Ar4 correspond to 3-3-10 in Table 4, it may be expressed as Compound 3-3-10 (3-11), and when corresponding to 3-3-20, it may be expressed as Compound 3-3-20 (3-11).
  • In addition, in the following Chemical Formula 3-12, when L2, Ar3 and Ar4 correspond to 3-3-10 in Table 4, it may be expressed as Compound 3-3-10 (3-12), and when corresponding to 3-3-20, it may be expressed as Compound 3-3-20 (3-12).
  • Furthermore, in the following Chemical Formula 3-13, when L2, Ar3 and Ar4 correspond to 3-3-10 in Table 4, it may be expressed as Compound 3-3-10 (3-13), and when corresponding to 3-3-20, it may be expressed as Compound 3-3-20 (3-13).
  • Figure US20180002256A1-20180104-C01898
  • According to one embodiment of the present specification, the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-4, and in the following Chemical Formula 3-4, L2, Ar3 and Ar4 are any one selected from among 3-4-1 to 3-4-104 of the following Table 5.
  • Figure US20180002256A1-20180104-C01899
  • TABLE 5
    Figure US20180002256A1-20180104-C01900
    Figure US20180002256A1-20180104-C01901
    Figure US20180002256A1-20180104-C01902
    3-4-1 Direct bond
    Figure US20180002256A1-20180104-C01903
    Figure US20180002256A1-20180104-C01904
    3-4-2 Direct bond
    Figure US20180002256A1-20180104-C01905
    Figure US20180002256A1-20180104-C01906
    3-4-3 Direct bond
    Figure US20180002256A1-20180104-C01907
    Figure US20180002256A1-20180104-C01908
    3-4-4 Direct bond
    Figure US20180002256A1-20180104-C01909
    Figure US20180002256A1-20180104-C01910
    3-4-5 Direct bond
    Figure US20180002256A1-20180104-C01911
    Figure US20180002256A1-20180104-C01912
    3-4-6 Direct bond
    Figure US20180002256A1-20180104-C01913
    Figure US20180002256A1-20180104-C01914
    3-4-7 Direct bond
    Figure US20180002256A1-20180104-C01915
    Figure US20180002256A1-20180104-C01916
    3-4-8 Direct bond
    Figure US20180002256A1-20180104-C01917
    Figure US20180002256A1-20180104-C01918
    3-4-9 Direct bond
    Figure US20180002256A1-20180104-C01919
    Figure US20180002256A1-20180104-C01920
    3-4-10 Direct bond
    Figure US20180002256A1-20180104-C01921
    Figure US20180002256A1-20180104-C01922
    3-4-11 Direct bond
    Figure US20180002256A1-20180104-C01923
    Figure US20180002256A1-20180104-C01924
    3-4-12
    Figure US20180002256A1-20180104-C01925
    Figure US20180002256A1-20180104-C01926
    Figure US20180002256A1-20180104-C01927
    3-4-13
    Figure US20180002256A1-20180104-C01928
    Figure US20180002256A1-20180104-C01929
    Figure US20180002256A1-20180104-C01930
    3-4-14
    Figure US20180002256A1-20180104-C01931
    Figure US20180002256A1-20180104-C01932
    Figure US20180002256A1-20180104-C01933
    3-4-15
    Figure US20180002256A1-20180104-C01934
    Figure US20180002256A1-20180104-C01935
    Figure US20180002256A1-20180104-C01936
    3-4-16
    Figure US20180002256A1-20180104-C01937
    Figure US20180002256A1-20180104-C01938
    Figure US20180002256A1-20180104-C01939
    3-4-17
    Figure US20180002256A1-20180104-C01940
    Figure US20180002256A1-20180104-C01941
    Figure US20180002256A1-20180104-C01942
    3-4-18
    Figure US20180002256A1-20180104-C01943
    Figure US20180002256A1-20180104-C01944
    Figure US20180002256A1-20180104-C01945
    3-4-19
    Figure US20180002256A1-20180104-C01946
    Figure US20180002256A1-20180104-C01947
    Figure US20180002256A1-20180104-C01948
    3-4-20
    Figure US20180002256A1-20180104-C01949
    Figure US20180002256A1-20180104-C01950
    Figure US20180002256A1-20180104-C01951
    3-4-21
    Figure US20180002256A1-20180104-C01952
    Figure US20180002256A1-20180104-C01953
    Figure US20180002256A1-20180104-C01954
    3-4-22
    Figure US20180002256A1-20180104-C01955
    Figure US20180002256A1-20180104-C01956
    Figure US20180002256A1-20180104-C01957
    3-4-23
    Figure US20180002256A1-20180104-C01958
    Figure US20180002256A1-20180104-C01959
    Figure US20180002256A1-20180104-C01960
    3-4-24
    Figure US20180002256A1-20180104-C01961
    Figure US20180002256A1-20180104-C01962
    Figure US20180002256A1-20180104-C01963
    3-4-25
    Figure US20180002256A1-20180104-C01964
    Figure US20180002256A1-20180104-C01965
    Figure US20180002256A1-20180104-C01966
    3-4-26
    Figure US20180002256A1-20180104-C01967
    Figure US20180002256A1-20180104-C01968
    Figure US20180002256A1-20180104-C01969
    3-4-27
    Figure US20180002256A1-20180104-C01970
    Figure US20180002256A1-20180104-C01971
    Figure US20180002256A1-20180104-C01972
    3-4-28
    Figure US20180002256A1-20180104-C01973
    Figure US20180002256A1-20180104-C01974
    Figure US20180002256A1-20180104-C01975
    3-4-29
    Figure US20180002256A1-20180104-C01976
    Figure US20180002256A1-20180104-C01977
    Figure US20180002256A1-20180104-C01978
    3-4-30
    Figure US20180002256A1-20180104-C01979
    Figure US20180002256A1-20180104-C01980
    Figure US20180002256A1-20180104-C01981
    3-4-31
    Figure US20180002256A1-20180104-C01982
    Figure US20180002256A1-20180104-C01983
    Figure US20180002256A1-20180104-C01984
    3-4-32
    Figure US20180002256A1-20180104-C01985
    Figure US20180002256A1-20180104-C01986
    Figure US20180002256A1-20180104-C01987
    3-4-33
    Figure US20180002256A1-20180104-C01988
    Figure US20180002256A1-20180104-C01989
    Figure US20180002256A1-20180104-C01990
    3-4-34
    Figure US20180002256A1-20180104-C01991
    Figure US20180002256A1-20180104-C01992
    Figure US20180002256A1-20180104-C01993
    3-4-35
    Figure US20180002256A1-20180104-C01994
    Figure US20180002256A1-20180104-C01995
    Figure US20180002256A1-20180104-C01996
    3-4-36
    Figure US20180002256A1-20180104-C01997
    Figure US20180002256A1-20180104-C01998
    Figure US20180002256A1-20180104-C01999
    3-4-37
    Figure US20180002256A1-20180104-C02000
    Figure US20180002256A1-20180104-C02001
    Figure US20180002256A1-20180104-C02002
    3-4-38
    Figure US20180002256A1-20180104-C02003
    Figure US20180002256A1-20180104-C02004
    Figure US20180002256A1-20180104-C02005
    3-4-39
    Figure US20180002256A1-20180104-C02006
    Figure US20180002256A1-20180104-C02007
    Figure US20180002256A1-20180104-C02008
    3-4-40
    Figure US20180002256A1-20180104-C02009
    Figure US20180002256A1-20180104-C02010
    Figure US20180002256A1-20180104-C02011
    3-4-41
    Figure US20180002256A1-20180104-C02012
    Figure US20180002256A1-20180104-C02013
    Figure US20180002256A1-20180104-C02014
    3-4-42
    Figure US20180002256A1-20180104-C02015
    Figure US20180002256A1-20180104-C02016
    Figure US20180002256A1-20180104-C02017
    3-4-43
    Figure US20180002256A1-20180104-C02018
    Figure US20180002256A1-20180104-C02019
    Figure US20180002256A1-20180104-C02020
    3-4-44
    Figure US20180002256A1-20180104-C02021
    Figure US20180002256A1-20180104-C02022
    Figure US20180002256A1-20180104-C02023
    3-4-45
    Figure US20180002256A1-20180104-C02024
    Figure US20180002256A1-20180104-C02025
    Figure US20180002256A1-20180104-C02026
    3-4-46
    Figure US20180002256A1-20180104-C02027
    Figure US20180002256A1-20180104-C02028
    Figure US20180002256A1-20180104-C02029
    3-4-47
    Figure US20180002256A1-20180104-C02030
    Figure US20180002256A1-20180104-C02031
    Figure US20180002256A1-20180104-C02032
    3-4-48
    Figure US20180002256A1-20180104-C02033
    Figure US20180002256A1-20180104-C02034
    Figure US20180002256A1-20180104-C02035
    3-4-49
    Figure US20180002256A1-20180104-C02036
    Figure US20180002256A1-20180104-C02037
    Figure US20180002256A1-20180104-C02038
    3-4-50
    Figure US20180002256A1-20180104-C02039
    Figure US20180002256A1-20180104-C02040
    Figure US20180002256A1-20180104-C02041
    3-4-51
    Figure US20180002256A1-20180104-C02042
    Figure US20180002256A1-20180104-C02043
    Figure US20180002256A1-20180104-C02044
    3-4-52
    Figure US20180002256A1-20180104-C02045
    Figure US20180002256A1-20180104-C02046
    Figure US20180002256A1-20180104-C02047
    3-4-53
    Figure US20180002256A1-20180104-C02048
    Figure US20180002256A1-20180104-C02049
    Figure US20180002256A1-20180104-C02050
    3-4-54
    Figure US20180002256A1-20180104-C02051
    Figure US20180002256A1-20180104-C02052
    Figure US20180002256A1-20180104-C02053
    3-4-55
    Figure US20180002256A1-20180104-C02054
    Figure US20180002256A1-20180104-C02055
    Figure US20180002256A1-20180104-C02056
    3-4-56
    Figure US20180002256A1-20180104-C02057
    Figure US20180002256A1-20180104-C02058
    Figure US20180002256A1-20180104-C02059
    3-4-57
    Figure US20180002256A1-20180104-C02060
    Figure US20180002256A1-20180104-C02061
    Figure US20180002256A1-20180104-C02062
    3-4-58
    Figure US20180002256A1-20180104-C02063
    Figure US20180002256A1-20180104-C02064
    Figure US20180002256A1-20180104-C02065
    3-4-59
    Figure US20180002256A1-20180104-C02066
    Figure US20180002256A1-20180104-C02067
    Figure US20180002256A1-20180104-C02068
    3-4-60
    Figure US20180002256A1-20180104-C02069
    Figure US20180002256A1-20180104-C02070
    Figure US20180002256A1-20180104-C02071
    3-4-61
    Figure US20180002256A1-20180104-C02072
    Figure US20180002256A1-20180104-C02073
    Figure US20180002256A1-20180104-C02074
    3-4-62
    Figure US20180002256A1-20180104-C02075
    Figure US20180002256A1-20180104-C02076
    Figure US20180002256A1-20180104-C02077
    3-4-63
    Figure US20180002256A1-20180104-C02078
    Figure US20180002256A1-20180104-C02079
    Figure US20180002256A1-20180104-C02080
    3-4-64
    Figure US20180002256A1-20180104-C02081
    Figure US20180002256A1-20180104-C02082
    Figure US20180002256A1-20180104-C02083
    3-4-65
    Figure US20180002256A1-20180104-C02084
    Figure US20180002256A1-20180104-C02085
    Figure US20180002256A1-20180104-C02086
    3-4-66
    Figure US20180002256A1-20180104-C02087
    Figure US20180002256A1-20180104-C02088
    Figure US20180002256A1-20180104-C02089
    3-4-67
    Figure US20180002256A1-20180104-C02090
    Figure US20180002256A1-20180104-C02091
    Figure US20180002256A1-20180104-C02092
    3-4-68
    Figure US20180002256A1-20180104-C02093
    Figure US20180002256A1-20180104-C02094
    Figure US20180002256A1-20180104-C02095
    3-4-69
    Figure US20180002256A1-20180104-C02096
    Figure US20180002256A1-20180104-C02097
    Figure US20180002256A1-20180104-C02098
    3-4-70
    Figure US20180002256A1-20180104-C02099
    Figure US20180002256A1-20180104-C02100
    Figure US20180002256A1-20180104-C02101
    3-4-71
    Figure US20180002256A1-20180104-C02102
    Figure US20180002256A1-20180104-C02103
    Figure US20180002256A1-20180104-C02104
    3-4-72
    Figure US20180002256A1-20180104-C02105
    Figure US20180002256A1-20180104-C02106
    Figure US20180002256A1-20180104-C02107
    3-4-73
    Figure US20180002256A1-20180104-C02108
    Figure US20180002256A1-20180104-C02109
    Figure US20180002256A1-20180104-C02110
    3-4-74
    Figure US20180002256A1-20180104-C02111
    Figure US20180002256A1-20180104-C02112
    Figure US20180002256A1-20180104-C02113
    3-4-75
    Figure US20180002256A1-20180104-C02114
    Figure US20180002256A1-20180104-C02115
    Figure US20180002256A1-20180104-C02116
    3-4-76
    Figure US20180002256A1-20180104-C02117
    Figure US20180002256A1-20180104-C02118
    Figure US20180002256A1-20180104-C02119
    3-4-77
    Figure US20180002256A1-20180104-C02120
    Figure US20180002256A1-20180104-C02121
    Figure US20180002256A1-20180104-C02122
    3-4-78
    Figure US20180002256A1-20180104-C02123
    Figure US20180002256A1-20180104-C02124
    Figure US20180002256A1-20180104-C02125
    3-4-79
    Figure US20180002256A1-20180104-C02126
    Figure US20180002256A1-20180104-C02127
    Figure US20180002256A1-20180104-C02128
    3-4-80
    Figure US20180002256A1-20180104-C02129
    Figure US20180002256A1-20180104-C02130
    Figure US20180002256A1-20180104-C02131
    3-4-81
    Figure US20180002256A1-20180104-C02132
    Figure US20180002256A1-20180104-C02133
    Figure US20180002256A1-20180104-C02134
    3-4-82
    Figure US20180002256A1-20180104-C02135
    Figure US20180002256A1-20180104-C02136
    Figure US20180002256A1-20180104-C02137
    3-4-83
    Figure US20180002256A1-20180104-C02138
    Figure US20180002256A1-20180104-C02139
    Figure US20180002256A1-20180104-C02140
    3-4-84
    Figure US20180002256A1-20180104-C02141
    Figure US20180002256A1-20180104-C02142
    Figure US20180002256A1-20180104-C02143
    3-4-85
    Figure US20180002256A1-20180104-C02144
    Figure US20180002256A1-20180104-C02145
    Figure US20180002256A1-20180104-C02146
    3-4-86
    Figure US20180002256A1-20180104-C02147
    Figure US20180002256A1-20180104-C02148
    Figure US20180002256A1-20180104-C02149
    3-4-87
    Figure US20180002256A1-20180104-C02150
    Figure US20180002256A1-20180104-C02151
    Figure US20180002256A1-20180104-C02152
    3-4-88
    Figure US20180002256A1-20180104-C02153
    Figure US20180002256A1-20180104-C02154
    Figure US20180002256A1-20180104-C02155
    3-4-89
    Figure US20180002256A1-20180104-C02156
    Figure US20180002256A1-20180104-C02157
    Figure US20180002256A1-20180104-C02158
    3-4-90
    Figure US20180002256A1-20180104-C02159
    Figure US20180002256A1-20180104-C02160
    Figure US20180002256A1-20180104-C02161
    3-4-91
    Figure US20180002256A1-20180104-C02162
    Figure US20180002256A1-20180104-C02163
    Figure US20180002256A1-20180104-C02164
    3-4-92
    Figure US20180002256A1-20180104-C02165
    Figure US20180002256A1-20180104-C02166
    Figure US20180002256A1-20180104-C02167
    3-4-93
    Figure US20180002256A1-20180104-C02168
    Figure US20180002256A1-20180104-C02169
    Figure US20180002256A1-20180104-C02170
    3-4-94
    Figure US20180002256A1-20180104-C02171
    Figure US20180002256A1-20180104-C02172
    Figure US20180002256A1-20180104-C02173
    3-4-95
    Figure US20180002256A1-20180104-C02174
    Figure US20180002256A1-20180104-C02175
    Figure US20180002256A1-20180104-C02176
    3-4-96
    Figure US20180002256A1-20180104-C02177
    Figure US20180002256A1-20180104-C02178
    Figure US20180002256A1-20180104-C02179
    3-4-97
    Figure US20180002256A1-20180104-C02180
    Figure US20180002256A1-20180104-C02181
    Figure US20180002256A1-20180104-C02182
    3-4-98
    Figure US20180002256A1-20180104-C02183
    Figure US20180002256A1-20180104-C02184
    Figure US20180002256A1-20180104-C02185
    3-4-99
    Figure US20180002256A1-20180104-C02186
    Figure US20180002256A1-20180104-C02187
    Figure US20180002256A1-20180104-C02188
    3-4-100
    Figure US20180002256A1-20180104-C02189
    Figure US20180002256A1-20180104-C02190
    Figure US20180002256A1-20180104-C02191
    3-4-101
    Figure US20180002256A1-20180104-C02192
    Figure US20180002256A1-20180104-C02193
    Figure US20180002256A1-20180104-C02194
    3-4-102
    Figure US20180002256A1-20180104-C02195
    Figure US20180002256A1-20180104-C02196
    Figure US20180002256A1-20180104-C02197
    3-4-103
    Figure US20180002256A1-20180104-C02198
    Figure US20180002256A1-20180104-C02199
    Figure US20180002256A1-20180104-C02200
    3-4-104
    Figure US20180002256A1-20180104-C02201
    Figure US20180002256A1-20180104-C02202
    Figure US20180002256A1-20180104-C02203
  • According to one embodiment of the present specification, the double spiro structure compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulae 3-14 to 3-16, and in the following Chemical Formulae 3-14 to 3-16, L2, Ar3 and Ar4 may be selected from Table 5. For example, in the following Chemical Formula 3-14, when L2, Ar3 and Ar4 correspond to 3-4-10 in Table 5, it may be expressed as Compound 3-4-10 (3-14), and when corresponding to 3-4-20, it may be expressed as Compound 3-4-20 (3-14).
  • In addition, in the following Chemical Formula 3-15, when L2, Ar3 and Ar4 correspond to 3-4-10 in Table 5, it may be expressed as Compound 3-4-10 (3-15), and when corresponding to 3-4-20, it may be expressed as Compound 3-4-20 (3-15).
  • Furthermore, in the following Chemical Formula 3-16, when L2, Ar3 and Ar4 correspond to 3-4-10 in Table 5, it may be expressed as Compound 3-4-10 (3-16), and when corresponding to 3-4-20, it may be expressed as Compound 3-4-20 (3-16).
  • Figure US20180002256A1-20180104-C02204
  • According to one embodiment of the present specification, the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 4-4, and in the following Chemical Formula 4-4, L3 and X4 are any one selected from among 4-4-1 to 4-4-22 of the following Table 6.
  • Figure US20180002256A1-20180104-C02205
  • TABLE 6
    X4
    Figure US20180002256A1-20180104-C02206
    4-4-1 O
    Figure US20180002256A1-20180104-C02207
    4-4-2 S
    Figure US20180002256A1-20180104-C02208
    X4
    Figure US20180002256A1-20180104-C02209
    Figure US20180002256A1-20180104-C02210
    4-4-3 NAr5
    Figure US20180002256A1-20180104-C02211
    Figure US20180002256A1-20180104-C02212
    4-4-4 NAr5
    Figure US20180002256A1-20180104-C02213
    Figure US20180002256A1-20180104-C02214
    4-4-5 NAr5
    Figure US20180002256A1-20180104-C02215
    Figure US20180002256A1-20180104-C02216
    4-4-6 NAr5
    Figure US20180002256A1-20180104-C02217
    Figure US20180002256A1-20180104-C02218
    4-4-7 NAr5
    Figure US20180002256A1-20180104-C02219
    Figure US20180002256A1-20180104-C02220
    4-4-8 NAr5
    Figure US20180002256A1-20180104-C02221
    Figure US20180002256A1-20180104-C02222
    4-4-9 NAr5
    Figure US20180002256A1-20180104-C02223
    Figure US20180002256A1-20180104-C02224
    4-4-10 NAr5
    Figure US20180002256A1-20180104-C02225
    Figure US20180002256A1-20180104-C02226
    4-4-11 NAr5
    Figure US20180002256A1-20180104-C02227
    Figure US20180002256A1-20180104-C02228
    4-4-12 NAr5
    Figure US20180002256A1-20180104-C02229
    Figure US20180002256A1-20180104-C02230
    4-4-13 NAr5
    Figure US20180002256A1-20180104-C02231
    Figure US20180002256A1-20180104-C02232
    4-4-14 NAr5
    Figure US20180002256A1-20180104-C02233
    Figure US20180002256A1-20180104-C02234
    4-4-15 NAr5
    Figure US20180002256A1-20180104-C02235
    Figure US20180002256A1-20180104-C02236
    4-4-16 NAr5
    Figure US20180002256A1-20180104-C02237
    Figure US20180002256A1-20180104-C02238
    4-4-17 NAr5
    Figure US20180002256A1-20180104-C02239
    Figure US20180002256A1-20180104-C02240
    4-4-18 NAr5
    Figure US20180002256A1-20180104-C02241
    Figure US20180002256A1-20180104-C02242
    4-4-19 NAr5
    Figure US20180002256A1-20180104-C02243
    Figure US20180002256A1-20180104-C02244
    4-4-20 NAr5
    Figure US20180002256A1-20180104-C02245
    Figure US20180002256A1-20180104-C02246
    4-4-21 NAr5
    Figure US20180002256A1-20180104-C02247
    Figure US20180002256A1-20180104-C02248
    4-4-22 NAr5
    Figure US20180002256A1-20180104-C02249
    Figure US20180002256A1-20180104-C02250
  • According to one embodiment of the present specification, the double spiro structure compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulae 4-5 to 4-7, and in the following Chemical Formulae 4-5 to 4-7, L3 and X4 may be selected from Table 6. For example, in the following Chemical Formula 4-5, when L3 and X4 correspond to 4-4-10 in Table 6, it may be expressed as Compound 4-4-10 (4-5), and when corresponding to 4-4-20, it may be expressed as Compound 4-4-20 (4-5).
  • In addition, in the following Chemical Formula 4-6, when L3 and X4 correspond to 4-4-10 in Table 6, it may be expressed as Compound 4-4-10 (4-6), and when corresponding to 4-4-20, it may be expressed as Compound 4-4-20 (4-6).
  • Furthermore, in the following Chemical Formula 4-7, when L3 and X4 correspond to 4-4-10 in Table 6, it may be expressed as Compound 4-4-10 (4-7), and when corresponding to 4-4-20, it may be expressed as Compound 4-4-20 (4-7).
  • Figure US20180002256A1-20180104-C02251
  • One embodiment of the present specification provides an organic light emitting device comprising an anode; a cathode provided opposite to the anode; and a light emitting layer and one or more organic material layers provided between the anode and the cathode, wherein the light emitting layer or one or more layers of the organic material layers comprise the double spiro structure compound represented by Chemical Formula 1.
  • The organic material layer of the organic light emitting device of the present specification may be formed in a single layer structure, but may be formed in a multilayer structure in which two or more organic material layers are laminated. For example, the organic light emitting device of the present invention may have a structure comprising a hole injection layer, a hole transfer layer, an electron blocking layer, a hole blocking layer, an electron transfer layer, an electron injection layer and the like as the organic material layer. However, the structure of the organic light emitting device is not limited thereto, and may comprise less numbers of organic material layers.
  • For example, the structure of the organic light emitting device of the present invention may be as shown in FIG. 1 and FIG. 2, but is not limited thereto.
  • FIG. 1 illustrates a structure of an organic light emitting device (10) in which an anode (30), a light emitting layer (40) and a cathode (50) are consecutively laminated on a substrate (20). FIG. 1 is an illustrative structure of the organic light emitting device according to one embodiment of the present specification, and other organic material layers may be further included therein.
  • FIG. 2 illustrates a structure of an organic light emitting device in which an anode (30), a hole injection layer (60), a hole transfer layer (70), a light emitting layer (40), an electron transfer layer (80), an electron injection layer (90) and a cathode (50) are consecutively laminated on a substrate (20). FIG. 2 is an illustrative structure of the organic light emitting device according to one embodiment of the present specification, and other organic material layers may be further included therein.
  • According to one embodiment of the present specification, the organic material layer comprises a hole injection layer or a hole transfer layer, and the hole injection layer or the hole transfer layer comprises the double spiro structure compound represented by Chemical Formula 1.
  • According to another embodiment of the present specification, the organic material layer comprises an electron blocking layer, and the electron blocking layer comprises the double spiro structure compound represented by Chemical Formula 1.
  • According to another embodiment of the present specification, the light emitting layer comprises the double spiro structure compound represented by Chemical Formula 1.
  • According to one embodiment of the present specification, the organic material layer comprises an electron transfer layer or an electron injection layer, wherein the electron transfer layer or the electron injection layer comprises the double spiro structure compound represented by Chemical Formula 1.
  • According to one embodiment of the present specification, the organic material layer comprises an electron transfer layer, an electron injection layer, or a layer carrying out electron transfer and electron injection at the same time, and the electron transfer layer, the electron injection layer, or the layer carrying out electron transfer and electron injection at the same time comprises the double spiro structure compound represented by Chemical Formula 1.
  • According to one embodiment of the present specification, the organic light emitting device comprises one or more organic material layers provided between the anode and the light emitting layer, wherein the organic material layer comprises a double spiro structure compound represented by the following Chemical Formula 2.
  • Figure US20180002256A1-20180104-C02252
  • In Chemical Formula 2,
  • L1 is a direct bond; a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, and
  • Ar1 and Ar2 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • According to one embodiment of the present specification, the double spiro structure compound represented by Chemical Formula 2 may be represented by any one of Chemical Formulae 2-1 to 2-3 described above.
  • According to one embodiment of the present specification, the organic light emitting device comprises one or more organic material layers provided between the cathode and the light emitting layer, and the light emitting layer and one or more layers of the organic material layers comprise a double spiro structure compound represented by the following Chemical Formula 3.
  • Figure US20180002256A1-20180104-C02253
  • In Chemical Formula 3,
  • X1 to X3 are the same as or different from each other, and each independently CH or N,
  • at least one of X1 to X3 is N,
  • L2 is a direct bond; a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or multicyclic heteroarylene group having 2 to 30 carbon atoms, and
  • Ar3 and Ar4 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • According to one embodiment of the present specification, the double spiro structure compound represented by Chemical Formula 3 may be represented by any one of Chemical Formulae 3-1 to 3-9 described above.
  • According to one embodiment of the present specification, the organic light emitting device comprises one or more organic material layers provided between the cathode and the light emitting layer, wherein the organic material layer comprises a double spiro structure compound represented by the following Chemical Formula 4.
  • Figure US20180002256A1-20180104-C02254
  • In Chemical Formula 4,
  • X4 is O, S or NAr5,
  • L3 is a direct bond; a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or multicyclic heteroarylene group having 2 to 30 carbon atoms,
  • Ar5 is selected from the group consisting of hydrogen; a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and
  • Cy1 is a substituted or unsubstituted monocyclic or multicyclic hydrocarbon ring having 3 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or multicyclic heteroring having 2 to 30 carbon atoms.
  • According to one embodiment of the present specification, the double spiro structure compound represented by Chemical Formula 4 may be represented by any one of Chemical Formulae 4-1 to 4-3 described above.
  • The organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that one or more layers of organic material layers comprise the double spiro structure compound of the present specification, that is, the double spiro structure compound represented by Chemical Formula 1.
  • When the organic light emitting device comprises a plurality of organic material layers, the organic material layers may be formed with the same material or with different materials.
  • For example, the organic light emitting device of the present specification may be manufactured by consecutively laminating an anode, an organic material layer and a cathode on a substrate. Herein, the organic light emitting device may be manufactured by forming the anode on the substrate by depositing a metal, a metal oxide having conductivity, or alloys thereof using a physical vapor deposition (PVD) method such as a sputtering method or an e-beam evaporation method, forming the organic material layer comprising a hole injection layer, a hole transfer layer, a light emitting layer and an electron transfer layer thereon, then depositing a material capable of being used as the cathode thereon. In addition to such a method, the organic light emitting device may be manufactured by consecutively depositing a cathode material, an organic material layer, and an anode material. Furthermore, when manufacturing the organic light emitting device, the double Spiro structure compound represented by Chemical Formula 1 may be formed as the organic material layer using a solution coating method as well as a vacuum deposition method. Herein, the solution coating method means spin coating, dip coating, doctor blading, ink jet printing, screen printing, a spray method, roll coating and the like, but is not limited thereto.
  • As the anode material, a material having large work function is normally preferable so that hole injection to the organic material layer is smooth. Specific examples of the anode material capable of being used in the present invention include metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylen-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • As the cathode material, a material having small work function is normally preferable so that electron injection to the organic material layer is smooth. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials such as LiF/Al, LiO2/Al or Mg/Ag, and the like, but are not limited thereto.
  • The hole injection layer is a layer that injects holes from an electrode, and the hole injection material is preferably a compound that has an ability to transfer holes, therefore, has a hole injection effect in an anode, has an excellent hole injection effect for a light emitting layer or a light emitting material, prevents excitons generated in the light emitting layer from moving to an electron injection layer or an electron injection material, and in addition, has an excellent thin film forming ability. The highest occupied molecular orbital (HOMO) of the hole injection material is preferably in between the work function of an anode material and the HOMO of surrounding organic material layers. Specific examples of the hole injection material include a metal porphyrin, oligothiophene, an arylamine-based organic material, a hexanitrile hexazatriphenylene-based organic material, a quinacridone-based organic material, a perylene-based organic material, anthraquinone, and a polyaniline- and a polythiophene-based conductive polymer, and the like, but are not limited thereto.
  • The hole transfer layer is a layer that receives holes from a hole injection layer and transfers the holes to a light emitting layer, and as the hole transfer material, a material capable of receiving holes from an anode or a hole injection layer, moving the holes to a light emitting layer, and having high mobility for the holes, is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, a block copolymer having conjugated parts and non-conjugated parts together, and the like, but are not limited thereto.
  • A light emitting material of the light emitting layer is a material capable of emitting light in a visible light region by receiving holes and electrons from a hole transfer layer and an electron transfer layer, respectively, and binding the holes and the electrons, and is preferably a material having favorable quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include a 8-hydroxy-quinoline aluminum complex (Alq3); a carbazole-based compound; a dimerized styryl compound; BAlq; a 10-hydroxybenzo quinoline-metal compound; a benzoxazole-, a benzthiazole- and a benzimidazole-based compound; a poly(p-phenylenevinylene) (PPV)-based polymer; a spiro compound; polyfluorene, rubrene, and the like, but are not limited thereto.
  • The light emitting layer may comprise a host material and a dopant material. The host material includes a fused aromatic ring derivative, a heteroring-containing compound or the like. Specifically, the fused aromatic ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound and the like, and the heteroring-containing compound includes a carbazole derivative, a dibenzofuran derivative, a ladder-type furan compound, a pyrimidine derivative and the like, but the material is not limited thereto.
  • The dopant material includes an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, a metal complex and the like. Specifically, the aromatic amine derivative is a fused aromatic ring derivative having a substituted or unsubstituted arylamino group and includes arylamino group-including pyrene, anthracene, crycene, peryflanthene and the like, and the styrylamine compound is a compound in which substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, and one, two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetramine or the like is included, but the styrylamine compound is not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex or the like, but is not limited thereto.
  • The electron transfer layer is a layer that receives electrons from an electron injection layer and transfers the electrons to a light emitting layer, and as the electron transfer material, a material capable of favorably receiving electrons from a cathode, moving the electrons to a light emitting layer, and having high mobility for the electrons, is suitable. Specific examples thereof include an Al complex of 8-hydroxyquinoline; a complex including Alq3; an organic radical compound; a hydroxyflavon-metal complex and the like, but are not limited thereto. The electron transfer layer may be used together with any desired cathode material as used according to existing technologies. Particularly, examples of the suitable cathode material include common materials that have small work function, and in which an aluminum layer or a silver layer follows. Specifically, the cathode material includes cesium, barium, calcium, ytterbium and samarium, and in each case, an aluminum layer or a silver layer follows.
  • The electron injection layer is a layer that injects electrons from an electrode, and the electron injection material is preferably a compound that has an ability to transfer electrons, has an electron injection effect from a cathode, has an excellent electron injection effect for a light emitting layer or a light emitting material, prevents excitons generated in the light emitting layer from moving to a hole injection layer, and in addition, has an excellent thin film forming ability. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone or the like, and derivatives thereof, a metal complex compound, a nitrogen-containing 5-membered ring derivative, and the like, but are not limited thereto.
  • The metal complex compound includes 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)berylium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium and the like, but is not limited thereto.
  • The organic light emitting device according to the present specification may be a top-emission type, a bottom-emission type or a dual-emission type depending on the materials used.
  • According to one embodiment of the present specification, the double spiro structure compound represented by Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.
  • Hereinafter, the present specification will be specifically described with reference to synthesis examples, preparation examples and examples. However, synthesis examples, preparation examples and examples according to the present specification may be modified to various other forms, and the scope of the present specification is not interpreted to be limited to synthesis examples, preparation examples and examples described below. The synthesis examples, the preparation examples and the examples of the present specification are provided in order to more completely describe the present specification to those having average knowledge in the art.
  • The double spiro structure compound represented by Chemical Formula 1 according to the present specification may be prepared through a multi-step chemical reaction. The preparation of the compounds is described by the following synthesis examples and preparation examples.
  • The double spiro structure compound represented by Chemical Formula 1 may be prepared to compounds corresponding to Chemical Formula 2, Chemical Formula 3 and Chemical Formula 4 using methods and orders as in the following Reaction Formula 1-1, Reaction Formula 1-2 and Reaction Formula 1-3, respectively, and although not limited to such reactions, reaction formulae are simply described in order to illuminate the present invention.
    • Synthesis Example
  • <Reaction Formula 1-1>
  • Preparation of Chemical Formula 2
  • Figure US20180002256A1-20180104-C02255
  • <Reaction Formula 1-2>
  • Preparation of Chemical Formula 3
  • Figure US20180002256A1-20180104-C02256
  • After completely dissolving Compound 1-A (19.5 g, 0.55 mol) in 200 ml of tetrahydrofuran in a 500 ml round bottom flask under nitrogen atmosphere, the temperature was lowered to −78° C., then 34 ml of n-BuLi was added thereto, the result was stirred for 30 minutes, and 10H-spiro[anthracene-9,9′-fluoren]-10-one (16.78 g, 0.55 mol) was slowly added thereto. The temperature was raised to room temperature after 3 hours had passed, and 200 ml of water was added thereto to terminate the reaction. The water layer was removed, and the result was dried with anhydrous magnesium sulfate, vacuum concentrated and recrystallized with 300 ml of ethanol to prepare Compound 1-B (28.65 g, yield: 88%).
  • MS[M+H]+=666
  • Preparation of the Following Compound 2-1-1 (2-1)
  • Figure US20180002256A1-20180104-C02257
  • <Reaction Formula 1-3>
  • Preparation of Chemical Formula 4
  • Figure US20180002256A1-20180104-C02258
  • In Reaction Formulae 1-1 to 1-3, compounds represented by Chemical Formulae 2 to 4 may be diversely prepared through varying L1 to L3, Ar1 to Ar4, Cy1, and X1 to X4.
    • Preparation Example 1-1
  • Preparation of Compound 1-A
  • Figure US20180002256A1-20180104-C02259
  • After completely dissolving 1-bromo-2-iodobenzene (15 g, 0.53 mol) and (4-(diphenylamino)phenyl)boronic acid (18.37 g, 0.64 mol) in 240 ml of tetrahydrofuran in a 500 ml round bottom flask under nitrogen atmosphere, a 2 M aqueous potassium carbonate solution (120 ml) and then tetrakis-(triphenylphosphine)palladium (1.22 g, 1.06 mmol) were added thereto, and then the result was heated and stirred for 2 hours. After lowering the temperature to room temperature, the water layer was removed, and the result was dried with anhydrous magnesium sulfate, vacuum concentrated, and then recrystallized with 300 ml of ethanol to prepare Compound 1-A (19.52 g, yield: 92%).
  • MS[M+H]+=401
  • Preparation of Compound 1-B
  • Figure US20180002256A1-20180104-C02260
  • After adding Compound 1-B (28.65 g, 0.43 mol) to 200 ml of acetic acid in a 500 ml round bottom flask under nitrogen atmosphere, 0.6 ml of HCl was slowly added thereto, and the result was heated and stirred for 2 hours. The temperature was lowered to room temperature, and the precipitated solid was filtered and washed with water. The filter cake was collected and dissolved in 1 L of chloroform. Water was added thereto and the water layer was separated. The result was recrystallized with 300 ml of ethanol to prepare Compound 2-1-1 (2-1) (25.78 g, yield: 89%).
  • MS[M+H]+=648
    • Preparation Example 1-2
  • Preparation of Compound 2-1-6 (2-1)
  • Figure US20180002256A1-20180104-C02261
  • Compound 2-1-6 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that phenylfluoreneaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=764
    • Preparation Example 1-3
  • Preparation of Compound 2-1-7 (2-1)
  • Figure US20180002256A1-20180104-C02262
  • Compound 2-1-7 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that biphenylfluoreneaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=841
    • Preparation Example 1-4
  • Preparation of Compound 2-1-10 (2-1)
  • Figure US20180002256A1-20180104-C02263
  • Compound 2-1-10 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that 1,1′-biphenylphenylaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=724
    • Preparation Example 1-5
  • Preparation of Compound 2-1-15 (2-1)
  • Figure US20180002256A1-20180104-C02264
  • Compound 2-1-15 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that bisbiphenylaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=801
    • Preparation Example 1-6
  • Preparation of Compound 2-1-20 (2-1)
  • Figure US20180002256A1-20180104-C02265
  • Compound 2-1-20 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that terphenylphenylaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=801
    • Preparation Example 1-7
  • Preparation of Compound 2-1-25 (2-1)
  • Figure US20180002256A1-20180104-C02266
  • Compound 2-1-25 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that orthobiphenylphenylaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=801
    • Preparation Example 1-8
  • Preparation of Compound 2-1-26 (2-1)
  • Figure US20180002256A1-20180104-C02267
  • Compound 2-1-26 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that orthobiphenylfluoreneaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=841
    • Preparation Example 1-9
  • Preparation of Compound 2-1-40 (2-1)
  • Figure US20180002256A1-20180104-C02268
  • Compound 2-1-40 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that 2-dibenzothiophenephenylaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=754
    • Preparation Example 1-10
  • Preparation of Compound 2-1-41 (2-1)
  • Figure US20180002256A1-20180104-C02269
  • Compound 2-1-41 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that 2-dibenzothiophenebiphenylaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=831
    • Preparation Example 1-11
  • Preparation of Compound 2-1-42 (2-1)
  • Figure US20180002256A1-20180104-C02270
  • Compound 2-1-42 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that 2-dibenzothiophenefluoreneaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=871
    • Preparation Example 1-12
  • Preparation of Compound 2-1-46 (2-1)
  • Figure US20180002256A1-20180104-C02271
  • Compound 2-1-46 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that 2-dibenzofuranphenylaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=738
    • Preparation Example 1-13
  • Preparation of Compound 2-1-47 (2-1)
  • Figure US20180002256A1-20180104-C02272
  • Compound 2-1-47 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that 2-dibenzofuranbiphenylaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=815
    • Preparation Example 1-14
  • Preparation of Compound 2-1-48 (2-1)
  • Figure US20180002256A1-20180104-C02273
  • Compound 2-1-48 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that 2-dibenzofuranfluoreneaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=855
    • Preparation Example 1-15
  • Preparation of Compound 2-1-52 (2-1)
  • Figure US20180002256A1-20180104-C02274
  • Compound 2-1-52 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that N-(4-(9H-carbazol-9-yl)phenyl)-9,9′-dimethyl-9H-fluoren-2-aminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=930
    • Preparation Example 1-16
  • Preparation of Compound 2-1-54 (2-1)
  • Figure US20180002256A1-20180104-C02275
  • Compound 2-1-54 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that N-(9,9′-dimethyl-9H-fluoren-2-yl)-9-phenyl-9H-carbazol-3-1-Amino)phenyl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=930
    • Preparation Example 1-17
  • Preparation of Compound 2-1-64 (2-1)
  • Figure US20180002256A1-20180104-C02276
  • Compound 2-1-64 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-(diphenylamino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=724
    • Preparation Example 1-18
  • Preparation of Compound 2-1-65 (2-1)
  • Figure US20180002256A1-20180104-C02277
  • Compound 2-1-65 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-([1,1′-biphenyl]-4-yl(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=801
    • Preparation Example 1-19
  • Preparation of Compound 2-1-66 (2-1)
  • Figure US20180002256A1-20180104-C02278
  • Compound 2-1-66 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-([1,1′:4′,1″-terphenyl]-4-yl(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=877
    • Preparation Example 1-20
  • Preparation of Compound 2-1-67 (2-1)
  • Figure US20180002256A1-20180104-C02279
  • Compound 2-1-67 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-(di([1,1′-biphenyl]-4-yl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=877
    • Preparation Example 1-21
  • Preparation of Compound 2-1-69 (2-1)
  • Figure US20180002256A1-20180104-C02280
  • Compound 2-1-69 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-([1,1′-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=917
    • Preparation Example 1-22
  • Preparation of Compound 2-1-75 (2-1)
  • Figure US20180002256A1-20180104-C02281
  • Compound 2-1-75 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-([1,1′-biphenyl]-2-yl([1,1′-biphenyl]-4-yl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=877
    • Preparation Example 1-23
  • Preparation of Compound 2-1-77 (2-1)
  • Figure US20180002256A1-20180104-C02282
  • Compound 2-1-77 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-((9,9-dimethyl-9H-fluoren-2-yl)(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=841
    • Preparation Example 1-24
  • Preparation of Compound 2-1-81 (2-1)
  • Figure US20180002256A1-20180104-C02283
  • Compound 2-1-81 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-([1,1′-biphenyl]-2-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=917
    • Preparation Example 1-25
  • Preparation of Compound 2-1-241 (2-1)
  • Figure US20180002256A1-20180104-C02284
  • Compound 2-1-241 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-(dibenzo[b,d]thiophen-2-yl(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=831
    • Preparation Example 1-26
  • Preparation of Compound 2-1-242 (2-1)
  • Figure US20180002256A1-20180104-C02285
  • Compound 2-1-242 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-(dibenzo[b,d]thiophen-4-yl(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=831
    • Preparation Example 1-27
  • Preparation of Compound 2-1-246 (2-1)
  • Figure US20180002256A1-20180104-C02286
  • Compound 2-1-246 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-(dibenzo[b,d]furan-4-yl(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=815
    • Preparation Example 1-28
  • Preparation of Compound 2-1-315 (2-1)
  • Figure US20180002256A1-20180104-C02287
  • Compound 2-1-315 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-((4′-(diphenylamino)-[1,1′-biphenyl]-4-yl)(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=968
    • Preparation Example 1-29
  • Preparation of Compound 2-1-316 (2-1)
  • Figure US20180002256A1-20180104-C02288
  • Compound 2-1-316 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-((4-(diphenylamino)phenyl)(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=892
    • Preparation Example 1-30
  • Preparation of Compound 2-1-311 (2-1)
  • Figure US20180002256A1-20180104-C02289
  • Compound 2-1-311 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-((4-([1,1′-biphenyl]-4-yl(phenyl)amino)phenyl)(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=968
    • Preparation Example 1-31
  • Preparation of Compound 2-1-318 (2-1)
  • Figure US20180002256A1-20180104-C02290
  • Compound 2-1-318 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-((4-(di([1,1′-biphenyl]-4-yl)amino)phenyl)(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=1044
    • Preparation Example 1-32
  • Preparation of Compound 2-1-320 (2-1)
  • Figure US20180002256A1-20180104-C02291
  • Compound 2-1-320 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-((4-([1,1′-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)phenyl)(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=1084
    • Preparation Example 2-1-1
  • Preparation of Compound 2-A
  • Figure US20180002256A1-20180104-C02292
  • After completely dissolving 1-bromo-2-iodobenzene (15 g, 0.53 mol) and (4-(4,6-diphenylpyridin-2-yl)phenyl)boronic acid (19.35 g, 0.64 mol) in 240 ml of tetrahydrofuran in a 500 ml round bottom flask under nitrogen atmosphere, a 2 M aqueous potassium carbonate solution (120 ml) and then tetrakis-(triphenylphosphine)palladium (1.22 g, 1.06 mmol) were added thereto, and then the result was heated and stirred for 2 hours. After lowering the temperature to room temperature, the water layer was removed, and the result was dried with anhydrous magnesium sulfate, vacuum concentrated, and then recrystallized with 300 ml of ethanol to prepare Compound 2-A (18.41 g, yield: 88%).
  • MS[M+H]+=463
  • Preparation of Compound 2-B
  • Figure US20180002256A1-20180104-C02293
  • After completely dissolving Compound 2-A (18.41 g, 0.55 mol) in 200 ml of tetrahydrofuran in a 500 ml round bottom flask under nitrogen atmosphere, the temperature was lowered to −78° C., then 34 ml of n-BuLi was added thereto, the result was stirred for 30 minutes, and 10H-spiro[anthracene-9,9′-fluoren]-10-one (16.78 g, 0.55 mol) was slowly added thereto. The temperature was raised to room temperature after 3 hours had passed, and 200 ml of water was added thereto to terminate the reaction. The water layer was removed, and the result was dried with anhydrous magnesium sulfate, vacuum concentrated and recrystallized with 300 ml of ethanol to prepare Compound 2-B (26.65 g, yield: 85%).
  • MS[M+H]+=728
  • Preparation of Compound 3-1-1 (3-5)
  • Figure US20180002256A1-20180104-C02294
  • After adding Compound 2-B (28.65 g, 0.43 mol) to 200 ml of acetic acid in a 500 ml round bottom flask under nitrogen atmosphere, 0.7 ml of HCl was slowly added thereto, and the result was heated and stirred for 2 hours. The temperature was lowered to room temperature, and the precipitated solid was filtered and washed with water. The filter cake was collected and dissolved in 1 L of chloroform. Water was added thereto and the water layer was separated. The result was recrystallized with 300 ml of ethanol to prepare Compound 3-1-1 (3-5) (23.12 g, yield: 84%).
  • MS[M+H]+=710
    • Preparation Example 2-1-2
  • Preparation of Compound 3-1-2 (3-5)
  • Figure US20180002256A1-20180104-C02295
  • Compound 3-1-2 (3-5) was prepared in the same manner as in Preparation Example 2-1-1 preparing Compound 3-1-1 (3-5) except that (4-(4-([1,1′-biphenyl]-4-yl)-6-phenylpyridin-2-yl)phenyl)boronic acid was used instead of (4-(4,6-diphenylpyridin-2-yl)phenyl)boronic acid.
  • MS[M+H]+=786
    • Preparation Example 2-1-3
  • Preparation of Compound 3-1-6 (3-5)
  • Figure US20180002256A1-20180104-C02296
  • Compound 3-1-6 (3-5) was prepared in the same manner as in Preparation Example 2-1-1 preparing Compound 3-1-1 (3-5) except that (4-4-(9,9-dimethyl-9H-fluoren-2-yl)-6-phenylpyridin-2-yl)phenyl)boronic acid was used instead of (4-(4, 6-diphenylpyridin-2-yl)phenyl)boronic acid.
  • MS[M+H]+=827
    • Preparation Example 2-1-4
  • Preparation of Compound 3-1-9 (3-5)
  • Figure US20180002256A1-20180104-C02297
  • Compound 3-1-9 (3-5) was prepared in the same manner as in Preparation Example 2-1-1 preparing Compound 3-1-1 (3-5) except that (4-(4,6-di([1,1′-biphenyl]-4-yl)pyridin-2-yl)phenyl)boronic acid was used instead of (4-(4,6-diphenylpyridin-2-yl)phenyl)boronic acid.
  • MS[M+H]+=863
    • Preparation Example 2-1-5
  • Preparation of Compound 3-1-15 (3-5)
  • Figure US20180002256A1-20180104-C02298
  • Compound 3-1-15 (3-5) was prepared in the same manner as in Preparation Example 2-1-1 preparing Compound 3-1-1 (3-5) except that (4′-(4,6-diphenylpyridin-2-yl)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(4,6-diphenylpyridin-2-yl)phenyl)boronic acid.
  • MS[M+H]+=786
    • Preparation Example 2-1-6
  • Preparation of Compound 3-1-16 (3-5)
  • Figure US20180002256A1-20180104-C02299
  • Compound 3-1-16 (3-5) was prepared in the same manner as in Preparation Example 2-1-1 preparing Compound 3-1-1 (3-5) except that (4′-(6-([1,1′-biphenyl]-4-yl)-4-phenylpyridin-2-yl)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(4,6-diphenylpyridin-2-yl)phenyl)boronic acid.
    • Preparation Example 2-1-7
  • Preparation of Compound 3-1-18 (3-5)
  • Figure US20180002256A1-20180104-C02300
  • Compound 3-1-18 (3-5) was prepared in the same manner as in Preparation Example 2-1-1 preparing Compound 3-1-1 (3-5) except that (4′-(4,6-di([1,1′-biphenyl]-4-yl)pyridin-2-yl)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(4,6-diphenylpyridin-2-yl)phenyl)boronic acid.
  • MS[M+H]+=939
    • Preparation Example 2-1-8
  • Preparation of Compound 3-1-20 (3-5)
  • Figure US20180002256A1-20180104-C02301
  • Compound 3-1-20 (3-5) was prepared in the same manner as in Preparation Example 2-1-1 preparing Compound 3-1-1 (3-5) except that (4′-(6-([1,1′-biphenyl]-4-yl)-4-(9,9-dimethyl-9H-fluoren-2-yl)pyridin-2-yl)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(4,6-diphenylpyridin-2-yl)phenyl)boronic acid.
  • MS[M+H]+=979
    • Preparation Examples 2-2-1 to 2-2-8
  • The following Compounds 3-2-1 (3-8), 3-2-2 (3-8), 3-2-6 (3-8), 3-2-9 (3-8), 3-2-15 (3-8), 3-2-16 (3-8), 3-2-18 (3-8) and 3-2-20 (3-8) were prepared in the same manner as in Preparation Example 2-1-1 except that 4-(4,6-diphenylpyrimidin-2-yl)phenylboronic acid, (4-(4-([1,1′-biphenyl]-4-yl)-6-phenylpyrimidin-2-yl)phenyl)boronic acid, (4-(4-(9,9-dimethyl-9H-fluoren-2-yl)-6-phenylpyrimidin-2-yl)phenyl)boronic acid, (4-(4,6-di([1,1′-biphenyl]-4-yl)pyrimidin-2-yl)phenyl)boronic acid, (4′-(4,6-diphenylpyrimidin-2-yl)-[1,1′-biphenyl]-4-acid, (4′-(6-([1,1′-biphenyl]-4-yl)-4-phenylpyrimidin-2-yl)-[1,1′-biphenyl]-4-yl)boronic acid, (4′-(4,6-di([1,1′-biphenyl]-4-yl)pyrimidin-2-yl)-[1,1′-biphenyl]-4-yl)boronic acid, or (4′-(6-([1,1′-biphenyl]-4-yl)-4-(9,9-dimethyl-9H-fluoren-2-yl)pyrimidin-2-yl)-[1,1′-biphenyl]-4-yl)boronic acid were used instead of (4-(4,6-diphenylpyridin-2-yl)phenyl)boronic acid.
  • Figure US20180002256A1-20180104-C02302
    Figure US20180002256A1-20180104-C02303
    Figure US20180002256A1-20180104-C02304
    • Preparation Examples 2-3-1 to 2-3-8
  • The following Compounds 3-3-1 (3-11), 3-3-2 (3-11), 3-3-6 (3-11), 3-3-9 (3-11), 3-3-15 (3-11), 3-3-16 (3-11), 3-3-18 (3-11) and 3-3-20 (3-11) were prepared in the same manner as in Preparation Example 2-1-1 except that 4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenylboronic acid, (4-(4-([1,1′-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)boronic acid, (4-(4-(9,9-dimethyl-9H-fluoren-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)boronic acid, (4-(4,6-di([1,1′-biphenyl]-4-yl)-1,3,5-triazin-2-yl)phenyl)boronic acid, (4′-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1′-biphenyl]-4-yl)boronic acid, (4′-(6-([1,1′-biphenyl]-4-yl)-4-phenyl-1,3,5-triazin-2-yl)-[1,1′-biphenyl]-4-yl)boronic acid, (4′-(4,6-di([1,1′-biphenyl]-4-yl)-1,3,5-triazin-2-yl)-[1,1′-biphenyl]-4-yl)boronic acid, or (4′-(6-([1,1′-biphenyl]-4-yl)-4-(9,9-dimethyl-9H-fluoren-2-yl)-1,3,5-triazin-2-yl)-[1,1′-biphenyl]-4-yl)boronic acid were used instead of (4-(4,6-diphenylpyridin-2-yl)phenyl)boronic acid.
  • Figure US20180002256A1-20180104-C02305
    Figure US20180002256A1-20180104-C02306
    Figure US20180002256A1-20180104-C02307
    • Preparation Examples 2-4-1 to 2-4-8
  • The following Compounds 3-4-1 (3-14), 3-4-2 (3-14), 3-4-6 (3-14), 3-4-9 (3-14), 3-4-15 (3-14), 3-4-16 (3-14), 3-4-18 (3-14) and 3-4-20 (3-14) were prepared in the same manner as in Preparation Example 2-1-1 except that 4-(2,6-diphenylpyrimidin-4-yl)phenylboronic acid, (4-(2-([1,1′-biphenyl]-4-yl)-6-phenylpyrimidin-2-yl)phenyl)boronic acid, (4-(2-(9,9-dimethyl-9H-fluoren-2-yl)-6-phenylpyrimidin-2-yl)phenyl)boronic acid, (4-(2,6-di([1,1′-biphenyl]-4-yl)pyrimidin-2-yl)phenyl)boronic acid, (4′-(2,6-diphenylpyrimidin-2-yl)-[1,1′-biphenyl]-4-yl)boronic acid, (4′-(6-([1,1′-biphenyl]-4-yl)-2-phenylpyrimidin-2-yl)-[1,1′-biphenyl]-4-yl)boronic acid, (4′-(2,6-di([1,1′-biphenyl]-4-yl)pyrimidin-2-yl)-[1,1′-biphenyl]-4-yl)boronic acid, or (4′-(6-([1,1′-biphenyl]-4-yl)-2-(9,9-dimethyl-9H-fluoren-2-yl)pyrimidin-2-yl)-[1,1′-biphenyl]-4-yl)boronic acid were used instead of (4-(4,6-diphenylpyridin-2-yl)phenyl)boronic acid.
  • Figure US20180002256A1-20180104-C02308
    Figure US20180002256A1-20180104-C02309
    Figure US20180002256A1-20180104-C02310
    • Preparation Example 3-1
  • Preparation of Compound 4-4-1 (4-5)
  • Figure US20180002256A1-20180104-C02311
  • Compound 4-4-1 (4-5) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that 4′-(benzo[d]oxazol-2-yl)biphenyl-4-ylboronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=674
    • Preparation Example 3-2
  • Preparation of Compound 4-4-2 (4-5)
  • Figure US20180002256A1-20180104-C02312
  • Compound 4-4-2 (4-5) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that 4′-(benzo[d]thiazol-2-yl)biphenyl-4-ylboronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • MS[M+H]+=690
    • Comparative Example 1
  • A glass substrate on which indium tin oxide (ITO) was coated as a thin film to a thickness of 1,000 Å was placed in detergent-dissolved distilled water and ultrasonic cleaned. Herein, a product of Fischer Co. was used as the detergent, and as the distilled water, distilled water filtered twice with a filter manufactured by Millipore Co. was used. After the ITO was cleaned for 30 minutes, ultrasonic cleaning was repeated twice using distilled water for 10 minutes. After the cleaning with distilled water was finished, the substrate was ultrasonic cleaned with solvents of isopropyl alcohol, acetone and methanol, then dried, and then transferred to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using oxygen plasma, and then transferred to a vacuum depositor.
  • On the transparent ITO electrode prepared as above, a hole injection layer was formed by thermal vacuum depositing hexanitrile hexaazatriphenylene (HAT) of the following chemical formula to a thickness of 500 Å.
  • Figure US20180002256A1-20180104-C02313
  • A hole transfer layer was formed on the hole injection layer by vacuum depositing the following compound 4-4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) (300 Å), a material transferring holes.
  • Figure US20180002256A1-20180104-C02314
  • Subsequently, an electron blocking layer was formed on the hole transfer layer to a film thickness of 100 Å by vacuum depositing the following compound N-([1,1′-bisphenyl]-4-yl)-N-(4-(11-([1,1′-biphenyl]-4-yl)-11H-benzo[a]carbazol-5-yl)phenyl)-[1,1′-biphenyl]-4-amine (EB1)(100 Å).
  • Figure US20180002256A1-20180104-C02315
  • Next, a light emitting layer was formed on the electron blocking layer to a film thickness of 300 Å by vacuum depositing BH and BD shown below in a weight ratio of 25:1.
  • Figure US20180002256A1-20180104-C02316
  • An electron injection and transfer layer was formed on the light emitting layer to a thickness of 300 Å by vacuum depositing the compound ET1 and the compound lithium quinolate (LiQ) in a weight ratio of 1:1. A cathode was formed on the electron injection and transfer layer by depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 2,000 Å in consecutive order.
  • An organic light emitting device was manufactured by maintaining, in the above-mentioned processes, the deposition rates of the organic materials at 0.4 Å/sec to 0.7 Å/sec, the deposition rates of the lithium fluoride and the aluminum of the cathode at 0.3 Å/sec and 2 Å/sec, respectively, and the degree of vacuum during the deposition at 2×10−7 torr to 5×10−6 torr.
    • Example 1-1
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-1 (2-1) was used instead of EB1.
    • Example 1-2
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-6 (2-1) was used instead of EB1.
    • Example 1-3
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-7 (2-1) was used instead of Compound EB1.
    • Example 1-4
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-10 (2-1) was used instead of Compound EB1.
    • Example 1-5
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-15 (2-1) was used instead of Compound EB1.
    • Example 1-6
  • same manner as in Comparative Example 1 except that Compound 2-1-20 (2-1) was used instead of Compound EB1.
    • Example 1-7
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-25 (2-1) was used instead of Compound EB1.
    • Example 1-8
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-26 (2-1) was used instead of EB1.
    • Example 1-9
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-40 (2-1) was used instead of Compound EB1.
    • Example 1-10
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-41 (2-1) was used instead of Compound EB1.
    • Example 1-11
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-42 (2-1) was used instead of Compound EB1.
    • Example 1-12
  • same manner as in Comparative Example 1 except that Compound 2-1-46 (2-1) was used instead of Compound EB1.
    • Example 1-13
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-47 (2-1) was used instead of Compound EB1.
    • Example 1-14
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-48 (2-1) was used instead of Compound EB1.
    • Example 1-15
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-52 (2-1) was used instead of Compound EB1.
    • Example 1-16
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-54 (2-1) was used instead of Compound EB1.
    • Example 1-17
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-64 (2-1) was used instead of Compound EB1.
    • Example 1-18
  • same manner as in Comparative Example 1 except that Compound 2-1-65 (2-1) was used instead of Compound EB1.
    • Example 1-19
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-66 (2-1) was used instead of Compound EB1.
    • Example 1-20
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-67 (2-1) was used instead of Compound EB1.
    • Example 1-21
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-69 (2-1) was used instead of Compound EB1.
    • Example 1-22
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-75 (2-1) was used instead of Compound EB1.
    • Example 1-23
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-77 (2-1) was used instead of Compound EB1.
    • Example 1-24
  • same manner as in Comparative Example 1 except that Compound 2-1-81 (2-1) was used instead of Compound EB1.
    • Example 1-25
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-241 (2-1) was used instead of Compound EB1.
    • Example 1-26
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-242 (2-1) was used instead of Compound EB1.
    • Example 1-27
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-246 (2-1) was used instead of Compound EB1.
    • Example 1-28
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-315 (2-1) was used instead of Compound EB1.
    • Example 1-29
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-316 (2-1) was used instead of Compound EB1.
    • Example 1-30
  • same manner as in Comparative Example 1 except that Compound 2-1-311 (2-1) was used instead of Compound EB1.
    • Example 1-31
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-318 (2-1) was used instead of Compound EB1.
    • Example 1-32
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-320 (2-1) was used instead of Compound EB1.
    • Comparative Example 1-1
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that a compound of the following HT1 was used instead of Compound EB1.
  • Figure US20180002256A1-20180104-C02317
    • Comparative Example 1-2
  • same manner as in Comparative Example 1 except that a compound of the following HT2 was used instead of Compound EB1.
  • Figure US20180002256A1-20180104-C02318
    • Comparative Example 1-3
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that a compound of the following HT3 was used instead of Compound EB1.
  • Figure US20180002256A1-20180104-C02319
    • Comparative Example 1-4
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that a compound of the following HT4 was used instead of Compound EB1.
  • Figure US20180002256A1-20180104-C02320
  • When a current was applied to the organic light emitting devices manufactured in Comparative Example 1, Examples 1-1 to 1-32 and Comparative Examples 1-1 to 1-4, results of Table 7 were obtained.
  • TABLE 7
    Compound
    (Electron Voltage Efficiency Color
    Blocking (V@10 (cd/A@10 Coordinate
    Layer) mA/cm2) mA/cm2) (x, y)
    Comparative EB1 4.11 5.33 (0.138,
    Example 1 0.127)
    Example 1-1 Compound 3.94 5.35 (0.139,
    2-1-1 (2-1) 0.122)
    Example 1-2 Compound 3.86 5.36 (0.138,
    2-1-6 (2-1) 0.126)
    Example 1-3 Compound 3.85 5.51 (0.138,
    2-1-7 (2-1) 0.127)
    Example 1-4 Compound 4.03 5.42 (0.137,
    2-1-10 (2-1) 0.125)
    Example 1-5 Compound 3.83 5.56 (0.136,
    2-1-15 (2-1) 0.125)
    Example 1-6 Compound 4.03 5.54 (0.136,
    2-1-20 (2-1) 0.127)
    Example 1-7 Compound 3.94 5.35 (0.136,
    2-1-25 (2-1) 0.125)
    Example 1-8 Compound 3.86 5.36 (0.137,
    2-1-26 (2-1) 0.125)
    Example 1-9 Compound 3.85 5.51 (0.138,
    2-1-40 (2-1) 0.125)
    Example 1-10 Compound 4.00 5.42 (0.136,
    2-1-41 (2-1) 0.125)
    Example 1-11 Compound 3.84 5.46 (0.137,
    2-1-42 (2-1) 0.125)
    Example 1-12 Compound 3.88 5.42 (0.136,
    2-1-46 (2-1) 0.125)
    Example 1-13 Compound 3.89 5.36 (0.138,
    2-1-47 (2-1) 0.126)
    Example 1-14 Compound 3.81 5.34 (0.137,
    2-1-48 (2-1) 0.125)
    Example 1-15 Compound 3.80 5.50 (0.136,
    2-1-52 (2-1) 0.127)
    Example 1-16 Compound 4.01 5.42 (0.135,
    2-1-54 (2-1) 0.127)
    Example 1-17 Compound 3.84 5.52 (0.138,
    2-1-64 (2-1) 0.127)
    Example 1-18 Compound 4.05 5.58 (0.137,
    2-1-65 (2-1) 0.125)
    Example 1-19 Compound 3.85 5.51 (0.138,
    2-1-66 (2-1) 0.127)
    Example 1-20 Compound 4.03 5.42 (0.137,
    2-1-67 (2-1) 0.125)
    Example 1-21 Compound 3.83 5.56 (0.136,
    2-1-69 (2-1) 0.125)
    Example 1-22 Compound 4.03 5.54 (0.136,
    2-1-75 (2-1) 0.127)
    Example 1-23 Compound 3.94 5.35 (0.136,
    2-1-77 (2-1) 0.125)
    Example 1-24 Compound 3.86 5.36 (0.137,
    2-1-81 (2-1) 0.125)
    Example 1-25 Compound 3.85 5.51 (0.138,
    2-1-241 (2-1) 0.125)
    Example 1-26 Compound 4.00 5.42 (0.136,
    2-1-242 (2-1) 0.125)
    Example 1-27 Compound 3.84 5.46 (0.137,
    2-1-246 (2-1) 0.125)
    Example 1-28 Compound 3.85 5.51 (0.138,
    2-1-315 (2-1) 0.125)
    Example 1-29 Compound 4.03 5.42 (0.137,
    2-1-316 (2-1) 0.125)
    Example 1-30 Compound 3.83 5.56 (0.136,
    2-1-311 (2-1) 0.125)
    Example 1-31 Compound 4.03 5.54 (0.136,
    2-1-318 (2-1) 0.127)
    Example 1-32 Compound 3.94 5.35 (0.136,
    2-1-320 (2-1) 0.125)
    Comparative HT1 4.53 4.68 (0.136,
    Example 1-1 0.127)
    Comparative HT2 4.63 4.82 (0.136,
    Example 1-2 0.127)
    Comparative HT3 4.35 4.85 (0.135,
    Example 1-3 0.125)
    Comparative HT4 4.37 4.89 (0.135,
    Example 1-4 0.130)
  • In Table 7, the devices of Examples 1-1 to 1-32 using compounds having the double spiro structure compound represented by Chemical Formula 2 as the core had a lower driving voltage and enhanced efficiency compared to the devices of Comparative Example 1-1 to 1-4, and the device of Comparative Example 1 using a material of Compound EB1 as an electron blocking layer.
  • When comparing the devices of Examples 1-1 to 1-32 and Comparative Examples 1-1 to 1-4, it was seen that the devices of Examples 1-1 to 1-32 had more superior properties compared to the structure in which the core of the double spiro structure compound represented by Chemical Formula 2 was substituted with two arylamine (Comparative Example 1-1 and Comparative Example 1-2) and the structure in which arylamine was linked to the spiro structure compound (Comparative Example 1-3 and Comparative Example 1-4). It was also seen that a lifespan property of the device was enhanced when a phenyl group was linked as the linking group.
  • As shown in the results of Table 7, it can be seen that amine linking various substituents (dibenzofuran, dibenzothiophene, carbazole derivatives and the like) to the core of the double spiro structure compound represented by Chemical Formula 2 of the present specification is suitable to be used as an electron blocking layer in an organic light emitting device by finely adjusting a LUMO level in the molecule.
  • Accordingly, it was identified that the double spiro structure compound according to the present specification had an excellent electron blocking ability and was capable of being used in an electron blocking layer of an organic light emitting device.
    • Examples 2-1 to 2-32
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that the compounds of Examples 1-1 to 32 were used instead of NPB as the hole transfer layer.
  • TABLE 8
    Compound Voltage Efficiency Color
    (Hole Transfer (V@10 (cd/A@10 Coordinate
    Layer) mA/cm2) mA/cm2) (x, y)
    Comparative NPB 4.31 5.53 (0.138,
    Example 1 0.127)
    Example 2-1 Compound 3.84 5.85 (0.139,
    2-1-1 (2-1) 0.122)
    Example 2-2 Compound 3.76 5.96 (0.138,
    2-1-6 (2-1) 0.126)
    Example 2-3 Compound 3.75 5.81 (0.138,
    2-1-7 (2-1) 0.127)
    Example 2-4 Compound 3.86 5.72 (0.137,
    2-1-10 (2-1) 0.125)
    Example 2-5 Compound 3.73 5.86 (0.136,
    2-1-15 (2-1) 0.125)
    Example 2-6 Compound 3.83 5.94 (0.136,
    2-1-20 (2-1) 0.127)
    Example 2-7 Compound 3.74 5.95 (0.136,
    2-1-25 (2-1) 0.125)
    Example 2-8 Compound 3.76 5.84 (0.137,
    2-1-26 (2-1) 0.125)
    Example 2-9 Compound 3.75 5.81 (0.138,
    2-1-40 (2-1) 0.125)
    Example 2-10 Compound 3.80 5.82 (0.136,
    2-1-41 (2-1) 0.125)
    Example 2-11 Compound 3.74 5.96 (0.137,
    2-1-42 (2-1) 0.125)
    Example 2-12 Compound 3.78 5.82 (0.136,
    2-1-46 (2-1) 0.125)
    Example 2-13 Compound 3.79 5.76 (0.138,
    2-1-47 (2-1) 0.126)
    Example 2-14 Compound 3.71 5.94 (0.137,
    2-1-48 (2-1) 0.125)
    Example 2-15 Compound 3.80 5.80 (0.136,
    2-1-52 (2-1) 0.127)
    Example 2-16 Compound 3.73 5.82 (0.135,
    2-1-54 (2-1) 0.127)
    Example 2-17 Compound 3.83 5.82 (0.138,
    2-1-64 (2-1) 0.127)
    Example 2-18 Compound 3.74 5.88 (0.137,
    2-1-65 (2-1) 0.125)
    Example 2-19 Compound 3.76 5.81 (0.138,
    2-1-66 (2-1) 0.127)
    Example 2-20 Compound 3.75 5.82 (0.137,
    2-1-67 (2-1) 0.125)
    Example 2-21 Compound 3.80 5.76 (0.136,
    2-1-69 (2-1) 0.125)
    Example 2-22 Compound 3.74 5.84 (0.136,
    2-1-75 (2-1) 0.127)
    Example 2-23 Compound 3.78 5.35 (0.136,
    2-1-77 (2-1) 0.125)
    Example 2-24 Compound 3.86 5.36 (0.137,
    2-1-81 (2-1) 0.125)
    Example 2-25 Compound 3.73 5.82 (0.138,
    2-1-241 (2-1) 0.125)
    Example 2-26 Compound 3.83 5.96 (0.136,
    2-1-242 (2-1) 0.125)
    Example 2-27 Compound 3.74 5.82 (0.137,
    2-1-246 (2-1) 0.125)
    Example 2-28 Compound 3.76 5.86 (0.138,
    2-1-315 (2-1) 0.125)
    Example 2-29 Compound 3.75 5.94 (0.137,
    2-1-316 (2-1) 0.125)
    Example 2-30 Compound 3.80 5.80 (0.136,
    2-1-311 (2-1) 0.125)
    Example 2-31 Compound 3.74 5.82 (0.136,
    2-1-318 (2-1) 0.127)
    Example 2-32 Compound 3.78 5.82 (0.136,
    2-1-320 (2-1) 0.125)
    Comparative HT1 4.73 4.68 (0.136,
    Example 1-1 0.127)
    Comparative HT2 4.73 4.72 (0.136,
    Example 1-2 0.127)
    Comparative HT3 4.85 4.65 (0.135,
    Example 1-3 0.125)
    Comparative HT4 4.87 4.89 (0.135,
    Example 1-4 0.130)
  • In Table 8, the devices of Examples 2-1 to 2-32 using compounds having the double spiro structure represented by Chemical Formula 2 as the core had a lower driving voltage and enhanced efficiency compared to the devices of Comparative Examples 1-1 to 1-4, and the device of Comparative Example 1 using a material of NPB as the hole transfer layer.
  • When comparing the devices of Examples 2-1 to 2-32 and Comparative Examples 1-1 to 1-4, it was seen that the devices of Examples 2-1 to 2-32 had more superior properties compared to the structure in which the core of the double spiro structure compound represented by Chemical Formula 2 was substituted with two arylamine (Comparative Example 1-1 and Comparative Example 1-2) and the structure in which arylamine was linked to the spiro structure compound (Comparative Example 1-3 and Comparative Example 1-4). It was also seen that a lifespan property of the device was enhanced when a phenyl group was linked as the linking group.
  • As shown in the results of Table 8, it can be seen that amine linking various substituents (dibenzofuran, dibenzothiophene, carbazole derivatives and the like) to the core of the double spiro structure compound represented by Chemical Formula 2 of the present specification is suitable to be used as a hole transfer layer in an organic light emitting device by adjusting a HOMO level and also having an influence on the hole mobility.
  • Accordingly, it was identified that the double spiro structure compound according to the present specification had an excellent hole transfer ability, and was capable of being used as a hole transfer layer in an organic light emitting device.
    • Comparative Example 2
  • A glass substrate on which indium tin oxide (ITO) was coated as a thin film to a thickness of 1,000 Å was placed in detergent-dissolved distilled water and ultrasonic cleaned. Herein, a product of Fischer Co. was used as the detergent, and as the distilled water, distilled water filtered twice with a filter manufactured by Millipore Co. was used. After the ITO was cleaned for 30 minutes, ultrasonic cleaning was repeated twice using distilled water for 10 minutes. After the cleaning with distilled water was finished, the substrate was ultrasonic cleaned with solvents of isopropyl alcohol, acetone and methanol, then dried, and then transferred to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using oxygen plasma, and then transferred to a vacuum depositor.
  • On the transparent ITO electrode prepared as above, a light emitting device was formed in order of m-MTDATA (60 nm)/TCTA (80 nm)/CBP+10% Ir(ppy)3 (300 nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) using CBP as a host to manufacture an organic light emitting device.
  • Structures of m-MTDATA, TCTA, Ir(ppy)3, CBP and BCP are as follows, respectively.
  • Figure US20180002256A1-20180104-C02321
    Figure US20180002256A1-20180104-C02322
    • Example 3-1
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-1-1 (3-5) was used instead of CBP.
    • Example 3-2
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-1-2 (3-5) was used instead of CBP.
    • Example 3-3
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-1-6 (3-5) was used instead of Compound CBP.
    • Example 3-4
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-1-9 (3-5) was used instead of Compound CBP.
    • Example 3-5
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-1-15 (3-5) was used instead of Compound CBP.
    • Example 3-6
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-1-16 (3-5) was used instead of Compound CBP.
    • Example 3-7
  • same manner as in Comparative Example 2 except that Compound 3-1-18 (3-5) was used instead of Compound CBP.
    • Example 3-8
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-1-20 (3-5) was used instead of CBP.
    • Example 3-9
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-2-1 (3-8) was used instead of CBP.
    • Example 3-10
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-2-2 (3-8) was used instead of CBP.
    • Example 3-11
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-2-6 (3-8) was used instead of Compound CBP.
    • Example 3-12
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-2-9 (3-8) was used instead of Compound CBP.
    • Example 3-13
  • same manner as in Comparative Example 2 except that Compound 3-2-15 (3-8) was used instead of Compound CBP.
    • Example 3-14
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-2-16 (3-8) was used instead of Compound CBP.
    • Example 3-15
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-2-18 (3-8) was used instead of Compound CBP.
    • Example 3-16
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-2-20 (3-8) was used instead of CBP.
    • Example 3-17
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-3-1 (3-11) was used instead of CBP.
    • Example 3-18
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-3-2 (3-11) was used instead of CBP.
    • Example 3-19
  • same manner as in Comparative Example 2 except that Compound 3-3-6 (3-11) was used instead of Compound CBP.
    • Example 3-20
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-3-9 (3-11) was used instead of Compound CBP.
    • Example 3-21
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-3-15 (3-11) was used instead of Compound CBP.
    • Example 3-22
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-3-16 (3-11) was used instead of Compound CBP.
    • Example 3-23
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-3-18 (3-11) was used instead of Compound CBP.
    • Example 3-24
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-3-20 (3-11) was used instead of CBP.
    • Example 3-25
  • same manner as in Comparative Example 2 except that Compound 3-4-1 (3-14) was used instead of CBP.
    • Example 3-26
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-4-2 (3-14) was used instead of CBP.
    • Example 3-27
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-4-6 (3-14) was used instead of Compound CBP.
    • Example 3-28
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-4-9 (3-14) was used instead of Compound CBP.
    • Example 3-29
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-4-15 (3-14) was used instead of Compound CBP.
    • Example 3-30
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-4-16 (3-14) was used instead of Compound CBP.
    • Example 3-31
  • same manner as in Comparative Example 2 except that Compound 3-4-18 (3-14) was used instead of Compound CBP.
    • Example 3-32
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-4-20 (3-14) was used instead of CBP.
    • Comparative Example 2-1
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that a compound of the following GH1 was used instead of Compound CBP.
  • Figure US20180002256A1-20180104-C02323
    • Comparative Example 2-2
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that a compound of the following GH2 was used instead of Compound CBP.
  • Figure US20180002256A1-20180104-C02324
    • Comparative Example 2-3
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that a compound of the following GH3 was used instead of Compound CBP.
  • Figure US20180002256A1-20180104-C02325
    • Comparative Example 2-4
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that a compound of the following GH4 was used instead of Compound CBP.
  • Figure US20180002256A1-20180104-C02326
    • Comparative Example 2-5
  • same manner as in Comparative Example 2 except that a compound of the following GH5 was used instead of Compound CBP.
  • Figure US20180002256A1-20180104-C02327
    • Comparative Example 2-6
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that a compound of the following GH6 was used instead of Compound CBP.
  • Figure US20180002256A1-20180104-C02328
    • Comparative Example 2-7
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that a compound of the following GH7 was used instead of Compound CBP.
  • Figure US20180002256A1-20180104-C02329
    • Comparative Example 2-8
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that a compound of the following GH8 was used instead of Compound CBP.
  • Figure US20180002256A1-20180104-C02330
  • When a current was applied to the organic light emitting devices manufactured in Comparative Example 2, Examples 3-1 to 3-32 and Comparative Examples 2-1 to 2-8, results of Table 9 were obtained.
  • TABLE 9
    Voltage Efficiency
    Compound (V@10 (cd/A@10 EL Peak
    (Host) mA/cm2) mA/cm2) (nm)
    Comparative CBP 6.75 45.18 516
    Example 2
    Example 3-1 Compound 6.88 44.93 517
    3-1-1 (3-5)
    Example 3-2 Compound 6.88 44.93 517
    3-1-2 (3-5)
    Example 3-3 Compound 6.86 45.24 516
    3-1-6 (3-5)
    Example 3-4 Compound 6.85 44.72 518
    3-1-9 (3-5)
    Example 3-5 Compound 6.89 44.65 517
    3-1-15 (3-5)
    Example 3-6 Compound 6.88 44.31 515
    3-1-16 (3-5)
    Example 3-7 Compound 6.83 44.63 516
    3-1-18 (3-5)
    Example 3-8 Compound 6.89 44.62 516
    3-1-20 (3-5)
    Example 3-9 Compound 6.87 44.64 517
    3-2-1 (3-8)
    Example 3-10 Compound 6.74 45.08 518
    3-2-2 (3-8)
    Example 3-11 Compound 6.96 44.72 517
    3-2-6 (3-8)
    Example 3-12 Compound 6.83 44.63 516
    3-2-9 (3-8)
    Example 3-13 Compound 6.89 44.62 516
    3-2-15 (3-8)
    Example 3-14 Compound 6.87 44.64 517
    3-2-16 (3-8)
    Example 3-15 Compound 6.74 45.08 518
    3-2-18 (3-8)
    Example 3-16 Compound 6.96 44.72 517
    3-2-20 (3-8)
    Example 3-17 Compound 6.87 44.64 517
    3-3-1 (3-11)
    Example 3-18 Compound 6.74 45.08 518
    3-3-2 (3-11)
    Example 3-19 Compound 6.96 44.72 517
    3-3-6 (3-11)
    Example 3-20 Compound 6.83 44.63 516
    3-3-9 (3-11)
    Example 3-21 Compound 6.89 44.62 516
    3-3-15 (3-11)
    Example 3-22 Compound 6.87 44.64 517
    3-3-16 (3-11)
    Example 3-23 Compound 6.74 45.08 518
    3-3-18 (3-11)
    Example 3-24 Compound 6.96 44.72 517
    3-3-20 (3-11)
    Example 3-25 Compound 6.87 44.64 517
    3-4-1 (3-14)
    Example 3-26 Compound 6.74 45.08 518
    3-4-2 (3-14)
    Example 3-27 Compound 6.96 44.72 517
    3-4-6 (3-14)
    Example 3-28 Compound 6.83 44.63 516
    3-4-9 (3-14)
    Example 3-29 Compound 6.89 44.62 516
    3-4-15 (3-14)
    Example 3-30 Compound 6.87 44.64 517
    3-4-16 (3-14)
    Example 3-31 Compound 6.74 45.08 518
    3-4-18 (3-14)
    Example 3-32 Compound 6.96 44.72 517
    3-4-20 (3-14)
    Comparative GH1 7.28 43.69 517
    Example 2-1
    Comparative GH2 7.35 41.70 518
    Example 2-2
    Comparative GH3 7.48 43.69 517
    Example 2-3
    Comparative GH4 7.45 42.71 518
    Example 2-4
    Comparative GH5 7.58 43.69 517
    Example 2-5
    Comparative GH6 7.38 42.70 518
    Example 2-6
    Comparative GH7 7.58 43.69 517
    Example 2-7
    Comparative GH8 7.65 40.70 518
    Example 2-8
  • In Table 9, it was identified that the green organic light emitting devices of Examples 3-1 to 3-32 manufactured using the double spiro structure compound according to the present specification exhibited excellent properties in terms of current efficiency and a driving voltage compared to the green organic light emitting devices of Comparative Example 2 and Comparative Examples 2-1 to 2-8 using existing CBP.
    • Examples 4-1 to 4-34
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that compounds of Examples 4-1 to 4-34 were used as in the following Table 10 instead of ET1 as the electron transfer layer.
  • TABLE 10
    Compound
    (Electron Voltage Efficiency Color
    Transfer (V@10 (cd/A@10 Coordinate
    Layer) mA/cm2) mA/cm2) (x, y)
    Comparative ET1 4.21 4.51 (0.138,
    Example 1 0.127)
    Example 4-1 Compound 3.95 5.15 (0.139,
    3-1-1 (3-5) 0.122)
    Example 4-2 Compound 3.86 5.04 (0.138,
    3-1-2 (3-5) 0.126)
    Example 4-3 Compound 3.85 4.72 (0.138,
    3-1-6 (3-5) 0.127)
    Example 4-4 Compound 3.89 4.65 (0.137,
    3-1-9 (3-5) 0.129)
    Example 4-5 Compound 3.95 4.64 (0.138,
    3-1-15 (3-5) 0.128)
    Example 4-6 Compound 3.90 4.62 (0.138,
    3-1-16 (3-5) 0.129)
    Example 4-7 Compound 3.96 4.55 (0.136,
    3-1-18 (3-5) 0.128)
    Example 4-8 Compound 3.98 4.52 (0.137,
    3-1-20 (3-5) 0.127)
    Example 4-9 Compound 3.85 5.15 (0.138,
    3-2-1 (3-8) 0.127)
    Example 4-10 Compound 3.86 5.04 (0.139,
    3-2-2 (3-8) 0.122)
    Example 4-11 Compound 3.85 4.82 (0.138,
    3-2-6 (3-8) 0.126)
    Example 4-12 Compound 3.89 4.95 (0.138,
    3-2-9 (3-8) 0.127)
    Example 4-13 Compound 3.95 4.84 (0.137,
    3-2-15 (3-8) 0.129)
    Example 4-14 Compound 3.90 4.82 (0.138,
    3-2-16 (3-8) 0.128)
    Example 4-15 Compound 3.75 5.15 (0.138,
    3-2-18 (3-8) 0.127)
    Example 4-16 Compound 3.86 5.04 (0.139,
    3-2-20 (3-8) 0.122)
    Example 4-17 Compound 3.85 4.72 (0.138,
    3-3-1 (3-11) 0.126)
    Example 4-18 Compound 3.89 4.65 (0.138,
    3-3-2 (3-11) 0.127)
    Example 4-19 Compound 3.95 4.64 (0.137,
    3-3-6 (3-11) 0.129)
    Example 4-20 Compound 3.90 4.62 (0.138,
    3-3-9 (3-11) 0.128)
    Example 4-21 Compound 3.96 4.75 (0.138,
    3-3-15 (3-11) 0.127)
    Example 4-22 Compound 3.98 4.52 (0.136,
    3-3-16 (3-11) 0.128)
    Example 4-23 Compound 3.96 4.75 (0.138,
    3-3-18 (3-11) 0.127)
    Example 4-24 Compound 3.98 4.62 (0.138,
    3-3-20 (3-11) 0.128)
    Example 4-25 Compound 3.85 5.25 (0.138,
    3-4-1 (3-14) 0.127)
    Example 4-26 Compound 3.86 5.04 (0.139,
    3-4-2 (3-14) 0.122)
    Example 4-27 Compound 3.85 4.82 (0.138,
    3-4-6 (3-14) 0.126)
    Example 4-28 Compound 3.89 4.65 (0.138,
    3-4-9 (3-14) 0.127)
    Example 4-29 Compound 3.85 5.15 (0.138,
    3-4-15 (3-14) 0.128)
    Example 4-30 Compound 3.86 5.04 (0.138,
    3-4-16 (3-14) 0.127)
    Example 4-31 Compound 3.85 4.72 (0.139,
    3-4-18 (3-14) 0.122)
    Example 4-32 Compound 3.89 4.65 (0.138,
    3-4-20 (3-14) 0.126)
    Example 4-33 Compound 3.95 4.94 (0.138,
    4-4-1 (4-5) 0.127)
    Example 4-34 Compound 3.90 4.72 (0.137,
    4-4-2 (4-5) 0.129)
  • In Table 10, it was identified that the double spiro structure compound represented by Chemical Formula 3 or Chemical Formula 4 according to the present specification had an excellent electron transfer ability and was capable of being used in an organic light emitting device.
  • Hereinbefore, preferred embodiments (electron blocking layer, hole transfer layer, green light emitting layer and electron transfer layer) of the present specification have been described, however, the present specification is not limited thereto, and may be modified in various other forms within the scope of the claims and the scope of the detailed descriptions of the present invention, and these modifications also fall into the scope of the present specification.
    • REFERENCE NUMERAL
      • 10, 11: Organic Light Emitting Device
      • 20: Substrate
      • 30: Anode
      • 40: Light Emitting Layer
      • 50: Cathode
      • 60: Hole Injection Layer
      • 70: Hole Transfer Layer
      • 80: Electron Transfer Layer
      • 90: Electron Injection Layer

Claims (20)

1. A double spiro structure compound represented by the following Chemical Formula 1:
Figure US20180002256A1-20180104-C02331
wherein, in Chemical Formula 1,
R1 is represented by any one of the following Chemical Formula A to Chemical Formula C,
Figure US20180002256A1-20180104-C02332
wherein, in Chemical Formula A to Chemical Formula C,
X1 to X3 are the same as or different from each other, and each independently CH or N;
at least one of X1 to X3 is N;
X4 is O, S or NAr5;
L1 to L3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms;
Ar1 to Ar5 are the same as or different from each other, and each independently selected from the group consisting of a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; and
Cy1 is a substituted or unsubstituted monocyclic or multicyclic hydrocarbon ring having 3 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or multicyclic heteroring having 2 to 30 carbon atoms.
2. The double spiro structure compound of claim 1, wherein the double spiro structure compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulae 1-1 to 1-3:
Figure US20180002256A1-20180104-C02333
wherein, in Chemical Formula 1-1 to Chemical Formula 1-3,
a definition of R1 is the same as in Chemical Formula 1.
3. The double spiro structure compound of claim 1, wherein Cy1 is a substituted or unsubstituted benzene ring.
4. The double spiro structure compound of claim 1, wherein L1 to L3 are the same as or different from each other and each independently a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylylene group.
5. The double spiro structure compound of claim 1, wherein Ar1 to Ar5 are the same as or different from each other, and each independently selected from the group consisting of a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenylyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted quaterphenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted terphenylenyl group; a substituted or unsubstituted dibenzothiophene group; and a substituted or unsubstituted dibenzofuran group.
6. The double spiro structure compound of claim 1, wherein Ar1 to Ar5 are the same as or different from each other, and each independently selected as any one among the following structural formulae:
Figure US20180002256A1-20180104-C02334
Figure US20180002256A1-20180104-C02335
Figure US20180002256A1-20180104-C02336
Figure US20180002256A1-20180104-C02337
Figure US20180002256A1-20180104-C02338
Figure US20180002256A1-20180104-C02339
Figure US20180002256A1-20180104-C02340
Figure US20180002256A1-20180104-C02341
wherein, in the structural formulae,
Figure US20180002256A1-20180104-P00001
means a site linking to other substituents.
7. The double spiro structure compound of claim 1, wherein the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 2, and in the following Chemical Formula 2, L1, Ar1 and Ar2 are any one selected from among 2-1-1 to 2-1-334 of the following Table 1:
Figure US20180002256A1-20180104-C02342
TABLE 1 − − −L1− − − − − −Ar1 − − −Ar2 2-1- 1 Direct bond
Figure US20180002256A1-20180104-C02343
Figure US20180002256A1-20180104-C02344
 2-1- 2 Direct bond
Figure US20180002256A1-20180104-C02345
Figure US20180002256A1-20180104-C02346
 2-1- 3 Direct bond
Figure US20180002256A1-20180104-C02347
Figure US20180002256A1-20180104-C02348
 2-1- 4 Direct bond
Figure US20180002256A1-20180104-C02349
Figure US20180002256A1-20180104-C02350
 2-1- 5 Direct bond
Figure US20180002256A1-20180104-C02351
Figure US20180002256A1-20180104-C02352
 2-1- 6 Direct bond
Figure US20180002256A1-20180104-C02353
Figure US20180002256A1-20180104-C02354
 2-1- 7 Direct bond
Figure US20180002256A1-20180104-C02355
Figure US20180002256A1-20180104-C02356
 2-1- 8 Direct bond
Figure US20180002256A1-20180104-C02357
Figure US20180002256A1-20180104-C02358
 2-1- 9 Direct bond
Figure US20180002256A1-20180104-C02359
Figure US20180002256A1-20180104-C02360
 2-1- 10 Direct bond
Figure US20180002256A1-20180104-C02361
Figure US20180002256A1-20180104-C02362
 2-1- 11 Direct bond
Figure US20180002256A1-20180104-C02363
Figure US20180002256A1-20180104-C02364
 2-1- 12 Direct bond
Figure US20180002256A1-20180104-C02365
Figure US20180002256A1-20180104-C02366
 2-1- 13 Direct bond
Figure US20180002256A1-20180104-C02367
Figure US20180002256A1-20180104-C02368
 2-1- 14 Direct bond
Figure US20180002256A1-20180104-C02369
Figure US20180002256A1-20180104-C02370
 2-1- 15 Direct bond
Figure US20180002256A1-20180104-C02371
Figure US20180002256A1-20180104-C02372
 2-1- 16 Direct bond
Figure US20180002256A1-20180104-C02373
Figure US20180002256A1-20180104-C02374
 2-1- 17 Direct bond
Figure US20180002256A1-20180104-C02375
Figure US20180002256A1-20180104-C02376
 2-1- 18 Direct bond
Figure US20180002256A1-20180104-C02377
Figure US20180002256A1-20180104-C02378
 2-1- 19 Direct bond
Figure US20180002256A1-20180104-C02379
Figure US20180002256A1-20180104-C02380
 2-1- 20 Direct bond
Figure US20180002256A1-20180104-C02381
Figure US20180002256A1-20180104-C02382
 2-1- 21 Direct bond
Figure US20180002256A1-20180104-C02383
Figure US20180002256A1-20180104-C02384
 2-1- 22 Direct bond
Figure US20180002256A1-20180104-C02385
Figure US20180002256A1-20180104-C02386
 2-1- 23 Direct bond
Figure US20180002256A1-20180104-C02387
Figure US20180002256A1-20180104-C02388
 2-1- 24 Direct bond
Figure US20180002256A1-20180104-C02389
Figure US20180002256A1-20180104-C02390
 2-1- 25 Direct bond
Figure US20180002256A1-20180104-C02391
Figure US20180002256A1-20180104-C02392
 2-1- 26 Direct bond
Figure US20180002256A1-20180104-C02393
Figure US20180002256A1-20180104-C02394
 2-1- 27 Direct bond
Figure US20180002256A1-20180104-C02395
Figure US20180002256A1-20180104-C02396
 2-1- 28 Direct bond
Figure US20180002256A1-20180104-C02397
Figure US20180002256A1-20180104-C02398
 2-1- 29 Direct bond
Figure US20180002256A1-20180104-C02399
Figure US20180002256A1-20180104-C02400
 2-1- 30 Direct bond
Figure US20180002256A1-20180104-C02401
Figure US20180002256A1-20180104-C02402
 2-1- 31 Direct bond
Figure US20180002256A1-20180104-C02403
Figure US20180002256A1-20180104-C02404
 2-1- 32 Direct bond
Figure US20180002256A1-20180104-C02405
Figure US20180002256A1-20180104-C02406
 2-1- 33 Direct bond
Figure US20180002256A1-20180104-C02407
Figure US20180002256A1-20180104-C02408
 2-1- 34 Direct bond
Figure US20180002256A1-20180104-C02409
Figure US20180002256A1-20180104-C02410
 2-1- 35 Direct bond
Figure US20180002256A1-20180104-C02411
Figure US20180002256A1-20180104-C02412
 2-1- 36 Direct bond
Figure US20180002256A1-20180104-C02413
Figure US20180002256A1-20180104-C02414
 2-1- 37 Direct bond
Figure US20180002256A1-20180104-C02415
Figure US20180002256A1-20180104-C02416
 2-1- 38 Direct bond
Figure US20180002256A1-20180104-C02417
Figure US20180002256A1-20180104-C02418
 2-1- 39 Direct bond
Figure US20180002256A1-20180104-C02419
Figure US20180002256A1-20180104-C02420
 2-1- 40 Direct bond
Figure US20180002256A1-20180104-C02421
Figure US20180002256A1-20180104-C02422
 2-1- 41 Direct bond
Figure US20180002256A1-20180104-C02423
Figure US20180002256A1-20180104-C02424
 2-1- 42 Direct bond
Figure US20180002256A1-20180104-C02425
Figure US20180002256A1-20180104-C02426
 2-1- 43 Direct bond
Figure US20180002256A1-20180104-C02427
Figure US20180002256A1-20180104-C02428
 2-1- 44 Direct bond
Figure US20180002256A1-20180104-C02429
Figure US20180002256A1-20180104-C02430
 2-1- 45 Direct bond
Figure US20180002256A1-20180104-C02431
Figure US20180002256A1-20180104-C02432
 2-1- 46 Direct bond
Figure US20180002256A1-20180104-C02433
Figure US20180002256A1-20180104-C02434
 2-1- 47 Direct bond
Figure US20180002256A1-20180104-C02435
Figure US20180002256A1-20180104-C02436
 2-1- 48 Direct bond
Figure US20180002256A1-20180104-C02437
Figure US20180002256A1-20180104-C02438
 2-1- 49 Direct bond
Figure US20180002256A1-20180104-C02439
Figure US20180002256A1-20180104-C02440
 2-1- 50 Direct bond
Figure US20180002256A1-20180104-C02441
Figure US20180002256A1-20180104-C02442
 2-1- 51 Direct bond
Figure US20180002256A1-20180104-C02443
Figure US20180002256A1-20180104-C02444
 2-1- 52 Direct bond
Figure US20180002256A1-20180104-C02445
Figure US20180002256A1-20180104-C02446
 2-1- 53 Direct bond
Figure US20180002256A1-20180104-C02447
Figure US20180002256A1-20180104-C02448
 2-1- 54 Direct bond
Figure US20180002256A1-20180104-C02449
Figure US20180002256A1-20180104-C02450
 2-1- 55 Direct bond
Figure US20180002256A1-20180104-C02451
Figure US20180002256A1-20180104-C02452
 2-1- 56 Direct bond
Figure US20180002256A1-20180104-C02453
Figure US20180002256A1-20180104-C02454
 2-1- 57 Direct bond
Figure US20180002256A1-20180104-C02455
Figure US20180002256A1-20180104-C02456
 2-1- 58 Direct bond
Figure US20180002256A1-20180104-C02457
Figure US20180002256A1-20180104-C02458
 2-1- 59 Direct bond
Figure US20180002256A1-20180104-C02459
Figure US20180002256A1-20180104-C02460
 2-1- 60 Direct bond
Figure US20180002256A1-20180104-C02461
Figure US20180002256A1-20180104-C02462
 2-1- 61 Direct bond
Figure US20180002256A1-20180104-C02463
Figure US20180002256A1-20180104-C02464
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Figure US20180002256A1-20180104-C02465
Figure US20180002256A1-20180104-C02466
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Figure US20180002256A1-20180104-C02467
Figure US20180002256A1-20180104-C02468
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Figure US20180002256A1-20180104-C02469
Figure US20180002256A1-20180104-C02470
Figure US20180002256A1-20180104-C02471
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Figure US20180002256A1-20180104-C02472
Figure US20180002256A1-20180104-C02473
Figure US20180002256A1-20180104-C02474
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Figure US20180002256A1-20180104-C02475
Figure US20180002256A1-20180104-C02476
Figure US20180002256A1-20180104-C02477
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Figure US20180002256A1-20180104-C02478
Figure US20180002256A1-20180104-C02479
Figure US20180002256A1-20180104-C02480
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Figure US20180002256A1-20180104-C02481
Figure US20180002256A1-20180104-C02482
Figure US20180002256A1-20180104-C02483
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Figure US20180002256A1-20180104-C02484
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Figure US20180002256A1-20180104-C02487
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Figure US20180002256A1-20180104-C02490
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Figure US20180002256A1-20180104-C02492
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Figure US20180002256A1-20180104-C02493
Figure US20180002256A1-20180104-C02494
Figure US20180002256A1-20180104-C02495
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Figure US20180002256A1-20180104-C02496
Figure US20180002256A1-20180104-C02497
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Figure US20180002256A1-20180104-C02499
Figure US20180002256A1-20180104-C02500
Figure US20180002256A1-20180104-C02501
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Figure US20180002256A1-20180104-C02502
Figure US20180002256A1-20180104-C02503
Figure US20180002256A1-20180104-C02504
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Figure US20180002256A1-20180104-C02505
Figure US20180002256A1-20180104-C02506
Figure US20180002256A1-20180104-C02507
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Figure US20180002256A1-20180104-C02508
Figure US20180002256A1-20180104-C02509
Figure US20180002256A1-20180104-C02510
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Figure US20180002256A1-20180104-C02511
Figure US20180002256A1-20180104-C02512
Figure US20180002256A1-20180104-C02513
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Figure US20180002256A1-20180104-C02514
Figure US20180002256A1-20180104-C02515
Figure US20180002256A1-20180104-C02516
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Figure US20180002256A1-20180104-C02517
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Figure US20180002256A1-20180104-C02519
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Figure US20180002256A1-20180104-C02520
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Figure US20180002256A1-20180104-C02523
Figure US20180002256A1-20180104-C02524
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Figure US20180002256A1-20180104-C02526
Figure US20180002256A1-20180104-C02527
Figure US20180002256A1-20180104-C02528
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Figure US20180002256A1-20180104-C02529
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Figure US20180002256A1-20180104-C02532
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Figure US20180002256A1-20180104-C02535
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Figure US20180002256A1-20180104-C02538
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Figure US20180002256A1-20180104-C02541
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Figure US20180002256A1-20180104-C02547
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Figure US20180002256A1-20180104-C02550
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Figure US20180002256A1-20180104-C02553
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Figure US20180002256A1-20180104-C02556
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Figure US20180002256A1-20180104-C02559
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Figure US20180002256A1-20180104-C02561
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Figure US20180002256A1-20180104-C02562
Figure US20180002256A1-20180104-C02563
Figure US20180002256A1-20180104-C02564
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Figure US20180002256A1-20180104-C02565
Figure US20180002256A1-20180104-C02566
Figure US20180002256A1-20180104-C02567
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Figure US20180002256A1-20180104-C02568
Figure US20180002256A1-20180104-C02569
Figure US20180002256A1-20180104-C02570
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Figure US20180002256A1-20180104-C02571
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Figure US20180002256A1-20180104-C02574
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Figure US20180002256A1-20180104-C02577
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Figure US20180002256A1-20180104-C02580
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Figure US20180002256A1-20180104-C02583
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Figure US20180002256A1-20180104-C02586
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Figure US20180002256A1-20180104-C02589
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Figure US20180002256A1-20180104-C02592
Figure US20180002256A1-20180104-C02593
Figure US20180002256A1-20180104-C02594
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Figure US20180002256A1-20180104-C02595
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Figure US20180002256A1-20180104-C02597
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Figure US20180002256A1-20180104-C02598
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Figure US20180002256A1-20180104-C02601
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Figure US20180002256A1-20180104-C02604
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Figure US20180002256A1-20180104-C02607
Figure US20180002256A1-20180104-C02608
Figure US20180002256A1-20180104-C02609
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Figure US20180002256A1-20180104-C02610
Figure US20180002256A1-20180104-C02611
Figure US20180002256A1-20180104-C02612
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Figure US20180002256A1-20180104-C02613
Figure US20180002256A1-20180104-C02614
Figure US20180002256A1-20180104-C02615
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Figure US20180002256A1-20180104-C02616
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Figure US20180002256A1-20180104-C02619
Figure US20180002256A1-20180104-C02620
Figure US20180002256A1-20180104-C02621
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Figure US20180002256A1-20180104-C02622
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Figure US20180002256A1-20180104-C02624
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Figure US20180002256A1-20180104-C02625
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Figure US20180002256A1-20180104-C02627
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Figure US20180002256A1-20180104-C02628
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Figure US20180002256A1-20180104-C02631
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Figure US20180002256A1-20180104-C02634
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Figure US20180002256A1-20180104-C02637
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Figure US20180002256A1-20180104-C02640
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Figure US20180002256A1-20180104-C02643
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Figure US20180002256A1-20180104-C02646
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Figure US20180002256A1-20180104-C02649
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Figure US20180002256A1-20180104-C02661
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Figure US20180002256A1-20180104-C02664
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Figure US20180002256A1-20180104-C02667
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Figure US20180002256A1-20180104-C02670
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Figure US20180002256A1-20180104-C02673
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Figure US20180002256A1-20180104-C02676
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Figure US20180002256A1-20180104-C02679
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Figure US20180002256A1-20180104-C02688
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Figure US20180002256A1-20180104-C02709
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Figure US20180002256A1-20180104-C02712
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Figure US20180002256A1-20180104-C02715
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Figure US20180002256A1-20180104-C02727
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Figure US20180002256A1-20180104-C02883
Figure US20180002256A1-20180104-C02884
Figure US20180002256A1-20180104-C02885
 2-1- 203
Figure US20180002256A1-20180104-C02886
Figure US20180002256A1-20180104-C02887
Figure US20180002256A1-20180104-C02888
 2-1- 204
Figure US20180002256A1-20180104-C02889
Figure US20180002256A1-20180104-C02890
Figure US20180002256A1-20180104-C02891
 2-1- 205
Figure US20180002256A1-20180104-C02892
Figure US20180002256A1-20180104-C02893
Figure US20180002256A1-20180104-C02894
 2-1- 206
Figure US20180002256A1-20180104-C02895
Figure US20180002256A1-20180104-C02896
Figure US20180002256A1-20180104-C02897
 2-1- 207
Figure US20180002256A1-20180104-C02898
Figure US20180002256A1-20180104-C02899
Figure US20180002256A1-20180104-C02900
 2-1- 208
Figure US20180002256A1-20180104-C02901
Figure US20180002256A1-20180104-C02902
Figure US20180002256A1-20180104-C02903
 2-1- 209
Figure US20180002256A1-20180104-C02904
Figure US20180002256A1-20180104-C02905
Figure US20180002256A1-20180104-C02906
 2-1- 210
Figure US20180002256A1-20180104-C02907
Figure US20180002256A1-20180104-C02908
Figure US20180002256A1-20180104-C02909
 2-1- 211
Figure US20180002256A1-20180104-C02910
Figure US20180002256A1-20180104-C02911
Figure US20180002256A1-20180104-C02912
 2-1- 212
Figure US20180002256A1-20180104-C02913
Figure US20180002256A1-20180104-C02914
Figure US20180002256A1-20180104-C02915
 2-1- 213
Figure US20180002256A1-20180104-C02916
Figure US20180002256A1-20180104-C02917
Figure US20180002256A1-20180104-C02918
 2-1- 214
Figure US20180002256A1-20180104-C02919
Figure US20180002256A1-20180104-C02920
Figure US20180002256A1-20180104-C02921
 2-1- 215
Figure US20180002256A1-20180104-C02922
Figure US20180002256A1-20180104-C02923
Figure US20180002256A1-20180104-C02924
 2-1- 216
Figure US20180002256A1-20180104-C02925
Figure US20180002256A1-20180104-C02926
Figure US20180002256A1-20180104-C02927
 2-1- 217
Figure US20180002256A1-20180104-C02928
Figure US20180002256A1-20180104-C02929
Figure US20180002256A1-20180104-C02930
 2-1- 218
Figure US20180002256A1-20180104-C02931
Figure US20180002256A1-20180104-C02932
Figure US20180002256A1-20180104-C02933
 2-1- 219
Figure US20180002256A1-20180104-C02934
Figure US20180002256A1-20180104-C02935
Figure US20180002256A1-20180104-C02936
 2-1- 220
Figure US20180002256A1-20180104-C02937
Figure US20180002256A1-20180104-C02938
Figure US20180002256A1-20180104-C02939
 2-1- 221
Figure US20180002256A1-20180104-C02940
Figure US20180002256A1-20180104-C02941
Figure US20180002256A1-20180104-C02942
 2-1- 222
Figure US20180002256A1-20180104-C02943
Figure US20180002256A1-20180104-C02944
Figure US20180002256A1-20180104-C02945
 2-1- 223
Figure US20180002256A1-20180104-C02946
Figure US20180002256A1-20180104-C02947
Figure US20180002256A1-20180104-C02948
 2-1- 224
Figure US20180002256A1-20180104-C02949
Figure US20180002256A1-20180104-C02950
Figure US20180002256A1-20180104-C02951
 2-1- 225
Figure US20180002256A1-20180104-C02952
Figure US20180002256A1-20180104-C02953
Figure US20180002256A1-20180104-C02954
 2-1- 226
Figure US20180002256A1-20180104-C02955
Figure US20180002256A1-20180104-C02956
Figure US20180002256A1-20180104-C02957
 2-1- 227
Figure US20180002256A1-20180104-C02958
Figure US20180002256A1-20180104-C02959
Figure US20180002256A1-20180104-C02960
 2-1- 228
Figure US20180002256A1-20180104-C02961
Figure US20180002256A1-20180104-C02962
Figure US20180002256A1-20180104-C02963
 2-1- 229
Figure US20180002256A1-20180104-C02964
Figure US20180002256A1-20180104-C02965
Figure US20180002256A1-20180104-C02966
 2-1- 230
Figure US20180002256A1-20180104-C02967
Figure US20180002256A1-20180104-C02968
Figure US20180002256A1-20180104-C02969
 2-1- 231
Figure US20180002256A1-20180104-C02970
Figure US20180002256A1-20180104-C02971
Figure US20180002256A1-20180104-C02972
 2-1- 232
Figure US20180002256A1-20180104-C02973
Figure US20180002256A1-20180104-C02974
Figure US20180002256A1-20180104-C02975
 2-1- 233
Figure US20180002256A1-20180104-C02976
Figure US20180002256A1-20180104-C02977
Figure US20180002256A1-20180104-C02978
 2-1- 234
Figure US20180002256A1-20180104-C02979
Figure US20180002256A1-20180104-C02980
Figure US20180002256A1-20180104-C02981
 2-1- 235
Figure US20180002256A1-20180104-C02982
Figure US20180002256A1-20180104-C02983
Figure US20180002256A1-20180104-C02984
 2-1- 236
Figure US20180002256A1-20180104-C02985
Figure US20180002256A1-20180104-C02986
Figure US20180002256A1-20180104-C02987
 2-1- 237
Figure US20180002256A1-20180104-C02988
Figure US20180002256A1-20180104-C02989
Figure US20180002256A1-20180104-C02990
 2-1- 238
Figure US20180002256A1-20180104-C02991
Figure US20180002256A1-20180104-C02992
Figure US20180002256A1-20180104-C02993
 2-1- 239
Figure US20180002256A1-20180104-C02994
Figure US20180002256A1-20180104-C02995
Figure US20180002256A1-20180104-C02996
 2-1- 240
Figure US20180002256A1-20180104-C02997
Figure US20180002256A1-20180104-C02998
Figure US20180002256A1-20180104-C02999
 2-1- 241
Figure US20180002256A1-20180104-C03000
Figure US20180002256A1-20180104-C03001
Figure US20180002256A1-20180104-C03002
 2-1- 242
Figure US20180002256A1-20180104-C03003
Figure US20180002256A1-20180104-C03004
Figure US20180002256A1-20180104-C03005
 2-1- 243
Figure US20180002256A1-20180104-C03006
Figure US20180002256A1-20180104-C03007
Figure US20180002256A1-20180104-C03008
 2-1- 244
Figure US20180002256A1-20180104-C03009
Figure US20180002256A1-20180104-C03010
Figure US20180002256A1-20180104-C03011
 2-1- 245
Figure US20180002256A1-20180104-C03012
Figure US20180002256A1-20180104-C03013
Figure US20180002256A1-20180104-C03014
 2-1- 246
Figure US20180002256A1-20180104-C03015
Figure US20180002256A1-20180104-C03016
Figure US20180002256A1-20180104-C03017
 2-1- 247
Figure US20180002256A1-20180104-C03018
Figure US20180002256A1-20180104-C03019
Figure US20180002256A1-20180104-C03020
 2-1- 248
Figure US20180002256A1-20180104-C03021
Figure US20180002256A1-20180104-C03022
Figure US20180002256A1-20180104-C03023
 2-1- 249
Figure US20180002256A1-20180104-C03024
Figure US20180002256A1-20180104-C03025
Figure US20180002256A1-20180104-C03026
 2-1- 250
Figure US20180002256A1-20180104-C03027
Figure US20180002256A1-20180104-C03028
Figure US20180002256A1-20180104-C03029
 2-1- 251
Figure US20180002256A1-20180104-C03030
Figure US20180002256A1-20180104-C03031
Figure US20180002256A1-20180104-C03032
 2-1- 252
Figure US20180002256A1-20180104-C03033
Figure US20180002256A1-20180104-C03034
Figure US20180002256A1-20180104-C03035
 2-1- 253
Figure US20180002256A1-20180104-C03036
Figure US20180002256A1-20180104-C03037
Figure US20180002256A1-20180104-C03038
 2-1- 254
Figure US20180002256A1-20180104-C03039
Figure US20180002256A1-20180104-C03040
Figure US20180002256A1-20180104-C03041
 2-1- 255
Figure US20180002256A1-20180104-C03042
Figure US20180002256A1-20180104-C03043
Figure US20180002256A1-20180104-C03044
 2-1- 256
Figure US20180002256A1-20180104-C03045
Figure US20180002256A1-20180104-C03046
Figure US20180002256A1-20180104-C03047
 2-1- 257
Figure US20180002256A1-20180104-C03048
Figure US20180002256A1-20180104-C03049
Figure US20180002256A1-20180104-C03050
 2-1- 258
Figure US20180002256A1-20180104-C03051
Figure US20180002256A1-20180104-C03052
Figure US20180002256A1-20180104-C03053
 2-1- 259
Figure US20180002256A1-20180104-C03054
Figure US20180002256A1-20180104-C03055
Figure US20180002256A1-20180104-C03056
 2-1- 260
Figure US20180002256A1-20180104-C03057
Figure US20180002256A1-20180104-C03058
Figure US20180002256A1-20180104-C03059
 2-1- 261
Figure US20180002256A1-20180104-C03060
Figure US20180002256A1-20180104-C03061
Figure US20180002256A1-20180104-C03062
 2-1- 262
Figure US20180002256A1-20180104-C03063
Figure US20180002256A1-20180104-C03064
Figure US20180002256A1-20180104-C03065
 2-1- 263
Figure US20180002256A1-20180104-C03066
Figure US20180002256A1-20180104-C03067
Figure US20180002256A1-20180104-C03068
 2-1- 264
Figure US20180002256A1-20180104-C03069
Figure US20180002256A1-20180104-C03070
Figure US20180002256A1-20180104-C03071
 2-1- 265
Figure US20180002256A1-20180104-C03072
Figure US20180002256A1-20180104-C03073
Figure US20180002256A1-20180104-C03074
 2-1- 266
Figure US20180002256A1-20180104-C03075
Figure US20180002256A1-20180104-C03076
Figure US20180002256A1-20180104-C03077
 2-1- 267
Figure US20180002256A1-20180104-C03078
Figure US20180002256A1-20180104-C03079
Figure US20180002256A1-20180104-C03080
 2-1- 268
Figure US20180002256A1-20180104-C03081
Figure US20180002256A1-20180104-C03082
Figure US20180002256A1-20180104-C03083
 2-1- 269
Figure US20180002256A1-20180104-C03084
Figure US20180002256A1-20180104-C03085
Figure US20180002256A1-20180104-C03086
 2-1- 270
Figure US20180002256A1-20180104-C03087
Figure US20180002256A1-20180104-C03088
Figure US20180002256A1-20180104-C03089
 2-1- 271
Figure US20180002256A1-20180104-C03090
Figure US20180002256A1-20180104-C03091
Figure US20180002256A1-20180104-C03092
 2-1- 272
Figure US20180002256A1-20180104-C03093
Figure US20180002256A1-20180104-C03094
Figure US20180002256A1-20180104-C03095
 2-1- 273
Figure US20180002256A1-20180104-C03096
Figure US20180002256A1-20180104-C03097
Figure US20180002256A1-20180104-C03098
 +- 2-1- 274
Figure US20180002256A1-20180104-C03099
Figure US20180002256A1-20180104-C03100
Figure US20180002256A1-20180104-C03101
 2-1- 275
Figure US20180002256A1-20180104-C03102
Figure US20180002256A1-20180104-C03103
Figure US20180002256A1-20180104-C03104
 2-1- 276
Figure US20180002256A1-20180104-C03105
Figure US20180002256A1-20180104-C03106
Figure US20180002256A1-20180104-C03107
 2-1- 277
Figure US20180002256A1-20180104-C03108
Figure US20180002256A1-20180104-C03109
Figure US20180002256A1-20180104-C03110
 2-1- 278
Figure US20180002256A1-20180104-C03111
Figure US20180002256A1-20180104-C03112
Figure US20180002256A1-20180104-C03113
 2-1- 279
Figure US20180002256A1-20180104-C03114
Figure US20180002256A1-20180104-C03115
Figure US20180002256A1-20180104-C03116
 2-1- 280
Figure US20180002256A1-20180104-C03117
Figure US20180002256A1-20180104-C03118
Figure US20180002256A1-20180104-C03119
 2-1- 281
Figure US20180002256A1-20180104-C03120
Figure US20180002256A1-20180104-C03121
Figure US20180002256A1-20180104-C03122
 2-1- 282
Figure US20180002256A1-20180104-C03123
Figure US20180002256A1-20180104-C03124
Figure US20180002256A1-20180104-C03125
 2-1- 283
Figure US20180002256A1-20180104-C03126
Figure US20180002256A1-20180104-C03127
Figure US20180002256A1-20180104-C03128
 2-1- 284
Figure US20180002256A1-20180104-C03129
Figure US20180002256A1-20180104-C03130
Figure US20180002256A1-20180104-C03131
 2-1- 285
Figure US20180002256A1-20180104-C03132
Figure US20180002256A1-20180104-C03133
Figure US20180002256A1-20180104-C03134
 2-1- 286
Figure US20180002256A1-20180104-C03135
Figure US20180002256A1-20180104-C03136
Figure US20180002256A1-20180104-C03137
 2-1- 287
Figure US20180002256A1-20180104-C03138
Figure US20180002256A1-20180104-C03139
Figure US20180002256A1-20180104-C03140
 2-1- 288
Figure US20180002256A1-20180104-C03141
Figure US20180002256A1-20180104-C03142
Figure US20180002256A1-20180104-C03143
 2-1- 289
Figure US20180002256A1-20180104-C03144
Figure US20180002256A1-20180104-C03145
Figure US20180002256A1-20180104-C03146
 2-1- 290
Figure US20180002256A1-20180104-C03147
Figure US20180002256A1-20180104-C03148
Figure US20180002256A1-20180104-C03149
 2-1- 291
Figure US20180002256A1-20180104-C03150
Figure US20180002256A1-20180104-C03151
Figure US20180002256A1-20180104-C03152
 2-1- 292
Figure US20180002256A1-20180104-C03153
Figure US20180002256A1-20180104-C03154
Figure US20180002256A1-20180104-C03155
 2-1- 293
Figure US20180002256A1-20180104-C03156
Figure US20180002256A1-20180104-C03157
Figure US20180002256A1-20180104-C03158
 2-1- 294
Figure US20180002256A1-20180104-C03159
Figure US20180002256A1-20180104-C03160
Figure US20180002256A1-20180104-C03161
 2-1- 295
Figure US20180002256A1-20180104-C03162
Figure US20180002256A1-20180104-C03163
Figure US20180002256A1-20180104-C03164
 2-1- 296
Figure US20180002256A1-20180104-C03165
Figure US20180002256A1-20180104-C03166
Figure US20180002256A1-20180104-C03167
 2-1- 297
Figure US20180002256A1-20180104-C03168
Figure US20180002256A1-20180104-C03169
Figure US20180002256A1-20180104-C03170
 2-1- 298
Figure US20180002256A1-20180104-C03171
Figure US20180002256A1-20180104-C03172
Figure US20180002256A1-20180104-C03173
 2-1- 299
Figure US20180002256A1-20180104-C03174
Figure US20180002256A1-20180104-C03175
Figure US20180002256A1-20180104-C03176
 2-1- 300
Figure US20180002256A1-20180104-C03177
Figure US20180002256A1-20180104-C03178
Figure US20180002256A1-20180104-C03179
 2-1- 301
Figure US20180002256A1-20180104-C03180
Figure US20180002256A1-20180104-C03181
Figure US20180002256A1-20180104-C03182
 2-1- 302
Figure US20180002256A1-20180104-C03183
Figure US20180002256A1-20180104-C03184
Figure US20180002256A1-20180104-C03185
 2-1- 303
Figure US20180002256A1-20180104-C03186
Figure US20180002256A1-20180104-C03187
Figure US20180002256A1-20180104-C03188
 2-1- 304
Figure US20180002256A1-20180104-C03189
Figure US20180002256A1-20180104-C03190
Figure US20180002256A1-20180104-C03191
 2-1- 305
Figure US20180002256A1-20180104-C03192
Figure US20180002256A1-20180104-C03193
Figure US20180002256A1-20180104-C03194
 2-1- 306
Figure US20180002256A1-20180104-C03195
Figure US20180002256A1-20180104-C03196
Figure US20180002256A1-20180104-C03197
 2-1- 307
Figure US20180002256A1-20180104-C03198
Figure US20180002256A1-20180104-C03199
Figure US20180002256A1-20180104-C03200
 2-1- 308
Figure US20180002256A1-20180104-C03201
Figure US20180002256A1-20180104-C03202
Figure US20180002256A1-20180104-C03203
 2-1- 309
Figure US20180002256A1-20180104-C03204
Figure US20180002256A1-20180104-C03205
Figure US20180002256A1-20180104-C03206
 2-1- 310
Figure US20180002256A1-20180104-C03207
Figure US20180002256A1-20180104-C03208
Figure US20180002256A1-20180104-C03209
 2-1- 311
Figure US20180002256A1-20180104-C03210
Figure US20180002256A1-20180104-C03211
Figure US20180002256A1-20180104-C03212
 2-1- 312
Figure US20180002256A1-20180104-C03213
Figure US20180002256A1-20180104-C03214
Figure US20180002256A1-20180104-C03215
 2-1- 313
Figure US20180002256A1-20180104-C03216
Figure US20180002256A1-20180104-C03217
Figure US20180002256A1-20180104-C03218
 2-1- 314
Figure US20180002256A1-20180104-C03219
Figure US20180002256A1-20180104-C03220
Figure US20180002256A1-20180104-C03221
 2-1- 315
Figure US20180002256A1-20180104-C03222
Figure US20180002256A1-20180104-C03223
Figure US20180002256A1-20180104-C03224
 2-1- 316
Figure US20180002256A1-20180104-C03225
Figure US20180002256A1-20180104-C03226
Figure US20180002256A1-20180104-C03227
 2-1- 317
Figure US20180002256A1-20180104-C03228
Figure US20180002256A1-20180104-C03229
Figure US20180002256A1-20180104-C03230
 2-1- 318
Figure US20180002256A1-20180104-C03231
Figure US20180002256A1-20180104-C03232
Figure US20180002256A1-20180104-C03233
 2-1- 319
Figure US20180002256A1-20180104-C03234
Figure US20180002256A1-20180104-C03235
Figure US20180002256A1-20180104-C03236
 2-1- 320
Figure US20180002256A1-20180104-C03237
Figure US20180002256A1-20180104-C03238
Figure US20180002256A1-20180104-C03239
 2-1- 321
Figure US20180002256A1-20180104-C03240
Figure US20180002256A1-20180104-C03241
Figure US20180002256A1-20180104-C03242
 2-1- 322
Figure US20180002256A1-20180104-C03243
Figure US20180002256A1-20180104-C03244
Figure US20180002256A1-20180104-C03245
 2-1- 323
Figure US20180002256A1-20180104-C03246
Figure US20180002256A1-20180104-C03247
Figure US20180002256A1-20180104-C03248
 2-1- 324
Figure US20180002256A1-20180104-C03249
Figure US20180002256A1-20180104-C03250
Figure US20180002256A1-20180104-C03251
 2-1- 325
Figure US20180002256A1-20180104-C03252
Figure US20180002256A1-20180104-C03253
Figure US20180002256A1-20180104-C03254
 2-1- 326
Figure US20180002256A1-20180104-C03255
Figure US20180002256A1-20180104-C03256
Figure US20180002256A1-20180104-C03257
 2-1- 327
Figure US20180002256A1-20180104-C03258
Figure US20180002256A1-20180104-C03259
Figure US20180002256A1-20180104-C03260
 2-1- 328
Figure US20180002256A1-20180104-C03261
Figure US20180002256A1-20180104-C03262
Figure US20180002256A1-20180104-C03263
 2-1- 329
Figure US20180002256A1-20180104-C03264
Figure US20180002256A1-20180104-C03265
Figure US20180002256A1-20180104-C03266
 2-1- 330
Figure US20180002256A1-20180104-C03267
Figure US20180002256A1-20180104-C03268
Figure US20180002256A1-20180104-C03269
 2-1- 331
Figure US20180002256A1-20180104-C03270
Figure US20180002256A1-20180104-C03271
Figure US20180002256A1-20180104-C03272
 2-1- 332
Figure US20180002256A1-20180104-C03273
Figure US20180002256A1-20180104-C03274
Figure US20180002256A1-20180104-C03275
 2-1- 333
Figure US20180002256A1-20180104-C03276
Figure US20180002256A1-20180104-C03277
Figure US20180002256A1-20180104-C03278
 2-1- 334
Figure US20180002256A1-20180104-C03279
Figure US20180002256A1-20180104-C03280
Figure US20180002256A1-20180104-C03281
8. The double Spiro structure compound of claim 1, wherein the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-1, and in the following Chemical Formula 3-1, L2, Ar3 and Ar4 are any one selected from among 3-1-1 to 3-1-104 of the following Table 2:
Figure US20180002256A1-20180104-C03282
TABLE 2
Figure US20180002256A1-20180104-C03283
Figure US20180002256A1-20180104-C03284
Figure US20180002256A1-20180104-C03285
 3-1-1 Direct bond
Figure US20180002256A1-20180104-C03286
Figure US20180002256A1-20180104-C03287
 3-1-2 Direct bond
Figure US20180002256A1-20180104-C03288
Figure US20180002256A1-20180104-C03289
 3-1-3 Direct bond
Figure US20180002256A1-20180104-C03290
Figure US20180002256A1-20180104-C03291
 3-1-4 Direct bond
Figure US20180002256A1-20180104-C03292
Figure US20180002256A1-20180104-C03293
 3-1-5 Direct bond
Figure US20180002256A1-20180104-C03294
Figure US20180002256A1-20180104-C03295
 3-1-6 Direct bond
Figure US20180002256A1-20180104-C03296
Figure US20180002256A1-20180104-C03297
 3-1-7 Direct bond
Figure US20180002256A1-20180104-C03298
Figure US20180002256A1-20180104-C03299
 3-1-8 Direct bond
Figure US20180002256A1-20180104-C03300
Figure US20180002256A1-20180104-C03301
 3-1-9 Direct bond
Figure US20180002256A1-20180104-C03302
Figure US20180002256A1-20180104-C03303
 3-1-10 Direct bond
Figure US20180002256A1-20180104-C03304
Figure US20180002256A1-20180104-C03305
 3-1-11 Direct bond
Figure US20180002256A1-20180104-C03306
Figure US20180002256A1-20180104-C03307
 3-1-12
Figure US20180002256A1-20180104-C03308
Figure US20180002256A1-20180104-C03309
Figure US20180002256A1-20180104-C03310
 3-1-13
Figure US20180002256A1-20180104-C03311
Figure US20180002256A1-20180104-C03312
Figure US20180002256A1-20180104-C03313
 3-1-14
Figure US20180002256A1-20180104-C03314
Figure US20180002256A1-20180104-C03315
Figure US20180002256A1-20180104-C03316
 3-1-15
Figure US20180002256A1-20180104-C03317
Figure US20180002256A1-20180104-C03318
Figure US20180002256A1-20180104-C03319
 3-1-16
Figure US20180002256A1-20180104-C03320
Figure US20180002256A1-20180104-C03321
Figure US20180002256A1-20180104-C03322
 3-1-17
Figure US20180002256A1-20180104-C03323
Figure US20180002256A1-20180104-C03324
Figure US20180002256A1-20180104-C03325
 3-1-18
Figure US20180002256A1-20180104-C03326
Figure US20180002256A1-20180104-C03327
Figure US20180002256A1-20180104-C03328
 3-1-19
Figure US20180002256A1-20180104-C03329
Figure US20180002256A1-20180104-C03330
Figure US20180002256A1-20180104-C03331
 3-1-20
Figure US20180002256A1-20180104-C03332
Figure US20180002256A1-20180104-C03333
Figure US20180002256A1-20180104-C03334
 3-1-21
Figure US20180002256A1-20180104-C03335
Figure US20180002256A1-20180104-C03336
Figure US20180002256A1-20180104-C03337
 3-1-22
Figure US20180002256A1-20180104-C03338
Figure US20180002256A1-20180104-C03339
Figure US20180002256A1-20180104-C03340
 3-1-23
Figure US20180002256A1-20180104-C03341
Figure US20180002256A1-20180104-C03342
Figure US20180002256A1-20180104-C03343
 3-1-24
Figure US20180002256A1-20180104-C03344
Figure US20180002256A1-20180104-C03345
Figure US20180002256A1-20180104-C03346
 3-1-25
Figure US20180002256A1-20180104-C03347
Figure US20180002256A1-20180104-C03348
Figure US20180002256A1-20180104-C03349
 3-1-26
Figure US20180002256A1-20180104-C03350
Figure US20180002256A1-20180104-C03351
Figure US20180002256A1-20180104-C03352
 3-1-27
Figure US20180002256A1-20180104-C03353
Figure US20180002256A1-20180104-C03354
Figure US20180002256A1-20180104-C03355
 3-1-28
Figure US20180002256A1-20180104-C03356
Figure US20180002256A1-20180104-C03357
Figure US20180002256A1-20180104-C03358
 3-1-29
Figure US20180002256A1-20180104-C03359
Figure US20180002256A1-20180104-C03360
Figure US20180002256A1-20180104-C03361
 3-1-30
Figure US20180002256A1-20180104-C03362
Figure US20180002256A1-20180104-C03363
Figure US20180002256A1-20180104-C03364
 3-1-31
Figure US20180002256A1-20180104-C03365
Figure US20180002256A1-20180104-C03366
Figure US20180002256A1-20180104-C03367
 3-1-32
Figure US20180002256A1-20180104-C03368
Figure US20180002256A1-20180104-C03369
Figure US20180002256A1-20180104-C03370
 3-1-33
Figure US20180002256A1-20180104-C03371
Figure US20180002256A1-20180104-C03372
Figure US20180002256A1-20180104-C03373
 3-1-34
Figure US20180002256A1-20180104-C03374
Figure US20180002256A1-20180104-C03375
Figure US20180002256A1-20180104-C03376
 3-1-35
Figure US20180002256A1-20180104-C03377
Figure US20180002256A1-20180104-C03378
Figure US20180002256A1-20180104-C03379
 3-1-36
Figure US20180002256A1-20180104-C03380
Figure US20180002256A1-20180104-C03381
Figure US20180002256A1-20180104-C03382
 3-1-37
Figure US20180002256A1-20180104-C03383
Figure US20180002256A1-20180104-C03384
Figure US20180002256A1-20180104-C03385
 3-1-38
Figure US20180002256A1-20180104-C03386
Figure US20180002256A1-20180104-C03387
Figure US20180002256A1-20180104-C03388
 3-1-39
Figure US20180002256A1-20180104-C03389
Figure US20180002256A1-20180104-C03390
Figure US20180002256A1-20180104-C03391
 3-1-40
Figure US20180002256A1-20180104-C03392
Figure US20180002256A1-20180104-C03393
Figure US20180002256A1-20180104-C03394
 3-1-41
Figure US20180002256A1-20180104-C03395
Figure US20180002256A1-20180104-C03396
Figure US20180002256A1-20180104-C03397
 3-1-42
Figure US20180002256A1-20180104-C03398
Figure US20180002256A1-20180104-C03399
Figure US20180002256A1-20180104-C03400
 3-1-43
Figure US20180002256A1-20180104-C03401
Figure US20180002256A1-20180104-C03402
Figure US20180002256A1-20180104-C03403
 3-1-44
Figure US20180002256A1-20180104-C03404
Figure US20180002256A1-20180104-C03405
Figure US20180002256A1-20180104-C03406
 3-1-45
Figure US20180002256A1-20180104-C03407
Figure US20180002256A1-20180104-C03408
Figure US20180002256A1-20180104-C03409
 3-1-46
Figure US20180002256A1-20180104-C03410
Figure US20180002256A1-20180104-C03411
Figure US20180002256A1-20180104-C03412
 3-1-47
Figure US20180002256A1-20180104-C03413
Figure US20180002256A1-20180104-C03414
Figure US20180002256A1-20180104-C03415
 3-1-48
Figure US20180002256A1-20180104-C03416
Figure US20180002256A1-20180104-C03417
Figure US20180002256A1-20180104-C03418
 3-1-49
Figure US20180002256A1-20180104-C03419
Figure US20180002256A1-20180104-C03420
Figure US20180002256A1-20180104-C03421
 3-1-50
Figure US20180002256A1-20180104-C03422
Figure US20180002256A1-20180104-C03423
Figure US20180002256A1-20180104-C03424
 3-1-51
Figure US20180002256A1-20180104-C03425
Figure US20180002256A1-20180104-C03426
Figure US20180002256A1-20180104-C03427
 3-1-52
Figure US20180002256A1-20180104-C03428
Figure US20180002256A1-20180104-C03429
Figure US20180002256A1-20180104-C03430
 3-1-53
Figure US20180002256A1-20180104-C03431
Figure US20180002256A1-20180104-C03432
Figure US20180002256A1-20180104-C03433
 3-1-54
Figure US20180002256A1-20180104-C03434
Figure US20180002256A1-20180104-C03435
Figure US20180002256A1-20180104-C03436
 3-1-55
Figure US20180002256A1-20180104-C03437
Figure US20180002256A1-20180104-C03438
Figure US20180002256A1-20180104-C03439
 3-1-56
Figure US20180002256A1-20180104-C03440
Figure US20180002256A1-20180104-C03441
Figure US20180002256A1-20180104-C03442
 3-1-57
Figure US20180002256A1-20180104-C03443
Figure US20180002256A1-20180104-C03444
Figure US20180002256A1-20180104-C03445
 3-1-58
Figure US20180002256A1-20180104-C03446
Figure US20180002256A1-20180104-C03447
Figure US20180002256A1-20180104-C03448
 3-1-59
Figure US20180002256A1-20180104-C03449
Figure US20180002256A1-20180104-C03450
Figure US20180002256A1-20180104-C03451
 3-1-60
Figure US20180002256A1-20180104-C03452
Figure US20180002256A1-20180104-C03453
Figure US20180002256A1-20180104-C03454
 3-1-61
Figure US20180002256A1-20180104-C03455
Figure US20180002256A1-20180104-C03456
Figure US20180002256A1-20180104-C03457
 3-1-62
Figure US20180002256A1-20180104-C03458
Figure US20180002256A1-20180104-C03459
Figure US20180002256A1-20180104-C03460
 3-1-63
Figure US20180002256A1-20180104-C03461
Figure US20180002256A1-20180104-C03462
Figure US20180002256A1-20180104-C03463
 3-1-64
Figure US20180002256A1-20180104-C03464
Figure US20180002256A1-20180104-C03465
Figure US20180002256A1-20180104-C03466
 3-1-65
Figure US20180002256A1-20180104-C03467
Figure US20180002256A1-20180104-C03468
Figure US20180002256A1-20180104-C03469
 3-1-66
Figure US20180002256A1-20180104-C03470
Figure US20180002256A1-20180104-C03471
Figure US20180002256A1-20180104-C03472
 3-1-67
Figure US20180002256A1-20180104-C03473
Figure US20180002256A1-20180104-C03474
Figure US20180002256A1-20180104-C03475
 3-1-68
Figure US20180002256A1-20180104-C03476
Figure US20180002256A1-20180104-C03477
Figure US20180002256A1-20180104-C03478
 3-1-69
Figure US20180002256A1-20180104-C03479
Figure US20180002256A1-20180104-C03480
Figure US20180002256A1-20180104-C03481
 3-1-70
Figure US20180002256A1-20180104-C03482
Figure US20180002256A1-20180104-C03483
Figure US20180002256A1-20180104-C03484
 3-1-71
Figure US20180002256A1-20180104-C03485
Figure US20180002256A1-20180104-C03486
Figure US20180002256A1-20180104-C03487
 3-1-72
Figure US20180002256A1-20180104-C03488
Figure US20180002256A1-20180104-C03489
Figure US20180002256A1-20180104-C03490
 3-1-73
Figure US20180002256A1-20180104-C03491
Figure US20180002256A1-20180104-C03492
Figure US20180002256A1-20180104-C03493
 3-1-74
Figure US20180002256A1-20180104-C03494
Figure US20180002256A1-20180104-C03495
Figure US20180002256A1-20180104-C03496
 3-1-75
Figure US20180002256A1-20180104-C03497
Figure US20180002256A1-20180104-C03498
Figure US20180002256A1-20180104-C03499
 3-1-76
Figure US20180002256A1-20180104-C03500
Figure US20180002256A1-20180104-C03501
Figure US20180002256A1-20180104-C03502
 3-1-77
Figure US20180002256A1-20180104-C03503
Figure US20180002256A1-20180104-C03504
Figure US20180002256A1-20180104-C03505
 3-1-78
Figure US20180002256A1-20180104-C03506
Figure US20180002256A1-20180104-C03507
Figure US20180002256A1-20180104-C03508
 3-1-79
Figure US20180002256A1-20180104-C03509
Figure US20180002256A1-20180104-C03510
Figure US20180002256A1-20180104-C03511
 3-1-80
Figure US20180002256A1-20180104-C03512
Figure US20180002256A1-20180104-C03513
Figure US20180002256A1-20180104-C03514
 3-1-81
Figure US20180002256A1-20180104-C03515
Figure US20180002256A1-20180104-C03516
Figure US20180002256A1-20180104-C03517
 3-1-82
Figure US20180002256A1-20180104-C03518
Figure US20180002256A1-20180104-C03519
Figure US20180002256A1-20180104-C03520
 3-1-83
Figure US20180002256A1-20180104-C03521
Figure US20180002256A1-20180104-C03522
Figure US20180002256A1-20180104-C03523
 3-1-84
Figure US20180002256A1-20180104-C03524
Figure US20180002256A1-20180104-C03525
Figure US20180002256A1-20180104-C03526
 3-1-85
Figure US20180002256A1-20180104-C03527
Figure US20180002256A1-20180104-C03528
Figure US20180002256A1-20180104-C03529
 3-1-86
Figure US20180002256A1-20180104-C03530
Figure US20180002256A1-20180104-C03531
Figure US20180002256A1-20180104-C03532
 3-1-87
Figure US20180002256A1-20180104-C03533
Figure US20180002256A1-20180104-C03534
Figure US20180002256A1-20180104-C03535
 3-1-88
Figure US20180002256A1-20180104-C03536
Figure US20180002256A1-20180104-C03537
Figure US20180002256A1-20180104-C03538
 3-1-89
Figure US20180002256A1-20180104-C03539
Figure US20180002256A1-20180104-C03540
Figure US20180002256A1-20180104-C03541
 3-1-90
Figure US20180002256A1-20180104-C03542
Figure US20180002256A1-20180104-C03543
Figure US20180002256A1-20180104-C03544
 3-1-91
Figure US20180002256A1-20180104-C03545
Figure US20180002256A1-20180104-C03546
Figure US20180002256A1-20180104-C03547
 3-1-92
Figure US20180002256A1-20180104-C03548
Figure US20180002256A1-20180104-C03549
Figure US20180002256A1-20180104-C03550
 3-1-93
Figure US20180002256A1-20180104-C03551
Figure US20180002256A1-20180104-C03552
Figure US20180002256A1-20180104-C03553
 3-1-94
Figure US20180002256A1-20180104-C03554
Figure US20180002256A1-20180104-C03555
Figure US20180002256A1-20180104-C03556
 3-1-95
Figure US20180002256A1-20180104-C03557
Figure US20180002256A1-20180104-C03558
Figure US20180002256A1-20180104-C03559
 3-1-96
Figure US20180002256A1-20180104-C03560
Figure US20180002256A1-20180104-C03561
Figure US20180002256A1-20180104-C03562
 3-1-97
Figure US20180002256A1-20180104-C03563
Figure US20180002256A1-20180104-C03564
Figure US20180002256A1-20180104-C03565
 3-1-98
Figure US20180002256A1-20180104-C03566
Figure US20180002256A1-20180104-C03567
Figure US20180002256A1-20180104-C03568
 3-1-99
Figure US20180002256A1-20180104-C03569
Figure US20180002256A1-20180104-C03570
Figure US20180002256A1-20180104-C03571
 3-1-100
Figure US20180002256A1-20180104-C03572
Figure US20180002256A1-20180104-C03573
Figure US20180002256A1-20180104-C03574
 3-1-101
Figure US20180002256A1-20180104-C03575
Figure US20180002256A1-20180104-C03576
Figure US20180002256A1-20180104-C03577
 3-1-102
Figure US20180002256A1-20180104-C03578
Figure US20180002256A1-20180104-C03579
Figure US20180002256A1-20180104-C03580
 3-1-103
Figure US20180002256A1-20180104-C03581
Figure US20180002256A1-20180104-C03582
Figure US20180002256A1-20180104-C03583
 3-1-104
Figure US20180002256A1-20180104-C03584
Figure US20180002256A1-20180104-C03585
Figure US20180002256A1-20180104-C03586
9. The double Spiro structure compound of claim 1, wherein the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-2, and in the following Chemical Formula 3-2, L2, Ar3 and Ar4 are any one selected from among 3-2-1 to 3-2-104 of the following Table 3:
Figure US20180002256A1-20180104-C03587
TABLE 3 − − −L2− − − − − −Ar3 − − −Ar4− − − 3-2-1 Direct bond
Figure US20180002256A1-20180104-C03588
Figure US20180002256A1-20180104-C03589
 3-2-2 Direct bond
Figure US20180002256A1-20180104-C03590
Figure US20180002256A1-20180104-C03591
 3-2-3 Direct bond
Figure US20180002256A1-20180104-C03592
Figure US20180002256A1-20180104-C03593
 3-2-4 Direct bond
Figure US20180002256A1-20180104-C03594
Figure US20180002256A1-20180104-C03595
 3-2-5 Direct bond
Figure US20180002256A1-20180104-C03596
Figure US20180002256A1-20180104-C03597
 3-2-6 Direct bond
Figure US20180002256A1-20180104-C03598
Figure US20180002256A1-20180104-C03599
 3-2-7 Direct bond
Figure US20180002256A1-20180104-C03600
Figure US20180002256A1-20180104-C03601
 3-2-8 Direct bond
Figure US20180002256A1-20180104-C03602
Figure US20180002256A1-20180104-C03603
 3-2-9 Direct bond
Figure US20180002256A1-20180104-C03604
Figure US20180002256A1-20180104-C03605
 3-2-10 Direct bond
Figure US20180002256A1-20180104-C03606
Figure US20180002256A1-20180104-C03607
 3-2-11 Direct bond
Figure US20180002256A1-20180104-C03608
Figure US20180002256A1-20180104-C03609
 3-2-12
Figure US20180002256A1-20180104-C03610
Figure US20180002256A1-20180104-C03611
Figure US20180002256A1-20180104-C03612
 3-2-13
Figure US20180002256A1-20180104-C03613
Figure US20180002256A1-20180104-C03614
Figure US20180002256A1-20180104-C03615
 3-2-14
Figure US20180002256A1-20180104-C03616
Figure US20180002256A1-20180104-C03617
Figure US20180002256A1-20180104-C03618
 3-2-15
Figure US20180002256A1-20180104-C03619
Figure US20180002256A1-20180104-C03620
Figure US20180002256A1-20180104-C03621
 3-2-16
Figure US20180002256A1-20180104-C03622
Figure US20180002256A1-20180104-C03623
Figure US20180002256A1-20180104-C03624
 3-2-17
Figure US20180002256A1-20180104-C03625
Figure US20180002256A1-20180104-C03626
Figure US20180002256A1-20180104-C03627
 3-2-18
Figure US20180002256A1-20180104-C03628
Figure US20180002256A1-20180104-C03629
Figure US20180002256A1-20180104-C03630
 3-2-19
Figure US20180002256A1-20180104-C03631
Figure US20180002256A1-20180104-C03632
Figure US20180002256A1-20180104-C03633
 3-2-20
Figure US20180002256A1-20180104-C03634
Figure US20180002256A1-20180104-C03635
Figure US20180002256A1-20180104-C03636
 3-2-21
Figure US20180002256A1-20180104-C03637
Figure US20180002256A1-20180104-C03638
Figure US20180002256A1-20180104-C03639
 3-2-22
Figure US20180002256A1-20180104-C03640
Figure US20180002256A1-20180104-C03641
Figure US20180002256A1-20180104-C03642
 3-2-23
Figure US20180002256A1-20180104-C03643
Figure US20180002256A1-20180104-C03644
Figure US20180002256A1-20180104-C03645
 3-2-24
Figure US20180002256A1-20180104-C03646
Figure US20180002256A1-20180104-C03647
Figure US20180002256A1-20180104-C03648
 3-2-25
Figure US20180002256A1-20180104-C03649
Figure US20180002256A1-20180104-C03650
Figure US20180002256A1-20180104-C03651
 3-2-26
Figure US20180002256A1-20180104-C03652
Figure US20180002256A1-20180104-C03653
Figure US20180002256A1-20180104-C03654
 3-2-27
Figure US20180002256A1-20180104-C03655
Figure US20180002256A1-20180104-C03656
Figure US20180002256A1-20180104-C03657
 3-2-28
Figure US20180002256A1-20180104-C03658
Figure US20180002256A1-20180104-C03659
Figure US20180002256A1-20180104-C03660
 3-2-29
Figure US20180002256A1-20180104-C03661
Figure US20180002256A1-20180104-C03662
Figure US20180002256A1-20180104-C03663
 3-2-30
Figure US20180002256A1-20180104-C03664
Figure US20180002256A1-20180104-C03665
Figure US20180002256A1-20180104-C03666
 3-2-31
Figure US20180002256A1-20180104-C03667
Figure US20180002256A1-20180104-C03668
Figure US20180002256A1-20180104-C03669
 3-2-32
Figure US20180002256A1-20180104-C03670
Figure US20180002256A1-20180104-C03671
Figure US20180002256A1-20180104-C03672
 3-2-33
Figure US20180002256A1-20180104-C03673
Figure US20180002256A1-20180104-C03674
Figure US20180002256A1-20180104-C03675
 3-2-34
Figure US20180002256A1-20180104-C03676
Figure US20180002256A1-20180104-C03677
Figure US20180002256A1-20180104-C03678
 3-2-35
Figure US20180002256A1-20180104-C03679
Figure US20180002256A1-20180104-C03680
Figure US20180002256A1-20180104-C03681
 3-2-36
Figure US20180002256A1-20180104-C03682
Figure US20180002256A1-20180104-C03683
Figure US20180002256A1-20180104-C03684
 3-2-37
Figure US20180002256A1-20180104-C03685
Figure US20180002256A1-20180104-C03686
Figure US20180002256A1-20180104-C03687
 3-2-38
Figure US20180002256A1-20180104-C03688
Figure US20180002256A1-20180104-C03689
Figure US20180002256A1-20180104-C03690
 3-2-39
Figure US20180002256A1-20180104-C03691
Figure US20180002256A1-20180104-C03692
Figure US20180002256A1-20180104-C03693
 3-2-40
Figure US20180002256A1-20180104-C03694
Figure US20180002256A1-20180104-C03695
Figure US20180002256A1-20180104-C03696
 3-2-41
Figure US20180002256A1-20180104-C03697
Figure US20180002256A1-20180104-C03698
Figure US20180002256A1-20180104-C03699
 3-2-42
Figure US20180002256A1-20180104-C03700
Figure US20180002256A1-20180104-C03701
Figure US20180002256A1-20180104-C03702
 3-2-43
Figure US20180002256A1-20180104-C03703
Figure US20180002256A1-20180104-C03704
Figure US20180002256A1-20180104-C03705
 3-2-44
Figure US20180002256A1-20180104-C03706
Figure US20180002256A1-20180104-C03707
Figure US20180002256A1-20180104-C03708
 3-2-45
Figure US20180002256A1-20180104-C03709
Figure US20180002256A1-20180104-C03710
Figure US20180002256A1-20180104-C03711
 3-2-46
Figure US20180002256A1-20180104-C03712
Figure US20180002256A1-20180104-C03713
Figure US20180002256A1-20180104-C03714
 3-2-47
Figure US20180002256A1-20180104-C03715
Figure US20180002256A1-20180104-C03716
Figure US20180002256A1-20180104-C03717
 3-2-48
Figure US20180002256A1-20180104-C03718
Figure US20180002256A1-20180104-C03719
Figure US20180002256A1-20180104-C03720
 3-2-49
Figure US20180002256A1-20180104-C03721
Figure US20180002256A1-20180104-C03722
Figure US20180002256A1-20180104-C03723
 3-2-50
Figure US20180002256A1-20180104-C03724
Figure US20180002256A1-20180104-C03725
Figure US20180002256A1-20180104-C03726
 3-2-51
Figure US20180002256A1-20180104-C03727
Figure US20180002256A1-20180104-C03728
Figure US20180002256A1-20180104-C03729
 3-2-52
Figure US20180002256A1-20180104-C03730
Figure US20180002256A1-20180104-C03731
Figure US20180002256A1-20180104-C03732
 3-2-53
Figure US20180002256A1-20180104-C03733
Figure US20180002256A1-20180104-C03734
Figure US20180002256A1-20180104-C03735
 3-2-54
Figure US20180002256A1-20180104-C03736
Figure US20180002256A1-20180104-C03737
Figure US20180002256A1-20180104-C03738
 3-2-55
Figure US20180002256A1-20180104-C03739
Figure US20180002256A1-20180104-C03740
Figure US20180002256A1-20180104-C03741
 3-2-56
Figure US20180002256A1-20180104-C03742
Figure US20180002256A1-20180104-C03743
Figure US20180002256A1-20180104-C03744
 3-2-57
Figure US20180002256A1-20180104-C03745
Figure US20180002256A1-20180104-C03746
Figure US20180002256A1-20180104-C03747
 3-2-58
Figure US20180002256A1-20180104-C03748
Figure US20180002256A1-20180104-C03749
Figure US20180002256A1-20180104-C03750
 3-2-59
Figure US20180002256A1-20180104-C03751
Figure US20180002256A1-20180104-C03752
Figure US20180002256A1-20180104-C03753
 3-2-60
Figure US20180002256A1-20180104-C03754
Figure US20180002256A1-20180104-C03755
Figure US20180002256A1-20180104-C03756
 3-2-61
Figure US20180002256A1-20180104-C03757
Figure US20180002256A1-20180104-C03758
Figure US20180002256A1-20180104-C03759
 3-2-62
Figure US20180002256A1-20180104-C03760
Figure US20180002256A1-20180104-C03761
Figure US20180002256A1-20180104-C03762
 3-2-63
Figure US20180002256A1-20180104-C03763
Figure US20180002256A1-20180104-C03764
Figure US20180002256A1-20180104-C03765
 3-2-64
Figure US20180002256A1-20180104-C03766
Figure US20180002256A1-20180104-C03767
Figure US20180002256A1-20180104-C03768
 3-2-65
Figure US20180002256A1-20180104-C03769
Figure US20180002256A1-20180104-C03770
Figure US20180002256A1-20180104-C03771
 3-2-66
Figure US20180002256A1-20180104-C03772
Figure US20180002256A1-20180104-C03773
Figure US20180002256A1-20180104-C03774
 3-2-67
Figure US20180002256A1-20180104-C03775
Figure US20180002256A1-20180104-C03776
Figure US20180002256A1-20180104-C03777
 3-2-68
Figure US20180002256A1-20180104-C03778
Figure US20180002256A1-20180104-C03779
Figure US20180002256A1-20180104-C03780
 3-2-69
Figure US20180002256A1-20180104-C03781
Figure US20180002256A1-20180104-C03782
Figure US20180002256A1-20180104-C03783
 3-2-70
Figure US20180002256A1-20180104-C03784
Figure US20180002256A1-20180104-C03785
Figure US20180002256A1-20180104-C03786
 3-2-71
Figure US20180002256A1-20180104-C03787
Figure US20180002256A1-20180104-C03788
Figure US20180002256A1-20180104-C03789
 3-2-72
Figure US20180002256A1-20180104-C03790
Figure US20180002256A1-20180104-C03791
Figure US20180002256A1-20180104-C03792
 3-2-73
Figure US20180002256A1-20180104-C03793
Figure US20180002256A1-20180104-C03794
Figure US20180002256A1-20180104-C03795
 3-2-74
Figure US20180002256A1-20180104-C03796
Figure US20180002256A1-20180104-C03797
Figure US20180002256A1-20180104-C03798
 3-2-75
Figure US20180002256A1-20180104-C03799
Figure US20180002256A1-20180104-C03800
Figure US20180002256A1-20180104-C03801
 3-2-76
Figure US20180002256A1-20180104-C03802
Figure US20180002256A1-20180104-C03803
Figure US20180002256A1-20180104-C03804
 3-2-77
Figure US20180002256A1-20180104-C03805
Figure US20180002256A1-20180104-C03806
Figure US20180002256A1-20180104-C03807
 3-2-78
Figure US20180002256A1-20180104-C03808
Figure US20180002256A1-20180104-C03809
Figure US20180002256A1-20180104-C03810
 3-2-79
Figure US20180002256A1-20180104-C03811
Figure US20180002256A1-20180104-C03812
Figure US20180002256A1-20180104-C03813
 3-2-80
Figure US20180002256A1-20180104-C03814
Figure US20180002256A1-20180104-C03815
Figure US20180002256A1-20180104-C03816
 3-2-81
Figure US20180002256A1-20180104-C03817
Figure US20180002256A1-20180104-C03818
Figure US20180002256A1-20180104-C03819
 3-2-82
Figure US20180002256A1-20180104-C03820
Figure US20180002256A1-20180104-C03821
Figure US20180002256A1-20180104-C03822
 3-2-83
Figure US20180002256A1-20180104-C03823
Figure US20180002256A1-20180104-C03824
Figure US20180002256A1-20180104-C03825
 3-2-84
Figure US20180002256A1-20180104-C03826
Figure US20180002256A1-20180104-C03827
Figure US20180002256A1-20180104-C03828
 3-2-85
Figure US20180002256A1-20180104-C03829
Figure US20180002256A1-20180104-C03830
Figure US20180002256A1-20180104-C03831
 3-2-86
Figure US20180002256A1-20180104-C03832
Figure US20180002256A1-20180104-C03833
Figure US20180002256A1-20180104-C03834
 3-2-87
Figure US20180002256A1-20180104-C03835
Figure US20180002256A1-20180104-C03836
Figure US20180002256A1-20180104-C03837
 3-2-88
Figure US20180002256A1-20180104-C03838
Figure US20180002256A1-20180104-C03839
Figure US20180002256A1-20180104-C03840
 3-2-89
Figure US20180002256A1-20180104-C03841
Figure US20180002256A1-20180104-C03842
Figure US20180002256A1-20180104-C03843
 3-2-90
Figure US20180002256A1-20180104-C03844
Figure US20180002256A1-20180104-C03845
Figure US20180002256A1-20180104-C03846
 3-2-91
Figure US20180002256A1-20180104-C03847
Figure US20180002256A1-20180104-C03848
Figure US20180002256A1-20180104-C03849
 3-2-92
Figure US20180002256A1-20180104-C03850
Figure US20180002256A1-20180104-C03851
Figure US20180002256A1-20180104-C03852
 3-2-93
Figure US20180002256A1-20180104-C03853
Figure US20180002256A1-20180104-C03854
Figure US20180002256A1-20180104-C03855
 3-2-94
Figure US20180002256A1-20180104-C03856
Figure US20180002256A1-20180104-C03857
Figure US20180002256A1-20180104-C03858
 3-2-95
Figure US20180002256A1-20180104-C03859
Figure US20180002256A1-20180104-C03860
Figure US20180002256A1-20180104-C03861
 3-2-96
Figure US20180002256A1-20180104-C03862
Figure US20180002256A1-20180104-C03863
Figure US20180002256A1-20180104-C03864
 3-2-97
Figure US20180002256A1-20180104-C03865
Figure US20180002256A1-20180104-C03866
Figure US20180002256A1-20180104-C03867
 3-2-98
Figure US20180002256A1-20180104-C03868
Figure US20180002256A1-20180104-C03869
Figure US20180002256A1-20180104-C03870
 3-2-99
Figure US20180002256A1-20180104-C03871
Figure US20180002256A1-20180104-C03872
Figure US20180002256A1-20180104-C03873
 3-2-100
Figure US20180002256A1-20180104-C03874
Figure US20180002256A1-20180104-C03875
Figure US20180002256A1-20180104-C03876
 3-2-101
Figure US20180002256A1-20180104-C03877
Figure US20180002256A1-20180104-C03878
Figure US20180002256A1-20180104-C03879
 3-2-102
Figure US20180002256A1-20180104-C03880
Figure US20180002256A1-20180104-C03881
Figure US20180002256A1-20180104-C03882
 3-2-103
Figure US20180002256A1-20180104-C03883
Figure US20180002256A1-20180104-C03884
Figure US20180002256A1-20180104-C03885
 3-2-104
Figure US20180002256A1-20180104-C03886
Figure US20180002256A1-20180104-C03887
Figure US20180002256A1-20180104-C03888
10. The double Spiro structure compound of claim 1, wherein in the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-3, and in the following Chemical Formula 3-3, L2, Ar3 and Ar4 are any one selected from among 3-3-1 to 3-3-104 of the following Table 4:
Figure US20180002256A1-20180104-C03889
TABLE 4 − − −L4− − − − − −Ar3 − − −Ar4 3-3-1 Direct bond
Figure US20180002256A1-20180104-C03890
Figure US20180002256A1-20180104-C03891
 3-3-2 Direct bond
Figure US20180002256A1-20180104-C03892
Figure US20180002256A1-20180104-C03893
 3-3-3 Direct bond
Figure US20180002256A1-20180104-C03894
Figure US20180002256A1-20180104-C03895
 3-3-4 Direct bond
Figure US20180002256A1-20180104-C03896
Figure US20180002256A1-20180104-C03897
 3-3-5 Direct bond
Figure US20180002256A1-20180104-C03898
Figure US20180002256A1-20180104-C03899
 3-3-6 Direct bond
Figure US20180002256A1-20180104-C03900
Figure US20180002256A1-20180104-C03901
 3-3-7 Direct bond
Figure US20180002256A1-20180104-C03902
Figure US20180002256A1-20180104-C03903
 3-3-8 Direct bond
Figure US20180002256A1-20180104-C03904
Figure US20180002256A1-20180104-C03905
 3-3-9 Direct bond
Figure US20180002256A1-20180104-C03906
Figure US20180002256A1-20180104-C03907
 3-3-10 Direct bond
Figure US20180002256A1-20180104-C03908
Figure US20180002256A1-20180104-C03909
 3-3-11 Direct bond
Figure US20180002256A1-20180104-C03910
Figure US20180002256A1-20180104-C03911
 3-3-12
Figure US20180002256A1-20180104-C03912
Figure US20180002256A1-20180104-C03913
Figure US20180002256A1-20180104-C03914
 3-3-13
Figure US20180002256A1-20180104-C03915
Figure US20180002256A1-20180104-C03916
Figure US20180002256A1-20180104-C03917
 3-3-14
Figure US20180002256A1-20180104-C03918
Figure US20180002256A1-20180104-C03919
Figure US20180002256A1-20180104-C03920
 3-3-15
Figure US20180002256A1-20180104-C03921
Figure US20180002256A1-20180104-C03922
Figure US20180002256A1-20180104-C03923
 3-3-16
Figure US20180002256A1-20180104-C03924
Figure US20180002256A1-20180104-C03925
Figure US20180002256A1-20180104-C03926
 3-3-17
Figure US20180002256A1-20180104-C03927
Figure US20180002256A1-20180104-C03928
Figure US20180002256A1-20180104-C03929
 3-3-18
Figure US20180002256A1-20180104-C03930
Figure US20180002256A1-20180104-C03931
Figure US20180002256A1-20180104-C03932
 3-3-19
Figure US20180002256A1-20180104-C03933
Figure US20180002256A1-20180104-C03934
Figure US20180002256A1-20180104-C03935
 3-3-20
Figure US20180002256A1-20180104-C03936
Figure US20180002256A1-20180104-C03937
Figure US20180002256A1-20180104-C03938
 3-3-21
Figure US20180002256A1-20180104-C03939
Figure US20180002256A1-20180104-C03940
Figure US20180002256A1-20180104-C03941
 3-3-22
Figure US20180002256A1-20180104-C03942
Figure US20180002256A1-20180104-C03943
Figure US20180002256A1-20180104-C03944
 3-3-23
Figure US20180002256A1-20180104-C03945
Figure US20180002256A1-20180104-C03946
Figure US20180002256A1-20180104-C03947
 3-3-24
Figure US20180002256A1-20180104-C03948
Figure US20180002256A1-20180104-C03949
Figure US20180002256A1-20180104-C03950
 3-3-25
Figure US20180002256A1-20180104-C03951
Figure US20180002256A1-20180104-C03952
Figure US20180002256A1-20180104-C03953
 3-3-26
Figure US20180002256A1-20180104-C03954
Figure US20180002256A1-20180104-C03955
Figure US20180002256A1-20180104-C03956
 3-3-27
Figure US20180002256A1-20180104-C03957
Figure US20180002256A1-20180104-C03958
Figure US20180002256A1-20180104-C03959
 3-3-28
Figure US20180002256A1-20180104-C03960
Figure US20180002256A1-20180104-C03961
Figure US20180002256A1-20180104-C03962
 3-3-29
Figure US20180002256A1-20180104-C03963
Figure US20180002256A1-20180104-C03964
Figure US20180002256A1-20180104-C03965
 3-3-30
Figure US20180002256A1-20180104-C03966
Figure US20180002256A1-20180104-C03967
Figure US20180002256A1-20180104-C03968
 3-3-31
Figure US20180002256A1-20180104-C03969
Figure US20180002256A1-20180104-C03970
Figure US20180002256A1-20180104-C03971
 3-3-32
Figure US20180002256A1-20180104-C03972
Figure US20180002256A1-20180104-C03973
Figure US20180002256A1-20180104-C03974
 3-3-33
Figure US20180002256A1-20180104-C03975
Figure US20180002256A1-20180104-C03976
Figure US20180002256A1-20180104-C03977
 3-3-34
Figure US20180002256A1-20180104-C03978
Figure US20180002256A1-20180104-C03979
Figure US20180002256A1-20180104-C03980
 3-3-35
Figure US20180002256A1-20180104-C03981
Figure US20180002256A1-20180104-C03982
Figure US20180002256A1-20180104-C03983
 3-3-36
Figure US20180002256A1-20180104-C03984
Figure US20180002256A1-20180104-C03985
Figure US20180002256A1-20180104-C03986
 3-3-37
Figure US20180002256A1-20180104-C03987
Figure US20180002256A1-20180104-C03988
Figure US20180002256A1-20180104-C03989
 3-3-38
Figure US20180002256A1-20180104-C03990
Figure US20180002256A1-20180104-C03991
Figure US20180002256A1-20180104-C03992
 3-3-39
Figure US20180002256A1-20180104-C03993
Figure US20180002256A1-20180104-C03994
Figure US20180002256A1-20180104-C03995
 3-3-40
Figure US20180002256A1-20180104-C03996
Figure US20180002256A1-20180104-C03997
Figure US20180002256A1-20180104-C03998
 3-3-41
Figure US20180002256A1-20180104-C03999
Figure US20180002256A1-20180104-C04000
Figure US20180002256A1-20180104-C04001
 3-3-42
Figure US20180002256A1-20180104-C04002
Figure US20180002256A1-20180104-C04003
Figure US20180002256A1-20180104-C04004
 3-3-43
Figure US20180002256A1-20180104-C04005
Figure US20180002256A1-20180104-C04006
Figure US20180002256A1-20180104-C04007
 3-3-44
Figure US20180002256A1-20180104-C04008
Figure US20180002256A1-20180104-C04009
Figure US20180002256A1-20180104-C04010
 3-3-45
Figure US20180002256A1-20180104-C04011
Figure US20180002256A1-20180104-C04012
Figure US20180002256A1-20180104-C04013
 3-3-46
Figure US20180002256A1-20180104-C04014
Figure US20180002256A1-20180104-C04015
Figure US20180002256A1-20180104-C04016
 3-3-47
Figure US20180002256A1-20180104-C04017
Figure US20180002256A1-20180104-C04018
Figure US20180002256A1-20180104-C04019
 3-3-48
Figure US20180002256A1-20180104-C04020
Figure US20180002256A1-20180104-C04021
Figure US20180002256A1-20180104-C04022
 3-3-49
Figure US20180002256A1-20180104-C04023
Figure US20180002256A1-20180104-C04024
Figure US20180002256A1-20180104-C04025
 3-3-50
Figure US20180002256A1-20180104-C04026
Figure US20180002256A1-20180104-C04027
Figure US20180002256A1-20180104-C04028
 3-3-51
Figure US20180002256A1-20180104-C04029
Figure US20180002256A1-20180104-C04030
Figure US20180002256A1-20180104-C04031
 3-3-52
Figure US20180002256A1-20180104-C04032
Figure US20180002256A1-20180104-C04033
Figure US20180002256A1-20180104-C04034
 3-3-53
Figure US20180002256A1-20180104-C04035
Figure US20180002256A1-20180104-C04036
Figure US20180002256A1-20180104-C04037
 3-3-54
Figure US20180002256A1-20180104-C04038
Figure US20180002256A1-20180104-C04039
Figure US20180002256A1-20180104-C04040
 3-3-55
Figure US20180002256A1-20180104-C04041
Figure US20180002256A1-20180104-C04042
Figure US20180002256A1-20180104-C04043
 3-3-56
Figure US20180002256A1-20180104-C04044
Figure US20180002256A1-20180104-C04045
Figure US20180002256A1-20180104-C04046
 3-3-57
Figure US20180002256A1-20180104-C04047
Figure US20180002256A1-20180104-C04048
Figure US20180002256A1-20180104-C04049
 3-3-58
Figure US20180002256A1-20180104-C04050
Figure US20180002256A1-20180104-C04051
Figure US20180002256A1-20180104-C04052
 3-3-59
Figure US20180002256A1-20180104-C04053
Figure US20180002256A1-20180104-C04054
Figure US20180002256A1-20180104-C04055
 3-3-60
Figure US20180002256A1-20180104-C04056
Figure US20180002256A1-20180104-C04057
Figure US20180002256A1-20180104-C04058
 3-3-61
Figure US20180002256A1-20180104-C04059
Figure US20180002256A1-20180104-C04060
Figure US20180002256A1-20180104-C04061
 3-3-62
Figure US20180002256A1-20180104-C04062
Figure US20180002256A1-20180104-C04063
Figure US20180002256A1-20180104-C04064
 3-3-63
Figure US20180002256A1-20180104-C04065
Figure US20180002256A1-20180104-C04066
Figure US20180002256A1-20180104-C04067
 3-3-64
Figure US20180002256A1-20180104-C04068
Figure US20180002256A1-20180104-C04069
Figure US20180002256A1-20180104-C04070
 3-3-65
Figure US20180002256A1-20180104-C04071
Figure US20180002256A1-20180104-C04072
Figure US20180002256A1-20180104-C04073
 3-3-66
Figure US20180002256A1-20180104-C04074
Figure US20180002256A1-20180104-C04075
Figure US20180002256A1-20180104-C04076
 3-3-67
Figure US20180002256A1-20180104-C04077
Figure US20180002256A1-20180104-C04078
Figure US20180002256A1-20180104-C04079
 3-3-68
Figure US20180002256A1-20180104-C04080
Figure US20180002256A1-20180104-C04081
Figure US20180002256A1-20180104-C04082
 3-3-69
Figure US20180002256A1-20180104-C04083
Figure US20180002256A1-20180104-C04084
Figure US20180002256A1-20180104-C04085
 3-3-70
Figure US20180002256A1-20180104-C04086
Figure US20180002256A1-20180104-C04087
Figure US20180002256A1-20180104-C04088
 3-3-71
Figure US20180002256A1-20180104-C04089
Figure US20180002256A1-20180104-C04090
Figure US20180002256A1-20180104-C04091
 3-3-72
Figure US20180002256A1-20180104-C04092
Figure US20180002256A1-20180104-C04093
Figure US20180002256A1-20180104-C04094
 3-3-73
Figure US20180002256A1-20180104-C04095
Figure US20180002256A1-20180104-C04096
Figure US20180002256A1-20180104-C04097
 3-3-74
Figure US20180002256A1-20180104-C04098
Figure US20180002256A1-20180104-C04099
Figure US20180002256A1-20180104-C04100
 3-3-75
Figure US20180002256A1-20180104-C04101
Figure US20180002256A1-20180104-C04102
Figure US20180002256A1-20180104-C04103
 3-3-76
Figure US20180002256A1-20180104-C04104
Figure US20180002256A1-20180104-C04105
Figure US20180002256A1-20180104-C04106
 3-3-77
Figure US20180002256A1-20180104-C04107
Figure US20180002256A1-20180104-C04108
Figure US20180002256A1-20180104-C04109
 3-3-78
Figure US20180002256A1-20180104-C04110
Figure US20180002256A1-20180104-C04111
Figure US20180002256A1-20180104-C04112
 3-3-79
Figure US20180002256A1-20180104-C04113
Figure US20180002256A1-20180104-C04114
Figure US20180002256A1-20180104-C04115
 3-3-80
Figure US20180002256A1-20180104-C04116
Figure US20180002256A1-20180104-C04117
Figure US20180002256A1-20180104-C04118
 3-3-81
Figure US20180002256A1-20180104-C04119
Figure US20180002256A1-20180104-C04120
Figure US20180002256A1-20180104-C04121
 3-3-82
Figure US20180002256A1-20180104-C04122
Figure US20180002256A1-20180104-C04123
Figure US20180002256A1-20180104-C04124
 3-3-83
Figure US20180002256A1-20180104-C04125
Figure US20180002256A1-20180104-C04126
Figure US20180002256A1-20180104-C04127
 3-3-84
Figure US20180002256A1-20180104-C04128
Figure US20180002256A1-20180104-C04129
Figure US20180002256A1-20180104-C04130
 3-3-85
Figure US20180002256A1-20180104-C04131
Figure US20180002256A1-20180104-C04132
Figure US20180002256A1-20180104-C04133
 3-3-86
Figure US20180002256A1-20180104-C04134
Figure US20180002256A1-20180104-C04135
Figure US20180002256A1-20180104-C04136
 3-3-87
Figure US20180002256A1-20180104-C04137
Figure US20180002256A1-20180104-C04138
Figure US20180002256A1-20180104-C04139
 3-3-88
Figure US20180002256A1-20180104-C04140
Figure US20180002256A1-20180104-C04141
Figure US20180002256A1-20180104-C04142
 3-3-89
Figure US20180002256A1-20180104-C04143
Figure US20180002256A1-20180104-C04144
Figure US20180002256A1-20180104-C04145
 3-3-90
Figure US20180002256A1-20180104-C04146
Figure US20180002256A1-20180104-C04147
Figure US20180002256A1-20180104-C04148
 3-3-91
Figure US20180002256A1-20180104-C04149
Figure US20180002256A1-20180104-C04150
Figure US20180002256A1-20180104-C04151
 3-3-92
Figure US20180002256A1-20180104-C04152
Figure US20180002256A1-20180104-C04153
Figure US20180002256A1-20180104-C04154
 3-3-93
Figure US20180002256A1-20180104-C04155
Figure US20180002256A1-20180104-C04156
Figure US20180002256A1-20180104-C04157
 3-3-94
Figure US20180002256A1-20180104-C04158
Figure US20180002256A1-20180104-C04159
Figure US20180002256A1-20180104-C04160
 3-3-95
Figure US20180002256A1-20180104-C04161
Figure US20180002256A1-20180104-C04162
Figure US20180002256A1-20180104-C04163
 3-3-96
Figure US20180002256A1-20180104-C04164
Figure US20180002256A1-20180104-C04165
Figure US20180002256A1-20180104-C04166
 3-3-97
Figure US20180002256A1-20180104-C04167
Figure US20180002256A1-20180104-C04168
Figure US20180002256A1-20180104-C04169
 3-3-98
Figure US20180002256A1-20180104-C04170
Figure US20180002256A1-20180104-C04171
Figure US20180002256A1-20180104-C04172
 3-3-99
Figure US20180002256A1-20180104-C04173
Figure US20180002256A1-20180104-C04174
Figure US20180002256A1-20180104-C04175
 3-3-100
Figure US20180002256A1-20180104-C04176
Figure US20180002256A1-20180104-C04177
Figure US20180002256A1-20180104-C04178
 3-3-101
Figure US20180002256A1-20180104-C04179
Figure US20180002256A1-20180104-C04180
Figure US20180002256A1-20180104-C04181
 3-3-102
Figure US20180002256A1-20180104-C04182
Figure US20180002256A1-20180104-C04183
Figure US20180002256A1-20180104-C04184
 3-3-103
Figure US20180002256A1-20180104-C04185
Figure US20180002256A1-20180104-C04186
Figure US20180002256A1-20180104-C04187
 3-3-104
Figure US20180002256A1-20180104-C04188
Figure US20180002256A1-20180104-C04189
Figure US20180002256A1-20180104-C04190
11. The double Spiro structure compound of claim 1, wherein the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-4, and in the following Chemical Formula 3-4, L2, Ar3 and Ar4 are any one selected from among 3-4-1 to 3-4-104 of the following Table 5:
Figure US20180002256A1-20180104-C04191
TABLE 5 —L2— —Ar3 —Ar4 3-4-1  Direct bond
Figure US20180002256A1-20180104-C04192
Figure US20180002256A1-20180104-C04193
 3-4-2  Direct bond
Figure US20180002256A1-20180104-C04194
Figure US20180002256A1-20180104-C04195
 3-4-3  Direct bond
Figure US20180002256A1-20180104-C04196
Figure US20180002256A1-20180104-C04197
 3-4-4  Direct bond
Figure US20180002256A1-20180104-C04198
Figure US20180002256A1-20180104-C04199
 3-4-5  Direct bond
Figure US20180002256A1-20180104-C04200
Figure US20180002256A1-20180104-C04201
 3-4-6  Direct bond
Figure US20180002256A1-20180104-C04202
Figure US20180002256A1-20180104-C04203
 3-4-7  Direct bond
Figure US20180002256A1-20180104-C04204
Figure US20180002256A1-20180104-C04205
 3-4-8  Direct bond
Figure US20180002256A1-20180104-C04206
Figure US20180002256A1-20180104-C04207
 3-4-9  Direct bond
Figure US20180002256A1-20180104-C04208
Figure US20180002256A1-20180104-C04209
 3-4-10  Direct bond
Figure US20180002256A1-20180104-C04210
Figure US20180002256A1-20180104-C04211
 3-4-11  Direct bond
Figure US20180002256A1-20180104-C04212
Figure US20180002256A1-20180104-C04213
 3-4-12 
Figure US20180002256A1-20180104-C04214
Figure US20180002256A1-20180104-C04215
Figure US20180002256A1-20180104-C04216
 3-4-13 
Figure US20180002256A1-20180104-C04217
Figure US20180002256A1-20180104-C04218
Figure US20180002256A1-20180104-C04219
 3-4-14 
Figure US20180002256A1-20180104-C04220
Figure US20180002256A1-20180104-C04221
Figure US20180002256A1-20180104-C04222
 3-4-15 
Figure US20180002256A1-20180104-C04223
Figure US20180002256A1-20180104-C04224
Figure US20180002256A1-20180104-C04225
 3-4-16 
Figure US20180002256A1-20180104-C04226
Figure US20180002256A1-20180104-C04227
Figure US20180002256A1-20180104-C04228
 3-4-17 
Figure US20180002256A1-20180104-C04229
Figure US20180002256A1-20180104-C04230
Figure US20180002256A1-20180104-C04231
 3-4-18 
Figure US20180002256A1-20180104-C04232
Figure US20180002256A1-20180104-C04233
Figure US20180002256A1-20180104-C04234
 3-4-19 
Figure US20180002256A1-20180104-C04235
Figure US20180002256A1-20180104-C04236
Figure US20180002256A1-20180104-C04237
 3-4-20 
Figure US20180002256A1-20180104-C04238
Figure US20180002256A1-20180104-C04239
Figure US20180002256A1-20180104-C04240
 3-4-21 
Figure US20180002256A1-20180104-C04241
Figure US20180002256A1-20180104-C04242
Figure US20180002256A1-20180104-C04243
 3-4-22 
Figure US20180002256A1-20180104-C04244
Figure US20180002256A1-20180104-C04245
Figure US20180002256A1-20180104-C04246
 3-4-23 
Figure US20180002256A1-20180104-C04247
Figure US20180002256A1-20180104-C04248
Figure US20180002256A1-20180104-C04249
 3-4-24 
Figure US20180002256A1-20180104-C04250
Figure US20180002256A1-20180104-C04251
Figure US20180002256A1-20180104-C04252
 3-4-25 
Figure US20180002256A1-20180104-C04253
Figure US20180002256A1-20180104-C04254
Figure US20180002256A1-20180104-C04255
 3-4-26 
Figure US20180002256A1-20180104-C04256
Figure US20180002256A1-20180104-C04257
Figure US20180002256A1-20180104-C04258
 3-4-27 
Figure US20180002256A1-20180104-C04259
Figure US20180002256A1-20180104-C04260
Figure US20180002256A1-20180104-C04261
 3-4-28 
Figure US20180002256A1-20180104-C04262
Figure US20180002256A1-20180104-C04263
Figure US20180002256A1-20180104-C04264
 3-4-29 
Figure US20180002256A1-20180104-C04265
Figure US20180002256A1-20180104-C04266
Figure US20180002256A1-20180104-C04267
 3-4-30 
Figure US20180002256A1-20180104-C04268
Figure US20180002256A1-20180104-C04269
Figure US20180002256A1-20180104-C04270
 3-4-31 
Figure US20180002256A1-20180104-C04271
Figure US20180002256A1-20180104-C04272
Figure US20180002256A1-20180104-C04273
 3-4-32 
Figure US20180002256A1-20180104-C04274
Figure US20180002256A1-20180104-C04275
Figure US20180002256A1-20180104-C04276
 3-4-33 
Figure US20180002256A1-20180104-C04277
Figure US20180002256A1-20180104-C04278
Figure US20180002256A1-20180104-C04279
 3-4-34 
Figure US20180002256A1-20180104-C04280
Figure US20180002256A1-20180104-C04281
Figure US20180002256A1-20180104-C04282
 3-4-35 
Figure US20180002256A1-20180104-C04283
Figure US20180002256A1-20180104-C04284
Figure US20180002256A1-20180104-C04285
 3-4-36 
Figure US20180002256A1-20180104-C04286
Figure US20180002256A1-20180104-C04287
Figure US20180002256A1-20180104-C04288
 3-4-37 
Figure US20180002256A1-20180104-C04289
Figure US20180002256A1-20180104-C04290
Figure US20180002256A1-20180104-C04291
 3-4-38 
Figure US20180002256A1-20180104-C04292
Figure US20180002256A1-20180104-C04293
Figure US20180002256A1-20180104-C04294
 3-4-39 
Figure US20180002256A1-20180104-C04295
Figure US20180002256A1-20180104-C04296
Figure US20180002256A1-20180104-C04297
 3-4-40 
Figure US20180002256A1-20180104-C04298
Figure US20180002256A1-20180104-C04299
Figure US20180002256A1-20180104-C04300
 3-4-41 
Figure US20180002256A1-20180104-C04301
Figure US20180002256A1-20180104-C04302
Figure US20180002256A1-20180104-C04303
 3-4-42 
Figure US20180002256A1-20180104-C04304
Figure US20180002256A1-20180104-C04305
Figure US20180002256A1-20180104-C04306
 3-4-43 
Figure US20180002256A1-20180104-C04307
Figure US20180002256A1-20180104-C04308
Figure US20180002256A1-20180104-C04309
 3-4-44 
Figure US20180002256A1-20180104-C04310
Figure US20180002256A1-20180104-C04311
Figure US20180002256A1-20180104-C04312
 3-4-45 
Figure US20180002256A1-20180104-C04313
Figure US20180002256A1-20180104-C04314
Figure US20180002256A1-20180104-C04315
 3-4-46 
Figure US20180002256A1-20180104-C04316
Figure US20180002256A1-20180104-C04317
Figure US20180002256A1-20180104-C04318
 3-4-47 
Figure US20180002256A1-20180104-C04319
Figure US20180002256A1-20180104-C04320
Figure US20180002256A1-20180104-C04321
 3-4-48 
Figure US20180002256A1-20180104-C04322
Figure US20180002256A1-20180104-C04323
Figure US20180002256A1-20180104-C04324
 3-4-49 
Figure US20180002256A1-20180104-C04325
Figure US20180002256A1-20180104-C04326
Figure US20180002256A1-20180104-C04327
 3-4-50 
Figure US20180002256A1-20180104-C04328
Figure US20180002256A1-20180104-C04329
Figure US20180002256A1-20180104-C04330
 3-4-51 
Figure US20180002256A1-20180104-C04331
Figure US20180002256A1-20180104-C04332
Figure US20180002256A1-20180104-C04333
 3-4-52 
Figure US20180002256A1-20180104-C04334
Figure US20180002256A1-20180104-C04335
Figure US20180002256A1-20180104-C04336
 3-4-53 
Figure US20180002256A1-20180104-C04337
Figure US20180002256A1-20180104-C04338
Figure US20180002256A1-20180104-C04339
 3-4-54 
Figure US20180002256A1-20180104-C04340
Figure US20180002256A1-20180104-C04341
Figure US20180002256A1-20180104-C04342
 3-4-55 
Figure US20180002256A1-20180104-C04343
Figure US20180002256A1-20180104-C04344
Figure US20180002256A1-20180104-C04345
 3-4-56 
Figure US20180002256A1-20180104-C04346
Figure US20180002256A1-20180104-C04347
Figure US20180002256A1-20180104-C04348
 3-4-57 
Figure US20180002256A1-20180104-C04349
Figure US20180002256A1-20180104-C04350
Figure US20180002256A1-20180104-C04351
 3-4-58 
Figure US20180002256A1-20180104-C04352
Figure US20180002256A1-20180104-C04353
Figure US20180002256A1-20180104-C04354
 3-4-59 
Figure US20180002256A1-20180104-C04355
Figure US20180002256A1-20180104-C04356
Figure US20180002256A1-20180104-C04357
 3-4-60 
Figure US20180002256A1-20180104-C04358
Figure US20180002256A1-20180104-C04359
Figure US20180002256A1-20180104-C04360
 3-4-61 
Figure US20180002256A1-20180104-C04361
Figure US20180002256A1-20180104-C04362
Figure US20180002256A1-20180104-C04363
 3-4-62 
Figure US20180002256A1-20180104-C04364
Figure US20180002256A1-20180104-C04365
Figure US20180002256A1-20180104-C04366
 3-4-63 
Figure US20180002256A1-20180104-C04367
Figure US20180002256A1-20180104-C04368
Figure US20180002256A1-20180104-C04369
 3-4-64 
Figure US20180002256A1-20180104-C04370
Figure US20180002256A1-20180104-C04371
Figure US20180002256A1-20180104-C04372
 3-4-65 
Figure US20180002256A1-20180104-C04373
Figure US20180002256A1-20180104-C04374
Figure US20180002256A1-20180104-C04375
 3-4-66 
Figure US20180002256A1-20180104-C04376
Figure US20180002256A1-20180104-C04377
Figure US20180002256A1-20180104-C04378
 3-4-67 
Figure US20180002256A1-20180104-C04379
Figure US20180002256A1-20180104-C04380
Figure US20180002256A1-20180104-C04381
 3-4-68 
Figure US20180002256A1-20180104-C04382
Figure US20180002256A1-20180104-C04383
Figure US20180002256A1-20180104-C04384
 3-4-69 
Figure US20180002256A1-20180104-C04385
Figure US20180002256A1-20180104-C04386
Figure US20180002256A1-20180104-C04387
 3-4-70 
Figure US20180002256A1-20180104-C04388
Figure US20180002256A1-20180104-C04389
Figure US20180002256A1-20180104-C04390
 3-4-71 
Figure US20180002256A1-20180104-C04391
Figure US20180002256A1-20180104-C04392
Figure US20180002256A1-20180104-C04393
 3-4-72 
Figure US20180002256A1-20180104-C04394
Figure US20180002256A1-20180104-C04395
Figure US20180002256A1-20180104-C04396
 3-4-73 
Figure US20180002256A1-20180104-C04397
Figure US20180002256A1-20180104-C04398
Figure US20180002256A1-20180104-C04399
 3-4-74 
Figure US20180002256A1-20180104-C04400
Figure US20180002256A1-20180104-C04401
Figure US20180002256A1-20180104-C04402
 3-4-75 
Figure US20180002256A1-20180104-C04403
Figure US20180002256A1-20180104-C04404
Figure US20180002256A1-20180104-C04405
 3-4-76 
Figure US20180002256A1-20180104-C04406
Figure US20180002256A1-20180104-C04407
Figure US20180002256A1-20180104-C04408
 3-4-77 
Figure US20180002256A1-20180104-C04409
Figure US20180002256A1-20180104-C04410
Figure US20180002256A1-20180104-C04411
 3-4-78 
Figure US20180002256A1-20180104-C04412
Figure US20180002256A1-20180104-C04413
Figure US20180002256A1-20180104-C04414
 3-4-79 
Figure US20180002256A1-20180104-C04415
Figure US20180002256A1-20180104-C04416
Figure US20180002256A1-20180104-C04417
 3-4-80 
Figure US20180002256A1-20180104-C04418
Figure US20180002256A1-20180104-C04419
Figure US20180002256A1-20180104-C04420
 3-4-81 
Figure US20180002256A1-20180104-C04421
Figure US20180002256A1-20180104-C04422
Figure US20180002256A1-20180104-C04423
 3-4-82 
Figure US20180002256A1-20180104-C04424
Figure US20180002256A1-20180104-C04425
Figure US20180002256A1-20180104-C04426
 3-4-83 
Figure US20180002256A1-20180104-C04427
Figure US20180002256A1-20180104-C04428
Figure US20180002256A1-20180104-C04429
 3-4-84 
Figure US20180002256A1-20180104-C04430
Figure US20180002256A1-20180104-C04431
Figure US20180002256A1-20180104-C04432
 3-4-85 
Figure US20180002256A1-20180104-C04433
Figure US20180002256A1-20180104-C04434
Figure US20180002256A1-20180104-C04435
 3-4-86 
Figure US20180002256A1-20180104-C04436
Figure US20180002256A1-20180104-C04437
Figure US20180002256A1-20180104-C04438
 3-4-87 
Figure US20180002256A1-20180104-C04439
Figure US20180002256A1-20180104-C04440
Figure US20180002256A1-20180104-C04441
 3-4-88 
Figure US20180002256A1-20180104-C04442
Figure US20180002256A1-20180104-C04443
Figure US20180002256A1-20180104-C04444
 3-4-89 
Figure US20180002256A1-20180104-C04445
Figure US20180002256A1-20180104-C04446
Figure US20180002256A1-20180104-C04447
 3-4-90 
Figure US20180002256A1-20180104-C04448
Figure US20180002256A1-20180104-C04449
Figure US20180002256A1-20180104-C04450
 3-4-91 
Figure US20180002256A1-20180104-C04451
Figure US20180002256A1-20180104-C04452
Figure US20180002256A1-20180104-C04453
 3-4-92 
Figure US20180002256A1-20180104-C04454
Figure US20180002256A1-20180104-C04455
Figure US20180002256A1-20180104-C04456
 3-4-93 
Figure US20180002256A1-20180104-C04457
Figure US20180002256A1-20180104-C04458
Figure US20180002256A1-20180104-C04459
 3-4-94 
Figure US20180002256A1-20180104-C04460
Figure US20180002256A1-20180104-C04461
Figure US20180002256A1-20180104-C04462
 3-4-95 
Figure US20180002256A1-20180104-C04463
Figure US20180002256A1-20180104-C04464
Figure US20180002256A1-20180104-C04465
 3-4-96 
Figure US20180002256A1-20180104-C04466
Figure US20180002256A1-20180104-C04467
Figure US20180002256A1-20180104-C04468
 3-4-97 
Figure US20180002256A1-20180104-C04469
Figure US20180002256A1-20180104-C04470
Figure US20180002256A1-20180104-C04471
 3-4-98 
Figure US20180002256A1-20180104-C04472
Figure US20180002256A1-20180104-C04473
Figure US20180002256A1-20180104-C04474
 3-4-99 
Figure US20180002256A1-20180104-C04475
Figure US20180002256A1-20180104-C04476
Figure US20180002256A1-20180104-C04477
 3-4-100
Figure US20180002256A1-20180104-C04478
Figure US20180002256A1-20180104-C04479
Figure US20180002256A1-20180104-C04480
 3-4-101
Figure US20180002256A1-20180104-C04481
Figure US20180002256A1-20180104-C04482
Figure US20180002256A1-20180104-C04483
 3-4-102
Figure US20180002256A1-20180104-C04484
Figure US20180002256A1-20180104-C04485
Figure US20180002256A1-20180104-C04486
 3-4-103
Figure US20180002256A1-20180104-C04487
Figure US20180002256A1-20180104-C04488
Figure US20180002256A1-20180104-C04489
 3-4-104
Figure US20180002256A1-20180104-C04490
Figure US20180002256A1-20180104-C04491
Figure US20180002256A1-20180104-C04492
12. The double Spiro structure compound of claim 1, wherein the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 4-4, and in the following Chemical Formula 4-4, L3 and X4 are any one selected from among 4-4-1 to 4-4-22 of the following Table 6:
Figure US20180002256A1-20180104-C04493
TABLE 6 X4 —L3— 4-4-1 O
Figure US20180002256A1-20180104-C04494
 4-4-2 S
Figure US20180002256A1-20180104-C04495
 X4 —L3— —Ar5 4-4-3  NAr5
Figure US20180002256A1-20180104-C04496
Figure US20180002256A1-20180104-C04497
 4-4-4  NAr5
Figure US20180002256A1-20180104-C04498
Figure US20180002256A1-20180104-C04499
 4-4-5  NAr5
Figure US20180002256A1-20180104-C04500
Figure US20180002256A1-20180104-C04501
 4-4-6  NAr5
Figure US20180002256A1-20180104-C04502
Figure US20180002256A1-20180104-C04503
 4-4-7  NAr5
Figure US20180002256A1-20180104-C04504
Figure US20180002256A1-20180104-C04505
 4-4-8  NAr5
Figure US20180002256A1-20180104-C04506
Figure US20180002256A1-20180104-C04507
 4-4-9  NAr5
Figure US20180002256A1-20180104-C04508
Figure US20180002256A1-20180104-C04509
 4-4-10 NAr5
Figure US20180002256A1-20180104-C04510
Figure US20180002256A1-20180104-C04511
 4-4-11 NAr5
Figure US20180002256A1-20180104-C04512
Figure US20180002256A1-20180104-C04513
 4-4-12 NAr5
Figure US20180002256A1-20180104-C04514
Figure US20180002256A1-20180104-C04515
 4-4-13 NAr5
Figure US20180002256A1-20180104-C04516
Figure US20180002256A1-20180104-C04517
 4-4-14 NAr5
Figure US20180002256A1-20180104-C04518
Figure US20180002256A1-20180104-C04519
 4-4-15 NAr5
Figure US20180002256A1-20180104-C04520
Figure US20180002256A1-20180104-C04521
 4-4-16 NAr5
Figure US20180002256A1-20180104-C04522
Figure US20180002256A1-20180104-C04523
 4-4-17 NAr5
Figure US20180002256A1-20180104-C04524
Figure US20180002256A1-20180104-C04525
 4-4-18 NAr5
Figure US20180002256A1-20180104-C04526
Figure US20180002256A1-20180104-C04527
 4-4-19 NAr5
Figure US20180002256A1-20180104-C04528
Figure US20180002256A1-20180104-C04529
 4-4-20 NAr5
Figure US20180002256A1-20180104-C04530
Figure US20180002256A1-20180104-C04531
 4-4-21 NAr5
Figure US20180002256A1-20180104-C04532
Figure US20180002256A1-20180104-C04533
 4-4-22 NAr5
Figure US20180002256A1-20180104-C04534
Figure US20180002256A1-20180104-C04535
13. An organic light emitting device comprising:
an anode;
a cathode provided opposite to the anode; and
a light emitting layer and one or more organic material layers provided between the anode and the cathode,
wherein the light emitting layer or one or more layers of the organic material layers comprise the double spiro structure compound of claim 1.
14. The organic light emitting device of claim 13, wherein the organic material layer comprises a hole injection layer or a hole transfer layer, and the hole injection layer or the hole transfer layer comprises the double spiro structure compound.
15. The organic light emitting device of claim 13, wherein the organic material layer comprises an electron blocking layer, and the electron blocking layer comprises the double spiro structure compound.
16. The organic light emitting device of claim 13, wherein the light emitting layer comprises the double spiro structure compound.
17. The organic light emitting device of claim 13, wherein the organic material layer comprises an electron transfer layer, an electron injection layer or a layer carrying out electron transfer and electron injection at the same time, and the electron transfer layer, the electron injection layer or the layer carrying out electron transfer and electron injection at the same time comprises the double spiro structure compound.
18. The organic light emitting device of claim 13 comprising one or more organic material layers provided between the anode and the light emitting layer, wherein the organic material layer comprises a double spiro structure compound represented by the following Chemical Formula 2:
Figure US20180002256A1-20180104-C04536
wherein, in Chemical Formula 2,
L1 is a direct bond; a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms; and
Ar1 and Ar2 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
19. The organic light emitting device of claim 13 comprising one or more organic material layers provided between the cathode and the light emitting layer, wherein the light emitting layer or the organic material layer comprises a double spiro structure compound represented by the following Chemical Formula 3:
Figure US20180002256A1-20180104-C04537
wherein, in Chemical Formula 3,
X1 to X3 are the same as or different from each other, and each independently CH or N;
at least one of X1 to X3 is N;
L2 is a direct bond; a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms; and
Ar3 and Ar4 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
20. The organic light emitting device of claim 13 comprising one or more organic material layers provided between the cathode and the light emitting layer, wherein the organic material layer comprises a double spiro structure compound represented by the following Chemical Formula 4:
Figure US20180002256A1-20180104-C04538
wherein, in Chemical Formula 4,
X4 is O, S or NAr5;
L3 is a direct bond; a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms;
Ar5 is selected from the group consisting of hydrogen; a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; and
Cy1 is a substituted or unsubstituted monocyclic or multicyclic hydrocarbon ring having 3 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or multicyclic heteroring having 2 to 30 carbon atoms.
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