WO2021020947A1 - Organic light-emitting device - Google Patents

Organic light-emitting device Download PDF

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WO2021020947A1
WO2021020947A1 PCT/KR2020/010175 KR2020010175W WO2021020947A1 WO 2021020947 A1 WO2021020947 A1 WO 2021020947A1 KR 2020010175 W KR2020010175 W KR 2020010175W WO 2021020947 A1 WO2021020947 A1 WO 2021020947A1
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carbon atoms
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French (fr)
Korean (ko)
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김명곤
허정오
홍완표
김경희
김은호
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주식회사 엘지화학
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Priority to CN202080006746.7A priority Critical patent/CN113196515B/en
Publication of WO2021020947A1 publication Critical patent/WO2021020947A1/en

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    • 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
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K50/00—Organic light-emitting devices
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K50/18—Carrier blocking layers

Definitions

  • the present specification relates to an organic light emitting device.
  • the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material.
  • An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • the present specification provides an organic light emitting device.
  • the present specification is a first electrode; A second electrode; And an organic material layer provided between the first electrode and the second electrode,
  • the organic material layer provides an organic light emitting device including a first organic material layer including a compound represented by Formula 1 below and a second organic material layer including a compound represented by Formula 2 below.
  • A1, A2, A3, B1 and B2 are the same as or different from each other, and each independently a hydrocarbon ring,
  • R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; Or a substituted or unsubstituted heterocyclic group; Represented by the following formula 3, at least one of R1 to R5 is represented by the following formula 3,
  • the dotted line is a portion connected to A1, A2, A3, B1 or B2,
  • X is C or Si
  • R6 to R8 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
  • n1 and n5 are each an integer of 0 to 4,
  • n2 and n4 are each an integer of 0 to 5
  • n3 is an integer from 0 to 3
  • n1 + n2 + n3 + n4 + n5 is 1 or more
  • n1 to n5 are 2 or more, the substituents in parentheses are the same as or different from each other,
  • Y31 and Y32 are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or combine with each other to form a substituted or unsubstituted ring,
  • R3-1 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or the following formula (4), or is bonded to each other with adjacent groups to form a hydrocarbon ring,
  • a31 is an integer from 0 to 8
  • R3-1 is the same as or different from each other
  • the dotted line is a part connected to the core
  • Ar 41 and Ar 42 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • X 1 to X 3 are the same as or different from each other, and each independently N or CR",
  • At least one of X 1 to X 3 is N,
  • R" is hydrogen; deuterium; halogen group; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkynyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted cyclo An alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aryloxy group; or a substituted or unsubstituted heterocyclic group,
  • L 1 to L 3 are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.
  • the organic light emitting device described in the present specification includes the compound represented by Formula 1 in the first organic material layer and the compound represented by Formula 2 in the second organic material layer, thereby having a low driving voltage, excellent efficiency characteristics, and excellent lifespan.
  • Low driving voltage, high efficiency, and lifespan may be improved by controlling the degree of electron transport through the adjustment of an appropriate HOMO energy level and LUMO energy level.
  • 1, 2, and 8 to 10 show examples of an organic light-emitting device according to an exemplary embodiment of the present specification.
  • 3 to 7 show examples of organic light emitting devices including two or more stacks.
  • hole injection layer/ 4 hole transport layer/ 4a: first hole transport layer/ 4b: second hole transport layer/ 4c: third hole transport layer/ 4d: fourth hole transport layer/ 4e: agent 5 hole transport layer/ 4f: sixth hole transport layer/ 4p: p-doped hole transport layer/ 4R: red hole transport layer/ 4G: green hole transport layer/ 4B: blue hole transport layer/ 5: electron blocking layer/ 6: light emitting layer/ 6a: First emitting layer/6b: second emitting layer 6c: third emitting layer 6BF: blue fluorescent emitting layer 6BFa: first blue fluorescent emitting layer 6BFb: second blue fluorescent emitting layer 6YGP: yellow green phosphorescent emitting layer 6RP: red phosphorescent emitting layer / 6GP: green phosphorescent emission layer/ 7: hole blocking layer/ 8: electron injection and transport layer/ 9: electron transport layer/ 9a: first electron transport layer/ 9b: second electron transport layer/ 9c: third electron transport layer/ 10: electron injection
  • the present specification provides an organic light emitting device including a first organic material layer including a compound represented by Formula 1 and a second organic material layer including a compound represented by Formula 2 at the same time.
  • the light-emitting layer containing the compound of Formula 1 has a shallow HOMO level, and the compound of Formula 2 has a deep HOMO and LUMO level, so electrons can be easily transferred to the light-emitting layer, thus exhibiting high efficiency and lifetime.
  • substituted means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted. , Two or more substituents may be the same or different from each other.
  • substituted or unsubstituted refers to deuterium; Halogen group; Cyano group (-CN); Nitro group; Hydroxy group; Silyl group; Boron group; Alkyl group; Alkenyl group; Alkynyl group; Alkoxy group; Alkylthio group; Aryloxy group; Arylthio group; Cycloalkyl group; Aryl group; Amine group; And it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, two or more of the substituents exemplified above are substituted with a connected substituent, or it means that no substituents are present.
  • connection of two or more substituents means that hydrogen of any one of the substituents is replaced with another substituent.
  • an isopropyl group and a phenyl group are connected or It may be a substituent of.
  • connection of three substituents is not only that (substituent 1)-(substituent 2)-(substituent 3) is continuously connected, but also (substituent 2) and (substituent 3) are Includes connections.
  • two phenyl groups and isopropyl groups are connected or It may be a substituent of. The same applies to those in which four or more substituents are connected.
  • substituted with A or B includes not only the case where A is substituted or only B is substituted, but also the case where A and B are substituted.
  • substituted or unsubstituted is deuterium; Halogen group; Cyano group (-CN); Nitro group; Hydroxy group; Silyl group; Boron group; An alkyl group having 1 to 10 carbon atoms; An alkenyl group having 2 to 10 carbon atoms; Alkynyl group having 2 to 10 carbon atoms; An alkoxy group having 1 to 10 carbon atoms; An alkylthio group having 1 to 10 carbon atoms; Aryloxy group having 6 to 30 carbon atoms; Arylthio group having 6 to 30 carbon atoms; A cycloalkyl group having 3 to 30 carbon atoms; Aryl group having 6 to 30 carbon atoms; Amine group; And it is substituted with one or more substituents selected from the group consisting of a heterocyclic group having 2 to 30 carbon atoms, or substituted with a substituent to which two or more groups selected from the group are connected, or not having any substituents.
  • substituted or unsubstituted is deuterium; Halogen group; Cyano group (-CN); Nitro group; Hydroxy group; Silyl group; Boron group; An alkyl group having 1 to 6 carbon atoms; An alkenyl group having 2 to 6 carbon atoms; Alkynyl group having 2 to 6 carbon atoms; An alkoxy group having 1 to 6 carbon atoms; An alkylthio group having 1 to 6 carbon atoms; Aryloxy group having 6 to 20 carbon atoms; Arylthio group having 6 to 20 carbon atoms; A cycloalkyl group having 3 to 20 carbon atoms; Aryl group having 6 to 20 carbon atoms; Amine group; And it is substituted with one or more substituents selected from the group consisting of a heterocyclic group having 2 to 20 carbon atoms, or substituted with a substituent to which two or more groups selected from the group are connected, or does not have any substituents.
  • examples of the halogen group include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).
  • the alkyl group includes a linear or branched chain, and the number of carbon atoms is not particularly limited, but is 1 to 60, 1 to 30, or 1 to 20.
  • Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and the like, and the alkyl group may be a straight chain or a branched chain.
  • propyl The group includes an n-propyl group and an isopropyl group
  • the butyl group includes an n-butyl group, an isobutyl group and a tert-butyl group.
  • the number of carbon atoms of the cycloalkyl group is not particularly limited, but is 3 to 60, 3 to 30, 3 to 20, or 3 to 10.
  • Cycloalkyl groups include monocyclic groups as well as bicyclic groups such as bridgeheads, fused rings, and spiro rings. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, and the like, but is not limited thereto.
  • cycloalkene is a cyclic group that has a double bond in the hydrocarbon ring, but is not aromatic, and the number of carbons is not particularly limited, but 3 to 60, 3 to 30, 3 to 20, or 3 to 10 to be.
  • Cycloalkenes include not only monocyclic groups, but also bicyclic groups such as bridgehead, fused ring, and spiro. Examples of the cycloalkene include cyclopropene, cyclobutene, cyclopentene, and cyclohexene, but are not limited thereto.
  • the alkoxy group is an aryl group connected to an oxygen atom
  • an arylthio group is an alkyl group connected to a sulfur atom
  • the above-described description of the alkyl group may be applied to the alkyl group of the alkoxy group and the alkylthio group.
  • the aryl group may be a monocyclic aryl group or a polycyclic aryl group, and the number of carbon atoms is not particularly limited, but 6 to 60, 6 to 30, or 6 to 20.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or a quarterphenyl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, fluoranthenyl group, triphenylenyl group, etc. , But is not limited thereto.
  • carbon atom 9 (C) of the fluorenyl group may be substituted with an alkyl group, an aryl group, etc., and two substituents may be bonded to each other to form a spiro structure such as cyclopentane and fluorene.
  • the substituted aryl group may include a form in which an aliphatic ring is condensed with an aryl group.
  • a tetrahydronaphthalene group having the following structure is included in a substituted aryl group.
  • one of the carbons of the benzene ring may be linked to another position.
  • an aryloxy group is an aryl group connected to an oxygen atom
  • an arylthio group is an aryl group connected to a sulfur atom
  • the aryl group described above may be applied to the aryl group of the aryloxy group and the arylthio group.
  • the aryl group of the aryloxy group is the same as the aryl group described above.
  • the aryloxy group includes a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3- Biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, and 9-phenanthryloxy group, and the arylthioxy group includes a phenylthioxy group, 2- Methylphenyl thioxy group, 4-tert-butylphenyl thioxy group, and the like, but are not limited thereto.
  • the silyl group may be represented by the formula of -SiY a Y b Y c , wherein Y a , Y b and Y c are each hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the silyl group is specifically trimethylsilyl group, triethylsilyl group, tert-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, dimethylphenylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.
  • the boron group may be represented by the formula of -BY d Y e , wherein Y d and Y e are each hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the silyl group includes a dimethyl boron group, a diethyl boron group, a tert-butylmethyl boron group, a vinyl methyl boron group, a propyl methyl boron group, a methylphenyl boron group, a diphenyl boron group, a phenyl boron group, etc., but is not limited thereto. .
  • the amine group may be represented by -NRaRb, wherein Ra and Rb are each hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or it may be a substituted or unsubstituted heteroaryl group, but is not limited thereto.
  • the amine group is selected from the group consisting of an alkylamine group, an alkylarylamine group, an arylamine group, a heteroarylamine group, an alkylheteroarylamine group, and an arylheteroarylamine group, depending on the type of the substituent (Ra, Rb) to be bonded. Can be.
  • the alkylamine group refers to an amine group substituted with an alkyl group, and the number of carbon atoms is not particularly limited, but may be 1 to 40 or 1 to 20.
  • Specific examples of the alkylamine group include a methylamine group, a dimethylamine group, an ethylamine group, and a diethylamine group, but are not limited thereto.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted arylheteroarylamine group.
  • the aryl group in the arylamine group may be a monocyclic or polycyclic aryl group.
  • Specific examples of the arylamine group include a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a bis(tert-butylphenyl)amine group, etc. , But is not limited thereto.
  • heteroarylamine group examples include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted arylheteroarylamine group.
  • the arylheteroarylamine group means an amine group substituted with an aryl group and a heteroaryl group, and descriptions of the aryl group and the heteroaryl group to be described later may be applied.
  • the heterocyclic group is a cyclic group including one or more of N, O, S, and Si as a hetero atom, and the number of carbon atoms is not particularly limited, but is 2 to 60, or 2 to 30.
  • the heterocyclic group include a pyridyl group; Quinoline group; Thiophene group; Dibenzothiophene group; Furan group; Dibenzofuran group; Naphthobenzofuran group; Carbazole; Benzocarbazole group; Naphthobenzothiophene group; Hexahydrocarbazole group; Dihydroacridine group; Dibenzoazacillin group; Phenoxazine; Phenothiazine; Dihydrodibenzoazacillin group; Spiro (dibenzosilol-dibenzoazacillin) group; Spiro (acridine-fluorene) group; Spiro (fluorene-x
  • heterocyclic group may be applied except that the heteroaryl group is aromatic.
  • adjacent The group may mean a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally close to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted.
  • the ring formed by bonding adjacent groups refers to a hydrocarbon ring; Or a hetero ring.
  • a 5-membered or 6-membered ring formed by bonding adjacent groups means that the ring including the substituent participating in the ring formation is 5 or 6 members. It may include condensation of an additional ring to the ring including the substituent participating in the ring formation.
  • the hydrocarbon ring may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and the description of the aryl group described above may be applied except that the aromatic hydrocarbon ring is not monovalent, and the aliphatic hydrocarbon ring Except that is not monovalent, the above description of the cycloalkyl group may be applied.
  • the aromatic and aliphatic condensed ring include a 1,2,3,4-tetrahydronaphthalene group, and a 2,3-dihydro-1H-indene group, but are not limited thereto.
  • heterocyclic group may be applied, except that the heterocycle is not monovalent.
  • the aromatic hydrocarbon ring refers to a ring in which pi electrons are completely conjugated and planar, and the description of the aryl group described above may be applied except for a divalent group.
  • the aliphatic hydrocarbon ring means all hydrocarbon rings except for an aromatic hydrocarbon ring, and may include a cycloalkyl ring. Except that the cycloalkyl ring is a divalent group, the above description of the cycloalkyl group can be applied.
  • the substituted aliphatic hydrocarbon ring also includes an aliphatic hydrocarbon ring condensed with an aromatic ring.
  • the description of the aryl group described above may be applied except that the arylene group is a divalent group.
  • the description of the cycloalkyl group may be applied except that the cycloalkylene group is a divalent group.
  • A1 to A3, B1 and B2 are the same as or different from each other, and each independently a monocyclic or bicyclic hydrocarbon ring.
  • A1 to A3, B1 and B2 are the same as or different from each other, and each independently a benzene ring or a naphthalene ring.
  • A1 to A3 are each a benzene ring.
  • B1 and B2 are each a benzene ring.
  • Formula 1 is represented by the following Formula 1-1.
  • R1 to R5 and n1 to n5 are as defined in Formula 1.
  • R1 to R5 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; Or a substituted or unsubstituted heterocyclic group, or is represented by the above formula (3).
  • R1, R2, R4, and R5 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or it is represented by Formula 3 above.
  • R1, R2, R4, and R5 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C1 to C30 alkylsilyl group; A substituted or unsubstituted arylsilyl group having 6 to 90 carbon atoms; A substituted or unsubstituted C1 to C20 alkylamine group; A substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; A substituted or unsubstituted C2 to C60 heteroarylamine group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Or it is represented
  • R1, R2, R4, and R5 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C 1 to C 6 alkyl group; A substituted or unsubstituted 3 to 20 cycloalkyl group; A substituted or unsubstituted C 1 to C 18 alkylsilyl group; A substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms; A substituted or unsubstituted C1-C12 alkylamine group; A substituted or unsubstituted arylamine group having 6 to 40 carbon atoms; A substituted or unsubstituted C2 to C40 heteroarylamine group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted C2 to C20 heterocyclic group; Or it is represented by Formula 3 above.
  • R1, R2, R4, and R5 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium; A cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with deuterium; Arylamine group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium; An aryl group having 6 to 30 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, and an alkyl group having 1 to 10 carbon atoms or a substituent connected with two or more groups selected from the group; A heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium; Or it is represented by Formula 3 above.
  • R1, R2, R4, and R5 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; A cycloalkyl group having 3 to 20 carbon atoms unsubstituted or substituted with deuterium; Arylamine group having 6 to 40 carbon atoms substituted or unsubstituted with deuterium; An aryl group having 6 to 20 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, and an alkyl group having 1 to 6 carbon atoms or a substituent connected with two or more groups selected from the group; A heterocyclic group having 2 to 20 carbon atoms substituted or unsubstituted with deuterium; Or it is represented by Formula 3 above.
  • R1, R2, R4, and R5 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; Cyano group' C1-C6 alkyl group unsubstituted or substituted with deuterium; A cycloalkyl group having 3 to 20 carbon atoms; Arylamine group having 6 to 40 carbon atoms; An aryl group having 6 to 20 carbon atoms unsubstituted or substituted with a deuterium, a halogen group, a nitrile group, an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms substituted with deuterium; A heterocyclic group having 2 to 20 carbon atoms; Or it is represented by Formula 3 above.
  • the heterocyclic group of R1, R2, R4 and R5 includes N as a hetero element.
  • R1, R2, R4, and R5 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Fluoro group; Cyano group; A methyl group unsubstituted or substituted with deuterium; Isopropyl group; tert-butyl group; Cyclohexyl group; Diphenylamine group; A phenyl group unsubstituted or substituted with deuterium, a fluoro group, a cyano group, a tert-butyl group, or a CD 3 ; Biphenyl group; Naphthyl group; Or a pyridine group.
  • R3 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; Or a substituted or unsubstituted heterocyclic group; It is represented by the following formula (3).
  • R3 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or it is represented by Formula 3 above.
  • R3 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C1 to C30 alkylsilyl group; A substituted or unsubstituted arylsilyl group having 6 to 90 carbon atoms; A substituted or unsubstituted C1 to C20 alkylamine group; A substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; A substituted or unsubstituted C2 to C60 heteroarylamine group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Or it is represented by Formula 3 above.
  • R3 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C 1 to C 6 alkyl group; A substituted or unsubstituted 3 to 20 cycloalkyl group; A substituted or unsubstituted C 1 to C 18 alkylsilyl group; A substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms; A substituted or unsubstituted C1-C12 alkylamine group; A substituted or unsubstituted arylamine group having 6 to 40 carbon atoms; A substituted or unsubstituted C2 to C40 heteroarylamine group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted C2 to C20 heterocyclic group; Or it is represented by Formula 3 above.
  • R3 is hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium; A cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with deuterium; 6 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen groups, cyano groups, alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 30 carbon atoms, and silyl groups, or a substituent connected with two or more groups selected from the group Arylamine group of to 60; An aryl group having 6 to 30 carbon atoms unsubstituted or substituted with deuterium, a halogen group, or a cyano group; A heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium; Or it is represented by
  • R3 is hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; A cycloalkyl group having 3 to 20 carbon atoms unsubstituted or substituted with deuterium; At least one substituent selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a silyl group, or 6 unsubstituted or substituted with a substituent connected with two or more groups selected from the group Arylamine group of to 40; An aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium, a halogen group, or a cyano group; A heterocyclic group having 2 to 20 carbon atoms substituted or unsubstituted with deuterium; Or it
  • R3 is hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; A cycloalkyl group having 3 to 20 carbon atoms; An arylamine group having 6 to 40 carbon atoms unsubstituted or substituted with a deuterium, an alkyl group having 1 to 6 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, or a triarylamine group having 18 to 60 carbon atoms; An aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium, a halogen group, or a cyano group; A heterocyclic group having 2 to 20 carbon atoms; Or it is represented by Formula 3 above.
  • the heterocyclic group of R3 includes N as a hetero element.
  • R3 is hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; tert-butyl group; Diphenylamine group unsubstituted or substituted with deuterium, tert-butyl group, trimethylsilyl group, or triphenylsilyl group; A phenyl group unsubstituted or substituted with deuterium or a fluoro group; Or carbazole group.
  • R1, R2, R4, and R5 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium; A cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with deuterium; Arylamine group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium; An aryl group having 6 to 30 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, and an alkyl group having 1 to 10 carbon atoms or a substituent connected with two or more groups selected from the group; A heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium; Or represented by Chemical Formula 3,
  • R3 is hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium; A cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with deuterium; 6 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen groups, cyano groups, alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 30 carbon atoms, and silyl groups, or a substituent connected with two or more groups selected from the group Arylamine group of to 60; An aryl group having 6 to 30 carbon atoms unsubstituted or substituted with deuterium, a halogen group, or a cyano group; A heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium; Or it is represented by Formula 3 above.
  • one of R2 is connected to a position in ortho orientation with respect to N to which B2 is connected.
  • one of R4 is connected to a position in ortho orientation with respect to N to which B2 is connected.
  • n1 is 1 or 2.
  • n2 is 1 to 4. In another exemplary embodiment, n2 is 1 to 3.
  • n3 is 1 or 2.
  • n4 is 1 to 4. In another exemplary embodiment, n4 is 1 to 3.
  • n5 is 1.
  • At least one of R1 to R5 is represented by Chemical Formula 3.
  • R1 to R5 are represented by Chemical Formula 3.
  • R1 to R5 are represented by Chemical Formula 3.
  • R1, R2, R4, and R5 are represented by Chemical Formula 3.
  • R1, R2, R4, and R5 are represented by Chemical Formula 3.
  • R1 is represented by Chemical Formula 3.
  • R2 is represented by Chemical Formula 3.
  • R3 is represented by Chemical Formula 3.
  • R4 is represented by Chemical Formula 3.
  • R5 is represented by Chemical Formula 3.
  • R6 to R8 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R6 to R8 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • R6 to R8 are the same as or different from each other, and each independently an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; Or substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a silyl group or a substituent connected with two or more groups selected from the group. Or an unsubstituted C6-C30 aryl group.
  • R6 to R8 are the same as or different from each other, and each independently an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; Or substituted or unsubstituted with at least one substituent selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a silyl group or a substituent connected with two or more groups selected from the group Or it is an unsubstituted C6-C20 aryl group.
  • R6 to R8 are the same as or different from each other, and each independently an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; Or a substituted or unsubstituted C6 to C6 group unsubstituted or substituted with a deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with deuterium, or a trialkylsilyl group having 3 to 18 carbon atoms It is an aryl group of 20.
  • R6 to R8 are the same as or different from each other, and each independently a methyl group; tert-butyl group; Or a phenyl group unsubstituted or substituted with deuterium, a fluoro group, a methyl group, a tert-butyl group, a CD 3 or a trimethylsilyl group.
  • X is C, and at least one of R6 to R8 is a substituted or unsubstituted alkyl group.
  • X is C, and at least two of R6 to R8 are substituted or unsubstituted alkyl groups.
  • X is C, and at least one of R6 to R8 is a substituted or unsubstituted aryl group.
  • X is C
  • R6 and R7 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group
  • R8 is a substituted or unsubstituted aryl group.
  • X is Si
  • at least one of R6 to R8 is a substituted or unsubstituted aryl group.
  • X is Si
  • at least two of R6 to R8 are substituted or unsubstituted aryl groups.
  • X is C
  • R6 and R7 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group
  • R8 is a substituted or unsubstituted alkyl group.
  • X is Si
  • R6 to R8 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group.
  • Chemical Formula 3 is represented by the following Chemical Formula 3-1 or 3-2.
  • R11 is a substituted or unsubstituted alkyl group
  • R12 is a substituted or unsubstituted aryl group
  • R13 to R16 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • R11 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
  • R11 is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.
  • R11 is an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium.
  • R11 is a methyl group.
  • R12 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R12 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • R12 is at least one substituent selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a silyl group, or two or more selected from the group. It is a substituted or unsubstituted substituted or unsubstituted aryl group having 6 to 20 carbon atoms with a group-linked substituent.
  • R12 is substituted or provided with a deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with deuterium, or a trialkylsilyl group having 3 to 18 carbon atoms. It is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • R12 is a phenyl group unsubstituted or substituted with deuterium, a fluoro group, a methyl group, a tert-butyl group, a CD 3 , or a trimethylsilyl group.
  • R13 to R16 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R13 to R16 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • R13 to R16 are the same as or different from each other, and each independently an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; Or substituted or unsubstituted with at least one substituent selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a silyl group or a substituent connected with two or more groups selected from the group Or it is an unsubstituted C6-C20 aryl group.
  • R13 to R16 are the same as or different from each other, and each independently a methyl group; tert-butyl group; Or a phenyl group unsubstituted or substituted with deuterium, a fluoro group, a methyl group, a tert-butyl group, a CD 3 or a trimethylsilyl group.
  • the compound represented by Formula 1 is any one selected from the following compounds.
  • Y31 and Y32 are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms Or combine with each other to form a ring.
  • Y31 and Y32 are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms Or combine with each other to form an aliphatic ring.
  • Y31 and Y32 are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms Or, by bonding to each other to form an aliphatic ring having 3 to 10 carbon atoms.
  • Y31 and Y32 are bonded to each other to form an aliphatic ring having 3 to 6 carbon atoms.
  • Y31 and Y32 are bonded to each other to form a cyclopentyl ring.
  • Y31 and Y32 are bonded to each other to form a ring in which an aliphatic and aromatic ring having 3 to 10 carbon atoms are fused.
  • Y31 and Y32 are bonded to each other to form a ring in which a cyclopentyl ring and a benzene ring are fused.
  • Y31 and Y32 are the same as or different from each other, and each independently hydrogen; An alkyl group having 1 to 10 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms.
  • Y31 and Y32 are the same as or different from each other, and each independently hydrogen; Methyl group; Ethyl group; Isopropyl group; Terbutyl group; Phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Phenanthrene group; Or an anthracene group,
  • the anthracene group is unsubstituted or substituted with a methyl group, ethyl group, isopropyl group, terbutyl group, phenyl group, biphenyl group, naphthyl group, terphenyl group, phenanthrene group, or anthracene group.
  • Y31 and Y32 are the same as or different from each other, and each independently hydrogen; Methyl group; Phenyl group; Naphthyl group; A phenyl group substituted with a methyl group; A naphthyl group substituted with a methyl group; A phenyl group substituted with a naphthyl group; It is a naphthyl group substituted with a phenyl group or is bonded to each other to form an aliphatic ring having 3 to 6 carbon atoms.
  • R3-1 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or the formula 4, or an adjacent group and Combined with each other to form a hydrocarbon ring.
  • R3-1 is hydrogen; heavy hydrogen; An alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or the above formula (4), or combined with an adjacent group to form a hydrocarbon ring having 3 to 20 carbon atoms.
  • R3-1 is hydrogen; Methyl group; Terbutyl group; Phenyl group; A phenyl group substituted with a methyl group; Biphenyl group; It is a naphthyl group or the above formula (4), or is combined with an adjacent group to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  • R3-1 is hydrogen; Methyl group; Terbutyl group; Phenyl group; Naphthyl group; Or the formula (4), or by bonding with adjacent groups to each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  • R3-1 is a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
  • a31 is an integer of 1 to 8, and at least one R3-1 is Chemical Formula 4.
  • Ar 41 and Ar 42 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted alkylsilyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 3 to C 30 heterocyclic group.
  • Ar 41 and Ar 42 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A silyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 3 to C 30 heterocyclic group.
  • Ar 41 and Ar 42 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 3 to C 30 heterocyclic group.
  • Ar 41 and Ar 42 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • Ar 41 and Ar 42 are the same as or different from each other, and each independently a methyl group; Ethyl group; Butyl group; Terbutyl group; Phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrene group; Triphenylene group; Perylene group; Fluorene group; Fluoroxanthene group; Carbazole; Benzocarbazole group; Indenocarbazole; Pyridine group; Pyrimidine group; Triazine group; Dibenzofuran group; Dibenzothiophene group; Quinoline group; Quinazoline; Quinoxalin group; Phenox camera; Phenothiazine group; Phenoxathiine; Is a trimethylsilyl group,
  • Ar 41 and Ar 42 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Or a phenanthrene group, and the phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Or the phenanthrene group is deuterium; CN; Alkyl group; Aryl group; Silyl group; Or substituted or unsubstituted with a heteroaryl group.
  • Ar 41 and Ar 42 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Or a phenanthrene group, and the phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Or the phenanthrene group is deuterium; CN; An alkyl group having 1 to 10 carbon atoms; Aryl group having 6 to 30 carbon atoms; An alkylsilyl group having 1 to 10 carbon atoms; Or it is unsubstituted or substituted with a C3-C30 heteroaryl group.
  • Ar 41 and Ar 42 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Or a phenanthrene group, and the phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Or the phenanthrene group is deuterium; CN; Methyl group; Ethyl group; Butyl group; Terbutyl group; Phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrene group; Anthracene group; Perylene group; Triphenylene group; Pyren group; Fluoranthene; Thiophene group; Furan group; Pyridine group; Pyrimidine group; Triazine group; Carbazole; It is unsubstituted or substituted with any one or more selected from a dibenzofuran group or a di
  • X 1 to X 3 are N.
  • the above X 1 to X 3 X 1 is N and the others are CR.
  • X 2 of X 1 to X 3 is N, and the rest are CR.
  • X 3 of X 1 to X 3 is N, and the rest are CR.
  • X 1 to X 3 in X 1 is CR, with the remainder being N.
  • X 2 of X 1 to X 3 is CR, and the rest are N.
  • X 3 of X 1 to X 3 is CR, and the rest are N.
  • R is hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; Or a substituted or unsubstituted heterocyclic group.
  • R is hydrogen; heavy hydrogen; Nitrile group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; Or a substituted or unsubstituted heterocyclic group.
  • R is hydrogen; It is a deuterium or nitrile group.
  • R is hydrogen
  • Formula 2 is represented by the following Formula 2-1.
  • Y is CR111R112, O, or S,
  • R111, R112, R3-2 and R3-3 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or It is the following formula (4), or combines with an adjacent group to form a hydrocarbon ring,
  • L31 and L32 are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
  • a32 is an integer from 0 to 8
  • b33 is an integer from 0 to 8
  • n33 is 0 or 1
  • a33 is 0.
  • a position capable of being substituted with R3-2 is substituted with hydrogen.
  • b33 is 0.
  • a position that can be substituted with R3-3 is substituted with hydrogen.
  • Y is O or S.
  • R3-2 is hydrogen
  • R3-3 is hydrogen
  • a33 is 1.
  • b33 is 1.
  • R3-2 is Formula 6 or 7.
  • R3-3 is the following Chemical Formula 6 or 7.
  • the dotted line is a part connected to the core
  • L4 and L5 are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
  • Ar5 and Ar6 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,
  • c and d are integers from 0 to 5
  • R3-2 and R3-3 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted Is a heteroaryl group, Formula 4, Formula 6, or Formula 7.
  • R3-2 and R3-3 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted carbon number.
  • a substituent other than Formula 4, Formula 6, or Formula 7 of R3-2 and R3-3 is a methyl group, terbutyl group, butyl group, phenyl group, naphthyl group, pyridine group, It is a pyrimidine group, a triazine group, a quinazoline group, a quinoline group, a quinoxaline group, a triphenylene group, and the phenyl group, a naphthyl group, a pyridine group, a pyrimidine group, a triazine group, a quinazoline group, a quinoline group, a quinoxaline group,
  • the triphenylene group is unsubstituted or substituted with any one or more substituents selected from deuterium, CN, an alkyl group, an aryl group, and a heteroaryl group.
  • a33 is 2, and R3-2 is the same as or different from each other.
  • b33 is 2, and R3-3 is the same as or different from each other.
  • a substituent other than Formula 4, Formula 6, or Formula 7 of the plurality of R3-2 is a methyl group, terbutyl group, butyl group, phenyl group, naphthyl group, pyridine group, and pyrimy.
  • the ene group is unsubstituted or substituted with any one or more substituents selected from deuterium, CN, an alkyl group, an aryl group, and a heteroaryl group.
  • a substituent other than Formula 4, Formula 6, or Formula 7 of the plurality of R3-3 is a methyl group, terbutyl group, butyl group, phenyl group, naphthyl group, pyridine group, and pyrimy.
  • the ene group is unsubstituted or substituted with any one or more substituents selected from deuterium, CN, an alkyl group, an aryl group, and a heteroaryl group.
  • L 1 to L 5 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.
  • L 1 to L 5 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 3 to C 30 heteroarylene group.
  • L 1 to L 5 are the same as or different from each other, and each independently a direct bond; Phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent fluorene group; A divalent phenoxy camera; Divalent naphthyl group; Divalent quinazole group; Divalent quinoline group; Divalent quinoxalin group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Divalent carbazole group; Divalent benzocarbazole group; Divalent indenocarbazole; A divalent phenothiazine group; Divalent phenoxathiine; Divalent dibenzosilol group; Divalent pyrrole group; Divalent furan group; Divalent thiophene group; A divalent pyridine group; Divalent pyrimidine group; Or a divalent triazine group,
  • L 1 to L 5 are the same as or different from each other, and each independently a direct bond; Phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent fluorene group; A divalent phenoxy camera; Divalent naphthyl group; Divalent quinazole group; Divalent quinoline group; Divalent quinoxalin group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Divalent carbazole group; Divalent benzocarbazole group; Divalent indenocarbazole; A divalent phenothiazine group; Divalent phenoxathiine; Divalent dibenzosilol group; Divalent pyrrole group; Divalent furan group; Divalent thiophene group; A divalent pyridine group; Divalent pyrimidine group; Or a divalent triazine group,
  • L 1 to L 5 are the same as or different from each other, and each independently a direct bond; Phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent fluorene group; A divalent phenoxy camera; Divalent naphthyl group; Divalent quinazole group; Divalent quinoline group; Divalent quinoxalin group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Divalent carbazole group; Divalent benzocarbazole group; Divalent indenocarbazole; A divalent phenothiazine group; Divalent phenoxathiine; Divalent dibenzosilol group; Divalent pyrrole group; Divalent furan group; Divalent thiophene group; A divalent pyridine group; Divalent pyrimidine group; Or a divalent triazine group, the phenylene group; Divalent biphenyl group; Divalent terphenyl
  • overlapped means that two or more substituents are sequentially bonded.
  • the phenylene group and the divalent carbazole group overlap means that -phenylene-divalent carbazole- is sequentially bonded.
  • L 1 to L 3 are the same as or different from each other, and each independently a direct bond; An arylene group having 6 to 30 carbon atoms; Or a heteroarylene group having 3 to 30 carbon atoms.
  • L 1 to L 3 are direct bonds.
  • L 1 to L 3 are the same as or different from each other, and each independently a direct bond; Phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent naphthyl group; Divalent quinazole group; Divalent quinoline group; Divalent quinoxalin group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Divalent carbazole group; Divalent dibenzosilol group; Divalent pyrrole group; Divalent furan group; Divalent thiophene group; Or a divalent pyridine group.
  • L 3 is a direct bond; Phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent naphthyl group; Divalent quinazole group; Divalent quinoline group; Divalent quinoxalin group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Divalent carbazole group; Divalent dibenzosilol group; Divalent pyrrole group; Divalent furan group; Divalent thiophene group; Or a divalent pyridine group.
  • L 3 is a direct bond or a phenylene group.
  • L31 and L32 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.
  • L31 and L32 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 3 to C 30 heteroarylene group.
  • L31 and L32 are the same as or different from each other, and each independently a direct bond; Phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent fluorene group; A divalent phenoxy camera; Divalent naphthyl group; Divalent quinazole group; Divalent quinoline group; Divalent quinoxalin group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Divalent carbazole group; Divalent benzocarbazole group; Divalent indenocarbazole; A divalent phenothiazine group; Divalent phenoxathiine; Divalent dibenzosilol group; Divalent pyrrole group; Divalent furan group; Divalent thiophene group; A divalent pyridine group; Divalent pyrimidine group; Or a divalent triazine group,
  • L31 and L32 are the same as or different from each other, and each independently a direct bond; Phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent fluorene group; A divalent phenoxy camera; Divalent naphthyl group; Divalent quinazole group; Divalent quinoline group; Divalent quinoxalin group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Divalent carbazole group; Divalent benzocarbazole group; Divalent indenocarbazole; A divalent phenothiazine group; Divalent phenoxathiine; Divalent dibenzosilol group; Divalent pyrrole group; Divalent furan group; Divalent thiophene group; A divalent pyridine group; Divalent pyrimidine group; Or a divalent triazine group, the phenylene group; Divalent biphenyl group; Divalent terphenyl
  • R3-2 is bonded to each other with adjacent groups to form a hydrocarbon ring.
  • R3-2 is combined with an adjacent group to form an aromatic hydrocarbon ring.
  • R3-2 is combined with an adjacent group to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  • R3-3 is bonded to each other with adjacent groups to form a hydrocarbon ring.
  • R3-3 is bonded to each other with adjacent groups to form an aromatic hydrocarbon ring.
  • R3-3 is bonded to each other with adjacent groups to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  • Formula 2-1 is represented by any one of Formulas 2-2 to 2-6 below.
  • R3-4 and R3-5 are the same as R3-3 of Formula 2-1,
  • a34 and a35 are the same as a33 in Chemical Formula 2-1.
  • one of the substituents other than Formula 4 in R3-2 and R3-3 is a substituted or unsubstituted aryl group.
  • one of the substituents other than Formula 4 in R3-2 and R3-3 is a substituted or unsubstituted fluorene group, or a substituted or unsubstituted benzo. It is a fluorene group.
  • one of the substituents other than Formula 4 in R3-2 and R3-3 is a fluorene group unsubstituted or substituted with deuterium, an alkyl group, or an alkylaryl group; Or a benzofluorene group unsubstituted or substituted with deuterium, an alkyl group, or an alkylaryl group.
  • R3-4 and R3-5 are hydrogen.
  • a34 and a35 are 0.
  • Ar 41 and Ar 42 are the same as or different from each other, and each independently a methyl group, a silyl group, a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a dibenzofuran group, and a dibenzothiophene.
  • Polycyclic heteroaryl including the methyl group, silyl group, phenyl group, biphenyl group, naphthyl group, terphenyl group, dibenzofuran group, dibenzothiophene group, carbazole group, silol group, or Si, N, O, or S
  • the group is deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted 3 to carbon number It is unsubstituted or substituted with 20 heteroaryl groups.
  • Ar 41 and Ar 42 are the same as or different from each other, and each independently a methyl group, a silyl group, a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a dibenzofuran group, and a dibenzothiophene.
  • Polycyclic heteroaryl including the methyl group, silyl group, phenyl group, biphenyl group, naphthyl group, terphenyl group, dibenzofuran group, dibenzothiophene group, carbazole group, silol group, or Si, N, O, or S
  • the group is deuterium, nitrile group, halogen group, substituted or unsubstituted methyl group, substituted or unsubstituted silyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted A substituted naphthyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstit
  • Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted It is a cyclic heteroaryl group.
  • Ar5 and Ar6 are the same as or different from each other, and each independently a methyl group, a silyl group, a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a dibenzofuran group, a dibenzothiophene group, It is a carbazole group, a silol group, or a polycyclic heteroaryl group containing Si, N, O, or S,
  • Polycyclic heteroaryl including the methyl group, silyl group, phenyl group, biphenyl group, naphthyl group, terphenyl group, dibenzofuran group, dibenzothiophene group, carbazole group, silol group, or Si, N, O, or S
  • the group is deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted 3 to carbon number It is unsubstituted or substituted with 20 heteroaryl groups.
  • Ar5 and Ar6 are the same as or different from each other, and each independently methyl group, silyl group, phenyl group, biphenyl group, naphthyl group, terphenyl group, dibenzofuran group, dibenzothiophene group, carba It is a sol group, a silol group, or a polycyclic heteroaryl group containing Si, N, O, or S,
  • Polycyclic heteroaryl including the methyl group, silyl group, phenyl group, biphenyl group, naphthyl group, terphenyl group, dibenzofuran group, dibenzothiophene group, carbazole group, silol group, or Si, N, O, or S
  • the group is deuterium, nitrile group, halogen group, substituted or unsubstituted methyl group, substituted or unsubstituted silyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted A substituted naphthyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstit
  • Ar5 and Ar6 are the same as or different from each other, and each independently methyl group, silyl group, phenyl group, biphenyl group, naphthyl group, terphenyl group, dibenzofuran group, dibenzothiophene group, carba It is a sol group, a silol group, or a tricyclic heteroaryl group containing Si, N, O, or S,
  • Tricyclic heteroaryl containing the methyl group, silyl group, phenyl group, biphenyl group, naphthyl group, terphenyl group, dibenzofuran group, dibenzothiophene group, carbazole group, silol group, or Si, N, O, or S Groups include deuterium, nitrile group, halogen group, methyl group, trifluoromethyl group, trifluoromethoxy group, methoxy group, trimethylsilyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, carbazole group, carbazole group substituted with phenyl group, It is unsubstituted or substituted with one or more substituents selected from dibenzofuran group, dibenzothiophene group, benzocarbazole group, indolocarbazole group, and pyridine group.
  • Ar5 and Ar6 are the same as or different from each other, and each independently
  • Ar 41 and Ar 42 are the same as or different from each other, and each independently a methyl group; Ethyl group; Butyl group; Terbutyl group; Phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrene group; Triphenylene group; Perylene group; Fluorene group; Fluoroxanthene group; Carbazole; Benzocarbazole group; Indenocarbazole; Pyridine group; Pyrimidine group; Triazine group; Dibenzofuran group; Dibenzothiophene group; Quinoline group; Quinazoline; Quinoxalin group; Phenox camera; A divalent phenothiazine group; Divalent phenoxatiin; Or a trimethylsilyl group,
  • Formula 2 is any one of the following compounds.
  • Chemical Formula 2 is any one of the compounds listed in the following table. In the table below, the dotted line is the position combined with Formula 4.
  • the compound of Formula 1 may be prepared as shown in Scheme 1 below, and the compound of Formula 2 may be prepared as in Scheme 2 below.
  • the following Schemes 1 and 2 describe the synthesis process of some compounds corresponding to Formulas 1 and 2 of the present application, but various compounds corresponding to Formulas 1 and 2 of the present application can be synthesized using a synthesis procedure such as Schemes 1 and 2 below.
  • the substituents may be bonded by methods known in the art, and the type, position and number of the substituents may be changed according to techniques known in the art.
  • R means a substituent connected to the core, and may be R1 to R3, B1 or B2 of the present invention, and the definition of the remaining substituents is as described above.
  • the definition of the substituent is as described above, and can be synthesized by a general coupling reaction. For example, it can be produced using a Suzuki coupling reaction or the like.
  • the organic light emitting device of the present specification except for forming a first organic material layer using the compound represented by Formula 1 and forming a second organic material layer using the compound represented by Formula 2 It can be manufactured by the manufacturing method and material of the light emitting device.
  • the first organic material layer including the compound represented by Formula 1 and the second organic material layer including the compound represented by Formula 2 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method.
  • the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
  • the organic material layer of the organic light-emitting device of the present specification may have a structure including only the first organic material layer and the second organic material layer, but may have a structure in which an additional organic material layer is further included.
  • an additional organic material layer one of a hole injection layer, a hole transport layer, a layer for both hole transport and hole injection, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer for simultaneously transporting and injecting electrons, and a hole blocking layer. It can be more than one layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number or a larger number of organic material layers.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first organic material layer is an emission layer
  • the second organic material layer is the second electrode and the first It is provided between the organic material layers. That is, the second organic material layer is provided between the cathode and the emission layer.
  • the first organic material layer is an emission layer.
  • the first organic material layer is an emission layer
  • the compound represented by Formula 1 is included as a dopant of the emission layer.
  • the first organic material layer is an emission layer
  • the compound represented by Chemical Formula 1 is used as a dopant of the emission layer, and further includes a fluorescent host or a phosphorescent host.
  • the dopant in the light emitting layer may be included in an amount of 1 to 50 parts by weight relative to 100 parts by weight of the host, preferably 0.1 to 30 parts by weight, more preferably 1 to 10 parts by weight. When within the above range, energy transfer from the host to the dopant occurs efficiently.
  • the host is an anthracene derivative.
  • the organic material layer includes two or more emission layers, and one of the two or more emission layers includes the compound represented by Formula 1 above.
  • the maximum emission peaks of the two or more emission layers are different from each other.
  • the light emitting layer including the compound represented by Formula 1 has a blue color, and the light emitting layer not including the compound represented by Formula 1 may include a blue, red, or green light emitting compound known in the art.
  • the emission layer including the compound represented by Formula 1 includes a fluorescent dopant, and the emission layer not including the compound represented by Formula 1 includes a phosphorescent dopant.
  • the maximum emission peak of the emission layer including the compound represented by Formula 1 is 400 nm to 500 nm. That is, the emission layer including the compound represented by Formula 1 emits blue light.
  • the organic material layer of the organic light emitting device includes two or more emission layers, the maximum emission peak of one emission layer (light emission layer 1) is 400 nm to 500 nm, and the emission layer of the other layer (light emission layer 2 ) The maximum emission peak of 510 nm to 580 nm; Alternatively, a maximum emission peak of 610 nm and 680 nm may be exhibited.
  • the emission layer 1 includes the compound represented by Chemical Formula 1.
  • the second organic material layer is an electron transport region.
  • the second organic material layer includes at least one layer selected from the group consisting of a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer.
  • the second organic material layer includes one or two layers selected from the group consisting of a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer.
  • the second organic material layer is a hole blocking layer, an electron transport layer, an electron injection layer, or an electron injection and transport layer.
  • the second organic material layer is a hole blocking layer.
  • the second organic material layer is an electron transport layer.
  • the second organic material layer is an electron injection and transport layer.
  • the second organic material layer includes a hole blocking layer and an electron injection and transport layer.
  • the hole blocking layer is provided adjacent to the light emitting layer
  • the electron injection and transport layer is provided adjacent to the cathode.
  • the second organic material layer is provided in contact with the first organic material layer.
  • the second organic material layer further includes one or two or more n-type dopants selected from alkali metals and alkaline earth metals.
  • the organic alkali metal compound or the organic alkaline earth metal compound When used as an n-type dopant, stability against holes from the light emitting layer can be secured, thereby improving the life of the organic light emitting device.
  • the electron mobility of the electron transport layer may be adjusted by adjusting the ratio of the organic alkali metal compound or the organic alkaline earth metal compound to maximize the balance between holes and electrons in the emission layer, thereby increasing luminous efficiency.
  • LiQ is more preferable as the n-type dopant used in the second organic material layer in the present specification.
  • the second organic material layer may include the compound of Formula 2 and the n-type dopant in a weight ratio of 1:9 to 9:1.
  • the compound of Formula 2 and the n-type dopant may be included in a ratio of 2:8 to 8:2, more preferably 3:7 to 7:3.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode
  • the organic light-emitting device may be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an inverted type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the structure of the organic light emitting device of the present specification may have a structure as shown in FIGS. 1, 2, and 8, but is not limited thereto.
  • a substrate 1 an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 8, and a cathode 11
  • the compound represented by Formula 1 may be included in the emission layer 6, and the compound represented by Formula 2 may be included in the hole blocking layer 7 or the electron injection and transport layer 8.
  • the compound represented by Formula 1 may be included in the emission layer 6, and the compound represented by Formula 2 may be included in the electron injection and transport layer 8.
  • FIG. 8 shows a substrate 1, an anode 2, a p-doped hole transport layer 4p, a hole transport layer 4R, 4G, 4B, a light emitting layer 6RP, 6GP, 6BF, a first electron transport layer 9a,
  • a structure of an organic light emitting diode in which the second electron transport layer 9b, the electron injection layer 10, the cathode 11, and the capping layer 14 are sequentially stacked is illustrated.
  • the compound represented by Formula 1 may be included in the emission layer (6RP, 6GP, 6BF), and the compound represented by Formula 2 is a first electron transport layer (9a), a second electron transport layer (9b) And one or more layers of the electron injection layer 10.
  • the organic light emitting device may have a tandem structure in which two or more independent devices are connected in series.
  • the tandem structure may be a form in which each organic light emitting device is bonded to a charge generation layer. Since the tandem device can be driven at a lower current than the unit device based on the same brightness, there is an advantage in that the lifespan of the device is greatly improved.
  • the organic material layer includes: a first stack including one or more emission layers; A second stack including one or more light emitting layers; And at least one charge generation layer provided between the first stack and the second stack.
  • the organic material layer includes: a first stack including one or more emission layers; A second stack including one or more light emitting layers; And a third stack including one or more emission layers, and between the first stack and the second stack; And one or more charge generation layers, respectively, between the second stack and the third stack.
  • a charge generating layer means a layer in which holes and electrons are generated when a voltage is applied.
  • the charge generation layer may be an N-type charge generation layer or a P-type charge generation layer.
  • the N-type charge generation layer refers to a charge generation layer located closer to the anode than the P-type charge generation layer
  • the P-type charge generation layer refers to a charge generation layer located closer to the cathode than the N-type charge generation layer.
  • the N-type charge generation layer and the P-type charge generation layer may be provided in contact with each other, and in this case, an NP junction is formed.
  • an NP junction is formed.
  • holes are easily formed in the P-type charge generation layer and electrons are easily formed in the N-type charge generation layer. Electrons are transported toward the anode through the LUMO level of the N-type charge generation layer, and holes are transported toward the cathode through the HOMO level of the P-type organic material layer.
  • Each of the first stack, the second stack, and the third stack includes one or more light emitting layers, and additionally, a hole injection layer, a hole transport layer, an electron blocking layer, an electron injection layer, an electron transport layer, a hole blocking layer, a hole transport and a hole
  • a hole injection layer a layer for simultaneous injection
  • an electron injection layer a layer for simultaneous electron transport and electron injection
  • an electron injection and transport layer a layer for simultaneous electron transport and electron injection
  • FIG. 3 An organic light-emitting device including the first stack and the second stack is illustrated in FIG. 3.
  • a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, an electron blocking layer 5, a first emission layer 6a, a first electron transport layer 9a, An N-type charge generation layer 12, a P-type charge generation layer 13, a second hole transport layer 4b, a second emission layer 6b, an electron injection and transport layer 8, and a cathode 11 are sequentially stacked.
  • the structure of the organic light emitting device is illustrated.
  • the compound represented by Formula 1 may be included in the first emission layer 6a or the second emission layer 6b
  • the compound represented by Formula 2 is the first electron transport layer 9a or electron injection. And it may be included in the transport layer (8).
  • Organic light-emitting devices including the first to third stacks are illustrated in FIGS. 4 to 7.
  • the structure of a light emitting device is illustrated.
  • the compound represented by Formula 1 may be included in the first emission layer 6a, the second emission layer 6b, and the third emission layer 6c, and the compound represented by Formula 2 is a first electron It may be included in one or more of the transport layer 9a, the second electron transport layer 9b, and the third electron transport layer 9c.
  • FIG. 5 shows a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, a second hole transport layer 4b, a first blue fluorescent light emitting layer 6BFa, and a first electron transport layer.
  • 9a first N-type charge generation layer (12a), first P-type charge generation layer (13a), third hole transport layer (4c), red phosphorescent emission layer (6RP), yellow green phosphorescence emission layer (6YGP), green phosphorescence Light-emitting layer (6GP), second electron transport layer (9b), second N-type charge generation layer (12b), second P-type charge generation layer (13b), fourth hole transport layer (4d), fifth hole transport layer (4e) ,
  • a structure of an organic light-emitting device in which the second blue fluorescent emission layer 6BFb, the third electron transport layer 9c, the electron injection layer 10, the cathode 11 and the capping layer 14 are sequentially stacked is illustrated.
  • the compound represented by Formula 1 may be included in the first blue fluorescent layer 6BFa or the second blue fluorescent layer 6BFb, and the compound represented by Formula 2 is the first electron transport layer 9a.
  • the second electron transport layer 9b, the third electron transport layer 9c, and the electron injection layer 10 may be included in one or more layers.
  • FIG. 6 shows a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, a second hole transport layer 4b, a first blue fluorescent light emitting layer 6BFa, and a first electron transport layer.
  • 9a) a first N-type charge generation layer (12a), a first P-type charge generation layer (13a), a third hole transport layer (4c), a red phosphorescent layer (6RP), a green phosphorescent layer (6GP), a second electron Transport layer 9b, second N-type charge generation layer 12b, second P-type charge generation layer 13b, fourth hole transport layer 4d, fifth hole transport layer 4e, second blue fluorescent light emitting layer 6BFb ), a third electron transport layer 9c, an electron injection layer 10, a cathode 11, and a capping layer 14 are sequentially stacked.
  • the compound represented by Formula 1 may be included in the first blue fluorescent layer 6BFa or the second blue fluorescent layer 6BFb, and the compound represented by Formula 2 is the first electron transport layer 9a.
  • the second electron transport layer 9b, the third electron transport layer 9c, and the electron injection layer 10 may be included in one or more layers.
  • FIG. 7 shows a substrate 1, an anode 2, a first p-doped hole transport layer 4pa, a first hole transport layer 4a, a second hole transport layer 4b, a first blue fluorescent light emitting layer 6BFa, First electron transport layer (9a), first N-type charge generation layer (12a), first P-type charge generation layer (13a), third hole transport layer (4c), fourth hole transport layer (4d), second blue fluorescence Light emitting layer (6BFb), second electron transport layer (9b), second N-type charge generation layer (12b), second P-type charge generation layer (13b), fifth hole transport layer (4e), sixth hole transport layer (4f) ,
  • a structure of an organic light-emitting device in which a third blue fluorescent emission layer 6BFc, a third electron transport layer 9c, an electron injection layer 10, a cathode 11 and a capping layer 14 are sequentially stacked is illustrated.
  • the compound represented by Formula 1 may be included in one or more layers of the first blue fluorescent light emitting layer 6BFa, the second blue fluorescent light emitting layer 6BFb, and the third clean fluorescent light emitting layer 6BFb,
  • the compound represented by Formula 2 may be included in one or more of the first electron transport layer 9a, the second electron transport layer 9c, the third electron transport layer 9c, and the electron injection layer 10.
  • FIG. 9 shows a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, an electron injection and transport layer (The structure of an organic light emitting device in which 8) and the cathode 11 are sequentially stacked is illustrated.
  • the compound represented by Formula 1 or 2 may be included in the light emitting layer 6, and the compound represented by Formula 3 may be included in the hole blocking layer 7 or the electron injection and transport layer 8 have.
  • organic light emission in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 6, an electron injection and transport layer 8, and a cathode 11 are sequentially stacked.
  • the structure of the device is illustrated.
  • the compound represented by Formula 1 or 2 may be included in the light emitting layer 6, and the compound represented by Formula 3 may be included in the electron injection and transport layer 8.
  • the N-type charge generation layer is 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), fluorine-substituted 3,4,9,10-P Lylenetetracarboxylic dianhydride (PTCDA), cyano-substituted PTCDA, naphthalenetetracarboxylic dianhydride (NTCDA), fluorine-substituted NTCDA, cyano-substituted NTCDA, hexaazatriphenylline derivative And the like, but is not limited thereto.
  • the N-type charge generation layer may include a benzoimidazophenanthrinine derivative and a metal of Li at the same time.
  • the P-type charge generation layer may simultaneously include an arylamine derivative and a compound containing a cyano group.
  • the organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that the organic material layer includes the compound.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light-emitting device according to the present specification forms an anode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and after forming an organic material layer including the first organic material layer and the second organic material layer described above, It can be manufactured by depositing a material that can be used as a cathode thereon.
  • an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the organic material layer including the first organic material layer and the second organic material layer further includes a hole injection layer, a hole transport layer, an electron injection and transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, etc. It may be a multi-layered structure.
  • the organic material layer is made of a variety of polymer materials, and is used in a smaller number of solvent processes, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be made in layers.
  • the anode is an electrode for injecting holes, and a material having a large work function is preferably used as the anode material to facilitate hole injection into an organic material layer.
  • the cathode material that can be 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); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode is an electrode for injecting electrons
  • the cathode material is usually a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multilayered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
  • the hole injection layer is a layer that facilitates injection of holes from the anode to the light emitting layer, and has a single layer or a multilayer structure of two or more layers.
  • the hole injection material is a material that can well inject holes from the anode at a low voltage, and it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances.
  • the hole injection layer has a two-layer structure, and each of the layers includes the same or different materials.
  • the hole transport layer may serve to facilitate the transport of holes, and has a single layer or a multilayer structure of two or more layers.
  • the hole transport material a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and having high mobility for holes is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.
  • the hole transport layer has a two-layer structure, and each of the layers includes the same or different materials.
  • an arylamine compound is used as the material of the hole transport layer.
  • the hole injection and transport layer is a layer that simultaneously transports and injects holes, and a hole transport layer material and/or a hole injection layer material known in the art may be used.
  • the electron injection and transport layer is a layer that simultaneously transports electrons and injects electrons, and an electron transport layer material and/or an electron injection layer material known in the art may be used.
  • An electron blocking layer may be provided between the hole transport layer and the emission layer. Materials known in the art may be used for the electron blocking layer.
  • the emission layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material.
  • a material capable of emitting light in a visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency against fluorescence or phosphorescence is preferable.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.
  • Alq3 8-hydroxy-quinoline aluminum complex
  • Carbazole-based compounds Dimerized styryl compounds
  • BAlq 10-hydroxybenzo quinoline-metal compound
  • Benzoxazole, benzthiazole, and benzimidazole-based compounds include Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.
  • Examples of the host material for the light emitting layer include a condensed aromatic ring derivative or a heterocyclic compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the emission dopants include PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium). ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a fluorescent material such as Alq 3 (tris(8-hydroxyquinolino)aluminum), but is not limited thereto.
  • a phosphor such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq 3 (tris(8-hydroxyquinolino)aluminum) may be used as the emission dopant.
  • a fluorescent material such as Alq 3 (tris(8-hydroxyquinolino)aluminum)
  • Alq 3 tris(8-hydroxyquinolino)aluminum
  • the light emitting dopant is a phosphorescent material such as (4,6-F 2 ppy) 2 Irpic, but spiro-DPVBi, spiro-6P, distillbenzene (DSB), distrylarylene (DSA ), a fluorescent material such as a PFO-based polymer or a PPV-based polymer may be used, but is not limited thereto.
  • a hole blocking layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used.
  • the electron transport layer serves to facilitate the transport of electrons.
  • the electron transport material a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high mobility for electrons is suitable.
  • Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron injection layer serves to facilitate injection of electrons.
  • the electron injection material a compound having an ability to transport electrons, an electron injection effect from the cathode, an excellent electron injection effect to a light emitting layer or a light emitting material, and excellent in thin film formation ability is preferable.
  • Complex compounds and nitrogen-containing 5-membered ring derivatives but are not limited thereto.
  • the metal complex compound examples include lithium 8-hydroxyquinolinato, 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)beryllium, 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, etc. It is not limited to this.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
  • 2-bromo-1,3-diiodo-5-methylbenzene [2-bromo-1,3-diiodo-5-methylbenzene] 20 g, amine A-2 38 g, sodium tertbutoxide (sodium tert-butoxide) 14 g, bis(tri-tertbutylphosphine)palladium(0) (Pd(P(t-Bu) 3 ) 2 ) 0.24 g was added to 450 mL of toluene, heated at 120 o C, and 4 Stir for hours.
  • reaction solution was kept at -78°C and stirred for about 1 hour, and then the organic layer was extracted with methylene chloride, treated with MgSO 4 (anhydrous), and filtered.
  • a glass substrate coated with a thin film of 1000 ⁇ of ITO (indium tin oxide) was put in distilled water dissolved in a detergent and washed with ultrasonic waves.
  • ITO indium tin oxide
  • a Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • the HI-A compound was thermally vacuum deposited to a thickness of 600 ⁇ on the prepared ITO transparent electrode to form a hole injection layer. 50 ⁇ of the HAT compound and 600 ⁇ of the HT-A compound were sequentially vacuum deposited on the hole injection layer to form a hole transport layer. On the hole transport layer, the following HT-B was vacuum-deposited to a thickness of 50 ⁇ to form an electron blocking layer.
  • BH-1 compound and Compound 1 with a film thickness of 200 ⁇ were vacuum-deposited at a weight ratio of 100:2 on the hole transport layer to form a light emitting layer.
  • Compound E1 was vacuum-deposited on the emission layer to form a hole blocking layer with a thickness of 50 ⁇ .
  • Compound ET and the following LiQ compound were vacuum-deposited at a weight ratio of 1:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300 ⁇ .
  • Lithium fluoride (LiF) in a thickness of 10 ⁇ and aluminum in a thickness of 1000 ⁇ were sequentially deposited on the electron injection and transport layer to form a negative electrode.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that the materials shown in Table 1 were used as the dopant material and the hole blocking layer material of the emission layer.
  • the Examples 1 to 18 and Comparative Examples 1 to were measured for 8 organic light emitting element driving voltage and luminous efficiency at a current density of 10 mA / cm 2 with respect to the (in terms of efficiency), initially at a current density of 15 mA / cm 2 The time (T95) to be 95% of the luminance was measured and displayed. The results are shown in Table 1 below.
  • Comparative Examples 1 to 3 used a compound different from the compounds of Formulas 1 and 2 of the present invention as the dopant and hole blocking layer material of the light emitting layer. As compared with Comparative Examples 1 to 3, Examples 1 to 14 show low voltage and high efficiency characteristics, and it can be confirmed that the lifespan is particularly increased to a high width.
  • any one of the dopant of the light emitting layer and the material of the hole blocking layer was used as the compound of the present invention.
  • Example 1 and Comparative Example 4 Example 4 and Comparative Example 5, and Example 12 and Comparative Example 6, respectively, the same material was used as the dopant material of the light emitting layer, but the material used for the hole blocking layer was different. It can be seen that the effect difference appears when applied to the device. It can be seen that Examples 1, 4, and 12 have low voltage, high efficiency, and high lifetime characteristics compared to Comparative Examples 4, 5, and 6.
  • Example 2 Comparative Example 7, Examples 9, 18, and 8 are device data using the same hole blocking material and different dopant materials, respectively. Due to the difference in the dopant material, it can be seen that Examples 2, 9 and 18 have low voltage, high efficiency, and long life characteristics compared to Comparative Examples 7 and 8.
  • a glass substrate coated with a thin film of 1000 ⁇ of ITO (indium tin oxide) was put in distilled water dissolved in a detergent and washed with ultrasonic waves.
  • ITO indium tin oxide
  • a Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • the following HI-A compound was thermally vacuum deposited to a thickness of 600 ⁇ on the prepared ITO transparent electrode to form a hole injection layer.
  • 50 ⁇ of the following HAT compound and 600 ⁇ of the following HT-A compound were sequentially vacuum-deposited to form a hole transport layer.
  • the BH-2 compound and the following Compound 2 with a film thickness of 200 ⁇ were vacuum-deposited at a weight ratio of 100:2 on the hole transport layer to form a light emitting layer.
  • LiQ compound E10 and the following LiQ compound were vacuum-deposited at a weight ratio of 1:1 on the emission layer to form an electron injection and transport layer with a thickness of 350 ⁇ .
  • Lithium fluoride (LiF) in a thickness of 10 ⁇ and aluminum in a thickness of 1000 ⁇ were sequentially deposited on the electron injection and transport layer to form a negative electrode.
  • the deposition rate of the organic material was maintained at 0.4 to 0.9 ⁇ /sec
  • the deposition rate of lithium fluoride at the cathode was 0.3 ⁇ /sec
  • the deposition rate of aluminum was 2 ⁇ /sec
  • the vacuum degree at the time of deposition was 1 ⁇ 10 -7.
  • an organic light emitting device was manufactured.
  • An organic light-emitting device was manufactured in the same manner as in Example 19, except that the dopant material of the emission layer and the material of the electron injection and transport layer were used in Table 2 below.
  • Comparative Examples 12 to 14 used the same dopant material as in Examples 19, 20, and 24, respectively, and different materials were used only for the electron injection and transport layers. Examples 19, 20, and 24 show characteristics of low voltage, high efficiency and long life, compared with Comparative Examples 12 to 14.
  • Comparative Examples 15 and 16 used the same electron injection and transport layer materials as Examples 24, 26, 23, and 28, respectively. However, since the dopant materials are different, Examples 24, 26, 23, and 38 are compared with Comparative Examples 15 and 16, respectively, and it can be seen that when applied to a device, more excellent effects are shown.
  • a glass substrate coated with a thin film of 1000 ⁇ of ITO (indium tin oxide) was put in distilled water dissolved in a detergent and washed with ultrasonic waves.
  • ITO indium tin oxide
  • a Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • the HI-A compound was thermally vacuum deposited to a thickness of 600 ⁇ on the prepared ITO transparent electrode to form a hole injection layer.
  • 50 ⁇ of the HAT compound and 600 ⁇ of the HT-A compound were sequentially vacuum deposited on the hole injection layer to form a hole transport layer.
  • the following HT-B was vacuum deposited to a thickness of 50 ⁇ to form an electron blocking layer.
  • a BH-3 compound and Compound 5 with a thickness of 200 ⁇ were vacuum-deposited at a weight ratio of 100:2 to form a light emitting layer.
  • Compound E10 was vacuum-deposited on the emission layer to form a hole blocking layer with a thickness of 50 ⁇ .
  • Compound E2 and the following LiQ compound were vacuum-deposited at a weight ratio of 1:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300 ⁇ .
  • Lithium fluoride (LiF) in a thickness of 10 ⁇ and aluminum in a thickness of 1000 ⁇ were sequentially deposited on the electron injection and transport layer to form a negative electrode.
  • the deposition rate of the organic material was maintained at 0.4 to 0.9 ⁇ /sec
  • the deposition rate of lithium fluoride at the cathode was 0.3 ⁇ /sec
  • the deposition rate of aluminum was 2 ⁇ /sec
  • the vacuum degree at the time of deposition was 1 ⁇ 10 -7.
  • an organic light emitting device was manufactured.
  • An organic light-emitting device was manufactured in the same manner as in Example 29, except that the materials shown in Table 3 below were used as the dopant material, the hole blocking layer material, and the electron injection and transport layer material of the emission layer.
  • Example 29 to 34 and Comparative Examples 17 to 19 was the measurement of driving voltage and light emission efficiency (conversion efficiency) at a current density of 10 mA / cm 2, the organic light emitting device, initially at a current density of 15 mA / cm 2
  • the time (T95) to be 95% of the luminance was measured and displayed. The results are shown in Table 3 below.
  • Comparative Example 17 is data using a compound other than the chemical formula of the present invention as a dopant material, a hole blocking layer material, an electron injection material, and a transport layer material. Comparative Example 18 uses the same hole blocking layer material as in Example 29, and differs only in the dopant material and the electron injection and transport layer material.
  • Comparative Example 19 the same material for the electron injection and transport layer as in Example 34 was used, and different materials were used for the dopant and the hole blocking layer. Accordingly, it can be confirmed that Examples 29 and 34 have excellent effects of low voltage, high efficiency, and long life compared to Comparative Examples 18 and 19.

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Abstract

The present specification pertains to an organic light-emitting device comprising: a first electrode; a second electrode provided facing the first electrode; and an organic material layer provided between the first electrode and the second electrode, wherein the organic material layer includes a layer containing a compound of chemical formula 1 and a layer containing a compound of chemical formula 2.

Description

유기 발광 소자 Organic light emitting element
본 명세서는 유기 발광 소자에 관한 것이다.The present specification relates to an organic light emitting device.
본 출원은 2019년 07월 31일 한국특허청에 제출된 한국 특허 출원 제10-2019-0093179 호의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.This application claims the benefit of the filing date of the Korean Patent Application No. 10-2019-0093179 filed with the Korean Intellectual Property Office on July 31, 2019, the entire contents of which are incorporated herein.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어 질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground.
상기와 같은 유기 발광 소자를 위한 새로운 재료의 개발이 계속 요구되고 있다.Development of a new material for the organic light emitting device as described above is continuously required.
본 명세서는 유기 발광 소자를 제공한다.The present specification provides an organic light emitting device.
본 명세서는 제1 전극; 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 유기물층을 포함하고,The present specification is a first electrode; A second electrode; And an organic material layer provided between the first electrode and the second electrode,
상기 유기물층은 하기 화학식 1로 표시되는 화합물을 포함하는 제1 유기물층 및 하기 화학식 2로 표시되는 화합물을 포함하는 제2 유기물층을 포함하는 유기 발광 소자를 제공한다.The organic material layer provides an organic light emitting device including a first organic material layer including a compound represented by Formula 1 below and a second organic material layer including a compound represented by Formula 2 below.
[화학식 1][Formula 1]
Figure PCTKR2020010175-appb-I000001
Figure PCTKR2020010175-appb-I000001
상기 화학식 1에 있어서,In Formula 1,
A1, A2, A3, B1 및 B2는 서로 같거나 상이하고, 각각 독립적으로 탄화수소고리이며,A1, A2, A3, B1 and B2 are the same as or different from each other, and each independently a hydrocarbon ring,
R1 내지 R5는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아릴옥시기; 또는 치환 또는 비치환된 헤테로고리기이거나; 하기 화학식 3으로 표시되고, R1 내지 R5 중 적어도 하나 이상은 하기 화학식 3으로 표시되고,R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; Or a substituted or unsubstituted heterocyclic group; Represented by the following formula 3, at least one of R1 to R5 is represented by the following formula 3,
[화학식 3][Formula 3]
Figure PCTKR2020010175-appb-I000002
Figure PCTKR2020010175-appb-I000002
상기 화학식 3에 있어서,In Chemical Formula 3,
상기 점선은 A1, A2, A3, B1 또는 B2와 연결되는 부위이고,The dotted line is a portion connected to A1, A2, A3, B1 or B2,
X는 C 또는 Si 이고,X is C or Si,
R6 내지 R8은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이며, R6 to R8 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
n1 및 n5는 각각 0 내지 4의 정수이고,n1 and n5 are each an integer of 0 to 4,
n2 및 n4는 각각 0 내지 5의 정수이고,n2 and n4 are each an integer of 0 to 5,
n3은 0 내지 3의 정수이고,n3 is an integer from 0 to 3,
n1 + n2 + n3 + n4 + n5는 1 이상이고,n1 + n2 + n3 + n4 + n5 is 1 or more,
n1 내지 n5가 2 이상인 경우, 괄호 내의 치환기는 서로 같거나 상이하고,When n1 to n5 are 2 or more, the substituents in parentheses are the same as or different from each other,
[화학식 2] [Formula 2]
Figure PCTKR2020010175-appb-I000003
Figure PCTKR2020010175-appb-I000003
상기 화학식 2에 있어서,In Formula 2,
Y31 및 Y32는 서로 같거나 상이하고, 각각 독립적으로 수소, 치환 또는 비치환된 알킬기, 또는 치환 또는 비치환된 아릴기이거나, 서로 결합하여 치환 또는 비치환된 고리를 형성하고,Y31 and Y32 are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or combine with each other to form a substituted or unsubstituted ring,
R3-1은 수소, 중수소, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 헤테로아릴기, 또는 하기 화학식 4이거나, 인접한 기와 서로 결합하여 탄화수소고리를 형성하고, R3-1 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or the following formula (4), or is bonded to each other with adjacent groups to form a hydrocarbon ring,
a31은 0 내지 8의 정수이고,a31 is an integer from 0 to 8,
a31이 복수일 때, R3-1은 서로 같거나 상이하고,when a31 is plural, R3-1 is the same as or different from each other,
[화학식 4][Formula 4]
Figure PCTKR2020010175-appb-I000004
Figure PCTKR2020010175-appb-I000004
상기 화학식 4에 있어서,In Formula 4,
상기 점선은 코어와 연결되는 부분이고,The dotted line is a part connected to the core,
Ar41 및 Ar42는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이며,Ar 41 and Ar 42 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
X1 내지 X3은 서로 같거나 상이하고, 각각 독립적으로 N 또는 CR"이며,X 1 to X 3 are the same as or different from each other, and each independently N or CR",
X1 내지 X3중 적어도 하나는 N이고,At least one of X 1 to X 3 is N,
R"은 수소; 중수소; 할로겐기; 니트릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아릴옥시기; 또는 치환 또는 비치환된 헤테로고리기이고,R" is hydrogen; deuterium; halogen group; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkynyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted cyclo An alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aryloxy group; or a substituted or unsubstituted heterocyclic group,
L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합, 치환 또는 비치환된 아릴렌기, 또는 치환 또는 비치환된 헤테로아릴렌기이다.L 1 to L 3 are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.
본 명세서에 기재된 유기 발광 소자는 제1 유기물층에 화학식 1로 표시되는 화합물을 포함하고, 제2 유기물층에 화학식 2로 표시되는 화합물을 포함함으로써, 낮은 구동전압을 가지고, 우수한 효율 특성, 및 우수한 수명을 갖는다. 구체적으로, 적절한 HOMO 에너지 준위와 LUMO 에너지 준위의 조절을 통하여 전자 수송 정도를 조절하여 낮은 구동 전압, 높은 효율 및 수명이 개선될 수 있다. The organic light emitting device described in the present specification includes the compound represented by Formula 1 in the first organic material layer and the compound represented by Formula 2 in the second organic material layer, thereby having a low driving voltage, excellent efficiency characteristics, and excellent lifespan. Have. Specifically, low driving voltage, high efficiency, and lifespan may be improved by controlling the degree of electron transport through the adjustment of an appropriate HOMO energy level and LUMO energy level.
도 1, 2 및 8 내지 10은 본 명세서의 일 실시상태에 따르는 유기 발광 소자의 예를 도시한 것이다.1, 2, and 8 to 10 show examples of an organic light-emitting device according to an exemplary embodiment of the present specification.
도 3 내지 7은 2 이상의 스택을 포함하는 유기 발광 소자의 예를 도시한 것이다.3 to 7 show examples of organic light emitting devices including two or more stacks.
[부호의 설명][Explanation of code]
1: 기판/ 2: 양극/ 3: 정공주입층/ 4: 정공수송층/ 4a: 제1 정공수송층/ 4b: 제2 정공수송층/ 4c: 제3 정공수송층/ 4d: 제4 정공수송층/ 4e: 제5 정공수송층/ 4f: 제6 정공수송층/ 4p: p-도핑된 정공수송층/ 4R: 적색 정공수송층/ 4G: 녹색 정공수송층/ 4B: 청색 정공수송층/ 5: 전자차단층/ 6: 발광층/ 6a: 제1 발광층/ 6b: 제2 발광층/ 6c: 제3 발광층/ 6BF: 청색 형광 발광층/ 6BFa: 제1 청색 형광 발광층/ 6BFb: 제2 청색 형광 발광층/ 6YGP: 황색 녹색 인광 발광층/ 6RP: 적색 인광 발광층/ 6GP: 녹색 인광 발광층/ 7: 정공차단층/ 8: 전자 주입 및 수송층/ 9: 전자수송층/ 9a: 제1 전자수송층/ 9b: 제2 전자수송층/ 9c: 제3 전자수송층/ 10: 전자주입층/ 11: 음극/ 12: N형 전하생성층/ 12a: 제1 N형 전하생성층/ 12b: 제2 N형 전하생성층/ 13: P형 전하생성층/ 13a: 제1 P형 전하생성층/ 13b: 제2 P형 전하생성층/ 14: 캡핑층1: substrate/ 2: anode/ 3: hole injection layer/ 4: hole transport layer/ 4a: first hole transport layer/ 4b: second hole transport layer/ 4c: third hole transport layer/ 4d: fourth hole transport layer/ 4e: agent 5 hole transport layer/ 4f: sixth hole transport layer/ 4p: p-doped hole transport layer/ 4R: red hole transport layer/ 4G: green hole transport layer/ 4B: blue hole transport layer/ 5: electron blocking layer/ 6: light emitting layer/ 6a: First emitting layer/6b: second emitting layer 6c: third emitting layer 6BF: blue fluorescent emitting layer 6BFa: first blue fluorescent emitting layer 6BFb: second blue fluorescent emitting layer 6YGP: yellow green phosphorescent emitting layer 6RP: red phosphorescent emitting layer / 6GP: green phosphorescent emission layer/ 7: hole blocking layer/ 8: electron injection and transport layer/ 9: electron transport layer/ 9a: first electron transport layer/ 9b: second electron transport layer/ 9c: third electron transport layer/ 10: electron injection Layer/ 11: Cathode/ 12: N-type charge generation layer/ 12a: First N-type charge generation layer/ 12b: Second N-type charge generation layer/ 13: P-type charge generation layer/ 13a: First P-type charge generation Layer/ 13b: second P-type charge generation layer/ 14: capping layer
이하, 본 명세서에 대하여 더욱 상세하게 설명한다.Hereinafter, the present specification will be described in more detail.
본 명세서는 화학식 1로 표시되는 화합물을 포함하는 제1 유기물층 및 화학식 2로 표시되는 화합물을 포함하는 제2 유기물층을 동시에 포함하는 유기 발광 소자를 제공한다. 상기 화학식 1의 화합물이 포함된 발광층은 얕은 HOMO준위를 가지고 있고 상기 화학식 2의 화합물은 깊은 HOMO, LUMO 준위를 가지고 있어 전자가 쉽게 발광층으로 전달 시킬 수 있어 높은 효율과 수명을 나타낸다.The present specification provides an organic light emitting device including a first organic material layer including a compound represented by Formula 1 and a second organic material layer including a compound represented by Formula 2 at the same time. The light-emitting layer containing the compound of Formula 1 has a shallow HOMO level, and the compound of Formula 2 has a deep HOMO and LUMO level, so electrons can be easily transferred to the light-emitting layer, thus exhibiting high efficiency and lifetime.
본 명세서에 있어서 치환기의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다.Examples of the substituents in the present specification are described below, but are not limited thereto.
본 명세서에 있어서, 어떤 부분이 어떤 구성요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성 요소를 더 포함할 수 있는 것을 의미한다.In the present specification, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless otherwise stated.
본 명세서에 있어서, 어떤 부재가 다른 부재 "상에" 위치하고 있다고 할 때, 이는 어떤 부재가 다른 부재에 접해 있는 경우뿐 아니라 두 부재 사이에 또 다른 부재가 존재하는 경우도 포함한다.In the present specification, when a member is said to be located "on" another member, this includes not only the case where the member is in contact with the other member, but also the case where another member exists between the two members.
본 명세서에 있어서, 점선 또는
Figure PCTKR2020010175-appb-I000005
는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In this specification, a dotted line or
Figure PCTKR2020010175-appb-I000005
Means a site bonded to another substituent or a bonding portion.
본 명세서에서 치환기의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다.Examples of the substituent in the present specification are described below, but are not limited thereto.
상기 “치환” 이라는 용어는 화합물의 탄소 원자에 결합된 수소 원자가 다른 치환기로 바뀌는 것을 의미하며, 치환되는 위치는 수소 원자가 치환되는 위치 즉, 치환기가 치환 가능한 위치라면 한정하지 않으며, 2 이상 치환되는 경우, 2 이상의 치환기는 서로 동일하거나 상이할 수 있다.The term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted. , Two or more substituents may be the same or different from each other.
본 명세서에서 “치환 또는 비치환된” 이라는 용어는 중수소; 할로겐기; 시아노기(-CN); 니트로기; 히드록시기; 실릴기; 붕소기; 알킬기; 알케닐기; 알키닐기; 알콕시기; 알킬티오기; 아릴옥시기; 아릴티오기; 시클로알킬기; 아릴기; 아민기; 및 헤테로고리기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되었거나, 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다. In the present specification, the term “substituted or unsubstituted” refers to deuterium; Halogen group; Cyano group (-CN); Nitro group; Hydroxy group; Silyl group; Boron group; Alkyl group; Alkenyl group; Alkynyl group; Alkoxy group; Alkylthio group; Aryloxy group; Arylthio group; Cycloalkyl group; Aryl group; Amine group; And it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, two or more of the substituents exemplified above are substituted with a connected substituent, or it means that no substituents are present.
본 명세서에 있어서, 2 이상의 치환기가 연결된다는 것은 어느 하나의 치환기의 수소가 다른 치환기로 대체된 것을 말한다. 예를 들어, 이소프로필기와 페닐기가 연결되어
Figure PCTKR2020010175-appb-I000006
또는
Figure PCTKR2020010175-appb-I000007
의 치환기가 될 수 있다. In the present specification, the connection of two or more substituents means that hydrogen of any one of the substituents is replaced with another substituent. For example, an isopropyl group and a phenyl group are connected
Figure PCTKR2020010175-appb-I000006
or
Figure PCTKR2020010175-appb-I000007
It may be a substituent of.
본 명세서에 있어서, 3개의 치환기가 연결되는 것은 (치환기 1)-(치환기 2)-(치환기 3)이 연속하여 연결되는 것뿐만 아니라, (치환기 1)에 (치환기 2) 및 (치환기 3)이 연결되는 것도 포함한다. 예를 들어, 2개의 페닐기 및 이소프로필기가 연결되어
Figure PCTKR2020010175-appb-I000008
또는
Figure PCTKR2020010175-appb-I000009
의 치환기가 될 수 있다. 4 이상의 치환기가 연결되는 것에도 전술한 것과 동일하게 적용된다.In the present specification, the connection of three substituents is not only that (substituent 1)-(substituent 2)-(substituent 3) is continuously connected, but also (substituent 2) and (substituent 3) are Includes connections. For example, two phenyl groups and isopropyl groups are connected
Figure PCTKR2020010175-appb-I000008
or
Figure PCTKR2020010175-appb-I000009
It may be a substituent of. The same applies to those in which four or more substituents are connected.
본 명세서에 있어서, “A 또는 B로 치환된”은 A로만 치환된 경우 또는 B로만 치환된 경우뿐만 아니라, A 및 B로 치환된 경우도 포함한다.In the present specification, "substituted with A or B" includes not only the case where A is substituted or only B is substituted, but also the case where A and B are substituted.
본 명세서에 있어서, “치환 또는 비치환된”은 중수소; 할로겐기; 시아노기(-CN); 니트로기; 히드록시기; 실릴기; 붕소기; 탄소수 1 내지 10의 알킬기; 탄소수 2 내지 10의 알케닐기; 탄소수 2 내지 10의 알키닐기; 탄소수 1 내지 10의 알콕시기; 탄소수 1 내지 10의 알킬티오기; 탄소수 6 내지 30의 아릴옥시기; 탄소수 6 내지 30의 아릴티오기; 탄소수 3 내지 30의 시클로알킬기; 탄소수 6 내지 30의 아릴기; 아민기; 및 탄소수 2 내지 30의 헤테로고리기로 이루어진 군에서 선택된 1 이상의 치환기로 치환되거나, 상기 군애서 선택된 2 이상의 기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다. In the present specification, "substituted or unsubstituted" is deuterium; Halogen group; Cyano group (-CN); Nitro group; Hydroxy group; Silyl group; Boron group; An alkyl group having 1 to 10 carbon atoms; An alkenyl group having 2 to 10 carbon atoms; Alkynyl group having 2 to 10 carbon atoms; An alkoxy group having 1 to 10 carbon atoms; An alkylthio group having 1 to 10 carbon atoms; Aryloxy group having 6 to 30 carbon atoms; Arylthio group having 6 to 30 carbon atoms; A cycloalkyl group having 3 to 30 carbon atoms; Aryl group having 6 to 30 carbon atoms; Amine group; And it is substituted with one or more substituents selected from the group consisting of a heterocyclic group having 2 to 30 carbon atoms, or substituted with a substituent to which two or more groups selected from the group are connected, or not having any substituents.
본 명세서에 있어서, “치환 또는 비치환된”은 중수소; 할로겐기; 시아노기(-CN); 니트로기; 히드록시기; 실릴기; 붕소기; 탄소수 1 내지 6의 알킬기; 탄소수 2 내지 6의 알케닐기; 탄소수 2 내지 6의 알키닐기; 탄소수 1 내지 6의 알콕시기; 탄소수 1 내지 6의 알킬티오기; 탄소수 6 내지 20의 아릴옥시기; 탄소수 6 내지 20의 아릴티오기; 탄소수 3 내지 20의 시클로알킬기; 탄소수 6 내지 20의 아릴기; 아민기; 및 탄소수 2 내지 20의 헤테로고리기로 이루어진 군에서 선택된 1 이상의 치환기로 치환되거나, 상기 군애서 선택된 2 이상의 기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다. In the present specification, "substituted or unsubstituted" is deuterium; Halogen group; Cyano group (-CN); Nitro group; Hydroxy group; Silyl group; Boron group; An alkyl group having 1 to 6 carbon atoms; An alkenyl group having 2 to 6 carbon atoms; Alkynyl group having 2 to 6 carbon atoms; An alkoxy group having 1 to 6 carbon atoms; An alkylthio group having 1 to 6 carbon atoms; Aryloxy group having 6 to 20 carbon atoms; Arylthio group having 6 to 20 carbon atoms; A cycloalkyl group having 3 to 20 carbon atoms; Aryl group having 6 to 20 carbon atoms; Amine group; And it is substituted with one or more substituents selected from the group consisting of a heterocyclic group having 2 to 20 carbon atoms, or substituted with a substituent to which two or more groups selected from the group are connected, or does not have any substituents.
상기 치환기들의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다. Examples of the substituents are described below, but are not limited thereto.
본 명세서에 있어서, 할로겐기의 예로는 불소(-F), 염소(-Cl), 브롬(-Br) 또는 요오드(-I)가 있다.In the present specification, examples of the halogen group include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).
본 명세서에 있어서, 알킬기는 직쇄 또는 분지쇄를 포함하며, 탄소수는 특별히 한정되지 않으나 1 내지 60, 1 내지 30, 또는 1 내지 20이다. 상기 알킬기의 구체적인 예로는 메틸기, 에틸기, 프로필기, 부틸기, 펜틸기, 헥실기, 헵틸기, 옥틸기, 노닐기 등이 있으며, 상기 알킬기는 직쇄 또는 분지쇄일 수 있으며, 일 예에 따르면, 프로필기는 n-프로필기 및 이소프로필기를 포함하고, 부틸기는 n-부틸기, 이소부틸기 및 tert-부틸기를 포함한다.In the present specification, the alkyl group includes a linear or branched chain, and the number of carbon atoms is not particularly limited, but is 1 to 60, 1 to 30, or 1 to 20. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and the like, and the alkyl group may be a straight chain or a branched chain. According to an example, propyl The group includes an n-propyl group and an isopropyl group, and the butyl group includes an n-butyl group, an isobutyl group and a tert-butyl group.
본 명세서에 있어서, 시클로알킬기의 탄소수는 특별히 한정되지 않으나, 3 내지 60, 3 내지 30, 3 내지 20, 또는 3 내지 10 이다. 시클로알킬기는 단일고리기뿐만 아니라 다리목(bridgehead), 접합고리(fused ring), 스피로고리(spiro)와 같은 이중고리기를 포함한다. 구체적으로 시클로프로필기, 시클로부틸기, 시클로펜틸기, 시클로헥실기, 시클로헵틸기, 시클로옥틸기, 아다만틸기 등이 있으나, 이에 한정되지 않는다. In the present specification, the number of carbon atoms of the cycloalkyl group is not particularly limited, but is 3 to 60, 3 to 30, 3 to 20, or 3 to 10. Cycloalkyl groups include monocyclic groups as well as bicyclic groups such as bridgeheads, fused rings, and spiro rings. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, and the like, but is not limited thereto.
본 명세서에 있어서, 시클로알켄(cycloalkene)은 탄화수소고리 내에 이중결합이 존재하나, 방향족이 아닌 고리기로서, 탄소수는 특별히 한정되지 않으나, 3 내지 60, 3 내지 30, 3 내지 20, 또는 3 내지 10 이다. 시클로알켄은 단일고리기뿐만 아니라 다리목(bridgehead), 접합고리(fused ring), 스피로고리(spiro)와 같은 이중고리기를 포함한다. 상기 시클로알켄의 예로는 시클로프로펜, 시클로뷰텐, 시클로펜텐, 시클로헥센등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, cycloalkene is a cyclic group that has a double bond in the hydrocarbon ring, but is not aromatic, and the number of carbons is not particularly limited, but 3 to 60, 3 to 30, 3 to 20, or 3 to 10 to be. Cycloalkenes include not only monocyclic groups, but also bicyclic groups such as bridgehead, fused ring, and spiro. Examples of the cycloalkene include cyclopropene, cyclobutene, cyclopentene, and cyclohexene, but are not limited thereto.
본 명세서에 있어서, 알콕시기는 산소원자에 아릴기가 연결된 것이며, 아킬티오기는 황원자에 알킬기가 연결된 것으로, 알콕시기 및 알킬티오기의 알킬기에는 전술한 알킬기에 관한 설명이 적용될 수 있다.In the present specification, the alkoxy group is an aryl group connected to an oxygen atom, an arylthio group is an alkyl group connected to a sulfur atom, and the above-described description of the alkyl group may be applied to the alkyl group of the alkoxy group and the alkylthio group.
본 명세서에 있어서, 아릴기는 단환식 아릴기 또는 다환식 아릴기일 수 있으며, 탄소수는 특별히 한정되지 않으나 6 내지 60, 6 내지 30이 또는 6 내지 20이다. 상기 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기, 쿼터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트레닐기, 파이레닐기, 페릴레닐기, 트리페닐기, 크라이세닐기, 플루오레닐기, 플루오란테닐기, 트리페닐레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the aryl group may be a monocyclic aryl group or a polycyclic aryl group, and the number of carbon atoms is not particularly limited, but 6 to 60, 6 to 30, or 6 to 20. The monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or a quarterphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, fluoranthenyl group, triphenylenyl group, etc. , But is not limited thereto.
본 명세서에 있어서, 플루오레닐기의 9번 탄소원자(C)는 알킬기, 아릴기 등으로 치환될 수 있고, 치환기 2개가 서로 결합하여 시클로펜탄, 플루오렌 등의 스피로 구조를 형성할 수 있다. In the present specification, carbon atom 9 (C) of the fluorenyl group may be substituted with an alkyl group, an aryl group, etc., and two substituents may be bonded to each other to form a spiro structure such as cyclopentane and fluorene.
본 명세서에 있어서, 치환된 아릴기는 아릴기에 지방족 고리가 축합된 형태도 포함할 수 있다. 예컨대, 하기 구조의 테트라하이드로나프탈렌기는 치환된 아릴기에 포함된다. 하기 구조에서, 벤젠고리의 탄소 중 하나가 다른 위치에 연결될 수 있다.In the present specification, the substituted aryl group may include a form in which an aliphatic ring is condensed with an aryl group. For example, a tetrahydronaphthalene group having the following structure is included in a substituted aryl group. In the following structure, one of the carbons of the benzene ring may be linked to another position.
Figure PCTKR2020010175-appb-I000010
Figure PCTKR2020010175-appb-I000010
본 명세서에 있어서, 아릴옥시기는 산소원자에 아릴기가 연결된 것이며, 아릴티오기는 황원자에 아릴기가 연결된 것으로, 아릴옥시기 및 아릴티오기의 아릴기에는 전술한 아릴기에 관한 설명이 적용될 수 있다. 아릴옥시기의 아릴기는 전술한 아릴기의 예시와 같다. 구체적으로 아릴옥시기로는 페녹시기, p-토릴옥시기, m-토릴옥시기, 3,5-디메틸-페녹시기, 2,4,6-트리메틸페녹시기, p-tert-부틸페녹시기, 3-바이페닐옥시기, 4-바이페닐옥시기, 1-나프틸옥시기, 2-나프틸옥시기, 4-메틸-1-나프틸옥시기, 5-메틸-2-나프틸옥시기, 1-안트릴옥시기, 2-안트릴옥시기, 9-안트릴옥시기, 1-페난트릴옥시기, 3-페난트릴옥시기, 9-페난트릴옥시기 등이 있고, 아릴티옥시기로는 페닐티옥시기, 2－메틸페닐티옥시기, 4－tert－부틸페닐티옥시기 등이 있으며, 이에 한정되는 것은 아니다.In the present specification, an aryloxy group is an aryl group connected to an oxygen atom, an arylthio group is an aryl group connected to a sulfur atom, and the aryl group described above may be applied to the aryl group of the aryloxy group and the arylthio group. The aryl group of the aryloxy group is the same as the aryl group described above. Specifically, the aryloxy group includes a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3- Biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, and 9-phenanthryloxy group, and the arylthioxy group includes a phenylthioxy group, 2- Methylphenyl thioxy group, 4-tert-butylphenyl thioxy group, and the like, but are not limited thereto.
본 명세서에 있어서, 실릴기는 -SiYaYbYc의 화학식으로 표시될 수 있고, 상기 Ya, Yb 및 Yc는 각각 수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 또는 치환 또는 비치환된 아릴기일 수 있다. 상기 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, tert-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 디메틸페닐실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다. In the present specification, the silyl group may be represented by the formula of -SiY a Y b Y c , wherein Y a , Y b and Y c are each hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group is specifically trimethylsilyl group, triethylsilyl group, tert-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, dimethylphenylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.
본 명세서에 있어서, 붕소기는 -BYdYe의 화학식으로 표시될 수 있고, 상기 Yd 및 Ye는 각각 수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 또는 치환 또는 비치환된 아릴기일 수 있다. 상기 실릴기는 구체적으로 디메틸붕소기, 디에틸붕소기, tert-부틸메틸붕소기, 비닐메틸붕소기, 프로필메틸붕소기, 메틸페닐붕소기, 디페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다. In the present specification, the boron group may be represented by the formula of -BY d Y e , wherein Y d and Y e are each hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or it may be a substituted or unsubstituted aryl group. Specifically, the silyl group includes a dimethyl boron group, a diethyl boron group, a tert-butylmethyl boron group, a vinyl methyl boron group, a propyl methyl boron group, a methylphenyl boron group, a diphenyl boron group, a phenyl boron group, etc., but is not limited thereto. .
본 명세서에 있어서, 아민기는 -NRaRb로 나타낼 수 있으며, 상기 Ra 및 Rb는 각각 수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기일 수 있으나, 이에 한정되지 않는다. 상기 아민기는 결합되는 치환기(Ra, Rb)의 종류에 따라, 알킬아민기, 알킬아릴아민기, 아릴아민기, 헤테로아릴아민기, 알킬헤테로아릴아민기, 및 아릴헤테로아릴아민기로 이루어진 군으로부터 선택될 수 있다.In the present specification, the amine group may be represented by -NRaRb, wherein Ra and Rb are each hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or it may be a substituted or unsubstituted heteroaryl group, but is not limited thereto. The amine group is selected from the group consisting of an alkylamine group, an alkylarylamine group, an arylamine group, a heteroarylamine group, an alkylheteroarylamine group, and an arylheteroarylamine group, depending on the type of the substituent (Ra, Rb) to be bonded. Can be.
본 명세서에 있어서, 알킬아민기는 알킬기로 치환된 아민기를 의미하며, 탄소수는 특별히 한정되지 않으나, 1 내지 40, 1 내지 20일 수 있다. 상기 알킬아민기의 구체적인 예로는 메틸아민기, 디메틸아민기, 에틸아민기, 디에틸아민기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the alkylamine group refers to an amine group substituted with an alkyl group, and the number of carbon atoms is not particularly limited, but may be 1 to 40 or 1 to 20. Specific examples of the alkylamine group include a methylamine group, a dimethylamine group, an ethylamine group, and a diethylamine group, but are not limited thereto.
본 명세서에 있어서, 아릴아민기의 예로는 치환 또는 비치환된 모노아릴아민기, 치환 또는 비치환된 디아릴아민기, 또는 치환 또는 비치환된 아릴헤테로아릴아민기가 있다. 상기 아릴아민기 중의 아릴기는 단환식 또는 다환식 아릴기일 수 있다. 상기 아릴아민기의 구체적인 예로는 페닐아민기, 나프틸아민기, 바이페닐아민기, 안트라세닐아민기, 디페닐아민기, 페닐나프틸아민기, 비스(tert-부틸페닐)아민기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted arylheteroarylamine group. The aryl group in the arylamine group may be a monocyclic or polycyclic aryl group. Specific examples of the arylamine group include a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a bis(tert-butylphenyl)amine group, etc. , But is not limited thereto.
본 명세서에 있어서, 헤테로아릴아민기의 예로는 치환 또는 비치환된 모노헤테로아릴아민기, 치환 또는 비치환된 디헤테로아릴아민기, 또는 치환 또는 비치환된 아릴헤테로아릴아민기가 있다.In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted arylheteroarylamine group.
본 명세서에 있어서, 아릴헤테로아릴아민기는 아릴기 및 헤테로아릴기로 치환된 아민기를 의미하여, 전술한 아릴기 및 후술할 헤테로아릴기에 관한 설명이 적용될 수 있다.In the present specification, the arylheteroarylamine group means an amine group substituted with an aryl group and a heteroaryl group, and descriptions of the aryl group and the heteroaryl group to be described later may be applied.
본 명세서에 있어서, 헤테로고리기는 이종원자로 N, O, S, 및 Si중 1개 이상을 포함하는 고리기로서, 탄소수는 특별히 한정되지 않으나 2 내지 60, 또는 2 내지 30이다. 상기 헤테로고리기의 예로는 예로는 피리딜기; 퀴놀린기; 티오펜기; 디벤조티오펜기; 퓨란기; 디벤조퓨란기; 나프토벤조퓨란기; 카바졸기; 벤조카바졸기; 나프토벤조티오펜기; 헥사하이드로카바졸기; 디하이드로아크리딘기; 디벤조아자실린기; 페녹사진기(phenoxazine); 페노싸이아진기(phenothiazine); 디하이드로디벤조아자실린기; 스피로(디벤조실롤-디벤조아자실린)기; 스피로(아크리딘-플루오렌)기; 스피로(플루오렌-잔텐)기; 스피로(플루오렌-싸이오잔텐) 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heterocyclic group is a cyclic group including one or more of N, O, S, and Si as a hetero atom, and the number of carbon atoms is not particularly limited, but is 2 to 60, or 2 to 30. Examples of the heterocyclic group include a pyridyl group; Quinoline group; Thiophene group; Dibenzothiophene group; Furan group; Dibenzofuran group; Naphthobenzofuran group; Carbazole; Benzocarbazole group; Naphthobenzothiophene group; Hexahydrocarbazole group; Dihydroacridine group; Dibenzoazacillin group; Phenoxazine; Phenothiazine; Dihydrodibenzoazacillin group; Spiro (dibenzosilol-dibenzoazacillin) group; Spiro (acridine-fluorene) group; Spiro (fluorene-xanthene) group; Spiro (fluorene-thioxanthene) and the like, but are not limited thereto.
Figure PCTKR2020010175-appb-I000011
Figure PCTKR2020010175-appb-I000011
본 명세서에 있어서, 헤테로아릴기는 방향족인 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다.In the present specification, the description of the aforementioned heterocyclic group may be applied except that the heteroaryl group is aromatic.
본 명세서에 있어서, “인접한” 기는 해당 치환기가 치환된 원자와 직접 연결된 원자에 치환된 치환기, 해당 치환기와 입체구조적으로 가깝게 위치한 치환기, 또는 해당 치환기가 치환된 원자에 치환된 다른 치환기를 의미할 수 있다.In this specification, "adjacent" The group may mean a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally close to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted.
본 명세서에 있어서, “인접한 기가 결합하여 형성된 고리”는 탄화수소 고리; 또는 헤테로 고리를 의미한다.In the present specification, "the ring formed by bonding adjacent groups" refers to a hydrocarbon ring; Or a hetero ring.
본 명세서에 있어서, “인접한 기가 결합하여 형성된 5원 또느 6원의 고리”는 고리 형성에 참여한 치환기를 포함한 고리가 5원 또는 6원인 것을 의미한다. 상기 고리 형성에 참여한 치환기를 포함한 고리에 추가의 고리가 축합되는 것을 포함할 수 있다.In the present specification, “a 5-membered or 6-membered ring formed by bonding adjacent groups” means that the ring including the substituent participating in the ring formation is 5 or 6 members. It may include condensation of an additional ring to the ring including the substituent participating in the ring formation.
본 명세서에 있엉서, 탄화수소 고리는 방향족, 지방족 또는 방향족과 지방족의 축합고리일 수 있으며, 상기 방향족 탄화수소 고리는 1가가 아닌 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있고, 상기 지방족 탄화수소고리는 1가가 아닌 것을 제외하고는 전술한 시클로알킬기에 관한 설명이 적용될 수 있다. 방향족과 지방족의 축합고리의 예로서 1,2,3,4-테트라하이드로나프탈렌기, 2,3-디하이드로-1H-인덴기 등을 들 수 있지만 이에 한정되는 것은 아니다. In the present specification, the hydrocarbon ring may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and the description of the aryl group described above may be applied except that the aromatic hydrocarbon ring is not monovalent, and the aliphatic hydrocarbon ring Except that is not monovalent, the above description of the cycloalkyl group may be applied. Examples of the aromatic and aliphatic condensed ring include a 1,2,3,4-tetrahydronaphthalene group, and a 2,3-dihydro-1H-indene group, but are not limited thereto.
본 명세서에 있어서, 헤테로고리는 1가가 아닌 것을 제외하고는 상기 헤테로고리기에 대한 설명이 적용될 수 있다.In the present specification, the description of the heterocyclic group may be applied, except that the heterocycle is not monovalent.
본 명세서에 있어서, 방향족 탄화수소 고리는 pi 전자가 완전히 컨쥬게이션되고 평면인 고리를 의미하는 것으로, 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다.In the present specification, the aromatic hydrocarbon ring refers to a ring in which pi electrons are completely conjugated and planar, and the description of the aryl group described above may be applied except for a divalent group.
본 명세서에 있어서, 지방족 탄화수소 고리는 방향족 탄화수소고리를 제외한 모든 탄화수소고리를 의미하는 것으로, 시클로알킬고리를 포함할 수 있다. 시클로알킬고리는 2가기인 것을 제외하고는 전술한 시클로알킬기에 관한 설명이 적용될 수 있다. 치환된 지방족 탄화수소 고리에는 방향족 고리가 축합된 지방족 탄화수소 고리도 포함된다. In the present specification, the aliphatic hydrocarbon ring means all hydrocarbon rings except for an aromatic hydrocarbon ring, and may include a cycloalkyl ring. Except that the cycloalkyl ring is a divalent group, the above description of the cycloalkyl group can be applied. The substituted aliphatic hydrocarbon ring also includes an aliphatic hydrocarbon ring condensed with an aromatic ring.
본 명세서에 있어서, 아릴렌기는 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다.In the present specification, the description of the aryl group described above may be applied except that the arylene group is a divalent group.
본 명세서에 있어서, 시클로알킬렌기는 2가기인 것을 제외하고는 전술한 시클로알킬기에 관한 설명이 적용될 수 있다.In the present specification, the description of the cycloalkyl group may be applied except that the cycloalkylene group is a divalent group.
이하, 화학식 1에 관하여 설명한다.Hereinafter, Formula 1 will be described.
[화학식 1][Formula 1]
Figure PCTKR2020010175-appb-I000012
Figure PCTKR2020010175-appb-I000012
본 명세서의 일 실시상태에 있어서, A1 내지 A3, B1 및 B2는 서로 같거나 상이하고, 각각 독립적으로 단환 또는 2환의 탄화수소고리이다.In the exemplary embodiment of the present specification, A1 to A3, B1 and B2 are the same as or different from each other, and each independently a monocyclic or bicyclic hydrocarbon ring.
본 명세서의 일 실시상태에 있어서, A1 내지 A3, B1 및 B2는 서로 같거나 상이하고, 각각 독립적으로 벤젠고리 또는 나프탈렌고리이다.In the exemplary embodiment of the present specification, A1 to A3, B1 and B2 are the same as or different from each other, and each independently a benzene ring or a naphthalene ring.
본 명세서의 일 실시상태에 있어서, A1 내지 A3는 각각 벤젠고리이다.In an exemplary embodiment of the present specification, A1 to A3 are each a benzene ring.
본 명세서의 일 실시상태에 있어서, B1 및 B2는 각각 벤젠고리이다.In an exemplary embodiment of the present specification, B1 and B2 are each a benzene ring.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1은 하기 화학식 1-1로 표시된다.In an exemplary embodiment of the present specification, Formula 1 is represented by the following Formula 1-1.
[화학식 1-1][Formula 1-1]
Figure PCTKR2020010175-appb-I000013
Figure PCTKR2020010175-appb-I000013
상기 화학식 1-1에 있어서, R1 내지 R5 및 n1 내지 n5는 상기 화학식 1에서 정의한 바와 같다.In Formula 1-1, R1 to R5 and n1 to n5 are as defined in Formula 1.
본 명세서의 일 실시상태에 있어서, R1 내지 R5는 서로 같거나 상이하고, 각각 독립적으로, 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아릴옥시기; 또는 치환 또는 비치환된 헤테로고리기이거나, 상기 화학식 3으로 표시된다.In the exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; Or a substituted or unsubstituted heterocyclic group, or is represented by the above formula (3).
본 명세서의 일 실시상태에 있어서, R1, R2, R4, 및 R5는 서로 같거나 상이하고, 각각 독립적으로, 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 헤테로고리기; 또는 상기 화학식 3으로 표시된다.In the exemplary embodiment of the present specification, R1, R2, R4, and R5 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or it is represented by Formula 3 above.
본 명세서의 일 실시상태에 있어서, R1, R2, R4, 및 R5는 서로 같거나 상이하고, 각각 독립적으로, 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 탄소수 1 내지 10의 알킬기; 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 치환 또는 비치환된 탄소수 1 내지 30의 알킬실릴기; 치환 또는 비치환된 탄소수 6 내지 90의 아릴실릴기; 치환 또는 비치환된 탄소수 1 내지 20의 알킬아민기; 치환 또는 비치환된 탄소수 6 내지 60의 아릴아민기; 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴아민기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기; 또는 상기 화학식 3으로 표시된다.In the exemplary embodiment of the present specification, R1, R2, R4, and R5 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C1 to C30 alkylsilyl group; A substituted or unsubstituted arylsilyl group having 6 to 90 carbon atoms; A substituted or unsubstituted C1 to C20 alkylamine group; A substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; A substituted or unsubstituted C2 to C60 heteroarylamine group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Or it is represented by Formula 3 above.
본 명세서의 일 실시상태에 있어서, R1, R2, R4, 및 R5는 서로 같거나 상이하고, 각각 독립적으로, 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 탄소수 1 내지 6의 알킬기; 치환 또는 비치환된 3 내지 20의 시클로알킬기; 치환 또는 비치환된 탄소수 1 내지 18의 알킬실릴기; 치환 또는 비치환된 탄소수 6 내지 60의 아릴실릴기; 치환 또는 비치환된 탄소수 1 내지 12의 알킬아민기; 치환 또는 비치환된 탄소수 6 내지 40의 아릴아민기; 치환 또는 비치환된 탄소수 2 내지 40 헤테로아릴아민기; 치환 또는 비치환된 탄소수 6 내지 20의 아릴기; 치환 또는 비치환된 탄소수 2 내지 20의 헤테로고리기; 또는 상기 화학식 3으로 표시된다.In the exemplary embodiment of the present specification, R1, R2, R4, and R5 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C 1 to C 6 alkyl group; A substituted or unsubstituted 3 to 20 cycloalkyl group; A substituted or unsubstituted C 1 to C 18 alkylsilyl group; A substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms; A substituted or unsubstituted C1-C12 alkylamine group; A substituted or unsubstituted arylamine group having 6 to 40 carbon atoms; A substituted or unsubstituted C2 to C40 heteroarylamine group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted C2 to C20 heterocyclic group; Or it is represented by Formula 3 above.
본 명세서의 일 실시상태에 있어서, R1, R2, R4, 및 R5는 서로 같거나 상이하고, 각각 독립적으로, 수소; 중수소; 할로겐기; 시아노기; 중수소로 치환 또는 비치환된 탄소수 1 내지 10의 알킬기; 중수소로 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 중수소로 치환 또는 비치환된 탄소수 6 내지 60의 아릴아민기; 중수소, 할로겐기, 시아노기 및 탄소수 1 내지 10의 알킬기로 이루어진 군에서 선택된 1 이상의 치환기 또는 상기 군에서 선택된 2 이상의 기가 연결된 치환기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 중수소로 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기; 또는 상기 화학식 3으로 표시된다.In the exemplary embodiment of the present specification, R1, R2, R4, and R5 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium; A cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with deuterium; Arylamine group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium; An aryl group having 6 to 30 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, and an alkyl group having 1 to 10 carbon atoms or a substituent connected with two or more groups selected from the group; A heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium; Or it is represented by Formula 3 above.
본 명세서의 일 실시상태에 있어서, R1, R2, R4, 및 R5는 서로 같거나 상이하고, 각각 독립적으로, 수소; 중수소; 할로겐기; 시아노기; 중수소로 치환 또는 비치환된 탄소수 1 내지 6의 알킬기; 중수소로 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기; 중수소로 치환 또는 비치환된 탄소수 6 내지 40의 아릴아민기; 중수소, 할로겐기, 시아노기 및 탄소수 1 내지 6의 알킬기로 이루어진 군에서 선택된 1 이상의 치환기 또는 상기 군에서 선택된 2 이상의 기가 연결된 치환기로 치환 또는 비치환된 탄소수 6 내지 20의 아릴기; 중수소로 치환 또는 비치환된 탄소수 2 내지 20의 헤테로고리기; 또는 상기 화학식 3으로 표시된다.In the exemplary embodiment of the present specification, R1, R2, R4, and R5 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; A cycloalkyl group having 3 to 20 carbon atoms unsubstituted or substituted with deuterium; Arylamine group having 6 to 40 carbon atoms substituted or unsubstituted with deuterium; An aryl group having 6 to 20 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, and an alkyl group having 1 to 6 carbon atoms or a substituent connected with two or more groups selected from the group; A heterocyclic group having 2 to 20 carbon atoms substituted or unsubstituted with deuterium; Or it is represented by Formula 3 above.
본 명세서의 일 실시상태에 있어서, R1, R2, R4, 및 R5는 서로 같거나 상이하고, 각각 독립적으로, 수소; 중수소; 할로겐기; 시아노기' 중수소로 치환 또는 비치환된 탄소수 1 내지 6의 알킬기; 탄소수 3 내지 20의 시클로알킬기; 탄소수 6 내지 40의 아릴아민기; 중수소, 할로겐기, 니트릴기, 탄소수 1 내지 6의 알킬기, 또는 중수소로 치환된 탄소수 1 내지 6의 알킬기로 치환 또는 비치환된 탄소수 6 내지 20의 아릴기; 탄소수 2 내지 20의 헤테로고리기; 또는 상기 화학식 3으로 표시된다.In the exemplary embodiment of the present specification, R1, R2, R4, and R5 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; Cyano group' C1-C6 alkyl group unsubstituted or substituted with deuterium; A cycloalkyl group having 3 to 20 carbon atoms; Arylamine group having 6 to 40 carbon atoms; An aryl group having 6 to 20 carbon atoms unsubstituted or substituted with a deuterium, a halogen group, a nitrile group, an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms substituted with deuterium; A heterocyclic group having 2 to 20 carbon atoms; Or it is represented by Formula 3 above.
본 명세서에 일 실시상태에 있어서, R1, R2, R4 및 R5의 헤테로고리기는 이종원소로서 N을 포함한다. In one embodiment of the present specification, the heterocyclic group of R1, R2, R4 and R5 includes N as a hetero element.
본 명세서의 일 실시상태에 있어서, R1, R2, R4, 및 R5는 서로 같거나 상이하고, 각각 독립적으로, 수소; 중수소; 플루오로기; 시아노기; 중수소로 치환 또는 비치환된 메틸기; 이소프로필기; tert-부틸기; 시클로헥실기; 디페닐아민기; 중수소, 플루오로기, 시아노기, tert-부틸기 또는 CD3로 치환 또는 비치환된 페닐기; 바이페닐기; 나프틸기; 또는 피리딘기이다.In the exemplary embodiment of the present specification, R1, R2, R4, and R5 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Fluoro group; Cyano group; A methyl group unsubstituted or substituted with deuterium; Isopropyl group; tert-butyl group; Cyclohexyl group; Diphenylamine group; A phenyl group unsubstituted or substituted with deuterium, a fluoro group, a cyano group, a tert-butyl group, or a CD 3 ; Biphenyl group; Naphthyl group; Or a pyridine group.
본 명세서의 일 실시상태에 있어서, R3은 수소; 중수소; 할로겐기; 니트릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아릴옥시기; 또는 치환 또는 비치환된 헤테로고리기이거나; 하기 화학식 3으로 표시된다.In an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; Or a substituted or unsubstituted heterocyclic group; It is represented by the following formula (3).
본 명세서의 일 실시상태에 있어서, R3는 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 헤테로고리기; 또는 상기 화학식 3으로 표시된다.In an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or it is represented by Formula 3 above.
본 명세서의 일 실시상태에 있어서, R3는 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 탄소수 1 내지 10의 알킬기; 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 치환 또는 비치환된 탄소수 1 내지 30의 알킬실릴기; 치환 또는 비치환된 탄소수 6 내지 90의 아릴실릴기; 치환 또는 비치환된 탄소수 1 내지 20의 알킬아민기; 치환 또는 비치환된 탄소수 6 내지 60의 아릴아민기; 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴아민기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기; 또는 상기 화학식 3으로 표시된다.In an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C1 to C30 alkylsilyl group; A substituted or unsubstituted arylsilyl group having 6 to 90 carbon atoms; A substituted or unsubstituted C1 to C20 alkylamine group; A substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; A substituted or unsubstituted C2 to C60 heteroarylamine group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Or it is represented by Formula 3 above.
본 명세서의 일 실시상태에 있어서, R3는 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 탄소수 1 내지 6의 알킬기; 치환 또는 비치환된 3 내지 20의 시클로알킬기; 치환 또는 비치환된 탄소수 1 내지 18의 알킬실릴기; 치환 또는 비치환된 탄소수 6 내지 60의 아릴실릴기; 치환 또는 비치환된 탄소수 1 내지 12의 알킬아민기; 치환 또는 비치환된 탄소수 6 내지 40의 아릴아민기; 치환 또는 비치환된 탄소수 2 내지 40 헤테로아릴아민기; 치환 또는 비치환된 탄소수 6 내지 20의 아릴기; 치환 또는 비치환된 탄소수 2 내지 20의 헤테로고리기; 또는 상기 화학식 3으로 표시된다.In an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C 1 to C 6 alkyl group; A substituted or unsubstituted 3 to 20 cycloalkyl group; A substituted or unsubstituted C 1 to C 18 alkylsilyl group; A substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms; A substituted or unsubstituted C1-C12 alkylamine group; A substituted or unsubstituted arylamine group having 6 to 40 carbon atoms; A substituted or unsubstituted C2 to C40 heteroarylamine group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted C2 to C20 heterocyclic group; Or it is represented by Formula 3 above.
본 명세서의 일 실시상태에 있어서, R3는 수소; 중수소; 할로겐기; 시아노기; 중수소로 치환 또는 비치환된 탄소수 1 내지 10의 알킬기; 중수소로 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 중수소, 할로겐기, 시아노기, 탄소수 1 내지 10의 알킬기, 탄소수 6 내지 30의 아릴기 및 실릴기로 이루어진 군에서 선택된 1 이상의 치환기 또는 상기 군에서 선택된 2 이상의 기가 연결된 치환기로 치환 또는 비치환된 탄소수 6 내지 60의 아릴아민기; 중수소, 할로겐기, 또는 시아노기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 중수소로 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기; 또는 상기 화학식 3으로 표시된다.In an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium; A cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with deuterium; 6 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen groups, cyano groups, alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 30 carbon atoms, and silyl groups, or a substituent connected with two or more groups selected from the group Arylamine group of to 60; An aryl group having 6 to 30 carbon atoms unsubstituted or substituted with deuterium, a halogen group, or a cyano group; A heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium; Or it is represented by Formula 3 above.
본 명세서의 일 실시상태에 있어서, R3는 수소; 중수소; 할로겐기; 시아노기; 중수소로 치환 또는 비치환된 탄소수 1 내지 6의 알킬기; 중수소로 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기; 중수소, 할로겐기, 시아노기, 탄소수 1 내지 6의 알킬기, 탄소수 6 내지 20의 아릴기 및 실릴기로 이루어진 군에서 선택된 1 이상의 치환기 또는 상기 군에서 선택된 2 이상의 기가 연결된 치환기로 치환 또는 비치환된 탄소수 6 내지 40의 아릴아민기; 중수소, 할로겐기, 또는 시아노기로 치환 또는 비치환된 탄소수 6 내지 20의 아릴기; 중수소로 치환 또는 비치환된 탄소수 2 내지 20의 헤테로고리기; 또는 상기 화학식 3으로 표시된다.In an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; A cycloalkyl group having 3 to 20 carbon atoms unsubstituted or substituted with deuterium; At least one substituent selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a silyl group, or 6 unsubstituted or substituted with a substituent connected with two or more groups selected from the group Arylamine group of to 40; An aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium, a halogen group, or a cyano group; A heterocyclic group having 2 to 20 carbon atoms substituted or unsubstituted with deuterium; Or it is represented by Formula 3 above.
본 명세서의 일 실시상태에 있어서, R3는 수소; 중수소; 할로겐기; 시아노기; 중수소로 치환 또는 비치환된 탄소수 1 내지 6의 알킬기; 탄소수 3 내지 20의 시클로알킬기; 중수소, 탄소수 1 내지 6의 알킬기, 탄소수 3 내지 18의 트리알킬실릴기, 또는 탄소수 18 내지 60의 트리아릴아민기로 치환 또는 비치환된 탄소수 6 내지 40의 아릴아민기; 중수소, 할로겐기, 또는 시아노기로 치환 또는 비치환된 탄소수 6 내지 20의 아릴기; 탄소수 2 내지 20의 헤테로고리기; 또는 상기 화학식 3으로 표시된다.In an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; A cycloalkyl group having 3 to 20 carbon atoms; An arylamine group having 6 to 40 carbon atoms unsubstituted or substituted with a deuterium, an alkyl group having 1 to 6 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, or a triarylamine group having 18 to 60 carbon atoms; An aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium, a halogen group, or a cyano group; A heterocyclic group having 2 to 20 carbon atoms; Or it is represented by Formula 3 above.
본 명세서의 일 실시상태에 있어서, R3의 헤테로고리기는 이종원소로서 N을 포함한다.In an exemplary embodiment of the present specification, the heterocyclic group of R3 includes N as a hetero element.
본 명세서의 일 실시상태에 있어서, R3는 수소; 중수소; 중수소로 치환 또는 비치환된 메틸기; tert-부틸기; 중수소, tert-부틸기, 트리메틸실릴기 또는 트리페닐실릴기로 치환 또는 비치환된 디페닐아민기; 중수소 또는 플루오로기로 치환 또는 비치환된 페닐기; 또는 카바졸기이다.In an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; tert-butyl group; Diphenylamine group unsubstituted or substituted with deuterium, tert-butyl group, trimethylsilyl group, or triphenylsilyl group; A phenyl group unsubstituted or substituted with deuterium or a fluoro group; Or carbazole group.
본 명세서의 일 실시상태에 있어서, R1, R2, R4, 및 R5는 서로 같거나 상이하고, 각각 독립적으로, 수소; 중수소; 할로겐기; 시아노기; 중수소로 치환 또는 비치환된 탄소수 1 내지 10의 알킬기; 중수소로 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 중수소로 치환 또는 비치환된 탄소수 6 내지 60의 아릴아민기; 중수소, 할로겐기, 시아노기 및 탄소수 1 내지 10의 알킬기로 이루어진 군에서 선택된 1 이상의 치환기 또는 상기 군에서 선택된 2 이상의 기가 연결된 치환기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 중수소로 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기; 또는 상기 화학식 3으로 표시되고,In the exemplary embodiment of the present specification, R1, R2, R4, and R5 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium; A cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with deuterium; Arylamine group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium; An aryl group having 6 to 30 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, and an alkyl group having 1 to 10 carbon atoms or a substituent connected with two or more groups selected from the group; A heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium; Or represented by Chemical Formula 3,
R3는 수소; 중수소; 할로겐기; 시아노기; 중수소로 치환 또는 비치환된 탄소수 1 내지 10의 알킬기; 중수소로 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 중수소, 할로겐기, 시아노기, 탄소수 1 내지 10의 알킬기, 탄소수 6 내지 30의 아릴기 및 실릴기로 이루어진 군에서 선택된 1 이상의 치환기 또는 상기 군에서 선택된 2 이상의 기가 연결된 치환기로 치환 또는 비치환된 탄소수 6 내지 60의 아릴아민기; 중수소, 할로겐기, 또는 시아노기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 중수소로 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기; 또는 상기 화학식 3으로 표시된다.R3 is hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium; A cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with deuterium; 6 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen groups, cyano groups, alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 30 carbon atoms, and silyl groups, or a substituent connected with two or more groups selected from the group Arylamine group of to 60; An aryl group having 6 to 30 carbon atoms unsubstituted or substituted with deuterium, a halogen group, or a cyano group; A heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium; Or it is represented by Formula 3 above.
본 명세서의 일 실시상태에 있어서, R2 중 하나는 B2가 연결된 N에 대하여 ortho 배향인 자리에 연결된다. In the exemplary embodiment of the present specification, one of R2 is connected to a position in ortho orientation with respect to N to which B2 is connected.
본 명세서의 일 실시상태에 있어서, R4 중 하나는 B2가 연결된 N에 대하여 ortho 배향인 자리에 연결된다. In the exemplary embodiment of the present specification, one of R4 is connected to a position in ortho orientation with respect to N to which B2 is connected.
본 명세서의 일 실시상태에 있어서, n1은 1 또는 2이다.In an exemplary embodiment of the present specification, n1 is 1 or 2.
본 명세서의 일 실시상태에 있어서, n2는 1 내지 4이다. 또하나의 실시상태에 있어서, n2는 1 내지 3 이다.In an exemplary embodiment of the present specification, n2 is 1 to 4. In another exemplary embodiment, n2 is 1 to 3.
본 명세서의 일 실시상태에 있어서, n3은 1 또는 2이다.In an exemplary embodiment of the present specification, n3 is 1 or 2.
본 명세서의 일 실시상태에 있어서, n4는 1 내지 4이다. 또하나의 실시상태에 있어서, n4는 1 내지 3 이다.In an exemplary embodiment of the present specification, n4 is 1 to 4. In another exemplary embodiment, n4 is 1 to 3.
본 명세서의 일 실시상태에 있어서, n5는 1 이다.In an exemplary embodiment of the present specification, n5 is 1.
본 명세서의 일 실시상태에 있어서, R1 내지 R5 중 적어도 하나 이상은 상기 화학식 3으로 표시된다.In an exemplary embodiment of the present specification, at least one of R1 to R5 is represented by Chemical Formula 3.
본 명세서의 일 실시상태에 있어서, R1 내지 R5 중 하나 내지 넷은 상기 화학식 3으로 표시된다.In an exemplary embodiment of the present specification, one to four of R1 to R5 are represented by Chemical Formula 3.
본 명세서의 일 실시상태에 있어서, R1 내지 R5 중 하나 또는 둘은 상기 화학식 3으로 표시된다.In an exemplary embodiment of the present specification, one or two of R1 to R5 are represented by Chemical Formula 3.
본 명세서의 일 실시상태에 있어서, R1, R2, R4 및 R5 중 하나 내지 넷은 상기 화학식 3으로 표시된다.In an exemplary embodiment of the present specification, one to four of R1, R2, R4, and R5 are represented by Chemical Formula 3.
본 명세서의 일 실시상태에 있어서, R1, R2, R4 및 R5 중 하나 또는 둘은 상기 화학식 3으로 표시된다.In an exemplary embodiment of the present specification, one or two of R1, R2, R4, and R5 are represented by Chemical Formula 3.
본 명세서의 일 실시상태에 있어서, R1은 상기 화학식 3으로 표시된다.In an exemplary embodiment of the present specification, R1 is represented by Chemical Formula 3.
본 명세서의 일 실시상태에 있어서, R2는 상기 화학식 3으로 표시된다.In the exemplary embodiment of the present specification, R2 is represented by Chemical Formula 3.
본 명세서의 일 실시상태에 있어서, R3은 상기 화학식 3으로 표시된다.In an exemplary embodiment of the present specification, R3 is represented by Chemical Formula 3.
본 명세서의 일 실시상태에 있어서, R4는 상기 화학식 3으로 표시된다.In an exemplary embodiment of the present specification, R4 is represented by Chemical Formula 3.
본 명세서의 일 실시상태에 있어서, R5는 상기 화학식 3으로 표시된다. In an exemplary embodiment of the present specification, R5 is represented by Chemical Formula 3.
본 명세서의 일 실시상태에 있어서, R6 내지 R8은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 10의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이다.In the exemplary embodiment of the present specification, R6 to R8 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, R6 내지 R8은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 6의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 20의 아릴기이다.In the exemplary embodiment of the present specification, R6 to R8 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 있어서, R6 내지 R8은 서로 같거나 상이하고, 각각 독립적으로 중수소로 치환 또는 비치환된 탄소수 1 내지 10의 알킬기; 또는 중수소, 할로겐기, 시아노기, 탄소수 1 내지 10의 알킬기, 탄소수 6 내지 30의 아릴기 및 실릴기로 이루어진 군에서 선택된 1 이상의 치환기 또는 상기 군에서 선택된 2 이상의 기가 연결된 치환기로 치환 또는 비치환된 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이다.In the exemplary embodiment of the present specification, R6 to R8 are the same as or different from each other, and each independently an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; Or substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a silyl group or a substituent connected with two or more groups selected from the group. Or an unsubstituted C6-C30 aryl group.
본 명세서의 일 실시상태에 있어서, R6 내지 R8은 서로 같거나 상이하고, 각각 독립적으로 중수소로 치환 또는 비치환된 탄소수 1 내지 6의 알킬기; 또는 중수소, 할로겐기, 시아노기, 탄소수 1 내지 6의 알킬기, 탄소수 6 내지 20의 아릴기 및 실릴기로 이루어진 군에서 선택된 1 이상의 치환기 또는 상기 군에서 선택된 2 이상의 기가 연결된 치환기로 치환 또는 비치환된 치환 또는 비치환된 탄소수 6 내지 20의 아릴기이다.In the exemplary embodiment of the present specification, R6 to R8 are the same as or different from each other, and each independently an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; Or substituted or unsubstituted with at least one substituent selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a silyl group or a substituent connected with two or more groups selected from the group Or it is an unsubstituted C6-C20 aryl group.
본 명세서의 일 실시상태에 있어서, R6 내지 R8은 서로 같거나 상이하고, 각각 독립적으로 중수소로 치환 또는 비치환된 탄소수 1 내지 6의 알킬기; 또는 중수소, 할로겐기, 시아노기, 탄소수 1 내지 6의 알킬기, 중수소로 치환된 탄소수 1 내지 6의 알킬기, 또는 탄소수 3 내지 18의 트리알킬실릴기로 치환 또는 비치환된 치환 또는 비치환된 탄소수 6 내지 20의 아릴기이다.In the exemplary embodiment of the present specification, R6 to R8 are the same as or different from each other, and each independently an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; Or a substituted or unsubstituted C6 to C6 group unsubstituted or substituted with a deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with deuterium, or a trialkylsilyl group having 3 to 18 carbon atoms It is an aryl group of 20.
본 명세서의 일 실시상태에 있어서, R6 내지 R8은 서로 같거나 상이하고, 각각 독립적으로 메틸기; tert-부틸기; 또는 중수소, 플루오로기, 메틸기, tert-부틸기, CD3, 또는 트리메틸실릴기로 치환 또는 비치환된 페닐기이다.In the exemplary embodiment of the present specification, R6 to R8 are the same as or different from each other, and each independently a methyl group; tert-butyl group; Or a phenyl group unsubstituted or substituted with deuterium, a fluoro group, a methyl group, a tert-butyl group, a CD 3 or a trimethylsilyl group.
본 명세서의 일 실시상태에 있어서, X는 C이고, R6 내지 R8 중 적어도 하나는 치환 또는 비치환된 알킬기이다.In an exemplary embodiment of the present specification, X is C, and at least one of R6 to R8 is a substituted or unsubstituted alkyl group.
본 명세서의 일 실시상태에 있어서, X는 C이고, R6 내지 R8 중 적어도 둘은 치환 또는 비치환된 알킬기이다.In an exemplary embodiment of the present specification, X is C, and at least two of R6 to R8 are substituted or unsubstituted alkyl groups.
본 명세서의 일 실시상태에 있어서, X는 C이고, R6 내지 R8 중 적어도 하나는 치환 또는 비치환된 아릴기이다.In an exemplary embodiment of the present specification, X is C, and at least one of R6 to R8 is a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 있어서, X는 C이고, R6 및 R7은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기이고, 상기 R8은 치환 또는 비치환된 아릴기이다.In the exemplary embodiment of the present specification, X is C, R6 and R7 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group, and R8 is a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 있어서, X는 Si이고, R6 내지 R8 중 적어도 하나는 치환 또는 비치환된 아릴기이다.In an exemplary embodiment of the present specification, X is Si, and at least one of R6 to R8 is a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 있어서, X는 Si이고, R6 내지 R8 중 적어도 둘은 치환 또는 비치환된 아릴기이다.In the exemplary embodiment of the present specification, X is Si, and at least two of R6 to R8 are substituted or unsubstituted aryl groups.
본 명세서의 일 실시상태에 있어서, X는 C이고, R6 및 R7은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이고, 상기 R8은 치환 또는 비치환된 알킬기이다.In the exemplary embodiment of the present specification, X is C, R6 and R7 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group, and R8 is a substituted or unsubstituted alkyl group.
본 명세서의 일 실시상태에 있어서, X는 Si이고, R6 내지 R8은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이다. In the exemplary embodiment of the present specification, X is Si, R6 to R8 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 있어서, 상기 화학식 3은 하기 화학식 3-1 또는 3-2로 표시된다.In an exemplary embodiment of the present specification, Chemical Formula 3 is represented by the following Chemical Formula 3-1 or 3-2.
[화학식 3-1][Formula 3-1]
Figure PCTKR2020010175-appb-I000014
Figure PCTKR2020010175-appb-I000014
[화학식 3-2][Chemical Formula 3-2]
Figure PCTKR2020010175-appb-I000015
Figure PCTKR2020010175-appb-I000015
상기 화학식 3-1 및 3-2에 있어서,In Formulas 3-1 and 3-2,
X는 Si이고,X is Si,
R11은 치환 또는 비치환된 알킬기이고,R11 is a substituted or unsubstituted alkyl group,
R12는 치환 또는 비치환된 아릴기이고,R12 is a substituted or unsubstituted aryl group,
R13 내지 R16은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이다.R13 to R16 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 있어서, R11 내지 R16에는 전술한 R6 내지 R8에 관한 설명이 적용될 수 있다.In the exemplary embodiment of the present specification, the description of R6 to R8 described above may be applied to R11 to R16.
본 명세서의 일 실시상태에 있어서, R11은 치환 또는 비치환된 탄소수 1 내지 10의 알킬기이다.In the exemplary embodiment of the present specification, R11 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
본 명세서의 일 실시상태에 있어서, R11은 치환 또는 비치환된 탄소수 1 내지 6의 알킬기이다.In the exemplary embodiment of the present specification, R11 is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.
본 명세서의 일 실시상태에 있어서, R11은 중수소로 치환 또는 비치환된 탄소수 1 내지 6의 알킬기이다.In the exemplary embodiment of the present specification, R11 is an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium.
본 명세서의 일 실시상태에 있어서, R11은 메틸기이다.In an exemplary embodiment of the present specification, R11 is a methyl group.
본 명세서의 일 실시상태에 있어서, R12는 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이다.In the exemplary embodiment of the present specification, R12 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, R12는 치환 또는 비치환된 탄소수 6 내지 20의 아릴기이다.In the exemplary embodiment of the present specification, R12 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 있어서, R12는 중수소, 할로겐기, 시아노기, 탄소수 1 내지 6의 알킬기, 탄소수 6 내지 20의 아릴기 및 실릴기로 이루어진 군에서 선택된 1 이상의 치환기 또는 상기 군에서 선택된 2 이상의 기가 연결된 치환기로 치환 또는 비치환된 치환 또는 비치환된 탄소수 6 내지 20의 아릴기이다.In an exemplary embodiment of the present specification, R12 is at least one substituent selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a silyl group, or two or more selected from the group. It is a substituted or unsubstituted substituted or unsubstituted aryl group having 6 to 20 carbon atoms with a group-linked substituent.
본 명세서의 일 실시상태에 있어서, R12는 중수소, 할로겐기, 시아노기, 탄소수 1 내지 6의 알킬기, 중수소로 치환된 탄소수 1 내지 6의 알킬기, 또는 탄소수 3 내지 18의 트리알킬실릴기로 치환 또는 비치환된 치환 또는 비치환된 탄소수 6 내지 20의 아릴기이다.In the exemplary embodiment of the present specification, R12 is substituted or provided with a deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with deuterium, or a trialkylsilyl group having 3 to 18 carbon atoms. It is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 있어서, R12는 중수소, 플루오로기, 메틸기, tert-부틸기, CD3, 또는 트리메틸실릴기로 치환 또는 비치환된 페닐기이다.In the exemplary embodiment of the present specification, R12 is a phenyl group unsubstituted or substituted with deuterium, a fluoro group, a methyl group, a tert-butyl group, a CD 3 , or a trimethylsilyl group.
본 명세서의 일 실시상태에 있어서, R13 내지 R16은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 10의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이다.In the exemplary embodiment of the present specification, R13 to R16 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, R13 내지 R16은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 6의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 20의 아릴기이다.In the exemplary embodiment of the present specification, R13 to R16 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 있어서, R13 내지 R16은 서로 같거나 상이하고, 각각 독립적으로 중수소로 치환 또는 비치환된 탄소수 1 내지 6의 알킬기; 또는 중수소, 할로겐기, 시아노기, 탄소수 1 내지 6의 알킬기, 탄소수 6 내지 20의 아릴기 및 실릴기로 이루어진 군에서 선택된 1 이상의 치환기 또는 상기 군에서 선택된 2 이상의 기가 연결된 치환기로 치환 또는 비치환된 치환 또는 비치환된 탄소수 6 내지 20의 아릴기이다.In the exemplary embodiment of the present specification, R13 to R16 are the same as or different from each other, and each independently an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; Or substituted or unsubstituted with at least one substituent selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a silyl group or a substituent connected with two or more groups selected from the group Or it is an unsubstituted C6-C20 aryl group.
본 명세서의 일 실시상태에 있어서, R13 내지 R16은 서로 같거나 상이하고, 각각 독립적으로 메틸기; tert-부틸기; 또는 중수소, 플루오로기, 메틸기, tert-부틸기, CD3, 또는 트리메틸실릴기로 치환 또는 비치환된 페닐기이다.In the exemplary embodiment of the present specification, R13 to R16 are the same as or different from each other, and each independently a methyl group; tert-butyl group; Or a phenyl group unsubstituted or substituted with deuterium, a fluoro group, a methyl group, a tert-butyl group, a CD 3 or a trimethylsilyl group.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물은 하기 화합물 중에서 선택된 어느 하나이다.In the exemplary embodiment of the present specification, the compound represented by Formula 1 is any one selected from the following compounds.
Figure PCTKR2020010175-appb-I000016
Figure PCTKR2020010175-appb-I000016
Figure PCTKR2020010175-appb-I000017
Figure PCTKR2020010175-appb-I000017
Figure PCTKR2020010175-appb-I000018
Figure PCTKR2020010175-appb-I000018
Figure PCTKR2020010175-appb-I000019
Figure PCTKR2020010175-appb-I000019
Figure PCTKR2020010175-appb-I000020
Figure PCTKR2020010175-appb-I000020
Figure PCTKR2020010175-appb-I000021
Figure PCTKR2020010175-appb-I000021
Figure PCTKR2020010175-appb-I000022
Figure PCTKR2020010175-appb-I000022
Figure PCTKR2020010175-appb-I000023
Figure PCTKR2020010175-appb-I000023
Figure PCTKR2020010175-appb-I000024
Figure PCTKR2020010175-appb-I000024
Figure PCTKR2020010175-appb-I000025
Figure PCTKR2020010175-appb-I000025
Figure PCTKR2020010175-appb-I000026
Figure PCTKR2020010175-appb-I000026
Figure PCTKR2020010175-appb-I000027
Figure PCTKR2020010175-appb-I000027
Figure PCTKR2020010175-appb-I000028
Figure PCTKR2020010175-appb-I000028
Figure PCTKR2020010175-appb-I000029
Figure PCTKR2020010175-appb-I000029
이하, 화학식 2에 관하여 설명한다.Hereinafter, Formula 2 will be described.
본 명세서의 일 실시상태에 있어서, 상기 Y31 및 Y32는 서로 같거나 상이하고, 각각 독립적으로 수소, 치환 또는 비치환된 탄소수 1 내지 10의 알킬기, 또는 탄소수 6 내지 30의 치환 또는 비치환된 아릴기이거나, 서로 결합하여 고리를 형성한다.In the exemplary embodiment of the present specification, Y31 and Y32 are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms Or combine with each other to form a ring.
본 명세서의 일 실시상태에 있어서, 상기 Y31 및 Y32는 서로 같거나 상이하고, 각각 독립적으로 수소, 치환 또는 비치환된 탄소수 1 내지 10의 알킬기, 또는 탄소수 6 내지 30의 치환 또는 비치환된 아릴기이거나, 서로 결합하여 지방족고리를 형성한다.In the exemplary embodiment of the present specification, Y31 and Y32 are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms Or combine with each other to form an aliphatic ring.
본 명세서의 일 실시상태에 있어서, 상기 Y31 및 Y32는 서로 같거나 상이하고, 각각 독립적으로 수소, 치환 또는 비치환된 탄소수 1 내지 10의 알킬기, 또는 탄소수 6 내지 30의 치환 또는 비치환된 아릴기이거나, 서로 결합하여 탄소수 3 내지 10의 지방족고리를 형성한다.In the exemplary embodiment of the present specification, Y31 and Y32 are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms Or, by bonding to each other to form an aliphatic ring having 3 to 10 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 Y31 및 Y32는 서로 결합하여 탄소수 3 내지 6의 지방족고리를 형성한다.In the exemplary embodiment of the present specification, Y31 and Y32 are bonded to each other to form an aliphatic ring having 3 to 6 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 Y31 및 Y32는 서로 결합하여 시클로펜틸고리를 형성한다.In the exemplary embodiment of the present specification, Y31 and Y32 are bonded to each other to form a cyclopentyl ring.
본 명세서의 일 실시상태에 있어서, 상기 Y31 및 Y32는 서로 결합하여 탄소수 3 내지 10의 지방족과 방향족 고리가 융합한 고리를 형성한다.In the exemplary embodiment of the present specification, Y31 and Y32 are bonded to each other to form a ring in which an aliphatic and aromatic ring having 3 to 10 carbon atoms are fused.
본 명세서의 일 실시상태에 있어서, 상기 Y31 및 Y32는 서로 결합하여 시클로펜틸고리과 벤젠고리가 융합한 고리를 형성한다. In the exemplary embodiment of the present specification, Y31 and Y32 are bonded to each other to form a ring in which a cyclopentyl ring and a benzene ring are fused.
본 명세서의 일 실시상태에 있어서, 상기 Y31 및 Y32는 서로 같거나 상이하고, 각각 독립적으로 수소; 탄소수 1 내지 10의 알킬기; 또는 탄소수 1 내지 10의 알킬기로 또는 탄소수 6 내지 30의 아릴기로 치환 또는 비치환된 탄소수 6 내지 30의 치환 또는 비치환된 아릴기이다.In the exemplary embodiment of the present specification, Y31 and Y32 are the same as or different from each other, and each independently hydrogen; An alkyl group having 1 to 10 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 Y31 및 Y32는 서로 같거나 상이하고, 각각 독립적으로 수소; 메틸기; 에틸기; 이소프로필기; 터부틸기; 페닐기; 비페닐기; 나프틸기; 터페닐기; 페난트렌기; 또는 안트라센기이고, In the exemplary embodiment of the present specification, Y31 and Y32 are the same as or different from each other, and each independently hydrogen; Methyl group; Ethyl group; Isopropyl group; Terbutyl group; Phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Phenanthrene group; Or an anthracene group,
상기 페닐기; 비페닐기; 나프틸기; 터페닐기; 페난트렌기; 또는 안트라센기는 메틸기, 에틸기, 이소프로필기, 터부틸기, 페닐기, 비페닐기, 나프틸기, 터페닐기, 페난트렌기, 또는 안트라센기로 치환 또는 비치환된다.The phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Phenanthrene group; Alternatively, the anthracene group is unsubstituted or substituted with a methyl group, ethyl group, isopropyl group, terbutyl group, phenyl group, biphenyl group, naphthyl group, terphenyl group, phenanthrene group, or anthracene group.
본 명세서의 일 실시상태에 있어서, 상기 Y31 및 Y32는 서로 같거나 상이하고, 각각 독립적으로 수소; 메틸기; 페닐기; 나프틸기; 메틸기로 치환된 페닐기; 메틸기로 치환된 나프틸기; 나프틸기로 치환된 페닐기; 페닐기로 치환된 나프틸기이거나 서로 결합하여 탄소수 3 내지 6의 지방족고리를 형성한다.In the exemplary embodiment of the present specification, Y31 and Y32 are the same as or different from each other, and each independently hydrogen; Methyl group; Phenyl group; Naphthyl group; A phenyl group substituted with a methyl group; A naphthyl group substituted with a methyl group; A phenyl group substituted with a naphthyl group; It is a naphthyl group substituted with a phenyl group or is bonded to each other to form an aliphatic ring having 3 to 6 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R3-1은 수소, 중수소, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 헤테로아릴기, 또는 상기 화학식 4이거나, 인접한 기와 서로 결합하여 탄화수소고리를 형성한다.In the exemplary embodiment of the present specification, R3-1 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or the formula 4, or an adjacent group and Combined with each other to form a hydrocarbon ring.
본 명세서의 일 실시상태에 있어서, 상기 R3-1은 수소; 중수소; 탄소수 1 내지 10의 알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기, 또는 상기 화학식 4이거나, 인접한 기와 서로 결합하여 탄소수 3 내지 20의 탄화수소고리를 형성한다.In the exemplary embodiment of the present specification, R3-1 is hydrogen; heavy hydrogen; An alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or the above formula (4), or combined with an adjacent group to form a hydrocarbon ring having 3 to 20 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R3-1은 수소; 메틸기; 터부틸기; 페닐기; 메틸기로 치환된 페닐기; 비페닐기; 나프틸기 또는 또는 상기 화학식 4이거나, 인접한 기와 서로 결합하여 탄소수 6 내지 20의 방향족 탄화수소고리를 형성한다. In the exemplary embodiment of the present specification, R3-1 is hydrogen; Methyl group; Terbutyl group; Phenyl group; A phenyl group substituted with a methyl group; Biphenyl group; It is a naphthyl group or the above formula (4), or is combined with an adjacent group to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R3-1은 수소; 메틸기; 터부틸기; 페닐기; 나프틸기; 또는 상기 화학식 4이거나, 인접한 기와 서로 결합하여 탄소수 6 내지 20의 방향족 탄화수소고리를 형성한다.In the exemplary embodiment of the present specification, R3-1 is hydrogen; Methyl group; Terbutyl group; Phenyl group; Naphthyl group; Or the formula (4), or by bonding with adjacent groups to each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R3-1은 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기이다. In the exemplary embodiment of the present specification, R3-1 is a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 a31은 1 내지 8의 정수이고, 하나 이상의 R3-1은 상기 화학식 4이다.In the exemplary embodiment of the present specification, a31 is an integer of 1 to 8, and at least one R3-1 is Chemical Formula 4.
본 명세서의 일 실시상태에 있어서, 상기 Ar41 및 Ar42는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 10의 알킬기; 치환 또는 비치환된 알킬실릴기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 3 내지 30의 헤테로고리기이다.In the exemplary embodiment of the present specification, Ar 41 and Ar 42 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted alkylsilyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 3 to C 30 heterocyclic group.
본 명세서의 일 실시상태에 있어서, 상기 Ar41 및 Ar42는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 10의 알킬기; 탄소수 1 내지 10의 알킬기 또는 탄소수 6 내지 30의 아릴기로 치환 또는 비치환된 실릴기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 3 내지 30의 헤테로고리기이다.In the exemplary embodiment of the present specification, Ar 41 and Ar 42 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A silyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 3 to C 30 heterocyclic group.
본 명세서의 일 실시상태에 있어서, 상기 Ar41 및 Ar42는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 3 내지 30의 헤테로고리기이다.In the exemplary embodiment of the present specification, Ar 41 and Ar 42 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 3 to C 30 heterocyclic group.
본 명세서의 일 실시상태에 있어서, 상기 Ar41 및 Ar42는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이다.In the exemplary embodiment of the present specification, Ar 41 and Ar 42 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 Ar41 및 Ar42는 서로 같거나 상이하고, 각각 독립적으로 메틸기; 에틸기; 부틸기; 터부틸기; 페닐기; 비페닐기; 터페닐기; 나프틸기; 페난트렌기; 트리페닐렌기; 페릴렌기; 플루오렌기; 플루오잔텐기; 카바졸기; 벤조카바졸기; 인데노카바졸기; 피리딘기; 피리미딘기; 트리아진기; 디벤조퓨란기; 디벤조티오펜기; 퀴놀린기; 퀴나졸린기; 퀴녹살린기; 페녹사진기; 페노티아진기; 페녹사티인(phenoxathiine); 트리메틸실릴기이고, In the exemplary embodiment of the present specification, Ar 41 and Ar 42 are the same as or different from each other, and each independently a methyl group; Ethyl group; Butyl group; Terbutyl group; Phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrene group; Triphenylene group; Perylene group; Fluorene group; Fluoroxanthene group; Carbazole; Benzocarbazole group; Indenocarbazole; Pyridine group; Pyrimidine group; Triazine group; Dibenzofuran group; Dibenzothiophene group; Quinoline group; Quinazoline; Quinoxalin group; Phenox camera; Phenothiazine group; Phenoxathiine; Is a trimethylsilyl group,
상기 페닐기; 비페닐기; 터페닐기; 나프틸기; 페난트렌기; 트리페닐렌기; 페릴렌기; 플루오렌기; 플루오잔텐기; 카바졸기; 벤조카바졸기; 인데노카바졸기; 피리딘기; 피리미딘기; 트리아진기; 디벤조퓨란기; 디벤조티오펜기; 퀴놀린기; 퀴나졸린기; 퀴녹살린기; 페녹사진기; 페노티아진기; 페녹사티인(phenoxathiine)는 중수소, CN, 메틸기, 터부틸기, 페닐기, 메틸기로 치환된 페닐기, 트리플루오로메틸기, 트리플루오로메톡시기, 피리딘기, 피리미딘기, 트리아진기, 디벤조퓨란기, 디벤조티오펜기, 트리메틸실릴기, 트리페닐실릴기, 및 카바졸기로 구성되는 그룹에서 선택되는 어느 하나 이상으로 치환 또는 비치환된다.The phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrene group; Triphenylene group; Perylene group; Fluorene group; Fluoroxanthene group; Carbazole; Benzocarbazole group; Indenocarbazole; Pyridine group; Pyrimidine group; Triazine group; Dibenzofuran group; Dibenzothiophene group; Quinoline group; Quinazoline; Quinoxalin group; Phenox camera; Phenothiazine group; Phenoxathiine is deuterium, CN, methyl group, terbutyl group, phenyl group, phenyl group substituted with methyl group, trifluoromethyl group, trifluoromethoxy group, pyridine group, pyrimidine group, triazine group, dibenzofuran It is substituted or unsubstituted with any one or more selected from the group consisting of a group, a dibenzothiophene group, a trimethylsilyl group, a triphenylsilyl group, and a carbazole group.
본 명세서의 일 실시상태에 있어서, 상기 Ar41 및 Ar42는 서로 같거나 상이하고, 각각 독립적으로 페닐기; 비페닐기; 터페닐기; 나프틸기; 또는 페난트렌기이고, 상기 페닐기; 비페닐기; 터페닐기; 나프틸기; 또는 페난트렌기는 중수소; CN; 알킬기; 아릴기; 실릴기; 또는 헤테로아릴기로 치환 또는 비치환된다.In the exemplary embodiment of the present specification, Ar 41 and Ar 42 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Or a phenanthrene group, and the phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Or the phenanthrene group is deuterium; CN; Alkyl group; Aryl group; Silyl group; Or substituted or unsubstituted with a heteroaryl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar41 및 Ar42는 서로 같거나 상이하고, 각각 독립적으로 페닐기; 비페닐기; 터페닐기; 나프틸기; 또는 페난트렌기이고, 상기 페닐기; 비페닐기; 터페닐기; 나프틸기; 또는 페난트렌기는 중수소; CN; 탄소수 1 내지 10의 알킬기; 탄소수 6 내지 30의 아릴기; 탄소수 1 내지 10의 알킬실릴기; 또는 탄소수 3 내지 30의 헤테로아릴기로 치환 또는 비치환된다.In the exemplary embodiment of the present specification, Ar 41 and Ar 42 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Or a phenanthrene group, and the phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Or the phenanthrene group is deuterium; CN; An alkyl group having 1 to 10 carbon atoms; Aryl group having 6 to 30 carbon atoms; An alkylsilyl group having 1 to 10 carbon atoms; Or it is unsubstituted or substituted with a C3-C30 heteroaryl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar41 및 Ar42는 서로 같거나 상이하고, 각각 독립적으로 페닐기; 비페닐기; 터페닐기; 나프틸기; 또는 페난트렌기이고, 상기 페닐기; 비페닐기; 터페닐기; 나프틸기; 또는 페난트렌기는 중수소; CN; 메틸기; 에틸기; 부틸기; 터부틸기; 페닐기; 비페닐기; 터페닐기; 나프틸기; 페난트렌기; 안트라센기; 페릴렌기; 트리페닐렌기; 파이렌기; 플루오란텐; 티오펜기; 퓨란기; 피리딘기; 피리미딘기; 트리아진기; 카바졸기; 디벤조퓨란기 또는 디벤조티오펜기 중 선택되는 어느 하나이상으로 치환 또는 비치환된다. In the exemplary embodiment of the present specification, Ar 41 and Ar 42 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Or a phenanthrene group, and the phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Or the phenanthrene group is deuterium; CN; Methyl group; Ethyl group; Butyl group; Terbutyl group; Phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrene group; Anthracene group; Perylene group; Triphenylene group; Pyren group; Fluoranthene; Thiophene group; Furan group; Pyridine group; Pyrimidine group; Triazine group; Carbazole; It is unsubstituted or substituted with any one or more selected from a dibenzofuran group or a dibenzothiophene group.
본 명세서의 일 실시상태에 있어서, 상기 X1 내지 X3은 N이다.In the exemplary embodiment of the present specification, X 1 to X 3 are N.
본 명세서의 일 실시상태에 있어서, 상기 X1 내지 X3 중 X1은 N이고, 나머지는 CR이다. In one embodiment of the present disclosure, the above X 1 to X 3 X 1 is N and the others are CR.
본 명세서의 일 실시상태에 있어서, 상기 X1 내지 X3 중 X2는 N이고, 나머지는 CR이다. In the exemplary embodiment of the present specification, X 2 of X 1 to X 3 is N, and the rest are CR.
본 명세서의 일 실시상태에 있어서, 상기 X1 내지 X3 중 X3은 N이고, 나머지는 CR이다. In the exemplary embodiment of the present specification, X 3 of X 1 to X 3 is N, and the rest are CR.
본 명세서의 일 실시상태에 있어서, 상기 X1 내지 X3 중 X1은 CR이고, 나머지는 N이다. In one embodiment of the present disclosure, wherein X 1 to X 3 in X 1 is CR, with the remainder being N.
본 명세서의 일 실시상태에 있어서, 상기 X1 내지 X3 중 X2는 CR이고, 나머지는 N이다. In the exemplary embodiment of the present specification, X 2 of X 1 to X 3 is CR, and the rest are N.
본 명세서의 일 실시상태에 있어서, 상기 X1 내지 X3 중 X3은 CR이고, 나머지는 N이다.In the exemplary embodiment of the present specification, X 3 of X 1 to X 3 is CR, and the rest are N.
본 명세서의 일 실시상태에 있어서, 상기 R은 수소; 중수소; 할로겐기; 니트릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아릴옥시기; 또는 치환 또는 비치환된 헤테로고리기이다.In an exemplary embodiment of the present specification, R is hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; Or a substituted or unsubstituted heterocyclic group.
본 명세서의 일 실시상태에 있어서, 상기 R은 수소; 중수소; 니트릴기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아릴옥시기; 또는 치환 또는 비치환된 헤테로고리기이다.In an exemplary embodiment of the present specification, R is hydrogen; heavy hydrogen; Nitrile group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; Or a substituted or unsubstituted heterocyclic group.
본 명세서의 일 실시상태에 있어서, 상기 R은 수소; 중수소 또는 니트릴기이다.In an exemplary embodiment of the present specification, R is hydrogen; It is a deuterium or nitrile group.
본 명세서의 일 실시상태에 있어서, 상기 R은 수소이다.In the exemplary embodiment of the present specification, R is hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 화학식 2은 하기 화학식 2-1로 표시된다.In an exemplary embodiment of the present specification, Formula 2 is represented by the following Formula 2-1.
[화학식 2-1][Formula 2-1]
Figure PCTKR2020010175-appb-I000030
Figure PCTKR2020010175-appb-I000030
상기 화학식 2-1에 있어서, In Formula 2-1,
Y는 CR111R112, O, 또는 S이고, Y is CR111R112, O, or S,
R111, R112, R3-2 및 R3-3은 서로 같거나 상이하고, 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 헤테로아릴기, 또는 하기 화학식 4이거나, 인접한 기와 서로 결합하여 탄화수소고리를 형성하고, R111, R112, R3-2 and R3-3 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or It is the following formula (4), or combines with an adjacent group to form a hydrocarbon ring,
L31 및 L32는 서로 같거나 상이하고, 각각 독립적으로 직접결합, 치환 또는 비치환된 아릴렌, 또는 치환 또는 비치환된 헤테로아릴렌이고,L31 and L32 are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
a32은 0 내지 8의 정수이고,a32 is an integer from 0 to 8,
b33은 0 내지 8의 정수이고,b33 is an integer from 0 to 8,
a33 및 b33이 각각 복수일 때, 괄호 안의 치환기는 서로 같거나 상이하고,When a33 and b33 are each plural, the substituents in parentheses are the same as or different from each other,
n33은 0 또는 1이고,n33 is 0 or 1,
n33이 0일 때, Y에 결합된 2개의 벤젠고리의 위치에는 각각 수소가 결합된다.When n33 is 0, hydrogen is bonded to each of the two benzene rings bonded to Y.
본 명세서의 일 실시상태에 있어서, 상기 a33은 0이다. a33가 0일 때, R3-2로 치환가능한 위치는 수소로 치환된다.In the exemplary embodiment of the present specification, a33 is 0. When a33 is 0, a position capable of being substituted with R3-2 is substituted with hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 b33은 0이다. b33가 0일 때, R3-3으로 치환가능한 위치는 수소로 치환된다.In the exemplary embodiment of the present specification, b33 is 0. When b33 is 0, a position that can be substituted with R3-3 is substituted with hydrogen.
본 명세서의 일 실시상태에 있어서,상기 Y는 O 또는 S이다.In the exemplary embodiment of the present specification, Y is O or S.
본 명세서의 일 실시상태에 있어서, 상기 R3-2는 수소이다.In the exemplary embodiment of the present specification, R3-2 is hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 R3-3은 수소이다.In the exemplary embodiment of the present specification, R3-3 is hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 a33은 1이다.In the exemplary embodiment of the present specification, a33 is 1.
본 명세서의 일 실시상태에 있어서, 상기 b33은 1이다.In the exemplary embodiment of the present specification, b33 is 1.
본 명세서의 일 실시상태에 있어서, 상기 R3-2는 상기 화학식 6 또는 7이다.In the exemplary embodiment of the present specification, R3-2 is Formula 6 or 7.
본 명세서의 일 실시상태에 있어서, 상기 R3-3은 하기 화학식 6 또는 7이다.In an exemplary embodiment of the present specification, R3-3 is the following Chemical Formula 6 or 7.
[화학식 6][Formula 6]
Figure PCTKR2020010175-appb-I000031
Figure PCTKR2020010175-appb-I000031
[화학식 7][Formula 7]
Figure PCTKR2020010175-appb-I000032
Figure PCTKR2020010175-appb-I000032
상기 화학식 6 및 7에 있어서, In Formulas 6 and 7,
상기 점선은 코어와 연결되는 부위이고,The dotted line is a part connected to the core,
L4 및 L5는 서로 같거나 상이하고, 각각 독립적으로 직접결합, 치환 또는 비치환된 아릴렌, 또는 치환 또는 비치환된 헤테로아릴렌이고,L4 and L5 are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
Ar5 및 Ar6은 서로 같거나 상이하고, 각각 독립적으로 수소, 중수소, 할로겐기, 니트릴기, 치환 또는 비치환된 아릴기 또는 치환 또는 비치환된 헤테로아릴기이고,Ar5 and Ar6 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,
c 및 d는 0 내지 5의 정수이고, c and d are integers from 0 to 5,
c 및 d가 복수일 때, 괄호 안의 치환기는 서로 같거나 상이하다.When c and d are plural, the substituents in parentheses are the same as or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 R3-2 및 R3-3은 서로 같거나 상이하고, 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 헤테로아릴기, 상기 화학식 4, 상기 화학식 6 또는 상기 화학식 7이다.In the exemplary embodiment of the present specification, R3-2 and R3-3 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted Is a heteroaryl group, Formula 4, Formula 6, or Formula 7.
본 명세서의 일 실시상태에 있어서, 상기 R3-2 및 R3-3은 서로 같거나 상이하고, 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 탄소수 6 내지 20의 아릴기, 치환 또는 비치환된 탄소수 3 내지 20의 헤테로아릴기, 상기 화학식 4, 상기 화학식 6 또는 상기 화학식 7이다.In the exemplary embodiment of the present specification, R3-2 and R3-3 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted carbon number. Heteroaryl group of 3 to 20, Formula 4, Formula 6, or Formula 7.
본 명세서의 일 실시상태에 있어서, 상기 R3-2 및 R3-3 중 상기 화학식 4, 상기 화학식 6 또는 상기 화학식 7가 아닌 치환기는 메틸기, 터부틸기, 부틸기, 페닐기, 나프틸기, 피리딘기, 피리미딘기, 트리아진기, 퀴나졸린기, 퀴놀린기, 퀴녹살린기, 트리페닐렌기이고, 상기 페닐기, 나프틸기, 피리딘기, 피리미딘기, 트리아진기, 퀴나졸린기, 퀴놀린기, 퀴녹살린기, 트리페닐렌기은 중수소, CN, 알킬기, 아릴기, 및 헤테로아릴기 중 선택되는 어느 하나 이상의 치환기로 치환 또는 비치환된다.In an exemplary embodiment of the present specification, a substituent other than Formula 4, Formula 6, or Formula 7 of R3-2 and R3-3 is a methyl group, terbutyl group, butyl group, phenyl group, naphthyl group, pyridine group, It is a pyrimidine group, a triazine group, a quinazoline group, a quinoline group, a quinoxaline group, a triphenylene group, and the phenyl group, a naphthyl group, a pyridine group, a pyrimidine group, a triazine group, a quinazoline group, a quinoline group, a quinoxaline group, The triphenylene group is unsubstituted or substituted with any one or more substituents selected from deuterium, CN, an alkyl group, an aryl group, and a heteroaryl group.
본 명세서의 일 실시상태에 있어서, 상기 a33은 2이고, 상기 R3-2는 서로 같거나 상이하다.In the exemplary embodiment of the present specification, a33 is 2, and R3-2 is the same as or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 b33은 2 이고, 상기 R3-3은 서로 같거나 상이하다.In the exemplary embodiment of the present specification, b33 is 2, and R3-3 is the same as or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 복수의 R3-2 중 상기 화학식 4, 상기 화학식 6 또는 상기 화학식 7가 아닌 치환기는 메틸기, 터부틸기, 부틸기, 페닐기, 나프틸기, 피리딘기, 피리미딘기, 트리아진기, 퀴나졸린기, 퀴놀린기, 퀴녹살린기, 트리페닐렌기이고, 상기 페닐기, 나프틸기, 피리딘기, 피리미딘기, 트리아진기, 퀴나졸린기, 퀴놀린기, 퀴녹살린기, 트리페닐렌기은 중수소, CN, 알킬기, 아릴기, 및 헤테로아릴기 중 선택되는 어느 하나 이상의 치환기로 치환 또는 비치환된다.In the exemplary embodiment of the present specification, a substituent other than Formula 4, Formula 6, or Formula 7 of the plurality of R3-2 is a methyl group, terbutyl group, butyl group, phenyl group, naphthyl group, pyridine group, and pyrimy. Dine group, triazine group, quinazoline group, quinoline group, quinoxaline group, triphenylene group, the phenyl group, naphthyl group, pyridine group, pyrimidine group, triazine group, quinazoline group, quinoline group, quinoxaline group, triphenyl The ene group is unsubstituted or substituted with any one or more substituents selected from deuterium, CN, an alkyl group, an aryl group, and a heteroaryl group.
본 명세서의 일 실시상태에 있어서, 상기 복수의 R3-3 중 상기 화학식 4, 상기 화학식 6 또는 상기 화학식 7가 아닌 치환기는 메틸기, 터부틸기, 부틸기, 페닐기, 나프틸기, 피리딘기, 피리미딘기, 트리아진기, 퀴나졸린기, 퀴놀린기, 퀴녹살린기, 트리페닐렌기이고, 상기 페닐기, 나프틸기, 피리딘기, 피리미딘기, 트리아진기, 퀴나졸린기, 퀴놀린기, 퀴녹살린기, 트리페닐렌기은 중수소, CN, 알킬기, 아릴기, 및 헤테로아릴기 중 선택되는 어느 하나 이상의 치환기로 치환 또는 비치환된다.In an exemplary embodiment of the present specification, a substituent other than Formula 4, Formula 6, or Formula 7 of the plurality of R3-3 is a methyl group, terbutyl group, butyl group, phenyl group, naphthyl group, pyridine group, and pyrimy. Dine group, triazine group, quinazoline group, quinoline group, quinoxaline group, triphenylene group, the phenyl group, naphthyl group, pyridine group, pyrimidine group, triazine group, quinazoline group, quinoline group, quinoxaline group, triphenyl The ene group is unsubstituted or substituted with any one or more substituents selected from deuterium, CN, an alkyl group, an aryl group, and a heteroaryl group.
본 명세서의 일 실시상태에 있어서, 상기 L1 내지 L5는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이다.In the exemplary embodiment of the present specification, L 1 to L 5 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.
본 명세서의 일 실시상태에 있어서, 상기 L1 내지 L5는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기; 또는 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴렌기이다.In the exemplary embodiment of the present specification, L 1 to L 5 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 3 to C 30 heteroarylene group.
본 명세서의 일 실시상태에 있어서, 상기 L1 내지 L5는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 페닐렌기; 2가의 비페닐기; 2가의 터페닐기; 2가의 플루오렌기; 2가의 페녹사진기; 2가의 나프틸기; 2가의 퀴나졸기; 2가의 퀴놀린기; 2가의 퀴녹살린기; 2가의 디벤조퓨란기; 2가의 디벤조티오펜기; 2가의 카바졸기; 2가의 벤조카바졸기; 2가의 인데노카바졸기; 2가의 페노티아진기; 2가의 페녹사티인(phenoxathiine); 2가의 디벤조실롤기; 2가의 피롤기; 2가의 퓨란기; 2가의 티오펜기; 2가의 피리딘기; 2가의 피리미딘기; 또는 2가의 트리아진기이고, In the exemplary embodiment of the present specification, L 1 to L 5 are the same as or different from each other, and each independently a direct bond; Phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent fluorene group; A divalent phenoxy camera; Divalent naphthyl group; Divalent quinazole group; Divalent quinoline group; Divalent quinoxalin group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Divalent carbazole group; Divalent benzocarbazole group; Divalent indenocarbazole; A divalent phenothiazine group; Divalent phenoxathiine; Divalent dibenzosilol group; Divalent pyrrole group; Divalent furan group; Divalent thiophene group; A divalent pyridine group; Divalent pyrimidine group; Or a divalent triazine group,
상기 페닐렌기; 2가의 비페닐기; 2가의 터페닐기; 2가의 플루오렌기; 2가의 페녹사진기; 2가의 나프틸기; 2가의 퀴나졸기; 2가의 퀴놀린기; 2가의 퀴녹살린기; 2가의 디벤조퓨란기; 2가의 디벤조티오펜기; 2가의 카바졸기; 2가의 벤조카바졸기; 2가의 인데노카바졸기; 2가의 페노티아진기; 2가의 페녹사티인(phenoxathiine); 2가의 디벤조실롤기; 2가의 피롤기; 2가의 퓨란기; 2가의 티오펜기; 2가의 피리딘기; 2가의 피리미딘기; 또는 2가의 트리아진기는 CN, 탄소수 1 내지 10의 알킬기, 탄소수 6 내지 20의 아릴기, 또는 탄소수 3 내지 30의 헤테로아릴기로 치환 또는 비치환될 수 있다. The phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent fluorene group; A divalent phenoxy camera; Divalent naphthyl group; Divalent quinazole group; Divalent quinoline group; Divalent quinoxalin group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Divalent carbazole group; Divalent benzocarbazole group; Divalent indenocarbazole; A divalent phenothiazine group; Divalent phenoxathiine; Divalent dibenzosilol group; Divalent pyrrole group; Divalent furan group; Divalent thiophene group; A divalent pyridine group; Divalent pyrimidine group; Alternatively, the divalent triazine group may be unsubstituted or substituted with CN, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 L1 내지 L5는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 페닐렌기; 2가의 비페닐기; 2가의 터페닐기; 2가의 플루오렌기; 2가의 페녹사진기; 2가의 나프틸기; 2가의 퀴나졸기; 2가의 퀴놀린기; 2가의 퀴녹살린기; 2가의 디벤조퓨란기; 2가의 디벤조티오펜기; 2가의 카바졸기; 2가의 벤조카바졸기; 2가의 인데노카바졸기; 2가의 페노티아진기; 2가의 페녹사티인(phenoxathiine); 2가의 디벤조실롤기; 2가의 피롤기; 2가의 퓨란기; 2가의 티오펜기; 2가의 피리딘기; 2가의 피리미딘기; 또는 2가의 트리아진기이고, In the exemplary embodiment of the present specification, L 1 to L 5 are the same as or different from each other, and each independently a direct bond; Phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent fluorene group; A divalent phenoxy camera; Divalent naphthyl group; Divalent quinazole group; Divalent quinoline group; Divalent quinoxalin group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Divalent carbazole group; Divalent benzocarbazole group; Divalent indenocarbazole; A divalent phenothiazine group; Divalent phenoxathiine; Divalent dibenzosilol group; Divalent pyrrole group; Divalent furan group; Divalent thiophene group; A divalent pyridine group; Divalent pyrimidine group; Or a divalent triazine group,
상기 페닐렌기; 2가의 비페닐기; 2가의 터페닐기; 2가의 플루오렌기; 2가의 페녹사진기; 2가의 나프틸기; 2가의 퀴나졸기; 2가의 퀴놀린기; 2가의 퀴녹살린기; 2가의 디벤조퓨란기; 2가의 디벤조티오펜기; 2가의 카바졸기; 2가의 벤조카바졸기; 2가의 인데노카바졸기; 2가의 페노티아진기; 2가의 페녹사티인(phenoxathiine); 2가의 디벤조실롤기; 2가의 피롤기; 2가의 퓨란기; 2가의 티오펜기; 2가의 피리딘기; 2가의 피리미딘기; 또는 2가의 트리아진기는 CN, 메틸기, 부틸기, 터부틸기, 페닐기, 나프틸기, 비페닐기 또는 터페닐기로 치환 또는 비치환될 수 있다. The phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent fluorene group; A divalent phenoxy camera; Divalent naphthyl group; Divalent quinazole group; Divalent quinoline group; Divalent quinoxalin group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Divalent carbazole group; Divalent benzocarbazole group; Divalent indenocarbazole; A divalent phenothiazine group; Divalent phenoxathiine; Divalent dibenzosilol group; Divalent pyrrole group; Divalent furan group; Divalent thiophene group; A divalent pyridine group; Divalent pyrimidine group; Alternatively, the divalent triazine group may be unsubstituted or substituted with CN, a methyl group, a butyl group, a terbutyl group, a phenyl group, a naphthyl group, a biphenyl group, or a terphenyl group.
본 명세서의 일 실시상태에 있어서, 상기 L1 내지 L5는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 페닐렌기; 2가의 비페닐기; 2가의 터페닐기; 2가의 플루오렌기; 2가의 페녹사진기; 2가의 나프틸기; 2가의 퀴나졸기; 2가의 퀴놀린기; 2가의 퀴녹살린기; 2가의 디벤조퓨란기; 2가의 디벤조티오펜기; 2가의 카바졸기; 2가의 벤조카바졸기; 2가의 인데노카바졸기; 2가의 페노티아진기; 2가의 페녹사티인(phenoxathiine); 2가의 디벤조실롤기; 2가의 피롤기; 2가의 퓨란기; 2가의 티오펜기; 2가의 피리딘기; 2가의 피리미딘기; 또는 2가의 트리아진기이고, 상기 페닐렌기; 2가의 비페닐기; 2가의 터페닐기; 2가의 플루오렌기; 2가의 페녹사진기; 2가의 나프틸기; 2가의 퀴나졸기; 2가의 퀴놀린기; 2가의 퀴녹살린기; 2가의 디벤조퓨란기; 2가의 디벤조티오펜기; 2가의 카바졸기; 2가의 벤조카바졸기; 2가의 인데노카바졸기; 2가의 페노티아진기; 2가의 페녹사티인(phenoxathiine); 2가의 디벤조실롤기; 2가의 피롤기; 2가의 퓨란기; 2가의 티오펜기; 2가의 피리딘기; 2가의 피리미딘기; 또는 2가의 트리아진기는 어느 2 이상이 중첩된 구조로 화합물 내에 존재할 수 있다.In the exemplary embodiment of the present specification, L 1 to L 5 are the same as or different from each other, and each independently a direct bond; Phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent fluorene group; A divalent phenoxy camera; Divalent naphthyl group; Divalent quinazole group; Divalent quinoline group; Divalent quinoxalin group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Divalent carbazole group; Divalent benzocarbazole group; Divalent indenocarbazole; A divalent phenothiazine group; Divalent phenoxathiine; Divalent dibenzosilol group; Divalent pyrrole group; Divalent furan group; Divalent thiophene group; A divalent pyridine group; Divalent pyrimidine group; Or a divalent triazine group, the phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent fluorene group; A divalent phenoxy camera; Divalent naphthyl group; Divalent quinazole group; Divalent quinoline group; Divalent quinoxalin group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Divalent carbazole group; Divalent benzocarbazole group; Divalent indenocarbazole; A divalent phenothiazine group; Divalent phenoxathiine; Divalent dibenzosilol group; Divalent pyrrole group; Divalent furan group; Divalent thiophene group; A divalent pyridine group; Divalent pyrimidine group; Alternatively, the divalent triazine group may exist in the compound in a structure in which any two or more are overlapped.
본 명세서에서 중첩된 구조라 함은 치환기 2 이상이 순차로 결합한 것을 뜻한다. 예컨대 '페닐렌기와 2가의 카바졸기가 중첩되었다'함은 -페닐렌-2가의 카바졸-이 순차로 결합한 것을 의미한다. In the present specification, the term "overlapped" means that two or more substituents are sequentially bonded. For example, "the phenylene group and the divalent carbazole group overlap" means that -phenylene-divalent carbazole- is sequentially bonded.
본 명세서의 일 실시상태에 있어서, 상기 L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 탄소수 6 내지 30의 아릴렌기; 또는 탄소수 3 내지 30의 헤테로아릴렌기이다.In the exemplary embodiment of the present specification, L 1 to L 3 are the same as or different from each other, and each independently a direct bond; An arylene group having 6 to 30 carbon atoms; Or a heteroarylene group having 3 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 L1 내지 L3은 직접결합이다.In the exemplary embodiment of the present specification, L 1 to L 3 are direct bonds.
본 명세서의 일 실시상태에 있어서, 상기 L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 페닐렌기; 2가의 비페닐기; 2가의 터페닐기; 2가의 나프틸기; 2가의 퀴나졸기; 2가의 퀴놀린기; 2가의 퀴녹살린기; 2가의 디벤조퓨란기; 2가의 디벤조티오펜기; 2가의 카바졸기; 2가의 디벤조실롤기; 2가의 피롤기; 2가의 퓨란기; 2가의 티오펜기; 또는 2가의 피리딘기이다. In the exemplary embodiment of the present specification, L 1 to L 3 are the same as or different from each other, and each independently a direct bond; Phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent naphthyl group; Divalent quinazole group; Divalent quinoline group; Divalent quinoxalin group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Divalent carbazole group; Divalent dibenzosilol group; Divalent pyrrole group; Divalent furan group; Divalent thiophene group; Or a divalent pyridine group.
본 명세서의 일 실시상태에 있어서, 상기 L3은 직접결합; 페닐렌기; 2가의 비페닐기; 2가의 터페닐기; 2가의 나프틸기; 2가의 퀴나졸기; 2가의 퀴놀린기; 2가의 퀴녹살린기; 2가의 디벤조퓨란기; 2가의 디벤조티오펜기; 2가의 카바졸기; 2가의 디벤조실롤기; 2가의 피롤기; 2가의 퓨란기; 2가의 티오펜기; 또는 2가의 피리딘기이다.In the exemplary embodiment of the present specification, L 3 is a direct bond; Phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent naphthyl group; Divalent quinazole group; Divalent quinoline group; Divalent quinoxalin group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Divalent carbazole group; Divalent dibenzosilol group; Divalent pyrrole group; Divalent furan group; Divalent thiophene group; Or a divalent pyridine group.
본 명세서의 일 실시상태에 있어서, 상기 L3은 직접결합, 또는 페닐렌기이다.In the exemplary embodiment of the present specification, L 3 is a direct bond or a phenylene group.
본 명세서의 일 실시상태에 있어서, 상기 L31 및 L32는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이다.In the exemplary embodiment of the present specification, L31 and L32 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.
본 명세서의 일 실시상태에 있어서, 상기 L31 및 L32는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기; 또는 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴렌기이다.In the exemplary embodiment of the present specification, L31 and L32 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 3 to C 30 heteroarylene group.
본 명세서의 일 실시상태에 있어서, 상기 L31 및 L32는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 페닐렌기; 2가의 비페닐기; 2가의 터페닐기; 2가의 플루오렌기; 2가의 페녹사진기; 2가의 나프틸기; 2가의 퀴나졸기; 2가의 퀴놀린기; 2가의 퀴녹살린기; 2가의 디벤조퓨란기; 2가의 디벤조티오펜기; 2가의 카바졸기; 2가의 벤조카바졸기; 2가의 인데노카바졸기; 2가의 페노티아진기; 2가의 페녹사티인(phenoxathiine); 2가의 디벤조실롤기; 2가의 피롤기; 2가의 퓨란기; 2가의 티오펜기; 2가의 피리딘기; 2가의 피리미딘기; 또는 2가의 트리아진기이고, In the exemplary embodiment of the present specification, L31 and L32 are the same as or different from each other, and each independently a direct bond; Phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent fluorene group; A divalent phenoxy camera; Divalent naphthyl group; Divalent quinazole group; Divalent quinoline group; Divalent quinoxalin group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Divalent carbazole group; Divalent benzocarbazole group; Divalent indenocarbazole; A divalent phenothiazine group; Divalent phenoxathiine; Divalent dibenzosilol group; Divalent pyrrole group; Divalent furan group; Divalent thiophene group; A divalent pyridine group; Divalent pyrimidine group; Or a divalent triazine group,
상기 페닐렌기; 2가의 비페닐기; 2가의 터페닐기; 2가의 플루오렌기; 2가의 페녹사진기; 2가의 나프틸기; 2가의 퀴나졸기; 2가의 퀴놀린기; 2가의 퀴녹살린기; 2가의 디벤조퓨란기; 2가의 디벤조티오펜기; 2가의 카바졸기; 2가의 벤조카바졸기; 2가의 인데노카바졸기; 2가의 페노티아진기; 2가의 페녹사티인(phenoxathiine); 2가의 디벤조실롤기; 2가의 피롤기; 2가의 퓨란기; 2가의 티오펜기; 2가의 피리딘기; 2가의 피리미딘기; 또는 2가의 트리아진기는 CN, 탄소수 1 내지 10의 알킬기, 탄소수 6 내지 20의 아릴기, 또는 탄소수 3 내지 30의 헤테로아릴기로 치환 또는 비치환될 수 있다. The phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent fluorene group; A divalent phenoxy camera; Divalent naphthyl group; Divalent quinazole group; Divalent quinoline group; Divalent quinoxalin group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Divalent carbazole group; Divalent benzocarbazole group; Divalent indenocarbazole; A divalent phenothiazine group; Divalent phenoxathiine; Divalent dibenzosilol group; Divalent pyrrole group; Divalent furan group; Divalent thiophene group; A divalent pyridine group; Divalent pyrimidine group; Alternatively, the divalent triazine group may be unsubstituted or substituted with CN, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 L31 및 L32는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 페닐렌기; 2가의 비페닐기; 2가의 터페닐기; 2가의 플루오렌기; 2가의 페녹사진기; 2가의 나프틸기; 2가의 퀴나졸기; 2가의 퀴놀린기; 2가의 퀴녹살린기; 2가의 디벤조퓨란기; 2가의 디벤조티오펜기; 2가의 카바졸기; 2가의 벤조카바졸기; 2가의 인데노카바졸기; 2가의 페노티아진기; 2가의 페녹사티인(phenoxathiine); 2가의 디벤조실롤기; 2가의 피롤기; 2가의 퓨란기; 2가의 티오펜기; 2가의 피리딘기; 2가의 피리미딘기; 또는 2가의 트리아진기이고, 상기 페닐렌기; 2가의 비페닐기; 2가의 터페닐기; 2가의 플루오렌기; 2가의 페녹사진기; 2가의 나프틸기; 2가의 퀴나졸기; 2가의 퀴놀린기; 2가의 퀴녹살린기; 2가의 디벤조퓨란기; 2가의 디벤조티오펜기; 2가의 카바졸기; 2가의 벤조카바졸기; 2가의 인데노카바졸기; 2가의 페노티아진기; 2가의 페녹사티인(phenoxathiine); 2가의 디벤조실롤기; 2가의 피롤기; 2가의 퓨란기; 2가의 티오펜기; 2가의 피리딘기; 2가의 피리미딘기; 또는 2가의 트리아진기는 어느 2 이상이 중첩된 구조로 화합물 내에 존재할 수 있다.In the exemplary embodiment of the present specification, L31 and L32 are the same as or different from each other, and each independently a direct bond; Phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent fluorene group; A divalent phenoxy camera; Divalent naphthyl group; Divalent quinazole group; Divalent quinoline group; Divalent quinoxalin group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Divalent carbazole group; Divalent benzocarbazole group; Divalent indenocarbazole; A divalent phenothiazine group; Divalent phenoxathiine; Divalent dibenzosilol group; Divalent pyrrole group; Divalent furan group; Divalent thiophene group; A divalent pyridine group; Divalent pyrimidine group; Or a divalent triazine group, the phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent fluorene group; A divalent phenoxy camera; Divalent naphthyl group; Divalent quinazole group; Divalent quinoline group; Divalent quinoxalin group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Divalent carbazole group; Divalent benzocarbazole group; Divalent indenocarbazole; A divalent phenothiazine group; Divalent phenoxathiine; Divalent dibenzosilol group; Divalent pyrrole group; Divalent furan group; Divalent thiophene group; A divalent pyridine group; Divalent pyrimidine group; Alternatively, the divalent triazine group may exist in the compound in a structure in which any two or more are overlapped.
본 명세서의 일 실시상태에 있어서, 상기 R3-2는 인접한 기와 서로 결합하여 탄화수소고리를 형성한다.In the exemplary embodiment of the present specification, R3-2 is bonded to each other with adjacent groups to form a hydrocarbon ring.
본 명세서의 일 실시상태에 있어서, 상기 R3-2는 인접한 기와 서로 결합하여 방향족 탄화수소고리를 형성한다.In the exemplary embodiment of the present specification, R3-2 is combined with an adjacent group to form an aromatic hydrocarbon ring.
본 명세서의 일 실시상태에 있어서, 상기 R3-2는 인접한 기와 서로 결합하여 탄소수 6 내지 20의 방향족 탄화수소고리를 형성한다.In the exemplary embodiment of the present specification, R3-2 is combined with an adjacent group to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R3-3은 인접한 기와 서로 결합하여 탄화수소고리를 형성한다.In the exemplary embodiment of the present specification, R3-3 is bonded to each other with adjacent groups to form a hydrocarbon ring.
본 명세서의 일 실시상태에 있어서, 상기 R3-3은 인접한 기와 서로 결합하여 방향족 탄화수소고리를 형성한다.In the exemplary embodiment of the present specification, R3-3 is bonded to each other with adjacent groups to form an aromatic hydrocarbon ring.
본 명세서의 일 실시상태에 있어서, 상기 R3-3은 인접한 기와 서로 결합하여 탄소수 6 내지 20의 방향족 탄화수소고리를 형성한다.In the exemplary embodiment of the present specification, R3-3 is bonded to each other with adjacent groups to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 화학식 2-1은 하기 화학식 2-2 내지 화학식 2-6 중 어느 하나로 표시된다.In an exemplary embodiment of the present specification, Formula 2-1 is represented by any one of Formulas 2-2 to 2-6 below.
[화학식 2-2][Formula 2-2]
Figure PCTKR2020010175-appb-I000033
Figure PCTKR2020010175-appb-I000033
[화학식 2-3][Formula 2-3]
Figure PCTKR2020010175-appb-I000034
Figure PCTKR2020010175-appb-I000034
[화학식 2-4][Formula 2-4]
Figure PCTKR2020010175-appb-I000035
Figure PCTKR2020010175-appb-I000035
[화학식 2-5][Formula 2-5]
Figure PCTKR2020010175-appb-I000036
Figure PCTKR2020010175-appb-I000036
상기 화학식 2-2 내지 2-6에 있어서, R3-2, L32 및 a33은 상기 화학식 2-1에서 정의한 바와 같고, In Formulas 2-2 to 2-6, R3-2, L32 and a33 are as defined in Formula 2-1,
R3-4 및 R3-5는 상기 화학식 2-1의 R3-3과 같고,R3-4 and R3-5 are the same as R3-3 of Formula 2-1,
a34 및 a35는 상기 화학식 2-1의 a33과 같다.a34 and a35 are the same as a33 in Chemical Formula 2-1.
본 명세서의 일 실시상태에 있어서, 상기 n이 0일 경우, 상기 R3-2 및 R3-3 중 상기 화학식 4가 아닌 치환기 중 하나는 치환 또는 비치환된 아릴기이다.In the exemplary embodiment of the present specification, when n is 0, one of the substituents other than Formula 4 in R3-2 and R3-3 is a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 있어서, 상기 n이 0일 경우, 상기 R3-2 및 R3-3 중 상기 화학식 4가 아닌 치환기 중 하나는 치환 또는 비치환된 플루오렌기, 또는 치환 또는 비치환된 벤조플루오렌기이다.In the exemplary embodiment of the present specification, when n is 0, one of the substituents other than Formula 4 in R3-2 and R3-3 is a substituted or unsubstituted fluorene group, or a substituted or unsubstituted benzo. It is a fluorene group.
본 명세서의 일 실시상태에 있어서, 상기 n이 0일 경우, 상기 R3-2 및 R3-3 중 상기 화학식 4가 아닌 치환기 중 하나는 중수소, 알킬기 또는 알킬아릴기로 치환 또는 비치환된 플루오렌기; 또는 중수소, 알킬기 또는 알킬아릴기로 치환 또는 비치환된 벤조플루오렌기이다. In the exemplary embodiment of the present specification, when n is 0, one of the substituents other than Formula 4 in R3-2 and R3-3 is a fluorene group unsubstituted or substituted with deuterium, an alkyl group, or an alkylaryl group; Or a benzofluorene group unsubstituted or substituted with deuterium, an alkyl group, or an alkylaryl group.
본 명세서의 일 실시상태에 있어서, 상기 R3-4 및 R3-5은 수소이다.In the exemplary embodiment of the present specification, R3-4 and R3-5 are hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 a34 및 a35는 0이다.In the exemplary embodiment of the present specification, a34 and a35 are 0.
본 명세서의 일 실시상태에 있어서, 상기 Ar41 및 Ar42는 서로 같거나 상이하고, 각각 독립적으로 메틸기, 실릴기, 페닐기, 비페닐기, 나프틸기, 터페닐기, 디벤조퓨란기, 디벤조티오펜기, 카바졸기, 실롤기, 또는 Si, N, O, 또는 S를 포함하는 다환의 헤테로아릴기이고,In the exemplary embodiment of the present specification, Ar 41 and Ar 42 are the same as or different from each other, and each independently a methyl group, a silyl group, a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a dibenzofuran group, and a dibenzothiophene. A group, a carbazole group, a silol group, or a polycyclic heteroaryl group containing Si, N, O, or S,
상기 메틸기, 실릴기, 페닐기, 비페닐기, 나프틸기, 터페닐기, 디벤조퓨란기, 디벤조티오펜기, 카바졸기, 실롤기, 또는 Si, N, O, 또는 S를 포함하는 다환의 헤테로아릴기는 중수소, 니트릴기, 할로겐기, 치환 또는 비치환된 탄소수 1 내지 10의 알킬기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 탄소수 6 내지 20의 아릴기, 치환 또는 비치환된 탄소수 3 내지 20의 헤테로아릴기로 치환 또는 비치환된다.Polycyclic heteroaryl including the methyl group, silyl group, phenyl group, biphenyl group, naphthyl group, terphenyl group, dibenzofuran group, dibenzothiophene group, carbazole group, silol group, or Si, N, O, or S The group is deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted 3 to carbon number It is unsubstituted or substituted with 20 heteroaryl groups.
본 명세서의 일 실시상태에 있어서, 상기 Ar41 및 Ar42는 서로 같거나 상이하고, 각각 독립적으로 메틸기, 실릴기, 페닐기, 비페닐기, 나프틸기, 터페닐기, 디벤조퓨란기, 디벤조티오펜기, 카바졸기, 실롤기, 또는 Si, N, O, 또는 S를 포함하는 다환의 헤테로아릴기이고,In the exemplary embodiment of the present specification, Ar 41 and Ar 42 are the same as or different from each other, and each independently a methyl group, a silyl group, a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a dibenzofuran group, and a dibenzothiophene. A group, a carbazole group, a silol group, or a polycyclic heteroaryl group containing Si, N, O, or S,
상기 메틸기, 실릴기, 페닐기, 비페닐기, 나프틸기, 터페닐기, 디벤조퓨란기, 디벤조티오펜기, 카바졸기, 실롤기, 또는 Si, N, O, 또는 S를 포함하는 다환의 헤테로아릴기는 중수소, 니트릴기, 할로겐기, 치환 또는 비치환된 메틸기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 페닐기, 치환 또는 비치환된 비페닐기, 치환 또는 비치환된 터페닐기, 치환 또는 비치환된 나프틸기, 치환 또는 비치환된 카바졸기, 치환 또는 비치환된 디벤조퓨란기, 치환 또는 비치환된 디벤조티오펜기, 치환 또는 비치환된 벤조카바졸기, 및 치환 또는 비치환된 피리딘기 중에서 선택되는 하나 이상의 치환기로 치환 또는 비치환된다.Polycyclic heteroaryl including the methyl group, silyl group, phenyl group, biphenyl group, naphthyl group, terphenyl group, dibenzofuran group, dibenzothiophene group, carbazole group, silol group, or Si, N, O, or S The group is deuterium, nitrile group, halogen group, substituted or unsubstituted methyl group, substituted or unsubstituted silyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted A substituted naphthyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted benzocarbazole group, and a substituted or unsubstituted pyridine It is unsubstituted or substituted with one or more substituents selected from groups.
본 명세서의 일 실시상태에 있어서, 상기 Ar5 및 Ar6은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 아릴기, 또는 치환 또는 비치환된 헤테로아릴기이다.In the exemplary embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted It is a cyclic heteroaryl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar5 및 Ar6은서로 같거나 상이하고, 각각 독립적으로 메틸기, 실릴기, 페닐기, 비페닐기, 나프틸기, 터페닐기, 디벤조퓨란기, 디벤조티오펜기, 카바졸기, 실롤기, 또는 Si, N, O, 또는 S를 포함하는 다환의 헤테로아릴기이고,In the exemplary embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and each independently a methyl group, a silyl group, a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a dibenzofuran group, a dibenzothiophene group, It is a carbazole group, a silol group, or a polycyclic heteroaryl group containing Si, N, O, or S,
상기 메틸기, 실릴기, 페닐기, 비페닐기, 나프틸기, 터페닐기, 디벤조퓨란기, 디벤조티오펜기, 카바졸기, 실롤기, 또는 Si, N, O, 또는 S를 포함하는 다환의 헤테로아릴기는 중수소, 니트릴기, 할로겐기, 치환 또는 비치환된 탄소수 1 내지 10의 알킬기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 탄소수 6 내지 20의 아릴기, 치환 또는 비치환된 탄소수 3 내지 20의 헤테로아릴기로 치환 또는 비치환된다.Polycyclic heteroaryl including the methyl group, silyl group, phenyl group, biphenyl group, naphthyl group, terphenyl group, dibenzofuran group, dibenzothiophene group, carbazole group, silol group, or Si, N, O, or S The group is deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted 3 to carbon number It is unsubstituted or substituted with 20 heteroaryl groups.
본 명세서의 일 실시상태에 있어서, 상기 Ar5 및 Ar6 서로 같거나 상이하고, 각각 독립적으로 메틸기, 실릴기, 페닐기, 비페닐기, 나프틸기, 터페닐기, 디벤조퓨란기, 디벤조티오펜기, 카바졸기, 실롤기, 또는 Si, N, O, 또는 S를 포함하는 다환의 헤테로아릴기이고,In the exemplary embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and each independently methyl group, silyl group, phenyl group, biphenyl group, naphthyl group, terphenyl group, dibenzofuran group, dibenzothiophene group, carba It is a sol group, a silol group, or a polycyclic heteroaryl group containing Si, N, O, or S,
상기 메틸기, 실릴기, 페닐기, 비페닐기, 나프틸기, 터페닐기, 디벤조퓨란기, 디벤조티오펜기, 카바졸기, 실롤기, 또는 Si, N, O, 또는 S를 포함하는 다환의 헤테로아릴기는 중수소, 니트릴기, 할로겐기, 치환 또는 비치환된 메틸기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 페닐기, 치환 또는 비치환된 비페닐기, 치환 또는 비치환된 터페닐기, 치환 또는 비치환된 나프틸기, 치환 또는 비치환된 카바졸기, 치환 또는 비치환된 디벤조퓨란기, 치환 또는 비치환된 디벤조티오펜기, 치환 또는 비치환된 벤조카바졸기, 및 치환 또는 비치환된 피리딘기 중에서 선택되는 하나 이상의 치환기로 치환 또는 비치환된다.Polycyclic heteroaryl including the methyl group, silyl group, phenyl group, biphenyl group, naphthyl group, terphenyl group, dibenzofuran group, dibenzothiophene group, carbazole group, silol group, or Si, N, O, or S The group is deuterium, nitrile group, halogen group, substituted or unsubstituted methyl group, substituted or unsubstituted silyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted A substituted naphthyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted benzocarbazole group, and a substituted or unsubstituted pyridine It is unsubstituted or substituted with one or more substituents selected from groups.
본 명세서의 일 실시상태에 있어서, 상기 Ar5 및 Ar6 서로 같거나 상이하고, 각각 독립적으로 메틸기, 실릴기, 페닐기, 비페닐기, 나프틸기, 터페닐기, 디벤조퓨란기, 디벤조티오펜기, 카바졸기, 실롤기, 또는 Si, N, O, 또는 S를 포함하는 3환의 헤테로아릴기이고,In the exemplary embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and each independently methyl group, silyl group, phenyl group, biphenyl group, naphthyl group, terphenyl group, dibenzofuran group, dibenzothiophene group, carba It is a sol group, a silol group, or a tricyclic heteroaryl group containing Si, N, O, or S,
상기 메틸기, 실릴기, 페닐기, 비페닐기, 나프틸기, 터페닐기, 디벤조퓨란기, 디벤조티오펜기, 카바졸기, 실롤기, 또는 Si, N, O, 또는 S를 포함하는 3환의 헤테로아릴기는 중수소, 니트릴기, 할로겐기, 메틸기, 트리플루오로메틸기, 트리플루오로메톡시기, 메톡시기, 트리메틸실릴기, 페닐기, 비페닐기, 터페닐기, 나프틸기, 카바졸기, 페닐기로 치환된 카바졸기, 디벤조퓨란기, 디벤조티오펜기, 벤조카바졸기, 인돌로카바졸기, 피리딘기 중에서 선택되는 하나 이상의 치환기로 치환 또는 비치환된다.Tricyclic heteroaryl containing the methyl group, silyl group, phenyl group, biphenyl group, naphthyl group, terphenyl group, dibenzofuran group, dibenzothiophene group, carbazole group, silol group, or Si, N, O, or S Groups include deuterium, nitrile group, halogen group, methyl group, trifluoromethyl group, trifluoromethoxy group, methoxy group, trimethylsilyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, carbazole group, carbazole group substituted with phenyl group, It is unsubstituted or substituted with one or more substituents selected from dibenzofuran group, dibenzothiophene group, benzocarbazole group, indolocarbazole group, and pyridine group.
본 명세서의 일 실시상태에 있어서, 상기 Ar5 및 Ar6 서로 같거나 상이하고, 각각 독립적으로 본 명세서의 일 실시상태에 있어서, 상기 Ar41 및 Ar42는 서로 같거나 상이하고, 각각 독립적으로 메틸기; 에틸기; 부틸기; 터부틸기; 페닐기; 비페닐기; 터페닐기; 나프틸기; 페난트렌기; 트리페닐렌기; 페릴렌기; 플루오렌기; 플루오잔텐기; 카바졸기; 벤조카바졸기; 인데노카바졸기; 피리딘기; 피리미딘기; 트리아진기; 디벤조퓨란기; 디벤조티오펜기; 퀴놀린기; 퀴나졸린기; 퀴녹살린기; 페녹사진기; 2가의 페노티아진기; 2가의 페녹사티인; 또는 트리메틸실릴기이고, In the exemplary embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and each independently In the exemplary embodiment of the present specification, Ar 41 and Ar 42 are the same as or different from each other, and each independently a methyl group; Ethyl group; Butyl group; Terbutyl group; Phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrene group; Triphenylene group; Perylene group; Fluorene group; Fluoroxanthene group; Carbazole; Benzocarbazole group; Indenocarbazole; Pyridine group; Pyrimidine group; Triazine group; Dibenzofuran group; Dibenzothiophene group; Quinoline group; Quinazoline; Quinoxalin group; Phenox camera; A divalent phenothiazine group; Divalent phenoxatiin; Or a trimethylsilyl group,
상기 페닐기; 비페닐기; 터페닐기; 나프틸기; 페난트렌기; 트리페닐렌기; 페릴렌기; 플루오렌기; 플루오잔텐기; 카바졸기; 벤조카바졸기; 인데노카바졸기; 피리딘기; 피리미딘기; 트리아진기; 디벤조퓨란기; 디벤조티오펜기; 퀴놀린기; 퀴나졸린기; 퀴녹살린기; 페녹사진기; 2가의 페노티아진기; 또는 2가의 페녹사티인 는 중수소, CN, 메틸기, 터부틸기, 페닐기, 메틸기로 치환된 페닐기, 트리플루오로메틸기, 트리플루오로메톡시기, 피리딘기, 피리미딘기, 트리아진기, 디벤조퓨란기, 디벤조티오펜기, 트리메틸실릴기, 트리페닐실릴기, 및 카바졸기로 구성되는 그룹에서 선택되는 어느 하나 이상으로 치환 또는 비치환된다.The phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrene group; Triphenylene group; Perylene group; Fluorene group; Fluoroxanthene group; Carbazole; Benzocarbazole group; Indenocarbazole; Pyridine group; Pyrimidine group; Triazine group; Dibenzofuran group; Dibenzothiophene group; Quinoline group; Quinazoline; Quinoxalin group; Phenox camera; A divalent phenothiazine group; Or divalent phenoxatiin is deuterium, CN, methyl group, terbutyl group, phenyl group, phenyl group substituted with methyl group, trifluoromethyl group, trifluoromethoxy group, pyridine group, pyrimidine group, triazine group, dibenzofuran It is substituted or unsubstituted with any one or more selected from the group consisting of a group, a dibenzothiophene group, a trimethylsilyl group, a triphenylsilyl group, and a carbazole group.
본 명세서의 일 실시상태에 있어서, 상기 화학식 2는 하기 화합물 중 어느 하나이다. In an exemplary embodiment of the present specification, Formula 2 is any one of the following compounds.
Figure PCTKR2020010175-appb-I000037
Figure PCTKR2020010175-appb-I000037
Figure PCTKR2020010175-appb-I000038
Figure PCTKR2020010175-appb-I000038
Figure PCTKR2020010175-appb-I000039
Figure PCTKR2020010175-appb-I000039
Figure PCTKR2020010175-appb-I000040
Figure PCTKR2020010175-appb-I000040
Figure PCTKR2020010175-appb-I000041
Figure PCTKR2020010175-appb-I000041
Figure PCTKR2020010175-appb-I000042
Figure PCTKR2020010175-appb-I000042
Figure PCTKR2020010175-appb-I000043
Figure PCTKR2020010175-appb-I000043
Figure PCTKR2020010175-appb-I000044
Figure PCTKR2020010175-appb-I000044
Figure PCTKR2020010175-appb-I000045
Figure PCTKR2020010175-appb-I000045
Figure PCTKR2020010175-appb-I000046
Figure PCTKR2020010175-appb-I000046
Figure PCTKR2020010175-appb-I000047
Figure PCTKR2020010175-appb-I000047
Figure PCTKR2020010175-appb-I000048
Figure PCTKR2020010175-appb-I000048
Figure PCTKR2020010175-appb-I000049
Figure PCTKR2020010175-appb-I000049
Figure PCTKR2020010175-appb-I000050
Figure PCTKR2020010175-appb-I000050
Figure PCTKR2020010175-appb-I000051
Figure PCTKR2020010175-appb-I000051
Figure PCTKR2020010175-appb-I000052
Figure PCTKR2020010175-appb-I000052
Figure PCTKR2020010175-appb-I000053
Figure PCTKR2020010175-appb-I000053
Figure PCTKR2020010175-appb-I000054
Figure PCTKR2020010175-appb-I000054
Figure PCTKR2020010175-appb-I000055
Figure PCTKR2020010175-appb-I000055
Figure PCTKR2020010175-appb-I000056
Figure PCTKR2020010175-appb-I000056
Figure PCTKR2020010175-appb-I000057
Figure PCTKR2020010175-appb-I000057
Figure PCTKR2020010175-appb-I000058
Figure PCTKR2020010175-appb-I000058
Figure PCTKR2020010175-appb-I000059
Figure PCTKR2020010175-appb-I000059
Figure PCTKR2020010175-appb-I000060
Figure PCTKR2020010175-appb-I000060
Figure PCTKR2020010175-appb-I000061
Figure PCTKR2020010175-appb-I000061
Figure PCTKR2020010175-appb-I000062
Figure PCTKR2020010175-appb-I000062
Figure PCTKR2020010175-appb-I000063
Figure PCTKR2020010175-appb-I000063
Figure PCTKR2020010175-appb-I000064
Figure PCTKR2020010175-appb-I000064
Figure PCTKR2020010175-appb-I000065
Figure PCTKR2020010175-appb-I000065
Figure PCTKR2020010175-appb-I000066
Figure PCTKR2020010175-appb-I000066
Figure PCTKR2020010175-appb-I000067
Figure PCTKR2020010175-appb-I000067
Figure PCTKR2020010175-appb-I000068
Figure PCTKR2020010175-appb-I000068
Figure PCTKR2020010175-appb-I000069
Figure PCTKR2020010175-appb-I000069
Figure PCTKR2020010175-appb-I000070
Figure PCTKR2020010175-appb-I000070
Figure PCTKR2020010175-appb-I000071
Figure PCTKR2020010175-appb-I000071
Figure PCTKR2020010175-appb-I000072
Figure PCTKR2020010175-appb-I000072
Figure PCTKR2020010175-appb-I000073
Figure PCTKR2020010175-appb-I000073
Figure PCTKR2020010175-appb-I000074
Figure PCTKR2020010175-appb-I000074
Figure PCTKR2020010175-appb-I000075
Figure PCTKR2020010175-appb-I000075
Figure PCTKR2020010175-appb-I000076
Figure PCTKR2020010175-appb-I000076
Figure PCTKR2020010175-appb-I000077
Figure PCTKR2020010175-appb-I000077
Figure PCTKR2020010175-appb-I000078
Figure PCTKR2020010175-appb-I000078
Figure PCTKR2020010175-appb-I000079
Figure PCTKR2020010175-appb-I000079
Figure PCTKR2020010175-appb-I000080
Figure PCTKR2020010175-appb-I000080
Figure PCTKR2020010175-appb-I000081
Figure PCTKR2020010175-appb-I000081
Figure PCTKR2020010175-appb-I000082
Figure PCTKR2020010175-appb-I000082
Figure PCTKR2020010175-appb-I000083
Figure PCTKR2020010175-appb-I000083
Figure PCTKR2020010175-appb-I000084
Figure PCTKR2020010175-appb-I000084
Figure PCTKR2020010175-appb-I000085
Figure PCTKR2020010175-appb-I000085
Figure PCTKR2020010175-appb-I000086
Figure PCTKR2020010175-appb-I000086
Figure PCTKR2020010175-appb-I000087
Figure PCTKR2020010175-appb-I000087
Figure PCTKR2020010175-appb-I000088
Figure PCTKR2020010175-appb-I000088
Figure PCTKR2020010175-appb-I000089
Figure PCTKR2020010175-appb-I000089
Figure PCTKR2020010175-appb-I000090
Figure PCTKR2020010175-appb-I000090
Figure PCTKR2020010175-appb-I000091
Figure PCTKR2020010175-appb-I000091
Figure PCTKR2020010175-appb-I000092
Figure PCTKR2020010175-appb-I000092
Figure PCTKR2020010175-appb-I000093
Figure PCTKR2020010175-appb-I000093
Figure PCTKR2020010175-appb-I000094
Figure PCTKR2020010175-appb-I000094
Figure PCTKR2020010175-appb-I000095
Figure PCTKR2020010175-appb-I000095
Figure PCTKR2020010175-appb-I000096
Figure PCTKR2020010175-appb-I000096
Figure PCTKR2020010175-appb-I000097
Figure PCTKR2020010175-appb-I000097
본 명세서의 일 실시상태에 있어서, 상기 화학식 2는 하기 표에 기재된 화합물 중 어느 하나이다. 하기 표에있어서, 점선은 화학식 4와 결합하는 위치이다.In an exemplary embodiment of the present specification, Chemical Formula 2 is any one of the compounds listed in the following table. In the table below, the dotted line is the position combined with Formula 4.
Figure PCTKR2020010175-appb-I000098
Figure PCTKR2020010175-appb-I000098
Figure PCTKR2020010175-appb-I000099
Figure PCTKR2020010175-appb-I000099
Figure PCTKR2020010175-appb-I000100
Figure PCTKR2020010175-appb-I000100
Figure PCTKR2020010175-appb-I000101
Figure PCTKR2020010175-appb-I000101
Figure PCTKR2020010175-appb-I000102
Figure PCTKR2020010175-appb-I000102
Figure PCTKR2020010175-appb-I000103
Figure PCTKR2020010175-appb-I000103
Figure PCTKR2020010175-appb-I000104
Figure PCTKR2020010175-appb-I000104
Figure PCTKR2020010175-appb-I000105
Figure PCTKR2020010175-appb-I000105
Figure PCTKR2020010175-appb-I000106
Figure PCTKR2020010175-appb-I000106
Figure PCTKR2020010175-appb-I000107
Figure PCTKR2020010175-appb-I000107
Figure PCTKR2020010175-appb-I000108
Figure PCTKR2020010175-appb-I000108
Figure PCTKR2020010175-appb-I000109
Figure PCTKR2020010175-appb-I000109
Figure PCTKR2020010175-appb-I000110
Figure PCTKR2020010175-appb-I000110
Figure PCTKR2020010175-appb-I000111
Figure PCTKR2020010175-appb-I000111
Figure PCTKR2020010175-appb-I000112
Figure PCTKR2020010175-appb-I000112
Figure PCTKR2020010175-appb-I000113
Figure PCTKR2020010175-appb-I000113
Figure PCTKR2020010175-appb-I000114
Figure PCTKR2020010175-appb-I000114
Figure PCTKR2020010175-appb-I000115
Figure PCTKR2020010175-appb-I000115
Figure PCTKR2020010175-appb-I000116
Figure PCTKR2020010175-appb-I000116
Figure PCTKR2020010175-appb-I000117
Figure PCTKR2020010175-appb-I000117
Figure PCTKR2020010175-appb-I000118
Figure PCTKR2020010175-appb-I000118
Figure PCTKR2020010175-appb-I000119
Figure PCTKR2020010175-appb-I000119
Figure PCTKR2020010175-appb-I000120
Figure PCTKR2020010175-appb-I000120
Figure PCTKR2020010175-appb-I000121
Figure PCTKR2020010175-appb-I000121
Figure PCTKR2020010175-appb-I000122
Figure PCTKR2020010175-appb-I000122
Figure PCTKR2020010175-appb-I000123
Figure PCTKR2020010175-appb-I000123
Figure PCTKR2020010175-appb-I000124
Figure PCTKR2020010175-appb-I000124
Figure PCTKR2020010175-appb-I000125
Figure PCTKR2020010175-appb-I000125
Figure PCTKR2020010175-appb-I000126
Figure PCTKR2020010175-appb-I000126
Figure PCTKR2020010175-appb-I000127
Figure PCTKR2020010175-appb-I000127
Figure PCTKR2020010175-appb-I000128
Figure PCTKR2020010175-appb-I000128
Figure PCTKR2020010175-appb-I000129
Figure PCTKR2020010175-appb-I000129
Figure PCTKR2020010175-appb-I000130
Figure PCTKR2020010175-appb-I000130
Figure PCTKR2020010175-appb-I000131
Figure PCTKR2020010175-appb-I000131
Figure PCTKR2020010175-appb-I000132
Figure PCTKR2020010175-appb-I000132
Figure PCTKR2020010175-appb-I000133
Figure PCTKR2020010175-appb-I000133
Figure PCTKR2020010175-appb-I000134
Figure PCTKR2020010175-appb-I000134
Figure PCTKR2020010175-appb-I000135
Figure PCTKR2020010175-appb-I000135
Figure PCTKR2020010175-appb-I000136
Figure PCTKR2020010175-appb-I000136
Figure PCTKR2020010175-appb-I000137
Figure PCTKR2020010175-appb-I000137
Figure PCTKR2020010175-appb-I000138
Figure PCTKR2020010175-appb-I000138
Figure PCTKR2020010175-appb-I000139
Figure PCTKR2020010175-appb-I000139
Figure PCTKR2020010175-appb-I000140
Figure PCTKR2020010175-appb-I000140
Figure PCTKR2020010175-appb-I000141
Figure PCTKR2020010175-appb-I000141
Figure PCTKR2020010175-appb-I000142
Figure PCTKR2020010175-appb-I000142
Figure PCTKR2020010175-appb-I000143
Figure PCTKR2020010175-appb-I000143
Figure PCTKR2020010175-appb-I000144
Figure PCTKR2020010175-appb-I000144
Figure PCTKR2020010175-appb-I000145
Figure PCTKR2020010175-appb-I000145
Figure PCTKR2020010175-appb-I000146
Figure PCTKR2020010175-appb-I000146
Figure PCTKR2020010175-appb-I000147
Figure PCTKR2020010175-appb-I000147
Figure PCTKR2020010175-appb-I000148
Figure PCTKR2020010175-appb-I000148
Figure PCTKR2020010175-appb-I000149
Figure PCTKR2020010175-appb-I000149
Figure PCTKR2020010175-appb-I000150
Figure PCTKR2020010175-appb-I000150
Figure PCTKR2020010175-appb-I000151
Figure PCTKR2020010175-appb-I000151
Figure PCTKR2020010175-appb-I000152
Figure PCTKR2020010175-appb-I000152
Figure PCTKR2020010175-appb-I000153
Figure PCTKR2020010175-appb-I000153
Figure PCTKR2020010175-appb-I000154
Figure PCTKR2020010175-appb-I000154
Figure PCTKR2020010175-appb-I000155
Figure PCTKR2020010175-appb-I000155
Figure PCTKR2020010175-appb-I000156
Figure PCTKR2020010175-appb-I000156
Figure PCTKR2020010175-appb-I000157
Figure PCTKR2020010175-appb-I000157
Figure PCTKR2020010175-appb-I000158
Figure PCTKR2020010175-appb-I000158
Figure PCTKR2020010175-appb-I000159
Figure PCTKR2020010175-appb-I000159
Figure PCTKR2020010175-appb-I000160
Figure PCTKR2020010175-appb-I000160
Figure PCTKR2020010175-appb-I000161
Figure PCTKR2020010175-appb-I000161
Figure PCTKR2020010175-appb-I000162
Figure PCTKR2020010175-appb-I000162
Figure PCTKR2020010175-appb-I000163
Figure PCTKR2020010175-appb-I000163
Figure PCTKR2020010175-appb-I000164
Figure PCTKR2020010175-appb-I000164
Figure PCTKR2020010175-appb-I000165
Figure PCTKR2020010175-appb-I000165
Figure PCTKR2020010175-appb-I000166
Figure PCTKR2020010175-appb-I000166
Figure PCTKR2020010175-appb-I000167
Figure PCTKR2020010175-appb-I000167
Figure PCTKR2020010175-appb-I000168
Figure PCTKR2020010175-appb-I000168
Figure PCTKR2020010175-appb-I000169
Figure PCTKR2020010175-appb-I000169
Figure PCTKR2020010175-appb-I000170
Figure PCTKR2020010175-appb-I000170
Figure PCTKR2020010175-appb-I000171
Figure PCTKR2020010175-appb-I000171
Figure PCTKR2020010175-appb-I000172
Figure PCTKR2020010175-appb-I000172
Figure PCTKR2020010175-appb-I000173
Figure PCTKR2020010175-appb-I000173
Figure PCTKR2020010175-appb-I000174
Figure PCTKR2020010175-appb-I000174
Figure PCTKR2020010175-appb-I000175
Figure PCTKR2020010175-appb-I000175
Figure PCTKR2020010175-appb-I000176
Figure PCTKR2020010175-appb-I000176
Figure PCTKR2020010175-appb-I000177
Figure PCTKR2020010175-appb-I000177
Figure PCTKR2020010175-appb-I000178
Figure PCTKR2020010175-appb-I000178
Figure PCTKR2020010175-appb-I000179
Figure PCTKR2020010175-appb-I000179
Figure PCTKR2020010175-appb-I000180
Figure PCTKR2020010175-appb-I000180
Figure PCTKR2020010175-appb-I000181
Figure PCTKR2020010175-appb-I000181
Figure PCTKR2020010175-appb-I000182
Figure PCTKR2020010175-appb-I000182
Figure PCTKR2020010175-appb-I000183
Figure PCTKR2020010175-appb-I000183
Figure PCTKR2020010175-appb-I000184
Figure PCTKR2020010175-appb-I000184
Figure PCTKR2020010175-appb-I000185
Figure PCTKR2020010175-appb-I000185
Figure PCTKR2020010175-appb-I000186
Figure PCTKR2020010175-appb-I000186
Figure PCTKR2020010175-appb-I000187
Figure PCTKR2020010175-appb-I000187
Figure PCTKR2020010175-appb-I000188
Figure PCTKR2020010175-appb-I000188
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 화합물은 하기 반응식 1과 같이 제조될 수 있으며, 상기 화학식 2의 화합물은 하기 반응식 2와 같이 제조될 수 있다. 하기 반응식 1 및 2는 본원 화학식 1 및 2에 해당하는 일부 화합물의 합성과정을 기재하고 있으나, 하기 반응식 1 및 2와 같은 합성과정을 이용하여 본원 화학식 1 및 2에 해당하는 다양한 화합물을 합성할 수 있고, 치환기는 당 기술분야에 알려져 있는 방법에 의하여 결합될 수 있으며, 치환기의 종류, 위치 및 개수는 당 기술분야에 알려져 있는 기술에 따라 변경될 수 있다.According to an exemplary embodiment of the present invention, the compound of Formula 1 may be prepared as shown in Scheme 1 below, and the compound of Formula 2 may be prepared as in Scheme 2 below. The following Schemes 1 and 2 describe the synthesis process of some compounds corresponding to Formulas 1 and 2 of the present application, but various compounds corresponding to Formulas 1 and 2 of the present application can be synthesized using a synthesis procedure such as Schemes 1 and 2 below. In addition, the substituents may be bonded by methods known in the art, and the type, position and number of the substituents may be changed according to techniques known in the art.
[반응식 1][Scheme 1]
Figure PCTKR2020010175-appb-I000189
Figure PCTKR2020010175-appb-I000189
[반응식 2][Scheme 2]
Figure PCTKR2020010175-appb-I000190
Figure PCTKR2020010175-appb-I000190
상기 반응식 1에 있어서, R은 코어에 연결되는 치환기를 의미하는 것으로, 본원 발명의 R1 내지 R3, B1 또는 B2 일 수 있으며, 나머지 치환기의 정의는 전술한 바와 같다. 상기 반응식 2에 있어서, 치환기의 정의는 전술한 바와 같고, 일반적인 커플링반응으로 합성이 가능하다. 예컨대 스즈키 커플링 반응 등을 이용하여 제조할 수 있다.In Scheme 1, R means a substituent connected to the core, and may be R1 to R3, B1 or B2 of the present invention, and the definition of the remaining substituents is as described above. In Scheme 2, the definition of the substituent is as described above, and can be synthesized by a general coupling reaction. For example, it can be produced using a Suzuki coupling reaction or the like.
본 명세서의 유기 발광 소자는 전술한 화학식 1로 표시되는 화합물을 이용하여 제1 유기물층을 형성하고, 전술한 화학식 2로 표시되는 화합물을 이용하여 제2 유기물층을 형성하는 것을 제외하고는, 통상의 유기 발광 소자의 제조방법 및 재료에 의하여 제조될 수 있다.In the organic light emitting device of the present specification, except for forming a first organic material layer using the compound represented by Formula 1 and forming a second organic material layer using the compound represented by Formula 2 It can be manufactured by the manufacturing method and material of the light emitting device.
상기 화학식 1로 표시되는 화합물을 포함하는 제1 유기물층 및 상기 화학식 2로 표시되는 화합물을 포함하는 제2 유기물층은, 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥 코팅, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들 만으로 한정되는 것은 아니다.The first organic material layer including the compound represented by Formula 1 and the second organic material layer including the compound represented by Formula 2 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
본 명세서의 유기 발광 소자의 유기물층은 상기 제1 유기물층 및 제2 유기물층만을 포함하는 구조로 이루어질 수도 있으나, 추가의 유기물층이 더 포함하는 구조로 이루어질 수 있다. 상기 추가의 유기물층으로서 정공주입층, 정공수송층, 정공수송 및 정공주입을 동시에 하는 층, 전자차단층, 발광층, 전자수송층, 전자주입층, 전자수송 및 전자주입을 동시에 하는 층, 정공차단층 중 1층 이상일 수 있다. 그러나, 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수 또는 더 많은 수의 유기물층을 포함할 수 있다.The organic material layer of the organic light-emitting device of the present specification may have a structure including only the first organic material layer and the second organic material layer, but may have a structure in which an additional organic material layer is further included. As the additional organic material layer, one of a hole injection layer, a hole transport layer, a layer for both hole transport and hole injection, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer for simultaneously transporting and injecting electrons, and a hole blocking layer. It can be more than one layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number or a larger number of organic material layers.
본 명세서의 일 실시상태에 따른 유기 발광 소자에서, 상기 제1 전극은 양극이고, 상기 제2 전극은 음극이며, 상기 제1 유기물층은 발광층이고, 상기 제2 유기물층은 상기 제2 전극과 상기 제1 유기물층 사이에 구비된다. 즉, 상기 제2 유기물층은 상기 음극과 상기 발광층 사이에 구비된다.본 명세서의 일 실시상태에 따른 유기 발광 소자에서, 상기 제1 유기물층은 발광층이다.In the organic light emitting device according to the exemplary embodiment of the present specification, the first electrode is an anode, the second electrode is a cathode, the first organic material layer is an emission layer, and the second organic material layer is the second electrode and the first It is provided between the organic material layers. That is, the second organic material layer is provided between the cathode and the emission layer. In the organic light emitting device according to the exemplary embodiment of the present specification, the first organic material layer is an emission layer.
본 명세서의 일 실시상태에 따른 유기 발광 소자에서, 상기 제1 유기물층은 발광층이고, 전술한 화학식 1로 표시되는 화합물은 발광층의 도펀트로 포함된다.In the organic light emitting device according to the exemplary embodiment of the present specification, the first organic material layer is an emission layer, and the compound represented by Formula 1 is included as a dopant of the emission layer.
본 명세서의 일 실시상태에 따른 유기 발광 소자에서, 상기 제1 유기물층은 발광층이고, 전술한 화학식 1로 표시되는 화합물은 발광층의 도펀트로 사용되며, 형광 호스트 또는 인광 호스트를 더 포함한다. 이때, 발광층 내의 도펀트는 호스트 100 중량부 대비 1 중량부 내지 50 중량부로 포함될 수 있으며, 바람직하게는 0.1 중량부 내지 30 중량부, 더욱 바람직하게는 1 중량부 내지 10 중량부로 포함될 수 있다. 상기 범위 내일 때, 호스트에서 도펀트로 에너지 전달이 효율적으로 일어난다.In the organic light emitting device according to the exemplary embodiment of the present specification, the first organic material layer is an emission layer, and the compound represented by Chemical Formula 1 is used as a dopant of the emission layer, and further includes a fluorescent host or a phosphorescent host. In this case, the dopant in the light emitting layer may be included in an amount of 1 to 50 parts by weight relative to 100 parts by weight of the host, preferably 0.1 to 30 parts by weight, more preferably 1 to 10 parts by weight. When within the above range, energy transfer from the host to the dopant occurs efficiently.
본 명세서의 일 실시상태에 있어서, 상기 호스트는 안트라센 유도체이다.In the exemplary embodiment of the present specification, the host is an anthracene derivative.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 2층 이상의 발광층을 포함하고, 상기 2층 이상의 발광층 중 1층은 상기 화학식 1로 표시되는 화합물을 포함한다. In the exemplary embodiment of the present specification, the organic material layer includes two or more emission layers, and one of the two or more emission layers includes the compound represented by Formula 1 above.
본 명세서의 일 실시상태에 있어서, 상기 2층 이상의 발광층의 최대 발광 피크는 서로 상이하다. 상기 화학식 1로 표시되는 화합물을 포함한 발광층은 청색을 띠며, 상기 화학식 1로 표시되는 화합물을 포함하지 않은 발광층은 당업계에 알려진 청색, 적색 또는 녹색 발광 화합물을 포함할 수 있다.In the exemplary embodiment of the present specification, the maximum emission peaks of the two or more emission layers are different from each other. The light emitting layer including the compound represented by Formula 1 has a blue color, and the light emitting layer not including the compound represented by Formula 1 may include a blue, red, or green light emitting compound known in the art.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물을 포함한 발광층은 형광 도펀트를 포함하고, 상기 화학식 1로 표시되는 화합물을 포함하지 않은 발광층은 인광 도펀트를 포함한다.In the exemplary embodiment of the present specification, the emission layer including the compound represented by Formula 1 includes a fluorescent dopant, and the emission layer not including the compound represented by Formula 1 includes a phosphorescent dopant.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물을 포함하는 발광층의 최대 발광 피크는 400 nm 내지 500 nm이다. 즉, 상기 화학식 1로 표시되는 화합물을 포함하는 발광층은 청색을 발광한다.In the exemplary embodiment of the present specification, the maximum emission peak of the emission layer including the compound represented by Formula 1 is 400 nm to 500 nm. That is, the emission layer including the compound represented by Formula 1 emits blue light.
본 명세서의 일 실시상태에 따른 유기 발광 소자의 유기물층은 2층 이상의 발광층을 포함하고, 한 층의 발광층(발광층 1)의 최대 발광 피크는 400 nm 내지 500 nm 이며, 다른 한 층의 발광층(발광층 2)의 최대 발광 피크는 510 nm 내지 580 nm; 또는 610 nm 680 nm의 최대 발광 피크를 나타낼 수 있다. 이때, 발광층 1은 상기 화학식 1로 표시되는 화합물을 포함한다.The organic material layer of the organic light emitting device according to the exemplary embodiment of the present specification includes two or more emission layers, the maximum emission peak of one emission layer (light emission layer 1) is 400 nm to 500 nm, and the emission layer of the other layer (light emission layer 2 ) The maximum emission peak of 510 nm to 580 nm; Alternatively, a maximum emission peak of 610 nm and 680 nm may be exhibited. In this case, the emission layer 1 includes the compound represented by Chemical Formula 1.
본 명세서의 일 실시상태에 따른 유기 발광 소자에서, 상기 제2 유기물층은 전자수송영역이다. 구체적으로, 상기 제2 유기물층은 정공차단층, 전자수송층, 전자주입층, 및 전자 주입 및 수송층으로 이루어진 군에서 선택된 1층 이상을 포함한다.In the organic light emitting device according to the exemplary embodiment of the present specification, the second organic material layer is an electron transport region. Specifically, the second organic material layer includes at least one layer selected from the group consisting of a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer.
또 하나의 실시상태에 따른 유기 발광 소자에서, 상기 제2 유기물층은 정공차단층, 전자수송층, 전자주입층, 및 전자 주입 및 수송층으로 이루어진 군에서 선택된 1층 또는 2층을 포함한다.In the organic light emitting device according to another exemplary embodiment, the second organic material layer includes one or two layers selected from the group consisting of a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer.
또 하나의 실시상태에 따른 유기 발광 소자에서, 상기 제2 유기물층은 정공차단층, 전자수송층, 전자주입층 또는 전자 주입 및 수송층이다.In the organic light emitting device according to another exemplary embodiment, the second organic material layer is a hole blocking layer, an electron transport layer, an electron injection layer, or an electron injection and transport layer.
또 하나의 실시상태에 따른 유기 발광 소자에서, 상기 제2 유기물층은 정공차단층이다. In the organic light emitting device according to another exemplary embodiment, the second organic material layer is a hole blocking layer.
또 하나의 실시상태에 따른 유기 발광 소자에서, 상기 제2 유기물층은 전자수송층이다.In the organic light emitting device according to another exemplary embodiment, the second organic material layer is an electron transport layer.
또 하나의 실시상태에 따른 유기 발광 소자에서, 상기 제2 유기물층은 전자 주입 및 수송층이다.In the organic light emitting device according to another exemplary embodiment, the second organic material layer is an electron injection and transport layer.
또 하나의 실시상태에 따른 유기 발광 소자에서, 상기 제2 유기물층은 정공차단층, 및 전자 주입 및 수송층을 포함한다. 이때, 정공차단층은 발광층에 인접하여 구비되고, 전자 주입 및 수송층은 음극에 인접하여 구비된다.In the organic light emitting device according to another exemplary embodiment, the second organic material layer includes a hole blocking layer and an electron injection and transport layer. In this case, the hole blocking layer is provided adjacent to the light emitting layer, and the electron injection and transport layer is provided adjacent to the cathode.
본 명세서의 일 실시상태에 있어서, 상기 제2 유기물층은 제1 유기물층에 접하여 구비된다.In the exemplary embodiment of the present specification, the second organic material layer is provided in contact with the first organic material layer.
본 명세서의 일 실시상태에 있어서, 상기 제2 유기물층은 알칼리 금속 및 알칼리토금속 중에서 선택되는 1종 또는 2종 이상의 n형 도펀트를 더 포함한다.In the exemplary embodiment of the present specification, the second organic material layer further includes one or two or more n-type dopants selected from alkali metals and alkaline earth metals.
유기 알칼리 금속 화합물 또는 유기 알칼리 토금속 화합물이 n 형 도펀트로 사용되는 경우에는 발광층으로부터 정공에 대한 안정성을 확보할 수 있어, 유기 발광 소자의 수명을 향상시킬 수 있다. 또한, 전자수송층의 전자이동도를 유기 알칼리 금속 화합물 또는 유기 알칼리 토금속 화합물의 비율을 조절하여 발광층에서 정공과 전자의 균형을 극대화시켜 발광 효율을 증가시킬 수 있다. When the organic alkali metal compound or the organic alkaline earth metal compound is used as an n-type dopant, stability against holes from the light emitting layer can be secured, thereby improving the life of the organic light emitting device. In addition, the electron mobility of the electron transport layer may be adjusted by adjusting the ratio of the organic alkali metal compound or the organic alkaline earth metal compound to maximize the balance between holes and electrons in the emission layer, thereby increasing luminous efficiency.
본 명세서에서 제2 유기물층에 사용되는 n형 도펀트로서 LiQ가 더욱 바람직하다. LiQ is more preferable as the n-type dopant used in the second organic material layer in the present specification.
상기 제2 유기물층은 화학식 2의 화합물 및 상기 n형 도펀트를 1:9 내지 9:1의 중량비로 포함할 수 있다. 바람직하게는 상기 화학식 2의 화합물과 상기 n형 도펀트를 2:8 내지 8:2로 포함할 수 있으며, 더욱 바람직하게는 3:7 내지 7:3으로 포함할 수 있다. The second organic material layer may include the compound of Formula 2 and the n-type dopant in a weight ratio of 1:9 to 9:1. Preferably, the compound of Formula 2 and the n-type dopant may be included in a ratio of 2:8 to 8:2, more preferably 3:7 to 7:3.
본 명세서의 일 실시상태에 있어서, 상기 제1 전극은 양극이고, 제2 전극은 음극이다.In the exemplary embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.
또 하나의 실시상태에 따르면, 상기 제1 전극은 음극이고, 제2 전극은 양극이다.According to another exemplary embodiment, the first electrode is a cathode, and the second electrode is an anode.
본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 기판 상에 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층된 구조(normal type)의 유기 발광 소자일 수 있다. In one embodiment of the present specification, the organic light-emitting device may be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 기판 상에 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층된 역방향 구조(inverted type)의 유기 발광 소자일 수 있다.In one embodiment of the present specification, the organic light emitting device may be an inverted type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
본 명세서의 유기 발광 소자의 구조는 도 1, 도 2 및 도 8에 나타난 것과 같은 구조를 가질 수 있으나 이에만 한정되는 것은 아니다.The structure of the organic light emitting device of the present specification may have a structure as shown in FIGS. 1, 2, and 8, but is not limited thereto.
도 1에는 기판(1), 양극(2), 정공주입층(3), 정공수송층(4), 발광층(6), 정공차단층(7), 전자 주입 및 수송층(8) 및 음극(11)이 순차적으로 적층된 유기 발광 소자의 구조가 예시 되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 발광층(6)에 포함될 수 있고, 상기 화학식 2로 표시되는 화합물은 정공차단층(7) 또는 전자 주입 및 수송층(8)에 포함될 수 있다.In FIG. 1, a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 8, and a cathode 11 The structure of the sequentially stacked organic light-emitting devices is illustrated. In such a structure, the compound represented by Formula 1 may be included in the emission layer 6, and the compound represented by Formula 2 may be included in the hole blocking layer 7 or the electron injection and transport layer 8.
도 2에는 기판(1), 양극(2), 정공주입층(3), 정공수송층(4), 전자차단층(5), 발광층(6), 전자 주입 및 수송층(8) 및 음극(11)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 발광층(6)에 포함될 수 있고, 상기 화학식 2로 표시되는 화합물은 전자 주입 및 수송층(8)에 포함될 수 있다.2, a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, an electron injection and transport layer 8, and a cathode 11 The structure of the sequentially stacked organic light emitting devices is illustrated. In such a structure, the compound represented by Formula 1 may be included in the emission layer 6, and the compound represented by Formula 2 may be included in the electron injection and transport layer 8.
도 8에는 기판(1), 양극(2), p-도핑된 정공수송층(4p), 정공수송층(4R, 4G, 4B), 발광층(6RP, 6GP, 6BF), 제1 전자수송층(9a), 제2 전자수송층(9b), 전자주입층(10), 음극(11) 및 캡핑층(14)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 발광층(6RP, 6GP, 6BF)에 포함될 수 있고, 상기 화학식 2로 표시되는 화합물은 제1 전자수송층(9a), 제2 전자수송층(9b) 및 전자주입층(10) 중 1층 이상의 층에 포함될 수 있다.8 shows a substrate 1, an anode 2, a p-doped hole transport layer 4p, a hole transport layer 4R, 4G, 4B, a light emitting layer 6RP, 6GP, 6BF, a first electron transport layer 9a, A structure of an organic light emitting diode in which the second electron transport layer 9b, the electron injection layer 10, the cathode 11, and the capping layer 14 are sequentially stacked is illustrated. In such a structure, the compound represented by Formula 1 may be included in the emission layer (6RP, 6GP, 6BF), and the compound represented by Formula 2 is a first electron transport layer (9a), a second electron transport layer (9b) And one or more layers of the electron injection layer 10.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 두 개 이상의 독립된 소자가 직렬로 연결된 탠덤 구조일 수 있다. 일 실시상태에 있어서, 상기 탠덤 구조는 각각의 유기 발광 소자가 전하생성층으로 접합된 형태일 수 있다. 탠덤 구조의 소자는 같은 밝기를 기준으로 단위 소자보다 낮은 전류에서 구동 가능하므로, 소자의 수명 특성이 크게 향상되는 장점이 있다.According to the exemplary embodiment of the present specification, the organic light emitting device may have a tandem structure in which two or more independent devices are connected in series. In one embodiment, the tandem structure may be a form in which each organic light emitting device is bonded to a charge generation layer. Since the tandem device can be driven at a lower current than the unit device based on the same brightness, there is an advantage in that the lifespan of the device is greatly improved.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 1층 이상의 발광층을 포함하는 제1 스택; 1층 이상의 발광층을 포함하는 제2 스택; 및 상기 제1 스택과 상기 제2 스택의 사이에 구비된 1층 이상의 전하생성층을 포함한다.According to an exemplary embodiment of the present specification, the organic material layer includes: a first stack including one or more emission layers; A second stack including one or more light emitting layers; And at least one charge generation layer provided between the first stack and the second stack.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 1층 이상의 발광층을 포함하는 제1 스택; 1층 이상의 발광층을 포함하는 제2 스택; 및 1층 이상의 발광층을 포함하는 제3 스택을 포함하고, 상기 제1 스택과 상기 제2 스택의 사이; 및 상기 제2 스택과 상기 제3 스택의 사이에 각각 1층 이상의 전하생성층을 포함한다.According to an exemplary embodiment of the present specification, the organic material layer includes: a first stack including one or more emission layers; A second stack including one or more light emitting layers; And a third stack including one or more emission layers, and between the first stack and the second stack; And one or more charge generation layers, respectively, between the second stack and the third stack.
본 명세서에 있어서, 전하생성층(Charge Generating layer)이란 전압을 걸면 정공과 전자가 발생하는 층을 의미한다. 상기 전하생성층은 N형 전하생성층 또는 P형 전하생성층일 수 있다. 본 명세서에서, N형 전하생성층이란 P형 전하생성층보다 양극에 가깝게 위치한 전하생성층을 의미하고, P형 전하생성층이란 N형 전하생성층보다 음극에 가깝게 위치한 전하생성층을 의미한다.In the present specification, a charge generating layer means a layer in which holes and electrons are generated when a voltage is applied. The charge generation layer may be an N-type charge generation layer or a P-type charge generation layer. In the present specification, the N-type charge generation layer refers to a charge generation layer located closer to the anode than the P-type charge generation layer, and the P-type charge generation layer refers to a charge generation layer located closer to the cathode than the N-type charge generation layer.
상기 N형 전하생성층 및 P형 전하생성층은 접하여 구비될 수 있으며, 이 경우 NP 접합을 형성한다. NP 접합에 의하여 P형 전하생성층 내에서 정공이, N형 전하생성층 내에서 전자가 용이하게 형성된다. 전자는 N형 전하생성층의 LUMO 준위를 통하여 양극 방향으로 수송되고, 정공은 P형 유기물층의 HOMO 준위를 통하여 음극 방향으로 수송된다.The N-type charge generation layer and the P-type charge generation layer may be provided in contact with each other, and in this case, an NP junction is formed. By the NP junction, holes are easily formed in the P-type charge generation layer and electrons are easily formed in the N-type charge generation layer. Electrons are transported toward the anode through the LUMO level of the N-type charge generation layer, and holes are transported toward the cathode through the HOMO level of the P-type organic material layer.
상기 제1 스택, 제2 스택 및 제3 스택은 각각 1층 이상의 발광층을 포함하며, 추가로 정공주입층, 정공수송층, 전자차단층, 전자주입층, 전자수송층, 정공차단층, 정공수송 및 정공주입을 동시에 하는 층(정공 주입 및 수송층), 및 전자수송 및 전자주입을 동시에 하는 층(전자 주입 및 수송층) 중 1층 이상의 층을 더 포함할 수 있다.Each of the first stack, the second stack, and the third stack includes one or more light emitting layers, and additionally, a hole injection layer, a hole transport layer, an electron blocking layer, an electron injection layer, an electron transport layer, a hole blocking layer, a hole transport and a hole One or more layers of a layer for simultaneous injection (hole injection and transport layer), and a layer for simultaneous electron transport and electron injection (electron injection and transport layer) may be further included.
상기 제1 스택 및 제2 스택을 포함하는 유기 발광 소자를 도 3에 예시하였다.An organic light-emitting device including the first stack and the second stack is illustrated in FIG. 3.
도 3에는 기판(1), 양극(2), 정공주입층(3), 제1 정공수송층(4a), 전자차단층(5), 제1 발광층(6a), 제1 전자수송층(9a), N형 전하생성층(12), P형 전하생성층(13), 제2 정공수송층(4b), 제2 발광층(6b), 전자 주입 및 수송층(8) 및 음극(11)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 제1 발광층(6a) 또는 제2 발광층(6b)에 포함될 수 있고, 상기 화학식 2로 표시되는 화합물은 제1 전자수송층(9a) 또는 전자 주입 및 수송층(8)에 포함될 수 있다.In FIG. 3, a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, an electron blocking layer 5, a first emission layer 6a, a first electron transport layer 9a, An N-type charge generation layer 12, a P-type charge generation layer 13, a second hole transport layer 4b, a second emission layer 6b, an electron injection and transport layer 8, and a cathode 11 are sequentially stacked. The structure of the organic light emitting device is illustrated. In such a structure, the compound represented by Formula 1 may be included in the first emission layer 6a or the second emission layer 6b, and the compound represented by Formula 2 is the first electron transport layer 9a or electron injection. And it may be included in the transport layer (8).
상기 제1 스택 내지 제 3 스택을 포함하는 유기 발광 소자를 도 4 내지 7에 예시하였다.Organic light-emitting devices including the first to third stacks are illustrated in FIGS. 4 to 7.
도 4에는 기판(1), 양극(2), 정공주입층(3), 제1 정공수송층(4a), 전자차단층(5), 제1 발광층(6a), 제1 전자수송층(9a), 제1 N형 전하생성층(12a), 제1 P형 전하생성층(13a), 제2 정공수송층(4b), 제2 발광층(6b), 제2 전자수송층(9b), 제2 N형 전하생성층(12b), 제2 P형 전하생성층(13b), 제3 정공수송층(4c), 제3 발광층(6c), 제3 전자수송층(9c) 및 음극(11)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 제1 발광층(6a), 제2 발광층(6b) 및 제3 발광층(6c)에 포함될 수 있고, 상기 화학식 2로 표시되는 화합물은 제1 전자수송층(9a), 제2 전자수송층(9b) 및 제3 전자수송층(9c) 중 1층 이상의 층에 포함될 수 있다.In FIG. 4, the substrate 1, the anode 2, the hole injection layer 3, the first hole transport layer 4a, the electron blocking layer 5, the first emission layer 6a, the first electron transport layer 9a, First N-type charge generation layer (12a), first P-type charge generation layer (13a), second hole transport layer (4b), second emission layer (6b), second electron transport layer (9b), second N-type charge An organic layer in which the generation layer 12b, the second P-type charge generation layer 13b, the third hole transport layer 4c, the third emission layer 6c, the third electron transport layer 9c, and the cathode 11 are sequentially stacked. The structure of a light emitting device is illustrated. In such a structure, the compound represented by Formula 1 may be included in the first emission layer 6a, the second emission layer 6b, and the third emission layer 6c, and the compound represented by Formula 2 is a first electron It may be included in one or more of the transport layer 9a, the second electron transport layer 9b, and the third electron transport layer 9c.
도 5에는 기판(1), 양극(2), 정공주입층(3), 제1 정공수송층(4a), 제2 정공수송층(4b), 제1 청색 형광 발광층(6BFa), 제1 전자수송층(9a), 제1 N형 전하생성층(12a), 제1 P형 전하생성층(13a), 제3 정공수송층(4c), 적색 인광 발광층(6RP), 황색 녹색 인광 발광층(6YGP), 녹색 인광 발광층(6GP), 제2 전자수송층(9b), 제2 N형 전하생성층(12b), 제2 P형 전하생성층(13b), 제4 정공수송층(4d), 제5 정공수송층(4e), 제2 청색 형광 발광층(6BFb), 제3 전자수송층(9c), 전자주입층(10), 음극(11) 및 캡핑층(14)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 제1 청색 형광 발광층(6BFa) 또는 제2 청색 형광 발광층(6BFb)에 포함될 수 있고, 상기 화학식 2로 표시되는 화합물은 제1 전자수송층(9a), 제2 전자수송층(9b), 제3 전자수송층(9c) 및 전자주입층(10) 중 1층 이상의 층에 포함될 수 있다.5 shows a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, a second hole transport layer 4b, a first blue fluorescent light emitting layer 6BFa, and a first electron transport layer. 9a), first N-type charge generation layer (12a), first P-type charge generation layer (13a), third hole transport layer (4c), red phosphorescent emission layer (6RP), yellow green phosphorescence emission layer (6YGP), green phosphorescence Light-emitting layer (6GP), second electron transport layer (9b), second N-type charge generation layer (12b), second P-type charge generation layer (13b), fourth hole transport layer (4d), fifth hole transport layer (4e) , A structure of an organic light-emitting device in which the second blue fluorescent emission layer 6BFb, the third electron transport layer 9c, the electron injection layer 10, the cathode 11 and the capping layer 14 are sequentially stacked is illustrated. In such a structure, the compound represented by Formula 1 may be included in the first blue fluorescent layer 6BFa or the second blue fluorescent layer 6BFb, and the compound represented by Formula 2 is the first electron transport layer 9a. ), the second electron transport layer 9b, the third electron transport layer 9c, and the electron injection layer 10 may be included in one or more layers.
도 6에는 기판(1), 양극(2), 정공주입층(3), 제1 정공수송층(4a), 제2 정공수송층(4b), 제1 청색 형광 발광층(6BFa), 제1 전자수송층(9a), 제1 N형 전하생성층(12a), 제1 P형 전하생성층(13a), 제3 정공수송층(4c), 적색 인광 발광층(6RP), 녹색 인광 발광층(6GP), 제2 전자수송층(9b), 제2 N형 전하생성층(12b), 제2 P형 전하생성층(13b), 제4 정공수송층(4d), 제5 정공수송층(4e), 제2 청색 형광 발광층(6BFb), 제3 전자수송층(9c), 전자주입층(10), 음극(11) 및 캡핑층(14)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 제1 청색 형광 발광층(6BFa) 또는 제2 청색 형광 발광층(6BFb)에 포함될 수 있고, 상기 화학식 2로 표시되는 화합물은 제1 전자수송층(9a), 제2 전자수송층(9b), 제3 전자수송층(9c) 및 전자주입층(10) 중 1층 이상의 층에 포함될 수 있다.6 shows a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, a second hole transport layer 4b, a first blue fluorescent light emitting layer 6BFa, and a first electron transport layer. 9a), a first N-type charge generation layer (12a), a first P-type charge generation layer (13a), a third hole transport layer (4c), a red phosphorescent layer (6RP), a green phosphorescent layer (6GP), a second electron Transport layer 9b, second N-type charge generation layer 12b, second P-type charge generation layer 13b, fourth hole transport layer 4d, fifth hole transport layer 4e, second blue fluorescent light emitting layer 6BFb ), a third electron transport layer 9c, an electron injection layer 10, a cathode 11, and a capping layer 14 are sequentially stacked. In such a structure, the compound represented by Formula 1 may be included in the first blue fluorescent layer 6BFa or the second blue fluorescent layer 6BFb, and the compound represented by Formula 2 is the first electron transport layer 9a. ), the second electron transport layer 9b, the third electron transport layer 9c, and the electron injection layer 10 may be included in one or more layers.
도 7에는 기판(1), 양극(2), 제1 p-도핑된 정공수송층(4pa), 제1 정공수송층(4a), 제2 정공수송층(4b), 제1 청색 형광 발광층(6BFa), 제1 전자수송층(9a), 제1 N형 전하생성층(12a), 제1 P형 전하생성층(13a), 제3 정공수송층(4c), 제4 정공수송층(4d), 제2 청색 형광 발광층(6BFb), 제2 전자수송층(9b), 제2 N형 전하생성층(12b), 제2 P형 전하생성층(13b), 제5 정공수송층(4e), 제6 정공수송층(4f), 제3 청색 형광 발광층(6BFc), 제3 전자수송층(9c), 전자주입층(10), 음극(11) 및 캡핑층(14)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 제1 청색 형광 발광층(6BFa), 제2 청색 형광 발광층(6BFb) 및 제3 청생 형광 발광층(6BFb) 중 1층 이상의 층에 포함될 수 있고, 상기 화학식 2로 표시되는 화합물은 제1 전자수송층(9a), 제2 전자수송층(9c), 제3 전자수송층(9c) 및 전자주입층(10) 중 1층 이상의 층에 포함될 수 있다.7 shows a substrate 1, an anode 2, a first p-doped hole transport layer 4pa, a first hole transport layer 4a, a second hole transport layer 4b, a first blue fluorescent light emitting layer 6BFa, First electron transport layer (9a), first N-type charge generation layer (12a), first P-type charge generation layer (13a), third hole transport layer (4c), fourth hole transport layer (4d), second blue fluorescence Light emitting layer (6BFb), second electron transport layer (9b), second N-type charge generation layer (12b), second P-type charge generation layer (13b), fifth hole transport layer (4e), sixth hole transport layer (4f) , A structure of an organic light-emitting device in which a third blue fluorescent emission layer 6BFc, a third electron transport layer 9c, an electron injection layer 10, a cathode 11 and a capping layer 14 are sequentially stacked is illustrated. In such a structure, the compound represented by Formula 1 may be included in one or more layers of the first blue fluorescent light emitting layer 6BFa, the second blue fluorescent light emitting layer 6BFb, and the third clean fluorescent light emitting layer 6BFb, The compound represented by Formula 2 may be included in one or more of the first electron transport layer 9a, the second electron transport layer 9c, the third electron transport layer 9c, and the electron injection layer 10.
도 9에는 기판(1), 양극(2), 정공주입층(3), 정공수송층(4), 전자차단층(5), 발광층(6), 정공차단층(7), 전자 주입 및 수송층(8) 및 음극(11)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1 또는 2로 표시되는 화합물은 발광층(6)에 포함될 수 있고, 상기 화학식 3으로 표시되는 화합물은 정공차단층(7) 또는 전자 주입 및 수송층(8)에 포함될 수 있다.9 shows a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, an electron injection and transport layer ( The structure of an organic light emitting device in which 8) and the cathode 11 are sequentially stacked is illustrated. In such a structure, the compound represented by Formula 1 or 2 may be included in the light emitting layer 6, and the compound represented by Formula 3 may be included in the hole blocking layer 7 or the electron injection and transport layer 8 have.
도 10에는 기판(1), 양극(2), 정공주입층(3), 정공수송층(4), 발광층(6), 전자 주입 및 수송층(8) 및 음극(11)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1 또는 2로 표시되는 화합물은 발광층(6)에 포함될 수 있고, 상기 화학식 3으로 표시되는 화합물은 전자 주입 및 수송층(8)에 포함될 수 있다.In FIG. 10, organic light emission in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 6, an electron injection and transport layer 8, and a cathode 11 are sequentially stacked. The structure of the device is illustrated. In such a structure, the compound represented by Formula 1 or 2 may be included in the light emitting layer 6, and the compound represented by Formula 3 may be included in the electron injection and transport layer 8.
상기 N형 전하생성층은 2,3,5,6-테트라플루오로-7,7,8,8-테트라시아노퀴노디메탄(F4TCNQ), 불소-치환된 3,4,9,10-페릴렌테트라카르복실릭 디안하이드라이드(PTCDA), 시아노-치환된 PTCDA, 나프탈렌테트라카르복실릭 디안하이드라이드(NTCDA), 불소-치환된 NTCDA, 시아노-치환된 NTCDA, 헥사아자트리페닐린 유도체 등일 수 있으나, 이에 한정되지 않는다. 일 실시상태에 있어서, 상기 N형 전하생성층은 벤조이미다조페난트리닌계 유도체와 Li의 금속을 동시에 포함할 수 있다.The N-type charge generation layer is 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), fluorine-substituted 3,4,9,10-P Lylenetetracarboxylic dianhydride (PTCDA), cyano-substituted PTCDA, naphthalenetetracarboxylic dianhydride (NTCDA), fluorine-substituted NTCDA, cyano-substituted NTCDA, hexaazatriphenylline derivative And the like, but is not limited thereto. In an exemplary embodiment, the N-type charge generation layer may include a benzoimidazophenanthrinine derivative and a metal of Li at the same time.
상기 P형 전하생성층은 아릴아민계 유도체와 시아노기를 포함하는 화합물을 동시에 포함할 수 있다.The P-type charge generation layer may simultaneously include an arylamine derivative and a compound containing a cyano group.
본 명세서의 유기 발광 소자는 유기물층이 상기 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. The organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that the organic material layer includes the compound.
상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다. 본 명세서에 따른 유기 발광 소자는 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 전술한 제1 유기물층 및 제2 유기물층을 포함하는 유기물층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수도 있다.When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials. The organic light-emitting device according to the present specification forms an anode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and after forming an organic material layer including the first organic material layer and the second organic material layer described above, It can be manufactured by depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
상기 제1 유기물층 및 제2 유기물층을 포함하는 유기물층은 정공주입층, 정공수송층, 전자 주입 및 수송층, 전자차단층, 발광층, 전자수송층, 전자주입층, 전자 주입 및 수송층, 정공차단층 등을 더 포함하는 다층 구조일 수 있다. 또한, 상기 유기물층은 다양한 고분자 소재를 사용하여 증착법이 아닌 용매 공정(solvent process), 예컨대 스핀 코팅, 딥 코팅, 닥터 블레이딩, 스크린 프린팅, 잉크젯 프린팅 또는 열 전사법 등의 방법에 의하여 더 적은 수의 층으로 제조할 수 있다.The organic material layer including the first organic material layer and the second organic material layer further includes a hole injection layer, a hole transport layer, an electron injection and transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, etc. It may be a multi-layered structure. In addition, the organic material layer is made of a variety of polymer materials, and is used in a smaller number of solvent processes, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be made in layers.
상기 양극은 정공을 주입하는 전극으로, 양극 물질로는 통상 유기물층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 본 발명에서 사용될 수 있는 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO, Indium Tin Oxide), 인듐아연 산화물(IZO, Indium Zinc Oxide)과 같은 금속 산화물; ZnO : Al 또는 SnO2 : Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.The anode is an electrode for injecting holes, and a material having a large work function is preferably used as the anode material to facilitate hole injection into an organic material layer. Specific examples of the cathode material that can be 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); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.
상기 음극은 전자를 주입하는 전극으로, 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다.The cathode is an electrode for injecting electrons, and the cathode material is usually a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multilayered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
상기 정공주입층은 양극으로부터 발광층으로 정공의 주입을 원활하게 하는 역할을 하는 층이며, 단층 또는 2층 이상의 다층 구조이다. 정공주입 물질로는 낮은 전압에서 양극으로부터 정공을 잘 주입 받을 수 있는 물질로서, 정공주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 정공주입 물질의 구체적인 예로는 금속 포피린(porphyrine), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴헥사아자트리페닐렌 계열의 유기물, 퀴나크리돈(quinacridone) 계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. 본 명세서의 일 실시상태에 있어서, 정공주입층은 2층 구조이며, 각각의 층은 서로 동일하거나 상이한 물질을 포함한다.The hole injection layer is a layer that facilitates injection of holes from the anode to the light emitting layer, and has a single layer or a multilayer structure of two or more layers. The hole injection material is a material that can well inject holes from the anode at a low voltage, and it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, etc., but are not limited thereto. In an exemplary embodiment of the present specification, the hole injection layer has a two-layer structure, and each of the layers includes the same or different materials.
상기 정공수송층은 정공의 수송을 원활하게 하는 역할을 할 수 있으며, 단층 또는 2층 이상의 다층 구조이다. 정공수송물질로는 양극이나 정공주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. 본 명세서의 일 실시상태에 있어서, 정공수송층은 2층 구조이며, 각각의 층은 서로 동일하거나 상이한 물질을 포함한다. 본 발명의 일 실시상태에 있어서, 상기 정공수송층의 물질로 아릴아민화합물을 사용한다.The hole transport layer may serve to facilitate the transport of holes, and has a single layer or a multilayer structure of two or more layers. As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and having high mobility for holes is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto. In the exemplary embodiment of the present specification, the hole transport layer has a two-layer structure, and each of the layers includes the same or different materials. In an exemplary embodiment of the present invention, an arylamine compound is used as the material of the hole transport layer.
상기 정공 주입 및 수송층은 정공수송 및 정공주입을 동시에 하는 층으로 당 기술분야에 알려져 있는 정공수송층 재료 및/또는 정공주입층 재료가 사용될 수 있다.The hole injection and transport layer is a layer that simultaneously transports and injects holes, and a hole transport layer material and/or a hole injection layer material known in the art may be used.
상기 전자 주입 및 수송층은 전자 수송 및 전자주입을 동시에 하는 층으로 당 기술분야에 알려져 있는 전자수송층 재료 및/또는 전자주입층 재료가 사용될 수 있다.The electron injection and transport layer is a layer that simultaneously transports electrons and injects electrons, and an electron transport layer material and/or an electron injection layer material known in the art may be used.
상기 정공수송층과 발광층 사이에 전자차단층이 구비될 수 있다. 상기 전자차단층은 당 기술분야에 알려져 있는 재료가 사용될 수 있다.An electron blocking layer may be provided between the hole transport layer and the emission layer. Materials known in the art may be used for the electron blocking layer.
상기 발광층은 적색, 녹색 또는 청색을 발광할 수 있으며, 인광 물질 또는 형광 물질로 이루어질 수 있다. 상기 발광 물질로는 정공수송층과 전자수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 구체적인 예로는 8-히드록시-퀴놀린 알루미늄 착물(Alq3); 카르바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자; 스피로(spiro) 화합물; 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다.The emission layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. As the light-emitting material, a material capable of emitting light in a visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency against fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.
발광층의 호스트 재료로는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 카바졸 유도체, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되지 않는다.Examples of the host material for the light emitting layer include a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
발광층이 적색 발광을 하는 경우, 발광 도펀트로는 PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum)와 같은 인광 물질이나, Alq3(tris(8-hydroxyquinolino)aluminum)와 같은 형광 물질이 사용될 수 있으나, 이에만 한정된 것은 아니다. 발광층이 녹색 발광을 하는 경우, 발광 도펀트로는 Ir(ppy)3(fac tris(2-phenylpyridine)iridium)와 같은 인광물질이나, Alq3(tris(8-hydroxyquinolino)aluminum)와 같은 형광 물질이 사용될 수 있으나, 이에만 한정된 것은 아니다. 발광층이 청색 발광을 하는 경우, 발광 도펀트로는 (4,6-F2ppy)2Irpic와 같은 인광 물질이나, spiro-DPVBi, spiro-6P, 디스틸벤젠(DSB), 디스트릴아릴렌(DSA), PFO계 고분자, PPV계 고분자와 같은 형광 물질이 사용될 수 있으나, 이에만 한정된 것은 아니다.When the emission layer emits red light, the emission dopants include PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium). ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a fluorescent material such as Alq 3 (tris(8-hydroxyquinolino)aluminum), but is not limited thereto. When the emission layer emits green light, a phosphor such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq 3 (tris(8-hydroxyquinolino)aluminum) may be used as the emission dopant. However, it is not limited thereto. When the light emitting layer emits blue light, the light emitting dopant is a phosphorescent material such as (4,6-F 2 ppy) 2 Irpic, but spiro-DPVBi, spiro-6P, distillbenzene (DSB), distrylarylene (DSA ), a fluorescent material such as a PFO-based polymer or a PPV-based polymer may be used, but is not limited thereto.
상기 전자수송층과 발광층 사이에 정공차단층이 구비될 수 있으며, 당 기술분야에 알려져 있는 재료가 사용될 수 있다.A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used.
상기 전자수송층은 전자의 수송을 원활하게 하는 역할을 한다. 전자수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al 착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다. The electron transport layer serves to facilitate the transport of electrons. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high mobility for electrons is suitable. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
상기 전자주입층은 전자의 주입을 원활하게 하는 역할을 한다. 전자주입 물질로는 전자를 수송하는 능력을 갖고, 음극으로부터의 전자주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 또한, 박막형성능력이 우수한 화합물이 바람직하다. 구체적으로는 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 함질소 5원환 유도체 등이 있으나, 이에 한정되지 않는다. The electron injection layer serves to facilitate injection of electrons. As the electron injection material, a compound having an ability to transport electrons, an electron injection effect from the cathode, an excellent electron injection effect to a light emitting layer or a light emitting material, and excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
상기 금속 착체 화합물로서는 8-하이드록시퀴놀리나토 리튬, 비스(8-하이드록시퀴놀리나토)아연, 비스(8-하이드록시퀴놀리나토)구리, 비스(8-하이드록시퀴놀리나토)망간, 트리스(8-하이드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-하이드록시퀴놀리나토)알루미늄, 트리스(8-하이드록시퀴놀리나토)갈륨, 비스(10-하이드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-하이드록시벤조[h]퀴놀리나토)아연, 비스(2-메틸-8-퀴놀리나토)클로로갈륨, 비스(2-메틸-8-퀴놀리나토)(o-크레졸라토)갈륨, 비스(2-메틸-8-퀴놀리나토)(1-나프톨라토)알루미늄, 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨 등이 있으나, 이에 한정되지 않는다.Examples of the metal complex compound include lithium 8-hydroxyquinolinato, 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)beryllium, 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, etc. It is not limited to this.
본 명세서 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
이하, 본 명세서를 구체적으로 설명하기 위해 실시예 및 비교예 등을 들어 상세하게 설명하기로 한다. 그러나, 본 명세서에 따른 실시예 및 비교예는 여러 가지 다른 형태로 변형될 수 있으며, 본 명세서의 범위가 아래에서 상술하는 실시예 및 비교예에 한정되는 것으로 해석되지 않는다. 본 명세서의 실시예 및 비교예는 당업계에서 평균적인 지식을 가진 자에게 본 명세서를 보다 완전하게 설명하기 위해 제공되는 것이다.Hereinafter, examples and comparative examples will be described in detail to describe the present specification in detail. However, the Examples and Comparative Examples according to the present specification may be modified in various other forms, and the scope of the present specification is not interpreted as being limited to the Examples and Comparative Examples described below. Examples and comparative examples in the present specification are provided to more completely describe the present specification to those of ordinary skill in the art.
제조예 1. 화합물 1의 합성Preparation Example 1. Synthesis of Compound 1
1) 중간체 1의 합성1) Synthesis of Intermediate 1
Figure PCTKR2020010175-appb-I000191
Figure PCTKR2020010175-appb-I000191
질소 분위기 하에서 1-브로모-2,3-디클로로-5-메틸벤젠 [1-bromo-2,3-dichloro-5-methylbenzene] 100 g, 아민 A-1 117 g, 소듐 터트부톡사이드 (sodium tert-butoxide) 60 g, 비스(트리-터트부틸포스핀)팔라듐(0) (Pd(P(t-Bu)3)2) 2.1 g을 톨루엔 3.0 L에 넣은 후, 120 oC에서 가열하고 2시간 동안 교반하였다. 반응 종료 후 반응액을 실온까지 냉각시키고, 물 및 NH4Cl을 가하여 분액한 후 MgSO4(무수) 처리하여 여과하였다. 여과한 용액을 감압 하에서 증류제거하고 재결정(톨루엔/헥산)으로 정제하여 중간체 1를 130 g 수득하였다. (수율 82%, Mass [M+]=441)In a nitrogen atmosphere, 1-bromo-2,3-dichloro-5-methylbenzene [1-bromo-2,3-dichloro-5-methylbenzene] 100 g, amine A-1 117 g, sodium tertbutoxide (sodium tert -butoxide) 60 g, bis(tri-tertbutylphosphine)palladium(0) (Pd(P(t-Bu) 3 ) 2 ) 2.1 g was added to 3.0 L of toluene, heated at 120 o C for 2 hours While stirring. After the reaction was completed, the reaction solution was cooled to room temperature, water and NH 4 Cl were added to separate the mixture, and then MgSO 4 (anhydrous) was treated and filtered. The filtered solution was distilled off under reduced pressure and purified with recrystallization (toluene/hexane) to obtain 130 g of Intermediate 1. (Yield 82%, Mass [M+]=441)
2) 중간체 2의 합성2) Synthesis of Intermediate 2
Figure PCTKR2020010175-appb-I000192
Figure PCTKR2020010175-appb-I000192
질소 분위기 하에서 중간체 1 30 g, 화합물 A-2 28g, 소듐 터트부톡사이드 (sodium tert-butoxide) 9.8 g, 비스(트리-터트부틸포스핀)팔라듐(0) (Pd(P(t-Bu)3)2) 0.7 g을 톨루엔 550 mL에 넣은 후, 150 oC에서 가열하고 8시간 동안 교반하였다. 반응 종료 후 반응액을 실온까지 냉각시키고, 물 및 NH4Cl을 가하여 분액한 후 MgSO4(무수) 처리하여 여과하였다. 여과한 용액을 감압 하에서 증류제거하고 재결정(톨루엔/헥산)으로 정제하여 중간체 2 를 42 g 수득하였다. (수율 76%, Mass [M+]=810)Intermediate 1 30 g, compound A-2 28 g, sodium tert-butoxide 9.8 g, bis(tri-tertbutylphosphine)palladium(0) (Pd(P(t-Bu) 3 ) ) 2 ) 0.7 g was added to 550 mL of toluene, heated at 150 o C, and stirred for 8 hours. After the reaction was completed, the reaction solution was cooled to room temperature, water and NH 4 Cl were added to separate the mixture, and then MgSO 4 (anhydrous) was treated and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain 42 g of intermediate 2. (Yield 76%, Mass [M+]=810)
3) 화합물 1의 합성3) Synthesis of compound 1
Figure PCTKR2020010175-appb-I000193
Figure PCTKR2020010175-appb-I000193
질소 분위기 하에서 0 oC로 냉각시킨 톨루엔(무수) 400 mL에 녹아있는 중간체 2 42 g이 담긴 플라스크에 터트-부틸리튬(t-BuLi(1.7M in pentane)) 122 mL을 천천히 적가 시켜준 다음 60 oC에서 3시간 동안 교반시켜 주었다. 리튬할로젠 교환반응이 완료되면, 다시 0 oC로 냉각하여 보론트리브로마이드 (BBr3) 7.5 mL를 천천히 적가시켜 준 다음 70 oC로 온도를 올리고 10시간 교반하였다. 반응 종료 후 반응액을 실온까지 냉각시키고, 물 및 NH4Cl을 가하여 분액한 후 MgSO4 (무수) 처리하여 여과하였다. 여과한 용액을 감압 하에서 증류제거하고 재결정(톨루엔/헥산)으로 정제하여 화합물 1을 9.5 g 수득하였다. (수율 23%, Mass [M+]=783)In a flask containing 42 g of intermediate 2 dissolved in 400 mL of toluene (anhydrous) cooled to 0 o C under a nitrogen atmosphere, 122 mL of tert-butyllithium (t-BuLi (1.7M in pentane)) was slowly added dropwise and then 60 It was stirred at o C for 3 hours. When the lithium halogen exchange reaction was completed, it was cooled to 0 ° C again, and 7.5 mL of boron tribromide (BBr 3 ) was slowly added dropwise, and the temperature was raised to 70 ° C and stirred for 10 hours. After the reaction was completed, the reaction solution was cooled to room temperature, water and NH 4 Cl were added to separate the mixture, and then MgSO 4 (anhydrous) was treated and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain 9.5 g of compound 1. (Yield 23%, Mass [M+]=783)
제조예 2. 화합물 2의 합성Preparation Example 2. Synthesis of Compound 2
1) 중간체 3의 합성1) Synthesis of Intermediate 3
Figure PCTKR2020010175-appb-I000194
Figure PCTKR2020010175-appb-I000194
질소 분위기 하에서 2-브로모-1,3-디아이오도-5-메틸벤젠 [2-bromo-1,3-diiodo-5-methylbenzene] 20 g, 아민 A-2 38 g, 소듐 터트부톡사이드 (sodium tert-butoxide) 14 g, 비스(트리-터트부틸포스핀)팔라듐(0) (Pd(P(t-Bu)3)2) 0.24 g을 톨루엔 450 mL에 넣은 후, 120 oC에서 가열하고 4시간 동안 교반하였다. 반응 종료 후 반응액을 실온까지 냉각시키고, 물 및 NH4Cl을 가하여 분액한 후 MgSO4 (무수) 처리하여 여과하였다. 여과한 용액을 감압 하에서 증류제거하고 재결정(톨루엔/헥산)으로 정제하여 중간체 3를 35 g 수득하였다. (수율 76%, Mass [M+]=979)Under a nitrogen atmosphere, 2-bromo-1,3-diiodo-5-methylbenzene [2-bromo-1,3-diiodo-5-methylbenzene] 20 g, amine A-2 38 g, sodium tertbutoxide (sodium tert-butoxide) 14 g, bis(tri-tertbutylphosphine)palladium(0) (Pd(P(t-Bu) 3 ) 2 ) 0.24 g was added to 450 mL of toluene, heated at 120 o C, and 4 Stir for hours. After the reaction was completed, the reaction solution was cooled to room temperature, water and NH 4 Cl were added to separate the mixture, and then MgSO 4 (anhydrous) was treated and filtered. The filtered solution was distilled off under reduced pressure and purified with recrystallization (toluene/hexane) to obtain 35 g of Intermediate 3. (Yield 76%, Mass [M+]=979)
2) 화합물 2의 합성2) Synthesis of compound 2
Figure PCTKR2020010175-appb-I000195
Figure PCTKR2020010175-appb-I000195
질소 분위기 하에서 0 oC로 냉각시킨 톨루엔 (무수) 300 mL에 녹아있는 중간체 3 35 g이 담긴 플라스크에 n-부틸리튬 (n-BuLi(2.5M in hexane)) 35 mL을 천천히 적가 시켜준 다음 60 oC에서 1시간 동안 교반시켜 주었다. 리튬할로젠 교환반응이 완료되면, 다시 0 oC로 냉각하여 보론트리브로마이드 (BBr3) 5.2 mL를 천천히 적가시켜 준 다음 70 oC로 온도를 올리고 6시간 교반하였다. 반응 종료 후 반응액을 실온까지 냉각시키고, 물 및 NH4Cl을 가하여 분액한 후 MgSO4 (무수) 처리하여 여과하였다. 여과한 용액을 감압 하에서 증류제거하고 재결정(톨루엔/헥산)으로 정제하여 화합물 2을 9.0 g 수득하였다. (수율 34%, Mass [M+]=908)In a flask containing 35 g of intermediate 3 dissolved in 300 mL of toluene (anhydrous) cooled to 0 o C under a nitrogen atmosphere, 35 mL of n-butyllithium (n-BuLi (2.5M in hexane)) was slowly added dropwise and then 60 It was stirred at o C for 1 hour. When the lithium halogen exchange reaction was completed, it was cooled to 0 ° C again, and 5.2 mL of boron tribromide (BBr 3 ) was slowly added dropwise, and the temperature was raised to 70 ° C and stirred for 6 hours. After the reaction was completed, the reaction solution was cooled to room temperature, water and NH 4 Cl were added to separate the mixture, and then MgSO 4 (anhydrous) was treated and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain 9.0 g of compound 2. (Yield 34%, Mass [M+]=908)
제조예 3. 화합물 3의 합성Preparation Example 3. Synthesis of Compound 3
1) 중간체 4 및 5의 합성1) Synthesis of intermediates 4 and 5
Figure PCTKR2020010175-appb-I000196
Figure PCTKR2020010175-appb-I000196
아민 A-1 대신 아민 A-3 18 g을 사용한 것을 제외하고 제조예 1.의 중간체 1의 제조법과 동일하게 제조하여 중간체 4 를 18 g 얻었다. (수율 75%, Mass [M+]=579)18 g of Intermediate 4 was obtained in the same manner as in Preparation Example 1, except that 18 g of amine A-3 was used instead of amine A-1. (Yield 75%, Mass [M+]=579)
또한, 중간체 1 대신 중간체 4 18 g을, 아민 A-2 대신 아민 A-1 8.8 g을 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 중간체 5를 18 g 수득하였다. (수율 70%, Mass [M+]=824)In addition, 18 g of intermediate 4 was used instead of intermediate 1, and 8.8 g of amine A-1 was used instead of amine A-2, and 18 g of intermediate 5 was obtained in the same manner as in the preparation method of intermediate 2 of Preparation Example 1. (Yield 70%, Mass [M+]=824)
2) 화합물 3의 합성2) Synthesis of compound 3
Figure PCTKR2020010175-appb-I000197
Figure PCTKR2020010175-appb-I000197
중간체 2 대신 중간체 5 18 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 3 4.0 g를 수득하였다. (수율 23%, Mass [M+]=797)In the same manner as in Preparation Example 1, except that 18 g of intermediate 5 was used instead of intermediate 2, 4.0 g of compound 3 was obtained. (Yield 23%, Mass [M+]=797)
제조예 4. 화합물 4의 합성Preparation Example 4. Synthesis of Compound 4
Figure PCTKR2020010175-appb-I000198
Figure PCTKR2020010175-appb-I000198
아민 A-2 대신 아민 A-4 9.5 g을 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 중간체 6를 14.5 g 수득하였다. (수율 78%, Mass [M+]=824) 14.5 g of Intermediate 6 was obtained in the same manner as in Preparation Example 1, except that 9.5 g of amine A-4 was used instead of amine A-2. (Yield 78%, Mass [M+]=824)
중간체 2 대신 중간체 6 14.5 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 4 3.1 g를 수득하였다. (수율 22%, Mass [M+]=797)In the same manner as in Preparation Example 1, except that 14.5 g of intermediate 6 was used instead of intermediate 2, 3.1 g of compound 4 was obtained. (Yield 22%, Mass [M+]=797)
제조예 5. 화합물 5의 합성Preparation Example 5. Synthesis of Compound 5
1) 중간체 7의 합성1) Synthesis of Intermediate 7
Figure PCTKR2020010175-appb-I000199
Figure PCTKR2020010175-appb-I000199
1-브로모-2,3-디클로로-5-메틸벤젠 [1-bromo-2,3-dichloro-5-methylbenzene] 대신 3-브로모-4,5-디클로로페놀 [3-bromo-4,5-dichlorophenol] 20 g을 사용한 것을 제외하고 제조예 1.의 중간체 1의 제조법과 동일하게 아민화반응을 한 다음, 정제 과정없이 다음 반응을 진행하였다. 3-bromo-4,5-dichlorophenol [3-bromo-4,5] instead of 1-bromo-2,3-dichloro-5-methylbenzene [1-bromo-2,3-dichloro-5-methylbenzene] -dichlorophenol] was subjected to an amination reaction in the same manner as in Preparation Example 1 of Intermediate 1 except for using 20 g, and then the next reaction was carried out without purification.
아민화 반응 생성물을 다이메틸폼아마이드 (dimethylformamide, DMF) 420 mL에 녹인 후 탄산 칼륨 (potassium carbonate) 34g 을 상온에서 추가한 다음, 0℃에서 퍼플루오로부탄설포닐 플로라이드 [perfluorobutanesulfonyl floride] 22 mL를 적가하였다. 2시간 동안 교반하여 반응 종료 후 물 400mL, 에틸아세테이트 200mL를 넣고 30분 동안 교반하였다. 유기층을 aq. NaCl을 이용하여 2차례 씻어준다. 분액한 유기층을 회수하여 Mg2SO4(anhydrous) 처리하여 여과하였다. 여과한 용액의 용매를 감압 증류 제거하고 재결정(에틸아세테이트/헥산)으로 정제하여 중간체 7를 40g을 수득하였다. (수율 77%, Mass [M+]=725)After dissolving the amination reaction product in 420 mL of dimethylformamide (DMF), 34 g of potassium carbonate was added at room temperature, and then 22 mL of perfluorobutanesulfonyl floride at 0℃ Was added dropwise. After the reaction was completed by stirring for 2 hours, 400 mL of water and 200 mL of ethyl acetate were added and stirred for 30 minutes. The organic layer to aq. Wash twice with NaCl. The separated organic layer was recovered, treated with Mg 2 SO 4 (anhydrous) and filtered. The solvent of the filtered solution was distilled off under reduced pressure and purified with recrystallization (ethyl acetate/hexane) to obtain 40 g of Intermediate 7. (Yield 77%, Mass [M+]=725)
2) 중간체 8의 합성2) Synthesis of Intermediate 8
Figure PCTKR2020010175-appb-I000200
Figure PCTKR2020010175-appb-I000200
중간체 7 20g, 아민 A-5 4.7g, 트리스(디벤질리덴아세톤)디팔라듐(0) [Palladium(0) bis(dibenzylideneacetone)] (Pd(dba)2) 0.16g, 2-Dicyclohexylphosphino-2',4′',6′'-triisopropylbiphenyl (Xphos) 0.26g, 탄산세슘 (cesium carbonate) 18g 및 자일렌 300 mL가 들어간 플라스크를 130℃에서 가열하고, 12시간 동안 교반하였다. 반응액을 실온까지 냉각시키고, sat. aq. NH4Cl 및 톨루엔을 가하여 분액한 후, 용매를 감압 하에서 증류 제거하였다. 컬럼 크로마토그래피 (ethylacetate/hexane)으로 정제하여 중간체 8 13 g을 수득하였다. (수율 77%, Mass [M+]=594)Intermediate 7 20g, amine A-5 4.7g, tris(dibenzylideneacetone)dipalladium(0) [Palladium(0) bis(dibenzylideneacetone)] (Pd(dba) 2 ) 0.16g, 2-Dicyclohexylphosphino-2', A flask containing 0.26 g of 4′′,6′′-triisopropylbiphenyl (Xphos), 18 g of cesium carbonate, and 300 mL of xylene was heated at 130° C. and stirred for 12 hours. The reaction solution was cooled to room temperature, and sat. aq. After separating by adding NH 4 Cl and toluene, the solvent was distilled off under reduced pressure. After purification by column chromatography (ethylacetate/hexane), 13 g of intermediate 8 was obtained. (Yield 77%, Mass [M+]=594)
3) 중간체 9의 합성3) Synthesis of Intermediate 9
Figure PCTKR2020010175-appb-I000201
Figure PCTKR2020010175-appb-I000201
중간체 1 대신 중간체 8 13g 을 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 중간체 9 를 17 g 수득하였다. (수율 81%, Mass [M+]=963)17 g of Intermediate 9 was obtained in the same manner as in Preparation Example 1, except that 13 g of Intermediate 8 was used instead of Intermediate 1. (Yield 81%, Mass [M+]=963)
4) 화합물 5의 합성4) Synthesis of compound 5
Figure PCTKR2020010175-appb-I000202
Figure PCTKR2020010175-appb-I000202
중간체 2 대신 중간체 9 17 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 5 3.5 g를 얻었다. (수율 21%, Mass [M+]=937)In the same manner as in Preparation Example 1, except that 17 g of Intermediate 9 was used instead of Intermediate 2, 3.5 g of Compound 5 was obtained. (Yield 21%, Mass [M+]=937)
제조예 6. 화합물 6의 합성Preparation Example 6. Synthesis of Compound 6
Figure PCTKR2020010175-appb-I000203
Figure PCTKR2020010175-appb-I000203
아민 A-2 대신 아민 A-6 11 g을 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 중간체 10를 15 g 수득하였다. (수율 75%, Mass [M+]=886) Except for using 11 g of amine A-6 instead of amine A-2, it was prepared in the same manner as in Preparation Example 1 of Intermediate 2 to obtain 15 g of Intermediate 10. (Yield 75%, Mass [M+]=886)
중간체 2 대신 중간체 10 15 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 6 3.0 g를 수득하였다. (수율 21%, Mass [M+]=860)In the same manner as in Preparation Example 1, except that 15 g of intermediate 10 was used instead of intermediate 2, 3.0 g of compound 6 was obtained. (Yield 21%, Mass [M+]=860)
제조예 7. 화합물 7의 합성Preparation Example 7. Synthesis of Compound 7
Figure PCTKR2020010175-appb-I000204
Figure PCTKR2020010175-appb-I000204
아민 A-2 대신 A-7 9.7 g을 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 중간체 11을 13 g 수득하였다. (수율 69%, Mass [M+]=830) 13 g of Intermediate 11 was obtained in the same manner as in Preparation Example 1, except that 9.7 g of A-7 was used instead of amine A-2. (Yield 69%, Mass [M+]=830)
중간체 2 대신 중간체 11 5.0 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 7 3.0 g를 수득하였다. (수율 24%, Mass [M+]=804) In the same manner as in Preparation Example 1, except that 5.0 g of Intermediate 11 was used instead of Intermediate 2, 3.0 g of Compound 7 was obtained. (Yield 24%, Mass [M+]=804)
제조예 8. 화합물 8의 합성Preparation Example 8. Synthesis of Compound 8
Figure PCTKR2020010175-appb-I000205
Figure PCTKR2020010175-appb-I000205
아민 A-2 대신 A-8 14 g을 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 중간체 12을 20 g 수득하였다. (수율 72%, Mass [M+]=820) 20 g of Intermediate 12 was obtained in the same manner as in Preparation Example 1, except that 14 g of A-8 was used instead of amine A-2. (Yield 72%, Mass [M+]=820)
중간체 2 대신 중간체 12 20 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 8 4.2 g를 수득하였다. (수율 22%, Mass [M+]=792) In the same manner as in Preparation Example 1, except that 20 g of Intermediate 12 was used instead of Intermediate 2, 4.2 g of Compound 8 was obtained. (Yield 22%, Mass [M+]=792)
제조예 9. 화합물 9의 합성Preparation Example 9. Synthesis of Compound 9
Figure PCTKR2020010175-appb-I000206
Figure PCTKR2020010175-appb-I000206
아민 A-5 대신 A-9 14 g을 사용한 것을 제외하고 제조예 5.의 중간체 8의 제조법과 동일하게 제조하여 중간체 13을 16 g 수득하였다. (수율 68%, Mass [M+]=853) 16 g of Intermediate 13 was obtained in the same manner as in Preparation Example 5, except that 14 g of A-9 was used instead of amine A-5 . (Yield 68%, Mass [M+]=853)
중간체 1 대신 중간체 13 16 g을 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 중간체 14을 18 g 수득하였다. (수율 78%, Mass [M+]=1222) 18 g of Intermediate 14 was obtained in the same manner as in Preparation Example 1, except that 16 g of Intermediate 13 was used instead of Intermediate 1. (Yield 78%, Mass [M+]=1222)
중간체 2 대신 중간체 14 18 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 9 3.6 g를 수득하였다. (수율 20%, Mass [M+]=1195) In the same manner as in Preparation Example 1, except that 18 g of Intermediate 14 was used instead of Intermediate 2, 3.6 g of Compound 9 was obtained. (Yield 20%, Mass [M+]=1195)
제조예 10. 화합물 10의 합성Preparation Example 10. Synthesis of Compound 10
Figure PCTKR2020010175-appb-I000207
Figure PCTKR2020010175-appb-I000207
아민 A-2 대신 A-10 28 g을 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 중간체 15을 43 g 수득하였다. (수율 77%, Mass [M+]=824) 43 g of intermediate 15 was obtained in the same manner as in Preparation Example 1, except that 28 g of A-10 was used instead of amine A-2. (Yield 77%, Mass [M+]=824)
중간체 2 대신 중간체 15 43 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 10 8.9 g를 수득하였다. (수율 21%, Mass [M+]=797) Except that 43 g of intermediate 15 was used instead of intermediate 2, 8.9 g of compound 10 was obtained in the same manner as in Preparation Example 1. (Yield 21%, Mass [M+]=797)
제조예 11. 화합물 11의 합성Preparation Example 11. Synthesis of Compound 11
Figure PCTKR2020010175-appb-I000208
Figure PCTKR2020010175-appb-I000208
아민 A-2 대신 A-11 29 g을 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 중간체 16을 41 g 수득하였다. (수율 72%, Mass [M+]=834) It was prepared in the same manner as in Preparation Example 1 of Intermediate 2, except that 29 g of A-11 was used instead of amine A-2 to obtain 41 g of Intermediate 16. (Yield 72%, Mass [M+]=834)
중간체 2 대신 중간체 16 41 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 11 6.7 g를 수득하였다. (수율 17%, Mass [M+]=807) 6.7 g of compound 11 was obtained in the same manner as in Preparation Example 1, except that 41 g of intermediate 16 was used instead of intermediate 2. (Yield 17%, Mass [M+]=807)
제조예 12. 화합물 12의 합성Preparation Example 12. Synthesis of Compound 12
Figure PCTKR2020010175-appb-I000209
Figure PCTKR2020010175-appb-I000209
아민 A-1 대신 A-2 17 g을 사용한 것을 제외하고 제조예 1.의 중간체 1의 제조법과 동일하게 제조하여 중간체 17을 18 g 수득하였다. (수율 76%, Mass [M+]=565) 18 g of Intermediate 17 was obtained in the same manner as in Preparation Example 1, except that 17 g of A-2 was used instead of amine A-1. (Yield 76%, Mass [M+]=565)
중간체 1 대신 중간체 17 18g, 아민 A-2 대신 A-12 17 g을 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 중간체 18을 24 g 수득하였다. (수율 72%, Mass [M+]=1046) Intermediate 18 was prepared in the same manner as in Preparation Example 1, except that 18 g of Intermediate 17 and 17 g of A-12 were used instead of Intermediate 1 and 24 g of Intermediate 18 was obtained. (Yield 72%, Mass [M+]=1046)
중간체 2 대신 중간체 18 24 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 12 5.1 g를 수득하였다. (수율 22%, Mass [M+]=1020) 5.1 g of compound 12 was obtained in the same manner as in Preparation Example 1, except that 24 g of intermediate 18 was used instead of intermediate 2. (Yield 22%, Mass [M+]=1020)
제조예 13. 화합물 13의 합성Preparation Example 13. Synthesis of Compound 13
Figure PCTKR2020010175-appb-I000210
Figure PCTKR2020010175-appb-I000210
1-브로모-2,3-디클로로-5-메틸벤젠 대신 1-브로모-2,3-디클로로-5-(메틸-d3)-벤젠 5.0g 을 사용한 것을 제외하고 제조예 1.의 중간체 1의 제조법과 동일하게 제조하여 중간체 19을 13 g 수득하였다. (수율 71%, Mass [M+]=444) Intermediate 1 of Preparation Example 1 except that 5.0 g of 1-bromo-2,3-dichloro-5-(methyl-d3)-benzene was used instead of 1-bromo-2,3-dichloro-5-methylbenzene It was prepared in the same manner as in the manufacturing method of to obtain 13 g of intermediate 19. (Yield 71%, Mass [M+]=444)
중간체 1 대신 중간체 19 13g, 아민 A-2 대신 A-13 8.8 g을 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 중간체 20을 14 g 수득하였다. (수율 67%, Mass [M+]=709) 14 g of Intermediate 20 was obtained in the same manner as in Preparation Example 1, except for using 13 g of Intermediate 19 instead of Intermediate 1 and 8.8 g of A-13 instead of amine A-2. (Yield 67%, Mass [M+]=709)
중간체 2 대신 중간체 20 14 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 13 3.4 g를 수득하였다. (수율 25%, Mass [M+]=682) In the same manner as in Preparation Example 1, except that 14 g of Intermediate 20 was used instead of Intermediate 2, 3.4 g of Compound 13 was obtained. (Yield 25%, Mass [M+]=682)
제조예 14. 화합물 14의 합성Preparation Example 14. Synthesis of Compound 14
Figure PCTKR2020010175-appb-I000211
Figure PCTKR2020010175-appb-I000211
아민 A-5 대신 A-14 6.2 g을 사용한 것을 제외하고 제조예 5.의 중간체 8의 제조법과 동일하게 제조하여 중간체 21을 13 g 수득하였다. (수율 72%, Mass [M+]=650) 13 g of Intermediate 21 was obtained in the same manner as in Preparation Example 5, except that 6.2 g of A-14 was used instead of amine A-5. (Yield 72%, Mass [M+]=650)
중간체 1 대신 중간체 21 16 g을 사용하고, 아민 A-2 대신 A-15 11g 를 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 중간체 22을 18 g 수득하였다. (수율 77%, Mass [M+]=1172) 18 g of Intermediate 22 was obtained in the same manner as in Preparation Example 1 except that 16 g of Intermediate 21 was used instead of Intermediate 1 and 11 g of A-15 was used instead of amine A-2. (Yield 77%, Mass [M+]=1172)
중간체 2 대신 중간체 22 18 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 14 4.0 g를 수득하였다. (수율 23%, Mass [M+]=1145) In the same manner as in Preparation Example 1, except that 18 g of Intermediate 22 was used instead of Intermediate 2, 4.0 g of Compound 14 was obtained. (Yield 23%, Mass [M+]=1145)
제조예 15. 화합물 15의 합성Preparation Example 15. Synthesis of Compound 15
Figure PCTKR2020010175-appb-I000212
Figure PCTKR2020010175-appb-I000212
아민 A-2 대신 A-16 9.9 g을 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 중간체 23을 14 g 수득하였다. (수율 73%, Mass [M+]=840) 14 g of Intermediate 23 was obtained in the same manner as in Preparation Example 1, except that 9.9 g of A-16 was used instead of amine A-2. (Yield 73%, Mass [M+]=840)
중간체 2 대신 중간체 23 14 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 15 2.7 g를 수득하였다. (수율 20%, Mass [M+]=814) In the same manner as in Preparation Example 1, except that 14 g of Intermediate 23 was used instead of Intermediate 2, 2.7 g of Compound 15 was obtained. (Yield 20%, Mass [M+]=814)
제조예 16. 화합물 16의 합성Preparation Example 16. Synthesis of Compound 16
Figure PCTKR2020010175-appb-I000213
Figure PCTKR2020010175-appb-I000213
아민 A-2 대신 A-17 13.3 g을 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 중간체 24을 15 g 수득하였다. (수율 67%, Mass [M+]=989) 15 g of Intermediate 24 was obtained in the same manner as in Preparation Example 1, except that 13.3 g of A-17 was used instead of amine A-2. (Yield 67%, Mass [M+]=989)
중간체 2 대신 중간체 24 15 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 16 3.0 g를 수득하였다. (수율 21%, Mass [M+]=963) In the same manner as in Preparation Example 1, except that 15 g of Intermediate 24 was used instead of Intermediate 2, 3.0 g of Compound 16 was obtained. (Yield 21%, Mass [M+]=963)
제조예 17. 화합물 17의 합성Preparation Example 17. Synthesis of Compound 17
Figure PCTKR2020010175-appb-I000214
Figure PCTKR2020010175-appb-I000214
아민 A-2 대신 A-18 17.1 g을 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 중간체 25을 20 g 수득하였다. (수율 65%, Mass [M+]=908) 20 g of Intermediate 25 was obtained in the same manner as in Preparation Example 1, except that 17.1 g of A-18 was used instead of amine A-2. (Yield 65%, Mass [M+]=908)
중간체 2 대신 중간체 25 20 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 17 4.1 g를 수득하였다. (수율 21%, Mass [M+]=882) 4.1 g of compound 17 was obtained in the same manner as in Preparation Example 1, except that 20 g of the intermediate 25 was used instead of the intermediate 2. (Yield 21%, Mass [M+]=882)
제조예 18. 화합물 18의 합성Preparation Example 18. Synthesis of Compound 18
Figure PCTKR2020010175-appb-I000215
Figure PCTKR2020010175-appb-I000215
아민 A-2 대신 A-19 12. g을 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 중간체 26을 14 g 수득하였다. (수율 66%, Mass [M+]=938) 14 g of Intermediate 26 was obtained in the same manner as in Preparation Example 1, except that 12. g of A-19 was used instead of amine A-2. (Yield 66%, Mass [M+]=938)
중간체 2 대신 중간체 26 14 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 18 2.9 g를 수득하였다. (수율 21%, Mass [M+]=912) 2.9 g of compound 18 was obtained in the same manner as in Preparation Example 1, except that 14 g of intermediate 26 was used instead of intermediate 2. (Yield 21%, Mass [M+]=912)
제조예 19. 화합물 19의 합성Preparation Example 19. Synthesis of Compound 19
Figure PCTKR2020010175-appb-I000216
Figure PCTKR2020010175-appb-I000216
아민 A-13 대신 A-20 17 g을 사용한 것을 제외하고 제조예 13.의 중간체 20의 제조법과 동일하게 제조하여 중간체 27을 19 g 수득하였다. (수율 62%, Mass [M+]=911) 19 g of Intermediate 27 was obtained in the same manner as in Preparation Example 13, except that 17 g of A-20 was used instead of amine A-13. (Yield 62%, Mass [M+]=911)
중간체 20 대신 중간체 27 19 g을 사용한 것을 제외하고 제조예 13.의 화합물 13의 제조법과 동일하게 제조하여 화합물 19 3.6 g를 수득하였다. (수율 20%, Mass [M+]=885) In the same manner as in Preparation Example 13, except that 19 g of Intermediate 27 was used instead of Intermediate 20, 3.6 g of Compound 19 was obtained. (Yield 20%, Mass [M+]=885)
제조예Manufacturing example 20. 화합물 20의 합성 20. Synthesis of compound 20
Figure PCTKR2020010175-appb-I000217
Figure PCTKR2020010175-appb-I000217
1-브로모-2,3-디클로로-5-메틸벤젠 대신 1-브로모-2,3-디클로로-5-터트부틸벤젠 10 g 을 사용한 것을 제외하고 제조예 1.의 중간체 1의 제조법과 동일하게 제조하여 중간체 28을 13 g 수득하였다. (수율 76%, Mass [M+]=483) Same as the preparation method of Intermediate 1 of Preparation Example 1. except that 10 g of 1-bromo-2,3-dichloro-5-tertbutylbenzene was used instead of 1-bromo-2,3-dichloro-5-methylbenzene To obtain 13 g of Intermediate 28. (Yield 76%, Mass [M+]=483)
중간체 1 대신 중간체 28 13g, 아민 A-2 대신 A-18 14 g을 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 중간체 29을 18 g 수득하였다. (수율 70%, Mass [M+]=950) 18 g of Intermediate 29 was obtained in the same manner as in Preparation Example 1 except that 13 g of Intermediate 28 and 14 g of A-18 were used instead of Intermediate 1 and 14 g of amine A-2 were used. (Yield 70%, Mass [M+]=950)
중간체 2 대신 중간체 29 18 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 20 3.4 g를 수득하였다. (수율 19%, Mass [M+]=924) In the same manner as in Preparation Example 1, except that 18 g of Intermediate 29 was used instead of Intermediate 2, 3.4 g of Compound 20 was obtained. (Yield 19%, Mass [M+]=924)
제조예 21. 화합물 21의 합성Preparation Example 21. Synthesis of Compound 21
Figure PCTKR2020010175-appb-I000218
Figure PCTKR2020010175-appb-I000218
A-1 대신 A-21 11g 을 사용한 것을 제외하고 제조예 1.의 중간체 1의 제조법과 동일하게 제조하여 중간체 30을 12 g 수득하였다. (수율 70%, Mass [M+]=413) 12 g of Intermediate 30 was obtained in the same manner as in Preparation Example 1, except that 11 g of A-21 was used instead of A-1. (Yield 70%, Mass [M+]=413)
중간체 1 대신 중간체 30 12g, 아민 A-2 대신 A-22 13.5 g을 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 중간체 31을 17 g 수득하였다. (수율 70%, Mass [M+]=839) 17 g of Intermediate 31 was obtained in the same manner as in Preparation Example 1 except for using 12 g of Intermediate 30 instead of Intermediate 1 and 13.5 g of A-22 instead of amine A-2. (Yield 70%, Mass [M+]=839)
중간체 2 대신 중간체 31 17 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 21 3.2 g를 수득하였다. (수율 19%, Mass [M+]=813) In the same manner as in Preparation Example 1, except that 17 g of Intermediate 31 was used instead of Intermediate 2, 3.2 g of Compound 21 was obtained. (Yield 19%, Mass [M+]=813)
제조예 22. 화합물 22의 합성Preparation Example 22. Synthesis of Compound 22
Figure PCTKR2020010175-appb-I000219
Figure PCTKR2020010175-appb-I000219
1- 브로모 -2,3- 디클로로 -5-메틸벤젠 대신 1- 브로모 -3- 클로로 -5-메틸벤젠 10g, 아민 A-1 대신 아민 A-23 22 g을 사용한 것을 제외하고 제조예 1.의 중간체 1의 제조법과 동일하게 제조하여 중간체 32을 21 g 수득하였다. (수율 74%, Mass [M+]=581) 1-bromo-2,3-dichloro-5-methyl-benzene instead of 1-bromo-3-chloro-5-methyl-benzene 10g, amine A-1 rather than an amine A-23 and 22 g Preparation Example 1, except for using It was prepared in the same manner as in the preparation method of Intermediate 1 of. To obtain 21 g of Intermediate 32. (Yield 74%, Mass [M+]=581)
질소 분위기 하에서 중간체 32 21 g, 2,4-디메틸아닐린 4.4 g, 소듐 터트부톡사이드 (sodium tert-butoxide) 5.2 g, 비스(트리-터트부틸포스핀)팔라듐(0) (Pd(P(t-Bu)3)2) 0.36 g을 톨루엔 300 mL에 넣은 후, 120 oC에서 가열하고 4시간 동안 교반하였다. 아민화 반응 종료 후, 바로 1-브로모-3-클로로벤젠 6.9 g 을 적가한 후, 2시간 동안 교반하였다. 반응 종료 후, 반응액을 실온까지 냉각시키고, 물 및 NH4Cl을 가하여 분액한 후 MgSO4 (무수) 처리하여 여과하였다. 여과한 용액을 감압 하에서 증류제거하고 재결정(톨루엔/헥산)으로 정제하여 중간체 33를 17 g 수득하였다. (수율 61%, Mass [M+]=776)In a nitrogen atmosphere, 21 g of intermediate 32, 4.4 g of 2,4-dimethylaniline, 5.2 g of sodium tert-butoxide, bis(tri-tertbutylphosphine)palladium(0) (Pd(P(t- Bu) 3 ) 2 ) 0.36 g was added to 300 mL of toluene, heated at 120 o C, and stirred for 4 hours. Immediately after completion of the amination reaction, 6.9 g of 1-bromo-3-chlorobenzene was added dropwise, followed by stirring for 2 hours. After completion of the reaction, the reaction solution was cooled to room temperature, water and NH 4 Cl were added to separate the mixture, and then MgSO 4 (anhydrous) was treated and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain 17 g of intermediate 33. (Yield 61%, Mass [M+]=776)
질소 분위기 하에서 중간체 33 17 g 을 디클로로벤젠에 녹여 보론 트리아이오다이드 (BI3) 14 g 을 적가한 후, 130 oC로 가열하여 4시간 교반하였다. 반응 종료 후 반응액을 실온까지 냉각시키고 톨루엔에 녹여 추출하여 MgSO4 (무수) 처리하여 여과하였다. 여과한 용액을 감압 하에서 증류제거하고 재결정(톨루엔/헥산)으로 정제하여 중간체 34을 5.5g 수득하였다. (수율 32%, Mass [M+]=784)In a nitrogen atmosphere, 17 g of the intermediate 33 was dissolved in dichlorobenzene, and 14 g of boron triiodide (BI 3 ) was added dropwise, followed by heating to 130 ° C. and stirring for 4 hours. After completion of the reaction, the reaction solution was cooled to room temperature, dissolved in toluene, extracted, treated with MgSO 4 (anhydrous), and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain 5.5 g of intermediate 34. (Yield 32%, Mass [M+]=784)
중간체 1 대신 중간체 34 5.5g, 아민 A-2 대신 A-5 1.2 g을 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 화합물 22을 17 g 수득하였다. (수율 81%, Mass [M+]=917) In the same manner as in Preparation Example 1, except for using 5.5 g of Intermediate 34 instead of Intermediate 1 and 1.2 g of A-5 instead of amine A-2, 17 g of Compound 22 was obtained. (Yield 81%, Mass [M+]=917)
제조예 23. 화합물 23의 합성Preparation Example 23. Synthesis of Compound 23
Figure PCTKR2020010175-appb-I000220
Figure PCTKR2020010175-appb-I000220
중간체 1 대신 중간체 8 15g, 아민 A-2 대신 A-18 13 g을 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 중간체 35을 20 g 수득하였다. (수율 75%, Mass [M+]=1061) 20 g of Intermediate 35 was obtained in the same manner as in Preparation Example 1 except for using 15 g of Intermediate 8 instead of Intermediate 1 and 13 g of A-18 instead of amine A-2. (Yield 75%, Mass [M+]=1061)
중간체 2 대신 중간체 35 20 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 23 3.5 g를 수득하였다. (수율 18%, Mass [M+]=1035) In the same manner as in Preparation Example 1, except that 20 g of the intermediate 35 was used instead of the intermediate 2, 3.5 g of the compound 23 was obtained. (Yield 18%, Mass [M+]=1035)
제조예 24. 화합물 24의 합성Preparation Example 24. Synthesis of Compound 24
Figure PCTKR2020010175-appb-I000221
Figure PCTKR2020010175-appb-I000221
질소 분위기 하에서 1.3-디브로모-2-클로로-5-아이오도벤젠 (1,3-dibromo-2-chloro-5-iodobenzene) 50.0 g를 테트라 하이드로 퓨란 (THF) 1.2 L에 녹인 후 온도를 -10℃로 유지하였다. 다음으로, 이소프로필마그네슘 클로라이드 (isopropylmagnesium chloride) 70 mL (2.0 M in THF)를 천천히 적가한 후, 0℃에서 1시간 교반하였다. 동일 온도에서 클로로트리페닐실란 37.2 g을 첨가하였다. 반응 용액을 0℃로 승온하여 약 1시간 동안 교반 후, 상온에서 추가로 12시간동안 교반하였다. 그 후, 에틸아세테이트로 희석 한 후 Saturated aq. NH4Cl을 넣어서 반응을 종료하고 유기물층을 추출하여 MgSO4 (무수) 처리하여 여과하였다. 여과한 용액을 감압 하에서 증류제거하고 재결정(톨루엔/헥산)으로 정제하여 중간체 36을 36g 수득하였다. (수율 54%, Mass [M+]=529)Dissolve 50.0 g of 1.3-dibromo-2-chloro-5-iodobenzene (1,3-dibromo-2-chloro-5-iodobenzene) in 1.2 L of tetrahydrofuran (THF) under a nitrogen atmosphere, and then reduce the temperature to − It was maintained at 10°C. Next, 70 mL (2.0 M in THF) of isopropylmagnesium chloride was slowly added dropwise, followed by stirring at 0° C. for 1 hour. At the same temperature, 37.2 g of chlorotriphenylsilane was added. The reaction solution was heated to 0° C. and stirred for about 1 hour, followed by stirring at room temperature for an additional 12 hours. After that, it was diluted with ethyl acetate and then Saturated aq. NH 4 Cl was added to terminate the reaction, and the organic layer was extracted, treated with MgSO 4 (anhydrous), and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain 36 g of Intermediate 36. (Yield 54%, Mass [M+]=529)
2-브로모-1,3-디아이오도-5-메틸벤젠 대신 중간체 36 20g, 아민 A-2 대신 아민 A-1 21 g을 사용한 것을 제외하고 제조예 2.의 중간체 3의 제조법과 동일하게 제조하여 중간체 37을 25 g 수득하였다. (수율 71%, Mass [M+]=930) Prepared in the same manner as in Preparation Example 2 of Intermediate 3, except that 20 g of intermediate 36 instead of 2-bromo-1,3-diaiodo-5-methylbenzene and 21 g of amine A-1 instead of amine A-2 were used. Thus, 25 g of intermediate 37 was obtained. (Yield 71%, Mass [M+]=930)
중간체 2 대신 중간체 37 25 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 24 4.6 g를 수득하였다. (수율 19%, Mass [M+]=904) In the same manner as in Preparation Example 1, except that 25 g of Intermediate 37 was used instead of Intermediate 2, 4.6 g of Compound 24 was obtained. (Yield 19%, Mass [M+]=904)
제조예Manufacturing example 25. 화합물 25의 합성 25. Synthesis of compound 25
Figure PCTKR2020010175-appb-I000222
Figure PCTKR2020010175-appb-I000222
2-브로모-1,3-디아이오도-5-메틸벤젠 대신 1,3-디브로모-2-클로로벤젠 15g 을 사용한 것을 제외하고 제조예 2.의 중간체 3의 제조법과 동일하게 제조하여 중간체 38을 28 g 수득하였다. (수율 75%, Mass [M+]=672)Intermediate was prepared in the same manner as in Preparation Example 2 of Intermediate 3, except that 15 g of 1,3-dibromo-2-chlorobenzene was used instead of 2-bromo-1,3-diaiodo-5-methylbenzene. 38 was obtained in 28 g. (Yield 75%, Mass [M+]=672)
중간체 2 대신 중간체 38 28 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 중간체 39 6.8 g를 수득하였다. (수율 25%, Mass [M+]=645) 6.8 g of Intermediate 39 was obtained in the same manner as in Preparation Example 1, except that 28 g of Intermediate 38 was used instead of Intermediate 2. (Yield 25%, Mass [M+]=645)
질소 분위기 하에서 중간체 39 6.8 g를 클로로포름 100 mL에 녹이고, N-브로모 숙신이미드 1.9 g를 30분에 걸쳐 첨가한 후, 4시간동안 상온에서 교반하였다. 반응 용액에 증류수를 가해 반응을 종료시키고 유기물 층을 추출하여 MgSO4 (무수) 처리하여 여과하였다. 여과한 용액을 감압 하에서 증류제거하고 컬럼크로마토그래피 (전개액: 헥산/에틸아세테이트 = 1:1(부피비))로 정제하여 중간체 40 5.2 g를 수득하였다. (수율 68%, Mass [M+]=724) 6.8 g of intermediate 39 was dissolved in 100 mL of chloroform under a nitrogen atmosphere, and 1.9 g of N -bromo succinimide was added over 30 minutes, followed by stirring at room temperature for 4 hours. Distilled water was added to the reaction solution to terminate the reaction, and the organic layer was extracted, treated with MgSO 4 (anhydrous), and filtered. The filtered solution was distilled off under reduced pressure and purified by column chromatography (developing solution: hexane/ethyl acetate = 1:1 (volume ratio)) to obtain 5.2 g of an intermediate 40. (Yield 68%, Mass [M+]=724)
질소 분위기 하에서 중간체 40 5.2 g 질소조건에서 테트라 하이드로 퓨란 (THF anhydrous) 60 mL에 녹인 후 -78℃로 온도를 낮추었다. 다음으로, n-부틸리튬 (n-BuLi (2.5M in hexane)) 5.7 mL를 천천히 적가한 후 1시간동안 교반하였다. 리튬할로젠 교환반응이 완료되면, 클로로트리메틸실란 1.2mL을 5 mL의 테트라하이드로퓨란(anhydrous)에 녹인 후 천천히 적가하였다. 반응용액을 -78℃로 유지한 상태로 약 1시간 동안 교반 후, 메틸렌 클로라이드를 이용하여 유기물층을 추출하여 MgSO4 (무수) 처리하여 여과하였다. 여과한 용액을 감압 하에서 증류제거하고 컬럼크로마토그래피 (전개액: 헥산/에틸아세테이트 = 1:1(부피비))로 정제하여 화합물 25 3.5 g를 수득하였다. (수율 68%, Mass [M+]=747).In a nitrogen atmosphere, 5.2 g of intermediate 40 was dissolved in 60 mL of tetrahydrofuran (THF anhydrous) under nitrogen conditions, and the temperature was lowered to -78°C. Next, 5.7 mL of n-butyllithium (n-BuLi (2.5M in hexane)) was slowly added dropwise, followed by stirring for 1 hour. When the lithium halogen exchange reaction was completed, 1.2 mL of chlorotrimethylsilane was dissolved in 5 mL of tetrahydrofuran (anhydrous), and then slowly added dropwise. The reaction solution was kept at -78°C and stirred for about 1 hour, and then the organic layer was extracted with methylene chloride, treated with MgSO 4 (anhydrous), and filtered. The filtered solution was distilled off under reduced pressure and purified by column chromatography (developing solution: hexane/ethyl acetate = 1:1 (volume ratio)) to obtain 3.5 g of compound 25. (Yield 68%, Mass [M+]=747).
제조예Manufacturing example 26. 화합물 26의 합성 26. Synthesis of compound 26
Figure PCTKR2020010175-appb-I000223
Figure PCTKR2020010175-appb-I000223
아민 A-2 대신 A-24 16 g을 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 중간체 41을 22 g 수득하였다. (수율 75%, Mass [M+]=860) Except that 16 g of A-24 was used instead of amine A-2, it was prepared in the same manner as in Preparation Example 1 of Intermediate 2 to obtain 22 g of Intermediate 41. (Yield 75%, Mass [M+]=860)
중간체 2 대신 중간체 41 14 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 26 4.2 g를 수득하였다. (수율 20%, Mass [M+]=833) In the same manner as in Preparation Example 1, except that 14 g of intermediate 41 was used instead of intermediate 2, 4.2 g of compound 26 was obtained. (Yield 20%, Mass [M+]=833)
제조예 27. 화합물 27의 합성Preparation Example 27. Synthesis of Compound 27
Figure PCTKR2020010175-appb-I000224
Figure PCTKR2020010175-appb-I000224
아민 A-2 대신 A-25 12.6 g을 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 중간체 42을 20 g 수득하였다. (수율 76%, Mass [M+]=773) 20 g of Intermediate 42 was obtained in the same manner as in Preparation Example 1, except that 12.6 g of A-25 was used instead of amine A-2. (Yield 76%, Mass [M+]=773)
중간체 2 대신 중간체 42 20 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 27 4.1 g를 수득하였다. (수율 21%, Mass [M+]=746) In the same manner as in Preparation Example 1, except that 20 g of Intermediate 42 was used instead of Intermediate 2, 4.1 g of Compound 27 was obtained. (Yield 21%, Mass [M+]=746)
제조예 28. 화합물 28의 합성Preparation Example 28. Synthesis of Compound 28
Figure PCTKR2020010175-appb-I000225
Figure PCTKR2020010175-appb-I000225
중간체 1 대신 중간체 21 15 g을 사용하고, 아민 A-2 대신 A-26 를 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 중간체 43을 17 g 수득하였다. (수율 67%, Mass [M+]=1106) 17 g of Intermediate 43 was obtained in the same manner as in Preparation Example 1, except that 15 g of Intermediate 21 was used instead of Intermediate 1 and A-26 was used instead of amine A-2. (Yield 67%, Mass [M+]=1106)
중간체 2 대신 중간체 43 17 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 28 3.6 g를 수득하였다. (수율 22%, Mass [M+]=1079) In the same manner as in Preparation Example 1, except that 17 g of Intermediate 43 was used instead of Intermediate 2, 3.6 g of Compound 28 was obtained. (Yield 22%, Mass [M+]=1079)
제조예 29. 화합물 29의 합성Preparation Example 29. Synthesis of Compound 29
Figure PCTKR2020010175-appb-I000226
Figure PCTKR2020010175-appb-I000226
A-1 대신 A-27 12.8g 을 사용한 것을 제외하고 제조예 1.의 중간체 1의 제조법과 동일하게 제조하여 중간체 44을 16 g 수득하였다. (수율 70%, Mass [M+]=365) 16 g of Intermediate 44 was obtained in the same manner as in Preparation Example 1, except that 12.8 g of A-27 was used instead of A-1. (Yield 70%, Mass [M+]=365)
중간체 1 대신 중간체 44 16g, 아민 A-2 대신 A-18 22 g을 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 중간체 45을 26 g 수득하였다. (수율 71%, Mass [M+]=832) In the same manner as in Preparation Example 1, except that 16 g of Intermediate 44 and 22 g of A-18 were used instead of Intermediate 1, 26 g of Intermediate 45 was obtained. (Yield 71%, Mass [M+]=832)
중간체 2 대신 중간체 45 17 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 29 4.1 g를 수득하였다. (수율 16%, Mass [M+]=805)In the same manner as in Preparation Example 1, except that 17 g of Intermediate 45 was used instead of Intermediate 2, 4.1 g of Compound 29 was obtained. (Yield 16%, Mass [M+]=805)
제조예 30. 화합물 30의 합성Preparation Example 30. Synthesis of Compound 30
Figure PCTKR2020010175-appb-I000227
Figure PCTKR2020010175-appb-I000227
아민 A-2 대신 A-28 17.8 g을 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 중간체 46을 22 g 수득하였다. (수율 70%, Mass [M+]=926) Except that 17.8 g of A-28 was used instead of amine A-2, it was prepared in the same manner as in Preparation Example 1 of Intermediate 2 to obtain 22 g of Intermediate 46. (Yield 70%, Mass [M+]=926)
중간체 2 대신 중간체 46 22 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 30 4.3 g를 수득하였다. (수율 20%, Mass [M+]=900) In the same manner as in Preparation Example 1, except that 22 g of intermediate 46 was used instead of intermediate 2, 4.3 g of compound 30 was obtained. (Yield 20%, Mass [M+]=900)
제조예 31. 화합물 31의 합성Preparation Example 31. Synthesis of Compound 31
Figure PCTKR2020010175-appb-I000228
Figure PCTKR2020010175-appb-I000228
중간체 7 20 g, 2-플루오로보로닉산 4.6 g, 인산 칼륨 [potassium phosphate] 11.7 g 1,4-디옥산 220 mL와 물 50 mL를 넣은 후 테트라키스(트리페닐포스핀)팔라듐(0)[tetrakis(triphenylhosphine)palladium(0)] Pd(PPh3)4 0.48 g을 첨가한 후, 16시간 동안 가열 교반하였다. 반응 종료 후 반응액을 실온까지 냉각시키고, 유기용매를 제거하고 톨루엔에 녹여 추출한 후, 유기용매를 MgSO4(anhydrous) 처리하여 여과하였다. 여과한 용액을 감압하에서 증류제거하고 재결정(toluene/hexane)으로 정제하여 중간체 47 9.5 g 수득하였다. (수율 66%, Mass [M+]=521)Intermediate 7 20 g, 2-fluoroboronic acid 4.6 g, potassium phosphate 11.7 g 1,4-dioxane 220 mL and 50 mL of water were added, and tetrakis(triphenylphosphine)palladium(0)[ After adding 0.48 g of tetrakis(triphenylhosphine)palladium(0)] Pd(PPh 3 ) 4 , it was heated and stirred for 16 hours. After the reaction was completed, the reaction solution was cooled to room temperature, the organic solvent was removed, dissolved in toluene, extracted, and the organic solvent was treated with MgSO 4 (anhydrous) and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain 9.5 g of intermediate 47. (Yield 66%, Mass [M+]=521)
아민 A-2 대신 A-29 9.1 g을 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 중간체 48을 14 g 수득하였다. (수율 78%, Mass [M+]=982) 14 g of Intermediate 48 was obtained in the same manner as in Preparation Example 1, except that 9.1 g of A-29 was used instead of amine A-2. (Yield 78%, Mass [M+]=982)
중간체 2 대신 중간체 48 14 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 31 3.2 g를 수득하였다. (수율 23%, Mass [M+]=956) In the same manner as in Preparation Example 1, except that 14 g of Intermediate 48 was used instead of Intermediate 2, 3.2 g of Compound 31 was obtained. (Yield 23%, Mass [M+]=956)
제조예 32. 화합물 32의 합성Preparation Example 32. Synthesis of Compound 32
Figure PCTKR2020010175-appb-I000229
Figure PCTKR2020010175-appb-I000229
아민 A-5 대신 A-30 4.6 g을 사용한 것을 제외하고 제조예 5.의 중간체 8의 제조법과 동일하게 제조하여 중간체 49을 12 g 수득하였다. (수율 73%, Mass [M+]=592) 12 g of Intermediate 49 was obtained in the same manner as in Preparation Example 5, except that 4.6 g of A-30 was used instead of amine A-5. (Yield 73%, Mass [M+]=592)
중간체 1 대신 중간체 49 12 g을 사용하고, 아민 A-2 대신 A-31 7.0g 를 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 중간체 50을 13 g 수득하였다. (수율 71%, Mass [M+]=899) 13 g of Intermediate 50 was obtained in the same manner as in Preparation Example 1 except that 12 g of Intermediate 49 was used instead of Intermediate 1, and 7.0 g of A-31 was used instead of amine A-2. (Yield 71%, Mass [M+]=899)
중간체 2 대신 중간체 50 13 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 32 2.9 g를 수득하였다. (수율 23%, Mass [M+]=873) 2.9 g of compound 32 was obtained in the same manner as in Preparation Example 1, except that 13 g of intermediate 50 was used instead of intermediate 2. (Yield 23%, Mass [M+]=873)
제조예 33. 화합물 33의 합성Preparation Example 33. Synthesis of Compound 33
Figure PCTKR2020010175-appb-I000230
Figure PCTKR2020010175-appb-I000230
아민 A-5 대신 A-31 8.7 g을 사용한 것을 제외하고 제조예 5.의 중간체 8의 제조법과 동일하게 제조하여 중간체 51을 14 g 수득하였다. (수율 69%, Mass [M+]=739) 14 g of intermediate 51 was obtained in the same manner as in Preparation Example 5, except that 8.7 g of A-31 was used instead of amine A-5. (Yield 69%, Mass [M+]=739)
중간체 1 대신 중간체 51 14 g을 사용한 것을 제외하고 제조예 1.의 중간체 2의 제조법과 동일하게 제조하여 중간체 52을 16 g 수득하였다. (수율 76%, Mass [M+]=1108) 16 g of Intermediate 52 was obtained in the same manner as in Preparation Example 1, except that 14 g of Intermediate 51 was used instead of Intermediate 1. (Yield 76%, Mass [M+]=1108)
중간체 2 대신 중간체 52 16 g을 사용한 것을 제외하고 제조예 1.의 화합물 1의 제조법과 동일하게 제조하여 화합물 33 3.4 g를 수득하였다. (수율 22%, Mass [M+]=1081) Except that 16 g of intermediate 52 was used instead of intermediate 2, 3.4 g of compound 33 was obtained in the same manner as in Preparation Example 1. (Yield 22%, Mass [M+]=1081)
제조예Manufacturing example 34: 화합물 E1의 제조 34: Preparation of compound E1
Figure PCTKR2020010175-appb-I000231
Figure PCTKR2020010175-appb-I000231
스파이로[플로렌-9,9'-싸이오잔텐]-1-일보로닉엑시드 10g과 상기 화합물 2-([1,1'-바이페닐]-4-일)-4-클로로-6-페닐-1,3,5-트리아진 8.8 g을 테트라하이드로퓨란 (200 mL)에 완전히 녹인 후, 탄산칼륨 10.6 g을 물 60 mL에 용해시켜 첨가하였다. 테트라키스트리페닐-포스피노팔라듐 0.9g을 넣은 후, 8 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 반응을 종결한 후, 탄산칼륨 용액을 제거하여 흰색 고체를 여과하였다. 여과된 흰색 고체를 테트라하이드로퓨란 및 에틸아세테이트로 세척하여 화합물 E1을 14 g (수율 84 %)제조하였다. MS [M+H]+ = 657Spiro[floren-9,9'-thioxanthene]-1-ylboronic acid 10g and the compound 2-([1,1'-biphenyl]-4-yl)-4-chloro-6- After 8.8 g of phenyl-1,3,5-triazine was completely dissolved in tetrahydrofuran (200 mL), 10.6 g of potassium carbonate was dissolved in 60 mL of water and added. After adding 0.9 g of tetrakistriphenyl-phosphinopalladium, the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and a white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate to prepare 14 g (yield 84%) of compound E1. MS [M+H] + = 657
제조예Manufacturing example 35: 화합물 E2의 제조 35: Preparation of compound E2
Figure PCTKR2020010175-appb-I000232
Figure PCTKR2020010175-appb-I000232
스파이로[플로렌-9,9'-잔텐]-2-일보로닉엑시드 10g과 상기 화합물 2-클로로-4,6-di(나프탈렌-1-일)-1,3,5-트리아진 9.8 g을 테트라하이드로퓨란 (200 mL)에 완전히 녹인 후, 탄산칼륨 11.1 g을 물 60 mL에 용해시켜 첨가하였다. 테트라키스트리페닐-포스피노팔라듐 0.9g을 넣은 후, 8 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 반응을 종결한 후, 탄산칼륨 용액을 제거하여 흰색 고체를 여과하였다. 여과된 흰색 고체를 테트라하이드로퓨란 및 에틸아세테이트로 세척하여 화합물 E2를 15 g (수율 85 %)제조하였다. MS [M+H]+ = 665Spiro[floren-9,9'-xanthene]-2-ylboronic acid 10g and the compound 2-chloro-4,6-di(naphthalen-1-yl)-1,3,5-triazine 9.8 After g was completely dissolved in tetrahydrofuran (200 mL), 11.1 g of potassium carbonate was dissolved in 60 mL of water and added. After adding 0.9 g of tetrakistriphenyl-phosphinopalladium, the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and a white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate to prepare 15 g (yield 85%) of compound E2. MS [M+H] + = 665
제조예Manufacturing example 36: 화합물 E3의 제조 36: Preparation of compound E3
Figure PCTKR2020010175-appb-I000233
Figure PCTKR2020010175-appb-I000233
스파이로[플로렌-9,9'-잔텐]-2-일보로닉엑시드 10g과 상기 화합물 4-(4-클로로페닐)-2-페닐퀴나졸린 8.5 g을 테트라하이드로퓨란 (200 mL)에 완전히 녹인 후, 탄산칼륨 11.1 g을 물 60 mL에 용해시켜 첨가하였다. 테트라키스트리페닐-포스피노팔라듐 0.9g을 넣은 후, 8 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 반응을 종결한 후, 탄산칼륨 용액을 제거하여 흰색 고체를 여과하였다. 여과된 흰색 고체를 테트라하이드로퓨란 및 에틸아세테이트로 세척하여 화합물 E3을 14 g (수율 86 %)제조하였다. MS [M+H]+ = 61410 g of spiro[floren-9,9'-xanthene]-2-ylboronic acid and 8.5 g of the compound 4-(4-chlorophenyl)-2-phenylquinazoline were completely in tetrahydrofuran (200 mL). After dissolving, 11.1 g of potassium carbonate was dissolved in 60 mL of water and added. After adding 0.9 g of tetrakistriphenyl-phosphinopalladium, the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and a white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate to prepare 14 g (86% yield) of compound E3. MS [M+H] + = 614
제조예Manufacturing example 37: 화합물 E4의 제조 37: Preparation of compound E4
Figure PCTKR2020010175-appb-I000234
Figure PCTKR2020010175-appb-I000234
스파이로[플로렌-9,9'-싸이오잔텐]-3-일보로닉엑시드 10g과 상기 화합물 4-(4-클로로페닐)-2,6-다이페닐피리미딘 8.5 g을 테트라하이드로퓨란 (200 mL)에 완전히 녹인 후, 탄산칼륨 10.6 g을 물 60 mL에 용해시켜 첨가하였다. 테트라키스트리페닐-포스피노팔라듐 0.9g을 넣은 후, 8 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 반응을 종결한 후, 탄산칼륨 용액을 제거하여 흰색 고체를 여과하였다. 여과된 흰색 고체를 테트라하이드로퓨란 및 에틸아세테이트로 세척하여 화합물 E4를 13g (수율 78 %)제조하였다. MS [M+H]+ = 65610 g of spiro[floren-9,9'-thioxanthene]-3-ylboronic acid and 8.5 g of the compound 4-(4-chlorophenyl)-2,6-diphenylpyrimidine were added to tetrahydrofuran ( 200 mL), then 10.6 g of potassium carbonate was dissolved in 60 mL of water and added. After adding 0.9 g of tetrakistriphenyl-phosphinopalladium, the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and a white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate to prepare 13 g of compound E4 (yield 78%). MS [M+H] + = 656
제조예Manufacturing example 38: 화합물 E5의 제조 38: Preparation of compound E5
Figure PCTKR2020010175-appb-I000235
Figure PCTKR2020010175-appb-I000235
스파이로[플로렌-9,9'-싸이오잔텐]-4-일보로닉엑시드 10g과 상기 화합물 2-클로로-4,6-다이페닐-1,3,5-트리아진 6.8g을 테트라 하이드로퓨란 (200 mL)에 완전히 녹인 후, 탄산칼륨 10.6 g을 물 60 mL에 용해시켜 첨가하였다. 테트라키스트리페닐-포스피노팔라듐 0.9g을 넣은 후, 8 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 반응을 종결한 후, 탄산칼륨 용액을 제거하여 흰색 고체를 여과하였다. 여과된 흰색 고체를 테트라하이드로퓨란 및 에틸아세테이트로 세척하여 화합물 E5를 11g (수율 77 %)제조하였다. MS [M+H]+ = 56510 g of spiro[floren-9,9'-thioxanthene]-4-ylboronic acid and 6.8 g of the compound 2-chloro-4,6-diphenyl-1,3,5-triazine were added to tetrahydro After completely dissolved in furan (200 mL), 10.6 g of potassium carbonate was dissolved in 60 mL of water and added. After adding 0.9 g of tetrakistriphenyl-phosphinopalladium, the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and a white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate to prepare 11 g of compound E5 (yield 77%). MS [M+H] + = 565
제조예Manufacturing example 39: 화합물 E6의 제조 39: Preparation of compound E6
Figure PCTKR2020010175-appb-I000236
Figure PCTKR2020010175-appb-I000236
스파이로[다이벤조[c,h]잔텐-7,9'-플로렌]-2'-일보로닉 엑시드 10g과 상기 화합물 2-클로로-4,6-다이페닐-1,3,5-트리아진 5.6g을 테트라 하이드로퓨란 (200 mL)에 완전히 녹인 후, 탄산칼륨 8.7 g을 물 60 mL에 용해시켜 첨가하였다. 테트라키스트리페닐-포스피노팔라듐 0.8g을 넣은 후, 8 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 반응을 종결한 후, 탄산칼륨 용액을 제거하여 흰색 고체를 여과하였다. 여과된 흰색 고체를 테트라하이드로퓨란 및 에틸아세테이트로 세척하여 화합물 E6을 11g (수율 79 %)제조하였다. MS [M+H]+ = 665Spiro[dibenzo[c,h]xanthene-7,9'-florene]-2'-ylboronic acid 10g and the compound 2-chloro-4,6-diphenyl-1,3,5-tri After 5.6 g of azine was completely dissolved in tetrahydrofuran (200 mL), 8.7 g of potassium carbonate was dissolved in 60 mL of water and added. After adding 0.8 g of tetrakistriphenyl-phosphinopalladium, the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and a white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate to prepare 11 g (79% yield) of compound E6. MS [M+H] + = 665
제조예Manufacturing example 40: 화합물 E7의 제조 40: Preparation of compound E7
Figure PCTKR2020010175-appb-I000237
Figure PCTKR2020010175-appb-I000237
스파이로[플로렌-9,9'-잔텐]-2-일보로닉엑시드 10g과 상기 화합물 9-(4-(6-클로로-2-페닐피리미딘-4-일)페닐)-9H-카바졸 11.5g을 테트라 하이드로퓨란 (200 mL)에 완전히 녹인 후, 탄산칼륨 11g을 물 60 mL에 용해시켜 첨가하였다. 테트라키스트리페닐-포스피노팔라듐 0.9g을 넣은 후, 8 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 반응을 종결한 후, 탄산칼륨 용액을 제거하여 흰색 고체를 여과하였다. 여과된 흰색 고체를 테트라하이드로퓨란 및 에틸아세테이트로 세척하여 화합물 E7을 14g (수율 72 %)제조하였다. MS [M+H]+ = 729Spiro[floren-9,9'-xanthene]-2-ylboronic acid 10g and the compound 9-(4-(6-chloro-2-phenylpyrimidin-4-yl)phenyl)-9H-carba After completely dissolving 11.5 g of sol in tetrahydrofuran (200 mL), 11 g of potassium carbonate was dissolved in 60 mL of water and added. After adding 0.9 g of tetrakistriphenyl-phosphinopalladium, the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and a white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate to prepare 14 g (72% yield) of compound E7. MS [M+H] + = 729
제조예Manufacturing example 41: 화합물 E8의 제조 41: Preparation of compound E8
Figure PCTKR2020010175-appb-I000238
Figure PCTKR2020010175-appb-I000238
스파이로[플로렌-9,9'-잔텐]-2-일보로닉엑시드 10g과 상기 화합물 2-클로로-4-페닐-6-(4'-(피리딘-4-일)-[1,1'-바이페닐]-3-일)-1,3,5-트리아진 11.2g을 테트라 하이드로퓨란 (200 mL)에 완전히 녹인 후, 탄산칼륨 11g을 물 60 mL에 용해시켜 첨가하였다. 테트라키스트리페닐-포스피노팔라듐 0.9g을 넣은 후, 8 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 반응을 종결한 후, 탄산칼륨 용액을 제거하여 흰색 고체를 여과하였다. 여과된 흰색 고체를 테트라하이드로퓨란 및 에틸아세테이트로 세척하여 화합물 E8을 14g (수율 73 %) 제조하였다. MS [M+H]+ = 718Spiro[floren-9,9'-xanthene]-2-ylboronic acid 10g and the compound 2-chloro-4-phenyl-6-(4'-(pyridin-4-yl)-[1,1] After completely dissolving 11.2 g of'-biphenyl]-3-yl)-1,3,5-triazine in tetrahydrofuran (200 mL), 11 g of potassium carbonate was dissolved in 60 mL of water and added. After adding 0.9 g of tetrakistriphenyl-phosphinopalladium, the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and a white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate to prepare 14 g (73% yield) of compound E8. MS [M+H] + = 718
제조예Manufacturing example 429: 화합물 E9의 제조 429: Preparation of compound E9
Figure PCTKR2020010175-appb-I000239
Figure PCTKR2020010175-appb-I000239
(3'-(2,6-다이페닐피리미딘-4-일)스파이로[플로렌-9,9'-잔텐]-2-일)보로닉 엑시드 10g과 상기 화합물 4-클로로-2,6-다이페닐피리미딘 4.4g을 테트라 하이드로퓨란 (200 mL)에 완전히 녹인 후, 탄산칼륨 6.9g을 물 60 mL에 용해시켜 첨가하였다. 테트라키스트리페닐-포스피노팔라듐 0.6g을 넣은 후, 8 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 반응을 종결한 후, 탄산칼륨 용액을 제거하여 흰색 고체를 여과하였다. 여과된 흰색 고체를 테트라하이드로퓨란 및 에틸아세테이트로 세척하여 화합물 E9를 10g (수율 76 %)제조하였다. MS [M+H]+ = 794(3'-(2,6-diphenylpyrimidin-4-yl)spiro[floren-9,9'-xanthene]-2-yl) 10 g of boronic acid and the compound 4-chloro-2,6 -After 4.4 g of diphenylpyrimidine was completely dissolved in tetrahydrofuran (200 mL), 6.9 g of potassium carbonate was dissolved in 60 mL of water and added. After adding 0.6 g of tetrakistriphenyl-phosphinopalladium, the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and a white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate to prepare 10 g of compound E9 (yield 76%). MS [M+H] + = 794
제조예Manufacturing example 43: 화합물 E10의 제조 43: Preparation of compound E10
Figure PCTKR2020010175-appb-I000240
Figure PCTKR2020010175-appb-I000240
스파이로[플로렌-9,9'-잔텐]-2'-일보로닉엑시드 10g과 상기 화합물 4-클로로-2,6-다이페닐피리미딘 11.5g을 테트라 하이드로퓨란 (200 mL)에 완전히 녹인 후, 탄산칼륨 11g을 물 60 mL에 용해시켜 첨가하였다. 테트라키스트리페닐-포스피노팔라듐 0.9g을 넣은 후, 8 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 반응을 종결한 후, 탄산칼륨 용액을 제거하여 흰색 고체를 여과하였다. 여과된 흰색 고체를 테트라하이드로퓨란 및 에틸아세테이트로 세척하여 화합물 E10을 16g (수율 82 %)제조하였다. MS [M+H]+ = 731Spiro[floren-9,9'-xanthene]-2'-ylboronic acid 10g and the compound 4-chloro-2,6-diphenylpyrimidine 11.5g completely dissolved in tetrahydrofuran (200 mL) Then, 11 g of potassium carbonate was dissolved in 60 mL of water and added. After adding 0.9 g of tetrakistriphenyl-phosphinopalladium, the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and a white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate to prepare 16 g (82% yield) of compound E10. MS [M+H] + = 731
제조예Manufacturing example 44: 화합물 E11의 제조 44: Preparation of compound E11
Figure PCTKR2020010175-appb-I000241
Figure PCTKR2020010175-appb-I000241
스파이로[플로렌-9,9'-잔텐]-3'-일보로닉엑시드 10g과 상기 화합물 2-(2-브로모나프탈렌-1-일)-4,6-다이페닐-1,3,5-트리아진 11.7g을 테트라 하이드로퓨란 (200 mL)에 완전히 녹인 후, 탄산칼륨 11g을 물 60 mL에 용해시켜 첨가하였다. 테트라키스트리페닐-포스피노팔라듐 0.9g을 넣은 후, 8 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 반응을 종결한 후, 탄산칼륨 용액을 제거하여 흰색 고체를 여과하였다. 여과된 흰색 고체를 테트라하이드로퓨란 및 에틸아세테이트로 세척하여 화합물 E11을 15g (수율 82 %)제조하였다. MS [M+H]+ = 691Spiro[floren-9,9'-xanthene]-3'-ylboronic acid 10g and the compound 2-(2-bromonaphthalen-1-yl)-4,6-diphenyl-1,3, After 11.7 g of 5-triazine was completely dissolved in tetrahydrofuran (200 mL), 11 g of potassium carbonate was dissolved in 60 mL of water and added. After adding 0.9 g of tetrakistriphenyl-phosphinopalladium, the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and a white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate to prepare 15 g (82% yield) of compound E11. MS [M+H] + = 691
제조예Manufacturing example 45: 화합물 E12의 제조 45: Preparation of compound E12
Figure PCTKR2020010175-appb-I000242
Figure PCTKR2020010175-appb-I000242
스파이로[플로렌-9,9'-잔텐]-3'-일보로닉엑시드 10g과 상기 화합물 2-(6-클로로피리딘-3-일)-4,6-다이페닐-1,3,5-트리아진 9.2g을 테트라 하이드로퓨란 (200 mL)에 완전히 녹인 후, 탄산칼륨 11g을 물 60 mL에 용해시켜 첨가하였다. 테트라키스트리페닐-포스피노팔라듐 0.9g을 넣은 후, 8 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 반응을 종결한 후, 탄산칼륨 용액을 제거하여 흰색 고체를 여과하였다. 여과된 흰색 고체를 테트라하이드로퓨란 및 에틸아세테이트로 세척하여 화합물 E12를 13g (수율 76 %)제조하였다. MS [M+H]+ = 642Spiro[floren-9,9'-xanthene]-3'-ylboronic acid 10g and the compound 2-(6-chloropyridin-3-yl)-4,6-diphenyl-1,3,5 -After 9.2 g of triazine was completely dissolved in tetrahydrofuran (200 mL), 11 g of potassium carbonate was dissolved in 60 mL of water and added. After adding 0.9 g of tetrakistriphenyl-phosphinopalladium, the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and a white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate to prepare 13g (76% yield) of compound E12. MS [M+H] + = 642
제조예Manufacturing example 46: 화합물 E13의 제조 46: Preparation of compound E13
Figure PCTKR2020010175-appb-I000243
Figure PCTKR2020010175-appb-I000243
스파이로[플로렌-9,9'-싸이오잔텐]-3'-일보로닉엑시드 10g과 상기 2-(5-브로모싸이오펜-2-일)-4,6-다이페닐-1,3,5-트리아진 10.1g을 테트라 하이드로퓨란 (200 mL)에 완전히 녹인 후, 탄산칼륨 11g을 물 60 mL에 용해시켜 첨가하였다. 테트라키스트리페닐-포스피노팔라듐 0.9g을 넣은 후, 8 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 반응을 종결한 후, 탄산칼륨 용액을 제거하여 흰색 고체를 여과하였다. 여과된 흰색 고체를 테트라하이드로퓨란 및 에틸아세테이트로 세척하여 화합물 E13을 13g (수율 77 %)제조하였다. MS [M+H]+ = 663Spiro[floren-9,9'-thioxanthene]-3'-ylboronic acid 10g and the above 2-(5-bromothiophen-2-yl)-4,6-diphenyl-1, 10.1 g of 3,5-triazine was completely dissolved in tetrahydrofuran (200 mL), and then 11 g of potassium carbonate was dissolved in 60 mL of water and added. After adding 0.9 g of tetrakistriphenyl-phosphinopalladium, the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and a white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate to prepare 13 g of compound E13 (yield 77%). MS [M+H] + = 663
제조예Manufacturing example 47: 화합물 E14의 제조 47: Preparation of compound E14
Figure PCTKR2020010175-appb-I000244
Figure PCTKR2020010175-appb-I000244
스파이로[플로렌-9,9'-싸이오잔텐]-4'-일보로닉엑시드 10g과 상기 10-(4-(4-클로로-6-페닐-1,3,5-트리아진-2-일)페닐)-10H-페노싸이아진 11.9g을 테트라 하이드로퓨란 (200 mL)에 완전히 녹인 후, 탄산칼륨 11g을 물 60 mL에 용해시켜 첨가하였다. 테트라키스트리페닐-포스피노팔라듐 0.9g을 넣은 후, 8 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 반응을 종결한 후, 탄산칼륨 용액을 제거하여 흰색 고체를 여과하였다. 여과된 흰색 고체를 테트라하이드로퓨란 및 에틸아세테이트로 세척하여 화합물 E14를 16g (수율 81 %)제조하였다. MS [M+H]+ = 778Spiro[floren-9,9'-thioxanthene]-4'-ylboronic acid 10g and the above 10-(4-(4-chloro-6-phenyl-1,3,5-triazine-2) -Yl)phenyl)-10H-phenothiazine 11.9 g was completely dissolved in tetrahydrofuran (200 mL), and then 11 g of potassium carbonate was dissolved in 60 mL of water and added. After adding 0.9 g of tetrakistriphenyl-phosphinopalladium, the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and a white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate to prepare 16 g of compound E14 (yield 81%). MS [M+H] + = 778
제조예Manufacturing example 48: 화합물 E15의 제조 48: Preparation of compound E15
Figure PCTKR2020010175-appb-I000245
Figure PCTKR2020010175-appb-I000245
스파이로[플로렌-9,9'-싸이오잔텐]-4'-일보로닉엑시드 10g과 상기 4'-(4-클로로-6-페닐-1,3,5-트리아진-2-일)-[1,1'-바이페닐]-2-카보나이트릴 9.4g을 테트라 하이드로퓨란 (200 mL)에 완전히 녹인 후, 탄산칼륨 11g을 물 60 mL에 용해시켜 첨가하였다. 테트라키스트리페닐-포스피노팔라듐 0.9g을 넣은 후, 8 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 반응을 종결한 후, 탄산칼륨 용액을 제거하여 흰색 고체를 여과하였다. 여과된 흰색 고체를 테트라하이드로퓨란 및 에틸아세테이트로 세척하여 화합물 E15를 14g (수율 81 %)제조하였다. MS [M+H]+ = 682Spiro[floren-9,9'-thioxanthene]-4'-ylboronic acid 10g and the 4'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl) )-[1,1'-biphenyl]-2-carbonitryl 9.4 g was completely dissolved in tetrahydrofuran (200 mL), and then 11 g of potassium carbonate was dissolved in 60 mL of water and added. After adding 0.9 g of tetrakistriphenyl-phosphinopalladium, the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and a white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate to prepare 14 g (yield 81%) of compound E15. MS [M+H] + = 682
제조예Manufacturing example 49: 화합물 E16의 제조 49: Preparation of compound E16
Figure PCTKR2020010175-appb-I000246
Figure PCTKR2020010175-appb-I000246
(13,13-다이메틸-13H-인데노[1,2-l]페나쓰렌-11-일)보로닉 엑시드 10g과 상기 2-([1,1'-바이페닐]-2-일)-4-클로로-6-페닐-1,3,5-트리아진 10.2g을 테트라 하이드로퓨란 (200 mL)에 완전히 녹인 후, 탄산칼륨 11g을 물 60 mL에 용해시켜 첨가하였다. 테트라키스트리페닐-포스피노팔라듐 1.0g을 넣은 후, 8 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 반응을 종결한 후, 탄산칼륨 용액을 제거하여 흰색 고체를 여과하였다. 여과된 흰색 고체를 테트라하이드로퓨란 및 에틸아세테이트로 세척하여 화합물 E16을 14g (수율 79 %)제조하였다. MS [M+H]+ = 603(13,13-dimethyl-13H-indeno[1,2-l]phenathren-11-yl)boronic acid 10g and the above 2-([1,1'-biphenyl]-2-yl)- After dissolving 10.2 g of 4-chloro-6-phenyl-1,3,5-triazine completely in tetrahydrofuran (200 mL), 11 g of potassium carbonate was dissolved in 60 mL of water and added. After adding 1.0 g of tetrakistriphenyl-phosphinopalladium, the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and a white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate to prepare 14 g (79% yield) of compound E16. MS [M+H] + = 603
제조예Manufacturing example 50: 화합물 E17의 제조 50: Preparation of compound E17
Figure PCTKR2020010175-appb-I000247
Figure PCTKR2020010175-appb-I000247
(9,9-다이페닐-9H-플로렌-4-일)보로닉 엑시드 10g과 2-([1,1':3',1''-터페닐]-5'-일)-4-클로로-6-페닐-1,3,5-트리아진 11.5g을 테트라 하이드로퓨란 (200 mL)에 완전히 녹인 후, 탄산칼륨 11g을 물 60 mL에 용해시켜 첨가하였다. 테트라키스트리페닐-포스피노팔라듐 1.0g을 넣은 후, 8 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 반응을 종결한 후, 탄산칼륨 용액을 제거하여 흰색 고체를 여과하였다. 여과된 흰색 고체를 테트라하이드로퓨란 및 에틸아세테이트로 세척하여 화합물 E17을 15g (수율 77 %)제조하였다. MS [M+H]+ = 703(9,9-diphenyl-9H-floren-4-yl) boronic acid 10g and 2-([1,1':3',1''-terphenyl]-5'-yl)-4- After completely dissolving 11.5 g of chloro-6-phenyl-1,3,5-triazine in tetrahydrofuran (200 mL), 11 g of potassium carbonate was dissolved in 60 mL of water and added. After adding 1.0 g of tetrakistriphenyl-phosphinopalladium, the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and a white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate to prepare 15 g of compound E17 (yield 77%). MS [M+H] + = 703
제조예Manufacturing example 51: 화합물 E18의 제조 51: Preparation of compound E18
Figure PCTKR2020010175-appb-I000248
Figure PCTKR2020010175-appb-I000248
(9,9-다이메틸-7-페닐-9H-플로렌-4-일)보로닉 엑시드 10g과 2-([1,1'-바이페닐]-4-일)-4-클로로-6-(나프탈렌-1-일)-1,3,5-트리아진 12.5g을 테트라 하이드로퓨란 (200 mL)에 완전히 녹인 후, 탄산칼륨 13.2g을 물 60 mL에 용해시켜 첨가하였다. 테트라키스트리페닐-포스피노팔라듐 1.1g을 넣은 후, 8 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 반응을 종결한 후, 탄산칼륨 용액을 제거하여 흰색 고체를 여과하였다. 여과된 흰색 고체를 테트라하이드로퓨란 및 에틸아세테이트로 세척하여 화합물 E18을 16g (수율 80 %)제조하였다. MS [M+H]+ = 629(9,9-dimethyl-7-phenyl-9H-floren-4-yl) boronic acid 10g and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6- 12.5 g of (naphthalen-1-yl)-1,3,5-triazine was completely dissolved in tetrahydrofuran (200 mL), and then 13.2 g of potassium carbonate was dissolved in 60 mL of water and added. After adding 1.1 g of tetrakistriphenyl-phosphinopalladium, it was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and a white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate to prepare 16 g of compound E18 (yield 80%). MS [M+H] + = 629
제조예Manufacturing example 52: 화합물 E19의 제조 52: Preparation of compound E19
Figure PCTKR2020010175-appb-I000249
Figure PCTKR2020010175-appb-I000249
(9,9-다이페닐-9H-플로렌-2-일)보로닉 엑시드 10g과 2-([1,1'-바이페닐]-3-일)-4-클로로-6-(페나트렌-9-일)-1,3,5-트리아진 12.3g을 테트라 하이드로퓨란 (200 mL)에 완전히 녹인 후, 탄산칼륨 13.2g을 물 60 mL에 용해시켜 첨가하였다. 테트라키스트리페닐-포스피노팔라듐 1.0g을 넣은 후, 8 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 반응을 종결한 후, 탄산칼륨 용액을 제거하여 흰색 고체를 여과하였다. 여과된 흰색 고체를 테트라하이드로퓨란 및 에틸아세테이트로 세척하여 화합물 E19를 15g (수율 75 %)제조하였다. MS [M+H]+ = 72710 g of (9,9-diphenyl-9H-floren-2-yl) boronic acid and 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-(phenathrene- 9-day)-1,3,5-triazine 12.3 g was completely dissolved in tetrahydrofuran (200 mL), and then 13.2 g of potassium carbonate was dissolved in 60 mL of water and added. After adding 1.0 g of tetrakistriphenyl-phosphinopalladium, the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and a white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate to prepare 15 g of compound E19 (75% yield). MS [M+H] + = 727
제조예Manufacturing example 53: 화합물 E20의 제조 53: Preparation of compound E20
Figure PCTKR2020010175-appb-I000250
Figure PCTKR2020010175-appb-I000250
(9,9-다이페닐-9H-플로렌-1-일)보로닉 엑시드 10g과 2-([1,1'-바이페닐]-2-일)-4-클로로-6-(나프탈렌-2-일)-1,3,5-트리아진 10.6g을 테트라 하이드로퓨란 (200 mL)에 완전히 녹인 후, 탄산칼륨 11.1g을 물 60 mL에 용해시켜 첨가하였다. 테트라키스트리페닐-포스피노팔라듐 0.9g을 넣은 후, 8 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 반응을 종결한 후, 탄산칼륨 용액을 제거하여 흰색 고체를 여과하였다. 여과된 흰색 고체를 테트라하이드로퓨란 및 에틸아세테이트로 세척하여 화합물 E20을 14g (수율 79 %)제조하였다. MS [M+H]+ = 677(9,9-diphenyl-9H-floren-1-yl) boronic acid 10g and 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-(naphthalene-2 -Yl)-1,3,5-triazine 10.6 g was completely dissolved in tetrahydrofuran (200 mL), and then 11.1 g of potassium carbonate was dissolved in 60 mL of water and added. After adding 0.9 g of tetrakistriphenyl-phosphinopalladium, the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and a white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate to prepare 14 g (79% yield) of compound E20. MS [M+H] + = 677
본 명세서의 실시예에 기재된 제조식과 상기 중간체들을 통상의 기술상식을 바탕으로 적절히 조합하면, 본 명세서에 기재되어 있는 상기 화학식 1 및 2의 헤테로고리 화합물들을 모두 제조할 수 있다.By appropriately combining the preparation formulas described in the examples of the present specification and the intermediates based on common technical knowledge, all of the heterocyclic compounds of Formulas 1 and 2 described herein can be prepared.
<소자예 1><Device Example 1>
실시예Example 1 One
ITO (indium tin oxide)가 1000 Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이때, 세제로는 피셔사 (Fischer Co.) 제품을 사용하였으며, 증류수로는 밀리포어사 (Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30 분간 세척한 후 증류수로 2 회 반복하여 초음파 세척을 10 분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5 분간 세정한 후 진공 증착기로 기판을 수송시켰다. A glass substrate coated with a thin film of 1000 Å of ITO (indium tin oxide) was put in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.
이렇게 준비된 ITO 투명 전극 위에 상기 HI-A 화합물을 600 Å의 두께로 열 진공 증착하여 정공주입층을 형성하였다. 상기 정공주입층 상에 상기 HAT 화합물 50 Å및 상기 HT-A 화합물 600Å를 순차적으로 진공 증착하여 정공수송층을 형성하였다. 상기 정공수송층 위에 하기 HT-B를 50Å의 두께로 진공 증착하여 전자차단층을 형성하였다.The HI-A compound was thermally vacuum deposited to a thickness of 600 Å on the prepared ITO transparent electrode to form a hole injection layer. 50 Å of the HAT compound and 600 Å of the HT-A compound were sequentially vacuum deposited on the hole injection layer to form a hole transport layer. On the hole transport layer, the following HT-B was vacuum-deposited to a thickness of 50 Å to form an electron blocking layer.
이어서, 상기 정공수송층 상에 막 두께 200 Å로 BH-1 화합물 및 Compound 1을 100:2의 중량비로 진공 증착하여 발광층을 형성하였다. Subsequently, a BH-1 compound and Compound 1 with a film thickness of 200 Å were vacuum-deposited at a weight ratio of 100:2 on the hole transport layer to form a light emitting layer.
상기 발광층 상에 화합물 E1을 진공 증착하여 50Å의 두께로 정공차단층을 형성하였다. 상기 정공차단층 상에 화합물 ET 과 하기 LiQ 화합물을 1:1의 중량비로 진공 증착하여 300Å의 두께로 전자 주입 및 수송층을 형성하였다. 상기 전자 주입 및 수송층 상에 순차적으로 10Å의 두께로 리튬 플루오라이드(LiF)와 1000Å두께로 알루미늄을 증착하여 음극을 형성하였다. Compound E1 was vacuum-deposited on the emission layer to form a hole blocking layer with a thickness of 50Å. Compound ET and the following LiQ compound were vacuum-deposited at a weight ratio of 1:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300Å. Lithium fluoride (LiF) in a thickness of 10 Å and aluminum in a thickness of 1000 Å were sequentially deposited on the electron injection and transport layer to form a negative electrode.
Figure PCTKR2020010175-appb-I000251
Figure PCTKR2020010175-appb-I000251
상기의 과정에서 유기물의 증착 속도는 0.4 내지 0.9 Å/sec를 유지하였고, 음극의 리튬 플루오라이드는 0.3Å/sec, 알루미늄은 2Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 1Х10-7 내지 5Х10-5 torr를 유지하여, 유기 발광 소자를 제조하였다.Was maintained at the deposition rate of the organic material in the above process, 0.4 to 0.9 Å / sec, the lithium fluoride of the cathode 0.3Å / sec, the deposition rate of aluminum was maintained 2Å / sec, the degree of vacuum during the deposition to 1Х10 -7 By maintaining 5Х10 -5 torr, an organic light emitting device was manufactured.
Figure PCTKR2020010175-appb-I000252
Figure PCTKR2020010175-appb-I000252
실시예Example 2 내지 18 및 2 to 18 and 비교예Comparative example 1 내지 8 1 to 8
발광층의 도펀트 물질 및 정공차단층 물질을 하기 표 1에 기재된 물질을 사용한 것을 제외하고, 상기 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that the materials shown in Table 1 were used as the dopant material and the hole blocking layer material of the emission layer.
상기 실시예 1 내지 18 및 비교예 1 내지 8의 유기 발광 소자에 대하여 10 mA/cm2의 전류 밀도에서 구동 전압과 발광 효율(환산 효율)을 측정하였고, 15 mA/cm2의 전류 밀도에서 초기 휘도 대비 95%가 되는 시간(T95)을 측정하여 표시하였다. 상기 결과를 하기 표 1에 나타내었다.The Examples 1 to 18 and Comparative Examples 1 to were measured for 8 organic light emitting element driving voltage and luminous efficiency at a current density of 10 mA / cm 2 with respect to the (in terms of efficiency), initially at a current density of 15 mA / cm 2 The time (T95) to be 95% of the luminance was measured and displayed. The results are shown in Table 1 below.
　 화합물compound 10mA/cm2 10mA / cm 2 15mA/cm2 15mA / cm 2
entryentry 도펀트Dopant 정공 차단층Hole blocking layer 전압Voltage 환산 효율(cd/A/y)Conversion efficiency (cd/A/y) T95, HrT95, Hr
실시예1Example 1 Compound1Compound1 E1E1 4.34.3 67.267.2 173173
실시예2Example 2 Compound3Compound3 E3E3 4.24.2 69.269.2 177177
실시예3Example 3 Compound4Compound4 E5E5 4.34.3 71.171.1 165165
실시예4Example 4 Compound5Compound5 E7E7 4.44.4 71.071.0 180180
실시예5Example 5 Compound7Compound7 E9E9 4.44.4 71.271.2 162162
실시예6Example 6 Compound9Compound9 E11E11 4.34.3 72.772.7 172172
실시예7Example 7 Compound10Compound10 E12E12 4.44.4 72.272.2 171171
실시예8Example 8 Compound13Compound13 E17E17 4.34.3 69.269.2 166166
실시예9Example 9 Compound15Compound15 E19E19 4.24.2 71.671.6 168168
실시예10Example 10 Compound16Compound16 E3E3 4.24.2 70.470.4 175175
실시예11Example 11 Compound18Compound18 E7E7 4.44.4 67.567.5 176176
실시예12Example 12 Compound23Compound23 E11E11 4.34.3 72.772.7 169169
실시예13Example 13 Compound24Compound24 E17E17 4.34.3 69.869.8 158158
실시예14Example 14 Compound25Compound25 E19E19 4.24.2 67.367.3 158158
실시예15Example 15 Compound27Compound27 E9E9 4.44.4 69.3069.30 176176
실시예16Example 16 Compound28Compound28 E12E12 4.44.4 73.4473.44 165165
실시예17Example 17 Compound31Compound31 E17E17 4.34.3 69.7769.77 164164
실시예18Example 18 Compound33Compound33 E19E19 4.24.2 74.0574.05 177177
비교예1Comparative Example 1 BD-ABD-A ET-BET-B 4.64.6 52.452.4 104104
비교예2Comparative Example 2 BD-BBD-B ET-AET-A 4.54.5 51.851.8 7676
비교예3Comparative Example 3 BD-CBD-C ET-DET-D 4.84.8 43.743.7 110110
비교예4Comparative Example 4 Compound1Compound1 ET-BET-B 4.64.6 61.861.8 112112
비교예5Comparative Example 5 Compound5Compound5 ET-DET-D 4.84.8 54.954.9 144144
비교예6Comparative Example 6 Compound23Compound23 ET-AET-A 4.54.5 64.864.8 126126
비교예7Comparative Example 7 BD-ABD-A E3E3 4.24.2 58.158.1 154154
비교예8Comparative Example 8 BD-CBD-C E19E19 4.24.2 59.459.4 132132
상기 표에서, 비교예 1 내지 3은 발광층의 도펀트 및 정공차단층 물질로 모두 본 발명의 화학식 1 및 2의 화합물과는 상이한 화합물을 사용하엿다. 실시예 1 내지 14는 비교예 1 내지 3과 비교하여, 저전압, 고효율 특성을보이며, 특히 수명이 높은 폭으로 증가하는 것을 확인 할 수 있다. In the above table, Comparative Examples 1 to 3 used a compound different from the compounds of Formulas 1 and 2 of the present invention as the dopant and hole blocking layer material of the light emitting layer. As compared with Comparative Examples 1 to 3, Examples 1 to 14 show low voltage and high efficiency characteristics, and it can be confirmed that the lifespan is particularly increased to a high width.
비교예 4 내지 8은 발광층의 도펀트 및 정공차단층 물질 중 어느 하나를 본 발명의 화합물을 사용한다. 실시예 1과 비교예 4, 실시예 4와 비교예 5, 실시예 12와 비교예 6을 각각 비교하면, 발광층의 도펀트 물질로 동일한 물질을 사용하나, 정공차단층에 사용되는 물질이 달라짐으로 인해 소자에 적용했을 때 효과차이가 나타남을 알 수 있다. 실시예 1, 4, 12는 비교예 4, 5, 6과 비교하여 저전압, 고효율 및 높은 수명 특성을 가지는 것을 확인할 수 있다. In Comparative Examples 4 to 8, any one of the dopant of the light emitting layer and the material of the hole blocking layer was used as the compound of the present invention. When comparing Example 1 and Comparative Example 4, Example 4 and Comparative Example 5, and Example 12 and Comparative Example 6, respectively, the same material was used as the dopant material of the light emitting layer, but the material used for the hole blocking layer was different. It can be seen that the effect difference appears when applied to the device. It can be seen that Examples 1, 4, and 12 have low voltage, high efficiency, and high lifetime characteristics compared to Comparative Examples 4, 5, and 6.
실시예 2와 비교예 7, 실시예 9, 18와 비교예 8은 각각 동일한 정공차단물질을 사용하고, 상이한 도펀트 물질을 이용한 소자자료이다. 도펀트 물질의 차이로 인하여, 실시예 2, 9 및 18은 비교예 7 및 8에 비하여 저전압, 고효율 및 장수명 특성을 가지는 것을 확인할 수 있다. Example 2, Comparative Example 7, Examples 9, 18, and 8 are device data using the same hole blocking material and different dopant materials, respectively. Due to the difference in the dopant material, it can be seen that Examples 2, 9 and 18 have low voltage, high efficiency, and long life characteristics compared to Comparative Examples 7 and 8.
<소자예 2><Device Example 2>
실시예Example 19 19
ITO (indium tin oxide)가 1000 Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이때, 세제로는 피셔사 (Fischer Co.) 제품을 사용하였으며, 증류수로는 밀리포어사 (Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30 분간 세척한 후 증류수로 2 회 반복하여 초음파 세척을 10 분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5 분간 세정한 후 진공 증착기로 기판을 수송시켰다. A glass substrate coated with a thin film of 1000 Å of ITO (indium tin oxide) was put in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.
이렇게 준비된 ITO 투명 전극 위에 하기 HI-A 화합물을 600 Å의 두께로 열 진공 증착하여 정공주입층을 형성하였다. 상기 정공주입층 상에 하기 HAT 화합물 50 Å및 하기 HT-A 화합물 600Å를 순차적으로 진공 증착하여 정공수송층을 형성하였다. The following HI-A compound was thermally vacuum deposited to a thickness of 600 Å on the prepared ITO transparent electrode to form a hole injection layer. On the hole injection layer, 50 Å of the following HAT compound and 600 Å of the following HT-A compound were sequentially vacuum-deposited to form a hole transport layer.
이어서, 상기 정공수송층 상에 막 두께 200 Å로 BH-2 화합물 및 하기 Compound 2을 100:2의 중량비로 진공 증착하여 발광층을 형성하였다. Subsequently, the BH-2 compound and the following Compound 2 with a film thickness of 200 Å were vacuum-deposited at a weight ratio of 100:2 on the hole transport layer to form a light emitting layer.
상기 발광층 상에 화합물 E10과 하기 LiQ 화합물을 1:1의 중량비로 진공 증착하여 350Å의 두께로 전자 주입 및 수송층을 형성하였다. 상기 전자 주입 및 수송층 상에 순차적으로 10Å의 두께로 리튬 플루오라이드(LiF)와 1000Å두께로 알루미늄을 증착하여 음극을 형성하였다. Compound E10 and the following LiQ compound were vacuum-deposited at a weight ratio of 1:1 on the emission layer to form an electron injection and transport layer with a thickness of 350Å. Lithium fluoride (LiF) in a thickness of 10 Å and aluminum in a thickness of 1000 Å were sequentially deposited on the electron injection and transport layer to form a negative electrode.
상기의 과정에서 유기물의 증착 속도는 0.4 내지 0.9 Å/sec를 유지하였고, 음극의 리튬 플루오라이드는 0.3 Å/sec, 알루미늄은 2 Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 1Х10-7 내지 5Х10-5 torr를 유지하여, 유기 발광 소자를 제조하였다.In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.9 Å/sec, the deposition rate of lithium fluoride at the cathode was 0.3 Å/sec, and the deposition rate of aluminum was 2 Å/sec, and the vacuum degree at the time of deposition was 1Х10 -7. To 5Х10 -5 torr was maintained, an organic light emitting device was manufactured.
Figure PCTKR2020010175-appb-I000253
Figure PCTKR2020010175-appb-I000253
실시예Example 20 내지 28 및 20 to 28 and 비교예Comparative example 9 내지 16 9 to 16
발광층의 도펀트 물질 및 전자 주입 및 수송층 물질을 하기 표 2에 기재된 물질을 사용한 것을 제외하고, 상기 실시예 19과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light-emitting device was manufactured in the same manner as in Example 19, except that the dopant material of the emission layer and the material of the electron injection and transport layer were used in Table 2 below.
Figure PCTKR2020010175-appb-I000254
Figure PCTKR2020010175-appb-I000254
상기 실시예 19 내지 28 및 비교예 9 내지 16의 유기 발광 소자에 대하여 10 mA/cm2의 전류 밀도에서 구동 전압과 발광 효율(환산 효율)을 측정하였고, 15 mA/cm2의 전류 밀도에서 초기 휘도 대비 95%가 되는 시간(T95)을 측정하여 표시하였다. 상기 결과를 하기 표 2에 나타내었다. The above Examples 19 to 28 and Comparative Examples 9 to 16 The organic light emitting element driving voltage and luminous efficiency at a current density of 10 mA / cm 2 with respect to the (in terms of efficiency) was measured, initially at a current density of 15 mA / cm 2 The time (T95) to be 95% of the luminance was measured and displayed. The results are shown in Table 2 below.
　 화합물compound 10mA/cm210mA/cm2 15mA/cm215mA/cm2
entryentry 도펀트Dopant 전자 주입및 수송층Electron injection and transport layer 전압Voltage 환산 효율(cd/A/y)Conversion efficiency (cd/A/y) T95, HrT95, Hr
실시예19Example 19 Compound2Compound2 E10E10 3.93.9 71.6071.60 161161
실시예20Example 20 Compound8Compound8 E6E6 4.04.0 68.4868.48 173173
실시예21Example 21 Compound12Compound12 E15E15 4.44.4 68.8068.80 211211
실시예22Example 22 Compound14Compound14 E2E2 4.54.5 71.7471.74 195195
실시예23Example 23 Compound19Compound19 E18E18 4.14.1 65.0965.09 181181
실시예24Example 24 Compound21Compound21 E4E4 3.93.9 71.6971.69 146146
실시예25Example 25 Compound26Compound26 E2E2 4.34.3 66.4466.44 188188
실시예26Example 26 Compound29Compound29 E4E4 4.24.2 72.3172.31 165165
실시예27Example 27 Compound30Compound30 E15E15 4.44.4 68.2168.21 217217
실시예28Example 28 Compound32Compound32 E18E18 4.44.4 67.9767.97 177177
비교예9Comparative Example 9 BD-ABD-A ET-BET-B 4.64.6 52.4452.44 104104
비교예10Comparative Example 10 BD-CBD-C ET-DET-D 4.84.8 43.6543.65 110110
비교예11Comparative Example 11 BD-DBD-D ET-CET-C 4.64.6 43.7443.74 9393
비교예12Comparative Example 12 Compound2Compound2 ET-DET-D 4.84.8 52.6552.65 140140
비교예13Comparative Example 13 Compound8Compound8 ET-BET-B 4.64.6 62.3862.38 121121
비교예14Comparative Example 14 Compound21Compound21 ET-CET-C 4.64.6 56.3856.38 125125
비교예15Comparative Example 15 BD-ABD-A E4E4 4.24.2 58.7158.71 146146
비교예16Comparative Example 16 BD-CBD-C E18E18 4.44.4 55.8755.87 135135
상기 표 2에서, 비교예 9 내지 11은 발광층의 도펀트 및 정공차단층 물질로 모두 본 발명의 화학식 1 및 2의 화합물과는 상이한 화합물을 사용하엿다. In Table 2, in Comparative Examples 9 to 11, a compound different from the compounds of Formulas 1 and 2 of the present invention was used as the dopant and the hole blocking layer material of the emission layer.
실시예 19 내지 28은 비교예 9 내지 11과 비교하여, 저전압, 고효율 및 장수명 특성을 보이는 것을 확인 할 수 있다. Examples 19 to 28 compared to Comparative Examples 9 to 11, it can be seen that the low voltage, high efficiency and long life characteristics.
비교예 12 내지 14는 각각 실시예 19, 20 및 24와 동일한 도펀트 물질을 사용하고, 전자주입 및 수송 층에만 상이한 물질을 사용한다. 실시예 19, 20 및 24은 비교예 12 내지 14와 비교하여, 저전압, 고효율 장수명의 특성을 보인다.Comparative Examples 12 to 14 used the same dopant material as in Examples 19, 20, and 24, respectively, and different materials were used only for the electron injection and transport layers. Examples 19, 20, and 24 show characteristics of low voltage, high efficiency and long life, compared with Comparative Examples 12 to 14.
비교예 15 및 16은 각각 실시예 24, 26 및 23, 28과 동일한 전자주입 및 수송 층 물질을 사용한다. 하지만 도펀트 물질이 상이하여, 실시예 24, 26, 23, 및 38은 각각 비교예 15 및 16과 비교하여, 소자에 적용했을 때 더 우수한 효과를 보이는 것을 확인할 수 있다.Comparative Examples 15 and 16 used the same electron injection and transport layer materials as Examples 24, 26, 23, and 28, respectively. However, since the dopant materials are different, Examples 24, 26, 23, and 38 are compared with Comparative Examples 15 and 16, respectively, and it can be seen that when applied to a device, more excellent effects are shown.
<소자예 3><Device Example 3>
실시예Example 29 29
ITO (indium tin oxide)가 1000 Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이때, 세제로는 피셔사 (Fischer Co.) 제품을 사용하였으며, 증류수로는 밀리포어사 (Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30 분간 세척한 후 증류수로 2 회 반복하여 초음파 세척을 10 분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5 분간 세정한 후 진공 증착기로 기판을 수송시켰다. A glass substrate coated with a thin film of 1000 Å of ITO (indium tin oxide) was put in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.
이렇게 준비된 ITO 투명 전극 위에 상기 HI-A 화합물을 600 Å의 두께로 열 진공 증착하여 정공주입층을 형성하였다. 상기 정공주입층 상에 상기 HAT 화합물 50 Å및 상기 HT-A 화합물 600Å를 순차적으로 진공 증착하여 정공수송층을 형성하였다. 상기 정공수송층 위에 하기 HT-B를 50 Å의 두께로 진공 증착하여 전자차단층을 형성 하였다.The HI-A compound was thermally vacuum deposited to a thickness of 600 Å on the prepared ITO transparent electrode to form a hole injection layer. 50 Å of the HAT compound and 600 Å of the HT-A compound were sequentially vacuum deposited on the hole injection layer to form a hole transport layer. On the hole transport layer, the following HT-B was vacuum deposited to a thickness of 50 Å to form an electron blocking layer.
이어서, 상기 정공수송층 상에 막 두께 200 Å로 BH-3 화합물 및 Compound 5을 100:2의 중량비로 진공 증착하여 발광층을 형성하였다. Subsequently, on the hole transport layer, a BH-3 compound and Compound 5 with a thickness of 200 Å were vacuum-deposited at a weight ratio of 100:2 to form a light emitting layer.
상기 발광층 상에 화합물 E10을 진공 증착하여 50Å의 두께로 정공차단층을 형성하였다. 상기 정공차단층 상에 화합물 E2과 하기 LiQ 화합물을 1:1의 중량비로 진공 증착하여 300Å의 두께로 전자 주입 및 수송층을 형성하였다. 상기 전자 주입 및 수송층 상에 순차적으로 10Å의 두께로 리튬 플루오라이드(LiF)와 1000Å두께로 알루미늄을 증착하여 음극을 형성하였다. Compound E10 was vacuum-deposited on the emission layer to form a hole blocking layer with a thickness of 50Å. Compound E2 and the following LiQ compound were vacuum-deposited at a weight ratio of 1:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300Å. Lithium fluoride (LiF) in a thickness of 10 Å and aluminum in a thickness of 1000 Å were sequentially deposited on the electron injection and transport layer to form a negative electrode.
상기의 과정에서 유기물의 증착 속도는 0.4 내지 0.9 Å/sec를 유지하였고, 음극의 리튬 플루오라이드는 0.3 Å/sec, 알루미늄은 2 Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 1Х10-7 내지 5Х10-5 torr를 유지하여, 유기 발광 소자를 제조하였다.In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.9 Å/sec, the deposition rate of lithium fluoride at the cathode was 0.3 Å/sec, and the deposition rate of aluminum was 2 Å/sec, and the vacuum degree at the time of deposition was 1Х10 -7. To 5Х10 -5 torr was maintained, an organic light emitting device was manufactured.
Figure PCTKR2020010175-appb-I000255
Figure PCTKR2020010175-appb-I000255
실시예Example 30 내지 34 및 30 to 34 and 비교예Comparative example 17 내지 19 17 to 19
발광층의 도펀트 물질, 정공차단층 물질 및 전자 주입 및 수송층 물질을 하기 표 3에 기재된 물질을 사용한 것을 제외하고, 상기 실시예 29와 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light-emitting device was manufactured in the same manner as in Example 29, except that the materials shown in Table 3 below were used as the dopant material, the hole blocking layer material, and the electron injection and transport layer material of the emission layer.
상기 실시예 29 내지 34 및 비교예 17 내지 19의 유기 발광 소자에 대하여 10 mA/cm2의 전류 밀도에서 구동 전압과 발광 효율(환산 효율)을 측정하였고, 15 mA/cm2의 전류 밀도에서 초기 휘도 대비 95%가 되는 시간(T95)을 측정하여 표시하였다. 상기 결과를 하기 표 3에 나타내었다.Example 29 to 34 and Comparative Examples 17 to 19 was the measurement of driving voltage and light emission efficiency (conversion efficiency) at a current density of 10 mA / cm 2, the organic light emitting device, initially at a current density of 15 mA / cm 2 The time (T95) to be 95% of the luminance was measured and displayed. The results are shown in Table 3 below.
Figure PCTKR2020010175-appb-I000256
Figure PCTKR2020010175-appb-I000256
　 화합물compound 10mA/cm2 10mA / cm 2 15mA/cm2 15mA / cm 2
entryentry 도펀트Dopant 정공차단층Hole blocking layer 전자 주입 및 수송층Electron injection and transport layer 전압Voltage 환산 효율(cd/A/y)Conversion efficiency (cd/A/y) T95, HrT95, Hr
실시예29Example 29 Compound5Compound5 E10E10 E2E2 4.54.5 73.1773.17 151151
실시예30Example 30 Compound6Compound6 E13E13 E4E4 4.34.3 72.4072.40 137137
실시예31Example 31 Compound11Compound11 E14E14 E6E6 4.54.5 67.6067.60 137137
실시예32Example 32 Compound17Compound17 E8E8 E15E15 4.54.5 68.0068.00 211211
실시예33Example 33 Compound20Compound20 E16E16 E18E18 4.44.4 67.0567.05 143143
실시예34Example 34 Compound22Compound22 E20E20 E7E7 4.44.4 67.3067.30 169169
비교예17Comparative Example 17 BD-ABD-A ET-AET-A ET-AET-A 4.74.7 46.1746.17 7474
비교예18Comparative Example 18 BD-ABD-A E10E10 ET-BET-B 4.74.7 53.4953.49 9494
비교예19Comparative Example 19 BD-CBD-C ET-CET-C E7E7 4.74.7 45.7345.73 9797
상기 표 3에 있어서, 비교예 17은 도펀트 물질, 정공차단층 물질, 전자주입 및 수송 층 물질로 모두 본 발명의 화학식이 아닌 화합물을 사용한 데이터이다. 비교예 18은 실시예 29와 동일한 정공차단층 물질을 사용하고, 도펀트 물질과 전자주입 및 수송층 물질만 다르다. In Table 3, Comparative Example 17 is data using a compound other than the chemical formula of the present invention as a dopant material, a hole blocking layer material, an electron injection material, and a transport layer material. Comparative Example 18 uses the same hole blocking layer material as in Example 29, and differs only in the dopant material and the electron injection and transport layer material.
비교예 19는 실시예 34과 동일한 전자주입 및 수송층 물질을 사용하고, 도펀트 및 정공차단층에는 다른 물질을 사용하였다. 그로인해 실시예 29 및 34는 비교예 18 및 19와 비교하여 저전압, 고효율, 장수명의 우수한 효과를 가지는 것을 확인 할 수 있다.In Comparative Example 19, the same material for the electron injection and transport layer as in Example 34 was used, and different materials were used for the dopant and the hole blocking layer. Accordingly, it can be confirmed that Examples 29 and 34 have excellent effects of low voltage, high efficiency, and long life compared to Comparative Examples 18 and 19.

Claims (12)

  1. 제1 전극; 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 유기물층을 포함하고,A first electrode; A second electrode; And an organic material layer provided between the first electrode and the second electrode,
    상기 유기물층은 하기 화학식 1로 표시되는 화합물을 포함하는 제1 유기물층 및 하기 화학식 2로 표시되는 화합물을 포함하는 제2 유기물층을 포함하는 유기 발광 소자:The organic material layer is an organic light-emitting device including a first organic material layer including a compound represented by Formula 1 below and a second organic material layer including a compound represented by Formula 2 below:
    [화학식 1][Formula 1]
    Figure PCTKR2020010175-appb-I000257
    Figure PCTKR2020010175-appb-I000257
    상기 화학식 1에 있어서,In Formula 1,
    A1, A2, A3, B1 및 B2는 서로 같거나 상이하고, 각각 독립적으로 탄화수소고리이며,A1, A2, A3, B1 and B2 are the same as or different from each other, and each independently a hydrocarbon ring,
    R1 내지 R5는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아릴옥시기; 또는 치환 또는 비치환된 헤테로고리기이거나; 하기 화학식 3으로 표시되고, R1 내지 R5 중 적어도 하나 이상은 하기 화학식 3으로 표시되고,R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; Or a substituted or unsubstituted heterocyclic group; Represented by the following formula 3, at least one of R1 to R5 is represented by the following formula 3,
    [화학식 3][Formula 3]
    Figure PCTKR2020010175-appb-I000258
    Figure PCTKR2020010175-appb-I000258
    상기 화학식 3에 있어서,In Chemical Formula 3,
    상기 점선은 A1, A2, A3, B1 또는 B2와 연결되는 부위이고,The dotted line is a portion connected to A1, A2, A3, B1 or B2,
    X는 C 또는 Si 이고,X is C or Si,
    R6 내지 R8은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이며, R6 to R8 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
    n1 및 n5는 각각 0 내지 4의 정수이고,n1 and n5 are each an integer of 0 to 4,
    n2 및 n4는 각각 0 내지 5의 정수이고,n2 and n4 are each an integer of 0 to 5,
    n3은 0 내지 3의 정수이고,n3 is an integer from 0 to 3,
    n1 + n2 + n3 + n4 + n5는 1 이상이고,n1 + n2 + n3 + n4 + n5 is 1 or more,
    n1 내지 n5가 2 이상인 경우, 괄호 내의 치환기는 서로 같거나 상이하고,When n1 to n5 are 2 or more, the substituents in parentheses are the same as or different from each other,
    [화학식 2] [Formula 2]
    Figure PCTKR2020010175-appb-I000259
    Figure PCTKR2020010175-appb-I000259
    상기 화학식 2에 있어서,In Formula 2,
    Y31 및 Y32는 서로 같거나 상이하고, 각각 독립적으로 수소, 치환 또는 비치환된 알킬기, 또는 치환 또는 비치환된 아릴기이거나, 서로 결합하여 치환 또는 비치환된 고리를 형성하고,Y31 and Y32 are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or combine with each other to form a substituted or unsubstituted ring,
    R3-1은 수소, 중수소, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 헤테로아릴기, 또는 하기 화학식 4이거나, 인접한 기와 서로 결합하여 탄화수소고리를 형성하고, R3-1 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or the following formula (4), or is bonded to each other with adjacent groups to form a hydrocarbon ring,
    a31은 0 내지 8의 정수이고,a31 is an integer from 0 to 8,
    a31이 복수일 때, R3-1은 서로 같거나 상이하고,when a31 is plural, R3-1 is the same as or different from each other,
    [화학식 4][Formula 4]
    Figure PCTKR2020010175-appb-I000260
    Figure PCTKR2020010175-appb-I000260
    상기 화학식 4에 있어서,In Formula 4,
    상기 점선은 코어와 연결되는 부분이고,The dotted line is a part connected to the core,
    Ar41 및 Ar42는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이며,Ar 41 and Ar 42 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
    X1 내지 X3은 서로 같거나 상이하고, 각각 독립적으로 N 또는 CR이며,X 1 to X 3 are the same as or different from each other, and each independently N or CR,
    X1 내지 X3중 적어도 하나는 N이고,At least one of X 1 to X 3 is N,
    R은 수소; 중수소; 할로겐기; 니트릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아릴옥시기; 또는 치환 또는 비치환된 헤테로고리기이고,R is hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; Or a substituted or unsubstituted heterocyclic group,
    L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합, 치환 또는 비치환된 아릴렌기, 또는 치환 또는 비치환된 헤테로아릴렌기이다.L 1 to L 3 are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.
  2. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 1-1로 표시되는 것인 유기 발광 소자: The organic light-emitting device of claim 1, wherein Formula 1 is represented by the following Formula 1-1:
    [화학식 1-1][Formula 1-1]
    Figure PCTKR2020010175-appb-I000261
    Figure PCTKR2020010175-appb-I000261
    상기 화학식 1-1에 있어서, R1 내지 R5 및 n1 내지 n5는 상기 화학식 1에서 정의한 바와 같다.In Formula 1-1, R1 to R5 and n1 to n5 are as defined in Formula 1.
  3. 청구항 1에 있어서,The method according to claim 1,
    R1, R2, R4, 및 R5는 서로 같거나 상이하고, 각각 독립적으로, 수소; 중수소; 할로겐기; 시아노기; 중수소로 치환 또는 비치환된 탄소수 1 내지 10의 알킬기; 중수소로 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 중수소로 치환 또는 비치환된 탄소수 6 내지 60의 아릴아민기; 중수소, 할로겐기, 시아노기 및 탄소수 1 내지 10의 알킬기로 이루어진 군에서 선택된 1 이상의 치환기 또는 상기 군에서 선택된 2 이상의 기가 연결된 치환기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 중수소로 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기; 또는 상기 화학식 3으로 표시되고,R1, R2, R4, and R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium; A cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with deuterium; Arylamine group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium; An aryl group having 6 to 30 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, and an alkyl group having 1 to 10 carbon atoms or a substituent connected with two or more groups selected from the group; A heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium; Or represented by Chemical Formula 3,
    R3는 수소; 중수소; 할로겐기; 시아노기; 중수소로 치환 또는 비치환된 탄소수 1 내지 10의 알킬기; 중수소로 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 중수소, 할로겐기, 시아노기, 탄소수 1 내지 10의 알킬기, 탄소수 6 내지 30의 아릴기 및 실릴기로 이루어진 군에서 선택된 1 이상의 치환기 또는 상기 군에서 선택된 2 이상의 기가 연결된 치환기로 치환 또는 비치환된 탄소수 6 내지 60의 아릴아민기; 중수소, 할로겐기, 또는 시아노기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 중수소로 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기; 또는 상기 화학식 3으로 표시되는 것인 유기 발광 소자.R3 is hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium; A cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with deuterium; 6 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen groups, cyano groups, alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 30 carbon atoms, and silyl groups, or a substituent connected with two or more groups selected from the group Arylamine group of to 60; An aryl group having 6 to 30 carbon atoms unsubstituted or substituted with deuterium, a halogen group, or a cyano group; A heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium; Or an organic light-emitting device represented by Formula 3 above.
  4. 청구항 1에 있어서, 상기 화학식 2은 하기 화학식 2-1로 표시되는 것인 유기 발광 소자:The organic light-emitting device of claim 1, wherein Formula 2 is represented by Formula 2-1:
    [화학식 2-1][Formula 2-1]
    Figure PCTKR2020010175-appb-I000262
    Figure PCTKR2020010175-appb-I000262
    상기 화학식 2-1에 있어서, In Formula 2-1,
    Y는 CR111R112, O, 또는 S이고, Y is CR111R112, O, or S,
    R111, R112, R3-2 및 R3-3은 서로 같거나 상이하고, 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 헤테로아릴기, 또는 하기 화학식 4이거나, 인접한 기와 서로 결합하여 탄화수소고리를 형성하고, R111, R112, R3-2 and R3-3 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or It is the following formula (4), or combines with an adjacent group to form a hydrocarbon ring,
    L31 및 L32는 서로 같거나 상이하고, 각각 독립적으로 직접결합, 치환 또는 비치환된 아릴렌, 또는 치환 또는 비치환된 헤테로아릴렌이고,L31 and L32 are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
    a32은 0 내지 8의 정수이고,a32 is an integer from 0 to 8,
    b33은 0 내지 8의 정수이고,b33 is an integer from 0 to 8,
    a33 및 b33이 각각 복수일 때, 괄호 안의 치환기는 서로 같거나 상이하고,When a33 and b33 are each plural, the substituents in parentheses are the same as or different from each other,
    n33은 0 또는 1이고,n33 is 0 or 1,
    n33이 0일 때, Y에 결합된 2개의 벤젠고리의 위치에는 각각 수소가 결합되고,When n33 is 0, hydrogen is bonded to each of the two benzene rings bonded to Y,
    [화학식 4] [Formula 4]
    Figure PCTKR2020010175-appb-I000263
    Figure PCTKR2020010175-appb-I000263
    상기 점선은 코어와 연결되는 부분이고,The dotted line is a part connected to the core,
    Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이며,Ar 1 and Ar 2 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
    X1 내지 X3은 서로 같거나 상이하고, 각각 독립적으로 N 또는 CR이며,X 1 to X 3 are the same as or different from each other, and each independently N or CR,
    X1 내지 X3중 적어도 하나는 N이고,At least one of X 1 to X 3 is N,
    R은 서로 같거나상이하고 각각 독립적으로, 수소; 중수소; 할로겐기; 니트릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아릴옥시기; 또는 치환 또는 비치환된 헤테로고리기이고,R is the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; Or a substituted or unsubstituted heterocyclic group,
    L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합, 치환 또는 비치환된 아릴렌기, 또는 치환 또는 비치환된 헤테로아릴렌기이다.L 1 to L 3 are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.
  5. 청구항 4에 있어서, Y는 O 또는 S인 것인 유기 발광 소자.The organic light-emitting device of claim 4, wherein Y is O or S.
  6. 청구항 1에 있어서, 상기 화학식 1로 표시되는 화합물은 하기 화합물 중에서 선택되는 어느 하나인 것인 유기 발광 소자:The organic light-emitting device of claim 1, wherein the compound represented by Formula 1 is any one selected from the following compounds:
    Figure PCTKR2020010175-appb-I000264
    Figure PCTKR2020010175-appb-I000265
    Figure PCTKR2020010175-appb-I000264
    Figure PCTKR2020010175-appb-I000265
    Figure PCTKR2020010175-appb-I000266
    Figure PCTKR2020010175-appb-I000266
    Figure PCTKR2020010175-appb-I000267
    Figure PCTKR2020010175-appb-I000267
    Figure PCTKR2020010175-appb-I000268
    Figure PCTKR2020010175-appb-I000268
    Figure PCTKR2020010175-appb-I000269
    Figure PCTKR2020010175-appb-I000269
    Figure PCTKR2020010175-appb-I000270
    Figure PCTKR2020010175-appb-I000270
    Figure PCTKR2020010175-appb-I000271
    Figure PCTKR2020010175-appb-I000271
    Figure PCTKR2020010175-appb-I000272
    Figure PCTKR2020010175-appb-I000272
    Figure PCTKR2020010175-appb-I000273
    Figure PCTKR2020010175-appb-I000273
    Figure PCTKR2020010175-appb-I000274
    Figure PCTKR2020010175-appb-I000274
    Figure PCTKR2020010175-appb-I000275
    Figure PCTKR2020010175-appb-I000275
    Figure PCTKR2020010175-appb-I000276
    Figure PCTKR2020010175-appb-I000276
    Figure PCTKR2020010175-appb-I000277
    Figure PCTKR2020010175-appb-I000277
    Figure PCTKR2020010175-appb-I000278
    Figure PCTKR2020010175-appb-I000278
    Figure PCTKR2020010175-appb-I000279
    Figure PCTKR2020010175-appb-I000279
  7. 청구항 1에 있어서, 상기 화학식 2는 하기 화합물들 중 어느 하나인 것인 유기 발광 소자:The organic light-emitting device of claim 1, wherein Formula 2 is any one of the following compounds:
    Figure PCTKR2020010175-appb-I000280
    Figure PCTKR2020010175-appb-I000280
    Figure PCTKR2020010175-appb-I000281
    Figure PCTKR2020010175-appb-I000281
    Figure PCTKR2020010175-appb-I000282
    Figure PCTKR2020010175-appb-I000282
    Figure PCTKR2020010175-appb-I000283
    Figure PCTKR2020010175-appb-I000283
    Figure PCTKR2020010175-appb-I000284
    Figure PCTKR2020010175-appb-I000284
    Figure PCTKR2020010175-appb-I000285
    Figure PCTKR2020010175-appb-I000285
    Figure PCTKR2020010175-appb-I000286
    Figure PCTKR2020010175-appb-I000286
    Figure PCTKR2020010175-appb-I000287
    Figure PCTKR2020010175-appb-I000287
    Figure PCTKR2020010175-appb-I000288
    Figure PCTKR2020010175-appb-I000288
    Figure PCTKR2020010175-appb-I000289
    Figure PCTKR2020010175-appb-I000289
    Figure PCTKR2020010175-appb-I000290
    Figure PCTKR2020010175-appb-I000290
    Figure PCTKR2020010175-appb-I000291
    Figure PCTKR2020010175-appb-I000291
    Figure PCTKR2020010175-appb-I000292
    Figure PCTKR2020010175-appb-I000292
    Figure PCTKR2020010175-appb-I000293
    Figure PCTKR2020010175-appb-I000293
    Figure PCTKR2020010175-appb-I000294
    Figure PCTKR2020010175-appb-I000294
    Figure PCTKR2020010175-appb-I000295
    Figure PCTKR2020010175-appb-I000295
    Figure PCTKR2020010175-appb-I000296
    Figure PCTKR2020010175-appb-I000296
    Figure PCTKR2020010175-appb-I000297
    Figure PCTKR2020010175-appb-I000297
    Figure PCTKR2020010175-appb-I000298
    Figure PCTKR2020010175-appb-I000298
    Figure PCTKR2020010175-appb-I000299
    Figure PCTKR2020010175-appb-I000299
    Figure PCTKR2020010175-appb-I000300
    Figure PCTKR2020010175-appb-I000300
    Figure PCTKR2020010175-appb-I000301
    Figure PCTKR2020010175-appb-I000301
    Figure PCTKR2020010175-appb-I000302
    Figure PCTKR2020010175-appb-I000302
    Figure PCTKR2020010175-appb-I000303
    Figure PCTKR2020010175-appb-I000303
    Figure PCTKR2020010175-appb-I000304
    Figure PCTKR2020010175-appb-I000304
    Figure PCTKR2020010175-appb-I000305
    Figure PCTKR2020010175-appb-I000305
    Figure PCTKR2020010175-appb-I000306
    Figure PCTKR2020010175-appb-I000306
    Figure PCTKR2020010175-appb-I000307
    Figure PCTKR2020010175-appb-I000307
    Figure PCTKR2020010175-appb-I000308
    Figure PCTKR2020010175-appb-I000308
    Figure PCTKR2020010175-appb-I000309
    Figure PCTKR2020010175-appb-I000309
    Figure PCTKR2020010175-appb-I000310
    Figure PCTKR2020010175-appb-I000310
    Figure PCTKR2020010175-appb-I000311
    Figure PCTKR2020010175-appb-I000311
    Figure PCTKR2020010175-appb-I000312
    Figure PCTKR2020010175-appb-I000312
    Figure PCTKR2020010175-appb-I000313
    Figure PCTKR2020010175-appb-I000313
    Figure PCTKR2020010175-appb-I000314
    Figure PCTKR2020010175-appb-I000314
    Figure PCTKR2020010175-appb-I000315
    Figure PCTKR2020010175-appb-I000315
    Figure PCTKR2020010175-appb-I000316
    Figure PCTKR2020010175-appb-I000316
    Figure PCTKR2020010175-appb-I000317
    Figure PCTKR2020010175-appb-I000317
    Figure PCTKR2020010175-appb-I000318
    Figure PCTKR2020010175-appb-I000318
    Figure PCTKR2020010175-appb-I000319
    Figure PCTKR2020010175-appb-I000319
    Figure PCTKR2020010175-appb-I000320
    Figure PCTKR2020010175-appb-I000320
    Figure PCTKR2020010175-appb-I000321
    Figure PCTKR2020010175-appb-I000321
    Figure PCTKR2020010175-appb-I000322
    Figure PCTKR2020010175-appb-I000322
    Figure PCTKR2020010175-appb-I000323
    Figure PCTKR2020010175-appb-I000323
    Figure PCTKR2020010175-appb-I000324
    Figure PCTKR2020010175-appb-I000324
    Figure PCTKR2020010175-appb-I000325
    Figure PCTKR2020010175-appb-I000325
    Figure PCTKR2020010175-appb-I000326
    Figure PCTKR2020010175-appb-I000326
    Figure PCTKR2020010175-appb-I000327
    Figure PCTKR2020010175-appb-I000327
    Figure PCTKR2020010175-appb-I000328
    Figure PCTKR2020010175-appb-I000328
    Figure PCTKR2020010175-appb-I000329
    Figure PCTKR2020010175-appb-I000329
    Figure PCTKR2020010175-appb-I000330
    Figure PCTKR2020010175-appb-I000330
    Figure PCTKR2020010175-appb-I000331
    Figure PCTKR2020010175-appb-I000331
    Figure PCTKR2020010175-appb-I000332
    Figure PCTKR2020010175-appb-I000332
    Figure PCTKR2020010175-appb-I000333
    Figure PCTKR2020010175-appb-I000333
    Figure PCTKR2020010175-appb-I000334
    Figure PCTKR2020010175-appb-I000334
    Figure PCTKR2020010175-appb-I000335
    Figure PCTKR2020010175-appb-I000335
    Figure PCTKR2020010175-appb-I000336
    Figure PCTKR2020010175-appb-I000336
    Figure PCTKR2020010175-appb-I000337
    Figure PCTKR2020010175-appb-I000337
    Figure PCTKR2020010175-appb-I000338
    Figure PCTKR2020010175-appb-I000338
    Figure PCTKR2020010175-appb-I000339
    Figure PCTKR2020010175-appb-I000339
    Figure PCTKR2020010175-appb-I000340
    .
    Figure PCTKR2020010175-appb-I000340
    .
  8. 청구항 1에 있어서, 상기 화학식 2는 하기 표에 기재된 화합물 중 어느 하나인 것인 유기발광소자:The organic light-emitting device of claim 1, wherein Formula 2 is any one of the compounds listed in the following table:
    Figure PCTKR2020010175-appb-I000341
    Figure PCTKR2020010175-appb-I000341
    Figure PCTKR2020010175-appb-I000342
    Figure PCTKR2020010175-appb-I000342
    Figure PCTKR2020010175-appb-I000343
    Figure PCTKR2020010175-appb-I000343
    Figure PCTKR2020010175-appb-I000344
    Figure PCTKR2020010175-appb-I000344
    Figure PCTKR2020010175-appb-I000345
    Figure PCTKR2020010175-appb-I000345
    Figure PCTKR2020010175-appb-I000346
    Figure PCTKR2020010175-appb-I000346
    Figure PCTKR2020010175-appb-I000347
    Figure PCTKR2020010175-appb-I000347
    Figure PCTKR2020010175-appb-I000348
    Figure PCTKR2020010175-appb-I000348
    Figure PCTKR2020010175-appb-I000349
    Figure PCTKR2020010175-appb-I000349
    Figure PCTKR2020010175-appb-I000350
    Figure PCTKR2020010175-appb-I000350
    Figure PCTKR2020010175-appb-I000351
    Figure PCTKR2020010175-appb-I000351
    Figure PCTKR2020010175-appb-I000352
    Figure PCTKR2020010175-appb-I000352
    Figure PCTKR2020010175-appb-I000353
    Figure PCTKR2020010175-appb-I000353
    Figure PCTKR2020010175-appb-I000354
    Figure PCTKR2020010175-appb-I000354
    Figure PCTKR2020010175-appb-I000355
    Figure PCTKR2020010175-appb-I000355
    Figure PCTKR2020010175-appb-I000356
    Figure PCTKR2020010175-appb-I000356
    Figure PCTKR2020010175-appb-I000357
    Figure PCTKR2020010175-appb-I000357
    Figure PCTKR2020010175-appb-I000358
    Figure PCTKR2020010175-appb-I000358
    Figure PCTKR2020010175-appb-I000359
    Figure PCTKR2020010175-appb-I000359
    Figure PCTKR2020010175-appb-I000360
    Figure PCTKR2020010175-appb-I000360
    Figure PCTKR2020010175-appb-I000361
    Figure PCTKR2020010175-appb-I000361
    Figure PCTKR2020010175-appb-I000362
    Figure PCTKR2020010175-appb-I000362
    Figure PCTKR2020010175-appb-I000363
    Figure PCTKR2020010175-appb-I000363
    Figure PCTKR2020010175-appb-I000364
    Figure PCTKR2020010175-appb-I000364
    Figure PCTKR2020010175-appb-I000365
    Figure PCTKR2020010175-appb-I000365
    Figure PCTKR2020010175-appb-I000366
    Figure PCTKR2020010175-appb-I000366
    Figure PCTKR2020010175-appb-I000367
    Figure PCTKR2020010175-appb-I000367
    Figure PCTKR2020010175-appb-I000368
    Figure PCTKR2020010175-appb-I000368
    Figure PCTKR2020010175-appb-I000369
    Figure PCTKR2020010175-appb-I000369
    Figure PCTKR2020010175-appb-I000370
    Figure PCTKR2020010175-appb-I000370
    Figure PCTKR2020010175-appb-I000371
    Figure PCTKR2020010175-appb-I000371
    Figure PCTKR2020010175-appb-I000372
    Figure PCTKR2020010175-appb-I000372
    Figure PCTKR2020010175-appb-I000373
    Figure PCTKR2020010175-appb-I000373
    Figure PCTKR2020010175-appb-I000374
    Figure PCTKR2020010175-appb-I000374
    Figure PCTKR2020010175-appb-I000375
    Figure PCTKR2020010175-appb-I000375
    Figure PCTKR2020010175-appb-I000376
    Figure PCTKR2020010175-appb-I000376
    Figure PCTKR2020010175-appb-I000377
    Figure PCTKR2020010175-appb-I000377
    Figure PCTKR2020010175-appb-I000378
    Figure PCTKR2020010175-appb-I000378
    Figure PCTKR2020010175-appb-I000379
    Figure PCTKR2020010175-appb-I000379
    Figure PCTKR2020010175-appb-I000380
    Figure PCTKR2020010175-appb-I000380
    Figure PCTKR2020010175-appb-I000381
    Figure PCTKR2020010175-appb-I000381
    Figure PCTKR2020010175-appb-I000382
    Figure PCTKR2020010175-appb-I000382
    Figure PCTKR2020010175-appb-I000383
    Figure PCTKR2020010175-appb-I000383
    Figure PCTKR2020010175-appb-I000384
    Figure PCTKR2020010175-appb-I000384
    Figure PCTKR2020010175-appb-I000385
    Figure PCTKR2020010175-appb-I000385
    Figure PCTKR2020010175-appb-I000386
    Figure PCTKR2020010175-appb-I000386
    Figure PCTKR2020010175-appb-I000387
    Figure PCTKR2020010175-appb-I000387
    Figure PCTKR2020010175-appb-I000388
    Figure PCTKR2020010175-appb-I000388
    Figure PCTKR2020010175-appb-I000389
    Figure PCTKR2020010175-appb-I000389
    Figure PCTKR2020010175-appb-I000390
    Figure PCTKR2020010175-appb-I000390
    Figure PCTKR2020010175-appb-I000391
    Figure PCTKR2020010175-appb-I000391
    Figure PCTKR2020010175-appb-I000392
    Figure PCTKR2020010175-appb-I000392
    Figure PCTKR2020010175-appb-I000393
    Figure PCTKR2020010175-appb-I000393
    Figure PCTKR2020010175-appb-I000394
    Figure PCTKR2020010175-appb-I000394
    Figure PCTKR2020010175-appb-I000395
    Figure PCTKR2020010175-appb-I000395
    Figure PCTKR2020010175-appb-I000396
    Figure PCTKR2020010175-appb-I000396
    Figure PCTKR2020010175-appb-I000397
    Figure PCTKR2020010175-appb-I000397
    Figure PCTKR2020010175-appb-I000398
    Figure PCTKR2020010175-appb-I000398
    Figure PCTKR2020010175-appb-I000399
    Figure PCTKR2020010175-appb-I000399
    Figure PCTKR2020010175-appb-I000400
    Figure PCTKR2020010175-appb-I000400
    Figure PCTKR2020010175-appb-I000401
    Figure PCTKR2020010175-appb-I000401
    Figure PCTKR2020010175-appb-I000402
    Figure PCTKR2020010175-appb-I000402
    Figure PCTKR2020010175-appb-I000403
    Figure PCTKR2020010175-appb-I000403
    Figure PCTKR2020010175-appb-I000404
    Figure PCTKR2020010175-appb-I000404
    Figure PCTKR2020010175-appb-I000405
    Figure PCTKR2020010175-appb-I000405
    Figure PCTKR2020010175-appb-I000406
    Figure PCTKR2020010175-appb-I000406
    Figure PCTKR2020010175-appb-I000407
    Figure PCTKR2020010175-appb-I000407
    Figure PCTKR2020010175-appb-I000408
    Figure PCTKR2020010175-appb-I000408
    Figure PCTKR2020010175-appb-I000409
    Figure PCTKR2020010175-appb-I000409
    Figure PCTKR2020010175-appb-I000410
    Figure PCTKR2020010175-appb-I000410
    Figure PCTKR2020010175-appb-I000411
    Figure PCTKR2020010175-appb-I000411
    Figure PCTKR2020010175-appb-I000412
    Figure PCTKR2020010175-appb-I000412
    Figure PCTKR2020010175-appb-I000413
    Figure PCTKR2020010175-appb-I000413
    Figure PCTKR2020010175-appb-I000414
    Figure PCTKR2020010175-appb-I000414
    Figure PCTKR2020010175-appb-I000415
    Figure PCTKR2020010175-appb-I000415
    Figure PCTKR2020010175-appb-I000416
    Figure PCTKR2020010175-appb-I000416
    Figure PCTKR2020010175-appb-I000417
    Figure PCTKR2020010175-appb-I000417
    Figure PCTKR2020010175-appb-I000418
    Figure PCTKR2020010175-appb-I000418
    Figure PCTKR2020010175-appb-I000419
    Figure PCTKR2020010175-appb-I000419
    Figure PCTKR2020010175-appb-I000420
    Figure PCTKR2020010175-appb-I000420
    Figure PCTKR2020010175-appb-I000421
    Figure PCTKR2020010175-appb-I000421
    Figure PCTKR2020010175-appb-I000422
    Figure PCTKR2020010175-appb-I000422
    Figure PCTKR2020010175-appb-I000423
    Figure PCTKR2020010175-appb-I000423
    Figure PCTKR2020010175-appb-I000424
    Figure PCTKR2020010175-appb-I000424
    Figure PCTKR2020010175-appb-I000425
    Figure PCTKR2020010175-appb-I000425
    Figure PCTKR2020010175-appb-I000426
    Figure PCTKR2020010175-appb-I000426
    Figure PCTKR2020010175-appb-I000427
    Figure PCTKR2020010175-appb-I000427
    Figure PCTKR2020010175-appb-I000428
    Figure PCTKR2020010175-appb-I000428
    Figure PCTKR2020010175-appb-I000429
    Figure PCTKR2020010175-appb-I000429
    Figure PCTKR2020010175-appb-I000430
    Figure PCTKR2020010175-appb-I000430
    Figure PCTKR2020010175-appb-I000431
    Figure PCTKR2020010175-appb-I000431
    ..
  9. 청구항 1에 있어서,The method according to claim 1,
    상기 제1 전극은 양극이고, 상기 제2 전극은 음극이며, 상기 제1 유기물층은 발광층이고, 상기 제2 유기물층은 상기 제2 전극과 상기 제1 유기물층 사이에 구비되는 것인 유기 발광 소자.The first electrode is an anode, the second electrode is a cathode, the first organic material layer is an emission layer, and the second organic material layer is provided between the second electrode and the first organic material layer.
  10. 청구항 1에 있어서,The method according to claim 1,
    상기 유기물층은 2층 이상의 발광층을 포함하고, 상기 2층 이상의 발광층 중 1층은 상기 화학식 1로 표시되는 화합물을 포함하는 것인 유기 발광 소자.The organic material layer includes two or more emission layers, and one of the two or more emission layers includes a compound represented by Formula 1 above.
  11. 청구항 1에 있어서,The method according to claim 1,
    상기 제2 유기물층은 알칼리 금속 및 알칼리토금속 중에서 선택되는 1종 또는 2종 이상의 n형 도펀트를 더 포함하는 것인 유기 발광 소자.The second organic material layer is an organic light-emitting device further comprising one or two or more n-type dopants selected from alkali metals and alkaline earth metals.
  12. 청구항 1에 있어서,The method according to claim 1,
    상기 제2 유기물층은 정공차단층, 전자수송층, 전자주입층, 및 전자주입 및 수송층으로 이루어진군에서 선택된 1층 이상을 포함하는 것인 유기 발광 소자.The second organic material layer is an organic light emitting device comprising at least one layer selected from the group consisting of a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer.
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