WO2018074881A1 - Composé polycyclique et élément électroluminescent organique le comprenant - Google Patents

Composé polycyclique et élément électroluminescent organique le comprenant Download PDF

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WO2018074881A1
WO2018074881A1 PCT/KR2017/011639 KR2017011639W WO2018074881A1 WO 2018074881 A1 WO2018074881 A1 WO 2018074881A1 KR 2017011639 W KR2017011639 W KR 2017011639W WO 2018074881 A1 WO2018074881 A1 WO 2018074881A1
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group
substituted
unsubstituted
light emitting
compound
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PCT/KR2017/011639
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English (en)
Korean (ko)
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차용범
김진주
홍성길
김성소
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주식회사 엘지화학
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Priority claimed from KR1020170135383A external-priority patent/KR101956790B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to EP17863069.5A priority Critical patent/EP3428163B1/fr
Priority to CN201780024271.2A priority patent/CN109071510B/zh
Priority to JP2018548912A priority patent/JP6780705B2/ja
Priority to US16/088,406 priority patent/US11718606B2/en
Publication of WO2018074881A1 publication Critical patent/WO2018074881A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene

Definitions

  • the present specification relates to a multicyclic compound and an organic light emitting device including the same.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon usually 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 to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • the present specification provides a multicyclic compound and an organic light emitting device including the same.
  • R1 and R2 are the same as or different from each other, and each independently an aryl group
  • R3 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • L1 and L2 are the same as or different from each other, and each independently a single bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • a and B are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted heteroaryl group; Substituted or unsubstituted silyl group; Or a substituted or unsubstituted phosphine oxide group.
  • the first electrode A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a compound represented by Chemical Formula 1. .
  • the compound according to the exemplary embodiment of the present specification may be used as a material of the organic material layer of the organic light emitting device, and by using the compound, it is possible to improve efficiency, low driving voltage, and / or lifespan characteristics in the organic light emitting device.
  • FIG. 1 illustrates an organic light emitting device according to an exemplary embodiment of the present specification.
  • FIG. 2 illustrates an organic light emitting diode according to another exemplary embodiment of the present specification.
  • 1 substrate, 2: anode, 3: light emitting layer, 4: cathode, 5: hole injection layer, 6: hole transport layer, 7: electron transport layer
  • An exemplary embodiment of the present specification provides a compound represented by Chemical Formula 1. Specifically, one embodiment of the present specification provides a multicyclic compound having a specific substituent at positions 2 and 3 of fluorene.
  • substituted means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.
  • substituted or unsubstituted is deuterium; Nitrile group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more of the substituents exemplified above are substituted with a substituent, or means that do not have any substitu
  • a substituent to which two or more substituents are linked may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, or the like.
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 30.
  • Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-o
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto. It is not.
  • the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like It may be, but is not limited thereto.
  • the amine group is -NH 2 ; Alkylamine group; N-alkylarylamine group; Arylamine group; N-aryl heteroaryl amine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, carbon number is not particularly limited, but is preferably 1 to 30.
  • Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group.
  • the N-alkylarylamine group means an amine group in which an alkyl group and an aryl group are substituted for N of the amine group.
  • the N-arylheteroarylamine group means an amine group in which an aryl group and a heteroaryl group are substituted for N in the amine group.
  • the N-alkylheteroarylamine group means an amine group in which an alkyl group and a heteroarylamine group are substituted for N of the amine group.
  • the alkyl group in the alkylamine group, the N-arylalkylamine group, the alkylthioxy group, the alkyl sulfoxy group, and the N-alkylheteroarylamine group is the same as the example of the alkyl group described above.
  • the alkenyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 30.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.
  • the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
  • the present invention is not limited thereto.
  • the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
  • the aryl group is a monocyclic aryl group
  • carbon number is not particularly limited, but is preferably 6 to 30 carbon atoms.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
  • Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-30.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, triphenyl group, pyrenyl group, penalenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto. no.
  • the fluorenyl group may be substituted, and adjacent groups may combine with each other to form a ring.
  • the aryl group in the aryloxy group, the N-arylalkylamine group, and the N-arylheteroarylamine group is the same as the aryl group described above.
  • the aryloxy group may be 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, 9-phenanthryloxy group, and the like.
  • the heteroaryl group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. Although carbon number is not particularly limited, it is preferably 2 to 30 carbon atoms, the heteroaryl group may be monocyclic or polycyclic.
  • heterocyclic group examples include thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, tria Zolyl group, acridil group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , Isoquinolinyl group, indolyl group, carbazolyl group, benzooxazolyl group, benzoimidazolyl group, benzothiazolyl group, benzocarbazolyl group, dibenzopyrrol
  • examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group.
  • the heteroarylamine group including two or more heteroaryl groups may simultaneously include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group.
  • the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroaryl group described above.
  • a and B of Formula 1 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted heteroaryl group; Substituted or unsubstituted silyl group; Or a substituted or unsubstituted phosphine oxide group.
  • a and B of Formula 1 are the same as or different from each other, each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; An amine group substituted or unsubstituted with an alkyl group, or an amine group substituted with a heteroaryl group including any one or more of N, O and S unsubstituted or substituted with an aryl group; A heteroaryl group including any one or more of N, O, and S of a substituted or unsubstituted monocyclic or polycyclic; A silyl group unsubstituted or substituted with an aryl group; Or a phosphine oxide group unsubstituted or substituted with an aryl group.
  • a and B of Formula 1 are the same as or different from each other, and each independently an alkyl group; Silyl groups substituted with alkyl groups; Heteroaryl groups unsubstituted or substituted with aryl groups; An aryl group unsubstituted or substituted with an alkyl group; An amine group substituted with an aryl group unsubstituted or substituted with an alkyl group; Or an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a phosphine oxide group substituted with an aryl group.
  • a and B of Formula 1 are the same as or different from each other, and each independently an alkyl group having 1 to 10 carbon atoms; Silyl groups substituted with methyl groups; An aryl group unsubstituted or substituted with an alkyl group, or an amine group substituted with a heteroaryl group unsubstituted or substituted with an aryl group; Phosphine oxide groups substituted with aryl groups; Or a C6-C30 aryl group unsubstituted or substituted with a nitrile group or an alkyl group, or a C6-substituted or unsubstituted heteroaryl group including any one or more of N, O, and S unsubstituted or substituted with an aryl group.
  • aryl group of 30 To aryl group of 30.
  • a and B of Formula 1 are the same as or different from each other, and each independently a methyl group; Turbutyl group; Silyl groups substituted with methyl groups; An aryl group unsubstituted or substituted with a methyl group, or an amine group substituted with a heteroaryl group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; Phosphine oxide groups substituted with an aryl group having 6 to 30 carbon atoms; A phenyl group unsubstituted or substituted with a nitrile group or an alkyl group; Phenanthrene group; Triphenylene group; Fluorene groups substituted with methyl groups; Naphthyl group; Dibenzofuran group; Dibenzothiophene group; Monocyclic or polycyclic N-containing heterocyclic groups unsubstituted or substituted with a phenyl group or a biphenyl group;
  • a and B of Formula 1 are the same as or different from each other, and each independently a methyl group; Turbutyl group; Trimethylsilyl group (TMS); An amine group substituted with a phenyl group, a biphenyl group, a terphenyl group, a dimethylfluorene group, a dibenzothiophene group, a dibenzofuran group, or a carbazole group substituted with a phenyl group; Diphenylphosphine oxide group; A phenyl group unsubstituted or substituted with a nitrile group; Phenanthrene group; Triphenylene group; Dimethyl fluorene group; Naphthyl group; Dibenzofuran group; Dibenzothiophene group; Benzocarbazole group; Carbazole groups; Triazine group unsubstituted or substituted with a phenyl group or a bipheny
  • a and B of Formula 1 are the same as or different from each other, each independently represent a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; An amine group substituted or unsubstituted with an alkyl group, or an amine group substituted with a heteroaryl group including any one or more of N, O and S unsubstituted or substituted with an aryl group; A heteroaryl group including any one or more of N, O, and S of a substituted or unsubstituted monocyclic or polycyclic; A silyl group unsubstituted or substituted with an aryl group; Or a phosphine oxide group unsubstituted or substituted with an aryl group.
  • a and B of Formula 1 are the same as or different from each other, and each independently An alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; An amine group substituted with a C6-C30 aryl group substituted or unsubstituted with a methyl group, or a C6-C30 heteroaryl group including any one or more of N, O and S unsubstituted or substituted with an aryl group; Heteroaryl group containing O or S substituted with an aryl group having 6 to 30 carbon atoms; Or a heteroaryl group including any one or more of N, O and S having 3 to 30 carbon atoms unsubstituted or substituted with a aryl group having 6 to 30 carbon atoms or a heteroaryl group containing any one of N, O, and S; A silyl group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms
  • a and B of Formula 1 are the same as or different from each other, and each independently a methyl group substituted with a phenyl group;
  • Dibenzofuran group unsubstituted or substituted with a phenyl group;
  • Dibenzothiophene group unsubstituted or substituted with a phenyl group; Benzonaphthofuran group; Benzonaphthothiophene group; Thiophene group substituted with phenyl group;
  • Carbazole groups unsubstituted or substituted with a phenyl
  • a and B of Formula 1 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a nitrile group; Dimethyl fluorene group; Dibenzofuran group; Dibenzothiophene group; Carbazole groups unsubstituted or substituted with a phenyl group; Triazine group unsubstituted or substituted with a phenyl group or a biphenyl group; A pyrimidine group unsubstituted or substituted with a phenyl group; A pyridine group unsubstituted or substituted with a phenyl group; Or an amine group substituted with a carbazole group substituted with a phenyl group, biphenyl group, terphenyl group, dimethylfluorene group, dibenzothiophene group, dibenzofuran group, or phenyl group.
  • a and B of Formula 1 may be any one of the following compounds.
  • R1 and R2 are a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R1 and R2 is a phenyl group.
  • R3 to R8 is hydrogen.
  • L1 and L2 of Formula 1 are the same as or different from each other, each independently a direct bond, an arylene group having 6 to 30 carbon atoms; Or an N-containing heteroarylene group having 3 to 30 carbon atoms.
  • L1 and L2 of Formula 1 is a direct bond, a phenylene group, a biphenylene group or a carbazolene group.
  • Formula 1 may be any one selected from the following compounds.
  • the compound of Formula 1 may be prepared according to the following reaction scheme, but is not limited thereto.
  • the type and number of substituents can be determined by appropriate selection of known starting materials. Reaction type and reaction conditions may be used those known in the art.
  • the first electrode A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound described above.
  • the organic material layer of the organic light emitting device of the present specification may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto and may include fewer or more organic layers.
  • the structure of the organic light emitting device of the present specification may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.
  • 1 illustrates a structure of an organic light emitting device in which a first electrode 2, a light emitting layer 3, and a second electrode 4 are sequentially stacked on a substrate 1.
  • 1 is an exemplary structure of an organic light emitting device according to an exemplary embodiment of the present specification, and may further include another organic material layer.
  • 2 shows a first electrode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7, an electron injection layer 8 and a second electrode on a substrate 1.
  • the structure of the organic light emitting element 4) is sequentially illustrated. 2 is an exemplary structure according to an exemplary embodiment of the present specification, and may further include another organic material layer.
  • the organic material layer includes a hole injection layer, a hole transport layer or an electron blocking layer, and the hole injection layer, the hole transport layer or the electron blocking layer includes a compound represented by Chemical Formula 1.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes a compound represented by Chemical Formula 1 as a host of the light emitting layer.
  • the organic material layer includes a hole blocking layer, an electron transport layer or an electron injection layer, and the hole blocking layer, the electron transport layer or the electron injection layer includes a compound represented by Chemical Formula 1.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by the following Chemical Formula 2.
  • Ar is a benzofluorene skeleton, a fluoranthene skeleton, a pyrene skeleton or a chrysene skeleton,
  • L3 is a single bond, an aryl group of C6 to C30 or a heterocyclic group of C5 to C30,
  • X1 and X2 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C5 to C30 heterocyclic group, a substituted or unsubstituted C1 to C30 alkyl group and a substitution Or an unsubstituted C7 to C30 arylalkyl group, X1 and X2 may combine with each other to form a saturated or unsaturated ring,
  • r is an integer of 1 or more
  • X 1 is the same as or different from each other
  • X 2 is the same or different from each other.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes the compound represented by Formula 2 as a dopant of the light emitting layer.
  • L3 is a direct bond.
  • the r is 2.
  • Ar is a divalent pyrene group unsubstituted or substituted with deuterium, a methyl group, an ethyl group, an isopropyl group, or a tert-butyl group; Or a divalent chrysene group unsubstituted or substituted with deuterium, methyl, ethyl or tert-butyl groups.
  • X1 and X2 are the same as or different from each other, each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • X1 and X2 are the same as or different from each other, and each independently substituted or unsubstituted with a silyl group substituted with a methyl group, ethyl group, isopropyl group, tert-butyl group, nitrile group or alkyl group It is a C6-C30 aryl group.
  • X1 and X2 are the same as or different from each other, and each independently represent an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a methyl group.
  • X1 and X2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted terphenyl group.
  • X1 and X2 are the same as or different from each other, and each independently substituted or unsubstituted with a silyl group substituted with a methyl group, ethyl group, isopropyl group, tert-butyl group, nitrile group or alkyl group It is a phenyl group.
  • X1 and X2 are the same as or different from each other, and each independently substituted or unsubstituted with a silyl group substituted with a methyl group, ethyl group, isopropyl group, tert-butyl group, nitrile group or alkyl group It is a biphenyl group.
  • X1 and X2 are the same as or different from each other, and each independently substituted or unsubstituted with a silyl group substituted with a methyl group, ethyl group, isopropyl group, tert-butyl group, nitrile group or alkyl group It is a terphenyl group.
  • X1 and X2 are the same as or different from each other, each independently represent a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms.
  • X1 and X2 are the same as or different from each other, and each independently substituted with a silyl group or a phenyl group substituted with a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a nitrile group, an alkyl group or It is an unsubstituted heteroaryl group having 6 to 30 carbon atoms.
  • X1 and X2 are the same as or different from each other, and each independently substituted with a silyl group or a phenyl group substituted with a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a nitrile group, an alkyl group or It is an unsubstituted dibenzofuran group.
  • X1 and X2 are the same as or different from each other, each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms.
  • X1 and X2 are the same as or different from each other, and each independently an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a methyl group; And a heteroaryl group having 6 to 30 carbon atoms unsubstituted or substituted with a silyl group substituted with a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a nitrile group, an alkyl group, or a phenyl group.
  • X1 and X2 are the same as or different from each other, and each independently a phenyl group substituted with a methyl group; And dibenzofuran groups.
  • Formula 2 is selected from the following compounds.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by the following Chemical Formula 3.
  • Ar11 and Ar12 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic aryl group; Or a substituted or unsubstituted polycyclic aryl group,
  • G1 to G8 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted monocyclic aryl group; Or a substituted or unsubstituted polycyclic aryl group.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes a compound represented by Chemical Formula 3 as a host of the light emitting layer.
  • Ar11 and Ar12 are the same as or different from each other, and each independently a substituted or unsubstituted polycyclic aryl group.
  • Ar11 and Ar12 are the same as or different from each other, and each independently represent a substituted or unsubstituted polycyclic aryl group having 10 to 30 carbon atoms.
  • Ar11 and Ar12 are the same as or different from each other, and each independently a substituted or unsubstituted naphthyl group.
  • Ar11 and Ar12 are the same as or different from each other, and each independently a substituted or unsubstituted 1-naphthyl group, or a substituted or unsubstituted 2-naphthyl group.
  • Ar11 is a 1-naphthyl group
  • Ar12 is a 2-naphthyl group.
  • the G1 to G8 is hydrogen.
  • Chemical Formula 3 is selected from the following compounds.
  • the light emitting layer includes a host.
  • the light emitting layer includes a dopant.
  • the light emitting layer includes a phosphorescent dopant.
  • the light emitting layer includes both a host and a dopant.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes the compound represented by Formula 2 as a dopant of the light emitting layer
  • the compound represented by Formula 3 as a host of the light emitting layer
  • the electron blocking layer includes the compound of Formula 1.
  • the electron transport layer comprises a compound of Formula 1.
  • the organic material layer may further include one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
  • the organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of the present specification, that is, the compound represented by Chemical Formula 1.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a physical vapor deposition PVD: physical vapor deposition
  • PVD physical vapor deposition
  • sputtering e-beam evaporation
  • a metal or conductive metal oxide or an alloy thereof on the substrate
  • It can be prepared by forming a first electrode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a second electrode thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate.
  • the compound represented by Chemical Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
  • 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 anode material a material having a large work function is usually preferred to facilitate hole injection into the organic material layer.
  • the positive electrode 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), indium zinc oxide (IZO); ZnO: Al or SnO 2 : Combination of metals and oxides such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode material is 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; Multilayer structure materials such as LiF / Al or LiO 2 / Al, Mg / Ag, and the like, but are not limited thereto.
  • the hole injection layer is a layer for injecting holes from an electrode with a hole injection material, and has a capability of transporting holes with a hole injection material, and thus has a hole injection effect at an anode, and an excellent hole injection effect with respect to a light emitting layer or a light emitting material.
  • generated in the light emitting layer to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable.
  • the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.
  • the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer.
  • the material is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the light emitting material of the light emitting layer is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzothiazole and benzoimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • the light emitting layer may include a host material and a dopant material.
  • the host material is a condensed aromatic ring derivative or a hetero ring-containing compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the dopant material examples include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and a styrylamine compound may be substituted or unsubstituted.
  • At least one arylvinyl group is substituted with the substituted arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
  • the electron transporting material of the electron transporting layer is a layer for receiving electrons from the electron injection layer and transporting electrons to the light emitting layer.
  • the electron transporting material is a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer. This large material is suitable. Specific examples thereof include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired cathode material as used in accordance with the prior art.
  • suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.
  • the electron injection layer is a layer that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer.
  • the compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) 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-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a double side emission type according to a material used.
  • Tetrahydrofuran with Compound A (6.23g, 9.09mmol), 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.34g, 8.64mmol) in 500ml round bottom flask under nitrogen atmosphere After dissolving completely in 160ml, 2M aqueous potassium carbonate solution (80ml) was added, tetrakis- (triphenylphosphine) palladium (0.32g, 0.27mmol) was added thereto, and the mixture was heated and stirred for 4 hours.
  • Tetrahydrofuran Compound A (7.75g, 11.31mmol), 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (4.16g, 10.75mmol) in 500ml round bottom flask in nitrogen atmosphere After dissolving completely in 220ml, 2M aqueous potassium carbonate solution (110ml) was added, tetrakis- (triphenylphosphine) palladium (0.39g, 0.34mmol) was added thereto, and the mixture was heated and stirred for 3 hours.
  • Tetrahydrofuran Compound B (11.45g, 15.90mmol), 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (5.35g, 13.82mmol) in 500ml round bottom flask in nitrogen atmosphere After completely dissolved in 240ml 2M potassium carbonate solution (120ml) was added, tetrakis- (triphenylphosphine) palladium (0.48g, 0.41mmol) was added and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 450 ml of acetone to prepare compound 16 (8.64 g, 69%).
  • a glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 ⁇ was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • ITO indium tin oxide
  • Fischer Co. product was used as a detergent
  • distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water.
  • ultrasonic washing was performed twice with distilled water for 10 minutes.
  • ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol dried and transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • hexanitrile hexaazatriphenylene (HAT) of the following formula was thermally vacuum deposited to a thickness of 500 kPa on the prepared ITO transparent electrode to form a hole injection layer.
  • the following Compound 7 was vacuum deposited on the hole transport layer to have a film thickness of 100 GPa to form an electron blocking layer.
  • BH and BD as described below were vacuum-deposited at a weight ratio of 25: 1 on the electron blocking layer to form a light emitting layer.
  • the compound ET1 and the compound LiQ were vacuum-deposited on the emission layer in a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 300 kPa.
  • lithium fluoride (LiF) and aluminum were deposited to a thickness of 12 kPa in order to form a cathode.
  • the organic light emitting device was manufactured by maintaining 7 to 5 ⁇ 10 ⁇ 6 torr.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 9 was used instead of compound 7 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 13 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 14 was used instead of compound 7 in Experimental Example 1-1.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1-1 except for using the following EB 1 compound instead of compound 7 in Experimental Example 1-1.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1-1 except for using the following EB 2 compound instead of compound 7 in Experimental Example 1-1.
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that the following compound of EB 3 was used instead of compound 7 in Experimental Example 1-1.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1-1 except for using the following EB 4 compound instead of compound 7 in Experimental Example 1-1.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1-1 except for using the following EB 5 compound instead of compound 7 in Experimental Example 1-1.
  • T95 means the time it takes for the luminance to decrease to 95% from the initial luminance (1300 nits).
  • the organic light emitting device manufactured by using the compound of the present invention as an electron blocking layer exhibits excellent characteristics in terms of efficiency, driving voltage, and / or stability of the organic light emitting device.
  • molecules having steric hindrance due to the close proximity of two substituents made by a synthetic method recently developed by the company have a twisted structure compared to a substance in which one substituent or two substituents are far apart. In order to change the morphology, the efficiency and lifespan are generally increased.
  • Comparative Examples 1 to 5 organic light emitting devices manufactured by using a compound having a substituent connected to both 9,9-diphenylfluorene separately separated or having only one substituent at positions 2 and 3 positioned as an electron blocking layer
  • Compounds of the present invention having a substituent connected to the adjacent positions 2 and 3 more than 5% increases the efficiency and shows a 10 to 30% increase in lifespan.
  • the compounds of Comparative Example 5, in which the substituents are connected at positions 1 and 4 apart from each other are increased in voltage and greatly deteriorated in life, and have no effect of increasing efficiency.
  • a glass substrate (corning 7059 glass) coated with ITO (Indium Tin Oxide) at a thickness of 1,000 kPa was placed in distilled water in which a dispersant was dissolved and washed with ultrasonic waves. Fischer Co. products were used for the detergent, and Millipore Co. Secondly filtered distilled water was used as a filter of the product. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried.
  • ITO Indium Tin Oxide
  • the hexanitrile hexaazatriphenylene was thermally vacuum deposited to a thickness of 500 kPa on the prepared ITO transparent electrode to form a hole injection layer.
  • HT1 300 kPa
  • EB1 100 kPa
  • Compound 1 and Ir (ppy) 3 dopant synthesized in Preparation Example 1 as a light emitting layer were vacuum deposited to a thickness of 200 Pa at 10% concentration.
  • the ET1 compound (300 Pa) was thermally vacuum deposited sequentially into the electron injection and transport layer.
  • lithium fluoride LiF
  • aluminum 12 ⁇ of lithium fluoride (LiF) and 2,000 ⁇ of aluminum were sequentially deposited on the electron transport layer to form a cathode, thereby manufacturing an organic light emitting device.
  • the deposition rate of the organic material was maintained at 1 ⁇ / sec
  • the lithium fluoride was 0.2 ⁇ / sec
  • the aluminum was maintained at a deposition rate of 3 to 7 ⁇ / sec.
  • HAT HAT
  • HT1 HT1
  • EB1 EB1
  • ET1 EB1
  • Compound 1 The structures of HAT, HT1, EB1, ET1, and Compound 1 are as follows.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 2 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 4 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 5 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 10 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 11 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 15 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 16 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 17 was used instead of compound 1 in Experimental Example 2-1.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 2-1 except for using the following GH 1 compound instead of compound 1 in Experimental Example 2-1.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 2-1 except for using the following GH 2 compound instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that the following compound of GH 3 was used instead of compound 1 in Experimental Example 2-1.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 2-1 except for using the following GH 4 compound instead of compound 1 in Experimental Example 2-1.
  • T95 means the time it takes for the luminance to decrease to 95% from the initial luminance (6000nit).
  • An organic light-emitting device was manufactured in the same manner as in Experimental Example 3-1, except that Compound ET 2 was used instead of Compound 1 in Experimental Example 3-1.
  • T95 means the time it takes for the luminance to decrease to 95% from the initial luminance (6000nit).
  • Comparative Example 10 The material of Comparative Example 10 in which the phosphine oxide and the triazine group are not adjacent to each other is maintained to some extent, but the voltage is measured very high and the efficiency is also reduced by more than 10%.

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Abstract

La présente invention concerne un composé polycyclique de formule chimique 1 et un élément électroluminescent organique le comprenant.
PCT/KR2017/011639 2016-10-20 2017-10-20 Composé polycyclique et élément électroluminescent organique le comprenant WO2018074881A1 (fr)

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EP17863069.5A EP3428163B1 (fr) 2016-10-20 2017-10-20 Composé polycyclique et élément électroluminescent organique le comprenant
CN201780024271.2A CN109071510B (zh) 2016-10-20 2017-10-20 多环化合物和包含其的有机发光元件
JP2018548912A JP6780705B2 (ja) 2016-10-20 2017-10-20 多重環化合物およびこれを含む有機発光素子
US16/088,406 US11718606B2 (en) 2016-10-20 2017-10-20 Polycyclic compound and organic light emitting element comprising same

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JP7351713B2 (ja) 2018-11-30 2023-09-27 関東化学株式会社 ２－置換フルオレン系化合物、該化合物を含有する正孔輸送材料および該化合物を正孔輸送層に含む有機電子デバイス
JP2022504972A (ja) * 2019-03-14 2022-01-13 エルジー・ケム・リミテッド 新規な化合物およびこれを利用した有機発光素子
JP7187752B2 (ja) 2019-03-14 2022-12-13 エルジー・ケム・リミテッド 新規な化合物およびこれを利用した有機発光素子
US11910711B2 (en) 2019-03-14 2024-02-20 Lg Chem, Ltd. Cyclic compound and organic light emitting device comprising same

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