WO2017099471A1 - Composé hétérocyclique et élément électroluminescent organique le comprenant - Google Patents

Composé hétérocyclique et élément électroluminescent organique le comprenant Download PDF

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WO2017099471A1
WO2017099471A1 PCT/KR2016/014307 KR2016014307W WO2017099471A1 WO 2017099471 A1 WO2017099471 A1 WO 2017099471A1 KR 2016014307 W KR2016014307 W KR 2016014307W WO 2017099471 A1 WO2017099471 A1 WO 2017099471A1
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group
substituted
unsubstituted
compound
formula
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PCT/KR2016/014307
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Korean (ko)
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차용범
조성미
김진주
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주식회사 엘지화학
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Priority claimed from KR1020160147542A external-priority patent/KR102076884B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to US15/780,880 priority Critical patent/US12041848B2/en
Priority to CN201680072920.1A priority patent/CN108368077B/zh
Publication of WO2017099471A1 publication Critical patent/WO2017099471A1/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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • 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

Definitions

  • the present specification relates to a heterocyclic 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 layer is often composed of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, a hole injection layer, a hole transport layer, an electron suppression layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. Can be.
  • Described herein is a heterocyclic compound and an organic light emitting device comprising the same.
  • An exemplary embodiment of the present specification provides a compound represented by the following formula (1).
  • X is O or S
  • At least one of A and B is a structure of Formula 1-1, the other is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • L1 is a direct bond; Or a substituted or unsubstituted arylene group,
  • Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron 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 alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstit
  • Formula 1 may be represented by the following Formula 1-A or Formula 1-B,
  • an exemplary embodiment of the present specification is an organic light emitting device including a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers is It provides an organic light emitting device comprising the compound of formula (1).
  • the compound described herein can be used as the material of the organic material layer of the organic light emitting device.
  • the compound according to at least one exemplary embodiment may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode.
  • the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, electron suppression, luminescence, hole suppression, electron transport, or electron injection material.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG.
  • FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
  • An exemplary embodiment of the present specification provides a compound represented by Chemical Formula 1.
  • the term "substituted or unsubstituted” is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; And it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group, or substituted or unsubstituted two or more substituents of the substituents exemp
  • a substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.
  • adjacent The group may mean a substituent substituted with an atom directly connected to an atom in which the corresponding substituent is substituted, a substituent positioned closest in structural conformation to the substituent, or another substituent substituted in an atom in which the substituent is substituted.
  • two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C40. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
  • carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • the silyl group may be represented by the formula of -SiRR'R '', wherein R, R 'and R' 'are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • Specific examples of the silyl group include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group, but are not limited thereto. Do not.
  • the boron group may be represented by the formula of -BR'R '', wherein R 'and R' 'are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • the boron group may include, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, and phenylboron group.
  • the germanium group may be represented by the chemical formula of —GeR a R b R c , wherein R a , R b and R c are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • the germanium group may include, but is not limited to, a trimethyl germanium group, a triethyl germanium group, a t-butyldimethyl germanium group, and the like.
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group 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-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
  • 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-C20. 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.
  • Substituents comprising alkyl groups, alkoxy groups and other alkyl group moieties described herein include both straight and pulverized forms.
  • the alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • 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.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group, may be a polycyclic aryl group.
  • the arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
  • arylamine group examples include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methyl-phenylamine, 4-methyl-naphthylamine, 2-methyl-biphenylamine, 9-methyl-anthra Cenylamine, diphenyl amine group, phenyl naphthyl amine group, ditolyl amine group, phenyl tolyl amine group, carbazole and triphenyl amine group and the like, but are not limited thereto.
  • 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 heteroaryl group in the heteroarylamine group may be a monocyclic heterocyclic group or may be a polycyclic heterocyclic group.
  • the heteroarylamine group including two or more heterocyclic groups may include a monocyclic heterocyclic group, a polycyclic heterocyclic group, or a monocyclic heterocyclic group and a polycyclic heterocyclic group.
  • the arylheteroarylamine group means an amine group substituted with an aryl group and a heterocyclic group.
  • the amine group is not particularly limited, but is preferably 1 to 30.
  • the amine group may be substituted with an N atom, such as an aryl group, an alkyl group, an arylalkyl group, and a heterocyclic group.
  • Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group and phenylamine.
  • examples of the arylphosphine group include a substituted or unsubstituted monoarylphosphine group, a substituted or unsubstituted diarylphosphine group, or a substituted or unsubstituted triarylphosphine group.
  • the aryl group in the arylphosphine group may be a monocyclic aryl group, may be a polycyclic aryl group.
  • the arylphosphine group containing two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
  • the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 40 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be, for example, a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, etc., but is not limited thereto.
  • polycyclic aryl group a naphthyl group, anthracenyl group, a phenanthrenyl group, a perrylenyl group, a fluoranthenyl group, a triphenylenyl group, a penalenyl group, a pyrenyl group, a tetrasenyl group, a chrysenyl group, a pentaxenyl group , Fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spiro fluorenyl group and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • Spirofluorenyl groups such as (9,9-dimethylfluorenyl group) and It may be a substituted fluorenyl group such as (9,9-diphenyl fluorenyl group).
  • the present invention is not limited thereto.
  • the heterocyclic group is a heterocyclic group containing one or more of N, O, P, S, Si, and Se as hetero atoms, and the carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 6 to 40 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 6 to 20 carbon atoms.
  • heterocyclic group examples include pyridyl group, pyrrole group, pyrimidyl group, pyridazinyl group, furanyl group, thiophenyl group, imidazole group, pyrazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, triazole group , Oxadiazole group, thiadiazole group, dithiazole group, tetrazole group, pyranyl group, thiopyranyl group, pyrazinyl group, oxazinyl group, thiazinyl group, dioxynyl group, triazinyl group, tetrazinyl group, quinolinyl group , Isoquinolinyl group, quinazolinyl group, quinoxalinyl group, naphthyridinyl group, acridil group, xanthenyl group, phenanthridinyl
  • the heterocyclic group has a number of 3 to 60 constituting a ring. In another exemplary embodiment, the heterocyclic group has 3 to 40 ring atoms. In one embodiment, the heterocyclic group has a number of 3 to 20 ring elements.
  • heterocyclic group may be applied except that the heteroaryl group is aromatic.
  • the aryl group in the aryloxy group, arylthioxy group, aryl sulfoxy group, aryl phosphine group, aralkyl group, aralkylamine group, aralkenyl group, alkylaryl group, arylamine group, arylheteroarylamine group is described above.
  • the description of one aryl group may apply.
  • the alkyl group among the alkyl thioxy group, the alkyl sulfoxy group, the aralkyl group, the aralkyl amine group, the alkyl aryl group, and the alkyl amine group may be described with respect to the alkyl group described above.
  • heteroaryl group a heteroarylamine group, and an arylheteroarylamine group among the heteroaryl group may be applied to the description of the aforementioned heterocyclic group.
  • alkenyl group of the alkenyl group may be applied to the description of the alkenyl group described above.
  • the description of the aryl group described above may be applied except that the arylene group is a divalent group.
  • the arylene has 6 to 30 carbon atoms.
  • the meaning of combining with adjacent groups to form a ring means combining with adjacent groups with each other for a substituted or unsubstituted aliphatic hydrocarbon ring; Substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aliphatic heterocycle; Substituted or unsubstituted aromatic heterocycle; Or to form a condensed ring thereof.
  • the aliphatic hydrocarbon ring means a ring composed only of carbon and hydrogen atoms as a ring which is not aromatic.
  • examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like. There is, but is not limited to these.
  • the aromatic hydrocarbon ring means an aromatic ring composed only of carbon and hydrogen atoms.
  • examples of the aromatic hydrocarbon ring include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, penalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaph Butylene, benzofluorene, spirofluorene and the like, but is not limited thereto.
  • the aliphatic heterocycle means an aliphatic ring containing one or more of the heteroatoms.
  • examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepan, Azocaine, thiocaine and the like, but are not limited to these.
  • the aromatic heterocycle means an aromatic ring including at least one of heteroatoms.
  • aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole , Thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinol, quinazoline, quinoxaline, naphthyridine, azine Cridine, phenanthridine, diazanaphthalene, triazaindene, indole, indolizine, benzothiazole, benzoxazole, benzoimid
  • the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic hetero ring and aromatic hetero ring may be monocyclic or polycyclic.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 11 to 14.
  • L 1, A, B, Ar 1 and Ar 2 are the same as in Formula 1 and Formula 1-1.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 21 to 24.
  • a and B are not represented by the structure of Formula 1-1 substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • a and B are not represented by the structure of Formula 1-1 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 40 carbon atoms.
  • a and B are not represented by the structure of Formula 1-1 is substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted perenyl group; A substituted or unsubstituted fluoranthenyl group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted penalenyl group; Substituted or unsubstituted pyrenyl group; A substituted or unsubstituted tetrasenyl group; Substituted or unsubstituted
  • a and B are not represented by the structure of Formula 1-1 is substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted fluorenyl group; Or a substituted or unsubstituted naphthyl group.
  • a phenyl group not represented by the structure of Formula 1-1 of A and B Biphenyl group; 9,9-dimethylfluorenyl group; 9,9-dimethylfluorenyl group; Spirobifluorenyl group; Or a naphthyl group.
  • the A and B are not represented by the structure of Formula 1-1 is a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.
  • the A and B are not represented by the structure of Formula 1-1, a substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted dibenzofuranyl group; Or a substituted or unsubstituted carbazole group.
  • the A and B are not represented by the structure of Formula 1-1, a dibenzothiophene group unsubstituted or substituted with an aryl group; Dibenzofuranyl group unsubstituted or substituted with an aryl group; Or a carbazole group unsubstituted or substituted with an aryl group.
  • the A and B are not represented by the structure of Formula 1-1 dibenzothiophene group; Dibenzofuranyl group; Or 9-phenylcarbazole group.
  • L1 is a direct bond or a substituted or unsubstituted arylene group.
  • L1 is a direct bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
  • L1 is a direct bond or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L1 is preferably a substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylylene group; Substituted or unsubstituted terphenylene group; A substituted or unsubstituted quarterphenylene group; Substituted or unsubstituted naphthylene group; Substituted or unsubstituted pyrenylene group; Substituted or unsubstituted phenanthrenylene group; Substituted or unsubstituted perenylene group; Substituted or unsubstituted tetrasenylene group; Substituted or unsubstituted triphenylene group; Substituted or unsubstituted fluoranthhenylene group; And it is unsubstituted or substituted with one or more substituents selected from the group consisting of a substituted or unsubstituted fluoranthheny
  • the L1 is a direct bond; Substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylylene group; Substituted or unsubstituted terphenylene group; A substituted or unsubstituted quarterphenylene group; Substituted or unsubstituted naphthylene group; Substituted or unsubstituted anthracenylene group; A substituted or unsubstituted fluorenylene group; Substituted or unsubstituted phenanthrenylene group; Or a substituted or unsubstituted triphenylene group.
  • L1 is a phenylene group, biphenylylene group, terphenylene group, quarterphenylene group, naphthylene group, anthracenyl group, 9,9-dimethylfluorenylene group, phenanthrenylene group Or a triphenylene group, which may be further substituted.
  • L1 is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amine groups; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl heteroaryl amine group; Aryl phosphine group; And it may be substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group.
  • L1 is preferably any one substituent selected from the following group, but is not limited thereto.
  • the structures are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amine groups; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl heteroaryl amine group; Aryl phosphine group; And it may be substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron 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 alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group;
  • Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Carbonyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Linear or branched, substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Linear or branched, substituted or unsubstituted alkenyl groups having 2 to 60 carbon atoms; Linear or branched, substituted or unsubstituted alkynyl groups having 2 to 60 carbon atoms; Monocyclic or polycyclic substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; Monocyclic or polycyclic substituted or unsubstituted aryl group having 6 to 60 carbon atoms; And it is selected from the group consisting of a monocyclic or polycyclic substituted or unsubstituted heterocyclic group having 2
  • Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 40 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; Aryl groups such as phenyl group, biphenyl group, naphthyl group, anthracenyl group, chrysenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, tetrasenyl group, pentaxenyl group, fluorenyl group; Or pyridyl group, pyrrole group, pyridyl group, pyridazinyl group, furanyl group, thiophene group, imidazole group, pyrazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, triazole group, pyrazinyl group, Triazine group, quinolinyl group, isoquinolinyl group, quinazoline group, quinoxalinyl group, naph
  • Aryl groups such as pheny
  • Ar1 and Ar2 are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amine groups; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl heteroaryl amine group; Aryl phosphine group; And it may be substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group.
  • Ar1 and Ar2 may be the same as or different from each other, and each independently one selected from the following structures.
  • the structures are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amine groups; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl heteroaryl amine group; Aryl phosphine group; And it may be substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group.
  • the compound of Formula 1 may be any one selected from the following compounds.
  • the conjugation length of the compound and the energy bandgap are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy bandgap.
  • compounds having various energy band gaps may be synthesized by introducing various substituents at positions A and B of the core structure.
  • the HOMO and LUMO energy levels of the compound may be controlled by introducing various substituents at positions A and B of the core structure.
  • the compound which has the intrinsic property of the introduced substituent can be synthesize
  • the organic light emitting device is an organic light emitting device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, at least one of the organic layer It is characterized by including the compound.
  • the organic light emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that at least one organic material layer is formed using the above-described compound.
  • the organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have 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 suppression layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic material layers.
  • the organic material layer may include at least one of a hole injection layer, an electron suppression layer, a hole transport layer, and a layer for simultaneously injecting holes and transporting holes, and at least one of the layers. It may include a compound represented by the 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 compound represented by Formula 1 may be included as a host of the light emitting layer.
  • the compound represented by Chemical Formula 1 may be included as a phosphorescent host of the emission layer.
  • the organic material layer including the compound represented by Chemical Formula 1 may include the compound represented by Chemical Formula 1 as a host, and may include another organic compound, a metal, or a metal compound as a dopant.
  • the organic material layer including the compound represented by Chemical Formula 1 may include the compound represented by Chemical Formula 1 as a host, and may be used together with an iridium-based (Ir) dopant.
  • the organic material layer may include one or more layers of an electron transport layer, an electron injection layer, and a layer for simultaneously transporting and transporting electrons, and one or more of the layers may include the compound.
  • the organic material layer of the organic electronic device includes a hole transport layer, and the hole transport layer includes a compound represented by Chemical Formula 1.
  • the compound may be included in a light emitting layer, a layer for simultaneously injecting / holes transporting and emitting light, a layer for simultaneously transporting holes and emitting light, or a layer for simultaneously transporting electrons and emitting light.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula A-1.
  • X1 is a substituted or unsubstituted monovalent or higher benzofluorene group; Substituted or unsubstituted monovalent or higher fluoranthene group; A substituted or unsubstituted monovalent or higher pyrene group; Or a substituted or unsubstituted monovalent or higher chrysene group,
  • L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • X2 and X3 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted aralkyl group; Or a substituted or unsubstituted heteroaryl group, or may combine with each other to form a substituted or unsubstituted ring,
  • r is an integer of 1 or more
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Chemical Formula A-1 as a dopant of the light emitting layer.
  • L is a direct bond
  • r is 2.
  • X1 is a substituted or unsubstituted divalent pyrene group.
  • X1 is a divalent pyrene group unsubstituted or substituted with an alkyl group.
  • X1 is a divalent pyrene group.
  • X2 and X3 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • X2 and X3 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • X2 and X3 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 germanium group.
  • it is a phenyl group unsubstituted or substituted with a trimethylgermanium group.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula A-2.
  • X4 is 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9- Phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 3-methyl-2-naphthyl group, 4-methyl- 1-naphthyl group, or ego,
  • X6 is a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 2-biphenylyl group , 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m -Terphenyl-3-yl group, m-terphenyl-2-yl group
  • X5 and X7 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • p2 is an integer from 1 to 5
  • p1 and p3 are each an integer of 1 to 4,
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula A-2 as a host of the light emitting layer.
  • X4 is 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 4-phenanthryl Group, 1-naphthasenyl group, or 1-pyrenyl group.
  • X4 is 1-naphthyl group, 2-naphthyl group or 1-anthryl group.
  • X4 is a 1-naphthyl group.
  • X6 is a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 4- Phenanthryl group, 1-naphthacenyl group, or 1-pyrenyl group.
  • X6 is a phenyl group, 1-naphthyl group, 2-naphthyl group or 1-anthryl group.
  • X6 is a 2-naphthyl group
  • p2 is 1.
  • X5 and X7 are hydrogen.
  • the structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.
  • FIG. 1 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1.
  • the compound may be included in the light emitting layer (3).
  • FIG. 2 illustrates an organic light emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4 are sequentially stacked on a substrate 1.
  • the structure is illustrated.
  • the compound may be included in the hole injection layer 5, the hole transport layer 6, the light emitting layer 7, or the electron transport layer 8.
  • the organic material layer includes at least one layer of an electron transporting layer, an electron injection layer, and a layer for simultaneously transporting and transporting electrons, and at least one of the layers is represented by Formula 1 Compound.
  • 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 at least one layer of a hole transport layer, an electron suppression layer, a hole transport and an electron suppression at the same time, one of the layers is a compound represented by the formula (1) It includes.
  • the organic material layer includes a hole transport layer and an electron suppression layer
  • the hole transport layer or the electron suppression layer includes a compound represented by Chemical Formula 1.
  • the organic material layer includes one or more layers of a hole injection layer, a hole transport layer, and a hole injection and hole transport at the same time, one of the layers is represented by the formula (1) It includes a compound which becomes.
  • the organic material layer includes the compound represented by Chemical Formula 1 as a host, and includes another organic compound, a metal, or a metal compound as a dopant.
  • the organic light emitting device uses a metal vapor deposition (PVD) method such as sputtering or e-beam evaporation, and has a metal oxide or a metal oxide or an alloy thereof on a substrate. It can be prepared by depositing an anode to form an anode, 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 cathode thereon.
  • PVD metal vapor deposition
  • 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 may have a multilayer structure including a hole injection layer, a hole transport layer, an electron suppression layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure.
  • the organic layer may be prepared by using a variety of polymer materials, and by using a method such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than a deposition method. It can be prepared in layers.
  • 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); A combination of a metal and an oxide such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly (3-methyl compound), poly [3,4- (ethylene-1,2-dioxy) compound] (PEDT), 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, and the like, but are not limited thereto.
  • the hole injection material is a material capable of well injecting holes from the anode at a low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer.
  • the hole injection material include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene-based organics, quinacridone-based organics, and perylene-based Organic compounds, anthraquinones and polyaniline and poly-compounds of conductive polymers, and the like, but are not limited thereto.
  • the hole transporting material a material capable of transporting holes from the anode or the hole injection layer to be transferred to the light emitting layer is suitable.
  • a material capable of transporting holes from the anode or the hole injection layer to be transferred to the light emitting layer 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 is a material capable of emitting light in the 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 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, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • the organic material layer including the compound represented by Chemical Formula 1 includes the compound represented by Chemical Formula 1 as a host, and may be used together with an iridium-based (Ir) dopant.
  • Iridium complex used as a dopant is as follows.
  • the electron transporting material is a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer.
  • a material having high mobility to electrons is suitable. Specific examples 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 organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • the compound according to the present invention may also operate on a principle similar to that applied to organic light emitting devices in organic electronic devices including organic solar cells, organic photoconductors, organic transistors, and the like.
  • the intermediate X may introduce an amine group in the A or B position of the formula (1) by the following reaction scheme.
  • the compound 11 (18.69, yield: 76) was prepared by lowering the temperature to room temperature, removing the water layer, drying with anhydrous magnesium sulfate, and concentrating under reduced pressure and recrystallization with 220 ml of ethyl acetate.
  • 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 1 was vacuum deposited to a film thickness of 100 kPa on the hole transport layer to form an electron suppressing layer.
  • the following BH and BD were vacuum-deposited at a weight ratio of 25: 1 on the electron suppression layer with a film thickness of 300 Pa 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 have a thickness of 12 kPa on the electron injection and transport layer sequentially 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 2 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 5 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 6 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 8 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 10 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 11 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 12 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 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 16 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 17 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 25 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 26 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 29 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 30 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 34 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 45 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 48 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 49 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 52 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 53 was used instead of compound 1 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 EB1 compound was used instead of Compound 1 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 EB2 compound instead of compound 1 in Experimental Example 1-1.
  • An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 1 was used instead of Compound 1 in Experimental Example 1-1.
  • the compound according to the present invention is excellent in electron suppression ability and applicable to an organic light emitting device.
  • An organic light-emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound HT1 was used instead of Compound 1 in Experimental Example 2-1.
  • An organic light-emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound HT2 was used instead of Compound 1 in Experimental Example 2-1.
  • An organic light-emitting device was manufactured in the same manner as in Experimental Example 2-1, except that the following HT3 compound was used instead of Compound 1 in Experimental Example 2-1.
  • the compound according to the present invention is not only excellent in electron suppression ability but also in hole transport ability, and thus can be applied to an organic light emitting device.

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Abstract

La présente invention concerne un composé hétérocyclique et un élément électroluminescent organique le comprenant.
PCT/KR2016/014307 2015-12-08 2016-12-07 Composé hétérocyclique et élément électroluminescent organique le comprenant WO2017099471A1 (fr)

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