WO2016195441A1 - 함질소 축합고리 화합물 및 이를 이용한 유기 발광 소자 - Google Patents
함질소 축합고리 화합물 및 이를 이용한 유기 발광 소자 Download PDFInfo
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- WO2016195441A1 WO2016195441A1 PCT/KR2016/005954 KR2016005954W WO2016195441A1 WO 2016195441 A1 WO2016195441 A1 WO 2016195441A1 KR 2016005954 W KR2016005954 W KR 2016005954W WO 2016195441 A1 WO2016195441 A1 WO 2016195441A1
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title abstract description 4
- 150000001923 cyclic compounds Chemical class 0.000 title abstract 2
- 239000000126 substance Substances 0.000 claims abstract description 150
- 125000003118 aryl group Chemical group 0.000 claims description 91
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- 238000002347 injection Methods 0.000 claims description 50
- 239000007924 injection Substances 0.000 claims description 50
- 125000001424 substituent group Chemical group 0.000 claims description 49
- 239000011368 organic material Substances 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 125000000623 heterocyclic group Chemical group 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 33
- 125000002560 nitrile group Chemical group 0.000 claims description 32
- 125000001931 aliphatic group Chemical group 0.000 claims description 31
- 125000003342 alkenyl group Chemical group 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 125000004104 aryloxy group Chemical group 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- 125000003282 alkyl amino group Chemical group 0.000 claims description 29
- 150000003974 aralkylamines Chemical group 0.000 claims description 29
- 125000005264 aryl amine group Chemical group 0.000 claims description 29
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
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- HXNPYGYILCHGTJ-UHFFFAOYSA-N 2-chloro-4-phenyl-[1]benzofuro[3,2-d]pyrimidine Chemical compound O1C2=C(C3=C1C(C1=CC=CC=C1)=NC(=N3)Cl)C=CC=C2 HXNPYGYILCHGTJ-UHFFFAOYSA-N 0.000 description 5
- ICQFFYYMWOOREK-UHFFFAOYSA-N 2-chloro-4-phenyl-[1]benzothiolo[3,2-d]pyrimidine Chemical compound S1C2=C(C3=C1C(C1=CC=CC=C1)=NC(=N3)Cl)C=CC=C2 ICQFFYYMWOOREK-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
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- 230000000052 comparative effect Effects 0.000 description 5
- SFKMVPQJJGJCMI-UHFFFAOYSA-N 2-chloro-4-phenylquinazoline Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1C1=CC=CC=C1 SFKMVPQJJGJCMI-UHFFFAOYSA-N 0.000 description 4
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- 229910052727 yttrium Inorganic materials 0.000 description 4
- SFUIGUOONHIVLG-UHFFFAOYSA-N (2-nitrophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1[N+]([O-])=O SFUIGUOONHIVLG-UHFFFAOYSA-N 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- BSWVSKQCYPFXJF-UHFFFAOYSA-N 2,4-dichloro-[1]benzothiolo[3,2-d]pyrimidine Chemical compound C1=CC=C2C3=NC(Cl)=NC(Cl)=C3SC2=C1 BSWVSKQCYPFXJF-UHFFFAOYSA-N 0.000 description 3
- ORPYLLUOBDZSEX-UHFFFAOYSA-N 2-bromo-1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=C(Br)C=CC2=C1 ORPYLLUOBDZSEX-UHFFFAOYSA-N 0.000 description 3
- OBHKONRNYCDRKM-UHFFFAOYSA-N 4-chloro-2-phenylquinazoline Chemical compound N=1C2=CC=CC=C2C(Cl)=NC=1C1=CC=CC=C1 OBHKONRNYCDRKM-UHFFFAOYSA-N 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- 238000006069 Suzuki reaction reaction Methods 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
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- 125000004429 atom Chemical group 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- JNGNMLBEAYGPRJ-UHFFFAOYSA-N (2-nitronaphthalen-1-yl)boronic acid Chemical compound C1=CC=C2C(B(O)O)=C([N+]([O-])=O)C=CC2=C1 JNGNMLBEAYGPRJ-UHFFFAOYSA-N 0.000 description 2
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- NDXQDKJSFNZMJK-UHFFFAOYSA-N 1-bromo-2-chloronaphthalene Chemical compound C1=CC=CC2=C(Br)C(Cl)=CC=C21 NDXQDKJSFNZMJK-UHFFFAOYSA-N 0.000 description 2
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
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- OFTIMOCFSCRJRA-UHFFFAOYSA-N 4-chloro-2-naphthalen-2-ylquinazoline Chemical compound ClC1=NC(=NC2=CC=CC=C12)C1=CC2=CC=CC=C2C=C1 OFTIMOCFSCRJRA-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
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- 238000007254 oxidation reaction Methods 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
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- 238000005240 physical vapour deposition Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
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- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
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- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
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- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
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- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 1
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- TUQSVSYUEBNNKQ-UHFFFAOYSA-N 2,4-dichloroquinazoline Chemical compound C1=CC=CC2=NC(Cl)=NC(Cl)=C21 TUQSVSYUEBNNKQ-UHFFFAOYSA-N 0.000 description 1
- QSQFNTJMMCLDFQ-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-phenyl-[1]benzofuro[3,2-d]pyrimidine Chemical compound ClC1=CC=C(C=C1)C=1N=C(C2=C(N=1)C1=C(O2)C=CC=C1)C1=CC=CC=C1 QSQFNTJMMCLDFQ-UHFFFAOYSA-N 0.000 description 1
- HODWNPKKKUZEPQ-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-phenyl-[1]benzothiolo[3,2-d]pyrimidine Chemical compound ClC1=CC=C(C=C1)C=1N=C(C2=C(N=1)C1=C(S2)C=CC=C1)C1=CC=CC=C1 HODWNPKKKUZEPQ-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- WONYVCKUEUULQN-UHFFFAOYSA-N 2-methyl-n-(2-methylphenyl)aniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1C WONYVCKUEUULQN-UHFFFAOYSA-N 0.000 description 1
- JTMODJXOTWYBOZ-UHFFFAOYSA-N 2-methyl-n-phenylaniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1 JTMODJXOTWYBOZ-UHFFFAOYSA-N 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
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- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
Definitions
- the present specification relates to a nitrogen-containing condensed ring compound and an organic light emitting device using the same.
- the organic light emitting phenomenon is an example of converting an electric current into visible light by an internal process of a specific organic molecule.
- the principle of the organic light emitting phenomenon is as follows.
- An organic light emitting device using this principle may generally be composed of an organic material layer including a cathode and an anode, and an organic material layer disposed therebetween, such as a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer.
- the materials used in the organic light emitting device are pure organic materials or complex compounds in which organic materials and metals are complexed, and depending on the purpose, hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials, etc. It can be divided into.
- the hole injection material or the hole transport material an organic material having a p-type property, that is, an organic material which is easily oxidized and has an electrochemically stable state during oxidation, is mainly used.
- organic materials having n-type properties that is, organic materials that are easily reduced and have an electrochemically stable state at the time of reduction are mainly used.
- the light emitting layer material a material having a p-type property and an n-type property at the same time, that is, a material having a stable form in both oxidation and reduction states, and a material having high luminous efficiency that converts it to light when excitons are formed desirable.
- the present specification provides a condensed ring compound and an organic light emitting device using the same.
- Ar is a bicyclic or substituted or unsubstituted heterocyclic group
- L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
- R 1 to R 13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted aromatic or aliphatic heterocyclic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted alkylarylamine group; Or a substituted or unsubstituted heteroarylamine group or combine with an adjacent substituent to
- Another embodiment of the present specification is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one organic material layer including a light emitting layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Chemical Formula 1 Provided is an element.
- the novel condensed ring compound according to the embodiments of the present specification has an appropriate energy level, and is excellent in electrochemical stability and thermal stability. Therefore, the organic light emitting device including the compound provides high efficiency and / or high driving stability and long life effect.
- 1 to 5 are cross-sectional views illustrating a structure of an organic light emitting diode according to an exemplary embodiment of the present specification.
- a compound represented by Chemical Formula 1 is provided. Since the novel core structure represented by Chemical Formula 1 has a flat structural characteristic, the glass transition temperature is higher than the known structures, and thus the thermal stability is excellent.
- the novel compounds are organic materials of the organic light emitting device, in particular, a host material of the light emitting layer. And / or as a hole transport material. In addition, it can act as a hole injection material, electron transport material, electron injection material.
- substituted or unsubstituted is deuterium; Nitrile group; An alkyl group; Alkenyl groups; Cycloalkyl group; Aryl group; Heterocyclic group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkenylaryl group; An alkoxy group; Aryloxy group; Alkylamine group; Aralkylamine groups; Arylamine group; Alkylarylamine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heteroarylamine groups, or substituted or unsubstituted with a substituent to which two or more substituents among the above-described substituents are linked.
- 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 and can be interpreted as a substituent to which two phenyl groups are linked.
- the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 50.
- 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 alkenyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 50.
- 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 cycloalkyl group is not particularly limited, but preferably 3 to 60 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. Do not.
- the aryl group may be a monocyclic aryl group or a polycyclic aryl group.
- the carbon number is not particularly limited, but is preferably 6 to 60 carbon atoms.
- the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
- the polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, 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.
- the heterocyclic group is an aromatic or aliphatic heterocyclic group including one or more of O, N, and S as heterologous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms.
- heterocyclic group examples include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, Acridine group, pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , Carbazole group, carboline group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group (phenan),
- 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.
- the aryl group in the aryloxy group is the same as the example of the aryl group described above. Specifically, as the aryloxy group, phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenyl Oxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthryloxy, 2-anthryl Oxy, 9-anthryloxy, 1-phenanthryloxy, 3-phenanthryloxy, 9-phenanthryloxy, and the like.
- the arylthioxy group include a phenylthioxy group, 2-methylphenylthioxy group, and 4-tert-butylphenyl. Thioxy group and the like, but is not limited there
- the alkylamine group, aralkylamine group, arylamine group, alkylarylamine group, and heteroarylamine group are amine groups substituted with alkyl group, aralkyl group, aryl group, alkylaryl group and heteroaryl group, respectively.
- the description of the alkyl and aryl groups described above for the alkyl and aryl may be applied, and the description for the aromatic heterocyclic group among the heterocyclic groups may be applied to the heteroaryl group.
- amine group examples include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 3-methyl-phenylamine, 4 -Methyl-naphthylamine, 2-methyl-biphenylamine, 9-methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, etc. There is, but is not limited to these.
- an arylene group means one having two bonding positions, that is, a divalent group.
- the description of the aforementioned aryl group can be applied except that they are each divalent.
- a heteroarylene group means a heteroaryl group having two bonding positions, that is, a divalent group.
- the description of the aforementioned aromatic heterocyclic group can be applied except that they are each divalent.
- 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; Or to form a substituted or unsubstituted aromatic heterocycle.
- adjacent group refers to a substituent substituted on an atom directly connected to an atom to which the corresponding substituent is substituted, a substituent positioned closest to the substituent stereoscopically, or another substituent substituted on an atom to 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”.
- the aliphatic hydrocarbon ring means a ring composed only of carbon and hydrogen atoms as a ring which is not aromatic.
- examples of the aromatic hydrocarbon ring include, but are not limited to, phenyl group, naphthyl group, anthracenyl group, and the like.
- an aliphatic heterocycle means an aliphatic ring containing at least one of N, O or S atoms as a hetero atom.
- the aromatic heterocycle means an aromatic ring containing at least one of N, O or S atoms as a hetero atom.
- the aliphatic ring, aromatic ring, aliphatic hetero ring and aromatic hetero ring may be monocyclic or polycyclic.
- the compound represented by Chemical Formula 1 may be represented by the following Chemical Formula 2 or 3.
- R 1 to R 13 , Ar, and L are the same as defined in Chemical Formula 1.
- Ar in Formulas 1 to 3 is a two or more substituted or unsubstituted heterocyclic group containing N.
- Ar in Formulas 1 to 3 is a two or more substituted or unsubstituted heterocyclic group containing two or more N.
- Ar in Chemical Formulas 1 to 3 is unsubstituted or substituted with an aryl group substituted with a nitrile group, an alkyl group, an aryl group, heteroaryl group, arylheteroaryl group, heteroarylaryl group, nitrile group It is a bicyclic or more unsubstituted heterocyclic group containing 2 or more of N.
- L in Formula 1 to 3 is a direct bond; Substituted or unsubstituted phenylene group; Or a substituted or unsubstituted monocyclic heteroarylene group.
- L in Formula 1 to 3 is a direct bond; Substituted or unsubstituted phenylene group; Or a substituted or unsubstituted monocyclic heteroarylene group.
- L in Formula 1 to 3 is a direct bond; Substituted or unsubstituted phenylene group; Or a substituted or unsubstituted N-containing monocyclic heteroarylene group.
- L in Formula 1 to 3 is a direct bond; Substituted or unsubstituted phenylene group; Substituted or unsubstituted pyridine group; Substituted or unsubstituted pyrimidine group; Or a substituted or unsubstituted triazine group.
- L in Formula 1 to 3 is a direct bond; Phenylene group; Pyridine group; Pyrimidine groups; Or a triazine group.
- L in Formula 1 to 3 is a direct bond; Phenylene group; Or a pyridine group.
- the phenylene group may be represented by the following structure.
- Ar in Chemical Formulas 1 to 3 is represented by one of the following Chemical Formulas A to F.
- Y 1 , Y 2 , Z 1 to Z 4 , Q 1 to Q 8 , T 1 , T 2 and U 1 to U 8 are the same as or different from each other, and are each independently N or CRd, provided that Q 1 to Q 4 One of them is C connected to L,
- X 2 is NAr 1 , S or O
- Ar 1 , Rd and R 300 to R 305 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted aromatic or aliphatic heterocyclic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted alkylarylamine group; Or a substituted or unsubstituted heteroarylamine group
- the formula A may be represented by the formula A-1.
- R 202 to R 205 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted aromatic or aliphatic heterocyclic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted alkylarylamine group; Or a substituted or unsubstituted heteroarylamine group or combine with an adjacent substitu
- Chemical Formula B may be represented by any one of the following Chemical Formulas B-1 to B-6-2.
- X 1 is a direct bond, C ( ⁇ O) or CRR ′,
- R 202 to R 207 , R, R ', Ra and Rb are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted aromatic or aliphatic heterocyclic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted alkylarylamine group; Or a substituted or unsubstitute
- At least one of Y 1 and Y 2 is N to be.
- one of Y 1 and Y 2 is N .
- At least one of U 1 to U 8 of the formula D is N.
- At least one of Q 1 to Q 8 of the general formula C is N.
- At least one of Q 1 to Q 4 of the formula C is N.
- one of Q 3 and Q 4 of the formula C is N.
- one of Q 3 and Q 4 of the formula C is N, X 2 is NAr 1 .
- Q 1 and Q 3 of the formula C is N.
- Q 1 And Q 3 In the formula C is N, X 2 Is O or S.
- At least one of U 1 to U 8 of the formula D is N.
- Chemical Formula B-1 may be represented by the following Chemical Formula B-7 or B-8.
- R 202 to R 207 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted aromatic or aliphatic heterocyclic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted alkylarylamine group; Or a substituted or unsubstituted heteroarylamine group or combine with an adjacent substitu
- the formula B-2 and B-3 may be represented by the following formula B-9 or B-10, respectively.
- R 202 to R 205 , R 208 and R 209 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted aromatic or aliphatic heterocyclic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted alkylarylamine group; Or a substituted or unsubstituted heteroary
- the formula B-4 may be represented by one of the following formula B-11 to B-13.
- R 210 to R 218 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted aromatic or aliphatic heterocyclic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted alkylarylamine group; Or a substituted or unsubstituted heteroarylamine group or combine with an adjacent substitu
- Chemical Formula C may be represented by one of the following Chemical Formulas C-1 to C-6.
- X2 and Rd are as described above, q is an integer of 0 to 6, and when q is 2 or more, Rd is the same or different.
- Chemical Formula C may be represented by one of the following structural formulas.
- Chemical Formula D may be represented by the following Chemical Formula D-1.
- R 312 to R 315 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted aromatic or aliphatic heterocyclic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted alkylarylamine group; Or a substituted or unsubstituted heteroarylamine group or combine with an adjacent substitu
- one or two or more of U 1 to U 4 of the formula D-1 is N.
- the formula D may be represented by the following formula D-2 or D-3.
- R 312 to R 319 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted aromatic or aliphatic heterocyclic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted alkylarylamine group; Or a substituted or unsubstituted heteroarylamine group or combine with an adjacent substitu
- Chemical Formula E may be represented by the following Chemical Formula E-1.
- T 1 and T 2 are as defined in formula E,
- R 300 to R 306 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted aromatic or aliphatic heterocyclic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted alkylarylamine group; Or a substituted or unsubstituted heteroarylamine group or combine with an adjacent substituent
- the formula E may be represented by one of the following formula E-2 to E-4.
- R 300 to R 312 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted aromatic or aliphatic heterocyclic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted alkylarylamine group; Or a substituted or unsubstituted heteroarylamine group or combine with an adjacent substituent
- adjacent two of R 1 to R 4 of Formulas 1 to 3 combine with each other to form a ring, such as an aromatic ring.
- Chemical Formula 2 may be represented by any one of the following Chemical Formulas 6 to 8.
- R 1 to R 13 , L and Ar are the same as defined in Formula 1,
- R 21 to R 32 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted aromatic or aliphatic heterocyclic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted alkylarylamine group; Or a substituted or unsubstituted heteroarylamine group or combine with an adjacent substituent to
- Chemical Formula 3 may be represented by any one of the following Chemical Formulas 9 to 11.
- R 1 to R 13 , L and Ar are the same as defined in Formula 1,
- R 33 to R 44 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted aromatic or aliphatic heterocyclic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted alkylarylamine group; Or a substituted or unsubstituted heteroarylamine group or combine with an adjacent substituent to
- At least one of R 3 , R 6 and R 7 in Formulas 1 to 3 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted biphenyl group to be.
- Chemical Formula 1 is represented by the following Chemical Formula 12 or 13.
- R 1 to R 5 , R 7 to R 13 , L and Ar are the same as defined in Formula 1,
- Rc is hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted aromatic or aliphatic heterocyclic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted alkylarylamine group; Or a substituted or unsubstituted heteroarylamine group or combine with an adjacent substituent to form a ring, and p is an integer of 1 to
- Chemical Formula 1 is represented by one of the following Chemical Formulas 14 and 15.
- R 1 to R 6 , R 8 to R 13 , L and Ar are the same as defined in Formula 1,
- Rc is hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted aromatic or aliphatic heterocyclic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted alkylarylamine group; Or a substituted or unsubstituted heteroarylamine group or combine with an adjacent substituent to form a ring, and p is an integer of 1 to
- the adjacent two of R 5 to R 8 in Formulas 1 to 3 combine with each other to form a ring, such as an aromatic ring.
- Formula 1 is represented by one of the following formula 16 and 17.
- R 1 to R 4 , R 7 to R 13 , L and Ar are the same as defined in Formula 1,
- R 69 to R 76 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted aromatic or aliphatic heterocyclic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted alkylarylamine group; Or a substituted or unsubstituted heteroarylamine group or combine with an adjacent substitu
- Formula 1 is represented by one of the formulas 18 and 19.
- R 1 to R 5 , R 8 to R 13 , L and Ar are the same as defined in Formula 1,
- R 85 to R 92 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted aromatic or aliphatic heterocyclic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted alkylarylamine group; Or a substituted or unsubstituted heteroarylamine group or combine with an adjacent substituent
- Formula 1 is represented by one of the formulas 20 and 21.
- R 1 to R 6 , R 9 to R 13 , L and Ar are the same as defined in Formula 1,
- R 101 to R 108 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted aromatic or aliphatic heterocyclic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted alkylarylamine group; Or a substituted or unsubstituted heteroarylamine group or combine with an adjacent substituent
- the adjacent two of R 9 to R 12 in Formulas 1 to 3 combine with each other to form a ring, such as an aromatic ring.
- Formula 1 is represented by one of the following formula 22 and 23.
- R 1 to R 10 , R 13 , L and Ar are the same as defined in Formula 1,
- R 117 to R 124 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted aromatic or aliphatic heterocyclic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted alkylarylamine group; Or a substituted or unsubstituted heteroarylamine group or combine with an adjacent substitu
- Formula 1 is represented by one of the following formula 24 and 25.
- R 1 to R 9 , R 12 , R 13 , L and Ar are the same as defined in Formula 1,
- R 133 to R 140 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted aromatic or aliphatic heterocyclic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted alkylarylamine group; Or a substituted or unsubstituted heteroarylamine group or combine with an adjacent substituent
- Formula 1 is represented by one of the following formula 26 and 27.
- R 1 to R 8 , R 11 to R 13 , L and Ar are the same as defined in Formula 1,
- R 149 to R 156 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted aromatic or aliphatic heterocyclic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted alkylarylamine group; Or a substituted or unsubstituted heteroarylamine group or combine with an adjacent substitu
- R 206 is hydrogen, substituted or unsubstituted alkyl group, such as methyl group, or substituted or unsubstituted aryl group, such as phenyl group, biphenylyl group, or naph Til group.
- R 207 is hydrogen, a substituted or unsubstituted alkyl group, such as a methyl group, or a substituted or unsubstituted aryl group, such as a phenyl group, biphenylyl group, or naph Til group.
- R 208 is hydrogen, substituted or unsubstituted alkyl group, such as methyl group, or substituted or unsubstituted aryl group, such as phenyl group, biphenylyl group, or naph Til group.
- R 209 is hydrogen, substituted or unsubstituted alkyl group, such as methyl group, or substituted or unsubstituted aryl group, such as phenyl group, biphenylyl group, or naph Til group.
- Y 1 is CR 219
- Y 2 is N or CR 220
- R 219 is hydrogen, substituted or unsubstituted alkyl group, such as methyl group, or substituted or unsubstituted Ring aryl group such as phenyl group, biphenylyl group, or naphthyl group
- R 220 is hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted aromatic or aliphatic heterocyclic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted or unsubstituted
- Y 1 is CR 219
- Y 2 is N
- R 219 is hydrogen, substituted or unsubstituted alkyl group, such as methyl group, or substituted or unsubstituted aryl Group, such as a phenyl group, a biphenylyl group, or a naphthyl group.
- Y 1 is CR 219
- Y 2 is N
- R 219 is a substituted or unsubstituted aryl group, such as a phenyl group, biphenylyl group, or naphthyl group .
- Ar may be a group represented by the following formula.
- Formula 1 is represented by any one of the following compounds
- the compound represented by Chemical Formula 1 may be subjected to amination by, for example, Ulmann or Buchwald-Hartwing coupling, and to Suzki or Heck coupling. Reaction can be used and Grignard reagent can be used. The rest of the formula can be synthesized by the same reaction.
- the core of Formula 2 may be prepared by Preparation Example 1
- the core of Formula 3 may be prepared by Preparation Example 2, but is not limited thereto.
- the introduction of further substituents can be carried out using materials and reaction conditions known in the art.
- the core of Formula 3 may be prepared by introducing a substituent Ar to Formula 2-d.
- Ar is the same as that of Formula 1 described above.
- L-Ar may be introduced instead of Ar.
- X, X 'and X are the same as or different from each other, and each independently a halogen group
- Ar has the same definition as in Chemical Formula 1.
- L-Ar may be introduced instead of Ar.
- an organic light emitting device including the compound represented by Chemical Formula 1.
- An organic light emitting device 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 of Formula 1.
- the organic material layer of the organic light emitting device 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 according to the exemplary embodiments of the present specification may have a structure including a hole injection layer, a hole transport 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 layers.
- the organic material layer includes an electron transport layer, an electron injection layer, a layer for simultaneously transporting electrons and electrons, a light emitting layer, a hole transport layer, a hole injection layer, or a layer for simultaneously transporting holes and holes,
- the electron transport layer, the electron injection layer, the layer for simultaneously transporting electrons and electrons, the light emitting layer, the hole transport layer, the hole injection layer or the layer for simultaneously transporting holes and hole injection includes the compound of formula (1).
- the organic material layer includes an electron transport layer, an electron injection layer, or a layer for simultaneously transporting and transporting electrons, and the electron transport layer, the electron injection layer, or the layer for simultaneously transporting and transporting electrons. It includes a compound of Formula 1.
- the light emitting layer includes the compound of Formula 1.
- the light emitting layer includes the compound of Formula 1 as a host.
- the light emitting layer including the compound of Formula 1 may further include a dopant.
- the dopant may use those known in the art.
- a phosphorescent dopant specifically an iridium-based complex, can be used.
- the dopant may be represented by the following compound, but is not limited thereto.
- the dopant compound is not limited only to the above examples.
- the organic material layer includes a hole injection layer, a hole transport layer, or a layer for simultaneously transporting holes and holes, and the hole injection layer, the hole transport layer, or the layer for simultaneously transporting holes and holes. It includes a compound of Formula 1.
- the organic material layer may further include a hole injection layer or a hole transport layer including a compound including an arylamino group, a carbazole group or a benzocarbazole group in addition to the organic material layer including the compound of Formula 1 .
- the organic material layer including the compound of Formula 1 may include the compound of Formula 1 as a host, and may include another organic compound, a metal, or a metal compound as a dopant.
- the organic light emitting diode may be an organic light emitting diode having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
- the organic light emitting diode may be an organic light emitting diode having an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
- FIGS. 1-10 For example, the structure of the organic light emitting device according to the present invention is illustrated in FIGS.
- FIG. 1 illustrates an organic light emitting device in which an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, and a cathode 7 are sequentially stacked on a substrate 1.
- the structure is illustrated.
- the compound represented by Chemical Formula 1 may be included in the hole injection layer 3, the hole transport layer 4, the light emitting layer 5, or the electron transport layer 6.
- FIG. 2 illustrates a structure of an organic light emitting device in which an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, and a cathode 7 are sequentially stacked on a substrate 1.
- the compound represented by Chemical Formula 1 may be included in the hole injection layer 3, the hole transport layer 4, or the light emitting layer 5.
- FIG 3 illustrates a structure of an organic light emitting device in which an anode 2, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, and a cathode 7 are sequentially stacked on a substrate 1.
- the compound represented by Formula 1 may be included in the hole transport layer 4, the light emitting layer 5 or the electron transport layer (6).
- FIG. 4 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 5, an electron transport layer 6, and a cathode 7 are sequentially stacked on a substrate 1.
- the compound represented by Chemical Formula 1 may be included in the emission layer 5 or the electron transport layer 6.
- FIG. 5 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 5, and a cathode 7 are sequentially stacked on a substrate 1.
- the compound represented by Chemical Formula 1 may be included in the emission layer 5.
- 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 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 of Formula 1.
- 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. At this time, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode. And 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 physical vapor deposition
- 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.
- an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on
- the compound of Formula 1 may be formed of 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.
- an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate (International Patent Application Publication No. 2003/012890).
- the manufacturing method is not limited thereto.
- the first electrode is an anode
- the second electrode is a cathode
- the first electrode is a cathode and 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, and the like, but are not limited thereto.
- the hole injection material is a layer for injecting holes from an electrode, and the hole injection material has a capability of transporting holes, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is generated in a light emitting layer.
- the compound which prevents the movement of the excited excitons 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 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 light emitting layer may include a host material and a dopant material.
- the host material is a condensed aromatic ring derivative or a heterocyclic containing compound.
- the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
- the heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
- Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like.
- 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 is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
- the electron transporting material is a material that can inject electrons well from the cathode and move them to the light emitting layer. This 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.
- 2-Chloro-4- (naphthalen-2-yl) quinazolin was synthesized through the Suzuki coupling reaction with naphthalen-2-ylboronic acid using 2,4-dichloroquinazolin as the starting material.
- 2-chloro-4-phenylbenzofuro [3,2-d] pyrimidine is a 2,4-dichlorobenzofuro [3,2-d] pyrimidine as a starting material, which is used to react phenylboronic acid and Suzuki coupling. Synthesized through.
- 2-Chloro-4-phenylbenzo [4,5] thieno [3,2-d] pyrimidine is prepared using 2,4-dichlorobenzothieno [3,2-d] pyrimidine as a starting material. It synthesize
- a red organic light emitting device was manufactured by the following method.
- a glass substrate (corning 7059 glass) coated with ITO (Indium Tin Oxide) with a thickness of 1,000 ⁇ was placed in distilled water in which a dispersant was dissolved, and ultrasonically washed. 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 substrate was mounted in a vacuum chamber, and the base pressure was 1 ⁇ 10 ⁇ 6 torr. Then, the organic material was deposited on the ITO with a hole injection layer (DNTPD (700 kPa)). After depositing ⁇ -NPB (300 kV) with the hole transporting layer thereon, the compound of Table 1 synthesized in the above-described Preparation Example was sublimed and purified and used as a host (95 wt%), and used as a dopant Dp-. 7 (5 wt%) was co-deposited (300 kPa) to deposit the light emitting layer.
- DNTPD hole injection layer
- BCP 50 mW
- ET-1 and ET-2 were evaporated at a 2: 1 rate to deposit 300 mW electron transport layer on the light emitting layer.
- An OLED device was manufactured in the order of ET-2 (5 kV) as the electron injection layer and Al cathode (1,000 kV).
- the organic light emitting device of Comparative Example 1 was manufactured in the same manner as in the organic light emitting device structures of Experimental Examples 1 to 12 except for using CBP, which is used as a general phosphorescent host material, instead of the compound of the present invention as a host of the light emitting layer.
- CBP which is used as a general phosphorescent host material
- the organic light emitting device using the compound of the present invention can be seen that the emission efficiency is improved while lowering the driving voltage and due to the lifetime increase effect. In general, it showed lower driving voltage and higher efficiency than CBP used as a comparative host material, and showed excellent results in terms of lifetime.
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Abstract
Description
화합물 | 구동전압(V) | 전류효율(cd/A) | 수명(T95) | CIE x | CIE y | |
실험예 1 | 1-d-1 | 4.2 | 42.7 | 250 | 0.686 | 0.331 |
실험예 2 | 1-d-3 | 4.4 | 47.2 | 100 | 0.685 | 0.313 |
실험예 3 | 1-d-7 | 4.1 | 44.3 | 280 | 0.687 | 0.337 |
실험예 4 | 2-d-4 | 4.2 | 46.80 | 95 | 0.686 | 0.314 |
실험예 5 | 2-d-8 | 3.8 | 50.8 | 390 | 0.688 | 0.313 |
실험예 6 | 2-d-9 | 3.9 | 52.3 | 390 | 0.678 | 0.322 |
실험예 7 | 2-d-11 | 3.7 | 47.0 | 110 | 0.686 | 0.314 |
실험예 8 | 2-d-12 | 4.0 | 57.5 | 410 | 0.688 | 0.312 |
실험예 9 | 2-d-13 | 4.1 | 52.2 | 405 | 0.684 | 0.346 |
실험예 10 | 2-d-15 | 4.3 | 51.6 | 105 | 0.682 | 0.318 |
실험예 11 | 6-d-1 | 3.5 | 42.0 | 320 | 0.686 | 0.312 |
실험예 12 | 6-d-4 | 3.6 | 46.6 | 120 | 0.688 | 0.312 |
비교예 1 | CBP | 6.1 | 20.7 | 57 | 0.675 | 0.330 |
Claims (13)
- 하기 화학식 1로 표시되는 화합물:[화학식 1]화학식 1에 있어서,Ar은 2환 이상의 치환 또는 비치환된 헤테로고리기이고,L은 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이며,R1 내지 R13은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 니트릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 또는 지방족의 헤테로고리기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아르알킬아민기; 치환 또는 비치환된 알킬아릴아민기; 또는 치환 또는 비치환된 헤테로아릴아민기이거나 인접한 치환기와 서로 결합하여 고리를 형성한다.
- 청구항 1에 있어서, Ar은 N을 함유하는 2환 이상의 치환 또는 비치환된 헤테로고리기인 것인 화합물.
- 청구항 1에 있어서, Ar은 N을 2개 이상 함유하는 2환 이상의 치환 또는 비치환된 헤테로고리기인 것인 화합물.
- 청구항 1에 있어서, Ar은 니트릴기, 알킬기, 아릴기, 헤테로아릴기, 아릴헤테로아릴기, 헤테로아릴아릴기, 니트릴기로 치환된 아릴기로 치환 또는 비치환된 N을 2개 이상 함유하는 2환 이상의 비치환된 헤테로고리기인 것인 화합물.
- 청구항 1에 있어서, Ar이 하기 화학식 A 내지 F 중 하나로 표시된 것인 화합물:[화학식 A][화학식 B][화학식 C][화학식 D][화학식 E][화학식 F]화학식 A 내지 F에 있어서,Y1, Y2, Z1 내지 Z4, Q1 내지 Q8, T1, T2 및 U1 내지 U8은 서로 같거나 상이하고, 각각 독립적으로 N 또는 CRd이고, 단 Q1 내지 Q4 중 하나는 L에 연결된 C이며,X2는 NAr1, S 또는 O이며, Ar1, Rd 및 R300 내지 R305는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 니트릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 또는 지방족의 헤테로고리기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아르알킬아민기; 치환 또는 비치환된 알킬아릴아민기; 또는 치환 또는 비치환된 헤테로아릴아민기이거나 인접한 치환기와 서로 결합하여 고리를 형성하고, n은 0 내지 2의 정수이며, m은 0 내지 3의 정수이고, n 또는 m이 2 일 때 R305는 서로 같거나 상이하다.
- 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 6 내지 11 중 하나로 표시되는 것인 화합물:[화학식 6][화학식 7][화학식 8][화학식 9][화학식 10][화학식 11]화학식 6 내지 11에 있어서,R1 내지 R13, L 및 Ar은 화학식 1에서 정의한 바와 같고,R21 내지 R44는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 니트릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 또는 지방족의 헤테로고리기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아르알킬아민기; 치환 또는 비치환된 알킬아릴아민기; 또는 치환 또는 비치환된 헤테로아릴아민기이거나 인접한 치환기와 서로 결합하여 고리를 형성한다.
- 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 16 내지 21중 하나로 표시되는 것인 화합물:[화학식 16][화학식 17][화학식 18][화학식 19][화학식 20][화학식 21]화학식 16 내지 21에 있어서,R1 내지 R13, L 및 Ar은 화학식 1에서 정의한 바와 같고,R69 내지 R108은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 니트릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 또는 지방족의 헤테로고리기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아르알킬아민기; 치환 또는 비치환된 알킬아릴아민기; 또는 치환 또는 비치환된 헤테로아릴아민기이거나 인접한 치환기와 서로 결합하여 고리를 형성한다.
- 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 22 내지 27 중 하나로 표시되는 것인 화합물:[화학식 22][화학식 23][화학식 24][화학식 25][화학식 26][화학식 27]화학식 22 내지 27에 있어서,R1 내지 R13, L 및 Ar은 화학식 1에서 정의한 바와 같고,R117 내지 R156은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 니트릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 방향족 또는 지방족의 헤테로고리기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아르알킬아민기; 치환 또는 비치환된 알킬아릴아민기; 또는 치환 또는 비치환된 헤테로아릴아민기이거나 인접한 치환기와 서로 결합하여 고리를 형성한다.
- 제1 전극; 상기 제1 전극과 대향하여 구비되는 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비되는 발광층을 포함한 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상이 청구항 1 내지 10 중 어느 한 항에 따른 화합물을 포함하는 것인 유기 발광 소자.
- 청구항 11에 있어서, 상기 유기물층은 전자수송층, 전자주입층, 전자수송 및 전자주입을 동시에 하는 층, 발광층, 정공수송층, 정공주입층 또는 정공수송 및 정공주입을 동시에 하는 층을 포함하고, 상기 전자수송층, 전자주입층, 전자수송 및 전자주입을 동시에 하는 층, 발광층, 정공수송층, 정공주입층 또는 정공수송 및 정공주입을 동시에 하는 층은 상기 화학식 1의 화합물을 포함하는 것인 유기 발광 소자.
- 청구항 11에 있어서, 상기 발광층은 상기 화학식 1의 화합물을 포함하는 것인 유기 발광 소자.
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Also Published As
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KR20190135446A (ko) | 2019-12-06 |
US10347845B2 (en) | 2019-07-09 |
TWI618708B (zh) | 2018-03-21 |
CN106661037B (zh) | 2019-10-11 |
US10580998B2 (en) | 2020-03-03 |
TW201708228A (zh) | 2017-03-01 |
KR102119352B1 (ko) | 2020-06-04 |
JP6501192B2 (ja) | 2019-04-17 |
JP2017538657A (ja) | 2017-12-28 |
EP3305792A4 (en) | 2019-01-16 |
US20190173022A1 (en) | 2019-06-06 |
KR20160142792A (ko) | 2016-12-13 |
CN106661037A (zh) | 2017-05-10 |
KR102174683B1 (ko) | 2020-11-05 |
EP3305792A1 (en) | 2018-04-11 |
EP3305792B1 (en) | 2024-04-10 |
US20170213984A1 (en) | 2017-07-27 |
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