WO2017160068A1 - Composé hétérocyclique et diode organique électroluminescente le comprenant - Google Patents

Composé hétérocyclique et diode organique électroluminescente le comprenant Download PDF

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WO2017160068A1
WO2017160068A1 PCT/KR2017/002763 KR2017002763W WO2017160068A1 WO 2017160068 A1 WO2017160068 A1 WO 2017160068A1 KR 2017002763 W KR2017002763 W KR 2017002763W WO 2017160068 A1 WO2017160068 A1 WO 2017160068A1
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차용범
조성미
김정범
홍성길
곽지원
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LG Chem Ltd
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LG Chem Ltd
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    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
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    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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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 material layer is often made of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • Described herein is a heterocyclic compound and an organic light emitting device comprising the same.
  • R 1 and R 2 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or R 1 and R 2 combine with each other to form a substituted or unsubstituted ring,
  • L 1 and L 2 are the same as or different from each other, and each independently a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • n and n are the same as or different from each other, and each independently an integer of 0 to 5,
  • L 1 is the same as or different from each other
  • L 2 is the same as or different from each other
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted aryl group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted phosphine oxide group,
  • R, R 'and R are the same as or different from each other, and each independently hydrogen, deuterium, halogen, nitrile, nitro, hydroxy, carbonyl, ester, imide, amino, substituted or unsubstituted silyl Substituted or unsubstituted boron group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryloxy group; substituted or unsubstituted alkoxy group; substituted or unsubstituted aryloxy group Substituted or unsubstituted alkenyl group; substituted or unsubstituted aralkyl group; substituted or unsubstituted alkylaryl group; substituted or unsubstituted alkylamine group; substituted or unsubstituted aralkylamine group; substituted or unsubstituted Heteroarylamine groups;
  • a and b are the same as or different from each other, and each independently an integer of 0 to 4,
  • R ' is the same as or different from each other
  • R is the same as or different from each other when b is two or more.
  • 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 materials.
  • 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.
  • 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 3, an electron transport layer 7 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; An alkyl group; 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 exe
  • a substituent to which two or more substituents are linked may be interpreted as an aryl group substituted with a heterocyclic group.
  • the "biphenyl group” may be one aryl group or may be interpreted as a phenyl group substituted with a phenyl group.
  • 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 40 carbon atoms or an aryl group having 6 to 30 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 -SiR 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.
  • 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. Do not.
  • the boron group may be represented by the formula of -BR a R b , wherein R a and R b 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 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 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-C40. 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.
  • 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 40 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 alkylamine group is not particularly limited in carbon number, but is preferably 1 to 40.
  • Specific examples of the alkylamine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine Groups, diphenylamine groups, phenylnaphthylamine groups, ditolylamine groups, phenyltolylamine groups, triphenylamine groups 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.
  • aryl amine 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 hetero ring group or may be a polycyclic hetero ring group.
  • the heteroarylamine group including two or more heterocyclic groups may simultaneously include a monocyclic hetero ring group, a polycyclic hetero ring group, or a monocyclic hetero ring group and a polycyclic hetero ring group.
  • the arylheteroarylamine group means an amine group substituted with an aryl group and a heterocyclic group.
  • 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 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a monocyclic aryl group, but 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.
  • 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 including one or more of N, O, P, S, Si, and Se as hetero atoms, and carbon number is not particularly limited, but is preferably 1 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 1 to 30 carbon atoms.
  • heterocyclic group examples include, for example, 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, deoxyyl group, triazinyl group, tetrazinyl group, qui Nolinyl group, isoquinolinyl group, quinolyl group, quinazolinyl group, quinoxalinyl group, naphthyridinyl group, acriridyl group, xanthenyl group
  • 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 3 to 20 ring atoms.
  • 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 groups 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.
  • heteroarylene group is an aromatic divalent group.
  • 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 hetero ring means an aliphatic ring including at least one of heteroatoms.
  • examples of aliphatic hetero rings include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepan, Azocaine, thiocaine and the like, but are not limited to these.
  • the aromatic hetero ring means an aromatic ring including at least one of heteroatoms.
  • aromatic hetero rings 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.
  • the compound represented by Chemical Formula 1 may be represented by the following Chemical Formula A or Chemical Formula B.
  • R 1 , R 2 , L 1 , L 2 , m, n, Ar 1 , Ar 2 , R, R ′, and R ′′ are the same as in Formula 1 and Formula 2.
  • L 1 and L 2 are the same as or different from each other, and each independently a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.
  • L 1 and L 2 are the same as or different from each other, and each independently preferably one of any one of the linking groups selected from the group below, but is not limited thereto, the structures below may be further substituted. .
  • the structures are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amine group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; An alkyl group; 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.
  • L 1 and L 2 are the same as or different from each other, and each independently a substituted or unsubstituted phenylene group; Substituted or unsubstituted pyridylene group; Substituted or unsubstituted pyrimidinylene group; Substituted or unsubstituted triazinylene group; Substituted or unsubstituted carbazolene group; Substituted or unsubstituted dibenzofuranylene group; Or a substituted or unsubstituted dibenzothiophenylene group.
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted aryl group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted phosphine oxide group.
  • Ar 1 and Ar 2 may be the same as or different from each other, and each independently may be any one selected from the following structures, and the following structures may be further substituted.
  • the structures are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amine group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; An alkyl group; 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.
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently hydrogen; Phenyl group; A phenyl group substituted with at least one substituent selected from the group consisting of a phenyl group, a pyridine group, a quinoline group and a quinazoline group; Biphenyl group; Naphthyl group; Anthracenyl group; Anthracenyl group substituted with a phenyl group; Pyridine group; A pyridine group substituted with at least one substituent selected from the group consisting of a phenyl group and a biphenyl group; Pyrimidine groups; A pyrimidine group substituted with at least one substituent selected from the group consisting of a phenyl group and a biphenyl group; Triazine group; Triazine groups substituted with one or more substituents selected from the group consisting of a phenyl group and a biphenyl group;
  • Ar 1 is a phenyl group; Naphthyl group; Pyridine group; A pyridine group substituted with at least one substituent selected from the group consisting of a phenyl group and a biphenyl group; Pyrimidine groups; A pyrimidine group substituted with at least one substituent selected from the group consisting of a phenyl group and a biphenyl group; Triazine group; Triazine groups substituted with one or more substituents selected from the group consisting of a phenyl group and a biphenyl group; Carbazole groups; Or a carbazole group substituted with at least one selected from the group consisting of a phenyl group, a biphenyl group and a naphthyl group.
  • Ar 2 is hydrogen; Phenyl group; A phenyl group substituted with at least one substituent selected from the group consisting of a phenyl group, a pyridine group, a quinoline group and a quinazoline group; Biphenyl group; Anthracenyl group; Anthracenyl group substituted with a phenyl group; Pyridine group; A pyridine group substituted with at least one substituent selected from the group consisting of a phenyl group and a biphenyl group; Pyrimidine groups; A pyrimidine group substituted with at least one substituent selected from the group consisting of a phenyl group and a biphenyl group; Triazine group; Triazine groups substituted with one or more substituents selected from the group consisting of a phenyl group and a biphenyl group; Benzimidazole groups; Benzimidazole groups substituted with phenyl groups; Quinoline groups
  • the R One And R 2 are the same as or different from each other, each independently represent a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or R 1 and R 2 may combine with each other to form a substituted or unsubstituted ring.
  • the R One And R 2 are the same as or different from each other, each independently represent a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • R 1 and R 2 are the same as or different from each other, and each independently an alkyl group or an aryl group.
  • the R 1 and R 2 are the same as or different from each other, and each independently a substituted or unsubstituted methyl group; Or a substituted or unsubstituted phenyl group.
  • R 1 and R 2 are the same as or different from each other, and each independently a methyl group; Or a phenyl group.
  • R, R 'and R are the same as or different from each other, and each independently hydrogen, an alkyl group, an aryl group, or a heterocyclic group.
  • R, R 'and R are all hydrogen.
  • 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 bandgaps can be synthesized by introducing various substituents into the core structure.
  • the HOMO and LUMO energy levels of the compound may be controlled by introducing various substituents into the core structure.
  • the compound represented by Formula A or Formula B may be synthesized using a reaction of the following general formula, but is not limited thereto.
  • Ar 3 to Ar 6 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted aryl group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted phosphine oxide group, the description of the Ar 1 and Ar 2 can be applied.
  • the compound which has the intrinsic property of the introduced substituent can be synthesize
  • a substituent mainly used in the hole injection layer material, the hole transport material, the light emitting layer material, and the electron transport layer material used in the manufacture of the organic light emitting device into the core structure, it is possible to synthesize a material satisfying the requirements of each organic material layer. Can be.
  • 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 compound may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, roll coating and the like, but is not limited thereto.
  • 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, 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 layer of a hole injection layer, a hole transport layer, and a layer for simultaneously injecting holes and transporting holes, wherein at least one of the layers is represented by Formula 1 It may include a compound represented by.
  • the organic material layer may include at least one layer of a hole injection layer, an electron suppression layer, a hole transport layer, and a layer for simultaneously injecting holes and transporting holes, wherein at least one of the layers is represented by Chemical Formula 1 It may include a compound represented by.
  • the organic material layer may include an electron suppression layer, and the electron suppression layer may include a compound represented by Chemical Formula 1.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.
  • the 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 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 3, an electron transport layer 7, 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 3, or the electron transport layer 7.
  • 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, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure.
  • the organic material layer may be formed 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 method, rather than a deposition method. It can be prepared in layers.
  • 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.
  • Iridium complex used as a dopant of a light emitting layer 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.
  • 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.
  • HAT-CN hexaazatriphenylene hexanitrile
  • the following compound 3 was vacuum-deposited to a film thickness of 100 kPa on the said hole transport layer, and the electron suppression layer was formed.
  • 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 a thickness of 12 kPa in order to form a cathode.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1, except that compound 5 was used instead of compound 3 in Experimental Example 1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1, except that compound 6 was used instead of compound 3 in Experimental Example 1.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the following EB1 compound instead of compound 1 in Experimental Example 1.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the following EB2 compound instead of compound 1 in Experimental Example 1.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the following EB3 compound instead of compound 3 in Experimental Example 1.
  • the organic light emitting device manufactured by using the compound of the present invention as an electron suppressing layer is a case of using the material of Comparative Example 1 and Comparative Example 2 in which the amine group is connected to another position of the core of the present invention and aryl Compared with the case of using the substance of Comparative Example 3, which is substituted with only a group, the compound of the present invention plays an electron suppressing role and thus exhibits excellent characteristics in terms of efficiency, driving voltage, and / or stability of the organic light emitting device.
  • Experimental Examples 1-1 to 1-3 have a driving voltage of 10% to 12% less than Comparative Examples 1 to 3, and show efficiency of 10% or more.
  • the compound according to the present invention was confirmed that the excellent electron suppression ability can be applied to the organic light emitting device.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 2 except for using the compound of EB1 instead of compound 3 in Experimental Example 2-1.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 2 except for using the compound of EB2 instead of compound 3 in Experimental Example 2-1.
  • the organic light emitting device manufactured by using the compound of the present invention as a hole transport layer compared with the case of using the material of Comparative Example 3 and Comparative Example 4 in which the amine group is connected to another position of the core of the present invention
  • the compound of the present invention plays a role of hole transport, it shows excellent properties in terms of efficiency, driving voltage and / or stability of the organic light emitting device.
  • Experimental Examples 2-1 to 2-3 show a driving voltage of 5% to 8% or more, and an efficiency of 7 to 10% or more than the comparative example.
  • 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.
  • a green organic light emitting device was manufactured by the following method.
  • 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.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2, except that compound 8 was used instead of CBP in Comparative Example 5.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 5, except that Compound 9 was used instead of Compound CBP in Comparative Example 5.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 5, except that Compound 10 was used instead of Compound CBP in Comparative Example 5.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 5, except that Compound 11 was used instead of Compound CBP in Comparative Example 5.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 5, except that Compound 12 was used instead of Compound CBP in Comparative Example 5.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 5, except that the following compound of GH1 was used instead of the compound CBP in Comparative Example 5.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 5, except that the following compound of GH2 was used instead of the compound CBP in Comparative Example 5.
  • the green organic light emitting device of Experimental Examples 3-1 to 3-5 using the compound of the present invention as a host material of the green light emitting layer is Comparative Example 5 using the conventional CBP and Comparative Example having a structure similar to the core of the present invention. It was confirmed that the organic light emitting device manufactured by using the compounds of 6 and 7 as the green host material showed superior performance in terms of current efficiency and driving voltage.

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Abstract

La présente invention concerne un composé hétérocyclique et une diode électroluminescente organique le comprenant.
PCT/KR2017/002763 2016-03-14 2017-03-14 Composé hétérocyclique et diode organique électroluminescente le comprenant Ceased WO2017160068A1 (fr)

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KR20150017605A (ko) * 2013-08-07 2015-02-17 제일모직주식회사 화합물, 이를 포함하는 발광 재료, 유기 광전자 소자 및 상기 유기 광전자 소자를 포함하는 표시장치
KR20160011582A (ko) * 2014-07-22 2016-02-01 롬엔드하스전자재료코리아유한회사 유기 전계 발광 소자
WO2016015810A1 (fr) * 2014-07-29 2016-02-04 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
KR101555680B1 (ko) * 2015-03-03 2015-09-25 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

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CN108779072A (zh) 2018-11-09
JP2019508427A (ja) 2019-03-28

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