WO2018056773A1 - Amine-based compound and organic light emitting device comprising same - Google Patents

Amine-based compound and organic light emitting device comprising same Download PDF

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WO2018056773A1
WO2018056773A1 PCT/KR2017/010533 KR2017010533W WO2018056773A1 WO 2018056773 A1 WO2018056773 A1 WO 2018056773A1 KR 2017010533 W KR2017010533 W KR 2017010533W WO 2018056773 A1 WO2018056773 A1 WO 2018056773A1
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이성재
하재승
홍성길
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주식회사 엘지화학
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Priority claimed from KR1020170122421A external-priority patent/KR102010893B1/en
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Priority to CN201780053790.1A priority Critical patent/CN109689618B/en
Priority to US16/322,730 priority patent/US11069858B2/en
Publication of WO2018056773A1 publication Critical patent/WO2018056773A1/en

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Definitions

  • the present specification relates to a compound and an organic light emitting device including the same.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • An exemplary embodiment of the present specification provides a compound represented by the following formula (1).
  • R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted thioalkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • n1 to n3 are each an integer of 0 to 4,
  • n4 is an integer of 0 to 2
  • p1 to p3 are each an integer of 0 to 3
  • L, L1 and L2 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
  • Ar1 is triphenylene
  • Ar2 is hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Substituted or unsubstituted arylalkyl group; Substituted or unsubstituted aryl alkenyl group; Or a substituted or unsubstituted heterocyclic group,
  • X1 is a substituted or unsubstituted aryl group; Substituted or unsubstituted arylalkyl group; Substituted or unsubstituted aryl alkenyl group; Or a substituted or unsubstituted heteroring group.
  • an exemplary embodiment of the present specification is an organic light emitting device including a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers is It provides an organic light emitting device comprising the compound of formula (1).
  • the compound described herein can be used as the material of the organic material layer of the organic light emitting device.
  • the compound according to at least one exemplary embodiment may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode.
  • the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, electron suppression, luminescence, hole suppression, electron transport, or electron injection material.
  • the efficiency of the organic light emitting device can be improved, the driving voltage can be lowered, and the life of the device can be obtained.
  • 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 a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 8, a light emitting layer 3, and a layer 7 for simultaneously transporting electrons and electrons.
  • an organic light emitting element composed of a cathode 4.
  • An exemplary embodiment of the present specification provides a compound represented by the following formula (1).
  • R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted thioalkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • n1 to n3 are each an integer of 0 to 4,
  • n4 is an integer of 0 to 2
  • p1 to p3 are each an integer of 0 to 3
  • L, L1 and L2 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
  • Ar1 is triphenylene
  • Ar2 is hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Substituted or unsubstituted arylalkyl group; Substituted or unsubstituted aryl alkenyl group; Or a substituted or unsubstituted heterocyclic group,
  • X1 is a substituted or unsubstituted aryl group; Substituted or unsubstituted arylalkyl group; Substituted or unsubstituted aryl alkenyl group; Or a substituted or unsubstituted heteroring group.
  • 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; Silyl groups; Boron group; Alkyl groups; Arylalkyl group; Cycloalkyl group; Alkenyl groups; Aryl alkenyl group; Aryl group; Amine groups; 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 exemplified above.
  • a substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.
  • 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 group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, pentyl group, n-pentyl group Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, n-nonyl, etc. There is, but is not limited to these.
  • 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 group, ethoxy group, n-propoxy group, isopropoxy group, i-propyloxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n-pentyloxy group , Neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group , Etc., 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.
  • 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 amine group is not particularly limited, but is preferably 1 to 30.
  • the amine group may be substituted with the aforementioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group and combinations thereof, and the like, and specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group and diethylamine.
  • phenylamine group 9,9-dimethylfluorenylphenylamine group, pyridylphenylamine group, diphenylamine group, phenylpyridylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, Dibenzofuranylphenylamine group, 9-methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, and the like, but are limited thereto. It is not.
  • 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 monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, or the like, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, triphenylenyl 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 fluorenyl group is substituted, (9,9-dimethylfluorenyl group), (9-methyl-9-phenylfluorenyl group), (9,9-diphenylfluorenyl group), , , Etc., but 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 is 2 to 60 the number of elements constituting the ring. In another exemplary embodiment, the heterocyclic group has 2 to 40 ring atoms. In one embodiment, the hetero ring group has 2 to 20 ring atoms.
  • an arylalkyl group and an aryl group in the arylalkenyl group may be described with respect to the aforementioned aryl group.
  • alkyl group in the arylalkyl group and the thioalkyl group may be described with respect to the alkyl group described above.
  • alkenyl group in the arylalkenyl group may be applicable to the description of the alkenyl group described above.
  • 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 group; Substituted or unsubstituted aliphatic heterocyclic group; Substituted or unsubstituted aromatic heterocyclic group; Or to form a condensed ring thereof.
  • the aliphatic hydrocarbon ring means a ring composed only of carbon and hydrogen atoms as a ring which is not aromatic.
  • examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like. There is, but is not limited to these.
  • the compound represented by Chemical Formula 1 may be represented by one of the following Chemical Formulas 2 to 4.
  • R1 to R4, X1, L, L1, L2, n1 to n4, p1 to p3, Ar1 and Ar2 are the same as defined in the formula (1).
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted divalent heterocyclic group having 2 to 60 carbon atoms.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted hetero ring group having 2 to 30 carbon atoms.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; Or the following structures.
  • R17 to R19 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; It is a substituted or unsubstituted phenylene group.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a phenylene group.
  • R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with an aryl group or a heterocyclic group; A cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with an alkyl group, an aryl group or a heterocyclic group; An aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group or a heterocyclic group; Or a heterocyclic group having 2 to 30 carbon atoms unsubstituted or substituted with an alkyl group or an aryl group.
  • L is any one selected from a direct bond or the following structures.
  • R17 to R19 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • R17 to R19 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • R17 to R19 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • R17 to R19 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • R17 to R19 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with an aryl group or a heterocyclic group; A cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with an alkyl group, an aryl group or a heterocyclic group; An aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group or a heterocyclic group; Or a heterocyclic group having 2 to 30 carbon atoms unsubstituted or substituted with an alkyl group or an aryl group.
  • X1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • X1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • X1 is an aryl group having 6 to 60 carbon atoms unsubstituted or substituted with an aryl group; Or a heterocyclic group having 2 to 60 carbon atoms unsubstituted or substituted with an aryl group.
  • X1 is an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a phenyl group; Or a heterocyclic group having 2 to 40 carbon atoms unsubstituted or substituted with a phenyl group.
  • X1 is a phenyl group unsubstituted or substituted with a phenyl group; A biphenyl group unsubstituted or substituted with a phenyl group; A naphthyl group unsubstituted or substituted with a phenyl group; Phenanthrenyl group unsubstituted or substituted with a phenyl group; Triphenylene group unsubstituted or substituted with a phenyl group; Dibenzothiophene group unsubstituted or substituted with a phenyl group; Dibenzofuran group unsubstituted or substituted with a phenyl group; Carbazolyl group unsubstituted or substituted with a phenyl group; Or a benzocarbazolyl group unsubstituted or substituted with a phenyl group.
  • X1 may be selected from the following structures.
  • R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring.
  • R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with an aryl group or a heterocyclic group; A cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with an alkyl group, an aryl group or a heterocyclic group; An aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group or a heterocyclic group; Or a heterocyclic group having 2 to 30 carbon atoms unsubstituted or substituted with an alkyl group or an aryl group.
  • R11 and R12 may be combined with each other to form a substituted or unsubstituted ring.
  • the R11 and R12 may be combined with each other to form a substituted or unsubstituted hydrocarbon ring.
  • R11 and R12 may combine with each other to form cyclopentane or cyclohexane.
  • Ar2 is hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • Ar2 is hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.
  • Ar2 is hydrogen; heavy hydrogen; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted triphenyl group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted carbazolyl group; Or a substituted or unsubstituted benzocarbazolyl group.
  • Ar2 may be selected from the following structures.
  • R14 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring.
  • R14 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • R14 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • R14 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • R14 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with an aryl group or a heterocyclic group; A cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with an alkyl group, an aryl group or a heterocyclic group; An aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group or a heterocyclic group; Or a heterocyclic group having 2 to 30 carbon atoms unsubstituted or substituted with an alkyl group or an aryl group.
  • R14 and R15 may be combined with each other to form a substituted or unsubstituted hydrocarbon ring.
  • the R14 and R15 may be combined with each other to form cyclopentane or cyclohexane.
  • the compound of Formula 1 may be selected from the following structures.
  • the compound of Formula 1 may be prepared in the core structure as shown in the following scheme.
  • Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.
  • 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.
  • a compound having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above.
  • the HOMO and LUMO energy levels of the compound may be controlled by introducing various substituents into the core structure of the above structure.
  • 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 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 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 includes a hole injection layer, a hole transport layer, a layer for simultaneously injecting and transporting holes, an emission layer, an electron transporting layer, an electron injecting layer, a layer for simultaneously injecting and transporting electrons, and an electron blocking layer as an organic material layer. It may have a structure including the.
  • 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 including the compound of Formula 1 is an organic light emitting device that is a hole injection layer or a light emitting layer.
  • the organic material layer including the compound of Formula 1 is an organic light emitting device that is a hole transport layer or an electron blocking layer.
  • the organic material layer may include a hole injection layer or a hole transport layer, one or more of the layers may include a compound represented by the formula (1).
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.
  • the compound represented by Formula 1 may be included as a dopant of the light emitting layer.
  • the organic material layer including the compound represented by Chemical Formula 1 may include the compound represented by Chemical Formula 1 as a dopant, and may include a fluorescent host or a phosphorescent host.
  • the organic material layer including the compound represented by Chemical Formula 1 includes the compound represented by Chemical Formula 1 as a dopant, includes a fluorescent host or a phosphorescent host, and other organic compounds, metals, or metal compounds. May be included as the dopant.
  • the organic material layer including the compound represented by Chemical Formula 1 may include the compound represented by Chemical Formula 1 as a dopant, include a fluorescent host or a phosphorescent host, and may be used with an iridium-based (Ir) dopant. have.
  • the organic material layer may include an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may include a compound represented by Chemical Formula 1.
  • the organic light emitting device may include an electron blocking layer, and the electron blocking layer may include a compound represented by Chemical Formula 1.
  • 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).
  • the 2 shows an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 8, a light emitting layer 3, and a layer 7 for simultaneously transporting electrons and electrons on a substrate 1.
  • the compound may be included in the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, or the electron blocking 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 layer may be prepared by using a variety of polymer materials, and by using a method such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than a deposition method. It can be prepared in layers.
  • the 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-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 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.
  • hole injecting materials include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene-based organics, quinacridone-based organics, and perylene-based Organic substances, anthraquinone and polyaniline and polythiophene-based conductive polymers, 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 emission layer may emit red, green, or blue light, and may be formed of a phosphor or a fluorescent material.
  • 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.
  • Alq 3 8-hydroxyquinoline aluminum complex
  • Carbazole series compounds Dimerized styryl compounds
  • BAlq 10-hydroxybenzoquinoline-metal compound
  • Benzoxazole, benzthiazole and benzimidazole series compounds include Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • 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.
  • 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.
  • 9,9'-spirobi [fluorene] -2-amine (50.00 g, 150.87 mmol) was dissolved in N, N-dimethylformamide (DMF) (200 ml) and the temperature was lowered to 0 ° C.
  • N-bromosuccinimide (NBS) (26.85 g, 150.87 mmol) was dissolved in N, N-dimethylformamide (DMF) (100 ml) and slowly added to the solution, followed by stirring. After completion of the reaction, the temperature was raised to room temperature, and water was added thereto, followed by reverse precipitation and filtration. The obtained solid was layered with chloroform and sodium thiosulfate solution. Recrystallization with hexane after solvent removal gave the compound 1-A (52.50 g, 84.81% yield).
  • a glass substrate coated with a thin film of ITO (Indium Tin Oxide) having a thickness of 1,400 kPa was put in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • ITO Indium Tin Oxide
  • Fischer Co. was used as a detergent
  • distilled water was filtered secondly as a filter of Millipore Co. as a 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.
  • a hole injection layer was formed by thermally vacuum depositing a compound represented by the following formula HAT on the prepared ITO transparent electrode to a thickness of 100 kPa.
  • the compound represented by the following formula HT1 was vacuum deposited to a thickness of 1150 kPa as a hole transport layer, and the following compound EB1 was thermally vacuum deposited to a thickness of 150 kPa as an electron blocking layer.
  • the compound represented by the following formula BH and the compound represented by the following formula BD were vapor deposited to a thickness of 200 kPa in a weight ratio of 25: 1 as a light emitting layer.
  • the compound represented by the following formula HB1 was vacuum deposited to a thickness of 50 kV as a hole blocking layer.
  • the compound represented by the following formula ET1 and the compound represented by the following Liq were thermally vacuum deposited to a thickness of 310 kPa in a weight ratio of 1: 1 as the electron transport layer and the electron injection layer.
  • the compound represented by Liq below was vacuum deposited to a thickness of 5 kPa.
  • lithium fluoride (LiF) and aluminum were deposited to a thickness of 1000 kW in order to form a cathode, thereby manufacturing an organic light emitting device.
  • the organic light emitting diodes of Examples 1-1 to 1-20 were manufactured by the same method as Comparative Example 1-1, except that Compound 1-1 was used instead of EB1 in Comparative Example 1-1.
  • T95 means the time it takes for the luminance to decrease to 95% from the initial luminance (6000 nit).
  • Example 1-1 Compound 1 3.53 6.31 0.140, 0.044 285 Example 1-2 Compound 2 3.51 6.21 0.141, 0.045 270 Example 1-3 Compound 3 3.45 6.30 0.140, 0.044 290 Example 1-4 Compound 4 3.55 6.15 0.141, 0.044 285 Example 1-5 Compound 5 3.48 6.28 0.142, 0.044 290 Example 1-6 Compound 6 3.52 6.12 0.141, 0.045 280 Example 1-7 Compound 7 3.51 6.13 0.142, 0.043 285 Example 1-8 Compound 8 3.48 6.17 0.139, 0.044 270 Example 1-9 Compound 9 3.53 6.11 0.140, 0.043 270 Example 1-10 Compound 10 3.48 6.23 0.139, 0.043 295 Example 1-11 Compound 11 3.55 6.21 0.143, 0.043 270
  • the compound according to the present invention was confirmed that the excellent electron blocking ability can be applied to the organic light emitting device.
  • T95 means the time it takes for the luminance to decrease to 95% from the initial luminance (6000 nit).
  • Example 2 Compound (hole transport layer) Voltage (V @ 10mA / cm 2 ) Efficiency (cd / A @ 10mA / cm 2 ) Color coordinates (x, y) Life (T95, hr)
  • Example 2-1 Compound 1 3.56 6.20 0.141, 0.043 290
  • Example 2-2 Compound 2 3.50 6.18 0.141, 0.045 275
  • Example 2-3 Compound 3 3.55 6.24 0.141, 0.045 285
  • Example 2-4 Compound 4 3.53 6.21 0.142, 0.043 270
  • Example 2-5 Compound 5 3.55 6.17 0.141, 0.044 285
  • Example 2-6 Compound 6 3.54 6.15 0.141, 0.044 275
  • Example 2-7 Compound 7 3.57 6.11 0.142, 0.043 285
  • Example 2-8 Compound 8 3.59 6.09 0.139, 0.045 270
  • Example 2-9 Compound 9 3.51 6.11 0.141, 0.043 285
  • Example 2-10 Compound 10 3.54 6.21 0.139, 0.0
  • the compound according to the present invention was confirmed that the excellent electron transport ability can be applied to the organic light emitting device.

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Abstract

The present specification provides a compound of formula 1 and an organic light emitting device comprising the same.

Description

아민계 화합물 및 이를 포함하는 유기 발광 소자Amine compound and organic light emitting device comprising the same
본 출원은 2016년 09월 23일 한국 특허청에 제출된 한국 특허 출원 제10-2016-0122409호 및 2017년 09월 22일 한국 특허청에 제출된 한국 특허 출원 제10-2017-0122421호의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.This application claims the benefit of the date of application of Korean Patent Application No. 10-2016-0122409 filed with the Korean Intellectual Property Office on September 23, 2016 and Korean Patent Application No. 10-2017-0122421 filed on September 22, 2017 with the Korean Patent Office. Claim, all of which are hereby incorporated by reference.
본 명세서는 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.The present specification relates to a compound and an organic light emitting device including the same.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어 질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. The organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows.
상기와 같은 유기 발광 소자를 위한 새로운 재료의 개발이 계속 요구되고 있다.There is a continuing need for the development of new materials for such organic light emitting devices.
본 명세서에는 아민계 화합물 및 이를 포함하는 유기 발광 소자가 기재된다.Herein, an amine compound and an organic light emitting device including the same are described.
본 명세서의 일 실시상태는 하기 화학식 1로 표시되는 화합물을 제공한다.An exemplary embodiment of the present specification provides a compound represented by the following formula (1).
[화학식 1] [Formula 1]
Figure PCTKR2017010533-appb-I000001
Figure PCTKR2017010533-appb-I000001
상기 화학식 1에 있어서,In Chemical Formula 1,
R1 내지 R4는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 실릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 티오알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이며,R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted thioalkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
n1 내지 n3는 각각 0 내지 4의 정수이고,n1 to n3 are each an integer of 0 to 4,
n1 내지 n3가 각각 2 이상인 경우, 괄호 내의 치환기는 서로 같거나 상이하며,when n1 to n3 are each 2 or more, the substituents in parentheses are the same as or different from each other,
n4는 0 내지 2의 정수이고,n4 is an integer of 0 to 2,
n4가 2 이상인 경우, 괄호 내의 치환기는 서로 같거나 상이하며,when n4 is 2 or more, the substituents in parentheses are the same as or different from each other,
p1 내지 p3는 각각 0 내지 3의 정수이고,p1 to p3 are each an integer of 0 to 3,
p1 내지 p3가 각각 2 이상인 경우, 괄호 내의 치환기는 서로 같거나 상이하며,when p1 to p3 are each 2 or more, the substituents in parentheses are the same as or different from each other,
L, L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 2가의 헤테로고리기이고,L, L1 and L2 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
Ar1은 트라이페닐렌이며,Ar1 is triphenylene,
Ar2는 수소; 중수소; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 아릴알케닐기; 또는 치환 또는 비치환된 헤테로고리기이고,Ar2 is hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Substituted or unsubstituted arylalkyl group; Substituted or unsubstituted aryl alkenyl group; Or a substituted or unsubstituted heterocyclic group,
X1은 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 아릴알케닐기; 또는 치환 또는 비치환된 헤테로고리기이다.X1 is a substituted or unsubstituted aryl group; Substituted or unsubstituted arylalkyl group; Substituted or unsubstituted aryl alkenyl group; Or a substituted or unsubstituted heteroring group.
또한, 본 명세서의 일 실시상태는 제1 전극, 제2 전극, 및 상기 제1 전극과 제2 전극 사이에 배치된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화학식 1의 화합물을 포함하는 것인 유기 발광 소자를 제공한다.In addition, 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).
본 명세서에 기재된 화합물은 유기 발광 소자의 유기물층의 재료로서 사용될 수 있다. 적어도 하나의 실시상태에 따른 화합물은 유기 발광 소자에서 효율의 향상, 낮은 구동전압 및/또는 수명 특성을 향상시킬 수 있다. 본 명세서에 기재된 화합물은 정공주입, 정공수송, 정공주입과 정공수송, 전자억제, 발광, 정공억제, 전자수송, 또는 전자주입 재료로 사용될 수 있다. The compound described herein can be used as the material of the organic material layer of the organic light emitting device. The compound according to at least one exemplary embodiment may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode. The compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, electron suppression, luminescence, hole suppression, electron transport, or electron injection material.
특히, 본 명세서에 기재된 화합물을 유기 발광 소자의 정공주입층, 정공수송층에 이용하는 경우에 유기 발광 소자의 효율을 향상시킬 수 있고, 구동전압이 낮아지며, 또한 소자의 수명이 길어지는 효과를 얻을 수 있다.In particular, when the compound described herein is used in the hole injection layer and the hole transport layer of the organic light emitting device, the efficiency of the organic light emitting device can be improved, the driving voltage can be lowered, and the life of the device can be obtained. .
도 1은 기판(1), 양극(2), 발광층(3) 및 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.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.
도 2는 기판 (1), 양극(2), 정공 주입층(5), 정공 수송층(6), 전자 저지층(8), 발광층(3), 전자 수송 및 전자 주입을 동시에 하는 층(7) 및 음극(4)로 이루어진 유기 발광 소자의 예를 도시한 것이다.2 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 8, a light emitting layer 3, and a layer 7 for simultaneously transporting electrons and electrons. And an example of an organic light emitting element composed of a cathode 4.
1: 기판1: substrate
2: 양극2: anode
3: 발광층3: light emitting layer
4: 음극4: cathode
5: 정공 주입층5: hole injection layer
6: 정공 수송층6: hole transport layer
7: 전자 수송 및 전자 주입을 동시에 하는 층7: layer to carry out electron transport and electron injection at the same time
8: 전자 저지층8: electron blocking layer
이하 본 명세서에 대하여 더욱 상세히 설명한다. Hereinafter, the present specification will be described in more detail.
본 명세서의 일 실시상태는 하기 화학식 1로 표시되는 화합물을 제공한다. An exemplary embodiment of the present specification provides a compound represented by the following formula (1).
[화학식 1] [Formula 1]
Figure PCTKR2017010533-appb-I000002
Figure PCTKR2017010533-appb-I000002
상기 화학식 1에 있어서,In Chemical Formula 1,
R1 내지 R4는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 실릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 티오알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이며,R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted thioalkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
n1 내지 n3는 각각 0 내지 4의 정수이고,n1 to n3 are each an integer of 0 to 4,
n1 내지 n3가 각각 2 이상인 경우, 괄호 내의 치환기는 서로 같거나 상이하며,when n1 to n3 are each 2 or more, the substituents in parentheses are the same as or different from each other,
n4는 0 내지 2의 정수이고,n4 is an integer of 0 to 2,
n4가 2 이상인 경우, 괄호 내의 치환기는 서로 같거나 상이하며,when n4 is 2 or more, the substituents in parentheses are the same as or different from each other,
p1 내지 p3는 각각 0 내지 3의 정수이고,p1 to p3 are each an integer of 0 to 3,
p1 내지 p3가 각각 2 이상인 경우, 괄호 내의 치환기는 서로 같거나 상이하며,when p1 to p3 are each 2 or more, the substituents in parentheses are the same as or different from each other,
L, L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 2가의 헤테로고리기이고,L, L1 and L2 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
Ar1은 트라이페닐렌이며,Ar1 is triphenylene,
Ar2는 수소; 중수소; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 아릴알케닐기; 또는 치환 또는 비치환된 헤테로고리기이고,Ar2 is hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Substituted or unsubstituted arylalkyl group; Substituted or unsubstituted aryl alkenyl group; Or a substituted or unsubstituted heterocyclic group,
X1은 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 아릴알케닐기; 또는 치환 또는 비치환된 헤테로고리기이다.X1 is a substituted or unsubstituted aryl group; Substituted or unsubstituted arylalkyl group; Substituted or unsubstituted aryl alkenyl group; Or a substituted or unsubstituted heteroring group.
상기 치환기들의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다. Examples of the substituents are described below, but are not limited thereto.
본 명세서의 “
Figure PCTKR2017010533-appb-I000003
” 및 “
Figure PCTKR2017010533-appb-I000004
”는 결합하는 위치를 의미한다.As used herein,
Figure PCTKR2017010533-appb-I000003
”And“
Figure PCTKR2017010533-appb-I000004
”Means position to join.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 포스핀옥사이드기; 알콕시기; 실릴기; 붕소기; 알킬기; 아릴알킬기; 시클로알킬기; 알케닐기; 아릴알케닐기; 아릴기; 아민기; 및 헤테로고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되거나, 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환 또는 비치환된 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 바이페닐기일 수 있다. 즉, 바이페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 있다.As used herein, 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; Silyl groups; Boron group; Alkyl groups; Arylalkyl group; Cycloalkyl group; Alkenyl groups; Aryl alkenyl group; Aryl group; Amine groups; 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 exemplified above. For example, "a substituent to which two or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.
본 명세서에서 카보닐기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 40인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.Although 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.
Figure PCTKR2017010533-appb-I000005
Figure PCTKR2017010533-appb-I000005
본 명세서에 있어서, 에스테르기는 에스테르기의 산소가 탄소수 1 내지 40의 직쇄, 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 30의 아릴기로 치환될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, 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.
Figure PCTKR2017010533-appb-I000006
Figure PCTKR2017010533-appb-I000006
본 명세서에 있어서, 이미드기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 25인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In this specification, although 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.
Figure PCTKR2017010533-appb-I000007
Figure PCTKR2017010533-appb-I000007
본 명세서에 있어서, 실릴기는 -SiRaRbRc의 화학식으로 표시될 수 있고, 상기 Ra, Rb 및 Rc는 각각 수소; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기일 수 있다. 상기 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다. In the present specification, 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.
본 명세서에 있어서, 붕소기는 -BRaRb의 화학식으로 표시될 수 있고, 상기 Ra 및 Rb는 각각 수소; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기일 수 있다. 상기 붕소기는 구체적으로 트리메틸붕소기, 트리에틸붕소기, t-부틸디메틸붕소기, 트리페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다.In the present specification, 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.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 6이다. 알킬기의 구체적인 예로는 메틸기, 에틸기, 프로필기, n-프로필기, 이소프로필기, 부틸기, n-부틸기, 이소부틸기, tert-부틸기, sec-부틸기, 펜틸기, n-펜틸기, 이소펜틸기, 네오펜틸기, tert-펜틸기, 헥실기, n-헥실기, 헵틸, n-헵틸, 시클로펜틸메틸, 시클로헥실메틸, 옥틸, n-옥틸, tert-옥틸, n-노닐 등이 있으나, 이들에 한정되지 않는다.In the present specification, 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. Specific examples of the alkyl group include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, pentyl group, n-pentyl group Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, n-nonyl, etc. There is, but is not limited to these.
본 명세서에 있어서, 상기 알콕시기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 40인 것이 바람직하다. 구체적으로, 메톡시기, 에톡시기, n-프로폭시기, 이소프로폭시기, i-프로필옥시기, n-부톡시기, 이소부톡시기, tert-부톡시기, sec-부톡시기, n-펜틸옥시기, 네오펜틸옥시기, 이소펜틸옥시기, n-헥실옥시기, 3,3-디메틸부틸옥시기, 2-에틸부틸옥시기, n-옥틸옥시기, n-노닐옥시기, n-데실옥시기, 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, 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 group, ethoxy group, n-propoxy group, isopropoxy group, i-propyloxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n-pentyloxy group , Neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group , Etc., but is not limited thereto.
본 명세서에 기재된 알킬기, 알콕시기 및 그 외 알킬기 부분을 포함하는 치환체는 직쇄 또는 분쇄 형태를 모두 포함한다.Substituents comprising alkyl groups, alkoxy groups and other alkyl group moieties described herein include both straight and pulverized forms.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 6이다. 구체적인 예로는 비닐기, 1-프로페닐기, 이소프로페닐기, 1-부테닐기, 2-부테닐기, 3-부테닐기 1-펜테닐기, 2-펜테닐기, 3-펜테닐기, 3-메틸-1-부테닐기, 1,3-부타디에닐기, 알릴기, 1-페닐비닐-1-일기, 2-페닐비닐-1-일기, 2,2-디페닐비닐-1-일기, 2-페닐-2-(나프틸-1-일)비닐-1-일기, 2,2-비스(디페닐-1-일)비닐-1-일기, 스틸베닐기, 스티레닐기 등이 있으나 이들에 한정되지 않는다.In the present specification, 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. As a specific example, a vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 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 group, 2,2-bis (diphenyl-1-yl) vinyl-1-yl group, stilbenyl group, styrenyl group and the like, but are not limited thereto.
본 명세서에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 40이다. 또 하나의 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 시클로프로필기, 시클로부틸기, 시클로펜틸기, 3-메틸시클로펜틸기, 2,3-디메틸시클로펜틸기, 시클로헥실기, 3-메틸시클로헥실기, 4-메틸시클로헥실기, 2,3-디메틸시클로헥실기, 3,4,5-트리메틸시클로헥실기, 4-tert-부틸시클로헥실기, 시클로헵틸기, 시클로옥틸기 등이 있으나, 이에 한정되지 않는다.In the present specification, 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. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2, 3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group, and the like, but are not limited thereto.
본 명세서에 있어서, 아민기는 탄소수는 특별히 한정되지 않으나, 1 내지 30인 것이 바람직하다. 아민기는 전술한 알킬기, 아릴기, 헤테로고리기, 알케닐기, 시클로알킬기 및 이들의 조합 등이 치환될 수 있으며, 아민기의 구체적인 예로는 메틸아민기, 디메틸아민기, 에틸아민기, 디에틸아민기, 페닐아민기, 9,9-디메틸플루오레닐페닐아민기, 피리딜페닐아민기, 디페닐아민기, 페닐피리딜아민기, 나프틸아민기, 바이페닐아민기, 안트라세닐아민기, 디벤조퓨라닐페닐아민기, 9-메틸-안트라세닐아민기, 디페닐아민기, 페닐나프틸아민기, 디톨릴아민기, 페닐톨릴아민기, 트리페닐아민기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the amine group is not particularly limited, but is preferably 1 to 30. The amine group may be substituted with the aforementioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group and combinations thereof, and the like, and specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group and diethylamine. Group, phenylamine group, 9,9-dimethylfluorenylphenylamine group, pyridylphenylamine group, diphenylamine group, phenylpyridylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, Dibenzofuranylphenylamine group, 9-methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, and the like, but are limited thereto. It is not.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기, 테트라페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 파이레닐기, 페릴레닐기, 크라이세닐기, 트리페닐레닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, 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. As the aryl group, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, or the like, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, triphenylenyl group, fluorenyl group, and the like, but is not limited thereto.
본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다. 상기 플루오레닐기가 치환되는 경우,
Figure PCTKR2017010533-appb-I000008
(9,9-디메틸플루오레닐기),
Figure PCTKR2017010533-appb-I000009
(9-메틸-9-페닐플루오레닐기),
Figure PCTKR2017010533-appb-I000010
(9,9-디페닐플루오레닐기),
Figure PCTKR2017010533-appb-I000011
,
Figure PCTKR2017010533-appb-I000012
,
Figure PCTKR2017010533-appb-I000013
등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,
Figure PCTKR2017010533-appb-I000008
(9,9-dimethylfluorenyl group),
Figure PCTKR2017010533-appb-I000009
(9-methyl-9-phenylfluorenyl group),
Figure PCTKR2017010533-appb-I000010
(9,9-diphenylfluorenyl group),
Figure PCTKR2017010533-appb-I000011
,
Figure PCTKR2017010533-appb-I000012
,
Figure PCTKR2017010533-appb-I000013
Etc., but is not limited thereto.
본 명세서에 있어서, 헤테로 고리기는 이종원자로 N, O, P, S, Si 및 Se 중 1개 이상을 포함하는 헤테로 고리기로서, 탄소수는 특별히 한정되지 않으나 탄소수 1 내지 60인 것이 바람직하다. 일 실시상태에 따르면, 상기 헤테로 고리기의 탄소수는 1 내지 30이다. 헤테로 고리기의 예로는 예로는 피리딜기, 피롤기, 피리미딜기, 피리다지닐기, 퓨라닐기, 티오페닐기, 이미다졸기, 피라졸기, 옥사졸기, 이소옥사졸기, 티아졸기, 이소티아졸기, 트리아졸기, 옥사디아졸기, 티아디아졸기, 디티아졸기, 테트라졸기, 피라닐기, 티오피라닐기, 피라지닐기, 옥사지닐기, 티아지닐기, 디옥시닐기, 트리아지닐기, 테트라지닐기, 퀴놀리닐기, 이소퀴놀리닐기, 퀴놀릴기, 퀴나졸리닐기, 퀴녹살리닐기, 나프티리디닐기, 아크리딜기, 크산테닐기, 페난트리디닐기, 디아자나프탈레닐기, 트리아자인데닐기, 인돌기, 인돌리닐기, 인돌리지닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 벤조티아졸기, 벤즈옥사졸기, 벤즈이미다졸기, 페나지닐기, 이미다조피리딘기, 페녹사지닐기, 페난트리딘기, 페난트롤린(phenanthroline)기, 페노티아진(phenothiazine)기, 이미다조피리딘기, 이미다조페난트리딘기. 벤조이미다조퀴나졸린기, 또는 벤조이미다조페난트리딘기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, 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. Examples of the heterocyclic group 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, phenanthridinyl group, diazanphthalenyl group, triazaininyl group, indole group , Indolinyl group, indolinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, benzothiazole group, benzoxazole group, benzimidazole group, phenazinyl group, Imidazopyridine group, phenoxazinyl group, phenanthridine group, I trawl Lin (phenanthroline) group, a phenothiazine (phenothiazine) group, an imidazopyridine group, dingi already jope I tree. Although there exists a benzoimidazoquinazoline group or a benzoimidazophenanthridine group, it is not limited only to these.
본 명세서에 있어서, 상기 헤테로 고리기는 고리를 이루는 원소의 수가 2 내지 60이다. 또 하나의 실시상태에 있어서, 상기 헤테로고리기는 고리를 이루는 원소의 수가 2 내지 40이다. 일 실시상태에 있어서, 상기 헤테로 고리기는 고리를 이루는 원소의 수가 2 내지 20이다.In the present specification, the heterocyclic group is 2 to 60 the number of elements constituting the ring. In another exemplary embodiment, the heterocyclic group has 2 to 40 ring atoms. In one embodiment, the hetero ring group has 2 to 20 ring atoms.
본 명세서에 있어서, 아릴알킬기, 아릴알케닐기 중의 아릴기는 전술한 아릴기에 관한 설명이 적용될 수 있다.In the present specification, an arylalkyl group and an aryl group in the arylalkenyl group may be described with respect to the aforementioned aryl group.
본 명세서에 있어서, 아릴알킬기, 티오알킬기 중의 알킬기는 전술한 알킬기에 관한 설명이 적용될 수 있다.In the present specification, the alkyl group in the arylalkyl group and the thioalkyl group may be described with respect to the alkyl group described above.
본 명세서에 있어서, 아릴알케닐기 중의 알케닐기는 전술한 알케닐기에 관한 설명이 적용될 수 있다.In the present specification, the alkenyl group in the arylalkenyl group may be applicable to the description of the alkenyl group described above.
본 명세서에 있어서, 인접하는 기와 서로 결합하여 고리를 형성한다는 의미는 인접하는 기와 서로 결합하여 치환 또는 비치환된 지방족 탄화수소고리; 치환 또는 비치환된 방향족 탄화수소고리기; 치환 또는 비치환된 지방족 헤테로고리기; 치환 또는 비치환된 방향족 헤테로고리기; 또는 이들의 축합고리를 형성하는 것을 의미한다.In the present specification, 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 group; Substituted or unsubstituted aliphatic heterocyclic group; Substituted or unsubstituted aromatic heterocyclic group; Or to form a condensed ring thereof.
본 명세서에 있어서, 지방족 탄화수소고리란 방향족이 아닌 고리로서 탄소와 수소 원자로만 이루어진 고리를 의미한다. 구체적으로, 지방족 탄화수소고리의 예로는 시클로프로판, 시클로부탄, 시클로부텐, 시클로펜탄, 시클로펜텐, 시클로헥산, 시클로헥센, 1,4-시클로헥사디엔, 시클로헵탄, 시클로헵텐, 시클로옥탄, 시클로옥텐 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the aliphatic hydrocarbon ring means a ring composed only of carbon and hydrogen atoms as a ring which is not aromatic. Specifically, 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.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물은 하기 화학식 2 내지 4 중 하나로 표시될 수 있다.In one embodiment of the present specification, the compound represented by Chemical Formula 1 may be represented by one of the following Chemical Formulas 2 to 4.
[화학식 2][Formula 2]
Figure PCTKR2017010533-appb-I000014
Figure PCTKR2017010533-appb-I000014
[화학식 3][Formula 3]
Figure PCTKR2017010533-appb-I000015
Figure PCTKR2017010533-appb-I000015
[화학식 4][Formula 4]
Figure PCTKR2017010533-appb-I000016
Figure PCTKR2017010533-appb-I000016
상기 화학식 2 내지 4에 있어서,In Chemical Formulas 2 to 4,
R1 내지 R4, X1, L, L1, L2, n1 내지 n4, p1 내지 p3, Ar1 및 Ar2는 상기 화학식 1에서의 정의와 같다.R1 to R4, X1, L, L1, L2, n1 to n4, p1 to p3, Ar1 and Ar2 are the same as defined in the formula (1).
본 명세서의 일 실시상태에 있어서, 상기 L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 탄소수 6 내지 60의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 2가의 헤테로 고리기이다.In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted divalent heterocyclic group having 2 to 60 carbon atoms.
또 하나의 일 실시상태에 있어서, 상기 L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로 고리기이다.In another exemplary embodiment, L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted hetero ring group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 하기 구조들 중에서 선택될 수 있다.In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; Or the following structures.
Figure PCTKR2017010533-appb-I000017
Figure PCTKR2017010533-appb-I000017
상기 구조들에 있어서,In the above structures,
R17 내지 R19은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 실릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.R17 to R19 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
본 명세서에 실시상태에 따르면, 상기 L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 페닐렌기이다.According to the exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; It is a substituted or unsubstituted phenylene group.
본 명세서의 일 실시상태에 있어서, 상기 L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 페닐렌기이다.In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a phenylene group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, -(L)p1-N[(L1)p2Ar1][(L2)p3Ar2]는 하기 화학식 5로 표시될 수 있다.According to an exemplary embodiment of the present specification, in the general formula 1,-(L) p1 -N [(L1) p2 Ar1] [(L2) p3 Ar2] may be represented by the following formula (5).
[화학식 5][Formula 5]
Figure PCTKR2017010533-appb-I000018
Figure PCTKR2017010533-appb-I000018
상기 화학식 5에 있어서, In Chemical Formula 5,
L, L2, p1, p3 및 Ar2의 정의는 상기 화학식 1에서의 정의와 같다.Definitions of L, L2, p1, p3, and Ar2 are the same as those defined in Chemical Formula 1.
본 명세서의 일 실시상태에 있어서, 상기 R1 내지 R4는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
본 명세서의 일 실시상태에 있어서, 상기 R1 내지 R4는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 40의 알킬기; 치환 또는 비치환된 탄소수 3 내지 60의 시클로알킬기; 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로고리기이다.In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R1 내지 R4는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기이다.In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R1 내지 R4는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 아릴기 또는 헤테로고리기로 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 알킬기, 아릴기 또는 헤테로고리기로 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 알킬기 또는 헤테로고리기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 알킬기 또는 아릴기로 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기이다.In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with an aryl group or a heterocyclic group; A cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with an alkyl group, an aryl group or a heterocyclic group; An aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group or a heterocyclic group; Or a heterocyclic group having 2 to 30 carbon atoms unsubstituted or substituted with an alkyl group or an aryl group.
본 명세서의 일 실시상태에 있어서, 상기 L은 직접결합 또는 하기 구조들 중에서 선택된 어느 하나이다.In one embodiment of the present specification, L is any one selected from a direct bond or the following structures.
Figure PCTKR2017010533-appb-I000019
Figure PCTKR2017010533-appb-I000019
상기 구조들에 있어서,In the above structures,
R17 내지 R19은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 실릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.R17 to R19 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
본 명세서의 일 실시상태에 있어서, 상기 R17 내지 R19는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.In one embodiment of the present specification, R17 to R19 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
본 명세서의 일 실시상태에 있어서, 상기 R17 내지 R19는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 40의 알킬기; 치환 또는 비치환된 탄소수 3 내지 60의 시클로알킬기; 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로고리기이다.In one embodiment of the present specification, R17 to R19 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
본 명세서의 일 실시상태에 있어서, R17 내지 R19는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기이다.In one embodiment of the present specification, R17 to R19 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, R17 내지 R19는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 아릴기 또는 헤테로고리기로 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 알킬기, 아릴기 또는 헤테로고리기로 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 알킬기 또는 헤테로고리기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 알킬기 또는 아릴기로 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기이다.In one embodiment of the present specification, R17 to R19 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with an aryl group or a heterocyclic group; A cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with an alkyl group, an aryl group or a heterocyclic group; An aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group or a heterocyclic group; Or a heterocyclic group having 2 to 30 carbon atoms unsubstituted or substituted with an alkyl group or an aryl group.
본 명세서의 일 실시상태에 따르면, 상기 X1은 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.According to an exemplary embodiment of the present specification, X1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
또 하나의 일 실시상태에 있어서, 상기 X1은 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로고리기이다.In another exemplary embodiment, X1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 X1은 아릴기로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 아릴기로 치환 또는 비치환된 탄소수 2 내지 60의 헤테로 고리기이다.In one embodiment of the present specification, X1 is an aryl group having 6 to 60 carbon atoms unsubstituted or substituted with an aryl group; Or a heterocyclic group having 2 to 60 carbon atoms unsubstituted or substituted with an aryl group.
본 명세서의 일 실시상태에 있어서, 상기 X1은 페닐기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 페닐기로 치환 또는 비치환된 탄소수 2 내지 40의 헤테로 고리기이다.In one embodiment of the present specification, X1 is an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a phenyl group; Or a heterocyclic group having 2 to 40 carbon atoms unsubstituted or substituted with a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 X1은 페닐기로 치환 또는 비치환된 페닐기; 페닐기로 치환 또는 비치환된 바이페닐기; 페닐기로 치환 또는 비치환된 나프틸기; 페닐기로 치환 또는 비치환된 페난트레닐기; 페닐기로 치환 또는 비치환된 트라이페닐렌기; 페닐기로 치환 또는 비치환된 디벤조티오펜기; 페닐기로 치환 또는 비치환된 디벤조퓨란기; 페닐기로 치환 또는 비치환된 카바졸릴기; 또는 페닐기로 치환 또는 비치환된 벤조카바졸릴기이다.According to an exemplary embodiment of the present specification, X1 is a phenyl group unsubstituted or substituted with a phenyl group; A biphenyl group unsubstituted or substituted with a phenyl group; A naphthyl group unsubstituted or substituted with a phenyl group; Phenanthrenyl group unsubstituted or substituted with a phenyl group; Triphenylene group unsubstituted or substituted with a phenyl group; Dibenzothiophene group unsubstituted or substituted with a phenyl group; Dibenzofuran group unsubstituted or substituted with a phenyl group; Carbazolyl group unsubstituted or substituted with a phenyl group; Or a benzocarbazolyl group unsubstituted or substituted with a phenyl group.
본 명세서의 일 실시상태에 있어서, 상기 X1은 하기 구조들 중에서 선택된 것일 수 있다.In one embodiment of the present specification, X1 may be selected from the following structures.
Figure PCTKR2017010533-appb-I000020
Figure PCTKR2017010533-appb-I000020
Figure PCTKR2017010533-appb-I000021
Figure PCTKR2017010533-appb-I000021
Figure PCTKR2017010533-appb-I000022
Figure PCTKR2017010533-appb-I000022
상기 구조들에 있어서, In the above structures,
R11 내지 R13은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 실릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 치환기는 서로 결합하여 치환 또는 비치환된 고리를 형성한다.R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring.
본 명세서의 일 실시상태에 있어서, 상기 R11 내지 R13은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.In one embodiment of the present specification, R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
본 명세서의 일 실시상태에 있어서, 상기 R11 내지 R13은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 40의 알킬기; 치환 또는 비치환된 탄소수 3 내지 60의 시클로알킬기; 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로고리기이다.In one embodiment of the present specification, R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R11 내지 R13은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기이다.In one embodiment of the present specification, R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R11 내지 R13은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 아릴기 또는 헤테로고리기로 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 알킬기, 아릴기 또는 헤테로고리기로 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 알킬기 또는 헤테로고리기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 알킬기 또는 아릴기로 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기이다.In one embodiment of the present specification, R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with an aryl group or a heterocyclic group; A cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with an alkyl group, an aryl group or a heterocyclic group; An aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group or a heterocyclic group; Or a heterocyclic group having 2 to 30 carbon atoms unsubstituted or substituted with an alkyl group or an aryl group.
본 명세서의 일 실시상태에 있어서, 상기 R11 및 R12는 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In one embodiment of the present specification, R11 and R12 may be combined with each other to form a substituted or unsubstituted ring.
본 명세서의 일 실시상태에 따르면, 상기 R11 및 R12는 서로 결합하여 치환 또는 비치환된 탄화수소고리를 형성할 수 있다.According to an exemplary embodiment of the present specification, the R11 and R12 may be combined with each other to form a substituted or unsubstituted hydrocarbon ring.
또 하나의 일 실시상태에 따르면, 상기 R11 및 R12는 서로 결합하여 시클로펜탄 또는 시클로헥산을 형성할 수 있다.According to another exemplary embodiment, R11 and R12 may combine with each other to form cyclopentane or cyclohexane.
본 명세서의 일 실시상태에 있어서, 상기 Ar2는 수소; 중수소; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.In one embodiment of the present specification, Ar2 is hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
본 명세서의 일 실시상태에 따르면, 상기 Ar2는 수소; 중수소; 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 40의 헤테로고리기이다.According to an exemplary embodiment of the present specification, Ar2 is hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 Ar2는 수소; 중수소; 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 페난트레닐기; 치환 또는 비치환된 트라이페닐기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 카바졸릴기; 또는 치환 또는 비치환된 벤조카바졸릴기이다.In one embodiment of the present specification, Ar2 is hydrogen; heavy hydrogen; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted triphenyl group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted carbazolyl group; Or a substituted or unsubstituted benzocarbazolyl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar2는 하기 구조들 중에서 선택된 것일 수 있다.In one embodiment of the present specification, Ar2 may be selected from the following structures.
Figure PCTKR2017010533-appb-I000023
Figure PCTKR2017010533-appb-I000023
Figure PCTKR2017010533-appb-I000024
Figure PCTKR2017010533-appb-I000024
상기 구조들에 있어서,In the above structures,
R14 내지 R16은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 실릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 치환기는 서로 결합하여 치환 또는 비치환된 고리를 형성한다.R14 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring.
본 명세서의 일 실시상태에 있어서, 상기 R14 내지 R16은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.In one embodiment of the present specification, R14 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
본 명세서의 일 실시상태에 있어서, 상기 R14 내지 R16은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 40의 알킬기; 치환 또는 비치환된 탄소수 3 내지 60의 시클로알킬기; 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로고리기이다.In one embodiment of the present specification, R14 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R14 내지 R16은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기이다.In one embodiment of the present specification, R14 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R14 내지 R16은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 아릴기 또는 헤테로고리기로 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 알킬기, 아릴기 또는 헤테로고리기로 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 알킬기 또는 헤테로고리기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 알킬기 또는 아릴기로 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기이다.In one embodiment of the present specification, R14 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with an aryl group or a heterocyclic group; A cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with an alkyl group, an aryl group or a heterocyclic group; An aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group or a heterocyclic group; Or a heterocyclic group having 2 to 30 carbon atoms unsubstituted or substituted with an alkyl group or an aryl group.
본 명세서의 일 실시상태에 있어서, 상기 R14 및 R15는 서로 결합하여 치환 또는 비치환된 탄화수소고리를 형성할 수 있다.In one embodiment of the present specification, R14 and R15 may be combined with each other to form a substituted or unsubstituted hydrocarbon ring.
본 명세서의 일 실시상태에 따르면, 상기 R14 및 R15는 서로 결합하여 시클로펜탄 또는 시클로헥산을 형성할 수 있다.According to an exemplary embodiment of the present specification, the R14 and R15 may be combined with each other to form cyclopentane or cyclohexane.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1의 화합물은 하기 구조들 중에서 선택된 것일 수 있다.In one embodiment of the present specification, the compound of Formula 1 may be selected from the following structures.
Figure PCTKR2017010533-appb-I000025
Figure PCTKR2017010533-appb-I000025
Figure PCTKR2017010533-appb-I000026
Figure PCTKR2017010533-appb-I000026
Figure PCTKR2017010533-appb-I000027
Figure PCTKR2017010533-appb-I000027
Figure PCTKR2017010533-appb-I000028
Figure PCTKR2017010533-appb-I000028
Figure PCTKR2017010533-appb-I000029
Figure PCTKR2017010533-appb-I000029
Figure PCTKR2017010533-appb-I000030
Figure PCTKR2017010533-appb-I000030
Figure PCTKR2017010533-appb-I000031
Figure PCTKR2017010533-appb-I000031
Figure PCTKR2017010533-appb-I000032
Figure PCTKR2017010533-appb-I000032
Figure PCTKR2017010533-appb-I000033
Figure PCTKR2017010533-appb-I000033
Figure PCTKR2017010533-appb-I000034
Figure PCTKR2017010533-appb-I000034
Figure PCTKR2017010533-appb-I000035
Figure PCTKR2017010533-appb-I000035
Figure PCTKR2017010533-appb-I000036
Figure PCTKR2017010533-appb-I000036
Figure PCTKR2017010533-appb-I000037
Figure PCTKR2017010533-appb-I000037
Figure PCTKR2017010533-appb-I000038
Figure PCTKR2017010533-appb-I000038
Figure PCTKR2017010533-appb-I000039
Figure PCTKR2017010533-appb-I000039
Figure PCTKR2017010533-appb-I000040
Figure PCTKR2017010533-appb-I000040
Figure PCTKR2017010533-appb-I000041
Figure PCTKR2017010533-appb-I000041
Figure PCTKR2017010533-appb-I000042
Figure PCTKR2017010533-appb-I000042
Figure PCTKR2017010533-appb-I000043
Figure PCTKR2017010533-appb-I000043
Figure PCTKR2017010533-appb-I000044
Figure PCTKR2017010533-appb-I000044
Figure PCTKR2017010533-appb-I000045
Figure PCTKR2017010533-appb-I000045
Figure PCTKR2017010533-appb-I000046
Figure PCTKR2017010533-appb-I000046
Figure PCTKR2017010533-appb-I000047
Figure PCTKR2017010533-appb-I000047
Figure PCTKR2017010533-appb-I000048
Figure PCTKR2017010533-appb-I000048
Figure PCTKR2017010533-appb-I000049
Figure PCTKR2017010533-appb-I000049
Figure PCTKR2017010533-appb-I000050
Figure PCTKR2017010533-appb-I000050
Figure PCTKR2017010533-appb-I000051
Figure PCTKR2017010533-appb-I000051
Figure PCTKR2017010533-appb-I000052
Figure PCTKR2017010533-appb-I000052
Figure PCTKR2017010533-appb-I000053
Figure PCTKR2017010533-appb-I000053
Figure PCTKR2017010533-appb-I000054
Figure PCTKR2017010533-appb-I000054
Figure PCTKR2017010533-appb-I000055
Figure PCTKR2017010533-appb-I000055
Figure PCTKR2017010533-appb-I000056
Figure PCTKR2017010533-appb-I000056
Figure PCTKR2017010533-appb-I000057
Figure PCTKR2017010533-appb-I000057
본 명세서의 일 실시상태에 따른 화합물은 후술하는 제조방법으로 제조될 수 있다.Compounds according to one embodiment of the present specification may be prepared by the preparation method described below.
예컨대 상기 화학식 1의 화합물은 하기 반응식과 같이 코어구조가 제조될 수 있다. 치환기는 당 기술분야에 알려져 있는 방법에 의하여 결합될 수 있으며, 치환기의 종류, 위치 또는 개수는 당 기술분야에 알려져 있는 기술에 따라 변경될 수 있다.For example, the compound of Formula 1 may be prepared in the core structure as shown in the following scheme. Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.
본 명세서에 따른 화합물은 하기와 같이 합성될 수 있다.Compounds according to the present specification can be synthesized as follows.
단계 1)Step 1)
스피로비플루오렌 아민과 N-브로모석시니미드(NBS)의 브로미네이션 반응을 통한 브롬 치환된 1차 아민 합성Bromine Substituted Primary Amine Synthesis through Bromination Reaction of Spirobifluorene Amine and N-bromosuccinimide (NBS)
Figure PCTKR2017010533-appb-I000058
Figure PCTKR2017010533-appb-I000058
단계 2)Step 2)
상기 단계 1에서 수득한 브롬 치환된 1차 아민과 X1-보론산의 커플링 반응을 통한 X1 치환된 1차 아민 합성X1-substituted primary amine synthesis through coupling reaction of bromine substituted primary amine and X1-boronic acid obtained in step 1
Figure PCTKR2017010533-appb-I000059
Figure PCTKR2017010533-appb-I000059
단계 3)Step 3)
상기 단계 2에서 수득한 X1 치환된 1차 아민과 트리페닐렌의 아미네이션 반응을 통한 2차 아민 합성(Xa=halide)Secondary amine synthesis (Xa = halide) through amination reaction of X1 substituted primary amine and triphenylene obtained in step 2
Figure PCTKR2017010533-appb-I000060
Figure PCTKR2017010533-appb-I000060
단계 4)Step 4)
상기 단계 3에서 수득한 2차 아민과 아릴할라이드(Ar2-(L2)p3-Xb)의 아미네이션 반응을 통한 3차 아민 합성(Xb=halide)Tertiary amine synthesis (Xb = halide) through amination reaction of secondary amine obtained in step 3 with aryl halide (Ar2- (L2) p3 -Xb)
Figure PCTKR2017010533-appb-I000061
Figure PCTKR2017010533-appb-I000061
화합물의 컨쥬게이션 길이와 에너지 밴드갭은 밀접한 관계가 있다. 구체적으로, 화합물의 컨쥬게이션 길이가 길수록 에너지 밴드갭이 작아진다. 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.
본 발명에서는 상기와 같이 코어 구조에 다양한 치환기를 도입함으로써 다양한 에너지 밴드갭을 갖는 화합물을 합성할 수 있다. 또한, 본 발명에서는 상기와 같은 구조의 코어 구조에 다양한 치환기를 도입함으로써 화합물의 HOMO 및 LUMO 에너지 준위도 조절할 수 있다.In the present invention, a compound having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above. In addition, in the present invention, the HOMO and LUMO energy levels of the compound may be controlled by introducing various substituents into the core structure of the above structure.
또한, 상기와 같은 구조의 코어 구조에 다양한 치환기를 도입함으로써 도입된 치환기의 고유 특성을 갖는 화합물을 합성할 수 있다. 예컨대, 유기 발광 소자 제조시 사용되는 정공 주입층 물질, 정공 수송용 물질, 발광층 물질 및 전자 수송층 물질에 주로 사용되는 치환기를 상기 코어 구조에 도입함으로써 각 유기물층에서 요구하는 조건들을 충족시키는 물질을 합성할 수 있다.Moreover, the compound which has the intrinsic property of the introduced substituent can be synthesize | combined by introducing various substituents into the core structure of the above structure. For example, by incorporating 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.
또한, 본 발명에 따른 유기 발광 소자는 제1 전극, 제2 전극, 및 상기 제1 전극과 제2 전극 사이에 배치된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화합물을 포함하는 것을 특징으로 한다.In addition, the organic light emitting device according to the present invention 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.
본 발명의 일 실시상태에 있어서, 상기 제1 전극은 양극이고, 상기 제2 전극은 음극이다.In one embodiment of the present invention, the first electrode is an anode, and the second electrode is a cathode.
또 하나의 일 실시상태에 따르면, 상기 제1 전극은 음극이고, 상기 제2 전극은 양극이다.According to another exemplary embodiment, the first electrode is a cathode and the second electrode is an anode.
본 발명의 유기 발광 소자는 전술한 화합물을 이용하여 한 층 이상의 유기물층을 형성하는 것을 제외하고는, 통상의 유기 발광 소자의 제조방법 및 재료에 의하여 제조될 수 있다.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.
상기 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥 코팅, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.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. Here, 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.
본 발명의 유기 발광 소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기 발광 소자는 유기물층으로서 정공 주입층, 정공 수송층, 정공 주입 및 정공 수송을 동시에 하는 층, 발광층, 전자 수송층, 전자 주입층, 전자 주입 및 전자 수송을 동시에 하는 층, 전자 저지층 등을 포함하는 구조를 가질 수 있다. 그러나, 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기물층을 포함할 수 있다.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. For example, the organic light emitting device of the present invention includes a hole injection layer, a hole transport layer, a layer for simultaneously injecting and transporting holes, an emission layer, an electron transporting layer, an electron injecting layer, a layer for simultaneously injecting and transporting electrons, and an electron blocking layer as an organic material layer. It may have a structure including the. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic material layers.
본 발명의 일 실시상태에 있어서, 상기 화학식 1의 화합물을 포함하는 유기물층은 정공 주입층 또는 발광층인 유기 발광 소자이다.In one embodiment of the present invention, the organic material layer including the compound of Formula 1 is an organic light emitting device that is a hole injection layer or a light emitting layer.
또 하나의 일 실시상태에 따르면, 상기 화학식 1의 화합물을 포함하는 유기물층은 정공 수송층 또는 전자 저지층인 유기 발광 소자이다.According to another exemplary embodiment, the organic material layer including the compound of Formula 1 is an organic light emitting device that is a hole transport layer or an electron blocking layer.
본 발명의 유기 발광 소자에서, 상기 유기물층은 정공 주입층 또는 정공 수송층을 포함할 수 있고, 상기 층들 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.In the organic light emitting device of the present invention, the organic material layer may include a hole injection layer or a hole transport layer, one or more of the layers may include a compound represented by the formula (1).
또 하나의 실시 상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층이 상기 화학식 1로 표시되는 화합물을 포함한다. 하나의 예로서, 상기 화학식 1로 표시되는 화합물은 발광층의 도펀트로서 포함될 수 있다. In another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1. As one example, the compound represented by Formula 1 may be included as a dopant of the light emitting layer.
또 하나의 예로서, 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 상기 화학식 1로 표시되는 화합물을 도펀트로서 포함하고, 형광 호스트 또는 인광 호스트를 포함할 수 있다. As another example, the organic material layer including the compound represented by Chemical Formula 1 may include the compound represented by Chemical Formula 1 as a dopant, and may include a fluorescent host or a phosphorescent host.
또 하나의 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 상기 화학식 1로 표시되는 화합물을 도펀트로서 포함하고, 형광 호스트 또는 인광 호스트를 포함하며, 다른 유기화합물, 금속 또는 금속화합물을 도펀트로 포함할 수 있다.In another exemplary embodiment, the organic material layer including the compound represented by Chemical Formula 1 includes the compound represented by Chemical Formula 1 as a dopant, includes a fluorescent host or a phosphorescent host, and other organic compounds, metals, or metal compounds. May be included as the dopant.
또 하나의 예로서, 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 상기 화학식 1로 표시되는 화합물을 도펀트로서 포함하고, 형광 호스트 또는 인광 호스트를 포함하며, 이리듐계(Ir) 도펀트와 함께 사용할 수 있다.As another example, the organic material layer including the compound represented by Chemical Formula 1 may include the compound represented by Chemical Formula 1 as a dopant, include a fluorescent host or a phosphorescent host, and may be used with an iridium-based (Ir) dopant. have.
본 발명의 유기 발광 소자에서, 상기 유기물층은 전자 주입층 또는 전자 수송층을 포함하고, 상기 전자 주입층 또는 전자 수송층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.In the organic light emitting device of the present invention, the organic material layer may include an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may include a compound represented by Chemical Formula 1.
또 하나의 일 예에 따른 유기 발광 소자에서, 상기 유기물층은 전자 저지층을 포함하고, 상기 전자 저지층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.In another embodiment, the organic light emitting device may include an electron blocking layer, and the electron blocking layer may include a compound represented by Chemical Formula 1.
본 발명의 유기 발광 소자의 구조는 도 1 및 도 2에 나타낸 것과 같은 구조를 가질 수 있으나, 이에만 한정되는 것은 아니다.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.
도 1에는 기판(1) 위에 양극(2), 발광층(3) 및 음극(4)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화합물은 상기 발광층(3)에 포함될 수 있다.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. In such a structure, the compound may be included in the light emitting layer (3).
도 2에는 기판(1) 위에 양극(2), 정공 주입층(5), 정공 수송층(6), 전자 저지층(8), 발광층(3), 전자 수송 및 전자 주입을 동시에 하는 층(7) 및 음극(4)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화합물은 상기 정공 주입층(5), 정공 수송층(6), 발광층(3) 또는 전자 저지층(7)에 포함될 수 있다.2 shows an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 8, a light emitting layer 3, and a layer 7 for simultaneously transporting electrons and electrons on a substrate 1. And a structure of an organic light emitting element in which the cathodes 4 are sequentially stacked. In such a structure, the compound may be included in the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, or the electron blocking layer 7.
예컨대, 본 발명에 따른 유기 발광 소자는 스퍼터링(sputtering)이나 전자빔 증발(e-beam evaporation)과 같은 PVD(physical vapor deposition) 방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층 및 전자 수송층을 포함하는 유기물층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수도 있다.For example, the organic light emitting device according to the present invention 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. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
상기 유기물층은 정공 주입층, 정공 수송층, 발광층 및 전자 수송층 등을 포함하는 다층 구조일 수도 있으나, 이에 한정되지 않고 단층 구조일 수 있다. 또한, 상기 유기물층은 다양한 고분자 소재를 사용하여 증착법이 아닌 용매 공정(solvent process), 예컨대 스핀 코팅, 딥 코팅, 닥터 블레이딩, 스크린 프린팅, 잉크젯 프린팅 또는 열 전사법 등의 방법에 의하여 더 적은 수의 층으로 제조할 수 있다.The organic material layer 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. In addition, the organic layer may be prepared by using a variety of polymer materials, and by using a method such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than a deposition method. It can be prepared in layers.
상기 양극 물질로는 통상 유기물층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 본 발명에서 사용될 수 있는 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO : Al 또는 SnO2 : Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.As the anode material, a material having a large work function is usually preferred to facilitate hole injection into the organic material layer. Specific examples of 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-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다.It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
상기 정공 주입 물질로는 낮은 전압에서 양극으로부터 정공을 잘 주입 받을 수 있는 물질로서, 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrine), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴헥사아자트리페닐렌 계열의 유기물, 퀴나크리돈(quinacridone) 계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.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. Specific examples of hole injecting materials include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene-based organics, quinacridone-based organics, and perylene-based Organic substances, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
상기 정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다.As 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. 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.
상기 발광층은 적색, 녹색 또는 청색을 발광할 수 있으며, 인광 물질 또는 형광 물질로 이루어질 수 있다. 상기 발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 구체적인 예로는 8-히드록시-퀴놀린 알루미늄 착물(Alq3); 카르바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자; 스피로(spiro) 화합물; 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다.The emission layer may emit red, green, or blue light, and may be formed of a phosphor or a fluorescent material. 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.
발광층의 호스트 재료로는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 카바졸 유도체, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되지 않는다.As a host material of a light emitting layer, a condensed aromatic ring derivative, a heterocyclic containing compound, etc. are mentioned. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and the heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
발광층의 도펀트로 사용되는 이리듐계 착물은 하기와 같다.Iridium complex used as a dopant of a light emitting layer is as follows.
Figure PCTKR2017010533-appb-I000062
Figure PCTKR2017010533-appb-I000062
Figure PCTKR2017010533-appb-I000063
Figure PCTKR2017010533-appb-I000063
상기 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al 착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다.The electron 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.
본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
본 발명에 따른 화합물은 유기 태양 전지, 유기 감광체, 유기 트랜지스터 등을 비롯한 유기 전자 소자에서도 유기 발광 소자에 적용되는 것과 유사한 원리로 작용할 수 있다.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.
<제조예><Production example>
제조예 1. 화합물 1의 합성Preparation Example 1 Synthesis of Compound 1
단계 1) 화합물 1-A의 합성Step 1) Synthesis of Compound 1-A
Figure PCTKR2017010533-appb-I000064
Figure PCTKR2017010533-appb-I000064
9,9'-스피로비[플루오렌]-2-아민 (50.00 g, 150.87 mmol)을 N,N-디메틸포름아마이드(DMF) (200 ml)에 용해 후 0℃로 온도를 하강시켰다. 상기 용액에 N-브로모석시니미드(NBS) (26.85 g, 150.87 mmol)을 N,N-디메틸포름아마이드(DMF) (100 ml)에 용해 후 천천히 투입하여 교반하였다. 반응 종결 후 온도를 상온으로 올리고, 물을 가하여 역침전 한 후 여과하였다. 얻은 고체를 클로로포름과 소듐티오설페이트 용액으로 층분리 하였다. 용매 제거 후 헥산으로 재결정하여 상기 화합물 1-A (52.50 g, 84.81 % 수율)를 수득하였다.9,9'-spirobi [fluorene] -2-amine (50.00 g, 150.87 mmol) was dissolved in N, N-dimethylformamide (DMF) (200 ml) and the temperature was lowered to 0 ° C. N-bromosuccinimide (NBS) (26.85 g, 150.87 mmol) was dissolved in N, N-dimethylformamide (DMF) (100 ml) and slowly added to the solution, followed by stirring. After completion of the reaction, the temperature was raised to room temperature, and water was added thereto, followed by reverse precipitation and filtration. The obtained solid was layered with chloroform and sodium thiosulfate solution. Recrystallization with hexane after solvent removal gave the compound 1-A (52.50 g, 84.81% yield).
단계 2) 화합물 1-B의 합성Step 2) Synthesis of Compound 1-B
Figure PCTKR2017010533-appb-I000065
Figure PCTKR2017010533-appb-I000065
상기 단계 1에서 수득한 화합물 1-A (52.5 g, 127.95 mmol)과 페닐보론 산 (15.60 g, 127.95 mmol)을 1,4-다이옥산(300 ml)에 용해 후, 포타슘 카보네이트 (53.05 g, 383.85 mmol : 물 150 ml) 용액을 가한 후, 15분 동안 가열 교반하였다. 상기 용액에 1,4-다이옥산(20 ml)에 용해시킨 1,1’-비스(디페닐포스피노)페로센디클로로팔라듐(II) (0.47 g, 0.64 mmol) 을 가한 후 1시간 동안 가열 교반하였다. 반응 종결 및 여과 후, 클로로포름과 물로 층분리 하였다. 용매 제거 후 헥산으로 재결정하여 상기 화합물 1-B (44.3 g, 84.96 % 수율)를 수득하였다.Compound 1-A (52.5 g, 127.95 mmol) and phenylboronic acid (15.60 g, 127.95 mmol) obtained in step 1 were dissolved in 1,4-dioxane (300 ml), followed by potassium carbonate (53.05 g, 383.85 mmol). : 150 ml of water) was added to the solution, followed by heating and stirring for 15 minutes. To the solution was added 1,1′-bis (diphenylphosphino) ferrocenedichloropalladium (II) (0.47 g, 0.64 mmol) dissolved in 1,4-dioxane (20 ml), followed by heating and stirring for 1 hour. After completion of the reaction and filtration, the reaction mixture was layered with chloroform and water. Recrystallization with hexane after removal of solvent gave compound 1-B (44.3 g, 84.96% yield).
단계 3) 화합물 1-C의 합성Step 3) Synthesis of Compound 1-C
Figure PCTKR2017010533-appb-I000066
Figure PCTKR2017010533-appb-I000066
상기 단계 2에서 수득한 화합물 1-B (44.3 g, 108.71 mmol), 2-브로모트리페닐렌 (33.40 g, 108.71 mmol) 그리고 소듐 터트-부톡사이드(14.63 g, 152.19 mmol)에 톨루엔(350 ml)을 가한 후, 15분 동안 가열 교반하였다. 상기 혼합물에 톨루엔(20ml)에 용해시킨 1,1’-비스(디페닐포스피노)페로센디클로로팔라듐(II) (0.40 g, 0.54 mmol)을 가한 후 1시간 동안 가열 교반하였다. 반응 종결 및 여과 후, 클로로포름과 물로 층분리 하였다. 용매 제거 후 에틸아세테이트로 재결정하여 상기 화합물 1-C (51.6 g, 74.89 % 수율)를 수득하였다.Toluene (350 ml) in Compound 1-B (44.3 g, 108.71 mmol), 2-bromotriphenylene (33.40 g, 108.71 mmol) and sodium tert-butoxide (14.63 g, 152.19 mmol) obtained in step 2 above. ) Was added and then stirred for 15 minutes by heating. To the mixture was added 1,1′-bis (diphenylphosphino) ferrocenedichloropalladium (II) (0.40 g, 0.54 mmol) dissolved in toluene (20 ml), followed by stirring for 1 hour. After completion of the reaction and filtration, the reaction mixture was layered with chloroform and water. After removal of the solvent, recrystallization with ethyl acetate to obtain the compound 1-C (51.6 g, 74.89% yield).
단계 4) 화합물 1의 합성Step 4) Synthesis of Compound 1
Figure PCTKR2017010533-appb-I000067
Figure PCTKR2017010533-appb-I000067
상기 단계 3에서 수득한 화합물 1-C (30.0 g, 47.33 mmol), 브로모벤젠 (7.43 g, 47.33 mmol) 그리고 소듐 터트-부톡사이드(6.37 g, 66.26 mmol)에 톨루엔(200 ml)을 가한 후, 15분 동안 가열 교반하였다. 상기 혼합물에 톨루엔(20ml)에 용해시킨 비스(트리-터트-부틸포스핀)팔라듐 (0.12 g, 0.24 mmol)을 가한 후 1시간 동안 가열 교반하였다. 반응 종결 및 여과 후, 톨루엔과 물로 층분리 하였다. 용매 제거 후 에틸아세테이트로 재결정하여 상기 화합물 1 (24.6 g, 73.22 % 수율)를 수득하였다. (MS[M+H] +=710)Toluene (200 ml) was added to Compound 1-C (30.0 g, 47.33 mmol), bromobenzene (7.43 g, 47.33 mmol) and sodium tert-butoxide (6.37 g, 66.26 mmol) obtained in step 3. And stirred for 15 minutes by heating. Bis (tri-tert-butylphosphine) palladium (0.12 g, 0.24 mmol) dissolved in toluene (20 ml) was added to the mixture, followed by heating and stirring for 1 hour. After completion of the reaction and filtration, layered with toluene and water. After removing the solvent and recrystallized with ethyl acetate to give the compound 1 (24.6 g, 73.22% yield). (MS [M + H] + = 710)
제조예 2. 화합물 2의 합성Preparation Example 2 Synthesis of Compound 2
Figure PCTKR2017010533-appb-I000068
Figure PCTKR2017010533-appb-I000068
상기 제조예 1의 단계 3에서 수득한 화합물 1-C (30.0 g, 47.33 mmol)와 4-브로모-1,1'-바이페닐 (11.03 g, 47.33 mmol)을 이용하여 상기 제조예 1의 단계 4와 동일한 방법으로 화합물 2 (26.0 g, 69.89 % 수율)를 수득하였다. (MS[M+H] +=786)Preparation Example 1 using Compound 1-C (30.0 g, 47.33 mmol) and 4-bromo-1,1'-biphenyl (11.03 g, 47.33 mmol) obtained in Step 3 of Preparation Example 1 Compound 2 (26.0 g, 69.89% yield) was obtained by the same method as 4. (MS [M + H] + = 786)
제조예 3. 화합물 3의 합성Preparation Example 3 Synthesis of Compound 3
Figure PCTKR2017010533-appb-I000069
Figure PCTKR2017010533-appb-I000069
상기 제조예 1의 단계 3에서 수득한 화합물 1-C (30.0 g, 47.33 mmol)와 2-브로모-1,1'-바이페닐 (11.03 g, 47.33 mmol)을 이용하여 상기 제조예 1의 단계 4와 동일한 방법으로 화합물 3 (22.5 g, 60.48 % 수율)를 수득하였다. (MS[M+H] +=786)Preparation Example 1 using Compound 1-C (30.0 g, 47.33 mmol) and 2-bromo-1,1'-biphenyl (11.03 g, 47.33 mmol) obtained in Step 3 of Preparation Example 1 Compound 3 (22.5 g, 60.48% yield) was obtained in the same manner as in 4. (MS [M + H] + = 786)
제조예 4. 화합물 4의 합성Preparation Example 4 Synthesis of Compound 4
Figure PCTKR2017010533-appb-I000070
Figure PCTKR2017010533-appb-I000070
상기 제조예 1의 단계 3에서 수득한 화합물 1-C (30.0 g, 47.33 mmol)와 2-(4-브로모페닐)나프탈렌 (13.40 g, 47.33 mmol)을 이용하여 상기 제조예 1의 단계 4와 동일한 방법으로 화합물 4 (29.3 g, 74.05 % 수율)를 수득하였다. (MS[M+H] +=836)Using the compound 1-C (30.0 g, 47.33 mmol) and 2- (4-bromophenyl) naphthalene (13.40 g, 47.33 mmol) obtained in step 3 of Preparation Example 1 and In the same manner, compound 4 (29.3 g, 74.05% yield) was obtained. (MS [M + H] + = 836)
제조예 5. 화합물 5의 합성Preparation Example 5 Synthesis of Compound 5
Figure PCTKR2017010533-appb-I000071
Figure PCTKR2017010533-appb-I000071
상기 제조예 1의 단계 3에서 수득한 화합물 1-C (30.0 g, 47.33 mmol)와 2-브로모-9,9-디메틸-9H-플루오렌 (12.93 g, 47.33 mmol)을 이용하여 상기 제조예 1의 단계 4와 동일한 방법으로 화합물 5 (25.1 g, 64.20 % 수율)를 수득하였다. (MS[M+H] +=826)Preparation Example 1 using Compound 1-C (30.0 g, 47.33 mmol) and 2-bromo-9,9-dimethyl- 9H -fluorene (12.93 g, 47.33 mmol) obtained in Step 3 of Preparation Example 1 above Compound 5 (25.1 g, 64.20% yield) was obtained by the same method as Step 4 of 1. (MS [M + H] + = 826)
제조예 6. 화합물 6의 합성Preparation Example 6 Synthesis of Compound 6
단계 1) 화합물 6-A의 합성Step 1) Synthesis of Compound 6-A
Figure PCTKR2017010533-appb-I000072
Figure PCTKR2017010533-appb-I000072
상기 제조예 1의 단계 1에서 수득한 화합물 1-A (50.0 g, 121.86 mmol)와 [1,1'-바이페닐]-4-일보론 산 (24.13 g, 121.86 mmol)을 이용하여 상기 제조예 1의 단계 2와 동일한 방법으로 화합물 6-A (51.7 g, 87.73 % 수율)를 수득하였다.Preparation Example 1 using Compound 1-A (50.0 g, 121.86 mmol) and [1,1'-biphenyl] -4-ylboronic acid (24.13 g, 121.86 mmol) obtained in Step 1 of Preparation Example 1 above Compound 6-A (51.7 g, 87.73% yield) was obtained by the same method as Step 2 of 1.
단계 2) 화합물 6-B의 합성Step 2) Synthesis of Compound 6-B
Figure PCTKR2017010533-appb-I000073
Figure PCTKR2017010533-appb-I000073
상기 단계 1에서 수득한 화합물 6-A (51.7 g, 106.90 mmol)와 2-브로모트리페닐렌 (32.84 g, 106.90 mmol)을 이용하여 상기 제조예 1의 단계 3과 동일한 방법으로 화합물 6-B (67.3 g, 88.68 % 수율)를 수득하였다.Using compound 6-A (51.7 g, 106.90 mmol) and 2-bromotriphenylene (32.84 g, 106.90 mmol) obtained in step 1, compound 6-B in the same manner as in step 3 of Preparation Example 1 (67.3 g, 88.68% yield) was obtained.
단계 3) 화합물 6의 합성Step 3) Synthesis of Compound 6
Figure PCTKR2017010533-appb-I000074
Figure PCTKR2017010533-appb-I000074
상기 단계 2에서 수득한 화합물 6-B (30.0 g, 42.26 mmol)와 브로모벤젠 (6.64 g, 42.26 mmol)을 이용하여 상기 제조예 1의 단계 4와 동일한 방법으로 화합물 6 (27.5 g, 82.79 % 수율)을 수득하였다. (MS[M+H] +=786)Using compound 6-B (30.0 g, 42.26 mmol) and bromobenzene (6.64 g, 42.26 mmol) obtained in step 2, compound 6 (27.5 g, 82.79%) in the same manner as in step 4 of Preparation Example 1 above Yield). (MS [M + H] + = 786)
제조예 7. 화합물 7의 합성Preparation Example 7 Synthesis of Compound 7
Figure PCTKR2017010533-appb-I000075
Figure PCTKR2017010533-appb-I000075
상기 제조예 6의 단계 2에서 수득한 화합물 6-B (30.0 g, 42.26 mmol)와 4-브로모-1,1'-바이페닐 (9.85 g, 42.26 mmol)을 이용하여 상기 제조예 1의 단계 4와 동일한 방법으로 화합물 7 (28.3 g, 77.68 % 수율)를 수득하였다. (MS[M+H] +=862) Step 6 of Preparation Example 1 using Compound 6-B (30.0 g, 42.26 mmol) and 4-bromo-1,1′-biphenyl (9.85 g, 42.26 mmol) obtained in Step 2 of Preparation Example 6 In the same manner as 4, compound 7 (28.3 g, 77.68% yield) was obtained. (MS [M + H] + = 862)
제조예 8. 화합물 8의 합성Preparation Example 8 Synthesis of Compound 8
Figure PCTKR2017010533-appb-I000076
Figure PCTKR2017010533-appb-I000076
상기 제조예 6의 단계 2에서 수득한 화합물 6-B (30.0 g, 42.26 mmol)와 2-브로모-1,1'-바이페닐 (9.85 g, 42.26 mmol)을 이용하여 상기 제조예 1의 단계 4와 동일한 방법으로 화합물 8 (26.4 g, 72.46 % 수율)를 수득하였다. (MS[M+H] +=862)Preparation Example 1 using Compound 6-B (30.0 g, 42.26 mmol) and 2-bromo-1,1'-biphenyl (9.85 g, 42.26 mmol) obtained in Step 2 of Preparation Example 6 In the same manner as 4, compound 8 (26.4 g, 72.46% yield) was obtained. (MS [M + H] + = 862)
제조예 9. 화합물 9의 합성Preparation Example 9 Synthesis of Compound 9
Figure PCTKR2017010533-appb-I000077
Figure PCTKR2017010533-appb-I000077
상기 제조예 6의 단계 2에서 수득한 화합물 6-B (30.0 g, 42.26 mmol)와 2-(4-브로모페닐)나프탈렌 (11.97 g, 42.26 mmol)을 이용하여 상기 제조예 1의 단계 4와 동일한 방법으로 화합물 9 (26.9 g, 69.78 % 수율)를 수득하였다. (MS[M+H] +=912)Using the compound 6-B (30.0 g, 42.26 mmol) and 2- (4-bromophenyl) naphthalene (11.97 g, 42.26 mmol) obtained in step 2 of Preparation Example 6 and In the same manner compound 9 (26.9 g, 69.78% yield) was obtained. (MS [M + H] + = 912)
제조예 10. 화합물 10의 합성Preparation Example 10 Synthesis of Compound 10
Figure PCTKR2017010533-appb-I000078
Figure PCTKR2017010533-appb-I000078
상기 제조예 6의 단계 2에서 수득한 화합물 6-B (30.0 g, 42.26 mmol)와 2-브로모-9,9-디메틸-9H-플루오렌 (11.54 g, 42.26 mmol)을 이용하여 상기 제조예 1의 단계 4와 동일한 방법으로 화합물 10 (27.1 g, 71.34 % 수율)를 수득하였다. (MS[M+H] +=902)Preparation Example 6-B (30.0 g, 42.26 mmol) and 2-bromo-9,9-dimethyl- 9H -fluorene (11.54 g, 42.26 mmol) obtained in step 2 of Preparation Example 6 above Compound 10 (27.1 g, 71.34% yield) was obtained by the same method as Step 4 of 1. (MS [M + H] + = 902)
제조예 11. 화합물 11의 합성Preparation Example 11 Synthesis of Compound 11
단계 1) 화합물 11-A의 합성Step 1) Synthesis of Compound 11-A
Figure PCTKR2017010533-appb-I000079
Figure PCTKR2017010533-appb-I000079
상기 제조예 1의 단계 1에서 수득한 화합물 1-A (50.0 g, 121.86 mmol)와 나프탈렌-2-일보론 산 (20.96 g, 121.86 mmol)을 이용하여 상기 제조예 1의 단계 2와 동일한 방법으로 화합물 11-A (49.6 g, 88.95 % 수율)를 수득하였다.Compound 1-A (50.0 g, 121.86 mmol) and naphthalen-2-ylboronic acid (20.96 g, 121.86 mmol) obtained in Step 1 of Preparation Example 1 were used in the same manner as in Step 2 of Preparation Example 1 Compound 11-A (49.6 g, 88.95% yield) was obtained.
단계 2) 화합물 11-B의 합성Step 2) Synthesis of Compound 11-B
Figure PCTKR2017010533-appb-I000080
Figure PCTKR2017010533-appb-I000080
상기 단계 1에서 수득한 화합물 11-A (49.6 g, 108.40 mmol)와 2-브로모트리페닐렌 (33.30 g, 108.40 mmol)을 이용하여 상기 제조예 1의 단계 3과 동일한 방법으로 화합물 11-B (62.9 g, 84.85 % 수율)를 수득하였다.Using compound 11-A (49.6 g, 108.40 mmol) and 2-bromotriphenylene (33.30 g, 108.40 mmol) obtained in step 1, compound 11-B in the same manner as in step 3 of Preparation Example 1 (62.9 g, 84.85% yield) was obtained.
단계 3) 화합물 11의 합성Step 3) Synthesis of Compound 11
Figure PCTKR2017010533-appb-I000081
Figure PCTKR2017010533-appb-I000081
상기 단계 2에서 수득한 화합물 11-B (30.0 g, 43.87 mmol)와 브로모벤젠 (6.89 g, 43.87 mmol)을 이용하여 상기 제조예 1의 단계 4와 동일한 방법으로 화합물 11 (26.4 g, 79.19 % 수율)를 수득하였다. (MS[M+H] +=760)Using compound 11-B (30.0 g, 43.87 mmol) and bromobenzene (6.89 g, 43.87 mmol) obtained in step 2, compound 11 (26.4 g, 79.19%) in the same manner as in step 4 of Preparation Example 1 above Yield). (MS [M + H] + = 760)
제조예 12. 화합물 12의 합성Preparation Example 12 Synthesis of Compound 12
Figure PCTKR2017010533-appb-I000082
Figure PCTKR2017010533-appb-I000082
상기 제조예 11의 단계 2에서 수득한 화합물 11-B (30.0 g, 43.87 mmol)와 4-브로모-1,1'-바이페닐 (10.23 g, 43.87 mmol)을 이용하여 상기 제조예 1의 단계 4와 동일한 방법으로 화합물 12 (28.6 g, 77.98 % 수율)를 수득하였다. (MS[M+H] +=836)Preparation Example 1 using Compound 11-B (30.0 g, 43.87 mmol) and 4-bromo-1,1'-biphenyl (10.23 g, 43.87 mmol) obtained in Step 2 of Preparation Example 11 above Compound 12 (28.6 g, 77.98% yield) was obtained in the same manner as in 4. (MS [M + H] + = 836)
제조예 13. 화합물 13의 합성Preparation Example 13 Synthesis of Compound 13
Figure PCTKR2017010533-appb-I000083
Figure PCTKR2017010533-appb-I000083
상기 제조예 11의 단계 2에서 수득한 화합물 11-B (30.0 g, 43.87 mmol)와 2-브로모-1,1'-바이페닐 (10.23 g, 43.87 mmol)을 이용하여 상기 제조예 1의 단계 4와 동일한 방법으로 화합물 13 (26.9 g, 73.34 % 수율)를 수득하였다. (MS[M+H] +=836)Preparation Example 1 using Compound 11-B (30.0 g, 43.87 mmol) and 2-bromo-1,1'-biphenyl (10.23 g, 43.87 mmol) obtained in Step 2 of Preparation Example 11 above In the same manner as 4, compound 13 (26.9 g, 73.34% yield) was obtained. (MS [M + H] + = 836)
제조예 14. 화합물 14의 합성Preparation Example 14 Synthesis of Compound 14
Figure PCTKR2017010533-appb-I000084
Figure PCTKR2017010533-appb-I000084
상기 제조예 11의 단계 2에서 수득한 화합물 11-B (30.0 g, 43.87 mmol)와 2-(4-브로모페닐)나프탈렌 (12.42 g, 43.87 mmol)을 이용하여 상기 제조예 1의 단계 4와 동일한 방법으로 화합물 14 (30.2 g, 77.69 % 수율)를 수득하였다. (MS[M+H] +=886)The compound 11-B (30.0 g, 43.87 mmol) and 2- (4-bromophenyl) naphthalene (12.42 g, 43.87 mmol) obtained in Step 2 of Preparation Example 11 were used to form Compound 1-B (30.0 g, 43.87 mmol). In the same manner, compound 14 (30.2 g, 77.69% yield) was obtained. (MS [M + H] + = 886)
제조예 15. 화합물 15의 합성Preparation Example 15 Synthesis of Compound 15
Figure PCTKR2017010533-appb-I000085
Figure PCTKR2017010533-appb-I000085
상기 제조예 11의 단계 2에서 수득한 화합물 11-B (30.0 g, 43.87 mmol)와 2-브로모-9,9-디메틸-9H-플루오렌 (11.98 g, 43.87 mmol)을 이용하여 상기 제조예 1의 단계 4와 동일한 방법으로 화합물 15 (25.9 g, 67.39 % 수율)를 수득하였다. (MS[M+H] +=876)Preparation Example 11 using Compound 11-B (30.0 g, 43.87 mmol) and 2-bromo-9,9-dimethyl- 9H -fluorene (11.98 g, 43.87 mmol) obtained in Step 2 of Preparation Example 11 above Compound 15 (25.9 g, 67.39% yield) was obtained by the same method as Step 4 of 1. (MS [M + H] + = 876)
제조예 16. 화합물 16의 합성Preparation Example 16 Synthesis of Compound 16
단계 1) 화합물 16-A의 합성Step 1) Synthesis of Compound 16-A
Figure PCTKR2017010533-appb-I000086
Figure PCTKR2017010533-appb-I000086
상기 제조예 1의 단계 1에서 수득한 화합물 1-A (50.0 g, 121.86 mmol)와 디벤조[b,d]퓨란-4-일보론 산 (25.84 g, 121.86 mmol)을 이용하여 상기 제조예 1의 단계 2와 동일한 방법으로 화합물 16-A (52.6 g, 86.75 % 수율)를 수득하였다.Preparation Example 1 using Compound 1-A (50.0 g, 121.86 mmol) and dibenzo [ b, d ] furan-4-ylboronic acid (25.84 g, 121.86 mmol) obtained in Step 1 of Preparation Example 1 above Compound 16-A (52.6 g, 86.75% yield) was obtained in the same manner as in Step 2 of.
단계 2) 화합물 16-B의 합성Step 2) Synthesis of Compound 16-B
Figure PCTKR2017010533-appb-I000087
Figure PCTKR2017010533-appb-I000087
상기 단계 1에서 수득한 화합물 16-A (52.6 g, 105.71 mmol)와 2-브로모트리페닐렌 (32.47 g, 105.71 mmol)을 이용하여 상기 제조예 1의 단계 3과 동일한 방법으로 화합물 16-B (65.1 g, 85.07 % 수율)를 수득하였다.Using Compound 16-A (52.6 g, 105.71 mmol) and 2-bromotriphenylene (32.47 g, 105.71 mmol) obtained in Step 1, Compound 16-B in the same manner as in Step 3 of Preparation Example 1 (65.1 g, 85.07% yield) was obtained.
단계 3) 화합물 16의 합성Step 3) Synthesis of Compound 16
Figure PCTKR2017010533-appb-I000088
Figure PCTKR2017010533-appb-I000088
상기 단계 2에서 수득한 화합물 16-B (30.0 g, 41.44 mmol)와 브로모벤젠 (6.51 g, 41.44 mmol)을 이용하여 상기 제조예 1의 단계 4와 동일한 방법으로 화합물 16 (24.8 g, 74.81 % 수율)를 수득하였다. (MS[M+H] +=800)Using compound 16-B (30.0 g, 41.44 mmol) and bromobenzene (6.51 g, 41.44 mmol) obtained in step 2, compound 16 (24.8 g, 74.81%) in the same manner as in step 4 of Preparation Example 1 Yield). (MS [M + H] + = 800)
제조예 17. 화합물 17의 합성Preparation Example 17 Synthesis of Compound 17
Figure PCTKR2017010533-appb-I000089
Figure PCTKR2017010533-appb-I000089
상기 제조예 16의 단계 2에서 수득한 화합물 16-B (30.0 g, 41.44 mmol)와 4-브로모-1,1'-바이페닐 (9.66 g, 41.44 mmol)을 이용하여 상기 제조예 1의 단계 4와 동일한 방법으로 화합물 17 (26.4 g, 72.72 % 수율)를 수득하였다. (MS[M+H] +=876)Preparation Example 1 using Compound 16-B (30.0 g, 41.44 mmol) and 4-bromo-1,1'-biphenyl (9.66 g, 41.44 mmol) obtained in Step 2 of Preparation Example 16 In the same manner as 4, compound 17 (26.4 g, 72.72% yield) was obtained. (MS [M + H] + = 876)
제조예 18. 화합물 18의 합성Preparation Example 18 Synthesis of Compound 18
Figure PCTKR2017010533-appb-I000090
Figure PCTKR2017010533-appb-I000090
상기 제조예 16의 단계 2에서 수득한 화합물 16-B (30.0 g, 41.44 mmol)와 2-브로모-1,1'-바이페닐 (9.66 g, 41.44 mmol)을 이용하여 상기 제조예 1의 단계 4와 동일한 방법으로 화합물 18 (24.6 g, 67.76 % 수율)를 수득하였다. (MS[M+H] +=876) Step 1 of Preparation Example 1 using Compound 16-B (30.0 g, 41.44 mmol) and 2-bromo-1,1′-biphenyl (9.66 g, 41.44 mmol) obtained in Step 2 of Preparation Example 16 Compound 18 (24.6 g, 67.76% yield) was obtained in the same manner as in 4. (MS [M + H] + = 876)
제조예 19. 화합물 19의 합성Preparation Example 19 Synthesis of Compound 19
Figure PCTKR2017010533-appb-I000091
Figure PCTKR2017010533-appb-I000091
상기 제조예 16의 단계 2에서 수득한 화합물 16-B (30.0 g, 41.44 mmol)와 2-(4-브로모페닐)나프탈렌 (11.73 g, 41.44 mmol)을 이용하여 상기 제조예 1의 단계 4와 동일한 방법으로 화합물 19 (27.1 g, 70.61 % 수율)를 수득하였다. (MS[M+H] +=926)Using the compound 16-B (30.0 g, 41.44 mmol) and 2- (4-bromophenyl) naphthalene (11.73 g, 41.44 mmol) obtained in step 2 of Preparation Example 16 and In the same manner compound 19 (27.1 g, 70.61% yield) was obtained. (MS [M + H] + = 926)
제조예 20. 화합물 20의 합성Preparation Example 20 Synthesis of Compound 20
Figure PCTKR2017010533-appb-I000092
Figure PCTKR2017010533-appb-I000092
상기 제조예 16의 단계 2에서 수득한 화합물 16-B (30.0 g, 41.44 mmol)와 2-브로모-9,9-디메틸-9H-플루오렌 (11.32 g, 41.44 mmol)을 이용하여 상기 제조예 1의 단계 4와 동일한 방법으로 화합물 20 (26.1 g, 68.75 % 수율)를 수득하였다. (MS[M+H] +=916)Preparation Example 16-B (30.0 g, 41.44 mmol) and 2-bromo-9,9-dimethyl- 9H -fluorene (11.32 g, 41.44 mmol) obtained in Step 2 of Preparation Example 16 above Compound 20 (26.1 g, 68.75% yield) was obtained by the same method as Step 4 of 1. (MS [M + H] + = 916)
<실험예>Experimental Example
비교예 1-1.Comparative Example 1-1.
ITO(Indium Tin Oxide)가 1,400Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀러포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다.A glass substrate coated with a thin film of ITO (Indium Tin Oxide) having a thickness of 1,400 kPa was put in distilled water in which detergent was dissolved and ultrasonically cleaned. In this case, Fischer Co. was used as a detergent, and distilled water was filtered secondly as a filter of Millipore Co. as a distilled water. After ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After washing the distilled water, ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
이렇게 준비된 ITO 투명 전극 위에 하기 화학식 HAT로 표시되는 화합물을 100Å의 두께로 열 진공 증착하여 정공주입층을 형성하였다. 그 위에 정공수송층으로 하기 화학식 HT1로 표시되는 화합물을 1150Å 두께로 진공 증착한 후 전자저지층으로 하기 화합물 EB1을 150Å의 두께로 열 진공 증착하였다. 이어서, 발광층으로 하기 화학식 BH로 표시되는 화합물 및 하기 화학식 BD로 표시되는 화합물을 25:1의 중량비로 200Å의 두께로 진공 증착하였다. 이어서, 정공저지층으로 하기 화학식 HB1으로 표시되는 화합물을 50Å의 두께로 진공 증착하였다. 이어서, 전자수송층과 전자주입층으로 하기 화학식 ET1로 표시되는 화합물과 하기 Liq로 표시되는 화합물을 1:1의 중량비로 310Å의 두께로 열 진공 증착하였다. 이어서, 하기 Liq로 표시되는 화합물을 5Å의 두께로 진공 증착하였다. 상기 전자 수송 및 전자 주입층 위에 순차적으로 12Å의 두께로 리튬플로라이드(LiF)와 1000Å 두께로 알루미늄을 증착하여 음극을 형성하여, 유기 발광 소자를 제조하였다.A hole injection layer was formed by thermally vacuum depositing a compound represented by the following formula HAT on the prepared ITO transparent electrode to a thickness of 100 kPa. The compound represented by the following formula HT1 was vacuum deposited to a thickness of 1150 kPa as a hole transport layer, and the following compound EB1 was thermally vacuum deposited to a thickness of 150 kPa as an electron blocking layer. Subsequently, the compound represented by the following formula BH and the compound represented by the following formula BD were vapor deposited to a thickness of 200 kPa in a weight ratio of 25: 1 as a light emitting layer. Subsequently, the compound represented by the following formula HB1 was vacuum deposited to a thickness of 50 kV as a hole blocking layer. Subsequently, the compound represented by the following formula ET1 and the compound represented by the following Liq were thermally vacuum deposited to a thickness of 310 kPa in a weight ratio of 1: 1 as the electron transport layer and the electron injection layer. Subsequently, the compound represented by Liq below was vacuum deposited to a thickness of 5 kPa. On the electron transporting and electron injection layer, lithium fluoride (LiF) and aluminum were deposited to a thickness of 1000 kW in order to form a cathode, thereby manufacturing an organic light emitting device.
Figure PCTKR2017010533-appb-I000093
Figure PCTKR2017010533-appb-I000093
비교예 1-2 내지 1-5Comparative Examples 1-2 to 1-5
상기 비교예 1-1에서 EB1 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 비교예 1-1과 동일한 방법으로 비교예 1-2 내지 1-5의 유기 발광 소자를 제작하였다.Except for using the compound shown in Table 1 in place of EB1 in Comparative Example 1-1, an organic light emitting device of Comparative Examples 1-2 to 1-5 was prepared in the same manner as in Comparative Example 1-1.
Figure PCTKR2017010533-appb-I000094
Figure PCTKR2017010533-appb-I000094
실시예 1-1 내지 1-20Examples 1-1 to 1-20
상기 비교예 1-1에서 EB1 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 비교예 1-1과 동일한 방법으로 실시예 1-1 내지 1-20의 유기 발광 소자를 제작하였다.The organic light emitting diodes of Examples 1-1 to 1-20 were manufactured by the same method as Comparative Example 1-1, except that Compound 1-1 was used instead of EB1 in Comparative Example 1-1.
실험예 1Experimental Example 1
상기 실시예 1-1 내지 1-20 및 비교예 1-1 내지 1-5에서 제조한 유기 발광 소자에 전류를 인가하였을 때, 전압, 효율, 색좌표 및 수명을 측정하고 그 결과를 하기 표 1에 나타내었다. T95는 휘도가 초기 휘도(6000 nit)에서 95%로 감소되는 데 소요되는 시간을 의미한다.When the current was applied to the organic light emitting diodes manufactured in Examples 1-1 to 1-20 and Comparative Examples 1-1 to 1-5, voltage, efficiency, color coordinate, and lifetime were measured, and the results are shown in Table 1 below. Indicated. T95 means the time it takes for the luminance to decrease to 95% from the initial luminance (6000 nit).
화합물(전자 저지층)Compound (electron blocking layer) 전압(V @ 10mA/cm2)Voltage (V @ 10mA / cm 2 ) 효율(cd/A @ 10mA/cm2)Efficiency (cd / A @ 10mA / cm 2 ) 색좌표 (x, y)Color coordinates (x, y) 수명(T95, hr)Life (T95, hr)
실시예 1-1Example 1-1 화합물 1Compound 1 3.533.53 6.316.31 0.140, 0.0440.140, 0.044 285285
실시예 1-2Example 1-2 화합물 2Compound 2 3.513.51 6.216.21 0.141, 0.0450.141, 0.045 270270
실시예 1-3Example 1-3 화합물 3Compound 3 3.453.45 6.306.30 0.140, 0.0440.140, 0.044 290290
실시예 1-4Example 1-4 화합물 4Compound 4 3.553.55 6.156.15 0.141, 0.0440.141, 0.044 285285
실시예 1-5Example 1-5 화합물 5Compound 5 3.483.48 6.286.28 0.142, 0.0440.142, 0.044 290290
실시예 1-6Example 1-6 화합물 6Compound 6 3.523.52 6.126.12 0.141, 0.0450.141, 0.045 280280
실시예 1-7Example 1-7 화합물 7Compound 7 3.513.51 6.136.13 0.142, 0.0430.142, 0.043 285285
실시예 1-8Example 1-8 화합물 8Compound 8 3.483.48 6.176.17 0.139, 0.0440.139, 0.044 270270
실시예 1-9Example 1-9 화합물 9Compound 9 3.533.53 6.116.11 0.140, 0.0430.140, 0.043 270270
실시예 1-10Example 1-10 화합물 10Compound 10 3.483.48 6.236.23 0.139, 0.0430.139, 0.043 295295
실시예 1-11Example 1-11 화합물 11Compound 11 3.553.55 6.216.21 0.143, 0.0430.143, 0.043 280280
실시예 1-12Example 1-12 화합물 12Compound 12 3.533.53 6.176.17 0.141, 0.0440.141, 0.044 280280
실시예 1-13Example 1-13 화합물 13Compound 13 3.503.50 6.116.11 0.140, 0.0440.140, 0.044 275275
실시예 1-14Example 1-14 화합물 14Compound 14 3.563.56 6.086.08 0.139, 0.0450.139, 0.045 280280
실시예 1-15Example 1-15 화합물 15Compound 15 3.513.51 6.186.18 0.140, 0.0440.140, 0.044 270270
실시예 1-16Example 1-16 화합물 16Compound 16 3.513.51 6.116.11 0.141, 0.0430.141, 0.043 285285
실시예 1-17Example 1-17 화합물 17Compound 17 3.513.51 6.166.16 0.141, 0.0440.141, 0.044 285285
실시예 1-18Example 1-18 화합물 18Compound 18 3.493.49 6.096.09 0.140, 0.0440.140, 0.044 290290
실시예 1-19Example 1-19 화합물 19Compound 19 3.563.56 6.176.17 0.142, 0.0430.142, 0.043 270270
실시예 1-20Example 1-20 화합물 20Compound 20 3.523.52 6.236.23 0.142, 0.0450.142, 0.045 265265
비교예 1-1Comparative Example 1-1 EB1EB1 3.893.89 5.745.74 0.143, 0.0450.143, 0.045 230230
비교예 1-2Comparative Example 1-2 EB2EB2 4.014.01 5.555.55 0.143, 0.0470.143, 0.047 210210
비교예 1-3Comparative Example 1-3 EB3EB3 4.054.05 5.495.49 0.144, 0.0480.144, 0.048 215215
비교예 1-4Comparative Example 1-4 EB4EB4 4.154.15 5.255.25 0.143, 0.0480.143, 0.048 180180
비교예 1-5Comparative Example 1-5 EB5EB5 4.104.10 5.335.33 0.144, 0.0480.144, 0.048 160160
상기 표 1에 나타난 바와 같이, 본 발명의 화합물을 전자 저지층으로 사용한 유기 발광 소자는 구동 전압, 효율, 수명 면에서 현저한 효과를 나타내는 것으로 확인되었다.As shown in Table 1, it was confirmed that the organic light emitting device using the compound of the present invention as the electron blocking layer exhibits significant effects in terms of driving voltage, efficiency, and lifetime.
상기 표 1의 결과와 같이, 본 발명에 따른 화합물은 전자 저지 능력이 우수하여 유기 발광 소자에 적용 가능함을 확인할 수 있었다.As shown in Table 1, the compound according to the present invention was confirmed that the excellent electron blocking ability can be applied to the organic light emitting device.
비교예Comparative example 2-1 내지 2-4 2-1 to 2-4
상기 비교예 1-1에서 HT1로 표시되는 화합물 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 비교예 1-1과 동일한 방법으로 비교예 2-1 내지 2-4의 유기 발광 소자를 제작하였다.The organic light emitting diodes of Comparative Examples 2-1 to 2-4 in the same manner as in Comparative Example 1-1, except that the compound shown in Table 1 was used instead of the compound represented by HT1 in Comparative Example 1-1. Was produced.
Figure PCTKR2017010533-appb-I000095
Figure PCTKR2017010533-appb-I000095
실시예Example 2-1 내지 2-15 2-1 to 2-15
상기 비교예 1-1에서 HT1로 표시되는 화합물 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 비교예 1-1과 동일한 방법으로 실시예 2-1 내지 2-15의 유기 발광 소자를 제작하였다.The organic light emitting diode of Examples 2-1 to 2-15 in the same manner as in Comparative Example 1-1 except for using the compound shown in Table 1 instead of the compound represented by HT1 in Comparative Example 1-1. Was produced.
실험예Experimental Example 2 2
상기 실시예 2-1 내지 2-15 및 비교예 1-1, 2-1 내지 2-4에서 제조한 유기 발광 소자에 전류를 인가하였을 때, 전압, 효율, 색좌표 및 수명을 측정하고 그 결과를 하기 표 2에 나타내었다. T95는 휘도가 초기 휘도(6000 nit)에서 95%로 감소되는 데 소요되는 시간을 의미한다.When current was applied to the organic light emitting diodes manufactured in Examples 2-1 to 2-15 and Comparative Examples 1-1 and 2-1 to 2-4, voltage, efficiency, color coordinates, and lifetime were measured, and the results were measured. It is shown in Table 2 below. T95 means the time it takes for the luminance to decrease to 95% from the initial luminance (6000 nit).
화합물(정공 수송층)Compound (hole transport layer) 전압(V @ 10mA/cm2)Voltage (V @ 10mA / cm 2 ) 효율(cd/A @ 10mA/cm2)Efficiency (cd / A @ 10mA / cm 2 ) 색좌표 (x, y)Color coordinates (x, y) 수명(T95, hr)Life (T95, hr)
실시예 2-1Example 2-1 화합물 1Compound 1 3.563.56 6.206.20 0.141, 0.0430.141, 0.043 290290
실시예 2-2Example 2-2 화합물 2Compound 2 3.503.50 6.186.18 0.141, 0.0450.141, 0.045 275275
실시예 2-3Example 2-3 화합물 3Compound 3 3.553.55 6.246.24 0.141, 0.0450.141, 0.045 285285
실시예 2-4Example 2-4 화합물 4Compound 4 3.533.53 6.216.21 0.142, 0.0430.142, 0.043 270270
실시예 2-5Example 2-5 화합물 5Compound 5 3.553.55 6.176.17 0.141, 0.0440.141, 0.044 285285
실시예 2-6Example 2-6 화합물 6Compound 6 3.543.54 6.156.15 0.141, 0.0440.141, 0.044 275275
실시예 2-7Example 2-7 화합물 7Compound 7 3.573.57 6.116.11 0.142, 0.0430.142, 0.043 285285
실시예 2-8Example 2-8 화합물 8Compound 8 3.593.59 6.096.09 0.139, 0.0450.139, 0.045 270270
실시예 2-9Example 2-9 화합물 9Compound 9 3.513.51 6.116.11 0.141, 0.0430.141, 0.043 285285
실시예 2-10Example 2-10 화합물 10Compound 10 3.543.54 6.216.21 0.139, 0.0450.139, 0.045 290290
실시예 2-11Example 2-11 화합물 11Compound 11 3.543.54 6.146.14 0.143, 0.0440.143, 0.044 280280
실시예 2-12Example 2-12 화합물 12Compound 12 3.513.51 6.186.18 0.142, 0.0430.142, 0.043 275275
실시예 2-13Example 2-13 화합물 13Compound 13 3.603.60 6.216.21 0.143, 0.0430.143, 0.043 275275
실시예 2-14Example 2-14 화합물 14Compound 14 3.613.61 6.196.19 0.139, 0.0440.139, 0.044 280280
실시예 2-15Example 2-15 화합물 15Compound 15 3.593.59 6.196.19 0.140, 0.0440.140, 0.044 275275
비교예 1-1Comparative Example 1-1 HT1HT1 3.893.89 5.745.74 0.143, 0.0450.143, 0.045 230230
비교예 2-1Comparative Example 2-1 HT2HT2 4.054.05 5.495.49 0.144, 0.0480.144, 0.048 210210
비교예 2-2Comparative Example 2-2 HT3HT3 4.084.08 5.425.42 0.143, 0.0470.143, 0.047 210210
비교예 2-3Comparative Example 2-3 HT4HT4 4.164.16 5.255.25 0.143, 0.0470.143, 0.047 175175
비교예 2-4Comparative Example 2-4 HT5HT5 4.164.16 5.345.34 0.144, 0.0480.144, 0.048 150150
상기 표 2에 나타난 바와 같이, 본 발명의 화합물을 정공수송층으로 사용한 유기 발광 소자는 구동 전압, 효율, 수명 면에서 현저한 효과를 나타내는 것으로 확인되었다.As shown in Table 2, it was confirmed that the organic light emitting device using the compound of the present invention as the hole transport layer exhibits significant effects in terms of driving voltage, efficiency, and lifetime.
상기 표 2의 결과와 같이, 본 발명에 따른 화합물은 전자 수송 능력이 우수하여 유기 발광 소자에 적용 가능함을 확인할 수 있었다.As shown in Table 2, the compound according to the present invention was confirmed that the excellent electron transport ability can be applied to the organic light emitting device.

Claims (15)

  1. 하기 화학식 1로 표시되는 화합물: Compound represented by the following formula (1):
    [화학식 1] [Formula 1]
    Figure PCTKR2017010533-appb-I000096
    Figure PCTKR2017010533-appb-I000096
    상기 화학식 1에 있어서,In Chemical Formula 1,
    R1 내지 R4는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 실릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 티오알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이며,R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted thioalkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
    n1 내지 n3는 각각 0 내지 4의 정수이고,n1 to n3 are each an integer of 0 to 4,
    n1 내지 n3가 각각 2 이상인 경우, 괄호 내의 치환기는 서로 같거나 상이하며,when n1 to n3 are each 2 or more, the substituents in parentheses are the same as or different from each other,
    n4는 0 내지 2의 정수이고,n4 is an integer of 0 to 2,
    n4가 2 이상인 경우, 괄호 내의 치환기는 서로 같거나 상이하며,when n4 is 2 or more, the substituents in parentheses are the same as or different from each other,
    p1 내지 p3는 각각 0 내지 3의 정수이고,p1 to p3 are each an integer of 0 to 3,
    p1 내지 p3가 각각 2 이상인 경우, 괄호 내의 치환기는 서로 같거나 상이하며,when p1 to p3 are each 2 or more, the substituents in parentheses are the same as or different from each other,
    L, L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 2가의 헤테로고리기이고,L, L1 and L2 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
    Ar1은 트라이페닐렌이며,Ar1 is triphenylene,
    Ar2는 수소; 중수소; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 아릴알케닐기; 또는 치환 또는 비치환된 헤테로고리기이고,Ar2 is hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Substituted or unsubstituted arylalkyl group; Substituted or unsubstituted aryl alkenyl group; Or a substituted or unsubstituted heterocyclic group,
    X1은 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 아릴알케닐기; 또는 치환 또는 비치환된 헤테로고리기이다.X1 is a substituted or unsubstituted aryl group; Substituted or unsubstituted arylalkyl group; Substituted or unsubstituted aryl alkenyl group; Or a substituted or unsubstituted heteroring group.
  2. 제1항에 있어서,The method of claim 1,
    상기 화학식 1로 표시되는 화합물은 하기 화학식 2 내지 4 중 하나로 표시되는 화합물:Compound represented by Formula 1 is a compound represented by one of the following formulas 2 to 4:
    [화학식 2][Formula 2]
    Figure PCTKR2017010533-appb-I000097
    Figure PCTKR2017010533-appb-I000097
    [화학식 3][Formula 3]
    Figure PCTKR2017010533-appb-I000098
    Figure PCTKR2017010533-appb-I000098
    [화학식 4][Formula 4]
    Figure PCTKR2017010533-appb-I000099
    Figure PCTKR2017010533-appb-I000099
    상기 화학식 2 내지 4에 있어서,In Chemical Formulas 2 to 4,
    R1 내지 R4, X1, L, L1, L2, n1 내지 n4, p1 내지 p3, Ar1 및 Ar2는 상기 화학식 1에서의 정의와 같다.R1 to R4, X1, L, L1, L2, n1 to n4, p1 to p3, Ar1 and Ar2 are the same as defined in the formula (1).
  3. 제1항에 있어서,The method of claim 1,
    상기 -(L)p1-N[(L1)p2Ar1][(L2)p3Ar2]는 하기 화학식 5로 표시되는 화합물: The- (L) p1 -N [(L1) p2 Ar1] [(L2) p3 Ar2] is a compound represented by the formula
    [화학식 5][Formula 5]
    Figure PCTKR2017010533-appb-I000100
    Figure PCTKR2017010533-appb-I000100
    상기 화학식 5에 있어서, In Chemical Formula 5,
    L, L2, p1, p3 및 Ar2의 정의는 상기 화학식 1에서의 정의와 같다.Definitions of L, L2, p1, p3, and Ar2 are the same as those defined in Chemical Formula 1.
  4. 제1항에 있어서, The method of claim 1,
    L은 직접결합 또는 하기 구조들 중에서 선택된 어느 하나인 화합물:L is a direct bond or any one selected from the following structures:
    Figure PCTKR2017010533-appb-I000101
    Figure PCTKR2017010533-appb-I000101
    상기 구조들에 있어서,In the above structures,
    R17 내지 R19은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 실릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.R17 to R19 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  5. 제1항에 있어서,The method of claim 1,
    X1은 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기인 화합물.X1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  6. 제1항에 있어서,The method of claim 1,
    X1은 하기 구조들 중에서 선택된 어느 하나인 화합물:X1 is any compound selected from the following structures:
    Figure PCTKR2017010533-appb-I000102
    Figure PCTKR2017010533-appb-I000102
    Figure PCTKR2017010533-appb-I000103
    Figure PCTKR2017010533-appb-I000103
    Figure PCTKR2017010533-appb-I000104
    Figure PCTKR2017010533-appb-I000104
    상기 구조들에 있어서, In the above structures,
    R11 내지 R13은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 실릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 치환기는 서로 결합하여 치환 또는 비치환된 고리를 형성한다.R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring.
  7. 제1항에 있어서,The method of claim 1,
    Ar2는 하기 구조들 중에서 선택된 어느 하나인 화합물:Ar 2 is a compound selected from the following structures:
    Figure PCTKR2017010533-appb-I000105
    Figure PCTKR2017010533-appb-I000105
    Figure PCTKR2017010533-appb-I000106
    Figure PCTKR2017010533-appb-I000106
    상기 구조들에 있어서,In the above structures,
    R14 내지 R16은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 실릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 치환기는 서로 결합하여 치환 또는 비치환된 고리를 형성한다.R14 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring.
  8. 제1항에 있어서,The method of claim 1,
    L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 하기 구조들 중에서 선택된 어느 하나인 화합물:L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a compound selected from the following structures:
    Figure PCTKR2017010533-appb-I000107
    Figure PCTKR2017010533-appb-I000107
    상기 구조들에 있어서,In the above structures,
    R17 내지 R19은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 실릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.R17 to R19 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  9. 제1항에 있어서, The method of claim 1,
    화학식 1로 표시되는 화합물은 하기 구조들 중에서 선택된 어느 하나인 화합물:Compound represented by Formula 1 is any one selected from the following structures:
    Figure PCTKR2017010533-appb-I000108
    Figure PCTKR2017010533-appb-I000108
    Figure PCTKR2017010533-appb-I000109
    Figure PCTKR2017010533-appb-I000109
    Figure PCTKR2017010533-appb-I000110
    Figure PCTKR2017010533-appb-I000110
    Figure PCTKR2017010533-appb-I000111
    Figure PCTKR2017010533-appb-I000111
    Figure PCTKR2017010533-appb-I000112
    Figure PCTKR2017010533-appb-I000112
    Figure PCTKR2017010533-appb-I000113
    Figure PCTKR2017010533-appb-I000113
    Figure PCTKR2017010533-appb-I000114
    Figure PCTKR2017010533-appb-I000114
    Figure PCTKR2017010533-appb-I000115
    Figure PCTKR2017010533-appb-I000115
    Figure PCTKR2017010533-appb-I000116
    Figure PCTKR2017010533-appb-I000116
    Figure PCTKR2017010533-appb-I000117
    Figure PCTKR2017010533-appb-I000117
    Figure PCTKR2017010533-appb-I000118
    Figure PCTKR2017010533-appb-I000118
    Figure PCTKR2017010533-appb-I000119
    Figure PCTKR2017010533-appb-I000119
    Figure PCTKR2017010533-appb-I000120
    Figure PCTKR2017010533-appb-I000120
    Figure PCTKR2017010533-appb-I000121
    Figure PCTKR2017010533-appb-I000121
    Figure PCTKR2017010533-appb-I000122
    Figure PCTKR2017010533-appb-I000122
    Figure PCTKR2017010533-appb-I000123
    Figure PCTKR2017010533-appb-I000123
    Figure PCTKR2017010533-appb-I000124
    Figure PCTKR2017010533-appb-I000124
    Figure PCTKR2017010533-appb-I000125
    Figure PCTKR2017010533-appb-I000125
    Figure PCTKR2017010533-appb-I000126
    Figure PCTKR2017010533-appb-I000126
    Figure PCTKR2017010533-appb-I000127
    Figure PCTKR2017010533-appb-I000127
    Figure PCTKR2017010533-appb-I000128
    Figure PCTKR2017010533-appb-I000128
    Figure PCTKR2017010533-appb-I000129
    Figure PCTKR2017010533-appb-I000129
    Figure PCTKR2017010533-appb-I000130
    Figure PCTKR2017010533-appb-I000130
    Figure PCTKR2017010533-appb-I000131
    Figure PCTKR2017010533-appb-I000131
    Figure PCTKR2017010533-appb-I000132
    Figure PCTKR2017010533-appb-I000132
    Figure PCTKR2017010533-appb-I000133
    Figure PCTKR2017010533-appb-I000133
    Figure PCTKR2017010533-appb-I000134
    Figure PCTKR2017010533-appb-I000134
    Figure PCTKR2017010533-appb-I000135
    Figure PCTKR2017010533-appb-I000135
    Figure PCTKR2017010533-appb-I000136
    Figure PCTKR2017010533-appb-I000136
    Figure PCTKR2017010533-appb-I000137
    Figure PCTKR2017010533-appb-I000137
    Figure PCTKR2017010533-appb-I000138
    Figure PCTKR2017010533-appb-I000138
    Figure PCTKR2017010533-appb-I000139
    Figure PCTKR2017010533-appb-I000139
    Figure PCTKR2017010533-appb-I000140
    .
    Figure PCTKR2017010533-appb-I000140
    .
  10. 제1 전극, 제2 전극, 및 상기 제1 전극과 제2 전극 사이에 배치된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 청구항 1 내지 9 중 어느 하나의 항에 따른 화합물을 포함하는 것을 특징으로 하는 유기 발광 소자.An organic light emitting device comprising 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 any one of claims 1 to 9. An organic light-emitting device comprising a compound according to.
  11. 제10항에 있어서,The method of claim 10,
    상기 유기물층은 정공 주입층 또는 정공 수송층을 포함하고, 상기 정공 주입층 또는 정공 수송층은 상기 화학식 1의 화합물을 포함하는 것인 유기 발광 소자.The organic material layer includes a hole injection layer or a hole transport layer, the hole injection layer or hole transport layer is an organic light emitting device comprising the compound of Formula 1.
  12. 제10항에 있어서,The method of claim 10,
    상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1의 화합물을 포함하는 것인 유기 발광 소자.The organic material layer comprises a light emitting layer, the light emitting layer is an organic light emitting device comprising the compound of Formula 1.
  13. 제10항에 있어서,The method of claim 10,
    상기 유기물층은 전자 주입층 또는 전자 수송층을 포함하고, 상기 전자 주입층 또는 전자 수송층은 상기 화학식 1의 화합물을 포함하는 것인 유기 발광 소자.The organic material layer includes an electron injection layer or an electron transport layer, and the electron injection layer or an electron transport layer comprises the compound of Formula 1.
  14. 제10항에 있어서,The method of claim 10,
    상기 유기물층은 전자 저지층을 포함하고, 상기 전자 저지층은 상기 화학식 1의 화합물을 포함하는 것인 유기 발광 소자.The organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound of Formula 1.
  15. 제10항에 있어서,The method of claim 10,
    상기 유기 발광 소자는 정공 주입층, 정공 수송층, 전자 수송층, 전자 주입층, 전자 저지층 및 정공 저지층으로 이루어진 군에서 선택되는 1층 또는 2층 이상을 더 포함하는 것인 유기 발광 소자.The organic light emitting device further comprises one or two or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron blocking layer and a hole blocking layer.
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