WO2018056773A1 - Composé à base d'amine et dispositif électroluminescent organique contenant ce composé - Google Patents

Composé à base d'amine et dispositif électroluminescent organique contenant ce composé 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/ko
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Priority to CN201780053790.1A priority Critical patent/CN109689618B/zh
Priority to US16/322,730 priority patent/US11069858B2/en
Publication of WO2018056773A1 publication Critical patent/WO2018056773A1/fr

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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

La présente invention concerne un composé de formule 1 et un dispositif électroluminescent organique le comprenant.
PCT/KR2017/010533 2016-09-23 2017-09-25 Composé à base d'amine et dispositif électroluminescent organique contenant ce composé WO2018056773A1 (fr)

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KR20130125575A (ko) * 2012-05-09 2013-11-19 덕산하이메탈(주) 트리페닐렌 유도체를 포함하는 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20150012488A (ko) * 2013-07-25 2015-02-04 롬엔드하스전자재료코리아유한회사 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
KR101614740B1 (ko) * 2015-12-17 2016-04-22 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20170088313A (ko) * 2016-01-22 2017-08-01 주식회사 엘지화학 아민계 화합물 및 이를 포함하는 유기 발광 소자

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JP7421494B2 (ja) 2018-11-29 2024-01-24 保土谷化学工業株式会社 有機エレクトロルミネッセンス素子

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