WO2019190235A1 - Composé et dispositif électroluminescent organique le comprenant - Google Patents

Composé et dispositif électroluminescent organique le comprenant Download PDF

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WO2019190235A1
WO2019190235A1 PCT/KR2019/003657 KR2019003657W WO2019190235A1 WO 2019190235 A1 WO2019190235 A1 WO 2019190235A1 KR 2019003657 W KR2019003657 W KR 2019003657W WO 2019190235 A1 WO2019190235 A1 WO 2019190235A1
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group
formula
light emitting
substituted
layer
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PCT/KR2019/003657
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Korean (ko)
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윤홍식
홍완표
김진주
강유진
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주식회사 엘지화학
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Priority to CN201980003800.XA priority Critical patent/CN111051283B/zh
Publication of WO2019190235A1 publication Critical patent/WO2019190235A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom

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).
  • X is a direct bond; O; Or S,
  • Y is NR; O; Or S,
  • R1 is a substituted or unsubstituted alkyl group having 2 to 60 carbon atoms; Or a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms,
  • R and R2 to R4 are each independently hydrogen; heavy hydrogen; Halogen group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • a 1 or 2
  • b 0 or 1
  • c and e are each independently an integer of 0 to 4,
  • d is an integer of 0 to 2
  • 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 a compound according to one embodiment of the specification.
  • 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 lifetime characteristics in the organic light emitting diode.
  • the compounds described herein can be used as the material of the light emitting layer.
  • the compound according to the exemplary embodiment of the present invention has a structure having a high electron accepting ability, and excellent heat resistance to maintain an appropriate deposition temperature when fabricating an organic light emitting device.
  • the sublimation temperature is high, high purity can be achieved by the sublimation refining method, and it does not cause contamination to the deposition apparatus or the organic light emitting device for deposition in manufacturing the organic light emitting device.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
  • An exemplary embodiment of the present specification provides a compound represented by Chemical Formula 1.
  • the compound represented by Formula 1 is a delayed fluorescent compound.
  • the number of excitons generated in the singlet and triplet is generated in the ratio of 25:75 (single term: triplet), and the fluorescence, phosphorescence, and thermal activation delayed fluorescence according to the emission form according to exciton movement It can be divided into luminescence.
  • the excitons in the triplet excited state move to the ground state and emit light.
  • the excitons in the singlet excited state are ground state ( The thermally activated delayed fluorescence emission is induced in the reverse interphase transition from the triplet excited state to the singlet excited state, and the singlet excited state This means that excitons move to the ground state and cause fluorescence.
  • the thermally activated delayed fluorescence emission is distinguished from fluorescence in that the peak position of the emission spectrum is the same as the fluorescence but the decay time is long, and the peak position of the emission spectrum is the phosphorescence spectrum and S 1 -T although the decay time is long. It differs from phosphorescence in that it differs by one energy difference. In this case, S 1 is a singlet energy level, and T 1 is a triplet energy level.
  • the difference ( ⁇ E ST ) between the singlet energy level and triplet energy level of the compound represented by Formula 1 is 0 eV or more and 0.3 eV or less, preferably Is 0 eV or more and 0.2 eV or less.
  • the excitons generated in the triplet are converted into singlet by the reverse interphase transition (RISC). Since the exciton stays in the triplet is reduced by increasing the rate and speed of the movement, there is an advantage that the efficiency and life of the organic light emitting device is increased.
  • the term "substituted or unsubstituted” is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; An alkyl group; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; And it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group, or substituted or unsubstituted two or more substituents of the substituents exe
  • a substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.
  • adjacent The group may mean a substituent substituted with an atom directly connected to an atom in which the corresponding substituent is substituted, a substituent positioned closest in structural conformation to the substituent, or another substituent substituted in an atom in which the substituent is substituted.
  • two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as “adjacent” to each other.
  • a substituent substituted for N in carbazole and a substituent of carbon 1 or carbon 8 of carbazole may be interpreted as “adjacent group”.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C40. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 40 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
  • carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • the silyl group may be represented by the formula of -SiR a R b R c , wherein R a , R b and R c are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • Specific examples of the silyl group include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group, but are not limited thereto. 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, a dimethyl boron group, a diethyl boron group, a t-butyl methyl boron group, a diphenyl boron group, a phenyl boron group, and the like.
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl
  • the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C40. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like It may be, but is not limited thereto.
  • Substituents comprising alkyl groups, alkoxy groups and other alkyl group moieties described herein include both straight and pulverized forms.
  • the alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group and the like, but are not limited thereto.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 40 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
  • the alkylamine group is not particularly limited in carbon number, but is preferably 1 to 40.
  • Specific examples of the alkylamine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine Groups, diphenylamine groups, phenylnaphthylamine groups, ditolylamine groups, phenyltolylamine groups, triphenylamine groups and the like, but are not limited thereto.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group, may be a polycyclic aryl group.
  • the arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
  • aryl amine group examples include phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 3-methyl-phenylamine group, 4-methyl-naphthylamine group, and 2-methyl-biphenylamine.
  • examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group.
  • the heteroaryl group in the heteroarylamine group may be a monocyclic heterocyclic group or may be a polycyclic heterocyclic group.
  • the heteroarylamine group including two or more heterocyclic groups may include a monocyclic heterocyclic group, a polycyclic heterocyclic group, or a monocyclic heterocyclic group and a polycyclic heterocyclic group.
  • the arylheteroarylamine group means an amine group substituted with an aryl group and a heterocyclic group.
  • examples of the arylphosphine group include a substituted or unsubstituted monoarylphosphine group, a substituted or unsubstituted diarylphosphine group, or a substituted or unsubstituted triarylphosphine group.
  • the aryl group in the arylphosphine group may be a monocyclic aryl group, may be a polycyclic aryl group.
  • the arylphosphine group containing two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
  • the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a monocyclic aryl group, but may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
  • the polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • Spirofluorenyl groups such as (9,9-dimethylfluorenyl group), and It may be a substituted fluorenyl group such as (9,9-diphenyl fluorenyl group).
  • the present invention is not limited thereto.
  • the heterocyclic group is a heterocyclic group containing one or more of N, O, P, S, Si, and Se as hetero atoms, and the carbon number is not particularly limited, but is preferably 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 number of atoms constituting the ring of the heterocyclic group is 2 to 25. In another embodiment, the number of atoms constituting the ring of the heterocyclic group is 5 to 17.
  • heterocyclic group may be applied except that the heteroaryl group is aromatic.
  • the aryl group in the aryloxy group, arylthioxy group, aryl sulfoxy group, aryl phosphine group, aralkyl group, aralkylamine group, aralkenyl group, alkylaryl group, arylamine group, arylheteroarylamine group is described above.
  • the description of one aryl group may apply.
  • the alkyl group among the alkyl thioxy group, the alkyl sulfoxy group, the aralkyl group, the aralkyl amine group, the alkyl aryl group, and the alkyl amine group may be described with respect to the alkyl group described above.
  • heteroaryl group a heteroarylamine group, and an arylheteroarylamine group among the heteroaryl group may be applied to the description of the aforementioned heterocyclic group.
  • alkenyl group of the alkenyl group may be applied to the description of the alkenyl group described above.
  • the description of the aryl group described above may be applied except that the arylene group is a divalent group.
  • heteroarylene group is a divalent group.
  • 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 rings; Substituted or unsubstituted aliphatic hetero ring; Substituted or unsubstituted aromatic hetero rings; Or to form a condensed ring thereof.
  • the aliphatic hydrocarbon ring means a ring composed only of carbon and hydrogen atoms as a ring which is not aromatic.
  • examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like. There is, but is not limited to these.
  • the aromatic hydrocarbon ring means an aromatic ring composed only of carbon and hydrogen atoms.
  • examples of the aromatic hydrocarbon ring include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, penalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaph Butylene, benzofluorene, spirofluorene and the like, but is not limited thereto.
  • the aliphatic hetero ring means an aliphatic ring including at least one of heteroatoms.
  • examples of aliphatic hetero rings include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepan, Azocaine, thiocaine and the like, but are not limited to these.
  • the aromatic hetero ring means an aromatic ring including at least one of heteroatoms.
  • aromatic hetero rings include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole , Thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinol, quinazoline, quinoxaline, naphthyridine, azine Cridine, phenanthridine, diazanaphthalene, triazaindene, indole, indolizine, benzothiazole, benzoxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, di
  • the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic hetero ring and aromatic hetero ring may be monocyclic or polycyclic.
  • R1 is a substituted or unsubstituted C2-C60 alkyl group; Or a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms.
  • R1 is a substituted or unsubstituted alkyl group having 2 to 30 carbon atoms; Or a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms.
  • R1 is a substituted or unsubstituted alkyl group having 2 to 15 carbon atoms; Or a substituted or unsubstituted cycloalkyl group having 3 to 15 carbon atoms.
  • R1 is a substituted or unsubstituted alkyl group having 2 to 15 carbon atoms.
  • R1 is a substituted or unsubstituted alkyl group having 3 to 15 carbon atoms.
  • R1 is a methyl group unsubstituted or substituted with a halogen group; Or an ethyl group unsubstituted or substituted with a halogen group.
  • R1 is a substituted or unsubstituted branched alkyl group having 3 to 15 carbon atoms.
  • R1 is a substituted or unsubstituted isopropyl group; Or a substituted or unsubstituted t-butyl group.
  • R1 is an isopropyl group unsubstituted or substituted with a carbazole group; Or a t-butyl group unsubstituted or substituted with a carbazole group.
  • R1 is a substituted or unsubstituted cycloalkyl group having 3 to 15 carbon atoms.
  • R1 is a substituted or unsubstituted cycloalkyl group having 6 to 15 carbon atoms.
  • R1 is a substituted or unsubstituted cyclohexane group.
  • R and R2 to R4 are each independently, hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • R and R2 to R4 are each independently, hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 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.
  • R and R2 to R4 are each independently, hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 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.
  • R and R2 to R4 are each independently, hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 15 carbon atoms; Substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.
  • R is a substituted or unsubstituted phenyl group.
  • the R2 to R4 are each independently, hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms.
  • the R2 to R4 are each independently, hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with a halogen group; Substituted or unsubstituted isopropyl group; Or a substituted or unsubstituted t-butyl group.
  • Formula 1 is represented by the following formula (2).
  • Chemical Formula 1 is represented by the following Chemical Formula 3 or 4.
  • Chemical Formula 1 is represented by the following Chemical Formula 5 or 6.
  • Formula 1 is represented by the following formula (7) or (8).
  • the compound of Formula 1 may be any one selected from the following compounds.
  • 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
  • the present inventors have found that the compound of Formula 1 having such characteristics is applied to an organic light emitting device material, that is, a light emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer or a charge generating layer, in particular, when applied to the light emitting layer, It has been found that low voltage and long life can be realized. In addition, it is easier to deposit than a material having a low molecular weight and high sublimation like F4TCNQ, and can form a stable interface with an electrode or an adjacent organic compound layer as compared with HAT-CN.
  • the compound of formula 1 described above may be prepared using materials and reaction conditions known in the art.
  • the organic light emitting device is an organic light emitting device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, at least one of the organic layer It is characterized by including the compound.
  • the organic light emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that at least one organic material layer is formed using the above-described compound.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes a dopant
  • the dopant includes a compound according to an exemplary embodiment of the present specification.
  • the light emitting material of the light emitting layer is a material capable of emitting light in the visible light region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, wherein the light emitting layer is the delayed fluorescent material described above.
  • the light emitting layer is the delayed fluorescent material described above.
  • a dopant of the light emitting layer at least one of the singlet excitation energy and the excitation triplet energy has a higher value than the light emitting material of the delayed fluorescent material described above, has a hole transporting ability, an electron transporting ability, and has a long wavelength of light emission. It is possible to prevent oxidation and include an organic compound having a high glass transition temperature as a host.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a host.
  • the triplet energy level of the host is 2.5 eV or more, preferably 2.7 eV or more and 3.1 eV or less. If the triplet energy level of the host meets the above range, host exciton energy is efficiently transferred to the dopant, and the triplet / single excitons of the host or dopant and the surrounding hole (or electron) -polaron The exciton quenching by the interaction of is minimized. Accordingly, the lifespan of the light emitting diode device can be prevented from being degraded by electro-oxidation and photo-oxidation, and thus a long-life light emitting device can be realized.
  • the organic material layer includes a host, and the host is at least one of the following structures, but is not limited thereto.
  • the organic material layer of the organic light emitting device of the present specification may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present specification may further have a structure including at least one of a hole injection layer, a hole buffer layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer in addition to the light emitting layer as the organic layer. have.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic light emitting device may be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an organic light emitting device having an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • the organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1, that is, the compound represented by Chemical Formula 1.
  • the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation
  • a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode.
  • PVD physical vapor deposition
  • an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon it can be prepared by depositing a material that can be used as a cathode thereon.
  • the compound of Formula 1 may be formed of an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate (International Patent Application Publication No. 2003/012890).
  • the manufacturing method is not limited thereto.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode and the second electrode is an anode.
  • the organic light emitting diode may have a laminated structure as described below, but is not limited thereto.
  • FIGS. 1 and 2 For example, the structure of an organic light emitting diode according to one embodiment of the present specification is illustrated in FIGS. 1 and 2.
  • FIG. 1 shows an example of an organic light emitting device composed of a substrate 1, an anode 2, a hole transport layer 6, a light emitting layer 3, and a cathode 4. As shown in FIG. In such a structure, the compound may be included in the light emitting layer.
  • FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
  • the compound may be included in the light emitting layer.
  • the anode 2 may be any one of an indium tin oxide (ITO), indium zinc oxide (IZO), or zinc oxide (ZnO) having a high work function as an electrode for injecting holes.
  • ITO indium tin oxide
  • IZO indium zinc oxide
  • ZnO zinc oxide
  • the anode 2 is a reflective electrode, the anode 2 is a reflective layer made of any one of aluminum (Al), silver (Ag), or nickel (Ni) under a layer made of any one of ITO, IZO, or ZnO. It may further include.
  • the hole injection layer 5 may play a role of smoothly injecting holes from the anode 2 to the light emitting layer 7.
  • the hole injection layer 5 may have a thickness of 1 to 150 nm.
  • the thickness of the hole injection layer 5 is 1 nm or more, there is an advantage that the hole injection characteristics can be prevented from deteriorating.
  • the hole injection layer 5 is too thick, the hole injection layer 5 is too thick to move the holes. There is an advantage that can be prevented from increasing the driving voltage to improve.
  • As the hole injection layer material hole injection materials known in the art may be used.
  • hole injection layer material CuPc (cupper phthalocyanine), PEDOT (poly (3,4) -ethylenedioxythiophene), PANI (polyaniline) and NPD (N, N-dinaphthyl-N, N'-diphenyl benzidine) Any one or more selected may be used, but is not limited thereto.
  • the hole transport layer 6 may serve to facilitate the transport of holes.
  • a hole transport material known in the art may be used.
  • the hole transport layer 6 may include NPD (N, N-dinaphthyl-N, N'-diphenylbenzidine), TPD (N, N'-bis- (3-methylphenyl) -N, N'-bis- (phenyl)- benzidine), s-TAD and MTDATA (4,4 ', 4 "-Tris (N-3-methylphenyl-N-phenyl-amino) -triphenylamine), but may be one or more selected from the group consisting of, but not limited to For example, as the hole transport layer material, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkaine derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino substituted chalcone derivatives,
  • a hole buffer layer may be further provided between the hole injection layer and the hole transport layer.
  • the hole buffer layer may comprise a hole injection or transport material known in the art.
  • An electron blocking layer may be provided between the hole transport layer and the light emitting layer, and the compound of Formula 1 or a material known in the art may be used.
  • a hole blocking layer may be provided between the electron transport layer and the light emitting layer, and a material known in the art may be used.
  • the electron transport layer 8 may serve to facilitate the transport of electrons. Materials known in the art such as Alq 3 (tris (8-hydroxyquinolino) aluminum), PBD, TAZ, spiro-PBD, BAlq, SAlq can be used.
  • the electron transport layer 8 may have a thickness of about 1 nm to about 50 nm. In this case, when the thickness of the electron transport layer 8 is 1 nm or more, there is an advantage of preventing the electron transport characteristics from being lowered. When the thickness of the electron transport layer 8 is 50 nm or less, the thickness of the electron transport layer 8 is too thick to improve the movement of electrons. In order to prevent the driving voltage from rising, there is an advantage.
  • the electron injection layer may play a role of smoothly injecting electrons.
  • Alq 3 tris (8-hydroxyquinolino) aluminum
  • PBD tris (8-hydroxyquinolino) aluminum
  • TAZ tris (tris (8-hydroxyquinolino) aluminum
  • spiro-PBD BAlq or SAlq
  • Metal compounds include metal halides, and storage can be used, for example, can be used LiQ, LiF, NaF, KF, RbF, CsF, FrF, BeF 2, MgF 2, CaF 2, SrF 2, BaF 2 and RaF 2 and the like.
  • the electron injection layer may have a thickness of about 1 nm to about 50 nm.
  • the thickness of the electron injection layer is 1 nm or more, there is an advantage that the electron injection characteristics can be prevented from being lowered.
  • the thickness of the electron injection layer is 50 nm or less, the thickness of the electron injection layer is too thick, and the driving voltage is increased to improve the movement of electrons. There is an advantage that can be prevented from being raised.
  • the cathode 4 is an electron injection electrode, and may be made of magnesium (Mg), calcium (Ca), aluminum (Al), silver (Ag), or an alloy thereof having a low work function.
  • the cathode 4 may be formed to a thickness thin enough to transmit light when the organic light emitting device is a front or double-sided light emitting structure, and may reflect light when the organic light emitting device is a rear light emitting structure. It can form thick enough.
  • the light emitting layers 3 and 7 may include the compound of Formula 1.
  • the light emitting layers 3 and 7 may be made of only the compound of Formula 1, but the compound of Formula 1 may be present in a mixed or doped state with other light emitting layer materials known in the art.
  • the compound of Formula 1 may be doped with 0.1 to 50% by weight of the light emitting layer.
  • the organic material layer may include two or more light emitting layers, and may include a charge generation layer including the compound of Formula 1 provided between the two light emitting layers.
  • one of the light emitting layers emits blue light and the other emits yellow light, thereby manufacturing an organic light emitting device that emits white light.
  • One or more organic material layers such as the above-described hole injection layer, hole buffer layer, hole transport layer, electron blocking layer, hole blocking layer, electron transport layer, electron injection layer, between the light emitting layer and the anode or cathode, and between the light emitting layer and the charge generation layer May be included.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • the organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • the compound according to the present invention may also operate on a principle similar to that applied to organic light emitting devices in organic electronic devices including organic solar cells, organic photoconductors, organic transistors and the like.
  • the compound represented by Chemical Formula 1 may be prepared by introducing a nitrogen compound into a fluorobenzene substituted with a cyano group by a SnAr reaction as follows.
  • the compounds of the embodiments were synthesized through the following procedure.
  • an organic light emitting device is manufactured by including the compound represented by Chemical Formula 1 according to one embodiment of the present specification in a light emitting layer with a host material (m-CBP) having a triplet energy value of 2.9 eV. Was evaluated.
  • m-CBP host material
  • a glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 ⁇ was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • ITO indium tin oxide
  • Fischer Co. product was used as a detergent
  • distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water.
  • ultrasonic washing was performed twice with distilled water for 10 minutes.
  • ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol dried and transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • Each thin film was deposited on the ITO transparent electrode thus prepared at a vacuum degree of 5 ⁇ 10 ⁇ 4 Pa by vacuum deposition.
  • the following compound HAT-CN was thermally vacuum deposited to a thickness of 500 kPa on ITO to form a hole injection layer.
  • the compound N-([1,1'-bisphenyl] -4-yl) -N- (4- (11-([1,1'-biphenyl] -4-yl) having a film thickness of 100 kPa on the hole transport layer ) -11H-benzo [a] carbazole-5-yl) phenyl)-[1,1'-biphenyl] -4-amine (EB1) (100 Pa) was vacuum deposited to form an electron blocking layer.
  • the following m-CBP and the compound 4CzIPN were vacuum-deposited at a weight ratio of 70:30 on the electron blocking layer with a film thickness of 300 Pa to form a light emitting layer.
  • Compound HB1 was vacuum deposited on the light emitting layer at a film thickness of 100 Pa to form a hole blocking layer.
  • the following compound ET1 and compound LiQ were vacuum deposited on the hole blocking layer in a weight ratio of 1: 1 to form an electron injection and transport layer at a thickness of 300 kPa.
  • lithium fluoride (LiF) and aluminum were deposited sequentially to have a thickness of 12 kW to form a cathode.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ / sec to 0.7 ⁇ / sec, the lithium fluoride at the cathode was maintained at 0.3 ⁇ / sec, and the aluminum at 2 ⁇ / sec.
  • the organic light emitting device was manufactured by maintaining the x10 -7 torr to 5 x 10 -6 torr.
  • An organic light emitting diode was manufactured according to the same method as Comparative Example 1 except for using the compound of Table 1 instead of the compound 4CzIPN in Comparative Example 1.
  • An organic light emitting diode was manufactured according to the same method as Comparative Example 1 except for using the following compound of T1 to T6 instead of compound 4CzIPN in Comparative Example 1.
  • HOMO and LUMO energy levels were determined by dissolving the measured compound in 5mM and electrolyte in 0.1M concentration in dimethylformamide (dimethylformamide, DMF) and confirming the oxidation and reduction potentials through CV device measurements based on ferrocene compounds. .
  • HOMO energy level of the compound and the LUMO energy level is a cyclic voltage comparing the oxidation and reduction potential of the dimethylformamide (DMF) solution in which the measured compound is dissolved at a concentration of 5 mM and the electrolyte is 0.1M. It was measured by cyclic voltammetry (CV). Specific measurement conditions are as follows.
  • Measuring solution Dimethylformamide (DMF) solution in which the measuring compound was dissolved at a concentration of 5 mM and an electrolyte (KNO 3 , Aldrich) at a concentration of 0.1 M
  • HOMO energy level (E (HOMO)) and LUMO energy level (E (LUMO)) were calculated through the following equation.
  • V solvent is the energy level of the solvent
  • E 1/2 (solvent) is the half wave level of the solvent
  • E onset ex is the point where the oxidation starts
  • E onset red is the point where the reduction begins.
  • Triplet energy (T 1 ) was measured at cryogenic conditions using the characteristics of triplet excitons with long lifespan. Specifically, after dissolving the compound in toluene solvent to prepare a sample having a concentration of 10 -5 M, the sample is put in a quartz kit and cooled to 77K, and the 300 nm light source is irradiated to the sample for measuring phosphorescence while changing the wavelength Measure the spectrum. The spectrophotometer (FP-8600 spectrophotometer, JASCO Corporation) was used for the measurement of the spectrum.
  • the vertical axis of the phosphorescence spectrum was phosphorescence intensity, and the horizontal axis was wavelength.
  • a tangent line was drawn for the rise of the short wavelength side of the phosphorescence spectrum, and the wavelength value ( ⁇ edge1 (nm)) of the intersection point of the tangent line and the horizontal axis was obtained, and the wavelength value was substituted into the following equation 1 to calculate the triplet energy. .
  • the tangent to the rise of the short wavelength side of the phosphorescence spectrum is drawn as follows. First, the maximum value of the shortest wavelength side of the maximum value of a spectrum is confirmed. At this time, the maximum point which has the peak intensity of 15% or less of the maximum peak intensity of a spectrum is not included in the maximum value of the shortest wavelength side mentioned above.
  • the tangent line at each point on the spectral curve from the short wavelength side of the phosphorescence spectrum to the maximum value is considered. Of these tangent lines, the tangent line having the largest slope value (that is, the tangent line at the inflection point) is a tangent line to the rise of the short wavelength side of the phosphorescence spectrum.
  • a 10 -5 M toluene solution of the compound to be measured was prepared, placed in a quartz cell, and the emission spectrum (vertical axis: light emission intensity, horizontal axis: wavelength) of the 300 nm light source of the sample was measured at room temperature (300 K).
  • the tangent line was drawn about the rise of the short wavelength side of this emission spectrum, and the singlet energy was computed by substituting the wavelength value ((lambda edge2 (nm)) of the intersection of this tangent line and a horizontal axis in following conversion formula 2).
  • the emission spectrum was measured by using a spectrophotometer (FP-8600 spectrophotometer) of JASCO.
  • the tangent to the rise of the short wavelength side of the emission spectrum is drawn as follows. First, the maximum value of the shortest wavelength side of the maximum value of a spectrum is confirmed. The tangent line at each point on the spectral curve from the short wavelength side of the emission spectrum to the maximum value is considered. Of these tangent lines, the tangent line having the largest slope value (that is, the tangent line at the inflection point) is a tangent line to the rise of the short wavelength side of the emission spectrum. The maximum point which has the peak intensity of 15% or less of the maximum peak intensity of a spectrum is not included in the maximum value of the shortest wavelength side mentioned above.
  • Compounds 1 to 9 used in the Examples of the present invention are all suitable as delayed fluorescent materials with ⁇ E ST of 0.3 eV or less.

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Abstract

La présente invention concerne un composé représenté par la formule chimique 1 et un dispositif électroluminescent organique le comprenant.
PCT/KR2019/003657 2018-03-28 2019-03-28 Composé et dispositif électroluminescent organique le comprenant WO2019190235A1 (fr)

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WO2022260119A1 (fr) 2021-06-10 2022-12-15 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique
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WO2023171688A1 (fr) * 2022-03-08 2023-09-14 出光興産株式会社 Composé, matériau d'élément électroluminescent organique, élément électroluminescent organique et dispositif électronique
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EP4174073A4 (fr) * 2020-06-24 2024-07-10 Idemitsu Kosan Co Composés, matériaux pour dispositifs électroluminescents organiques, dispositifs électroluminescents organiques et dispositifs électroniques

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KR20220042624A (ko) * 2020-09-28 2022-04-05 엘지디스플레이 주식회사 유기발광다이오드 및 유기발광장치
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