WO2019078700A1 - Composé et dispositif électroluminescent organique le comprenant - Google Patents

Composé et dispositif électroluminescent organique le comprenant Download PDF

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WO2019078700A1
WO2019078700A1 PCT/KR2018/012503 KR2018012503W WO2019078700A1 WO 2019078700 A1 WO2019078700 A1 WO 2019078700A1 KR 2018012503 W KR2018012503 W KR 2018012503W WO 2019078700 A1 WO2019078700 A1 WO 2019078700A1
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group
compound
light emitting
layer
formula
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Korean (ko)
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윤홍식
이준엽
이호중
홍완표
김진주
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주식회사 엘지화학
성균관대학교산학협력단
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Priority to CN201880042703.7A priority Critical patent/CN110799507B/zh
Publication of WO2019078700A1 publication Critical patent/WO2019078700A1/fr

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    • H—ELECTRICITY
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    • 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
    • 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
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • 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]
    • H10K50/14—Carrier transporting layers
    • H—ELECTRICITY
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    • 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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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    • 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
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    • 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
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • 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

Definitions

  • the present invention relates to a compound and an organic light emitting device including the same.
  • the organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes couple to each other in the organic thin film and form a pair, which then extinguishes and emits light.
  • the organic thin film may be composed of a single layer or a multilayer, if necessary.
  • organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.
  • An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • Nitrogen ring compounds and organic light emitting devices containing them are described in this specification.
  • An embodiment of the present invention provides a compound represented by the following formula (1).
  • R1 and R2 are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group,
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group,
  • a and b are each independently an integer of 0 to 4,
  • c is an integer of 1 to 4,
  • a + b is 1 or more
  • a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes a compound represented by Formula 1 do.
  • the compound described in this specification can be used as a material of an organic layer of an organic light emitting device.
  • the compound according to at least one embodiment can improve the efficiency, lower driving voltage and / or lifetime characteristics in the organic light emitting device.
  • the compounds described herein can be used as hole injecting, hole transporting, hole injecting and hole transporting, electron suppressing, luminescence, hole blocking, electron transporting, or electron injecting materials.
  • the compound according to one embodiment of the present invention has a structure having a high electron accepting ability and is excellent in heat resistance, so that an appropriate deposition temperature can be maintained in the production of an organic light emitting device.
  • the sublimation temperature is high, it is possible to achieve high purity by the sublimation purification method, and does not cause contamination of the vapor deposition film forming apparatus or the organic light emitting device in manufacturing the organic light emitting device.
  • Fig. 1 shows an example of an organic light-emitting device comprising 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 comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is.
  • FIG. 3 is a graph for confirming the synthesis of a compound according to one embodiment of the present invention.
  • the present invention provides a compound represented by the above formula (1).
  • the compound represented by the following formula (1) has a small energy difference between the triplet and the singlet, so that the exciton migration (RISC) from the triplet to the singlet occurs efficiently. Therefore, When used for an organic material layer, not only the efficiency of the organic light emitting device is improved, but also a low driving voltage and an excellent lifetime characteristic.
  • a member when a member is located on another member, it includes not only the case where the member is in contact with the other member but also the case where another member exists between the two members.
  • Quot means a moiety bonded to another substituent or compound.
  • substituted means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, , Two or more substituents may be the same as or different from each other.
  • substituted or unsubstituted A halogen group; Cyano; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or that at least two of the substituents exemplified above are substituted with a substituent to which they are linked, or have no substituent.
  • a substituent to which at least two substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.
  • examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).
  • 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; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • the silyl group specifically includes a trimethylsilyl group (TMS), a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, But is not limited thereto.
  • the boron group may be represented by the formula of -BR d R e , wherein R d and R e are each hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, a n-butyl group, an isobutyl group, Hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-tert-butylpentyl group, 1-methylbutyl group, Methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, ethylhexyl group, 1-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, Propyl group,
  • the alkoxy group may be linear, branched or cyclic.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but it is 1 to 40 carbon atoms and, according to one embodiment, has 1 to 20 carbon atoms.
  • Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.
  • Substituents comprising the alkyl groups, alkoxy groups and other alkyl moieties described herein include both straight chain and branched forms.
  • the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another 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, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 40 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
  • cyclopropyl cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.
  • 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 one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto.
  • polycyclic aryl group examples include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a klycenyl group and a fluorenyl group.
  • a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • the heterocyclic group is a heterocyclic group and is a heterocyclic group containing at least one of N, O, P, S, Si and Se.
  • the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30.
  • heterocyclic group examples include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophenyl group, an imidazole group, a pyrazole group, an oxazole group, an isoxazole group, a thiazole group, A thiadiazole group, a thiadiazole group, a tetrazolyl group, a pyranyl group, a thiopyranyl group, a pyrazinyl group, an oxazinyl group, a thiazinyl group, a dioxinyl group, a triazinyl group, a tetrazinyl group, A phenanthridinyl group, a diazanaphthalenyl group, a triazinylidene group, an indole group, a thioph
  • the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from the examples of the cycloalkyl group or the aryl group except the univalent hydrocarbon ring.
  • formula (1) may be represented by the following formula (2).
  • R1, R2, Ar1, Ar2 and c are as defined in the formula (1).
  • R 1 and R 2 are each independently a substituted or unsubstituted aryl group.
  • R 1 and R 2 are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
  • R 1 and R 2 are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R 1 and R 2 are each independently a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
  • R 1 and R 2 are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group or a substituted or unsubstituted naphthyl group.
  • R 1 and R 2 are each independently a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenyl group.
  • Ar1 and Ar2 each independently represent a substituted or unsubstituted heterocyclic group.
  • Ar1 and Ar2 each independently represent a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • Ar1 and Ar2 each independently represent a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • Ar1 and Ar2 each independently represent a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.
  • Ar1 and Ar2 each independently represent a substituted or unsubstituted carbazole group.
  • c in Formula 1 is an integer of 1 to 4, meaning that at least one cyano group is substituted.
  • each of a and b is independently an integer of 1 to 4.
  • a and b are 1.
  • c is 1 or 2.
  • the formula (1) may be represented by any one of the following structures.
  • the conjugation length of the compound and the energy band gap are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy bandgap.
  • the HOMO and LUMO energy levels of the compound can be controlled by introducing the core structure having the above structure.
  • the organic light emitting device includes a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound of Formula 1.
  • the organic light emitting device of the present invention can be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that one or more organic compound layers are formed using the above-described compounds.
  • the compound may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
  • the organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.
  • the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include a compound represented by the above formula (1).
  • the organic material layer may include a hole injecting layer or a hole transporting layer, and the hole injecting layer or the hole transporting layer may include the compound represented by the above formula (1).
  • the organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the general formula (1).
  • the organic layer includes a light emitting layer
  • the light emitting layer may include the compound represented by Formula 1 as a dopant in the light emitting layer.
  • the organic material layer may include a light emitting layer
  • the light emitting layer may include a compound represented by Formula 1 as a dopant
  • the dopant may be 100 parts by weight May be 1 to 50 parts by weight.
  • the compound of Formula 1 may be used as a thermally activated delayed fluorescence (TADF), and the compound of Formula 1 may have a DELTA E st value of retarded fluorescence of less than 0.2 eV and an orientation factor characteristic of more than 0.7 It is possible to realize an organic light emitting device capable of emitting light of a high luminance, having a low driving voltage, and having a long life span.
  • TADF thermally activated delayed fluorescence
  • the thermally activated delayed fluorescence means a phenomenon in which transit transition is induced from triplet excited state to singlet excited state due to heat energy and exciton of singlet excited state moves to the ground state to cause fluorescence emission .
  • E st means the absolute value of singlet energy - triplet energy.
  • the organic layer includes a light-emitting layer
  • the light-emitting layer includes a compound represented by Formula 1 as a dopant, a fluorescent host or a phosphorescent host, have.
  • the dopant content may be 1 to 50 parts by weight based on 100 parts by weight of the host, and the fluorescent emitter may be 0 to 10 parts by weight based on 100 parts by weight of the host.
  • the compound represented by Formula 1 transmits an exciton energy to the fluorescent emitter and causes a luminescence phenomenon in the fluorescent emitter, so that it is possible to emit a high luminance, It is possible to manufacture an organic light emitting device having low and long lifetime characteristics.
  • fluorescent materials such as an anthracene-based compound, a pyrene-based compound, and a boron-based compound may be used, but the present invention is not limited thereto.
  • the first electrode is an anode and the second electrode is a cathode.
  • the first electrode is a cathode and the second electrode is a cathode.
  • the structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but the present invention is not limited thereto.
  • FIG. 1 illustrates the structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially laminated on a substrate 1.
  • the compound may be included in the light emitting layer (3).
  • FIG. 2 shows an organic light emitting device in which an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 are sequentially laminated on a substrate 1 Structure is illustrated.
  • the compound may be included in the hole injecting layer 5, the hole transporting layer 6, the light emitting layer 7, or the electron transporting layer 8.
  • the organic light emitting device may be formed by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal oxide or a metal oxide having conductivity on the substrate,
  • a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal oxide or a metal oxide having conductivity on the substrate
  • an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer, and an electron transporting layer is formed on the anode, and a material which can be used as a cathode is deposited thereon.
  • an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
  • the organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure.
  • the organic material layer may be formed using a variety of polymeric materials by a method such as a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, Layer.
  • the anode material a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer.
  • the cathode 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), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; A conductive polymer such as poly (3-methyl) compound, poly [3,4- (ethylene-1,2-dioxy)] (PEDT) compound and polypyrrole and polyaniline.
  • PEDT poly[3,4- (ethylene-1,2-dioxy)]
  • the negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO 2 / Al, but are not limited thereto.
  • the hole injecting material it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material is between the work function of the anode material and the HOMO of the surrounding organic layer.
  • the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene , An anthraquinone, and a conductive polymer of polyaniline and a poly-compound, but the present invention is not limited thereto.
  • the hole transporting material a material capable of transporting holes from the anode or the hole injecting layer to the light emitting layer and having high mobility to holes is suitable.
  • Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the light emitting layer may emit red, green or blue light, and may be formed of a phosphor or a fluorescent material.
  • the light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.
  • Alq 3 8-hydroxy-quinoline aluminum complex
  • Carbazole-based compounds Dimerized styryl compounds
  • BAlq 10-hydroxybenzoquinoline-metal compounds
  • Compounds of the benzoxazole, benzothiazole and benzimidazole series Polymers of poly (p-phenylenevinylene) (PPV) series
  • Spiro compounds Polyfluorene, rubrene, and the like, but are not limited thereto.
  • Examples of the host material of the light emitting layer include a condensed aromatic ring derivative or a heterocyclic compound.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds.
  • Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the above-mentioned formula (1) can be used together with the following compounds as a host material of the light emitting layer.
  • Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group.
  • styrylamine compound examples include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like.
  • the metal complex examples include iridium complex, platinum complex, and the like, but are not limited thereto.
  • the electron transporting material a material capable of transferring electrons from the cathode well into the light emitting layer, which is suitable for electrons, is suitable.
  • Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the organic light emitting device may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.
  • the process for preparing the material of the present invention starts from the reaction of introducing various kinds of triazine groups from a fluorophenylboronic liquid seed in which a cyano group is substituted as described below. After introducing the triazine group, biscarbazole or triscarbazole was finally introduced to synthesize the compounds of the specific examples.
  • the triazine group and the carbazoles were variously introduced through the same synthesis procedure as the above reaction formula to synthesize the substances in the specific examples.
  • the orientation of the transient dipole moments has received much attention as one of the important factors limiting external quantum efficiency.
  • a number of different orientation measurement methods have been used and reported in recent literature. The reported method is an angular optical luminescence profile measurement followed by an optical simulation; EEG measurement of an integral element of an EL element with / without an outcoupling lens using a device having a series of ETL thickness; And monochromatic electroluminescent far-field angle pattern measurements. All of these methods use commercial optical simulation software for data calculation and interpretation.
  • the methods described below are designed to evaluate the horizontal alignment factor of a number of materials used in devices having a standard set of materials.
  • CzTrz doped with m-CBP is deposited on a silica fused substrate made of hemispheres.
  • a 300 nm light which can be excited on the deposited substrate is irradiated to set a range in which the detector is positioned in a direction in which light is emitted.
  • the horizontal alignment factor was measured in the same manner as in Experimental Example 1, except that Compound 8 was used instead of Compound CzTrz in Experimental Example 1.
  • the horizontal alignment factor was measured in the same manner as in Experimental Example 1, except that BCzTrz was used in place of the compound CzTrz in Experimental Example 1.
  • an organic light emitting device was fabricated by including the host material (m-CBP) having a triplet value of 2.5 eV or more in Formula 1 according to one embodiment of the present invention to evaluate its characteristics.
  • m-CBP host material having a triplet value of 2.5 eV or more in Formula 1 according to one embodiment of the present invention to evaluate its characteristics.
  • the glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 ⁇ was immersed in distilled water containing detergent and washed with ultrasonic waves.
  • Fischer Co. was used as a detergent
  • distilled water filtered by a filter of Millipore Co. was used as distilled water.
  • the ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.
  • Each thin film was laminated on the prepared ITO transparent electrode by a vacuum deposition method with a degree of vacuum of 5.0 X 10 < -4 > Pa.
  • hexanitrile hexaazatriphenylene (HAT) was thermally vacuum deposited on ITO to a thickness of 500 ⁇ to form a hole injection layer.
  • N-phenylamino] biphenyl 300 ⁇ was vacuum-deposited on the hole injection layer to form a hole transport layer, which is a material for transporting holes, and the following compound 4-4'-bis [N- (1-naphthyl) Respectively.
  • m-CBP and 4CzIPN were vacuum deposited on the electron blocking layer to a thickness of 300 ANGSTROM at a weight ratio of 70:30 to form a light emitting layer.
  • Compound HB1 was vacuum deposited on the light emitting layer to a thickness of 100 ⁇ to form a hole blocking layer.
  • Compound ET1 and compound LiQ were vacuum deposited on the hole blocking layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 300 ⁇ .
  • Lithium fluoride (LiF) and aluminum were deposited to a thickness of 2000 ⁇ on the electron injecting and transporting layer sequentially to form a cathode.
  • the compound of the present invention is applicable to a delayed fluorescent organic light emitting device because of its excellent light emitting ability and high color purity.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé de formule 1 et un dispositif électroluminescent organique le comprenant.
PCT/KR2018/012503 2017-10-20 2018-10-22 Composé et dispositif électroluminescent organique le comprenant WO2019078700A1 (fr)

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KR102534666B1 (ko) * 2017-11-30 2023-05-18 엘지디스플레이 주식회사 유기 화합물과 이를 포함하는 유기발광다이오드 및 유기발광 표시장치
CN111825660A (zh) * 2019-04-19 2020-10-27 北京鼎材科技有限公司 化合物、热活化延迟荧光材料、有机电致发光器件及应用

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