WO2019132545A1 - Dispositif électroluminescent organique - Google Patents

Dispositif électroluminescent organique Download PDF

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WO2019132545A1
WO2019132545A1 PCT/KR2018/016773 KR2018016773W WO2019132545A1 WO 2019132545 A1 WO2019132545 A1 WO 2019132545A1 KR 2018016773 W KR2018016773 W KR 2018016773W WO 2019132545 A1 WO2019132545 A1 WO 2019132545A1
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compound
group
substituted
light emitting
emitting device
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PCT/KR2018/016773
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English (en)
Korean (ko)
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이정하
박태윤
조성미
이동훈
정민우
한수진
김서연
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주식회사 엘지화학
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Priority claimed from KR1020180169819A external-priority patent/KR102163072B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201880063481.7A priority Critical patent/CN111183204B/zh
Priority to US16/753,497 priority patent/US11581494B2/en
Publication of WO2019132545A1 publication Critical patent/WO2019132545A1/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
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene

Definitions

  • the present invention relates to an organic light emitting device.
  • organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.
  • Organic light emitting devices which utilize organic light emitting phenomenon have a wide viewing angle, excellent contrast , fast response time, excellent characteristics of luminance, driving voltage and response speed, and much research has been conducted.
  • the organic light emitting device generally has a structure including an anode and a cathode, and an organic layer between the anode and the cathode.
  • the organic material layer may have a multilayer structure composed of different materials.
  • the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • Patent Document 0001 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to an organic light emitting device.
  • the present invention provides the following organic light emitting device:
  • anode Anode; A negative electrode opposed to the positive electrode; And at least one organic material layer provided between the anode and the cathode,
  • the organic layer includes a light emitting layer
  • the light emitting layer comprises a compound represented by the following formula (1) and a compound represented by the following formula (2)
  • Substituted or unsubstituted 0 3-60 cycloalkyl Substituted or unsubstituted 0 1-60 alkyl, substituted or unsubstituted 0 6-60 aryl; Or a substituted or unsubstituted one 0 2-60 heteroaryl group containing one or more heteroatoms 0, selected from the group consisting of and,
  • 2 and 3 are each independently hydrogen, cyano, substituted or unsubstituted 01 60 alkyl, substituted or unsubstituted 0 6-60 aryl; Or a substituted or unsubstituted one 0 2-60 heteroaryl group containing one or more heteroatoms 0, selected from the group consisting of and, 2019/132545 1 »(: 1 ⁇ 1 ⁇ 2018/016773
  • 3 is 11 ⁇ 2 11 ⁇ 2 -1 2 ⁇ 1 and the - or 22- 2, 4 3 ⁇ 4 2-21 / 1 and 3 ⁇ 4 4 is - except ⁇ 2 Ann crying, - 2
  • 3 and 4 are each independently a substituted or unsubstituted 0 6-60 aryl; Or a substituted or unsubstituted 0, and either 0 2-60 heteroaryl group containing one or more hetero atoms selected from the configuration in doeneungun, 2019/132545 1 is selected from the group consisting of:
  • Lt; / RTI > are each independently or predominant, at least one of the groups is N,
  • 5 , 6 and 7 are each independently a substituted or unsubstituted 0 6-60 aryl; Or 0 2-60 heteroaryl group containing one or more hetero atoms selected from substituted or unsubstituted 0, and configured to doeneungun ring.
  • the organic light emitting device described above can improve the efficiency, the lower the driving voltage and / or the lifetime characteristics of the organic light emitting device by controlling the compound included in the light emitting layer.
  • 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 cross-sectional view of a light emitting device according to a first embodiment of the present invention, which includes a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, an electron blocking layer 9, a light emitting layer 7, an electron transporting layer 8, And a cathode (4).
  • the substrate 1 shows an example in which the substrate 1, the anode 2, the hole injecting layer 5, the hole transporting layer 6, the light emitting layer 7, the hole blocking layer 11, the electron transporting layer 8, And a cathode (4).
  • the ester group may be substituted with a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group.
  • it may be a compound of the following structural formula, but is not limited thereto. 2019/132545 1 »(: 1 ⁇ 1 ⁇ 2018/016773
  • the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms.
  • it may be a compound having the following structure, but it is not limited to the following.
  • the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group A silyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.
  • the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a 1-butyldimethylboron group, a triphenylboron group, a phenylboron group and the like.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. Work 2019/132545 1 »(: 1 ⁇ 1 ⁇ 2018/016773
  • 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. Specific examples of the alkyl group roneun methyl, ethyl, propyl, 11-propyl, isopropyl, butyl, 11-butyl, isobutyl, 1-butyl-6 _, 1-methyl-butyl, 1-ethyl-butyl, pentyl, 11-pentyl, isopentyl, neopentyl, La ⁇ pendoel, haeksil, 11 haeksil, 1-methylpentyl, 2-methylpentyl,
  • 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-
  • 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 30 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. Specifically, mention may be made of 4-methylcyclohexyl, 3-methylcyclohexyl, 3-methylcyclohexyl, 3-methylcyclohexyl, 3-methylcyclopentyl, 2019/132545 1 »(: 1 ⁇ 1 ⁇ 2018/016773
  • Haeksil methylcyclohexyl, 2, 3-dimethyl-bicyclo haeksil, 3,4, 5-trimethyl-bicyclo haeksil, 4 Ah 61 ⁇ _ butyl cycloalkyl include but haeksil, cycloheptyl, cyclooctyl, and the like.
  • 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.
  • Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl 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. When the fluorenyl group is substituted,
  • the number of carbon atoms is not particularly limited, but is preferably 2 to 6 ⁇ ⁇ .
  • the heterocyclic group include a thiophene group, a furan group, a pyrrolyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, , A pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyranyl group, a pyrazinopyranyl group, an isoquinoline group, , A carbazole group, a benzoxazole group, a benzo
  • An isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group but is not limited thereto.
  • the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group and the arylamine group is the same as the aforementioned aryl group.
  • the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the alkyl group described above.
  • the heteroaryl among the heteroarylamines can be applied to the description of the above-mentioned heterocyclic groups.
  • the alkenyl group in the aralkenyl group is the same as the above-mentioned alkenyl group.
  • the description of the aryl group described above can be applied, except that the arylthene is divalent.
  • the description of the above-mentioned heterocyclic group can be applied except that the heteroarylene is a divalent group .
  • the description of the aryl group or the cycloalkyl group described above can be applied, except that the hydrocarbon ring is not a monocyclic and the two substituents are bonded to each other.
  • the description of the above-mentioned heterocyclic group can be applied, except that the heterocyclic ring is not a monovalent group and two substituents are bonded to each other.
  • the organic light emitting device according to the present invention can improve the efficiency, the driving voltage and / or the lifetime of the organic light emitting device by controlling the compound included in the light emitting layer.
  • the present invention will be described in detail.
  • the anode material a material having a large work function is preferably used so that hole injection can be smoothly conducted to the organic material layer.
  • the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, rhodium oxide, indium tin oxide ((1), indium zinc oxide (1-0) A combination of the same metal and oxide; Poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene;
  • the negative electrode material is preferably 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; Layer structure materials such as LiF / Al or Li ⁇ l l, but the present invention is not limited thereto.
  • a hole injection layer may be further included on the anode.
  • the hole injecting layer is formed of a hole injecting material.
  • the hole injecting material has a hole injecting effect on the anode, an excellent hole injecting effect on the light emitting layer or the light emitting material due to its ability to transport holes, A compound which prevents migration to the electron injection layer or the electron injecting material and is excellent in the thin film forming ability is preferable. It is preferable that the work function of the highest occupied molecular orbital (H0M0) of the hole injecting material is between the HOMO of the surrounding organic layer.
  • the hole injecting material include organic materials such as metal porphyrin, oligothiophene, arylamine-based organic materials, quinacridone-based organic materials, quinacridone-based organic materials, perylene perylene series organic matter, 2019/132545 1 »(: 1 ⁇ 1 ⁇ 2018/016773
  • Hole transport layer Anthraquinone, polyaniline and a polythiophene-based conductive polymer, but are not limited thereto.
  • the hole transport layer used in the present invention is a layer for transporting holes from a hole injection layer formed on an anode or an anode to a light emitting layer and transporting holes from the anode or the hole injection layer to the light emitting layer
  • Materials with high mobility to holes are 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 material contained in the light emitting layer 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.
  • the light emitting layer may include a host material and a dopant material.
  • the host material includes the compound represented by Formula 1 and the compound represented by Formula 2 in the present invention.
  • silver is a single bond or phenylene.
  • 2 is a single bond or phenylene.
  • a substituted or unsubstituted dibenzothiophene such as phenyl substituted with cyano, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylenyl, dimethylfluorenyl, pyridinyl, dibenzofuranyl, dibenzothiophenyl, Phenyl, or 9-phenylcarbazolyl.
  • 2 3 ⁇ 4 and 3 ⁇ 4 3 are each independently hydrogen, cyano, tert-phenyl-carbazolyl-butyl, phenyl, cyano substituted phenyl, pyridinyl, or 9.
  • 3 ⁇ 4 4 is phenyl, or biphenylyl.
  • Representative examples of the compound represented by the formula (1) are as follows:
  • the compound represented by the formula (1) can be prepared by the following reaction scheme 1.
  • nu 21 is a single bond or phenylene.
  • 2 is a single bond or phenylene.
  • 3 and 4 are each independently phenyl, biphenyl, biphenyl substituted with cyano, or dibenzofuranyl. 2019/132545 1 »(: 1 ⁇ 1 ⁇ 2018/016773
  • 5 and 6 are each independently selected from the group consisting of phenyl, phenyl substituted with carbazolyl, biphenyl, biphenylyl substituted with cyano, dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, or 9 - < / RTI > phenylcarbazolyl.
  • 7 is phenyl, phenyl substituted with fluoro, phenyl substituted with trifluoromethyl, phenyl substituted with cyano, or biphenyl.
  • Representative examples of the compound represented by the formula (2) are as follows:
  • the reaction is carried out in the Suzuki coupling reaction in the presence of a palladium catalyst and in the presence of a base, in the presence of a base,
  • the compound represented by the general formula (1) and the compound represented by the general formula (1) in the light-emitting layer may be the same as those in the general formula 2 is preferably from 99: 1 to 1:99, or from 95: 5 to 5:95. 2019/132545 1 »(: 1 ⁇ 1 ⁇ 2018/016773
  • examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • 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. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto. Electron transport layer
  • the electron transporting layer is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer.
  • the electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Do. Specific examples include: a 1-complex of 8-hydroxyquinoline; Complexes including show 13; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the electron transporting layer can be used with any desired cathode material as used according to the prior art.
  • an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or silver oxide. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer. Electron injection layer
  • the organic light emitting device may include an electron injection layer between the electron transport layer and the cathode, if necessary.
  • the electron injection layer is a layer for injecting electrons from the electrode.
  • the electron injection layer has the ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material.
  • a compound having excellent thin film forming ability is preferable.
  • Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A nitrogen-containing 5-membered ring derivative, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10 -hydroxybenzo [ Bis (2-methyl-8-quinolinato), bis (2-methyl-8-quinolinato) ( 0- cresolato ), Gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) .
  • Organic light emitting device 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10 -hydroxybenzo [ Bis (2-methyl-8-quinolinato), bis (2-methyl-8-quinolinato) (
  • FIG. 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.
  • the compound represented by Formula 1 and the compound represented by Formula 2 may be included in the light emitting layer.
  • 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.
  • the compound represented by Formula 1 and the compound represented by Formula 2 may be included in the light emitting layer.
  • 3 is a cross-sectional view of a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, 2019/132545 1 »(: 1 ⁇ 1 ⁇ 2018/016773
  • Emitting layer composed of an electron blocking layer 9, a light-emitting layer 7, an electron transporting layer 8, an electron injection layer 10, and a cathode 4 are shown.
  • the compound represented by Formula 1 and the compound represented by Formula 2 may be included in the light emitting layer.
  • 4 shows an example in which the substrate 1, the anode 2, the hole injecting layer 5, the hole transporting layer 6, the light emitting layer 7, the hole blocking layer 11, the electron transporting layer 8, And a cathode (4).
  • the compound represented by Formula 1 and the compound represented by Formula 2 may be included in the light emitting layer.
  • the organic electroluminescent device is characterized in that the above- 11) method, a metal or a metal oxide having conductivity or an alloy thereof is deposited on a substrate to form a positive electrode, and the above-mentioned layers are formed thereon, and then a material usable as a negative electrode is deposited thereon Can be manufactured.
  • an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate. Further, the light emitting layer can be formed by a solution coating method as well as a vacuum deposition method for the host and the dopant.
  • the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.
  • an organic light emitting device can be manufactured by sequentially depositing an organic material layer and a cathode material on a substrate from a cathode material.
  • the manufacturing method is not limited thereto.
  • the organic light emitting diode according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used. The production of the organic light-emitting device according to the present invention will be described in detail below. However, the following specific details are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.
  • Compound 34-4 (34.1) was obtained in the same manner as in the preparation of Compound Show-4 except that Compound 03 (for 42.2, 170.9 _01) was used instead of Compound Show- 2019/132545 1 »(: 1 ⁇ 1 ⁇ 2018/016773
  • Compound 5 was prepared in the same manner as Compound 1 except that Compound 1) -4 and 2-chloro-4,6-diphenylpyrimidine were used instead of Compound 4 and 2-chloro-4,6-diphenyltriazine respectively.
  • the compound 2 was prepared in the same manner as in the preparation of the compound 1-1 except that [1,1'-biphenyl] -4-ylboronic acid was used in place of the phenylboronic acid.
  • Production Example 9-3 Preparation of Intermediate-3 Compound
  • the compound I-3 was prepared in the same manner as in the preparation of the compound 1-1.
  • Production Example 9-4 Preparation of Intermediate 1 to 4 Compound
  • the starting materials were prepared in the same manner as in Example 1, except that the starting materials were changed according to the following Tables 1 and 2 to prepare the compounds 2 to 43.
  • the structure, shape, yield, and 3 ⁇ 4 are summarized in the following table.
  • ⁇ 0, 1111 (16) into a thin film-coated glass substrate to a thickness of 1,300 were dissolved in distilled water ⁇ detergent and washed with ultrasonic waves.
  • the detergent was used as a Fischer Inc. (nyora 0. 0) was used as a product is in millimeters of distilled water pore Inc. ( ⁇ 11 0 0 0) 2 filtered distilled water to a filter drive () of the product.
  • the plate was washed twice with distilled water and ultrasonically cleaned for 10 minutes.
  • 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.
  • the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.
  • the following compound was thermally vacuum-deposited to a thickness of 50 to form a hole injection layer.
  • a hole transport layer was formed by thermally vacuum depositing the following compound (1) in a thickness of 250 angstroms, and an electron blocking layer was formed thereon by vacuum evaporation of the following compound:
  • Compound 1 (host), compound 2-5 (host), and compound-1 (phosphorescent dopant) shown below were co-deposited at a weight ratio of 44:44:12 2019/132545 1 »(: 1/10 ⁇ 018/016773
  • a light-emitting layer having a thickness of 400 was formed.
  • the following compound (1) was vacuum deposited on the light emitting layer to a thickness of 250 angstroms.
  • the following ET-2 compound was co-deposited with a dye having a thickness of 100% to a thickness of 2% to form an electron transport layer and an electron injection layer.
  • Aluminum was deposited on the electron injecting layer to a thickness of 1,000 to form a cathode.
  • the deposition rate of the organic material is 0.4 0.7
  • An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the host compound used in forming the light emitting layer was used as shown in Table 3 below.
  • the compounds 01, 02 and 03 are respectively as follows. 2019/132545 1 »(: 1 ⁇ 1 ⁇ 2018/016773
  • the voltage, efficiency, color coordinates, and lifetime were measured by applying current to the organic light emitting device manufactured in Experimental Examples 1 to 14 and Comparative Experimental Examples 1 to 13, and the results are shown in Table 3 below.
  • 195 denotes the time required for the luminance to be reduced to 95% from the initial luminance.
  • the organic luminescent device manufactured using the compound of the present invention as a host of the luminescent layer exhibits excellent performance in terms of driving voltage and lifetime in comparison with the organic luminescent device of the comparative example .
  • the compound represented by the formula (1) and the compound represented by the formula (2) were used together, it was confirmed that the compound exhibited the high efficiency and long life characteristics as compared with the case without the compound.
  • a hole injection layer was formed by thermal vacuum deposition at a thickness of 500 angstroms.
  • the following compound-1 was thermally vacuum-deposited on the hole injection layer to a thickness of 800 pixels, and the following compound-3 was sequentially vacuum-deposited to a thickness of 500 to form a hole transport layer.
  • Compound (host), Compound 2-3 (host) and Compound (00) (phosphorescent dopant) prepared above were co-deposited on the hole transport layer at a weight ratio of 47: 47: 6 to form a 350 nm thick light emitting layer.
  • the seedlings 3 on the light emitting compound to the vacuum vapor deposition to form a hole blocking layer, and to increase on the hole blocking -4 compounds and needle ninae ⁇ TM 0 11 ⁇ 01 ⁇ 6 ) with a thickness of 1 to 50: 1 in a weight ratio of Vacuum evaporation was performed to form an electron transport layer having a thickness of 250 mm.
  • Lithium fluoride (Ni) was sequentially deposited on the electron transport film to a thickness of 10, and aluminum was deposited thereon to a thickness of 1,000 to form a cathode.
  • An organic light emitting device was prepared in the same manner as in Experimental Example 15, except that the host compound used in forming the light emitting layer was used as shown in Table 4 below. When a mixture of two kinds of compounds is used as a host, parentheses mean the weight ratio between the host compounds. Comparative Experimental Examples 14 to 30
  • An organic light emitting device was prepared in the same manner as in Experimental Example 15, except that the host compound used in forming the light emitting layer was used as shown in Table 4 below.
  • Table 4 When a mixture of two kinds of compounds is used as a host, parentheses mean the weight ratio between the host compounds.
  • compounds 01, 02 and 03 are the same compounds as those used in Table 3, respectively.
  • 195 represents the time required for the luminance to be reduced to 95% from the initial luminance.
  • the emissive layer exhibits excellent characteristics in terms of driving voltage and lifetime similarly to the experiment described above.
  • Electron blocking layer 10 electron injection layer

Abstract

La présente invention concerne un dispositif électroluminescent organique.
PCT/KR2018/016773 2017-12-27 2018-12-27 Dispositif électroluminescent organique WO2019132545A1 (fr)

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CN111072637A (zh) * 2019-12-27 2020-04-28 吉林奥来德光电材料股份有限公司 有机发光化合物、其制备方法及有机发光器件
CN112125892A (zh) * 2020-09-01 2020-12-25 烟台显华化工科技有限公司 一种化合物、电子传输材料和有机电致发光器件
CN112204034A (zh) * 2019-01-04 2021-01-08 株式会社Lg化学 新的化合物和包含其的有机发光器件
CN112409276A (zh) * 2019-08-20 2021-02-26 北京鼎材科技有限公司 一种化合物及其应用
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KR20240023022A (ko) 2021-06-18 2024-02-20 닛테츠 케미컬 앤드 머티리얼 가부시키가이샤 유기 전계 발광 소자용 재료 및 유기 전계 발광 소자

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CN112204034A (zh) * 2019-01-04 2021-01-08 株式会社Lg化学 新的化合物和包含其的有机发光器件
CN112409276A (zh) * 2019-08-20 2021-02-26 北京鼎材科技有限公司 一种化合物及其应用
CN111072637A (zh) * 2019-12-27 2020-04-28 吉林奥来德光电材料股份有限公司 有机发光化合物、其制备方法及有机发光器件
CN111072637B (zh) * 2019-12-27 2023-04-07 吉林奥来德光电材料股份有限公司 有机发光化合物、其制备方法及有机发光器件
WO2021135182A1 (fr) * 2019-12-30 2021-07-08 陕西莱特光电材料股份有限公司 Composé azoté, dispositif électroluminescent organique et dispositif électronique
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CN112125892A (zh) * 2020-09-01 2020-12-25 烟台显华化工科技有限公司 一种化合物、电子传输材料和有机电致发光器件
CN112125892B (zh) * 2020-09-01 2023-08-25 烟台显华化工科技有限公司 一种化合物、电子传输材料和有机电致发光器件
KR20240023022A (ko) 2021-06-18 2024-02-20 닛테츠 케미컬 앤드 머티리얼 가부시키가이샤 유기 전계 발광 소자용 재료 및 유기 전계 발광 소자

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