WO2019135665A1 - Dispositif électroluminescent organique - Google Patents

Dispositif électroluminescent organique Download PDF

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WO2019135665A1
WO2019135665A1 PCT/KR2019/000264 KR2019000264W WO2019135665A1 WO 2019135665 A1 WO2019135665 A1 WO 2019135665A1 KR 2019000264 W KR2019000264 W KR 2019000264W WO 2019135665 A1 WO2019135665 A1 WO 2019135665A1
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group
substituted
unsubstituted
compound
carbon atoms
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PCT/KR2019/000264
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English (en)
Korean (ko)
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하재승
김동헌
허동욱
권대견
이재구
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주식회사 엘지화학
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Priority claimed from KR1020190001735A external-priority patent/KR102404399B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201980005023.2A priority Critical patent/CN111201625B/zh
Publication of WO2019135665A1 publication Critical patent/WO2019135665A1/fr

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    • 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
    • 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

Definitions

  • the present invention is based on the Korean Patent Application No. 10-2018-0002284 filed on January 08, 2018 and the Korean Patent Application No. 10-2019-0001735 filed on January 07, 2019 The contents of which are incorporated herein by reference.
  • This application 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.
  • 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.
  • the present application is intended to provide an organic light emitting device.
  • the first organic material layer comprises a compound represented by the following general formula (1) or (2)
  • the second organic compound layer comprises a compound represented by the following general formula (3).
  • L1 to L3 each independently represent a direct bond; Or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms,
  • Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms,
  • R1 to R4 each independently represent hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted C1 to C60 haloalkyl; A substituted or unsubstituted haloalkoxy group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms,
  • a to d are each independently an integer of 0 to 4,
  • a to d are each independently an integer of 2 or more, a plurality of R1 to R4 are the same or different from each other,
  • adjacent R < 1 > may combine with each other to form a ring
  • L4 to L6 each independently represent a direct bond; Or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms,
  • Ar 3 to Ar 5 each independently represent a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms,
  • R5 and R6 are independently selected from the group consisting of hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted C1 to C60 haloalkyl; A substituted or unsubstituted haloalkoxy group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms,
  • e, f, p, q and r are each independently an integer of 0 to 4,
  • R 5, R 6, and L 4 to L 6 are the same or different from each other when e, f, p, q, and r are each independently an integer of 2 or more,
  • X1 to X6 each independently represent N or CR11
  • At least one of X1 to X3 and at least one of X4 to X6 is N,
  • R7 to R11 each independently represent hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted C1 to C60 haloalkyl; A substituted or unsubstituted haloalkoxy group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms,
  • Ar 6 to Ar 9 each independently represent a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms,
  • i and j are each independently an integer of 0 to 4,
  • g and h are each independently an integer of 0 to 3
  • a plurality of R7 to R10 are the same or different from each other.
  • An organic light emitting device using a compound according to one embodiment of the present application is capable of low driving voltage, high luminous efficiency, and long life.
  • FIG. 1 shows an example of an organic light emitting device in which a substrate 1, a first electrode 11, a first organic material layer 12, a second organic material layer 13, and a second electrode 14 are sequentially stacked.
  • FIG. 2 shows an example of an organic light emitting device in which a substrate 1, a first electrode 11, a second organic material layer 13, a first organic material layer 12, and a second electrode 14 are sequentially stacked.
  • FIG. 3 shows an example of an organic light emitting element in which a substrate 1, a first electrode 11, a first organic layer 12, a light emitting layer 3, a second organic layer 13, and a second electrode 14 are sequentially layered FIG.
  • FIG. 4 shows an example of an organic light emitting element in which a substrate 1, a first electrode 11, a second organic layer 13, a light emitting layer 3, a first organic layer 12, and a second electrode 14 are sequentially stacked FIG.
  • FIG. 5 shows an organic light emitting device in which a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 3, an electron transporting layer 7 and a cathode 4 are sequentially laminated FIG.
  • FIG. 6 is a plan view of the substrate 1, the anode 2, the hole injection layer 5, the hole transport layer 6, the hole control layer 8, the light emitting layer 3, the electron control layer 9, And a cathode (4) are sequentially laminated on a substrate (1).
  • substrate 2 anode
  • Electron transport layer 8 Hole control layer
  • first electrode 12 first organic layer
  • 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; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted amine 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.
  • the "substituent group to which two or more substituents are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the number of carbon atoms of the ester group is not particularly limited, but is preferably 1 to 50 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
  • the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 50 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60.
  • Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, Cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methyl
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert- butylcyclohexyl, cycloheptyl, Do not.
  • the alkoxy group may be linear, branched or cyclic.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 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.
  • 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.
  • 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 aryl group is a monocyclic aryl group
  • the number of carbon atoms is not particularly limited, but is preferably 6 to 25 carbon atoms.
  • Specific examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, and the like.
  • the aryl group is a polycyclic aryl group
  • the number of carbon atoms is not particularly limited. And preferably has 10 to 24 carbon atoms.
  • Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, klychenyl, fluorenyl, and the like.
  • the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
  • the heterocyclic group includes at least one non-carbon atom or hetero atom, and specifically, the hetero atom may include at least one atom selected from the group consisting of O, N, Se and S, and the like.
  • the number of carbon atoms of the heterocyclic group is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • heterocyclic group examples include a thiophene group, a furane group, a furyl 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 pyrazinopyrazinyl group, an isoquinoline group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, A benzothiazole group, a benzothiophene group, a dibenzothiophene group, a
  • the heterocyclic group includes at least one non-carbon atom or hetero atom, and specifically, the hetero atom may include at least one atom selected from the group consisting of O, N, Se and S, and the like.
  • the number of carbon atoms of the heterocyclic group is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • heterocyclic group examples include a thiophene group, a furane group, a furyl 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 pyrazinopyrazinyl group, an isoquinoline group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, A benzothiazole group, a benzothiophene group, a dibenzothiophene group, a
  • L1 to L3 each independently represent a direct bond; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
  • L1 to L3 each independently represent a direct bond; Or a substituted or unsubstituted arylene group having 6 to 15 carbon atoms.
  • L1 to L3 each independently represent a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted anthracenylene group; A substituted or unsubstituted phenanthrylene group; A substituted or unsubstituted triphenylene group; Or a substituted or unsubstituted fluorenylene group.
  • Ar1 and Ar2 are each independently selected from the group consisting of hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • Ar1 and Ar2 are each independently selected from the group consisting of hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • Ar1 and Ar2 are each independently selected from the group consisting of hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.
  • the aryl group of Ar1 and Ar2 is preferably a phenyl group; A biphenyl group; A terphenyl group; Naphthyl group; Anthracenyl group; A phenanthryl group; A triphenyl group; Or a fluorenyl group.
  • L4 to L6 each independently represent a direct bond; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
  • L4 to L6 each independently represent a direct bond; Or a substituted or unsubstituted arylene group having 6 to 15 carbon atoms.
  • each of L4 to L6 independently represents a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted terphenylene group; Or a substituted or unsubstituted naphthylene group.
  • each of Ar3 to Ar5 independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • each of Ar3 to Ar5 independently represents a substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.
  • each of Ar3 to Ar5 independently represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted carbazole group.
  • each of X1 to X6 is independently N or CR11. At least one of X1 to X3 and at least one of X4 to X6 is N.
  • each of R1 to R11 independently represents hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C1 to C30 haloalkyl; A substituted or unsubstituted C1 to C30 haloalkoxy group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C2 to C30 alkenyl group; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or when a is 2 or more, adjacent R1's are bonded to each other to form a ring.
  • each of R1 to R11 independently represents hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 15 carbon atoms; A substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms, or when a is 2 or more, adjacent R1's are bonded to each other to form a ring.
  • each of R1 to R11 independently represents hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms, or when a is 2 or more, adjacent R1's are bonded to each other to form a ring.
  • each of R1 to R11 independently represents hydrogen; Or when de is a deuterium or when a is 2 or more, R1 adjacent to each other are bonded to each other to form a ring.
  • R1 to R11 are hydrogen or when a is 2 or more, R1 adjacent to each other are bonded to each other to form a ring.
  • R1 to R11 are hydrogen or a is 2 or more, adjacent R1's are bonded to each other to form an aromatic ring.
  • Formula 1 is selected from the following structural formulas.
  • Formula 2 is selected from the following structural formulas.
  • Formula 3 is selected from the following formulas.
  • the first and second organic layers of the organic light emitting device of the present application may have a single layer structure, but may have a multilayer structure in which two or more organic layers are stacked.
  • the first organic material layer of the present application may consist of one to three layers.
  • the organic light emitting element of the present application may have a structure including a hole injection layer, a light emitting layer, an electron transporting layer, and the like 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 first organic layer may include a hole injection layer, and the hole injection layer may include a compound represented by Formula 1 or Formula 2.
  • the first organic layer includes a hole adjusting layer
  • the hole adjusting layer includes a compound represented by the above formula (1) or (2).
  • the first organic material layer includes two or more hole control layers, and the two or more hole control layers include a compound represented by the above formula (1) or (2), respectively.
  • the materials other than the compounds represented by the general formula (1) or (2) may be the same or different.
  • the second organic layer may include an electron transporting layer
  • the electron transporting layer may include a compound represented by the general formula (3).
  • the second organic material layer includes two or more electron transporting layers, and the electron transporting layer of two or more layers includes the compound represented by Formula 3, respectively.
  • the materials other than the compound represented by the general formula (3) may be the same or different from each other.
  • the organic light emitting device includes a first electrode; A second electrode facing the first electrode; A light emitting layer provided between the first electrode and the second electrode; A first or second organic material layer provided between the light emitting layer and the first electrode and between the light emitting layer and the second electrode; And a first or second organic material layer provided between the light emitting layer and the first electrode and between the light emitting layer and the second electrode, wherein the first organic material layer includes a compound represented by the formula 1 or 2 And the second organic compound layer comprises the compound represented by the general formula (3).
  • the organic light emitting device includes a first electrode; A second electrode facing the first electrode; A light emitting layer provided between the first electrode and the second electrode; A first organic layer provided between the light emitting layer and the first electrode; And a second organic compound layer disposed between the light emitting layer and the second electrode, wherein the first organic compound layer includes the compound represented by Formula 1 or Formula 2, and the second organic compound layer comprises the compound represented by Formula 3 .
  • the organic light emitting device includes a first electrode; A second electrode facing the first electrode; A light emitting layer provided between the first electrode and the second electrode; A second organic layer provided between the light emitting layer and the first electrode; And a first organic layer disposed between the light emitting layer and the second electrode, wherein the first organic layer includes a compound represented by Formula 1 or 2, and the second organic layer comprises a compound represented by Formula 3 .
  • the organic light emitting element is a hole injecting layer, a hole transporting layer.
  • the hole-transporting layer is different from the hole-transporting layer and can control the movement of holes.
  • the electron-transporting layer is different from the electron-transporting layer and can control the movement of electrons.
  • the organic material layer may contain, in addition to the organic material layer containing the compound represented by any one of Chemical Formulas 1 to 3, a hole injecting layer or a hole transporting layer containing a compound containing an arylamino group, a carbazole group or a benzocarbazole group .
  • the organic light emitting device may be a normal type organic light emitting device in which an anode, at least one organic layer, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an inverted type organic light emitting device in which a cathode, at least one organic material layer, and an anode are sequentially stacked on a substrate.
  • FIG. 1 shows an example of an organic light emitting device in which a substrate 1, a first electrode 11, a first organic material layer 12, a second organic material layer 13, and a second electrode 14 are sequentially stacked.
  • FIG. 2 shows an example of an organic light emitting device in which a substrate 1, a first electrode 11, a second organic material layer 13, a first organic material layer 12, and a second electrode 14 are sequentially stacked.
  • FIG. 3 shows an example of an organic light emitting element in which a substrate 1, a first electrode 11, a first organic layer 12, a light emitting layer 3, a second organic layer 13, and a second electrode 14 are sequentially layered FIG.
  • FIG. 4 shows an example of an organic light emitting element in which a substrate 1, a first electrode 11, a second organic layer 13, a light emitting layer 3, a first organic layer 12, and a second electrode 14 are sequentially stacked FIG.
  • FIG. 5 shows an organic light emitting device in which a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 3, an electron transporting layer 7 and a cathode 4 are sequentially laminated Structure is illustrated.
  • the hole injecting layer 5, the hole transporting layer 6, the light emitting layer 3 and the electron transporting layer 7 may contain a compound represented by the formula 1 or 2
  • at least one of the other layers may contain a compound represented by the general formula (3).
  • the 6 is a plan view of the substrate 1, the anode 2, the hole injection layer 5, the hole transport layer 6, the hole control layer 8, the light emitting layer 3, the electron control layer 9, And a cathode (4) are sequentially laminated on a substrate (1).
  • the compound is formed on at least one of the hole injection layer 5, the hole transport layer 6, the hole control layer 8, the light emitting layer 3, the electron control layer 9 and the electron transport layer 7 May contain a compound represented by the formula (1) or (2), and at least one of the others may include a compound represented by the formula (3).
  • the hole-transporting layer 8 may include a compound represented by Chemical Formula 1 or 2
  • the electron-transporting layer 7 may include a compound represented by Chemical Formula 3.
  • the organic luminescent device of the present application is formed by a material and a method known in the art except that the first organic layer includes a compound represented by the formula 1 or 2 and the second organic layer comprises a compound represented by the formula 3 .
  • the organic light emitting device of the present application can be manufactured by sequentially laminating a first electrode, a first and a second organic material layer, and a second electrode on a substrate.
  • a PVD (physical vapor deposition) method such as a sputtering method or an e-beam evaporation method
  • a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate to form a positive electrode
  • an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon, and depositing a material usable as a cathode thereon.
  • 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.
  • the compounds of Chemical Formulas 1 to 3 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, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.
  • an organic light emitting device may be fabricated by sequentially depositing an organic material layer and a cathode material on a substrate from a cathode material (International Patent Application Publication No. 2003/012890).
  • the manufacturing method 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 anode material is preferably a material having a large work function so that injection of holes into the first organic material layer can be smoothly performed.
  • 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; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.
  • the negative electrode material is preferably a material having a small work function to facilitate electron injection into the second 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 layer is a layer for injecting holes from an electrode.
  • the hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material.
  • a compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer.
  • HOMO highest occupied molecular orbital
  • the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.
  • the hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer.
  • the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer.
  • the material 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 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 (Alq3); 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.
  • the electron transporting layer is a layer that receives electrons from the cathode or electron injection 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, Is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq3; 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 a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.
  • the electron transporting layer may include a compound represented by the general formula (3), and may further include an additional electron transporting material.
  • the electron transport layer may include a compound represented by Formula 3 and LiQ (Lithium Quinolate).
  • the weight ratio of the compound represented by Formula 3 to LiQ (Lithium Quinolate) may be 10: 1 to 1:10, and may be 5: 1 to 1: 5, more specifically 2: 1 to 1: 2, preferably 1: 1.
  • the electron injecting layer is a layer for injecting electrons from an electrode.
  • the electron injecting layer has an ability to transport electrons as an electron injecting material, has an electron injecting effect from the cathode, and has an excellent electron injecting effect on the light emitting layer or the light emitting material.
  • a compound which prevents migration of excitons to the hole injection layer and is excellent in a thin film forming ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, 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- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.
  • the hole blocking layer prevents holes from reaching the cathode, and may be formed under the same conditions as those of the hole injecting layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes and the like.
  • 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.
  • Phenanthrene-9-ol 50 g, 257.4 mmol
  • chloroform 400 ml
  • NBS 45.8 g, 257.4 mmol
  • the white solid was recrystallized from hexane to obtain the compound B1 (63.27 g, yield, 90%).
  • B2-1 was synthesized in the same manner as in the synthesis of A1 except for using B1 instead of 9- (2-bromophenyl) -9H-carbazole and phenylboronic acid instead of chlorophenylboronic acid .
  • B3-1 was synthesized in the same manner as in the synthesis of B2-1 except that [1,1'-biphenyl] -4-ylboronic acid was used in place of phenylboronic acid.
  • B2-3 was prepared in the same manner as B2-3 except for using B2-2 instead of B1 and 4-chlorophenylboronic acid instead of phenylboronic acid in the synthesis of B2-1.
  • B3-2 was synthesized by the same method except that B3-1 was used instead of B2-1 in the synthesis of B2-2.
  • B3-3 was synthesized by the same method except that B3-2 was used instead of B2-2 in the synthesis of B2-3.
  • Compound 6 was synthesized by the same method except that B2-3 was used instead of A1 in the synthesis of Compound 1 above.
  • Compound 10 was prepared by the same method except that B3-3 was used instead of B2-3 in the synthesis of Compound 6 above.
  • C2-2 was synthesized by the same method except that C2-1 was used instead of C1-1 in the synthesis of C1-2.
  • C1-2 was used instead of 4-chlorophenylboronic acid and 4-bromonaphthalen- C1-3 was synthesized by the same method except for using.
  • C1-5 was synthesized in the same manner as in the synthesis of B2-2 except that C1-3 was used instead of B2-1.
  • C1-6 was synthesized by the same method except that C1-4 was used instead of C1-3 in the synthesis of C1-5.
  • Compound 14 was synthesized in the same manner as Compound 14 except that 1,8-dibromonaphthalene was used instead of 1,4-dibromonaphthalene.
  • Compound 16 was prepared by the same method except that 2,3-dibromonaphthalene was used in place of 1,4-dibromonaphthalene in the synthesis of the compound 14.
  • Compound 17 was synthesized in the same manner as Compound 14 except that C1-5 was used instead of C1-2 and C2-2 was used instead of 1,4-dibromonaphthalene.
  • Compound 18 was synthesized by the same method except that C1-6 was used instead of C1-5 in the synthesis of Compound 17.
  • a glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) at a thickness of 1,000 ⁇ was immersed in distilled water containing a dispersing agent and washed with ultrasonic waves.
  • the detergent was a product of Fischer Co.
  • the distilled water was supplied by Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. After the distilled water was washed, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying.
  • Hexanitrile hexaazatriphenylene was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 ⁇ to form a hole injection layer.
  • HT1 900 ⁇
  • Compound 1 synthesized in Production Example 1 was vacuum deposited on the hole transport layer to form a hole control layer.
  • a host BH1 and a dopant BD1 compound (25: 1) were vacuum deposited as a compound emitting layer to a thickness of 300 ⁇ .
  • an ET1 compound (50 ANGSTROM) was formed as an electron control layer, and vacuum evaporation was performed using Compound 14 synthesized in Production Example 3 and LiQ (1: 1, 310 ANGSTROM) to form an electron transport layer sequentially.
  • Lithium fluoride (LiF), Mg and Ag (10: 1, 150 ANGSTROM) were sequentially deposited on the electron transport layer, and aluminum of 1,000 ANGSTROM thickness was deposited thereon to form a cathode.
  • the deposition rate of the organic material was maintained at 1 ⁇ / sec
  • the deposition rate of lithium fluoride was 0.2 ⁇ / sec
  • the deposition rate of aluminum was 3 to 7 ⁇ / sec.
  • Example 1 The same experiment was carried out as in Example 1 except that Compound 2 was used instead of Compound 1 as the hole control layer and Compound 17 was used as the electron transport layer instead of Compound 14.
  • Example 1 The same experiment was conducted as in Example 1 except that Compound 3 was used instead of Compound 1 as the hole control layer and Compound 15 was used instead of Compound 14 as the electron transport layer.
  • Example 1 The same experiment was conducted as in Example 1 except that Compound 9 was used instead of Compound 1 as the hole control layer and Compound 15 was used as the electron transport layer instead of Compound 14.
  • Example 1 The same experiment was conducted as in Example 1 except that Compound 10 was used instead of Compound 1 as the hole control layer and Compound 17 was used as the electron transport layer instead of Compound 14.
  • Example 1 The same experiment was conducted as in Example 1 except that Compound 12 was used instead of Compound 1 as the hole control layer and Compound 15 was used as the electron transport layer instead of Compound 14.
  • Example 14 The same experiment was conducted as in Example 14 except that Compound 2 was used instead of Compound 1 as the hole control layer and Compound 15 was used as the electron transport layer instead of Compound 14.
  • Example 14 The same experiment was conducted as in Example 14 except that Compound 4 was used instead of Compound 1 as the hole control layer and Compound 15 was used instead of Compound 14 as the electron transport layer.
  • Example 14 The same experiment was conducted as in Example 14 except that Compound 11 was used instead of Compound 1 as the hole control layer and Compound 17 was used as the electron transport layer instead of Compound 14.
  • Example 14 The same experiment was conducted as in Example 14 except that Compound 12 was used instead of Compound 1 as the hole control layer and Compound 15 was used as the electron transport layer instead of Compound 14.
  • Example 14 The same experiment was conducted as in Example 14 except that Compound 13 was used instead of Compound 1 as the hole control layer and Compound 15 was used instead of Compound 14 as the electron transport layer.
  • Example 1 The same experiment was conducted as in Example 1 except that Compound 10 was used instead of Compound 1 as the hole control layer and the ratio of the electron transporting layer and LiQ was 1: 1 to 2: 1.
  • Example 14 Except that in Example 14, instead of compound 1 as the hole-controlling layer, the electron-transporting layer was used in place of the compound 14, and the ratio of the electron-transporting layer to the LiQ was 1: 1 to 1: 2 Respectively.
  • Example 14 The same experiment was carried out as in Example 14 except that Compound 13 was used instead of Compound 1 as the hole control layer, and the ratio of the electron transporting layer and LiQ was 1: 1 to 2: 1.
  • Table 1 shows the results of the organic light emitting device manufactured by using each compound as a hole transporting layer material as in Examples 1 to 32 and Comparative Examples 1 to 12.
  • Examples 1 to 32 of the compound according to one embodiment of the present invention show low driving voltage, high efficiency and lifetime characteristics as compared with Comparative Examples 1 to 12 .

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé de formule chimique 1 et un dispositif électroluminescent organique le comprenant.
PCT/KR2019/000264 2018-01-08 2019-01-08 Dispositif électroluminescent organique WO2019135665A1 (fr)

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WO2020004235A1 (fr) * 2018-06-25 2020-01-02 保土谷化学工業株式会社 Composé ayant une structure triarylamine et dispositif électroluminescent
CN110950762A (zh) * 2019-09-10 2020-04-03 北京鼎材科技有限公司 有机化合物及含有其的有机电致发光器件
WO2021045347A1 (fr) * 2019-09-03 2021-03-11 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique le comprenant
WO2021091165A1 (fr) * 2019-11-05 2021-05-14 주식회사 엘지화학 Dispositif électroluminescent organique
US20210253546A1 (en) * 2018-05-10 2021-08-19 Idemitsu Kosan Co.,Ltd. Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device
WO2021177022A1 (fr) * 2020-03-03 2021-09-10 保土谷化学工業株式会社 Élément électroluminescent organique
WO2021256515A1 (fr) * 2020-06-19 2021-12-23 保土谷化学工業株式会社 Élément électroluminescent organique
EP4129972A4 (fr) * 2020-03-31 2024-04-17 Idemitsu Kosan Co Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique

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US20210253546A1 (en) * 2018-05-10 2021-08-19 Idemitsu Kosan Co.,Ltd. Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device
JP7406486B2 (ja) 2018-06-25 2023-12-27 保土谷化学工業株式会社 トリアリールアミン構造を有する化合物および有機エレクトロルミネッセンス素子
CN112154136B (zh) * 2018-06-25 2024-04-26 保土谷化学工业株式会社 具有三芳基胺结构的化合物及有机电致发光元件
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WO2021045347A1 (fr) * 2019-09-03 2021-03-11 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique le comprenant
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CN110950762A (zh) * 2019-09-10 2020-04-03 北京鼎材科技有限公司 有机化合物及含有其的有机电致发光器件
WO2021091165A1 (fr) * 2019-11-05 2021-05-14 주식회사 엘지화학 Dispositif électroluminescent organique
WO2021177022A1 (fr) * 2020-03-03 2021-09-10 保土谷化学工業株式会社 Élément électroluminescent organique
EP4129972A4 (fr) * 2020-03-31 2024-04-17 Idemitsu Kosan Co Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique
WO2021256515A1 (fr) * 2020-06-19 2021-12-23 保土谷化学工業株式会社 Élément électroluminescent organique

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