WO2012115394A2 - Composé, dispositif électronique organique utilisant celui-ci et dispositif électronique associé - Google Patents

Composé, dispositif électronique organique utilisant celui-ci et dispositif électronique associé Download PDF

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WO2012115394A2
WO2012115394A2 PCT/KR2012/001191 KR2012001191W WO2012115394A2 WO 2012115394 A2 WO2012115394 A2 WO 2012115394A2 KR 2012001191 W KR2012001191 W KR 2012001191W WO 2012115394 A2 WO2012115394 A2 WO 2012115394A2
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group
substituted
unsubstituted
organic
aryl
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WO2012115394A3 (fr
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김동하
이선희
문성윤
이범성
최대혁
박정환
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덕산하이메탈(주)
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Publication of WO2012115394A2 publication Critical patent/WO2012115394A2/fr
Publication of WO2012115394A3 publication Critical patent/WO2012115394A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers

Definitions

  • the present invention relates to a compound, an organic electronic device using the same, and an electronic device thereof.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
  • Materials used as the organic material layer in the organic electric element may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, electron injection materials, and the like, depending on their functions.
  • the light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. Can be.
  • the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.
  • the maximum emission wavelength is shifted to a long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect.
  • a host / dopant system may be used.
  • the principle is that when a small amount of dopant having an energy band gap smaller than that of the host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant, thereby producing high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.
  • a material constituting the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material.
  • a stable and efficient organic material layer for an organic electric element has not yet been made sufficiently, and therefore, the development of new materials is continuously required.
  • An object of the present invention is to provide a compound capable of improving high luminous efficiency, low driving voltage, color purity, and lifetime of an element, an organic electric element using the same, and an electronic device thereof.
  • the present invention solves the problems of the prior art described above, in order to achieve the object of the present invention to improve the luminous efficiency, low driving voltage, color purity, stability and life of the device represented by the formula (1) to provide.
  • L is a single bond; C 6 -C 60 aryl unsubstituted or substituted with one or more substituents selected from the group consisting of nitro, nitrile, halogen, C 1 -C 20 alkyl, C 1 -C 20 alkoxy and amino groups Ren group; C 2 -C 60 hetero-substituted or unsubstituted with one or more substituents selected from the group consisting of a nitro group, a nitrile group, a halogen group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group and an amino group Ring groups; And divalent substituted or unsubstituted aliphatic hydrocarbons.
  • B is directly bonded to A.
  • L may be bonded to at least one position of Ar 1 , R 1 to R 6 , and may be one selected from the group consisting of the following formulae.
  • n is an integer of 1-7. Since L is bonded to L when L is not a single bond, the maximum value of n may be determined according to the substituent type of L. In addition, when L is a single bond (not present), since B is directly bonded to A, the value of n may be 1 to 7 , and L may be bonded to a position of R 1 to R 7 .
  • Ar 1 to Ar 3 , R 1 to R 6 are the same as or different from each other, and each independently
  • Hydrogen, deuterium, halogen group C 1 ⁇ C 60 alkyl group, C 1 ⁇ C 60 alkoxy group, C 1 ⁇ C 60 alkylamine group, C 1 ⁇ C 60 arylamine group, C 1 ⁇ C 60 Alkyl thiophene group, C 6 -C 60 aryl thiophene group, C 2 -C 60 alkenyl group, C 2 -C 60 alkynyl group, C 3 -C 60 cycloalkyl group, C 6 -C 60 aryl A group, a C 6 to C 60 aryl group substituted with deuterium, a C 8 to C 60 arylalkenyl group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted germanium group, and C 6 ⁇ C 60 aryl group unsubstituted or substituted with one or more groups selected from the group consisting of a
  • Arylamine group C 6 ⁇ C 60 aryl group, C 6 ⁇ C 20 aryl group substituted with deuterium, C 7 ⁇ C 20 arylalkyl group, C 8 ⁇ C 20 aryl alkenyl group, C 2 ⁇ C 20 It is selected from the group consisting of; C 2 ⁇ C 20 Alkenyl group unsubstituted or substituted with one or more substituents in the group consisting of a heterocyclic group, a nitrile group and an acetylene group.
  • X is one of NR 10 , O, S, P, Si (R 11 ) (R 12 ), C (R 13 ) (R 14 ),
  • R 10 to R 14 are the same as or different from each other, and each independently
  • Hydrogen atom Halogen atom; A substituted or unsubstituted C 1 -C 20 alkyl group;
  • Hydrogen, deuterium, halogen group C 1 ⁇ C 60 alkyl group, C 1 ⁇ C 60 alkoxy group, C 1 ⁇ C 60 alkylamine group, C 1 ⁇ C 60 arylamine group, C 1 ⁇ C 60 Alkylthiophene group, C 6 -C 60 aryl thiophene group, C 2 -C 60 alkenyl group, C 2 -C 60 alkynyl group, C 3 -C 60 cycloalkyl group, C 6 -C 60 aryl A group, a C 6 to C 60 aryl group substituted with deuterium, a C 8 to C 60 arylalkenyl group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted germanium group, and C 6 ⁇ C 60 aryl group unsubstituted or substituted with one or more groups selected from the group consisting of a substitute
  • It is selected from the group consisting of a condensed ring group of C 6 ⁇ C 60 aromatic ring and C 4 ⁇ C 60 Aliphatic ring.
  • Ar 1 to Ar 3 , R 1 to R 6 may be bonded to adjacent groups, respectively, to form a substituted or unsubstituted saturated or unsaturated ring.
  • the term 'neighborhood group' includes not only a substituent attached to the mother nucleus but also the mother nucleus itself.
  • R 1 and R 4 may form a saturated or unsaturated ring by combining or reacting with a neighboring substituent or functional group, a functional group forming the mother nucleus, or carbon included in the mother nucleus.
  • Saturated or unsaturated ring is a concept including alicyclic, aromatic, heterocycle, heterocyclic ring and the like.
  • the present invention solves the problems of the prior art described above, in order to achieve the object of the present invention to improve the luminous efficiency, low driving voltage, color purity, stability and life of the device to the compound represented by the formula (2) to provide.
  • Ar One To Ar 3 , R One To R 6 , X, L are the same as defined in the formula (1).
  • the linking group L group in which the amine group is bonded may be bonded to one of the carbons of the five-membered heterocycle including X. That is, connector L group is R 5 Or R 6 Can be coupled to a location.
  • the formula (1) represents a compound represented by one of the following formula.
  • the compounds represented by Chemical Formula 1 may be one of the compounds represented by Chemical Formula, but are not limited thereto.
  • each substituent of the compounds represented by the formula (1) is practically difficult to exemplify all the compounds in a broad relationship, exemplary compounds have been described by way of example, but compounds represented by the formula (1) not shown in the above example formula Can be part of.
  • the present invention provides an organic electroluminescent device including the organic material layer comprising the above compound and an electronic device thereof.
  • the present invention can be used as at least one of hole injection, hole transport, electron injection, electron transport, light emitting material or passivation (kepping) material in the organic electronic device as a compound.
  • the present invention can be used as a host or a dopant in the light emitting material and the host / dopant, can be used as a hole injection, a hole transport layer.
  • the compound of the present invention improves the efficiency, life and stability of the organic electronic device, and lowers the driving voltage.
  • the present invention can provide a hole injection layer and a transport layer material having low driving voltage characteristics, high heat resistance and long life, an organic electric element including the same, and an electronic device thereof.
  • aryl group means a monocyclic or heterocyclic monovalent aromatic hydrocarbon group, and includes an aromatic ring formed by neighboring substituents participating in a bond or a reaction.
  • heterocyclic group means an aromatic or alicyclic monocyclic or heterocyclic ring containing a heteroatom (heteroatom) instead of a carbon forming a ring, a hetero formed by neighboring substituents participating in the bond or reaction Aromatic or cycloaliphatic rings.
  • the intermediate b, the intermediate 4c, and Pd (PPh 3 ) 4 were added with K 2 CO 3 in 500 ml of THF and 250 ml of water, and refluxed for 24 hours.
  • the obtained solid was washed with water and methanol and then separated by silica gel column chromatography to give the product A-8, a white solid, in 71% yield.
  • Table 2 shows the results of confirming the composition by mass spectrometry (FD-MS) of the final compounds synthesized according to the above preparation examples.
  • the mixture is heated to reflux at 80 ° C to 90 ° C. After the reaction is completed, distilled water is diluted at room temperature. Thereafter, the mixture was extracted with methylene chloride and water, the organic layer was dried over MgSO 4 , concentrated, and the resulting compound was purified by silicagel column and recrystallized to obtain a product in 65% yield.
  • Table 4 shows the results of confirming the composition by mass spectrometry (FD-MS) of the final compounds synthesized according to the above preparation examples.
  • an organic light emitting device was manufactured according to a conventional method.
  • 4T-NATA 4,4'4 "tris (N- (2-naphthyl) -N-phenylamino) -triphenylamine
  • 2T-NATA 4,4'4 "tris (N- (2-naphthyl) -N-phenylamino) -triphenylamine
  • 2T-NATA 4,4'4 "tris (N- (2-naphthyl) -N-phenylamino) -triphenylamine
  • the compound according to the invention was then vacuum deposited to a thickness of 30 nm as the hole transport compound to form a hole transport layer.
  • a light emitting layer doped with 7% of BD-052X (Idemitus) having a thickness of 45 nm on the hole transport layer (where BD-052X is blue fluorescent light) 9,10-di (naphthalene-2-anthracene (AND)) was used as the dopant and the light emitting host material.
  • BAlq (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinolineoleito) aluminum
  • BAlq (2-methyl-8-quinolineoleito) aluminum
  • BAlq 3 Tris (8-quinolinol) aluminum
  • LiF an alkali metal halide
  • Al was deposited to a thickness of 150 nm to use an Al / LiF as a cathode to prepare an organic light emitting device.
  • an organic electroluminescent device having the same structure as that of the experimental example was manufactured using a compound represented by the following formula (hereinafter abbreviated as NPB) as a hole transport material instead of the compound of the present invention.
  • NPB a compound represented by the following formula
  • the organic electroluminescent device using the organic electroluminescent device material of the present invention has high efficiency and color purity as well as long life blue light emission is obtained as a hole transporting material of the organic electroluminescent device Can be used to significantly improve the low driving voltage, high luminous efficiency and lifetime.
  • Triphenylphosphinepalladium was added to 2-neck in Sub 1-1 dissolved in oxodichlorobenzene, and the mixture was refluxed and stirred for 24 hours. Thereafter, the mixture was heated to room temperature, concentrated and separated by silica gel column chromatography to obtain Sub 1-2 as 85%.
  • Ar-Br examples of Ar-Br are as follows, but are not necessarily limited thereto.
  • Sub 2 is as follows, but is not limited thereto.
  • L is specifically a single bond; C 6 -C 60 aryl unsubstituted or substituted with one or more substituents selected from the group consisting of nitro, nitrile, halogen, C 1 -C 20 alkyl, C 1 -C 20 alkoxy and amino groups Ren group; C 2 -C 60 hetero-substituted or unsubstituted with one or more substituents selected from the group consisting of a nitro group, a nitrile group, a halogen group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group and an amino group Ring groups; And divalent substituted or unsubstituted aliphatic hydrocarbons.
  • a group consisting of divalent functional groups such as phenylene, biphenylene, naphthylene, pyridinylene, pyrimidinylene, pyrazinylene, piperidinylene, piperazinylene, pyrrolidenylene, pyrrolene, fluoreneylene and the like
  • the synthesis method is the same.
  • An organic light emitting diode was manufactured according to a conventional method using the compound of the present invention obtained through synthesis as a hole transport layer.
  • 2T-NATA 4,4 ', 4 "-tris (N- (2-naphthyl) -N-phenylamino) -triphenylamine
  • 2T-NATA 4 "-tris (N- (2-naphthyl) -N-phenylamino) -triphenylamine
  • a light emitting layer 7% doped with BD-052X (Idemitus Co., Ltd.) having a thickness of 45 nm (where BD-052X is a blue fluorescent dopant, and 9,10-die (naphthalene-2) is used as a light emitting host material.
  • Anthracene (AND) was used as (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinolineoleito) aluminum (abbreviated as BAlq) as the hole blocking layer.
  • Vacuum deposition was carried out to a thickness of 10 nm, and then tris (8-quinolinol) aluminum (hereinafter abbreviated to Alq3) was deposited to a thickness of 40 nm with an electron injection layer. Thereafter, LiF, an alkali metal halide, was deposited at a thickness of 0.2 nm, and then Al was deposited at a thickness of 150 nm to use an Al / LiF as a cathode to prepare an organic EL device.
  • Alq3 tris (8-quinolinol) aluminum
  • An organic light emitting diode was manufactured according to a conventional method using a compound obtained through synthesis as a light emitting host material of a light emitting layer.
  • a copper phthalocyanine (hereinafter abbreviated as CuPc) film was vacuum-deposited on the ITO layer (anode) formed on the glass substrate to form a thickness of 10 nm.
  • 4,4-bis [N- (1-naphthyl) -N-phenylamino] biphenyl hereinafter abbreviated as -NPD was vacuum-deposited to a thickness of 30 nm as a hole transporting compound on the membrane to form a hole transport layer. Formed.
  • the compound according to the present invention was deposited on the hole transport layer as a phosphorescent host material to form a light emitting layer, and then tris (2-phenylpyridine) iridium (hereinafter, I r) was used as a phosphorescent Ir metal complex dopant. (abbreviated to (ppy) 3)). At this time, the concentration of Ir (ppy) 3 in the light emitting layer was 5% by weight.
  • As a hole blocking layer (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm, and electron injection was performed.
  • Tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was deposited into the layer to a thickness of 40 nm. Subsequently, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm to manufacture an organic light emitting device using the Al / LiF as a cathode.
  • the organic light emitting device using the organic light emitting device material of the present invention can be used as a light emitting host, a hole transporting material can significantly improve the low driving voltage, color purity, high luminous efficiency and lifespan. have.
  • the compounds of the present invention are used in other organic material layers of the organic light emitting device, for example, a light emitting auxiliary layer, an electron injection layer, an electron transport layer, and a hole injection layer, it is obvious that the same effect can be obtained.
  • each of the substituents of the compounds represented by the formula (1) has a broad relationship, exemplarily described the synthesis examples of the representative compounds, the compounds represented by the formula (1) not illustrated by way of example as a synthesis example Can be configured.
  • the compound which has the intrinsic property of the introduced substituent can be synthesize
  • substituents used in the hole injection layer material, the hole transport layer material, the light emitting layer material, and the electron transport layer material used in the manufacture of the organic electric device, including the organic light emitting device to satisfy the conditions required for each organic material layer Materials can be prepared.
  • the compound according to the present invention can be used for various purposes in the organic electroluminescent device according to the type and nature of the substituent.
  • the compounds of the present invention can act as various layers other than the host of the phosphorescent or fluorescent light emitting layer because they are freely controlled by the core and the substituents.
  • the organic electric device of the present invention may be manufactured by a conventional method and material for manufacturing an organic electric device except for forming one or more organic material layers using the above-described compounds.
  • the compounds of the present invention are used in other organic material layers of the organic electroluminescent device, for example, a light emitting auxiliary layer, an electron injection layer, an electron transport layer, and a hole injection layer, it is obvious that the same effect can be obtained.
  • the compound of the present invention can be used in a soluble process.
  • the compound may form an organic material layer of the organic electronic device, which will be described later, by a solution process.
  • the organic material layer may be formed by using various polymer materials, rather than a solution process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be produced in fewer layers by the method.
  • Organic electroluminescent devices in which the compounds of the present invention may be used include, for example, organic electroluminescent devices (OLEDs), organic solar cells, organic photoconductor (OPC) drums, organic transistors (organic TFTs), and the like.
  • organic electroluminescent device As an example of the organic electroluminescent device to which the compounds of the present invention can be applied, an organic electroluminescent device (OLED) will be described.
  • OLED organic electroluminescent device
  • the present invention is not limited thereto, and the above-described compounds may be applied to various organic electroluminescent devices.
  • Another embodiment of the present invention is an organic electroluminescent device comprising a first electrode, a second electrode and an organic material layer disposed between the electrodes, wherein at least one of the organic material layer comprises an organic electroluminescent device comprising the compounds of the present invention to provide.
  • 1 to 6 show examples of the organic electroluminescent device to which the compound of the present invention can be applied.
  • the organic electroluminescent device except that at least one layer of the organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer to include the compound of the present invention.
  • a hole injection layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer to include the compound of the present invention.
  • reference numeral 101 denotes a substrate, 102 an anode, 103 a hole injection layer (HIL), 104 a hole transport layer (HTL), 105 a light emitting layer (EML), 106 an electron injection layer (EIL), 107 an electron transport layer ( ETL), 108 represents a negative electrode.
  • HIL hole injection layer
  • HTL hole transport layer
  • EML electron injection layer
  • ETL electron transport layer
  • the organic electroluminescent device further includes a hole blocking layer (HBL) that prevents the movement of holes, an electron blocking layer (EBL) that prevents the movement of electrons, a light emitting auxiliary layer that helps or assists light emission, and a protective layer. It may be located.
  • the protective layer may be formed to protect the organic material layer or the cathode at the uppermost layer.
  • the compound of the present invention may be included in one or more of an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer.
  • the compound of the present invention is used in place of or in combination with one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer and a protective layer It may be used to form.
  • the organic layer may be used not only in one layer but also in two or more layers.
  • it can be used as a hole injection material, a hole transport material, an electron injection material, an electron transport material, a luminescent material and a passivation (kepping) material according to the compound of the present invention, in particular a host or in a luminescent material and host / dopant alone Can be used as a dopant, can be used as a hole injection, a hole transport layer.
  • the organic electroluminescent device is a metal having metal or conductivity on a substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation.
  • PVD physical vapor deposition
  • An oxide or an alloy thereof is deposited to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer is formed thereon, and then a material that can be used as a cathode is deposited thereon.
  • PVD physical vapor deposition
  • an organic electronic device may be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, but is not limited thereto and may have a single layer structure.
  • the organic layer may be formed using a variety of polymer materials, but not by a deposition process or a solvent process, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be made with a small number of layers.
  • the organic electroluminescent device according to another embodiment of the present invention may be used in a solution process such as spin coating or ink jet process.
  • the substrate is a support of the organic electroluminescent device, and a silicon wafer, a quartz or glass plate, a metal plate, a plastic film or sheet, or the like can be used.
  • the positive electrode material may be a material having a large work function to facilitate hole injection into the organic material layer.
  • Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SnO 2: Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the hole injection layer is located on the anode.
  • the conditions required for the material of the hole injection layer are high hole injection efficiency from the anode, it should be able to transport the injected holes efficiently. This requires a small ionization potential, high transparency to visible light, and excellent hole stability.
  • the hole injection material is a material that can be injected well from the anode at a low voltage, the highest occupied molecular orbital (HOMO) of the hole injection material may be between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • HOMO occupied molecular orbital
  • Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene, quinacridone-based organics, perylene-based organics, Anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is positioned on the hole injection layer.
  • the hole transport layer receives holes from the hole injection layer and transports the holes to the organic light emitting layer located thereon, and serves to prevent high hole mobility, hole stability, and electrons.
  • applications for vehicle body display require heat resistance to the device, and may be a material having a glass transition temperature (Tg) of 70 ° C. or higher.
  • NPD NPB
  • spiro-arylamine compounds perylene-arylamine compounds
  • azacycloheptatriene compounds bis (diphenylvinylphenyl) anthracene and silicon germanium oxide.
  • the organic light emitting layer is positioned on the hole transport layer.
  • the organic light emitting layer is a layer for emitting light by recombination of holes and electrons injected from the anode and the cathode, respectively, and is made of a material having high quantum efficiency.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and may be a material having good quantum efficiency for fluorescence or phosphorescence.
  • Substances or compounds that satisfy these conditions include Alq3 for green, Balq (8-hydroxyquinoline beryllium salt) for blue, DPVBi (4,4'-bis (2,2-diphenylethenyl) -1,1'- biphenyl) series, Spiro material, Spiro-DPVBi (Spiro-4,4'-bis (2,2-diphenylethenyl) -1,1'-biphenyl), LiPBO (2- (2-benzoxazoyl) -phenollithium salt ), Bis (diphenylvinylphenylvinyl) benzene, aluminum-quinoline metal complex, metal complexes of imidazole, thiazole and oxazole, and the like, perylene, and BczVBi (3,3 '[ (1,1'-biphenyl) -4,4'-diyldi-2,1-ethenediyl] bis (9-ethyl) -9H-carbazole; D
  • DCJTB [2- (1,1-dimethylethyl) -6- [2- (2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H, 5H
  • doping such as -benzo (ij) quinolizin-9-yl) ethenyl] -4H-pyran-4-ylidene] -propanedinitrile
  • a polymer of polyphenylene vinylene (PPV) -based polymer or poly fluorene may be used for the organic light emitting layer.
  • the electron transport layer is positioned on the organic light emitting layer.
  • the electron transport layer needs a material having high electron injection efficiency from the cathode positioned thereon and capable of efficiently transporting the injected electrons. To this end, it must be made of a material having high electron affinity and electron transfer speed and excellent stability to electrons.
  • Examples of the electron transport material that satisfies such conditions include Al complexes of 8-hydroxyquinoline; Complexes including Alq3; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron injection layer is stacked on the electron transport layer.
  • the electron injection layer is a metal complex compound such as Balq, Alq3, Be (bq) 2, Zn (BTZ) 2, Zn (phq) 2, PBD, spiro-PBD, TPBI, Tf-6P, aromatic compound with imidazole ring, It can be produced using a low molecular weight material containing boron compounds and the like.
  • the electron injection layer may be formed in a thickness range of 100 ⁇ 300 ⁇ .
  • the cathode is positioned on the electron injection layer. This cathode serves to inject electrons.
  • the material used as the cathode may use the material used for the anode, and may be a metal having a low work function for efficient electron injection.
  • a suitable metal such as tin, magnesium, indium, calcium, sodium, lithium, aluminum, silver, or a suitable alloy thereof can be used.
  • electrodes having a two-layer structure such as lithium fluoride and aluminum, lithium oxide and aluminum, strontium oxide and aluminum having a thickness of 100 ⁇ m or less may also be used.
  • the compound of the present invention can be used as a hole injection material, a hole transport material, a light emitting material, an electron transport material, and an electron injection material suitable for fluorescence and phosphorescent devices of all colors such as red, green, blue, and white, It can be used as a host or dopant material of various colors.
  • the organic electroluminescent device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • the present invention includes a display device including the organic electric element described above, and a terminal including a control unit for driving the display device.
  • This terminal means a current or future wired or wireless communication terminal.
  • the terminal according to the present invention described above may be a mobile communication terminal such as a mobile phone, and includes all terminals such as a PDA, an electronic dictionary, a PMP, a remote control, a navigation device, a game machine, various TVs, various computers, and the like.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention se rapporte à un composé, à un dispositif électronique organique utilisant celui-ci et à un dispositif électronique associé.
PCT/KR2012/001191 2011-02-24 2012-02-17 Composé, dispositif électronique organique utilisant celui-ci et dispositif électronique associé WO2012115394A2 (fr)

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WO2014042006A1 (fr) * 2012-09-13 2014-03-20 保土谷化学工業株式会社 Nouveau dérivé thiéno-indole et élément électroluminescent organique utilisant ledit dérivé
WO2014051244A1 (fr) * 2012-09-25 2014-04-03 제일모직 주식회사 Composé pour dispositif optoélectronique organique, dispositif électroluminescent organique le comprenant et dispositif d'affichage comprenant ledit dispositif électroluminescent organique
JP2017537902A (ja) * 2014-11-18 2017-12-21 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセンス素子のための材料
CN108017662A (zh) * 2016-10-28 2018-05-11 学校法人关西学院 硼酸或硼酸酯、或者使用它们制造多环芳香族化合物或多环芳香族多聚体化合物的方法
CN111433216A (zh) * 2018-02-23 2020-07-17 株式会社Lg化学 杂环化合物和包含其的有机发光器件
CN113121361A (zh) * 2021-03-31 2021-07-16 吉林奥来德光电材料股份有限公司 具有菲类双芳胺结构的空穴传输材料及其制备方法和应用
CN114573538A (zh) * 2022-03-07 2022-06-03 京东方科技集团股份有限公司 一种芳胺类化合物、发光器件和显示装置
DE102020135118A1 (de) 2020-12-30 2022-06-30 Heliatek Gmbh Verbindung für ein optoelektronisches Bauelement und optoelektronisches Bauelement enthaltend die Verbindung

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Cited By (15)

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Publication number Priority date Publication date Assignee Title
WO2014042006A1 (fr) * 2012-09-13 2014-03-20 保土谷化学工業株式会社 Nouveau dérivé thiéno-indole et élément électroluminescent organique utilisant ledit dérivé
JPWO2014042006A1 (ja) * 2012-09-13 2016-08-18 保土谷化学工業株式会社 新規なチエノインドール誘導体及び該誘導体を用いた有機エレクトロルミネッセンス素子
WO2014051244A1 (fr) * 2012-09-25 2014-04-03 제일모직 주식회사 Composé pour dispositif optoélectronique organique, dispositif électroluminescent organique le comprenant et dispositif d'affichage comprenant ledit dispositif électroluminescent organique
US10510960B2 (en) 2014-11-18 2019-12-17 Merck Patent Gmbh Materials for organic electroluminescent devices
JP2017537902A (ja) * 2014-11-18 2017-12-21 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセンス素子のための材料
CN108017662A (zh) * 2016-10-28 2018-05-11 学校法人关西学院 硼酸或硼酸酯、或者使用它们制造多环芳香族化合物或多环芳香族多聚体化合物的方法
JP2018076281A (ja) * 2016-10-28 2018-05-17 学校法人関西学院 ボロン酸またはボロン酸エステル、もしくはそれらを用いて多環芳香族化合物または多環芳香族多量体化合物を製造する方法
JP7030302B2 (ja) 2016-10-28 2022-03-07 学校法人関西学院 ボロン酸またはボロン酸エステル、もしくはそれらを用いて多環芳香族化合物または多環芳香族多量体化合物を製造する方法
CN111433216A (zh) * 2018-02-23 2020-07-17 株式会社Lg化学 杂环化合物和包含其的有机发光器件
US11631821B2 (en) 2018-02-23 2023-04-18 Lg Chem, Ltd. Polycyclic aromatic compounds containing a 1,11-dioxa-,1,11-dithia-, or 1-oxa-11-thia-4,8-diaza-11b-boradicyclopenta[a,j]phenalene core and organic light-emitting device comprising same
CN111433216B (zh) * 2018-02-23 2023-07-18 株式会社Lg化学 杂环化合物和包含其的有机发光器件
DE102020135118A1 (de) 2020-12-30 2022-06-30 Heliatek Gmbh Verbindung für ein optoelektronisches Bauelement und optoelektronisches Bauelement enthaltend die Verbindung
WO2022144423A1 (fr) 2020-12-30 2022-07-07 Heliatek Gmbh Composé pour composant optoélectronique et composant optoélectronique contenant le composé
CN113121361A (zh) * 2021-03-31 2021-07-16 吉林奥来德光电材料股份有限公司 具有菲类双芳胺结构的空穴传输材料及其制备方法和应用
CN114573538A (zh) * 2022-03-07 2022-06-03 京东方科技集团股份有限公司 一种芳胺类化合物、发光器件和显示装置

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