WO2015041416A1 - Élément électrique organique utilisant des composés pour un élément électrique organique et dispositif électronique pour ce dernier - Google Patents

Élément électrique organique utilisant des composés pour un élément électrique organique et dispositif électronique pour ce dernier Download PDF

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WO2015041416A1
WO2015041416A1 PCT/KR2014/008098 KR2014008098W WO2015041416A1 WO 2015041416 A1 WO2015041416 A1 WO 2015041416A1 KR 2014008098 W KR2014008098 W KR 2014008098W WO 2015041416 A1 WO2015041416 A1 WO 2015041416A1
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organic
layer
formula
electrode
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이범성
이선희
문성윤
박정철
김대성
김석현
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덕산네오룩스 주식회사
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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
    • 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
    • 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
    • H10K85/60—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
    • 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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K99/00—Subject matter not provided for in other groups of this subclass
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to an organic electric device using the compound for organic electric devices 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 layer is often made of a multi-layer 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.
  • the material used as the organic material layer in the organic electric element may be classified into a light emitting material and a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.
  • Efficiency, lifespan, and driving voltage are related to each other, and as efficiency increases, the driving voltage decreases relatively, and as the driving voltage decreases, crystallization of organic materials due to Joule heating generated during driving decreases. It shows a tendency to increase the life.
  • a light emitting auxiliary layer must exist between the hole transport layer and the light emitting layer, and different light emission auxiliary according to each light emitting layer (R, G, B) is required. It is time to develop the floor.
  • electrons are transferred from the electron transport layer to the light emitting layer, and holes are transferred from the hole transport layer to the light emitting layer to generate excitons by recombination.
  • the material used in the hole transport layer has a low TMO value because it has to have a low HOMO value, which causes the exciton generated in the light emitting layer to pass to the hole transport layer, resulting in charge unbalance in the light emitting layer. This causes light emission at the hole transport layer interface.
  • the OLED device is mainly formed by a deposition method, which requires development of a material that can withstand a long time during deposition, that is, a material having strong heat resistance.
  • the materials 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, a light emitting auxiliary layer material, etc.
  • a hole injection material such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a light emitting auxiliary layer material, etc.
  • the material should be preceded, but development of a stable and efficient organic material layer for an organic electric device has not been made yet. Therefore, the development of new materials is continuously required, and in particular, the development of material combinations of the light emitting auxiliary layer and the hole transport layer is urgently required.
  • An object of the present invention is to provide an organic electric device using the compound which can improve the high luminous efficiency, low driving voltage, high heat resistance, color purity and life of the device and its electronic device.
  • the present invention provides an organic electronic device using the compound represented by the following formula and an electronic device thereof.
  • the light emitting auxiliary layer provides an organic electric device including the compound represented by the following Chemical Formula 2.
  • FIG. 1 is an exemplary view of an organic electroluminescent device according to the present invention.
  • a component such as a layer, film, region, plate, etc.
  • it is not only when the other component is “on top of” but also another component in between. It is to be understood that this may also include cases.
  • a component is said to be “directly above” another part, it should be understood to mean that there is no other part in the middle.
  • halo or halogen as used herein is fluorine (F), bromine (Br), chlorine (Cl) or iodine (I) unless otherwise indicated.
  • alkyl or “alkyl group” has a single bond of 1 to 60 carbon atoms, unless otherwise indicated, and is a straight chain alkyl group, branched chain alkyl group, cycloalkyl (alicyclic) group, alkyl-substituted cyclo Radicals of saturated aliphatic functional groups, including alkyl groups, cycloalkyl-substituted alkyl groups.
  • alkenyl group or “alkynyl group”, unless stated otherwise, has a double or triple bond of 2 to 60 carbon atoms, and includes a straight or branched chain group, and is not limited thereto. It is not.
  • cycloalkyl refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.
  • alkoxyl group means an alkyl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 1 to 60, and is limited herein. It is not.
  • aryloxyl group or “aryloxy group” means an aryl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 6 to 60, but is not limited thereto.
  • aryl group and “arylene group” have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto.
  • an aryl group or an arylene group means an aromatic of a single ring or multiple rings, and includes an aromatic ring formed by neighboring substituents participating in a bond or a reaction.
  • the aryl group may be a phenyl group, a biphenyl group, a fluorene group, a spirofluorene group.
  • aryl or "ar” means a radical substituted with an aryl group.
  • an arylalkyl group is an alkyl group substituted with an aryl group
  • an arylalkenyl group is an alkenyl group substituted with an aryl group
  • the radical substituted with an aryl group has the carbon number described herein.
  • an arylalkoxy group means an alkoxy group substituted with an aryl group
  • an alkoxylcarbonyl group means a carbonyl group substituted with an alkoxyl group
  • an arylcarbonylalkenyl group means an alkenyl group substituted with an arylcarbonyl group.
  • the arylcarbonyl group is a carbonyl group substituted with an aryl group.
  • heteroalkyl means an alkyl including one or more heteroatoms unless otherwise indicated.
  • heteroaryl group or “heteroarylene group” means an aryl group or arylene group having 2 to 60 carbon atoms, each containing one or more heteroatoms, unless otherwise specified. It may include at least one of a single ring and multiple rings, and may be formed by combining adjacent functional groups.
  • heterocyclic group includes one or more heteroatoms, unless otherwise indicated, and has from 2 to 60 carbon atoms, and includes at least one of single and multiple rings, heteroaliphatic rings and hetero Aromatic rings. Adjacent functional groups may be formed in combination.
  • heteroatom refers to N, O, S, P or Si unless otherwise stated.
  • Heterocyclic groups may also include rings comprising SO 2 in place of the carbon forming the ring.
  • a “heterocyclic group” includes the following compounds.
  • aliphatic as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms
  • aliphatic ring means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.
  • ring refers to a fused ring consisting of an aliphatic ring having 3 to 60 carbon atoms or an aromatic ring having 6 to 60 carbon atoms or a hetero ring having 2 to 60 carbon atoms or a combination thereof. Saturated or unsaturated rings.
  • heterocompounds or heteroradicals other than the aforementioned heterocompounds include, but are not limited to, one or more heteroatoms.
  • carbonyl used in the present invention is represented by -COR ', wherein R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and 3 to 30 carbon atoms. Cycloalkyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.
  • substituted in the term “substituted or unsubstituted” as used in the present invention is deuterium, halogen, amino group, nitrile group, nitro group, C 1 ⁇ C 20 alkyl group, C 1 ⁇ C 20 alkoxyl group, C 1 ⁇ C 20 alkylamine group, C 1 ⁇ C 20 alkylthiophene group, C 6 ⁇ C 20 arylthiophene group, C 2 ⁇ C 20 alkenyl group, C 2 ⁇ C 20 alkynyl, C 3 ⁇ C 20 cycloalkyl group, C 6 ⁇ C 20 aryl group, of a C 6 ⁇ C 20 substituted by deuterium aryl group, a C 8 ⁇ C 20 aryl alkenyl group, a silane group, a boron Group, germanium group, and C 2 ⁇ C 20 It is meant to be substituted with one or more substituents selected from the group consist
  • the substituent R 1 when a is an integer of 0, the substituent R 1 is absent, when a is an integer of 1, one substituent R 1 is bonded to any one of carbons forming the benzene ring, and a is an integer of 2 or 3 are each bonded as follows, where R 1 may be the same or different from each other, and when a is an integer from 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while the indication of hydrogen bonded to the carbon forming the benzene ring Is omitted.
  • FIG. 1 is an exemplary view of an organic electric device according to an embodiment of the present invention.
  • the organic electric device 100 includes a first electrode 120, a second electrode 180, a first electrode 110, and a second electrode 180 formed on a substrate 110.
  • the first electrode 120 may be an anode (anode)
  • the second electrode 180 may be a cathode (cathode)
  • the first electrode may be a cathode and the second electrode may be an anode.
  • the organic layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 on the first electrode 120 in sequence. At this time, the remaining layers except for the light emitting layer 150 may not be formed.
  • the hole blocking layer, the electron blocking layer, the light emitting auxiliary layer 151, the buffer layer 141 may be further included, and the electron transport layer 160 may serve as the hole blocking layer.
  • the organic electric device according to the present invention may further include a protective layer or a light efficiency improving layer (Capping layer) formed on one surface of the at least one surface of the first electrode and the second electrode opposite to the organic material layer.
  • a protective layer or a light efficiency improving layer Capping layer
  • the compound according to the present invention applied to the organic material layer of the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, the electron injection layer 170, the host of the dopant or light efficiency improvement layer of the light emitting layer 150 It may be used as a material.
  • the compound of the present invention may be used as the light emitting layer 150, hole transport layer 140 and / or light emitting auxiliary layer 151.
  • the hole transport layer in the organic electroluminescent device it is preferable to form a light emitting auxiliary layer between the hole transport layer and the light emitting layer, and according to each of the light emitting layers R, G, and B, It is time to develop different emission auxiliary layers. Meanwhile, in the case of the light emitting auxiliary layer, it is difficult to infer the characteristics of the organic material layer used even if a similar core is used, since the correlation between the hole transport layer and the light emitting layer (host) must be understood.
  • a light emitting layer or an auxiliary light emitting layer using a compound represented by the formula (1) by optimizing the energy level (level) and T1 value between each organic material layer, the intrinsic properties (mobility, interface characteristics, etc.) of the organic material
  • the life and efficiency of the electric device can be improved at the same time.
  • the organic electroluminescent device may be manufactured using a PVD method.
  • the anode 120 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, and the electron transport layer are formed thereon.
  • the organic material layer including the 160 and the electron injection layer 170 it can be prepared by depositing a material that can be used as the cathode 180 thereon.
  • the organic material layer is a solution or solvent process (e.g., spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blading) using various polymer materials. It can be produced in fewer layers by methods such as ding process, screen printing process, or thermal transfer method. Since the organic material layer according to the present invention may be formed in various ways, the scope of the present invention is not limited by the forming method.
  • the organic electric element 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.
  • WOLED White Organic Light Emitting Device
  • Various structures for white organic light emitting devices mainly used as backlight devices have been proposed and patented. Representatively, a side-by-side method in which R (Red), G (Green) and B (Blue) light emitting parts are mutually planarized, and a stacking method in which R, G, and B light emitting layers are stacked up and down. And a color conversion material (CCM) method using photo-luminescence of an inorganic phosphor by using electroluminescence by a blue (B) organic light emitting layer and light therefrom. May also be applied to these WOLEDs.
  • CCM color conversion material
  • the organic electroluminescent device according to the present invention may be one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a monochromatic or white illumination device.
  • OLED organic electroluminescent device
  • OPC organic photoconductor
  • organic TFT organic transistor
  • Another embodiment of the present invention may include a display device including the organic electric element of the present invention described above, and an electronic device including a control unit for controlling the display device.
  • the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.
  • the first electrode Second electrode; And an organic material layer disposed between the first electrode and the second electrode, the organic material layer including at least a hole transport layer and a light emitting auxiliary layer, wherein the hole transport layer comprises a compound represented by the following Chemical Formula 1,
  • the light emitting auxiliary layer provides an organic electric device including the compound represented by the following Chemical Formula 2.
  • Ar 1 , Ar 2 , Ar 4 to Ar 8 are i) independently of each other a C 6 ⁇ C 60 aryl group; Fluorenyl group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; C 1 ⁇ C 50 Alkyl group; C 2 ⁇ C 20 Alkenyl group; Alkynyl groups of C 2 to C 20 ; C 1 -C 30 alkoxyl group; C 6 -C 30 aryloxy group; And -LN (R a ) (R b ); or ii) Ar 1 and Ar 2 and Ar 4 and Ar 5 may be bonded to each other to form a ring, wherein the 'ring' is carbon number It refers to a fused ring consisting of an aliphatic ring of 3 to 60 or an aromatic ring of 6 to 60 carbon atom
  • n and o are integers from 0 to 3
  • n, p, q, r and s are integers from 0 to 4
  • R 1 to R 7 are i) independently of each other deuterium; halogen; C 6 ⁇ C 60 Aryl group; Fluorenyl group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; C 1 ⁇ C 50 Alkyl group; C 2 ⁇ C 20 Alkenyl group; Alkynyl groups of C 2 to C 20 ; C 1 -C 30 alkoxyl group; C 6 -C 30 aryloxy group; And -LN (R a ) (R b ); or ii) when m, n, o, p, q, r and s are each an integer of 2 or more, R 1 to R 7 are each neighbor Substituents may be bonded to each other to form at least one ring, wherein the 'ring' is composed of an aliphatic
  • R 'and R are independently of each other i) hydrogen; C 1 -C 50 alkyl group; C 6 -C 60 aryl group; fluorenyl group; at least one heteroatom of O, N, S, Si and P It may be selected from the group consisting of; C 2 ⁇ C 60 heterocyclic group, or ii) R 'and R "may be bonded to each other to form a spiro compound with fluorene to which they are bonded.
  • L 1 to L 4 and L are independently of each other a single bond; C 6 ⁇ C 60 arylene group; Fluorenylene groups; Fused ring group of an aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; And a C 2 to C 60 heterocyclic group including at least one heteroatom of O, N, S, Si, and P; wherein L 2 and L 4 exclude a single bond.
  • R a and R b are each independently a C 6 ⁇ C 60 aryl group; Fluorenyl group; Fused ring group of an aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; And a C 2 -C 60 heterocyclic group including at least one heteroatom of O, N, S, Si, and P.
  • the compound represented by Formula 1 of the hole transport layer may be one of those represented by the following formula (3).
  • R 5 to R 7 , L 2 to L 4 , Ar 1 , Ar 2 , Ar 6 to Ar 8 , q, r and s are the same as defined in Formula 1 above.
  • the compound represented by Chemical Formula 2 of the light emitting auxiliary layer may be one of the following Chemical Formulas 6 to 8.
  • R 1 to R 4 , L 1 , Ar 4 , Ar 5 , m, n, o and p are the same as defined in the formula (2).
  • the compound represented by Formula 3 to Formula 5 of the Formula 1 or Formula 1 of the hole transport layer may be one of the following compounds.
  • the compound represented by Formula 6 to Formula 8 of the Formula 2 or Formula 2 of the light emitting auxiliary layer may be one of the following compounds.
  • an organic electric device comprising a light efficiency improving layer formed on at least one side of the one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer
  • the organic material layer is provided by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process and a roll-to-roll process do.
  • the light emitting auxiliary layer includes a display device including an organic electric element including the compound represented by Chemical Formula 2; And a controller for driving the display device.
  • the organic electroluminescent device according to the present invention is at least one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a device for monochrome or white illumination It can be one.
  • OLED organic electroluminescent device
  • OPC organic photoconductor
  • organic TFT organic transistor
  • a device for monochrome or white illumination It can be one.
  • the compound represented by Formula 1 according to the present invention (Final Product 1) may be synthesized by the reaction route of Scheme 1 below, but is not limited thereto.
  • L is L 2 or L 4 as defined in Ar 3 of Formula 1.
  • Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2, but is not limited thereto.
  • S1 to S7 are as follows.
  • Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 3, but is not limited thereto.
  • Sub 3 of Scheme 1 may be synthesized by the reaction route of Scheme 4, but is not limited thereto.
  • N- (4'-bromo- [1,1'-biphenyl] -4-yl) -N-phenylnaphthalen-1-amine (10.8 g, 24 mmol) is dissolved in toluene, followed by N-phenylnaphthalen-1-amine (4.4 g, 20 mmol), Pd 2 (dba) 3 (0.05 equiv), PPh 3 (0.1 equiv) and NaO t -Bu (3 equiv) were then added and stirred under reflux at 100 ° C. for 24 hours.
  • the compound represented by Formula 2 according to the present invention (Final Product 2) may be synthesized by the reaction route of Scheme 5, but is not limited thereto.
  • Sub 4 of Scheme 5 may be synthesized by the reaction route of Scheme 6, but is not limited thereto.
  • N 1- (naphthalen-2-yl) -N 4 , N 4 -bis (4- (naphthalen-2-yl (phenyl) amino) phenyl) -N 1- phenylbenzene-1,4-diamine (hereinafter abbreviated as "2-TNATA") was vacuum deposited to a thickness of 60 nm to form a hole injection layer, and then the compound represented by Formula 1 of the present invention on the hole injection layer Vacuum deposition to a thickness of 60nm to form a hole transport layer.
  • the compound represented by Chemical Formula 2 of the present invention was vacuum-deposited to a thickness of 20 nm on the hole transport layer to form a light emitting auxiliary layer.
  • CBP 4,4'-N, N'-dicarbazole-biphenyl
  • host bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate
  • (piq) 2 Ir (acac)) as a dopant, and the mixture doped at 95: 5 weight was vacuum deposited to a thickness of 30 nm to form a light emitting layer.
  • BAlq (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinolineoleito) aluminum
  • BAlq 3 tris (8-quinolinol) aluminum
  • LiF an alkali metal halide
  • the forward bias DC voltage was applied to the organic electroluminescent devices according to Experimental Example I (Experimental Example (1) to Experimental Example 30) and Comparative Example I (Comparative Example (1) to Comparative Example (3)) prepared as described above.
  • the electroluminescence (EL) characteristics were measured with a PR-650 photoresearch company, and T95 life was measured using a life-time measurement device manufactured by McScience Inc. at a luminance of 2500 cd / m 2.
  • Table 6 shows device fabrication of Experimental Example I (Experimental Example (1) to Experimental Example (30)) and Comparative Example I (Comparative Example (1) to Comparative Example (3)) to which the compound according to the present invention was applied. And the evaluation result.
  • a hole injection layer is formed by vacuum depositing 2-TNATA with a thickness of 60 nm on an ITO layer (anode) formed on a glass substrate, and then vacuuming the compound represented by Formula 1 of the present invention on the hole injection layer with a thickness of 60 nm. It was deposited to form a hole transport layer. Subsequently, the compound represented by Chemical Formula 2 of the present invention was vacuum-deposited to a thickness of 20 nm on the hole transport layer to form a light emitting auxiliary layer.
  • LiF an alkali metal halide
  • the forward bias DC voltage was applied to the organic electroluminescent devices according to Experimental Example II (Experimental Example (31) to Experimental Example (60)) and Comparative Example II (Comparative Example (4) to Comparative Example (6)) prepared as described above.
  • the electroluminescence (EL) characteristics were measured with a PR-650 photoresearch company, and the T95 life was measured using a life-time measurement device manufactured by McScience Inc. at a luminance of 5000 cd / m 2.
  • Table 7 shows device fabrication for Experimental Example II (Experimental Example (31) to Experimental Example (60)) and Comparative Example II (Comparative Example (4) to Comparative Example (6)) to which the compound according to the present invention was applied. And the evaluation result.
  • a hole injection layer is formed by vacuum depositing 2-TNATA with a thickness of 60 nm on an ITO layer (anode) formed on a glass substrate, and then vacuuming the compound represented by Formula 1 of the present invention on the hole injection layer with a thickness of 60 nm. It was deposited to form a hole transport layer. Subsequently, the compound represented by Chemical Formula 2 of the present invention was vacuum-deposited to a thickness of 20 nm on the hole transport layer to form a light emitting auxiliary layer.
  • a mixture doped with 9,10-di (naphthalen-2-yl) anthracene as a host and BD-052X (manufactured by Idemitsukosan) as a dopant at 93: 7 weight was 30 nm thick.
  • Evaporation was carried out in vacuo to form a light emitting layer.
  • BAlq was vacuum deposited on the emission layer to form a hole blocking layer, and Alq 3 was deposited on the hole blocking layer to 40 nm in thickness to form an electron transport layer.
  • LiF an alkali metal halide
  • An organic electric device was manufactured in the same manner as in Experimental Example III, except that the light emitting auxiliary layer was not formed.
  • the forward bias DC voltage was applied to the organic electroluminescent devices according to Experimental Example III (Experimental Example (61) to Experimental Example 90) and Comparative Example III (Comparative Example (7) to Comparative Example (9)) prepared as described above.
  • the electroluminescence (EL) characteristics were measured with a PR-650 photoresearch company, and T95 life was measured using a life measurement device manufactured by McScience Inc. at a luminance of 500 cd / m 2.
  • Table 8 shows device fabrication for Experimental Example III (Experimental Example (61) to Experimental Example (90)) and Comparative Example III (Comparative Example (7) to Comparative Example (9)) to which the compound according to the present invention was applied. And the evaluation result.
  • the compound of the present invention in which fluorene is substituted at position 9 of Carbazole, is used alone as a light emitting auxiliary layer, it has a high T1 energy level and a deep HOMO energy level. This is because charge balance is achieved and light is emitted inside the light emitting layer instead of the hole transport layer interface to maximize the efficiency.

Abstract

L'invention porte sur un élément électrique organique contenant des composés représentés par la formule chimique 1 et la formule chimique 2. L'élément électrique organique comporte : une première électrode ; une seconde électrode ; une couche de matériau organique comportant au moins une couche de transport de trous et une couche auxiliaire électroluminescente entre la première électrode et la seconde électrode, la couche de transport de trous contenant un composé représenté par la formule chimique 1 et la couche auxiliaire électroluminescente contenant un composé représenté par la formule chimique 2. Lorsque la couche de transport de trous contient le composé représenté par la formule chimique 1 et que la couche auxiliaire électroluminescente contient le composé représenté par la formule 2, l'efficacité d'électroluminescence, la stabilité et la durée de vie de l'élément peuvent être améliorées.
PCT/KR2014/008098 2013-09-17 2014-08-29 Élément électrique organique utilisant des composés pour un élément électrique organique et dispositif électronique pour ce dernier WO2015041416A1 (fr)

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CN113016088A (zh) * 2019-01-14 2021-06-22 株式会社Lg化学 有机发光二极管
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