WO2016175533A2 - Composé pour élément électronique organique, élément électronique organique utilisant celui-ci et dispositif électronique comprenant celui-ci - Google Patents

Composé pour élément électronique organique, élément électronique organique utilisant celui-ci et dispositif électronique comprenant celui-ci Download PDF

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WO2016175533A2
WO2016175533A2 PCT/KR2016/004347 KR2016004347W WO2016175533A2 WO 2016175533 A2 WO2016175533 A2 WO 2016175533A2 KR 2016004347 W KR2016004347 W KR 2016004347W WO 2016175533 A2 WO2016175533 A2 WO 2016175533A2
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WO2016175533A3 (fr
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박남진
박정철
김기원
김슬기
박성제
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덕산네오룩스 주식회사
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • 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 for an organic electric device, an organic electric 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 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.
  • 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. .
  • 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.
  • a host / dopant system may be used as the light emitting material to increase the light emitting efficiency through the light emitting material.
  • 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.
  • 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.
  • Efficiency, lifespan, and driving voltage are related to each other, and as the efficiency increases, the driving voltage decreases relatively, and the crystallization of organic materials due to Joule heating generated during driving decreases as the driving voltage decreases.
  • the lifespan tends to increase.
  • simply improving the organic material layer does not maximize the efficiency. This is because long life and high efficiency can be achieved at the same time when an optimal combination of energy level and T1 value and intrinsic properties (mobility, interfacial properties, etc.) of each organic material layer is achieved.
  • 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 material, Supported by 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 the hole transport layer and the light emitting auxiliary layer material is also urgently required.
  • An object of the present invention is to provide a compound capable of improving high luminous efficiency, low driving voltage and lifetime of an element, an organic electric element using the same, and an electronic device thereof.
  • the present invention provides a compound represented by the following formula.
  • the present invention provides an organic electronic device using the compound represented by the above formula and an electronic device thereof.
  • FIG. 1 is an exemplary view of an organic electroluminescent device according to the present invention.
  • 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.
  • heteroalkyl group means that at least one of the carbon atoms constituting the alkyl group has been replaced with a heteroatom.
  • 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.
  • alkenoxyl group means an alkenyl group to which an oxygen radical is attached, and unless otherwise stated, it is 2 to 60 It has carbon number of, It is not limited to this.
  • 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, biphenyl group, terphenyl group, naphthyl group, anthracenyl group, fluorene group, spirofluorene group, spirobifluorene 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.
  • ether as used herein is represented by -RO-R ', wherein R or R' are each independently of each other hydrogen, an alkyl group having 1 to 20 carbon atoms, It is an aryl group, a C3-C30 cycloalkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, 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
  • Compound according to the present invention applied to the organic layer is a hole injection layer 130, a hole transport layer 140, an electron transport layer 160, an electron injection layer 170, a light emitting auxiliary layer 151, a host of the light emitting layer 150 Or it may be used as a material of the dopant or the light efficiency improving layer.
  • the compound of the present invention may be used as the hole transport layer 140 and the light emitting auxiliary layer 151.
  • the hole transport layer and the light emitting auxiliary layer are formed using the compound represented by Chemical Formula 1 to optimize energy levels and T1 values between the organic material layers, and intrinsic properties (mobility, interfacial properties, etc.) of the organic materials.
  • the lifetime and efficiency of the organic electric element 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 conductive metal oxide or an alloy thereof on the substrate, and the hole injection layer 130, the hole transport layer 140, the light emitting auxiliary layer 151, and the light emitting layer thereon.
  • the organic material layer including the 150, the electron transport layer 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.
  • Ar 3 is ego
  • Ar 4 is to be.
  • Ar 1 , Ar 2 and Ar 5 are each independently a C 6 ⁇ C 60 aryl group; Fluorenyl group; C 2 to C 60 containing at least one heteroatom of O, N, S, Si, and P Heterocyclic group; C 1 ⁇ C 60 Alkyl groups; And it may be selected from the group consisting of a fused ring group of C 6 ⁇ C 60 aromatic ring and C 3 ⁇ C 60 Aliphatic ring, Ar 1 may be further substituted with R 5 , Ar 2 is R 6 It may further be substituted by.
  • R 1 to R 6 are each independently heavy hydrogen; Tritium; Halogen group; Cyano group; Nitro group; 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; And it may be selected from the group consisting of C 6 ⁇ C 30 aryloxy group,
  • R 1 to R 6 when a plurality of R 1 to R 6 are present, a plurality of R 1 , a plurality of R 2 , a plurality of R 3 , a plurality of R 4 , a plurality of R 5 , or a plurality of R 6 are the same as or different from each other, And the adjacent R 1 and R 1 together, the adjacent R 2 Between R 2 , adjacent R 3 and R 3 , adjacent R 4 and R 4 , adjacent R 5 and R 5 , adjacent R 6 and R 6 or adjacent R 5 and R 6 may be bonded to each other to form at least one ring. At this time, R 1 to R 6 which do not form a ring may be defined in the same manner as defined above.
  • X is O or S.
  • L 1 and L 2 are independently of each other a single bond; C 6 ⁇ C 60 arylene group; Fluorenylene groups; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; It may be selected from the group consisting of a bivalent fused ring group of C 3 ⁇ C 60 Aliphatic ring and C 6 ⁇ C 60 Aromatic ring.
  • a and c are integers of 0-4, b and d are integers of 0-3.
  • Ar 1 , Ar 2 , Ar 5 , R 1 to R 6 , L 1 and L 2 are an aryl group or an arylene group
  • Ar 1 , Ar 2 , Ar 5 , R 1 to R 6 , L 1 and L 2 may be independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a pyrenyl group or a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a phenanthrylene group, a pyrenylene group, or the like.
  • the aryl group, fluorenyl group, arylene group, fluorenylene group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl group and aryloxy group are each deuterium, halogen, silane group, siloxane group , Boron group, germanium group, cyano group, nitro group, -L'-N (R a ) (R b ) (wherein L 'is a single bond; C 6 ⁇ C 60 arylene group; fluorenylene group; C A fused ring group of an aliphatic ring of 3 to C 60 and an aromatic ring of C 6 to C 60 , and a heterocyclic group of C 2 to C 60 ; wherein R a and R b are each independently selected from C Aryl group of 6 to C 60 ; fluorenyl group; fused ring group of C 3 to C 60 aliphatic ring and C 6 to C
  • the carbon number may be 6 to 60, preferably 6 to 40 carbon atoms, more preferably an aryl group having 6 to 30 carbon atoms,
  • heterocyclic group has 2 to 60 carbon atoms, preferably 2 to 30 carbon atoms, more preferably a hetero ring having 2 to 20 carbon atoms,
  • the carbon number may be 6 to 60, preferably 6 to 30 carbon atoms, more preferably an arylene group having 6 to 20 carbon atoms,
  • the carbon number may be 1 to 50, preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably an alkyl group having 1 to 10 carbon atoms.
  • Ar 3 of Formula 1 may be represented by one of the following formula.
  • Ar 5 , R 1 , R 2 , L 1 , a and b may be defined in the same manner as defined in Formula 1. However, in the case of Chemical Formula a-1, even if a plurality of R 1 or a plurality of R 2 exists, adjacent R 1 may be adjacent to each other. R 2 does not form a ring.
  • Ar 4 of Formula 1 may be represented by one of the following formula.
  • X, R 3 , R 4 , L 2 , c and d may be defined the same as defined in the formula (1). However, in the case of Formula b-1, even if a plurality of R 3 or a plurality of R 4 present, adjacent R 3 , adjacent R 4 does not form a ring.
  • Chemical Formula 1 may be represented by one of the following chemical formulas.
  • n and m are integers from 0 to 4.
  • Ar 1 , Ar 2 , Ar 5 , R 1 to R 6 , X, L 1 , L 2 , a, b, c and d may be defined in the same manner as defined in Chemical Formula 1.
  • the compound represented by Formula 1 to Formula 3 may be any one of the following compounds.
  • the present invention provides a compound for an organic electric device represented by Chemical Formula 1.
  • the present invention provides an organic electric device containing the compound represented by the formula (1).
  • the organic electric element includes a first electrode; Second electrode; And an organic material layer disposed between the first electrode and the second electrode.
  • the organic material layer may include a compound represented by Chemical Formula 1, and the compound represented by Chemical Formula 1 may be a hole injection layer or a hole transport layer of the organic material layer.
  • the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer may be contained in at least one layer.
  • the compound represented by Formula 1 may be included in the hole transport layer and the light emitting auxiliary layer.
  • the compound represented by Formula 1 may be used as a material of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer or an electron injection layer.
  • the compound represented by Formula 1 may be used as a material for the hole transport layer and the light emitting auxiliary layer.
  • an organic electroluminescent device comprising one of the compounds represented by Formula 2 and Formula 3 in the organic material layer, more specifically, It provides an organic electroluminescent device comprising a compound represented by the individual formulas (1-1 to 1-96) in the organic material layer.
  • the compound is contained alone or in at least one of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer of the organic material layer,
  • an organic electroluminescent device characterized in that a compound is contained in a combination of two or more different from each other, or the compound is contained in a combination of two or more.
  • each of the layers may include a compound corresponding to Formula 1 to Formula 3 alone, may include a mixture of two or more compounds of Formula 1 to Formula 3, the compounds of claims 1 to 5, Mixtures with compounds that do not correspond to the invention may be included.
  • the compound not corresponding to the present invention may be a single compound or two or more compounds.
  • the other compound when the compound is contained in a combination of two or more kinds of other compounds, the other compound may be a known compound of each organic material layer, or a compound to be developed in the future.
  • the compound contained in the organic material layer may be made only of the same kind of compound, but may be a mixture of two or more kinds of the compound represented by the formula (1).
  • the present invention provides 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. It provides an organic electric element further comprising.
  • Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2, but is not limited thereto.
  • Sub 1-VII of Scheme 2 may be synthesized by, but are not limited to, the reaction route of Scheme 3 below.
  • M in Scheme 2 may be synthesized by the reaction pathways of Schemes 4 to 7, but is not limited thereto.
  • Sub 1-IV-31 (15.7g, 54.6mmol) was added to a round bottom flask, 1,3,5-tribromobenzene (17.2g, 54.6mmol), Pd (PPh 3 ) 4 (0.6g, 0.55mmol), NaOH (3.3 g, 81.96 mmol), THF (240 mL) and water (120 mL) were used to obtain 17.5 g of the product using the Sub 1-VII-64 synthesis method. (Yield: 67%)
  • the compound belonging to M may be the following compound, but is not limited thereto, and Table 1 shows FD-MS values of compounds belonging to M-1 to M-30.
  • the compound belonging to Sub 1 may be a compound as follows, but is not limited thereto.
  • Scheme 1 may be synthesized by, but not limited to, the following Scheme 8 and Scheme 9.
  • Naphthalen-2-ylboronic acid (3.05g, 25mmol), THF (110ml), 2-bromo-1-nitronaphthalene (6.3g, 25mmol), Pd (PPh 3 ) 4 (0.87g, 0.75mmol), K 2 CO 3 (6.91 g, 50 mmol) and water (55 ml) were obtained using 6.66 g (yield: 89%) of the product using the Sub 2-I-45 synthesis method.
  • Sub 2 is as follows, but is not limited thereto.
  • An organic electroluminescent device was manufactured according to a conventional method using the compound of the present invention as a hole transport layer material.
  • vacuum 4,4 ', 4''-Tris [2-naphthyl (phenyl) amino] triphenylamine (hereinafter abbreviated as "2-TNATA”) on an ITO layer (anode) formed on an organic substrate was vacuumed to a thickness of 60 nm.
  • Compound 1-1 of the present invention was vacuum deposited to a thickness of 60 nm on the hole injection layer to form a hole transport layer.
  • CBP 4,4'-N, N'-dicarbazole-biphenyl
  • Ir (ppy) ) 3 tris (2-phenylpyridine) -iridium
  • BAlq (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinolineoleito) aluminum
  • BAlq 3 tris (8-quinolinol) aluminum
  • LiF which is an alkali metal halide
  • Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.
  • An organic electroluminescent device was manufactured according to the same method as Example 1 except for using the compounds 1-4 to 1-94 of the present invention shown in Table 5 below instead of the compound 1-1 of the present invention as the hole transport layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 1 was used instead of Compound 1-1 of the present invention as a hole transport layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compounds 2 to 4 were used instead of Compound 1-1 of the present invention as a hole transport layer material.
  • Electroluminescence (EL) characteristics by PR-650 of photoresearch by applying a forward bias DC voltage to the organic electroluminescent devices prepared by Examples 1 to 38 and Comparative Examples 1 to 4 of the present invention The T95 lifetime was measured using a lifespan measuring instrument manufactured by McScience Inc. at 5000 cd / m 2 reference luminance, and the measurement results are shown in Table 5 below.
  • Comparative Example 3 increases the driving voltage, and decreases the efficiency and lifespan, which may be due to lower hole mobility of Carbazole No. 9 than Carbazole No. 3, and from this result, the position of carbazole substitution (N -carbazole / C-carbazol) showed that the characteristics of the device is different.
  • Comparative Example 4 having a hetero ring was similar in driving voltage, but the efficiency was increased by about 115% and the lifespan was increased by about 133%.
  • the compound of the present invention having a carbazole and a heterocycle in the central phenyl has a significant increase in efficiency and lifespan. It is believed that the mobility and thermal properties of the charge are increased due to the C-carbazole and the heterocyclic ring having high hole transporting ability, thereby significantly increasing the efficiency and lifespan.
  • An organic electroluminescent device was manufactured according to a conventional method using the compound of the present invention as a light emitting auxiliary layer material.
  • 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 a hole transport layer is formed by vacuum depositing NPB with a thickness of 60 nm on the hole injection layer. It was.
  • Compound 1-1 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, and then 9,10-Di (2-naphthyl) anthracene (hereinafter referred to as a light emitting auxiliary layer).
  • ADN Abbreviation “ADN”) is used as a host material
  • BD-052X manufactured by Idemitsu kosan
  • BD-052X manufactured by Idemitsu kosan
  • a dopant material is doped at a weight ratio of 93: 7 to form a light emitting layer by vacuum deposition to a thickness of 30 nm.
  • a hole blocking layer was formed by vacuum depositing BAlq to a thickness of 10 nm on the light emitting layer, and an electron transport layer was formed by vacuum depositing Alq3 to 40 nm on the hole blocking layer.
  • LiF which is an alkali metal halide
  • Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.
  • Example 40 to [ Example 85] Blue organic electroluminescent device ( Luminous auxiliary layer )
  • An organic electroluminescent device was manufactured according to the same method as Example 39 except for using the compound 1-1 to 1-96 of the present invention shown in Table 6 as a light emitting auxiliary layer instead of the compound 1-1 of the present invention. .
  • An organic electroluminescent device was manufactured in the same manner as in Example 39, except that the light emitting auxiliary layer material was not used.
  • An organic electroluminescent device was manufactured in the same manner as in Example 39, except that one of Comparative Compounds 2 to 4 was used instead of Compound 1-1 of the present invention.
  • An organic electroluminescent device was manufactured in the same manner as in Example 39, except that Comparative Compound 5 was used instead of Compound 1-1 of the present invention as a light emitting auxiliary layer material.
  • Electroluminescence (EL) characteristics by PR-650 of photoresearch by applying a forward bias DC voltage to the organic electroluminescent devices prepared in Examples 39 to 85 and Comparative Examples 5 to 9 of the present invention The T95 life was measured using the life measurement equipment manufactured by McScience Inc. at a luminance of 500 cd / m 2 , and the measurement results are shown in Table 6 below.
  • the organic electroluminescent device using the compound of the present invention as a light emitting auxiliary layer has a slightly higher driving voltage than the organic electroluminescent devices of Comparative Examples 5 to 9, The service life is significantly improved.
  • the efficiency is improved because the HOMO energy level of the compound of the present invention has an appropriate difference from the material used as the HTL, and as a result, holes are more smoothly transported to the light emitting layer. It is believed that excitons are more easily generated in the light emitting layer to improve efficiency and lifespan.
  • the evaluation results of the above-described device fabrication the device characteristics of applying the compound of the present invention to only one of the hole transport layer and the light emitting auxiliary layer, but the compound of the present invention can be used by applying to both the hole transport layer and the light emitting auxiliary layer have.
  • the materials used as the hole transport layer and the light emitting auxiliary layer are generally the above-described electron injection layer, hole injection layer, and electron transport layer.
  • an organic material layer of an organic electric element, such as a light emitting layer may be used in combination with a single or another material. Therefore, the compounds of the present invention can be used in a single or other materials mixed with other organic material layers, for example, electron injection layer and hole injection layer, electron transport layer and light emitting layer in addition to the hole transport layer and the light emitting auxiliary layer.

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

Abstract

L'objectif de la présente invention consiste à produire : un composé ayant une efficacité d'émission de lumière élevée, une faible tension d'entraînement et une durée de vie améliorée d'un élément ; un élément électronique organique l'utilisant ; et un appareil électronique comprenant celui-ci.
PCT/KR2016/004347 2015-04-27 2016-04-26 Composé pour élément électronique organique, élément électronique organique utilisant celui-ci et dispositif électronique comprenant celui-ci WO2016175533A2 (fr)

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US20170288148A1 (en) * 2016-04-01 2017-10-05 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof
CN109749735A (zh) * 2017-11-08 2019-05-14 Sfc株式会社 胺取代的萘衍生物和包含其的有机发光二极管
WO2019114610A1 (fr) * 2017-12-14 2019-06-20 广州华睿光电材料有限公司 Composé organique de type carbazole-tribenzène, superpolymère, mélange et composition et utilisation correspondante
EP3508472A1 (fr) * 2018-01-04 2019-07-10 Samsung Display Co., Ltd. Dispositif électroluminescent organique et composé de monoamine pour dispositif électroluminescent organique
WO2019146781A1 (fr) * 2018-01-29 2019-08-01 出光興産株式会社 Composé et élément électroluminescent organique l'utilisant
CN110577508A (zh) * 2018-06-07 2019-12-17 江苏三月光电科技有限公司 一种以三芳胺为核心的化合物及其应用
CN110577511A (zh) * 2018-06-07 2019-12-17 江苏三月光电科技有限公司 一种以三芳胺结构为核心的化合物及其制备方法
CN111440156A (zh) * 2020-05-07 2020-07-24 吉林奥来德光电材料股份有限公司 一种发光辅助材料、其制备方法及有机电致发光器件
CN112479978A (zh) * 2019-09-11 2021-03-12 江苏三月光电科技有限公司 一种以咔唑衍生物为核心的有机化合物及其应用
WO2021193654A1 (fr) * 2020-03-25 2021-09-30 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique
US11233202B2 (en) * 2016-06-17 2022-01-25 Duk San Neolux Co., Ltd. Compound for organic electric element, organic electric element comprising the same and electronic device thereof
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US20170288148A1 (en) * 2016-04-01 2017-10-05 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof
US10573819B2 (en) * 2016-04-01 2020-02-25 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof
US11233202B2 (en) * 2016-06-17 2022-01-25 Duk San Neolux Co., Ltd. Compound for organic electric element, organic electric element comprising the same and electronic device thereof
CN109749735A (zh) * 2017-11-08 2019-05-14 Sfc株式会社 胺取代的萘衍生物和包含其的有机发光二极管
WO2019114610A1 (fr) * 2017-12-14 2019-06-20 广州华睿光电材料有限公司 Composé organique de type carbazole-tribenzène, superpolymère, mélange et composition et utilisation correspondante
CN111247133A (zh) * 2017-12-14 2020-06-05 广州华睿光电材料有限公司 咔唑三苯有机化合物、高聚物、混合物、组合物及其应用
EP3508472A1 (fr) * 2018-01-04 2019-07-10 Samsung Display Co., Ltd. Dispositif électroluminescent organique et composé de monoamine pour dispositif électroluminescent organique
JPWO2019146781A1 (ja) * 2018-01-29 2021-01-28 出光興産株式会社 化合物及びそれを用いた有機エレクトロルミネッセンス素子
WO2019146781A1 (fr) * 2018-01-29 2019-08-01 出光興産株式会社 Composé et élément électroluminescent organique l'utilisant
US11730054B2 (en) 2018-01-29 2023-08-15 Idemitsu Kosan Co., Ltd. Compound having dibenzofuran and naphthalene structures, and organic electroluminescent element using same
CN110577508A (zh) * 2018-06-07 2019-12-17 江苏三月光电科技有限公司 一种以三芳胺为核心的化合物及其应用
CN110577508B (zh) * 2018-06-07 2021-11-05 江苏三月科技股份有限公司 一种以三芳胺为核心的化合物及其应用
CN110577511A (zh) * 2018-06-07 2019-12-17 江苏三月光电科技有限公司 一种以三芳胺结构为核心的化合物及其制备方法
US11440902B2 (en) * 2018-06-08 2022-09-13 Samsung Display Co., Ltd. Amine-based compound and organic light-emitting device including the same
CN112479978A (zh) * 2019-09-11 2021-03-12 江苏三月光电科技有限公司 一种以咔唑衍生物为核心的有机化合物及其应用
CN112479978B (zh) * 2019-09-11 2023-11-28 江苏三月科技股份有限公司 一种以咔唑衍生物为核心的有机化合物及其应用
WO2021193654A1 (fr) * 2020-03-25 2021-09-30 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique
CN111440156A (zh) * 2020-05-07 2020-07-24 吉林奥来德光电材料股份有限公司 一种发光辅助材料、其制备方法及有机电致发光器件
CN115925661A (zh) * 2022-12-28 2023-04-07 吉林奥来德光电材料股份有限公司 一种发光辅助材料及制备方法与其在有机电致发光器件中的应用
CN115925661B (zh) * 2022-12-28 2024-03-26 吉林奥来德光电材料股份有限公司 一种发光辅助材料及制备方法与其在有机电致发光器件中的应用

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