WO2021141356A1 - Composé pour élément électronique organique, élément électronique organique faisant appel à celui-ci, et dispositif électronique associé - Google Patents

Composé pour élément électronique organique, élément électronique organique faisant appel à celui-ci, et dispositif électronique associé Download PDF

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WO2021141356A1
WO2021141356A1 PCT/KR2021/000079 KR2021000079W WO2021141356A1 WO 2021141356 A1 WO2021141356 A1 WO 2021141356A1 KR 2021000079 W KR2021000079 W KR 2021000079W WO 2021141356 A1 WO2021141356 A1 WO 2021141356A1
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organic
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송형근
김원삼
오대환
이세훈
오현지
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덕산네오룩스 주식회사
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    • 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
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    • C07C23/00—Compounds containing at least one halogen atom bound to a ring other than a six-membered aromatic ring
    • C07C23/18—Polycyclic halogenated hydrocarbons
    • C07C23/20—Polycyclic halogenated hydrocarbons with condensed rings none of which is aromatic
    • C07C23/38—Polycyclic halogenated hydrocarbons with condensed rings none of which is aromatic with three condensed rings
    • C07C23/40—Halogenated completely or partially hydrogenated fluorenes
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    • 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
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
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    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
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    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • C07D319/24—[b,e]-condensed with two six-membered rings
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    • 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
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • 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
    • C07D409/12—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 chain containing hetero atoms as chain links
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
    • 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
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    • 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
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    • 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
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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

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.
  • the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material.
  • An organic electric device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic material layer therebetween.
  • the organic layer is often formed of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
  • Efficiency, lifespan, and driving voltage are related to each other, and if the efficiency is increased, the driving voltage is relatively decreased, and as the driving voltage is decreased, crystallization of organic materials due to Joule heating generated during driving decreases, resulting in a decrease in the driving voltage. It shows a tendency to increase the lifespan.
  • the efficiency cannot be maximized simply by improving the organic material layer. This is because, when the energy level and T1 value between each organic material layer, and the intrinsic properties (mobility, interfacial properties, etc.) of materials are optimally combined, long lifespan and high efficiency can be achieved at the same time.
  • a light emitting auxiliary layer is formed between the hole transport layer and the light emitting layer, and different light emission according to each light emitting layer (R, G, B) is preferable. Development of the auxiliary layer is necessary.
  • An object of the present invention is to provide a compound capable of improving luminous efficiency and lifespan of a device, an organic electric device 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 electric device and an electronic device using the compound represented by the above formula.
  • both the luminous efficiency and lifespan of the organic electric device can be improved.
  • 1 to 3 are exemplary views of an organic electroluminescent device according to the present invention.
  • organic electric device 110 first electrode
  • first hole transport layer 340 first light emitting layer
  • second charge generation layer 420 second hole injection layer
  • aryl group and arylene group used in the present invention have 6 to 60 carbon atoms, respectively, unless otherwise specified, but are not limited thereto.
  • the aryl group or the arylene group may include a monocyclic type, a ring aggregate, a fused multiple ring system, a spiro compound, and the like.
  • the aryl group may include a fluorenyl group and the arylene group may include a fluorenylene group.
  • fluorenyl group refers to a substituted or unsubstituted fluorenyl group
  • fluorenylene group refers to a substituted or unsubstituted fluorenyl group
  • the fluorenyl group or The fluorenylene group includes a case in which R and R' are bonded to each other in the following structure to form a spiro compound together with the carbon to which they are bonded.
  • Substituted fluorenyl group means that at least one of R, R', R" in the following structure is a substituent other than hydrogen, and in the present specification, regardless of the valence, a fluorenyl group , a fluorenylene group, a fluorentriyl group, etc. may all be called a fluorene group.
  • the term "spiro compound" has a 'spiro linkage', and the spiro linkage means a linkage formed by sharing only one atom between two rings. At this time, the atoms shared by the two rings are called 'spiro atoms', and they are respectively 'monospiro-', 'dispiro-', 'trispiro-', depending on the number of spiro atoms in a compound. ' It's called a compound.
  • heterocyclic group used in the present invention includes not only aromatic rings such as “heteroaryl group” or “heteroarylene group” but also non-aromatic rings, and unless otherwise specified, the number of carbon atoms each containing at least one heteroatom It means a ring of 2 to 60, but is not limited thereto.
  • heteroatom refers to N, O, S, P or Si, unless otherwise specified, and the heterocyclic group is a monocyclic group including a heteroatom, a ring aggregate, a fused multiple ring system, a spy means a compound or the like.
  • aliphatic ring group used in the present invention refers to a cyclic hydrocarbon other than an aromatic hydrocarbon, and includes a monocyclic type, a ring aggregate, a fused multiple ring system, a spiro compound, etc., unless otherwise specified, the number of carbon atoms It means a ring of 3 to 60, but is not limited thereto. For example, even when benzene, which is an aromatic ring, and cyclohexane, which is a non-aromatic ring, are fused, it corresponds to an aliphatic ring.
  • the 'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc. exemplified as examples of each symbol and its substituent may be described as 'the name of the group reflecting the valence' You may.
  • the monovalent 'group' is 'phenanthryl' and the divalent group is 'phenanthrylene'. Regardless, it can also be described as the name of the parent compound, 'phenanthrene'.
  • pyrimidine regardless of the valence, it can be described as 'pyrimidine', or as the 'name of the group' of the valence, such as a pyrimidinyl group in the case of monovalent, or pyrimidinylene in the case of divalent. have.
  • the substituent R 1 means that it does not exist, that is, when a is 0, it means that all hydrogens are bonded to the carbons forming the benzene ring, and in this case, the indication of hydrogen bonded to carbon is shown. Chemical formulas or compounds may be omitted.
  • R 1 when a is an integer of 1, one substituent R 1 is bonded to any one of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it may be bonded as follows, for example, a is 4 to 6 Even if it is an integer of , it is bonded to the carbon of the benzene ring in a similar manner, and when a is an integer of 2 or more, R 1 may be the same or different from each other.
  • the number in 'number-condensed ring' indicates the number of rings to be condensed.
  • a form in which three rings are condensed with each other, such as anthracene, phenanthrene, benzoquinazoline, etc. may be expressed as a 3-condensed ring.
  • a ring when expressed in the form of a 'numeric atom' such as a 5-membered ring, a 6-membered ring, etc., the number in 'number-atom' indicates the number of elements forming the ring.
  • thiophene or furan may correspond to a 5-membered ring
  • benzene or pyridine may correspond to a 6-membered ring.
  • the ring formed by bonding adjacent groups to each other is a C 6 ⁇ C 60 aromatic ring group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; And C 3 ⁇ C 60
  • An aliphatic ring group may be selected from the group consisting of.
  • 'neighboring groups' refers to each other when describing the following chemical formula as an example, R 1 and R 2 each other , R 2 and R 3 each other , R 3 and R 4 each other , Not only R 5 and R 6 but also R 7 and R 8 sharing one carbon are included, and not immediately adjacent, such as R 1 and R 7 , R 1 and R 8 , or R 4 and R 5 , etc. Substituents bonded to ring constituents (such as carbon or nitrogen) may also be included.
  • substituents on a ring constituent element such as carbon or nitrogen immediately adjacent to it, they may be a neighboring group, but if no substituent is bonded to a ring constituent element at the immediately adjacent position, it is bonded to the next ring constituent element It can be a group adjacent to the substituent group, and also the substituents bonded to the same ring constituent carbon can be said to be adjacent groups.
  • the expression 'neighboring groups may combine with each other to form a ring' is used in the same meaning as 'neighboring groups combine with each other to selectively form a ring', and at least one pair of It means a case where adjacent groups are bonded to each other to form a ring.
  • a component such as a layer, membrane, region, plate, etc.
  • 1 to 3 are exemplary views of an organic electric device according to an embodiment of the present invention.
  • an organic electric device 100 includes a first electrode 110 , a second electrode 170 , and a first electrode 110 formed on a substrate (not shown). ) and an organic material layer formed between the second electrode 170 .
  • the first electrode 110 may be an anode (anode)
  • the second electrode 170 may be a cathode (cathode)
  • the first electrode may be a cathode and the second electrode may be an anode.
  • the organic material layer may include a hole injection layer 120 , a hole transport layer 130 , a light emitting layer 140 , an electron transport layer 150 , and an electron injection layer 160 .
  • the hole injection layer 120 , the hole transport layer 130 , the light emitting layer 140 , the electron transport layer 150 , and the electron injection layer 160 may be sequentially formed on the first electrode 110 .
  • the light efficiency improving layer 180 may be formed on one side of both surfaces of the first electrode 110 or the second electrode 170 not in contact with the organic material layer, and when the light efficiency improving layer 180 is formed The light efficiency of the organic electric device may be improved.
  • the light efficiency improving layer 180 may be formed on the second electrode 170 .
  • the light efficiency improving layer 180 is formed to form the second electrode 170 .
  • the light efficiency improvement layer 180 serves as a buffer for the second electrode 170 . can do.
  • a buffer layer 210 or a light emitting auxiliary layer 220 may be further formed between the hole transport layer 130 and the light emitting layer 140 , which will be described with reference to FIG. 2 .
  • the organic electric device 200 includes a hole injection layer 120 , a hole transport layer 130 , a buffer layer 210 sequentially formed on the first electrode 110 , It may include a light emitting auxiliary layer 220 , a light emitting layer 140 , an electron transport layer 150 , an electron injection layer 160 , and a second electrode 170 , and a light efficiency improving layer 180 is formed on the second electrode.
  • a light emitting auxiliary layer 220 a light emitting layer 140 , an electron transport layer 150 , an electron injection layer 160 , and a second electrode 170 , and a light efficiency improving layer 180 is formed on the second electrode.
  • an electron transport auxiliary layer may be further formed between the light emitting layer 140 and the electron transport layer 150 .
  • the organic material layer may have a form in which a plurality of stacks including a hole transport layer, a light emitting layer, and an electron transport layer are formed. This will be described with reference to FIG. 3 .
  • an organic electric device 300 includes two stacks ST1 and ST2 of an organic material layer formed of a multilayer between the first electrode 110 and the second electrode 170 . More than one set may be formed, and a charge generating layer (CGL) may be formed between stacks of organic material layers.
  • CGL charge generating layer
  • the organic electric device includes a first electrode 110 , a first stack ST1 , a charge generation layer (CGL), a second stack ST2, and a second electrode. 170 and the light efficiency improving layer 180 may be included.
  • the first stack ST1 is an organic material layer formed on the first electrode 110 , which is a first hole injection layer 320 , a first hole transport layer 330 , a first emission layer 340 , and a first electron transport layer 350 .
  • the second stack ST2 may include a second hole injection layer 420 , a second hole transport layer 430 , a second emission layer 440 , and a second electron transport layer 450 .
  • the first stack and the second stack may be organic material layers having the same stacked structure or organic material layers having different stacked structures.
  • a charge generation layer CGL may be formed between the first stack ST1 and the second stack ST2 .
  • the charge generation layer CGL may include a first charge generation layer 360 and a second charge generation layer 361 .
  • the charge generating layer CGL is formed between the first light emitting layer 340 and the second light emitting layer 440 to increase the efficiency of current generated in each light emitting layer and smoothly distribute charges.
  • the first light-emitting layer 340 may include a light-emitting material including a blue fluorescent dopant in a blue host, and the second light-emitting layer 440 includes a material in which a green host is doped with a greenish yellow dopant and a red dopant. may be included, but the material of the first light emitting layer 340 and the second light emitting layer 440 according to an embodiment of the present invention is not limited thereto.
  • n may be an integer of 1 to 5.
  • the charge generation layer CGL and the third stack may be additionally stacked on the second stack ST2 .
  • an organic electroluminescent device that emits white light by the mixing effect of light emitted from each light emitting layer can be manufactured as well as light of various colors. It is also possible to manufacture an organic electroluminescent device that emits light.
  • the compound represented by Formula 1 of the present invention is a hole injection layer (120, 320, 420), a hole transport layer (130, 330, 430), a buffer layer 210, a light emitting auxiliary layer 220, an electron transport layer (150, 350) , 450), the electron injection layer 160, the light emitting layers 140, 340, 440 or the light efficiency improvement layer 180 may be used as a material, preferably, the light emission auxiliary layer 220 and / or the light efficiency improvement layer 180 ) can be used as a material for
  • the energy level and T 1 value between each organic material layer, and the intrinsic properties of the material (mobility) , interface characteristics, etc.) can be optimized to simultaneously improve the lifetime and efficiency of the organic electric device.
  • the organic electroluminescent device may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD or CVD, for example, by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form the anode 110, and the hole injection layer 120 thereon , after forming an organic material layer including the hole transport layer 130, the light emitting layer 140, the electron transport layer 150 and the electron injection layer 160, it can be manufactured by depositing a material that can be used as the cathode 170 thereon. have.
  • a deposition method such as PVD or CVD
  • an auxiliary light emitting layer 220 may be formed between the hole transport layer 130 and the light emitting layer 140 , and an electron transport auxiliary layer (not shown) may be further formed between the light emitting layer 140 and the electron transport layer 150 . It can also be formed in a stack structure as shown.
  • the organic layer is a solution process or a solvent process rather than a deposition method using various polymer materials, such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll-to-roll process, Dr. Blay It can be manufactured with a smaller number of layers by a method such as a printing process, a screen printing process, or a thermal transfer method. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the formation method.
  • the organic electric device may be a top emission type, a back emission type, or a double-sided emission type depending on the material used.
  • the organic electric device may be selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting device, and a quantum dot display device.
  • Another embodiment of the present invention may include a display device including the organic electric device 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/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 control, a navigation system, a game machine, various TVs, and various computers.
  • the compound according to one aspect of the present invention is represented by the following formula (1).
  • X is O, S, N(R 1 ), or C(R 2 )(R 3 ) to be.
  • R 1 to R 4 are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; C 6 ⁇ C 60 Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; C 3 ⁇ C 60 aliphatic group; C 1 ⁇ C 30 Alkyl group; C 2 ⁇ C 30 Alkenyl group; C 2 ⁇ C 30 Alkynyl group; C 1 ⁇ C 30 An alkoxyl group; C 6 ⁇ C 30 Aryloxy group; and -L′-N(R a )(R b ), and adjacent groups may be bonded to each other to form a ring.
  • a ring formed by bonding adjacent groups to each other is a C 6 ⁇ C 60 aromatic ring, O, N, S, Si and P including at least one heteroatom of at least one C 2 ⁇ C 60 heterocyclic ring, or C 3 ⁇ It may be a C 60 aliphatic ring.
  • neighboring R 1 , neighboring R 2 , neighboring R 3 , or neighboring R 4 combine with each other to form an aromatic ring, preferably a C 6 ⁇ C 20 aromatic ring, more preferably A C 6 ⁇ C 14 aromatic ring, such as benzene, naphthalene, phenanthrene, and the like may be formed.
  • a to c are each an integer of 0 to 4
  • d is an integer from 0 to 5
  • each of R 1 , each of R 2 , each of R 3 , and each of R 4 are the same as or different from each other .
  • L 1 is a single bond; C 6 ⁇ C 60 Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; And C 3 ⁇ C 60 It is selected from the group consisting of an aliphatic cyclic group.
  • Ar 1 and Ar 2 are each independently a C 6 ⁇ C 60 aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; And C 3 ⁇ C 60 It is selected from the group consisting of an aliphatic cyclic group.
  • the R 1 , R a and R b are each independently a C 6 ⁇ C 60 aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; And C 3 ⁇ C 60 It is selected from the group consisting of an aliphatic cyclic group.
  • the R 2 and R 3 are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; C 6 ⁇ C 60 Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; C 3 ⁇ C 60 aliphatic group; C 1 ⁇ C 30 Alkyl group; C 2 ⁇ C 30 Alkenyl group; C 2 ⁇ C 30 Alkynyl group; C 1 ⁇ C 30 An alkoxyl group; And C 6 ⁇ C 30 It is selected from the group consisting of an aryloxy group, R 2 And R 3 may be bonded to each other to form a ring. When R 2 and R 3 combine with each other to form a ring, a spiro compound is formed.
  • the L' is a single bond; C 6 ⁇ C 60 Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; And C 3 ⁇ C 60 It is selected from the group consisting of an aliphatic cyclic group.
  • the arylene group is, for example, C 6 ⁇ C 30 , C 6 ⁇ C 28 , C 6 ⁇ C 26 , C 6 ⁇ C 25 , C 6 ⁇ C 24 , C 6 ⁇ C 23 , C 6 ⁇ C 22 , C 6 ⁇ C 21 , C 6 ⁇ C 20 , C 6 ⁇ C 19 , C 6 ⁇ C 18 , C 6 ⁇ C 17 , C 6 ⁇ C 16 , C 6 ⁇ C 15 , C 6 ⁇ C 14 , C 6 ⁇ C 13 , C 6 ⁇ C 12 , C 6 ⁇ C 11 , C 6 ⁇ C 10 , C 6 , C 10 , C 12 , C 13 , C 14 , It may be an arylene group such as C 15 , C 16 , C 17 , C 18 , and specifically, phenylene, biphenyl, naphthylene, terphenyl, phenanthrene
  • the heterocyclic group is, for example, C 2 to C 30 , C 2 ⁇ C 26 , C 2 ⁇ C 25 , C 2 ⁇ C 24 , C 2 ⁇ C 23 , C 2 ⁇ C 22 , C 2 ⁇ C 21 , C 2 ⁇ C 20 , C 2 ⁇ C 19 , C 2 ⁇ C 18 , C 2 ⁇ C 17 , C 2 ⁇ C 16 , C 2 ⁇ C 15 , C 2 ⁇ C 14 , C 2 ⁇ C 13 , C 2 ⁇ C 12 , C 2 ⁇ C 11 , C 2 ⁇ C 10 , C 2 ⁇ C 9 , C 2 ⁇ C 8 , C 2 ⁇ C 7 , C 2 ⁇ C 6 , C 2 ⁇ C 5 , C 2 ⁇ C 4 , C 2
  • At least one of R 1 to R 4 , R 1 to R 3 , Ar 1 , Ar 2 , R a , R b is a fluorenyl group or at least one of L 1 , L′ is a fluorenylene group, the flu Orenyl group or fluorenylene group is 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro [benzo [ b ] flu -11,9'- fluorene fluorene], benzo [b] fluorene, diphenyl-11,11- -11 H - benzo [b] fluorene, 9- (naphthalen-2-yl) -9 H 9-phenyl - It may be fluorene or the like.
  • the alkyl group is, for example, C 1 to C 20 , C 1 to C 10 , C 1 to C 4 , C 1 , C 2 , C 3 , may be an alkyl group such as C 4 , specifically methyl, ethyl, propyl, t-butyl, and the like.
  • the alkenyl group is, for example, C 2 to C 20 , C 2 to C 10 , C 2 to C 4 , C 2 , C 3 , It may be an alkenyl group such as C 4 , and specifically may be ethylene, propylene, t-butylene, or the like.
  • the aryl group, an arylene group, a fluorenyl group, a fluorenylene group, a heterocyclic group, an aliphatic ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyl group, an aryloxy group, a ring formed by bonding adjacent groups to each other, and R 2 and R 3 are bonded to each other to form a ring and the like are each deuterium; halogen; a silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; Phosphine oxide unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; siloxane group; cyano group; nitro group; C 1 -C 20 Alkylthio group; C 1 -C 20 An alkoxyl group; C 6 -C
  • the aryl group is, for example, C 6 ⁇ C 20 , C 6 ⁇ C 19 , C 6 ⁇ C 18 , C 6 ⁇ C 17 , C 6 ⁇ C 16 , C 6 ⁇ C 15 , C 6 ⁇ C 14 , C 6 ⁇ C 13 , C 6 ⁇ C 12 , C 6 ⁇ C 11 , C 6 ⁇ C 10 , C 6 , C 10 , C 12 , It may be an aryl group such as C 13 , C 14 , C 15 , C
  • the heterocyclic group is, for example, C 2 ⁇ C 20 , C 2 ⁇ C 19 , C 2 ⁇ C 18 , C 2 ⁇ C 17 , C 2 ⁇ C 16 , C 2 ⁇ C 15 , C 2 ⁇ C 14 , C 2 ⁇ C 13 , C 2 ⁇ C 12 , C 2 ⁇ C 11 , C 2 ⁇ C 10 , C 2 ⁇ C 9 , C 2 ⁇ C 8 , C 2 ⁇ C 7 , C 2 ⁇ C 6 , C 2
  • the alkyl group is, for example, C 1 ⁇ C 20 , C 1 ⁇ C 10 , C 1 ⁇ C 4 , C 1 , C 2 , It may be an alkyl group such as C 3 , C 4 .
  • Formula 1 may be represented by Formula 2 below.
  • Formula 1 may be represented by Formula 3 below.
  • X, R 1 to R 4 , a to d, L 1 , Ar 2 are the same as defined in Formula 1 above.
  • L 2 is a single bond; C 6 ⁇ C 60 Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom selected from the group consisting of C 2 ⁇ C 60 A heterocyclic group; And C 3 ⁇ C 60 It is selected from the group consisting of an aliphatic cyclic group.
  • Y is O, S, N(R 4 ) or C(R 5 )(R 6 ).
  • R 8 , R 9 , R 5 and R 6 are each independently hydrogen; heavy hydrogen; halogen; a silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; Phosphine oxide unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; siloxane group; cyano group; nitro group; C 1 -C 20 Alkylthio group; C 1 -C 20 An alkoxyl group; C 6 -C 20 aryloxy group; C 6 -C 20 Arylthio group; C 1 -C 20 Alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 alkynyl group; C 6 -C 20 Aryl group; fluorenyl group; C 2 -C 20 A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N,
  • each R 8 , each R 9 is the same as or different from each other.
  • R 4 is a C 6 -C 20 aryl group; fluorenyl group; C 2 -C 20 A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; And C 3 -C 20 It is selected from the group consisting of an aliphatic cyclic group.
  • the compound represented by Formula 1 may be one of the following compounds, but is not limited thereto.
  • the present invention provides an organic electric device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer is a compound represented by Formula 1 includes
  • the present invention provides an organic electric device including a first electrode, a second electrode, an organic material layer formed between the first electrode and the second electrode, and a light efficiency improving layer.
  • the light efficiency improving layer is formed on one side of both surfaces of the first electrode or both sides of the second electrode that is not in contact with the organic material layer, and the organic material layer or the light efficiency improving layer contains the compound represented by Formula 1 above.
  • the organic layer includes at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, and preferably, the compound may be included in the light emission auxiliary layer.
  • the organic material layer may include two or more stacks including a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the first electrode, and may further include a charge generating layer formed between the two or more stacks.
  • an electronic device including a display device including the organic electric device represented by Formula 1, and a control unit for driving the display device.
  • the compound (Final product) represented by Formula 1 according to the present invention may be synthesized by reacting Sub 1 and Sub 2 as shown in Scheme 1 below, but is not limited thereto.
  • Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2 below, but is not limited thereto.
  • the compound belonging to Sub 1 may be a compound as follows, but is not limited thereto, and Table 1 shows FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds.
  • Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 3 below, but is not limited thereto.
  • the compound belonging to Sub 2 of Scheme 1 may be a compound as follows, but is not limited thereto, and Table 2 shows FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds.
  • a -diamine hereinafter abbreviated as '2-TNATA'
  • N,N'-Bis(1-naphthalenyl)-N,N'-bis-phenyl- A (1,1'-biphenyl)-4,4'-diamine hereinafter abbreviated as 'NPB' film was vacuum-deposited to a thickness of 60 nm to form a hole transport layer.
  • 'CBP' 4,4'-N,N'-dicarbazole-biphenyl
  • 'Ir(ppy) 3 ' tris(2-phenylpyridine)-iridium
  • 'BAlq' (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum
  • 'BAlq 3 tris-(8-hydroxyquinoline)aluminum
  • LiF was deposited to a thickness of 0.2 nm to form an electron injection layer, and then 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 in the same manner as in Example 1, except that the compound of the present invention described in Table 4 was used instead of the compound P-3 of the present invention as a light emitting auxiliary layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 1 below was used instead of Compound P-3 of the present invention as a light emitting auxiliary layer material.
  • the compound of the present invention and Comparative Compound 1 are similar in that a heteroaryl group such as dibenzofuran is bonded to the 9th position of the fluorene group, but the bonding position of the amine group is different from each other.
  • the light emitting auxiliary layer it is necessary to understand the correlation between the hole transport layer and the light emitting layer (host). Even if a similar core is used, it is difficult for a person skilled in the art to infer the characteristics of the light emitting auxiliary layer in which the compound of the present invention is used. It will be very difficult.
  • the compound of the present invention may be applied to the hole transport layer or both the hole transport layer and the light emission auxiliary layer.

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Abstract

La présente invention concerne : un composé représenté par la formule chimique 1 ; un élément électronique organique comprenant une première électrode, une seconde électrode et une couche organique entre la première électrode et la seconde électrode ; et un dispositif électronique comprenant l'élément électronique organique. La couche organique comprend le composé représenté par la formule chimique 1, et le rendement lumineux et la durée de vie de l'élément électronique organique peuvent ainsi être améliorés.
PCT/KR2021/000079 2020-01-10 2021-01-05 Composé pour élément électronique organique, élément électronique organique faisant appel à celui-ci, et dispositif électronique associé WO2021141356A1 (fr)

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CN113698340A (zh) * 2021-09-26 2021-11-26 长春海谱润斯科技股份有限公司 一种咔唑衍生物及其有机电致发光器件
KR102374470B1 (ko) * 2021-07-21 2022-03-15 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
CN114394929A (zh) * 2022-01-25 2022-04-26 长春海谱润斯科技股份有限公司 一种基于咔唑的三芳胺类衍生物及其有机电致发光器件
WO2023078824A1 (fr) 2021-11-04 2023-05-11 Dottikon Es Holding Ag Composés de type spiro-(indane-fluorène) et leur utilisation dans l'électronique organique
WO2023247416A1 (fr) 2022-06-21 2023-12-28 Dottikon Es Holding Ag Composés de type tétraarylbenzidine et leur utilisation en électronique organique

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CN113773328B (zh) * 2021-09-16 2022-09-02 南京邮电大学 一种芴基咔唑大环化合物及其制备方法和应用
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WO2023003234A1 (fr) * 2021-07-21 2023-01-26 덕산네오룩스 주식회사 Composé pour élément électrique organique, élément électrique organique faisant appel à celui-ci, et dispositif électronique associé
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CN113651785A (zh) * 2021-09-17 2021-11-16 长春海谱润斯科技股份有限公司 一种杂环化合物及其有机发光器件
CN113651785B (zh) * 2021-09-17 2024-01-26 长春海谱润斯科技股份有限公司 一种杂环化合物及其有机发光器件
CN113698340A (zh) * 2021-09-26 2021-11-26 长春海谱润斯科技股份有限公司 一种咔唑衍生物及其有机电致发光器件
WO2023078824A1 (fr) 2021-11-04 2023-05-11 Dottikon Es Holding Ag Composés de type spiro-(indane-fluorène) et leur utilisation dans l'électronique organique
CN114394929A (zh) * 2022-01-25 2022-04-26 长春海谱润斯科技股份有限公司 一种基于咔唑的三芳胺类衍生物及其有机电致发光器件
CN114394929B (zh) * 2022-01-25 2024-01-26 长春海谱润斯科技股份有限公司 一种基于咔唑的三芳胺类衍生物及其有机电致发光器件
WO2023247416A1 (fr) 2022-06-21 2023-12-28 Dottikon Es Holding Ag Composés de type tétraarylbenzidine et leur utilisation en électronique organique

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