WO2020138726A1 - Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique comprenant ledit élément électrique organique - Google Patents

Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique comprenant ledit élément électrique organique Download PDF

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WO2020138726A1
WO2020138726A1 PCT/KR2019/016193 KR2019016193W WO2020138726A1 WO 2020138726 A1 WO2020138726 A1 WO 2020138726A1 KR 2019016193 W KR2019016193 W KR 2019016193W WO 2020138726 A1 WO2020138726 A1 WO 2020138726A1
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박형근
전진우
이윤석
박정환
조민지
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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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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
    • 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 element, an organic electric element using the same, and an electronic device thereof.
  • the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material.
  • An organic electric device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween.
  • the organic material layer is often composed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
  • Materials used as the organic material layer in the organic electric device may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on the function.
  • the luminescent material may be classified into a high molecular weight type and a low molecular weight type according to the molecular weight, and may be classified into a fluorescent material derived from the singlet excited state of the electron and a phosphorescent material derived from the triplet excited state of the electron according to the light emission mechanism. have.
  • the luminescent material may be divided into blue, green, and red luminescent materials and yellow and orange luminescent materials necessary for realizing a better natural color according to the luminous color.
  • a host/dopant system may be used as a luminescent material.
  • the principle is that when a small amount of the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with the light emitting layer, excitons generated in the light emitting layer are transported to the dopant to produce light with high efficiency.
  • the wavelength of the host moves to the wavelength of the dopant, light of a desired wavelength can be obtained according to the type of dopant used.
  • Efficiency, life, and driving voltage are related to each other.
  • the efficiency increases, the driving voltage decreases relatively, and as the driving voltage decreases, crystallization of organic substances due to Joule heating generated during driving decreases, and as a result, It shows a tendency to increase life.
  • simply improving the organic layer does not maximize efficiency. This is because long life and high efficiency can be achieved at the same time when the energy level and T 1 value between each organic material layer and the intrinsic properties of materials (mobility, interfacial properties, etc.) are optimally combined. .
  • An object of the present invention is to provide a compound capable of lowering the driving voltage of a device and improving the luminous efficiency and life of the device, an organic electrical 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 using the compound represented by the formula and an electronic device thereof.
  • the compound according to the embodiment of the present invention By using the compound according to the embodiment of the present invention, not only the driving voltage of the device can be lowered, but also the luminous efficiency and lifetime of the device can be greatly improved.
  • FIG. 1 is an exemplary view of an organic electroluminescent device according to the present invention.
  • organic electrical element 110 substrate
  • aryl group and arylene group used in the present invention have 6 to 60 carbon atoms, respectively, and are not limited thereto unless otherwise specified.
  • an aryl group or an arylene group may include a monocyclic, ring aggregate, several conjugated ring systems, spiro compounds, and the like.
  • the aryl group may include a fluorenyl group and the arylene group may include a fluorenylene group.
  • fluorenyl group used in the present invention means a substituted or unsubstituted fluorenyl group
  • fluorenylene group means a substituted unsubstituted fluorenylene group unless otherwise specified.
  • Unsubstituted fluorenyl group or unsubstituted fluorenylene group means a monovalent or divalent functional group in which R, R'and R" are all hydrogen in the following structure, and a substituted fluorenyl group or a substituted fluorenylene group In the following structure, it means that at least one of R, R'and R" is a substituent other than hydrogen.
  • fluorenyl group or “fluorenylene group” used in the present invention includes the case where R and R'are bonded to each other in the following structure to form a spy compound together with the carbon to which they are attached.
  • spyro compound as used in the present invention has a'spyro linkage', and a spiro linkage refers to a linkage formed by two rings sharing only one atom. At this time, the atoms shared by the two rings are called'spyro atoms', and these are'monospyro-','dispiro-', and'trispyro' depending on the number of spy atoms in a compound. It is called a compound.
  • heterocyclic group used in the present invention includes aromatic rings such as “heteroaryl group” or “heteroarylene group”, as well as non-aromatic rings, and each carbon number containing one or more heteroatoms unless otherwise specified. 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, ring aggregate, heterozygous multiple ring system, spy containing heteroatoms. Means a compound and the like.
  • aliphatic ring group used in the present invention means a cyclic hydrocarbon excluding aromatic hydrocarbons, and includes monocyclic, ring aggregates, conjugated multiple ring systems, spiro compounds, and the like, unless otherwise indicated. It means a 3 to 60 ring, but is not limited thereto. For example, even when the aromatic ring benzene and the non-aromatic ring cyclohexane are fused, it corresponds to the aliphatic ring.
  • the'group name' corresponding to an aryl group, an arylene group, a heterocyclic group, etc. exemplified as an example of each symbol and its substituent may describe'the name of a group reflecting a singer', but is described as a'parent compound name' You may.
  • the monovalent'group' is'phenanthryl', and the divalent group can be classified as a singer such as'phenanthrylene', etc.
  • the parent compound name may be described as'phenanthrene'.
  • pyrimidine it can be described as'pyrimidine' regardless of the singer, or in the case of monovalent pyrimidinyl group, in the case of divalent pyrimidineylene, etc., as the'group name' of the corresponding singer. have.
  • a number, an alphabet, etc. indicating a position may be omitted.
  • pyrido[4,3-d]pyrimidine as pyridopyrimidine
  • benzofuro[2,3-d]pyrimidine as benzofuropyrimidine
  • 9,9-dimethyl-9H-flu Oren can be described as dimethylfluorene or the like. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be described as benzoquinoxaline.
  • the substituent R 1 means non-existent, that is, when a is 0, it means that hydrogen is bonded to all the carbons forming the benzene ring.
  • the formula or compound may be omitted.
  • a is an integer of 1
  • one substituent R 1 is bound to any one of carbons forming a benzene ring, and when a is an integer of 2 or 3, for example, it can be bonded as follows, and a is 4 to 6 Even in the case of an integer, 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.
  • the rings formed by bonding with adjacent groups are C 6 ⁇ C 60 aromatic ring groups; Fluorenyl group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C 3 ⁇ C 60 aliphatic ring group; C 3 ⁇ C 60 aliphatic ring and C 6 ⁇ C 60 aromatic ring fused ring group; And combinations thereof.
  • a component such as a layer, film, region, plate, etc. is said to be “above” or “on” another component, it is not only when the other component is “directly above”, but also with another component in the middle. It should be understood that the case may be included. Conversely, it should be understood that when a component is said to be “just above” another part, it means that there is no other part in between.
  • FIG. 1 is an exemplary view of an organic electric device according to an embodiment of the present invention.
  • an organic electric device 100 includes a first electrode 120, a second electrode 180, and a first electrode 120 formed on a substrate 110. Between the second electrode 180 includes an organic material layer containing the compound according to the present invention.
  • 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 material 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 sequentially stacked on the first electrode 120. . At this time, at least one of these layers may be omitted, or may further include a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, an electron transport auxiliary layer, a buffer layer 141, etc., and the electron transport layer 160, etc. It can also serve as a hole blocking layer.
  • the organic electric device may further include a protective layer or a light efficiency improving layer.
  • the light efficiency improving layer may be formed on a surface of both surfaces of the first electrode that does not contact the organic material layer or a surface of both surfaces of the second electrode that does not contact the organic material layer.
  • the compound according to an embodiment of the present invention applied to the organic layer is a hole injection layer 130, a hole transport layer 140, a light emitting auxiliary layer 151, an electron transport auxiliary layer, an electron transport layer 160, an electron injection layer ( 170), a host or dopant of the light-emitting layer 150, or may be used as a material for a light efficiency improving layer, but preferably, the compound according to Formula 1 of the present invention is used as a host of the light-emitting layer.
  • the band gap, electrical characteristics, and interfacial characteristics may vary depending on which substituent is attached to which position, and thus, the selection of the core and the combination of sub-substituents coupled thereto. It is necessary to study, especially when the energy level and T 1 value between each organic material layer and the intrinsic properties of materials (mobility, interfacial properties, etc.) are optimally combined, long life and high efficiency can be achieved simultaneously.
  • the energy level and T 1 value between each organic material layer are optimized to optimize the life of the organic electric device. And efficiency can be improved at the same time.
  • the organic electroluminescent device may be manufactured using various deposition methods. It may be manufactured using a deposition method such as PVD or CVD, for example, by depositing a metal or conductive metal oxide or an alloy thereof on a substrate to form the anode 120, and a hole injection layer 130 thereon , After forming an organic material layer including the hole transport layer 140, the light emitting layer 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. have.
  • the light emitting auxiliary layer 151 may be further formed between the hole transport layer 140 and the light emitting layer 150
  • the electron transport auxiliary layer may be further formed between the light emitting layer 150 and the electron transport layer 160.
  • the organic material layer is a solution process or a solvent process (e.g., spin coating process), nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blade using various polymer materials It can be produced with fewer layers by a method such as a ding process, a screen printing process, or a thermal transfer method. Since the organic material layer according to the present invention can be formed in various ways, the scope of the present invention is not limited by the formation method.
  • the organic electric device may be a front emission type, a back emission type, or a double-sided emission type depending on the material used.
  • the organic electroluminescent 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 an electronic device including a display device including the above-described organic electric element of the present invention and 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 mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation, game machines, various TVs, and various computers.
  • R 1 to R 4 are independently of each other hydrogen; heavy hydrogen; halogen; Cyano group; 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; C 3 ⁇ C 60 aliphatic ring group; C 1 ⁇ C 50 alkyl group; C 2 ⁇ C 20 alkenyl group; C 2 ⁇ C 20 alkynyl group; C 1 ⁇ C 30 Alkoxy group; C 6 ⁇ C 30 Aryloxy group; And -L'-N (R a ) (R b ); is selected from the group consisting of, adjacent groups may be bonded to each other to form a ring.
  • Rings formed by combining adjacent R 1 , neighboring R 2 , neighboring R 3 or neighboring R 4 may include C 6 to C 60 aromatic hydrocarbons; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C 3 ⁇ C 60 aliphatic ring group; And combinations thereof.
  • aromatic hydrocarbon preferably C 6 ⁇ C 30 aromatic hydrocarbons, more preferably C 6 ⁇ C 14 aromatic hydrocarbons, such as benzene, naphthalene, phenanthrene, anthracene, etc. Can form.
  • adjacent groups are bonded to each other to form a heterocycle, preferably a C 2 ⁇ C 30 heterocyclic group, more preferably a C 2 ⁇ C 14 heterocyclic group, such as benzofuran, benzothiophene , Indole, phenyl-indole, and the like.
  • adjacent R 3 may be bonded to each other to form a heterocycle.
  • a, b, c, and d are each integers of 0 to 4, and when each of these is an integer of 2 or more, each of R 1, each of R 2, each of R 3, and each of R 4 is the same or different.
  • R 1 to R 4 are aryl groups, preferably, C 6 to C 30 aryl groups, more preferably C 6 to C 18 aryl groups, such as phenyl, biphenyl, naphthyl, terphenyl, and the like.
  • R 1 to R 4 are heterocyclic groups, preferably C 2 to C 30 heterocyclic groups, more preferably C 2 to C 18 heterocyclic groups, such as pyridine, pyrimidine, triazine, carbazole, Phenylcarbazole, quinoxaline, and the like.
  • R 1 to R 4 are an alkyl group, preferably an alkyl group of C 1 to C 10 may be used, for example, methyl, t-butyl, and the like.
  • Ar 1 is 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; C 3 ⁇ C 60 aliphatic ring group; C 1 ⁇ C 50 alkyl group; C 2 ⁇ C 20 alkenyl group; C 2 ⁇ C 20 alkynyl group; C 1 ⁇ C 30 Alkoxy group; C 6 ⁇ C 30 Aryloxy group; And -L'-N (R a ) (R b ); It may be selected from the group consisting of.
  • Ar 1 is an aryl group, preferably an aryl group of C 6 to C 30 , more preferably an aryl group of C 6 to C 18 , such as phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, triphenylene , Fluoranthene, pyrene, and the like.
  • Ar 1 is a heterocyclic group, preferably a C 2 to C 30 heterocyclic group, more preferably a C 2 to C 24 heterocyclic group, such as pyridine, pyrimidine, triazine, quinazoline, quinoxaline, Benzoquinoxaline, dibenzoquinoxaline, quinoline, benzothiophene, dibenzothiophene, benzonaphthothiophene, benzofuran, dibenzofuran, benzonaphthofuran, carbazole, phenyl-carbazole, benzothieno Pyrimidine, benzofuropyrimidine, indolopyrimidine, indolopyrazine, imidazopyridine, benzoimidazopyridine, dihydrophenazine, dihydro-diphenylphenazine, phenoxazine, phenothiazine, thiarene , Dihydro-dimethyl-phenyl acro
  • Ar 1 is a fluorenyl group, it may be 9,9-dimethyl-9 H -fluorene, 9,9-diphenyl-9 H -fluorenyl group, 9,9'-spirobifluorene, or the like.
  • L 1 and L' are each independently a single bond; C 6 ⁇ C 60 Arylene group; Fluorylene group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; And C 3 ⁇ C 60 It may be selected from the group consisting of an aliphatic ring group.
  • L 1 and L'are arylene groups preferably an arylene group of C 6 to C 30 , more preferably an arylene group of C 6 to C 18 , such as phenylene, biphenyl, naphthalene, terphenyl, etc. .
  • L 1 and L'are heterocyclic groups preferably a heterocyclic group of C 2 to C 30 , more preferably a heterocyclic group of C 2 to C 21 , such as pyridine, pyrimidine, triazine, quinoline, carba Sol, phenylcarbazole, quinazoline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline, benzothienopyrimidine, benzofuropyrimidine, indolopyrimidine, indole, dihydrophenazine, dihydro-di Methyl acrodine, dihydro-phenyl acrodine, phenoxazin, phenothiazine, thiarene, and the like.
  • R a and R b are independently of each other 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; And C 3 ⁇ C 60 Aliphatic ring group; may be selected from the group consisting of.
  • R 1 ⁇ R 4 , L 1 , Ar 1 , L', R a , R b , rings formed by bonding adjacent groups to each other are deuterium; halogen; A silane group unsubstituted or substituted with an alkyl group of C 1 -C 20 or an aryl group of C 6 -C 20 ; Siloxane groups; Boron group; Germanium group; Phosphine oxide unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; Cyano group; Nitro group; C 1 -C 20 alkylthio; C 1 -C 20 Alkoxy group; C 6 -C 20 Aryloxy group; C 1 -C 20 alkyl group; Alkenyl group of C 2 -C 20 ; Alkynyl group of C 2 -C 20 ; C 6 -C 20 Aryl group;
  • Chemical Formula 1 may be represented by one of the following Chemical Formulas 2 to 7.
  • R 1 to R 4 , Ar 1 , L 1 , a, b, c, d are as defined in Formula 1.
  • 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 including 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 represented by Chemical Formula 1 It includes one single compound or two or more compounds.
  • the organic material layer includes at least one layer 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, preferably the compound is included in the light emitting layer, more preferably It is used as a host material for the light emitting layer.
  • the present invention provides an electronic device including a display device including the organic electroluminescent device represented by Chemical Formula 1 and a control unit driving the display device.
  • the compound represented by Chemical Formula 1 according to the present invention (final product 1) may be prepared by reacting Sub 1 and Sub 2 as shown in Reaction Scheme 1 below, but is not limited thereto.
  • the compound belonging to Sub 1 of Reaction Scheme 1 may be the following compound, but is not limited thereto.
  • Sub 1 of Reaction Scheme 1 may be synthesized by the reaction route of Reaction Scheme 2 below, but is not limited thereto.
  • Sub 1-IV (25.2 g, 60.8 mmol) was dissolved in 200 mL of toluene, 2-chloroaniline (8.5 g, 66.8 mmol), Pd(dba) 3 (1.7 g, 1.8 mmol), NaOt-bu (17.5 g, 182.2) mmol), tri tert-butylphosphine (1.2 g, 6.1 mmol) was added and stirred at 120°C. After the reaction was completed, the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 , concentrated, and the resulting compound was separated by a silica gel column and recrystallized to obtain 24.6 g of product (yield: 80%).
  • Sub 1-II instead of Sub 1-II-2 (33.3 g, 73.3 mmol) was used to proceed in the same manner as in the synthesis method of Sub 1-III to obtain 19.5 g of product (yield: 68%).
  • Sub 1-III instead of Sub 1-II-3 (19.5g, 49.8 mmol) was used and 1,2-dichlorobenzene (8.1g, 54.9 mmol) was used to proceed in the same way as in the synthesis of Sub 1-IV. 18.6 g of product (yield: 80%) was obtained.
  • Sub 1-IV instead of Sub 1-II-4 (18.6 g, 39.9 mmol) was used and 2-chloroaniline (5.6 g, 44 mmol) was used to proceed in the same way as in the synthesis method of Sub 1-V to give 17.8 g of product. (Yield: 80%).
  • Sub 1-V instead of Sub 1-II-5 (17.8 g, 32.0 mmol) was used to proceed in the same manner as in the synthesis method of Sub 1-1 to obtain 11.3 g of the product (yield: 68%).
  • Sub 1-IV instead of Sub 1-IV (40 g, 96.4 mmol) was used and 2,4-dichloroaniline (17.2 g, 106.1 mmol) was used to proceed in the same manner as the synthesis method of Sub 1-V, resulting in 41.7 g of product ( Yield: 80%).
  • Sub 1-V instead of Sub 1-III-1 (41.7 g, 77.1 mmol) was used to proceed in the same manner as the synthesis method of Sub 1-1 to obtain 26.4 g of the product (yield: 68%).
  • Sub 1-III (40.0g, 117.4 mmol) was used, and instead of 1,2-dichlorobenzene, 2,3-dichlorodibenzo[b,d]furan (30.6g, 237.1 mmol) was used to synthesize Sub 1-IV. Proceed in the same way to give the product 47.4 g (yield: 80%).
  • Sub 1-II instead of Sub 1-IV-2 (42.8 g, 72.3 mmol) was used to proceed in the same manner as the synthesis method of Sub 1-III to obtain 27.5 g of the product (yield: 68%).
  • the compound belonging to Sub 2 may be the following compound, but is not limited thereto.
  • Sub 1-22 (5 g, 9.6 mmol) instead of Sub 1-1, Sub 2-7 [Cas. 68820-91-7] (2.3g, 10.6 mmol) was used to proceed in the same manner as in the synthesis method of P-1 to obtain 5.2 g of the product (yield: 77%).
  • Sub 1-1 (5 g, 10.6 mmol) instead of Sub 1-1, Sub 2-33 [Cas. 7342-86-1] (2.0 g, 11.7 mmol) was used to proceed in the same manner as in the synthesis method of P-1 to obtain 4.9 g (yield: 77%) of the product.
  • Sub 1-2 (5g, 10.6 mmol) instead of Sub 1-1, Sub 2-52 [Cas. 1373116-37-0] (4.1 g, 11.7 mmol) was used to proceed in the same manner as in the synthesis method of P-1 to obtain 6.4 g (yield: 77%) of the product.
  • 2-TNATA 4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine
  • 2-TNATA 4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine
  • 2-TNATA 4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine
  • 2-TNATA 4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine
  • BAlq (1,1'-bisphenyl)-4-oleito)bis(2-methyl-8-quinolineoleito)aluminum
  • BAlq 2 bis(10-hydroxybenzo[h]quinolinato)beryllium
  • BeBq 2 bis(10-hydroxybenzo[h]quinolinato)beryllium
  • an organic electroluminescent device was manufactured by depositing LiF on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and then depositing Al to a thickness of 150 nm to form a cathode.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of the present invention shown in Table 4 below was used instead of the compound P-1 as a host material of the light emitting layer.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the following Comparative Compound 1 or Comparative Compound 2 was used instead of Compound P-1 of the present invention as the host material of the light emitting layer.
  • Electro-luminescence (EL) characteristics of the organic electroluminescent device manufactured by Examples 1 to 25 and Comparative Examples 1 and 2 of the present invention were applied to PR-650 manufactured by Photoresearch by applying a direct bias DC voltage.
  • the T95 lifespan was measured through a life measurement equipment of Max Science at a reference luminance of 2500 cd/m 2 . The measurement results are shown in Table 4 below.
  • the comparative compound 2 which is an 8-ring heterocyclic compound
  • CBP Comparative Compound 1
  • device characteristics are excellent.
  • the condensed compound of the present invention was used as a host material, it showed better results in terms of driving voltage, efficiency, and life.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé représenté par la formule chimique 1 ; un élément électrique organique comprenant une première électrode, une seconde électrode, et une couche organique placée entre la première électrode et la seconde électrode ; et un dispositif électronique comprenant l'élément électrique organique. La couche organique fournie par la présente invention comprend le composé représenté par la formule chimique 1, ce qui permet de réduire la tension de commande de l'élément électrique organique, et d'améliorer l'efficacité d'émission de lumière ainsi que la durée de vie.
PCT/KR2019/016193 2018-12-28 2019-11-22 Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique comprenant ledit élément électrique organique WO2020138726A1 (fr)

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CN112375082A (zh) * 2020-11-23 2021-02-19 北京八亿时空液晶科技股份有限公司 系列咔唑衍生物及其应用
CN112442041A (zh) * 2020-11-23 2021-03-05 北京八亿时空液晶科技股份有限公司 咔唑衍生物及其应用
CN112442046A (zh) * 2020-11-23 2021-03-05 北京八亿时空液晶科技股份有限公司 萘桥联咔唑衍生物及其应用
CN112480128A (zh) * 2020-11-23 2021-03-12 北京八亿时空液晶科技股份有限公司 一种咔唑衍生物及其应用
CN112480136A (zh) * 2020-11-23 2021-03-12 北京八亿时空液晶科技股份有限公司 杂原子桥联咔唑衍生物及其应用
CN112521340A (zh) * 2020-11-23 2021-03-19 北京八亿时空液晶科技股份有限公司 一种有机电致发光材料及其应用
WO2022152213A1 (fr) * 2021-01-13 2022-07-21 浙江光昊光电科技有限公司 Composé organique, son utilisation dans un dispositif électronique organique et composition

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KR102638039B1 (ko) * 2019-03-25 2024-02-20 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
CN114874228A (zh) * 2021-02-05 2022-08-09 上海和辉光电股份有限公司 一种有机电致发光化合物及其应用

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CN112321598A (zh) * 2020-11-02 2021-02-05 北京八亿时空液晶科技股份有限公司 一种咔唑衍生物及其应用
CN112321598B (zh) * 2020-11-02 2022-10-28 北京八亿时空液晶科技股份有限公司 一种咔唑衍生物及其应用
CN112375082A (zh) * 2020-11-23 2021-02-19 北京八亿时空液晶科技股份有限公司 系列咔唑衍生物及其应用
CN112442041A (zh) * 2020-11-23 2021-03-05 北京八亿时空液晶科技股份有限公司 咔唑衍生物及其应用
CN112442046A (zh) * 2020-11-23 2021-03-05 北京八亿时空液晶科技股份有限公司 萘桥联咔唑衍生物及其应用
CN112480128A (zh) * 2020-11-23 2021-03-12 北京八亿时空液晶科技股份有限公司 一种咔唑衍生物及其应用
CN112480136A (zh) * 2020-11-23 2021-03-12 北京八亿时空液晶科技股份有限公司 杂原子桥联咔唑衍生物及其应用
CN112521340A (zh) * 2020-11-23 2021-03-19 北京八亿时空液晶科技股份有限公司 一种有机电致发光材料及其应用
CN112480128B (zh) * 2020-11-23 2022-12-13 北京八亿时空液晶科技股份有限公司 一种咔唑衍生物及其应用
CN112480136B (zh) * 2020-11-23 2022-12-13 北京八亿时空液晶科技股份有限公司 杂原子桥联咔唑衍生物及其应用
CN112442041B (zh) * 2020-11-23 2023-01-06 北京八亿时空液晶科技股份有限公司 咔唑衍生物及其应用
WO2022152213A1 (fr) * 2021-01-13 2022-07-21 浙江光昊光电科技有限公司 Composé organique, son utilisation dans un dispositif électronique organique et composition

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