WO2013069939A1 - Composé pour élément électronique organique, élément électronique organique comprenant celui-ci, dispositif électronique de celui-ci - Google Patents

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

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WO2013069939A1
WO2013069939A1 PCT/KR2012/009261 KR2012009261W WO2013069939A1 WO 2013069939 A1 WO2013069939 A1 WO 2013069939A1 KR 2012009261 W KR2012009261 W KR 2012009261W WO 2013069939 A1 WO2013069939 A1 WO 2013069939A1
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substituted
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aryl
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박정환
이선희
문성윤
김대성
정화순
김원삼
변지훈
이범성
김동하
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덕산하이메탈(주)
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    • 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
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • 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
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    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms

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 electrical device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
  • Materials used as the organic material layer in the organic electric element may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on their functions.
  • the deposition method is the mainstream in the formation of the OLED device, a situation that requires a material that can withstand a long time, that is, a material having a strong heat resistance characteristics.
  • a material constituting the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material.
  • a stable and efficient organic material layer for an organic electric device has not been made sufficiently, and therefore, the development of new materials is still required.
  • An object of the present invention is to provide a compound containing an five-membered hetero ring capable of improving the luminous efficiency, low driving voltage, color purity, and lifetime of the 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 electronic device using the compound represented by the above formula and an electronic device thereof.
  • the driving voltage of the device can be lowered, and color purity, luminous efficiency and lifetime can be greatly improved.
  • FIG. 1 is an exemplary view of an organic electroluminescent device according to an embodiment of the present invention.
  • halo or halogen as used herein include fluorine, chlorine, bromine, and iodine unless otherwise stated.
  • alkyl or “alkyl group” has a carbon number of 1 to 60 unless otherwise specified, but is not limited thereto.
  • alkenyl or “alkynyl” has a double bond or a triple bond having 2 to 60 carbon atoms, respectively, unless otherwise specified, but is not limited thereto.
  • cycloalkyl refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.
  • alkoxy group used in the present invention has a carbon number of 1 to 60 unless otherwise stated, it 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.
  • the aryl group or arylene group in the present invention means a monocyclic or heterocyclic aromatic, for example, the aryl group may be a phenyl group, biphenyl group, fluorene group, spirofluorene 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 3 to 60 carbon atoms, each of which includes one or more heteroatoms, unless otherwise specified. In addition, it includes not only a single ring but also a heterocycle, and adjacent groups may be formed by bonding.
  • heterocycloalkyl and “heterocyclic group” include one or more heteroatoms, unless otherwise specified, have a carbon number from 2 to 60, and include heterocycles as well as monocycles. Adjacent groups may be formed in combination.
  • heterocyclic group may mean an alicyclic and / or aromatic including a heteroatom.
  • heteroatom refers to at least one of N, O, S, P, and Si unless otherwise indicated.
  • 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.
  • saturated or unsaturated ring as used herein means a saturated or unsaturated aliphatic ring or an aromatic ring or heterocyclic ring having 6 to 60 carbon atoms.
  • heterocompounds or heteroradicals other than the aforementioned heterocompounds include, but are not limited to, one or more heteroatoms.
  • 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 alkoxy group, C 1 ⁇ C 20 alkyl amine group, C 1 ⁇ C 20 coming of the alkyl group, C 6 ⁇ C 20 coming aryl Ti, C 2 ⁇ C 20 alkenyl group, C 2 ⁇ C 20 of the Alkynyl group, C 3 ⁇ C 20 cycloalkyl group, C 6 ⁇ C 60 aryl group, C 6 ⁇ C 20 aryl group substituted with deuterium, C 8 ⁇ C 20 aryl alkenyl group, silane group, boron group, It means that it is substituted with one or more substituents selected from the group consisting of a germanium group, and a C 5 ⁇ C 20 heterocyclic group
  • 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.
  • An organic material layer containing a compound represented by the formula (1) between) is provided.
  • 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 electronic device according to the present invention may further include a protective layer formed on one surface of the first electrode and the second electrode opposite to the organic material layer.
  • the compound according to the present invention applied to the organic material layer is a hole injection layer 130, a hole transport layer 140, an electron transport layer 160, the electron injection layer 170, the host of the light emitting layer 150 or the material of the dopant or capping layer Can be used as Preferably, the compound of the present invention may be used as the light emitting layer 150, hole transport layer 140 and / or light emitting auxiliary layer 151.
  • the light emitting layer is formed using the compound represented by Chemical Formula 1 to optimize the energy level and T1 value between each organic material layer, the intrinsic properties (mobility, interfacial properties, etc.) of the organic layers, and thus the lifetime of the organic electric device. And efficiency can be improved at the same time.
  • the organic electroluminescent device may be manufactured using a PVD method.
  • the anode 120 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, and the electron transport layer are formed thereon.
  • the organic material layer including the 160 and the electron injection layer 170 it can be prepared by depositing a material that can be used as the cathode 180 thereon.
  • the organic layer may be prepared by using a variety of polymer materials, but not by a deposition process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing or thermal transfer. It can be prepared in a number of layers. 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.
  • the organic electroluminescent device according to the present invention may be one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a monochromatic or white illumination device.
  • OLED organic electroluminescent device
  • OPC organic photoconductor
  • organic TFT organic transistor
  • Another embodiment of the present invention may include a display device including the organic electric element of the present invention described above, and an electronic device including a control unit for controlling the display device.
  • the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.
  • the compound according to one aspect of the present invention is represented by the following formula (1).
  • R 1 to R 10 is i) independent of each other, hydrogen, deuterium, halogen, C 6 ⁇ aryl group of C 60, a fluorene group, a fused aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60 C 2 -C 60 heterocyclic group including a ring group, O, N, S, Si and P heteroatoms, -LN (R ') (R "), C 1 ⁇ C 50 Alkyl group, Selected from the group consisting of a C 2 to C 20 alkenyl group, a C 1 to C 30 alkoxy group and a C 6 to C 30 aryloxy group, or ii) adjacent groups combine with each other to form at least one ring Where the groups which do not form a ring are as defined in i).
  • R 1 ⁇ R 4 of must be at least one of both is not a hydrogen R 7 ⁇ R 10 hydrogen and, R 7 ⁇ R or at least one hydrogen of 10 R 1 ⁇ R 4 may be all hydrogen, R 1 Except when R 4 and R 7 to R 10 are both hydrogen at the same time.
  • R 1 to R 4 and R 7 to R 10 are all hydrogen at the same time, for example, i) when R 1 to R 4 are all hydrogen, at least one of R 7 to R 10 is hydrogen in the substituent. It means a substituent other than or when adjacent groups of R 7 ⁇ R 10 combine with each other to form a ring, or ii) when R 7 ⁇ R 10 are all hydrogen, at least one of R 1 ⁇ R 4 is The substituent refers to a substituent other than hydrogen or a case in which adjacent groups in R 1 to R 4 combine with each other to form a ring.
  • Adjacent groups of R 1 and R 10 combine with each other to form at least one ring: R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 7 and R 8 are bonded to each other, R 8 and R 9 and / or R 9 and R 10 are bonded to each other to form a ring.
  • R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 7 and R 8 are bonded to each other
  • R 8 and R 9 and / or R 9 and R 10 are bonded to each other to form a ring.
  • the ring formed by bonding of adjacent groups of R 1 and R 10 to each other may be a monocyclic or polycyclic aromatic ring or a heterocyclic ring containing at least one heteroatom, or a fused aromatic ring with an aliphatic ring.
  • adjacent groups of R 1 and R 10 may be bonded to each other to form an aromatic ring such as benzene, naphthalene, phenanthrene, and the like.
  • a phenanthrene form may be formed together with the benzene ring of the mother nucleus to which they are bonded.
  • R 1 and R 10 may be bonded to each other to form a hetero ring such as thiophene, furan, pyridine, indole, quinoline, etc., wherein the carbon number may be 2 to 60.
  • the ring may be fused to each other, a plurality of rings may not be fused to each other, or a ring in which the fused and non-fused forms are mixed.
  • X and Y are each independently S, O or SiR 31 R 32 .
  • R 31 and R 32 are independently of each other hydrogen, a C 6 ⁇ C 60 aryl group, C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P, Or a C 1 to C 50 alkyl group.
  • L is 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; And divalent aliphatic hydrocarbon group; It is selected from the group consisting of.
  • Ar 1 is a C 2 ⁇ C 60 heterocyclic group, a C 6 ⁇ C 60 aryl group, fluorenyl group or -N (R containing at least one hetero atom of O, N, S, Si and P ') (R ”).
  • R 'and R are independently of each other O, N, S, Si and P containing at least one heteroatom of C 2 ⁇ C 60 heterocyclic group, C 6 ⁇ C 60 aryl group or fluorenyl group Can be.
  • R One ⁇ R 12 , Ar One When R 'and R "are aryl groups, they are deuterium, halogen, silane group, boron group, germanium group, cyano group, nitro group, C One ⁇ C 20 Alkylthio, C One ⁇ C 20 Alkoxyl, C One ⁇ C 20 Alkyl group, C 2 ⁇ C 20 Alkenyl, C 2 ⁇ C 20 Alkynyl, C 6 ⁇ C 20 Aryl group of C, substituted with deuterium 6 ⁇ C 20 Aryl group, C 2 ⁇ C 20 Heterocyclic group, C 3 ⁇ C 20 Cycloalkyl group, C 7 ⁇ C 20 of Arylalkyl group and C 8 ⁇ C 20 May be substituted with one or more substituents selected from the group consisting of arylalkenyl groups,
  • R 1 to R 10 , Ar 1 , R ′ and R ′′ are fluorenyl groups, they are deuterium, halogen, silane groups, cyano groups, C 1 to C 20 alkyl groups, and C 2 to C 20 alkenyl groups (alkenyl ), C aryl group of 6 ⁇ C 20, of a C 6 ⁇ C 20 substituted by deuterium aryl group, C 2 ⁇ C 20 of the heterocyclic group and C 3 ⁇ one or more substituents selected from the group consisting of a cycloalkyl group of C 20 May be substituted with
  • R One ⁇ R 1O If is a fused ring group, it is deuterium, halogen, silane group, boron group, germanium group, cyano group, nitro group, C One ⁇ C 20 Alkylthio, C One ⁇ C 20 Alkoxyl, C One ⁇ C 20 Alkyl group, C 2 ⁇ C 20 Alkenyl, C 2 ⁇ C 20 Alkynyl, C 6 ⁇ C 20 Aryl group of C, substituted with deuterium 6 ⁇ C 20 Aryl group, C 2 ⁇ C 20 Heterocyclic group, C 3 ⁇ C 20 Cycloalkyl group, C 7 ⁇ C 20 of Arylalkyl group and C 8 ⁇ C 20 May be substituted with one or more substituents selected from the group consisting of arylalkenyl groups,
  • R One ⁇ R 12 When is an alkyl group, it is halogen, silane group, boron group, cyano group, C One ⁇ C 20 Alkoxyl, C One ⁇ C 20 Alkyl group, C 2 ⁇ C 20 Alkenyl, C 6 ⁇ C 20 Aryl group of C, substituted with deuterium 6 ⁇ C 20 Aryl group, C 2 ⁇ C 20 Heterocyclic group, C 7 ⁇ C 20 of Arylalkyl group and C 8 ⁇ C 20 May be substituted with one or more substituents selected from the group consisting of arylalkenyl groups,
  • R One ⁇ R 10 When it is an alkenyl group, it is deuterium, a halogen, a silane group, a cyano group, C One ⁇ C 20 Alkoxyl, C One ⁇ C 20 Alkyl group, C 2 ⁇ C 20 Alkenyl, C 6 ⁇ C 20 Aryl group of C, substituted with deuterium 6 ⁇ C 20 Aryl group, C 2 ⁇ C 20 Heterocyclic group, C 3 ⁇ C 20 Cycloalkyl group, C 7 ⁇ C 20 of Arylalkyl group and C 8 ⁇ C 20 May be substituted with one or more substituents selected from the group consisting of arylalkenyl groups,
  • R 1 ⁇ R 10 is an alkoxy group, which is heavy hydrogen, a halogen, a silane group, a C 1 ⁇ C 20 alkyl group, C 6 ⁇ C 20 aryl group, a C 6 ⁇ C 20 substituted with a heavy hydrogen of the aryl group, C 2 ⁇ C 20 It may be substituted with one or more substituents selected from the group consisting of a heterocyclic group and C 3 ⁇ C 20 cycloalkyl group,
  • R 1 ⁇ R 10 is an aryloxy group cases, this deuterium, a silane group, a cyano group, C of 1 ⁇ C 20 alkyl group, a C 6 ⁇ C 20 substituted with an aryl group, a heavy hydrogen of C 6 ⁇ C 20 aryl group , C 2 ⁇ C 20 It may be substituted with one or more substituents selected from the group consisting of a heterocyclic group and C 3 ⁇ C 20 cycloalkyl group.
  • the compound represented by Chemical Formula 1 may be represented by one of the following chemical formulas.
  • R 1 ⁇ R 10 , X, Y, L and Ar 1 are the same as defined in formula (1).
  • the compound represented by Formula 1 or 2 may be one of the following compounds.
  • R 1 ⁇ R 4 , R 7 ⁇ R 10 , X, Y, L and Ar 1 are as defined in formula (1).
  • a compound according to the present invention may be prepared by reacting Sub 5 with one of Sub 1, Sub 2, Sub 3 or Sub 4, as shown in Scheme 1 below.
  • Scheme 1 the following synthesis examples are only examples, so the scope of the present invention is not limited thereto.
  • Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2 below.
  • Triphenylphosphine (87.53 g, 333.7 mmol) and o -dichlorobenzene in M 1-2'-18 (51.98 g, 133.5 mmol) obtained in the above synthesis were obtained using 33.87 g (yield) of the product using Sub 1-2 synthesis of Example 1. : 71%).
  • Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 5 below.
  • Sub 4 of Scheme 1 may be synthesized by the reaction route of Scheme 9 below.
  • Sub 1, Sub 2, Sub 3, and Sub 4 are as follows, but are not limited thereto, and their FD-MSs are shown in Table 1 below.
  • Sub 1 or Sub 2 or Sub 3 or Sub 4 (1 equiv) was dissolved in toluene in a round bottom flask, then Sub 5 (1.2 equiv), Pd 2 (dba) 3 (0.03 equiv), P ( t -Bu) 3 (0.08 equiv), NaO t -Bu (3 equiv) were added and stirred at 100 ° C. After completion of the reaction, the mixture was extracted with CH 2 Cl 2 and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting compound was purified by silicagel column and recrystallization to obtain final products.
  • Sub 1 or Sub 2 or Sub 3 or Sub 4 (1 equiv) was dissolved in dimethyl sulfoxide in a round bottom flask, then Sub 5 (1.1 equiv) and K 2 CO 3 (6 equiv) were added and stirred at 150 ° C. . After completion of the reaction, the mixture was extracted with CH 2 Cl 2 and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting compound was purified by silicagel column and recrystallization to obtain final products.
  • Sub 1-2 (7.18 g, 18 mmol) obtained in the above synthesis was dissolved in toluene in a round bottom flask, and then Sub 5-7 (8.35 g, 21.6 mmol), Pd 2 (dba) 3 (0.49 g, 0.5 mmol) , 50% P ( t- Bu) 3 (0.7ml, 1.4 mmol), NaO t- Bu (5.18 g, 53.9 mmol) was added and stirred at 100 ° C.
  • An organic light emitting diode was manufactured according to a conventional method using a compound obtained through synthesis as a light emitting host material of a light emitting layer.
  • a phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) film was vacuum deposited to form a hole injection layer having a thickness of 60 nm.
  • BAlq (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum
  • BAlq is vacuum-deposited to a thickness of 10 nm on the light emitting layer.
  • a stop layer was formed, and tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq 3 ) was deposited to a thickness of 40 nm to form an electron transport layer.
  • LiF an alkali metal halide
  • Al an alkali metal halide
  • An organic light emitting diode was manufactured in the same manner as in Experimental Example 1, except that Comparative Compound 1 was used as a light emitting host material instead of the compound of the present invention to form a light emitting layer.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example 1, except that the comparative compound 3 (12- (4- (4,6-diphenylpyrimidin-2-yl) phenyl) -12H-benzo [4,5] was used instead of the compound of the present invention. ] thieno [2,3-a] carbazole) was used as a light emitting host material to form a light emitting layer.
  • Electroluminescent (EL) characteristics were measured by PR-650 of photoresearch by applying a forward bias DC voltage to the organic electroluminescent device manufactured by Experimental Example 1 and Comparative Examples, and the measurement result was 300 cd / m 2.
  • the T95 lifetime was measured using a life-time measuring instrument manufactured by McScience Inc. at the reference luminance.
  • Table 4 below shows device fabrication and evaluation results of Examples and Comparative Examples to which the compound according to the invention is applied.
  • the organic electroluminescent device using the organic electroluminescent device material of the present invention as a light emitting host material has remarkably improved color purity, high luminous efficiency and lifetime.
  • the compounds of the present invention are used in other organic material layers of the organic light emitting device, for example, a light emitting auxiliary layer, an electron injection layer, an electron transport layer, and a hole injection layer, it is obvious that the same effect can be obtained.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention porte sur un nouveau composé qui comprend un hétérocycle à 5 éléments apte à améliorer un rendement d'émission de lumière, une stabilité et une durée de vie d'éléments, un élément électronique organique utilisant celui-ci et un dispositif électronique de celui-ci.
PCT/KR2012/009261 2011-11-07 2012-11-06 Composé pour élément électronique organique, élément électronique organique comprenant celui-ci, dispositif électronique de celui-ci WO2013069939A1 (fr)

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KR10-2011-0115427 2011-11-07
KR20110115427 2011-11-07
KR10-2011-0129127 2011-12-05
KR20110129127 2011-12-05
KR10-2012-0121380 2012-10-30
KR1020120121380A KR101948145B1 (ko) 2011-11-07 2012-10-30 유기전기소자용 화합물, 이를 포함하는 유기전기소자 및 그 전자 장치

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CN103467450A (zh) * 2013-09-04 2013-12-25 吉林奥来德光电材料股份有限公司 一类新型有机电致发光材料及其在器件中的应用
EP2772493A1 (fr) * 2013-02-28 2014-09-03 Samsung Display Co., Ltd. Benzoindoles condensés et dispositif électroluminescent organique les comportant
WO2014200244A1 (fr) * 2013-06-11 2014-12-18 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les comprenant
WO2016119992A1 (fr) * 2015-01-30 2016-08-04 Merck Patent Gmbh Matières pour dispositifs électroniques
CN107406381A (zh) * 2015-09-14 2017-11-28 株式会社Lg化学 杂环化合物和包含其的有机发光器件
CN107849442A (zh) * 2015-07-10 2018-03-27 德山新勒克斯有限公司 有机电气元件用化合物、利用其的有机电气元件及其电子装置
WO2018158659A1 (fr) * 2017-03-03 2018-09-07 株式会社半導体エネルギー研究所 Composé organique, élément électroluminescent, dispositif électroluminescent, appareil électronique et dispositif d'éclairage
CN108779120A (zh) * 2016-03-24 2018-11-09 德山新勒克斯有限公司 有机电子元件用化合物、利用该化合物的有机电子元件及其电子装置
CN108948028A (zh) * 2018-08-22 2018-12-07 宇瑞(上海)化学有限公司 一种含氧硫杂环三芳胺化合物的有机光电器件及其应用
CN109326741A (zh) * 2017-08-01 2019-02-12 江苏三月光电科技有限公司 一种含有氮杂苯类化合物的有机发光器件
CN110446714A (zh) * 2017-03-16 2019-11-12 德山金属株式会社 用于有机电子元件的化合物、使用所述化合物的有机电子元件及其电子设备

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WO2010131855A2 (fr) * 2009-05-13 2010-11-18 덕산하이메탈(주) Composé contenant un hétérocycle à 5 éléments, diode électroluminescente organique dans laquelle il est employé, et borne destinée à cette dernière
KR20100122798A (ko) * 2009-05-13 2010-11-23 덕산하이메탈(주) 오원자 헤테로 고리를 포함하는 화합물 및 이를 이용한 유기전기소자, 그 단말
KR20110016288A (ko) * 2009-08-11 2011-02-17 덕산하이메탈(주) 오원자 헤테로 고리를 포함하는 화합물 및 이를 이용한 유기전기소자, 그 단말
KR20110100877A (ko) * 2010-03-05 2011-09-15 덕산하이메탈(주) 2개 이상의 오원자 헤테로고리를 포함하는 화합물이 2개 이상 포함하는 화합물 및 이를 이용한 유기전기소자, 그 단말

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WO2010131855A2 (fr) * 2009-05-13 2010-11-18 덕산하이메탈(주) Composé contenant un hétérocycle à 5 éléments, diode électroluminescente organique dans laquelle il est employé, et borne destinée à cette dernière
KR20100122798A (ko) * 2009-05-13 2010-11-23 덕산하이메탈(주) 오원자 헤테로 고리를 포함하는 화합물 및 이를 이용한 유기전기소자, 그 단말
KR20110016288A (ko) * 2009-08-11 2011-02-17 덕산하이메탈(주) 오원자 헤테로 고리를 포함하는 화합물 및 이를 이용한 유기전기소자, 그 단말
KR20110100877A (ko) * 2010-03-05 2011-09-15 덕산하이메탈(주) 2개 이상의 오원자 헤테로고리를 포함하는 화합물이 2개 이상 포함하는 화합물 및 이를 이용한 유기전기소자, 그 단말

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2772493A1 (fr) * 2013-02-28 2014-09-03 Samsung Display Co., Ltd. Benzoindoles condensés et dispositif électroluminescent organique les comportant
WO2014200244A1 (fr) * 2013-06-11 2014-12-18 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les comprenant
CN103467450A (zh) * 2013-09-04 2013-12-25 吉林奥来德光电材料股份有限公司 一类新型有机电致发光材料及其在器件中的应用
JP2018507194A (ja) * 2015-01-30 2018-03-15 メルク パテント ゲーエムベーハー 電子素子のための材料
WO2016119992A1 (fr) * 2015-01-30 2016-08-04 Merck Patent Gmbh Matières pour dispositifs électroniques
CN107849442B (zh) * 2015-07-10 2020-05-19 德山新勒克斯有限公司 有机电气元件用化合物、利用其的有机电气元件及其电子装置
CN107849442A (zh) * 2015-07-10 2018-03-27 德山新勒克斯有限公司 有机电气元件用化合物、利用其的有机电气元件及其电子装置
CN107406381A (zh) * 2015-09-14 2017-11-28 株式会社Lg化学 杂环化合物和包含其的有机发光器件
EP3351531A4 (fr) * 2015-09-14 2019-05-08 LG Chem, Ltd. Composé hétérocyclique et dispositif électroluminescent organique contenant ce composé
CN107406381B (zh) * 2015-09-14 2021-01-29 株式会社Lg化学 杂环化合物和包含其的有机发光器件
US10421721B2 (en) 2015-09-14 2019-09-24 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising same
US10995069B2 (en) 2016-03-24 2021-05-04 Duk San Neolux Co., Ltd. Compound for organic electric element, organic electric element using same, and electronic device comprising same
CN108779120A (zh) * 2016-03-24 2018-11-09 德山新勒克斯有限公司 有机电子元件用化合物、利用该化合物的有机电子元件及其电子装置
JPWO2018158659A1 (ja) * 2017-03-03 2020-02-06 株式会社半導体エネルギー研究所 有機化合物、発光素子、発光装置、電子機器、および照明装置
WO2018158659A1 (fr) * 2017-03-03 2018-09-07 株式会社半導体エネルギー研究所 Composé organique, élément électroluminescent, dispositif électroluminescent, appareil électronique et dispositif d'éclairage
JP7175259B2 (ja) 2017-03-03 2022-11-18 株式会社半導体エネルギー研究所 有機化合物、発光素子、発光装置、電子機器、および照明装置
CN110446714A (zh) * 2017-03-16 2019-11-12 德山金属株式会社 用于有机电子元件的化合物、使用所述化合物的有机电子元件及其电子设备
CN110446714B (zh) * 2017-03-16 2022-03-11 德山金属株式会社 用于有机电子元件的化合物、使用所述化合物的有机电子元件及其电子设备
CN109326741A (zh) * 2017-08-01 2019-02-12 江苏三月光电科技有限公司 一种含有氮杂苯类化合物的有机发光器件
CN108948028A (zh) * 2018-08-22 2018-12-07 宇瑞(上海)化学有限公司 一种含氧硫杂环三芳胺化合物的有机光电器件及其应用
CN108948028B (zh) * 2018-08-22 2021-09-14 宇瑞(上海)化学有限公司 一种含氧硫杂环三芳胺化合物的有机光电器件及其应用

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