WO2014003336A1 - Composé, dispositif électro-organique utilisant ce composé, et dispositif électronique ainsi réalisé - Google Patents

Composé, dispositif électro-organique utilisant ce composé, et dispositif électronique ainsi réalisé Download PDF

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WO2014003336A1
WO2014003336A1 PCT/KR2013/005099 KR2013005099W WO2014003336A1 WO 2014003336 A1 WO2014003336 A1 WO 2014003336A1 KR 2013005099 W KR2013005099 W KR 2013005099W WO 2014003336 A1 WO2014003336 A1 WO 2014003336A1
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group
organic
sub
aryl
substituted
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PCT/KR2013/005099
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English (en)
Korean (ko)
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변지훈
이선희
박정환
김대성
박보람
오대환
이범성
여승원
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덕산하이메탈(주)
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Publication of WO2014003336A1 publication Critical patent/WO2014003336A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07D417/04—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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—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
    • H10K99/00—Subject matter not provided for in other groups of this subclass
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to a compound, an organic electric element comprising the same, and an electronic device thereof.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic layer is often made of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
  • the material used as the organic material layer in the organic electric element may be classified into a light emitting material and a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.
  • the 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 element has not yet been made sufficiently, and therefore, the development of new materials is continuously required.
  • An object of the present invention is to provide a compound capable of improving high luminous efficiency, low driving voltage, high heat resistance, color purity, and lifetime of an element, an organic electric element using the same, and an electronic device thereof.
  • the present invention provides a compound represented by the following formula (1).
  • the present invention provides an organic electronic device using the compound represented by Formula 1 and an electronic device thereof.
  • FIG. 1 is an exemplary view of an organic electroluminescent device according to the present invention.
  • halo or halogen as used herein 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.
  • an aryl group or an arylene group means a monocyclic or polycyclic aromatic, and includes an aromatic ring formed by neighboring substituents participating in a bond or a reaction.
  • the aryl group may be a phenyl group, a biphenyl group, a fluorene group, a spirofluorene group.
  • 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 single ring but also multiple rings, and adjacent groups may be formed by combining.
  • heterocycloalkyl includes one or more heteroatoms, unless otherwise indicated, having from 2 to 60 carbon atoms, including single rings as well as multicycles. Adjacent groups may be formed in combination.
  • heterocyclic group may mean an alicyclic and / or aromatic including a heteroatom.
  • heteroatom refers to 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 groups, C 1 to C 20 alkylamine groups, C 1 to C 20 alkylthiophene groups, C 6 to C 20 arylthiophene groups, C 2 to C 20 alkenyl groups, C 2 to C 20 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, germanium group, and C 5 ⁇ C 20 It is meant to be substituted with one or more substituents selected from the group consisting of, but not limited to these substituents.
  • 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
  • the organic electroluminescent device may be manufactured using a PVD method.
  • the anode 120 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, and the electron transport layer are formed thereon.
  • the organic material layer including the 160 and the electron injection layer 170 it can be prepared by depositing a material that can be used as the cathode 180 thereon.
  • the organic material layer using a variety of polymer materials is less by a solution process or solvent process, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing or thermal transfer method, rather than deposition 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).
  • Chemical Formula 1 Can be.
  • X and Y are selected from N, NH or S, and in the case of N can form a double bond with a neighboring carbon,
  • R One To R 7 Is hydrogen; heavy hydrogen; Tritium; Halogen group;
  • n is an integer of 1 or 2, when n is 2, R 6 may be the same or different, respectively,
  • R 1 , R 2 , R 3 , R 4 and R 6 may each combine with a neighboring group to form a saturated or unsaturated ring.
  • A is a benzene ring condensed with two adjacent rings and B is a pentagonal ring containing heteroatoms X, Y and fused with A
  • B is
  • the compound represented by Formula 1 may be one of the following Formulas (2) to (7).
  • the compound represented by Formula 1 may be one of the following compounds 1-1 to 6-26.
  • Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2 below.
  • Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 3 below.
  • Sub 3 and Sub 6 of Scheme 1 may be synthesized by the reaction route of Scheme 4 below.
  • Sub 4 and Sub 5 of Scheme 1 may be synthesized by the reaction route of Scheme 5.
  • Sub 1-3, Sub 2-2, Sub 3-2, and Sub 4-2 are as follows, but are not limited thereto, and their FD-MS are shown in Table 1 below.
  • Sub 1-4, Sub 2-3, Sub 3-3, and Sub 4-3 are as follows, but are not limited thereto, and their FD-MS are shown in Table 2 below.
  • Sub 1-5, Sub 2-4, Sub 3-4, and Sub 4-4 are as follows, but are not limited thereto, and their FD-MS are shown in Table 3 below.
  • Sub 1, Sub 2, Sub 3, Sub 4, Sub 5, and Sub 6 are as follows, but are not limited thereto, and their FD-MS are shown in Table 4 below.
  • CuPc copper phthalocyanine
  • ITO layer anode
  • -NPD N- (1-naphthyl) -N -phenylamino] biphenyl
  • a compound according to the present invention is used as a phosphorescent host material on the hole transport layer, and 5 weights of tris (2-phenylpyridine) iridium (hereinafter abbreviated as Ir (ppy) 3 ) as an Ir metal complex dopant is used as a phosphorescent dopant material. It was added at a concentration of 30% by vacuum deposition to a thickness of 30nm to form a light emitting layer.
  • BAlq (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinolinoleito) aluminum
  • An organic electroluminescent device was manufactured in the same manner as in [Example 7], except that CBP, which is the following comparative compound, was used instead of the compound of the present invention as a light emitting host material of the light emitting layer.
  • An organic electroluminescent device was manufactured in the same manner as in [Example 7], except that Comparative Compound A was used instead of the compound of the present invention as a light emitting host material of the light emitting layer.
  • An organic light emitting device was manufactured in the same manner as in [Example 7], except that Comparative Compound B was used instead of the compound of the present invention as a light emitting host material of the light emitting layer.
  • the compound of the present invention having thiazolocarbazole as a core as the light emitting layer material was prepared according to [Example 7] from the results of Table 7 above, as compared with the organic electric device manufactured by [Comparative Example 1] to [Comparative Example 3]. It can be seen that the efficiency and lifespan of the organic electric device are significantly improved.
  • a copper phthalocyanine (hereinafter abbreviated as CuPc) is vacuum-deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer having a thickness of 40 nm, followed by 4,4-bis [on the hole injection layer.
  • N- (1-naphthyl) -N -phenylamino] biphenyl (hereinafter abbreviated as -NPD) was vacuum deposited to a thickness of 20 nm to form a hole transport layer.
  • the compound of the present invention was vacuum-deposited to a thickness of 20 nm on the hole transport layer to form a light emission auxiliary layer.
  • BAlq (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinolinoleito) aluminum
  • An organic light emitting display device was manufactured in the same manner as in [Example 8], except that the light emitting auxiliary layer was omitted. That is, the organic light emitting display device was manufactured in the same manner as in [Example 8], except that the light emitting auxiliary layer was not formed.
  • An organic light emitting display device was manufactured in the same manner as in [Example 8], except that the Comparative Compound A was used to form the emission auxiliary layer instead of the compound of the present invention.
  • Example 8 (Examples 157 to 166) and [Comparative Example 4] (Comparative Example (4)) and [Comparative Example 5] (Comparative Example (5)) prepared as described above
  • the electroluminescence (EL) characteristics were measured with a PR-650 photoresearch company by applying a forward bias DC voltage to the organic electroluminescent devices, and as a result, the life measurement equipment manufactured by McScience Inc. at a luminance of 300 cd / m2 The T95 lifetime was measured through.
  • the organic electroluminescent device using the organic electroluminescent device material of the present invention is used as a light emitting auxiliary layer, the device of [Comparative Example 4] or [Comparative Example] in which the light emitting auxiliary layer is not used.
  • Compound A of 5] can significantly improve the lower driving voltage, higher luminous efficiency and lifetime than the device used as the luminous auxiliary layer.
  • the compound of the present invention when used alone as a light emitting auxiliary layer, it has a high T1 energy level, and due to the deep HOMO energy level, it is possible to obtain the effect of improving the low voltage, high luminous efficiency and device life of the organic electroluminescent device. have.
  • the compound according to the present invention is not only an organic electroluminescent device (OLED), but also a display device, an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a monochromatic or white lighting element, etc.
  • OPC organic photoconductor
  • organic TFT organic transistor
  • the same effect can be obtained when the compounds of the present invention are used in other organic material layers of the organic light emitting device, for example, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer.

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

Abstract

L'invention concerne un nouveau composé, un dispositif électro-organique utilisant ce composé, et un dispositif électronique ainsi réalisé. L'invention permet, d'une part d'accroître l'efficacité de l'émission de lumière, la pureté des couleurs, et la durée de vie d'un dispositif, et d'autre part de diminuer la tension d'excitation.
PCT/KR2013/005099 2012-06-27 2013-06-11 Composé, dispositif électro-organique utilisant ce composé, et dispositif électronique ainsi réalisé WO2014003336A1 (fr)

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KR10-2012-0069237 2012-06-27
KR1020120069237A KR101982746B1 (ko) 2012-06-27 2012-06-27 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

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US20150200371A1 (en) * 2014-01-14 2015-07-16 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
WO2016064102A1 (fr) * 2014-10-22 2016-04-28 주식회사 두산 Dispositif électroluminescent organique
WO2017114317A1 (fr) * 2015-12-30 2017-07-06 南京中硼联康医疗科技有限公司 Composé pour la liaison spécifique avec une protéine ss-amyloïde
CN108239100A (zh) * 2016-12-23 2018-07-03 南京中硼联康医疗科技有限公司 用于制备和β淀粉样蛋白特异性结合的化合物的化合物、制备方法及其应用
CN108239101A (zh) * 2016-12-23 2018-07-03 南京中硼联康医疗科技有限公司 用于制备和β淀粉样蛋白特异性结合的化合物的化合物、制备方法及其应用
CN109651291A (zh) * 2019-01-22 2019-04-19 湘潭大学 一种多取代萘并[1,2-d]噻唑及衍生物及其合成方法
WO2021177616A1 (fr) * 2020-03-04 2021-09-10 덕산네오룩스 주식회사 Dispositif électronique organique comprenant une couche de recouvrement et appareil électronique le comprenant
CN114702484A (zh) * 2022-04-18 2022-07-05 上海传勤新材料有限公司 一种含有唑类的有机化合物及其应用
WO2022157343A1 (fr) * 2021-01-25 2022-07-28 Merck Patent Gmbh Composés azotés pour dispositifs électroluminescents organiques
WO2022211498A1 (fr) * 2021-03-30 2022-10-06 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique le comprenant
WO2023182775A1 (fr) * 2022-03-23 2023-09-28 에스에프씨 주식회사 Nouveau composé hétérocyclique et diode électroluminescente organique le comprenant
WO2024010336A1 (fr) * 2022-07-04 2024-01-11 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique le comprenant

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KR101571597B1 (ko) * 2013-08-05 2015-11-24 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
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KR102656922B1 (ko) * 2017-12-28 2024-04-16 솔루스첨단소재 주식회사 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR102446406B1 (ko) * 2019-07-09 2022-09-22 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기 발광 소자
WO2021006652A1 (fr) * 2019-07-09 2021-01-14 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique l'utilisant
US20230363266A1 (en) * 2020-12-14 2023-11-09 Lg Chem, Ltd. Novel compound and organic light emitting device comprising the same
CN116323621A (zh) * 2020-12-14 2023-06-23 株式会社Lg化学 新的化合物和包含其的有机发光器件
CN116157407A (zh) * 2020-12-17 2023-05-23 株式会社Lg化学 新化合物和包含其的有机发光器件
WO2022131869A1 (fr) * 2020-12-17 2022-06-23 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique le comprenant
KR20220138357A (ko) * 2021-04-05 2022-10-12 주식회사 엘지화학 유기 발광 소자
US20240138256A1 (en) * 2021-04-05 2024-04-25 Lg Chem, Ltd. Organic light emitting device
CN113173934B (zh) * 2021-04-13 2023-05-19 武汉市晟承宇科技有限公司 一种有机化合物及其应用、有机电致发光器件
KR20230020926A (ko) * 2021-08-04 2023-02-13 주식회사 엘지화학 신규한 화합물 및 이를 포함한 유기 발광 소자

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WO2022157343A1 (fr) * 2021-01-25 2022-07-28 Merck Patent Gmbh Composés azotés pour dispositifs électroluminescents organiques
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JP7532742B2 (ja) 2021-03-30 2024-08-14 エルジー・ケム・リミテッド 新規な化合物およびこれを利用した有機発光素子
WO2023182775A1 (fr) * 2022-03-23 2023-09-28 에스에프씨 주식회사 Nouveau composé hétérocyclique et diode électroluminescente organique le comprenant
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WO2024010336A1 (fr) * 2022-07-04 2024-01-11 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique le comprenant

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