WO2013055132A2 - Composé pour dispositif électrique organique, dispositif électrique organique l'utilisant et dispositif électronique correspondant - Google Patents

Composé pour dispositif électrique organique, dispositif électrique organique l'utilisant et dispositif électronique correspondant Download PDF

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WO2013055132A2
WO2013055132A2 PCT/KR2012/008278 KR2012008278W WO2013055132A2 WO 2013055132 A2 WO2013055132 A2 WO 2013055132A2 KR 2012008278 W KR2012008278 W KR 2012008278W WO 2013055132 A2 WO2013055132 A2 WO 2013055132A2
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organic
aryl
compound
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WO2013055132A3 (fr
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박정환
이선희
문성윤
김대성
정화순
김원삼
변지훈
이범성
최대혁
김동하
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덕산하이메탈(주)
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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    • H10K85/649—Aromatic compounds comprising a hetero atom
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
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    • 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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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 light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. Can be.
  • the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.
  • 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 host / dopant system may be used. The principle is that when a small amount of dopant having an energy band gap smaller than that of the host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant, thereby producing high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.
  • 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 capable of improving high luminous efficiency, low driving voltage, 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.
  • the present invention provides an organic electric device comprising the formula (1) and an electronic device using the same.
  • FIG. 1 is an exemplary view of an organic electroluminescent device according to an embodiment of the present invention.
  • halo or halogen includes fluorine, chlorine, bromine, and iodine unless otherwise noted.
  • 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 heterocyclic 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 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 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 Preferably, the compound according to the present invention may be used as a host material of the light emitting layer 150 or a material for forming the hole transport layer 140.
  • the organic electroluminescent device can be manufactured using a PVD (physical vapor deposition) 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.
  • An organic electric device includes an anode, a cathode, and an organic material layer formed between the anode and the cathode.
  • the emission layer may be formed of a compound represented by the following Chemical Formula 1.
  • a ring is C 6 ⁇ C 60
  • R 1 to R 11 are each independently hydrogen, deuterium, halogen, nitrile group, nitro group, -LN (Ar 1 ) (Ar 2 ), C 6 ⁇ C 60 aryl group, fluorenyl group, C 2 ⁇ C 60 heterocyclic group, C 1 ⁇ C 30 Alkoxy group, C 6 ⁇ C 30 It may be selected from the group consisting of aryloxy group and C 1 ⁇ C 50 Alkyl group, X is S, SO or SO 2 to be.
  • L is a direct bond (that is, absent), C 6 ⁇ C 60 arylene group, fluorenylene group, C 6 ⁇ C 60 aromatic ring and C 3 ⁇ C 60 of aliphatic and may be selected from the group consisting of fused rings, C 2 ⁇ C 60 heterocyclic group or a divalent aliphatic hydrocarbon group,
  • Ar 1 and Ar 2 are each independently of the C 6 ⁇ C 60 aryl group, C 2 ⁇ C 60 heterocyclic group, fluorenyl group, C 1 ⁇ C 30 alkoxy group, C 6 ⁇ C 30 aryloxy group And it is selected from the group consisting of C 1 ⁇ C 50 Alkyl group.
  • Y, R 1 to R 11 , L, Ar 1, and Ar 2 may be further substituted with specific substituents.
  • Y, R 1 to R 11 , Ar 1 and Ar 2 is a C 6 ⁇ C 60 aryl group
  • Y, R 1 to R 11 , Ar 1 and Ar 2 is a fluorenyl group
  • these are deuterium, halogen, silane group, boron group, germanium group, C 1 ⁇ C 20 Alkylthio group, C 6 ⁇ C 20 arylthio group, C 1 -C 20 alkoxy group, -N (Ar 1 ) (Ar 2 ), C 1 -C 20 alkyl group, C7-C20 arylalkyl group, C 2 -C 20 alkenyl group , C 8 ⁇ C 20 aryl alkenyl group, C 2 ⁇ C 20 alkynyl group, C 3 ⁇ C 20 cycloalkyl group, C 6 ⁇ C 20
  • the C 6 ⁇ C 60 heterocyclic group of the Y, R 1 to R 11 , L, Ar 1 and Ar 2 includes at least one hetero atom of O, N, S, Si and P, deuterium, halogen Group, -N (Ar 1 ) (Ar 2 ), C 1 -C 20 alkyl group, C 7 -C 20 arylalkyl group, C 2 -C 20 alkenyl group, C 8 -C 20 arylalkenyl group, C It may be substituted with one or more substituents selected from the group consisting of 1 to C 20 alkoxy group, C 6 ⁇ C 60 aryl group, C 6 ⁇ C 20 aryl group substituted with deuterium, a nitrile group and an acetylene group.
  • the C 1 to C 30 alkoxy group and the C 6 to C 30 aryloxy group of the Y, R 1 to R 11 , Ar 1 and Ar 2 may be deuterium, halogen, amino, nitrile, nitro or C 1.
  • the C 1 to C 50 alkyl group of Y, R 1 to R 11 , r 1, and Ar 2 may be C 2 to C 20 alkenyl group, C 1 to C 20 alkoxy group, C 6 to C 20 aryl A C 6 to C 20 aryl group, a C 7 to C 20 arylalkyl group, a C 8 to C 20 arylalkenyl group, a C 2 to C 20 heterocyclic group, a nitrile group and an acetylene group It may be substituted with one or more substituents selected from the group.
  • Formula 1 may be represented by one of the following formula.
  • R 1 ⁇ R 11 and X are as defined in formula (1).
  • Y may be selected from the group of monovalent substituents in the definition of Y in Formula 1
  • Y may be a direct bond or may be selected from the group of divalent substituents in the definition of Y in Formula 1.
  • L, Ar 1 and Ar 2 are the same as defined in Chemical Formula 1.
  • Formula 1 when A ring is a benzene ring, Formula 1 may be represented by one of the following Formulas 5 to 7.
  • R 1 to R 8 and X are the same as defined in Chemical Formula 1.
  • Y in Formula 5 may be selected from the group of monovalent substituents in the Y definition of Formula 1
  • Y in Formula 6 may be a direct bond, or may be selected from a divalent substituent group in the Y definition of Formula 1
  • Formula 7 L, Ar 1 and Ar 2 are as defined in formula (1).
  • Formula 1 may be one of the following compounds, but is not limited to these compounds, any compound satisfying Formula 1 will belong to the present invention.
  • Chemical Formula 1 may be synthesized by the following Chemical Formula 1.
  • Sub 1-6 may be synthesized by Scheme 2 below.
  • Sub 1-1 to Sub 1-6 of Scheme 2 may be synthesized by the following synthesis method, but is not limited thereto.
  • Sub 1-1 (36.0 g, 140 mmol) obtained in the above synthesis was dissolved in 980 mL of DMF, followed by bispinacolborate (39.1 g, 154 mmol), PdCl 2 (dppf) catalyst (3.43 g, 4.2 mmol), KOAc (41.3 g, 420 mmol) was added sequentially, followed by stirring for 24 hours to synthesize the borate compound.
  • the obtained compound was separated through a silica gel column and recrystallized, and then the borate compound was 29.81 g (70%) of Sub 1-2.
  • Sub 1-3 was dissolved in dichloromethane, 30% aqueous hydroxyperoxide solution and acetic acid were added, followed by stirring at 30 ° C. for 4 hours. After the reaction was completed, extracted with chloroform and water, the organic layer was dried, silicagel column and recrystallization to obtain Sub 1-4 76%.
  • Sub 1-5 was dissolved in 600 mL of methylene chloride, and then 0.05 equivalent of BPO (Benzoyl peroxide) and NBS (N-bromosuccinimide) (35.60 g, 200 mmol) were added slowly, followed by stirring at room temperature for 24 hours. After the reaction was completed, 300 mL of 5% HCl was added, followed by 300 mL of water to remove residual NBS, and extracted with ether and water. The organic layer was dried over MgSO 4 and concentrated. The resulting organic material was silicagel column and recrystallized to obtain Sub 1-6 78%.
  • BPO Benzoyl peroxide
  • NBS N-bromosuccinimide
  • Sub 2 in Scheme 1 may be one of the following compounds, but is not limited thereto.
  • the final compound of the present invention can be prepared by the following scheme 3.
  • Sub 3 may be one of the following compounds, but is not necessarily limited thereto.
  • Sub 1-7 compound (1 equivalent) was added to a round bottom flask, and the amine compound Sub 3 (1.1 equivalent), Pd (PPh 3 ) 4 (0.03 to 0.05 equivalent), NaOH (3 equivalent), THF (3 mL / 1 mmol), water (1.5 mL / 1 mmol) is added. Thereafter, the mixture is heated to reflux at 80 ° C to 90 ° C. When the reaction is complete, distilled water is diluted at room temperature and extracted with methylene chloride and water. The organic layer was dried over MgSO 4 , concentrated, and the resulting compound was recrystallized from a silicagel column. FD-MS of the final compound thus synthesized is shown in Table 4 below.
  • each of the substituents of the compounds represented by the formula (1) has a broad relationship, exemplarily described the synthesis examples of the representative compounds, the compounds represented by the formula (1) not illustrated by way of example as a synthesis example Can be configured.
  • the compound which has the intrinsic property of the introduced substituent can be synthesize
  • substituents used in the hole injection layer material, the hole transport layer material, the light emitting layer material, and the electron transport layer material used in the manufacture of the organic electric device, including the organic light emitting device to satisfy the conditions required for each organic material layer Materials can be prepared.
  • the compound according to the present invention may be used in various applications in the organic electroluminescent device according to the type and nature of the substituent. That is, the compound of the present invention can be applied to various layers other than the host of the phosphorescent or fluorescent light emitting layer because it is free to be controlled by the core and the substituent.
  • a copper phthalocyanine (CuPc) film was vacuum deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer having a thickness of 10 nm.
  • a hole injection layer having a thickness of 10 nm.
  • 4,4-bis [ N- (1-naphthyl) -N -phenylamino] biphenyl was vacuum deposited to a thickness of 30 nm on the hole injection layer to form a hole transport layer.
  • a light emitting layer having a thickness of 30 nm was formed on the hole transport layer by doping at 95: 5 weight using a compound of the present invention as a host material and Ir (ppy) 3 [tris (2-phenylpyridine) -iridium] as a dopant material.
  • Ir (ppy) 3 tris (2-phenylpyridine) -iridium]
  • ((1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer
  • Tris (8-quinolinol) aluminum was deposited to a thickness of 40 nm on the hole blocking layer to form an electron injection layer.
  • LiF an alkali metal halide
  • Al was deposited to a thickness of 150 nm
  • an organic light emitting diode was manufactured by forming an Al / LiF cathode.
  • An organic electroluminescent device was manufactured in the same manner as in Experiment 1, except that the compound represented by Comparative Compound 2 was used as a host material instead of the compound of the present invention when forming the emission layer.
  • a 4,4'4 "-tris (N- (2-naphthyl) -N-phenylamino) -triphenylamine (hereinafter abbreviated as 2T-NATA) film was formed on an ITO layer (anode) formed on a glass substrate. Vacuum deposition was performed to form a 10 nm thick hole injection layer. Subsequently, the compound of the present invention was vacuum deposited on the hole injection layer to form a hole transport layer having a thickness of 30 nm. In addition, a 45 nm-thick light emitting layer doped with BD-052X (Idemitus, Inc.) 7% was formed on the hole transport layer. 2-anthracene (AND))).
  • An organic light emitting display device was manufactured in the same manner as in Experiment 2, except that the compound represented by Comparative Compound 2 was used instead of the compound of the present invention when forming the hole injection layer.
  • the driving voltage of the organic light emitting device can be lowered, and color purity, luminous efficiency and lifespan can be remarkably improved. Can be. Even if 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Manufacturing & Machinery (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention porte sur un nouveau composé apte à améliorer le rendement lumineux, la stabilité et la durée de vie d'un dispositif, et un dispositif électrique organique l'utilisant et un dispositif électronique correspondant.
PCT/KR2012/008278 2011-10-13 2012-10-11 Composé pour dispositif électrique organique, dispositif électrique organique l'utilisant et dispositif électronique correspondant WO2013055132A2 (fr)

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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014034793A1 (fr) * 2012-08-30 2014-03-06 出光興産株式会社 Dérivé d'amine aromatique et élément électroluminescent organique utilisant ledit dérivé
WO2014181878A1 (fr) * 2013-05-10 2014-11-13 東ソー株式会社 Composé arylamine et son utilisation
US20160099423A1 (en) * 2014-10-06 2016-04-07 Samsung Display Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
US20160322581A1 (en) * 2015-04-30 2016-11-03 Samsung Display Co., Ltd. Organic light-emitting device
KR20160129191A (ko) * 2015-04-29 2016-11-09 삼성디스플레이 주식회사 유기 발광 소자
WO2017022729A1 (fr) * 2015-07-31 2017-02-09 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique
US20170186974A1 (en) * 2015-12-24 2017-06-29 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
WO2017209297A1 (fr) * 2016-06-02 2017-12-07 国立大学法人名古屋大学 Composé triarylène et son procédé de production
CN111499618A (zh) * 2020-05-15 2020-08-07 上海天马有机发光显示技术有限公司 一种化合物及包含其的有机光电装置
JP2020152655A (ja) * 2019-03-19 2020-09-24 東ソー株式会社 縮環基を有するベンゾヘテロフェナントレン化合物及びその用途
US11038124B2 (en) 2018-10-03 2021-06-15 Luminescence Technology Corp. Organic compound and organic electroluminescence device using the same
CN113330096A (zh) * 2018-10-03 2021-08-31 马克斯·普朗克索赔科学公司 取代或未取代的多环芳烃化合物用于高分辨率显微术的用途
CN113330096B (zh) * 2018-10-03 2024-05-31 马克斯·普朗克索赔科学公司 取代或未取代的多环芳烃化合物用于高分辨率显微术的用途

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6223558B2 (ja) * 2013-06-14 2017-11-01 エルジー・ケム・リミテッド 有機太陽電池およびその製造方法
KR102212965B1 (ko) * 2014-06-18 2021-02-05 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20160030001A (ko) * 2014-09-05 2016-03-16 삼성디스플레이 주식회사 축합환 화합물 및 이를 포함한 유기 발광 소자
WO2018021854A1 (fr) 2016-07-27 2018-02-01 주식회사 엘지화학 Composé polycyclique et élément électroluminescent organique le comprenant
KR102564917B1 (ko) * 2020-12-21 2023-08-09 엘티소재주식회사 헤테로 고리 화합물, 이를 포함하는 유기전계발광소자, 및 유기물층용 조성물

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011037429A2 (fr) * 2009-09-28 2011-03-31 덕산하이메탈(주) Composés ayant des dérivés hétérocycliques à cycle aryle condensé de 5 chaînons, dispositif électronique organique utilisant les composés, et terminal comprenant le dispositif électronique organique

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101219481B1 (ko) * 2009-09-28 2013-01-15 덕산하이메탈(주) 아릴 고리가 축합된 복소환 5원자고리 유도체를 가지는 화합물 및 이를 이용한 유기전기소자, 그 단말

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011037429A2 (fr) * 2009-09-28 2011-03-31 덕산하이메탈(주) Composés ayant des dérivés hétérocycliques à cycle aryle condensé de 5 chaînons, dispositif électronique organique utilisant les composés, et terminal comprenant le dispositif électronique organique

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
FRACHE. G. ET AL.: 'Post-source Decay of Alkylated and Functionalized Polycyclic Aromatic Compounds' RAPID COMMUNICATIONS IN MASS SPECTROMETRY vol. 21, 2007, ISSN 0951-4198 pages 2601 - 2607 *
KITAMURA, T ET AL.: 'Exclusive Cyclization at Sulfur in Photolysis of beta-[o-arylthio)phenyl] vinyl Bromides' CHEMISTRY LETTERS 1986, ISSN 0366-7022 pages 839 - 842 *
KITAMURA, T. ET AL.: 'Phenyl Migration to Thiophene Ring in Photolysis of 1-Phenylbenzo [b]thiophenium Salts' TETRAHEDRON LETTERS vol. 38, no. 29, 1997, ISSN 0040-4039 pages 5157 - 5160 *
LIANG, F. ET AL.: 'Determination of Polycyclic Aromatic Sulfur Heterocycles in Diesel Particulate Matter and Diesel Fuel by Gas Chromatography with Atomic Emission Detection' JOURNAL OF CHROMATOGRAPHY A vol. 1114, 2006, ISSN 0021-9673 pages 145 - 153 *
NAGAO, I. ET AL.: '9-Stannafluorenes: 1,4-Dimetal Equivalents for Aromatic Annulation by Double Cross-Coupling' ANGEWANDTE CHEMIE vol. 48, 2009, ISSN 1433-7851 pages 7573 - 7576 *

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WO2014034793A1 (fr) * 2012-08-30 2014-03-06 出光興産株式会社 Dérivé d'amine aromatique et élément électroluminescent organique utilisant ledit dérivé
US10985325B2 (en) 2012-08-30 2021-04-20 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescent element using same
WO2014181878A1 (fr) * 2013-05-10 2014-11-13 東ソー株式会社 Composé arylamine et son utilisation
JP2015096484A (ja) * 2013-05-10 2015-05-21 東ソー株式会社 アリールアミン化合物及びその用途
US9856243B2 (en) 2014-10-06 2018-01-02 Samsung Display Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
US20160099423A1 (en) * 2014-10-06 2016-04-07 Samsung Display Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
CN105481829A (zh) * 2014-10-06 2016-04-13 三星显示有限公司 稠环化合物及包含它的有机发光装置
EP3006436A1 (fr) * 2014-10-06 2016-04-13 Samsung Display Co., Ltd. Composé cyclique condensé et dispositif électroluminescent organique comprenant celui-ci
KR20160129191A (ko) * 2015-04-29 2016-11-09 삼성디스플레이 주식회사 유기 발광 소자
US20160329501A1 (en) * 2015-04-29 2016-11-10 Samsung Display Co., Ltd. Organic light emitting device
KR102370354B1 (ko) 2015-04-29 2022-03-07 삼성디스플레이 주식회사 유기 발광 소자
US9923147B2 (en) * 2015-04-29 2018-03-20 Samsung Display Co., Ltd. Organic light emitting device
US20160322581A1 (en) * 2015-04-30 2016-11-03 Samsung Display Co., Ltd. Organic light-emitting device
US9859503B2 (en) * 2015-04-30 2018-01-02 Samsung Display Co., Ltd. Organic light-emitting device
US11117857B2 (en) 2015-07-31 2021-09-14 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent elements, organic electroluminescent element and electronic device
WO2017022729A1 (fr) * 2015-07-31 2017-02-09 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique
US11939279B2 (en) 2015-07-31 2024-03-26 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent elements, organic electroluminescent element and electronic device
US9960367B2 (en) * 2015-12-24 2018-05-01 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
US20170186974A1 (en) * 2015-12-24 2017-06-29 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
WO2017209297A1 (fr) * 2016-06-02 2017-12-07 国立大学法人名古屋大学 Composé triarylène et son procédé de production
US11038124B2 (en) 2018-10-03 2021-06-15 Luminescence Technology Corp. Organic compound and organic electroluminescence device using the same
CN113330096A (zh) * 2018-10-03 2021-08-31 马克斯·普朗克索赔科学公司 取代或未取代的多环芳烃化合物用于高分辨率显微术的用途
CN113330096B (zh) * 2018-10-03 2024-05-31 马克斯·普朗克索赔科学公司 取代或未取代的多环芳烃化合物用于高分辨率显微术的用途
JP2020152655A (ja) * 2019-03-19 2020-09-24 東ソー株式会社 縮環基を有するベンゾヘテロフェナントレン化合物及びその用途
CN111499618A (zh) * 2020-05-15 2020-08-07 上海天马有机发光显示技术有限公司 一种化合物及包含其的有机光电装置

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