WO2013009079A1 - Composé à base de triphénylène et diode électroluminescente organique l'utilisant - Google Patents

Composé à base de triphénylène et diode électroluminescente organique l'utilisant Download PDF

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WO2013009079A1
WO2013009079A1 PCT/KR2012/005474 KR2012005474W WO2013009079A1 WO 2013009079 A1 WO2013009079 A1 WO 2013009079A1 KR 2012005474 W KR2012005474 W KR 2012005474W WO 2013009079 A1 WO2013009079 A1 WO 2013009079A1
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배형찬
김성무
손효석
김태형
라종규
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주식회사 두산
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Definitions

  • the present invention relates to a triphenylene-based organic electroluminescent device material having a specific structure and to the organic electroluminescent device having improved characteristics such as luminous efficiency, brightness, thermal stability, driving voltage, lifetime by including the material in at least one organic material layer It is about.
  • the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.
  • the light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to achieve better natural colors, depending on the light emission color.
  • a host / dopant system may be used as a light emitting material.
  • Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. Since the luminous efficiency can be improved up to 4 times compared to the phosphorescent dopant, a lot of research on phosphorescent host materials has been conducted.
  • NPB, BCP, Alq 3 and the like are widely known as the hole blocking layer and the electron transport layer, and anthracene derivatives have been reported as fluorescent dopant / host materials as light emitting materials.
  • phosphorescent materials having a great advantage in terms of efficiency improvement among the light emitting materials include metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2, such as blue, green, and red dopant materials.
  • CBP is a phosphorescent host material and has shown high characteristics to date.
  • existing materials have advantages in terms of luminescence properties, but the glass transition temperature is low and thermal stability is not very good, and thus it is not satisfactory in terms of lifespan in OLED devices. Therefore, the development of more excellent materials is required.
  • the present invention has been made to solve the above problems, and an object thereof is to provide a novel organic compound having an improved glass transition temperature and excellent thermal stability.
  • an object of the present invention is to provide an organic electroluminescent device having improved characteristics such as luminous efficiency, brightness, power efficiency, thermal stability, driving voltage, device life, including the novel organic compound.
  • the present invention provides a compound represented by the following formula (1), preferably a triphenylene series organic electroluminescent device material.
  • X is selected from the group consisting of CR 16 R 17 , O, S, SiR 18 R 19 , S ( ⁇ O), and S ( ⁇ O) 2 ;
  • R 1 to R 19 are the same or different, each independently represent hydrogen, deuterium, a halogen, an amino group, a nitro group, a nitrile group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 aryl group, C 5 ⁇ C 40 heteroaryl group, C 1 ⁇ C 40 alkoxy group, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyl Amino group, C 6 ⁇ C 40 arylamino group, C 6 ⁇ C 40 diarylamino group, C 5 ⁇ C 40 heteroarylamino group, C 5 ⁇ C 40 diheteroarylamino group, C 6 ⁇ C 40 arylalkyl group , C 5 to C 40 heteroarylalkyl group, C 3 to C 40 cycloalkyl group, C 1 to C 40 halogenalkyl group, C 3 to C 40 heterocycl
  • R 1 to R 19 may each be fused to an adjacent substituent or may form a ring.
  • the present invention is an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, a compound represented by the formula (1) It provides an organic electroluminescent device comprising at least one compound selected from the group consisting of.
  • the organic material layer including the compound represented by Chemical Formula 1 may be at least one selected from the group consisting of a light emitting layer, a hole injection layer, and a hole transporting layer, and more preferably, a phosphorescent or fluorescent host material of the light emitting layer.
  • Compound represented by the formula (1) of the present invention is excellent in brightness, power efficiency, heat resistance, hole or electron transport, injection performance, and can exhibit an increase in color purity and luminous efficiency to the light emitting layer, it is a hole and charge injection of the organic EL device It can be applied to at least one of a host, a dopant of phosphorescence and fluorescence of the layer, the transport layer and the light emitting layer.
  • OLED organic electroluminescent device
  • FIG. 1 is a schematic cross-sectional view of an organic EL device according to an embodiment of the present invention.
  • NPB N4, N4′-di (naphthalene-1-yl) -N4, N4′-diphenylbiphenyl-4,4′-diamine
  • CBP 4,4- dicarbazolybiphenyl
  • the compound represented by Formula 1 has an effect of stably forming triplet energy levels through orbital mixing by connecting a fused heterocyclic moiety to a triphenylene base skeleton.
  • the energy level is controlled by a variety of substituents to have a wide bandgap (sky blue ⁇ red).
  • the phosphorescence property of the device may be improved, and the electron and / or hole transport ability, the luminous efficiency, the driving voltage, and the lifespan characteristics may be improved. Therefore, the present invention may be applied to a hole transport layer, an electron transport layer, a host, and the like by introducing various substituents as well as the light emitting layer.
  • the wide bandgap derived from the triphenylene base skeleton may exhibit excellent properties as a host material, and due to the introduction of substituents such as tertiary amines, it may exhibit excellent properties as a hole transport layer (HTL) material. have.
  • HTL hole transport layer
  • the molecular weight of the compound is significantly increased due to the various aromatic ring substituents introduced into the triphenylene-based skeleton, so that the glass transition temperature is improved, which may have higher thermal stability than conventional NPB or CBP. have. Therefore, the device containing the triphenylene-based compound of the present invention can exhibit durability and lifespan improvement.
  • the compound represented by the compound of Formula 1 according to the present invention can greatly contribute to the performance improvement and lifespan improvement of the organic light emitting device, and in particular, the device life improvement has a great effect on maximizing performance in the full color organic light emitting panel.
  • R 1 to R 19 are the same as defined in Chemical Formula 1.
  • the compound of formula (I) including S as X may be more specified by the formulas illustrated below.
  • the compound represented by Formula 1 of the present invention is not limited to those illustrated below.
  • the compound of the formula (1) comprising O as X may be more specified by the formulas illustrated below.
  • the compound represented by Formula 1 of the present invention is not limited to those illustrated below.
  • the compound of formula (I) comprising CR 16 R 17 as X may be more specified by the formulas illustrated below.
  • the compound represented by Formula 1 of the present invention is not limited to those illustrated below.
  • the compound of formula 1 comprising SiR 18 R 19 as X may be more embodied by the formulas illustrated below.
  • the compound represented by Formula 1 of the present invention is not limited to those illustrated below.
  • the compound of formula (I) including S ⁇ O as X may be more specified by the formulas illustrated below.
  • the compound represented by Formula 1 of the present invention is not limited to those illustrated below.
  • the compound of formula (I) comprising SO 2 as X may be more specified by the formulas illustrated below.
  • the compound represented by Formula 1 of the present invention is not limited to those illustrated below.
  • the compounds represented by Formulas 1 to 7 of the present invention may be synthesized according to a general synthesis method. (see chem. Rev. , 60 : 313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995)) A detailed synthesis procedure for the compounds of the present invention is described This will be described in detail.
  • Another aspect of the invention relates to an organic electroluminescent device comprising a compound represented by Formula 1, preferably Formula 2 to Formula 7, according to the present invention described above.
  • the present invention is an anode (anode); Cathode; And at least one organic material layer interposed between the anode and the cathode, wherein at least one of the at least one organic material layer is represented by Formula 1, preferably, Formulas 2 to 7. It is characterized by including a compound.
  • the compound of Formula 1 to Formula 7 may be included alone or in plurality.
  • the organic material layer including the compound represented by Chemical Formula 1, preferably Chemical Formulas 2 to 7, may be any one or more of a hole injection layer, a hole transport layer, and a light emitting layer.
  • it can be included in the organic EL element as a hole injection layer and a hole transport layer material.
  • the organic EL device can maximize the hole injection / transport ability.
  • by being used as a light emitting layer material of an organic EL device it is possible to provide improved efficiency and lifetime.
  • the light emitting layer may include a phosphorescent guest material or a fluorescent guest material.
  • the compound represented by Formula 1 to Formula 7 may be included in the organic light emitting device as a blue, green and / or red phosphorescent host, a fluorescent host, a hole transport material and / or a hole transport material.
  • the triphenylene compound according to the present invention is preferable as a host material.
  • Compounds of formula (1) into which substituents such as tertiary amines are introduced are preferred as hole transport layer (HTL) materials.
  • the compound represented by Formula 1, preferably, Formulas 2 to 7, according to the present invention has a high glass transition temperature of 150 °C or more. Therefore, when the compound is used as an organic material layer of the organic light emitting device, since crystallization in the organic light emitting device is minimized, the driving voltage of the device can be lowered, and the luminous efficiency, thermal stability, and lifespan characteristics can be improved.
  • a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and a cathode may be sequentially stacked.
  • at least one of the emission layer, the hole injection layer, and the hole transport layer may include the compound represented by Chemical Formula 1.
  • An electron injection layer may be positioned on the electron transport layer.
  • the organic light emitting device may not only have a structure in which an anode, at least one organic layer, and a cathode are sequentially stacked, but an insulating layer or an adhesive layer may be inserted at an interface between the electrode and the organic layer.
  • the organic layer including the compound of Formula 1 to Formula 7 may be formed by a vacuum deposition method or a solution coating method.
  • the solution application include spin coating, dip coating, doctor blading, inkjet printing or thermal transfer method, but is not limited thereto.
  • the organic electroluminescent device according to the present invention is an organic material layer and an electrode using conventional materials and methods known in the art, except that at least one layer of the organic material layer is formed to include the compound represented by Chemical Formula 1 above. It can be prepared by forming.
  • a silicon wafer, quartz, glass plate, metal plate, plastic film or sheet may be used as the substrate.
  • the anode material may be a metal such as vanadium, chromium, copper, zinc, gold or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but is not limited thereto.
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SnO 2 : Sb
  • Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT),
  • Cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection layer, the hole transport layer and the electron injection layer is not particularly limited, and conventional materials known in the art may be used.
  • An organic EL device was manufactured in the following manner.
  • the glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 ⁇ was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol and the like was dried and transferred to a plasma cleaner, and then the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • ITO Indium tin oxide
  • the light emitting device was NPB (40 nm) / CBP + 10% Ir (ppy) 3 (20 nm) / BCP (10 nm) / Alq 3 (40 nm) / LiF (1 nm) / Al. After the configuration, the luminescence properties were evaluated in the same manner as in Examples 1 to 11.
  • NPB, CBP, Ir (ppy) 3 and BCP are as follows.
  • An organic EL device was manufactured in the following manner.
  • the glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, and the like was dried, transferred to a plasma cleaner, and then the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.

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

Abstract

Cette invention concerne un nouveau composé électroluminescent organique et une diode électroluminescente organique le contenant, et plus particulièrement, un nouveau composé électroluminescent organique qui est utilisé à titre de matériau pour injecter et transférer des trous ou des électrons et émettre une lumière, et une diode électroluminescente organique l'utilisant.
PCT/KR2012/005474 2011-07-11 2012-07-11 Composé à base de triphénylène et diode électroluminescente organique l'utilisant WO2013009079A1 (fr)

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US20160190472A1 (en) * 2014-12-30 2016-06-30 Luminescence Technology Corp. Organic material and organic electroluminescent device using the same
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JP2016153394A (ja) * 2015-02-17 2016-08-25 機光科技股▲分▼有限公司 有機エレクトロルミネセンス素子用インデノトリフェニレン系アミン誘導体
JP2016525512A (ja) * 2013-07-10 2016-08-25 サムスン エスディアイ カンパニー, リミテッドSamsung Sdi Co., Ltd. 有機化合物、有機光電子素子および表示装置
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CN106831622A (zh) * 2015-12-03 2017-06-13 机光科技股份有限公司 有机材料及使用其的有机电激发光组件
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US10807972B2 (en) 2018-10-15 2020-10-20 Feng-wen Yen Indenotriphenylene-based amine derivative and organic electroluminescence device using the same
CN112961140A (zh) * 2021-02-08 2021-06-15 北京云基科技有限公司 一种萘醌杂环化合物及应用
CN113004243A (zh) * 2021-02-08 2021-06-22 北京云基科技有限公司 一种含萘醌的杂环化合物及其应用
CN113004262A (zh) * 2021-02-08 2021-06-22 北京云基科技有限公司 一种有机材料及其应用
CN113004261A (zh) * 2021-02-08 2021-06-22 北京云基科技有限公司 一种含多杂环结构的化合物及其应用
US11177446B2 (en) * 2017-09-14 2021-11-16 Beijing Summer Sprout Technology Co., Ltd. Silicon containing organic fluorescent materials
TWI747141B (zh) * 2019-01-17 2021-11-21 機光科技股份有限公司 有機化合物及使用其的有機電致發光器件
TWI792166B (zh) * 2021-01-29 2023-02-11 機光科技股份有限公司 有機化合物和以其作為材料的紅光有機發光裝置
CN116003356A (zh) * 2022-12-30 2023-04-25 宁波卢米蓝新材料有限公司 含有三亚苯的多环杂芳族基团的化合物及其有机电致发光材料及其应用

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KR102253441B1 (ko) 2014-03-10 2021-05-20 삼성디스플레이 주식회사 화합물 및 이를 포함한 유기 발광 소자
KR101503796B1 (ko) * 2014-05-08 2015-03-18 성균관대학교산학협력단 유기 발광 화합물, 이의 제조 방법 및 이를 포함하는 유기 전계 발광 소자
KR101904299B1 (ko) 2014-05-12 2018-10-04 제일모직 주식회사 유기 화합물, 유기 광전자 소자 및 표시 장치
US10312451B2 (en) * 2015-01-26 2019-06-04 Luminescence Technology Corporation Compound for organic electroluminescent device
KR102018238B1 (ko) 2016-09-21 2019-09-04 삼성에스디아이 주식회사 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치
KR101962756B1 (ko) 2016-09-29 2019-03-27 삼성에스디아이 주식회사 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치
WO2019013509A1 (fr) * 2017-07-10 2019-01-17 주식회사 엘지화학 Nouveau composé hétérocyclique et dispositif électroluminescent organique l'utilisant
CN111087416B (zh) * 2018-10-24 2024-05-14 北京夏禾科技有限公司 含硅的电子传输材料及其应用

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WO2014094954A1 (fr) * 2012-12-18 2014-06-26 Merck Patent Gmbh Composés à base d'indénophénanthrène
US10032990B2 (en) 2013-07-10 2018-07-24 Samsung Sdi Co., Ltd. Organic composition, and organic optoelectronic element and display device
JP2016525512A (ja) * 2013-07-10 2016-08-25 サムスン エスディアイ カンパニー, リミテッドSamsung Sdi Co., Ltd. 有機化合物、有機光電子素子および表示装置
US20160190472A1 (en) * 2014-12-30 2016-06-30 Luminescence Technology Corp. Organic material and organic electroluminescent device using the same
CN105732594A (zh) * 2014-12-30 2016-07-06 机光科技股份有限公司 有机材料和使用其的有机电致发光装置
JP2016155797A (ja) * 2014-12-30 2016-09-01 機光科技股▲分▼有限公司 有機材料およびそれを用いた有機エレクトロルミネッセンス素子
TWI564290B (zh) * 2014-12-30 2017-01-01 機光科技股份有限公司 有機材料及使用此材料之有機電激發光裝置
US9793493B2 (en) * 2014-12-30 2017-10-17 Luminescence Technology Corp. Organic material and organic electroluminescent device using the same
CN105801430A (zh) * 2015-01-19 2016-07-27 机光科技股份有限公司 菲并[9,10-b]联亚四苯衍生物以及其用途
CN105801430B (zh) * 2015-01-19 2018-08-28 机光科技股份有限公司 菲并[9,10-b]联亚四苯衍生物以及其用途
US10164194B2 (en) * 2015-01-26 2018-12-25 Luminescence Technology Corporation Compound for organic electroluminescent device
JP2016153394A (ja) * 2015-02-17 2016-08-25 機光科技股▲分▼有限公司 有機エレクトロルミネセンス素子用インデノトリフェニレン系アミン誘導体
US20170012211A1 (en) * 2015-07-10 2017-01-12 Samsung Display Co., Ltd. Organic light-emitting device
TWI619690B (zh) * 2015-11-23 2018-04-01 機光科技股份有限公司 有機化合物及使用其的有機電激發光元件
TWI617547B (zh) * 2015-12-03 2018-03-11 Luminescence Technology Corporation 有機材料及使用其的有機電激發光元件
CN106831622A (zh) * 2015-12-03 2017-06-13 机光科技股份有限公司 有机材料及使用其的有机电激发光组件
CN106986813A (zh) * 2016-01-06 2017-07-28 机光科技股份有限公司 用于有机电场发光装置的基于茚并三亚苯的胺衍生物
CN110546143A (zh) * 2017-07-10 2019-12-06 株式会社Lg化学 新型杂环化合物及包含其的有机发光器件
US11177446B2 (en) * 2017-09-14 2021-11-16 Beijing Summer Sprout Technology Co., Ltd. Silicon containing organic fluorescent materials
CN110526825B (zh) * 2018-05-25 2023-04-07 江苏三月科技股份有限公司 一种以异屈与三芳胺结构为核心的化合物及其应用
CN110526825A (zh) * 2018-05-25 2019-12-03 江苏三月光电科技有限公司 一种以异屈与三芳胺结构为核心的化合物及其应用
US10807972B2 (en) 2018-10-15 2020-10-20 Feng-wen Yen Indenotriphenylene-based amine derivative and organic electroluminescence device using the same
TWI728502B (zh) * 2018-10-15 2021-05-21 機光科技股份有限公司 基於茚並三亞苯的胺衍生物及使用其的有機電激發光裝置
CN111320607B (zh) * 2018-12-17 2021-11-19 机光科技股份有限公司 以含有三亚苯的多环杂芳族基团为核心的有机化合物及其应用
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CN113004243A (zh) * 2021-02-08 2021-06-22 北京云基科技有限公司 一种含萘醌的杂环化合物及其应用
CN113004261B (zh) * 2021-02-08 2023-02-17 北京云基科技股份有限公司 一种含多杂环结构的化合物及其应用
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