WO2010150988A2 - Dérivés d’anthracène et dispositif électroluminescent organique les utilisant - Google Patents

Dérivés d’anthracène et dispositif électroluminescent organique les utilisant Download PDF

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WO2010150988A2
WO2010150988A2 PCT/KR2010/003528 KR2010003528W WO2010150988A2 WO 2010150988 A2 WO2010150988 A2 WO 2010150988A2 KR 2010003528 W KR2010003528 W KR 2010003528W WO 2010150988 A2 WO2010150988 A2 WO 2010150988A2
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WO2010150988A3 (fr
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이은정
김경수
김태형
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주식회사 두산
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    • 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
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Definitions

  • the present invention relates to a novel anthracene derivative and an organic electroluminescent device using the same. More specifically, the present invention provides an N, O or S element as a substituent having an electron transfer ability to the core while having a core in which an anthracene moiety having excellent device characteristics and a moiety such as fluorene having excellent fluorescent properties are fused with each other.
  • the novel compounds include the C 2 ⁇ C 40 heteroaryl group is substituted for;
  • it relates to an organic electroluminescent device including the organic material layer containing the compound improved characteristics such as luminous efficiency, brightness, thermal stability, driving voltage, lifespan.
  • organic light emitting phenomenon refers to a phenomenon in which light appears when electric energy is applied to an organic material. That is, when the organic material layer is positioned between the anode and the cathode, a voltage is applied between the two electrodes, and holes are injected into the organic material and electrons are injected into the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall back to the ground, they shine.
  • an organic electroluminescent device As one method for making an organic electroluminescent device efficiently, research has been conducted to manufacture an organic material layer in a multi-layer structure instead of a single layer.
  • Tang presented an organic electroluminescent device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer, and most organic electroluminescent devices currently used are hole injections that receive holes as a substrate, an anode, and an anode. It consists of a layer, a hole transport layer for transferring holes, a light emitting layer for recombining holes and electrons to emit light, an electron transport layer for transferring electrons, an electron injection layer for receiving electrons from a cathode, and a cathode.
  • the reason why the organic electroluminescent device is manufactured in multiple layers is that the movement speed of the holes and the electrons is different. Therefore, if the appropriate hole injection layer, the transfer layer, the electron transfer layer, and the electron injection layer are made, the holes and the electrons can be effectively transferred. This is because light emission efficiency can be improved by balancing holes and electrons in the device.
  • the earliest reports on the material of electron transport include oxadiazole derivatives (PBDs). It has since been reported that triazole derivatives (TAZ) and phenanthroline derivatives (BCP) exhibit electron transport properties.
  • PBDs oxadiazole derivatives
  • TEZ triazole derivatives
  • BCP phenanthroline derivatives
  • the electron transport layer is a good candidate for the organic monomolecular materials such as organometallic complexes having excellent electron stability and electron transfer speed, and Alq3 having high stability and electron affinity is the best candidate. Is being used.
  • the electron transport materials disclosed in Japanese Patent Application Laid-Open No. 11-345686 report that they contain oxazole groups and thiazole groups and can be applied to the light emitting layer, but have reached practical use in terms of driving voltage, luminance, and lifetime of the device. I can't.
  • the present invention is to provide a novel compound that can be applied to the organic electroluminescent device.
  • the present invention is to provide an organic electroluminescent device that includes a novel compound is low in driving voltage, the luminous efficiency, brightness, thermal stability, lifespan, and the like.
  • the present invention provides a compound represented by the following formula (1).
  • R 1 to R 7 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, nitrile group, nitro group, amino group, silyl group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, C 2 ⁇ C 40 heterocycloalkyl group, C 6 ⁇ C 40 aryl group, C 1 ⁇ alkyloxy group of C 40 of the, C 5 ⁇ C 40 An aryloxy group, a C 5 to C 40 arylamino group, a C 5 to C 40 diarylamino group, a C 5 to C 40 aryl group, or a C 2 to C 40 heteroaryl group; Or a group which forms a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group;
  • R 1 , R 2 , R 3 and R 4 is a C 2 to C 40 heteroaryl group containing at least one element selected from the group consisting of N, O and S;
  • Ar 1 to Ar 4 are the same as or different from each other, and are each independently an arylene group of C 5 to C 40 , or a hetero arylene group of C 2 to C 40 ;
  • a, b, c and d are the same as or different from each other, and are each independently an integer of 0 to 3;
  • the present invention is an anode; cathode; And one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is an organic material layer including the compound represented by Formula 1 of the present invention.
  • An organic electroluminescent device is provided.
  • the organic material layer containing the compound represented by Formula 1 is preferably an electron transport layer.
  • the compound represented by Chemical Formula 1 according to the present invention has excellent electron transport performance, when it is adopted as an electron transport layer material of an organic light emitting device, the compound exhibits superior performance in terms of voltage and efficiency than conventional Alq3. Therefore, the compound represented by Chemical Formula 1 according to the present invention can greatly contribute to improving performance and lifespan of the organic light emitting device, and in particular, the improvement of electron transport performance has a great effect on maximizing performance in a full color organic light emitting panel.
  • the compound represented by Formula 1 of the present invention is a core in which an anthracene moiety having excellent device characteristics and a moiety such as fluorene having excellent fluorescence properties are fused to each other (for example, indenoanthracene ( and a heteroaryl group of C 2 to C 40 containing an N, O or S element as a substituent having an electron transfer capability, and having an indenoanthracene core), and a kind of anthracene derivative.
  • an anthracene moiety having excellent device characteristics and a moiety such as fluorene having excellent fluorescence properties are fused to each other (for example, indenoanthracene ( and a heteroaryl group of C 2 to C 40 containing an N, O or S element as a substituent having an electron transfer capability, and having an indenoanthracene core), and a kind of anthracene derivative.
  • the compound represented by Chemical Formula 1 of the present invention may be used as a hole injection material, a hole transport material, a light emitting material, an electron transport material or an electron injection material in an organic light emitting device, preferably an electron transport material, or an electron injection material and It can be used as a transport material.
  • the amino group, the C 5 -C 40 diarylamino group, the C 5 -C 40 aryl group, or the C 2 -C 40 heteroaryl group are each independently deuterium, halogen, nitrile group, nitro group, amino group, silyl group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 1 ⁇ C 40 alkoxy group, C 1
  • At least one of R 1 , R 2 , R 3 and R 4 is at least one element selected from the group consisting of N (nitrogen), O (oxygen) and S (sulfur) C 2 ⁇ C 40 It is a heteroaryl group containing.
  • the heteroaryl group of C 2 ⁇ C 40 is not particularly limited, but may be selected from the group consisting of the structural formulas of Formula 2 below.
  • an aryl group of C 5 ⁇ C 40 in R 1 to R 7 is not particularly limited, but may be selected from the group consisting of the following structural formula (3).
  • Q 1 to Q 4 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen, a nitrile group, a nitro group, C 1 ⁇ alkenyl group of the C 40 alkyl group, C 2 ⁇ C 40 of, C 2 ⁇ C 40 of the alkynyl group, C 1 ⁇ C 40 alkoxy group, C 1 ⁇ C 40 of the amino group, C of 3 ⁇ C 40 cycloalkyl group, C of 3 ⁇ C 40 heterocycloalkyl group, C 6 ⁇ C 40 aryl An alkyl group, a C 5 -C 40 aryl group, or a C 5 -C 40 heteroaryl group.
  • a cycloalkyl group, a C 3 to C 40 heterocycloalkyl group, a C 6 to C 40 aryl group and a C 5 to C 40 heteroaryl group are each independently deuterium, halogen, nitrile group, nitro group, C 1 to C 40 Alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 1 ⁇ C 40 alkoxy group, C 1 ⁇ C 40 amino group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ It may be substituted with a C 40 heterocycloalkyl group, a C 6 ⁇ C 40 arylalkyl group, a C 5 ⁇ C 40 aryl group, or
  • Ar 1 to Ar 4 are each independently a C 5 ⁇ C 40 arylene group or C 2 ⁇ C 40 heteroarylene group, preferably C 5 ⁇ C 40 Arylene group.
  • the arylene group of C 5 ⁇ C 40 may be an arylene group selected from the group consisting of the formula of Formula 3,
  • C 2 ⁇ C 40 heteroarylene group is a heteroaryl selected from the group consisting of the formula It may be a Rengi.
  • the present invention is an anode; cathode; And one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is an organic material layer including the compound represented by Formula 1 of the present invention.
  • An organic light emitting device is provided.
  • the compound represented by Formula 1 may include one kind or two or more kinds.
  • the organic material layer including the compound represented by Formula 1 of the present invention may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
  • the compound represented by Chemical Formula 1 may be included in the organic electroluminescent device as an electron transport material or an electron injection and transport material, in which case the organic electroluminescent device has a low driving voltage, luminous efficiency, luminance, Thermal stability and lifespan can be improved. Therefore, preferably, the organic material layer including the compound represented by Chemical Formula 1 is an electron transport layer.
  • the organic electroluminescent device according to the present invention may include any one or more or all of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer in addition to the organic material layer containing a compound represented by the formula (1) of the present invention. Can be.
  • 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, and the electron transport layer may be a chemical structure of the organic electroluminescent device according to the present invention. It includes the compound represented by 1.
  • An electron injection layer may be positioned on the electron transport layer.
  • the organic EL device according to the present invention may not only have a structure in which an anode, one or more organic material layers, 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 material layer.
  • the organic material layer including the compound represented by Chemical Formula 1 may be formed by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
  • the organic electroluminescent device of the present invention is formed using a hole injection layer, a hole using 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 Formula 1 of the present invention. It can be produced by forming an organic layer and an electrode, such as a transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • Example 1-2 to Example 1-26 Synthesis of Compound of Formula 4-002 to Formula 4-026]
  • the compounds of Formula 4-002 to Formula 4-026 may be synthesized using the same method as in Example 1-1 (Synthesis of Compound of 4-001), respectively, and were obtained as a pale yellow solid. .
  • Example 2-2 to Example 2-14 Synthesis of Compounds of Chemical Formula 5-002 to Chemical Formula 5-014
  • Example 3-2 to Example 3-48 Synthesis of Compounds of Chemical Formula 6-002 to Chemical Formula 6-048
  • the compounds of Formulas 6-002 to 6-648 may be synthesized using the same method as in Example 3-1 (Synthesis of Compounds of Formula 6-001), respectively, and were obtained as a pale yellow solid. .
  • the compounds of Formulas 7-002 to 7-011 were each synthesized using the same method as in Example 4-1 (Synthesis of Compounds of Formula 7-001), and were obtained as a pale yellow solid. .
  • Example 5-1 to Example 5-31 Fabrication of organic light emitting device
  • Product name DS-205 (Doosan Corporation) was vacuum deposited on an ITO transparent electrode to a thickness of 800 kPa to form a hole injection layer, and on top of it, NPB ( N , N- di (naphthalene-1-yl) -N , N- diphenylbenzidine) was deposited to a thickness of 150 ⁇ to form a hole transport layer.
  • ADN (9,10-di (naphthalen-2-yl) anthracene) was used as a host thereon, and a light emitting layer was formed by doping DS-405 (Doosan Co., Ltd.) 5% with a dopant to a thickness of 300 Pa.
  • Each of the electron transporting materials synthesized in Examples 1 to 4 was deposited on the light emitting layer to a thickness of 250 kPa to form an electron transporting layer.
  • 10F thick LiF was deposited on the electron transport layer to form an electron injection layer, and 2,000V thick Al was deposited thereon to form a cathode to manufacture a device.
  • the device When forming the electron transport layer, the device was manufactured in the same manner as in Example 5 except that Alq3 (aluminum tris (8-hydroxyquinoline)) was used instead of the material synthesized in Examples 1 to 4 as the electron transporting material.
  • Alq3 aluminum tris (8-hydroxyquinoline)
  • the organic light emitting device (Examples 5-1 to 5-31) using the compound according to the present invention as an electron transporting material is more voltage and efficiency than the organic light emitting device (Comparative Example 1) using Alq3. We can see that it shows superior performance in.

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  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
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  • Optics & Photonics (AREA)
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Abstract

La présente invention concerne des dérivés d’anthracène et un dispositif électroluminescent organique les utilisant. Plus spécifiquement, la présente invention concerne : un composé innovant qui comporte un cœur (par exemple un cœur d’indénoanthracène), aussi bien un groupe caractéristique anthracène présentant des caractéristiques de dispositif supérieures qu’un groupe caractéristique comme le fluor présentant des caractéristiques de fluorescence supérieures étant fusionnés, et un groupe hétéroaryle comportant 2 à 40 atomes de carbone contenant des éléments N, O ou S est substitué au cœur comme substituant présentant des capacités de transfert d’électron ; et un dispositif électroluminescent organique utilisant le composé innovant.
PCT/KR2010/003528 2009-06-22 2010-06-01 Dérivés d’anthracène et dispositif électroluminescent organique les utilisant WO2010150988A2 (fr)

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US20120161615A1 (en) * 2009-06-19 2012-06-28 Doosan Corporation Aminoanthracene derivative and an organic electroluminescent element employing the same
CN102766011A (zh) * 2012-08-07 2012-11-07 吉林奥来德光电材料股份有限公司 一种芴基蒽衍生物、制备方法及由其制成的有机电发光器件
US20120286249A1 (en) * 2011-05-13 2012-11-15 Jae-Yong Lee Condensed-cyclic compound, organic light-emitting device comprising the same, and flat panel display apparatus including the device
US20120286246A1 (en) * 2011-05-13 2012-11-15 Samsung Mobile Display Co., Ltd. Condensed-cyclic compound, organic light-emitting device comprising the same, and flat panel display apparatus
CN103045232A (zh) * 2012-10-18 2013-04-17 吉林奥来德光电材料股份有限公司 二氢并五苯烯烃类有机发光材料及其制备方法和应用
CN103497164A (zh) * 2013-09-23 2014-01-08 西安近代化学研究所 一种蒽衍生物及其制备方法
US20140239263A1 (en) * 2013-02-25 2014-08-28 Samsung Display Co., Ltd. Anthracene-based compound and organic light emitting diode comprising the same
CN104151314A (zh) * 2014-08-15 2014-11-19 郑州大学 一种萘并咪唑并吡啶类化合物及其制备方法
WO2017014226A1 (fr) * 2015-07-21 2017-01-26 Jnc株式会社 Composé contenant un cycle azoline, matériau pour des couches de transport/d'injection d'électrons contenant ce dernier et élément électroluminescent organique l'utilisant
CN108440525A (zh) * 2018-04-25 2018-08-24 长春海谱润斯科技有限公司 一种苝衍生物及其有机电致发光器件

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KR101319631B1 (ko) * 2011-12-19 2013-10-17 주식회사 두산 아자인데노안트라센 유도체 및 이를 이용한 유기 전계 발광 소자
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KR102115070B1 (ko) * 2017-09-21 2020-05-25 주식회사 엘지화학 화합물, 이를 포함하는 코팅 조성물, 이를 이용한 유기 발광 소자 및 이의 제조방법

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Publication number Priority date Publication date Assignee Title
US20120161615A1 (en) * 2009-06-19 2012-06-28 Doosan Corporation Aminoanthracene derivative and an organic electroluminescent element employing the same
US9115112B2 (en) * 2009-06-19 2015-08-25 Doosan Corporation Aminoanthracene derivative and an organic electroluminescent element employing the same
US8999525B2 (en) * 2011-05-13 2015-04-07 Samsung Display Co., Ltd. Condensed-cyclic compound, organic light-emitting device comprising the same, and flat panel display apparatus including the device
US20120286249A1 (en) * 2011-05-13 2012-11-15 Jae-Yong Lee Condensed-cyclic compound, organic light-emitting device comprising the same, and flat panel display apparatus including the device
US20120286246A1 (en) * 2011-05-13 2012-11-15 Samsung Mobile Display Co., Ltd. Condensed-cyclic compound, organic light-emitting device comprising the same, and flat panel display apparatus
US9012042B2 (en) * 2011-05-13 2015-04-21 Samsung Display Co., Ltd. Condensed-cyclic compound, organic light-emitting device comprising the same, and flat panel display apparatus
CN102766011A (zh) * 2012-08-07 2012-11-07 吉林奥来德光电材料股份有限公司 一种芴基蒽衍生物、制备方法及由其制成的有机电发光器件
CN103045232A (zh) * 2012-10-18 2013-04-17 吉林奥来德光电材料股份有限公司 二氢并五苯烯烃类有机发光材料及其制备方法和应用
US20140239263A1 (en) * 2013-02-25 2014-08-28 Samsung Display Co., Ltd. Anthracene-based compound and organic light emitting diode comprising the same
CN103497164A (zh) * 2013-09-23 2014-01-08 西安近代化学研究所 一种蒽衍生物及其制备方法
CN103497164B (zh) * 2013-09-23 2015-12-23 西安近代化学研究所 一种蒽衍生物及其制备方法
CN104151314A (zh) * 2014-08-15 2014-11-19 郑州大学 一种萘并咪唑并吡啶类化合物及其制备方法
WO2017014226A1 (fr) * 2015-07-21 2017-01-26 Jnc株式会社 Composé contenant un cycle azoline, matériau pour des couches de transport/d'injection d'électrons contenant ce dernier et élément électroluminescent organique l'utilisant
JPWO2017014226A1 (ja) * 2015-07-21 2018-04-26 Jnc株式会社 アゾリン環含有化合物、これを含有する電子輸送／注入層用材料およびこれを用いた有機電界発光素子
US11342511B2 (en) 2015-07-21 2022-05-24 Sk Materials Jnc Co., Ltd. Azoline ring-containing compound, electron transport/injection layer material containing the same, and organic electroluminescent element using the same
CN108440525A (zh) * 2018-04-25 2018-08-24 长春海谱润斯科技有限公司 一种苝衍生物及其有机电致发光器件

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