WO2011031086A2 - 신규한 헤테로고리 유도체 및 이를 이용한 유기 발광 소자 - Google Patents
신규한 헤테로고리 유도체 및 이를 이용한 유기 발광 소자 Download PDFInfo
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- WO2011031086A2 WO2011031086A2 PCT/KR2010/006167 KR2010006167W WO2011031086A2 WO 2011031086 A2 WO2011031086 A2 WO 2011031086A2 KR 2010006167 W KR2010006167 W KR 2010006167W WO 2011031086 A2 WO2011031086 A2 WO 2011031086A2
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- 238000007740 vapor deposition Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Definitions
- the present invention relates to a novel compound and an organic light emitting device using the same.
- the organic light emitting phenomenon is an example of converting an electric current into visible light by an internal process of a specific organic molecule.
- the principle of the organic light emitting phenomenon is as follows. When the organic material layer is placed between the anode and the cathode, when a voltage is applied between the two electrodes, electrons and holes are injected into the organic material layer from the cathode and the anode, respectively. Electrons and holes injected into the organic material layer recombine to form excitons, and the excitons fall back to the ground to shine.
- An organic light emitting device using this principle may generally be composed of an organic material layer including a cathode and an anode, and an organic material layer disposed therebetween, such as a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer.
- the materials used in the organic light emitting device are pure organic materials or complex compounds in which organic materials and metals are complexed, and depending on the purpose, hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials, etc. It can be divided into.
- the hole injection material or the hole transport material an organic material having a p-type property, that is, an organic material which is easily oxidized and has an electrochemically stable state during oxidation, is mainly used.
- organic materials having n-type properties that is, organic materials that are easily reduced and have an electrochemically stable state at the time of reduction are mainly used.
- the light emitting layer material a material having a p-type property and an n-type property at the same time, that is, a material having a stable form in both oxidation and reduction states, and a material having high luminous efficiency that converts it to light when excitons are formed desirable.
- the material used in the organic light emitting device additionally have the following properties.
- the material used in the organic light emitting device is preferably excellent in thermal stability. This is because joule heating occurs due to the movement of charges in the organic light emitting diode.
- NPB which is mainly used as a hole transport layer material, has a glass transition temperature of 100 ° C. or less, and thus is difficult to use in an organic light emitting device requiring a high current.
- the material used for the organic light emitting device should have an appropriate band gap and HOMO or LUMO energy level.
- PEDOT PSS, which is currently used as a hole transport material in organic light emitting devices manufactured by the solution coating method, has a low LUMO energy level compared to the LUMO energy level of organic materials used as a light emitting layer material. There is difficulty.
- the material used in the organic light emitting device should be excellent in chemical stability, charge mobility, interface characteristics between the electrode and the adjacent layer. That is, the material used in the organic light emitting device should be less deformation of the material by moisture or oxygen. In addition, by having an appropriate hole or electron mobility it should be able to maximize the exciton formation by balancing the density of holes and electrons in the light emitting layer of the organic light emitting device. In addition, for the stability of the device should be able to improve the interface with the electrode containing a metal or metal oxide.
- the present inventors can satisfy the conditions required for the materials that can be used in the organic light emitting device, such as appropriate energy level, electrochemical stability and thermal stability, and the chemistry that can play various roles required in the organic light emitting device depending on the substituent. It is an object to provide a novel heterocyclic derivative having a structure and an organic light emitting device using the same.
- the present invention provides a compound represented by Formula 1:
- L is a linking group connected to at least one A, a substituted or unsubstituted C 6 ⁇ C 60 arylene group, a substituted or unsubstituted fluorene group, or a substituted or unsubstituted C 3 ⁇ C 60 heteroarylene group,
- Y 1 and Y 2 are the same as or different from each other, and each independently a substituted or unsubstituted C 6 to C 60 aryl group, or a substituted or unsubstituted C 3 to C 60 heteroaryl group,
- p is an integer from 1 to 10
- At least one of X 1 to X 7 is connected to L, and the rest are each independently hydrogen deuterium halogen cyano group nitro group hydroxyl group substituted or unsubstituted C 1 to C 50 alkyl group substituted or unsubstituted C 1 to C 50 alkoxy group substituted or unsubstituted C 3 to C 50 cycloalkyl group substituted or unsubstituted C 3 to C 60 heterocycloalkyl group substituted or unsubstituted C 6 to C 60 aryl group substituted or unsubstituted C 3 to C 60 Heteroaryl group substituted or unsubstituted arylamine group or substituted or unsubstituted silicone group.
- the present invention is an organic light emitting device comprising a first electrode, at least one organic material layer including a light emitting layer and a second electrode in a stacked form, wherein at least one layer of the organic material layer comprises a compound of Formula 1 Provided is an organic light emitting device.
- the compound of the present invention can be used as an organic layer material, in particular a light emitting material, a hole injection material and / or a hole transport material in the organic light emitting device, when the compound is used in the organic light emitting device lowers the driving voltage of the device, improving the light efficiency In addition, it is possible to improve the life characteristics of the device by the thermal stability of the compound.
- the light emitting layer of the organic light emitting device according to the present invention may include a phosphorescent or fluorescent dopant of red, green, blue or white.
- the phosphorescent dopant may be an organometallic compound including one or more elements selected from the group consisting of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, and Tm.
- FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG.
- FIG. 2 shows an example of an organic light emitting device consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4. It is.
- One embodiment of the compound according to the present invention is represented by the formula (1).
- the aryl group may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 60.
- the monocyclic aryl group include phenyl group, biphenyl group, terphenyl group, stilbene, and the like
- examples of the polycyclic aryl group include naphthyl group, anthracenyl group, phenanthrene group, pyrenyl group, peryleneyl group, and chrysenyl group. Etc., but the scope of the present invention is not limited only to these examples.
- a heterocyclic group such as a heterocycloalkyl group or a heteroaryl group is a ring group containing O, N or S as a hetero atom, and the carbon number is not particularly limited, but is preferably 3 to 60.
- the heteroaryl group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, pyrazine group, quinolinyl group, isoquinoline group, acryri Dill group, etc., but is not limited to these.
- heterocyclic groups are preferable as the substituted or unsubstituted heteroarylene group, but are not limited thereto.
- the fluorene group is preferably the following structure, but is not limited thereto.
- an alkyl group or an alkoxy group includes a straight or branched chain.
- substituted or unsubstituted is deuterium halogen cyano group nitro group hydroxyl group C 1 ⁇ C 50 alkyl group C 1 ⁇ C 50 alkoxy group C 3 ⁇ C 50 cycloalkyl group C 3 ⁇ C 60 heterocycloalkyl group C 6 ⁇ C 60
- Arylamine group Means unsubstituted or substituted with at least one substituent selected from the group consisting of a fluorene group and a silicone group.
- X 1 is connected to L and X 2 is an aryl group.
- X 1 is linked to L and X 2 and X 3 are an aryl group.
- X 2 is connected to L and X 1 is an aryl group.
- X 2 is connected to L and X 1 and X 3 are an aryl group.
- Specific examples of the compound of Formula 1 may be a compound represented by the following formula, but is not limited thereto.
- R1 to R4 are the same as the definitions of X 1 to X 7 in Formula 1, and n is an integer of 1 to 4.
- Formula A prepared in Scheme 1 may be subjected to Suzuki coupling, introduction of an amine group, and bromination reaction under a Pd catalyst to prepare a compound represented by Formula 1.
- the compound represented by Chemical Formula 1 according to the present invention may be prepared by a multistage chemical reaction.
- the preparation of the compounds is described by the following preparation. As shown in the preparation examples, some intermediate compounds are prepared first, and compounds represented by the formula (1) are prepared from the intermediate compounds.
- the organic electronic device according to the present invention is an organic electronic device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, one or more of the organic layer It is characterized by including a compound represented by the formula (1).
- the organic electronic device of the present invention may be manufactured by a conventional method and material for manufacturing an organic electronic device, except that one or more organic material layers are formed using the above-described compounds.
- the compound represented by Chemical Formula 1 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of an organic electronic device.
- the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, roll coating and the like, but is not limited thereto.
- the organic material layer of the organic electronic device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
- the organic electronic device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic material layer.
- the structure of the organic electronic device is not limited thereto and may include a smaller number of organic material layers.
- the organic material layer may include a hole injection layer and a hole transport layer
- the hole injection layer or hole transport layer may include a compound represented by the formula (1).
- the organic material layer may include a light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1.
- the compound represented by Chemical Formula 1 in the multilayer organic material layer may form an organic material layer that plays at least one role of light emission, hole injection, hole transport, electron transport, and electron injection.
- the organic electronic device according to the present invention is included in a light emitting layer, a hole injection and / or a transport layer, or a layer which simultaneously emits light and holes.
- the light emitting layer of the organic light emitting device according to the present invention may include a phosphorescent or fluorescent dopant including red, green, blue or white.
- the phosphorescent dopant may be an organometallic compound including one or more elements selected from the group consisting of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, and Tm.
- the structure of the organic light emitting device of the present invention may have a structure as shown in FIG. 1 or 2, but is not limited thereto.
- FIG. 1 shows an example of an organic light emitting device having a structure in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked.
- 2 shows an example of an organic light emitting device consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4. It is.
- FIG. 1 and 2 illustrate a normal structure in which an anode is positioned on a substrate.
- the present invention is not limited thereto, and the present invention also includes an inverted structure in which a cathode is positioned on a substrate.
- the organic light emitting device uses a metal vapor deposition (PVD) method such as sputtering or e-beam evaporation, and has a metal oxide or a metal oxide or an alloy thereof on a substrate. It can be prepared by depositing an anode to form an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
- PVD metal vapor deposition
- an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
- the organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure.
- the organic layer may be prepared by using a variety of polymer materials, and by using a method such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than a deposition method. It can be prepared in layers.
- anode material a material having a large work function is usually preferred to facilitate hole injection into the organic material layer.
- the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof, such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO).
- Oxides Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb Poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) compound (PEDT), polypyrrole and polyaniline Conductive polymers and the like, but are not limited thereto.
- the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
- the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or multilayered structures such as alloys thereof LiF / Al or LiO 2 / Al. Substances and the like, but are not limited thereto.
- the hole injection material is a material capable of well injecting holes from the anode at a low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
- the hole injection material include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene-based organics, quinacridone-based organics, and perylene-based Organic substances, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
- the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer, and is a material having high mobility to holes. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
- the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
- Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole family compound dimerized styryl compounds BAlq; 10-hydroxybenzo quinoline-metal compound benzoxazole, benzthiazole and benzimidazole-based compound poly (p-phenylenevinylene) (PPV) -based polymer spiro compound polyfluorene, rubrene and the like
- the present invention is not limited thereto.
- the electron transport material a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer is suitable.
- Specific examples include, but are not limited to, complex organic radical compounds hydroxyflavone-metal complexes including Al complex Alq 3 of 8-hydroxyquinoline.
- the organic light emitting device 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.
- N-biphenyl-1-naphtylamine N-biphenyl-1-naphtylamine, 8.0 g, 27.15 mmol
- N-biphenyl-1-naphtylamine 8.0 g, 27.15 mmol
- sodium-butoxy-butoxide 3.56 g, 37 mmol
- 0.13 g (0.247 mmol) of Pd [P (t-Bu) 3 ] 2 were added and then refluxed under nitrogen stream for 5 hours.
- Distilled water was added to the reaction solution to terminate the reaction, and the organic layer was extracted.
- Normal-hexane / tetrahydrofuran 10/1 was separated by column, and then stirred in petroleum ether and dried in vacuo to obtain the formula 1-2 (6.8g, 49% yield).
- a glass substrate (corning 7059 glass) coated with ITO (Indium Tin Oxide) with a thickness of 1,000 ⁇ was placed in distilled water in which a dispersant was dissolved, and ultrasonically washed. Fischer Co. products were used for the detergent, and Millipore Co. Secondly filtered distilled water was used as a filter of the product. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried.
- ITO Indium Tin Oxide
- Hexitrile hexaazatriphenylene was thermally vacuum deposited to a thickness of 500 kPa on the prepared ITO transparent electrode to form a hole injection layer.
- Chemical Formula 1-1 400 kPa synthesized in the above Preparation Example as a material for transporting holes thereon
- the host H1 and the dopant D1 compound were vacuum deposited to a thickness of (300 kPa) as a light emitting layer.
- an E1 compound 300 kV
- An organic light emitting device was manufactured by sequentially depositing 12 ⁇ thick lithium fluoride (LiF) and 2,000 ⁇ thick aluminum on the electron injection and transport layer to form a cathode.
- the deposition rate of the organic material was maintained at 1 ⁇ / sec
- the lithium fluoride was 0.2 ⁇ / sec
- the aluminum was maintained at a deposition rate of 3 to 7 ⁇ / sec.
- the compound derivative of the formula according to the present invention may serve as hole injection, hole transport, electron injection and transport, or a light emitting material in an organic electric device including an organic light emitting device, and the device according to the present invention has efficiency, driving voltage, and stability. Excellent properties in terms of appearance.
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Abstract
Description
Claims (10)
- 하기 화학식 1로 표시되는 화합물:[화학식 1]상기 화학식 1에 있어서,L은 적어도 하나의 A와 연결되는 연결기로서, 치환 또는 비치환된 C6 ~ C60 아릴렌기, 치환 또는 비치환된 플루오렌기, 또는 치환 또는 비치환된 C3 ~ C60 헤테로아릴렌기이며,Y1 및 Y2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 C6 ~ C60 아릴기, 또는 치환 또는 비치환된 C3 ~ C60 헤테로아릴기이며,p는 1 내지 10의 정수이고,X1 내지 X7 중 적어도 하나는 상기 L과 연결되고, 나머지는 각각 독립적으로 수소 중수소 할로겐 시아노기 니트로기 히드록실기 치환 또는 비치환된 C1 ~ C50 알킬기 치환 또는 비치환된 C1 ~ C50 알콕시기 치환 또는 비치환된 C3 ~ C50 사이클로알킬기 치환 또는 비치환된 C3 ~ C60 헤테로사이클로알킬기 치환 또는 비치환된 C6 ~ C60 아릴기 치환 또는 비치환된 C3 ~ C60 헤테로아릴기 치환 또는 비치환된 아릴아민기 또는 치환 또는 비치환된 실리콘기이다.
- 청구항 1에 있어서, 상기 화학식 1의 아릴기는 페닐기, 바이페닐, 터페닐기, 스틸벤, 나프틸기, 안트라세닐기, 페나트렌기, 파이레닐기, 페릴레닐기, 또는 크라이세닐기인 것인 화합물.
- 청구항 1에 있어서, 상기 화학식 1의 헤테로아릴기는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 피라다진기, 퀴놀리닐기, 이소퀴놀린기, 또는 아크리딜기인 것인 화합물.
- 제1 전극, 발광층을 포함하는 1층 이상의 유기물층 및 제2 전극을 적층된 형태로 포함하는 유기 발광 소자에 있어서, 상기 유기물층 중 1층 이상이 청구항 1의 화합물을 포함하는 것인 유기 발광 소자.
- 청구항 8에 있어서, 상기 발광층은 적색, 녹색, 청색 또는 백색의 인광 또는 형광 도펀트를 포함하는 것인 유기 발광 소자.
- 청구항 9에 있어서, 상기 인광 도펀트는 Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb 및 Tm으로 이루어진 군으로부터 선택된 하나 이상의 원소를 포함하는 유기 금속 화합물인 것인 유기 발광 소자.
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CN201080040255.0A CN102482575B (zh) | 2009-09-10 | 2010-09-10 | 新的杂环衍生物及使用其的有机电致发光器件 |
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JP5905584B2 (ja) | 2012-02-27 | 2016-04-20 | エルジー・ケム・リミテッド | 有機発光素子 |
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JP2014240396A (ja) | 2014-12-25 |
KR101117938B1 (ko) | 2012-02-29 |
EP2476738A2 (en) | 2012-07-18 |
KR20110027635A (ko) | 2011-03-16 |
WO2011031086A3 (ko) | 2011-08-04 |
EP2476738A4 (en) | 2014-09-10 |
US8673460B2 (en) | 2014-03-18 |
CN102482575A (zh) | 2012-05-30 |
JP2013504568A (ja) | 2013-02-07 |
US20120161612A1 (en) | 2012-06-28 |
EP2476738B1 (en) | 2017-11-01 |
CN102482575B (zh) | 2015-01-21 |
JP5638612B2 (ja) | 2014-12-10 |
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