KR100525408B1 - organic electroluminescence device - Google Patents

organic electroluminescence device Download PDF

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KR100525408B1
KR100525408B1 KR10-2003-0020465A KR20030020465A KR100525408B1 KR 100525408 B1 KR100525408 B1 KR 100525408B1 KR 20030020465 A KR20030020465 A KR 20030020465A KR 100525408 B1 KR100525408 B1 KR 100525408B1
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light emitting
formula
organic
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KR20040057862A (en
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오형윤
서정대
이경훈
김희정
박춘건
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엘지전자 주식회사
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Priority to EP03029661.0A priority Critical patent/EP1437395B2/en
Priority to US10/743,778 priority patent/US7700201B2/en
Priority to CNB2003101244058A priority patent/CN100481574C/en
Priority to JP2003428297A priority patent/JP3926791B2/en
Publication of KR20040057862A publication Critical patent/KR20040057862A/en
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Publication of KR100525408B1 publication Critical patent/KR100525408B1/en
Priority to JP2006245563A priority patent/JP4778384B2/en
Priority to US12/714,639 priority patent/US8436344B2/en

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H10K2102/10—Transparent electrodes, e.g. using graphene
    • H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
    • H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/917—Electroluminescent

Abstract

본 발명은 색순도가 우수한 청색 발광 물질을 사용하는 유기 전계 발광 소자에 관한 것으로, 전자 주입 전극(음극)과 정공 주입 전극(양극) 사이에 발광층을 포함하고, 이 발광층이 청색 발광물질인 하기 화학식 1의 물질을 포함하는 유기 전계 발광 소자를 제공한다.The present invention relates to an organic electroluminescent device using a blue light emitting material having excellent color purity, comprising a light emitting layer between an electron injection electrode (cathode) and a hole injection electrode (anode), wherein the light emitting layer is a blue light emitting material. It provides an organic electroluminescent device comprising a substance.

Description

유기 전계 발광 소자{organic electroluminescence device}Organic electroluminescence device

본 발명은 유기 전계 발광 소자에 관한 것으로서, 특히 유기발광층의 청색 발광 물질로서 하기 화학식 1의 구조를 갖는 화합물을 포함하는 유기 전계 발광 소자에 관한 것이다.The present invention relates to an organic electroluminescent device, and more particularly, to an organic electroluminescent device comprising a compound having a structure of Formula 1 as a blue light emitting material of the organic light emitting layer.

(상기 식에서, A1과 A2는 각각 독립적으로 치환되거나 치환되지 않은 방향족 그룹, 이형고리 그룹, 지방족 그룹 또는 수소로부터 선택될 수 있다) (Wherein A 1 and A 2 may be each independently selected from a substituted or unsubstituted aromatic group, heterocyclic group, aliphatic group or hydrogen)

최근 표시장치의 대형화에 따라 공간 점유가 적은 평면표시소자의 요구가 증대되고 있는데, 이러한 평면표시소자 중 하나로서 유기발광다이오드(organic light emitting diode: OLED)라고도 불리는 유기 전계 발광 소자의 기술이 빠른 속도로 발전하고 있으며, 이미 여러 시제품들이 발표된 바 있다.Recently, as the size of the display device increases, the demand for a flat display device having less space is increasing. As one of the flat display devices, an organic light emitting diode (OLED), also called an organic light emitting diode (OLED), has a high speed. It has been developed and several prototypes have already been announced.

유기 전계 발광 소자는 전자 주입 전극(음극)과 정공 주입 전극(양극) 사이에 형성된 유기막에 전하를 주입하면 전자와 정공이 쌍을 이룬 후 소멸하면서 빛을 내는 소자이다. 플라스틱과 같은 휠 수 있는(flexible) 투명 기판 위에도 소자를 형성할 수 있을 뿐 아니라, 플라즈마 디스플레이 패널(Plasma Display Panel)이나 무기 전계 발광(EL) 디스플레이에 비해 낮은 전압에서 (10V이하) 구동이 가능하고, 또한 전력 소모가 비교적 적으며, 색감이 뛰어나다는 장점이 있다. 또한 유기 전계 발광(EL) 소자는 녹색, 청색, 적색의 3가지 색을 나타낼 수가 있어 차세대의 풍부한 색 디스플레이 소자로 많은 사람들의 관심의 대상이 되고 있다. 그러나, 종래의 유기 전계 발광 소자에서의 청색 발광 물질은 색순도가 떨어지고 그 수명이 짧다는 단점이 있다. An organic electroluminescent device is a device that emits light when electrons and holes are paired and then disappear when electrons are injected into an organic film formed between an electron injection electrode (cathode) and a hole injection electrode (anode). Not only can the device be formed on a flexible transparent substrate such as plastic, but it can also be driven at a lower voltage (less than 10V) compared to a plasma display panel or an inorganic electroluminescent (EL) display. In addition, it has the advantage of relatively low power consumption and excellent color. In addition, the organic electroluminescent (EL) device can display three colors of green, blue, and red, and thus, has become a target of many people as a next-generation rich color display device. However, the blue light emitting material in the conventional organic EL device has a disadvantage in that the color purity is low and the life thereof is short.

한편, 유기 EL 소자를 제작하는 일반적인 과정을 살펴보면,Meanwhile, looking at the general process of manufacturing the organic EL device,

(1) 먼저, 투명기판 위에 양극 물질을 입힌다. 상기 양극 물질로는 흔히 ITO(indium tin oxide)가 사용된다.(1) First, an anode material is coated on a transparent substrate. Indium tin oxide (ITO) is commonly used as the cathode material.

(2) 그 위에 정공주입층(HIL:hole injecting layer)을 입힌다. 상기 정공주입층으로는 주로 구리 프탈로시아닌(copper phthalocyanine(CuPC))을 10nm 내지 30nm 두께로 입힌다.(2) Apply a hole injecting layer (HIL) on it. As the hole injection layer, copper phthalocyanine (CuPC) is mainly coated with a thickness of 10 nm to 30 nm.

(3) 다음으로 정공수송층(HTL:hole transport layer)을 도입한다. 이러한 정공수송층으로는 4,4'-비스[N-(1-나프틸)-N-페닐아미노]바이페닐(4,4'-bis[N-(1-naphthyl)-N-phenthylamino]-biphenyl(NPB)을 30nm 내지 60nm 정도 증착하여 입힌다.(3) Next, a hole transport layer (HTL) is introduced. As the hole transport layer, 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (4,4'-bis [N- (1-naphthyl) -N-phenthylamino] -biphenyl (NPB) is deposited by depositing about 30 nm to 60 nm.

(4) 그 위에 유기발광층 (organic emitting layer)을 형성한다. 이때 필요에 따라 불순물(dopant)을 첨가한다. 예를 들어, 녹색(green) 발광의 경우 호스트(host)로 트리스(8-하이드록시퀴놀레이트)알루미늄(Alq3)(tris(8-hydroxy-quinolatealuminum)을, 불순물(dopant)로 MQD(N-메틸퀴나크리돈)(N-Meth ylquinacridone) 또는 쿠마린(Coumarine)유도체를 1~2% 도핑하여 20nm-40nm정도의 발광층을 형성한다. 또한 청색 발광의 경우는 발광층 호스트(host)로 PBD, DPVBi와 같은 물질을 사용하고 불순물(dopant)로는 페릴렌(Perylene), 쿠마린(coumarine), 파이렌 (pyrene)과 같은 물질을 통상 1-3% 수준으로 도핑하여 제작한다.(4) Form an organic emitting layer thereon. At this time, a dopant is added as necessary. For example, in the case of green light emission, tris (8-hydroxyquinolate) aluminum (Alq 3 ) is used as the host, and MQD (N- is used as the dopant). Doping 1 ~ 2% of N-Meth ylquinacridone) or coumarin derivative forms a light emitting layer of about 20nm-40nm, and in the case of blue light emission, PBD, DPVBi and The same material is used, and as a dopant, materials such as perylene, coumarine and pyrene are usually doped by 1-3%.

(5) 그 위에 전자수송층(ETL:electron transport layer) 및 전자주입층(EIL: electron injecting layer)을 연속적으로 입힌다. (5) An electron transport layer (ETL) and an electron injecting layer (EIL) are successively coated thereon.

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한편, 상기 (4)의 Alq3는 전자 주입 및 수송 능력을 동시에 가지므로 전자 주입층을 따로 사용하지 않기도 한다.On the other hand, Alq 3 in the above (4) may have an electron injection and transport capability at the same time, and may not use an electron injection layer separately.

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(6) 다음으로 음극(cathode)을 입힌다. 이때 전자 주입을 보다 용이하게 하기 위하여 LiF, Li2O 등의 알칼리 산화물을 얇게 입힌 후 Al을 입힌다. 마지막으로 보호막을 덧 씌운다.(6) Next, a cathode is coated. At this time, in order to make electron injection easier, Al oxide is applied after thinly coating alkali oxides such as LiF and Li 2 O. Finally, a protective shield is added.

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하지만 유기 EL 소자를 제작하는 과정에서 상기한 종래의 청색 발광 물질을 사용하는 경우 진한 청색(deep blue)을 얻기가 어렵고 단파장으로 갈수록 발광 수명이 짧아지는 문제점이 있어 천연색의 풀컬러 디스플레이(full color display)를 구현하는 데 있어 진한 청색(deep blue)재료의 개발이 절실히 요구된다. However, when using the above-mentioned conventional blue light emitting material in the process of fabricating an organic EL device, it is difficult to obtain deep blue and the light emission life is shortened toward shorter wavelengths. The development of deep blue materials is urgently needed.

이에 본 발명은 상기와 같은 문제점을 해결하기 위해 안출된 것으로, 청색발광 물질로 새로운 물질을 합성하여 청색의 색순도가 우수하여 발광 특성이 향상된 유기 전계 발광 소자를 제공하는데 그 목적이 있다. Accordingly, an object of the present invention is to provide an organic electroluminescent device having improved light emission characteristics by synthesizing a new material with a blue light emitting material and excellent blue color purity.

상기한 목적을 달성하기 위해서, 본 발명은 음극/정공주입층/정공수송층/발광층/전자수송층/전자주입층/양극으로 구성되는 일반적인 유기 전계 발광 소자에 있어서, 아래의 구조를 가지는 물질을 발광층의 청색 발광 물질로 사용하는 것을 특징으로 한다.In order to achieve the above object, the present invention is a general organic electroluminescent device consisting of a cathode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / anode, the material having the structure of It is used as a blue light emitting material.

[화학식 1][Formula 1]

(상기 식에서, A1과 A2는 각각 독립적으로 치환되거나 치환되지 않은 방향족 그룹, 이형고리 그룹, 지방족 그룹 또는 수소로부터 선택될 수 있다) 특히 상기 화학식 1에서 A1과 A2는 치환되거나 치환되지 않은 페닐(phenyl), 바이페닐(biphenyl), 파이리디닐(pyridyl), 나프틸(naphthyl), 퀴놀릴(quinolyl), 이소퀴놀릴 (isoquinolyl), 플로레닐(fluorenyl), 터페닐(terphenyl) 및 메틸(methyl), 에틸(ethyl), 프로필(propyl), 이소프로필(i-propyl), t-부틸(t-buthyl) 등으로부터 선택될 수 있다. 또한 이때 A1 및 A2에 치환되는 치환기는 각각 1개 이상일 수 있고, 알킬(alkyl), 알콕시(alkoxy), 알킬아미노(alkylamino), 알킬실릴(alkylsilyl), 할로겐(halogen), 아릴(aryl), 아릴옥시(aryloxy), 아릴아미노(arylamino), 아릴실릴 (arylsilyl)기 중에서 선택될 수 있다. 예를 들면 A1, A2의 치환기로는 메틸(methyl), 에틸(ethyl), 프로필(propyl), 이소프로필(i-propyl), t-부틸(t-butyl), 사이클로헥실(cyclohexyl), 메톡시(methoxy), 에톡시(ethoxy), 프로폭시(propoxy), 부톡시(butoxy), 디메틸아미노 (dimethylamino), 디에틸아미노(diethylamino), 트리메틸실릴(trimethylsilyl), 불소, 염소, 페녹시(phenoxy), 토릴옥시(tolyoxy), 디페닐아미노(diphenylamino), 트리페닐실릴(triphenylsilyl)이 선택될 수 있다.예를 들면, 치환되거나 치환되지 않은 A1 및 A2는 하기 화학식 3과 같은 구조를 갖는 물질로부터 선택될 수 있다. 이러한 치환기 A1과 A2를 갖는 화학식 1의 물질은, 예를 들면 다음 화학식 4와 같은 구조를 갖는다. 또한, 상기 화학식 1의 발광 물질은 한가지 이상의 다른 물질과 혼합하여 사용될 수 있으며, 혼합하여 사용시 상기 물질은 발광층의 총 중량을 기준으로 질량%가 0.1 ~ 90 질량%이다. Wherein A 1 and A 2 may be each independently selected from a substituted or unsubstituted aromatic group, heterocyclic group, aliphatic group or hydrogen. Particularly, in Formula 1, A 1 and A 2 may be substituted or unsubstituted. Phenyl, biphenyl, pyridyl, naphthyl, quinolyl, isoquinolyl, fluorenyl, terphenyl and Methyl, ethyl, propyl, isopropyl, t-butyl, and the like can be selected. In addition, at this time, the substituents substituted in A 1 and A 2 may each be one or more, alkyl (alkyl), alkoxy (alkyl), alkylamino (alkylamino), alkylsilyl (halogen), aryl (aryl) , Aryloxy, arylamino, arylsilyl may be selected from the group. For example, substituents of A1 and A2 include methyl, ethyl, propyl, isopropyl, t-butyl, cyclohexyl and methoxy. (methoxy), ethoxy, propoxy, butoxy, dimethylamino, diethylamino, trimethylsilyl, fluorine, chlorine, phenoxy , Tolyoxy, diphenylamino, triphenylsilyl may be selected. For example, substituted or unsubstituted A1 and A2 may be selected from materials having a structure such as Can be. The substance of the formula (1) having such substituents A 1 and A 2 has a structure such as the following formula (4). In addition, the light emitting material of Formula 1 may be used in combination with one or more other materials, when used in combination, the material is a mass% of 0.1 to 90% by mass based on the total weight of the light emitting layer.

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상기 발광층으로 함께 혼합하여 사용되는 물질은 바람직하게는 다음과 같은 구조를 가진다. B1 - X - B2 The material used by mixing together into the light emitting layer preferably has the following structure. B1-X-B2

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상기 식에서 X는 융합된 방향족 화합물(fused Aromatic compounds)로부터 선택될 수 있으며, 특히 나프탈렌(naphthalene), 안트라센 (anthracene) 페난트렌(phenanthrene), 파이렌(pyrene), 페릴렌(perylene) 및 퀴놀린(quinoline) 그룹으로 부터 선택될 수 있다. Wherein X may be selected from fused Aromatic compounds, in particular naphthalene, anthracene phenanthrene, pyrene, perylene and quinoline ) Can be selected from the group.

또한, B1 및 B2는 각각 아릴(aryl), 알킬아릴(alkylaryl), 알콕시아릴(alkoxyaryl), 아릴아미노아릴(arylaminoaryl), 알킬아미노아릴(alkylaminoaryl) 및 아릴알릴(arylallyl)기로 이루어진 그룹으로부터 선택될 수 있으며, 특히 페닐(phenyl), 바이페닐(biphenyl), 파이리딜 (pyridyl), 나프틸(naphthyl), 트리틸페닐(tritylphenyl), 바이페닐레닐(biphenylenyl), 안트릴 (anthryl), 페난트릴(phenanthryl), 파이레닐 (pyrenyl), 퍼릴렌일(perylenyl), 퀴놀릴 (quinolyl), 아이소퀴놀릴 (isoquinolyl), 플로레닐(fluorenyl), 터페닐(terphenyl), 톨릴(tolyl), 자일릴(Xylyl), 메틸나프틸 (methylnaphthyl) 그룹 및 수소로부터 선택될 수 있다. In addition, B1 and B2 may be selected from the group consisting of aryl, alkylaryl, alkoxyaryl, arylaminoaryl, alkylaminoaryl, and arylallyl groups, respectively. Especially, phenyl, biphenyl, pyridyl, naphthyl, tritylphenyl, biphenylenyl, anthryl, phenanthryl ), Pyrenyl, perylenyl, quinolyl, quinolyl, isoquinolyl, fluorenyl, terphenyl, tolyl, xylyl, Methylnaphthyl group and hydrogen.

예를 들면, 상기 화학식 2의 물질로 다음과 같은 물질이 사용될 수 있다. For example, the following materials may be used as the material of Chemical Formula 2.

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본 발명에 따른 유기 전계 발광 소자에 있어서 청색 발광 물질로 사용될 수 있는 물질 중 N,N'-Bis-(4-tert-butyl-phenyl)-N,N'-di-pyridin-2-yl-pyrene-1,6-diamine은 다음의 방법에 따라 얻어질 수 있다. N, N'-Bis- (4-tert-butyl-phenyl) -N, N'-di-pyridin-2-yl-pyrene among materials that can be used as a blue light emitting material in the organic electroluminescent device according to the present invention -1,6-diamine can be obtained according to the following method.

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1) 1,6-Dibromopyrene의 합성1) Synthesis of 1,6-Dibromopyrene

먼저 3구 둥근 바닥 플라스크에 파이렌(pyrene)(10g, 0.049mol)을 CCl4(300mL)에 녹인다. 그런 다음 상기 둥근 바닥 플라스크에 설치된 적하 깔대기(dropping funnel)에 Br2(17.38g, 0.108mol)와 CCl4(50mL)을 넣은 후 이것을 둥근 바닥 플라스크에 4시간에 걸쳐 천천히 적하시키며 N2를 주입 발생되는 HBr을 제거한다. 적하(dropping)가 끝나면 1시간을 N2 기류 하에서 교반시킨 후 반응이 종결되면 생성된 침전물을 그대로 필터한 후 이 침전물을 다시 톨루엔을 사용하여 재결정하여 1,6-Dibromopyrene의 녹색 고체(6.05g, 34%)와 1,8-Dibromopyrene(5g, 28%)의 흰색 고체를 얻었다.First dissolve pyrene (10 g, 0.049 mol) in CCl 4 (300 mL) in a three neck round bottom flask. Then, Br 2 (17.38 g, 0.108 mol) and CCl 4 (50 mL) were added to a dropping funnel installed in the round bottom flask, and the mixture was slowly added to the round bottom flask over 4 hours, and N 2 was injected. Remove HBr. After dropping, the mixture was stirred for 1 hour under N 2 stream, and when the reaction was completed, the resultant precipitate was filtered as it is, and the precipitate was recrystallized again using toluene to give a green solid of 1,6-Dibromopyrene (6.05g, 34%) and 1,8-Dibromopyrene (5 g, 28%) were obtained.

2)N,N,N',N'-Tetraphenyl-pyrene-1,6-diamine의 합성2) Synthesis of N, N, N ', N'-Tetraphenyl-pyrene-1,6-diamine

2구 둥근 바닥 플라스크에 상기 1)에서 얻은 1,6-Dibromopyrene(3g, 0.0083mol)과, Diphenylamine(4.23g, 0.029mol), BINAP([2,2'-bis(diphenylphosphino)-1,1'-binaphthyl])(0.052g, 1% mol), Pd(OAC)2[Palladium(∥)acetate](0.019g, 1% mol)과 NaOtBu[Sodium tert-butoxide](2.3g, 0.029mol)를 톨루엔(80mL)에 녹인 후 24시간 환류한다(reflux). 반응이 종결되면, 둥근 바닥 플라스크를 냉각시키고, 반응 용매인 톨루엔 40mL를 제거한 후 여기에 메탄올(100mL)을 첨가하면 침전물이 생성된다. 얻어진 침전물을 필터하여 원하는 N,N,N',N'-Tetraphenyl-pyrene-1,6-diamine(3.22g, 72%)의 노란색 고체를 얻었다.In a two-necked round bottom flask, 1,6-Dibromopyrene (3g, 0.0083mol) obtained in 1), Diphenylamine (4.23g, 0.029mol) and BINAP ([2,2'-bis (diphenylphosphino) -1,1 ' -binaphthyl]) (0.052g, 1% mol), Pd (OAC) 2 [Palladium (∥) acetate] (0.019g, 1% mol) and NaO t Bu [Sodium tert-butoxide ] (2.3g, 0.029mol) Was dissolved in toluene (80 mL) and refluxed for 24 hours (reflux). At the end of the reaction, the round bottom flask was cooled, 40 mL of toluene, the reaction solvent was removed, and methanol (100 mL) was added thereto to form a precipitate. The precipitate obtained was filtered to give a yellow solid of the desired N, N, N ', N'-Tetraphenyl-pyrene-1,6-diamine (3.22 g, 72%).

3) (4-Bromo-phenyl)-trimethyl-silane의 합성3) Synthesis of (4-Bromo-phenyl) -trimethyl-silane

먼저 3구 둥근 바닥 플라스크에 적하 깔대기를 설치하고, 감압 하에서 건조시킨다. 그 후 둥근 바닥 플라스크에 1,4-Dibromobenzene(12,7g, 0.053mol)과 건조된 diethylether(300mL)를 넣고 용해시킨다. 그리고 드라이아이스 배스(bath)를 설치한 후 적하 깔대기에 n-BuLi(33,58mL, 0.0537mol)를 넣은 후 천천히 적하한다. 그 후에 -78℃에서 0℃로 온도를 1시간에 걸쳐 올리고 여기에 Chloro trimethylsilane(7,51mL, 0.059mol)을 천천히 적하하고 다시 온도를 상온으로 1시간에 걸쳐 올린다. 반응이 종결되면 물과 diethylether를 사용하여 추출하고 MgSO4를 사용하여 물을 제거한 후 용매를 제거하고 그 후 감압 하에서 분별증류를 하여(4-Bromo-phenyl)-trimethyl-silane(11.3g, 92%)을 얻었다.First, a dropping funnel is installed in a three-necked round bottom flask and dried under reduced pressure. Then, 1,4-Dibromobenzene (12,7g, 0.053mol) and dried diethylether (300mL) were dissolved in a round bottom flask. After installing a dry ice bath, n-BuLi (33,58 mL, 0.0537 mol) was added to the dropping funnel and slowly added dropwise. After that, increase the temperature from -78 ° C to 0 ° C over 1 hour, and slowly drop Chloro trimethylsilane (7,51mL, 0.059mol) to it and raise the temperature to room temperature over 1 hour. After completion of the reaction, the mixture was extracted with water and diethylether, water was removed using MgSO 4 , solvent was removed, and then distilled under reduced pressure (4-Bromo-phenyl) -trimethyl-silane (11.3g, 92%). )

4) (4-tert-Butyl-phenyl)-(4-trimethylsilanyl-phenyl)-amine의 합성4) Synthesis of (4-tert-Butyl-phenyl)-(4-trimethylsilanyl-phenyl) -amine

2구 둥근 바닥 플라스크에 4-tert-Butyl-phenylamine(1.2mL, 0.0076mol), 상기 3)에서 얻은 (4-Bromo-phenyl)-trimethyl-silane(1g,0.0044mol), BINAP(0.03g, 1%mol), Pd(OAc)2(0.01g, 1%mol)과 NaOtBu(1.5g, 0.016mol)를 톨루엔(50mL)에 녹인후 24시간 환류한다. 반응이 종결되면, 둥근 바닥 플라스크를 냉각시키고, 반응용액인 톨루엔을 제거한 후 물과 methylene chloride를 사용하여 추출하고 MgSO4로 물을 제거하고 methylene chloride를 감압으로 제거하고 hexane을 사용하여 silica gel short column을 하고 에탄올과 물을 사용하여 침전이 생기면 이것을 필터하여 흰색 고체인 4-(4-tert-Butyl-phenyl)-(4-trimethylsilanyl-phenyl)-amine(1.12g,86%)을 얻을 수 있다.In a two-neck round bottom flask, 4-tert-Butyl-phenylamine (1.2 mL, 0.0076 mol), (4-Bromo-phenyl) -trimethyl-silane (1 g, 0.0044 mol) obtained from 3), BINAP (0.03 g, 1 % mol), Pd (OAc) 2 (0.01 g, 1% mol) and NaO t Bu (1.5 g, 0.016 mol) are dissolved in toluene (50 mL) and refluxed for 24 hours. After the reaction was completed, the round bottom flask was cooled, the reaction solution was removed toluene, extracted with water and methylene chloride, water was removed with MgSO 4 , methylene chloride was removed under reduced pressure, and hexane was used for silica gel short column. When precipitation occurs using ethanol and water, this can be filtered to obtain 4- (4-tert-Butyl-phenyl)-(4-trimethylsilanyl-phenyl) -amine (1.12 g, 86%) as a white solid.

5) N,N'-Bis-(4-tert-butyl-phenyl)-N,N'-bis-(4-trimethylsilanyl-phenyl)-pyrene-1,6-diamine의 합성5) Synthesis of N, N'-Bis- (4-tert-butyl-phenyl) -N, N'-bis- (4-trimethylsilanyl-phenyl) -pyrene-1,6-diamine

2구 둥근 바닥 플라스크에 상기 1)에서 얻은 1,6-Dibromopyrene(0.787g, 0.0022mol), 상기 4)에서 얻은 (4-tert-Butyl-phenyl)-(4-trimethylsilanyl-phenyl)-amine(1,56g, 0.00525mol), BINAP(0.054g, 4%mol), Pd(OAc)2(0.015g, 3%mol)와 NaOtBu(0.93g, 0.0096mol)를 톨루엔(40mL)에 녹인 후 24시간 환류한다. 반응이 종결되면, 둥근 바닥 플라스크를 냉각시키고, 반응 용매인 톨루엔을 제거한 후 물과 methylene chloride를 사용하여 추출하고 MgSO4로 물을 제거하고 methylene chloride를 감압으로 제거하고 silica gel chromatography를 용매 hexane:methylene chloride(6:1)을 사용하여 분리한다. 그런 다음 용매를 제거한 후 hexane을 사용하여 고체를 필터하면 녹색빛깔의 노란 고체인 N,N'-Bis-(4-tert-butyl-phenyl)-N,N'-bis-(4-trimethylsilanyl-phenyl)-pyrene-1,6-diamine(1.09g, 63%)을 얻을 수 있다.1,6-Dibromopyrene (0.787 g, 0.0022 mol) obtained in 1) and (4-tert-Butyl-phenyl)-(4-trimethylsilanyl-phenyl) -amine (1) obtained in 4) in a two-neck round bottom flask. , 56g, 0.00525mol), BINAP (0.054g, 4% mol), Pd (OAc) 2 (0.015g, 3% mol) and NaO t Bu (0.93g, 0.0096mol) dissolved in toluene (40mL) Time to reflux. After the reaction was completed, the round bottom flask was cooled, the reaction solvent toluene was removed, extracted with water and methylene chloride, the water was removed with MgSO 4 , the methylene chloride was removed under reduced pressure, and the silica gel chromatography was subjected to solvent hexane: methylene. Separate with chloride (6: 1). Then remove the solvent and filter the solid using hexane. N, N'-Bis- (4-tert-butyl-phenyl) -N, N'-bis- (4-trimethylsilanyl-phenyl ) -pyrene-1,6-diamine (1.09 g, 63%).

6) N,N'-Diphenyl-N,N'-di-pyridin-2-yl-pyrene-1,6-diamine의 합성6) Synthesis of N, N'-Diphenyl-N, N'-di-pyridin-2-yl-pyrene-1,6-diamine

2구 둥근 바닥 플라스크에 상기 1)에서 얻은 1,6-Dibromopyrene(1.2g, 0.0033mol), Phenyl-pyridin-2-yl-amine(1,36g, 0.008mol), BINAP(0.083g, 4%mol), Pd(OAc)2(0.022g, 3%mol)와 NaOtBu(1.28g, 0.013mol)를 톨루엔(50mL)에 녹인 후 24시간 환류한다. 반응이 종결되면 고체가 생성된다. 이것을 먼저 톨루엔을 50%정도 제거한 후 여기에 메탄올(70mL)을 첨가하여 필터를 하게 되면 노란색 고체인 N,N'-Diphenyl-N,N'-di-pyridin-2-yl-pyrene-1,6-diamine(0.81g, 45%)을 얻을 수 있다.1,6-Dibromopyrene (1.2g, 0.0033mol), Phenyl-pyridin-2-yl-amine (1,36g, 0.008mol), BINAP (0.083g, 4% mol) obtained in 1) in a two-neck round bottom flask ), Pd (OAc) 2 (0.022 g, 3% mol) and NaO t Bu (1.28 g, 0.013 mol) are dissolved in toluene (50 mL) and refluxed for 24 hours. At the end of the reaction a solid is produced. First, remove 50% of toluene, and then add methanol (70mL) and filter it to yellow solid N, N'-Diphenyl-N, N'-di-pyridin-2-yl-pyrene-1,6 -diamine (0.81g, 45%) is obtained.

7) (4-terr-Butyl-phenyl)-pyridin-2-yl-amine의 합성7) Synthesis of (4-terr-Butyl-phenyl) -pyridin-2-yl-amine

2구 둥근 바닥 플라스크에 4-tert-Butyl-phenylamine(1.2mL, 0.0076mol), 2-Bromo pyridine(1mL, 0.01mol), BINAP(0.06g, 4%mol), Pd(OAc)2(0.02g, 3%mol)과 NaOtBu(1.5g, 0.016mol)를 톨루엔(50mL)에 녹인 후 24시간 환류한다. 반응이 종결되면, 둥근 바닥 플라스크를 냉각시키고, 반응 용매인 톨루엔을 제거한 후 물과 methylene chloride를 사용하여 추출한다. 그리고 MgSO4로 물을 제거하고 methylene chloride를 감압으로 제거하고 methylene chloride를 사용하여 silica gel short column을 하고 hexane을 사용하여 침전이 생기면 이것을 필터하여 흰색 고체인 (4-tert-Butyl-phenyl)-pyridin-2-yl-amine(1.32g, 73%)을 얻을 수 있다.4-tert-Butyl-phenylamine (1.2 mL, 0.0076 mol), 2-Bromo pyridine (1 mL, 0.01 mol), BINAP (0.06 g, 4% mol), Pd (OAc) 2 (0.02 g) in a 2 -neck round bottom flask , 3% mol) and NaO t Bu (1.5 g, 0.016 mol) are dissolved in toluene (50 mL) and refluxed for 24 hours. After the reaction is completed, the round bottom flask is cooled, the toluene, the reaction solvent, is removed, and extracted with water and methylene chloride. Remove water with MgSO 4 , remove methylene chloride under reduced pressure, use silica gel short column with methylene chloride, and precipitate with hexane, filter it and filter it to white solid (4-tert-Butyl-phenyl) -pyridin 2-yl-amine (1.32 g, 73%) is obtained.

8)N,N'-Bis-(4-tert-butyl-phenyl)-N,N'-di-pyridin-2yl-pyrene-1,6-diamine의 합성8) Synthesis of N, N'-Bis- (4-tert-butyl-phenyl) -N, N'-di-pyridin-2yl-pyrene-1,6-diamine

2구 둥근 바닥 플라스크에 1,6-Dibromopyrene(1g, 0.0028mol), 상기 7)에서 얻은 (4-tert-Butyl-phenyl)-pyridin-2-yl-amine(1.51g, 0.0067mol), BINAP(0.07g, 4%mol), Pd(OAc)2(0.02g, 3%mol)와 NaOtBu(1.18g, 0.012mol)를 톨루엔(45mL)에 녹인 후 24시간 환류한다. 반응이 종결되면 고체가 생성된다. 이것을 먼저 톨루엔을 50%정도 제거한 후 여기에 메탄올(70mL)을 첨가하여 필터를 하고 methylene chloride를 사용하여 silica gel short column을 하여 용매를 제거하면 N,N'-Bis-(4-tert-butyl-Phenyl)-N,N'-di-pyridin-2-yl-pyrene-1,6-diamine(0.99g, 60%)을 얻을 수 있다.In a two-neck round bottom flask, (4-tert-Butyl-phenyl) -pyridin-2-yl-amine (1.51 g, 0.0067 mol) obtained from 1,6-Dibromopyrene (1 g, 0.0028 mol), 7), BINAP ( after 0.07g, 4% mol), Pd (OAc) 2 (0.02g, 3% mol) and NaO t Bu (1.18g, 0.012mol) was dissolved in toluene (45mL) and refluxed for 24 hours. At the end of the reaction a solid is produced. Remove 50% of toluene first, filter it by adding methanol (70mL), and remove the solvent by silica gel short column using methylene chloride. N, N'-Bis- (4-tert-butyl- Phenyl) -N, N'-di-pyridin-2-yl-pyrene-1,6-diamine (0.99g, 60%) can be obtained.

이하, 본 발명에 따른 유기 전계 발광 소자의 바람직한 양태를 실시예로 설명한다.Hereinafter, the preferable aspect of the organic electroluminescent element which concerns on this invention is demonstrated to an Example.

실시예Example

ITO(Indium Tin Oxide)(산화인듐주석) 기판(glass)의 발광 면적이 3mm×3mm 크기가 되도록 패터닝(patterning)한 후 세정한다. 상기 기판을 진공 챔버에 장착한 후 기본 압력이 1×10-6torr가 되도록 한 후 유기물을 ITO위에 CuPC(200Å), NPB(500Å), 발광층(300Å), Alq3(200Å), LiF(5Å), Al(1000Å)의 순서로 성막하였다. 이때 발광층의 제 1 HOST로는 아래 물질(HOST-1)을 사용했으며, 불순물로는 본 발명의 화학식 1에 따른 물질 S-28을 사용하였고 HOST-1과 S-28의 혼합비는 1:0.01로 하였다.The light emitting area of the Indium Tin Oxide (ITO) (glass) substrate is patterned so as to have a size of 3 mm x 3 mm and then cleaned. After mounting the substrate in a vacuum chamber, the basic pressure was 1 × 10 −6 torr, and then organic materials were placed on ITO, CuPC (200Å), NPB (500Å), light emitting layer (300Å), Alq 3 (200Å), and LiF (5Å). Film formation in the order of Al (1000 mW). At this time, the following material (HOST-1) was used as the first HOST of the emission layer, and the material S-28 according to Chemical Formula 1 of the present invention was used as an impurity, and the mixing ratio of HOST-1 and S-28 was set to 1: 0.01. .

이렇게 얻어진 발광층에 1mA의 전류를 흘려 주었을 때 3.4cd/A을 얻었고, 이때 CIE는 x=0.15, y=0.196이었다.3.4 cd / A was obtained when 1 mA of current was flowed through the obtained light emitting layer, and CIE was x = 0.15 and y = 0.196.

또한 다른 조건은 동일하게 하고 불순물로 상기 S-28 대신에 본 발명의 화학식 1에 따른 물질 S-26을 사용하는 경우에는 1mA의 전류를 흘려 주었을 때 3.2cd/A을 얻었고, 이때 CIE는 x=0.146, y=0.205이었다.In addition, other conditions were the same, and in the case of using S-26 according to Chemical Formula 1 of the present invention instead of S-28 as an impurity, 3.2 cd / A was obtained when a current of 1 mA was applied, where CIE was x = 0.146, y = 0.205.

2. 비교예2. Comparative Example

ITO 기판(glass)의 발광 면적이 3mm×3mm크기가 되도록 패터닝한 후 세정하였다. 상기 기판을 진공 챔버에 장착한 후 기본 압력이 1×10-6torr가 되도록 한 후 유기물을 ITO위에 CuPC(200Å), NPB(300Å), 발광층(host-1:200Å), Alq3(400Å), LiF(5Å), Al(1000Å)의 순서로 성막하였다. 1mA에서 1.8cd/A을 나타내었으며 이때 CIE는 x=0.194, y=0.297을 나타내었다.The light emitting area of the ITO substrate (glass) was patterned to have a size of 3 mm x 3 mm and then washed. After mounting the substrate in a vacuum chamber, the basic pressure was 1 × 10 −6 torr, and then organic materials were placed on ITO, CuPC (200Å), NPB (300Å), light emitting layer (host-1: 200Å), and Alq 3 (400Å). The film was formed in the order of LiF (5 kV) and Al (1000 kV). 1.8 cd / A at 1 mA, where CIE showed x = 0.194 and y = 0.297.

본 발명은 유기발광체의 청색발광물질로서 상기와 같이 색순도가 높은 화합물을 사용함으로써 청색의 색순도가 높은 유기 전계 발광 소자를 얻을 수 있다.The present invention can obtain an organic electroluminescent device having a high color purity of blue by using a compound having a high color purity as described above as a blue light emitting material of the organic light emitting body.

이상 설명한 내용을 통해 당업자라면 본 발명의 기술 사상을 일탈하지 아니하는 범위에서 다양한 변경 및 수정이 가능함을 알 수 있을 것이다.Those skilled in the art will appreciate that various changes and modifications can be made without departing from the spirit of the present invention.

따라서, 본 발명의 기술적 범위는 실시예에 기재된 내용으로 한정되는 것이 아니라 특허 청구의 범위에 의하여 정해져야 한다.Therefore, the technical scope of the present invention should not be limited to the contents described in the embodiments, but should be defined by the claims.

Claims (11)

전자 주입 전극(음극)과 정공 주입 전극(양극) 사이에 발광층을 포함하는 유기전계 발광 소자로서, 상기 발광층의 청색 발광물질로 하기 화학식 1로 나타내어지는 물질을 포함하는 것을 특징으로 하는 유기 전계 발광 소자: An organic electroluminescent device comprising a light emitting layer between an electron injection electrode (cathode) and a hole injection electrode (anode), the organic light emitting device comprising a material represented by the following formula (1) as a blue light emitting material of the light emitting layer : [화학식 1][Formula 1] (상기 식에서, A1 및 A2는 각각 독립적으로 치환되거나 치환되지 않은 C6-C20의 방향족 그룹 또는 N, S 또는 O를 포함하는 C5-C19의 이형고리 그룹이다).Wherein A 1 and A 2 are each independently a substituted or unsubstituted aromatic group of C 6 -C 20 or a heterocyclic group of C 5 -C 19 comprising N, S or O. 삭제delete 제 1 항에 있어서,The method of claim 1, 상기 발광층이 화학식 1의 물질과 하기 화학식 2의 물질을 혼합하여 사용하는 것을 특징으로 하는 유기 전계 발광 소자: An organic electroluminescent device, characterized in that the light emitting layer is used by mixing the material of Formula 1 and the material of Formula 2: [화학식 2] [Formula 2] B1 - X - B2B1-X-B2 (상기 식에서, X는 나프탈렌, 안트라센 및 페난트렌으로 이루어지는 그룹으로부터 선택되고, B1 및 B2는 각각 독립적으로 C6-C25의 아릴, C6-C25의 알킬아릴, C6-C25의 아릴아미노아릴 및 C6-C25의 아릴알릴기로 이루어진 그룹으로부터 선택된다).Wherein X is selected from the group consisting of naphthalene, anthracene and phenanthrene, and B1 and B2 are each independently C 6 -C 25 aryl, C 6 -C 25 alkylaryl, C 6 -C 25 aryl Aminoaryl and C 6 -C 25 arylallyl group). 삭제delete 삭제delete 제 3 항에 있어서,The method of claim 3, wherein 상기 화학식 2의 물질이 다음 중 어느 하나인 것을 특징으로 하는 유기 전계 발광 소자: An organic EL device, characterized in that the material of Formula 2 is any one of the following: 삭제delete 제 1 항에 있어서,The method of claim 1, 상기 A1 및 A2에 치환되는 치환기는 각각 1개 이상이며, C1-C10의 알킬, C1-C10의 알콕시, C1-C10의 알킬아미노, C1-C10의 알킬실릴, 할로겐, C6-C10의 아릴, C6-C10의 아릴옥시, C6-C10의 아릴아미노, C6-C10의 아릴실릴 그룹 및 수소로 이루어진 그룹으로부터 선택되는 것을 특징으로 하는 유기 전계 발광 소자.One or more substituents substituted for A1 and A2 are each C 1 -C 10 alkyl, C 1 -C 10 alkoxy, C 1 -C 10 alkylamino, C 1 -C 10 alkylsilyl, halogen , An organic electric field selected from the group consisting of C 6 -C 10 aryl, C 6 -C 10 aryloxy, C 6 -C 10 arylamino, C 6 -C 10 arylsilyl group and hydrogen Light emitting element. 삭제delete 삭제delete 제 1 항에 있어서, The method of claim 1, 상기 화학식 1의 물질이 다음 중 어느 하나인 것을 특징으로 하는 유기 전계 발광 소자:An organic EL device, characterized in that the material of Formula 1 is any one of the following: : : . .
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