KR20040005416A - Compound For Blue Light Emitting Material And Organic Electroluminescent Device Comprising The Same - Google Patents
Compound For Blue Light Emitting Material And Organic Electroluminescent Device Comprising The Same Download PDFInfo
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Abstract
Description
본 발명은 유기 전계 발광 소자의 청색 발광 물질용 화합물 및 이를 포함한 유기 전계 발광 소자에 관한 것으로, 상세하게는 유기 전계 발광 소자에서 청색 발광 물질로 사용될 수 있는 화합물 및 이를 이용하여 형광 효율을 높이고 청색파장의 빛을 얻을 수 있는 유기 전계 발광 소자에 관한 것이다.The present invention relates to a compound for a blue light emitting material of an organic electroluminescent device and an organic electroluminescent device including the same, and more particularly, a compound which can be used as a blue light emitting material in an organic electroluminescent device, and to increase the fluorescence efficiency and blue wavelength using the The present invention relates to an organic electroluminescent device capable of obtaining light.
21세기는 고도의 정보화 사회가 될 것으로 예상된다. 이에 따라 언제 어디서나 많은 정보를 쉽고 빠르게 얻어야 하는 필요성으로 인하여, 멀티 미디어용 고성능 평판 디스플레이의 중요성이 점차 커지고 있다. 현재까지는 평판 디스플레이 수용의 대부분을 LCD(Liquid Crystal Display)가 공급하고 있으나, 보다 값싸고 성능이 뛰어나면서 LCD와 차별화된 새로운 평판 디스플레이를 개발하려는 노력이 전세계적으로 활발히 진행되고 있다.The 21st century is expected to be a highly information society. Accordingly, the importance of high performance flat panel displays for multimedia is increasing due to the need to obtain a lot of information easily and quickly anytime and anywhere. Until now, most of flat panel display has been supplied by liquid crystal displays (LCDs), but efforts are being made to develop new flat panel displays that are different from LCDs because they are cheaper and have higher performance.
최근 차세대 평판 디스플레이로 각광을 받고 있는 유기 전계 발광(EL) 디스플레이는 발광 효율이 높으면서, 15V 이내에서 구동이 가능하고, 여러 가지 색을 구현할 수 있으며, 자체 발광형으로 시야각이 160도 이상이라는 장점을 갖고 있다. 또한, 유기 EL 디스플레이는 모듈의 총 두께를 2mm 이내로 만들 수 있고, 0.3mm 이하의 플라스틱 기판 위에 제작할 수 있기 때문에, 휴대형 단말기의 박형, 경량화 추세에도 손쉽게 대응할 수 있을뿐만 아니라, 응답 속도가 빨라서 제작 공정이 복잡한 박막 트랜지스터를 채용하지 않고도, 그래픽이나 동화상 표현이 가능하므로 양산시 제작 비용이 TFT-LCD보다 저렴하다는 장점을 갖고 있다.The organic electroluminescent (EL) display, which has recently been in the spotlight as the next-generation flat panel display, has high luminous efficiency, can be driven within 15V, realizes various colors, and has a self-luminous type that has a viewing angle of more than 160 degrees. Have In addition, the organic EL display can be made within 2mm of the total thickness of the module, and can be manufactured on a plastic substrate of 0.3mm or less, so that it is not only able to cope with the trend of thinner and lighter portable terminals, but also has a fast response speed, thus making the manufacturing process easier. Since it is possible to display graphics or moving images without adopting this complicated thin film transistor, the production cost is lower than that of TFT-LCD in mass production.
이러한 유기 EL 디스플레이는 전자 주입 전극과 정공 주입 전극 사이에 형성된 유기막에 전하를 주입하면 전자와 정공이 쌍을 이룬 후 소멸하면서 빛을 내는 소자이다. 유기 EL 디스플레이는 정공 주입 전극, 전자 주입 전극, 그리고 두 전극 사이에 형성된 발광 매체로 구성되어 있다. 상기 발광 매체는 일반적으로 전자를 주입하고 수송하는 층(전자주입층 및/또는 전자수송층), 정공을 주입하고 수송하는 층(정공주입층 및/또는 정공수송층), 그리고 빛을 발생시키는 층(발광층)을 포함하는 다층으로 구성되어 있다.Such an organic EL display is a device that emits light by dissipating electrons and holes after pairing when an electric charge is injected into an organic film formed between the electron injection electrode and the hole injection electrode. The organic EL display is composed of a hole injection electrode, an electron injection electrode, and a light emitting medium formed between the two electrodes. The light emitting medium is generally a layer for injecting and transporting electrons (electron injection layer and / or electron transport layer), a layer for injecting and transporting holes (hole injection layer and / or hole transport layer), and a layer for generating light (light emitting layer) It is composed of a multilayer including).
상술한 바와 같은 구조를 갖는 유기 EL 소자의 구동 원리는 다음과 같다.The driving principle of the organic EL element having the structure as described above is as follows.
상기 정공 주입 전극 및 전자 주입 전극 간에 전압을 인가하면 정공 주입 전극으로부터 주입된 정공은 정공수송층을 경유하여 발광층에 이동된다. 한편, 전자는 전자 주입 전극으로부터 전자수송층을 경유하여 발광층에 주입되고, 발광층 영역에서 캐리어들이 재결합하여 엑시톤(exiton)을 생성한다. 이 엑시톤이 여기 상태에서 기저 상태로 변화되고, 이로 인하여 발광층의 형광성 분자가 발광함으로써 화상이 형성된다.When a voltage is applied between the hole injection electrode and the electron injection electrode, holes injected from the hole injection electrode are moved to the light emitting layer via the hole transport layer. On the other hand, electrons are injected into the emission layer from the electron injection electrode via the electron transport layer, and carriers are recombined in the emission layer to generate excitons. The excitons change from the excited state to the ground state, whereby the fluorescent molecules in the light emitting layer emit light to form an image.
유기 EL 디스플레이와 같이 발광 매체에 유기물질을 사용하는 경우 다양한 물질의 합성이 용이하여 발광색을 다양화할 수 있다는 장점을 가진다. 이와 같은 유기물질은 고분자 물질과 저분자 물질로 나눌 수 있으며, 저분자 물질을 이용하는 것이 고분자 물질보다 균일한 박막을 얻을 수 있고, 휘도 및 발광효율이 우수하며 풀칼라(full color)화가 용이하기 때문에 바람직하다. 저분자 물질로는 디아민, TPD 유도체, 스티릴기 등 다양한 구조의 물질을 사용할 수 있다.In the case of using an organic material for a light emitting medium such as an organic EL display, the synthesis of various materials is easy, and thus the light emission color can be diversified. Such organic materials can be divided into high molecular materials and low molecular materials. It is preferable to use low molecular materials because they can obtain a thin film more uniform than high molecular materials, and are excellent in brightness and luminous efficiency and easy to full color. . As the low molecular weight material, various structures such as diamine, TPD derivative, and styryl group may be used.
유기 EL 디스플레이 소자는 다른 디스플레이 소자에서는 찾아볼 수 없는 특징을 가지고 있어 풀칼라 평판 디스플레이 소자에서 응용이 기대되고 있다.Organic EL display elements have characteristics that are not found in other display elements, and thus are expected to be applied in full color flat panel display elements.
그러나, 종래의 청색 발광 화합물들은 적색이나 황색과 같은 다른 색상의 발광 화합물들에 비해 발광 효율이 떨어지며 박막 안정성이 더 개선되어야만 하므로 청색 발광 소자나 총천연색 발광 소자를 개발하기 위해서는 새로운 청색 발광 화합물의 개발이 시급한 해결 과제가 되고 있다.However, conventional blue light emitting compounds have lower luminous efficiency and thin film stability than other light emitting compounds such as red or yellow. Therefore, in order to develop a blue light emitting device or a full color light emitting device, it is necessary to develop a new blue light emitting compound. It is an urgent solution.
이러한 문제점들을 해결하기 위해, 본 발명은 발광 휘도가 높고 안정한 청색 발광이 가능한 유기 화합물을 얻는 것을 그 목적으로 하고 있다.In order to solve these problems, an object of the present invention is to obtain an organic compound having high emission luminance and stable blue light emission.
본 발명의 다른 목적은 이러한 유기 화합물을 유기 EL 소자의 발광층 또는 정공전달층에 적용시켜, 형광 효율이 높고 안정한 청색파장의 빛을 얻을 수 있는유기 EL 소자를 제공하는 것이다.Another object of the present invention is to provide an organic EL device capable of obtaining stable blue wavelength light with high fluorescence efficiency by applying such an organic compound to a light emitting layer or a hole transporting layer of an organic EL device.
도 1은 본 발명에 따른 청색 발광 물질용 화합물의 합성 과정의 한 예를 나타낸 도면이다.1 is a view showing an example of the synthesis process of a compound for a blue light emitting material according to the present invention.
상기와 같은 목적을 달성하기 위해, 본 발명의 한 측면에서는 하기 구조식 1을 갖는 유기 전계 발광 소자의 청색 발광 물질용 화합물이 제공된다.In order to achieve the above object, in one aspect of the invention there is provided a compound for a blue light emitting material of an organic electroluminescent device having the following structural formula (1).
(구조식 1)(Formula 1)
상기 구조식 1에서, R은 수소원자(H), 알킬기(alkyl), 페닐기(phenyl), 헤테로환기(heterocyclic), 피리딘기(pyridine), 나프틸기(naphthyl), 안트라센기(anthracene), 피렌기(pyrene), 바이페닐기(biphenyl), 티오펜기(thiophene), 스티릴기(styryl) 및 스티릴렌(styrylene)기로 이루어진 군으로부터 선택되는 어느 하나이다.In Formula 1, R is a hydrogen atom (H), an alkyl group (alkyl), a phenyl group (phenyl), a heterocyclic group (pyrodine), pyridine, naphthyl, anthracene group (anthracene), pyrene group ( It is any one selected from the group consisting of a pyrene, a biphenyl group, a thiophene group, a styryl group, and a styryl group.
바람직하게, 본 발명에 따른 청색 발광 물질용 화합물은 하기 구조식 2를 갖는다.Preferably, the compound for blue light emitting material according to the present invention has the following structural formula 2.
(구조식 2)(Formula 2)
또 다른 예로, 본 발명에 따른 청색 발광 물질용 화합물은 하기 구조식 3, 4 또는 5를 갖는다.As another example, the compound for blue light emitting material according to the present invention has the following structural formula 3, 4 or 5.
(구조식 3)(Structure 3)
(구조식 4)(Formula 4)
(구조식 5)(Structure 5)
본 발명의 다른 측면에서는 제1전극, 제2전극 및 상기 양 전극 사이에 형성된 유기 발광층을 포함하는 유기 전계 발광 소자에 있어서, 상기 유기 발광층이 상기 구조식 1 내지 5 중 어느 하나의 청색 발광 물질용 화합물로 이루어진 유기 전계 발광 소자가 제공된다.In another aspect of the present invention, in the organic electroluminescent device comprising an organic light emitting layer formed between the first electrode, the second electrode and the positive electrode, the organic light emitting layer is a compound for a blue light emitting material of any one of the formulas 1 to 5 There is provided an organic electroluminescent element.
본 발명의 또 다른 측면에서는 제1전극, 제2전극 및 상기 양 전극 사이에 형성된 유기 발광층을 포함하는 유기 전계 발광 소자에 있어서, 상기 유기 발광층이 상기 구조식 1 내지 5 중 어느 하나의 청색 발광 물질용 화합물을 도판트로 포함하는 유기 전계 발광 소자가 제공된다.In another aspect of the present invention, in the organic electroluminescent device comprising an organic light emitting layer formed between the first electrode, the second electrode and the positive electrode, the organic light emitting layer for any one of the blue light emitting material of the formula 1 to 5 An organic electroluminescent device comprising a compound as a dopant is provided.
본 발명의 또 다른 측면에서는 또한 제1전극, 제2전극 및 상기 양 전극 사이에 형성된 정공전달층을 포함하는 유기 전계 발광 소자에 있어서, 상기 정공전달층이 제1항 내지 제5항 중 어느 한 항의 청색 발광 물질용 화합물을 포함하는 유기 전계 발광 소자가 제공된다. 상기 정공전달층은 정공주입층과 정공수송층 중 어느 한 층일 수도 있고, 두 층 모두일 수도 있다.In still another aspect of the present invention, in the organic electroluminescent device comprising a hole transport layer formed between the first electrode, the second electrode and the positive electrode, the hole transport layer is any one of claims 1 to 5 Provided is an organic electroluminescent device comprising the compound for blue light emitting material of claim. The hole transport layer may be any one of a hole injection layer and a hole transport layer, or both layers.
본 발명에 따른 유기 전계 발광 소자는 투명 기판 위에 제1전극, 제1전극 위에 형성되는 정공주입층과, 수송층과, 상기 수송층 위에 형성되는 발광층과, 상기 발광층 위에 형성되는 전자수송층 및 전자주입층과, 상기 전자수송층 위에 형성되는 제2전극으로 이루어진다.The organic electroluminescent device according to the present invention includes a first electrode, a hole injection layer formed on the first electrode, a transport layer, a light emitting layer formed on the transport layer, an electron transport layer and an electron injection layer formed on the light emitting layer; And a second electrode formed on the electron transport layer.
또한, 이러한 유기 전계 발광 소자 제작 과정은 다음과 같다.In addition, the manufacturing process of the organic EL device is as follows.
투명 기판 위에 제1전극으로 입히는 물질로는 ITO를 일반적으로 사용한다. 제1전극 위에 정공주입층을 입히는데 주로 카파프탈로시아닌(copper phthalocyanine)을 20∼80 Å 정도 두께로 입힌다. 그 위에 NPD(4,4'-bis[N-(1-naphthyl)-N-phenylamino]-biphenyl)를 300∼500 Å 정도 증착하여 정공수송층을 형성시킨다. 수송층 위에 유기 발광층으로써 합성된 화합물을 100∼300 Å 증착하였다. 그리고 상기 발광층 위에 Alq3(tris(8-hydroxy-quinolate)aluminum)을 300∼500 Å 정도 증착하여 전자수송층과 주입층을 형성한다. 다음으로 제2전극을 입히고 보호막을 씌우게 된다.ITO is generally used as a material coated on the transparent substrate as the first electrode. A hole injection layer is coated on the first electrode, and a copper phthalocyanine is usually coated with a thickness of about 20 to 80 Å. NPD (4,4'-bis [N- (1-naphthyl) -N-phenylamino] -biphenyl) is deposited thereon at about 300 to 500 Å to form a hole transport layer. A compound synthesized as an organic light emitting layer was deposited on the transport layer at 100 to 300 Hz. In addition, Alq 3 (tris (8-hydroxy-quinolate) aluminum) is deposited on the emission layer at about 300 to 500 Å to form an electron transport layer and an injection layer. Next, a second electrode is coated and a protective film is covered.
이하, 본 발명은 합성예와 실시예를 참고로 자세히 설명될 것이다. 하기 합성예 및 실시예는 본 발명의 이해를 돕기 위한 것으로, 단지 예시적이며, 본 발명을 한정하는 것은 아니다. 또한 본 발명은 본 발명의 취지 및 범위를 벗어나지 않는 한도내에서 변형 및 변경이 가능한 것으로 이해되어야 할 것이다.Hereinafter, the present invention will be described in detail with reference to synthesis examples and examples. The following Synthesis Examples and Examples are provided to aid the understanding of the present invention and are merely exemplary and do not limit the present invention. It is also to be understood that the present invention may be modified and changed without departing from the spirit and scope of the invention.
하기 합성예는 본 발명에 따른 구조식 2의 청색 발광 물질용 화합물의 제조방법에 관한 것이고, 하기 실시예는 본 발명에 따른 구조식 2의 청색 발광 물질용 화합물을 이용한 유기 EL 소자의 제작에 관한 것이다.The following Synthesis Example relates to a method for preparing a compound for blue light emitting material of Structural Formula 2 according to the present invention, and the following Example relates to the fabrication of an organic EL device using the compound for blue light emitting material of Structural Formula 2 according to the present invention.
합성예Synthesis Example
본 발명에 따른 구조식 2의 화합물의 합성 방법은 다음과 같다. 도 1에는 구조식 2의 화합물의 합성 과정이 도시되어 있다.The synthesis method of the compound of formula 2 according to the present invention is as follows. 1 shows the synthesis process of the compound of formula 2.
(1) 중간체 (a)의 합성(1) Synthesis of Intermediate (a)
카르바졸(carbazole) 5 g (0.03 mol), 1-브로모-4-요오드벤젠 11 g (0.039 mol), 1,10-페난트롤린 0.3 g (0.0015 mol), 그리고 CuCl 0.15 g (0.0015 mol)을 톨루엔 50 ml에 용해시켰다. 완전히 용해시킨 후, 이 용액에 KOH 13.5 g (0.24mol)을 넣고 12시간 동안 환류시켰다. 그렇게 만들어진 용액을 실온으로 냉각시킨 후, 물을 넣어 상분리시켰다. 유기층을 분리시킨 후, 용매를 제거했다. 칼럼 크로마토그래피를 이용하여 정제해서 생성물 (a) 4.2 g을 얻었다.5 g (0.03 mol) of carbazole, 11 g (0.039 mol) of 1-bromo-4-iodinebenzene, 0.3 g (0.0015 mol) of 1,10-phenanthroline, and 0.15 g (0.0015 mol) of CuCl Was dissolved in 50 ml of toluene. After complete dissolution, 13.5 g (0.24 mol) of KOH was added to the solution and refluxed for 12 hours. The solution thus made was cooled to room temperature and water was added to phase separate. After the organic layer was separated, the solvent was removed. Purification by column chromatography gave 4.2 g of product (a).
(2) 생성물 (b)의 합성(2) Synthesis of Product (b)
삼구플라스크에 콘덴서(condenser)와 적하 깔때기(dropping funnel)를 연결한 후, 완전히 건조시켰다. 완전 건조된 플라스크에 THF와 마그네슘 0.06 g (0.0024 mol)을 넣고 천천히 교반시켰다. 반응물 (a)를 THF에 녹인 후, 적하 깔때기를 이용하여 천천히 떨어뜨렸다. 완전히 떨어뜨린 다음, 가열하여 그리냐르(Grignard) 시약을 만들었다. 이 시약을 9,10-디브로모안트라센 0.31 g (0.00091 mol)과 [1,3-비스(디페닐포스피노)-프로판]디클로로니켈(Ⅱ) 0.002 g을 THF에 용해되어 있는 플라스크에 캐뉼라(cannula)를 통해 부가하였다. 완전히 부가한 후, 5시간 동안 환류시켰다. 실온으로 냉각시킨 후, 물을 첨가하여 상분리시켰다. 이어서 유기층을 분리하여 용매를 제거한 후, 헥산에서 재결정하여 생성물 (b)를 0.43 g을 얻었다.The condenser and dropping funnel were connected to a three-necked flask, and then completely dried. THF and 0.06 g (0.0024 mol) of magnesium were added to the completely dried flask and stirred slowly. The reaction (a) was dissolved in THF and then slowly dropped using a dropping funnel. After dropping completely, it was heated to produce Grignard reagent. 0.31 g (0.00091 mol) of 9,10-dibromoanthracene and 0.002 g of [1,3-bis (diphenylphosphino) -propane] dichloronickel (II) cannula into a flask dissolved in THF. cannula). After complete addition, it was refluxed for 5 hours. After cooling to room temperature, the phases were separated by the addition of water. The organic layer was then separated to remove the solvent, and then recrystallized from hexane to obtain 0.43 g of product (b).
실시예Example
유리 기판 상에 ITO 전극을 형성하였다. 그런 다음, 상기 전극 상부에 카파프탈로시아닌을 50 Å 증착하고, 그 위에 NPD를 400 Å 증착하여 정공주입층과 정공수송층을 형성하였다. 상기 정공수송층 위에 본 발명에 따른 화합물을 200 Å 증착하여 발광층을 형성하였다. 이어서 상기 발광층 위에 Alq3를 약 400 Å 정도 증착하여 전자수송 및 주입층을 형성하였고, 그 위에 알루미늄을 증착시켜 전극을 형성하였다.An ITO electrode was formed on the glass substrate. Then, 50 kPa of kappaphthalocyanine was deposited on the electrode, and 400 kW of NPD was deposited thereon to form a hole injection layer and a hole transport layer. The light emitting layer was formed by depositing 200 Å of the compound according to the present invention on the hole transport layer. Subsequently, Alq 3 was deposited on the emission layer to form an electron transport and injection layer, and aluminum was deposited thereon to form an electrode.
EL 피크의 최대치는 460 nm였다.The maximum value of the EL peak was 460 nm.
10 V 전압을 걸었을 때, 휘도는 3120 cd/㎡이고, 발광 효율은 3.52 cd/A이었다.When the voltage was applied at 10 V, the luminance was 3120 cd / m 2 and the luminous efficiency was 3.52 cd / A.
본 발명은 발광 휘도가 높고 안정한 청색 발광 물질용 화합물을 제공하고, 또한 이를 유기 EL 소자의 발광층에 이용함으로써 발광 효율이 높고, 청색 파장의 빛을 얻을 수 있는 청색 유기 EL 소자를 제공할 수 있다.The present invention can provide a blue organic EL device having a high luminescence brightness and having a stable compound for blue light emitting materials, and using the same for a light emitting layer of an organic EL device, and having a high luminous efficiency and obtaining light having a blue wavelength.
Claims (9)
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| KR100662599B1 (en) * | 2004-12-16 | 2007-01-02 | 엘지전자 주식회사 | Organic electroluminescent device having superior efficiency |
| KR100696006B1 (en) * | 2004-12-14 | 2007-03-15 | 에스케이씨 주식회사 | Blue phosphorescent host material and organic electroluminescent device using same |
| KR100700425B1 (en) * | 2004-12-14 | 2007-03-27 | 네오뷰코오롱 주식회사 | Blue luminescent organic compound and organic light-emitting diode including the same |
| US7839076B2 (en) | 2004-07-29 | 2010-11-23 | Samsung Mobile Display Co., Ltd. | Organic electroluminescent device |
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| JPH11323323A (en) * | 1998-05-20 | 1999-11-26 | Toppan Printing Co Ltd | Luminescent material |
| JP2000182775A (en) * | 1998-12-09 | 2000-06-30 | Eastman Kodak Co | Organic electroluminescence element |
| KR100274871B1 (en) * | 1998-11-12 | 2000-12-15 | 김순택 | Photoluminescence compound and display device adopting photoluminescence compound as color-developing substance |
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| WO2002038524A1 (en) * | 2000-11-08 | 2002-05-16 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent element |
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| JPH11323323A (en) * | 1998-05-20 | 1999-11-26 | Toppan Printing Co Ltd | Luminescent material |
| KR100274871B1 (en) * | 1998-11-12 | 2000-12-15 | 김순택 | Photoluminescence compound and display device adopting photoluminescence compound as color-developing substance |
| JP2000182775A (en) * | 1998-12-09 | 2000-06-30 | Eastman Kodak Co | Organic electroluminescence element |
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| US7839076B2 (en) | 2004-07-29 | 2010-11-23 | Samsung Mobile Display Co., Ltd. | Organic electroluminescent device |
| KR100696006B1 (en) * | 2004-12-14 | 2007-03-15 | 에스케이씨 주식회사 | Blue phosphorescent host material and organic electroluminescent device using same |
| KR100700425B1 (en) * | 2004-12-14 | 2007-03-27 | 네오뷰코오롱 주식회사 | Blue luminescent organic compound and organic light-emitting diode including the same |
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