KR100686109B1 - Iridium complex and Organic electroluminescent device with iridium complex - Google Patents

Iridium complex and Organic electroluminescent device with iridium complex Download PDF

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KR100686109B1
KR100686109B1 KR1020010016470A KR20010016470A KR100686109B1 KR 100686109 B1 KR100686109 B1 KR 100686109B1 KR 1020010016470 A KR1020010016470 A KR 1020010016470A KR 20010016470 A KR20010016470 A KR 20010016470A KR 100686109 B1 KR100686109 B1 KR 100686109B1
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carbon atoms
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KR20020076545A (en
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김동욱
김성훈
오형윤
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엘지전자 주식회사
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    • C—CHEMISTRY; METALLURGY
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • 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
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    • 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
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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Abstract

본 발명은 벤조퀴놀린 리간드를 갖는 이리듐착체 화합물 및 이를 포함하는 유기전계발광소자를 제공하기 위한 것으로서, 상기 유기전계발광소자는 제 1전극과 제 2전극 사이에 벤조퀴놀린 리간드를 갖는 이리듐착체 화합물을 포함함으로서 유기전계발광소자의 유기발광층에 적용되어 소자의 안정성을 향상시키고 우수한 발광효율을 가지는 효과를 나타낸다.The present invention is to provide an iridium complex compound having a benzoquinoline ligand and an organic electroluminescent device comprising the same, the organic electroluminescent device comprises an iridium complex compound having a benzoquinoline ligand between the first electrode and the second electrode By applying to the organic light emitting layer of the organic light emitting device to improve the stability of the device and exhibits an effect having excellent luminous efficiency.

유기전계발광소자Organic light emitting diode

Description

이리듐착체 화합물 및 이를 포함하는 유기전계발광소자{Iridium complex and Organic electroluminescent device with iridium complex}Iridium complex compound and organic electroluminescent device including the same {Iridium complex and Organic electroluminescent device with iridium complex}

도 1은 일반적인 유기전계발광소자의 구조를 보여주는 단면도이며,1 is a cross-sectional view showing the structure of a conventional organic light emitting display device,

도 2는 본 발명에 따른 유기전계발광소자의 구조를 보여주는 단면도이다.2 is a cross-sectional view showing the structure of an organic light emitting display device according to the present invention.

도 3은 본 발명에 따른 화합물의 광발광 세기 측정도이다.3 is a photoluminescence intensity measurement diagram of a compound according to the present invention.

<도면의 주요부분에 대한 부호의 설명><Description of the symbols for the main parts of the drawings>

1 : 기판1: substrate

2 : 제 1전극2: first electrode

3 : 유기막층(발광층 및 수송층)3: organic film layer (light emitting layer and transport layer)

4 : 제 2전극4: second electrode

5 : 정공주입층5: hole injection layer

6 : 정공수송층6: hole transport layer

7 : 유기발광층7: organic light emitting layer

8 : 전자수송층8: electron transport layer

9 : 전자주입층9: electron injection layer

본 발명은 유기전계발광소자에 관한 것으로, 상세하게는 벤조퀴놀린 리간드를 갖는 이리듐착체 화합물 및 이를 발광물질로서 사용하는 유기전계발광소자에 관한 것이다.The present invention relates to an organic electroluminescent device, and more particularly, to an iridium complex compound having a benzoquinoline ligand and an organic electroluminescent device using the same as a light emitting material.

최근 표시장치(디스플레이)의 대형화에 따라 공간 점유가 적은 평면표시소자의 요구가 증대되고 있는데, 이러한 평면표시소자 중의 하나가 전계발광소자이다.Recently, as the size of display devices (displays) increases, the demand for flat display devices with less space is increasing. One of the flat display devices is an electroluminescent device.

상기 전계발광소자는 사용하는 재료에 따라 무기전계발광소자와 유기전계발광소자로 크게 나뉜다.The electroluminescent device is classified into inorganic electroluminescent device and organic electroluminescent device according to the material used.

상기 무기전계발광소자는 일반적으로 발광부에 높은 전계를 인가함으로서 전자를 가속시키고, 이에 따라 가속된 전자가 발광중심에 충돌되는 것에 의해 발광중심이 여기됨으로써 발광하는 소자이다.In general, the inorganic electroluminescent device is a device that accelerates electrons by applying a high electric field to a light emitting part, and thus emits light by exciting the light emitting center by colliding the accelerated electrons with the light emitting center.

유기전계발광소자의 발광 메카니즘은 양전극(cathode)으로부터 주입된 정공과 전자가 유기물층에서 재결합될 때 발생되는 열이 발광색소를 여기시키며, 여기된 색소가 바닥상태로 떨어지면서 형광을 방출하는 것이다.The light emitting mechanism of the organic electroluminescent device is that heat generated when holes and electrons injected from a cathode are recombined in an organic material layer excites a light emitting pigment, and the excited pigment falls to the ground state to emit fluorescence.

일반적으로 분자가 단일항(singlet) 여기상태로부터 바닥상태로 떨어질 때 빛을 방출하는 것을 형광이라고 하고 삼중항(triplet) 여기상태로부터 바닥상태로 떨어질 때 빛을 방출하는 것을 인광이라고 한다. 분자가 여기상태로부터 빛을 방출할 최대효율은 형광의 경우 25%이고, 인광의 경우 75% 이상이 된다.In general, fluorescence is what emits light when a molecule falls from a singlet excited state to the ground state, and phosphorescence is what emits light when it falls from a triplet excited state to the ground state. The maximum efficiency at which a molecule emits light from an excited state is 25% for fluorescence and 75% or more for phosphorescence.

유기전계발광소자의 구조는 전자주입전극(음극)과 정공주입전극(양극(하부 전극)) 사이에 형성된 유기막에 전하를 주입하면 전자와 정공이 쌍을 이룬 후 소멸 하면서 빛을 내는 소자로서 낮은 전압에서 구동이 가능하고, 또한 전력 소모가 적은 것이 특징이다.The structure of the organic light emitting device is a device that emits light when electrons and holes are paired and extinguished when charge is injected into the organic film formed between the electron injection electrode (cathode) and the hole injection electrode (anode (lower electrode)). It can be driven at voltage and consumes less power.

도 1 은 제 1전극/전하수송층 및 발광층/제 2전극으로 구성된 일반적인 유기전계발광소자의 단면도이다.1 is a cross-sectional view of a general organic electroluminescent device composed of a first electrode / charge transport layer and a light emitting layer / second electrode.

좀 더 구체적으로, 유기전계발광소자는 제 1전극/정공주입층/정공수송층/발광층/전자수송층/전자주입층/제 2전극으로 구성될 수 있다.More specifically, the organic light emitting diode may include a first electrode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / second electrode.

현재, 일반적으로 정공수송층으로서 사용되고 있는 물질은 트리페닐아민유도체들이고, 전자수송층으로서 사용되고 있는 물질은 유기금속착체 화합물들 또는 헤테로 고리화합물들이 사용되어지고 있다. 발광층으로서는 유기화합물들 또는 유기금속착체 화합물들이 발광층의 발광물질로서 사용되거나 발광층의 메트릭스로서 사용된다. 이러한 유기화합물들 혹은 유기금속착체 화합물들이 발광층의 메트릭스로서 사용될 때에는 도판트로서 형광물질 혹은 금속착체형 유기형광물질들을 사용하여 발광색을 조절한다.Currently, materials generally used as hole transport layers are triphenylamine derivatives, and materials used as electron transport layers are organometallic complex compounds or heterocyclic compounds. As the light emitting layer, organic compounds or organometallic complex compounds are used as the light emitting material of the light emitting layer or as a matrix of the light emitting layer. When such organic compounds or organometallic complex compounds are used as the matrix of the light emitting layer, fluorescent materials or metal complex organic fluorescent materials are used as dopants to control the emission color.

유기전계발광소자가 풀칼라디스플레이로 실용화되기 위하여는 현재 상용화되어 있는 녹색발광소자 이외에 적색발광소자 및 청색발광소자도 필요하다. 그리고 유기전계발광소자는 무기전계발광소자보다 다양한 색상을 발현할 수 있다.In order for the organic light emitting display device to be used as a full color display, a red light emitting device and a blue light emitting device are required in addition to the green light emitting device that is currently commercially available. In addition, the organic light emitting display device can express various colors than the inorganic light emitting display device.

유기전계발광소자를 위한 인광물질로 이리듐착체 유기화합물에 대한 연구가 진행되고 있다. 이 물질을 발광층의 도핑물질로 사용한 유기전계발광소자는 구동시 높은 발광효율을 가지는 것으로 평가되고 있다. 여기서 발광층을 구성하는 분자구조에 따라서 발광의 색이 달라지며, 발광층에서의 발광은 발광층을 이루는 물질 즉 인광분자 자체의 발광과 발광층으로 사용되는 메트릭스에 도핑한 인광물질에 의한 발광 등으로 나눌 수 있다.Research on iridium complex organic compounds as a phosphor for organic electroluminescent devices is in progress. An organic light emitting display device using this material as a doping material for a light emitting layer is evaluated to have a high luminous efficiency during driving. Here, the color of light emission varies depending on the molecular structure of the light emitting layer, and light emission in the light emitting layer may be classified into a light emitting layer, that is, light emitted by a phosphor molecule and light emitted by a phosphor doped into a matrix used as a light emitting layer. .

그런데, 종래의 이리듐착체 화합물은 상대적으로 밝기 및 효율이 많이 떨어지며 장파장의 빛을 내기 위하여 도핑을 많이 할 경우 장파장의 빛을 얻을 수는 있으나 농도소광(concentration quenching)에 의하여 발광효율이 급격히 감소한다는 문제점이 있다.By the way, the conventional iridium complex compound is relatively low in brightness and efficiency, and when doping a lot of light to obtain a long wavelength of light can be obtained a long wavelength, but the luminous efficiency is sharply reduced by the concentration quenching (problem) There is this.

따라서 본 발명은 상기와 같은 문제점을 해결하기 위해 안출한 것으로, 새로운 유기전계발광물질인 벤조퀴놀린 리간드를 갖는 이리듐착체 화합물들을 개발하고, 상기 이리듐착체 화합물을 유기전계발광소자의 발광층으로 사용함으로써 소자의 구동수명을 연장시키고 높은 발광효율을 얻을 수 있는 유기전계발광소자를 제공하는데 그 목적이 있다.Therefore, the present invention has been made to solve the above problems, by developing iridium complex compounds having a benzoquinoline ligand, a new organic electroluminescent material, and using the iridium complex compound as the light emitting layer of the organic electroluminescent device It is an object of the present invention to provide an organic light emitting device that can extend the driving life and obtain a high luminous efficiency.

상기 목적을 달성하기 위하여, 본 발명은 치환되거나 치환되지 않은 벤조퀴놀린 리간드를 갖는 이리듐착체 유기화합물을 제공한다.In order to achieve the above object, the present invention provides an iridium complex organic compound having a substituted or unsubstituted benzoquinoline ligand.

또한, 하기 화학식 1의 벤조퀴놀린 리간드를 갖는 이리듐착체 화합물을 제공한다. Also provided is an iridium complex compound having a benzoquinoline ligand of formula (1).                     

Figure 112001007070199-pat00001
Figure 112001007070199-pat00001

상기 화학식 1에서, R1, R2, R3, R4, R5, R6 , R7 및 R8은 치환되거나 치환되지 않은 알킬기(탄소수 1-18개), 치환되거나 치환되지 않은 아릴기(탄소수 6-18개), 시클로 알킬기(탄소수 3-18개), 방향족헤테로고리기, 할로겐기, 니트로기, 시아노기, 포밀기, 카르복시기, 에스테르기, 아미드기, 비닐기, 치환된 비닐기, 치환되거나 치환되지 않은 아세틸렌기, 치환되거나 치환되지 않은 티올기, 아미노기, 치환되거나 치환되지 않은 아릴아미노기(탄소수 6-18개), 수산기, 알콕시기(탄소수 1-18개) 및 치환되거나 치환되지 않은 아릴옥시기(탄소수 6-18개)로 이루어진 군에서 각각 독립적으로 선택되는 어느 하나이며, 이때, R1 내지 R8은 서로 동일할 수도 있고 또는 상이할 수도 있다.In Chemical Formula 1, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are substituted or unsubstituted alkyl groups (1-18 carbon atoms), substituted or unsubstituted aryl groups (6-18 carbon atoms), cycloalkyl group (3-18 carbon atoms), aromatic heterocyclic group, halogen group, nitro group, cyano group, formyl group, carboxyl group, ester group, amide group, vinyl group, substituted vinyl group , Substituted or unsubstituted acetylene group, substituted or unsubstituted thiol group, amino group, substituted or unsubstituted arylamino group (6-18 carbon atoms), hydroxyl group, alkoxy group (1-18 carbon atoms) and substituted or unsubstituted It is any one selected independently from the group consisting of an aryloxy group (6-18 carbon atoms), wherein R 1 to R 8 may be the same as or different from each other.

한편, 상기 R1과 R2, R2와 R3, R3과 R4, R4와 R5, R5와 R6, R6과 R7 그리고 R 7과 R8은 각각 독립적으로 또는 상호 연결되어 지방족 고리(탄소수 1-18개)를 형성할 수 있다.Meanwhile, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7, and R 7 and R 8 are each independently or mutually Can be linked to form an aliphatic ring (1-18 carbon atoms).

또한, 상기 R1과 R2, R2와 R3, R3과 R4, R4와 R5, R5와 R6, R6과 R7 그리고 R 7과 R8은 각각 독립적으로 또는 상호 연결되어 방향족 고리(탄소수 1-18개)를 형성할 수 있다.R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7, and R 7 and R 8 are each independently or mutually Can be linked to form an aromatic ring (1-18 carbon atoms).

또한, 상기 R1과 R2, R2와 R3, R3과 R4, R4와 R5, R5와 R6, R6과 R7 그리고 R 7과 R8은 각각 독립적으로 또는 상호 연결되어 헤테로고리(탄소 및 헤테로 원자수 1-18개)를 형성할 수 있다.R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7, and R 7 and R 8 are each independently or mutually Can be linked to form a heterocycle (carbon and hetero atoms 1-18).

이리듐착체 화합물은 새로운 유기전계발광용 고성능 발광재료로 평가되고 있다. 본 발명에서는 새로운 부류의 벤조퀴놀린 계열의 이리듐착체 화합물을 설계 및 합성하였다. 또한 합성된 물질의 소자에서의 발광 특성에 대한 평가를 행하였다.Iridium complex compounds are being evaluated as new high performance light emitting materials for organic electroluminescence. In the present invention, a new class of benzoquinoline-based iridium complex compounds were designed and synthesized. In addition, evaluation of the luminescence properties of the synthesized material in the device was performed.

본 발명의 벤조퀴놀린 리간드를 갖는 이리듐착체 화합물의 바람직한 예로서 하기 화학식 2를 갖는 화합물을 들 수 있다. As a preferable example of the iridium complex compound which has the benzoquinoline ligand of this invention, the compound which has following formula (2) is mentioned.                     

Figure 112001007070199-pat00002
Figure 112001007070199-pat00002

상기 화학식 2는 상기 화학식 1에서 R1, R2, R3, R4, R5 , R6, R7 및 R8은 모두 수소(H)인 경우이다.In Chemical Formula 2, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7, and R 8 in Chemical Formula 1 are all hydrogen (H).

또한, 본 발명은 제 1전극, 제 2전극 및 다수의 유기막층을 포함하는 유기전계발광소자에 있어 상기한 화합물 중 어느 하나가 함유된 발광층을 포함하여 구성될 수 있는 유기전계발광소자를 제공한다.The present invention also provides an organic electroluminescent device which may include a light emitting layer containing any one of the above compounds in an organic electroluminescent device comprising a first electrode, a second electrode and a plurality of organic film layers. .

다음의 실시예는 상기 화학식 2의 화합물의 합성과 분석 및 유기전계발광소자에의 적용을 나타낸 것으로, 본 발명은 하기의 실시예들을 통해 더욱 상세히 설명될 수 있으나, 이들 실시예들에만 제한되는 것은 아니다.The following examples show the synthesis and analysis of the compound of Formula 2 and application to the organic light emitting device, the present invention can be described in more detail through the following examples, but is not limited only to these examples no.

실시예 1 : 벤조퀴놀린 리간드를 지닌 이리듐착체 화합물의 합성Example 1 Synthesis of Iridium Complex Compound with Benzoquinoline Ligand

상기 화학식 2의 화합물을 합성하기 위해서 먼저 이리듐(Ⅲ) 아세틸아세토네 이트(Iridium(Ⅲ) acetylacetonate, Ir(acac)3) 1g(0.00204 mol)과 7,8-벤조퀴놀린 2.23g(0.0124 mol)을 100 ml의 글리세롤(glycerol)이 들어있는 1L 플라스크에 넣은 후, 25분간 질소(N2 ) 가스를 통과시켜 글리세롤과 플라스크 속을 질소(N2 ) 가스로 채웠다. 그 후 반응용기를 환류 온도에서 15시간 동안 가열한 후 냉각시켰다. 상기 반응 용기를 냉각한 다음, 1M의 염산(HCl) 용액 600 ml를 교반하면서 상기 반응액에 첨가시켰다. 이때 발생하는 침전물을 여과하여 얻었다. 얻어진 침전물을 1M의 염산 용액 400 ml로 세척한 후, 증류수 500 ml로 다시 세척하였다. 이렇게 얻어진 침전물을 30 ml의 디클로로메탄(CH2Cl2)에 부유시킨 후, 이 현탁액에 50 ml의 메탄올을 부어 여과한 후 건조하였다. 건조 후 0.57g의 생성물이 얻어졌다.In order to synthesize the compound of Formula 2, Iridium (III) acetylacetonate (Iridium (III) acetylacetonate, Ir (acac) 3 ) 1g (0.00204 mol) and 7,8-benzoquinoline 2.23g (0.0124 mol) Into a 1 L flask containing 100 ml of glycerol, and then passed through nitrogen (N 2 ) gas for 25 minutes to allow the glycerol and the flask into nitrogen (N 2 ). Filled with gas. Thereafter, the reaction vessel was heated at reflux for 15 hours and then cooled. After the reaction vessel was cooled, 600 ml of 1 M hydrochloric acid (HCl) solution was added to the reaction solution with stirring. The precipitate generated at this time was obtained by filtration. The precipitate obtained was washed with 400 ml of 1 M hydrochloric acid solution and then again with 500 ml of distilled water. The precipitate thus obtained was suspended in 30 ml of dichloromethane (CH 2 Cl 2 ), and 50 ml of methanol was poured into the suspension, followed by filtration and drying. 0.57 g of product was obtained after drying.

실시예 2 : 벤조퀴놀린 리간드를 갖는 이리듐착체 화합물의 분석Example 2 Analysis of Iridium Complex Compounds Having Benzoquinoline Ligands

상기 실시예 1에서 얻어진 신물질은 용매에 대한 용해성이 좋지 않아서 NMR 분석 대신 원소분석(Elemental Analysis)에 의하여 합성 여부를 판단하였다. 상기 물질의 원소분석 결과는 다음과 같으며, 이러한 결과로 인해 새로운 이리듐착체 화합물이 합성되었음을 확인하였다.The new material obtained in Example 1 was poor in solubility in a solvent, and thus was determined by elemental analysis instead of NMR analysis. Elemental analysis of the material is as follows, it was confirmed that the new iridium complex compound was synthesized by this result.

계산 수치(Cal.): C - 64.45 %, H - 3.33 %, N - 5.77 %Calculated Cal .: C-64.45%, H-3.33%, N-5.77%

실험 수치(Obs.): C - 64.20 %, H - 3.52 %, N - 5.32 %Experimental figures (Obs.): C-64.20%, H-3.52%, N-5.32%

한편, 상기 실시예 1과 같이 합성된 물질은 유기전계발광소자로 사용하기 위해 진공승화장치로 승화 정제되었다. 그 결과로 얻어진 물질은 옅은 갈색을 띤 고체였으며, 유기전계발광소자에서 발광층 또는 발광층을 위한 도판트(dopant)로서 사용된다.On the other hand, the material synthesized as in Example 1 was sublimed and purified by a vacuum sublimation device for use as an organic light emitting device. The resulting material was a light brownish solid and used as a light emitting layer or dopant for the light emitting layer in organic electroluminescent devices.

또한, 이리듐착체의 다른 유도체들도 실시예 1과 유사한 방법으로 합성되며, 그 결과로 합성된 물질들도 발광층 또는 발광층을 위한 도판트로 사용될 수 있다. In addition, other derivatives of the iridium complex are also synthesized in a similar manner to Example 1, and as a result, the synthesized materials can be used as a light emitting layer or a dopant for the light emitting layer.

실시예 3 : 본 발명에 따른 유기전계발광소자의 구조Example 3 Structure of Organic Electroluminescent Device According to the Present Invention

실시예 3에서는 상기 승화 정제된 발광 물질을 유기전계발광소자의 발광층츨 위한 도판트로 사용하였다. 유기전계발광소자는 적층구조로 제작될 수 있으며, 제작 방법은 다음과 같다.In Example 3, the sublimed purified light emitting material was used as a dopant for emitting the light emitting layer of the organic light emitting device. The organic light emitting display device may be manufactured in a laminated structure, and a manufacturing method thereof is as follows.

(1) 투명 기판 위에 형성된 약 10 내지 400 nm 두께의 제 1 전극을 형성하였다.(1) A first electrode of about 10 to 400 nm thickness formed on the transparent substrate was formed.

(2) 그 위에 정공 주입층을 약 1 nm 내지 100 nm 두께로 입혔다. 이때 Copper phthalocyanine(CuPc)을 사용할 수 있다.(2) A hole injection layer was coated thereon with a thickness of about 1 nm to 100 nm. Copper phthalocyanine (CuPc) can be used.

(3) 그 위에 정공 수송층을 약 1 nm - 100 nm 두께로 입힌다. NPD(N,N'-dinaphthyl-N,N'-phenyl-(1,1'-biphenyl)-4,4'-diamine) 등이 사용되어질 수 있다.(3) On it, a hole transport layer is coated with a thickness of about 1 nm-100 nm. NPD (N, N'-dinaphthyl-N, N'-phenyl- (1,1'-biphenyl) -4,4'-diamine) and the like can be used.

(4) 다음 발광층을 약 1 nm 내지 200 nm 두께로 입힌다. 이때 사용되는 발광층으로는 Alq3(tris(8-hydroxy-quinolate)aluminium), 또는 CPB(4, 4'-N,N'-dicarbazole-biphenyl) 등을 사용할 수 있다. 이 발광층에 1 - 10 % 정도로 본발명에서 합성한 인광물질을 도핑(doping)하였다.(4) The next light emitting layer is coated with a thickness of about 1 nm to 200 nm. In this case, Alq 3 (tris (8-hydroxy-quinolate) aluminum), or CPB (4, 4'-N, N'-dicarbazole-biphenyl) may be used as the light emitting layer. The light emitting layer was doped with the phosphor synthesized in the present invention at about 1-10%.

(5) 다음 정공 정지층을 1 nm 내지 100 nm 두께로 형성할 수 있다. BCP(Bathocuproin)를 사용할 수 있으며, 필요에 따라 이 층을 생략할 수도 있다. (5) The following hole stopping layer can be formed with a thickness of 1 nm to 100 nm. BCP (Bathocuproin) can be used, and this layer can be omitted if necessary.                     

(6) 다음 전자 수송층을 1 nm 내지 200 nm 의 두께로 입힌다. 전자 수송층으로는 Alq3가 사용될 수 있다.(6) The following electron transport layer is coated with a thickness of 1 nm to 200 nm. Alq 3 may be used as the electron transport layer.

(7) 다음 1 nm 내지 100 nm 두께의 알칼리금속 또는 알칼리토금속 화합물로 이루어진 전자주입층을 형성한다.(7) Next, an electron injection layer made of an alkali metal or alkaline earth metal compound having a thickness of 1 nm to 100 nm is formed.

(8) 약 10 nm 내지 100 nm 두께의 제 2전극을 입힌다.(8) A second electrode of about 10 nm to 100 nm thickness is coated.

Figure 112001007070199-pat00003
Figure 112001007070199-pat00003

이리듐착체 화합물은 우수한 발광효율을 가지는 것으로 평가되어지고 있다. 따라서, 본 발명에서는 새로운 부류의 벤조퀴놀린 리간드를 가진 화합물을 합성하였으며 이들 화합물은 각각의 리간드와 금속이 인광을 발생하고, 또 이리듐과 리간드의 착체가 형성되었을 때 분자량이 크므로 선택규칙(selection rule)에 반하여 인광을 발생할 수 있는 특성을 가진다. Iridium complex compounds are evaluated to have excellent luminous efficiency. Therefore, in the present invention, a compound having a new class of benzoquinoline ligands has been synthesized, and these compounds have a high molecular weight when each ligand and a metal generate phosphorescence, and a complex of iridium and a ligand forms a selection rule. ) Has the property of generating phosphorescence.

본 발명의 유기전계발광소자에 적용되는 화합물 중 하나인 상기 화합물을 350nm 파장 근처에서 여기시켰을 때 광발광(photoluminescence) 세기를 측정한 결과를 도 3에 도시 하였다. 도 3에 도시된 바와 같이, 상기 화합물은 664nm의 발광 세기를 나타내었으며, 이러한 발광 세기는 상기 화합물이 유기전계발광소자의 발광층에 도핑되었을 때 높은 전계발광효율을 가질 수 있음을 나타낸다.FIG. 3 shows the results of measuring photoluminescence intensity when the compound, which is one of the compounds applied to the organic light emitting device of the present invention, is excited at 350 nm wavelength. As shown in FIG. 3, the compound exhibits a light emission intensity of 664 nm, which indicates that the compound may have high electroluminescence efficiency when the compound is doped in the light emitting layer of the organic light emitting device.

따라서, 본 발명에서의 벤조퀴놀린 리간드를 가진 화합물을 유기전계발광소자의 발광물질로 사용함으로써 소자의 안정성을 높여 소자의 수명이 향상되고 발광효율이 우수한 유기전계발광소자를 제공할 수 있다.

Therefore, by using the compound having a benzoquinoline ligand in the present invention as a light emitting material of the organic light emitting device, it is possible to provide an organic light emitting device having improved device stability and improved device life and excellent luminous efficiency.

Claims (7)

치환되거나 치환되지 않은 벤조퀴놀린 리간드를 갖는 이리듐착체 화합물.Iridium complex compounds having a substituted or unsubstituted benzoquinoline ligand. 제 1항에 있어서, 상기 화합물은 하기의 화학식을 갖는 것임을 특징으로 하는 벤조퀴놀린 리간드를 갖는 이리듐착체 화합물:The iridium complex compound having a benzoquinoline ligand according to claim 1, wherein the compound has the formula:
Figure 112001007070199-pat00004
Figure 112001007070199-pat00004
 이때, 상기 R1, R2, R3, R4, R5, R6, R7 및 R8가 수소(H), 치환되거나 치환되지 않은 알킬기(탄소수 1-18개), 치환되거나 치환되지 않은 아릴기(탄소수 6-18개), 시클로 알킬기(탄소수 3-18개), 방향족헤테로고리기, 할로겐기, 니트로기, 시아노기, 포밀기, 카르복시기, 에스테르기, 아미드기, 비닐기, 치환된 비닐기, 치환되거나 치환되지 않은 아세틸렌기, 치환되거나 치환되지 않은 티올기, 아미노기, 치환 되거나 치환되지 않은 아릴아미노기(탄소수 6-18개), 수산기, 알콕시기(탄소수 1-18개) 및 치환되거나 치환되지 않은 아릴옥시기(탄소수 6-18개)로 이루어진 군에서 각각 독립적으로 선택되는 어느 하나이며;In this case, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 is hydrogen (H), substituted or unsubstituted alkyl group (1-18 carbon atoms), substituted or unsubstituted Unsubstituted aryl group (6-18 carbon atoms), cycloalkyl group (3-18 carbon atoms), aromatic heterocyclic group, halogen group, nitro group, cyano group, formyl group, carboxyl group, ester group, amide group, vinyl group, substitution Vinyl group, substituted or unsubstituted acetylene group, substituted or unsubstituted thiol group, amino group, substituted or unsubstituted arylamino group (6-18 carbon atoms), hydroxyl group, alkoxy group (1-18 carbon atoms) and substituted Each independently selected from the group consisting of a substituted or unsubstituted aryloxy group having 6 to 18 carbon atoms; 상기 R1 내지 R8은 서로 동일 또는 상이해도 좋음.R 1 to R 8 may be the same or different from each other. 제 2항에 있어서, 상기 R1과 R2, R2와 R3, R3과 R4, R4와 R5, R5와 R6, R6과 R7 그리고 R7과 R8은 각각 독립적으로 또는 상호 연결되어 지방족고리(탄소수 1-18개)를 형성하는 것임을 특징으로 하는 벤조퀴놀린 리간드를 갖는 화합물.According to claim 2, wherein R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 and R 7 and R 8 are respectively A compound having a benzoquinoline ligand, characterized in that independently or interconnected to form an aliphatic ring (1-18 carbon atoms). 제 2항에 있어서, 상기 R1과 R2, R2와 R3, R3과 R4, R4와 R5, R5와 R6, R6과 R7 그리고 R7과 R8은 각각 독립적으로 또는 상호 연결되어 방향족고리(탄소수 1-18개)를 형성하는 것임을 특징으로 하는 벤조퀴놀린 리간드를 갖는 화합물.According to claim 2, wherein R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 and R 7 and R 8 are respectively A compound having a benzoquinoline ligand, characterized in that independently or interconnected to form an aromatic ring (1-18 carbon atoms). 제 2항에 있어서, 상기 R1과 R2, R2와 R3, R3과 R4, R4와 R5, R5와 R6, R6과 R7 그리고 R7과 R8은 각각 독립적으로 또는 상호 연결되어 헤테로고리(탄소 및 헤테로 원자수 1-18개)를 형성하는 것임을 특징으로 하는 벤조퀴놀린 리간드를 갖는 화합물.According to claim 2, wherein R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 and R 7 and R 8 are respectively A compound having a benzoquinoline ligand, characterized in that it is independently or interconnected to form a heterocycle (carbon and 1-18 hetero atoms). 제 2항에 있어서, 상기 R1, R2, R3, R4, R5, R6 , R7 및 R8은 수소(H)인 것임을 특징으로 하는 벤조퀴놀린 리간드를 갖는 화합물.The compound having a benzoquinoline ligand according to claim 2, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are hydrogen (H). 제 1전극, 제 2전극 및 다수의 유기막층을 포함하는 유기전계발광소자에 있어서, 제 1항 내지 제 6항 중 어느 한 항의 화합물이 함유된 발광층을 포함하여 구성됨을 특징으로 하는 유기전계발광소자.An organic light emitting display device comprising a first electrode, a second electrode and a plurality of organic film layers, the organic light emitting display device comprising a light emitting layer containing the compound of any one of claims 1 to 6. .
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US9416107B2 (en) 2011-06-29 2016-08-16 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100947699B1 (en) * 2007-05-08 2010-03-16 광주과학기술원 Iridium Complex having Ligands and Polymer using the Iridium Complex
US9416107B2 (en) 2011-06-29 2016-08-16 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same

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