KR20100108924A - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents
Novel organic electroluminescent compounds and organic electroluminescent device using the same Download PDFInfo
- Publication number
- KR20100108924A KR20100108924A KR1020090027256A KR20090027256A KR20100108924A KR 20100108924 A KR20100108924 A KR 20100108924A KR 1020090027256 A KR1020090027256 A KR 1020090027256A KR 20090027256 A KR20090027256 A KR 20090027256A KR 20100108924 A KR20100108924 A KR 20100108924A
- Authority
- KR
- South Korea
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- ring
- aryl
- Prior art date
Links
- ZZAJEWDISXDSMC-UHFFFAOYSA-N Brc1c(cccc2)c2c(c2ccccc2[n]2C3C=CC=CC3)c2c1 Chemical compound Brc1c(cccc2)c2c(c2ccccc2[n]2C3C=CC=CC3)c2c1 ZZAJEWDISXDSMC-UHFFFAOYSA-N 0.000 description 1
- KNJJGSGPSKPDBR-UHFFFAOYSA-N Brc1cc([nH]c2c3cccc2)c3c2ccccc12 Chemical compound Brc1cc([nH]c2c3cccc2)c3c2ccccc12 KNJJGSGPSKPDBR-UHFFFAOYSA-N 0.000 description 1
- DDGPPAMADXTGTN-UHFFFAOYSA-N Clc1nc(-c2ccccc2)nc(-c2ccccc2)n1 Chemical compound Clc1nc(-c2ccccc2)nc(-c2ccccc2)n1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 1
- VKDDHLJWNUYWTL-UHFFFAOYSA-N [O-][N+](C1=CC=CCC1Br)=O Chemical compound [O-][N+](C1=CC=CCC1Br)=O VKDDHLJWNUYWTL-UHFFFAOYSA-N 0.000 description 1
- GKLRATMPBWWYCZ-UHFFFAOYSA-N [O-][N+](c(cccc1)c1-c(cc1)c(cccc2)c2c1Br)=O Chemical compound [O-][N+](c(cccc1)c1-c(cc1)c(cccc2)c2c1Br)=O GKLRATMPBWWYCZ-UHFFFAOYSA-N 0.000 description 1
- WWKCGWQJBPFVIG-UHFFFAOYSA-N [O-][N+](c(cccc1)c1-c1c(cccc2)c2ccc1)=O Chemical compound [O-][N+](c(cccc1)c1-c1c(cccc2)c2ccc1)=O WWKCGWQJBPFVIG-UHFFFAOYSA-N 0.000 description 1
- UUOLETYDNTVQDY-UHFFFAOYSA-N [O-][N+](c(cccn1)c1Cl)=O Chemical compound [O-][N+](c(cccn1)c1Cl)=O UUOLETYDNTVQDY-UHFFFAOYSA-N 0.000 description 1
- GEALTJGFPPNOJE-UHFFFAOYSA-N [O-][N+](c1c(-c2ccccc2)nccc1)=O Chemical compound [O-][N+](c1c(-c2ccccc2)nccc1)=O GEALTJGFPPNOJE-UHFFFAOYSA-N 0.000 description 1
- NSBVOLBUJPCPFH-UHFFFAOYSA-N c(cc1)cc2c1[nH]c1c2nccc1 Chemical compound c(cc1)cc2c1[nH]c1c2nccc1 NSBVOLBUJPCPFH-UHFFFAOYSA-N 0.000 description 1
- QCOBIYTWKFFPQI-UHFFFAOYSA-N c(cc1)ccc1-c1cc([n](c2ccccc22)-c3ccccc3)c2c2c1cccc2 Chemical compound c(cc1)ccc1-c1cc([n](c2ccccc22)-c3ccccc3)c2c2c1cccc2 QCOBIYTWKFFPQI-UHFFFAOYSA-N 0.000 description 1
- FPYFMYUXGHWHJZ-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-[n]2c3cccnc3c3c2cccc3)nc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c1nc(-[n]2c3cccnc3c3c2cccc3)nc(-c2ccccc2)n1 FPYFMYUXGHWHJZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- 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
-
- 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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
본 발명은 신규한 유기 발광 화합물 및 이를 포함하고 있는 유기 전계 발광 소자 에 관한 것으로, 상세하게는 본 발명에 따른 유기 발광 화합물은 하기 화학식 1로 표시되는 것을 특징으로 한다.The present invention relates to a novel organic light emitting compound and an organic electroluminescent device comprising the same, in detail, the organic light emitting compound according to the invention is characterized in that represented by the formula (1).
[화학식 1][Formula 1]
[상기 화학식 1에서, A 고리 및 B 고리는 서로 독립적으로 단일환 또는 다환의 방향족 고리, 단일환 또는 다환의 헤테로 방향족 고리, 방향족 고리가 융합된 5원 내지 6원의 헤테로 방향족 고리, 5원 내지 6원의 헤테로 방향족 고리가 융합된 단일환 또는 다환의 방향족 고리이고, 단 A 고리와 B 고리가 동시에 단일환의 방향족 고리인 경우는 제외한다.][In Formula 1, A ring and B ring are independently of each other monocyclic or polycyclic aromatic ring, monocyclic or polycyclic heteroaromatic ring, 5- to 6-membered heteroaromatic ring fused with an aromatic ring, 5-membered to A six-membered heteroaromatic ring is a fused monocyclic or polycyclic aromatic ring, except where the A and B rings are monocyclic aromatic rings at the same time.]
표시 소자 중, 전기 발광 소자(electroluminescence device: EL device)는 자체 발광형 표시 소자로서 시야각이 넓고 콘트라스트가 우수할 뿐만 아니라 응답속도가 빠르다는 장점을 가지고 있으며, 1987년 이스트만 코닥(Eastman Kodak)사에서는 발광층 형성용 재료로서 저분자인 방향족 디아민과 알루미늄 착물을 이용하고 있는 유기 EL 소자를 처음으로 개발하였다[Appl. Phys. Lett. 51, 913, 1987].Among the display elements, an electroluminescence device (EL device) is a self-luminous display element that has a wide viewing angle, excellent contrast, and high response speed.Eastman Kodak Co., Ltd. in 1987 An organic EL device using a low molecular aromatic diamine and an aluminum complex as a light emitting layer formation material was first developed [Appl. Phys. Lett. 51, 913, 1987].
유기 EL 소자는 전자 주입 전극(음극) 과 정공 주입 전극(양극) 사이에 형성된 유기막에 전하를 주입하면 전자와 정공이 쌍을 이루어 여기자를 생성한다. 여기자의 비활성시의 발광(인광 또는 형광)을 이용함으로써 빛이 방출된다. 유기 EL 소자는 약 10V의 전압과 약 100∼10,000cd/㎡의 높은 휘도로 편광을 방출하며, 단순히 형광물질을 선택함으로써 파란색에서 빨간색까지의 스펙트럼으로 빛을 방출한다는 특징이 있다. 플라스틱 같은 휠 수 있는(flexible) 투명 기판 위에도 소자를 형성할 수 있을 뿐 아니라, 플라즈마 디스플레이 패널(Plasma Display Panel)이나 무기 EL 디스플레이에 비해 낮은 전압에서 (10V이하) 구동이 가능하고, 전력 소모가 비교적 적으며, 색감이 뛰어나다는 장점이 있다. The organic EL element injects charge into an organic film formed between the electron injection electrode (cathode) and the hole injection electrode (anode) to generate excitons by pairing electrons and holes. Light is emitted by using light emission (phosphorescence or fluorescence) when the excitons are inactive. The organic EL device emits polarized light with a voltage of about 10 V and a high luminance of about 100 to 10,000 cd / m 2, and emits light in a spectrum from blue to red by simply selecting a fluorescent material. The device can be formed on a flexible transparent substrate such as plastic, and can be driven at a lower voltage (less than 10V) compared to a plasma display panel or an inorganic EL display, and has a relatively low power consumption. It has a small and excellent color.
유기 EL 소자에서 발광 효율, 수명 등의 성능을 결정하는 가장 중요한 요인은 발광 재료로서, 이러한 발광 재료에 요구되는 몇 가지 특성으로는 고체상태에서 형광 양자 수율이 커야하고, 전자와 정공의 이동도가 높아야 하며, 진공 증착시 쉽게 분해되지 않아야 하고, 균일한 박막을 형성, 안정해야한다. The most important factor that determines the performance of light emission efficiency, lifespan, etc. in the organic EL device is a light emitting material. Some characteristics required for such a light emitting material include a high fluorescence quantum yield in the solid state, and mobility of electrons and holes. It should be high, not easily decomposed during vacuum deposition, and should form and stabilize a uniform thin film.
유기 발광 재료는 크게 고분자 재료와 저분자 재료로 나눌 수 있는데, 저분자 계열의 재료는 분자 구조 면에서 금속 착화합물과 금속을 포함하지 않는 순수 유기 발광 재료가 있다. 이러한 발광 재료로는 트리스(8-퀴놀리놀라토)알루미늄 착 제 등의 킬레이트 착제, 쿠마린 유도체, 테트라페닐부타디엔 유도체, 비스스타이릴아릴렌 유도체, 옥사다이아졸 유도체 등의 발광 재료가 알려져 있고, 이들로부터는 청색에서 적색까지의 가시 영역 발광을 얻을 수 있다고 보고되었다.Organic light emitting materials can be classified into high molecular materials and low molecular materials. Low molecular materials include pure organic light emitting materials that do not contain metal complexes and metals in terms of molecular structure. As such light emitting materials, light emitting materials such as chelate complexes such as tris (8-quinolinolato) aluminum complexes, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives and oxadiazole derivatives are known. Has been reported to obtain visible region luminescence from blue to red.
풀칼라 OLED 디스플레이의 구현을 위해서는 RGB 3가지의 발광재료를 사용하게 되는데 유기 EL 전체의 특성을 향상시키는데 고효율 장수명의 RGB 발광재료의 개발이 중요한 과제라고 할 수 있다. 발광재료는 기능적인 측면에서 호스트 재료와 도판트 재료로 구분될 수 있는데 일반적으로 EL 특성이 가장 우수한 소자 구조로는 호스트에 도판트를 도핑하여 발광층을 만드는 것으로 알려져 있다. 최근에 고효율, 장수명 유기 EL 소자의 개발이 시급한 과제로 대두되고 있으며, 특히 중대형 OLED 패널에서 요구하고 있는 EL 특성 수준을 고려해 볼 때 기존의 발광재료에 비해 매우 우수한 재료의 개발이 시급한 실정이다. 이러한 측면에서 호스트 재료의 개발이 해결해야 할 가장 중요한 요소 중의 하나이다. 이때 고체 상태의 용매 및 에너지 전달자 역할을 하는 호스트 물질의 바람직한 특성은 순도가 높아야하며, 진공증착이 가능하도록 적당한 분자량을 가져야 한다. 또한 유리 전이온도와 열분해온도가 높아 열적 안정성을 확보해야하며, 장수명화를 위해 높은 전기화학적 안정성이 요구되며, 무정형박막을 형성하기 용이해야 하며, 인접한 다른 층의 재료들과는 접착력이 좋은 반면 층간이동은 하지 않아야 한다.In order to realize a full color OLED display, three kinds of RGB light emitting materials are used, and development of high efficiency long life RGB light emitting materials is an important task to improve the characteristics of the entire organic EL. The light emitting material can be classified into a host material and a dopant material in terms of its function. In general, a device structure having excellent EL characteristics is known to make a light emitting layer by doping a host with a dopant. Recently, the development of high efficiency and long life organic EL devices has emerged as an urgent task, and considering the level of EL characteristics required in medium and large OLED panels, it is urgent to develop materials that are much superior to existing light emitting materials. In this respect, the development of host materials is one of the most important factors to be solved. In this case, the desirable properties of the host material serving as a solvent and energy transporter in the solid state should be high in purity and have an appropriate molecular weight to enable vacuum deposition. In addition, high glass transition temperature and pyrolysis temperature should ensure thermal stability, high electrochemical stability is required for long life, easy to form amorphous thin film, good adhesion with other adjacent materials, Should not.
유기 EL 소자를 도핑기술을 사용하여 제조하는 경우 여기상태에서 호스트분자로부터 도판트로의 에너지전달은 100%가 되지 못하고, 도판트뿐만 아니라 호스트물질도 빛을 방출하게 된다. 특히 적색발광소자인 경우에는 호스트물질이 도판트보 다 가시성이 큰 파장범위에서 빛을 방출하기 때문에 색순도가 호스트물질의 흐린 광방출에 의해 악화된다. 또 실제로 적용하는 경우 발광수명 및 지속성이 개선될 필요가 있다.When an organic EL device is manufactured using a doping technique, energy transfer from the host molecule to the dopant in the excited state is less than 100%, and not only the dopant but also the host material emits light. In particular, in the case of a red light emitting device, since the host material emits light in a wavelength range that is more visible than that of the dopant, color purity is deteriorated by the light emission of the host material. In addition, the light emission life and the sustainability need to be improved in practical application.
한편, 인광 발광체의 호스트 재료로는 현재까지 CBP가 가장 널리 알려져 있으며, BCP 및 BAlq 등의 정공차단층을 적용한 고효율의 OLED가 공지되어 있으며, 일본의 파이오니어 등에서는 BAlq 유도체를 호스트로 이용한 고성능의 OLED가 공지되어 있다.On the other hand, CBP is the most widely known host material for phosphorescent emitters, and high-efficiency OLEDs using a hole blocking layer such as BCP and BAlq are known, and high-performance OLEDs using BAlq derivatives as a host are known in Pioneer, Japan. Is known.
그러나 기존의 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮고 열적 안정성이 매우 좋지 않아서, 진공 하에서 고온 증착 공정을 거칠 때, 물질이 변하는 등 단점을 갖고 있다. OLED에서 전력효율 = (π/전압) × 전류효율 이므로, 전력효율은 전압에 반비례하는데, OLED의 소비 전력이 낮으려면 전력 효율이 높아야한다. 실제 인광 발광 재료를 사용한 OLED는 형광 발광 재료를 사용한 OLED에 비해 전류 효율(cd/A)이 상당히 높으나, 인광 발광 재료의 호스트로 BAlq 나 CBP 등 종래의 재료를 사용할 경우, 형광재료를 사용한 OLED에 비해 구동 전압이 높아서 전력 효율(lm/w)면에서 큰 이점이 없었다.However, existing materials have advantages in terms of luminescence properties, but the glass transition temperature is low and the thermal stability is not very good, and thus has a disadvantage such that the material changes when undergoing a high temperature deposition process under vacuum. Since power efficiency = (π / voltage) × current efficiency in OLEDs, power efficiency is inversely proportional to voltage. However, low power consumption of OLEDs requires high power efficiency. Actually, OLEDs using phosphorescent materials have significantly higher current efficiency (cd / A) than OLEDs using fluorescent materials.However, when a conventional material such as BAlq or CBP is used as a host of phosphorescent materials, OLEDs using fluorescent materials Compared with the higher driving voltage, there was no significant advantage in terms of power efficiency (lm / w).
또한, OLED 소자에서의 수명 측면에서도 결코 만족할만한 수준이 되질 못하여 더욱 안정되고, 더욱 성능이 뛰어난 호스트 재료의 개발이 요구되고 있다.In addition, in terms of lifespan in OLED devices, they are never satisfactory, and development of a more stable and more excellent host material is required.
따라서 본 발명의 목적은 첫째로, 상기한 문제점들을 해결하기 위하여 기존의 재료보다 발광 효율 및 소자 수명이 좋으며, 적절한 색좌표를 갖는 우수한 골격의 유기 발광 화합물을 제공하는 것이며 둘째로, 상기 유기 발광 화합물을 발광 재료로서 채용하는 고효율 및 장수명의 유기 전계 발광 소자를 제공하는 것이다. Accordingly, an object of the present invention is to firstly provide an organic light emitting compound having excellent luminous efficiency and device life, and having an appropriate color coordinate, in order to solve the above problems, and secondly, to solve the above organic light emitting compound. It is to provide a high efficiency and long life organic electroluminescent element employed as a light emitting material.
본 발명은 하기 화학식 1로 표시되는 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로서, 본 발명에 따른 유기 발광 화합물은 발광효율이 좋고 재료의 색순도 및 수명특성이 뛰어나 구동수명이 매우 우수한 OLED 소자를 제조할 수 있는 장점이 있다.The present invention relates to an organic light emitting compound represented by the following Chemical Formula 1 and an organic electroluminescent device comprising the same, the organic light emitting compound according to the present invention has excellent luminous efficiency and excellent color purity and life characteristics of the material OLED very excellent driving life There is an advantage to manufacture the device.
[화학식 1][Formula 1]
[상기 화학식 1에서, A 고리 및 B 고리는 서로 독립적으로 단일환 또는 다환의 방향족 고리, 단일환 또는 다환의 헤테로 방향족 고리, 방향족 고리가 융합된 5원 내지 6원의 헤테로 방향족 고리, 5원 내지 6원의 헤테로 방향족 고리가 융합된 단일환 또는 다환의 방향족 고리이고, 단 A 고리와 B 고리가 동시에 단일환의 방향족 고리인 경우는 제외하고;[In Formula 1, A ring and B ring are independently of each other monocyclic or polycyclic aromatic ring, monocyclic or polycyclic heteroaromatic ring, 5- to 6-membered heteroaromatic ring fused with an aromatic ring, 5-membered to The six-membered heteroaromatic ring is a fused monocyclic or polycyclic aromatic ring, except that the A and B rings are simultaneously monocyclic aromatic rings;
R1, R2 및 R3은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)헤테로아릴, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬, 치환 또는 비치환된 아다만틸, 치환 또는 비치환된(C7-C30)바이시클로알킬, 시아노, NR11R12, BR13R14, PR15R16, P(=O)R17R18[R11 내지 R18은 서로 독립적으로 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 치환 또는 비치환된(C3-C30)헤테로아릴이다.], 치환 또는 비치환된 트리(C1-C30)알킬실릴, 치환 또는 비치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환 또는 비치환된 트리(C6-C30)아릴실릴, 치환 또는 비치환된 (C6-C30)아르(C1-C30)알킬, 치환 또는 비치환된(C1-C30)알킬옥시, 치환 또는 비치환된(C1-C30)알킬티오, 치환 또는 비치환된(C6-C30)아릴옥시, 치환 또는 비치환된(C6-C30)아릴티오, 치환 또는 비치환된(C1-C30)알콕시카보닐, 치환 또는 비치환된(C1-C30)알킬카보닐, 치환 또는 비치환된(C6-C30)아릴카보닐, 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C2-C30)알키닐, 치환 또는 비치환된(C6-C30)아릴옥시카보닐, 치환 또는 비치환된(C1-C30)알콕시카보닐옥시, 치환 또는 비치환된(C1-C30)알킬카보닐옥시, 치환 또는 비치환된(C6-C30)아릴카보닐옥시, 치환 또는 비치환된(C6-C30)아릴옥시카보닐옥시, 카르복실, 나이트로, 하이드록시이거나, 인접한 치환체와 융합고리를 포함하거 나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며; R 1 , R 2 and R 3 are Each one independently Hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5 member 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted aromatic ring, wherein one to seven membered heterocycloalkyl, substituted or unsubstituted aromatic rings are fused. Is at least one fused (C3-C30) cycloalkyl, substituted or unsubstituted adamantyl, substituted or unsubstituted (C7-C30) bicycloalkyl, cyano, NR 11 R 12 , BR 13 R 14 , PR 15 R 16 , P (= O) R 17 R 18 [R 11 to R 18 are independently of each other substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted Substituted (C3-C30) heteroaryl], substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted ring Tri (C6-C30) arylsilyl, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkyloxy, substituted or unsubstituted (C1-C30) Alkylthio, substituted or unsubstituted (C6-C30) aryloxy, substituted or unsubstituted (C6-C30) arylthio, substituted or unsubstituted (C1-C30) alkoxycarbonyl, substituted or unsubstituted (C1 -C30) alkylcarbonyl, substituted or unsubstituted (C6-C30) arylcarbonyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted Substituted (C6-C30) aryloxycarbonyl, substituted or unsubstituted (C1-C30) alkoxycarbonyloxy, substituted or unsubstituted (C1-C30) alkylcarbonyloxy, substituted or unsubstituted (C6- C30) arylcarbonyloxy, substituted or unsubstituted (C6-C30) aryloxycarbonyloxy, carboxyl, nitro, hydroxy, with or without adjacent substituents and fused rings (C3-C30) Alkylene or (C3-C30) alkenylene Connecting the alicyclic ring, or a monocyclic or polycyclic, and may form a ring;
A 고리 및 B 고리의 수소원자는 중수소로 더 치환될 수 있다.]The hydrogen atoms of the A and B rings may be further substituted with deuterium.]
본 발명에 기재된 “알킬”, “알콕시” 및 그 외 “알킬”부분을 포함하는 치환체는 직쇄 또는 분쇄 형태를 모두 포함한다. Substituents comprising the "alkyl", "alkoxy" and other "alkyl" moieties described herein include both straight and pulverized forms.
본 발명에 기재된 「아릴」은 하나의 수소 제거에 의해서 방향족 탄화수소로부터 유도된 유기 라디칼로, 각 고리에 적절하게는 4 내지 7개, 바람직하게는 5 또는 6개의 고리원자를 포함하는 단일 또는 융합고리계를 포함하며, 다수개의 아릴이 단일결합으로 연결되어 있는 형태까지 포함한다. 구체적인 예로 페닐, 나프틸, 비페닐, 안트릴, 인데닐(indenyl), 플루오레닐, 페난트릴, 트리페닐레닐, 피렌일, 페릴렌일, 크라이세닐, 나프타세닐, 플루오란텐일 등을 포함하지만, 이에 한정되지 않는다. 상기 나프틸은 1-나프틸 및 2-나프틸을 포함하며, 안트릴은 1-안트릴, 2-안트릴 및 9-안트릴을 포함하며, 플루오레닐은 1-플루오레닐, 2-플루오레닐, 3-플루오레닐, 4-플루오레닐 및 9-플루오레닐을 모두 포함한다. 본 발명에 기재된 「헤테로아릴」은 방향족 고리 골격 원자로서 B, N, O, S, P(=O), Si 및 P로부터 선택되는 1 내지 4개의 헤테로원자를 포함하고, 나머지 방향족 고리 골격 원자가 탄소인 아릴 그룹을 의미하는 것으로, 5 내지 6원 단환 헤테로아릴, 및 하나 이상의 벤젠 환과 축합된 다환식 헤테로아릴이며, 부분적으로 포화될 수도 있다. 또한, 본 발명에서의 헤테로아릴은 하나 이상의 헤테로아릴이 단일결합으로 연걸된 형태도 포함한다. 상기 헤테로아릴기는 고리내 헤테로원자가 산화되거나 사원화되어, 예를 들어 N-옥사이드 또는 4차 염을 형성하는 2가 아릴 그룹을 포함한다. 구체적인 예로 퓨릴, 티오펜일, 피롤릴, 이미다졸릴, 피라졸릴, 티아졸릴, 티아디아졸릴, 이소티아졸릴, 이속사졸릴, 옥사졸릴, 옥사디아졸릴, 트리아진일, 테트라진일, 트리아졸릴, 테트라졸릴, 퓨라잔일, 피리딜, 피라진일, 피리미딘일, 피리다진일 등의 단환 헤테로아릴, 벤조퓨란일, 벤조티오펜일, 이소벤조퓨란일, 벤조이미다졸릴, 벤조티아졸릴, 벤조이소티아졸릴, 벤조이속사졸릴, 벤조옥사졸릴, 이소인돌릴, 인돌릴, 인다졸릴, 벤조티아디아졸릴, 퀴놀릴, 이소퀴놀릴, 신놀리닐, 퀴나졸리닐, 퀴녹살리닐, 카바졸릴, 페난트리딘일, 벤조디옥솔릴 등의 다환식 헤테로아릴 및 이들의 상응하는 N-옥사이드(예를 들어, 피리딜 N-옥사이드, 퀴놀릴 N-옥사이드), 이들의 4차 염 등을 포함하지만, 이에 한정되지 않는다."Aryl" described in the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, and a single or fused ring containing 4 to 7, preferably 5 or 6 ring atoms in each ring as appropriate. It includes a system, including a form in which a plurality of aryl is connected by a single bond. Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, peryleneyl, chrysenyl, naphthasenyl, fluoranthenyl, and the like. It is not limited to this. Said naphthyl includes 1-naphthyl and 2-naphthyl, anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, and fluorenyl is 1-fluorenyl, 2- Fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl. The "heteroaryl" described in the present invention contains 1 to 4 heteroatoms selected from B, N, O, S, P (= O), Si, and P as aromatic ring skeleton atoms, and the remaining aromatic ring skeleton atoms are carbon. Meaning an aryl group which is 5 to 6 membered monocyclic heteroaryl, and polycyclic heteroaryl condensed with one or more benzene rings, which may be partially saturated. In addition, the heteroaryl in the present invention also includes a form in which one or more heteroaryls are linked by a single bond. Such heteroaryl groups include divalent aryl groups in which heteroatoms in the ring are oxidized or quaternized to form, for example, N-oxides or quaternary salts. Specific examples include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetra Monocyclic heteroaryl such as zolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoisothia Zolyl, Benzoisoxazolyl, Benzoxazolyl, Isoindoleyl, Indolyl, Indazolyl, Benzothiadiazolyl, Quinolyl, Isoquinolyl, Cinolinyl, Quinazolinyl, Quinoxalinyl, Carbazolyl, Phenantridinyl , Polycyclic heteroaryls such as benzodioxolyl and the like, and their corresponding N-oxides (eg, pyridyl N-oxides, quinolyl N-oxides), quaternary salts thereof, and the like. .
또한, 본 발명에 기재되어 있는 “(C1-C30)알킬, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬옥시, (C1-C30)알킬티오, (C1-C30)알킬옥시카보닐, (C1-C30)알킬카보닐, (C1-C30)알킬옥시카보닐옥시, (C1-C30)알킬카보닐옥시” 등의 알킬은 탄소수 1 내지 20개로 제한될 수 있고, 탄소수 1 내지 10개로 제한될 수 있다. “(C6-C30)아릴, 디(C1-C30)알킬(C6-C30)아릴실릴, 트리(C6-C30)아릴실릴, (C6-C30)아르(C1-C30)알킬, (C6-C30)아릴옥시, (C6-C30)아릴티오, (C6-C30)아릴카보닐, (C6-C30)아릴옥시카보닐, (C6-C30)아릴카보닐옥시, (C6-C30)아릴옥시카보닐옥시”등의 아릴은 탄소수 6 내지 20개로 제한될 수 있고, 탄소수 6 내지 12개로 제한될 수 있다. “(C3-C30)헤테로아 릴”의 헤테로아릴은 탄소수 4 내지 20개로 제한될 수 있고, 탄소수 4 내지 12개로 제한될 수 있다. “(C3-C30)시클로알킬”의 헤테로아릴은 탄소수 3 내지 20개로 제한될 수 있고, 탄소수 3 내지 7개로 제한될 수 있다. “(C2-C30)알케닐 또는 알키닐””의 알케닐 또는 알키닐은 탄소수 2 내지 20개로 제한될 수 있고, 탄소수 2 내지 10개로 제한될 수 있다.Also described herein are “(C1-C30) alkyl, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C6-C30) ar (C1-C30) ) Alkyl, (C1-C30) alkyloxy, (C1-C30) alkylthio, (C1-C30) alkyloxycarbonyl, (C1-C30) alkylcarbonyl, (C1-C30) alkyloxycarbonyloxy, ( Alkyl, such as "C1-C30) alkylcarbonyloxy", may be limited to 1 to 20 carbon atoms, and may be limited to 1 to 10 carbon atoms. “(C6-C30) aryl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, (C6-C30) ar (C1-C30) alkyl, (C6-C30) Aryloxy, (C6-C30) arylthio, (C6-C30) arylcarbonyl, (C6-C30) aryloxycarbonyl, (C6-C30) arylcarbonyloxy, (C6-C30) aryloxycarbonyloxy Aryl such as ”may be limited to 6 to 20 carbon atoms, and may be limited to 6 to 12 carbon atoms. Heteroaryl of "(C3-C30) heteroaryl" may be limited to 4 to 20 carbon atoms, it may be limited to 4 to 12 carbon atoms. Heteroaryl of "(C3-C30) cycloalkyl" may be limited to 3 to 20 carbon atoms, it may be limited to 3 to 7 carbon atoms. Alkenyl or alkynyl of "(C2-C30) alkenyl or alkynyl" "may be limited to 2 to 20 carbon atoms, and may be limited to 2 to 10 carbon atoms.
또한 본 발명에 기재되어 있는 “치환 또는 비치환”이라는 기재는 상기 R1 내지 R3 및 R11 내지 R18의 치환기가 각각 독립적으로 중수소, 할로겐, 할로겐이 치환 또는 비치환된 (C1-C30)알킬, (C6-C30)아릴, (C6-C30)아릴이 치환 또는 비치환된 (C3-C30)헤테로아릴, 5원 내지 7원의 헤테로시클로알킬, 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, (C3-C30)시클로알킬, 방향족고리가 하나이상 융합된 (C6-C30)시클로알킬, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, 트리(C6-C30)아릴실릴, 아다만틸, (C7-C30)바이시클로알킬, (C2-C30)알케닐, (C2-C30)알키닐, 시아노, 카바졸릴, NR21R22, BR23R24, PR25R26, P(=O)R27R28[R21 내지 R28은 서로 독립적으로 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴 또는 치환 또는 비치환된 (C3-C30)헤테로아릴이다.], (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, (C1-C30)알킬옥시, (C1-C30)알킬티오, (C6-C30)아릴옥시, (C6-C30)아릴티오, (C1-C30)알콕시카보닐, (C1-C30)알킬카보닐, (C6-C30)아릴카보닐, (C6-C30)아릴옥시카보닐, (C1-C30)알콕시카보닐옥시, (C1-C30)알킬카보닐옥시, (C6-C30)아릴카보닐옥시, (C6-C30)아릴옥시카보닐옥시, 카르 복실, 나이트로 또는 하이드록시로 이루어진 군으로부터 선택되는 하나 이상으로 더 치환되거나, 서로 인접한 치환체가 연결되어 고리를 형성하는 것을 의미한다.In addition, the description of "substituted or unsubstituted" described in the present invention is that the substituents of R 1 to R 3 and R 11 to R 18 are each independently deuterium, halogen, halogen substituted or unsubstituted (C1-C30) (C3-C30) heteroaryl substituted or unsubstituted with alkyl, (C6-C30) aryl, (C6-C30) aryl, 5- to 7-membered heterocycloalkyl, 5- to 7 fused with one or more aromatic rings Original heterocycloalkyl, (C3-C30) cycloalkyl, (C6-C30) cycloalkyl fused with one or more aromatic rings, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) Arylsilyl, tri (C6-C30) arylsilyl, adamantyl, (C7-C30) bicycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, carbazolyl, NR 21 R 22 , BR 23 R 24 , PR 25 R 26 , P (= O) R 27 R 28 [R 21 to R 28 are independently of each other substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6 -C30) aryl or substituted or unsubstituted (C3-C30) hete Aryl], (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, (C1-C30) alkyloxy, (C1-C30) alkylthio, (C6- C30) aryloxy, (C6-C30) arylthio, (C1-C30) alkoxycarbonyl, (C1-C30) alkylcarbonyl, (C6-C30) arylcarbonyl, (C6-C30) aryloxycarbonyl, (C1-C30) alkoxycarbonyloxy, (C1-C30) alkylcarbonyloxy, (C6-C30) arylcarbonyloxy, (C6-C30) aryloxycarbonyloxy, carboxyl, nitro or hydroxy It is further substituted with one or more selected from the group consisting of, or means that adjacent substituents are connected to form a ring.
본 발명에 따른 화학식 1의 유기 발광 화합물은 하기 화학식 2 내지 6으로 표시되는 유기 발광 화합물을 포함한다.The organic light emitting compound of Formula 1 according to the present invention includes an organic light emitting compound represented by the following Chemical Formulas 2 to 6.
[화학식 2][Formula 2]
[화학식 3](3)
[화학식 4][Formula 4]
[화학식 5][Chemical Formula 5]
[화학식 6][Formula 6]
[상기 화학식 2 내지 6에서, B 고리, R1 및 R3는 상기 화학식 1에서의 정의와 동일하며;[In Formulas 2 to 6, the B ring, R 1 and R 3 are the same as the definition in Formula 1;
R41 내지 R44는 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)헤테로아릴, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬, 치환 또는 비치환된 아다만틸, 치환 또는 비치환된(C7-C30)바이시클로알킬, 시아노, NR21R22, BR23R24, PR25R26, P(=O)R27R28[R21 내지 R28은 서로 독립적으로 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴 또는 치환 또는 비치환된 (C3-C30)헤테로아릴이다.], 치환 또는 비치환된 트리(C1-C30)알킬실릴, 치환 또는 비치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환 또는 비치환된 트리(C6-C30)아릴실릴, 치환 또는 비치환된 (C6-C30)아르(C1-C30)알킬, 치환 또는 비치환된(C1-C30)알킬옥시, 치환 또는 비치환된(C1-C30)알킬티오, 치환 또는 비치환된(C6-C30)아릴옥시, 치환 또는 비치환된(C6-C30)아릴티오, 치환 또는 비 치환된(C1-C30)알콕시카보닐, 치환 또는 비치환된(C1-C30)알킬카보닐, 치환 또는 비치환된(C6-C30)아릴카보닐, 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C2-C30)알키닐, 치환 또는 비치환된(C6-C30)아릴옥시카보닐, 치환 또는 비치환된(C1-C30)알콕시카보닐옥시, 치환 또는 비치환된(C1-C30)알킬카보닐옥시, 치환 또는 비치환된(C6-C30)아릴카보닐옥시, 치환 또는 비치환된(C6-C30)아릴옥시카보닐옥시, 카르복실, 나이트로, 하이드록시이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있다.]R 41 to R 44 are each independently Hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5 member 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted aromatic ring, wherein one to seven membered heterocycloalkyl, substituted or unsubstituted aromatic rings are fused. Is at least one fused (C3-C30) cycloalkyl, substituted or unsubstituted adamantyl, substituted or unsubstituted (C7-C30) bicycloalkyl, cyano, NR 21 R 22 , BR 23 R 24 , PR 25 R 26 , P (═O) R 27 R 28 [R 21 to R 28 are independently of each other substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted Substituted (C3-C30) heteroaryl], substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted Tri (C6-C30) arylsilyl, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkyloxy, substituted or unsubstituted (C1-C30 Alkylthio, substituted or unsubstituted (C6-C30) aryloxy, substituted or unsubstituted (C6-C30) arylthio, substituted or unsubstituted (C1-C30) alkoxycarbonyl, substituted or unsubstituted ( C1-C30) alkylcarbonyl, substituted or unsubstituted (C6-C30) arylcarbonyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, substituted or Unsubstituted (C6-C30) aryloxycarbonyl, substituted or unsubstituted (C1-C30) alkoxycarbonyloxy, substituted or unsubstituted (C1-C30) alkylcarbonyloxy, substituted or unsubstituted (C6 (C3-C30) arylcarbonyloxy, substituted or unsubstituted (C6-C30) aryloxycarbonyloxy, carboxyl, nitro, hydroxy, with or without fused ring with adjacent substituents Alkylene or (C3-C30) alkenylene Is connected to the can to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring.]
상기 
본 발명에 따른 유기 발광 화합물은 하기 화합물로부터 선택되어지나, 이에 한정되는 것은 아니다.The organic light emitting compound according to the present invention is selected from the following compounds, but is not limited thereto.
[R1은 화학식 1에서의 정의와 동일하고, R41 내지 R44은 화학식 2 내지 화학식 6에서의 정의와 동일하며;[R 1 is as defined in Formula 1, and R 41 to R 44 are as defined in Formula 2 to Formula 6;
R45 내지 R66은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)헤테로아릴, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬, 치환 또는 비치환된 아다만틸, 치환 또는 비치환된(C7-C30)바이시클로알킬, 시아노, NR21R22, BR23R24, PR25R26, P(=O)R27R28[R21 내지 R28은 서로 독 립적으로 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴 또는 치환 또는 비치환된 (C3-C30)헤테로아릴이다.], 치환 또는 비치환된 트리(C1-C30)알킬실릴, 치환 또는 비치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환 또는 비치환된 트리(C6-C30)아릴실릴, 치환 또는 비치환된 (C6-C30)아르(C1-C30)알킬, 치환 또는 비치환된(C1-C30)알킬옥시, 치환 또는 비치환된(C1-C30)알킬티오, 치환 또는 비치환된(C6-C30)아릴옥시, 치환 또는 비치환된(C6-C30)아릴티오, 치환 또는 비치환된(C1-C30)알콕시카보닐, 치환 또는 비치환된(C1-C30)알킬카보닐, 치환 또는 비치환된(C6-C30)아릴카보닐, 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C2-C30)알키닐, 치환 또는 비치환된(C6-C30)아릴옥시카보닐, 치환 또는 비치환된(C1-C30)알콕시카보닐옥시, 치환 또는 비치환된(C1-C30)알킬카보닐옥시, 치환 또는 비치환된(C6-C30)아릴카보닐옥시, 치환 또는 비치환된(C6-C30)아릴옥시카보닐옥시, 카르복실, 나이트로, 하이드록시이거나 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있다.]R 45 to R 66 are each independently Hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5 member 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted aromatic ring, wherein one to seven membered heterocycloalkyl, substituted or unsubstituted aromatic rings are fused. Is at least one fused (C3-C30) cycloalkyl, substituted or unsubstituted adamantyl, substituted or unsubstituted (C7-C30) bicycloalkyl, cyano, NR 21 R 22 , BR 23 R 24 , PR 25 R 26 , P (═O) R 27 R 28 [R 21 to R 28 are independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or Unsubstituted (C3-C30) heteroaryl], substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or Beach Substituted tri (C6-C30) arylsilyl, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkyloxy, substituted or unsubstituted (C1-C30 Alkylthio, substituted or unsubstituted (C6-C30) aryloxy, substituted or unsubstituted (C6-C30) arylthio, substituted or unsubstituted (C1-C30) alkoxycarbonyl, substituted or unsubstituted ( C1-C30) alkylcarbonyl, substituted or unsubstituted (C6-C30) arylcarbonyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, substituted or Unsubstituted (C6-C30) aryloxycarbonyl, substituted or unsubstituted (C1-C30) alkoxycarbonyloxy, substituted or unsubstituted (C1-C30) alkylcarbonyloxy, substituted or unsubstituted (C6 -C30) arylcarbonyloxy, substituted or unsubstituted (C6-C30) aryloxycarbonyloxy, carboxyl, nitro, (C3-C30) alkyl with or without hydroxy or fused ring with adjacent substituents Lene or (C3-C30) alkenylene To form an alicyclic ring and a monocyclic or polycyclic aromatic ring.]
본 발명에 따른 유기 발광 화합물은 보다 구체적으로 하기의 화합물로서 예시될 수 있으나, 하기 화합물이 본 발명을 한정하는 것은 아니다.The organic light emitting compound according to the present invention may be more specifically exemplified as the following compound, but the following compound does not limit the present invention.
본 발명에 따른 유기 발광 화합물은 하기 반응식 1 내지 3에 나타난 바와 같이, 제조될 수 있다.The organic light emitting compound according to the present invention can be prepared, as shown in Schemes 1 to 3.
[반응식 1]Scheme 1
[반응식 2]Scheme 2
[반응식 3]Scheme 3
[상기 반응식 1 내지 3에서 A고리, B고리 및 R1 내지 R3는 상기 화학식 1에서의 정의와 동일하다.][A ring, ring B and R 1 to R 3 in Schemes 1 to 3 are the same as defined in Formula 1 above.]
본 발명은 유기 전계 발광 소자를 제공하며, 본 발명에 따른 유기 전계 발광 소자는 제1전극; 제2전극; 및 상기 제1전극 및 제2전극 사이에 개재되는 1층 이상의 유기물층으로 이루어진 유기 전계 발광 소자에 있어서, 상기 유기물층은 상기 화학식 1의 유기 발광 화합물을 하나 이상 포함하는 것을 특징으로 한다. The present invention provides an organic electroluminescent device, the organic electroluminescent device according to the present invention comprises a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes at least one organic light emitting compound of Formula 1.
또한, 상기 유기물층은 발광층을 포함하며, 상기 발광층은 상기 화학식 1의 하나 이상의 유기 발광 화합물 이외에 하나 이상의 도판트를 더 포함하는 것을 특징으로 하며, 본 발명의 유기 발광 소자에 적용되는 도판트는 특별히 제한되지는 않는다.The organic material layer may include a light emitting layer, and the light emitting layer may further include one or more dopants in addition to the one or more organic light emitting compounds of Formula 1, and the dopant applied to the organic light emitting device of the present invention is not particularly limited. Does not.
본 발명의 유기 전계 발광 소자에 적용되는 도판트는 하기 화학식 7 의 화합물로부터 선택되는 것이 바람직하다.The dopant applied to the organic electroluminescent device of the present invention is preferably selected from the compound of formula (7).
[화학식 7][Formula 7]
MM 1One LL 101101 LL 102102 LL 103103
여기서 M1은 7족, 8족, 9족, 10족, 11족, 13족, 14족, 15족 및 16족의 금속으로 이루어진 군으로부터 선택되고, 리간드 L101, L102 및 L103 는 서로 독립적으로 하기 구조로부터 선택되어진다.Wherein M 1 is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16, and the ligands L 101 , L 102 and L 103 Are independently selected from the following structures.
[R201 내지 R203은 서로 독립적으로 수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬, (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴 또는 할로겐이고;[R 201 to R 203 are each independently hydrogen, (C1-C30) alkyl unsubstituted or substituted, (C6-C30) aryl or unsubstituted (C6-C30) aryl or halogen;
R204 내지 R219는 서로 독립적으로 수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C1-C30)알콕시, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또 는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된 모노 또는 치환 또는 비치환된 디-(C1-C30)알킬아미노, 치환 또는 비치환된 모노 또는 디-(C6-C30)아릴아미노, SF5, 치환 또는 비치환된 트리(C1-C30)알킬실릴, 치환 또는 비치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환 또는 비치환된 트리(C6-C30)아릴실릴, 시아노 또는 할로겐이고, R 204 to R 219 are each independently hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or Is unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted mono or substituted or unsubstituted di- (C1-C30) alkylamino, substituted or unsubstituted Mono or di- (C6-C30) arylamino, SF 5 , substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, Substituted or unsubstituted tri (C6-C30) arylsilyl, cyano or halogen,
R220 내지 R223는 서로 독립적으로 수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬 또는 (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴이고;R 220 to R 223 are each independently hydrogen, a substituted or unsubstituted (C1-C30) alkyl, or a (C1-C30) aryl optionally substituted (C6-C30) aryl;
R224 및 R225는 서서로 독립적으로 수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 할로겐이거나, R224와 R225는 융합고리를 포함하거나 포함하지 않는 (C3-C12)알킬렌 또는 (C3-C12)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성하며; R 224 and R 225 are each independently hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen, or R 224 and R 225 contain fused rings Linked with (C3-C12) alkylene or (C3-C12) alkenylene not containing to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
R226은 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C5-C30)헤테로아릴 또는 할로겐이고;R 226 is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C5-C30) heteroaryl or halogen;
R227 내지 R229은 서로 독립적으로 수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 할로겐이고;R 227 to R 229 are each independently hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen;
Q는 
상기 화학식 7의 도판트 화합물은 하기 구조의 화합물로 예시될 수 있으나, 이에 한정되는 것은 아니다. The dopant compound of Formula 7 may be exemplified as a compound having the following structure, but is not limited thereto.
본 발명의 유기 전계 발광 소자에 있어서, 화학식 1의 유기 발광 화합물을 포함하고, 동시에 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 화합물을 포함할 수 있다. 상기 아릴아민계 화합물 또는 스티릴아릴아민계 화합물은 출원번호 제10-2008-0123276호, 제10-2008-0107606호 또는 제10-2008-0118428호에 예시되어 있으나, 이에 한정되지는 않는다. In the organic electroluminescent device of the present invention, it may include one or more compounds selected from the group consisting of an organic light emitting compound of formula (1) and at the same time an arylamine compound or styrylarylamine compound. The arylamine-based compound or styrylarylamine-based compound is exemplified in Patent Application Nos. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but is not limited thereto.
또한, 본 발명의 유기 전계 발광 소자에 있어서, 유기물층에 상기 화학식 1의 유기 발광 화합물 이외에 1족, 2족, 4주기, 5주기 전이금속, 란탄계열금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속 또는 착체화합물을 더 포함할 수도 있고, 상기 유기물층은 발광층 및 전하생성층을 포함할 수 있다.In addition, in the organic electroluminescent device of the present invention, in the organic material layer, in addition to the organic light emitting compound of Chemical Formula 1, a group consisting of Group 1, Group 2, 4 cycle, 5 cycle transition metal, lanthanide series metal and organic metal of d-transition element It may further comprise one or more metals or complex compounds selected from, the organic material layer may include a light emitting layer and a charge generating layer.
또한, 상기 유기물층에 상기 유기 발광 화합물 이외에 적색, 녹색 또는 청색 발광을 하는 유기발광층 하나 이상을 동시에 포함하여 백색 유기 전계 발광 소자를 형성할수 있다. 상기 청색, 녹색 또는 적색 발광을 하는 화합물은 출원번호 제10-2008-0123276호, 제10-2008-0107606호 또는 제10-2008-0118428호에 예시되어 있으나, 이에 한정되지는 않는다. In addition, the organic layer may include at least one organic light emitting layer emitting red, green, or blue light in addition to the organic light emitting compound to form a white organic electroluminescent device. The compound emitting blue, green, or red light is exemplified in Application Nos. 10-2008-0123276, 10-2008-0107606, or 10-2008-0118428, but is not limited thereto.
본 발명의 유기 전계 발광 소자에 있어서, 한 쌍의 전극의 적어도 한쪽의 내측표면에, 칼코제나이드(chalcogenide)층, 할로겐화 금속층 및 금속 산화물층으로부터 선택되는 일층(이하, 이들을 "표면층"이라고 지칭함) 이상을 배치하는 것이 바람직하다. 구체적으로는, 발광 매체층 측의 양극 표면에 규소 및 알루미늄의 금속의 칼코제나이드(산화물을 포함한다)층을, 또한 발광매체층 측의 음극 표면에 할로겐화 금속층 또는 금속 산화물층을 배치하는 것이 바람직하다. 이것에 의해, 구동의 안정화를 얻을 수 있다. 상기 칼코제나이드로서는 예컨대 SiOx(1≤X≤2), AlOX(1≤X≤1.5), SiON, SiAlON 등을 바람직하게 들 수 있으며, 할로겐화 금속으로서는 예컨대 LiF, MgF2, CaF2, 불화 희토류 금속 등을 바람직하게 들 수 있으며, 금속 산화물로서는 예컨대 Cs2O, Li2O, MgO, SrO, BaO, CaO 등을 바람직하게 들 수 있다.In the organic electroluminescent device of the present invention, at least one inner surface of a pair of electrodes is selected from a chalcogenide layer, a halogenated metal layer, and a metal oxide layer (hereinafter, these are referred to as "surface layers"). It is preferable to arrange | position the above. Specifically, it is preferable to dispose a chalcogenide (containing oxide) layer of a metal of silicon and aluminum on the anode surface of the light emitting medium layer side and a metal halide or metal oxide layer on the cathode surface of the light emitting medium layer side. Do. As a result, drive stabilization can be obtained. Examples of the chalcogenide include SiO x (1 ≦ X ≦ 2 ), AlO X (1 ≦ X ≦ 1.5), SiON, SiAlON, and the like, and examples of the metal halide include LiF, MgF 2 , CaF 2 , and fluoride. Rare earth metals and the like are preferable. Examples of the metal oxides include Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO and the like.
또한, 본 발명의 유기 전계 발광 소자에 있어서, 이렇게 제작된 한 쌍의 전극의 적어도 한쪽의 표면에 전자 전달 화합물과 환원성 도판트의 혼합 영역 또는 정공 전달 화합물과 산화성 도판트의 혼합 영역을 배치하는 것도 바람직하다. 이러한 방식으로, 전자 전달 화합물이 음이온으로 환원되므로 혼합 영역으로부터 발광 매체에 전자를 주입 및 전달하기 용이해진다. 또한, 정공 전달 화합물은 산화되어 양이온으로 되므로 혼합 영역으로부터 발광 매체에 정공을 주입 및 전달하기 용이해진다. 바람직한 산화성 도판트로서는 각종 루이스산 및 억셉터(acceptor) 화합물을 들 수 있다. 바람직한 환원성 도판트로서는 알칼리 금속, 알칼리 금속 화합물, 알칼리 토류 금속, 희토류 금속 및 이들의 혼합물을 들 수 있다. 또한 환원성 도판트층을 전하생성층으로 사용하여 두 개 이상의 발광층을 가진 백색 유기 전계 발광소자를 제작할수 도 있다.Further, in the organic electroluminescent device of the present invention, disposing a mixed region of an electron transfer compound and a reducing dopant or a mixed region of a hole transfer compound and an oxidative dopant on at least one surface of the pair of electrodes thus produced desirable. In this way, the electron transfer compound is reduced to an anion, thereby facilitating injection and transfer of electrons from the mixed region into the light emitting medium. In addition, since the hole transport compound is oxidized to become a cation, it is easy to inject and transfer holes from the mixed region to the light emitting medium. Preferred oxidative dopants include various Lewis acids and acceptor compounds. Preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals and mixtures thereof. In addition, the reducing dopant layer It is also possible to manufacture a white organic electroluminescent device having two or more light emitting layers by using it as a charge generating layer.
본 발명에 따른 유기 발광 화합물은 발광효율이 좋고 재료의 색순도 및 수명특성이 뛰어나 소자의 구동수명이 매우 우수한 OLED 소자를 제조할 수 있는 장점이 있다.The organic light emitting compound according to the present invention has an advantage in that an OLED device can be manufactured having excellent luminous efficiency and excellent color purity and life characteristics of materials, and having excellent driving life of the device.
이하에서, 본 발명의 상세한 이해를 위하여 본 발명의 대표 화합물을 들어 본 발명에 따른 유기 발광 화합물, 이의 제조방법 및 소자의 발광특성을 설명하나, 이는 단지 그 실시 양태를 예시하기 위한 것일 뿐, 본 발명의 범위를 한정하는 것은 아니다.Hereinafter, the organic light emitting compound according to the present invention, a method for preparing the same and a light emitting property of the device are described for the detailed understanding of the present invention, but the present invention is only intended to illustrate the embodiments of the present invention. It does not limit the scope of the invention.
[제조예 1]화합물 1의 제조Preparation Example 1 Preparation of Compound 1
화합물 compound 1-11-1 의 제조Manufacture
1-나프탈렌보론산 10.2 g(59.4 mmol), 1-브로모-2-나이트로벤젠 10.0 g(49.5 mmol), Pd(PPh3)4 1.7 g(1.4 mmol), 2M K2CO3 수용액 70 mL, 톨루엔 200 mL 및 에탄올 100 mL를 넣고 12시간 환류 교반시켰다. 증류수로 씻어 주고 EA로 추출하고, 무수 MgSO4으로 건조하고 감압 증류시켜 얻어진 잔사를 컬럼 분리하여 화합물 1-1 9.0 g(36.1 mmol, 73.7 %)을 얻었다. 10.2 g (59.4 mmol) of 1-naphthaleneboronic acid, 10.0 g (49.5 mmol) of 1-bromo-2-nitrobenzene, 1.7 g (1.4 mmol) of Pd (PPh 3 ) 4 , 70 mL of 2M K 2 CO 3 aqueous solution 200 mL of toluene and 100 mL of ethanol were added thereto, and the mixture was stirred under reflux for 12 hours. The mixture was washed with distilled water, extracted with EA, dried over anhydrous MgSO 4 , and distilled under reduced pressure, and the residue was separated by column to obtain 9.0 g (36.1 mmol, 73.7%) of Compound 1-1 .
화합물 compound 1-21-2 의 제조Manufacture
화합물 1-1 9.0 g(36.1 mmol)과 N-브로모쑥시니이미드 7.6 g(43.3 mmol)을 디클로로메탄 300 mL에 녹이고 12시간 상온에서 교반시켰다. 감압 증류하고 얻어진 고체를 증류수, 메탄올 및 헥산으로 차례로 세척한 후 화합물 1-2 9.6 g(29.3 mmol, 81.3 %)을 얻었다. 9.0 g (36.1 mmol) of Compound 1-1 and 7.6 g (43.3 mmol) of N-bromosuccinimide were dissolved in 300 mL of dichloromethane and stirred at room temperature for 12 hours. After distillation under reduced pressure and washing the solid obtained in turn with distilled water, methanol and hexane gave Compound 1-2 9.6 g (29.3 mmol, 81.3 %).
화합물 compound 1-31-3 의 제조Manufacture
화합물 1-2 9.6 g(29.3 mmol), iron oxalate dihydrate 72.2 g(175.5 mmol) 을 섞고 205℃로 30분 가열시킨 후 상온으로 냉각시키고 EA로 추출하고 증류수로 세척하였다. 톨루엔으로 재결정하여 화합물 1-3 5.2 g(17.6 mmol, 60.5 %) 을 얻었다. Compound 1-2 9.6 g (29.3 mmol) and iron oxalate dihydrate 72.2 g (175.5 mmol) were mixed, heated to 205 ° C. for 30 minutes, cooled to room temperature, extracted with EA, and washed with distilled water. Recrystallization from toluene afforded 5.2 g (17.6 mmol, 60.5%) of compound 1-3 .
화합물 compound 1-41-4 의 제조Manufacture
화합물 1-3 5.2 g(17.6 mmol), 구리 0.6 g(8.8 mmol), 18-크라운-6 0.2 g(0.9 mmol), K2CO3 4.8 g(35.1 mmol) 및 1,2-디클로로벤젠 100 mL을 섞고 180℃에서 12시간동안 환류교반시켰다. 상온으로 냉각시키고 감압 증류한 후 MC로 추출하고 증류수로 세척하였다. 무수 MgSO4으로 건조하고 감압 증류하여 얻어진 잔사를 컬럼 분리하여 화합물 1-4 5.0 g(13.4 mmol, 76.5 %)을 얻었다.Compound 1-3 5.2 g (17.6 mmol), 0.6 g (8.8 mmol) copper, 0.2 g (0.9 mmol) 18-crown-6, 4.8 g (35.1 mmol) K 2 CO 3 and 100 mL 1,2-dichlorobenzene The mixture was stirred and refluxed at 180 ° C. for 12 hours. After cooling to room temperature and distillation under reduced pressure, the mixture was extracted with MC and washed with distilled water. The residue obtained by drying over anhydrous MgSO 4 and distillation under reduced pressure was separated by column to obtain 5.0 g (13.4 mmol, 76.5%) of compound 1-4 .
화합물 compound 1One 의 제조Manufacture
화합물 1-4 5.0 g(13.4 mmol), 9-페닐-안트라센-10-보론산 4.8 g(16.1 mmol), Pd(PPh3)4 0.8 g(0.7 mmol), 2M K2CO3 수용액 20 mL, 톨루엔 100 mL 및 에탄올 50 mL를 넣고 12시간 환류 교반시켰다. 증류수로 씻어 주고 EA로 추출한 후 무수 MgSO4으로 건조하고 감압 증류하여 얻어진 잔사를 컬럼 분리하여 화합물 1 4.3 g(7.9 mmol, 58.8 %)을 얻었다. 5.0 g (13.4 mmol) of Compound 1-4 , 4.8 g (16.1 mmol) of 9-phenyl-anthracene-10-boronic acid, 0.8 g (0.7 mmol) of Pd (PPh 3 ) 4 , 20 mL of 2M K 2 CO 3 aqueous solution, 100 mL of toluene and 50 mL of ethanol were added thereto, and the mixture was stirred under reflux for 12 hours. The mixture was washed with distilled water, extracted with EA, dried over anhydrous MgSO 4 , and distilled under reduced pressure to obtain a compound 1 (4.3 g, 7.9 mmol, 58.8%).
[제조예 2]화합물 13의 제조Preparation Example 2 Preparation of Compound 13
화합물 compound 2-12-1 의 제조Manufacture
시아누르산 클로라이드(Cyanuric chloride) 10.0 g(54.22 mmol)을 THF 35 mL에 녹인 후 0℃로 냉각한다. 페닐마그네슘 브로마이드(3.0M in diethylether) 45.1 mL(135.56 mmol)을 천천히 넣어주고 상온에서 3시간 교반한다. 이때 생성된 고체를 감압여과하고 메탄올과 헥산으로 씻어준다. 화합물 2-1 9g (62%)얻었다.Dissolve 10.0 g (54.22 mmol) of cyanuric chloride in 35 mL of THF and cool to 0 ° C. Slowly add 45.1 mL (135.56 mmol) of phenylmagnesium bromide (3.0M in diethylether) and stir at room temperature for 3 hours. The resulting solid was filtered under reduced pressure and washed with methanol and hexane. 9g (62%) of compound 2-1 was obtained.
화합물 compound 2-22-2 의 제조Manufacture
1-나프탈렌보론산 10.2 g(59.4 mmol), 1-브로모-2-나이트로벤젠 10.0 g(49.5 mmol), Pd(PPh3)4 1.7 g(1.4 mmol), 2M K2CO3 수용액 70 mL, 톨루엔 200 mL 및 에탄올100 mL를 넣고 12시간 환류 교반시켰다. 증류수로 씻어 주고 EA로 추출하고, 무수 MgSO4으로 건조하고 감압 증류시켜 얻어진 잔사를 컬럼 분리하여 화합물 2-2 9.0 g(36.1 mmol, 73.7 %)을 얻었다. 10.2 g (59.4 mmol) of 1-naphthaleneboronic acid, 10.0 g (49.5 mmol) of 1-bromo-2-nitrobenzene, 1.7 g (1.4 mmol) of Pd (PPh 3 ) 4 , 70 mL of 2M K 2 CO 3 aqueous solution 200 mL of toluene and 100 mL of ethanol were added thereto, and the mixture was stirred under reflux for 12 hours. The mixture was washed with distilled water, extracted with EA, dried over anhydrous MgSO 4 , and distilled under reduced pressure. The residue was separated by column to obtain 9.0 g (36.1 mmol, 73.7%) of Compound 2-2 .
화합물 compound 2-32-3 의 제조Manufacture
화합물 2-2 9.6 g(29.3 mmol), iron oxalate dihydrate 72.2 g(175.5 mmol) 을 섞고 205 ℃로 30분 가열시킨 후 상온으로 냉각시키고 EA로 추출하고 증류수로 세척하였다. 톨루엔으로 재결정하여 화합물 2-3 5.2 g(17.6 mmol, 60.5 %) 을 얻었다. 9.6 g (29.3 mmol) of Compound 2-2 and 72.2 g (175.5 mmol) of iron oxalate dihydrate were mixed, heated to 205 ° C. for 30 minutes, cooled to room temperature, extracted with EA, and washed with distilled water. Recrystallized with toluene to give compound 2-3 5.2 g (17.6 mmol, 60.5%).
화합물 compound 1313 의 제조Manufacture
NaH(60% in minera oil) 575 mg(14.38 mmol)을 DMF 30 mL에 희석 시킨다. 화합물 13 2.5 g(11.50 mmol)을 DMF 20 mL에 녹인 후 상기 용액에 첨가 한다. 그 후 한시간 동안 상온에서 교반 후 화합물 2-1 3.0 g(11.50 mmol)을 DMF 20 mL에 녹인 후 상기 용액에 첨가한다. 상온에서 3시간 교반 후 물 50 mL 를 넣어주고 생성된 고체를 감압여과 한다. 얻어진 고체를 DMF 및 EA로 재결정한다. 화합물 13 2.8 g(54 %)얻었다.575 mg (14.38 mmol) of NaH (60% in minera oil) are diluted in 30 mL of DMF. 2.5 g (11.50 mmol) of compound 13 are dissolved in 20 mL of DMF and added to the solution. After stirring at room temperature for 1 hour, 3.0 g (11.50 mmol) of Compound 2-1 were dissolved in 20 mL of DMF, and then added to the solution. After stirring for 3 hours at room temperature, 50 mL of water was added and the resulting solid was filtered under reduced pressure. The obtained solid is recrystallized from DMF and EA. Compound 13 obtained 2.8 g (54%).
[제조예 3]화합물 33의 제조Preparation Example 3 Preparation of Compound 33
화합물 compound 3-13-1 의 제조Manufacture
4-플루오로페닐하이드라진 하이드로클로라이드 10.0 g(61.5 mmol)을 메탄올 143 mL, 물 47 mL에 넣고 5분간 교반한다. b-테트랄론 8.7 mL(65.8 mmol)을 첨가하고 상온에서 한시간 동안 격렬하게 교반한다. MC로 유기층을 추출한다. 무수 MgSO4으로 건조하고 감압 증류한다. 컬럼 분리하여 화합물 3-1 9.7 g(66 %)을 얻었다.10.0 g (61.5 mmol) of 4-fluorophenylhydrazine hydrochloride was added to 143 mL of methanol and 47 mL of water, followed by stirring for 5 minutes. Add 8.7 mL (65.8 mmol) of b-tetralone and stir vigorously at room temperature for 1 hour. The organic layer is extracted with MC. It is dried over anhydrous MgSO 4 and distilled under reduced pressure. 9.7 g (66%) of compound 3-1 was obtained by column separation.
화합물 compound 3-23-2 의 제조Manufacture
화합물 3-1 9.7 g(40.53mmol), Pd/C(10%) 11.6 g, 크실렌 135 mL를 넣고 150 ℃ 환류 교반 12시간 한다. 상온으로 식힌 후 MC로 유기층을 추출한다. 무수 MgSO4으로 건조하고 감압 증류한다. 컬럼 분리하여 화합물 3-2 8.3 g(87 %)을 얻었다. 9.7 g (40.53 mmol) of Compound 3-1 , 11.6 g of Pd / C (10%), and 135 mL of xylene were added thereto, followed by stirring at reflux at 150 ° C for 12 hours. After cooling to room temperature, the organic layer is extracted with MC. It is dried over anhydrous MgSO 4 and distilled under reduced pressure. Compound 3-2 8.3 g (87%) was obtained by column separation.
화합물 compound 3333 의 제조Manufacture
NaH(60% in minera oil) 531 mg(13.28 mmol)을 DMF 20 mL에 희석 시킨다. 화합물 3-2 2.5 g(10.6 mmol)을 DMF 20 mL에 녹인 후 상기 용액에 첨가 한다. 그 후 한시간 동안 상온에서 교반 후 화합물 2-1 2.8 g(10.6 mmol)을 DMF 30 mL에 녹인 후 상기 용액에 첨가한다. 상온에서 3시간 교반 후 물 50 mL 를 넣어주고 생성된 고체를 감압여과 한다. 얻어진 고체를 DMF 및 EA로 재결정한다. 화합물 33 2.8 g(56 %)얻었다.531 mg (13.28 mmol) of NaH (60% in minera oil) are diluted in 20 mL of DMF. 2.5 g (10.6 mmol) of compound 3-2 are dissolved in 20 mL of DMF and added to the solution. After stirring for 1 hour at room temperature, 2.8 g (10.6 mmol) of Compound 2-1 was dissolved in 30 mL of DMF, and then added to the solution. After stirring for 3 hours at room temperature, 50 mL of water was added and the resulting solid was filtered under reduced pressure. The obtained solid is recrystallized from DMF and EA. Compound 33 obtained 2.8 g (56%).
[제조예 4]화합물 124의 제조Preparation Example 4 Preparation of Compound 124
화합물 compound 4-14-1 의제조Manufacturing
2-클로로-3-니트로피리딘 25 g(157.6 mmol), 페닐보론산 24.9 g(204.9 mmol), Pd(PPh3)4 5.4 g(4.73 mmol), K2CO3 54.48 g(394.2 mmol), 증류수 150 mL, 톨루엔 300 mL, 에탄올 100 mL을 넣고 환류 교반 하였다. 12시간 후 상온으로 냉각하고 증류수를 넣는다. MC로 추출하고 무수 MgSO4으로 건조한다. 감압 증류 후 컬럼 분리한다. 화합물 4-1 30 g(149.85 mmol, 95.45 %) 을 얻었다. 25 g (157.6 mmol) of 2-chloro-3-nitropyridine, 24.9 g (204.9 mmol) of phenylboronic acid, 5.4 g (4.73 mmol) of Pd (PPh 3 ) 4 , 54.48 g (394.2 mmol) of K 2 CO 3 , distilled water 150 mL, toluene 300 mL and ethanol 100 mL were added and stirred under reflux. After 12 hours, cool to room temperature and add distilled water. Extract with MC and dry with anhydrous MgSO 4 . After distillation under reduced pressure, the column is separated. 30 g (149.85 mmol, 95.45%) of compound 4-1 was obtained.
화합물 compound 4-24-2 의 제조Manufacture
화합물 4-1 30 g(149.85 mmol)을 트리에틸포스파이트 150 mL에 섞고 180℃로 4시간 교반한다. 상온으로 냉각 후 감압 증류한다. 컬럼 분리하여 화합물 4-2 2.1 g(12.48 mmol, 8.37 %)을 얻었다. 30 g (149.85 mmol) of compound 4-1 are mixed with 150 mL of triethylphosphite, and stirred at 180 ° C for 4 hours. After cooling to room temperature, distillation under reduced pressure. 2.1 g (12.48 mmol, 8.37%) of Compound 4-2 was obtained by column separation.
화합물 compound 124124 의 제조Manufacture
NaH 0.45 g(18.72 mmol, 60% in mineral oil)과 DMF 12 mL을 섞고 화합물 4-2 2.1 g(12.48 mmol)을 DMF 20 mL에 녹여 넣는다. 30분 교반 후 화합물 2-1 3.6 g(13.73 mmol)을 DMF 25 mL에 녹여 넣는다. 12시간 교반 후 증류수를 넣고 생성된 고체를 감압 여과한다. EA로 재결정하여 화합물 124 2.6 g(6.50 mmol, 54.24 %)을 얻었다. Mix 0.45 g (18.72 mmol, 60% in mineral oil) with 12 mL of DMF and dissolve 2.1 g (12.48 mmol) of compound 4-2 in 20 mL of DMF. After stirring for 30 minutes, 3.6 g (13.73 mmol) of Compound 2-1 are dissolved in 25 mL of DMF. After stirring for 12 hours, distilled water was added and the resulting solid was filtered under reduced pressure. Recrystallization from EA gave 2.6 g (6.50 mmol, 54.24%) of Compound 124 .
[제조예 5]화합물 125의 제조Preparation Example 5 Preparation of Compound 125
화합물 compound 5-15-1 의 제조Manufacture
2-클로로피리딘 10 g(74.87 mmol), 2-클로로아닐린 11.4 g(89.85 mmol), Pd2(dba)3 4.0 g(4.40 mmol), 트리-tert-부틸포스핀(P(t-Bu)3) 50% in 자일렌 11.7 mL(17.61 mmol), KOt-Bu 69 g(616.46 mmol), 1.4-다이옥산 50 mL을 가압 플라스크 에 넣고 120℃에서 20시간 가열한다. MC로 유기층을 추출한다. 무수 MgSO4으로 건조하고 감압 증류한다. 컬럼 분리하여 화합물 5-1 1.3g(10%)을 얻었다. 10 g (74.87 mmol) of 2-chloropyridine, 11.4 g (89.85 mmol) of 2-chloroaniline, 4.0 g (4.40 mmol) of Pd 2 (dba) 3 , tri-tert-butylphosphine (P (t-Bu) 3 ) 50% in xylene 11.7 mL (17.61 mmol), 69 g (616.46 mmol) KOt-Bu, 50 mL 1.4-dioxane were placed in a pressurized flask and heated at 120 ° C. for 20 hours. The organic layer is extracted with MC. It is dried over anhydrous MgSO 4 and distilled under reduced pressure. Compound 5-1 1.3g (10%) was obtained by column separation.
화합물 compound 125125 의 제조Manufacture
NaH(60% in minera oil) 594 mg(14.86 mmol)을 DMF 20 mL에 희석 시킨다. 화합물 5-1 2.0 g(11.89 mmol)을 DMF 20 mL에 녹인 후 상기 용액에 첨가 한다. 그 후 한시간 동안 상온에서 교반 후 화합물 2-1 3.1 g(11.89 mmol)을 DMF 30 mL에 녹인 후 상기 용액에 첨가한다. 상온에서 3시간 교반 후 물 50 mL를 넣어주고 생성된 고체를 감압여과 한다. 얻어진 고체를 DMF 및 EA로 재결정하여 화합물 125 3.7 g(77 %)얻었다.Dilute 594 mg (14.86 mmol) of NaH (60% in minera oil) in 20 mL of DMF. 2.0 g (11.89 mmol) of Compound 5-1 are dissolved in 20 mL of DMF and added to the solution. After stirring at room temperature for 1 hour, 3.1 g (11.89 mmol) of Compound 2-1 were dissolved in 30 mL of DMF, and then added to the solution. After stirring for 3 hours at room temperature, 50 mL of water was added and the resulting solid was filtered under reduced pressure. The resulting solid was recrystallized from DMF and EA to give 3.7 g (77%) of compound 125 .
상기 제조예 1 의 방법을 이용하여 유기 발광 화합물 1 내지 화합물 128을 제조하였으며, 표 1에 제조된 유기 발광 화합물들의 1H NMR 및 MS/FAB를 나타내었다.The organic light emitting compounds 1 to 128 were prepared using the method of Preparation Example 1, and the 1 H NMR and the MS / FAB of the organic light emitting compounds prepared in Table 1 are shown.
[표 1]TABLE 1
[실시예 1] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작Example 1 Fabrication of an OLED Device Using an Organic Light Emitting Compound According to the Present Invention
본 발명의 발광 재료를 이용한 구조의 OLED 소자를 제작하였다.An OLED device having a structure using the light emitting material of the present invention was produced.
우선, OLED용 글래스(삼성-코닝사 제조)로부터 얻어진 투명전극 ITO 박막(15 Ω/□)을, 트리클로로에틸렌, 아세톤, 에탄올, 증류수를 순차적으로 사용하여 초음파 세척을 실시한 후, 이소프로판올에 넣어 보관한 후 사용하였다.First, a transparent electrode ITO thin film (15 Ω / □) obtained from an OLED glass (manufactured by Samsung Corning Corporation) was subjected to ultrasonic cleaning using trichloroethylene, acetone, ethanol and distilled water sequentially, and then stored in isopropanol. It was used after.
다음으로, 진공 증착 장비의 기판 폴더에 ITO 기판을 설치하고, 진공 증착 장비 내의 셀에 하기 구조의 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA)을 넣고, 챔버 내의 진공도가 10-6 torr에 도달할 때까지 배기시킨 후, 셀에 전류를 인가하여 2-TNATA를 증발시켜 ITO 기판 상에 60 nm 두께의 정공주입층을 증착하였다.Next, an ITO substrate is installed in the substrate folder of the vacuum deposition apparatus, and 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenylamine (2) having the structure -TNATA), evacuated until the vacuum in the chamber reached 10 -6 torr, and then applied a current to the cell to evaporate 2-TNATA to deposit a 60 nm thick hole injection layer on the ITO substrate.
이어서, 진공 증착 장비 내의 다른 셀에 하기구조 N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB)을 넣고, 셀에 전류를 인가하여 NPB를 증발시켜 정공주입층 위에 20 nm 두께의 정공전달층을 증착하였다.The NPB -diphenyl-4,4'-diamine into the (NPB), by applying a current to the cell - Then, to another cell of the vacuum vapor-deposit device structure, N, N 'N, N -bis (α-naphthyl)' A 20 nm thick hole transport layer was deposited on the hole injection layer by evaporation.
정공주입층, 정공전달층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착시켰다. 진공 증착 장비 내의 한쪽 셀에 호스트로서 본 발명에 따른 화합물 13를 넣고, 또 다른 셀에는 도판트로서 하기 구조의 화합물 (piq)2Ir(acac)를 각각 넣은 후, 두 셀을 같이 가열, (piq)2Ir(acac)의 증착속도 비율을 4 내지 10 중량%로 증착함으로써 상기 정공 전달층 위에 30 nm 두께의 발광층을 증착하였다.After the hole injection layer and the hole transport layer were formed, the light emitting layer was deposited thereon as follows. Compound 13 according to the present invention is put into one cell in a vacuum deposition apparatus as a host, and compound (piq) 2 Ir (acac) having the following structure is respectively added as a dopant in another cell, and then the two cells are heated together (piq A light emitting layer having a thickness of 30 nm was deposited on the hole transport layer by depositing a ratio of 2 Ir (acac) at a rate of 4 to 10 wt%.
이어서 상기 발광층 위에 정공차단층으로 Bis(2-methyl-8-quinolinato)Subsequently, Bis (2-methyl-8-quinolinato) is used as a hole blocking layer on the light emitting layer.
(p-phenylphenolato)aluminum(III) (BAlq)을 5 nm의 두께로 증착시키고, 전자전달층으로써 하기 구조의 tris(8-hydroxyquinoline)-aluminum(III) (Alq)를 20 nm 두께로 증착한 다음, 전자주입층으로 하기 구조의 화합물 lithium quinolate (Liq)를 1 내지 2 nm 두께로 증착한 후, 다른 진공 증착 장비를 이용하여 Al 음극을 150 nm의 두께로 증착하여 OLED를 제작하였다. ( p -phenylphenolato) aluminum (III) (BAlq) was deposited to a thickness of 5 nm, and tris (8-hydroxyquinoline) -aluminum (III) (Alq) having the following structure was deposited to a thickness of 20 nm as an electron transport layer. After the deposition of the compound lithium quinolate (Liq) having a thickness of 1 to 2 nm as an electron injection layer, using another vacuum deposition equipment by depositing the Al cathode to a thickness of 150 nm to produce an OLED.
재료 별로 각 화합물은 10-6 torr 하에서 진공 승화 정제하여 OLED 발광재료로 사용하였다.Each compound was vacuum sublimated and purified under 10 -6 torr to be used as an OLED light emitting material.
[실시예 2]본 발명에 따른 유기발광화합물을 이용한 OLED 소자 제작Example 2 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention
정공차단층을 제외한 나머지는 실시예 1과 동일한 방법으로 OLED를 제작하였다. Except for the hole blocking layer, an OLED was manufactured in the same manner as in Example 1.
[비교예 1] 종래의 발광 재료를 이용한 OLED 소자의 발광 특성[Comparative Example 1] Light emission characteristics of OLED device using conventional light emitting material
상기 실시예 1과 동일한 방법으로 정공주입층 및 정공전달층을 형성시킨 후, 상기 진공 증착 장비 내의 다른 셀에 발광 호스트 재료로서 CBP를 넣고, 또 다른 셀에는 (piq)2Ir(acac)를 각각 넣은 후, 두 셀을 같이 가열, (piq)2Ir(acac)의 증착속도 비율을 4 내지 10 중량%로 증착함으로써 상기 정공 전달층 위에 30 nm 두께의 발광층을 증착하였다.After the hole injection layer and the hole transport layer were formed in the same manner as in Example 1, CBP was added as a light emitting host material to another cell in the vacuum deposition apparatus, and (piq) 2 Ir (acac) was added to another cell, respectively. After the two cells were heated together, a light emitting layer having a thickness of 30 nm was deposited on the hole transport layer by depositing a ratio of (piq) 2 Ir (acac) at a rate of 4 to 10% by weight.
이어서 상기 발광층 위에 정공차단층으로 Bis(2-methyl-8-quinolinato)Subsequently, Bis (2-methyl-8-quinolinato) is used as a hole blocking layer on the light emitting layer.
(p-phenylphenolato)aluminum(III) (BAlq)을 5 nm의 두께로 증착시키고, 전 자전달층으로써 하기 구조의 tris(8-hydroxyquinoline)-aluminum(III) (Alq)를 20 nm 두께로 증착한 다음, 전자주입층으로 하기 구조의 화합물 lithium quinolate (Liq)를 1 내지 2 nm 두께로 증착한 후, 다른 진공 증착 장비를 이용하여 Al 음극을 150 nm의 두께로 증착하여 OLED를 제작하였다. ( p- phenylphenolato) aluminum (III) (BAlq) was deposited to a thickness of 5 nm, and tris (8-hydroxyquinoline) -aluminum (III) (Alq) having the following structure was deposited to a thickness of 20 nm as an electron transport layer. Next, after depositing a compound lithium quinolate (Liq) having a structure of 1 to 2 nm thickness as an electron injection layer, using another vacuum deposition equipment to deposit an Al cathode to a thickness of 150 nm to produce an OLED.
상기 실시예 1 및 2와 비교예 1에서 제조된 본 발명에 따른 유기 발광 화합물과 종래의 발광 화합물을 함유하는 OLED 소자의 발광 효율을 각각 1,000 cd/m2 에서 측정하여 하기 표 2에 나타내었다. Below with the Examples 1 and 2 and Comparative Examples the organic electroluminescent compounds according to the present invention produced in the first and each of the luminous efficiency of the OLED device containing a conventional light-emitting compound measured at 1,000 cd / m 2 it is shown in Table 2 below.
[표 2]TABLE 2
상기 표 2로부터 본 발명에서 개발한 유기 발광 화합물들의 발광 특성이 종래의 재료 대비 우수한 특성을 보이는 것을 확인할 수 있었다. 또한 본 발명에 따른 유기 발광 화합물을 호스트 재료로 사용한 소자는 발광특성이 뛰어날 뿐만 아니라 구동전압을 강하시켜줌으로써 1.7~3.2 lm/W의 전력효율의 상승을 유도하여 소비전력을 개선시킬 수 있다.It can be seen from Table 2 that the luminescent properties of the organic light emitting compounds developed in the present invention show superior properties compared to conventional materials. In addition, the device using the organic light emitting compound according to the present invention as a host material is not only excellent in the light emission characteristics, but also by lowering the driving voltage can lead to an increase in power efficiency of 1.7 ~ 3.2 lm / W to improve the power consumption.
Claims (10)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020090027256A KR101603070B1 (en) | 2009-03-31 | 2009-03-31 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| PCT/KR2010/001897 WO2010114264A2 (en) | 2009-03-31 | 2010-03-29 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| TW099109821A TW201105774A (en) | 2009-03-31 | 2010-03-31 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020090027256A KR101603070B1 (en) | 2009-03-31 | 2009-03-31 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020150172073A Division KR20150141179A (en) | 2015-12-04 | 2015-12-04 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20100108924A true KR20100108924A (en) | 2010-10-08 |
| KR101603070B1 KR101603070B1 (en) | 2016-03-14 |
Family
ID=42828823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020090027256A KR101603070B1 (en) | 2009-03-31 | 2009-03-31 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
Country Status (3)
| Country | Link |
|---|---|
| KR (1) | KR101603070B1 (en) |
| TW (1) | TW201105774A (en) |
| WO (1) | WO2010114264A2 (en) |
Cited By (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20130011446A (en) * | 2011-07-21 | 2013-01-30 | 롬엔드하스전자재료코리아유한회사 | Novel organic electroluminescence compounds and organic electroluminescence device using the same |
| US8455867B2 (en) | 2010-10-26 | 2013-06-04 | Samsung Display Co., Ltd. | Organic light-emitting device |
| US8546793B2 (en) | 2010-10-26 | 2013-10-01 | Samsung Display Co., Ltd. | Organic light-emitting device |
| KR101328977B1 (en) * | 2010-10-26 | 2013-11-13 | 삼성디스플레이 주식회사 | Organic light emitting device |
| KR101328978B1 (en) * | 2010-10-26 | 2013-11-13 | 삼성디스플레이 주식회사 | Organic light emitting device |
| KR20140083412A (en) * | 2012-12-26 | 2014-07-04 | 엘지디스플레이 주식회사 | Red Phosphorescent Host Material and Organic Electroluminescent Device Using the Same |
| US8771844B2 (en) | 2011-06-22 | 2014-07-08 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting diode and flat display device including the heterocyclic compound |
| KR20140120089A (en) * | 2013-04-02 | 2014-10-13 | 에스에프씨 주식회사 | An organoelectro luminescent compounds and organoelectro luminescent device using the same |
| US8986857B2 (en) | 2011-07-22 | 2015-03-24 | Semiconductor Energy Laboratory Co., Ltd. | Dibenzo[c,g]carbazole compound, light-emitting element, light-emitting device, display device, lighting device and electronic device |
| US9006721B2 (en) | 2013-02-08 | 2015-04-14 | Samsung Display Co., Ltd. | Organic light-emitting diode |
| US9005777B2 (en) | 2011-10-19 | 2015-04-14 | Samsung Display Co., Ltd. | Heterocyclic compound, organic light-emitting diode including the heterocyclic compound, and flat display device including the organic light-emitting diode |
| KR20150052705A (en) * | 2013-11-06 | 2015-05-14 | 주식회사 두산 | Organic compounds and organic electro luminescence device comprising the same |
| KR20150111534A (en) * | 2014-03-25 | 2015-10-06 | 삼성디스플레이 주식회사 | Heterocyclic compound and organic light emitting device comprising the same |
| WO2015178731A1 (en) | 2014-05-23 | 2015-11-26 | Rohm And Haas Electronic Materials Korea Ltd. | An organic electroluminescent compound and an organic electroluminescent device comprising the same |
| KR20150135109A (en) | 2014-05-23 | 2015-12-02 | 롬엔드하스전자재료코리아유한회사 | An organic electroluminescent compound and an organic electroluminescent device comprising the same |
| KR20160034804A (en) * | 2014-09-22 | 2016-03-30 | 주식회사 엘지화학 | Hetero-cyclic compound and organic light emitting device comprising the same |
| KR20160037107A (en) | 2014-09-26 | 2016-04-05 | 롬엔드하스전자재료코리아유한회사 | Organic Electroluminescent Compound, and Organic Electroluminescent Material and Organic Electroluminescent Device Comprising the Same |
| KR20160046703A (en) * | 2014-10-21 | 2016-04-29 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| US9385327B2 (en) | 2012-08-01 | 2016-07-05 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
| WO2016064088A3 (en) * | 2014-10-21 | 2016-08-11 | 덕산네오룩스 주식회사 | Compound for organic electric device, organic electric device using same, and electronic device using same |
| US9416107B2 (en) | 2011-06-29 | 2016-08-16 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
| KR20160099471A (en) * | 2015-02-12 | 2016-08-22 | 롬엔드하스전자재료코리아유한회사 | Organic Electroluminescent Compounds and Organic Electroluminescent Device Comprising the Same |
| US9515271B2 (en) | 2014-12-03 | 2016-12-06 | Samsung Display Co., Ltd. | Organic light-emitting device |
| US9525144B2 (en) | 2013-02-08 | 2016-12-20 | Samsung Display Co., Ltd. | Organic light-emitting diode |
| WO2017043797A1 (en) * | 2015-09-09 | 2017-03-16 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using same, and electronic device thereof |
| WO2017047992A1 (en) * | 2015-09-14 | 2017-03-23 | 주식회사 엘지화학 | Heterocyclic compound and organic light emitting device comprising same |
| KR20170042423A (en) * | 2015-10-08 | 2017-04-19 | 삼성디스플레이 주식회사 | Condensed-cyclic compound and organic light emitting device comprising the same |
| WO2017086696A1 (en) * | 2015-11-17 | 2017-05-26 | 주식회사 엘지화학 | Heterocyclic compound and organic light-emitting element comprising same |
| US9691992B2 (en) | 2013-01-30 | 2017-06-27 | Samsung Displey Co., Ltd. | Organic light-emitting diode |
| US9722182B2 (en) | 2012-10-30 | 2017-08-01 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
| US9722185B2 (en) | 2013-08-12 | 2017-08-01 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
| US9893301B2 (en) | 2012-07-25 | 2018-02-13 | Samsung Display Co., Ltd. | Heterocyclic compounds and organic light-emitting devices including the same |
| KR20180031385A (en) * | 2016-09-20 | 2018-03-28 | 에스에프씨 주식회사 | Novel organic compounds and organic light-emitting diode therewith |
| US10062848B2 (en) | 2013-06-18 | 2018-08-28 | Samsung Display Co., Ltd. | Organic light-emitting device |
| US20180305337A1 (en) * | 2015-10-22 | 2018-10-25 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compounds and organic electroluminescent device comprising the same |
| WO2018236182A1 (en) * | 2017-06-23 | 2018-12-27 | 주식회사 엘지화학 | Compound and organic electroluminescent device comprising same |
| KR20190013605A (en) * | 2017-07-28 | 2019-02-11 | 주식회사 엘지화학 | Compound and organic light emitting device comprising the same |
| US10211407B2 (en) | 2015-03-16 | 2019-02-19 | Samsung Display Co., Ltd. | Condensed cyclic compound and organic light-emitting device including the same |
| WO2019039723A1 (en) * | 2017-08-25 | 2019-02-28 | 주식회사 두산 | Organic compound and organic electroluminescent device comprising same |
| US10224487B2 (en) | 2013-09-17 | 2019-03-05 | Samsung Display Co., Ltd. | Organic light-emitting device |
| US10249824B2 (en) | 2012-05-03 | 2019-04-02 | Samsung Display Co., Ltd. | Condensed-cyclic compound and organic light-emitting diode comprising the same |
| KR20190064441A (en) | 2017-11-30 | 2019-06-10 | 솔브레인 주식회사 | Organic compound, organic light emitting diode including the same and display including the organic light emitting diode |
| US10361380B2 (en) | 2012-11-01 | 2019-07-23 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
| US10421721B2 (en) | 2015-09-14 | 2019-09-24 | Lg Chem, Ltd. | Heterocyclic compound and organic light emitting device comprising same |
| US10446765B2 (en) | 2014-06-30 | 2019-10-15 | Heesung Material Ltd. | Heterocyclic compound and organic light emitting element using same |
| KR20200038282A (en) * | 2017-08-10 | 2020-04-10 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | Organic compounds, light-emitting elements, light-emitting devices, electronic devices, and lighting devices |
| WO2020096421A1 (en) * | 2018-11-08 | 2020-05-14 | 엘티소재주식회사 | Heterocyclic compound and organic light-emitting diode comprising same |
| CN113801057A (en) * | 2021-08-13 | 2021-12-17 | 浙江大学 | chrysene radical aza [7] spiroalkene compound, preparation method and application |
| DE102021117968A1 (en) | 2020-07-14 | 2022-01-20 | Rohm And Haas Electronic Materials Korea Ltd. | MULTIPLE HOST MATERIALS AND THIS COMPREHENSIVE ORGANIC ELECTROLUMINESCING DEVICE |
| US11641777B2 (en) | 2017-11-24 | 2023-05-02 | Semiconductor Energy Laboratory Co., Ltd. | Dibenzo[c,g]carbazole derivative, light-emitting device, light-emitting apparatus, electronic device, and lighting device |
| US11678576B2 (en) | 2018-09-28 | 2023-06-13 | Lt Materials Co., Ltd. | Heterocyclic compound and organic light emitting element comprising same |
Families Citing this family (64)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101117724B1 (en) * | 2009-09-04 | 2012-03-07 | 삼성모바일디스플레이주식회사 | Organic light emitting device |
| KR101202347B1 (en) * | 2009-10-09 | 2012-11-16 | 삼성디스플레이 주식회사 | A condensed-cyclic compound and an organic light emitting diode employing an organic layer comprising the same |
| EP2489664A4 (en) | 2009-10-16 | 2013-04-03 | Idemitsu Kosan Co | Fluorene-containing aromatic compound, material for organic electroluminescent element, and organic electroluminescent element using same |
| TWI491602B (en) * | 2009-12-03 | 2015-07-11 | Jnc Corp | Benzo(c)carbazole compound having substituent including pyridine and organic electroluminescent device |
| KR101736987B1 (en) | 2010-04-06 | 2017-05-18 | 삼성디스플레이 주식회사 | Heterocyclic compound and organic light emitting device comprising the same |
| KR101758328B1 (en) | 2010-04-06 | 2017-07-17 | 삼성디스플레이 주식회사 | Heterocyclic compound and organic light emitting device comprising the same |
| WO2011132684A1 (en) | 2010-04-20 | 2011-10-27 | 出光興産株式会社 | Bis-carbazole derivative, material for organic electroluminescent element and organic electroluminescent element using same |
| KR20120006811A (en) * | 2010-07-13 | 2012-01-19 | 삼성모바일디스플레이주식회사 | Organic light emitting device |
| US20140054564A1 (en) * | 2010-07-30 | 2014-02-27 | Rohm And Haas Electronic Materials Korea Ltd. | Electroluminescent device using electroluminescent compound as luminescent material |
| KR101810045B1 (en) * | 2010-10-25 | 2017-12-19 | 삼성디스플레이 주식회사 | Heterocyclic compound and Organic light emitting device containing same |
| TWI504722B (en) * | 2010-12-03 | 2015-10-21 | Jnc Corp | Benzo[c]carbazole compound having pyridine substituent and organic electroluminescent device |
| KR101720444B1 (en) | 2011-02-07 | 2017-03-27 | 이데미쓰 고산 가부시키가이샤 | Biscarbazole derivative and organic electroluminescent element using same |
| KR20120109744A (en) * | 2011-03-25 | 2012-10-09 | 롬엔드하스전자재료코리아유한회사 | Novel compounds for organic electronic material and organic electroluminescence device using the same |
| WO2012150826A1 (en) * | 2011-05-03 | 2012-11-08 | Rohm And Haas Electronic Materials Korea Ltd. | Novel organic electroluminescent compounds and an organic electroluminescent device using the same |
| KR101396171B1 (en) * | 2011-05-03 | 2014-05-27 | 롬엔드하스전자재료코리아유한회사 | Novel organic electroluminescent compounds and an organic electroluminescent device using the same |
| JP6347909B2 (en) * | 2011-08-22 | 2018-06-27 | ユー・ディー・シー アイルランド リミテッド | ORGANIC ELECTROLUMINESCENT ELEMENT, ELEMENT MATERIAL, AND LIGHT EMITTING DEVICE, DISPLAY DEVICE AND LIGHTING DEVICE USING THE ELEMENT |
| KR20130025190A (en) * | 2011-09-01 | 2013-03-11 | 롬엔드하스전자재료코리아유한회사 | Novel compounds for organic electronic material and organic electroluminescent device using the same |
| KR20130042901A (en) * | 2011-10-19 | 2013-04-29 | 삼성디스플레이 주식회사 | A condensed-cyclic compound and an organic light emitting diode comprising the same |
| KR20130055216A (en) * | 2011-11-18 | 2013-05-28 | 롬엔드하스전자재료코리아유한회사 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| CN103959503B (en) | 2011-12-05 | 2016-08-24 | 出光兴产株式会社 | Material for organic electroluminescent element and organic electroluminescent element |
| WO2013089424A1 (en) * | 2011-12-12 | 2013-06-20 | 제일모직 주식회사 | Compound for an organic optoelectric device, organic light-emitting diode including same, and display device including the organic light-emitting diode |
| KR102102620B1 (en) | 2012-06-12 | 2020-04-21 | 도레이 카부시키가이샤 | Material for light-emitting element and light-emiting element |
| KR101431645B1 (en) * | 2012-06-26 | 2014-08-20 | 롬엔드하스전자재료코리아유한회사 | Light-Emitting Layer and Organic Electroluminescence Device comprising the same |
| KR101946891B1 (en) | 2012-07-05 | 2019-02-12 | 도레이 카부시키가이샤 | Light emitting elment material and light emitting element |
| CN104797571A (en) * | 2012-12-04 | 2015-07-22 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compounds and organic electroluminescent device comprising the same |
| TWI602901B (en) | 2012-12-11 | 2017-10-21 | 半導體能源研究所股份有限公司 | Light-emitting element, light-emitting device, electronic device, and lighting device |
| JP5897050B2 (en) * | 2013-01-31 | 2016-03-30 | 富士フイルム株式会社 | Organic thin film transistor, organic semiconductor thin film and organic semiconductor material |
| CN107739352B (en) * | 2013-03-22 | 2024-05-14 | 默克专利有限公司 | Material for electronic devices |
| KR101656559B1 (en) * | 2013-04-29 | 2016-09-09 | 주식회사 엘지화학 | Aromatic compounds and organic electronic device using the same |
| KR101656560B1 (en) * | 2013-04-29 | 2016-09-09 | 주식회사 엘지화학 | Aromatic compounds and organic electronic device using the same |
| CN104178125A (en) * | 2013-05-28 | 2014-12-03 | 海洋王照明科技股份有限公司 | Blue light phosphorescent host material containing tetraphenyl-silicon unit, preparation method and organic electroluminescent device thereof |
| KR101682844B1 (en) * | 2013-06-04 | 2016-12-05 | 이데미쓰 고산 가부시키가이샤 | Nitrogen-containing heterocyclic derivative, organic electroluminescence element material using same, and organic electroluminescence element and electronic device using same |
| US9673401B2 (en) | 2013-06-28 | 2017-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| KR102100929B1 (en) | 2013-09-04 | 2020-04-14 | 삼성전자주식회사 | Condensed compound and organic light emitting diode including the same |
| CN104513661B (en) * | 2013-09-30 | 2018-07-06 | 北京鼎材科技有限公司 | A kind of luminous organic material and its application |
| KR20150042387A (en) * | 2013-10-11 | 2015-04-21 | 에스에프씨 주식회사 | An electroluminescent compound and an electroluminescent device comprising the same |
| US10396294B2 (en) | 2013-12-27 | 2019-08-27 | Samsung Electronics Co., Ltd. | Carbazole compound and organic light-emitting device including the same |
| KR101754715B1 (en) * | 2014-04-08 | 2017-07-10 | 롬엔드하스전자재료코리아유한회사 | Multi-component host material and organic electroluminescence device comprising the same |
| WO2015174738A1 (en) * | 2014-05-14 | 2015-11-19 | Rohm And Haas Electronic Materials Korea Ltd. | Multi-component host material and organic electroluminescent device comprising the same |
| KR20150130928A (en) * | 2014-05-14 | 2015-11-24 | 롬엔드하스전자재료코리아유한회사 | Multi-component host material and organic electroluminescent device comprising the same |
| KR102576858B1 (en) * | 2015-06-18 | 2023-09-12 | 롬엔드하스전자재료코리아유한회사 | A plurality of host materials and organic electroluminescent device comprising the same |
| KR101905970B1 (en) * | 2015-09-24 | 2018-10-10 | 주식회사 엘지화학 | Compound and organic electronic device comprising the same |
| KR102292768B1 (en) * | 2015-10-13 | 2021-08-25 | 롬엔드하스전자재료코리아유한회사 | Organic Electroluminescent Compounds and Organic Electroluminescent Devices Comprising the Same |
| CN108349914B9 (en) * | 2015-10-27 | 2021-09-03 | 株式会社Lg化学 | Organic light emitting device |
| US10207992B2 (en) | 2015-10-30 | 2019-02-19 | Semiconductor Energy Laboratory Co., Ltd. | Dibenzocarbazole compound, light-emitting element, light-emitting device, display device, electronic device, and lighting device |
| JP6371320B2 (en) * | 2016-02-12 | 2018-08-08 | ユー・ディー・シー アイルランド リミテッド | ORGANIC ELECTROLUMINESCENT ELEMENT, ELEMENT MATERIAL, AND LIGHT EMITTING DEVICE, DISPLAY DEVICE AND LIGHTING DEVICE USING THE ELEMENT |
| KR102544984B1 (en) * | 2016-03-18 | 2023-06-20 | 삼성디스플레이 주식회사 | Compound and Organic light emitting device comprising same |
| WO2017183859A1 (en) | 2016-04-18 | 2017-10-26 | Rohm And Haas Electronic Materials Korea Ltd. | A plurality of host materials and organic electroluminescent device comprising the same |
| KR102479135B1 (en) * | 2016-04-18 | 2022-12-21 | 롬엔드하스전자재료코리아유한회사 | A plurality of host materials and organic electroluminescent device comprising the same |
| KR102122340B1 (en) | 2016-12-02 | 2020-06-12 | 삼성에스디아이 주식회사 | Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device |
| US10629820B2 (en) | 2017-01-18 | 2020-04-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN107721903A (en) * | 2017-11-13 | 2018-02-23 | 长春海谱润斯科技有限公司 | A kind of electroluminescent organic material and its organic luminescent device |
| CN111886231B (en) * | 2018-04-05 | 2023-08-01 | 株式会社Lg化学 | Carbazole-based compound and organic light emitting device including the same |
| KR20190139754A (en) * | 2018-06-08 | 2019-12-18 | 롬엔드하스전자재료코리아유한회사 | A plurality of host materials and organic electroluminescent device comprising the same |
| KR20200013600A (en) * | 2018-07-30 | 2020-02-07 | 롬엔드하스전자재료코리아유한회사 | A plurality of host materials and organic electroluminescent device comprising the same |
| EP3680242A1 (en) | 2019-01-10 | 2020-07-15 | Idemitsu Kosan Co., Ltd. | Organic light emitting device and compounds for use in same |
| KR102430048B1 (en) | 2019-06-13 | 2022-08-04 | 삼성에스디아이 주식회사 | Compound for optoelectronic device and organic optoelectronic device and display device |
| CN112110896B (en) * | 2019-06-19 | 2024-02-09 | 北京鼎材科技有限公司 | Organic electroluminescent material and application thereof |
| CN110483500A (en) * | 2019-07-10 | 2019-11-22 | 南京友斯贝特光电材料有限公司 | A kind of OLED material of main part and preparation method thereof and OLED device |
| CN110964019B (en) * | 2019-12-12 | 2021-05-04 | 西安瑞联新材料股份有限公司 | Compound taking 6-phenyl-6H-indolo [2,3-b ] quinoxaline as receptor and application thereof |
| CN111129330A (en) * | 2019-12-26 | 2020-05-08 | 武汉华星光电半导体显示技术有限公司 | Display panel and preparation method thereof |
| KR102511932B1 (en) * | 2020-01-31 | 2023-03-20 | 주식회사 엘지화학 | Novel compound and organic light emitting device comprising the same |
| CN114373872A (en) * | 2020-10-15 | 2022-04-19 | 江苏三月科技股份有限公司 | Organic electroluminescent device |
| CN113402524A (en) * | 2021-07-26 | 2021-09-17 | 中国科学院宁波材料技术与工程研究所 | Thermal activation delayed fluorescence micromolecule material, organic electroluminescent device and manufacturing method |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20070073868A (en) * | 2004-11-04 | 2007-07-10 | 이데미쓰 고산 가부시키가이샤 | Compound containing fused ring and organic electroluminescent element employing the same |
| KR20080047210A (en) * | 2006-11-24 | 2008-05-28 | 삼성전자주식회사 | Organic light emitting compound and organic light emitting device comprising the same |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100573137B1 (en) * | 2004-04-02 | 2006-04-24 | 삼성에스디아이 주식회사 | Fluorene-based compound and organic electroluminescent display device using the same |
| KR100787425B1 (en) * | 2004-11-29 | 2007-12-26 | 삼성에스디아이 주식회사 | Phenylcarbazole-based compound and Organic electroluminescence display employing the same |
| KR101372850B1 (en) * | 2006-05-10 | 2014-03-11 | 삼성디스플레이 주식회사 | Dimethylenecyclohexane compound, method for preparing the same and organic light emitting device comprising the same |
| KR100841253B1 (en) * | 2006-08-23 | 2008-06-25 | 대주전자재료 주식회사 | Aromatic Amine Compounds And Organic Electroluminescence Using Them |
| KR101359630B1 (en) * | 2006-10-23 | 2014-02-10 | 삼성디스플레이 주식회사 | Organoelectroluminescent compound and organoelectroluminescent device employing the same |
| KR20080047209A (en) * | 2006-11-24 | 2008-05-28 | 삼성전자주식회사 | Organic light emitting compound and organic light emitting device comprising the same |
-
2009
- 2009-03-31 KR KR1020090027256A patent/KR101603070B1/en active IP Right Grant
-
2010
- 2010-03-29 WO PCT/KR2010/001897 patent/WO2010114264A2/en active Application Filing
- 2010-03-31 TW TW099109821A patent/TW201105774A/en unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20070073868A (en) * | 2004-11-04 | 2007-07-10 | 이데미쓰 고산 가부시키가이샤 | Compound containing fused ring and organic electroluminescent element employing the same |
| KR20080047210A (en) * | 2006-11-24 | 2008-05-28 | 삼성전자주식회사 | Organic light emitting compound and organic light emitting device comprising the same |
Cited By (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8455867B2 (en) | 2010-10-26 | 2013-06-04 | Samsung Display Co., Ltd. | Organic light-emitting device |
| US8546793B2 (en) | 2010-10-26 | 2013-10-01 | Samsung Display Co., Ltd. | Organic light-emitting device |
| KR101328977B1 (en) * | 2010-10-26 | 2013-11-13 | 삼성디스플레이 주식회사 | Organic light emitting device |
| KR101328978B1 (en) * | 2010-10-26 | 2013-11-13 | 삼성디스플레이 주식회사 | Organic light emitting device |
| US8771844B2 (en) | 2011-06-22 | 2014-07-08 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting diode and flat display device including the heterocyclic compound |
| US9416107B2 (en) | 2011-06-29 | 2016-08-16 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
| KR20130011446A (en) * | 2011-07-21 | 2013-01-30 | 롬엔드하스전자재료코리아유한회사 | Novel organic electroluminescence compounds and organic electroluminescence device using the same |
| US9240558B2 (en) | 2011-07-22 | 2016-01-19 | Semiconductor Energy Laboratory Co., Ltd. | Dibenzole[c,g]carbazole compound, light-emitting element, light-emitting device, display device, lighting device and electronic device |
| US8986857B2 (en) | 2011-07-22 | 2015-03-24 | Semiconductor Energy Laboratory Co., Ltd. | Dibenzo[c,g]carbazole compound, light-emitting element, light-emitting device, display device, lighting device and electronic device |
| US9005777B2 (en) | 2011-10-19 | 2015-04-14 | Samsung Display Co., Ltd. | Heterocyclic compound, organic light-emitting diode including the heterocyclic compound, and flat display device including the organic light-emitting diode |
| US10249824B2 (en) | 2012-05-03 | 2019-04-02 | Samsung Display Co., Ltd. | Condensed-cyclic compound and organic light-emitting diode comprising the same |
| US9893301B2 (en) | 2012-07-25 | 2018-02-13 | Samsung Display Co., Ltd. | Heterocyclic compounds and organic light-emitting devices including the same |
| US9385327B2 (en) | 2012-08-01 | 2016-07-05 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
| US9722182B2 (en) | 2012-10-30 | 2017-08-01 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
| US10361380B2 (en) | 2012-11-01 | 2019-07-23 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
| KR20140083412A (en) * | 2012-12-26 | 2014-07-04 | 엘지디스플레이 주식회사 | Red Phosphorescent Host Material and Organic Electroluminescent Device Using the Same |
| US9691992B2 (en) | 2013-01-30 | 2017-06-27 | Samsung Displey Co., Ltd. | Organic light-emitting diode |
| US9006721B2 (en) | 2013-02-08 | 2015-04-14 | Samsung Display Co., Ltd. | Organic light-emitting diode |
| US9525144B2 (en) | 2013-02-08 | 2016-12-20 | Samsung Display Co., Ltd. | Organic light-emitting diode |
| KR20140120089A (en) * | 2013-04-02 | 2014-10-13 | 에스에프씨 주식회사 | An organoelectro luminescent compounds and organoelectro luminescent device using the same |
| US11063220B2 (en) | 2013-06-18 | 2021-07-13 | Samsung Display Co., Ltd. | Organic light-emitting device |
| US10062848B2 (en) | 2013-06-18 | 2018-08-28 | Samsung Display Co., Ltd. | Organic light-emitting device |
| US9722185B2 (en) | 2013-08-12 | 2017-08-01 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
| US10224487B2 (en) | 2013-09-17 | 2019-03-05 | Samsung Display Co., Ltd. | Organic light-emitting device |
| KR20150052705A (en) * | 2013-11-06 | 2015-05-14 | 주식회사 두산 | Organic compounds and organic electro luminescence device comprising the same |
| KR20150111534A (en) * | 2014-03-25 | 2015-10-06 | 삼성디스플레이 주식회사 | Heterocyclic compound and organic light emitting device comprising the same |
| KR20150135109A (en) | 2014-05-23 | 2015-12-02 | 롬엔드하스전자재료코리아유한회사 | An organic electroluminescent compound and an organic electroluminescent device comprising the same |
| WO2015178731A1 (en) | 2014-05-23 | 2015-11-26 | Rohm And Haas Electronic Materials Korea Ltd. | An organic electroluminescent compound and an organic electroluminescent device comprising the same |
| US10446765B2 (en) | 2014-06-30 | 2019-10-15 | Heesung Material Ltd. | Heterocyclic compound and organic light emitting element using same |
| KR20160034804A (en) * | 2014-09-22 | 2016-03-30 | 주식회사 엘지화학 | Hetero-cyclic compound and organic light emitting device comprising the same |
| US10886474B2 (en) | 2014-09-26 | 2021-01-05 | Rohm And Haas Electronic Materials Korea Ltd | Organic electroluminescent compound, and organic electroluminescent material and organic electroluminescent device comprising the same |
| KR20160037107A (en) | 2014-09-26 | 2016-04-05 | 롬엔드하스전자재료코리아유한회사 | Organic Electroluminescent Compound, and Organic Electroluminescent Material and Organic Electroluminescent Device Comprising the Same |
| WO2016064088A3 (en) * | 2014-10-21 | 2016-08-11 | 덕산네오룩스 주식회사 | Compound for organic electric device, organic electric device using same, and electronic device using same |
| KR20160046703A (en) * | 2014-10-21 | 2016-04-29 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| US9515271B2 (en) | 2014-12-03 | 2016-12-06 | Samsung Display Co., Ltd. | Organic light-emitting device |
| KR20160099471A (en) * | 2015-02-12 | 2016-08-22 | 롬엔드하스전자재료코리아유한회사 | Organic Electroluminescent Compounds and Organic Electroluminescent Device Comprising the Same |
| US10211407B2 (en) | 2015-03-16 | 2019-02-19 | Samsung Display Co., Ltd. | Condensed cyclic compound and organic light-emitting device including the same |
| KR20170030291A (en) * | 2015-09-09 | 2017-03-17 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof |
| WO2017043797A1 (en) * | 2015-09-09 | 2017-03-16 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using same, and electronic device thereof |
| US10968208B2 (en) | 2015-09-09 | 2021-04-06 | Duk San Neolux Co., Ltd. | Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof |
| WO2017047992A1 (en) * | 2015-09-14 | 2017-03-23 | 주식회사 엘지화학 | Heterocyclic compound and organic light emitting device comprising same |
| US10421721B2 (en) | 2015-09-14 | 2019-09-24 | Lg Chem, Ltd. | Heterocyclic compound and organic light emitting device comprising same |
| KR20170042423A (en) * | 2015-10-08 | 2017-04-19 | 삼성디스플레이 주식회사 | Condensed-cyclic compound and organic light emitting device comprising the same |
| US20180305337A1 (en) * | 2015-10-22 | 2018-10-25 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compounds and organic electroluminescent device comprising the same |
| US20220081419A1 (en) * | 2015-10-22 | 2022-03-17 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compounds and organic electroluminescent device comprising the same |
| US10800969B2 (en) | 2015-11-17 | 2020-10-13 | Lg Chem, Ltd. | Heterocyclic compound and organic light emitting element comprising same |
| WO2017086696A1 (en) * | 2015-11-17 | 2017-05-26 | 주식회사 엘지화학 | Heterocyclic compound and organic light-emitting element comprising same |
| KR20180031385A (en) * | 2016-09-20 | 2018-03-28 | 에스에프씨 주식회사 | Novel organic compounds and organic light-emitting diode therewith |
| WO2018236182A1 (en) * | 2017-06-23 | 2018-12-27 | 주식회사 엘지화학 | Compound and organic electroluminescent device comprising same |
| KR20190013605A (en) * | 2017-07-28 | 2019-02-11 | 주식회사 엘지화학 | Compound and organic light emitting device comprising the same |
| US11396494B2 (en) | 2017-07-28 | 2022-07-26 | Lg Chem, Ltd. | Compound and organic light emitting element comprising same |
| KR20200038282A (en) * | 2017-08-10 | 2020-04-10 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | Organic compounds, light-emitting elements, light-emitting devices, electronic devices, and lighting devices |
| KR20190022113A (en) * | 2017-08-25 | 2019-03-06 | 주식회사 두산 | Organic compounds and organic electro luminescence device comprising the same |
| WO2019039723A1 (en) * | 2017-08-25 | 2019-02-28 | 주식회사 두산 | Organic compound and organic electroluminescent device comprising same |
| US11641777B2 (en) | 2017-11-24 | 2023-05-02 | Semiconductor Energy Laboratory Co., Ltd. | Dibenzo[c,g]carbazole derivative, light-emitting device, light-emitting apparatus, electronic device, and lighting device |
| KR20190064441A (en) | 2017-11-30 | 2019-06-10 | 솔브레인 주식회사 | Organic compound, organic light emitting diode including the same and display including the organic light emitting diode |
| US11678576B2 (en) | 2018-09-28 | 2023-06-13 | Lt Materials Co., Ltd. | Heterocyclic compound and organic light emitting element comprising same |
| WO2020096421A1 (en) * | 2018-11-08 | 2020-05-14 | 엘티소재주식회사 | Heterocyclic compound and organic light-emitting diode comprising same |
| DE102021117968A1 (en) | 2020-07-14 | 2022-01-20 | Rohm And Haas Electronic Materials Korea Ltd. | MULTIPLE HOST MATERIALS AND THIS COMPREHENSIVE ORGANIC ELECTROLUMINESCING DEVICE |
| KR20220008518A (en) | 2020-07-14 | 2022-01-21 | 롬엔드하스전자재료코리아유한회사 | A plurality of host materials and organic electroluminescent device comprising the same |
| CN113801057A (en) * | 2021-08-13 | 2021-12-17 | 浙江大学 | chrysene radical aza [7] spiroalkene compound, preparation method and application |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2010114264A2 (en) | 2010-10-07 |
| WO2010114264A3 (en) | 2010-11-25 |
| TW201105774A (en) | 2011-02-16 |
| KR101603070B1 (en) | 2016-03-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101603070B1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| KR101741415B1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| KR101477613B1 (en) | Novel Compounds for Organic Electronic Material and Organic Electronic Device Using the Same | |
| JP5781499B2 (en) | Novel organic electroluminescent compound and organic electroluminescent device using the same | |
| KR20100118700A (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| JP2017031169A (en) | Novel compounds for organic electronic material and organic electroluminescent device using the same | |
| KR20110116635A (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| KR20110112098A (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| KR20110132721A (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| KR20100109050A (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| KR20100106014A (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| KR101784147B1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| JP2015216382A (en) | New organic electroluminescent compound and organic electroluminescent element using the same | |
| KR20120038060A (en) | Novel compounds for organic electronic material and organic electroluminescent device using the same | |
| KR20110008784A (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| KR20110113297A (en) | Novel compounds for organic electronic material and organic electroluminescent device using the same | |
| KR20100137198A (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| KR20120020816A (en) | Novel compounds for organic electronic material and organic electroluminescent device using the same | |
| KR20110066494A (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| KR20110008619A (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| KR20110120994A (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| KR20120038056A (en) | Novel compounds for organic electronic material and organic electroluminescent device using the same | |
| KR20120020901A (en) | Novel compounds for organic electronic material and organic electroluminescent device using the same | |
| KR20110093055A (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| KR20110134581A (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| N231 | Notification of change of applicant | ||
| A201 | Request for examination | ||
| A302 | Request for accelerated examination | ||
| E902 | Notification of reason for refusal | ||
| AMND | Amendment | ||
| E902 | Notification of reason for refusal | ||
| AMND | Amendment | ||
| E902 | Notification of reason for refusal | ||
| AMND | Amendment | ||
| E601 | Decision to refuse application | ||
| AMND | Amendment | ||
| J201 | Request for trial against refusal decision | ||
| A107 | Divisional application of patent | ||
| B701 | Decision to grant | ||
| GRNT | Written decision to grant | ||
| FPAY | Annual fee payment |
Payment date: 20200218 Year of fee payment: 5 |