KR20090041019A - Red phosphorescent compound and organic electroluminescent device using same - Google Patents
Red phosphorescent compound and organic electroluminescent device using sameDownload PDFInfo
- Publication number
- KR20090041019A KR20090041019AKR1020070106495AKR20070106495AKR20090041019AKR 20090041019 AKR20090041019 AKR 20090041019AKR 1020070106495 AKR1020070106495 AKR 1020070106495AKR 20070106495 AKR20070106495 AKR 20070106495AKR 20090041019 AKR20090041019 AKR 20090041019A
- Authority
- KR
- South Korea
- Prior art keywords
- light emitting
- group
- phosphorescent compound
- red phosphorescent
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Images
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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
- 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
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
- 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
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
- 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
- H10K85/30—Coordination compounds
- H10K85/381—Metal complexes comprising a group IIB metal element, e.g. comprising cadmium, mercury or zinc
- 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
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- 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
- C09K2211/18—Metal complexes
- C09K2211/186—Metal complexes of the light metals other than alkali metals and alkaline earth metals, i.e. Be, Al or Mg
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Translated fromKorean
Description
Translated fromKorean본 발명은 적색 인광 화합물 및 이를 이용한 유기 전계 발광 소자에 관한 것이다.The present invention relates to a red phosphorescent compound and an organic electroluminescent device using the same.
일반적으로, 유기 전계 발광 소자는 전자 주입을 위한 음극과 정공 주입을 위한 양극 사이에 형성된 유기막에 전하를 주입하면 전자와 정공이 쌍을 이룬 후 소멸하면서 빛을 내는 소자이다.In general, when an electric charge is injected into an organic film formed between a cathode for electron injection and an anode for hole injection, the organic electroluminescent device emits light while pairing with electrons and holes.
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 (약 10V 이하) 구동이 가능하고, 또한 전력 소모가 비교적 적으며, 색감이 뛰어나다는 장점이 있다.Not only can the device be formed on a flexible transparent substrate such as plastic, but it can also be driven at a lower voltage (about 10V or less) than plasma display panels or inorganic EL displays, and it also consumes power. Is relatively small, and the color is excellent.
또한, 유기 전계 발광 소자는 녹색, 청색, 적색의 3가지 색을 나타낼 수가 있어 차세대 풀 컬러 디스플레이(full color display) 소자로 많은 사람들의 많은 관심의 대상이 되고 있다.In addition, the organic electroluminescent device can display three colors of green, blue, and red, and thus, has become a subject of much interest as a next generation full color display device.
여기서, 유기 EL 소자를 제작하는 과정을 간단히 살펴보면 다음과 같다.Here, the process of manufacturing the organic EL device will be briefly described as follows.
먼저, 투명기판 위에 양극(anode)을 형성한다.First, an anode is formed on a transparent substrate.
여기서, 양극 물질로는 흔히 ITO (indium tin oxide)가 사용된다.Here, indium tin oxide (ITO) is often used as the anode material.
이어, 양극(2) 위에 정공주입층(HIL:hole injecting layer)을 형성한다.Next, a hole injecting layer (HIL) is formed on the anode 2.
여기서, 정공주입층은 주로 구리 프탈로시안(copper phthalocyanine(CuPc))을 사용하고, 약 10 ~ 30nm 두께로 형성한다.Here, the hole injection layer is mainly formed of copper phthalocyanine (CuPc), and is formed to a thickness of about 10 ~ 30nm.
다음, 정공주입층 위에 정공수송층(HTL: hole transport layer)을 형성한다.Next, a hole transport layer (HTL) is formed on the hole injection layer.
여기서, 정공수송층은 4,4'-비스[N-(1-나프틸)-N-페닐아미노]-바이페닐(4,4'-bis[N-(1-naphthyl)-N-phenylamino]-biphenyl(NPB))을 사용하고, 약 30 ~ 60nm 두께로 형성한다.Here, the hole transport layer is 4,4'-bis [N- (1-naphthyl) -N-phenylamino] -biphenyl (4,4'-bis [N- (1-naphthyl) -N-phenylamino]- biphenyl (NPB)) is used to form a thickness of about 30 ~ 60nm.
그리고, 정공수송층 위에 유기발광층(organic emitting layer)을 형성한다.In addition, an organic light emitting layer is formed on the hole transport layer.
이때, 필요에 따라 도펀트(dopant)를 첨가한다.At this time, a dopant is added as needed.
인광 적색 발광의 경우, 흔히 유기발광층은 4,4'-N,N'-디카바졸-바이페닐(4,4'-N,N'-dicarbazole-biphenyl(CBP))을 두께 약 30 ~ 60nm 정도로 형성하고, 도펀트(dopant)로는 이리듐 콤플렉스(Iridium complex)를 많이 사용한다.In the case of phosphorescent red light emission, the organic light emitting layer often has 4,4'-N, N'-dicarbazole-biphenyl (4,4'-N, N'-dicarbazole-biphenyl (CBP)) in a thickness of about 30 to 60 nm. The iridium complex is used a lot as the dopant.
이어, 유기발광층 위에 전자수송층(ETL: electron transport layer) 및 전자주입층(EIL: electron injecting layer)을 연속적으로 형성하거나, 또는 전자주입 수송층을 형성한다.Subsequently, an electron transport layer (ETL) and an electron injecting layer (EIL) are continuously formed on the organic light emitting layer, or an electron injection transport layer is formed.
여기서, 전자수송층은 트리스(8-하이드록시-퀴놀레이트)알루미늄(tris(8-hydroxy-quinolate)aluminum(Alq3))을 주로 많이 사용한다.Here, the electron transport layer mainly uses tris (8-hydroxy-quinolate) aluminum (Alq3).
다음, 전자주입층 위에 음극(cathode)을 형성하고, 그 위에 보호막을 형성한 다.Next, a cathode is formed on the electron injection layer, and a protective film is formed thereon.
이와 같이 형성된 소자는 발광층의 형성 방식에 따라 청색, 녹색, 적색의 발광 소자를 각각 구현 할 수가 있다.The devices formed as described above may implement blue, green, and red light emitting devices, respectively, according to a method of forming the light emitting layer.
소자의 발광층에서는 양쪽 전극에서부터 주입된 전자와 정공의 재결합에 의해 여기자가 형성된다.In the light emitting layer of the device, excitons are formed by recombination of electrons and holes injected from both electrodes.
여기자는 일중항과 삼중항의 비율이 1:3 으로 존재하며, 형광의 경우 일중항 여기자만 이용되고, 인광의 경우 일중항과 삼중항을 모두 사용하여 보다 뛰어난 발광효율을 얻을 수 있다.The excitons have a ratio of 1: 3 to singlet and triplet, and in the case of fluorescence, only singlet excitons are used, and in the case of phosphorescence, both singlet and triplet can be used to obtain more excellent luminous efficiency.
이와 같이 인광 재료는 형광재료에 비해 매우 높은 양자효율을 가질 수 있으므로, 유기 전계 발광 소자의 효율을 높이는 중요한 방법으로 많이 연구되고 있다.As such, the phosphorescent material may have a very high quantum efficiency compared to the fluorescent material, and thus, much research has been conducted as an important method for increasing the efficiency of the organic EL device.
외부발광효율(ηle : luminance efficiency)은 다음과 같은 식으로 표현될 수 있다.External luminance efficiency (ηle ) can be expressed as follows.
ηle = k ·ηint ·ηoutηle = k ηint ηout
여기서, k는 색감에 따른 사람 눈의 민감도, ηint는 내부양자효율(internal quantum efficiency), ηout는 광학출력효율(outcoupling efficiency)이다.Where k is the sensitivity of the human eye according to color, ηint is the internal quantum efficiency, and ηout is the outcoupling efficiency.
높은 외부발광효율 얻기 위해서는 내부양자효율이 우수해야 하지만, 높은 순도의 적색(CIE 색좌표 X값이 큼)의 경우, 도 1에서 나타난 것과 같이, 시감도가 떨어지는 문제가 있으므로, 같은 내부양자효율로는 같은 외부양자효율을 얻기가 어려운 문제가 있다.The internal quantum efficiency should be excellent in order to obtain a high external light emission efficiency, but in the case of high purity red (the CIE color coordinate X value is large), as shown in FIG. It is difficult to obtain external quantum efficiency.
이에 따라, 색순도(CIE 색순도 X = 0.65이상)가 높으면서도 높은 발광효율 및 긴 발광수명의 특징을 가지는 적색 인광화합물의 개발이 요구되고 있다.Accordingly, there is a demand for the development of a red phosphorescent compound having high color purity (CIE color purity X = 0.65 or more) while having high light emission efficiency and long light emission life.
본 발명의 목적은 이러한 문제들을 해결하기 위한 것으로, 발광층의 도펀트로 사용되는 화학식 1을 합성하여 색순도를 높이고, 높은 발광효율 및 긴 발광수명을 가질 수 있는 적색 인광 화합물 및 이를 이용한 유기 전계 발광 소자를 제공하는데 있다.SUMMARY OF THE INVENTION An object of the present invention is to solve the above problems, by synthesizing the general formula (1) used as the dopant of the light emitting layer to increase the color purity, red phosphorescent compound that can have a high luminous efficiency and long emission life and an organic electroluminescent device using the same To provide.
본 발명에 따른 적색 인광 화합물은 하기 화학식 1로 표시되는 적색 인광 화합물일 수 있다.The red phosphorescent compound according to the present invention may be a red phosphorescent compound represented by Formula 1 below.
[화학식1][Formula 1]
(상기 화학식 1에서
그리고, R1, R2, R3, R4는 각각 독립적으로 수소, C1 내지 C6의 알킬기, C1 내지 C4의 알콕시기로부터 선택될 수 있고, 적어도 하나는 C1 내지 C6의 알킬기일 수 있다.In addition, R1, R2, R3, and R4 may each independently be selected from hydrogen, an alkyl group of C1 to C6, an alkoxy group of C1 to C4, and at least one may be an alkyl group of C1 to C6.
또한, R5, R6, R7은 각각 독립적으로 수소, C1 내지 C6의 알킬기, C1 내지 C4의 알콕시기로부터 선택될 수 있고, 그 중 적어도 두 개가 선택될 수 있다.In addition, R5, R6, R7 may be each independently selected from hydrogen, an alkyl group of C1 to C6, an alkoxy group of C1 to C4, at least two of them may be selected.
여기서, C1 내지 C6의 알킬기는 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸 및 t-부틸로 이루어진 그룹으로부터 선택될 수 있으며, C1 내지 C4의 알콕시기는 메톡시, 에톡시, n-프로톡시, i-프로톡시, n-부톡시, i-부톡시 및 t-부톡시로 이루어진 그룹으로부터 선택될 수 있다.Wherein the alkyl group of C1 to C6 may be selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl and t-butyl, wherein the alkoxy group of C1 to C4 is methoxy, It may be selected from the group consisting of oxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy and t-butoxy.
그리고, 본 발명에 따른 유기전계발광소자는 양극과 음극 사이에 발광층을 포함하여 이루어질 수 있고, 화학식 1의 화합물을 발광층의 도펀트로 사용할 수 있다.The organic light emitting device according to the present invention may include a light emitting layer between an anode and a cathode, and the compound of Formula 1 may be used as a dopant of the light emitting layer.
여기서, 발광층은 Al, Zn 금속 착물 및 카바졸 유도체 중 어느 하나를 호스트로 사용할 수 있다.Here, the light emitting layer may use any one of Al, Zn metal complex and carbazole derivatives as a host.
본 발명의 다른 목적, 특징 및 잇점들은 첨부한 도면을 참조한 실시예들의 상세한 설명을 통해 명백해질 것이다.Other objects, features and advantages of the present invention will become apparent from the following detailed description of embodiments taken in conjunction with the accompanying drawings.
본 발명에 따른 적색 인광 화합물을 화학식 1과 같은 구조식을 갖는 화합물로 제작하고, 이 화합물을 유기전계발광소자의 발광층에 사용함으로써, 고색순도, 고휘도, 장수명인 유기전계발광소자를 얻을 수 있는 효과가 있다.By producing a red phosphorescent compound according to the present invention to a compound having the structure of formula (1), and using the compound in the light emitting layer of the organic light emitting device, there is an effect of obtaining an organic electroluminescent device of high color purity, high brightness, long life have.
이하, 첨부도면을 참조하여 본 발명의 바람직한 실시예를 상세히 설명한다.Hereinafter, exemplary embodiments of the present invention will be described in detail with reference to the accompanying drawings.
본 발명은 페닐기에 적어도 하나의 알킬기를 치환하여 색순도를 높이고, 퀴놀린기에는 질소를 포함하지 않은 페닐기에 알킬, 알콕시기를 적어도 2개 치환하여 높은 발광효율 및 긴 발광수명을 가질 수 있는 적색 인광 화합물을 개발하였다.The present invention improves color purity by substituting at least one alkyl group for a phenyl group, and at least two alkyl and alkoxy groups for a phenyl group that does not contain nitrogen in a quinoline group to provide a red phosphorescent compound having a high luminous efficiency and a long luminous lifetime. Developed.
본 발명은 하기 화학식 1로 표시되는 적색 인광 화합물을 제공한다.The present invention provides a red phosphorescent compound represented by the following formula (1).
[화학식1][Formula 1]
여기서, 화학식 1에서
그리고, R1, R2, R3, R4는 각각 독립적으로 수소, C1 내지 C6의 알킬기, C1 내지 C4의 알콕시기로부터 선택될 수 있고, 적어도 하나는 C1 내지 C6의 알킬기일 수 있다.In addition, R1, R2, R3, and R4 may each independently be selected from hydrogen, an alkyl group of C1 to C6, an alkoxy group of C1 to C4, and at least one may be an alkyl group of C1 to C6.
또한, R5, R6, R7은 각각 독립적으로 수소, C1 내지 C6의 알킬기, C1 내지 C4의 알콕시기로부터 선택될 수 있고, 그 중 적어도 두 개가 선택될 수 있다.In addition, R5, R6, R7 may be each independently selected from hydrogen, an alkyl group of C1 to C6, an alkoxy group of C1 to C4, at least two of them may be selected.
여기서, C1 내지 C6의 알킬기는 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸 및 t-부틸로 이루어진 그룹으로부터 선택될 수 있으며, C1 내지 C4의 알콕시기는 메톡시, 에톡시, n-프로톡시, i-프로톡시, n-부톡시, i-부톡시 및 t-부톡시로 이루어진 그룹으로부터 선택될 수 있다.Wherein the alkyl group of C1 to C6 may be selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl and t-butyl, wherein the alkoxy group of C1 to C4 is methoxy, It may be selected from the group consisting of oxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy and t-butoxy.
본 발명 화학식 1에서,
다음, 본 발명의 화학식 1에서,
중 어느 하나일 수 있다.It may be any one of.
그리고, 상기 화학식 1의 화합물은 하기 화합물들,And, the compound of Formula 1 is the following compounds,
중 어느 하나일 수 있다.It may be any one of.
한편, 본 발명에 따른 유기전계발광소자는 양극과 음극 사이에 발광층을 포함하는 구조로 이루어지고, 상기 화학식 1의 화합물을 발광층의 도펀트로 사용할 수 있다.On the other hand, the organic light emitting device according to the invention is made of a structure including a light emitting layer between the anode and the cathode, the compound of Formula 1 can be used as a dopant of the light emitting layer.
여기서, 발광층은 Al, Zn 금속 착물 및 카바졸 유도체 중 어느 하나를 호스 트로 사용할 수 있다.Here, the light emitting layer may be any one of Al, Zn metal complex and carbazole derivatives as a host.
이때, Al, Zn 금속착물의 리간드는 퀴놀닐, 바이페닐닐, 아이소퀴놀닐, 페닐닐, 메틸퀴놀닐, 다이메틸퀴놀닐, 다이메틸아이소퀴놀닐기 중 어느 하나로 이루어지고, 카바졸 유도체는 CBP로 이루어지는 것이 바람직하다.At this time, the ligand of the Al, Zn metal complex is made of any of quinolyl, biphenylyl, isoquinolyl, phenylyl, methylquinolyl, dimethylquinolyl, dimethylisoquinolyl group, carbazole derivative is CBP It is preferable to make.
그리고, 본 발명에서, 발광층의 도펀트 사용량은 약 0.1 중량% - 50 중량%인 것이 바람직하다.In the present invention, the amount of dopant used in the light emitting layer is preferably about 0.1% by weight to 50% by weight.
이하에서, 본 발명에 따른 유기전계발광소자에 사용되는 적색 인광 화합물들 중 일부 화합물에 대한 합성 방법을 설명하기로 한다.Hereinafter, a synthesis method for some of the red phosphorescent compounds used in the organic light emitting device according to the present invention will be described.
합성예Synthesis Example
(1) 2-(1-메틸페닐)-6-디메틸퀴놀린의 합성방법(1) Synthesis method of 2- (1-methylphenyl) -6-dimethylquinoline
건조된 2구 둥근 바닥 플라스크(two-neck-r.b.f)에 3-메틸페닐붕산(13mmol), 2-클로로-5,7-디메틸퀴놀린(10mmol), 테트라키스(트라이페닐포스핀)팔라 듐(0)(0.5mmol)과 포타시움 카보네이트(15g)를, 테트라하이드로퓨란(30ml)과 증류수(10ml)에 녹인 후, 약 100도에서 약 24시간 교반시킨 다음, 반응이 종료되면, 테트라하이드로퓨란과 톨루엔을 제거한다.3-methylphenylboric acid (13 mmol), 2-chloro-5,7-dimethylquinoline (10 mmol), tetrakis (triphenylphosphine) palladium (0) in a dried two-neck round bottom flask (two-neck-rbf) (0.5 mmol) and potassium carbonate (15 g) were dissolved in tetrahydrofuran (30 ml) and distilled water (10 ml), stirred at about 100 degrees for about 24 hours, and after the reaction was completed, tetrahydrofuran and toluene were removed. do.
이어, 다이클로로메테인과 물을 사용하여 추출한 후, 감압 증류하여 실리카겔 컬럼한다.Subsequently, the mixture was extracted using dichloromethane and water, and then distilled under reduced pressure to perform silica gel column.
다음, 용매를 감압 증류하고, 다이클로로메테인과 석유 에테르를 사용하여 재결정하여 필터를 하면, 생성물인 2-(3-메틸페닐)-5,7-디메틸퀴놀린을 약 1.9g 얻었다.Subsequently, the solvent was distilled off under reduced pressure, and the residue was recrystallized using dichloromethane and petroleum ether to give a filter to obtain about 1.9 g of 2- (3-methylphenyl) -5,7-dimethylquinoline as a product.
(2) 클로로-가교 다이머 착물의 합성방법(2) Synthesis method of chloro-crosslinked dimer complex
이리듐(III) 클로라이드(5mmol)와 2-(3-메틸페닐)-5,7-디메틸퀴놀린(10mmol)을, 2-에톡시에탄올 : 증류수가 3:1로 혼합된 용액(30ml)에 넣고, 약 24시간 동안 환류시킨다.Iridium (III) chloride (5 mmol) and 2- (3-methylphenyl) -5,7-dimethylquinoline (10 mmol) were added to a solution (30 ml) in which 2-ethoxyethanol: distilled water was mixed at 3: 1. Reflux for 24 hours.
다음, 물을 첨가하여 형성된 고체를 여과한 후, 메탄올과 석유 에테르로 세 척하여 클로로 가교 다이머 착물을 얻었다.Next, the solid formed by adding water was filtered and then washed with methanol and petroleum ether to obtain a chloro-crosslinked dimer complex.
(3) 이리듐(III) (2-(3-메틸페닐)-5,7-디메틸퀴놀린-N,C2')(2,4-펜테인다이오네이트-O,O)(A-1)의 합성방법(3) Synthesis of Iridium (III) (2- (3-methylphenyl) -5,7-dimethylquinoline-N, C2 ' ) (2,4-pentanedionate-O, O) (A-1) Way
클로로-가교 다이머 착물(1mmol), 2,4-펜테인다이온(3mmol)과 탄산나트륨 (Na2C03)(6mmol)을, 2-에톡시에탄올(30ml)에 넣고 약 24시간 동안 환류시킨다.Chloro-crosslinked dimer complex (1 mmol), 2,4-pentanedione (3 mmol) and sodium carbonate (Na2 CO3 ) (6 mmol) were added to 2-ethoxyethanol (30 ml) and refluxed for about 24 hours.
다음, 이를 상온으로 식힌 후, 증류수를 첨가하여 여과 후 고체를 얻었다.Then, after cooling to room temperature, distilled water was added to give a solid after filtration.
이와 같이, 형성된 고체를 다이클로로메테인에 녹인 후 실리카겔을 이용하여 여과하였고, 다이클로로메테인을 감압제거 후 메탄올과 석유 에테르로 세척하여 화합물을 얻었다.Thus, the formed solid was dissolved in dichloromethane and filtered using silica gel, and dichloromethane was removed under reduced pressure and washed with methanol and petroleum ether to obtain a compound.
실시예Example
실시예 1Example 1
ITO 유리(glass) 기판의 발광 면적이 3mm X 3mm 크기가 되도록 패터닝(patterning)한 후 세정하였다.The light emitting area of the ITO glass substrate was patterned to be 3 mm × 3 mm in size, and then washed.
이어, 기판을 진공 챔버에 장착한 후, 기본 압력(base pressure)이 1 X 10-6torr가 되도록 한다.Subsequently, after mounting the substrate in a vacuum chamber, the base pressure is 1 × 10−6 torr.
다음, 유기물을 ITO 유리 기판 위에 CuPC(200Å), NPD(400Å), BAlq + A-1 (5%)(200Å), Alq3(300Å), LiF(5Å), Al(1000Å)의 순서로 성막하였다. Next, an organic material was formed on an ITO glass substrate in the order of CuPC (200 Pa), NPD (400 Pa), BAlq + A-1 (5%) (200 Pa), Alq3 (300 Pa), LiF (5 Pa), Al (1000 Pa). .
상기와 같이 제작된 소자는 약 0.9mA에서 약 1665cd/m2(5.6V)를 나타내었으며, 이때 CIE x = 0.642, y = 0.348을 나타내었다.The device manufactured as described above exhibited about 1665 cd / m2 (5.6 V) at about 0.9 mA, where CIE x = 0.642 and y = 0.348.
또한, 수명(초기휘도의 반)은 약 2000cd/m2에서 약 7000 시간이었다.In addition, the lifetime (half of the initial luminance) was about 7000 hours at about 2000 cd / m2 .
실시예 2Example 2
ITO 유리(glass) 기판의 발광 면적이 3mm X 3mm 크기가 되도록 패터닝(patterning)한 후 세정하였다.The light emitting area of the ITO glass substrate was patterned to be 3 mm × 3 mm in size, and then washed.
이어, 기판을 진공 챔버에 장착한 후, 기본 압력(base pressure)이 약 1 X 10-6 torr가 되도록 한다.Subsequently, after mounting the substrate in a vacuum chamber, the base pressure is about 1 × 10−6 torr.
다음, 유기물을 ITO 유리 기판 위에 CuPC(200Å), NPD(400Å), BAlq + A-4 (5%)(200Å), Alq3(300Å), LiF(5Å), Al(1000Å)의 순서로 성막하였다.Next, an organic material was formed on an ITO glass substrate in the following order: CuPC (200 kPa), NPD (400 kPa), BAlq + A-4 (5%) (200 kPa), Alq3 (300 kPa), LiF (5 kPa), Al (1000 kPa). .
상기와 같이 제작된 소자는 약 0.9mA에서 약 1310cd/m2(5.8V)를 나타내었으며, 이때 CIE x = 0.657, y = 0.351을 나타내었다.The device manufactured as described above exhibited about 1310 cd / m2 (5.8 V) at about 0.9 mA, where CIE x = 0.657 and y = 0.351.
또한, 수명(초기휘도의 반)은 약 2000cd/m2에서 약 6500 시간이었다.In addition, the lifetime (half the initial luminance) was about 6500 hours at about 2000 cd / m2 .
실시예 3Example 3
ITO 유리(glass) 기판의 발광 면적이 3mm X 3mm 크기가 되도록 패터닝(patterning)한 후 세정하였다.The light emitting area of the ITO glass substrate was patterned to be 3 mm × 3 mm in size, and then washed.
이어, 기판을 진공 챔버에 장착한 후, 기본 압력(base pressure)이 1 X 10-6 torr가 되도록 한다.Subsequently, after mounting the substrate in a vacuum chamber, the base pressure is 1 × 10−6 torr.
다음, 유기물을 ITO 유리 기판 위에 CuPC(200Å), NPD(400Å), Balq + A-17 (5%)(200Å), Alq3(300Å), LiF(5Å), Al(1000Å)의 순서로 성막하였다.Next, the organic material was formed on an ITO glass substrate in the order of CuPC (200 kPa), NPD (400 kPa), Balq + A-17 (5%) (200 kPa), Alq3 (300 kPa), LiF (5 kPa), Al (1000 kPa). .
상기와 같이 제작된 소자는 약 0.9mA에서 약 1715cd/m2(5.7V)를 나타내었으며, 이때 CIE x = 0.640, y = 0.349를 나타내었다.The device manufactured as described above exhibited about 1715 cd / m2 (5.7 V) at about 0.9 mA, where CIE x = 0.640 and y = 0.349.
또한, 수명(초기휘도의 반)은 약 2000cd/m2에서 약 7500 시간이었다.In addition, the lifetime (half of the initial luminance) was about 7500 hours at about 2000 cd / m2 .
실시예 4Example 4
ITO 유리(glass) 기판의 발광 면적이 3mm X 3mm 크기가 되도록 패터닝(patterning)한 후 세정하였다.The light emitting area of the ITO glass substrate was patterned to be 3 mm × 3 mm in size, and then washed.
이어, 기판을 진공 챔버에 장착한 후, 기본 압력(base pressure)이 1 X 10-6 torr가 되도록 한다.Subsequently, after mounting the substrate in a vacuum chamber, the base pressure is 1 × 10−6 torr.
다음, 유기물을 ITO 유리 기판 위에 CuPC(200Å), NPD(400Å), Balq + A-67 (5%)(200Å), Alq3(300Å), LiF(5Å), Al(1000Å)의 순서로 성막하였다.Next, an organic material was formed on an ITO glass substrate in the order of CuPC (200 kPa), NPD (400 kPa), Balq + A-67 (5%) (200 kPa), Alq3 (300 kPa), LiF (5 kPa), Al (1000 kPa). .
상기와 같이 제작된 소자는 약 0.9mA에서 약 1741cd/m2(5.9V)를 나타내었으 며, 이때 CIE x = 0.648, y = 0.330을 나타내었다.The device manufactured as described above exhibited about 1741 cd / m2 (5.9 V) at about 0.9 mA, where CIE x = 0.648 and y = 0.330.
또한, 수명(초기휘도의 반)은 약 2000cd/m2에서 약 7000 시간이었다.In addition, the lifetime (half of the initial luminance) was about 7000 hours at about 2000 cd / m2 .
비교예 1Comparative Example 1
ITO 유리(glass) 기판의 발광 면적이 3mm X 3mm 크기가 되도록 패터닝(patterning)한 후 세정하였다.The light emitting area of the ITO glass substrate was patterned to be 3 mm × 3 mm in size, and then washed.
이어, 기판을 진공 챔버에 장착한 후, 기본 압력(base pressure)이 1 X 10-6 torr가 되도록 한다.Subsequently, after mounting the substrate in a vacuum chamber, the base pressure is 1 × 10−6 torr.
다음, 유기물을 ITO 유리 기판 위에 CuPC(200Å), NPD(400Å), BAlq + RD1(7%)(200Å), Alq3(300Å), LiF(5Å), Al(1000Å)의 순서로 성막하였다.Next, an organic material was formed on an ITO glass substrate in the following order: CuPC (200 kPa), NPD (400 kPa), BAlq + RD1 (7%) (200 kPa), Alq3 (300 kPa), LiF (5 kPa), Al (1000 kPa).
상기와 같이 제작된 소자는 약 0.9mA에서 약 780cd/m2(7.5V)를 나타내었으며, 이때 CIE x = 0.659, y = 0.329를 나타내었다.The device manufactured as described above exhibited about 780 cd / m2 (7.5 V) at about 0.9 mA, where CIE x = 0.659 and y = 0.329.
또한, 수명(초기휘도의 반)은 약 2000cd/m2에서 약 2500 시간이었다.In addition, the lifetime (half of the initial luminance) was about 2500 hours at about 2000 cd / m2 .
비교예 2Comparative Example 2
ITO 유리(glass) 기판의 발광 면적이 3mm X 3mm 크기가 되도록 패터닝(patterning)한 후 세정하였다.The light emitting area of the ITO glass substrate was patterned to be 3 mm × 3 mm in size, and then washed.
이어, 기판을 진공 챔버에 장착한 후, 기본 압력(base pressure)이 1 X 10-6 torr가 되도록 한다.Subsequently, after mounting the substrate in a vacuum chamber, the base pressure is 1 × 10−6 torr.
다음, 유기물을 ITO 유리 기판 위에 CuPC(200Å), NPD(400Å), BAlq + RD2(7%)(200Å), Alq3(300Å), LiF(5Å), Al(1000Å)의 순서로 성막하였다.Next, an organic material was formed on an ITO glass substrate in the order of CuPC (200 Pa), NPD (400 Pa), BAlq + RD2 (7%) (200 Pa), Alq3 (300 Pa), LiF (5 Pa), Al (1000 Pa).
상기와 같이 제작된 소자는 약 0.9mA에서 약 1173cd/m2(6.0V)를 나타내었으며, 이때 CIE x = 0.606, y = 0.375를 나타내었다.The device manufactured as described above exhibited about 1173 cd / m2 (6.0 V) at about 0.9 mA, wherein CIE x = 0.606, y = 0.375.
또한, 수명(초기휘도의 반)은 약 2000cd/m2에서 약 4000 시간이었다.In addition, the lifetime (half the initial luminance) was about 4000 hours at about 2000 cd / m2 .
상기 실시예와 비교예에 따라, 제작된 유기전계발광소자의 효율 특성, 색좌표, 휘도특성, 수명특성을 정리하여 표 1에 나타내었다.According to the above Examples and Comparative Examples, the efficiency characteristics, color coordinates, luminance characteristics, and lifetime characteristics of the fabricated organic light emitting display device are summarized in Table 1 below.
이와 같이, 본 발명의 유기전계발광소자는 구동전압을 적어도 약 6.0V 이하로 하고, 휘도는 적어도 약 1300cd/m2 이상이며, 수명은 약 6500 시간 이상일 수 있다.As described above, the organic light emitting display device of the present invention may have a driving voltage of at least about 6.0 V or less, a luminance of at least about 1300 cd / m2 or more, and a lifespan of about 6500 hours or more.
이상 설명한 내용을 통해 당업자라면 본 발명의 기술 사상을 일탈하지 아니하는 범위에서 다양한 변경 및 수정이 가능함을 알 수 있을 것이다. 따라서, 본 발명의 기술적 범위는 실시예에 기재된 내용으로 한정되는 것이 아니라 특허 청구의 범위에 의하여 정해져야 한다.Those skilled in the art will appreciate that various changes and modifications can be made without departing from the spirit of the present invention. Therefore, the technical scope of the present invention should not be limited to the contents described in the embodiments, but should be defined by the claims.
도 1은 일반적인 유기전계발광소자의 색순도가 높아질수록 시감도가 저하되는 것을 보여주는 그래프1 is a graph showing that the visibility decreases as the color purity of a conventional organic light emitting display device increases
도 2는 본 발명의 실시예에서 사용되는 화합물들의 구조식을 보여주는 그래프Figure 2 is a graph showing the structural formula of the compounds used in the examples of the present invention
Claims (9)
Translated fromKorean
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20070106495AKR101493218B1 (en) | 2007-10-23 | 2007-10-23 | Red phosphorescent compound and organic electroluminescent device using the same |
| US12/239,005US8956737B2 (en) | 2007-09-27 | 2008-09-26 | Red phosphorescent compound and organic electroluminescent device using the same |
| CN200810173713.2ACN101397311B (en) | 2007-09-27 | 2008-09-27 | Red phosphorescent compound and use the organic electroluminescence device of described compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20070106495AKR101493218B1 (en) | 2007-10-23 | 2007-10-23 | Red phosphorescent compound and organic electroluminescent device using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20090041019Atrue KR20090041019A (en) | 2009-04-28 |
| KR101493218B1 KR101493218B1 (en) | 2015-02-16 |
Family
ID=40764214
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR20070106495AActiveKR101493218B1 (en) | 2007-09-27 | 2007-10-23 | Red phosphorescent compound and organic electroluminescent device using the same |
Country Status (1)
| Country | Link |
|---|---|
| KR (1) | KR101493218B1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20130056198A (en)* | 2011-11-21 | 2013-05-29 | 유니버셜 디스플레이 코포레이션 | Organic light emitting materials |
| US10749118B2 (en) | 2014-06-26 | 2020-08-18 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6835469B2 (en)* | 2001-10-17 | 2004-12-28 | The University Of Southern California | Phosphorescent compounds and devices comprising the same |
| KR100509603B1 (en) | 2002-12-28 | 2005-08-22 | 삼성에스디아이 주식회사 | Red emitting compound and organic electroluminescence device |
| KR100797469B1 (en)* | 2005-03-08 | 2008-01-24 | 엘지전자 주식회사 | Red phosphorescent compound and organic light emitting device using the same |
| KR100747572B1 (en)* | 2005-11-07 | 2007-08-08 | 엘지전자 주식회사 | Red phosphorescent compound and organic light emitting device using the same |
- 2007
- 2007-10-23KRKR20070106495Apatent/KR101493218B1/enactiveActive
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20130056198A (en)* | 2011-11-21 | 2013-05-29 | 유니버셜 디스플레이 코포레이션 | Organic light emitting materials |
| US10749118B2 (en) | 2014-06-26 | 2020-08-18 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
Also Published As
| Publication number | Publication date |
|---|---|
| KR101493218B1 (en) | 2015-02-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100662378B1 (en) | Red phosphorescent compound and organic light emitting device using the same | |
| KR100803125B1 (en) | Red phosphorescent compound and organic light emitting device using the same | |
| KR100797469B1 (en) | Red phosphorescent compound and organic light emitting device using the same | |
| KR101281750B1 (en) | Red color phosphorescent material and Organic electroluminescent device using the same | |
| EP1783132B1 (en) | Red phosphorescent compounds and organic electromuninescent devices using the same | |
| KR101348699B1 (en) | Red color phosphorescent material and Organic electroluminescent device using the same | |
| EP1784057B1 (en) | Red phosphorescent compounds and organic electroluminescent devices using the same | |
| KR20070097139A (en) | Red phosphorescent compound and organic light emitting device using the same | |
| KR20110077350A (en) | Red phosphorescent compound, organic electroluminescent device using same and manufacturing method thereof | |
| KR20110077173A (en) | Red phosphorescent compound, organic electroluminescent device using same and manufacturing method thereof | |
| KR20090032250A (en) | Red phosphorescent compound and organic electroluminescent device using same | |
| KR102028503B1 (en) | Phosphorescent material and organic light emitting diode device using the same | |
| KR20100047588A (en) | Red color phosphorescent material and organic electroluminescent device using the same | |
| KR20070105080A (en) | Red phosphorescent compound and organic light emitting device using the same | |
| KR20120036560A (en) | Red color phosphorescent host material and organic electroluminescent display device using the same | |
| KR101630317B1 (en) | Red phosphorescence compound and Organic Electroluminescence Device using the same | |
| KR101519860B1 (en) | Green color phosphorescent material and Organic electroluminescent device using the same | |
| KR20080105870A (en) | Red phosphorescent compound and organic electroluminescent device using same | |
| KR101493218B1 (en) | Red phosphorescent compound and organic electroluminescent device using the same | |
| KR100662379B1 (en) | Red phosphorescent compound and organic light emitting device using the same | |
| KR100662377B1 (en) | Red phosphorescent compound and organic light emitting device using the same | |
| KR100662430B1 (en) | Red phosphorescent compound and organic light emitting device using the same | |
| KR100747572B1 (en) | Red phosphorescent compound and organic light emitting device using the same | |
| KR100662381B1 (en) | Red phosphorescent compound and organic light emitting device using the same | |
| KR20070105079A (en) | Red phosphorescent compound and organic light emitting device using the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0109 | Patent application | Patent event code:PA01091R01D Comment text:Patent Application Patent event date:20071023 | |
| N231 | Notification of change of applicant | ||
| PN2301 | Change of applicant | Patent event date:20080122 Comment text:Notification of Change of Applicant Patent event code:PN23011R01D | |
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination | Patent event code:PA02012R01D Patent event date:20120926 Comment text:Request for Examination of Application Patent event code:PA02011R01I Patent event date:20071023 Comment text:Patent Application | |
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection | Comment text:Notification of reason for refusal Patent event date:20131224 Patent event code:PE09021S01D | |
| AMND | Amendment | ||
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection | Comment text:Notification of reason for refusal Patent event date:20140520 Patent event code:PE09021S01D | |
| AMND | Amendment | ||
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent | Patent event date:20141117 Comment text:Decision to Refuse Application Patent event code:PE06012S01D Patent event date:20140520 Comment text:Notification of reason for refusal Patent event code:PE06011S01I Patent event date:20131224 Comment text:Notification of reason for refusal Patent event code:PE06011S01I | |
| AMND | Amendment | ||
| J201 | Request for trial against refusal decision | ||
| PJ0201 | Trial against decision of rejection | Patent event date:20141217 Comment text:Request for Trial against Decision on Refusal Patent event code:PJ02012R01D Patent event date:20141117 Comment text:Decision to Refuse Application Patent event code:PJ02011S01I Appeal kind category:Appeal against decision to decline refusal Decision date:20150205 Appeal identifier:2014101007773 Request date:20141217 | |
| PB0901 | Examination by re-examination before a trial | Comment text:Amendment to Specification, etc. Patent event date:20141217 Patent event code:PB09011R02I Comment text:Request for Trial against Decision on Refusal Patent event date:20141217 Patent event code:PB09011R01I Comment text:Amendment to Specification, etc. Patent event date:20140721 Patent event code:PB09011R02I Comment text:Amendment to Specification, etc. Patent event date:20140224 Patent event code:PB09011R02I | |
| B701 | Decision to grant | ||
| PB0701 | Decision of registration after re-examination before a trial | Patent event date:20150205 Comment text:Decision to Grant Registration Patent event code:PB07012S01D Patent event date:20150119 Comment text:Transfer of Trial File for Re-examination before a Trial Patent event code:PB07011S01I | |
| PR0701 | Registration of establishment | Comment text:Registration of Establishment Patent event date:20150209 Patent event code:PR07011E01D | |
| PR1002 | Payment of registration fee | Payment date:20150210 End annual number:3 Start annual number:1 | |
| PG1601 | Publication of registration | ||
| PR1001 | Payment of annual fee | Payment date:20180115 Start annual number:4 End annual number:4 | |
| FPAY | Annual fee payment | Payment date:20190114 Year of fee payment:5 | |
| PR1001 | Payment of annual fee | Payment date:20190114 Start annual number:5 End annual number:5 | |
| FPAY | Annual fee payment | Payment date:20200116 Year of fee payment:6 | |
| PR1001 | Payment of annual fee | Payment date:20200116 Start annual number:6 End annual number:6 | |
| PR1001 | Payment of annual fee | Payment date:20210118 Start annual number:7 End annual number:7 | |
| PR1001 | Payment of annual fee | Payment date:20220120 Start annual number:8 End annual number:8 | |
| PR1001 | Payment of annual fee | Payment date:20230116 Start annual number:9 End annual number:9 | |
| PR1001 | Payment of annual fee | Payment date:20240115 Start annual number:10 End annual number:10 | |
| PR1001 | Payment of annual fee | Payment date:20250115 Start annual number:11 End annual number:11 |