KR19980030142A - Novel benzoxazinone-based light emitting complex and preparation method thereof - Google Patents
Novel benzoxazinone-based light emitting complex and preparation method thereof Download PDFInfo
- Publication number
- KR19980030142A KR19980030142A KR1019960049516A KR19960049516A KR19980030142A KR 19980030142 A KR19980030142 A KR 19980030142A KR 1019960049516 A KR1019960049516 A KR 1019960049516A KR 19960049516 A KR19960049516 A KR 19960049516A KR 19980030142 A KR19980030142 A KR 19980030142A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- complex
- light emitting
- substituents
- compound
- Prior art date
Links
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical compound C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 238000002360 preparation method Methods 0.000 title description 2
- 238000010668 complexation reaction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 10
- 125000001424 substituent group Chemical group 0.000 claims abstract description 9
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 8
- 238000000859 sublimation Methods 0.000 claims abstract description 5
- 230000008022 sublimation Effects 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 4
- 230000009918 complex formation Effects 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
- 239000000463 material Substances 0.000 claims description 11
- 239000010409 thin film Substances 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000003446 ligand Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 229910001510 metal chloride Inorganic materials 0.000 claims description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052790 beryllium Inorganic materials 0.000 claims description 2
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052733 gallium Inorganic materials 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- 229910052738 indium Inorganic materials 0.000 claims 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 238000004020 luminiscence type Methods 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910001449 indium ion Inorganic materials 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/006—Beryllium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/06—Zinc compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/003—Compounds containing elements of Groups 3 or 13 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/069—Aluminium compounds without C-aluminium linkages
-
- 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
- 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
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/326—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising gallium
-
- 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
- C09K2211/181—Metal complexes of the alkali metals and alkaline earth metals
-
- 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)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
본 발명은 하기 화학식 1로 표시되며 발광성을 나타내는 신규한 벤즈옥사지논계 착화합물 및 그의 제조방법에 관한 것이다. 본 발명은 또한, 화학식 1의 착화합물을 유기 발광소자의 제조에 사용하는 방법에 관한 것이다.The present invention relates to a novel benzoxazinone-based complex compound represented by the following Chemical Formula 1 and showing luminescence, and a method for preparing the same. The present invention also relates to a method of using the complex compound of the formula (1) in the manufacture of an organic light emitting device.
[화학식 1][Formula 1]
상기식에서,In the above formula,
R1내지 R8은 각각 독립적으로 수소, 할로겐, 저급알킬, 저급알콕시, 아미노, 니트로, 저급알카노일 또는 아릴을 나타내며,R 1 to R 8 each independently represent hydrogen, halogen, lower alkyl, lower alkoxy, amino, nitro, lower alkanoyl or aryl,
M은 2가 또는 3가의 금속이온을 나타내고,M represents a divalent or trivalent metal ion,
n은 2 또는 3의 정수를 나타내며,n represents an integer of 2 or 3,
단, 상기 치환체중 스테릭 힌더런스(steric hindrance)나 전자밀도의 영향으로 착화합물 형성을 방해하는 치환체나, 승화점보다 낮은 온도에서 분해되는 치환체는 제외된다.However, the substituents that hinder complex formation due to the influence of steric hindrance or electron density or substituents decomposed at a temperature lower than the sublimation point are excluded.
Description
본 발명은 하기 화학식 1로 표시되며 발광성을 나타내는 신규한 벤즈옥사지논계 착화합물 및 그의 제조방법에 관한 것이다.The present invention relates to a novel benzoxazinone-based complex compound represented by the following Chemical Formula 1 and showing luminescence, and a method for preparing the same.
상기식에서,In the above formula,
R1내지 R8은 각각 독립적으로 수소, 할로겐, 저급알킬, 저급알콕시, 아미노, 니트로, 저급알카노일 또는 아릴을 나타내며,R 1 to R 8 each independently represent hydrogen, halogen, lower alkyl, lower alkoxy, amino, nitro, lower alkanoyl or aryl,
M은 2가 또는 3가의 금속이온을 나타내고,M represents a divalent or trivalent metal ion,
n은 2 또는 3의 정수를 나타내며,n represents an integer of 2 or 3,
단, 상기 치환체중 스테릭 힌더릭스(steric hinrance)나 전자밀도의 영향으로 착화합물 형성을 방해하는 치환제나, 승화점보다 낮은 온도에서 분해되는 치환체는 제외된다.'However, among the substituents, substituents that interfere with complex formation under the influence of steric hinrance or electron density, or substituents decomposed at a temperature lower than the sublimation point are excluded.
본 발명은 또한, 상기 화학식 1의 착화합물을 유기 발광소자의 제조에 사용하는 방법에 관한 것이다.The present invention also relates to a method of using the complex of Formula 1 for the manufacture of an organic light emitting device.
종래에도 일부 착화합물은 유기 발광소자를 구성하는 물질로 사용되어 왔다. 예를들어, 미합중국 특허 제 4,539,507 호에서는 현재 가장 널리 알려진 8-하이드록시 퀴놀린계의 리간드와 2가(+2) 또는 3가(+3) 금속과의 착물에 대하여 기술하고 있는데, 이 물질은 주로 녹색 발광을 하는 유기발광 다이오드를 제작하는데 사용되는 것으로서 가장 우수한 물질이다. 이 물질은 소자내에서 전자를 이송함과 동시에 전자와 정공의 결합시 고효율로 빛을 내는 역할을 수행한다. 또한 열적 안정성이 높고 박막의 결정화 속도가 극히 느리므로 아주 우수한 물질로 평가되고 있다.Some complex compounds have conventionally been used as materials constituting organic light emitting devices. For example, US Pat. No. 4,539,507 describes the complexes of the most widely known 8-hydroxy quinoline ligands with divalent (+2) or trivalent (+3) metals. It is the best material to be used to fabricate an organic light emitting diode that emits green light. This material transports electrons in the device and at the same time plays a role of emitting light with high efficiency when combining electrons and holes. In addition, it is evaluated as a very excellent material because of its high thermal stability and extremely low crystallization rate of the thin film.
또한, 최근의 미합중국 특허 제 5.486,406 호에서는 상기 착화합물과는 다른 분자구조를 가지면서도 유사한 성질을 나타내는 녹색 발광착물에 대하여 기술하고 있는데, 이 물질은 2가(+2) 금속과 트리아졸 계통의 리간드간의 착물이다. 이 물질 역시 전자를 전달함과 동시에 자체적으로 발광하는 성질을 갖고 있다. 한편, 이와 다른 종류로서 벤즈옥사졸계의 착물이 일본특허공개 소 63-36586 호에 기술되어 있으며, 이 물질은 청색 발광소자에 사용될 수 있고 안정성도 우수한 것으로 보고되어 있다.In addition, US Pat. No. 5,486,406 describes a green light-emitting complex having a different molecular structure and similar properties to that of the complex, which is a divalent (+2) metal and a triazole-based compound. It is a complex between ligands. This material also transmits electrons and emits light itself. On the other hand, benzoxazole-based complexes are described in Japanese Patent Laid-Open No. 63-36586 as another kind, and this material can be used in blue light emitting devices and is reported to have excellent stability.
이에, 본 발명자들은 상기한 바와 같은 선행기술을 바탕으로 하여 보다 고효율의 발광성을 나타낼 뿐아니라 열적 안정성 또한 우수한 새로운 구조의 유기 착화합물을 개발하고자 집중적인 연구를 수행한 결과, 상기 화학식 1의 착화합물이 이러한 목적에 부합됨을 발견하고 본 발명을 완성하게 되었다.Accordingly, the present inventors conducted intensive studies to develop organic complex compounds having a new structure having excellent thermal stability and excellent thermal stability based on the prior art as described above. The present invention has been found to be consistent with the purpose.
이하, 본 발명의 구성을 상세히 설명한다.Hereinafter, the configuration of the present invention will be described in detail.
도 1 은 단순화된 소자의 개략도를 나타낸 것이다.1 shows a schematic diagram of a simplified device.
본 발명은 하기 화학식 1로 표시되며 발광성을 나타내는 신규한 벤즈옥사지논계 착화합물에 관한 것이다.The present invention relates to a novel benzoxazinone-based complex compound represented by the following formula (1) exhibiting luminescence.
화학식 1Formula 1
상기식에서,In the above formula,
R1내지 R8은 각각 독립적으로 수소, 할로겐, 저급알킬, 저급알콕시, 아미노, 니트로, 저급알카노일 또는 아릴을 나타내며,R 1 to R 8 each independently represent hydrogen, halogen, lower alkyl, lower alkoxy, amino, nitro, lower alkanoyl or aryl,
M은 2가 또는 3가의 금속이온을 나타내고,M represents a divalent or trivalent metal ion,
n은 2 또는 3의 정수를 나타내며,n represents an integer of 2 or 3,
단, 상기 치환체중 스테릭 힌더런스(steric hindrance)나 전자밀도의 영향으로 착화합물 형성을 방해하는 치환체나, 승화점보다 낮은 온도에서 분해되는 최한체는 제외된다.However, the substituents that hinder complex formation due to the influence of steric hindrance or electron density or the limiting substance decomposed at a temperature lower than the sublimation point are excluded.
상기 화학식 1의 착화합물 중에서도 바람직한 화합물은 M이 베릴륨, 아연 또는 마그네슘 이온과 같은 2가 금속이온이거나 알루미늄, 갈륨 또는 인듐 이온과 같은 3가 금속이온을 나타내는 화합물이며, n은 착물을 이루는 금속의 산화상태를 나타낸다.Among the complex compounds of Formula 1, a preferable compound is a compound in which M is a divalent metal ion such as beryllium, zinc or magnesium ion, or a trivalent metal ion such as aluminum, gallium or indium ion, and n is the oxidation state of the metal constituting the complex. Indicates.
본 발명에 따른 상기 화학식 1의 착화합물은 하기 화학식 2의 화합물로부터 제조될 수 있으며, 따라서 본 발명은 또한 화학식 1의 화합물을 제조하는 방법을 제공함을 목적으로 한다.The complex of Formula 1 according to the present invention may be prepared from the compound of Formula 2, and therefore the present invention also aims to provide a method for preparing the compound of Formula 1.
상기식에서, R1내지 R8은 앞에서 정의한 바와 같다.Wherein R 1 to R 8 are as defined above.
본 발명의 제조방법에 따르면, 상기 화학식 2의 리간드 화합물을 용매중에서 금속클로라이드 또는 금속알콕사이드와 함께 반응시켜 화학식 1의 착화합물을 형성할 수 있다. 이때, 반응물질인 금속클로라이드 또는 금속알콕사이드에서 금속은 상기 M에 대해 설명한 것과 동일한 것을 의미하며, 용매로는 에탄올 또는 톨루엔을 사용할 수 있고 사용되는 용매의 환류 조건에서 반응을 수행한다. 또한, 화학식 1의 화합물은 반응이 완결된 후 승화를 이용함으로써 정제하여 사용한다.According to the preparation method of the present invention, the ligand compound of Formula 2 may be reacted with a metal chloride or a metal alkoxide in a solvent to form a complex compound of Formula 1. At this time, the metal in the metal chloride or metal alkoxide which is a reactant means the same as described for M, ethanol or toluene may be used as a solvent and the reaction is carried out under reflux conditions of the solvent used. In addition, the compound of formula 1 is purified by using sublimation after the reaction is complete.
한편, 본 발명에 따른 제조방법에서 출발물질로 사용된 화학식 2의 화합물은 하기 반응식 1에 나타낸 방법에 따라 제조하여 사용한다.On the other hand, the compound of formula 2 used as a starting material in the production method according to the invention is used according to the method shown in Scheme 1 below.
상기식에서,In the above formula,
R1내지 R8은 앞에서 정의한 바와 같고,R 1 to R 8 are as defined above,
R9는 메틸 또는 하이드록시보호기를 나타낸다.R 9 represents a methyl or hydroxyprotecting group.
즉, 반응식 1에 도시한 바와 같이 화학식 2의 화합물은 화합물[2]를 피리딘과 같은 용매중에서 R9치환기에 의해 보호된 화합물[3]과 환류 반응시켜 화합물[4]를 제조한 다음, 고체상태의 화합물[4]를 탈보호기화시킴으로써 제조한다.In other words, as shown in Scheme 1, the compound of Formula 2 was reacted with Compound [3] at a solvent such as pyridine to be protected by R 9 substituent to prepare Compound [4], and then in a solid state. It is prepared by deprotecting compound [4].
이상 설명한 바에 따라 제조된 본 발명의 착화합물은 유기 발광소자의 제조시 전극사이에 박막의 형태로 증착되어 사용될 수 있으며, 따라서 본 발명은 화학식 1의 착화합물을 유기 발광소자의 제조에 사용하는 방법을 제공한다.The complex compound of the present invention prepared as described above may be used in the form of a thin film deposited between the electrodes in the manufacture of the organic light emitting device, and thus the present invention provides a method of using the complex of the formula (1) in the manufacture of the organic light emitting device do.
단순화된 소자의 개략도는 도 1에 나타낸 바와 같다. 통상의 유기발광 소자는 전도성 투명전극(2)이 입혀진 유리기판(1)위에 정공을 받거나 이송하는 물질(3)을 증착시키고 다시 그 위에 전자를 이송하는 박막(4)를 진공 증착법에 의하여 형성시킴으로써 제조되며, 이 소자에 적절한 전위차를 가하면 전자와 정공이 소자에 주입되어 발광을 한다.A schematic diagram of the simplified device is as shown in FIG. 1. A conventional organic light emitting device is formed by depositing a material (3) for receiving or transporting holes on a glass substrate (1) on which a conductive transparent electrode (2) is coated and again forming a thin film (4) for transporting electrons thereon by vacuum deposition. When an appropriate potential difference is applied to the device, electrons and holes are injected into the device to emit light.
본 발명에 따른 화학식 1의 착화합물은 그 자체로 또는 발광성의 조절을 목적으로 하여 저농도의 타 발광물질이 도핑된 상태로, 전자를 이송함과 동시에 발광을 하는 박막(4)을 구성하는 물질로 사용될 수 있다. 박막을 형성하는 경우, 도 1에 세분하여 나타낸 바와 같이 정공을 이송하는 층(3)과 전자를 주입하는 전극(5)사이에 삽입되는 박막으로 형성될 수도 있고, 단순히 두 전극(2)와 (5)사이에 삽입됨으로써 전자와 정공을 이송시키는 작용을 하는 동시에 발광을 하는 박막으로 형성될 수도 있다.The complex of Formula 1 according to the present invention can be used as a material constituting the thin film 4 which emits light at the same time by transporting electrons while being doped by another light emitting material of low concentration for itself or for the purpose of controlling luminescence. Can be. When the thin film is formed, as shown in detail in FIG. 1, the thin film may be formed as a thin film inserted between the layer 3 for transporting holes and the electrode 5 for injecting electrons, or simply the two electrodes 2 and ( 5) may be formed into a thin film that emits light while simultaneously transferring electrons and holes.
따라서, 본 발명에 따른 신규한 구조의 착화합물은 유기 발광소자에 포함되는 박막을 구성하는 물질로서 매우 유용하게 사용될 수 있을 것으로 기대된다.Therefore, the novel complex structure according to the present invention is expected to be very useful as a material constituting the thin film included in the organic light emitting device.
Claims (5)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019960049516A KR19980030142A (en) | 1996-10-29 | 1996-10-29 | Novel benzoxazinone-based light emitting complex and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019960049516A KR19980030142A (en) | 1996-10-29 | 1996-10-29 | Novel benzoxazinone-based light emitting complex and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR19980030142A true KR19980030142A (en) | 1998-07-25 |
Family
ID=66315966
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019960049516A KR19980030142A (en) | 1996-10-29 | 1996-10-29 | Novel benzoxazinone-based light emitting complex and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| KR (1) | KR19980030142A (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0652273A1 (en) * | 1993-11-09 | 1995-05-10 | Shinko Electric Industries Co. Ltd. | Organic material for electroluminescent device and electroluminescent device |
| EP0700917A2 (en) * | 1994-09-12 | 1996-03-13 | Motorola, Inc. | New organometallic complexes for use in light emitting devices |
| KR960017671A (en) * | 1994-11-07 | 1996-06-17 | 빈센트 비. 인그라시아 | Green-emitting organometallic complex for use in light emitting devices |
| EP0726304A2 (en) * | 1995-02-13 | 1996-08-14 | Motorola, Inc. | Organometallic complexes with built-in fluorescent dyes for use in light emitting devices |
-
1996
- 1996-10-29 KR KR1019960049516A patent/KR19980030142A/en not_active Application Discontinuation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0652273A1 (en) * | 1993-11-09 | 1995-05-10 | Shinko Electric Industries Co. Ltd. | Organic material for electroluminescent device and electroluminescent device |
| EP0700917A2 (en) * | 1994-09-12 | 1996-03-13 | Motorola, Inc. | New organometallic complexes for use in light emitting devices |
| KR960017671A (en) * | 1994-11-07 | 1996-06-17 | 빈센트 비. 인그라시아 | Green-emitting organometallic complex for use in light emitting devices |
| EP0726304A2 (en) * | 1995-02-13 | 1996-08-14 | Motorola, Inc. | Organometallic complexes with built-in fluorescent dyes for use in light emitting devices |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US10297769B2 (en) | Organic electroluminescent materials and devices | |
| JP4049832B2 (en) | Fluorescent organometallic complexes with internal fluorescent dyes for use in light emitting devices | |
| US9831437B2 (en) | Organic electroluminescent materials and devices | |
| US8987451B2 (en) | Synthesis of cyclometallated platinum(II) complexes | |
| EP3327100B1 (en) | Phosphorescent materials | |
| EP3623444B1 (en) | Organic electroluminescent devices and metal complex compounds | |
| KR100732823B1 (en) | Organic metal compounds which the compounds for host and the compounds for dopant were connected, organic electroluminescence display devices using the compounds and method for preparation of the devices | |
| US7625639B2 (en) | Metal-complex compound and organic electroluminescence device using the compound | |
| EP2866273B1 (en) | Organic electrolumiescent materials and devices | |
| US20080074033A1 (en) | Electroluminescent iridium compounds with silylated, germanylated, and stannylated ligands, and devices made with such compounds | |
| EP0710655A1 (en) | Green-emitting benzotriazole metallic complexes for use in light emitting devices | |
| KR20000051826A (en) | New organomattalic complex molecule for the fabrication of organic light emitting diodes | |
| KR20030077556A (en) | Use of boron and aluminum compounds in electronic components | |
| KR20100070320A (en) | Novel red electroluminescent compounds and organic electroluminescent device using the same | |
| US20130317212A1 (en) | Light emitting materials for electronics | |
| EP1992631A1 (en) | Metal complex compound and organic electroluminescent device using same | |
| KR101071328B1 (en) | METHOD FOR PRODUCING TRIS-ORTHO-METALLATED COMPLEXES AND USE OF SUCH COMPLEXES IN OLEDs | |
| KR100734500B1 (en) | Phosphors with high luminus efficiency and Display device containing them | |
| KR100729739B1 (en) | Metallic compound and organic electroluminescence device comprising the same | |
| KR100695976B1 (en) | Electroluminescent materials comprised with mixture and Display device containing the same | |
| US6613924B1 (en) | Silver precursors for CVD processes | |
| KR19980030142A (en) | Novel benzoxazinone-based light emitting complex and preparation method thereof | |
| JP2003129045A (en) | Phosphorescent material | |
| KR100596132B1 (en) | Phenyl pyridine-iridium metal complex compounds for organic electroluminescent device, process for preparing thereof and organic electroluminescent device using thereof | |
| US20220185826A1 (en) | Tandem Carbene Phosphors |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| N231 | Notification of change of applicant | ||
| E902 | Notification of reason for refusal | ||
| E601 | Decision to refuse application |