KR100488495B1 - Synthetic method of electroluminescent material by the use of naphthaquinone and naphthacenedione derivatives - Google Patents
Synthetic method of electroluminescent material by the use of naphthaquinone and naphthacenedione derivatives Download PDFInfo
- Publication number
- KR100488495B1 KR100488495B1 KR10-2002-0047187A KR20020047187A KR100488495B1 KR 100488495 B1 KR100488495 B1 KR 100488495B1 KR 20020047187 A KR20020047187 A KR 20020047187A KR 100488495 B1 KR100488495 B1 KR 100488495B1
- Authority
- KR
- South Korea
- Prior art keywords
- alq
- electroluminescent material
- naphthaquinone
- mmol
- naphthacenedione
- Prior art date
Links
- 239000000463 material Substances 0.000 title claims description 16
- 150000002791 naphthoquinones Chemical class 0.000 title claims description 4
- 238000010189 synthetic method Methods 0.000 title 1
- 239000000243 solution Substances 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 5
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 claims description 5
- QECAURYYBPUIFF-UHFFFAOYSA-N 6,11-dihydroxytetracene-5,12-dione Chemical compound C1=CC=C2C(O)=C(C(=O)C=3C(=CC=CC=3)C3=O)C3=C(O)C2=C1 QECAURYYBPUIFF-UHFFFAOYSA-N 0.000 claims description 4
- 239000011343 solid material Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 14
- 229910052782 aluminium Inorganic materials 0.000 abstract description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract description 2
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 238000001308 synthesis method Methods 0.000 abstract description 2
- 239000003446 ligand Substances 0.000 abstract 2
- 239000007983 Tris buffer Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 238000002798 spectrophotometry method Methods 0.000 abstract 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 abstract 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical class C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- GMQVFHZSXKJCIV-UHFFFAOYSA-N 2,2,2-trifluoro-n-(2,2,2-trifluoroacetyl)acetamide Chemical compound FC(F)(F)C(=O)NC(=O)C(F)(F)F GMQVFHZSXKJCIV-UHFFFAOYSA-N 0.000 description 1
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 1
- -1 aluminum metals Chemical class 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 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
- 150000004059 quinone derivatives Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 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
-
- 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
-
- 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
-
- 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 현재 발광소자로 폭넓게 사용되고 있는 Alq3 [Tris(8-hydroxyquinone)aluminum complex]의 성질을 개선시켜 응용성을 높이기 위한 연구결과로서 보다 더 넓은 범위의 파장을 발광하는 물질로 사용하기 위하여 Alq3와 착물형성이 가능한 리간드(1)과 (2)를 용액상태에서 Alq3와 반응시켜 얻어진 새로운 모델의 발광소자의 합성법과 그 생성물에 속한다. Alq3와 반응한 리간드는 이 화합물이 가지는 색깔의 범위와는 다른 범위에서 발광하는 것으로 확인되었으며 반응생성물의 확인은 NMR과 UV/Vis 분광광도기로 측정하였다.The present invention is to improve the properties of Alq 3 [Tris (8-hydroxyquinone) aluminum complex] widely used as a light emitting device to improve the applicability of the present invention. It belongs to the synthesis method of the new model of light emitting element obtained by reacting ligand (1) and (2) which can form complex with 3 in the solution state with Alq 3 and its product. Ligands reacted with Alq 3 were found to emit light in a range different from the color range of the compound. The reaction product was determined by NMR and UV / Vis spectrophotometry.
Description
본 발명은 나프타퀸논유도체와 나프타센디온유도체를 이용한 전자발광물질의 제조방법에 관한 것으로서, 더욱 상세히는 유기발광소자의 소재물질을 새롭게 디자인하고 이들의 합성법을 개발하는 한가지 방법으로 지금까지 많이 알려져 있는 Alq3계 화합물의 개량을 위하여 나프타퀸논(naphtaquinone)과 나프타센디온(naphtacenedione)을 이용하여 분자량을 증가시켜 그 결과로 인해 발생되는 이동이 가능한 파이전자의 기능이 강화되어 전자발광의 기능을 획기적으로 변화시킬 수 있는 전자발광물질의 제조방법을 제공코자 하는 것이다.The present invention relates to a method for manufacturing an electroluminescent material using a naphthaquinone derivative and a naphthasendione derivative, and more particularly, a method of newly designing a material of an organic light emitting device and developing a synthesis method thereof. In order to improve Alq 3 compounds, naphtaquinone and naphtacenedione were used to increase the molecular weight, resulting in the enhancement of the function of the migrating pi electrons, resulting in dramatically improved electroluminescence. An object of the present invention is to provide a method of manufacturing an electroluminescent material that can be changed.
본 발명이 속한 종래 기술로는 전자발광소재로서 Alq3, BAlq2, Beq2, Zn(BTZ)2, Tb(ACAC)3, Snq2, Snq4, Snq2P2 , Er(TTA)3(Phen), Dy(BTFA)3(Phen)와 같은 유기금속성 화합물들이 주로 이용되어 왔으나 그 중에서도 Alq3가 가지는 특성이 지금까지는 가장 탁월한 발광효과를 가지고 있다고 알려져 있다.In the prior art to which the present invention belongs, Alq 3 , BAlq 2 , Beq 2 , Zn (BTZ) 2 , Tb (ACAC) 3 , Snq 2 , Snq 4 , Snq 2 P 2 , Er (TTA) 3 ( Organometallic compounds such as Phen) and Dy (BTFA) 3 (Phen) have been mainly used, but among them, Alq 3 is known to have the most excellent luminous effect.
그러나 아직까지 알려진 문헌 등에서는 Alq3의 성능개선을 위한 시도가 없었으며 이 화합물의 발광범위를 넓히기 위한 시도 역시 없었던 것이다.However, there are no attempts to improve the performance of Alq 3 in the literature and the like, and there have been no attempts to widen the emission range of the compound.
[참고문헌] [references]
1. Conference Program and Abstract of the 2nd International Conference on Electroluminescence from Molecular Materials and Related Phenomena, 1999, Shefield, UK.1.Conference Program and Abstract of the 2nd International Conference on Electroluminescence from Molecular Materials and Related Phenomena, 1999, Shefield, UK.
2. Abstract and Conference program of the 5th International Symposium on Functioal p Electron Systems, Ulm, 2002, Germany.Abstract and Conference program of the 5th International Symposium on Functioal p Electron Systems, Ulm, 2002, Germany.
본 발명에서 제시한 화합물들은 종전에 Alq3가 가지고 있던 발광 범위를 획기적으로 개선하여 백색광에서 적색광까지의 범위를 가지고 있다.The compounds presented in the present invention have a range from white light to red light by dramatically improving the emission range that Alq 3 previously had.
본 발명은 현재까지 발견된 알루미늄-큐논계의 유기 EL화합물들이 가지고 있는 특성을 개선하기 위해서 개발되었으며, 특히 Alq3의 특성을 바꿔보기 위한 시도로 출발하여 새로운 화합물을 합성하였다.The present invention was developed to improve the properties of the aluminum-cunon-based organic EL compounds found so far, and in particular, starting from an attempt to change the properties of Alq 3 synthesized a new compound.
이들의 결과물들인 새롭게 합성된 Alq2-Nq와 Alq2-Ncd는 Alq3가 가지고 있는 파장과는 다른 파장대에서 흡광이 일어나고 있어 새로운 유기EL소재로서 용도가 기대된다.As a result, the newly synthesized Alq 2 -Nq and Alq 2 -Ncd are absorbed at wavelengths different from those of Alq 3 , and thus are expected to be used as new organic EL materials.
따라서 본 발명에서는 이러한 새로운 2종류의 소재물질의 합성방법을 개발하고 이들이 가지고 있는 EL재료 화합물로의 특성을 규명코자 한다.Therefore, the present invention is to develop a method for synthesizing these two new material materials and to characterize them as EL material compounds.
본 발명자는 발광성 소재물질로서 Alq3을 개량한 새로운 화합물을 합성하고자 하였으며,The present inventors attempted to synthesize a new compound improved Alq 3 as a luminescent material,
작용기로는 5,8-dihydroxy-1,4-naphtaquinone과,Examples of functional groups include 5,8-dihydroxy-1,4-naphtaquinone,
6,11-dihydroxy-5,12-naphtacenedione을 기존의 Alq3에 반응시켜 새로운 기능을 가지는 유기알루미늄-큐논계 발광소자를 제공코자 하는 것이다.The purpose of the present invention is to provide an organoaluminum-cunon-based light emitting device having a new function by reacting 6,11-dihydroxy-5,12-naphtacenedione with existing Alq 3 .
본 발명은 도 1에서 제시한 분자식 중 Alq2-Nq과 Alq2-Ncd으로 표시되는 화합물의 합성법(도 1참조)과 그 반응 생성물에 관한 것이다.The present invention relates to the synthesis of the compounds represented by Alq 2 -Nq and Alq 2 -Ncd in the molecular formula shown in Figure 1 (see Figure 1) and the reaction product thereof.
상기 화학식에서 중앙에 존재하는 1,4-naphthaquinone유도체(1)과 naphthacenedione유도체(2)는 각각 2개의 aluminum metal을 가지며, 이것은 다시 2개씩의 quinone 유도체를 가지게 된다.1,4-naphthaquinone derivatives (1) and naphthacenedione derivatives (2) present in the center of the formula has two aluminum metals, which in turn have two quinone derivatives.
이 분자는 Alq3가 가질 수 있는 발광성을 중앙에 있는 naphtaquinone 유도체와 naphtacenedione 유도체가 작용하여 여러 파장대의 발광성 기능을 가지게 된다.This molecule will have a luminance function of the number of wavelengths by the naphtaquinone naphtacenedione derivative and derivatives with a luminescent Alq 3 to have a central action.
(실시예 1)(Example 1)
*분자식 1Molecular Formula 1
Alq2-Nq의 합성Synthesis of Alq 2 -Nq
5,8-Dihydroxy-1,4-naphthaquinone 0.21g(1.08 mmol)를 25ml THF에 녹이고 Tris(8-hydroxyquinoline)aluminum complex 1.01g(2.17 mmol)을 천천히 첨가하여 상온에서 30분 동안 교반하였다.0.21 g (1.08 mmol) of 5,8-Dihydroxy-1,4-naphthaquinone was dissolved in 25 ml THF, and 1.01 g (2.17 mmol) of Tris (8-hydroxyquinoline) aluminum complex was slowly added thereto, followed by stirring at room temperature for 30 minutes.
점진적으로 붉은 색 용액이 보라색으로 변화하는 현상을 관찰한 후 다시 30분 동안 환류교반하였다. After gradually gradual change of the red solution to purple, the mixture was stirred under reflux for another 30 minutes.
이때 시료용액이 보라색에서 진한 보라로 변화하는 현상을 관찰하게 된다.At this time, the phenomenon that the sample solution changes from purple to dark violet is observed.
합성된 화합물의 확인을 위한 스펙트럼은 다음과 같다.The spectrum for the identification of the synthesized compound is as follows.
UV-Vis (nm, in THF): 244, 259, 318, 387, 517, 553, 597.UV-Vis (nm, in THF): 244, 259, 318, 387, 517, 553, 597.
(참고: 5,8-Dihydroxy-1,4-naphthaquinone: 269, 489, 517. Hydroxyquinoline: 203, 239, 317.). Tris(8-hydroxyquinoline)aluminum: 237, 260, 320, 335, 392.) (Note: 5,8-Dihydroxy-1,4-naphthaquinone: 269, 489, 517. Hydroxyquinoline: 203, 239, 317.). Tris (8-hydroxyquinoline) aluminum: 237, 260, 320, 335, 392.)
1H-NMR (ppm, CDCl3): 6.78~6.84, 6.98~7.18, 7.18~7.38, 7.38~7.60, 8.10~8.22, 8.22~8.36, 8.58~8.66, 8.74~8.86, 8.86~8.90. 1 H-NMR (ppm, CDCl 3 ): 6.78 ~ 6.84, 6.98 ~ 7.18, 7.18 ~ 7.38, 7.38 ~ 7.60, 8.10 ~ 8.22, 8.22 ~ 8.36, 8.58 ~ 8.66, 8.74 ~ 8.86, 8.86 ~ 8.90.
(실시예 2)(Example 2)
*분자식Molecular formula
Alq2-Ncd의 합성Synthesis of Alq 2 -Ncd
6,11-Dihydroxy-5,12-naphthacenedione 2.1g(8.3 mmol)을 25ml THF에 녹이고 Tris(8-hydroxyquinoline)aluminum 7.6g(16.6 mmol)을 천천히 가하여 상온에서 교반 한 다음 1시간 동안 환류 교반하였다.6,11-Dihydroxy-5,12-naphthacenedione 2.1g (8.3 mmol) was dissolved in 25ml THF, Tris (8-hydroxyquinoline) aluminum 7.6g (16.6 mmol) was added slowly, the mixture was stirred at room temperature, and stirred under reflux for 1 hour.
이때 시료는 오렌지색에서 붉은색으로 점차 변하면서 잘 녹지않았던 6,11-Dihydroxy-5,12-naphthacenedione이 완전히 녹는다.At this time, 6,11-Dihydroxy-5,12-naphthacenedione, which did not melt well, gradually changed from orange to red.
시료 중에 고형물질이 완전히 사라진 다음 다시 2시간 동안 환류 교반하여 반응을 완결하였다.Solids disappeared completely from the sample and then the mixture was stirred under reflux for 2 hours to complete the reaction.
합성된 화합물의 확인을 위한 스펙트럼은 다음과 같다.The spectrum for the identification of the synthesized compound is as follows.
Uv-vis (nm, in THF): 243, 261, 390, 478, 505, 541.Uv-vis (nm, in THF): 243, 261, 390, 478, 505, 541.
(참고: 6,11-Dihydroxy-5,12-naphthacenedione: 263, 455, 482, 516. AlQ3: 237, 260, 320, 335, 392. (Note: 6,11-Dihydroxy-5,12-naphthacenedione: 263, 455, 482, 516. AlQ3: 237, 260, 320, 335, 392.
1H-NMR (ppm, CDCl3): 6.99~7.18, 7.18~7.28, 7.28~7.76, 7.76~7.92, 7.92~8.04, 8.14~8.28, 8.28~8.54, 8.76~8.90. 1 H-NMR (ppm, CDCl 3 ): 6.99 to 7.18, 7.18 to 7.28, 7.28 to 7.76, 7.76 to 7.72, 7.92 to 8.04, 8.14 to 8.28, 8.28 to 8.54, 8.76 to 8.90.
본 발명에 의해서 합성된 화합물들은 작용성 기능기로서 naphthaquinone유도체와 naphthacenedione유도체를 화합물의 중앙에 가지게 되며 주위에 알루미늄에 2개의 큐논계 화합물이 배위된 Alq2를 가지게 되어 Alq3 보다 더 큰 분자량과 많은 파이전자를 가지게 되며, 이 전자는 Alq3 보다 넓은 공간을 소유하는 구조적인 특징을 가지게 되어 성능이 향상된 발광소자로 응용될 수 있는 것이다.The synthesized compound by the present invention are acting as a functional group, and have a naphthaquinone derivative and naphthacenedione derivative at the center of the compound is to have two queues nongye the compound is coordinated Alq 2, the aluminum around the higher molecular weight and higher than Alq 3 It will have a pi-electron, which has a structural feature that has a larger space than Alq 3 can be applied as a light emitting device with improved performance.
도 1은 본 발명의 주재가 되는 Alq2-Nq와 Alq2-Ncd의 화학식과 제법화학식1 is a chemical formula and formula of Alq 2 -Nq and Alq 2 -Ncd that is the subject of the present invention
도 2는 Alq2-Nq의 UV 분광분석도2 is a UV spectrogram of Alq 2 -Nq
도 3은 Alq2-Ncd의 UV 분광분석도3 is a UV spectrogram of Alq 2 -Ncd
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2002-0047187A KR100488495B1 (en) | 2002-08-09 | 2002-08-09 | Synthetic method of electroluminescent material by the use of naphthaquinone and naphthacenedione derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2002-0047187A KR100488495B1 (en) | 2002-08-09 | 2002-08-09 | Synthetic method of electroluminescent material by the use of naphthaquinone and naphthacenedione derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20040014021A KR20040014021A (en) | 2004-02-14 |
| KR100488495B1 true KR100488495B1 (en) | 2005-05-11 |
Family
ID=37321274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR10-2002-0047187A KR100488495B1 (en) | 2002-08-09 | 2002-08-09 | Synthetic method of electroluminescent material by the use of naphthaquinone and naphthacenedione derivatives |
Country Status (1)
| Country | Link |
|---|---|
| KR (1) | KR100488495B1 (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07138266A (en) * | 1993-11-19 | 1995-05-30 | Pioneer Electron Corp | Aluminum chelate complex and organic electroluminescence element using the same |
| US5466392A (en) * | 1993-06-02 | 1995-11-14 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and compound having an aluminum complex structure |
| JP2001081090A (en) * | 1999-03-09 | 2001-03-27 | Hayashibara Biochem Lab Inc | Pyran derivative |
-
2002
- 2002-08-09 KR KR10-2002-0047187A patent/KR100488495B1/en not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5466392A (en) * | 1993-06-02 | 1995-11-14 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and compound having an aluminum complex structure |
| JPH07138266A (en) * | 1993-11-19 | 1995-05-30 | Pioneer Electron Corp | Aluminum chelate complex and organic electroluminescence element using the same |
| JP2001081090A (en) * | 1999-03-09 | 2001-03-27 | Hayashibara Biochem Lab Inc | Pyran derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20040014021A (en) | 2004-02-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5305637B2 (en) | Organometallic complex, organic light emitting device using the same, and display device | |
| US8512877B2 (en) | Naphthyl carbazole derivatives, KL host material, the organic light emitting device employing the same, the display device and the illumination device employing the same | |
| JP2003096072A (en) | Light-emitting element | |
| JP4713864B2 (en) | Binuclear organometallic complex and organic electroluminescence device using the same | |
| CN107722061B (en) | Fluorenyl oxadiazole iridium complex and preparation method and application thereof | |
| CN113402561A (en) | High-color-purity platinum (II) complex luminescent material based on spirofluorene structure and application thereof | |
| US6355365B1 (en) | Molecular compound, luminous material using the same, and luminous element | |
| CN108997438A (en) | Red phosphorescent compound and the organic light emitting diode device for using the compound | |
| JP2003206278A (en) | Tetraphenylmethane derivative and light-emitting element containing the same | |
| US20220093879A1 (en) | Organoiridium complex for organic electroluminescent elements | |
| JP2003012676A (en) | Pypromethane metal complex and light emitting device material and light emitting device using the same | |
| CN107406473A (en) | Miscellaneous luminescent material and organic illuminating element with iridium complex, with using the compound | |
| JP5729851B2 (en) | Organic light emitting diode | |
| KR100488495B1 (en) | Synthetic method of electroluminescent material by the use of naphthaquinone and naphthacenedione derivatives | |
| CN110845421A (en) | Electron transport compound, synthesis method thereof and organic electroluminescent device | |
| JP6249210B2 (en) | Organic fluorescent material | |
| JP2001261796A (en) | Alkoxypolythiophene and alkoxythiophene | |
| WO2015199141A1 (en) | Coumalin-based condensed ring compound exhibiting luminescence/semiconductor properties, and method for manufacturing same | |
| JP2017149888A (en) | Light-emitting material comprising compound showing phosphorescence and delayed fluorescence | |
| CN111349040B (en) | Organic room temperature phosphor and white light luminescent material and preparation method thereof | |
| KR100376320B1 (en) | A red dopant for organic electroluminscene device and the organic electroluminscene device using the same | |
| RU2650529C1 (en) | Zinc and cadmium complexes of n-[2-(alkyliminomethyl)phenyl]-4-methylbenzenesulfamides having luminescent activity | |
| DE102014004224A1 (en) | Arylborane compound, its method of preparation and its use | |
| KR100481461B1 (en) | An organotin compound | |
| KR100367719B1 (en) | Blue light-emitting compounds, preparing method thereof and display device employing the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| E701 | Decision to grant or registration of patent right | ||
| N231 | Notification of change of applicant | ||
| GRNT | Written decision to grant | ||
| FPAY | Annual fee payment | ||
| FPAY | Annual fee payment | ||
| LAPS | Lapse due to unpaid annual fee |