KR19980035036A - Light Emitting Diode Using Polymer-Polymer Blend, Manufacturing Method thereof and Method of Improving Luminous Efficiency of Light Emitting Diode - Google Patents
Light Emitting Diode Using Polymer-Polymer Blend, Manufacturing Method thereof and Method of Improving Luminous Efficiency of Light Emitting Diode Download PDFInfo
- Publication number
- KR19980035036A KR19980035036A KR1019960053261A KR19960053261A KR19980035036A KR 19980035036 A KR19980035036 A KR 19980035036A KR 1019960053261 A KR1019960053261 A KR 1019960053261A KR 19960053261 A KR19960053261 A KR 19960053261A KR 19980035036 A KR19980035036 A KR 19980035036A
- Authority
- KR
- South Korea
- Prior art keywords
- light emitting
- polymer
- emitting diode
- anode
- conjugated
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- 229920002959 polymer blend Polymers 0.000 title claims abstract description 12
- 229920000642 polymer Polymers 0.000 claims abstract description 64
- 239000000758 substrate Substances 0.000 claims abstract description 16
- 238000002156 mixing Methods 0.000 claims abstract description 9
- 239000010409 thin film Substances 0.000 claims abstract description 8
- 239000000463 material Substances 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 238000001771 vacuum deposition Methods 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
- 239000010931 gold Substances 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 238000004528 spin coating Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 7
- 229920001940 conductive polymer Polymers 0.000 abstract description 2
- 239000002322 conducting polymer Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- 239000011368 organic material Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- -1 2, 5-bis (chloromethyl) -methoxy-4- (2-ethylhexyloxy) benzene [2, 5-bis (chlorometh-yl) -methoxy-4- (2-ethylhexyloxy) benzene] Chemical compound 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 230000005684 electric field Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000005215 recombination Methods 0.000 description 3
- 230000006798 recombination Effects 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229920000547 conjugated polymer Polymers 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NZWIYPLSXWYKLH-UHFFFAOYSA-N 3-(bromomethyl)heptane Chemical compound CCCCC(CC)CBr NZWIYPLSXWYKLH-UHFFFAOYSA-N 0.000 description 1
- ILKNNHYSEPMBSD-UHFFFAOYSA-N 4-methoxyphenol Chemical compound COC1=CC=C(O)C=C1.COC1=CC=C(O)C=C1 ILKNNHYSEPMBSD-UHFFFAOYSA-N 0.000 description 1
- 229920000109 alkoxy-substituted poly(p-phenylene vinylene) Polymers 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/02—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor bodies
- H01L33/26—Materials of the light emitting region
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/36—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the electrodes
- H01L33/40—Materials therefor
Landscapes
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
본 발명은 다공액화(polyconjugation)된 발광 고분자와 일정 공액화 길이를 지닌 발과 고분자의 블렌드를 발광층으로 사용한 우수한 발광효율을 지닌 발광 다이오드, 그의 제조방법 및 발광 다이오드의 발광효율을 향상시키는 방법에 관한 것이다. 본 발명에 따른 발광 다이오드의 발광효율 향상방법은, 다공액화된 발광 고분자와 일정한 공액화 길이를 지닌 발광 고분자 2종 이상을 블렌드하여 발광 다이오드의 발광층으로 사용하는 과정을 포함하고, 본 발명의 발광 다이오드는, 기판과, 기판 상에 위치한 양극과, 양극 상에 위치한 발광층과, 발광층 상에 위치한 음극으로 구성된 발광 다이오드에 있어서, 다공액화된 발광 고분자와 일정한 공액화 길이를 지닌 발광 고분자 2종 이상을 블렌드하여 제조된 고분자-고분자 블렌드를 발광 다이오드의 발광층으로 사용한 것을 특징으로 하며, 본 발명에 따른 발광 다이오드의 제조방법은, 상기한 양극 상에, 다공액화된 발광 고분자와 일정한 공액화 길이를 지닌 발광 고분자 2종 이상을 블렌드하여 제조된 고분자-고분자 블렌드로 이루어진 박막을 형성하는 단계를 포함하는 것을 특징으로 한다.The present invention relates to a light emitting diode having excellent luminous efficiency using a blend of a polyconjugated light emitting polymer, a foot and a polymer having a constant conjugated length as a light emitting layer, a method of manufacturing the same, and a method of improving the light emitting efficiency of the light emitting diode. will be. The method of improving the luminous efficiency of a light emitting diode according to the present invention includes a process of blending two or more kinds of light emitting polymers having a constant conjugated length with a porous conjugated light emitting polymer and using the same as a light emitting layer of the light emitting diode. Is a light emitting diode comprising a substrate, an anode on the substrate, a light emitting layer on the anode, and a cathode on the light emitting layer, wherein the light-conducting polymer is blended with at least two light emitting polymers having a constant conjugated length. It characterized in that the polymer-polymer blend prepared as a light emitting layer of the light emitting diode, characterized in that the manufacturing method of the light emitting diode according to the present invention, a light-emitting polymer having a constant conjugated length and a conjugated light-emitting polymer on the anode To form a thin film made of a polymer-polymer blend prepared by blending two or more kinds Is characterized in that it comprises a step.
Description
본 발명은 매우 향상된 양자효율(quantum efficiency) 및 밝기(brightness)를 갖는 발광소자에 관한 것으로, 특히, 다공액화(polyconjugation)된 발광 고분자와 일정 공액화 길이를 지닌 발광 고분자의 블렌드를 발광층으로 사용한 우수한 발광효율을 지닌 발광 다이오드, 그의 제조방법 및 발광 다이오드의 발광효율을 향상시키는 방법에 관한 것이다.BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a light emitting device having very improved quantum efficiency and brightness, and in particular, to a light emitting layer using a blend of a polyconjugated light emitting polymer and a light emitting polymer having a constant conjugation length as a light emitting layer. A light emitting diode having a light emitting efficiency, a method of manufacturing the same and a method of improving the light emitting efficiency of the light emitting diode.
현재까지 개발된 정보 표시소자 중 가장 널리 사용되고 있는 것은 텔레비젼의 브라운관, 즉, 음극선관(cathode-ray tube: CRT)과 액정표시(liquid crystal display: LCD)장치이나, 음극선관은 부피가 크고 중량이 무거운 문제점이 있으며, 액정표시 장치는 시야각이 좁고, 제품 생산성이 떨어지며, 가격이 매우 높다는 단점이 있었다.The most widely used information display devices developed to date are the cathode ray tube (CRT) and liquid crystal display (LCD) devices of televisions, but the cathode ray tube is bulky and heavy. There is a heavy problem, the liquid crystal display device has a disadvantage that the viewing angle is narrow, product productivity is low, and the price is very high.
앞으로는, 가볍고 얇은 평판 디스플레이 등의 표시장치가 첨단 미래형 TV나 모니터 이용될 것이라는 점을 감안할 때, 유기고분자 필름막을 이용한 발광 다이오드(light emitting diode: LED)의 개발은 필연적이라 할 수 있다.In the future, considering that light and thin display devices such as flat panel displays will be used in advanced futuristic TVs and monitors, development of light emitting diodes (LEDs) using organic polymer film layers is inevitable.
종래의 발광 다이오드는 무기를 결정을 발광소자로서 이용하고 있는데, 이러한 무기물 발광다이오드는 칼라화 및 대형화에 한계가 있을 뿐 아니라, 구동전압이 높고 발광효율이 매우 낮으며 청색 영역의 빛을 얻기 힘들다는 치명적인 단점을 지니고 있었다.Conventional light emitting diodes use inorganic crystals as light emitting elements, and these inorganic light emitting diodes have limitations in colorization and enlargement, as well as high driving voltage, very low luminous efficiency, and difficulty in obtaining blue light. It had a fatal flaw.
따라서, 상기한 무기물 발광다이오드의 한계를 극복하기 위하여, 발광 다이오드의 소재로서 유기물 또는 고분자를 이용하는 연구가 집중되고 있는 추세로, 최근에, 이와 같은 유기물 또는 고분자를 이용하여 전기장 발광소자를 제조하려는 다양한 시도가 행하여져 왔다.Accordingly, in order to overcome the limitations of the inorganic light emitting diode, researches using organic materials or polymers as light emitting diodes have been focused. In recent years, various methods for manufacturing an electric field light emitting device using such organic materials or polymers have been made. Attempts have been made.
이와 같은 유기물, 특히, 유기물 고분자를 발광소자로 이용한 표시장치는, 무기물의 경우에 비하여 가공이 용이하고 저가이며 합성이 용이할 뿐 아니라, 다양한 색상의 구현이 가능하다는 장점을 지니고 있다. 특히, 무기물로는 거의 제작이 불가능한 대형 평판 디스플레이의 개발에 대한 요구가 증대됨에 따라, 유기물 또는 고분자를 이용한 전기장 발광소자에 대한 연구가 급증하고 있다. 이와 같은 유기물 또는 고분자를 이용한 전기장 발광소자에서는, 양 전극으로부터 인가된 전자와 정공이 발광층인 유기물 또는 고분자 필름 내에서 재결합(recombination)함으로써 발광이 일어난다.Such an organic material, in particular, a display device using an organic polymer as a light emitting device has advantages in that processing is easier, cheaper and easier to synthesize than in the case of inorganic materials, and various colors can be realized. In particular, as the demand for development of a large flat panel display which is almost impossible to manufacture with inorganic materials is increasing, research on electric field light emitting devices using organic materials or polymers is rapidly increasing. In an electric field light emitting device using such an organic material or a polymer, light emission is caused by recombination of electrons and holes applied from both electrodes in an organic material or a polymer film which is a light emitting layer.
한편, 유기 전도성 고분자(conjugated polymer) 또는 유기물 색소체 분자(dyes)를 이용하여 전기장 발광소자를 제조함에 있어서, 소자의 발광효율은 정공 또는 전자가 주입되어 재결합하여 여기자를 형성한 후, 이 여기자가 얼마나 오랜 수명을 갖는가에 따라 좌우된다. 즉, 효율적인 발광소멸(radiative decay)을 위해서는, 형성된 여기자가 발광소멸을 하기 전까지 발광 고분자 내에서 충분히 오랜 수명을 갖고 있어야 한다. 이때, 여기자가 오랜 수명을 갖도록 하기 위해서는, 생성된 여기자를 다른 입자나 운반자와 충돌하지 않도록 속박을 시켜주어야 한다.On the other hand, when manufacturing an electric field light emitting device using an organic conductive polymer (conjugated polymer) or organic dye molecules (dyes), the luminous efficiency of the device is how holes or electrons are injected to recombine to form an exciton, and then the excitons It depends on whether you have a long life. In other words, for efficient radiative decay, the formed excitons should have a sufficiently long life in the light emitting polymer until they disappear. At this time, in order for the excitons to have a long life, it is necessary to bind the generated excitons so as not to collide with other particles or carriers.
상기한 연구의 일환으로, 저전압에서 구동이 가능하며 높은 효율을 지닌 발광 다이오드를 제조하기 위하여, 종래에는, 다공액화된 발광 고분자와 비발광 절연체 고분자를 블렌드하여 제조한 발광물질을 발광소자로서 사용하여 발광 다이오드를 제조하려는 시도가 있었다.As part of the above research, in order to manufacture a light emitting diode capable of driving at a low voltage and having high efficiency, conventionally, a light emitting material prepared by blending a porous conjugated light emitting polymer and a non-light emitting insulator polymer is used as a light emitting device. Attempts have been made to produce light emitting diodes.
그러나, 다공액화된 발광 고분자에 있어서는, 발광소자에 인가된 전자와 정공이 발광 고분자의 비편재화된 분자사슬을 통해 쉽게 이동하여 낮은 전압에서도 발광이 일어날 수 있는 반면에, 공액화 길이가 길어질수록 비발광 재결합(nonradiative recombination)이 발생하여 발광소자의 발광효율이 감소하기 때문에, 상기한 종래의 발광 다이오드는 제한된 발광효율을 지닌다는 결정적인 문제점을 지니고 있었다.However, in the conjugated light emitting polymer, electrons and holes applied to the light emitting device can easily move through the delocalized molecular chain of the light emitting polymer, so that light emission can occur at a low voltage. Since non-radiative recombination occurs and the luminous efficiency of the light emitting device is reduced, the above-described conventional light emitting diode has a critical problem that it has a limited luminous efficiency.
본 발명자들은, 다공액화된 발광 고분자를 사용한 발광 다이오드는 저전압에서 발광이 일어나지만 제한된 발광효율을 지닌다는 문제점을 지닌 반면에, 일정한 공액화 길이를 지닌 발광 고분자의 경우에는, 정공이나 전자의 고분자 사슬 내로의 주입(injection)이 힘드므로, 빛을 방출하기 위해서는 보다 높은 전압이 필요하지만, 공액화 길이가 길지 않으기 때문에, 비발광 재결합이 다공액화 고분자에 비해 상대적으로 감소하여 더 높은 발광효율을 나타낼 수 있다는 점에 착안하여, 다공액화된 발광 고분자와 일정한 공액화 길이를 지니도록 공액 길이가 조절된 발광 고분자를 농도 및 무게비를 변화시키면서 블렌드하여 발광 다이오드의 발광층으로 사용한 결과, 발광효율이 대폭적으로 향상될 뿐 아니라, 발광소자의 내구성이 증가됨은 물론, 저전압 구동이 가능한 발광 다이오드를 얻을 수 있다는 것을 알아내고, 예의 연구를 거듭하여 본 발명을 완성하기에 이르렀다.The inventors of the present invention have the problem that light-emitting diodes using a porous conjugated light-emitting polymer have a light emission at low voltage but have a limited luminous efficiency, whereas in the case of a light-emitting polymer having a constant conjugated length, a polymer chain of holes or electrons is used. Because injection is difficult, a higher voltage is required to emit light, but since the conjugated length is not long, non-luminescent recombination is relatively reduced compared to the porous conjugated polymer, resulting in higher luminous efficiency. In view of the fact that the conjugated light-emitting polymer and the conjugated light-controlled polymer having a constant conjugated length are blended with varying concentration and weight ratio, and used as the light emitting layer of the light emitting diode, the luminous efficiency is greatly improved. In addition, the durability of the light emitting device is increased, as well as the low voltage Leading to the possible to find out that it is possible to obtain a light-emitting diode, it completed the present invention intensive studies.
결국, 본 발명은 상기한 종래기술의 한계를 극복하기 위해 안출한 것으로, 본 발명의 주된 목적은, 발광소자에 주입된 전자와 정공의 결합에 의해 형성된 여기자가 보다 충분히 오랜 수명을 갖도록 할 뿐만 아니라, 일정한 공액 길이를 갖는 발광 고분자에서 형성된 여기자가 다공액화된 발광 고분자 내로 용이하게 전이될 수 있도록 고분자를 선정하여 블렌드시킨 고분자 물질을 발광층으로 이용함으로써, 발광 다이오드의 발광효율을 대폭적으로 향상시킬 수 있는 방법을 제공함에 있다.As a result, the present invention has been made to overcome the above limitations of the prior art, and the main object of the present invention is not only to make the excitons formed by the combination of electrons and holes injected into the light emitting device have a sufficiently long lifetime. By using a polymer material selected and blended as a light emitting layer so that the excitons formed in the light emitting polymer having a constant conjugate length can be easily transferred into the conjugated light emitting polymer, the light emitting efficiency of the light emitting diode can be significantly improved. In providing a method.
본 발명의 또 다른 목적은 우수한 발광효율을 지닐 뿐 아니라, 내구성이 증가된 발광 다이오드와 그의 제조방법을 제공함에 있다.Still another object of the present invention is to provide a light emitting diode and a method of manufacturing the same, which have not only excellent luminous efficiency but also increased durability.
도 1은 본 발명의 바람직한 실시예에 따라 제조된 발광 다이오드의 개략적인 단면도.1 is a schematic cross-sectional view of a light emitting diode manufactured according to a preferred embodiment of the present invention.
*도면의 주요부분에 대한 부호의 설명** Description of the symbols for the main parts of the drawings *
1:기판2:양극1: Substrate 2: Anode
3:발광층4:음극3: light emitting layer 4: cathode
상기한 목적을 달성하는, 본 발명에 따른 발광 다이오드의 발광효율 향상방법은, 다공액화된 발광 고분자와 일정한 공액화 길이를 지닌 발광 고분자 2종 이상을 블렌드하여 발광 다이오드의 발광층으로 사용하는 과정을 포함하는 것을 특징으로 한다.A method of improving the luminous efficiency of a light emitting diode according to the present invention, which achieves the above object, includes a process of blending two or more light emitting polymers having a constant conjugated length with a conjugated light emitting polymer and using the same as a light emitting layer of the light emitting diode. Characterized in that.
또한, 본 발명의 발광 다이오드는, 기판과, 기판 상에 위치한 양극과, 양극 상에 위치한 발광층과, 발광층 상에 위치한 음극으로 구성된 발광 다이오드에 있어서, 다공액화된 발광 고분자와 일정한 공액화 길이를 지닌 발광 고분자 2종 이상을 블렌드하여 제조된 고분자-고분자 블렌드를 상기한 발광 다이오드의 발광층으로 사용한 것을 특징으로 한다.In addition, the light emitting diode of the present invention is a light emitting diode comprising a substrate, an anode disposed on the substrate, a light emitting layer disposed on the anode, and a cathode disposed on the light emitting layer, the light emitting diode having a conjugated light emitting polymer and a constant conjugated length. The polymer-polymer blend prepared by blending two or more kinds of light emitting polymers is used as the light emitting layer of the light emitting diode.
이때, 상기한 양극으로는 금, 백금, ITO 등과 같은 높은 일함수를 갖는 물질을 사용하는 것이 바람직하며, 음극으로는 알루미늄, 마그네슘, 칼슘 등과 같은 상대적으로 낮은 일함수를 갖는 안정한 금속을 사용하는 것이 바람직하다.In this case, it is preferable to use a material having a high work function such as gold, platinum, ITO, etc. as the anode, and to use a stable metal having a relatively low work function such as aluminum, magnesium, calcium, etc. as the cathode. desirable.
또한, 적층 구조를 지닌 발광 다이오드를 형성하기 위하여, 상기한 고분자 블렌드 발광층과 상기한 전극 사이에 전하 수송층을 추가로 형성할 수도 있다.In addition, in order to form a light emitting diode having a stacked structure, a charge transport layer may be further formed between the polymer blend light emitting layer and the electrode.
아울러, 본 발명에 따른 발광 다이오드의 제조방법은, 기판과, 기판 상에 위치한 양극과, 양극 상에 위치한 발광층과, 발광층 상에 위치한 음극으로 구성된 발광 다이오드의 제조방법에 있어서, 상기한 양극 상에, 다공액화된 발광 고분자와 일정한 공액화 길이를 지닌 발광 고분자 2종 이상을 블렌드하여 제조된 고분자-고분자 블렌드로 이루어진 박막을 형성하는 단계를 포함하는 것을 특징으로 한다.In addition, the method of manufacturing a light emitting diode according to the present invention, in the method of manufacturing a light emitting diode comprising a substrate, an anode located on the substrate, a light emitting layer located on the anode, and a cathode located on the light emitting layer, And forming a thin film made of a polymer-polymer blend prepared by blending two or more light emitting polymers having a constant conjugated length with the porous conjugated light emitting polymer.
이때, 상기한 박막 형성방법으로는, 스핀코팅(spin coating)법 또는 진공증착법을 사용하는 것이 바람직하다.At this time, it is preferable to use the spin coating method or the vacuum deposition method as the thin film forming method.
이하, 본 발명에 따른 발광 다이오드와 그의 제조방법에 대한 바람직한 실시예를 통하여 본 발명을 보다 상세히 설명한다. 이하의 실시예는 본 발명을 보다 구체적으로 설명하기 위해 주어진 것으로, 본 발명의 요지에 따라, 본 발명의 하기 실시예에 의해 제한되지 않는다는 것은 본 발명이 속한 기술분야의 당업자에게 있어서 자명할 것이다.Hereinafter, the present invention will be described in more detail with reference to preferred embodiments of the light emitting diode and its manufacturing method according to the present invention. The following examples are given to illustrate the present invention in more detail, and according to the gist of the present invention, it will be obvious to those skilled in the art that the present invention is not limited by the following examples.
I. 단량체의 합성:I. Synthesis of Monomers:
(1) 1-(2-에틸헥실올기)-4-메톡시 벤젠[1-(2-ethylhexyloxy)-4-methoxy benzene] (IV)의 합성:(1) Synthesis of 1- (2-ethylhexylol) -4-methoxy benzene [1- (2-ethylhexyloxy) -4-methoxy benzene] (IV):
4-메톡시 페놀(4-methoxyphenol)과 수산화칼륨을 메탄올에 용해시킨 후, 2-에틱헥시리 브로마이드(2-ethylhexyl bromide)를 가하여 80℃에서 반응시켰다. 반응이 종료하면, 클로로포름으로 추출한 후, 감압증류하여 하기 식 (IV)로 표시되는 화합물을 얻었다.4-methoxy phenol (4-methoxyphenol) and potassium hydroxide were dissolved in methanol, and 2-ethylhexyl bromide was added thereto and reacted at 80 ° C. When the reaction was completed, the mixture was extracted with chloroform and then distilled under reduced pressure to obtain a compound represented by the following formula (IV).
1H-NMR(CDCl3): δ 6.8(s, 4H), 3.8(d, 2H), 3.7(s, 3H), 1.6-1.2(m, 9H), 0.9(m, 6H). 1 H-NMR (CDCl 3 ): δ 6.8 (s, 4H), 3.8 (d, 2H), 3.7 (s, 3H), 1.6-1.2 (m, 9H), 0.9 (m, 6H).
(2) 2, 5-비스(클로로메틸)-메톡시-4-(2-에틸헥실옥시) 벤젠[2, 5-bis(chlorometh-yl)-methoxy-4-(2-ethylhexyloxy) benzene] (IV)의 합성:(2) 2, 5-bis (chloromethyl) -methoxy-4- (2-ethylhexyloxy) benzene [2, 5-bis (chlorometh-yl) -methoxy-4- (2-ethylhexyloxy) benzene] Synthesis of (IV):
상기에서 얻어진 화합물 (IV)와 과량의 염산 및 포름알데히드를 디옥산(dioxane)에 용해시킨 후, 90℃에서 반응시켰다. 반응이 종료하면, 클로로포름으로 추출한 후, 메탄올에서 결정화하여 침전물을 여과한 다음, 진공건조하여 하기 식( V)로 표시되는 화합물을 얻었다.Compound (IV) obtained above, excess hydrochloric acid and formaldehyde were dissolved in dioxane, followed by reaction at 90 ° C. After the reaction was completed, the mixture was extracted with chloroform, crystallized in methanol, the precipitate was filtered off, and then dried in vacuo to obtain a compound represented by the following formula (V).
1H-NMR(CDCl3): δ 6.8(d, 2H), 4.5(s, 4H), 3.8(d, 2H), 3.8(s, 3H), 1.6-1.3(m, 9H), 0.9(m, 6H). 1 H-NMR (CDCl 3 ): δ 6.8 (d, 2H), 4.5 (s, 4H), 3.8 (d, 2H), 3.8 (s, 3H), 1.6-1.3 (m, 9H), 0.9 (m , 6H).
(3) MEH-PPV 단량체[MEH-PPV monomer] (VI)의 합성:(3) Synthesis of MEH-PPV monomer [VI]:
상기에서 얻어진 화합물 (V)와 테트라히드로티오펜(tetrahydrothiophene)을 소량의 메탄올에 용해시킨 후, 50℃에서 반응시켰다. 반응이 종료하면, 용액을 농축한 후, 아세톤에서 결정화하여 하기 식 (VI)으로 표시되는 화합물을 얻었다.Compound (V) and tetrahydrothiophene obtained above were dissolved in a small amount of methanol and then reacted at 50 ° C. When the reaction was completed, the solution was concentrated, and then crystallized in acetone to obtain a compound represented by the following formula (VI).
1H-NMR(D2O): δ 7.1(s, 2H), 4.3(d, 4H), 3.8(d, 2H), 3.7(s, 3H), 3.4(m, 8H), 2.2(m, 8H), 1.6-1.3(m, 9H), 0.7(m, 6H). 1 H-NMR (D 2 O): δ 7.1 (s, 2H), 4.3 (d, 4H), 3.8 (d, 2H), 3.7 (s, 3H), 3.4 (m, 8H), 2.2 (m, 8H), 1.6-1.3 (m, 9H), 0.7 (m, 6H).
(4) 2, 5-비스(트리메틸실릴)-1, 4-크실렌비스(트리페닐포스포늄 브로마이드)[2, 5-bis(trimethylsilyl)-1, 4-xylenebis(triphenylphosphonium bromide)] (VII)의 합성:(4) 2,5-bis (trimethylsilyl) -1,4-xylenebis (triphenylphosphonium bromide) [2,5-bis (trimethylsilyl) -1,4-xylenebis (triphenylphosphonium bromide)] of (VII) synthesis:
2, 5-비스(트리메틸실릴)-1, 4-비스(브로모메틸) 벤진[2, 5-bis(trimethylsilyl)-1, 4-bis(bromomthyl) benzene]과 트리페닐포스핀(triphenyphosphine)을 디메틸포름아미드(DMF)에서 반응시킨 다음, 디에틸에테르에서 결정화시켰다. 침전물을 여과하고 진공건조하여, 하기 식 (VII)로 표시되는 화합물을 얻었다.2, 5-bis (trimethylsilyl) -1, 4-bis (bromomethyl) benzine [2, 5-bis (trimethylsilyl-1), 4-bis (bromomthyl) benzene] and triphenylphosphine The reaction was carried out in dimethylformamide (DMF) and then crystallized in diethyl ether. The precipitate was filtered off and dried in vacuo to give the compound represented by the following formula (VII).
1H-NMR(DMSO-d5): δ 7.94-7.55(m, 30H), 7.05(s, 2H), 5.01(d, 4H), -0.31(s, 18H), 원소분석: 계산치(C: 64.35, H: 5.79), 측정기(C: 63.02, H: 6.04). 1 H-NMR (DMSO-d 5 ): δ 7.94-7.55 (m, 30H), 7.05 (s, 2H), 5.01 (d, 4H), -0.31 (s, 18H), Elemental Analysis: Calculated (C: 64.35, H: 5.79), meter (C: 63.02, H: 6.04).
(5) 1, 3-비스(4-포르밀페녹시)알칸[1, 3-bis(4-formylphenoxy)alkane] (VIII)의 합성:(5) Synthesis of 1, 3-bis (4-formylphenoxy) alkane [1, 3-bis (4-formylphenoxy) alkane] (VIII):
4-히드록시벤즈알데히드(4-hydroxybenzaldehyde)와 디브로모알칸(dibromoalkane) 및 탄산칼륨을 DMF 용액에서 반응시켰다. 반응이 종료하면, 냉각시킨 후, 증류수에서 결정화하고 에탄올에서 재결정하여, 하기 식 (VIII)로 표시되는 화합물을 얻었다.4-hydroxybenzaldehyde, dibromoalkane, and potassium carbonate were reacted in a DMF solution. When the reaction was completed, the mixture was cooled, then crystallized in distilled water and recrystallized in ethanol to obtain a compound represented by the following formula (VIII).
1H-NMR(CDCl3): δ 9.80(s, 2H), 7.91(s, 2H), 7.79(d, 4H), 6.83(d, 4H), 4.22(t, 4H), 2.30(q, 2H), 원소분석: 계산치(C: 71.82, H: 5.67), 측정기(C: 70.43, H: 5.60). 1 H-NMR (CDCl 3 ): δ 9.80 (s, 2H), 7.91 (s, 2H), 7.79 (d, 4H), 6.83 (d, 4H), 4.22 (t, 4H), 2.30 (q, 2H ), Elemental Analysis: Calculated Value (C: 71.82, H: 5.67), Meter (C: 70.43, H: 5.60).
II. 고분자의 합성:II. Synthesis of Polymers:
(1) P-1의 합성:(1) Synthesis of P-1:
상기한 과정에서 합성된 단량체 (VI)을 적당량의 증류수에 용해시킨 후, 0℃로 냉각시켰다. 냉각이 이루어진 다음, 동량의 수산화나트륨을 가하여 젤 형태(gel-type)의 고분자를 형성시키고, 이를 과량의 메탄올로 용해시킨 다음, 승온시켜 선중합체(prepolymer)를 합성하였다. 이를 클로로포름/n-헥산에서 재결정하여 유기용매에 녹는 선중합체를 얻었다. 선중합체를 1,2,3-트리클로로벤젠(1,2,3-trichlorobenzene)에 용해시킨 다음, 소량의 아세트산(acetic acid)을 촉매로 하여 200℃에서 24시간 동안 제거반응시켜 하기 식 (P-1)으로 표시되는 최종 고분자를 얻었다.The monomer (VI) synthesized in the above procedure was dissolved in an appropriate amount of distilled water and then cooled to 0 ° C. After cooling, an equal amount of sodium hydroxide was added to form a gel-type polymer, dissolved in an excess of methanol, and then heated to synthesize a prepolymer. This was recrystallized in chloroform / n-hexane to obtain a prepolymer soluble in an organic solvent. The prepolymer was dissolved in 1,2,3-trichlorobenzene, and then a small amount of acetic acid was used as a catalyst to remove the reaction at 200 ° C. for 24 hours. The final polymer represented by -1) was obtained.
(2) P-2의 합성:(2) Synthesis of P-2:
동일한 당량의 상기한 과정에서 합성된 단량체 (VII)과 단량체 (VIII)을 에탄올과 클로로포름에 완전히 용해시킨 다음, 약간 과량의 에톡시화 나트륨(sodiumethoxide)을 가하고 상온에서 반응시켰다. 반응이 완결되면, 클로로포름으로 추출한 다음, 메탄올에 침전시켜, 하기 식 (P-2)로 표시되는 고분자를 얻었다.The same amount of monomer (VII) and monomer (VIII) synthesized in the above-described procedure were completely dissolved in ethanol and chloroform, and then a slight excess of sodium ethoxide was added and reacted at room temperature. When the reaction was completed, the mixture was extracted with chloroform and then precipitated in methanol to obtain a polymer represented by the following formula (P-2).
(3) 고분자 블렌드:(3) polymer blends:
상기에서 합성된 고분자 P-1과 P-2의 무게비를 변화시키면서, 적정한 농도에서, 상온에서 1,2-디클로로에탄(1,2-dichloroethane) 내에서 5시간 정도 교반하면서 용해시켜 블렌드하였다. 블렌드된 고분자 용액은 맑고 투명하였다.While varying the weight ratio of the polymer P-1 and P-2 synthesized above, the mixture was dissolved by stirring for about 5 hours in 1,2-dichloroethane at room temperature at an appropriate concentration. The blended polymer solution was clear and transparent.
III. 발광 다이오드의 제작:III. Fabrication of Light Emitting Diodes:
상기한 과정에서 얻어진 고분자 P-1과 P-2의 비율을 각각 변화시키면서 용해된 고분자 블렌드를 발광물질로 이용하여, 도 1에 도시된 바와 같이, 기판(1)과, 기판(1) 상에 위치한 양극(2)과, 양극(2) 상에 위치한 발광층(3)과, 발광층(3) 상에 위치한 음극(4)으로 구성된 발광 다이오드를 제조하였다.As shown in FIG. 1, the dissolved polymer blend is used as a light emitting material while varying the ratio of the polymers P-1 and P-2 obtained in the above-described process, respectively, on the substrate 1 and the substrate 1. A light emitting diode composed of an anode (2) located, a light emitting layer (3) located on the anode (2), and a cathode (4) located on the light emitting layer (3) were manufactured.
본 발명에서는, 고분자 블렌드를 양극(2)이 얇게 피복된 유리 등의 재질을 지닌 기판(1) 상에 스핀 코팅 또는 진공증착하여 얇은 박막의 발광층(3)을 형성한 후, 발광층(3) 상에 금속 박막의 음극(4)을 형성하는데, 이때, 각 층은 박막 형성후 반응 또는 건조과정이 필요할 수 있다.In the present invention, the polymer blend is spin-coated or vacuum-deposited on a substrate 1 having a material such as glass coated with a thin film of the anode 2 to form a thin light emitting layer 3, and then on the light emitting layer 3. The cathode 4 of the metal thin film is formed in this case, where each layer may require a reaction or drying process after the thin film is formed.
상기한 본 발명의 발광 다이오드에서는, 음극(4)과 양극(2) 사이에 전압을 가했을 때, 전자 또는 정공은 상대 전극 쪽으로 발광층(3)을 통하여 이동하다가 만나게 됨으로써, 발광을 일으키게 된다.In the light emitting diode of the present invention described above, when a voltage is applied between the cathode 4 and the anode 2, electrons or holes move through the light emitting layer 3 toward the counter electrode, whereby light is generated.
[실시예 1]Example 1
22.0㎎의 고분자 P-1과 8.6㎎의 고분자 P-2를 5ml의 1,2-디클로로에탄에서 10시간 동안 교반한 후 완전히 용해시켜, 두 고분자의 무게비가 (P-1)/(P-2)=7/3으로 블렌드된 고분자를 얻었다. 상기에서 얻어진 고분자를 마이크로 필터로 여과하여 먼지를 제거한 후, ITO 코팅된 유리 기판 상에 2,000rpm으로 회전시키면서 스핀코팅하였다.22.0 mg of polymer P-1 and 8.6 mg of polymer P-2 were stirred in 5 ml of 1,2-dichloroethane for 10 hours and completely dissolved. The weight ratio of the two polymers was (P-1) / (P-2). ) = 7/3 to obtain a polymer blended. The obtained polymer was filtered through a micro filter to remove dust, and then spin-coated while rotating at 2,000 rpm on an ITO coated glass substrate.
고분자가 코팅된 기판의 용매를 제거하기 위하여, 100℃의 오븐에서 1시간 동안 건조시키 다음, 진공증착법에 의해서 알루미늄을 증착하여 지름이 5mm인 구형 전극을 형성함으로써, 본 발명의 발광 다이오드를 제조하였다.In order to remove the solvent of the polymer-coated substrate, the light emitting diode of the present invention was manufactured by drying in an oven at 100 ° C. for 1 hour and then depositing aluminum by vacuum deposition to form a 5 mm diameter spherical electrode. .
얻어진 발광 다이오드의 발광효율을 측정한 결과, 본 발명의 발광 다이오드의 상대적 발광효율은 상기한 고분자 P-1을 사용하여 제조된 발광 다이오드에 비하여 5배 증가된 효율을 나타내었다.As a result of measuring the luminous efficiency of the obtained light emitting diode, the relative luminous efficiency of the light emitting diode of the present invention showed a 5 times increase in efficiency compared to the light emitting diode manufactured using the polymer P-1.
[실시예 2]Example 2
10.0㎎의 고분자 P-1과 23.0㎎의 고분자 P-2를 5ml의 1,2-디클로로에탄에서 10시간 동안 교반한 후 완전히 용해시켜, 두 고분자의 무게비가 (P-1)/(P-2)=3/7로 블렌드된 고분자를 얻었다.10.0 mg of polymer P-1 and 23.0 mg of polymer P-2 were stirred in 5 ml of 1,2-dichloroethane for 10 hours and completely dissolved, so that the weight ratio of the two polymers was (P-1) / (P-2). A polymer blended with) = 3/7 was obtained.
이어, 상기 실시예 1과 동일한 방법을 사용하여 발광 다이오드를 제조하여, 발광파장 및 발광효율을 측정하였다. 측졍 결과, 본 발명의 발광 다이오드는 상기한 고분자 P-1을 사용하여 제조된 발광 다이오드에 비하여 17배 증가된 발광효율을 지닌 것으로 밝혀졌다.Subsequently, a light emitting diode was manufactured using the same method as in Example 1, and the light emission wavelength and light emission efficiency were measured. As a result of the measurement, the light emitting diode of the present invention was found to have a luminous efficiency 17 times higher than that of the light emitting diode manufactured using the polymer P-1.
[실시예 3]Example 3
4.0㎎의 고분자 P-1과 60.0㎎의 고분자 P-2를 5ml의 1,2-디클로로에탄에서 10시간 동안 교반한 후 완전히 용해시켜, 두 고분자의 무게비가 (P-1)/(P-2)=1/15로 블렌드된 고분자를 얻었다.4.0 mg of polymer P-1 and 60.0 mg of polymer P-2 were stirred in 5 ml of 1,2-dichloroethane for 10 hours and completely dissolved. The weight ratio of the two polymers was (P-1) / (P-2). ) = 1/15 to obtain a polymer blended.
이어, 상기 실시예 1과 동일한 방법을 사용하여 발광 다이오드를 제조하여, 발광파장 및 발광효율을 측정하였다. 측정 결과, 본 발명의 발광 다이오드는 상기한 고분자 P-1을 사용하여 제조된 발광 다이오드에 비하여 480배 증가된 발광효율을 지닌 것으로 밝혀졌다.Subsequently, a light emitting diode was manufactured using the same method as in Example 1, and the light emission wavelength and light emission efficiency were measured. As a result of the measurement, the light emitting diode of the present invention was found to have a light emission efficiency increased by 480 times compared to the light emitting diode manufactured using the polymer P-1.
이상에서 알 수 있는 바와 같이, 본 발명에 따라 제조된 발광 다이오드는 블렌드하지 않은 고분자를 사용하여 제조된 발광 고분자에 비하여, 매우 높은 발광효율을 나타내는 것으로 밝혀졌다.As can be seen from the above, the light emitting diode prepared according to the present invention was found to exhibit a very high luminous efficiency, compared to the light emitting polymer prepared using the unblended polymer.
본 발명에서는, 발광 다이오드의 발광층에 발광 고분자의 블렌드 물질을 도입함으로써, 전자나 정공의 주입후 생성되는 여기자의 수명 및 여기자의 전이가 증대되어, 발광 다이오드의 발광효율을 대폭적으로 증가시킬 수 있을 뿐 아니라, 발광소자의 내구성을 증대시킬 수 있는 등의 효과가 있다. 따라서, 발광소자의 상품화 가능성을 더욱 높일 수 있음은 물론, 기존의 발광소자를 적극적으로 대체할 수 있는 효과가 있다.In the present invention, by introducing a blended material of the light emitting polymer into the light emitting layer of the light emitting diode, the lifetime of the excitons generated after the injection of electrons or holes and the transition of the excitons can be increased, which can greatly increase the luminous efficiency of the light emitting diodes. In addition, there is an effect that the durability of the light emitting device can be increased. Therefore, the possibility of commercialization of the light emitting device can be further increased, and there is an effect of actively replacing the existing light emitting device.
Claims (8)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019960053261A KR100226425B1 (en) | 1996-11-11 | 1996-11-11 | A light emitting diode and a fabrication method thereof, and a method for improving the light-emitting efficiency thereof using polymer blend |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019960053261A KR100226425B1 (en) | 1996-11-11 | 1996-11-11 | A light emitting diode and a fabrication method thereof, and a method for improving the light-emitting efficiency thereof using polymer blend |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR19980035036A true KR19980035036A (en) | 1998-08-05 |
| KR100226425B1 KR100226425B1 (en) | 1999-10-15 |
Family
ID=19481445
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019960053261A KR100226425B1 (en) | 1996-11-11 | 1996-11-11 | A light emitting diode and a fabrication method thereof, and a method for improving the light-emitting efficiency thereof using polymer blend |
Country Status (1)
| Country | Link |
|---|---|
| KR (1) | KR100226425B1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100626660B1 (en) * | 1999-06-28 | 2006-09-22 | 한국전자통신연구원 | High Efficiency Polymeric Electroluminescent Device using a Phase Separation Process |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3102867B2 (en) * | 1989-07-24 | 2000-10-23 | 三井化学株式会社 | Light emitting element |
-
1996
- 1996-11-11 KR KR1019960053261A patent/KR100226425B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR100226425B1 (en) | 1999-10-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3121282B2 (en) | Fluorene-based polymer for EL element and EL element using the same | |
| US6638646B2 (en) | Substituted poly(arylenevinylenes), process for their preparation, and their use in electroluminescent elements | |
| US6124046A (en) | Organic electroluminescent polymer for light emitting diode | |
| JP4283447B2 (en) | Conjugated polymers containing specific fluorenyl units and having improved properties | |
| US5514878A (en) | Polymers for electroluminescent devices | |
| US6686066B2 (en) | Light-emitting compound and display device adopting light-emitting compound as color-developing substance | |
| JP3188885B2 (en) | Highly efficient electroluminescent polymer with excellent color tuning | |
| KR20020094735A (en) | White Electroluminescent Polymer And Organic Electroluminescent Device Using Thereof | |
| US7951965B2 (en) | Phenanthrene derivatives and organic light-emitting diodes containing said phenanthrene derivative | |
| US6395411B1 (en) | Display device adopting light-emitting compound as color-developing substance | |
| US6337150B1 (en) | Light-emitting compound and display device adopting light-emitting compound as color-developing substance | |
| KR100528322B1 (en) | Blue Electroluminescent Polymer And Organo-electroluminescent Device Using Thereof | |
| US6338909B1 (en) | Light-emitting compound and display device adopting light-emitting compound as color-developing substance | |
| JPH0963767A (en) | Organic electroluminescent element | |
| JP5196747B2 (en) | Polymer for luminescence | |
| KR0155863B1 (en) | Blue luminescent polymer and luminescent diode using the same | |
| US6967255B2 (en) | Phenanthrene compounds | |
| KR100226425B1 (en) | A light emitting diode and a fabrication method thereof, and a method for improving the light-emitting efficiency thereof using polymer blend | |
| JP2940606B2 (en) | A display element that uses a light emitting polymer as a coloring material | |
| JP3272230B2 (en) | Blue light emitting polymer and method of manufacturing blue light emitting diode using the same | |
| KR100260075B1 (en) | Full conjugated electroluminescent polymers containing fluorinated aryl group and a process for producing the polymers | |
| KR100237310B1 (en) | Electroluminescence polymer composition with oxadiazole and the method of the preparation thereof | |
| KR100553734B1 (en) | Organic silicone compound, light-emitting compound formed therefrom and display device employing the light-emitting compound as color-developing substance | |
| JPH0559356A (en) | Organic luminescent element | |
| KR100394509B1 (en) | High Functional Light Emitting Polymers Containing Tetra-substituted Phenylene unit for Use in Electroluminescent Devices |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| E902 | Notification of reason for refusal | ||
| E701 | Decision to grant or registration of patent right | ||
| GRNT | Written decision to grant | ||
| FPAY | Annual fee payment |
Payment date: 20070702 Year of fee payment: 9 |
|
| LAPS | Lapse due to unpaid annual fee |