CN100470874C - Glow organic electroluminescent device and manufacturing method thereof - Google Patents

Glow organic electroluminescent device and manufacturing method thereof Download PDF

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CN100470874C
CN100470874C CNB2003101158739A CN200310115873A CN100470874C CN 100470874 C CN100470874 C CN 100470874C CN B2003101158739 A CNB2003101158739 A CN B2003101158739A CN 200310115873 A CN200310115873 A CN 200310115873A CN 100470874 C CN100470874 C CN 100470874C
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alq
dye
electroluminescence device
organic electroluminescence
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马东阁
陈江山
周全国
陈振宇
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Changchun Institute of Applied Chemistry of CAS
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Abstract

The invention relate to red light organic electroluminescence device and its manufacture method. By intermingling fluorescence dye C545T(density: 0.2%-2%) which function as sensitizer and red light organic dye(density: 0.5%-5%) with 8- hydroxyl quinoline aluminium, electroluminescence device with a structure of IT0/NPB/ALq3:C545T:red light dye/Alq3/liF/Al can be produced. The device is driven by direct current, producing the luminescence of red light dye. Compared with the electroluminescence device without sensitizer C545T, its luminescence efficiency and brightness has been improved markedly, thus commendably realizing red organic electroluminescence.

Description

The ruddiness organic electroluminescence device
Technical field
The present invention relates to a kind of ruddiness organic electroluminescence device.
Background technology
Along with the fast development of electronics and information industry, display is being played the part of vital role as the requisite interface of man-machine interaction.Continuing to bring out of the continuous progress of Display Technique and new technology driven the great-leap-forward development that shows industry.As flat panel display of new generation---organic elctroluminescent device, because the characteristics of himself, simple as preparation technology, cut-in voltage is low, brightness is high, efficient is high, response speed is fast, active illuminating, the big plane of wide, radiationless, easy realization, visual angle and flexible curved and cheap etc., the progress that obtains aspect industrialization has brought infinite commercial opportunities for flat panel display market in recent years.Yet, for ORGANIC ELECTROLUMINESCENCE DISPLAYS,, and there is product to come out though the performance of red, green, blue organic electroluminescence device is significantly improved, but its efficient and stability still remain further to be improved, and particularly the ruddiness organic electroluminescence device faces a severe challenge especially.Therefore, how to solve the emphasis that the problems referred to above are these area researches from material and device architecture design.
It is to prepare the most frequently used method of ruddiness organic electroluminescence device at present that red dye is entrained in the organic molecule material of main part, as calendar year 2001, people such as S.T.Lee have delivered on Applied Physics Letters and have utilized 2,9-dimethyl-4,7-diphenyl-1,10-neck Fei Luolin (BCP) is as hole blocking layer, with red dye 2-{2-[2-(4-dimethyl amido-phenyl)-vinyl]-6-methyl-pyrans-4-inner salt alkene }-malononitrile (DCM) is doped to oxine aluminium (Alq 3) lining, having prepared a kind of double-heterostructure ruddiness device, its current efficiency has reached 5.66cd/A; 2002, people such as Qiu Yong on Applied Physics Letters, delivered utilize gallium binuclear complex as material of main part (host material), the 2-{2-tert-butyl group-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydrochysene-1H, 5H-pyrido [3,2,1-ij] quinoline-9-yl)-vinyl]-pyrans-4-inner salt alkene }-malononitrile (DCJTB) is as dopant, prepared the ruddiness electroluminescent device, and high-high brightness is 7260cd/cm 2, current efficiency is 2.04cd/A.But, this single ruddiness organic electroluminescence device that mixes and realize, except lower electroluminescent efficiency, glow color often causes the problem of colorimetric purity difference owing to the influence of the organic molecule material of main part character that is subjected to dopant dye concentration and selection.In recent years, bibliographical information is arranged, method by two dyestuff codopes, being about to red dye is doped in the material of main part with second dopant that is referred to as sensitizing dyestuff simultaneously, utilization has improved the colorimetric purity of device to the waterfall energy delivery mechanism of red dye again from the material of main part to the sensitizing dyestuff, as 1999, people such as Yuji Hamada have delivered 5 on Applied Physics Letters, 6,11,12-tetraphenyl-naphthonaphthalene (Rubrene) and red dye 2-{2-methyl-6-[2-(2,3,6,7-tetrahydrochysene-1H, 5H-pyrido [3,2,1-ij] quinoline-9-yl)-vinyl]-pyrans-4-inner salt alkene }-malononitrile (DCM2) mixes oxine aluminium (Alq simultaneously 3) lining, prepared pure ruddiness electroluminescent device, but high-high brightness has only 7800cd/cm 22002, people such as S.Y.liu delivered on Applied Physics Letters quinacridone (Quinacridone) and DCJTB have been mixed oxine aluminium (Alq altogether 3) lining, also prepared pure ruddiness organic electroluminescence device, but maximal efficiency has only 3cd/A.Can see,, not obtain substantive the improvement though can solve the colorimetric purity problem of single doping ruddiness device by the waterfall energy delivery with the codope method.
Summary of the invention
The purpose of this invention is to provide a kind of ruddiness organic electroluminescence device;
Another object of the present invention provides a kind of preparation method of ruddiness organic electroluminescence device.
The present invention obtains high efficiency, high color purity ruddiness organic electroluminescence device with two dyestuff codopes by waterfall carrier capture mechanism.
Ruddiness organic dyestuff among the present invention is a kind of among DCJTI, DCJTB, DCM, the Nile red; Sensitizing dyestuff is C545T; The main body organic molecule material is Alq 3
C545T and Alq 3Glow green does not have overlappingly between their absorption spectrum and the fluorescence spectrum, show not have energy transfer process between them.DCJTI, DCJTB, DCM, Nile red dyestuff burn red, their absorption spectrum and C545T, Alq 3Emission spectrum stack is arranged, therefore, from C545T and Alq 3To red dye energy delivery is arranged.According to C545T, Alq 3With the level of energy of red dye, can infer, be entrained in Alq 3: the C545T in the red dye mixed system only plays the carrier capture effect in the electroluminescence process.Like this, whole electroluminescence may comprise two processes: a kind of C545T of being is at first from Alq 3Capture injected electrons and hole, the electronics and the hole that are captured on C545T are then captured by red dye again, finally cause emitting red light, so-called waterfall carrier capture process that Here it is; Another kind is that the electronics and the hole that are captured on C545T at first are compounded to form exciton, again energy delivery is given red dye and is caused red dye luminous.Test verifiedly, above-mentioned two kinds of processes are present in the whole electroluminescence process simultaneously, and are main process with the waterfall carrier capture.Can see, the existence of this waterfall carrier capture process not only can improve colorimetric purity effectively, importantly, it can also more effectively reduce the device luminous efficiency degenerate problem that the accumulation of excess space electric charge is caused, thereby produces high color purity, high efficiency ruddiness organic electroluminescence device.
The main body organic molecule material that the present invention uses is oxine aluminium (Alq 3), its molecular structure is as follows:
Figure C200310115873D00061
The molecular structural formula of sensitization organic dyestuff is as follows:
Figure C200310115873D00062
10-(2-[4-morpholinodithio base)-2,3,6,7-tetrahydrochysene-1,1,7,7-tetramethyl-1H, 5H, 11H-(1)-benzo give a tongue-lashing the ketone group of muttering-(6,7,8-ij) quinolizine-11-ketone (C545T)
The molecular structural formula of ruddiness dopant is as follows:
Figure C200310115873D00063
2-{2-isopropyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydrochysene-1H, 5H-pyrido [3,2,1-ij] quinoline-9-yl)-vinyl]-pyrans-4-inner salt alkene }-malononitrile (DCJTI)
Figure C200310115873D00071
The 2-{2-tert-butyl group-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydrochysene-1H, 5H-pyrido [3,2,1-ij] quinoline-9-yl)-vinyl]-pyrans-4-inner salt alkene }-malononitrile (DCJTB)
Figure C200310115873D00072
2-{2-[2-(4-dimethyl amido-phenyl)-vinyl]-6-methyl-pyrans-4-inner salt alkene }-malononitrile (DCM)
Figure C200310115873D00073
9-diethylamide-7a, 12a-dihydro-benzo [α] phenoxazine-5-ketone (Nile red)
Preparation process
Sensitizing dyestuff C545T and ruddiness organic dyestuff DCJTB, DCJTI, DCM or Nile red are doped to Alq simultaneously according to the concentration of 0.2%-2%, 0.5%-5% respectively 3In, being prepared into structure is ITO/NPB/Alq 3: C545T: red dye/Alq 3The electroluminescent device of/LiF/ metal electrode, organic layer and metal electrode are in vacuum degree 10 -4Evaporation under the pressure of handkerchief, the evaporation rate of organic layer is controlled at , the evaporation rate of LiF is controlled at
Figure C200310115873D0008114308QIETU
, the evaporation of metals rate controlled exists
Figure C200310115873D0008114322QIETU
Wherein, the NPB layer thickness is 50nm, Alq 3: C545T: the red dye layer thickness is 30nm, Alq 3Layer is 20nm, and the LiF layer is 1nm, and metal A l is 100nm.The obtained device direct voltage drive has obtained the luminous red electroluminescence that comes fully to red dye, and maximum power efficiency has reached 9.4Lm/W, maximum current efficient 11.2cd/A, high-high brightness 29500cd/m 2, than the efficient and the brightness of single adulterated lighting part significant raising having been arranged, these can obtain authentication from accompanying drawing 2-6.
Advantage of the present invention is the another kind of sensitization organic dyestuff that mixes in luminescent layer, utilizes waterfall energy delivery mechanism in the colorimetric purity that guarantees the ruddiness organic electroluminescence device, has further improved electroluminescent properties.
Another advantage of the present invention is to have the characteristics of high color purity, high efficiency, high brightness by the ruddiness organic electroluminescence device that the doping of sensitization organic dyestuff prepares.
Description of drawings
Fig. 1 is the structural profile schematic diagram of electroluminescent device: 1, luminescent layer 5, electron transfer layer 6, resilient coating 7, the metallic cathode of glass substrate 2, ITO electrode 3, hole transmission layer 4, doping.
Fig. 2 is the comparison curves of codope and single doping ruddiness electroluminescent device I-E characteristic.
Fig. 3 is the comparison curves of codope and single doping ruddiness electroluminescent device brightness-voltage characteristic.
Fig. 4 is the comparison curves of codope and single doping ruddiness electroluminescent device power efficiency-voltage characteristic.
Fig. 5 is the comparison curves of codope and single doping ruddiness electroluminescent device current efficiency-voltage characteristic.
Fig. 6 is the electroluminescent spectrum of device, and spectrum all derives from the emission of red dye, and main peak is at 615nm.
Embodiment:
Embodiment 1:
C545T and DCJTI are doped to Alq 3In as luminescent layer, being prepared into structure is ITO/NPB/Alq 3: C545T:DCJTI/Alq 3The electroluminescent device of/LiF/Al.10 -4Organic and the metal electrode layer of evaporation under the vacuum of handkerchief, the evaporation rate controlled of organic layer exists , the evaporation rate control of LiF
Figure C200310115873D0009114401QIETU
, the evaporation rate controlled of metal exists
Figure C200310115873D0009114408QIETU
Alq 3: the doping content ratio of C545T:DCJTI is controlled at 1:0.5%:2%.Wherein, the NPB layer thickness is 50nm, and the luminescent layer of doping is 30nm, Alq 3Layer is 20nm, and the LiF layer is 1nm, and the Al layer is 100nm.The obtained device direct voltage drive can obtain the emitting red light of DCJTI, and maximum power efficiency is 9.4lm/W, and maximum current efficient is 11.2cd/A, and high-high brightness can reach 29500cd/m 2, luminous main peak is 615nm.And the maximum power efficiency that does not add the device of C545T under the same terms only is 2.9lm/W, and maximum current efficient only is 6.3cd/A, and high-high brightness only is 10450cd/m 2
Embodiment 2:
C545T and DCJTI are doped to Alq 3In as luminescent layer, being prepared into structure is ITO/NPB/Alq 3: C545T:DCJTI/Alq 3The electroluminescent device of/LiF/Al.10 -4Organic and the metal electrode layer of evaporation under the vacuum of handkerchief, the evaporation rate controlled of organic layer exists , the evaporation rate control of LiF
Figure C200310115873D0010114440QIETU
, the evaporation rate controlled of metal exists
Figure C200310115873D0010114448QIETU
Alq 3: the doping content ratio of C545T:DCJTI is controlled at 1:0.5%:1%.Wherein, the NPB layer thickness is 50nm, and the luminescent layer of doping is 30nm, Alq 3Layer is 20nm, and the LiF layer is 1nm, and the Al layer is 100nm.The obtained device direct voltage drive can obtain the emitting red light of DCJTI, and maximum power efficiency is 8.91m/W, and maximum current efficient is 12.6cd/A, and high-high brightness can reach 33200cd/m 2, luminous main peak is 607nm.And the maximum power efficiency that does not add the device of C545T under the same terms only is 2.7lm/W, and maximum current efficient only is 7.2cd/A, and high-high brightness only is 19600cd/m 2
Embodiment 3:
C545T and DCJTB are doped to Alq 3In as luminescent layer, being prepared into structure is ITO/NPB/Alq 3: C545T:DCJTB/Alq 3The electroluminescent device of/LiF/Al.10 -4Handkerchief vacuum under the organic and metal electrode layer of evaporation, the evaporation rate controlled of organic layer exists , the evaporation rate control of LiF
Figure C200310115873D0010114525QIETU
, the evaporation rate controlled of metal exists
Figure C200310115873D0010114531QIETU
Alq 3: the doping content ratio of C545T:DCJTB is controlled at 1:0.5%:0.5%.Wherein, the NPB layer thickness is 50nm, and the luminescent layer of doping is 30nm, Alq 3Layer is 20nm, and the LiF layer is 1nm, and the Al layer is 100nm.The obtained device direct voltage drive can obtain the emitting red light of DCJTB, and maximum power efficiency is 10.9lm/W, and maximum current efficient is 11.7cd/A, and high-high brightness can reach 23700cd/m 2, luminous main peak is 612nm.And the maximum power efficiency that does not add the device of C545T under the same terms only is 3.9lm/W, and maximum current efficient only is 8.3cd/A, and high-high brightness only is 13300cd/m 2, and the obvious blue shift of spectrum, at 520nm Alq is arranged 3Light.
Embodiment 4:
C545T and DCJTB are doped to Alq 3In as luminescent layer, being prepared into structure is ITO/NPB/Alq 3: C545T:DCJTB/Alq 3The electroluminescent device of/LiF/Al is 10 -4Organic and the metal electrode layer of evaporation under the vacuum of handkerchief, the evaporation rate controlled of organic layer exists
Figure C200310115873D0011114557QIETU
, the evaporation rate control of LiF
Figure C200310115873D0011114607QIETU
, the evaporation rate controlled of metal exists
Figure C200310115873D0011114616QIETU
Alq 3: the doping content ratio of C545T:DCJTB is controlled at 1:1%:1%.Wherein, the NPB layer thickness is 50nm, and the luminescent layer of doping is 30nm, Alq 3Layer is 20nm, and the LiF layer is 1nm, and the Al layer is 100nm.The obtained device direct voltage drive can obtain the emitting red light of DCJTB, and maximum power efficiency is 3.9lm/W, and maximum current efficient is 6.7cd/A, and high-high brightness can reach 23500cd/m 2, luminous main peak is 617nm.And the maximum power efficiency that does not add the device of C545T under the same terms only is 1.2lm/W, and maximum current efficient only is 3.1cd/A, and high-high brightness only is 9750cd/m 2
Embodiment 5:
C545T and DCM are doped to Alq 3In as luminescent layer, being prepared into structure is ITO/NPB/Alq 3: C545T:DCM/Alq 3The electroluminescent device of/LiF/Al is 10 -4Organic and the metal electrode layer of evaporation under the vacuum of handkerchief, the evaporation rate controlled of organic layer exists , the evaporation rate control of LiF
Figure C200310115873D0011114653QIETU
, the evaporation rate controlled of metal exists
Figure C200310115873D0011114701QIETU
Alq 3: the doping content ratio of C545T:DCM is controlled at 1:1%:2%.Wherein, the NPB layer thickness is 50nm, and the luminescent layer of doping is 30nm, Alq 3Layer is 20nm, and the LiF layer is 1nm, and the Al layer is 100nm.The obtained device direct voltage drive can obtain the emitting red light of DCM, and maximum power efficiency is 4.3lm/W, and maximum current efficient is 6.3cd/A, and high-high brightness can reach 16000cd/m 2, luminous main peak is 608nm.And the maximum power efficiency that does not add the device of C545T under the same terms only is 0.9lm/W, and maximum current efficient only is 2.8cd/A, and high-high brightness only is 8380cd/m 2, and the obvious blue shift of spectrum.
Embodiment 6:
C545T and Nile red are doped to Alq 3In as luminescent layer, being prepared into structure is ITO/NPB/Alq 3: C545T:Nile red/Alq 3The electroluminescent device of/LiF/Al is 10 -4Organic and the metal electrode layer of evaporation under the vacuum of handkerchief, the evaporation rate controlled of organic layer exists
Figure C200310115873D0012114726QIETU
, the evaporation rate control of LiF
Figure C200310115873D0012114734QIETU
, the evaporation rate controlled of metal exists
Figure C200310115873D0012114740QIETU
Alq 3: the doping content ratio of C545T:Nile red is controlled at 1:1%:1%.Wherein, the NPB layer thickness is 50nm, and the luminescent layer of doping is 30nm, Alq 3Layer is 20nm, and the LiF layer is 1nm, and the Al layer is 100nm.The obtained device direct voltage drive can obtain the emitting red light of Nile red, and maximum power efficiency is 0.8lm/W, and maximum current efficient is 1.5cd/A, and high-high brightness is 4950cd/m 2, luminous main peak is 618nm.And the maximum power efficiency that does not add the device of C545T under the same terms only is 0.22lm/W, and maximum current efficient only is 0.66cd/A, and high-high brightness only is 1770cd/m 2

Claims (4)

1, a kind of ruddiness organic electroluminescence device, it is characterized in that device is by 1) glass substrate, 2) ITO electrode layer, 3) hole transmission layer, 4) two dye adulterated luminescent layers, 5) electron transfer layer, 6) lithium fluoride (LiF) layer, 7) the metallic cathode layer forms, and wherein pair dye adulterated luminescent layers are by material of main part oxine aluminium (Alq 3) and play the green glow fluorescent dye 10-(2-[4-morpholinodithio base)-2,3,6 of carrier capture effect, 7-tetrahydrochysene-1,1,7,7-tetramethyl-1H, 5H, 11H-(1)-benzo is given a tongue-lashing the ketone group of muttering-(6,7,8-ij) quinolizine-11-ketone (C545T) and the red dye 2-{2-isopropyl-6-[2-(1 that plays luminous effect, 1,7,7-tetramethyl-2,3,6,7-tetrahydrochysene-1H, 5H-pyrido [3,2,1-ij] quinoline-9-yl)-vinyl]-pyrans-4-inner salt alkene }-malononitrile (DCJTI), the 2-{2-tert-butyl group-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydrochysene-1H, 5H-pyrido [3,2,1-ij] quinoline-9-yl)-vinyl]-pyrans-4-inner salt alkene }-malononitrile (DCJTB), 2-{2-[2-(4-dimethyl amido-phenyl)-vinyl]-6-methyl-pyrans-4-inner salt alkene }-malononitrile (DCM) or 9-diethylamide-7a, 12a-dihydro-benzo [any composition in the α] phenoxazine-5-ketone (Nile red).
2, ruddiness organic electroluminescence device as claimed in claim 1 is characterized in that the dyestuff that plays auxiliary carrier capture in pair dye adulterated luminescent layer is to be entrained in simultaneously in the main body organic molecule material by the method that is total to evaporation with the dyestuff that plays luminous effect.
3, ruddiness organic electroluminescence device as claimed in claim 1 is characterized in that hole transmission layer is NPB, and electron transfer layer is oxine aluminium (Alq 3), metallic cathode is aluminium (Al).
4, ruddiness organic electroluminescence device as claimed in claim 1, the thickness that it is characterized in that hole transmission layer is 50nm, and two dye adulterated light emitting layer thickness are 30nm, and the thickness of electron transfer layer is 20nm, the thickness of lithium fluoride (LiF) is 1nm, and the thickness of metallic cathode is 100nm.
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CN100424909C (en) * 2006-05-25 2008-10-08 中国科学院长春应用化学研究所 Metal-base polar organic transistor and preparing method
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CN106571378B (en) * 2015-10-10 2020-03-17 清华大学 Organic memory, press monitoring system and preparation method thereof
CN106654034B (en) * 2017-01-16 2019-01-01 中国科学院长春应用化学研究所 A kind of Green organic light emitting diode and preparation method thereof
CN106816542B (en) * 2017-01-16 2018-10-16 中国科学院长春应用化学研究所 A kind of white color organic electroluminescence device and preparation method thereof

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JP2001357975A (en) * 2000-06-16 2001-12-26 Rohm Co Ltd Organic el element
WO2002044302A1 (en) * 2000-11-29 2002-06-06 Nessdisplay Co., Ltd. Novel red fluorescent material and organic electroluminescent device containing same

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JP2001357975A (en) * 2000-06-16 2001-12-26 Rohm Co Ltd Organic el element
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