CN1580180A - Method for preparing organic electroluminescent device of copper (I) phosphorescence material - Google Patents
Method for preparing organic electroluminescent device of copper (I) phosphorescence material Download PDFInfo
- Publication number
- CN1580180A CN1580180A CN 200410010864 CN200410010864A CN1580180A CN 1580180 A CN1580180 A CN 1580180A CN 200410010864 CN200410010864 CN 200410010864 CN 200410010864 A CN200410010864 A CN 200410010864A CN 1580180 A CN1580180 A CN 1580180A
- Authority
- CN
- China
- Prior art keywords
- carbonatoms
- title complex
- luminescent layer
- copper
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000463 material Substances 0.000 title claims abstract description 44
- 238000000034 method Methods 0.000 title claims abstract description 10
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 title claims description 15
- 239000000203 mixture Substances 0.000 claims abstract description 9
- -1 quinolyl copper complexes Chemical class 0.000 claims abstract description 5
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 claims description 71
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 claims description 12
- 239000011521 glass Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
- 238000004528 spin coating Methods 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 11
- 230000005540 biological transmission Effects 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 238000005401 electroluminescence Methods 0.000 claims description 9
- 150000002500 ions Chemical class 0.000 claims description 9
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 9
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 9
- 239000004793 Polystyrene Substances 0.000 claims description 8
- 239000003446 ligand Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 150000003384 small molecules Chemical class 0.000 claims description 8
- 239000010949 copper Substances 0.000 claims description 6
- 239000004417 polycarbonate Substances 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 229910020366 ClO 4 Inorganic materials 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- OAFXFZNYKPMZBJ-UHFFFAOYSA-N copper(1+);phosphane Chemical compound P.[Cu+] OAFXFZNYKPMZBJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 229920002223 polystyrene Polymers 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
- ZSYMVHGRKPBJCQ-UHFFFAOYSA-N 1,1'-biphenyl;9h-carbazole Chemical group C1=CC=CC=C1C1=CC=CC=C1.C1=CC=C2C3=CC=CC=C3NC2=C1 ZSYMVHGRKPBJCQ-UHFFFAOYSA-N 0.000 claims description 3
- 238000005516 engineering process Methods 0.000 claims description 3
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 229920000515 polycarbonate Polymers 0.000 claims description 3
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 claims description 2
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 claims description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229920001002 functional polymer Polymers 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims description 2
- 238000012986 modification Methods 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229920001088 polycarbazole Polymers 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 229920006389 polyphenyl polymer Polymers 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 claims description 2
- 125000005259 triarylamine group Chemical group 0.000 claims description 2
- 238000001291 vacuum drying Methods 0.000 claims description 2
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 claims 1
- 239000010410 layer Substances 0.000 abstract description 126
- 239000002356 single layer Substances 0.000 abstract description 35
- 150000001879 copper Chemical class 0.000 abstract 1
- 229920002521 macromolecule Polymers 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 description 10
- 229910052782 aluminium Inorganic materials 0.000 description 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
- 239000011575 calcium Substances 0.000 description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 230000004044 response Effects 0.000 description 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- 150000003624 transition metals Chemical class 0.000 description 4
- 238000007738 vacuum evaporation Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000004699 copper complex Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 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
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Images
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to the application of four co ordinations quinolyl copper complexes with counter ion as phosophosrescence material in organic eletrolumniescence furniture. Tow craft is adopted. First, film by self no doping liquor. Second, film by macromolecule as main material cross blend liquorl. Use two methods, lead copper complexes to luminescent layer, and then add carrier transfer material to luminescent layer or lead single carrier transfer material to form monolayer or multilayer furniture. Thus, the organic eletrolumniescence furniture can gives off highly active light from red to green.
Description
Technical field
The invention belongs to have counter ion the four-coordination univalent copper complex as the application of phosphor material in organic electroluminescence device.
Technical background
The principle of work of organic electroluminescence device is based on the hole and electronics injects from positive and negative electrode respectively, is compounded to form exciton at luminescent layer, and the exciton attenuation is luminous.According to the spin statistical theory, singlet exciton and triplet excitons respectively account for 25% and 75%.Be different from the organic molecule fluorescent material that can only utilize the singlet energy, transition metal organic coordination compound phosphor material is owing to have very strong spin-track coupling, can make full use of all form of energy that comprise singlet and triplet state, break through 25% energy limited, increase substantially the efficient of organic electroluminescence device, promptly utilized transition metal organic coordination compound phosphor material can make the internal quantum of organic electroluminescence device reach 100%.
But on concrete device is implemented,, understand owing to concentration quenching causes luminous efficiency low if phosphor material is resembled the most fluorescent material independent luminescent layer of doing, even not luminous.Common way be with phosphor material with low concentration doping in having carrier transport and the energy level material of main part higher than phosphor material, by exciton energy is delivered to phosphor material from material of main part, realize the efficiently luminous of phosphor material.On the preparation technology of electro phosphorescent device luminescent layer, general now vacuum vapour deposition film forming and these two kinds of methods of solution spin-coating method film forming of adopting.With vacuum vapour deposition film forming ratio, solution spin-coating method film forming is more economical, easy, be fit to preparation big area display screen, adopt the film forming device of vacuum vapour deposition, this film to become the trend of organic electroluminescence device development from now on although adopt the performance of the device of solution spin-coating film it would be better at present.Electrophosphorescent device for adopting the solution spin-coating film can adopt single layer structure, promptly has only luminescent layer between two electrolysis; Also can adopt multilayered structure further to optimize, promptly on the luminescent layer that has revolved again on the evaporation one to two-layer hole blocking layer and electron transfer layer, be only metal electrode at last.
In the selection of electrophosphorescent material, the title complex of using at present that mainly contains Ir (III), Pt (II), Os (II), Re heavy metals such as (I) is wherein with the most outstanding based on the device performance of Ir (III) title complex.
With respect to the 5th, the noble metal of period 6, period 4 transition metal aboundresources, cheap and easy to get, and toxicity is less.Copper (I) title complex is typical case's representative of period 4 transition metal title complex, before two more than ten years its photoluminescence performance is just carried out extensively and systematic research.But the electroluminescent phosphorescence research about copper (I) title complex in the document is few, only has Jilin University to carry out its preliminary study (Advanced Materials, 11,852-857,1999) in 1999.They adopt four caryogamy compounds of a kind of copper (I) to do phosphorescent coloring, mix up in the Polyvinyl carbazole material of main part, and the multilayer device of preparation is 50cd/m at luminosity
2Situation under external quantum efficiency have only 0.1%, also do not show the superiority of using as electromechanical phosphorescent material.
Summary of the invention
The preparation method who the purpose of this invention is to provide the organic electroluminescence device of a kind of copper (I) phosphor material.
The present invention adopts self non-doped solution film forming or with two kinds of methods of polymer main body material blend solution film forming copper (I) title complex is introduced luminescent layer, by in luminescent layer, mixing up carrier transmission material, or the carrier blocking layers that induces one independent beyond luminescent layer structure single or multiple lift device, realize organic electroluminescence device efficiently luminous from the green to the redness.Significantly different with other phosphor material is that copper (I) phosphor material that the present invention adopts uses as luminescent layer with non-doping, also can obtain high device efficiency, is 100cd/m at luminosity
2Situation under current efficiency reach as high as 29cd/A.
The copper that the present invention chooses (I) title complex is monokaryon four-coordination structure, has following two kinds of base types:
Among the general structure I
Representative is the bidentate ligand of ligating atom with nitrogen, can be a kind of in the following part:
X is oxygen or sulphur atom in the formula; R
1Can be the alkyl of hydrogen, trifluoromethyl, carbonatoms 1-8 or the alkoxyl group of carbonatoms 1-10; R
2, R
3Can be the alkyl of hydrogen, phenyl, phenoxy group, phenylacetylene base, carbazyl, carbonatoms 1-8 or the alkoxyl group of carbonatoms 1-10; R
4Can be hydrogen or methyl; R
5It can be the alkyl of hydrogen, phenyl or carbonatoms 1-8; R
1, R
2, R
3, R
4, R
5Also can further be replaced,, at most only should be replaced simultaneously at two places therein being substituted the part that base replaces in a plurality of positions;
Representing two (2-diphenylphosphino) phenyl ethers or two independent triphenylphosphine ligands, can be a group in following four group ligands:
R in the formula
1Can be hydrogen, N, the alkyl of N '-hexichol amido, carbazyl, carbonatoms 1-8 or the alkoxyl group of carbonatoms 1-10; R
2Can be the alkyl of carbonatoms 1-8 or the alkoxyl group of carbonatoms 1-10, R
1, R
2Also can further be replaced; Ac
-Be the negative ion that contends with, be ClO
4 -, BF
4 -Or FP
6 -Part
And the negative ion Ac that contends with
-But three's arbitrary combination;
Among the general structure II
Represent 1 of 2,9 replacements, 10-phenanthroline part, two in the complex molecule
Part can be identical, also can be different, adhere to following two kinds of situations separately:
In the structural formula 1: R
1Can be the alkyl of phenyl, trifluoromethyl, phenylacetylene base, carbonatoms 1-8 or the alkoxyl group of carbonatoms 1-10; R
2Can be the alkyl of hydrogen, phenyl, phenoxy group, phenylacetylene base, carbazyl, carbonatoms 1-8 or the alkoxyl group of carbonatoms 1-10; In the structural formula 2: R
3, R
4Can be the alkyl of hydrogen, carbonatoms 1-8 or the alkoxyl group of carbonatoms 1-10, R
3, R
4Can be identical, also can be different; R
1, R
2, R
3, R
4Also can further be replaced; Ac
-Be the negative ion that contends with, be ClO
4 -, BF
4 -Or FP
6 -
All Cu (I) title complex all closes copper by the ligand exchange method from the tetrem nitrile of being with the negative ion acid group and makes indirectly.
The luminescent layer of device adopts the preparation of solution spin-coating film method, and technology is as follows: copper (I) title complex is dissolved in CH
2Cl
2Solution is spin-coated under the condition of 1500 rev/mins of rotating speeds through polythiofuran derivative (PEDOT) and modifies or without the ito glass surface of its modification, vacuum-drying; The concentration range that is used for copper (I) complex solution of spin coating is 20mg/ml-100mg/ml; Also can be at the CH of copper (I) title complex
2Cl
2Add polymer main body material in the solution, the blend spin coating prepares luminescent layer, and selected polymer main body material is general purpose polyester or the functional polymer with carrier transmission characteristics: polymethylmethacrylate, polystyrene, polycarbonate, polyphenyl, Polyvinyl carbazole, polycarbazole or poly-fluorenes; Copper (I) title complex and polymer main body material are at CH
2Cl
2Weight ratio in the solution is 1: 0.15-100; By regulating the concentration of mixing solutions, with the gauge control of luminescent layer at 100 ± 30nm; Also can further mix small molecules carrier transmission material: 2-(4-phenylbenzene)-5-(4-tert-butyl-phenyl)-1 in the luminescent layer of copper (I) title complex and polymer main body material blend preparation, 3,4-oxadiazole (PBD), 1,3,5-three (2-N-phenyl benzimidazolyl-) benzene (TPBI), 3-(4-phenylbenzene)-5-(4-tert-butyl-phenyl)-4-(4-ethylphenyl)-1,2,4-triazole (TAZ), N, N '-two (3-aminomethyl phenyl)-N, N '-phenylbenzene-1,1 '-phenylbenzene-4,4 '-diamines (TPD), N, N '-two (how basic 1-is)-N, N '-phenylbenzene-1,1 '-phenylbenzene-4,4 '-diamines (NPD) or 4,4-N, N-two carbazole biphenyl (CBP); The small molecules carrier transmission material is not limited thereto, and can be the small molecules of any band triarylamine, carbazyl Huo oxadiazole base; Small molecules carrier transmission material and polymer main body material are at CH
2Cl
2Weight ratio in the solution is 1: 0.3-3.
Load onto in set of devices, direct evaporation metal electrode behind the intact luminescent layer of spin coating is made single layer device; Also the vacuum available vapour deposition method further introduces one to two-layer organic molecule layer with hole barrier or electric transmission function between metal electrode and luminescent layer, the structure multilayer device.
Description of drawings
To be device ITO/PEDOT/ be current efficiency and the power efficiency figure of the pairing complex molecule formula of embodiment 4/Ca/Al with accompanying drawing 1, and there is the response time delay phenomenon of similar luminescent electrochemical cell (LEC) in device, this figure correspondence be the state of device after stable.
To be device ITO/PEDOT/ title complexs be voltage-luminance graph of the pairing molecular formula 4/Ca/Al of embodiment with accompanying drawing 2, and there is the response time delay phenomenon in device, this figure correspondence be the state of device after stable.
Accompanying drawing 3 is device ITO/PEDOT/PVK: title complex is the current efficiency figure of the pairing molecular formula 42/TPBI/LiF/Al of embodiment, and energising back device moment rises bright.
Accompanying drawing 4 is device ITO/PEDOT/PVK: title complex is voltage-luminance graph of the pairing molecular formula 42/TPBI/LiF/Al of embodiment, and energising back device moment rises bright.
Embodiment
The pairing molecular formula of each embodiment is as follows:
Embodiment 1: be the multilayer device of luminescent layer with title complex 1/PVK
Device architecture is: ITO/PEDOT/ luminescent layer/BCP/Alq
3/ LiF/Al.Assembling condition is: at ito glass surface spin coating last layer conducting polymer---the polythiofuran derivative (PEDOT) of cleaning, following dry 30 minutes at 120 ℃ subsequently under the condition of 3000 rev/mins of rotating speeds.With PVK (Polyvinyl carbazole) and title complex 1 at CH
2Cl
2Be made into weight ratio in the solution and be 100/1 solution, under the condition of 1500 rev/mins of rotating speeds, be spin-coated on the glass electrode surface of modifying through PEDOT.After under the condition of high vacuum dry 2 hours, the BCP of 10nm (2,9-dimethyl-4,7-phenylbenzene-1,10-phenanthroline) on the evaporation successively, the Alq of 50nm
3The LiF of (oxine aluminium), 1nm and the metallic aluminium of 100nm.The multilayer device performance is as follows: trigger voltage 10V, high-high brightness 1000cd/m
2, maximum current efficient 2.5cd/A, maximum luminous peak position 543nm.
Embodiment 2: be the single layer device of luminescent layer with title complex 2/PVK/PBD
Device architecture is: ITO/PEDOT/ luminescent layer/Ca/Al.Assembling condition is: with PVK, PBD (2-(4-phenylbenzene)-5-(4-tert-butyl-phenyl)-1,3,4-oxadiazole) and title complex 2 at CH
2Cl
2Be made into weight ratio in the solution and be 100/40/2 solution, under the condition of 1500 rev/mins of rotating speeds, be spin-coated on the ito glass electrode surface of modifying through PEDOT.After under the condition of high vacuum dry 2 hours, the metallic aluminium of the calcium metal of 1nm and 100nm on the evaporation.The single layer device performance is as follows: trigger voltage 10V, high-high brightness 1200cd/m
2, maximum current efficient 2.8cd/A, maximum luminous peak position 555nm.
Embodiment 3: be the multilayer device of luminescent layer with title complex 3/PVK
The weight ratio of PVK and title complex 2 is 100/2 in the multilayer device luminescent layer, and other assembling condition is with embodiment 1.The multilayer device performance is as follows: trigger voltage 11V, high-high brightness 1400cd/m
2, maximum current efficient 3.2cd/A, maximum luminous peak position 525nm.
Embodiment 4: be the non-doping single layer device of luminescent layer with title complex 4
Device architecture is: ITO/PEDOT/ luminescent layer/Ca/Al.Assembling condition is: with title complex 4 at CH
2Cl
2In be made into the solution of 60mg/ml, under the condition of 1500 rev/mins of rotating speeds, be spin-coated on the ito glass electrode surface of modifying through PEDOT.After under the condition of high vacuum dry 2 hours, the metallic aluminium of the calcium metal of 1nm and 100nm in the vacuum evaporation.The single layer device performance is as follows: trigger voltage 3V, high-high brightness 5000cd/m
2, maximum current efficient 28cd/A, there is the response time delay phenomenon in maximum luminous peak position 524nm, referring to accompanying drawing 1,2.
Embodiment 5: be the non-doping single layer device of luminescent layer with title complex 4
Device architecture is: ITO/ luminescent layer/Al.Assembling condition is: with title complex 4 at CH
2Cl
2In be made into the solution of 100mg/ml, under the condition of 1500 rev/mins of rotating speeds, be spin-coated on the ito glass electrode surface that cleaned.After under the condition of high vacuum dry 2 hours, the metallic aluminium of 100nm in the vacuum evaporation.The single layer device performance is as follows: trigger voltage 5V, high-high brightness 1800cd/m
2, maximum current efficient 8cd/A, there is the response time delay phenomenon in maximum luminous peak position 524nm.
Embodiment 6: be the multilayer device of luminescent layer with title complex 5/PMMA
Device architecture is: ITO/PEDOT/ luminescent layer/Ca/Al.Assembling condition is: with polymethylmethacrylate (PMMA) and title complex 4 at CH
2Cl
2Be made into weight ratio in the solution and be 15/85 solution, under the condition of 1500 rev/mins of rotating speeds, be spin-coated on the ito glass electrode surface of modifying through PEDOT.After under the condition of high vacuum dry 2 hours, the metallic aluminium of the calcium metal of 1nm and 100nm in the vacuum evaporation.The single layer device performance is as follows: trigger voltage 4V, high-high brightness 6000cd/m
2, maximum current efficient 29cd/A, there is the response time delay phenomenon in maximum luminous peak position 525nm.
Embodiment 7: be the multilayer device of luminescent layer with title complex 6/PVK
The weight ratio of PVK and title complex 6 is 100/5 in the multilayer device luminescent layer.Other assembling condition is with embodiment 1.The multilayer device performance is as follows: trigger voltage 16V, high-high brightness 600cd/m
2, maximum current efficient 2.3cd/A, maximum luminous peak position 505nm.
Embodiment 8: be the bi-layer devices of luminescent layer with title complex 7/PVK
Device architecture is: ITO/PEDOT/ luminescent layer/TPBI/LiF/Al.Assembling condition is: with PVK and title complex 1 at CH
2Cl
2Be made into weight ratio in the solution and be 100/60 solution, under the condition of 1500 rev/mins of rotating speeds, be spin-coated on the ito glass electrode surface of modifying through PEDOT.After under the condition of high vacuum dry 2 hours, successively on the evaporation 1,3 of 60nm, 5-three (2-N-phenyl benzimidazolyl-) benzene (TPBI), the LiF of 1nm and the metallic aluminium of 100nm.The bi-layer devices performance is as follows: trigger voltage 11V, high-high brightness 3900cd/m
2, maximum current efficient 14cd/A, maximum luminous peak position 535nm.
Embodiment 9: be the multilayer device of luminescent layer with title complex 8/PVK
The weight ratio of PVK and title complex 8 is 100/10 in the multilayer device luminescent layer.Other assembling condition is with embodiment 1.The multilayer device performance is as follows: trigger voltage 12V, high-high brightness 2800cd/m
2, maximum current efficient 5.5cd/A, maximum luminous peak position 545nm.
Embodiment 10: be the single layer device of luminescent layer with title complex 9/PVK/PBD
The weight ratio of PVK, PBD and title complex 9 is 100/40/10 in the single layer device luminescent layer.Other assembling condition is with embodiment 2.The single layer device performance is as follows: trigger voltage 11V, high-high brightness 3600cd/m
2, maximum current efficient 7.0cd/A, maximum luminous peak position 545nm.
Embodiment 11: be the bi-layer devices of luminescent layer with title complex 10/PS
Device architecture is: ITO/PEDOT/ luminescent layer/TPBI/LiF/Al.Assembling condition is: with PS (polystyrene) and title complex 10 at CH
2Cl
2Be made into weight ratio in the solution and be 1/3 solution, under the condition of 1500 rev/mins of rotating speeds, be spin-coated on the glass electrode surface of modifying through PEDOT.After under the condition of high vacuum dry 2 hours, the metallic aluminium of the LiF of the TPBI of 60nm, 1nm and 100nm on the evaporation successively.The bi-layer devices performance is as follows: trigger voltage 6V, high-high brightness 1800cd/m
2, maximum current efficient 5cd/A, maximum luminous peak position 515nm.
Embodiment 12: be the multilayer device of luminescent layer with title complex 11/PVK
The weight ratio of PVK and title complex 11 is 100/10 in the multilayer device luminescent layer.Other assembling condition is with embodiment 1.The multilayer device performance is as follows: trigger voltage 8V, high-high brightness 2300cd/m
2, maximum current efficient 3.9cd/A, maximum luminous peak position 515nm.
Embodiment 13: be the non-doping single layer device of luminescent layer with title complex 12
Device architecture is: ITO/ luminescent layer/Ca/Al.Assembling condition is: with title complex 12 at CH
2Cl
2In be made into the solution of 20mg/ml, under the condition of 1500 rev/mins of rotating speeds, be spin-coated on the ito glass surface of cleaning.After under the condition of high vacuum dry 2 hours, the metallic aluminium of the calcium metal of 1nm and 100nm in the vacuum evaporation.The single layer device performance is as follows: trigger voltage 5V, high-high brightness 500cd/m
2, maximum current efficient 2cd/A, there is the response time delay phenomenon in maximum luminous peak position 519nm.
Embodiment 14: be the multilayer device of luminescent layer with title complex 13/PVK
The weight ratio of PVK and title complex 13 is 100/5 in the multilayer device luminescent layer.Other assembling condition is with embodiment 1.The multilayer device performance is as follows: trigger voltage 17V, high-high brightness 700cd/m
2, maximum current efficient 1.5cd/A, maximum luminous peak position 525nm.
Embodiment 15: be the multilayer device of luminescent layer with title complex 14/PVK
The weight ratio of PVK and title complex 14 is 100/10 in the multilayer device luminescent layer.Other assembling condition is with embodiment 1.The multilayer device performance is as follows: trigger voltage 10V, high-high brightness 800cd/m
2, maximum current efficient 3.0cd/A, maximum luminous peak position 538nm.
Embodiment 16: be the single layer device of luminescent layer with title complex 15/PVK/PBD
The weight ratio of PVK, PBD and title complex 15 is 100/50/10 in the single layer device luminescent layer.Other assembling condition is with embodiment 2.The single layer device performance is as follows: trigger voltage 11V, high-high brightness 3700cd/m
2, maximum current efficient 12cd/A, maximum luminous peak position 535nm.
Embodiment 17: be the multilayer device of luminescent layer with title complex 16/PVK
The weight ratio of PVK and title complex 16 is 100/5 in the multilayer device luminescent layer.Other assembling condition is with embodiment 1.The multilayer device performance is as follows: trigger voltage 11V, high-high brightness 2900cd/m
2, maximum current efficient 5.5cd/A, maximum luminous peak position 560nm.
Embodiment 18: be the single layer device of luminescent layer with title complex 17/PS/TAZ
PS in the single layer device luminescent layer (polystyrene), TAZ (3-(4-phenylbenzene)-5-(4-tert-butyl-phenyl)-4-(4-ethylphenyl)-1,2,4-triazole) are 30/30/40 with the weight ratio of title complex 17.Other assembling condition is with embodiment 2.The single layer device performance is as follows: trigger voltage 15V, high-high brightness 500cd/m
2, maximum current efficient 1.0cd/A, maximum luminous peak position 563nm.
Embodiment 19: be the bi-layer devices of luminescent layer with title complex 18/PVK
Device architecture is: ITO/PEDOT/ luminescent layer/TAZ/LiF/Al.Assembling condition is: with PVK and title complex 18 at CH
2Cl
2Be made into weight ratio in the solution and be 100/20 solution, under the condition of 1500 rev/mins of rotating speeds, be spin-coated on the glass electrode surface of modifying through PEDOT.After under the condition of high vacuum dry 2 hours, the metallic aluminium of the LiF of the TAZ of 50nm, 1nm and 100nm on the evaporation successively.The bi-layer devices performance is as follows: trigger voltage 13V, high-high brightness 1100cd/m
2, maximum current efficient 3.0cd/A, maximum luminous peak position 560nm.
Embodiment 20: be the multilayer device of luminescent layer with title complex 19/PVK
The weight ratio of PVK and title complex 19 is 100/10 in the multilayer device luminescent layer.Other assembling condition is with embodiment 1.The multilayer device performance is as follows: trigger voltage 12V, high-high brightness 4700cd/m
2, maximum current efficient 13cd/A, maximum luminous peak position 515nm.
Embodiment 21: be the multilayer device of luminescent layer with title complex 20/PVK
The weight ratio of PVK and title complex 20 is 100/5 in the multilayer device luminescent layer.Other assembling condition is with embodiment 1.The multilayer device performance is as follows: trigger voltage 13V, high-high brightness 800cd/m
2, maximum current efficient 1.9cd/A, maximum luminous peak position 564nm.
Embodiment 22: be the bi-layer devices of luminescent layer with title complex 21/PVK
The weight ratio of PVK and title complex 21 is 100/10 in the multilayer device luminescent layer.Other assembling condition is with embodiment 8.The bi-layer devices performance is as follows: trigger voltage 14V, high-high brightness 2300cd/m
2, maximum current efficient 4.5cd/A, maximum luminous peak position 564nm.
Embodiment 23: be the multilayer device of luminescent layer with title complex 22/PVK
The weight ratio of PVK and title complex 22 is 100/10 in the multilayer device luminescent layer.Other assembling condition is with embodiment 1.The multilayer device performance is as follows: trigger voltage 14V, high-high brightness 500cd/m
2, maximum current efficient 1.2cd/A, maximum luminous peak position 546nm.
Embodiment 24: be the single layer device of luminescent layer with title complex 23/PVK/PBD
The weight ratio of PVK, PBD and title complex 23 is 100/40/10 in the single layer device luminescent layer.Other assembling condition is with embodiment 2.The single layer device performance is as follows: trigger voltage 12V, high-high brightness 600cd/m
2, maximum current efficient 1.2cd/A, maximum luminous peak position 528nm.
Embodiment 25: be the multilayer device of luminescent layer with title complex 24/PVK
The weight ratio of PVK and title complex 24 is 100/10 in the multilayer device luminescent layer.Other assembling condition is with embodiment 1.The multilayer device performance is as follows: trigger voltage 12V, high-high brightness 300cd/m
2, maximum current efficient 0.4cd/A, maximum luminous peak position 558nm.
Embodiment 26: be the multilayer device of luminescent layer with title complex 25/PVK
The weight ratio of PVK and title complex 25 is 100/10 in the multilayer device luminescent layer.Other assembling condition is with embodiment 1.The multilayer device performance is as follows: trigger voltage 11V, high-high brightness 100cd/m
2, maximum current efficient 0.3cd/A, maximum luminous peak position 611nm.
Embodiment 27: be the single layer device of luminescent layer with title complex 26/PC
The weight ratio of polycarbonate in the single layer device luminescent layer (PC) and title complex 26 is 25/75.Other assembling condition is with embodiment 6.The single layer device performance is as follows: trigger voltage 3V, high-high brightness 4900cd/m
2, maximum current efficient 18cd/A, there is the response time delay phenomenon in maximum luminous peak position 525nm.
Embodiment 28: be the multilayer device of luminescent layer with title complex 27/PVK
The weight ratio of PVK and title complex 27 is 100/10 in the multilayer device luminescent layer.Other assembling condition is with embodiment 1.The multilayer device performance is as follows: trigger voltage 12V, high-high brightness 900cd/m
2, maximum current efficient 1.5cd/A, maximum luminous peak position 635nm.
Embodiment 29: be the multilayer device of luminescent layer with title complex 28/PVK
The weight ratio of PVK and title complex 28 is 100/10 in the multilayer device luminescent layer.Other assembling condition is with embodiment 1.The multilayer device performance is as follows: trigger voltage 14V, high-high brightness 300cd/m
2, maximum current efficient 0.4cd/A, maximum luminous peak position 623nm.
Embodiment 30: be the multilayer device of luminescent layer with title complex 29/PVK
The weight ratio of PVK and title complex 29 is 100/10 in the multilayer device luminescent layer.Other assembling condition is with embodiment 1.The multilayer device performance is as follows: trigger voltage 14V, high-high brightness 600cd/m
2, maximum current efficient 0.7cd/A, maximum luminous peak position 625nm.
Embodiment 31: be the multilayer device of luminescent layer with title complex 30/PMMA/CBP
PMMA, CBP in the multilayer device luminescent layer (4,4-N, N-two carbazole biphenyl) are 10/10/1 with the weight ratio of title complex 30.Other assembling condition is with embodiment 1.The multilayer device performance is as follows: trigger voltage 9V, high-high brightness 1000cd/m
2, maximum current efficient 2.2cd/A, maximum luminous peak position 545nm.
Embodiment 32: be the multilayer device of luminescent layer with title complex 31/PVK
The weight ratio of PVK and title complex 31 is 100/5 in the multilayer device luminescent layer.Other assembling condition is with embodiment 1.The multilayer device performance is as follows: trigger voltage 10V, high-high brightness 700cd/m
2, maximum current efficient 1.6cd/A, maximum luminous peak position 540nm.
Embodiment 33: be the single layer device of luminescent layer with title complex 32/PMMA/PBD
The weight ratio of PMMA, PBD and title complex 32 is 1/2/2 in the single layer device luminescent layer.Other assembling condition is with embodiment 2.The single layer device performance is as follows: trigger voltage 7V, high-high brightness 1800cd/m
2, maximum current efficient 2.7cd/A, maximum luminous peak position 540nm.
Embodiment 34: be the multilayer device of luminescent layer with title complex 33/PVK
The weight ratio of PVK and title complex 33 is 100/10 in the multilayer device luminescent layer.Other assembling condition is with embodiment 1.The multilayer device performance is as follows: trigger voltage 11V, high-high brightness 400cd/m
2, maximum current efficient 0.8cd/A, maximum luminous peak position 598nm.
Embodiment 35: be the bi-layer devices of luminescent layer with title complex 34/PVK
The weight ratio of PVK and title complex 34 is 100/10 in the bi-layer devices luminescent layer.Other assembling condition is with embodiment 8.The bi-layer devices performance is as follows: trigger voltage 11V, high-high brightness 300cd/m
2, maximum current efficient 0.6cd/A, maximum luminous peak position 602nm.
Embodiment 36: be the multilayer device of luminescent layer with title complex 35/PVK
The weight ratio of PVK and title complex 35 is 100/10 in the multilayer device luminescent layer.Other assembling condition is with embodiment 1.The multilayer device performance is as follows: trigger voltage 14V, high-high brightness 600cd/m
2, maximum current efficient 0.8cd/A, maximum luminous peak position 635nm.
Embodiment 37: be the single layer device of luminescent layer with title complex 36/PVK/PBD
The weight ratio of PVK, PBD and title complex 36 is 100/40/10 in the multilayer device luminescent layer.Other assembling condition is with embodiment 2.The single layer device performance is as follows: trigger voltage 16V, high-high brightness 500cd/m
2, maximum current efficient 0.5cd/A, maximum luminous peak position 640nm.
Embodiment 38: be the single layer device of luminescent layer with title complex 37/PF
PF in the single layer device luminescent layer (poly-fluorenes) is 100/10 with the weight ratio of title complex 37.Other assembling condition is with embodiment 2.The single layer device performance is as follows: trigger voltage 16V, high-high brightness 600cd/m
2, maximum current efficient 0.4cd/A, maximum luminous peak position 645nm.
Embodiment 39: be the multilayer device of luminescent layer with title complex 38/PVK
The weight ratio of PVK and title complex 38 is 100/10 in the multilayer device luminescent layer.Other assembling condition is with embodiment 1.The multilayer device performance is as follows: trigger voltage 17V, high-high brightness 200cd/m
2, maximum current efficient 0.2cd/A, maximum luminous peak position 655nm.
Embodiment 40: be the bi-layer devices of luminescent layer with title complex 39/PVK
The weight ratio of PVK and title complex 39 is 100/10 in the bi-layer devices luminescent layer.Other assembling condition is with embodiment 19.The bi-layer devices performance is as follows: trigger voltage 17V, high-high brightness 500cd/m
2, maximum current efficient 0.4cd/A, maximum luminous peak position 645nm.
Embodiment 41: be the multilayer device of luminescent layer with title complex 40/PVK
The multilayer device assembling condition is with embodiment 1.The multilayer device performance is as follows: trigger voltage 16V, high-high brightness 200cd/m
2, maximum current efficient 0.2cd/A, maximum luminous peak position 660nm.
Embodiment 42: be the multilayer device of luminescent layer with title complex 41/PVK
The weight ratio of PVK and title complex 41 is 100/10 in the multilayer device luminescent layer.Other assembling condition is with embodiment 1.The multilayer device performance is as follows: trigger voltage 16V, high-high brightness 1000cd/m
2, maximum current efficient 1.2cd/A, maximum luminous peak position 625nm.
Embodiment 43: be the bi-layer devices of luminescent layer with title complex 42/PVK
The weight ratio of PVK and title complex 42 is 100/10 in the bi-layer devices luminescent layer.Other assembling condition is with embodiment 8.The bi-layer devices performance is as follows: trigger voltage 14V, high-high brightness 1400cd/m
2, maximum current efficient 1.8cd/A, maximum luminous peak position 625nm is referring to accompanying drawing 1,2.
Claims (1)
1. the preparation method of the organic electroluminescence device of a copper (I) phosphor material, the copper of choosing (I) title complex is monokaryon four-coordination structure, has following two kinds of base types:
Among the general structure I
Representative is the bidentate ligand of ligating atom with nitrogen, can be a kind of in the following part:
X is oxygen or sulphur atom in the formula; R
1Can be the alkyl of hydrogen, trifluoromethyl, carbonatoms 1-8 or the alkoxyl group of carbonatoms 1-10; R
2, R
3Can be the alkyl of hydrogen, phenyl, phenoxy group, phenylacetylene base, carbazyl, carbonatoms 1-8 or the alkoxyl group of carbonatoms 1-10; R
4Can be hydrogen or methyl; R
5It can be the alkyl of hydrogen, phenyl or carbonatoms 1-8; R
1, R
2, R
3, R
4, R
5Also can further be replaced,, at most only should be replaced simultaneously at two places therein being substituted the part that base replaces in a plurality of positions;
Representing two (2-diphenylphosphino) phenyl ethers or two independent triphenylphosphine ligands, can be a group in following four group ligands:
R in the formula
1Can be hydrogen, N, the alkyl of N '-hexichol amido, carbazyl, carbonatoms 1-8 or the alkoxyl group of carbonatoms 1-10; R
2Can be the alkyl of carbonatoms 1-8 or the alkoxyl group of carbonatoms 1-10, R
1, R
2Also can further be replaced; Ac
-Be the negative ion that contends with, be ClO
4 -, BF
4 -Or FP
6 -Part
And the negative ion Ac that contends with
-But three's arbitrary combination;
Among the general structure II
Represent 1 of 2,9 replacements, 10-phenanthroline part, two in the complex molecule
Part can be identical, also can be different, adhere to following two kinds of situations separately:
In the structural formula 1: R
1Can be the alkyl of phenyl, trifluoromethyl, phenylacetylene base, carbonatoms 1-8 or the alkoxyl group of carbonatoms 1-10; R
2Can be the alkyl of hydrogen, phenyl, phenoxy group, phenylacetylene base, carbazyl, carbonatoms 1-8 or the alkoxyl group of carbonatoms 1-10; In the structural formula 2: R
3, R
4Can be the alkyl of hydrogen, carbonatoms 1-8 or the alkoxyl group of carbonatoms 1-10, R
3, R
4Can be identical, also can be different; R
1, R
2, R
3, R
4Also can further be replaced; Ac
-Be the negative ion that contends with, be ClO
4 -, BF
4 -Or FP
6 -
All Cu (I) title complex all closes copper by the ligand exchange method from the tetrem nitrile of being with the negative ion acid group and makes indirectly;
The luminescent layer of device adopts the preparation of solution spin-coating film method, and technology is as follows: copper (I) title complex is dissolved in CH
2Cl
2Solution is spin-coated under the condition of 1500 rev/mins of rotating speeds through polythiofuran derivative (PEDOT) and modifies or without the ito glass surface of its modification, vacuum-drying; The concentration range that is used for copper (I) complex solution of spin coating is 20mg/ml-100mg/ml; Also can be at the CH of copper (I) title complex
2Cl
2Add polymer main body material in the solution, the blend spin coating prepares luminescent layer, and selected polymer main body material is polyester or the functional polymer with carrier transmission characteristics: polymethylmethacrylate, polystyrene, polycarbonate, polyphenyl, Polyvinyl carbazole, polycarbazole or poly-fluorenes; Copper (I) title complex and polymer main body material are at CH
2Cl
2Weight ratio in the solution is 1: 0.15-100; By regulating the concentration of mixing solutions, with the gauge control of luminescent layer at 100 ± 30nm; Also can further mix small molecules carrier transmission material: 2-(4-phenylbenzene)-5-(4-tert-butyl-phenyl)-1 in the luminescent layer of copper (I) title complex and polymer main body material blend preparation, 3,4-oxadiazole (PBD), 1,3,5-three (2-N-phenyl benzimidazolyl-) benzene (TPBI), 3-(4-phenylbenzene)-5-(4-tert-butyl-phenyl)-4-(4-ethylphenyl)-1,2,4-triazole (TAZ), N, N '-two (3-aminomethyl phenyl)-N, N '-phenylbenzene-1,1 '-phenylbenzene-4,4 '-diamines (TPD), N, N '-two (how basic 1-is)-N, N '-phenylbenzene-1,1 '-phenylbenzene-4,4 '-diamines (NPD) or 4,4-N, N-two carbazole biphenyl (CBP); The small molecules carrier transmission material can be the small molecules of any band triarylamine, carbazyl Huo oxadiazole base; Small molecules carrier transmission material and polymer main body material are at CH
2Cl
2Weight ratio in the solution is 1: 0.3-3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100108648A CN1307281C (en) | 2004-05-20 | 2004-05-20 | Method for preparing organic electroluminescent device of copper (I) phosphorescence material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100108648A CN1307281C (en) | 2004-05-20 | 2004-05-20 | Method for preparing organic electroluminescent device of copper (I) phosphorescence material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1580180A true CN1580180A (en) | 2005-02-16 |
| CN1307281C CN1307281C (en) | 2007-03-28 |
Family
ID=34581642
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2004100108648A Expired - Fee Related CN1307281C (en) | 2004-05-20 | 2004-05-20 | Method for preparing organic electroluminescent device of copper (I) phosphorescence material |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1307281C (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100467462C (en) * | 2006-03-31 | 2009-03-11 | 北京大学 | Terdentate ligand contg. heteroaryl pyrazole, its Eu complex and electroluminescent element |
| WO2010082924A1 (en) * | 2009-01-14 | 2010-07-22 | Universal Display Corporation | Cross-linkable copper phthalocyanine complexes |
| CN101787276A (en) * | 2010-02-26 | 2010-07-28 | 光景生物科技(苏州)有限公司 | Phosphorescent microballoon with functionalized surface, kit containing phosphorescent maicroballoon and application |
| CN102851024A (en) * | 2012-09-28 | 2013-01-02 | 太原理工大学 | Organic electroluminescent material based on bis(2-diphenylphosphinophenyl)ether serving as ligand |
| CN102876320A (en) * | 2012-10-10 | 2013-01-16 | 中国计量学院 | Cuprous complex luminescent material and preparation method thereof |
| CN102899029A (en) * | 2012-09-04 | 2013-01-30 | 中国计量学院 | Luminescent material of cuprous iodide complex and preparation method thereof |
| CN103588794A (en) * | 2013-11-22 | 2014-02-19 | 中国计量学院 | Cuprous complex luminescence material and preparation method thereof |
| CN103626789A (en) * | 2013-11-22 | 2014-03-12 | 中国计量学院 | Binuclear cuprous complex luminescent material and preparation method thereof |
| CN103880867A (en) * | 2014-03-03 | 2014-06-25 | 中国计量学院 | Di-nuclear cuprous complex green luminescent material and preparation method thereof |
| CN104892645A (en) * | 2015-06-17 | 2015-09-09 | 中国计量学院 | Cuprous complex phosphor material of methyl substitution benzoxazolyl pyridine |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001244077A (en) * | 2000-03-01 | 2001-09-07 | Fuji Photo Film Co Ltd | Organic light emitting device |
| JP2004095443A (en) * | 2002-09-02 | 2004-03-25 | Dainippon Printing Co Ltd | Organic el element |
-
2004
- 2004-05-20 CN CNB2004100108648A patent/CN1307281C/en not_active Expired - Fee Related
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100467462C (en) * | 2006-03-31 | 2009-03-11 | 北京大学 | Terdentate ligand contg. heteroaryl pyrazole, its Eu complex and electroluminescent element |
| WO2010082924A1 (en) * | 2009-01-14 | 2010-07-22 | Universal Display Corporation | Cross-linkable copper phthalocyanine complexes |
| CN101787276A (en) * | 2010-02-26 | 2010-07-28 | 光景生物科技(苏州)有限公司 | Phosphorescent microballoon with functionalized surface, kit containing phosphorescent maicroballoon and application |
| CN101787276B (en) * | 2010-02-26 | 2013-01-09 | 光景生物科技(苏州)有限公司 | Phosphorescent microballoon with functionalized surface, kit containing phosphorescent maicroballoon and application |
| CN102899029A (en) * | 2012-09-04 | 2013-01-30 | 中国计量学院 | Luminescent material of cuprous iodide complex and preparation method thereof |
| CN102851024A (en) * | 2012-09-28 | 2013-01-02 | 太原理工大学 | Organic electroluminescent material based on bis(2-diphenylphosphinophenyl)ether serving as ligand |
| CN102876320A (en) * | 2012-10-10 | 2013-01-16 | 中国计量学院 | Cuprous complex luminescent material and preparation method thereof |
| CN102876320B (en) * | 2012-10-10 | 2014-01-08 | 中国计量学院 | Cuprous complex luminescent material and preparation method thereof |
| CN103588794A (en) * | 2013-11-22 | 2014-02-19 | 中国计量学院 | Cuprous complex luminescence material and preparation method thereof |
| CN103626789A (en) * | 2013-11-22 | 2014-03-12 | 中国计量学院 | Binuclear cuprous complex luminescent material and preparation method thereof |
| CN103588794B (en) * | 2013-11-22 | 2016-06-01 | 中国计量学院 | A kind of univalent copper complex luminescent material and its preparation method |
| CN103880867A (en) * | 2014-03-03 | 2014-06-25 | 中国计量学院 | Di-nuclear cuprous complex green luminescent material and preparation method thereof |
| CN104892645A (en) * | 2015-06-17 | 2015-09-09 | 中国计量学院 | Cuprous complex phosphor material of methyl substitution benzoxazolyl pyridine |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1307281C (en) | 2007-03-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN100484353C (en) | Organic electroluminescent part | |
| CN100335462C (en) | Carbazole derivative and its application in electroluminescent device | |
| CN106316924A (en) | Thermally activated delayed fluorescence material | |
| CN1773746A (en) | Organic electroluminescent device | |
| CN1389934A (en) | Organic luminescent device containing coloured neutral dopant in hole transfer layer and/or electronic transfer layer | |
| CN1897325A (en) | White organic light emitting diode | |
| CN1482691A (en) | Display device with anthracene and triazine derivatives | |
| CN1517427A (en) | Compound with red light and organic electroluminescence device using the compound | |
| CN1725918A (en) | Organic light emitting device | |
| CN101635334A (en) | Red organic electroluminescence device and preparation method thereof | |
| CN1623990A (en) | Carbazole-containing compound and organic electroluminescence display device using the compound | |
| CN100470877C (en) | Organic electro phosphorescent device and its preparation method | |
| CN102651454A (en) | Electroluminescent device, display device and preparation method of electroluminescent device | |
| CN101009364B (en) | Composition for electron transport layer, electron transport layer manufactured thereof, and organic electroluminescent device including the electron transport layer | |
| CN106328828A (en) | Organic electroluminescent device | |
| CN1161002C (en) | Organic electroluminescent device | |
| CN1643109A (en) | Organic electroluminescence element | |
| CN1580180A (en) | Method for preparing organic electroluminescent device of copper (I) phosphorescence material | |
| Li et al. | Green organic light-emitting devices with external quantum efficiency up to nearly 30% based on an iridium complex with a tetraphenylimidodiphosphinate ligand | |
| CN103531714A (en) | Electron transport layer, organic electroluminescent device comprising same and preparation thereof | |
| CN101079471A (en) | An organic EL part | |
| CN100495761C (en) | Organic electro-white light device and producing method thereof | |
| CN1749352A (en) | Organic rare-earth ligand capable of regulating carrier transport power and its preparing method and use | |
| CN101030625A (en) | Organic electroluminescent device | |
| CN101394696A (en) | Organic EL device |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20070328 |