CN100554366C - The organic electroluminescence device of the complex of iridium of dendroid green light, its method for making and this title complex - Google Patents
The organic electroluminescence device of the complex of iridium of dendroid green light, its method for making and this title complex Download PDFInfo
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Abstract
The invention belongs to technical field of organic electroluminescence, relate to the organic electroluminescence device of complex of iridium, its method for making and this title complex of dendroid green light.This compound has following structure: this compound adopts the two step method preparation.At first, part and IrCl
33H
2The O reaction forms the precursor of chlorine bridge, and chlorine bridge precursor at high temperature is converted into final product then.By the non-doping electric electroluminescence device of this compound, luminous efficiency is up to 53.2cd/A, and maximum power efficiency is 42.4lm/W, and maximum external quantum efficiency is 15.8%, and high-high brightness is 17600cd/m
2
Description
Technical field
The invention belongs to technical field of organic electroluminescence, relate to the organic electroluminescence device of complex of iridium, its method for making and this title complex of dendroid green light.
Technical background
Electroluminescent organic material and device are current international forward position research fields.At present, the commercialization of many electroluminescent organic materials, part organic display spare has also obtained application at aspects such as mobile phone, automobile audios.
According to the difference of principle of luminosity, electroluminescent organic material can be divided into fluorescent material and phosphor material two big classes.For phosphor material, owing to can make full use of all form of energy that comprise singlet and triplet state, increase substantially the efficient of device, can make the internal quantum efficiency of device reach 100% in theory.Therefore, utilize transition metal complex to become a kind of good methods that improves device efficiency as luminescent material.
Yet for the efficient that obtains, this class phosphor material generally is entrained in the material of main part in certain proportion and uses.This has just caused in the preparation of devices process, how to choose suitable material of main part and has become a big problem.For example need to consider problem of phase separation, the matching problem between the triplet between material of main part and the phosphor material, carrier transport problem of material of main part etc.Simultaneously, how accurate controlled doping concentration has also become the big difficult point of one in the device preparation technology.For this reason, the exploitation solution processable, phosphor material efficiently, and be used to construct non-adulterated organic electroluminescence device, become a major challenge of academia and industrial community.
Summary of the invention
For solving above-mentioned technical problem, the present invention is based on the characteristics of dendrimer, with the carbazole unit with cavity transmission ability is branch, develop the complex of iridium of dendroid green light, and being used to construct non-adulterated organic electroluminescence device, the efficient of its device can compare favourably with the doping device.
The complex of iridium that the purpose of this invention is to provide the dendroid green light.
Another object of the present invention provides the preparation method of the complex of iridium of dendroid green light.
The 3rd purpose of the present invention provides the purposes of the complex of iridium of dendroid green light: be manufactured with organic electroluminescence devices with this title complex.
The complex of iridium of dendroid green light provided by the present invention, its chemical formula is shown in (1):
The preparation method of the complex of iridium of dendroid green light is described below, and its step and condition are as follows:
1, ligand L G and IrCl
33H
2The O reaction forms chlorine bridge precursor: ligand L G and title complex IrCl
33H
2The mol ratio of O is 2～5, preferred 2～2.5; Temperature of reaction is 100 ℃～140 ℃, and the reaction times is 24～72 hours; Reaction solvent uses the mixed solvent of ethylene glycol monomethyl ether and water, and both volume ratios are 3: 1; In order to improve the solvability of system, can add 0～50% tetrahydrofuran (THF); The chemical formula of described ligand L G is shown in (2);
2, the complex of iridium of the dendroid green light that obtains of chlorine bridge precursor that is obtained by above step 1 and ligand L G reaction: the mol ratio of ligand L G and chlorine bridge precursor is 2～5, preferred 2～2.5; Catalyzer uses basic cpd, as K
2CO
3, Na
2CO
3, Cs
2CO3 or CF
3SO
3Ag, preferred K
2CO
3Temperature of reaction is 200 ℃～250 ℃, and the reaction times is 48～96 hours; Reaction solvent uses high boiling alcohol derivatives, as 1, and 2-propylene glycol or glycerine, preferably glycerine; In order to improve the solvability of system, can add 10～50% glycol ether, Triethylene glycol or tetraethylene-glycol derivative, preferred tetraethylene-glycol.
In order to realize three of purpose of the present invention, provide a kind of organic electroluminescence device that uses the complex of iridium of above-mentioned dendroid green light.
Use above-mentioned dendroid green light complex of iridium organic EL device structure as shown in Figure 1.
A kind of organic electroluminescence device for preparing by the complex of iridium of described dendroid green light, has one or more layers organic layer between first electrode (102) that is connected with substrate (101) and second electrode (108), it is characterized in that, wherein having one deck organic layer at least is emission layer (104), and emission layer (104) is the complex of iridium of described dendroid green light.
A kind of organic electroluminescence device for preparing by the complex of iridium of described dendroid green light, it is characterized in that, having the multilayer organic layer between described first electrode (102) that is connected with substrate (101) and second electrode (108) is: hole injection layer (103), emission layer (104), hole blocking layer (105), electron transfer layer (106), electron injecting layer (107), they connect successively, described substrate (102) is connected with hole injection layer (103), and electron injecting layer (107) is connected with second electrode (108).
A kind of organic electroluminescence device of the complex of iridium preparation by described dendroid green light, its substrate 101, as the material of substrate be transparent, be easy to handle and waterproof and the surface plastic of glass substrate or transparent flexibility uniformly; Form first electrode 102 of figure on the surface of substrate 101, first electrode 102 is made of the conducting metal that is easy to inject in the hole or the metal oxide of conduction, and the material that is suitable for first electrode 102 is indium tin oxide (ITO), indium-zinc oxide (IZO), nickel (Ni), platinum (Pt) or gold (Au); Optionally form hole injection layer (HIL) 103 on first electrode 102, the material of HIL103 comprises water miscible PEDOT (poly-(3, the 4-Ethylenedioxy Thiophene)) or PSS (poly styrene sulfonate); Form EML layer 104 on HIL layer 103, EML layer 104 is made by the complex of iridium of the dendroid green light of above-mentioned chemical formula (1) separately; On EML layer 104,, form hole blocking layer (HBL) 105 by vacuum-deposited method, the material that is applicable to HBL105 comprises that (it is preferably 2 to the phenanthroline derivative, 9-dimethyl-4,7-phenylbenzene-1,10-phenanthroline (BCP)), triazole derivative, oxadiazole derivative or aluminium complex; Material Wei oxazole, oxadiazole, isoxazole, triazole, thiadiazoles, imidazoles or the aluminium complex of electron transfer layer 106; Form electron injecting layer (EIL) 107 on ETL106, the material that is used for EIL107 comprises LiF, NaCl, NaOH, CsF, Cs
2CO
3Or Ca (acac)
3Deposition second electrode 108 on EIL107, the material that is suitable for second electrode 108 is generally low work function metal, as Ca, Ba, Al, Mg or Ag.
Organic EL device structure of the present invention as shown in Figure 1, wherein HIL103, HBL105, ETL106 or EIL107 can select to use or do not use.
Below, will describe the method for making organic EL device in detail.
With reference to the accompanying drawings 1, at first form first electrode 102 of figure on the surface of substrate 101.General material as substrate be transparent, be easy to handle and waterproof and surface glass substrate or transparent, flexible plastic uniformly.Substrate 101 preferably has the thickness of 0.3～0.7mm.
Cleaning has the substrate 101 of first electrode 102, with an organic solvent, and as Virahol or acetone.After the cleaning, substrate 101 is carried out ultraviolet ray/ozonize.
Then, on first electrode 102 of substrate 101, optionally form hole injection layer (HIL) 103.HIL103 can reduce the contact resistance between first electrode 102 and the emission layer (EML) 104, increases the injectability in hole.The material that preferably is suitable for HIL103 is water miscible PEDOT (poly-(3, the 4-Ethylenedioxy Thiophene)) or PSS (poly styrene sulfonate).When applying first electrode 102, answer heat drying to form HIL103 with this material.Wherein, when PEDOT is used for HIL103, preferred dry coating under 100～250 ℃ temperature.
Then, on HIL103, form EML104.EML104 is made by the complex of iridium of the dendroid green light of above-mentioned chemical formula (1) separately.Emission layer EML104 adopts the method preparation of solution spin coating, and organic solvent can use chloroform, toluene or chlorobenzene.
On EML104,, form hole blocking layer (HBL) 105 by vacuum-deposited method.HBL105 can prevent that exciton or hole migration are in electron transfer layer (ETL) 106.The material that is applicable to HBL105 is the phenanthroline derivative, and it is preferably 2,9-dimethyl-4,7-phenylbenzene-1,10-phenanthroline, triazole derivative, oxadiazole derivative or aluminium complex.
On HBL105,, form electron transfer layer (ETL) 106 by vacuum-deposited method.The suitable material Wei oxazole, oxadiazole, isoxazole, triazole, thiadiazoles, imidazoles or the aluminium complex that are used for ETL106.
Then, forming the material that electron injecting layer (EIL) 107. is used for EIL107 on ETL106 is LiF, NaCl, NaOH, CsF, Cs
2CO
3Or Ca (acac)
3, the thickness of preferred EIL107 is 1-
At last, deposition second electrode 108 is finished the manufacturing of organic EL device on EIL107.The material that is suitable for second electrode 108 is for low work function metal, as Ca, Ba, Al, Mg or Ag.The thickness of preferred second electrode 108 is 800-
Beneficial effect: the complex of iridium of the dendroid green light of design of the present invention and synthetic chemical formula (1) is as non-adulterated phosphor material solution processable, efficient, have high thin-film light emitting efficient, can under the condition of the main consuming body material not, realize excellent device performance; Simultaneously, it has good film-forming properties and solution processing characteristics, can prepare organic electroluminescence device based on the technology of solution by solution spin coating, spray ink Printing, silk screen printing etc.By the non-doping electric electroluminescence device of this compound, luminous efficiency is up to 53.2cd/A, and maximum power efficiency is 42.4lm/W, and maximum external quantum efficiency is 15.8%, and high-high brightness is 17600cd/m
2
Description of drawings
Fig. 1 is the structural representation of organic electroluminescence device of the complex of iridium of dendroid green light.
Fig. 2 provides the current density-voltage-luminosity response of the organic EL device of embodiment 1 manufacturing;
Fig. 3 provides the change curve of the luminous efficiency of the organic EL device that embodiment 1 makes with current density;
Fig. 4 provides the change curve of the power efficiency of the organic EL device that embodiment 1 makes with current density;
Fig. 5 provides the change curve of the external quantum efficiency of the organic EL device that embodiment 1 makes with current density;
Fig. 6 provides the EL spectrum of the organic EL device of embodiment 1 manufacturing.
Embodiment
Preparation embodiment 1: the compound of chemical formula (1) synthetic
Reaction formula 1:
1), chlorine bridge precursor is synthetic
Ligand L G (908mg, 1.10mmol) and IrCl
33H
2(176mg 0.50mmol) is dissolved in 15mL ethylene glycol monomethyl ether, 5mL distilled water to O, takes a breath repeatedly 3 times, and stirring heating under argon shield behind the back flow reaction 48h, is filtered, and the precipitation that obtains is with ethanol and distilled water wash, and drying obtains impure chlorine bridge precursor.
2), the compound of chemical formula (1) is synthetic
The chlorine bridge precursor that step 1) is obtained, ligand L G (495mg, 0.60mmol), Anhydrous potassium carbonate (345mg, 2.50mmol), glycerine 25mL and tetraethylene-glycol 5mL; add in the 50ml round-bottomed flask; under argon shield, be warming up to 210 ℃, reacted 72 hours.Cool to room temperature adds distilled water, uses dichloromethane extraction, washing repeatedly, anhydrous Na
2SO
4Drying is filtered, and rotary evaporation falls solvent, and post separates purifies, and obtains the complex of iridium 133mg (productive rate 11%) of the dendroid green light of chemical formula (1).
3), the structural analysis of the compound of chemical formula (1)
Determined the structure of this dendroid title complex by NMR, MALDI-TOF and ultimate analysis.
1H?NMR(300MHz，CDCl
3)[ppm]：δ8.15(s，15H)，7.79(s，6H)，7.45-7.60(m，24H)，7.28(d，J＝8.2Hz，3H)，7.15(d，J＝7.4Hz，3H)，7.03-7.05(m，6H)，6.85(t，J＝7.1Hz，3H)，6.67-6.72(m，6H)，6.61(d，J＝8.0Hz，3H)，1.47(s，108H).
MALDI-TOF(m/z)：2663.6[M
++H].
Anal.Calcd?for?C
177H
177N
12Ir：C，79.78；H，6.70；N，6.31.Found：C，79.51；H，6.75；N，6.28.
El element prepares embodiment 1:
Use the complex of iridium of the dendroid green light of chemical formula (1) to form emission layer.The structure of device is: the complex of iridium/TPBI (60nm) of the dendroid green light of ITO/PEDOT (50nm)/chemical formula (1)/LiF (1nm)/Al (100nm).The packaging technology of device is as follows:
1, to have 100 Ω/cm
2Indium tin oxide (ITO) substrate as anode.Water miscible polythiofuran derivative (PEDOT) is spin-coated on the anode with 3000 rev/mins speed, dries by the fire 30min down at 120 ℃, forms the thick hole injection layer of 50nm.
2, the complex of iridium of the dendroid green light of chemical formula (1) is dissolved in the chlorobenzene, is made into the solution of 5 mg/ml, is spin-coated on PEDOT with 1200 rev/mins speed and goes up as emission layer.
3, on luminescent layer evaporation 60nm thick 1,3,5-three (2-N-phenyl benzimidazolyl-) benzene (TPBI) is as hole barrier and electron transfer layer.
4, the thick Al electrode of LiF that 1nm is thick on evaporation on the electron transfer layer successively and 100nm is finished the preparation of organic EL device.
The performance of the El element of gained is as follows: maximum luminous efficiency is 53.2cd/A, and maximum power efficiency is 42.4lm/W, and maximum external quantum efficiency is 15.8%, high-high brightness 17600cd/m
2, emission peak is 532nm, chromaticity coordinates CIE value x=0.39, y=0.58.
Claims (13)
1. the complex of iridium of dendroid green light is characterized in that, its chemical formula is shown in (1):
2. the preparation method of the complex of iridium of a dendroid green light as claimed in claim 1 is characterized in that preparation process and condition are:
1) ligand L G and IrCl
33H
2The O reaction forms chlorine bridge precursor: ligand L G and title complex IrCl
33H
2The mol ratio of O is 2～5, and temperature of reaction is 100 ℃～140 ℃, and the reaction times is 24～72 hours; Reaction solvent uses the mixed solvent of ethylene glycol monomethyl ether and water, and both volume ratios are 3: 1;
2) chlorine bridge precursor that is obtained by above step 1) and ligand L G reaction obtains the complex of iridium of the dendroid green light of chemical formula (1): the mol ratio of ligand L G and chlorine bridge precursor is 2～5, and catalyzer uses basic cpd to be K
2CO
3, Na
2CO
3, Cs
2CO3 or CF
3SO
3Ag, temperature of reaction is 200 ℃～250 ℃, the reaction times is 48～96 hours; It is 1 that reaction solvent uses high boiling alcohol derivatives, 2-propylene glycol or glycerine;
3. the preparation method of the complex of iridium of a dendroid green light as claimed in claim 2 is characterized in that, described step 1), ligand L G and title complex IrCl
33H
2The mol ratio of O is 2～2.5.
4. the preparation method of the complex of iridium of a dendroid green light as claimed in claim 2 is characterized in that, described step 1) in order to improve the solvability of system, adds 0～50% tetrahydrofuran (THF).
5. the preparation method of the complex of iridium of a dendroid green light as claimed in claim 2 is characterized in that, described step 2), the mol ratio of ligand L G and chlorine bridge precursor is 2～2.5.
6. the preparation method of the complex of iridium of a dendroid green light as claimed in claim 2 is characterized in that, described step 2), catalyzer uses basic cpd to be K
2CO
3
7. the preparation method of the complex of iridium of a dendroid green light as claimed in claim 2 is characterized in that, described step 2), reaction solvent uses high boiling alcohol derivatives to be glycerine.
8. the preparation method of the complex of iridium of a dendroid green light as claimed in claim 2, it is characterized in that, described step 2), in order to improve the solvability of system, add 10～50% glycol ether, Triethylene glycol or tetraethylene-glycol derivative.
9. the preparation method of the complex of iridium of a dendroid green light as claimed in claim 8 is characterized in that, described step 2), in order to improve the solvability of system, add tetraethylene-glycol.
10. the organic electroluminescence device of the complex of iridium of a dendroid green light as claimed in claim 1 preparation, has one or more layers organic layer between first electrode (102) that is connected with substrate (101) and second electrode (108), it is characterized in that, wherein having one deck organic layer at least is emission layer (104), and emission layer (104) is the complex of iridium of described dendroid green light.
11. the organic electroluminescence device of the complex of iridium of dendroid green light as claimed in claim 10 preparation, it is characterized in that, having the multilayer organic layer between described first electrode (102) that is connected with substrate (101) and second electrode (108) is: hole injection layer (103), emission layer (104), hole blocking layer (105), electron transfer layer (106), electron injecting layer (107), they connect successively, described substrate (102) is connected with hole injection layer (103), and electron injecting layer (107) is connected with second electrode (108).
12. the organic electroluminescence device of the complex of iridium of dendroid green light as claimed in claim 11 preparation is characterized in that, it is characterized in that, the material of described substrate (101) is the plastics of glass or transparent flexibility; First electrode (102) is for being easy to nickel, platinum or the gold that the hole is injected; Perhaps, indium tin oxide or indium-zinc oxide; The material of hole injection layer (103) is water miscible poly-(3, the 4-Ethylenedioxy Thiophene) or poly styrene sulfonate; Emission layer (104) is made by the complex of iridium of the dendroid green light of above-mentioned chemical formula (1) separately; The material of hole blocking layer (105) is phenanthroline derivative, triazole derivative, oxadiazole derivative or aluminium complex; Material Wei oxazole, oxadiazole, isoxazole, triazole, thiadiazoles, imidazoles or the aluminium complex of electron transfer layer (106); Electron injecting layer (107), material be LiF, NaCl, NaOH, CsF, Cs
2CO
3Or Ca (acac)
3Second electrode (108), material be low work function metal Ca, Ba, Al, Mg or Ag.
13. the organic electroluminescence device of the complex of iridium of described dendroid green light as claimed in claim 12 preparation is characterized in that the material of described hole blocking layer (105) is 2,9-dimethyl-4,7-phenylbenzene-1,10-phenanthroline.
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| US8815415B2 (en) * | 2008-12-12 | 2014-08-26 | Universal Display Corporation | Blue emitter with high efficiency based on imidazo[1,2-f] phenanthridine iridium complexes |
| CN102596939B (en) | 2009-09-16 | 2014-08-13 | 日东电工株式会社 | Compounds for organic light emitting diode emissive layers |
| US8808879B2 (en) | 2010-07-19 | 2014-08-19 | Nitto Denko Corporation | Phototherapy devices and methods comprising substituted carbazole compounds |
| CN102916135A (en) * | 2011-08-05 | 2013-02-06 | 海洋王照明科技股份有限公司 | Inverted organic light-emitting device and preparation method thereof |
| KR101474797B1 (en) * | 2011-08-08 | 2014-12-19 | 제일모직 주식회사 | Compound for organic optoelectronic device and organic light emitting diode including the same |
| JP5839912B2 (en) * | 2011-09-22 | 2016-01-06 | 株式会社半導体エネルギー研究所 | Light emitting element, light emitting device |
| CN105742520A (en) * | 2016-03-29 | 2016-07-06 | 北京大学深圳研究生院 | Color-changeable OLED device and preparation method therefor |
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| CN108658948A (en) * | 2017-03-29 | 2018-10-16 | 中国科学院长春应用化学研究所 | A kind of dendroid organometallic complex, preparation method and application |
| CN109912662B (en) * | 2019-04-11 | 2021-10-19 | 东南大学 | Solution-processable dendritic iridium complex electroluminescent material and synthesis method thereof |
| CN113105510B (en) * | 2021-04-16 | 2022-07-08 | 吉林省元合电子材料有限公司 | Metal iridium complex and organic electroluminescent device with complex as luminescent layer |
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| CN1772757A (en) * | 2005-09-16 | 2006-05-17 | 中国科学院长春应用化学研究所 | Dendritic iridium complex and organic electroluminescent device therewith |
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