CN103819511A - Aggregation-induced phosphorescence emission iridium complex and electroluminescence device thereof - Google Patents
Aggregation-induced phosphorescence emission iridium complex and electroluminescence device thereof Download PDFInfo
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Abstract
The invention provides an aggregation-induced phosphorescence emission iridium complex having a structure shown as the formula (I). The invention also provides a preparation method of the iridium complex and applications of the iridium complex in an electroluminescence device. An auxiliary ligand O^N the triplet state energy level of which is lower than that of a main ligand C-N^N is introduced, and therefore the iridium complex has strong aggregation-induced phosphorescence emission property, and is not needed to be doped into a host material or can be doped with high concentration without causing the generation of luminescent quenching phenomena, thus simplifying the device preparation, reducing the manufacturing cost of the device and increasing the luminous efficiency of the device.
Description
Technical field
The present invention relates to a kind of luminous organic material and application thereof, relate in particular to and a kind ofly there is aggregation inducing and issue the phosphor material of photoeffect and the application in electroluminescent device thereof.
Background technology
Compared with liquid-crystal display, Organic Light Emitting Diode (OLED) has the advantages such as response is fast, wide, the flexible demonstration in visual angle, compared with cathode ray tube (CRT) technology, OLED has that volume is little, lightweight, high brightness, low voltage drive, be easy to realize the advantages such as the panchromatic demonstration of big area, therefore, to the Tang of Kodak in 1987 and nineteen ninety Cambridge University Burrongges release respectively organic and high molecule electroluminescent material and device since, OLED is fast-developing becomes the most competitive technology in third generation flat pannel display.
The structure of simple Organic Light Emitting Diode is individual layer sandwich, is mainly made up of anode, negative electrode, organic luminous layer, in order to improve charge transfer efficiency, keeps the injection balance in electronics and hole, and the device of some multilayered structures is developed in succession.Organic thin film electroluminescent is injection type luminescent device, electronics and hole are injected into luminescent layer from negative electrode (the low work function metal such as Mg/Al alloy) and anode (ITO) respectively, and on luminescent material, be compounded to form exciton, then send visible ray by radiative transition.
Luminescent material for OLED can be divided into fluorescent material and phosphor material, according to spin quantum statistical theory, after electronics and hole-recombination, the formation probability ratio of singlet state exciton and triplet exciton is 1: 3, be singlet state exciton 25%, 75% " electron-hole pair " that only account for " electron-hole pair " owing to having formed triplet exciton that spin prohibits to " electroluminescent " not contribution.Therefore, rely on merely the luminous fluorescence luminescent material of singlet state exciton attenuation, its electroluminescent maximum internal quantum efficiency is only 25%.
Phosphor material can pass through intersystem crossing, realizes and has mixed singlet state and the luminous phosphorescent emissions of triplet state, and the OLED internal quantum efficiency that utilizes in theory phosphor material to make can reach 100%, and its luminous efficiency improves three times than fluorescent material.1999, three (2-phenylpyridine) iridium is doped to 4,4 '-N by Thompson etc., in N '-bis-carbazole biphenyl (CBP), make OLED device, the highest external quantum efficiency is up to 8%, and luminous efficiency reaches 31lm/W, and this research has caused the very big interest of people to complex of iridium.
Research discovery, phosphorescent lifetime is relatively short, luminous quantum efficiency advantages of higher owing to having for phosphorescent iridium complex, is acknowledged as the phosphor material that has application potential at present most.But there is stronger state of aggregation quenching effect in this material in the time being applied to electroluminescent device, be that it is luminous very strong in dilute solution, but along with the increase of concentration, its transmitting weakens on the contrary, in the time of solid-state or state of aggregation, owing to existing strong molecular interaction to cause strong nonradiative transition, its luminous intensity significantly reduces, this causes must being entrained in material of main part time prepared by device, it is complicated that this prepares device, also cause device preparation cost to rise simultaneously, limit to a great extent the application of complex of iridium in electroluminescent device.
Calendar year 2001, the Tang Benzhong of Hong Kong University of Science and Thchnology has found aggregation inducing luminescence phenomenon, be that luminescent dye is luminous very weak even not luminous in solution, and in the time of state of aggregation, present on the contrary very strong luminous, that is to say, the formation of state of aggregation does not only cause concentration quenching to be conducive on the contrary improve fluorescent emission.New approach has been opened up in the application of luminescent material in Sony ericsson mobile comm ab that be found to be of this phenomenon.
But the dyestuff with aggregation inducing luminosity of exploitation is mostly fluorescent material at present, as mentioned above, the maximum internal quantum efficiency of fluorescent material can only reach 25% conventionally, well below the maximum internal quantum efficiency of theory of phosphor material 100%, therefore, the material that exploitation has strong aggregation inducing phosphorescent emissions performance will be conducive to simplify device preparation, reduce device cost of manufacture, have very important practical significance.
Summary of the invention
For defects such as the existing state of aggregation quenching effects of current phosphor material, the invention provides a kind of phosphor material with aggregation inducing phosphorescent emissions character and good thermal stability, and the application in OLED device of described phosphor material.
First aspect of the present invention is to provide a kind of aggregation inducing phosphorescent emissions complex of iridium, and it has the structure shown in structural formula (I):
In the present invention, in structural formula (I)
be also referred to as 3-phenyl pyridazine part;
also claimed salicylaldimine ligand;
be also referred to as C-N^N part;
also claimed N^O part.
Wherein, R
1, R
2, R
3, R
4can be identical or different, and respectively independently selected from: hydrogen atom, halogen atom, nitro, cyano group, cyano group alkyl, acyl group, straight chained alkyl, branched-chain alkyl, cycloalkyl, haloalkyl, aromatic base, halogenated aromatic base, alky-substituted aromatic base, aromatic base substituted alkyl, cycloalkenyl group, alkoxyl group, aromatic base oxygen base, replace silica-based, replace siloxy, fragrant amido, fat amido, heterocyclic radical; Or R
1, R
2part or all of formation ring texture with 3-phenyl pyridazine part; Or R
3, R
4part or all of formation ring texture with salicylaldimine ligand.
In content of the present invention, term " ring texture " is preferably and is selected from any one or a few in benzene, pyridine, furans, thiophene, pyrroles, pyrazoles, pyrans, pyrazine, oxazole, thiazole, imidazoles, pyrimidine, carbazole, quinoline, isoquinoline 99.9, indoles, pteridine, acridine, azophenlyene, thiodiphenylamine, purine.
In content of the present invention, term " alkyl " is preferably the alkyl of C1-C20, the more preferably alkyl of C1-18, the more preferably alkyl of C1-C12, the more preferably alkyl of C1-C10, the more preferably alkyl of C1-C8, as methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, the tertiary butyl, amyl group, isopentyl, n-hexyl, n-heptyl, n-octyl etc.
In content of the present invention, term " cycloalkyl " is preferably (alkyl replacement) cycloalkyl of naphthenic hydrocarbon and/or the C3-C20 of C3-C20, more preferably (alkyl replacement) cycloalkyl of the naphthenic hydrocarbon of C3-C18 and/or C3-C18, more preferably (alkyl replacement) cycloalkyl of the naphthenic hydrocarbon of C3-C12 and/or C3-C12, more preferably (alkyl replacement) cycloalkyl of the naphthenic hydrocarbon of C3-C10 and/or C3-C10, as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, suberyl, methylcyclopentyl, methylcyclohexyl etc.
In content of the present invention, term " cycloalkenyl group " is preferably the cycloalkenyl group of C3-C20, and/or (alkyl replacement) cycloalkenyl group of C3-C20, the more preferably cycloalkenyl group of C3-C18, and/or (alkyl replacement) cycloalkenyl group of C3-C18, the more preferably cycloalkenyl group of C3-C12, and/or (alkyl replacement) cycloalkenyl group of C3-C12, the more preferably cycloalkenyl group of C3-C10, and/or (alkyl replacement) cycloalkenyl group of C3-C10, as cyclopropenyl radical, cyclobutene base, cyclopentenyl, cyclohexenyl, cycloheptenyl, methyl cyclopentene base, methyl cyclohexane thiazolinyl, cyclopentadienyl, cyclobutadiene base, cyclohexadienyl etc.
In content of the present invention, term " aromatic base " can be monocycle, encircle or condensed ring group more, and be preferably the aromatic base of C6-C20, the more preferably aromatic base of C6-C15, the more preferably aromatic base of C6-12, the more preferably aromatic base of C6-C10, as phenyl, naphthyl, xenyl etc.
In content of the present invention, term " acyl group " is preferably alkyl acyl and/or aromatic base acyl group, and the definition of alkyl and aromatic base is described above.Described acyl group is as formyl radical, ethanoyl, benzoyl, benzenesulfonyl etc.
In content of the present invention, term " haloalkyl " can be any one or a few in chloro alkyl, bromo alkyl, fluoro-alkyl, iodo-alkyl, and the definition of described alkyl is described above.Described haloalkyl is as chloromethyl, dichloromethyl, trichloromethyl, trifluoromethyl, brooethyl, two brooethyls, iodomethyl, 1,2-Dichloroethyl, 2,2-Dichloroethyl etc.
In content of the present invention, term " heterocyclic radical " refers on the carbocyclic ring of aromatic base, cycloalkyl or cycloalkenyl group to have at least a carbon atom to be replaced by heteroatoms, and the definition of described aromatic base, cycloalkyl, cycloalkenyl group is described above.
In content of the present invention, term " heteroatoms " is preferably and is selected from any one or a few in Si, N, O, P, S.
Second aspect of the present invention is to provide the method that one is prepared aggregation inducing phosphorescent emissions complex of iridium shown in structural formula (I), comprising:
Under oxygen free condition, the salt of metal iridium, C-N^N part back flow reaction in solvent; After reaction finishes, add water, produce precipitation;
Described precipitation and N^O part are dissolved in solvent, back flow reaction under basic catalyst exists;
The solid collection purifying of separating out is obtained to described complex of iridium.
Wherein, described solvent is preferably the mixed solvent of water, organic solvent or organic solution and water.
Described organic solvent is as ethanol, ethylene glycol, propyl alcohol, propylene glycol, glycerine, Virahol, ethyl acetate, butylacetate, acetone, cellosolvo, butoxy ethanol etc.
Wherein, the salt of described metal iridium can be any water-soluble inorganic acid salt or organic acid salt, as iridium chloride, bromination iridium, nitric acid iridium, formic acid iridium, iridium acetate etc.
Wherein, the salt of metal iridium and C-N^N part mol ratio are preferably 1: 2.5-5.
Wherein, the salt of metal iridium and N^O part mol ratio are preferably 1: 2-5.
Most preferably, the salt of metal iridium, C-N^N part, N^O part mol ratio are preferably 1: 2.5-5: 2-5.
Wherein, described basic catalyst is preferably any one or a few in alkali metal hydroxide, alkali metal weak, as sodium carbonate, sodium bicarbonate, sodium hydroxide, salt of wormwood, saleratus, potassium hydroxide etc.
Wherein, the salt of metal iridium and C-N^N part reflux time are preferably and are at least 12 hours, and more preferably at least 15 hours, more preferably 12-48 hour, more preferably 16-32 hour.
Wherein, described precipitation and N^O part reflux time are preferably at least 3 hours, and more preferably at least 5 hours, more preferably 6-24 hour, more preferably 8-16 hour.
Third aspect of the present invention is to provide a kind of electroluminescent device, comprises multi-layer film structure, and described multi-layer film structure comprises hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer in order; Wherein, at least one deck in described multi-layer film structure comprises the aggregation inducing phosphorescent emissions complex of iridium shown in structural formula (I), and is preferably at least luminescent layer and comprises described aggregation inducing phosphorescent emissions complex of iridium.
In a kind of preferred embodiment of third aspect of the present invention, between described hole transmission layer and luminescent layer, can also comprise buffer layer or blocking layer.
In a kind of preferred embodiment of third aspect of the present invention, between described electron transfer layer and luminescent layer, can also comprise buffer layer or blocking layer.
Should be understood that, all respects of foregoing of the present invention and various preferred embodiment thereof can combine mutually, and various combination is also within the scope of the invention.
Beneficial effect of the present invention is:
1. owing to having lower than the mainly introducing of the assistant ligand O^N of the triplet of part C-N^N, this complex of iridium has strong aggregation inducing phosphorescent emissions character, has high solid luminescent quantum yield.
In 2.C-N^N part, owing to also having N atom with coordination N atom adjacent atom, while having avoided take pyridine as part, H atom pairs N on adjacent C atom and the interference of metal iridium complexing, this part and the sterically hindered of iridium atom center reduce, and cause part to be combined closelyr with metal center, are conducive to the transmitting of MLCT process, the thermostability that also can improve material simultaneously, is applicable to utilizing evaporation mode film forming.
3. can be by changing R
1, R
2, R
3, R
4functional group regulates the emission wavelength of complex of iridium, thereby regulates the emission wavelength of title complex.
4. can, by introducing all kinds of functional groups with electrons injection or transport property at C-N^N part and/or O^N part, change the electric property of this class complex of iridium.
5. complex of iridium of the present invention is not luminous or luminous very weak in solution, and luminous enhancing under solid-state or state of aggregation, thereby improve Sony ericsson mobile comm ab quantum yield, make it there is application potential in fields such as LCD backlight source, ORGANIC ELECTROLUMINESCENCE DISPLAYS and illumination, flexible display and flexible lights.
Because this complex of iridium has strong aggregation inducing phosphorescent emissions character, while being applied to ORGANIC ELECTROLUMINESCENCE DISPLAYS, LCD backlight source and organic solid lighting field, do not need to be doped in material of main part or can high-concentration dopant and do not cause the generation of luminous quenching phenomenon, simplify device preparation, reduce element manufacturing cost, improved device luminous efficiency.
Accompanying drawing explanation
Fig. 1 is complex of iridium of the present invention (A) and lower luminous contrast of solid state (B) in solution;
Fig. 2 is that complex of iridium of the present invention is at THF(A), THF/H
2o(B) luminous contrast in solvent;
Fig. 3 is that complex of iridium of the present invention is at THF/H
2luminous intensity curve in O mixed solvent.
Embodiment
the preparation of N^O part:
With R
3for C
12h
15, R
4for H is example, preparation method is as follows for N^O part: salicylic aldehyde (22mmol) is dissolved in 20mL ethanol, after n-dodecylamine (22mmol) is dissolved in 10mL ethanol, dropwise join in salicylic aldehyde ethanolic soln, add 1 acetic acid as catalyzer, stirring reaction 2 hours under room temperature.Remove after reaction solvent and unreacting material concentrated mixed solution, use sherwood oil: methylene dichloride (volume ratio 1: 1) is eluent, obtains orange-yellow oily thing 5.86g by column chromatography for separation.
1H?NMR(400MHz,CDCl
3)δ=13.72(s,1H;),8.33(s,1H),7.23-7.29(m,2H),6.95(d,1H),6.86(t,1H),3.58(t,2H;NCH
2),1.69(m,2H;CH
2),1.26(m,18H;CH
2),0.88ppm(t,3H;CH
3).
13C?NMR(100MHz,CDCl
3):δ=14.14,22.72,27.22,29.39,29.40,29.60,29.66,29.67,29.70,30.91,31.96,59.56,117.03,118.35,118.84,131.06,131.99,161.43,164.43
Reaction formula is as follows:
the preparation of complex of iridium:
Under condition of nitrogen gas, iridous chloride hydrate (1mol) is dissolved in cellosolvo/water mixed solvent with 3-phenyl pyridazine (3mol), back flow reaction 20 hours under agitation condition.Be cooled to room temperature, add water, separate out precipitation, collecting precipitation after filtering, the dry intermediate that obtains such as infrared grade.
By described intermediate and gained N^O part (3mol) and K
2cO
3be dissolved in cellosolvo, stir lower backflow 12 hours, separate out thick product.
The solid that collection is separated out, washing, column chromatography obtains complex of iridium.
The triplet of C-N^N part, higher than the triplet of O^N part, makes the excited state of this title complex in solution by the control of O^N part, thereby causes it not luminous in solution, as shown in Fig. 1 (A).
But under solid state, due to molecular interaction, cause the triplet of C-N^N part to reduce, make C-N^N part participate in the excited state of complex of iridium, thereby cause it solid-state lower luminous, as shown in Fig. 1 (B).
At THF/H
2in O mixing solutions, test luminescent properties, in THF solution, described complex of iridium does not phosphoresce, as shown in Figure 2 (A) shows.But H
2in O and THF mixed solvent, send yellow phosphorescence, (H as shown in Fig. 2 (B)
2o and THF volume ratio are 9: 1).As shown in Figure 3, when the content of water in the THF of complex of iridium solution is lower than 60% time, solution is not almost launched, when the content of water is higher than 70% time, solution sends faint yellow phosphorescence, along with the continuation of water-content increases, emissive porwer strengthens gradually, when the content of water reaches 90%, luminously reach the strongest, luminous intensity is while being 60% 66 times of water-content.
In addition, in complex of iridium of the present invention, R
3can adopt other organic aminated compounds to react acquisition with reference to aforesaid method.R
1, R
2and R
4can implement with reference to prior art the replacement of phenyl ring.By changing R
1, R
2, R
3, R
4functional group can regulate the emission wavelength of complex of iridium, thereby obtains the color in whole visible-range from blue light to ruddiness.
Above specific embodiments of the invention be have been described in detail, but it is just as example, the present invention is not restricted to specific embodiment described above.To those skilled in the art, any equivalent modifications that the present invention is carried out and alternative also all among category of the present invention.Therefore, equalization conversion and the modification done without departing from the spirit and scope of the invention, all should contain within the scope of the invention.
Claims (16)
1. an aggregation inducing phosphorescent emissions complex of iridium, is characterized in that, it has the structure shown in structural formula (I):
Wherein, R
1, R
2, R
3, R
4respectively independently selected from: hydrogen atom, halogen atom, nitro, cyano group, cyano group alkyl, acyl group, straight chained alkyl, branched-chain alkyl, cycloalkyl, haloalkyl, aromatic base, halogenated aromatic base, alky-substituted aromatic base, aromatic base substituted alkyl, cycloalkenyl group, alkoxyl group, aromatic base oxygen base, replace silica-based, replace siloxy, fragrant amido, fat amido, heterocyclic radical; Or R
1, R
2part or all of formation ring texture with 3-phenyl pyridazine part; Or R
3, R
4part or all of formation ring texture with salicylaldimine ligand.
2. complex of iridium according to claim 1, it is characterized in that, described ring texture is selected from any one or a few in benzene, pyridine, furans, thiophene, pyrroles, pyrazoles, pyrans, pyrazine, oxazole, thiazole, imidazoles, pyrimidine, carbazole, quinoline, isoquinoline 99.9, indoles, pteridine, acridine, azophenlyene, thiodiphenylamine, purine.
3. complex of iridium according to claim 1, is characterized in that, the alkyl that described alkane is C1-C20.
4. complex of iridium according to claim 1, is characterized in that, (alkyl replacement) cycloalkyl of the naphthenic hydrocarbon that described cycloalkyl is C3-C20 and/or C3-C20.
5. complex of iridium according to claim 1, is characterized in that, the heteroatoms in described heterocyclic radical is selected from any one or a few in Si, N, O, P, S.
6. complex of iridium according to claim 1, is characterized in that, the aromatic base that described aromatic base is C6-C20.
7. complex of iridium according to claim 1, is characterized in that, (alkyl replacement) cycloalkenyl group of the cycloalkenyl group that described cycloalkenyl group is C3-C20 and/or C3-C20.
8. a method for aggregation inducing phosphorescent emissions complex of iridium shown in structural formula (I), is characterized in that, comprising:
Under oxygen free condition, C-N^N part back flow reaction in solvent shown in the salt of metal iridium, structural formula (II); After reaction finishes, add water, produce precipitation;
Described precipitation and structural formula (III) N^O part is dissolved in solvent, back flow reaction under basic catalyst exists; The solid collection purifying of separating out is obtained to described complex of iridium.
9. method according to claim 8, is characterized in that, described solvent is the mixed solvent of water, organic solvent or organic solution and water.
10. method according to claim 8, is characterized in that, the salt of metal iridium, C-N^N part, N^O part mol ratio are 1: 2.5-5: 2-5.
11. methods according to claim 8, is characterized in that, described basic catalyst is any one or a few in alkali metal hydroxide, alkali metal weak.
12. methods according to claim 8, is characterized in that, the salt of described metal iridium and C-N^N part reflux time are preferably and are at least 12 hours.
13. methods according to claim 8, is characterized in that, described precipitation and N^O part reflux time are preferably 3 hours.
14. 1 kinds of electroluminescent devices, is characterized in that, comprise multi-layer film structure, and described multi-layer film structure comprises hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer in order; Wherein, at least one deck in described multi-layer film structure comprises the aggregation inducing phosphorescent emissions complex of iridium shown in structural formula (I).
15. electroluminescent devices according to claim 14, is characterized in that, between described hole transmission layer and luminescent layer, can also comprise buffer layer or blocking layer.
16. according to the electroluminescent device described in claims 14 or 15, it is characterized in that, between described electron transfer layer and luminescent layer, can also comprise buffer layer or blocking layer.
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| CN108948094A (en) * | 2018-08-02 | 2018-12-07 | 常州大学 | The C^N bidentate organic conjugated ligand and its annular metal iridium complex unimolecule white light emitting material of one kind mounting " butterfly " structure |
| CN112608341A (en) * | 2020-12-24 | 2021-04-06 | 玉林师范学院 | Mixed quinoline derivative iridium (III) complex and preparation method and application thereof |
| CN112898962A (en) * | 2021-01-30 | 2021-06-04 | 西安交通大学 | (C ^ N) Pt (II) (N-Donor) Cl type multi-core aggregation-induced phosphorescence enhanced luminescent material |
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Application publication date: 20140528 |