CN104292436A - Bipolar blue light emitting host material, preparation method thereof and organic electroluminescent device - Google Patents
Bipolar blue light emitting host material, preparation method thereof and organic electroluminescent device Download PDFInfo
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Abstract
The invention belongs to the field of organic semiconductors, and discloses a bipolar blue light emitting host material, a preparation method thereof and an organic electroluminescent device. The structural general formula of the host material is shown in the specification. In the formula, R is a C1-C20 alkyl group, and n is an integer from 17 to 100. In the bipolar blue light emitting host material, triazole is an electron transfer unit, and is in favor of transferring charges; and carbazole is an important electroluminescent material and has an excellent hole transport performance, N can be modified with an alkyl group to improve the dissolving performance and the film forming performance of copolymerized carbazole, and triazole is introduced to the main chain of a carbazyl polymer to realize the carrier balance of the organic electroluminescent device in order to solve the low efficiency problem of the organic electroluminescent device.
Description
Technical field
The present invention relates to organic semiconductor material field, particularly relate to a kind of bipolarity Blue-light emitting host material and preparation method thereof.The invention still further relates to a kind of this bipolarity Blue-light emitting host material that uses as the organic electroluminescence device of luminescent layer material of main part.
Background technology
Prepared with Alq by evaporation coating method from people's reported first such as Kodak C.W.Tang in 1987
3since bi-layer devices structure for luminescent material, organic electroluminescent just obtains the very big concern of people.Organic electroluminescent can be divided into fluorescence and phosphorescence electroluminescent.According to spin quantum statistical theory, the formation probability ratio of singlet excitons and triplet exciton is 1:3, and namely singlet excitons only accounts for 25% of " electron-hole pair ".Therefore, the fluorescence coming from the radiative transition of singlet excitons just only accounts for 25% of total input energy, and the electroluminescent of phosphor material just can utilize the energy of whole exciton, thus has larger superiority.Mostly adopt Subjective and Objective structure in present electrophosphorescence device, by phosphorescent emissions material with certain doped in concentrations profiled in main substance, to avoid burying in oblivion of triplet state-triplet state, improve phosphorescent emissions efficiency.At present, the material of main part in electroluminescent device mainly contains small molecule host material and polymer host material two class, its poor heat stability, and luminous efficiency is low.
Summary of the invention
Based on the problems referred to above, problem to be solved by this invention is to provide a kind of Heat stability is good, the bipolarity Blue-light emitting host material that luminous efficiency is high.
Technical scheme of the present invention is as follows:
A kind of bipolarity Blue-light emitting host material provided by the invention, its general structure is as follows:
In formula, R is C
1~ C
20alkyl, n is the integer of 17 ~ 100
Another object of the embodiment of the present invention is the preparation method providing a kind of bipolarity Blue-light emitting host material, comprises the steps:
The compd A providing following structural formula to represent respectively and B,
A:
i.e. N-alkyl-2,7-bis-tetramethyl ethylene ketone boric acid ester carbazole;
B:
i.e. 3,5-bis-(3-bromophenyl)-4-phenyl-4H-1,2,4-triazole;
Under oxygen-free environment (oxygen-free environment of at least one gas composition in preferred argon gas, nitrogen), be after dissolving during the compd A of 1:1 ~ 1.2 and B are added into containing catalyzer and alkaline solution organic solvent by mol ratio, Suzuki coupling reaction is carried out 12 ~ 96 hours at 70 ~ 130 DEG C, polyreaction is stopped after cooling, through separating-purifying reaction solution, obtain the described bipolarity Blue-light emitting host material of following general structure:
In formula, R is C
1~ C
20alkyl, n is the integer of 17 ~ 100.
Wherein, described catalyzer is described catalyzer is bis-triphenylphosphipalladium palladium dichloride, tetra-triphenylphosphine palladium; Or
Palladium and the tri-o-tolyl phosphine mixture of described catalyzer to be mol ratio be 1:4 ~ 8, or mol ratio is three or two argon benzyl acetone two palladiums and the 2-dicyclohexyl phosphine-2 of 1:4 ~ 8 ', 6 '-dimethoxy-biphenyl mixture;
The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
Described alkaline solution is selected from least one in sodium carbonate solution, solution of potassium carbonate and sodium hydrogen carbonate solution, and in described alkaline solution, the mol ratio of alkali solute and compd A is 20:1.
In a preferred embodiment, organic solvent is selected from solvent is at least one in toluene, DMF, tetrahydrofuran (THF).
In a preferred embodiment, Suzuki coupling reaction at 90 ~ 120 DEG C, reaction within 36 ~ 60 hours, carry out.
In a preferred embodiment, separating-purifying reaction solution comprises step:
After reaction stops, methyl alcohol precipitating is added in reaction solution, methyl alcohol and normal hexane extracting is used successively after being filtered by apparatus,Soxhlet's, then be that solvent extraction is to colourless with chloroform, collect chloroformic solution and be spin-dried for and obtain powder, powder after collection under vacuo after 50 DEG C of dry 24h, obtains described bipolarity Blue-light emitting host material again.
The present invention also provides a kind of organic electroluminescence device, the material of its luminescent layer is two (4,6-difluorophenyl pyridinato-N, C2) pyridinecarboxylic close iridium (III) according to 8% mass percent be doped to the dopant mixture formed in the bipolarity Blue-light emitting host material of following structural formula:
In formula, R is C
1~ C
20alkyl, n is the integer of 17 ~ 100.
In bipolarity Blue-light emitting host material of the present invention, triazole is an electric transmission unit, is conducive to transferring charge; Carbazole is the important electroluminescent material of a class, and it has good hole transport performance, and N is upper can carry out alkyl modified, thus improves solubility property and the film forming properties of copolymerization carbazole.Carbazolyl polymers main chain introduces triazole, realizes the carrier balance of electroluminescent device, thus solve organic electroluminescence device low efficiency problem.
The preparation method of above-mentioned bipolarity Blue-light emitting host material, have employed better simply synthetic route, thus reduces technical process, and starting material are cheap and easy to get, and manufacturing cost is reduced; And obtained polymeric material constructions is novel, solubility property is good, and film forming properties is excellent, is applicable to organic electroluminescence device.This material has higher electroluminescent efficiency.
Accompanying drawing explanation
Fig. 1 is the thermogravimetic analysis (TGA) figure of the bipolarity Blue-light emitting host material that embodiment 1 obtains;
Fig. 2 is the structural representation of the organic electroluminescence device that embodiment 6 obtains.
Embodiment
In order to understand the content of patent of the present invention better, technology case of the present invention is further illustrated below by concrete example and legend, specifically comprise material preparation and device preparation, but these embodiments do not limit the present invention, wherein compd A commercially obtains, the disclosed method synthesis of compound reference literature (Synth.Met.2007,157,743.) obtains.
Embodiment 1:
The bipolarity Blue-light emitting host material of the present embodiment, i.e. poly-{ N-normal hexane base-2,7-bis-base carbazole-co-3,5-bis-(3-base-phenyl)-4-phenyl-4H-1,2,4-triazole } (representing with P1) (wherein, R is normal hexane base, n=39), its structural formula is as follows:
The preparation process of above-mentioned polymkeric substance is as follows:
Reaction formula is as follows:
Under argon shield, by N-normal hexane base-2,7-bis-tetramethyl ethylene ketone boric acid ester carbazole (101mg, 0.2mmol), 3,5-bis-(3-bromophenyl)-4-phenyl-4H-1,2,4-triazole (91mg, 0.2mmol) add in the flask filling 10ml toluene solvant, after abundant dissolving, salt of wormwood (2mL, 2mol/L) solution is joined in flask, vacuumize deoxygenation and be filled with argon gas, then bis-triphenylphosphipalladium palladium dichloride (5.6mg, 0.008mmol) is added; Flask is heated to 100 DEG C and carries out Suzuki coupling reaction 48h.Subsequently, after cooling, stop polyreaction, drip in flask in 50ml methyl alcohol and carry out sedimentation; Methyl alcohol and normal hexane extracting 24h is used successively after being filtered by apparatus,Soxhlet's.Then be that solvent extraction is extremely colourless with chloroform, collect chloroformic solution and be spin-dried for obtain red powder, after collection, 50 DEG C of dry 24h obtain P1 product under vacuo, productive rate 86%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=31.4kDa, M
w/ M
n=2.3.
Fig. 1 is the thermogravimetic analysis (TGA) figure of the bipolarity Blue-light emitting host material that embodiment 1 obtains; Wherein, thermogravimetic analysis (TGA) is completed by the measurement of Perkin-Elmer Series7 Thermo System, and all measurements all complete in atmosphere at room temperature.As shown in Figure 1, the thermal weight loss temperature (T of bipolarity Blue-light emitting host material 5%
d) be 421 DEG C.
Embodiment 2:
The bipolarity Blue-light emitting host material of the present embodiment, i.e. poly-{ N-methyl-2,7-bis-base carbazole-co-3,5-bis-(3-base-phenyl)-4-phenyl-4H-1,2,4-triazole } (representing with P2) (wherein, R is methyl, n=100), its structural formula is as follows:
The preparation process of above-mentioned polymkeric substance is as follows:
Reaction formula is as follows:
Under nitrogen and argon gas gas mixture are protected; by N-methyl-2; 7-bis-tetramethyl ethylene ketone boric acid ester carbazole (130mg; 0.3mmol), 3; 5-bis-(3-bromophenyl)-4-phenyl-4H-1; 2; 4-triazole (137mg; 0.3mmol) add in the two-mouth bottle of 50mL specification with 15mL tetrahydrofuran (THF); after the gas mixture air-discharging passing into nitrogen and argon gas after abundant dissolving is about 20min, then tetra-triphenylphosphine palladium (4mg, 0.003mmol) is added wherein; sodium bicarbonate (3mL, 2mol/L) solution is added again after abundant dissolving.After the gas mixture air-discharging of fully logical nitrogen and argon gas is about 10min again, two-mouth bottle is joined 70 DEG C and carry out Suzuki coupling reaction 96h.Subsequently, after cooling, stop polyreaction, in two-mouth bottle, add 40mL methyl alcohol precipitating, after being filtered by apparatus,Soxhlet's, use methyl alcohol and normal hexane extracting 24h successively.Then be solvent extraction with chloroform to colourless, collect chloroformic solution and be spin-dried for and obtain red solid, after collection, obtain P2 product after 50 DEG C of dry 24h under vacuo.Productive rate is 83%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=52.7kDa, M
w/ M
n=2.0.
Embodiment 3:
The bipolarity Blue-light emitting host material of the present embodiment, i.e. poly-{ N-NSC 62789 base-2,7-bis-base carbazole-co-3,5-bis-(3-base-phenyl)-4-phenyl-4H-1,2,4-triazole } (representing with P3) (wherein, R is NSC 62789 base, n=73), its structural formula is as follows:
The preparation process of above-mentioned polymkeric substance is as follows:
Reaction formula is as follows:
Under nitrogen protection, by N-NSC 62789 base-2,7-bis-tetramethyl ethylene ketone boric acid ester carbazole (210mg, 0.3mmol), 3,5-bis-(3-bromophenyl)-4-phenyl-4H-1,2,4-triazole (150mg, 0.33mmol), palladium (3.5mg, 0.015mmol) and three (o-methoxyphenyl) phosphine (21mg, 0.06mmol) joins the N filling 12mL, in the flask of dinethylformamide, salt of wormwood (3mL, 2mol/L) solution is added, after logical nitrogen purge gas is about 30min in flask subsequently after abundant dissolving; Flask is heated to 130 DEG C and carries out Suzuki coupling reaction 12h.Subsequently, after cooling, stop polyreaction, in flask, add 40mL methyl alcohol precipitating, after being filtered by apparatus,Soxhlet's, use methyl alcohol and normal hexane extracting 24h successively; Then be solvent extraction with chloroform to colourless, collect chloroformic solution and be spin-dried for and obtain red powder, after collection under vacuo after 50 DEG C of dry 24h, be P3 product, productive rate 83%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=57.2kDa, M
w/ M
n=2.1.
Embodiment 4:
The bipolarity Blue-light emitting host material of the present embodiment, i.e. poly-{ N-normal butane base-2,7-bis-base carbazole-co-3,5-bis-(3-base-phenyl)-4-phenyl-4H-1,2,4-triazole } (representing with P4) (wherein, R is normal butane base, n=17), its structural formula is as follows:
The preparation process of above-mentioned polymkeric substance is as follows:
Reaction formula is as follows:
Under nitrogen protection; by N-normal butane base-2; 7-bis-tetramethyl ethylene ketone boric acid ester carbazole (143mg; 0.3mmol), 3; 5-bis-(3-bromophenyl)-4-phenyl-4H-1; 2; 4-triazole (164mg; 0.36mmol), three or two argon benzyl acetones two palladium (9mg, 0.009mmol) and 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl (29mg; 0.072mmol) join the N filling 12mL; in the flask of dinethylformamide, after fully dissolving, add sodium bicarbonate (3mL, 2mol/L) solution.After in flask, logical nitrogen purge gas is about 30min subsequently; Flask is heated to 120 DEG C and carries out Suzuki coupling reaction 36h.Subsequently, after cooling, stop polyreaction, in flask, add 40mL methyl alcohol precipitating, after being filtered by apparatus,Soxhlet's, use methyl alcohol and normal hexane extracting 24h successively; Then be solvent extraction with chloroform to colourless, collect chloroformic solution and be spin-dried for and obtain red powder, after collection under vacuo after 50 DEG C of dry 24h, be P4 product, productive rate is 80%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=14.8kDa, M
w/ M
n=2.4.
Embodiment 5:
The bipolarity Blue-light emitting host material of the present embodiment, i.e. poly-{ N-dodecyl-2,7-bis-base carbazole-co-3,5-bis-(3-base-phenyl)-4-phenyl-4H-1,2,4-triazole } (representing with P5) (wherein, R is dodecyl, n=56), its structural formula is as follows:
The preparation process of above-mentioned polymkeric substance is as follows:
Reaction formula is as follows:
Under nitrogen and argon gas gas mixture are protected; by N-dodecyl-2; 7-bis-tetramethyl ethylene ketone boric acid ester carbazole (176mg; 0.3mmol), 3; 5-bis-(3-bromophenyl)-4-phenyl-4H-1; 2; 4-triazole (164mg; 0.36mmol) add in the two-mouth bottle of 50mL specification with 15mL toluene; after the gas mixture air-discharging passing into nitrogen and argon gas after abundant dissolving is about 20min, then tetra-triphenylphosphine palladium (8mg, 0.006mmol) is added wherein; add salt of wormwood (3mL, 2mol/L) solution again.After the gas mixture air-discharging of fully logical nitrogen and argon gas is about 10min again, two-mouth bottle is joined 90 DEG C and carry out Suzuki coupling reaction 60h.Subsequently, after cooling, stop polyreaction, in two-mouth bottle, add 40mL methyl alcohol precipitating, after being filtered by apparatus,Soxhlet's, use methyl alcohol and normal hexane extracting 24h successively.Then be solvent extraction with chloroform to colourless, collect chloroformic solution and be spin-dried for and obtain red solid, after collection, obtain P5 product after 50 DEG C of dry 24h under vacuo.Productive rate is 75%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=43.1kDa, M
w/ M
n=2.2.
Embodiment 6:
The present embodiment is organic electroluminescence device, the bipolarity Blue-light emitting host material that its luminescent layer adopts embodiment 1 obtained, i.e. poly-{ N-normal hexane base-2,7-bis-base carbazole-co-3,5-bis-(3-base-phenyl)-4-phenyl-4H-1,2,4-triazole } as the material of main part of luminescent layer, certainly, the arbitrary obtained bipolarity Blue-light emitting host material of embodiment 2 to 5 can also be selected.
As shown in Figure 2, this organic electroluminescence device comprises the structure stacked gradually: conductive substrate layer 1, hole injection layer 2, luminescent layer 3, hole blocking layer 4, electron transfer layer 5, electron injecting layer 6, cathode layer 7; Wherein, the material of each functional layer and thickness as follows:
Conductive substrate layer 1 comprises substrate, and is deposited on the anode layer of substrate surface; In the present embodiment, the material of substrate is preferably glass, and the material of anode layer is indium tin oxide (ITO), and itself and glass combine, and is called for short ito glass, and conventional ITO replaces; The thickness of ITO is 150nm;
The material of hole injection layer 2 is poly-3,4-ethylenedioxy thiazoles (PEDOT) and the mixture of polystyrene-sulfonic acid matrix material (PSS), is expressed as PEDOT:PSS; The thickness of hole injection layer 2 is 30nm;
The material of luminescent layer 3 is two (4,6-difluorophenyl pyridinato-N, C2) pyridinecarboxylic closes iridium (III) (FIrpic) according to the obtained multipolymer Blue-light emitting host material of the embodiment 1 that is doped to of mass percent of 8%, i.e. poly-{ N-normal hexane base-2,7-bis-base carbazole-co-3,5-bis-(3-base-phenyl)-4-phenyl-4H-1,2,4-triazole } dopant mixture of composition in (representing with P1); Be expressed as P1:FIrpic; The thickness of luminescent layer 3 is 20nm;
The material of hole blocking layer 4 is 2,9-dimethyl-4,7-phenylbenzene-1,10-phenanthroline (BCP), and the thickness of hole blocking layer 4 is 30nm;
The material of electron transfer layer 5 is three-oxine aluminium (Alq
3), the thickness of electron transfer layer 5 is 30nm;
The material of electron injecting layer 6 is LiF; The thickness of electron injecting layer 6 is 1.5nm;
The material of cathode layer 7 is aluminium, and the thickness of cathode layer 7 is 150nm.
The structure of this organic electroluminescence device can be expressed as:
Ito glass/PEDOT:PSS/P1:FIrpic/BCP/Alq
3/ LiF/Al; Wherein, brace "/" represents laminate structure.
The concrete grammar that this organic electroluminescence device makes is:
Spin coating PEDOT:PSS successively on conductive glass (ITO) substrate through cleaning, evaporation P1:FIrpic, BCP, Alq successively on its surface again after to be dried
3, LiF, Al, obtained organic electroluminescence device.
In room temperature, air, adopt Keithley source measuring system (Keithley2400Sourcemeter, Keithley2000Cuirrentmeter) with correcting silicon photoelectric diode, electroluminescent spectrum, by French JY company SPEX CCD3000 spectrometer measurement, carries out current versus brightness-voltage characteristic to the organic electroluminescence device of preparation and measures; Test result shows, and the maximum current efficiency of this organic electroluminescence device is 6.2cd/A, and high-high brightness is 16580cd/m
2.
Should be understood that, the above-mentioned statement for present pre-ferred embodiments is comparatively detailed, and therefore can not think the restriction to scope of patent protection of the present invention, scope of patent protection of the present invention should be as the criterion with claims.
Claims (9)
1. a bipolarity Blue-light emitting host material, is characterized in that, its general structure is as follows:
In formula, R is C
1~ C
20alkyl, n is the integer of 17 ~ 100.
2. a preparation method for bipolarity Blue-light emitting host material, is characterized in that, comprises the steps:
The compd A providing following structural formula to represent respectively and B,
A：
B：
Under oxygen-free environment, be dissolve mol ratio during the compd A of 1:1 ~ 1.2 and B are added into containing catalyzer and alkaline solution organic solvent, Suzuki coupling reaction is carried out 12 ~ 96 hours at 70 ~ 130 DEG C, polyreaction is stopped after cooling, separating-purifying reaction solution, obtains the described bipolarity Blue-light emitting host material of following general structure:
In formula, R is C
1~ C
20alkyl, n is the integer of 17 ~ 100.
3. the preparation method of bipolarity Blue-light emitting host material according to claim 2, is characterized in that, described catalyzer is bis-triphenylphosphipalladium palladium dichloride, tetra-triphenylphosphine palladium; The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
4. the preparation method of bipolarity Blue-light emitting host material according to claim 2, it is characterized in that, palladium and the tri-o-tolyl phosphine mixture of described catalyzer to be mol ratio be 1:4 ~ 8, or mol ratio is three or two argon benzyl acetone two palladiums and the 2-dicyclohexyl phosphine-2 of 1:4 ~ 8 ', 6 '-dimethoxy-biphenyl mixture; The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
5. the preparation method of bipolarity Blue-light emitting host material according to claim 2, is characterized in that, described alkaline solution is at least one in sodium carbonate solution, solution of potassium carbonate and sodium hydrogen carbonate solution; In described alkaline solution, the mol ratio of alkali solute and compd A is 20:1.
6. the preparation method of bipolarity Blue-light emitting host material according to claim 2, is characterized in that, described organic solvent is selected from least one in toluene, DMF, tetrahydrofuran (THF).
7. the preparation method of bipolarity Blue-light emitting host material according to claim 2, is characterized in that, Suzuki coupling reaction at 90 ~ 120 DEG C, reaction within 36 ~ 60 hours, carry out.
8. the preparation method of bipolarity Blue-light emitting host material according to claim 2, is characterized in that, separating-purifying reaction solution comprises step:
After reaction stops, methyl alcohol precipitating is added in reaction solution, methyl alcohol and normal hexane extracting is used successively after being filtered by apparatus,Soxhlet's, then be that solvent extraction is to colourless with chloroform, collect chloroformic solution and be spin-dried for and obtain powder, powder after collection under vacuo after 50 DEG C of dry 24h, obtains described bipolarity Blue-light emitting host material again.
9. an organic electroluminescence device, it is characterized in that, the material of its luminescent layer be two (4,6-difluorophenyl pyridinato-N, C2) pyridinecarboxylic close iridium according to 8% mass percent be doped to the dopant mixture formed in the bipolarity Blue-light emitting host material of following structural formula:
In formula, R is C
1~ C
20alkyl, n is the integer of 17 ~ 100.
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Application publication date: 20150121 |