CN104592982A - Blue organic electroluminescence material, preparation method thereof and organic electroluminescent device - Google Patents
Blue organic electroluminescence material, preparation method thereof and organic electroluminescent device Download PDFInfo
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- 0 *C(*)(C1=*2)c3cc(-c(cc4)ccc4I)ccc3C1NC(C1(*)*)=C2c(cc2)c1cc2C1=CC=C(*)CC1 Chemical compound *C(*)(C1=*2)c3cc(-c(cc4)ccc4I)ccc3C1NC(C1(*)*)=C2c(cc2)c1cc2C1=CC=C(*)CC1 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Cc1ccccc1 Chemical compound Cc1ccccc1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- LAELQVHJIAQDSE-QXMHVHEDSA-N C(C1)C=CC=C1/C=C\C1C=CC=CC1 Chemical compound C(C1)C=CC=C1/C=C\C1C=CC=CC1 LAELQVHJIAQDSE-QXMHVHEDSA-N 0.000 description 1
- ZPUQNDQAFFLJQX-UHFFFAOYSA-N C(C1C=CCCC1)C1=CCCC=C1 Chemical compound C(C1C=CCCC1)C1=CCCC=C1 ZPUQNDQAFFLJQX-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N C(c1ccccc1)c1ccccc1 Chemical compound C(c1ccccc1)c1ccccc1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- ROZFGYSIJVTDKH-UHFFFAOYSA-N c(cc1)ccc1[IH]c1ccccc1 Chemical compound c(cc1)ccc1[IH]c1ccccc1 ROZFGYSIJVTDKH-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention belongs to the field of organic electroluminescent device materials, and discloses a blue organic electroluminescence material, a preparation method thereof and an organic electroluminescent device. The structural formula of the material is shown in the specification; and in the formula, R is a C1-C20 alkyl group. In the blue organic electroluminescence material, diindenopyrazine has good rigidity, flatness and heat stability; and triphenylamine has an excellent hole transport performance, so the organic electroluminescent devices based on the material are in favor of improving the luminescence efficiency.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, particularly relate to a kind of blue-ray organic electroluminescent material and its preparation method and application.
Background technology
Organic electroluminescent has the features such as low-voltage direct-current drives, brightness is high, diopter is wide, be considered to one of most promising flat panel display technology of future generation (C.W.Tang and S.A.Vanslyke.Appl.Phys.Lett., 1987,51 (12): 913-915).Organic molecule electroluminescent device is made up of more than two layers organic molecular films mostly, and they have electronics and hole transport performance respectively.And organic polymer electroluminescent device only needs individual layer organic film (J.H.Burroughes, D.D.C.Bradley, A.R.Brown, R.N.Marks, K.Mackay, R.H.Friend, P.L.Burns and A.B.Holms.Nature, 1990,347:539-541), thus its preparation technology is more convenient.The minimizing at molecular layer part interface, favourable to the stability of device.Organic molecule electroluminescent device needs two-layer with upper film, and be the restriction of the carrier transmission characteristics due to the organic molecule used, or they are based on transmission electronic, or based on transporting holes.The performance of organic molecule depends on its structure, its carrier transmission characteristics is relevant with the conjugated system of molecule, polyaromatic conjugated system often has electronic transmission performance, and triarylamine quasi-molecule has cavity transmission ability, although can molecular designing be passed through at present, obtain luminescent organic molecule material that is of a great variety, different properties, but have that such as price is high, preparation is complicated, second-order transition temperature (T
g) low, the not high deficiency of carrier transmission performance.
Summary of the invention
Problem to be solved by this invention is to provide that a kind of second-order transition temperature is higher, the good blue-ray organic electroluminescent material of carrier transmission performance.
For achieving the above object, blue-ray organic electroluminescent material provided by the invention, its structure is such as formula as follows:
4,4 ' namely-(6,6,12,12-tetraalkyl-6,12-dihydro two indenes [2,1-b:2 ', 1 '-e] pyrazine-2,8-bis-base) two (N, N-phenylbenzene aniline); In formula, R is C
1~ C
20alkyl.
Another object of the present invention is to provide the preparation method of the blue-ray organic electroluminescent material that a kind of synthetic route is simple, material is cheap and easy to get, described preparation method comprises the steps:
The compd A providing following structural formula to represent respectively and B,
in formula, R is C
1~ C
20alkyl;
Under oxygen-free environment, be dissolve mol ratio during the compd A of 1:2 ~ 2.4 and B are added into containing catalyzer and alkaline solution organic solvent, the mixing solutions obtained after dissolving carries out Suzuki coupling reaction 12 ~ 48 hours at 70 ~ 130 DEG C, stopped reaction cool to room temperature, separating-purifying reaction solution, obtains blue-ray organic electroluminescent material described in following structural formula:
in formula, R is C
1~ C
20alkyl.
Wherein, described catalyzer is bis-triphenylphosphipalladium palladium dichloride or tetra-triphenylphosphine palladium; Or,
Described catalyzer is the mixture of organic palladium and organophosphorus ligand, and the mol ratio of described organic palladium and organophosphorus ligand is 1:4 ~ 8; Preferably, described organic palladium is palladium or three or two argon benzyl acetone two palladiums, and described organophosphorus ligand is three (o-methyl-phenyl-) phosphines or 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl; More have choosing, described mixture is the mixture of palladium and tri-o-tolyl phosphine, or described mixture is three or two argon benzyl acetone two palladiums and 2-dicyclohexyl phosphine-2 ', the mixture of 6 '-dimethoxy-biphenyl.
The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
In described preparation method, described alkaline solution is selected from 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 described 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, the temperature of reaction of Suzuki coupling reaction is 90 ~ 120 DEG C, and the reaction times is 24 ~ 36 hours.
In a preferred embodiment, described separating-purifying reaction solution comprises:
After Suzuki coupling reaction stops, with dichloromethane extraction repeatedly and merge organic phase, after this organic phase is spin-dried for after anhydrous magnesium sulfate drying, obtain crude product, this crude product adopts volume ratio to be that sherwood oil and the ethyl acetate of 10:1 mixes leacheate (can be expressed as its structure is sherwood oil: ethyl acetate (10:1)) and be separated through silica gel column chromatography and obtain crystalline substance, this crystalline substance, under vacuo after 50 DEG C of dry 24h, obtains described blue-ray organic electroluminescent material.
In described preparation method, oxygen-free environment is made up of at least one gas in argon gas, nitrogen.
Above-mentioned preparation method's principle is simple, easy and simple to handle, low for equipment requirements, can wide popularization and application.
Another object of the present invention is to provide the application of above-mentioned blue-ray organic electroluminescent material in organic electroluminescence device luminescent layer.
The structure of this organic electroluminescence device comprises conductive anode substrate and is sequentially laminated on the hole injection layer of conductive anode substrate, hole transport/electronic barrier layer, luminescent layer, electric transmission/hole blocking layer, electron injecting layer, cathode layer; Wherein:
Conductive anode substrate comprises with substrate of glass, and is deposited on the conductive anode layer of glass basic surface, and the material changing conductive anode layer is indium tin oxide (ITO), and therefore, this conductive anode substrate is also called ito glass, or is directly called for short ITO;
The material making hole injection layer is PEDOT:PSS;
The material of hole transport/electronic barrier layer is N, N'-phenylbenzene-N, N'-bis-(3-aminomethyl phenyl)-1,1'-biphenyl-4,4'-diamines (TPD);
The material of luminescent layer is blue-ray organic electroluminescent material described above, namely 4,4 '-(6,6,12,12-tetraalkyl-6,12-dihydro two indenes [2,1-b:2 ', 1 '-e] pyrazine-2,8-bis-base) two (N, N-phenylbenzene aniline);
The material of electric transmission/hole blocking layer is 4,7-phenylbenzene-1,10-phenanthroline (BPhen);
The material of electron injecting layer is LiF;
The material of cathode layer is Al.
In described blue-ray organic electroluminescent material of the present invention, two indeno pyrazines have good rigidity and planarity, and thermal stability is good; Triphenylamine has excellent hole transport performance; Therefore the raising of luminous efficiency is conducive to based on the organic electroluminescence device of this material.
Separately, the preparation method of above-mentioned blue-ray organic electroluminescent 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:
Accompanying drawing explanation
Fig. 1 is the differential scanning calorimetric curve of the blue-ray organic electroluminescent material that embodiment 1 obtains;
Fig. 2 is the organic electroluminescence device structural representation that embodiment 5 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, compd B are all purchased from scientific and technological in lark prestige.
Embodiment 1: the blue-ray organic electroluminescent material of the present embodiment, namely 4,4'-(6,6,12,12-tetra-(normal-butyl)-6,12-dihydro two indenes [2,1-b:2', 1'-e] pyrazine-2,8-bis-base) two (N, N-phenylbenzene aniline) are (wherein, R is normal butane base), preparation process is as follows:
Under argon shield, by 6,6,12,12-tetra-(normal butane base)-2,8-bis-tetramethyl ethylene ketone boric acid ester-6,12-dihydro two indenes [2,1-b:2', 1'-e] pyrazine (146mg, 0.2mmol), 4-bromo-N, N-phenylbenzene aniline (129mg, 0.4mmol) 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 120 DEG C and carries out Suzuki coupling reaction 24h.Stopped reaction cool to room temperature, with dichloromethane extraction three times, merge organic phase, be spin-dried for after anhydrous magnesium sulfate drying, crude product adopts sherwood oil: ethyl acetate (10:1) obtains white crystal for leacheate is separated through silica gel column chromatography.The lower 50 DEG C of dry 24h of last vacuum, obtain blue-ray organic electroluminescent material.Productive rate is 82%.Mass spectrum: m/z799.0(M
++ 1); Ultimate analysis (%) C
58h
46n
4: theoretical value: C87.19, H5.80, N7.01; Measured value: C87.25, H5.73, N7.08.
Fig. 1 is the differential scanning calorimetric curve of the blue-ray organic electroluminescent material that embodiment 1 obtains; Differential scanning calorimetric curve (DSC) is completed by the measurement of Perkin-Elmer DSC-7 Thermo System, and all measurements all complete in atmosphere at room temperature.As shown in Figure 1, the second-order transition temperature (T of blue-ray organic electroluminescent material
g) be 124 DEG C.
Embodiment 2: the blue-ray organic electroluminescent material of the present embodiment, namely 4,4'-(6,6,12,12-tetramethyl--6,12-dihydro two indenes [2,1-b:2', 1'-e] pyrazine-2,8-bis-base) two (N, N-phenylbenzene aniline) (wherein, R is methyl), preparation process is as follows:
Under nitrogen and argon gas gas mixture are protected; by 6; 6; 12; 12-tetramethyl--2,8-bis-tetramethyl ethylene ketone boric acid ester-6,12-dihydro two indenes [2; 1-b:2'; 1'-e] pyrazine (169mg, 0.3mmol), 4-bromo-N, N-phenylbenzene aniline (214mg; 0.66mmol) 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 48h.Stopped reaction cool to room temperature, with dichloromethane extraction three times, merge organic phase, be spin-dried for after anhydrous magnesium sulfate drying, crude product adopts sherwood oil: ethyl acetate (10:1) obtains white crystal for leacheate is separated through silica gel column chromatography.The lower 50 DEG C of dry 24h of last vacuum, obtain blue-ray organic electroluminescent material.Productive rate is 79%.
Embodiment 3: the blue-ray organic electroluminescent material of the present embodiment, namely 4,4'-(6,6,12,12-tetra-(dodecyl)-6,12-dihydro two indenes [2,1-b:2', 1'-e] pyrazine-2,8-bis-base) two (N, N-phenylbenzene aniline) are (wherein, R is dodecyl), preparation process is as follows:
Under nitrogen protection, by 6,6,12,12-tetra-(dodecyl)-2,8-bis-tetramethyl ethylene ketone boric acid ester-6,12-dihydro two indenes [2,1-b:2', 1'-e] pyrazine (354mg, 0.3mmol), the bromo-N of 4-, N-phenylbenzene aniline (224mg, 0.69mmol), palladium (3.5mg, 0.015mmol) and three (o-methyl-phenyl-) 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.Stopped reaction cool to room temperature, with dichloromethane extraction three times, merge organic phase, be spin-dried for after anhydrous magnesium sulfate drying, crude product adopts sherwood oil: ethyl acetate (10:1) obtains white crystal for leacheate is separated through silica gel column chromatography.The lower 50 DEG C of dry 24h of last vacuum, obtain blue-ray organic electroluminescent material.Productive rate is 76%.
Embodiment 4: the blue-ray organic electroluminescent material of the present embodiment, namely 4,4'-(6,6,12,12-tetra-(NSC 62789 base)-6,12-dihydro two indenes [2,1-b:2', 1'-e] pyrazine-2,8-bis-base) two (N, N-phenylbenzene aniline) are (wherein, R is NSC 62789 base), preparation process is as follows:
Under nitrogen protection; by 6; 6; 12,12-tetra-(NSC 62789 base)-2,8-bis-tetramethyl ethylene ketone boric acid ester-6; 12-dihydro two indenes [2; 1-b:2', 1'-e] pyrazine (489mg, 0.3mmol), the bromo-N of 4-; N-phenylbenzene aniline (233mg; 0.72mmol), 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 carbonate (3mL, 2mol/L) solution.After in flask, logical nitrogen purge gas is about 30min subsequently; Flask is heated to 90 DEG C and carries out Suzuki coupling reaction 36h.Stopped reaction cool to room temperature, with dichloromethane extraction three times, merge organic phase, be spin-dried for after anhydrous magnesium sulfate drying, crude product adopts sherwood oil: ethyl acetate (10:1) obtains white crystal for leacheate is separated through silica gel column chromatography.The lower 50 DEG C of dry 24h of last vacuum, obtain blue-ray organic electroluminescent material.Productive rate is 85%.
Embodiment 5:
The present embodiment is organic electroluminescence device, the material of its luminescent layer is the blue-ray organic electroluminescent material that the present invention obtains, preferred embodiment 1 obtained 4,4'-(6,6,12,12-tetra-(normal-butyl)-6,12-dihydro two indenes [2,1-b:2', 1'-e] pyrazine-2,8-bis-base) two (N, N-phenylbenzene aniline) (representing with P).
As shown in Figure 2, the structure of this organic electroluminescence device comprises conductive anode substrate 1 and is sequentially laminated on the hole injection layer 2 of conductive anode substrate, hole transport/electronic barrier layer 3, luminescent layer 4, electric transmission/hole blocking layer 5, electron injecting layer 6, cathode layer 7; Wherein:
Conductive anode substrate comprises with substrate of glass, and is deposited on the conductive anode layer of glass basic surface, and the material changing conductive anode layer is indium tin oxide (ITO), and therefore, this conductive anode substrate is also called ito glass, or is directly called for short ITO;
The material making hole injection layer is PEDOT:PSS;
The material of hole transport/electronic barrier layer is N, N'-phenylbenzene-N, N'-bis-(3-aminomethyl phenyl)-1,1'-biphenyl-4,4'-diamines (TPD);
The material of luminescent layer is 4,4 '-(6,6,12,12-tetraalkyl-6,12-dihydro two indenes [2,1-b:2 ', 1 '-e] pyrazine-2,8-bis-base) two (N, N-phenylbenzene aniline);
The material of electric transmission/hole blocking layer is 4,7-phenylbenzene-1,10-phenanthroline (BPhen);
The material of electron injecting layer is LiF;
The material of cathode layer is Al.
The concrete grammar that this organic electroluminescence device makes is:
At conductive anode layer (ITO) the spin coating PEDOT:PSS on the surface of the conductive anode substrate through cleaning, obtained hole injection layer;
Then, level evaporation hole transport/electronic barrier layer (TPD), luminescent layer (P), electric transmission/hole blocking layer (BPhen), electron injecting layer (LiF) cathode layer (Al) successively on hole injection layer surface.
The structure of this organic electroluminescence device also can be expressed as follows:
Glass/ITO(150nm)/PEDOT:PSS (30nm)/TPD (40nm)/P(30nm)/BPhen (35nm)/LiF (1.5nm)/Al (150nm); Wherein, brace represents laminate structure, numerical value in bracket, is the one-tenth-value thickness 1/10 of each functional layer.
Current versus brightness-the voltage characteristic of this organic electroluminescence device is tested, test completes by with Keithley source measuring system (Keithley2400Sourcemeter, Keithley2000Cuirrentmeter) correcting silicon photoelectric diode, and all measurements all complete in atmosphere at room temperature.Test result shows: the maximum luminous efficiency of device is 9.7cd/A, and high-high brightness is 18720cd/m
2.
The above embodiment only have expressed several embodiment of the present invention, and it describes comparatively concrete and detailed, but therefore can not be interpreted as the restriction to the scope of the claims of the present invention.It should be pointed out that for the person of ordinary skill of the art, without departing from the inventive concept of the premise, can also make some distortion and improvement, these all belong to protection scope of the present invention.Therefore, the protection domain of patent of the present invention should be as the criterion with claims.
Claims (10)
1. a blue-ray organic electroluminescent material, is characterized in that, its structure is such as formula as follows:
In formula, R is C
1~ C
20alkyl.
2. a preparation method for blue-ray organic electroluminescent material as claimed in claim 1, is characterized in that, its step is as follows:
The compd A providing following structural formula to represent respectively and B,
Under oxygen-free environment, be dissolve mol ratio during the compd A of 1:2 ~ 2.4 and B are added into containing catalyzer and alkaline solution organic solvent, the mixing solutions obtained carries out Suzuki coupling reaction 12 ~ 48 hours at 70 ~ 130 DEG C, stopped reaction cool to room temperature, separating-purifying reaction solution, obtains the described blue-ray organic electroluminescent material described in following structural formula:
In formula, R is C
1~ C
20alkyl.
3. the preparation method of blue-ray organic electroluminescent material according to claim 2, is characterized in that, described catalyzer is bis-triphenylphosphipalladium palladium dichloride or tetra-triphenylphosphine palladium; The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
4. the preparation method of blue-ray organic electroluminescent material according to claim 2, is characterized in that, described catalyzer is the mixture of organic palladium and organophosphorus ligand, and the mol ratio of described organic palladium and organophosphorus ligand is 1:4 ~ 8; The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
5. the preparation method of blue-ray organic electroluminescent material according to claim 4, it is characterized in that, described organic palladium is palladium or three or two argon benzyl acetone two palladiums, described organophosphorus ligand is three (o-methyl-phenyl-) phosphines or 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl.
6. the preparation method of blue-ray organic electroluminescent material according to claim 5, it is characterized in that, described mixture is the mixture of palladium and tri-o-tolyl phosphine, or described mixture is three or two argon benzyl acetone two palladiums and 2-dicyclohexyl phosphine-2 ', the mixture of 6 '-dimethoxy-biphenyl.
7. the preparation method of blue-ray organic electroluminescent material according to claim 2, is characterized in that, described alkaline solution is selected from 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 described compd A is 20:1.
8. the preparation method of blue-ray organic electroluminescent material according to claim 2, is characterized in that, described organic solvent is selected from as at least one in toluene, DMF, tetrahydrofuran (THF).
9. the preparation method of blue-ray organic electroluminescent material according to claim 2, is characterized in that, described separating-purifying reaction solution comprises:
After Suzuki coupling reaction stops, with dichloromethane extraction repeatedly and merge organic phase, after this organic phase is spin-dried for after anhydrous magnesium sulfate drying, obtain crude product, this crude product adopts volume ratio to be that sherwood oil and the ethyl acetate of 10:1 mixes leacheate and be separated through silica gel column chromatography and obtain crystalline substance, this crystalline substance, under vacuo after 50 DEG C of dry 24h, obtains described blue-ray organic electroluminescent material.
10. the application of blue-ray organic electroluminescent material as claimed in claim 1 in organic electroluminescence device luminescent layer.
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|---|---|---|---|---|
| JP2019069939A (en) * | 2017-10-10 | 2019-05-09 | 出光興産株式会社 | Novel compound and organic electroluminescent element |
| CN113321659A (en) * | 2021-05-27 | 2021-08-31 | 武汉尚赛光电科技有限公司 | Organic electroluminescent material and device thereof |
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2013
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2019069939A (en) * | 2017-10-10 | 2019-05-09 | 出光興産株式会社 | Novel compound and organic electroluminescent element |
| CN113321659A (en) * | 2021-05-27 | 2021-08-31 | 武汉尚赛光电科技有限公司 | Organic electroluminescent material and device thereof |
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Application publication date: 20150506 |