CN108484608A - A kind of Pyrazolopyrimidine compound and application thereof and luminescent device - Google Patents

A kind of Pyrazolopyrimidine compound and application thereof and luminescent device Download PDF

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CN108484608A
CN108484608A CN201810266637.3A CN201810266637A CN108484608A CN 108484608 A CN108484608 A CN 108484608A CN 201810266637 A CN201810266637 A CN 201810266637A CN 108484608 A CN108484608 A CN 108484608A
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黄锦海
苏建华
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Shanghai Taoe Chemical Technology Co Ltd
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Abstract

The present invention provides a kind of Pyrazolopyrimidine compounds, have the following structure formula：The Pyrazolopyrimidine compound has preferable thermal stability, high-luminous-efficiency, high luminance purity, can be applied to organic electroluminescence device, solar cell, Organic Thin Film Transistors or organophotoreceptorswith field.The present invention also provides a kind of organic electroluminescence devices, the device includes anode, cathode and organic layer, organic layer includes at least one layer in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, the at least one layer Pyrazolopyrimidine compound containing such as structural formula I in organic layer has high efficiency and optical purity using the organic electroluminescence device that Pyrazolopyrimidine compound makes.

Description

A kind of Pyrazolopyrimidine compound and application thereof and luminescent device
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of Pyrazolopyrimidine compound and application thereof, Further relate to a kind of luminescent device.
Background technology
Organic electroluminescence device (OLEDs) is between two metal electrodes by spin coating or vacuum evaporation deposition one The device that layer organic material is prepared, a classical three layer organic electroluminescence device include hole transmission layer, luminescent layer And electron transfer layer.The electronics generated by cathode is followed to be incorporated in through electron transfer layer through hole transmission layer in the hole generated by anode Luminescent layer forms exciton, then shines.Organic electroluminescence device can be adjusted as desired by the material for changing luminescent layer Section emits the light of various needs.
Organic electroluminescence device has self-luminous, wide viewing angle, low energy consumption, efficiency as a kind of novel display technology High, thin, rich in color, fast response time, Applicable temperature range be wide, low driving voltage, can make flexible with it is transparent Display panel and the particular advantages such as environmental-friendly can be applied on flat-panel monitor and a new generation's illumination, be can also be used as The backlight of LCD.
Since the invention at the bottom of the 1980s, organic electroluminescence device is industrially applied, such as As screens such as camera and mobile phones, but current OLED device, since efficiency is low, it is wider that the factors such as service life is short restrict it General application, especially large screen display.And it is exactly in organic electroluminescence device to restrict one of key factor The performance of electroluminescent organic material.Additionally, due to OLED device when applying voltage-operated, Joule heat will produce so that Organic material is easy to happen crystallization, affects service life and the efficiency of device, therefore, it is also desirable to develop the organic electroluminescence of stability and high efficiency Luminescent material.
Organic electrophosphorescenpolymer phenomenon, breaches theoretical limitation of the organic electroluminescent quantum efficiency less than 25%, and promotion is arrived 100% (Baldo M.A., Forrest S.R.Et al, Nature, 1998,395,151-154), application also greatly carry The high efficiency of organic electroluminescence device.Usually, electroluminescent phosphorescence needs to use host-guest system technology, is commonly used as phosphorus The CBP (4,4'-bis (9-carbazolyl)-biphenyl) of light material of main part has efficient and high triplet energy level, when its work Based on material when, triplet energy state effectively can be transferred to object phosphorescent light-emitting materials from light emitting host material.But by In the characteristic of the hole of CBP easily transmission and the flowing of electronics difficulty so that as a result the charge unbalance of luminescent layer reduces the effect of device Rate.
Invention content
It is the compound for having the following structure Formulas I the present invention provides a kind of Pyrazolopyrimidine compound：
Wherein, R1Selected from substitution either two aromatic aminos of unsubstituted C12-C30, substitution or unsubstituted C18- The indoles of the triaromatic amine base of C30, the substitution either carbazyl of unsubstituted C12-C30, substitution or unsubstituted C8-C30 Base；
R2And R3Independently selected from hydrogen, deuterium, the alkyl of C1-C12, the alkoxy of C1-C8, substitution or unsubstituted C6- The aryl of C30, the substitution either heteroaryl of unsubstituted C3-C30, substitution or the fragrant phosphino- of unsubstituted C6-C30, substitution Either the triaromatic amine base of two aromatic aminos of unsubstituted C12-C30, substitution or unsubstituted C18-C30, substitution or The indyl of the carbazyl of unsubstituted C12-C30, substitution or unsubstituted C8-C30.
Optionally, R2Selected from hydrogen, phenyl, cyano-phenyl, fluorine substituted-phenyl, xenyl, diphenyl substituted-phenyl, naphthalene, Three simultaneously phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (substitutions or unsubstituted of 9,9- bis- Aryl) fluorenyl, 9,9- be Spirofluorene-based, dibenzothiophene, dibenzofuran group, pyridyl group, pyrimidine radicals, pyridazinyl, triazine radical, miaow Oxazolyl, oxazolyls, thiazolyl, thiadiazolyl group, quinolyl, isoquinolyl, quinazolyl, quinoxalinyl, azepine dibenzofurans Base, azepine dibenzothiophene, imidazole radicals, carbazyl, two aromatic aminos, triaromatic amine base, indyl and the above aryl or miscellaneous Aryl replaces gained group by the alkyl of C1-C12.
Optionally, R3Selected from hydrogen, phenyl, methyl, tertiary butyl.
Further alternative, Pyrazolopyrimidine compound is the compound of following structural 1-34：
The Pyrazolopyrimidine compound of the present invention can be applied to organic electroluminescence device, solar cell, organic thin Film transistor or organophotoreceptorswith field.
The present invention also provides a kind of organic electroluminescence device, which includes anode, cathode and organic layer, organic layer Including at least one in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer Layer, at least one layer of Pyrazolopyrimidine compound containing as described in structural formula I in the organic layer.
Wherein organic layer is luminescent layer；
Or organic layer is luminescent layer and electron transfer layer；
Or organic layer is luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole transmission layer and luminescent layer；
Or organic layer is hole injection layer, hole transmission layer and luminescent layer；
Or organic layer is hole transmission layer, luminescent layer and electron transfer layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer and electron transfer layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole injection layer, hole transmission layer, barrier layer, luminescent layer, electron transfer layer and electron injection Layer；
Or organic layer is hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and hole blocking layer；
Or organic layer is hole transmission layer, luminescent layer, electron injecting layer and hole blocking layer.
Further alternative, the layer where the Pyrazolopyrimidine compound is luminescent layer.
Pyrazolopyrimidine compound as described in structural formula I is used alone, or is used in mixed way with other compounds；Such as structure Pyrazolopyrimidine compound described in Formulas I can be used alone one such compound, can also use in structural formula I simultaneously Two or more compound；A kind of Pyrazolopyrimidine compound selected from structural formula 1-34 is used alone, or simultaneously Use the two or more Pyrazolopyrimidine compounds selected from structural formula 1-34.
Still optionally further, organic electroluminescence device of the invention include anode, hole injection layer, hole transmission layer, Luminescent layer, electron transfer layer, electron injecting layer and cathode contain one or more kinds of structural formula I's wherein in luminescent layer Compound；It is further preferred that the compound containing one or more kinds of structural formula 1-34 in luminescent layer.
The overall thickness of the organic electroluminescence device organic layer of the present invention is 1-1000nm, preferably 50-500nm.
When having the compound of structural formula I using the present invention, can arrange in pairs or groups makes the organic electroluminescence device of the present invention With other materials, such as in hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and barrier layer Deng, and obtain blue and green light, yellow light, feux rouges or white light.
The hole transmission layer and hole injection layer of organic electroluminescence device of the present invention, material requested have good hole Transmission performance can effectively be transferred to hole on luminescent layer from anode.May include that other small molecules and macromolecule are organic Compound, including but not limited to carbazole compound, triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanine Class compound, six cyano, six miscellaneous triphen (hexanitrilehexaazatriphenylene), 2,3,5,6- tetra- fluoro- 7,7', 8, Tetra- cyanogen dimethyl-parabenzoquinones (F4-TCNQ) of 8'-, polyvinyl carbazole, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of the organic electroluminescence device of the present invention has the good characteristics of luminescence, can be adjusted according to the needs The range of visible light.In addition to the present invention is with Compounds of structural formula I, following compound can also be contained, but not limited to this, Naphthalene compounds, pyrene compound, compound of fluorene class, luxuriant and rich with fragrance class compound,Class compound, glimmering anthracene compound, anthracene class chemical combination Object, pentacene class compound, class compound, two aromatic ethylene class compounds, triphenylamine ethylene compounds, aminated compounds, Benzimidazoles compound, furfuran compound, organic metal chelate complex.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires good electronic transmission performance, energy In reaching effectively electronics from cathode transport to luminescent layer, there is prodigious electron mobility.In addition to that can use with this hair Outside bright compound, it is also an option that following compound, but not limited to this：Oxa- oxazole, thiazole compound, triazole Compound, three nitrogen piperazine class compounds, triazine class compound, quinoline class compound, phenodiazine anthracene compound, siliceous heterocyclic Compound, quinolines, ferrosin class compound, metallo-chelate (such as Alq3), fluorine substituted benzene compound, benzo miaow Azole compounds.
Electronics effectively can be injected into organic layer by the electron injecting layer of organic electroluminescence device of the present invention from cathode In, it is mainly selected from the alkali metal either compound of alkali metal or the compound selected from alkaline-earth metal or alkaline-earth metal or alkali Metal complex can select following compound, and but not limited to this：Alkali metal, alkaline-earth metal, rare earth metal, alkali metal Oxide either halide, the oxide of alkaline-earth metal or halide, the oxide of rare earth metal or halide, alkali metal Or the organic complex of alkaline-earth metal；Preferably lithium, lithium fluoride, lithia, lithium nitride, 8-hydroxyquinoline lithium, caesium, carbonic acid Caesium, 8-hydroxyquinoline caesium, calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, magnesia, these compounds can individually make With can also mixture use, can also be used cooperatively with other electroluminescent organic materials.
Each layer of organic layer in the organic electroluminescence device of the present invention can be steamed by vacuum vapour deposition, molecular beam It is prepared by the modes such as plating method, the dip coating for being dissolved in solvent, spin-coating method, stick coating method or inkjet printing.Metal motor can be made It is prepared with vapour deposition method or sputtering method.
Device experimental shows Pyrazolopyrimidine compound of the present invention as described in structural formula I, have preferable thermal stability, High-luminous-efficiency, high luminance purity.There is electroluminescent hair using the organic electroluminescence device that the Pyrazolopyrimidine compound makes The advantages of light efficiency is good and excitation purity is excellent and long lifespan.
Description of the drawings
Fig. 1 is a kind of organic electroluminescence device structural schematic diagram of the present invention,
Wherein, 110 be glass substrate, and 120 be anode, and 130 be hole injection layer, and 140 be hole transmission layer, and 150 be resistance Barrier, 160 be luminescent layer, and 170 be electron transfer layer, and 180 be electron injecting layer, and 190 be cathode.
Specific implementation mode
In order to describe the present invention in more detail, spy lifts following example, and but not limited to this.
Embodiment 1
The synthetic route of compound 7
The synthetic method of compound 7
In flask, iodo- 6- bromines pyrazolo [1, the 5-a] pyrimidines (1g, 3.1mmol) of 3-, 4- hexichol amido phenyl boric acids is added (1.8g, 6.2mmol), potassium carbonate (0.86g, 6.2mmol), tetra-triphenylphosphine palladium (50mg), tetrahydrofuran (20mL) and water (10mL) is heated to reflux 12 hours under nitrogen protection, is cooled down, is extracted with dichloromethane, is dry, concentrated, crude product is through column layer Analysis purifying obtains product 1.59g, yield 85%.
Embodiment 2
The synthetic route of compound 10
The synthetic method of intermediate 10-1
For its synthetic method as the synthetic method of compound 7, raw materials used is that the iodo- 6- bromines pyrazolos [1,5-a] of 3- are phonetic Pyridine and 2- benzophenanthrene boric acid, yield 67%.
The synthetic method of compound 10
For its synthetic method as the synthetic method of compound 7, raw materials used is intermediate 10-1 and 4- carbazyl benzene boron Acid, yield 78%.
Embodiment 3
The synthetic route of compound 11
For its synthetic method as the synthetic method of compound 7, raw materials used is that the iodo- 6- bromines pyrazolos [1,5-a] of 3- are phonetic Pyridine and 4- carbazyl phenyl boric acids, yield 82%.
Embodiment 4
The synthesis of compound 15
For its synthetic method as the synthetic method of compound 7, raw materials used is that the iodo- 6- bromines pyrazolos [1,5-a] of 3- are phonetic Pyridine and 3- carbazyl phenyl boric acids, yield 74%.
Embodiment 5
The synthetic route of compound 23
The synthetic method of compound 23-1
For its synthetic method as the synthetic method of compound 7, raw materials used is that the iodo- 6- bromines pyrazolos [1,5-a] of 3- are phonetic Pyridine and 3,5- diphenyl benzene boric acid, yield 73%.
The synthetic method of compound 23
Its synthetic method as the synthetic method of compound 7, it is raw materials used be intermediate 23-1 and fluorenes indole boronic acid ester, Yield 76%.
Embodiment 6
The synthetic route of compound 25
For its synthetic method as the synthetic method of compound 7, raw materials used is that the iodo- 6- bromines pyrazolos [1,5-a] of 3- are phonetic Pyridine and 9- phenyl-carbazole boric acid, yield 72%.
Embodiment 7
The synthetic route of compound 29
Its synthetic method as the synthetic method of compound 7, it is raw materials used be 6- bromines pyrazolo [1,5-a] pyrimidine and 3, Bis- carbazyl phenyl boric acids of 5-, yield 72%.
Embodiment 8-14
The preparation of organic electroluminescence device
OLED is prepared using the compound of above-described embodiment
First, by electrically conducting transparent ito glass substrate 110 (carrying anode 120 above) (the limited public affairs of South China glass group share Department) it passes through successively：Deionized water, ethyl alcohol, acetone and deionized water were cleaned, then with oxygen plasma treatment 30 seconds.
Then, the MnO of 3nm thickness is deposited on ITO3(molybdenum oxide) is hole injection layer 130.
Then, the TAPC that 50nm thickness is deposited on hole injection layer is hole mobile material 140.
Then, TCTA is deposited, forms the electronic barrier layer 150 of 5nm thickness.
Then, the luminescent layer 160 of 20nm thickness is deposited on electronic barrier layer, wherein shine based on the compounds of this invention Material, and the Ir (ppy) for being 3% with weight ratio3Guest materials is adulterated as phosphorescence.
Then, the BmPYPB of 40nm thickness is deposited on the light-emitting layer as electron transfer layer 170.
Finally, vapor deposition 1nm LiF are electron injecting layer 180 and 80nm Al as device cathodes 190.
Prepared device (structural schematic diagram is shown in Fig. 1) with Photo Research PR650 spectrometers measure 5000cd/m2Brightness under current efficiency be such as table 1.
Comparative example 1
Except use CBP replace the compounds of this invention as material of main part in addition to, other steps are according to the device of embodiment 8-14 Preparation method prepares device.
Table 1
Embodiment Compound Current efficiency (cd/A) Luminescent color
8 7 49 Green light
9 10 54 Green light
10 11 52 Green light
11 15 54 Green light
12 23 55 Green light
13 25 53 Green light
14 29 56 Green light
Comparative example 1 CBP 45 Green light
The structural formula of compound described in device is as follows：
From table 1 it follows that the compounds of this invention is used for organic electroluminescence device, operating voltage can be reduced, is carried High device efficiency is the phosphorescent light body material with excellent performance.As described above, the compound of the present invention has high stabilization Property, the organic electroluminescence device of preparation has high efficiency and optical purity.
The preferred embodiment of the present invention has been described in detail above.It should be appreciated that those skilled in the art without It needs creative work according to the present invention can conceive and makes many modifications and variations.Therefore, all technologies in the art Personnel are available by logical analysis, reasoning, or a limited experiment on the basis of existing technology under this invention's idea Technical solution, all should be in the protection domain being defined in the patent claims.

Claims (10)

1. a kind of Pyrazolopyrimidine compound, which is characterized in that be the compound for having the following structure Formulas I：
Wherein, R1Selected from substitution either two aromatic aminos of unsubstituted C12-C30, substitution or unsubstituted C18-C30 three The indyl of aromatic amino, the substitution either carbazyl of unsubstituted C12-C30, substitution or unsubstituted C8-C30；
R2And R3Independently selected from hydrogen, deuterium, the alkyl of C1-C12, the alkoxy of C1-C8, substitution or unsubstituted C6-C30 Aryl, the substitution either fragrant phosphino- of the heteroaryl of unsubstituted C3-C30, substitution or unsubstituted C6-C30, substitution or not Two aromatic aminos of substituted C12-C30, the substitution either triaromatic amine base of unsubstituted C18-C30, substitution or unsubstituted The carbazyl of C12-C30, substitution or unsubstituted C8-C30 indyl.
2. Pyrazolopyrimidine compound as described in claim 1, which is characterized in that R2It is taken selected from hydrogen, phenyl, cyano-phenyl, fluorine For phenyl, xenyl, diphenyl substituted-phenyl, naphthalene, three and phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, (9,9- bis- Alkyl) fluorenyl, (9,9- bis- substitution or unsubstituted aryl) fluorenyl, 9,9- be Spirofluorene-based, dibenzothiophene, dibenzofurans Base, pyridyl group, pyrimidine radicals, pyridazinyl, triazine radical, imidazole radicals, oxazolyls, thiazolyl, thiadiazolyl group, quinolyl, isoquinolyl, Quinazolyl, quinoxalinyl, azepine dibenzofuran group, azepine dibenzothiophene, imidazole radicals, carbazyl, two aromatic aminos, Triaromatic amine base, indyl and the above aryl or heteroaryl replace gained group by the alkyl of C1-C12.
3. Pyrazolopyrimidine compound as described in claim 1, which is characterized in that R3Selected from hydrogen, phenyl, methyl, tertiary butyl.
4. Pyrazolopyrimidine compound as described in claim 1, which is characterized in that be the compound of following structural 1-34：
5. application of the Pyrazolopyrimidine compound described in claim 1 in organic electroluminescence device.
6. a kind of organic electroluminescence device, which includes anode, cathode and organic layer, and organic layer includes luminescent layer, hole At least one layer in implanted layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, which is characterized in that institute It states at least one layer in organic layer and contains Pyrazolopyrimidine compound as described in claim 1.
7. organic electroluminescence device as claimed in claim 6, which is characterized in that pyrazolopyrimidine described in claim 1 Layer where compound is luminescent layer.
8. organic electroluminescence device as claimed in claim 6, which is characterized in that pyrazolopyrimidine described in claim 1 Compound is used alone, or is used in mixed way with other compounds.
9. organic electroluminescence device as claimed in claim 6, which is characterized in that be used alone a kind of selected from such as claim The Pyrazolopyrimidine compound of structural formula 1-34 described in 4, or simultaneously using two or more selected from knot as claimed in claim 4 The Pyrazolopyrimidine compound of structure formula 1-34.
10. organic electroluminescence device as claimed in claim 6, which is characterized in that the overall thickness of the organic layer is 1- 1000nm。
CN201810266637.3A 2018-03-28 2018-03-28 A kind of Pyrazolopyrimidine compound and application thereof and luminescent device Pending CN108484608A (en)

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Application publication date: 20180904