CN112851591A - Triphenylene-based organic compound, organic electroluminescent material and device - Google Patents
Triphenylene-based organic compound, organic electroluminescent material and device Download PDFInfo
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Abstract
The invention discloses a triphenylene-based organic compound, an organic electroluminescent material and a device, and the structural formula of the organic compound is shown as the following formula (I):wherein R is any one of hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted C1-C5 alkyl group, a substituted or unsubstituted C6-C30 aromatic group and a substituted or unsubstituted C5-C30 heteroaromatic group; x, Y, Z are each independently CH or N, and at least one of X, Y, Z is N; m, s and n are each independently 0 or 1; the organic compound is used as an electron transport layer, so that the driving voltage of the device can be greatly reduced, the consumption of electric energy is greatly reduced, the luminous efficiency is obviously improved, and in addition, the service life of the organic electroluminescent device is obviously prolonged by reducing the driving voltage.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to an organic compound based on triphenylene, an organic electroluminescent material and an organic electroluminescent device.
Background
Organic Light Emitting Diodes (OLEDs), originally discovered in the laboratory by professor dunqing cloud of chinese ethnic origin, have since developed and studied OLEDs. OLEDs have two major application areas: illumination and display.
The OLED is a current-type organic light emitting device, and emits light by injection and recombination of carriers, and the intensity of light emission is proportional to the injected current. Under the action of an electric field, holes generated by an anode and electrons generated by a cathode move, are respectively injected into a hole transport layer and an electron transport layer, and migrate to a light emitting layer. When the two meet at the light emitting layer, energy excitons are generated, thereby exciting the light emitting molecules to finally generate visible light.
An OLED device generally includes a cathode, an anode, a Hole Injection Layer (HIL), an Electron Injection Layer (EIL), a Hole Transport Layer (HTL), an Electron Transport Layer (ETL), and an emission layer (EML). The selective use of each layer of organic electroluminescent material plays a decisive role in the performance of the OLED device, at present, the OLED device also has the defects of high starting voltage, low luminous efficiency, short service life and the like, the search for the organic electroluminescent material with more excellent performance becomes the current primary task, the performance of the OLED device can be greatly improved through the reasonable use of the organic electroluminescent material, and the application prospect is improved.
Disclosure of Invention
The purpose of the invention is as follows: in view of the above technical problems, the present invention provides a triphenylene-based organic compound, and an organic electroluminescent material and device.
In order to achieve the purpose of the invention, the technical scheme adopted by the invention is as follows:
a triphenylene-based organic compound having the formula (I):
wherein R is any one of hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted C1-C5 alkyl group, a substituted or unsubstituted C6-C30 aromatic group and a substituted or unsubstituted C5-C30 heteroaromatic group;
x, Y, Z are each independently CH or N, and at least one of X, Y, Z is N;
m, s and n are each independently 0 or 1.
Further, the structural formula of the organic compound is one of the following formulas (II), (III), (IV) and (V):
wherein R is any one of hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted C1-C5 alkyl group, a substituted or unsubstituted C6-C30 aromatic group and a substituted or unsubstituted C5-C30 heteroaromatic group;
m, s and n are each independently 0 or 1.
Further, R is hydrogen, deuterium, a fluorine atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a triphenylene group, a fluorenyl group, a dibenzoenyl group, a 9, 9-dimethylfluorenyl group, a 9,9' -spirobifluorene group, a 9, 9-diphenylfluorenyl group, a dibenzoenyl group, a carbazolyl group, an N-phenylcarbazolyl group;
the methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylene, fluorenyl, dibenzoyl, 9-dimethylfluorenyl, 9' -spirobifluorene, 9-diphenylfluorenyl, dibenzoyl sulfide, carbazolyl, N-phenylcarbazolyl are unsubstituted or are obtained by substituting at least one hydrogen with deuterium.
Further, the structure of the organic compound is as follows:
an organic electroluminescent material comprising at least one of the above organic compounds.
The organic electroluminescent material is applied to the preparation of organic electroluminescent devices.
An organic electroluminescent device comprising: a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are sequentially stacked; the electron transport layer contains the organic electroluminescent material.
The invention discloses an organic electroluminescent display device containing the organic electroluminescent device.
The invention also discloses an organic electroluminescent lighting device containing the organic electroluminescent device.
The room temperature of the invention is 25 +/-5 ℃.
The invention has the beneficial effects that:
the triphenylene group has excellent electron transfer rate and good rigidity and thermal stability, and the Tg value of the material can be greatly improved by adding the triphenylene group, so that the material has good thermal stability, chemical stability and morphological stability, and the crystallization of the material can be prevented. Meanwhile, the introduction of an electron-withdrawing substituent cyano group can further increase the electron transmission rate of the device, so that the efficiency of the device is improved, the driving voltage of the device is reduced, and the effect of saving energy is achieved.
Drawings
Fig. 1 is a schematic structural diagram of an organic electroluminescent device provided by the present invention;
the reference numbers in the figures represent respectively:
1-cathode, 2-electron injection layer, 3-electron transport layer, 4-luminescent layer, 5-hole transport layer, 6-hole injection layer, 7-anode.
FIG. 2 is a TGA spectrum of the organic compound (1) of the present invention, and it can be seen from FIG. 2 that the Td value of the organic compound (1) of the present invention is 384.50 ℃.
Detailed Description
The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
Example 1:
the synthesis method of the organic compound (1) is as follows:
S1:
adding compound 1-a (5g, 317.76g/mol, 15.89mmol), compound 1-b (1.1eq, 2.57g, 146.94g/mol, 17.47mmol) and sodium carbonate (2eq, 3.37g, 105.99g/mol, 31.77mmol) to ethylene glycol diethyl ether (100g, 20 times of the mass of compound 1-a) and water (100g, 20 times of the mass of compound 1-a), stirring, adding tri (o-tolyl) phosphine (5% eq, 0.24g, 304.37g/mol, 0.79mmol) and palladium (II) acetate (1% eq, 0.04g, 224.51g/mol, 0.16mmol) in sequence, heating to reflux for 15h, separating the organic phase, washing with water, concentrating under reduced pressure to obtain crude product, and performing EI column chromatography to obtain compound 1-c (4.96g, yield), (MS 91.8%): 339(M +).
S2:
Compounds 1-c (4g, 339.97g/mol, 11.84mmol), compounds 1-d (1.1eq, 4.53g,
348.20g/mol, 13.02mmol) and sodium carbonate (2eq, 2.51g, 105.99g/mol, 23.68mmol) are added to ethylene glycol diamine ether (80g, 20 times the mass of compound 1-c) and water (80g, 20 times the mass of compound 1-c), after stirring and mixing uniformly, tri (o-tolyl) phosphine (5% eq, 0.18g, 304.37g/mol, 0.59mmol) and palladium (II) acetate (1% eq, 0.03g, 224.51g/mol, 0.12mmol) are sequentially added, after heating to reflux reaction for 15h, the organic phase is separated, washed with water and concentrated under reduced pressure to obtain a crude product, which is subjected to column chromatography to obtain compound 1-e (4.68g, yield 70.2%), ms (ei): 563(M +).
S3:
Adding compound 1-e (4g, 563.45g/mol, 7.12mmol), compound 1-f (1.1eq, 1.15g, 121.93g/mol, 7.83mmol) and sodium carbonate (2eq, 1.51g, 105.99g/mol, 14.23mmol) into ethylene glycol diethyl ether (80g, 20 times of the mass of compound 1-e) and water (80g, 20 times of the mass of compound 1-e), stirring and mixing uniformly, adding tri (o-tolyl) phosphine (5% eq, 0.11g, 304.37g/mol, 0.36mmol) and palladium (II) acetate (1% eq, 0.02g, 224.51g/mol, 0.07mmol) in sequence, heating to reflux for 15h, separating out the organic phase, washing with water and concentrating under reduced pressure to obtain crude EI, and performing column chromatography to obtain crude organic electroluminescent material (1) (3.51g, yield 88.1%), MS): 560(M +).
Example 2:
the synthesis method of the organic compound (6) is as follows:
adding compound 2-a (4g, 563.45g/mol, 7.12mmol), compound 2-b (1.1eq, 1.39g, 178.04g/mol, 7.83mmol) and sodium carbonate (2eq, 1.51g, 105.99g/mol, 14.23mmol) to ethylene glycol diamine ether (80g, 20 times of the mass of compound 2-a) and water (80g, 20 times of the mass of compound 2-a), stirring and mixing uniformly, adding tri (o-tolyl) phosphine (5% eq, 0.11g, 304.37g/mol, 0.36mmol) and palladium (II) acetate (1% eq, 0.02g, 224.51g/mol, 0.07mmol) in sequence, heating to reflux for 15h, separating out the organic phase, washing with water and concentrating under reduced pressure to obtain crude el, and subjecting the crude el to column chromatography to obtain organic electroluminescent material (6) (3.79g, yield 86.5%), ms): 616(M +).
Example 3:
the synthesis method of the organic compound (7) is as follows:
adding compound 3-a (4g, 563.45g/mol, 7.12mmol), compound 3-b (1.1eq, 1.55g, 198.03g/mol, 7.83mmol) and sodium carbonate (2eq, 1.51g, 105.99g/mol, 14.23mmol) to ethylene glycol diamine ether (80g, 20 times of the mass of compound 3-a) and water (80g, 20 times of the mass of compound 3-a), stirring and mixing uniformly, adding tri (o-tolyl) phosphine (5% eq, 0.11g, 304.37g/mol, 0.36mmol) and palladium (II) acetate (1% eq, 0.02g, 224.51g/mol, 0.07mmol) in sequence, heating to reflux for 15h, separating out the organic phase, washing with water and concentrating under reduced pressure to obtain crude el, and subjecting the crude el to column chromatography to obtain organic electroluminescent material (7) (3.9g, yield 86.1%), ms): 636(M +).
Example 4:
the synthesis method of the organic compound (8) is as follows:
adding compound 4-a (4g, 563.45g/mol, 7.12mmol), compound 4-b (1.1eq, 1.94g, 248.08g/mol, 7.83mmol) and sodium carbonate (2eq, 1.51g, 105.99g/mol, 14.23mmol) to ethylene glycol diamine ether (80g, 20 times of the mass of compound 4-a) and water (80g, 20 times of the mass of compound 4-a), stirring, mixing, adding tri (o-tolyl) phosphine (5% eq, 0.11g, 304.37g/mol, 0.36mmol) and palladium (II) acetate (1% eq, 0.02g, 224.51g/mol, 0.07mmol), heating to reflux for 15h, separating the organic phase, washing with water, concentrating under reduced pressure to obtain crude el, and subjecting the crude el to column chromatography to obtain organic electroluminescent material (8) (3.99g, 81.7%) yield: 686(M +).
Example 5:
the synthesis of the organic compound (10) is as follows:
adding compound 5-a (4g, 339.97g/mol, 11.84mmol), compound 5-b (2.1eq, 8.65g348.20g/mol, 24.86mmol) and sodium carbonate (4eq, 5.02g, 105.99g/mol, 47.35mmol) into ethylene glycol diethyl ether (80g, 20 times of the mass of compound 5-a) and water (80g, 20 times of the mass of compound 5-a), stirring and mixing uniformly, sequentially adding tri (o-tolyl) phosphine (5% eq, 0.18g, 304.37g/mol, 0.59mmol) and palladium (II) acetate (1% eq, 0.03g, 224.51g/mol, 0.12mmol), heating to reflux for 15h, separating out the organic phase, washing with water, concentrating under reduced pressure to obtain a crude product, and performing column chromatography to obtain organic compound ei (10) (6.16g, 66.2%), yield (ms): 786(M +).
Example 6:
the synthesis of organic compound (12) is as follows:
adding compound 6-a (4g, 563.45g/mol, 7.12mmol), compound 6-b (1.1eq, 2.26g, 288.11g/mol, 7.83mmol) and sodium carbonate (2eq, 1.51g, 105.99g/mol, 14.23mmol) to ethylene glycol diethyl ether (80g, 20 times the mass of compound 6-a) and water (80g, 20 times the mass of compound 6-a), stirring, adding tri (o-tolyl) phosphine (5% eq, 0.11g, 304.37g/mol, 0.36mmol) and palladium (II) acetate (1% eq, 0.02g, 224.51g/mol, 0.07mmol), heating to reflux for 15h, separating the organic phase, washing with water, concentrating under reduced pressure to obtain crude EI (12) (3.73g, yield 72.2%), and performing column chromatography to obtain organic compound EI (12): 726(M +).
Example 7:
the synthesis of the organic compound (13) is as follows:
adding compound 7-a (4g, 563.45g/mol, 7.12mmol), compound 7-b (1.1eq, 2.46g, 314.19g/mol, 7.83mmol) and sodium carbonate (2eq, 1.51g, 105.99g/mol, 14.23mmol) to ethylene glycol diethyl ether (80g, 20 times the mass of compound 7-a) and water (80g, 20 times the mass of compound 7-a), stirring, adding tri (o-tolyl) phosphine (5% eq, 0.11g, 304.37g/mol, 0.36mmol) and palladium (II) acetate (1% eq, 0.02g, 224.51g/mol, 0.07mmol), heating to reflux for 15h, separating the organic phase, washing with water, concentrating under reduced pressure to obtain crude product, and performing column chromatography to obtain organic compound ei (13) (3.78g, yield 70.6%), ms (70.6%): 752(M +).
Example 8:
the synthesis of organic compound (19) is as follows:
adding 8-a (4g, 563.45g/mol, 7.12mmol), 8-b (1.1eq, 1.09g, 138.97g/mol, 7.83mmol) and sodium carbonate (2eq, 1.51g, 105.99g/mol, 14.23mmol) to ethylene glycol diethyl ether (80g, 20 times the mass of compound 8-a) and water (80g, 20 times the mass of compound 8-a), stirring, adding tri (o-tolyl) phosphine (5% eq, 0.11g, 304.37g/mol, 0.36mmol) and palladium (II) acetate (1% eq, 0.02g, 224.51g/mol, 0.07mmol), heating to reflux for 15h, separating the organic phase, washing with water, concentrating under reduced pressure to obtain crude EI (19) (3.71g, yield 90.2%), and performing column chromatography to obtain organic compound EI (19) (3.71%, MS (90.2%): 577(M +).
Example 9:
the synthesis of organic compound (21) was as follows:
S1:
adding a compound 9-a (4g, 339.97g/mol, 11.84mmol), a compound 9-b (1.1eq, 4.53g, 348.20g/mol, 13.02mmol) and sodium carbonate (2eq, 2.51g, 105.99g/mol, 23.68mmol) into ethylene glycol diamine ether (80g, 20 times of the mass of the compound 9-a) and water (80g, 20 times of the mass of the compound 9-a), stirring and mixing uniformly, adding tri (o-tolyl) phosphine (5% eq, 0.18g, 304.37g/mol, 0.59mmol) and palladium acetate (II) (1% eq, 0.03g, 224.51g/mol, 0.12mmol) in sequence, heating to reflux for 15h, separating out the organic phase, washing with water, concentrating under reduced pressure to obtain a crude product, and performing column chromatography to obtain a compound 9-c (4.78g, yield 71.8%), MS (71.8%): 563(M +).
S2:
Adding a compound 9-c (4g, 563.45g/mol, 7.12mmol), a compound 9-d (1.1eq, 1.15g, 121.93g/mol, 7.83mmol) and sodium carbonate (2eq, 1.51g, 105.99g/mol, 14.23mmol) into ethylene glycol diethyl ether (80g, 20 times of the mass of the compound 9-c) and water (80g, 20 times of the mass of the compound 9-c), stirring and mixing uniformly, adding tri (o-tolyl) phosphine (5% eq, 0.11g, 304.37g/mol, 0.36mmol) and palladium (II) acetate (1% eq, 0.02g, 224.51g/mol, 0.07mmol) in sequence, heating to reflux for 15h, separating out the organic phase, washing with water and concentrating under reduced pressure to obtain a crude product, and performing column chromatography to obtain an organic compound EI (21) (3.33g, yield 83.5%), MS: 560(M +).
Example 10:
the synthesis of organic compound (41) was as follows:
S1:
adding 10-a (5g, 317.76g/mol, 15.89mmol), 10-b (1.1eq, 3.9g, 223.03g/mol, 17.47mmol) and sodium carbonate (2eq, 3.37g, 105.99g/mol, 31.77mmol) to ethylene glycol diethyl ether (100g, 20 times the mass of compound 10-a) and water (100g, 20 times the mass of compound 10-a), stirring, adding tri (o-tolyl) phosphine (5% eq, 0.24g, 304.37g/mol, 0.79mmol) and palladium (II) acetate (1% eq, 0.04g, 224.51g/mol, 0.16mmol) in sequence, heating to reflux for 15h, separating the organic phase, washing with water, concentrating under reduced pressure to obtain crude EI, and performing column chromatography to obtain compound 10-c (5.59g, yield), (MS 84.5%): 416(M +).
S2:
Adding 10-c (5g, 416.07g/mol, 12.08mmol), 10-d (1.1eq, 4.63g, 348.20g/mol, 13.29mmol) and sodium carbonate (2eq, 2.56g, 105.99g/mol, 24.16mmol) to ethylene glycol diethyl ether (100g, 20 times of the mass of compound 10-c) and water (100g, 20 times of the mass of compound 10-c), stirring, adding tri (o-tolyl) phosphine (5% eq, 0.18g, 304.37g/mol, 0.6mmol) and palladium (II) acetate (1% eq, 0.03g, 224.51g/mol, 0.12mmol) in sequence, heating to reflux for 15h, separating the organic phase, washing with water, concentrating under reduced pressure to obtain crude EI, and performing column chromatography to obtain compound 10-e (5.16g, 66.9% yield (MS): 639(M +).
S3:
Adding 10-e (5g, 639.54g/mol, 7.84mmol), 10-f (1.1eq, 1.05g, 121.93g/mol, 8.62mmol) and sodium carbonate (2eq, 1.66g, 105.99g/mol, 15.67mmol) to ethylene glycol diethyl ether (100g, 20 times the mass of compound 10-e) and water (100g, 20 times the mass of compound 10-e), stirring, adding tri (o-tolyl) phosphine (5% eq, 0.12g, 304.37g/mol, 0.39mmol) and palladium (II) acetate (1% eq, 0.02g, 224.51g/mol, 0.08mmol), heating to reflux for 15h, separating out the organic phase, washing with water, concentrating under reduced pressure to obtain crude EI (41) (4.22g, 84.6%) after column chromatography: 636(M +).
Example 11:
the synthesis of organic compound (41) was as follows:
S1:
adding compound 11-a (5g, 317.76g/mol, 15.89mmol), compound 11-b (1.1eq, 3.9g, 223.03g/mol, 17.47mmol) and sodium carbonate (2eq, 3.37g, 105.99g/mol, 31.77mmol) to ethylene glycol diethyl ether (100g, 20 times the mass of compound 11-a) and water (100g, 20 times the mass of compound 11-a), stirring, adding tri (o-tolyl) phosphine (5% eq, 0.24g, 304.37g/mol, 0.79mmol) and palladium (II) acetate (1% eq, 0.04g, 224.51g/mol, 0.16mmol) in sequence, heating to reflux for 15h, separating the organic phase, washing with water, concentrating under reduced pressure to obtain crude product, and performing column chromatography to obtain compound 11-c (5.62g, 85%) EI: 416(M +).
S2:
Adding 11-c (5g, 416.07g/mol, 12.08mmol), 11-d (1.1eq, 4.63g, 348.20g/mol, 13.29mmol) and sodium carbonate (2eq, 2.56g, 105.99g/mol, 24.16mmol) to ethylene glycol diethyl ether (100g, 20 times of the mass of compound 11-c) and water (100g, 20 times of the mass of compound 11-c), stirring, adding tri (o-tolyl) phosphine (5% eq, 0.18g, 304.37g/mol, 0.6mmol) and palladium (II) acetate (1% eq, 0.03g, 224.51g/mol, 0.12mmol) in sequence, heating to reflux for 15h, separating the organic phase, washing with water, concentrating under reduced pressure to obtain crude EI, and performing EI column chromatography to obtain compound 11-e (4.96g, yield 64.4%), MS (64.4%): 639(M +).
S3:
Adding 11-e (4g, 639.54g/mol, 6.27mmol), 11-f (1.1eq, 1.05g, 436.31g/mol, 6.9mmol) and sodium carbonate (2eq, 1.33g, 105.99g/mol, 12.54mmol) to ethylene glycol diethyl ether (80g, 20 times the mass of compound 11-e) and water (80g, 20 times the mass of compound 11-e), stirring, adding tri (o-tolyl) phosphine (5% eq, 0.10g, 304.37g/mol, 0.31mmol) and palladium (II) acetate (1% eq, 0.01g, 224.51g/mol, 0.06mmol), heating to reflux for 15h, separating the organic phase, washing with water, concentrating under reduced pressure to obtain crude EI (54) (3.72g, 62.4%), and performing column chromatography to obtain organic compound EI (54) (3.72g, 62.4%), yield (MS): 951(M +).
Example 12:
the synthesis of organic compound (69) was as follows:
S1:
adding 12-a (5g, 317.76g/mol, 15.89mmol), 12-b (1.1eq, 3.9g, 223.03/mol, 17.47mmol) and sodium carbonate (2eq, 3.37g, 105.99g/mol, 31.77mmol) to ethylene glycol diamine ether (100g, 20 times the mass of compound 12-a) and water (100g, 20 times the mass of compound 12-a), stirring, adding tri (o-tolyl) phosphine (5% eq, 0.24g, 304.37g/mol, 0.79mmol) and palladium (II) acetate (1% eq, 0.04g, 224.51g/mol, 0.16mmol) in sequence, heating to reflux for 15h, separating the organic phase, washing with water, concentrating under reduced pressure to obtain crude product, and performing column chromatography to obtain crude product of EI (12-c (5.51g, yield 83.4%), MS (83.4%): 416(M +).
S2:
Adding 12-c (5g, 416.07g/mol, 12.08mmol), 12-d (1.1eq, 4.63g, 348.20g/mol, 13.29mmol) and sodium carbonate (2eq, 2.56g, 105.99g/mol, 24.16mmol) to ethylene glycol diethyl ether (100g, 20 times of the mass of compound 12-c) and water (100g, 20 times of the mass of compound 12-c), stirring, adding tri (o-tolyl) phosphine (5% eq, 0.18g, 304.37g/mol, 0.6mmol) and palladium (II) acetate (1% eq, 0.03g, 224.51g/mol, 0.12mmol) in sequence, heating to reflux for 15h, separating the organic phase, washing with water, concentrating under reduced pressure to obtain crude EI, and performing EI column chromatography to obtain 12-e (4.99g, 64.8% yield): 639(M +).
S3:
Adding 12-e (4g, 639.54g/mol, 6.27mmol), 12-f (1.1eq, 2.06g, 298.14g/mol, 6.9mmol) and sodium carbonate (2eq, 1.33g, 105.99g/mol, 12.54mmol) to ethylene glycol diethyl ether (80g, 20 times the mass of compound 12-e) and water (80g, 20 times the mass of compound 12-e), stirring, adding tri (o-tolyl) phosphine (5% eq, 0.10g, 304.37g/mol, 0.31mmol) and palladium (II) acetate (1% eq, 0.01g, 224.51g/mol, 0.06mmol), heating to reflux for 15h, separating the organic phase, washing with water, concentrating under reduced pressure to obtain crude EI (69) (3.25g, 63.8%), and performing column chromatography to obtain organic compound EI (69) (3.25g, 63.8%), yield (MS): 812(M +).
Example 13:
the synthesis of the organic compound (81) is as follows:
S1:
adding compound 13-a (5g, 317.76g/mol, 15.89mmol), compound 13-b (1.1eq, 2.57g, 146.94g/mol, 17.47mmol) and sodium carbonate (2eq, 3.37g, 105.99g/mol, 31.77mmol) to ethylene glycol diethyl ether (100g, 20 times the mass of compound 13-a) and water (100g, 20 times the mass of compound 13-a), stirring, mixing, sequentially adding tri (o-tolyl) phosphine (5% eq, 0.24g, 304.37g/mol, 0.79mmol) and palladium (II) acetate (1% eq, 0.04g, 224.51g/mol, 0.16mmol), heating to reflux for 15h, separating the organic phase, washing with water, concentrating under reduced pressure to obtain crude product, and performing EI column chromatography to obtain compound 13-c (4.58g, yield) (MS 84.8%): 339(M +).
S2:
Adding a compound 13-c (4g, 339.97g/mol, 11.84mmol), a compound 13-d (1.1eq, 3.54g, 272.11g/mol, 13.02mmol) and sodium carbonate (2eq, 2.51g, 105.99g/mol, 23.68mmol) into ethylene glycol diamine ether (80g, 20 times of the mass of the compound 13-c) and water (80g, 20 times of the mass of the compound 13-c), stirring and mixing uniformly, then adding tri (o-tolyl) phosphine (5% eq, 0.18g, 304.37g/mol, 0.59mmol) and palladium (II) acetate (1% eq, 0.03g, 224.51g/mol, 0.12mmol) in sequence, heating to reflux reaction for 15h, separating an organic phase, washing with water, concentrating under reduced pressure to obtain a crude product, and performing column chromatography to obtain a compound 13-e (4.06g, yield 70.3%), ms (m): 487(M +).
S3:
Adding compound 13-e (4g, 487.35g/mol, 8.23mmol), compound 13-f (1.1eq, 1.1g, 121.93g/mol, 9.06mmol) and sodium carbonate (2eq, 1.74g, 105.99g/mol, 16.46mmol) to ethylene glycol diethyl ether (80g, 20 times the mass of compound 13-e) and water (80g, 20 times the mass of compound 13-e), stirring, adding tri (o-tolyl) phosphine (5% eq, 0.13g, 304.37g/mol, 0.41mmol) and palladium (II) acetate (1% eq, 0.02g, 224.51g/mol, 0.08mmol), heating to reflux for 15h, separating out the organic phase, washing with water, concentrating under reduced pressure to obtain crude EI (81) (3.56g, 89.4%), and (MS): 484(M +).
Example 14:
the synthesis of organic compound (93) is as follows:
adding 14-a (4g, 487.35g/mol, 8.23mmol), 14-a (1.1eq, 2.84g, 314.19g/mol, 9.06mmol) and sodium carbonate (2eq, 1.74g, 105.99g/mol, 16.46mmol) to ethylene glycol diethyl ether (80g, 20 times of the mass of 14-a) and water (80g, 20 times of the mass of 14-a), stirring, adding tri (o-tolyl) phosphine (5% eq, 0.13g, 304.37g/mol, 0.41mmol) and palladium (II) acetate (1% eq, 0.02g, 224.51g/mol, 0.08mmol), heating to reflux for 15h, separating out the organic phase, washing with water, concentrating under reduced pressure to obtain crude EI (93) (4.26g, yield, 76.5%), and performing column chromatography to obtain organic compound EI (93) (4.26g, 76.5%): 676(M +).
Example 15:
the synthesis of organic compound (97) was as follows:
adding 15-a (4g, 487.35g/mol, 8.23mmol), 15-b (1.1eq, 2.84g, 287.12g/mol, 9.06mmol) and sodium carbonate (2eq, 1.74g, 105.99g/mol, 16.46mmol) to ethylene glycol diethyl ether (80g, 20 times the mass of compound 15-a) and water (80g, 20 times the mass of compound 15-a), stirring, adding tri (o-tolyl) phosphine (5% eq, 0.13g, 304.37g/mol, 0.41mmol) and palladium (II) acetate (1% eq, 0.02g, 224.51g/mol, 0.08mmol), heating to reflux for 15h, separating out the organic phase, washing with water, concentrating under reduced pressure to obtain crude EI (97) after column chromatography, obtaining organic compound (EI) (4.26g, yield), (MS 76.5%): 649(M +).
Example 16:
the synthesis of organic compound (101) is as follows:
S1:
adding 16-a (5g, 317.76g/mol, 15.94mmol), 16-b (1.1eq, 2.58g, 146.94g/mol, 17.53mmol) and sodium carbonate (2eq, 3.38g, 105.99g/mol, 31.87mmol) to ethylene glycol diethyl ether (100g, 20 times of the mass of compound 16-a) and water (100g, 20 times of the mass of compound 16-a), stirring, mixing, adding tri (o-tolyl) phosphine (5% eq, 0.24g, 304.37g/mol, 0.8mmol) and palladium (II) acetate (1% eq, 0.04g, 224.51g/mol, 0.16mmol), heating to reflux for 15h, separating the organic phase, washing with water, concentrating under reduced pressure to obtain crude EI, performing column chromatography to obtain compound 16-c (4.70g, yield 86.7%), and (MS): 339(M +).
S2:
Adding 16-c (4g, 339.97g/mol, 11.87mmol), 16-d (1.1eq, 4.55g, 348.20g/mol, 13.06mmol) and sodium carbonate (2eq, 2.51g, 105.99g/mol, 23.68mmol) into ethylene glycol diamine ether (80g, 20 times of the mass of compound 16-c) and water (80g, 20 times of the mass of compound 16-c), stirring, adding tri (o-tolyl) phosphine (5% eq, 0.18g, 304.37g/mol, 0.59mmol) and palladium (II) acetate (1% eq, 0.03g, 224.51g/mol, 0.12mmol), heating to reflux for 15h, separating the organic phase, washing with water, concentrating under reduced pressure to obtain crude EI, and performing column chromatography to obtain compound 16-e (4.36g, yield 65.2%), MS (65.2%): 563(M +).
S3:
Adding 16-e (4g, 563.45g/mol, 7.13mmol), 16-f (1.1eq, 0.96g, 121.93g/mol, 7.84mmol) and sodium carbonate (2eq, 1.51g, 105.99g/mol, 14.26mmol) to ethylene glycol diethyl ether (80g, 20 times of the mass of compound 16-e) and water (80g, 20 times of the mass of compound 16-e), stirring, mixing, adding tri (o-tolyl) phosphine (5% eq, 0.11g, 304.37g/mol, 0.36mmol) and palladium (II) acetate (1% eq, 0.02g, 224.51g/mol, 0.07mmol), heating to reflux for 15h, separating the organic phase, washing with water, concentrating under reduced pressure to obtain crude EI (101) (3.07g, yield 77.1%), performing column chromatography to obtain organic compound EI (101) (MS): 560(M +).
Example 17:
the synthesis of organic compound (190) is as follows:
S1:
adding compound 17-a (4g, 338.99g/mol, 11.87mmol), compound 17-b (1.1eq, 3.55g, 272.11g/mol, 13.06mmol) and sodium carbonate (2eq, 2.51g, 105.99g/mol, 23.68mmol) to ethylene glycol diamine ether (80g, 20 times the mass of compound 17-a) and water (80g, 20 times the mass of compound 17-a), stirring, adding tri (o-tolyl) phosphine (5% eq, 0.18g, 304.37g/mol, 0.59mmol) and palladium (II) acetate (1% eq, 0.03g, 224.51g/mol, 0.12mmol) in sequence, heating to reflux for 15h, separating the organic phase, washing with water, concentrating under reduced pressure to obtain crude product, and performing column chromatography to obtain compound 17-c (4.31g, yield 74.9%), ms (9%): 486(M +).
S2:
Adding a compound 17-c (4g, 486.36g/mol, 7.13mmol), a compound 17-d (1.1eq, 0.96g, 348.20g/mol, 7.84mmol) and sodium carbonate (2eq, 1.51g, 105.99g/mol, 14.26mmol) into ethylene glycol diethyl ether (80g, 20 times of the mass of the compound 17-c) and water (80g, 20 times of the mass of the compound 17-c), stirring and mixing uniformly, adding tri (o-tolyl) phosphine (5% eq, 0.11g, 304.37g/mol, 0.36mmol) and palladium (II) acetate (1% eq, 0.02g, 224.51g/mol, 0.07mmol) in sequence, heating to reflux for 15h, separating out the organic phase, washing with water, concentrating under reduced pressure to obtain a crude EI, and performing column chromatography to obtain an organic compound (190% (3.22g, 63.6%), MS): 709(M +).
And (3) testing the material properties:
ETL-1 and the organic compounds 1, 6, 7, 8, 10, 12, 13, 19, 21, 41, 54, 69, 81, 93, 97, 101, 190 of the present invention were tested for the thermal weight loss temperature Td, and the test results are shown in table 1 below.
Note: the thermal weight loss temperature Td is the temperature of 5% weight loss in the nitrogen atmosphere, and is measured on a WRT-11 series thermogravimetric analyzer at great distance from northern light, and the nitrogen flow is 10mL/min during the test.
Table 1:
the data show that the thermal stability of the organic compound is superior to that of the comparative example ETL-1, which shows that the organic compound conforming to the structural general formula of the invention has good thermal stability, the good thermal stability is more favorable for being used as an organic electroluminescent material, and the service life and the luminous efficiency of an organic electroluminescent device prepared by using the material can be improved.
And (3) performance testing:
application example 1:
adopting ITO as the anode substrate material of the reflecting layer, and sequentially using water, acetone and N2Carrying out surface treatment on the glass substrate by plasma;
depositing HAT-CN with the thickness of 10nm to form a Hole Injection Layer (HIL) above the ITO anode substrate;
evaporating NPD above the Hole Injection Layer (HIL) to form a Hole Transport Layer (HTL) with the thickness of 120 nm;
evaporating 9,10-Bis (2-naphthyl) Anthracene (ADN) as a blue light main body material and BD-1 as a blue light doping material (the dosage of the BD-1 is 5 percent of the weight of the ADN) at different rates to form a light-emitting layer with the thickness of 20nm on a Hole Transport Layer (HTL);
evaporating the organic compound (1) of the invention on a luminescent layer to obtain an Electron Transport Layer (ETL) with the thickness of 35nm, and evaporating LiQ with the thickness of 2nm above the Electron Transport Layer (ETL) to form an Electron Injection Layer (EIL);
then magnesium (Mg) and silver (Ag) are mixed and evaporated in a ratio of 9:1 to obtain a cathode with the thickness of 15nm, DNTPD with the thickness of 65 nm is deposited on the sealing layer of the cathode, and in addition, the surface of the cathode is sealed by UV hardening adhesive and sealing film (seal cap) containing a moisture remover so as to protect the organic electroluminescent device from being influenced by oxygen or moisture in the atmosphere, thus preparing the organic electroluminescent device.
Application examples 2 to 17
Comparative example
The difference from application example 1 is that ETL-1 was used as an Electron Transport Layer (ETL), and the rest is the same as application example 1.
The characteristics of the organic electroluminescent element manufactured in the above application example and the organic electroluminescent element manufactured in the comparative example were that the current density was 10mA/cm2The results of measurements under the conditions of (1) are shown in Table 2.
Table 2:
as can be seen from the experimental comparison data in table 2 above, the organic electroluminescent device prepared by using the organic compound of the present invention as an Electron Transport Layer (ETL) has a reduced driving voltage, and significantly improved luminous efficiency and lifespan, as compared to the comparative example. Therefore, the organic compound provided by the invention can be used as an Electron Transport Layer (ETL) to greatly reduce the driving voltage of the device, greatly reduce the consumption of electric energy and obviously improve the luminous efficiency, and in addition, the service life of the organic electroluminescent device is obviously prolonged by reducing the driving voltage.
Claims (9)
1. A triphenylene-based organic compound having a structural formula represented by the following formula (I):
wherein R is any one of hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted C1-C5 alkyl group, a substituted or unsubstituted C6-C30 aromatic group and a substituted or unsubstituted C5-C30 heteroaromatic group;
x, Y, Z are each independently CH or N, and at least one of X, Y, Z is N;
m, s and n are each independently 0 or 1.
2. The triphenylene-based organic compound according to claim 1, wherein the structural formula is one of the following formulae (II), (III), (IV), (V):
wherein R is any one of hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted C1-C5 alkyl group, a substituted or unsubstituted C6-C30 aromatic group and a substituted or unsubstituted C5-C30 heteroaromatic group;
m, s and n are each independently 0 or 1.
3. The triphenylene-based organic compound according to claim 1, wherein R is hydrogen, deuterium, a fluorine atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a triphenylene group, a fluorenyl group, a dibenzoenyl group, a 9, 9-dimethylfluorenyl group, a 9,9' -spirobifluorene group, a 9, 9-diphenylfluorenyl group, a dibenzoyl group, a carbazolyl group, an N-phenylcarbazolyl group;
the methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylene, fluorenyl, dibenzoyl, 9-dimethylfluorenyl, 9' -spirobifluorene, 9-diphenylfluorenyl, dibenzoyl sulfide, carbazolyl, N-phenylcarbazolyl are unsubstituted or are obtained by substituting at least one hydrogen with deuterium.
5. an organic electroluminescent material, comprising at least one organic compound according to any one of claims 1 to 4.
6. Use of the organic electroluminescent material as claimed in claim 5 for the preparation of organic electroluminescent devices.
7. An organic electroluminescent device, characterized in that the organic electroluminescent device comprises: a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are sequentially stacked; the organic electroluminescent material as claimed in claim 5 is contained in the electron transport layer.
8. An organic electroluminescent display device characterized by comprising the organic electroluminescent device according to claim 7.
9. An organic electroluminescent lighting device characterized by comprising the organic electroluminescent element as claimed in claim 7.
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CN109326733A (en) * | 2017-07-31 | 2019-02-12 | 三星电子株式会社 | Organic luminescent device |
WO2019066340A1 (en) * | 2017-09-29 | 2019-04-04 | 삼성에스디아이 주식회사 | Organic compound, composition, organic optoelectronic device, and display device |
CN110003127A (en) * | 2017-12-27 | 2019-07-12 | 三星Sdi株式会社 | Composition, organic optoelectronic device and display device |
WO2019146938A1 (en) * | 2018-01-24 | 2019-08-01 | 삼성에스디아이 주식회사 | Compound, composition, organic optoelectronic diode, and display device |
CN111655679A (en) * | 2018-01-24 | 2020-09-11 | 三星Sdi株式会社 | Compound, composition, organic optoelectronic diode and display device |
KR101966306B1 (en) * | 2018-06-18 | 2019-04-05 | 주식회사 엘지화학 | Organic light emitting diode |
CN108997239A (en) * | 2018-07-25 | 2018-12-14 | 上海道亦化工科技有限公司 | A kind of compound of cyano-containing and application thereof and organic electroluminescence device |
CN112106217A (en) * | 2018-08-14 | 2020-12-18 | 株式会社Lg化学 | Organic light emitting device |
CN111868948A (en) * | 2018-09-21 | 2020-10-30 | 株式会社Lg化学 | Organic light emitting device |
CN109535093A (en) * | 2018-12-24 | 2019-03-29 | 上海道亦化工科技有限公司 | A kind of trisubstituted benzene based compound and organic electroluminescence device |
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CN113549023A (en) * | 2021-08-25 | 2021-10-26 | 武汉天马微电子有限公司 | Organic compound and application thereof |
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CN114957133A (en) | 2022-08-30 |
CN115215812A (en) | 2022-10-21 |
CN112851591B (en) | 2022-09-23 |
CN115124482A (en) | 2022-09-30 |
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