CN114957133A - 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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- CN114957133A CN114957133A CN202210309399.6A CN202210309399A CN114957133A CN 114957133 A CN114957133 A CN 114957133A CN 202210309399 A CN202210309399 A CN 202210309399A CN 114957133 A CN114957133 A CN 114957133A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 96
- 239000000463 material Substances 0.000 title claims abstract description 28
- 125000005580 triphenylene group Chemical group 0.000 title claims abstract description 17
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 title claims abstract description 12
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 9
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 7
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 5
- 238000002347 injection Methods 0.000 claims description 12
- 239000007924 injection Substances 0.000 claims description 12
- -1 9, 9-dimethylfluorenyl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 230000005525 hole transport Effects 0.000 claims description 6
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000005561 phenanthryl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 claims description 3
- SNFCXVRWFNAHQX-UHFFFAOYSA-N 9,9'-spirobi[fluorene] Chemical group C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 SNFCXVRWFNAHQX-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- KIHBJERLDDVXHD-UHFFFAOYSA-N s-benzoyl benzenecarbothioate Chemical compound C=1C=CC=CC=1C(=O)SC(=O)C1=CC=CC=C1 KIHBJERLDDVXHD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 3
- 230000002035 prolonged effect Effects 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 106
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 63
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 62
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 62
- 238000010438 heat treatment Methods 0.000 description 31
- 239000012074 organic phase Substances 0.000 description 31
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 31
- 238000010992 reflux Methods 0.000 description 31
- 229910000029 sodium carbonate Inorganic materials 0.000 description 31
- 238000003756 stirring Methods 0.000 description 31
- 238000005406 washing Methods 0.000 description 31
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 30
- 238000004440 column chromatography Methods 0.000 description 30
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 29
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 238000002156 mixing Methods 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000012043 crude product Substances 0.000 description 10
- 150000004985 diamines Chemical class 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 238000001308 synthesis method Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
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- 101000687716 Drosophila melanogaster SWI/SNF-related matrix-associated actin-dependent regulator of chromatin subfamily A containing DEAD/H box 1 homolog Proteins 0.000 description 3
- 101000687741 Mus musculus SWI/SNF-related matrix-associated actin-dependent regulator of chromatin subfamily A containing DEAD/H box 1 Proteins 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 1
- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
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- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
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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 hydrogen, deuterium, halogen atom, cyanoAny one of substituted or unsubstituted C1-C5 alkyl, substituted or unsubstituted C6-C30 aromatic group and 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
The application is a divisional application with the name of an organic compound based on a triphenylene group, an organic electroluminescent material and a device, wherein the divisional application is the application number of 2019111862550, application date 2019, 11 month and 28 day.
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 laboratories by professor lugdong 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, halogen atom, cyano-group, substituted or unsubstituted C1-C5 alkyl group, substituted or unsubstituted C6-C30 aromatic group and 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 from FIG. 2, it can be seen 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：
Adding compound 1-c (4g, 339.97g/mol, 11.84mmol), compound 1-d (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 compound 1-c) and water (80g, 20 times of the mass of compound 1-c), stirring, 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), heating to reflux for 15h, separating out the organic phase, washing with water, concentrating under reduced pressure to obtain crude EI, and performing column chromatography to obtain compound 1-e (4.68g, yield 70.2%), MS (1-2%): 563(M +).
S3：
Adding a compound 1-e (4g, 563.45g/mol, 7.12mmol), a 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-fold mass of the compound 1-e) and water (80g, 20-fold mass of the 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 an organic phase, washing with water, concentrating under reduced pressure to obtain a crude EI, and carrying out column chromatography to obtain an 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 method of the organic compound (10) is as follows:
adding compound 5-a (4g, 339.97g/mol, 11.84mmol), compound 5-b (2.1eq, 8.65g, 348.20g/mol, 24.86mmol) and sodium carbonate (4eq, 5.02g, 105.99g/mol, 47.35mmol) to ethylene glycol diamine ether (80g, 20 times the mass of compound 5-a) and water (80g, 20 times the mass of compound 5-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 organic compound ei (10) (6.16g, 66.2%), ms (2%): 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 method 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 a compound 13-a (5g, 317.76g/mol, 15.89mmol), a compound 13-b (1.1eq, 2.57g, 146.94g/mol, 17.47mmol) and sodium carbonate (2eq, 3.37g, 105.99g/mol, 31.77mmol) into ethylene glycol diethyl ether (100g, 20-fold mass of the compound 13-a) and water (100g, 20-fold mass of the compound 13-a), stirring and mixing uniformly, then 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 an organic phase, washing with water and concentrating under reduced pressure to obtain a crude EI, and performing column chromatography to obtain a compound 13-c (4.58g, 84.8%), MS (yield): 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 method of the 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 N 2 Carrying 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/cm 2 The 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 structure 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 two of X, Y, Z are N;
m and s are each independently 0 or 1, and n is 0.
2. The triphenylene-based organic compound according to claim 1, having a structural formula of one of the following formulae (III), (IV), (V):
wherein, R is any one of hydrogen, deuterium, halogen atom, cyano-group, substituted or unsubstituted C1-C5 alkyl group, substituted or unsubstituted C6-C30 aromatic group and substituted or unsubstituted C5-C30 heteroaromatic group;
m and s are each independently 0 or 1, and n is 0.
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.
4. The triphenylene-based organic compound of claim 1, wherein the organic compound has a structure represented by:
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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