CN111574565B - Compound and preparation method and application thereof - Google Patents
Compound and preparation method and application thereof Download PDFInfo
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- CN111574565B CN111574565B CN202010456332.6A CN202010456332A CN111574565B CN 111574565 B CN111574565 B CN 111574565B CN 202010456332 A CN202010456332 A CN 202010456332A CN 111574565 B CN111574565 B CN 111574565B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 78
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 51
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 239000000463 material Substances 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
- 150000002894 organic compounds Chemical class 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 5
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000005561 phenanthryl group Chemical group 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000006267 biphenyl group Chemical group 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- -1 methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, t-butoxy, n-pentoxy, isopentoxy, t-pentoxy, n-hexoxy, phenyl Chemical group 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract description 2
- 239000011574 phosphorus Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 44
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- 238000012360 testing method Methods 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000012074 organic phase Substances 0.000 description 15
- 239000012043 crude product Substances 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
- 239000012267 brine Substances 0.000 description 10
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 230000005540 biological transmission Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 238000000859 sublimation Methods 0.000 description 5
- 230000008022 sublimation Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000010586 diagram Methods 0.000 description 4
- 230000005684 electric field Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003775 Density Functional Theory Methods 0.000 description 3
- SCHRRICRQNJJKN-UHFFFAOYSA-N P.[O] Chemical group P.[O] SCHRRICRQNJJKN-UHFFFAOYSA-N 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 229910052769 Ytterbium Inorganic materials 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 230000006978 adaptation Effects 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 238000004088 simulation Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 2
- 238000004057 DFT-B3LYP calculation Methods 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 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 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical group [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
- C07F9/65685—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine oxide or thioxide
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
- C07F9/65683—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6578—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and sulfur atoms with or without oxygen atoms, as ring hetero atoms
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
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Abstract
The application discloses a compound and a preparation method and application thereof, wherein the compound has a structure shown in a formula (I), namely, a specific nitrogen-containing heterocyclic skeleton structure and a P=O double bond or phosphorus-containing annular structure are matched with each other to obtain a device prepared by taking the compound as a raw material, so that the starting voltage of an OLED device is reduced, the working voltage of the OLED device is reduced, and the efficiency and the service life of the device are improved.
Description
Technical Field
The application relates to the field of organic electroluminescent materials, in particular to a compound, a preparation method and application thereof.
Background
In the organic electroluminescent material, the material for the electron transport layer (ET material) is to avoid absorbing visible light, and in order to receive electrons from the cathode, LUMO energy of 2.4 to 3.0eV is required (calculation result under mass production condition is 1.4 to 2.0 eV).
The ET material commonly used in the prior art is Alq3, has good thermal stability, but has lower electron mobility, is easy to crystallize under the condition that the device works for a long time, and reduces the efficiency and the service life of the device. Researchers have applied nitrogen-containing heterocyclic molecules to electron transport materials in order to further enhance electron mobility and achieve good electron transport properties. The electron transport layer material can effectively improve the electron mobility through the coordination effect of the non-shared electron pair of the nitrogen atom and the metal doped in the electron transport layer material.
However, the ET material containing nitrogen heterocycle has better molecular flatness, which results in stronger intermolecular interaction force, and requires higher temperature in the evaporation process, so that chemical bonds in the molecules are broken. Thereby affecting the properties of the ET material. Therefore, the ET material with better stability and electron transmission performance in the evaporation process is obtained, and has important significance.
Disclosure of Invention
In view of the above, the technical problem to be solved by the present application is to provide a compound, a preparation method and application thereof, wherein the compound has a general structure shown in chemical formula 1:
wherein Ar is a C3-C50 heterocyclic group containing P or P=O;
X 1 、X 2 、X 3 、X 4 、X 5 、X 6 independently selected from CH or N; and X is 1 And X 2 At least one of which is N, X 4 And X 5 At least one of which is N;
alternatively, X 1 And X 5 Forms a 5-7 membered ring with the carbon in which they are located, and X 1 And X 2 At least one of which is N, X 4 And X 5 At least one of which is N;
alternatively, X 2 And X 4 And where they are locatedCarbon forms a 5-7 membered ring and X 1 And X 2 At least one of which is N, X 4 And X 5 At least one of which is N;
R 1 、R 2 independently selected from C1-C30 alkyl, C1-C30 alkoxy, C6-C30 aromatic ring group or C3-C30 aromatic heterocyclic group;
l is an aryl group of 6 to 30 carbon atoms;
n、n 1 、n 2 independently selected from 0, 1, 2, 3 or 4.
The compound provided by the application is used as an electron transport layer of an organic electroluminescent material to obtain an electron luminescent device with high efficiency and service life. The compound provided by the application has the advantages that a specific structure is selected, and experimental results show that the compound provided by the application can be well complexed with Yb metal, so that the situation that the metal moves due to heat and electric field generated in the driving process of the obtained device is relieved. Compared with the prior known electron transport layer material, the device obtained by using the compound as the electron transport layer material has lower starting voltage and working voltage, higher current efficiency and longer working life. In addition, the compound disclosed by the application has relatively stable properties in the experimental process, and the phenomenon of evaporation blocking in the evaporation process of preparing a device is avoided. In summary, the device prepared by the compound of the application not only reduces the starting voltage of the OLED device and reduces the working voltage of the OLED device, but also improves the efficiency and service life of the device.
Drawings
Fig. 1 is a schematic structural view of an organic light emitting device according to the present application;
fig. 2 is a schematic diagram of a display device provided by the present application.
Detailed Description
The application provides a compound which has a structure shown in a formula (I),
wherein Ar is a C3-C50 heterocyclic group containing P or P=O;
X 1 、X 2 、X 3 、X 4 、X 5 、X 6 independently selected from CH or N; and X is 1 And X 2 At least one of which is N, X 4 And X 5 At least one of which is N;
alternatively, X 1 And X 5 Forms a 5-7 membered ring with the carbon in which they are located, and X 1 And X 2 At least one of which is N, X 4 And X 5 At least one of which is N;
alternatively, X 2 And X 4 Forms a 5-7 membered ring with the carbon in which they are located, and X 1 And X 2 At least one of which is N, X 4 And X 5 At least one of which is N;
the R is 1 、R 2 Independently selected from C1-C30 alkyl, C1-C30 alkoxy, C6-C30 aromatic ring group or C3-C30 aromatic heterocyclic group;
l is an aryl group of C6-C30;
the n, n 1 、n 2 Independently selected from 0, 1, 2, 3 or 4.
It should be noted that X 1 And X is 5 The dashed lines therebetween indicate the presence or absence, which means that they are linked together to form a loop.
In this context, -R 1 and-R 2 R in (a) 1 、R 2 Indicating any one of its positions on the ring.
The compound with the structure shown in the formula (I) provided by the application has a multi-tooth nitrogen-containing ligand, and the multi-tooth nitrogen-containing ligand is complexed with metal, so that the situation that the metal moves due to heat and electric field generated in the driving process of the prepared device is relieved. In addition, in the molecule designed in the scheme, a specific nitrogen-containing heterocyclic skeleton structure and a P=O double bond or phosphorus-containing annular structure are matched with each other, so that the organic compound has larger rigid distortion, and the phenomenon of vapor deposition blocking caused by intermolecular attraction increase due to an excessively planarized structure of an electron transport material is avoided.
According to one embodiment of the compounds of the application, ar is selected from the group consisting of formula (Ar-1), formula (Ar-2) and formula (Ar-3),
wherein A is 1 Ring, A 2 Ring, A 3 Ring, A 4 Ring, A 5 Ring, A 6 Ring, A 7 The ring is selected from C6-C30 aromatic ring, C8-C2 aromatic ring, benzene, naphthalene, anthracene or phenanthrene.
# represents the connection position with L;
l is an aryl group of C6-C30;
R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 independently selected from hydrogen, C1-C30 alkyl, C1-C30 alkoxy, C6-C30 aromatic ring group or C3-C30 aromatic heterocyclic group, wherein the hetero atom in the aromatic heterocyclic group is nitrogen, oxygen or sulfur, optionally R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 Independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, isopentyl, t-pentyl, n-hexyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, t-butoxy, n-pentoxy, isopentoxy, t-pentoxy, n-hexoxy, phenyl, diphenyl, naphthyl, anthracenyl, phenanthryl, furyl, pyranyl, pyridyl, piperidinyl or thienyl.
Y is oxygen or nitrogen;
said n 3 、n 4 、n 5 、n 6 、n 7 、n 8 、n 9 Independently selected from 0, 1, 2 or 3.
According to the application, experiments of the applicant show that the specific Ar is adopted as an aromatic phosphine (oxygen) functional group to be matched with a specific nitrogen-containing heterocyclic ring skeleton structure, so that the compound has strong coordination capacity, and the phosphine (oxygen) group endows the coordination mode of the complex with diversity, so that various photoelectric functions are realized; meanwhile, 3 aryl groups in the aromatic phosphine (oxygen) groups in the compound can provide rich combination of modification sites and group proportions, so that the multifunctional integration of the compound is realized; in addition, P=O bonds are introduced into the molecules of the application, and the molecules respectively have moderate electron-withdrawing induction effect, so that the molecules can be effectively polarized, and the main structure of the application is matched, so that the carrier transmission capacity of the material is enhanced.
According to one embodiment of the compounds of the application, ar is any one of the following structures:
wherein R is 3 ’、R 4 ’、R 5 ’、R 6 ’、R 7 ’、R 8 ’、R 9 ’、R 10 ’、R 11 ’、R 12 ’、R 13 ’、R 14 ’、R 15 ’、R 16 ’、R 17 ’、R 18 ’、R 19 ’、R 20 ’、R 21 ’、R 22 ’、R 23 ’、R 24 ’、R 25 ’、R 26 ’、R 27 ’、R 28 ’、R 29 ’、R 30 ’、R 31 ’、R 32 ’、R 3 ”、R 4 ”、R 5 ”、R 6 ”、R 7 ”、R 8 ”、R 9 ”、R 10 ”、R 11 ”、R 12 ”、R 13 ”、R 14 ”、R 15 ”、R 16 ”、R 17 ”、R 18 ”、R 19 ”、R 20 ”、R 21 ”、R 22 ”、R 23 ”、R 24 ”、R 25 ”、R 26 ”、R 27 ”、R 28 ”、R 29 ”、R 30 ”、R 31 ”、R 32 "independently selected from hydrogen or C1-C6 alkyl, optionally hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl; or R is 3 ’、R 4 ’、R 5 ’、R 6 ’、R 7 ’、R 8 ’、R 9 ’、R 10 ’、R 11 ’、R 12 ’、R 13 ’、R 14 ’、R 15 ’、R 16 ’、R 17 ’、R 18 ’、R 19 ’、R 20 ’、R 21 ’、R 22 ’、R 23 ’、R 24 ’、R 25 ’、R 26 ’、R 27 ’、R 28 ’、R 29 ’、R 30 ’、R 31 ’、R 32 ’、R 3 ”、R 4 ”、R 5 ”、R 6 ”、R 7 ”、R 8 ”、R 9 ”、R 10 ”、R 11 ”、R 12 ”、R 13 ”、R 14 ”、R 15 ”、R 16 ”、R 17 ”、R 18 ”、R 19 ”、R 20 ”、R 21 ”、R 22 ”、R 23 ”、R 24 ”、R 25 ”、R 26 ”、R 27 ”、R 28 ”、R 29 ”、R 30 ”、R 31 ”、R 32 Any two adjacent groups in the' and the carbon where the adjacent groups are positioned form C6-C18 aryl; the R is 100 、R 200 、R 300 Independently selected from hydrogen or C1-C6 alkyl, and can be selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl and n-hexyl; and Y is oxygen or nitrogen.
According to one embodiment of the compounds according to the application, X 1 And X 5 Forms a 5-7 membered ring with the carbon in which they are located, optionally forming a 6 membered ring; wherein the ring formed may be selected from aromatic or heteroaromatic. X is X 2 And X 4 With the carbon in which they are locatedForming a 5-7 membered ring, optionally a 6 membered ring; wherein the ring formed may be selected from aromatic or heteroaromatic.
According to one embodiment of the compound according to the application, L is optionally a C10-C25 aryl group, optionally a C12-C20 aryl group, optionally a phenyl, naphthyl, biphenyl, terphenyl, anthryl or phenanthryl group; wherein, the aryl is selected for L, which can further improve the electron transmission property and further improve the performance of the electron transmission layer material.
According to one embodiment of the compounds of the application, the R 1 Or R is 2 The hetero atom in the C3-C30 aromatic heterocyclic group defined in (2) is nitrogen, oxygen or sulfur, optionally, the R 1 、R 2 Optionally independently selected from C2-C15 alkyl, C3-C15 alkoxy, C10-C20 aromatic ring group or C4-C15 aromatic heterocyclic group, said R 1 、R 2 Independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, isopentyl, t-pentyl, n-hexyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, t-butoxy, n-pentoxy, isopentoxy, t-pentoxy, n-hexoxy, phenyl, diphenyl, naphthyl, anthracenyl, phenanthryl, furyl, pyranyl, pyridyl, piperidinyl or thienyl.
Specifically, the compound of the application can be selected as a structure shown in a formula (I-1) or a formula (I-2),
wherein Ar is a C3-C50 heterocyclic group containing P or P=O;
X 1 、X 2 、X 3 、X 4 、X 5 、X 6 independently selected from CH or N; and X is 1 And X 2 At least one of which is N, X 4 And X 5 At least one of which is N;
the R is 1 、R 2 Independently selected from C1-C30 alkyl, C1-C30 alkoxy, C6-C30 aromatic ring group or C3-a C30 aromatic heterocyclic group;
l is an aryl group of C6-C30;
the n, n 1 、n 2 Independently selected from 0, 1, 2, 3 or 4.
According to the experimental study, the compound is found that the compound contains at least two nitrogen ligands, and the device prepared by the compound is found that the situation that heat and an electric field generated in the driving process can cause metal movement is relieved, and the performance of the device is improved. More specifically, the compounds of the present application may optionally have the following structure:
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experiments show that the organic compound has a proper space structure, a specific composition and a molecular weight, the molecular weight is in the range of 600-1200 g/mol, the vapor deposition rate is controlled, the accumulation caused by the increase of intermolecular attraction can be restrained, the starting voltage of an OLED device is reduced, the working voltage of the OLED device is reduced, the efficiency is improved, and the service life is prolonged.
The application also provides a preparation method of the compound, which comprises the following steps:
combining a compound of formula (II) with Ar-Y 1 The reaction gives a compound of the formula (I), the conditions of which are not particularly critical in the present application, and the skilled person can choose a suitable preparation method according to the general knowledge in the art.
Wherein Ar is a C3-C50 heterocyclic group containing P or P=O;
X 1 、X 2 、X 3 、X 4 、X 5 、X 6 independently selected from CH or N; and X is 1 And X 2 At least one of which is N, X 4 And X 5 At least one of which is N;
alternatively, X 1 And X 5 Forms a 5-7 membered ring with the carbon in which they are located, and X 1 And X 2 At least one of which is N, X 4 And X 5 At least one of which is N;
alternatively, X 2 And X 4 Forms a 5-7 membered ring with the carbon in which they are located, and X 1 And X 2 At least one of which is N, X 4 And X 5 At least one of which is N;
the R is 1 、R 2 Independently selected from C1-C30 alkyl, C1-C30 alkoxy, C6-C30 aromatic ring group or C3-C30 aromatic heterocyclic group;
l is an aryl group of C6-C30;
the n, n 1 、n 2 Independently selected from 0, 1, 2, 3 or 4;
the Y is 1 、Y 2 Independently selected from halogen.
The application also provides a display panel comprising an organic light emitting device comprising an anode, a cathode, at least one organic compound layer between the anode and the cathode, the organic compound of the organic compound layer comprising at least one of the compounds according to the application; wherein the organic compound layer comprises an electron transport layer, and the electron transport layer is at least one of the compounds. The schematic structural diagram of the organic light emitting device is shown in fig. 1, fig. 1 is a schematic structural diagram of the organic light emitting device provided by the application, wherein 101 is an anode layer, 103 is a cathode layer, and 102 is an organic compound layer.
The application also provides an organic light emitting display device comprising an organic light emitting display panel as described above.
In the present application, an organic light emitting device (OLED device) may be used in a display apparatus, wherein the organic light emitting display apparatus may be a mobile phone display screen, a computer display screen, a television display screen, a smart watch display screen, a smart car display panel, a VR or AR helmet display screen, display screens of various smart devices, or the like. Specifically, as shown in fig. 2, fig. 2 is a schematic diagram of the display device provided by the present application, in which 30 is a smart phone and 20 is an organic light emitting display panel.
The following description of embodiments of the present application will be made clearly and fully with reference to the accompanying drawings, in which it is shown, however, only some, but not all embodiments of the application are shown. All other embodiments, which can be made by those skilled in the art based on the embodiments of the application without making any inventive effort, are intended to be within the scope of the application.
Example 1
Synthesis of Compound P001
In a 500mL three-necked flask, compound X1 (10.0 mmol) was weighed and dissolved in 250mL THF, and nBuLi (2.4M in n-hexane, 11.0 mmol) was added to the solution at-78℃and stirred for 2h. Compound X2 (11.2 mmol) was weighed and dissolved in THF (100 mL), and a THF solution of X2 was added to the X1 flask with a syringe, stirred for 1h, then slowly warmed to room temperature, and stirred overnight. After the reaction was completed, 250mL of ethyl acetate was added, and the mixture was washed with 25mL of brine, extracted using a separating funnel, and the organic phase was collected. Anhydrous Na for organic phase 2 SO 4 And (5) drying. The solvent was removed by distillation under the reduced pressure to give a crude product, which was recrystallized from n-hexane/dichloromethane to give intermediate X3 (6.7 mmol, 67%).
Structure of test intermediate X3: MALDI-TOF MS (m/z) C by matrix assisted laser desorption ionization time-of-flight mass spectrometry 28 H 19 N 2 P calculated 414.1 and tested 414.3.
X3 (2.0 mmol) was dissolved in dichloromethane (17.5 mL) and cooled to 5℃with an ice bath. Hydrogen peroxide (6.0 mmol) was slowly added to the solution. The ice bath was removed and the solution was stirred at room temperature overnight. After the reaction was completed, the reaction mixture was washed with brine. The organic phase was collected, dried over anhydrous sodium sulfate, filtered and the solvent was evaporated. The crude product was recrystallized from n-hexane/dichloromethane (95:5, vol/vol), filtered, washed with n-hexane and dried under vacuum to give the title compound P001 (1.84 mmol, 92%) by sublimation purification.
Structure of test target product P001: MALDI-TOF MS (m/z) was obtained by matrix assisted laser desorption ionization time-of-flight mass spectrometry: c (C) 28 H 19 N 2 OP, calculated 430.1 and tested 430.4.
Elemental analysis: theoretical value C,78.13; h,4.45; n,6.51; test value C,78.18; h,4.42; n,6.48.
1 H-NMR(400MHz，CDCl 3 )：δ(ppm)9.16(s,1H),9.04-9.08(m,2H),8.95(d,1H),8.14(m,1H),7.98-8.04(m,4H),7.60-7.64(m,6H),7.40-7.45(m,3H),7.32-7.37(m,1H)。
Example 2
Synthesis of Compound P077
In a 500mL three-necked flask, compound X4 (5.0 mmol) was weighed and dissolved in 120mL THF, and nBuLi (2.4M in n-hexane, 5.6 mmol) was added to the solution at-78℃and stirred for 2h. Compound X5 (5.6 mmol) was weighed and dissolved in THF (50 mL), and a THF solution of X5 was added to the X4 flask with a syringe, stirred for 1h, then slowly warmed to room temperature, and stirred overnight. After the reaction was completed, 120mL of ethyl acetate was added, and the mixture was washed with 12mL of brine, extracted with a separating funnel, and the organic phase was collected. Anhydrous Na for organic phase 2 SO 4 And (5) drying. The solvent was removed by distillation under the reduced pressure to give a crude product, which was recrystallized from n-hexane/dichloromethane to give intermediate X6 (3.65 mmol, 73%).
Structure of test intermediate X6: MALDI-TOF MS (m/z) was obtained by matrix assisted laser desorption ionization time-of-flight mass spectrometry: c (C) 27 H 18 N 3 OP, calculated 431.1 and tested 431.3.
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X6 (2.5 mmol) was dissolved in dichloromethane (25 mL) and cooled to 5℃with an ice bath. Hydrogen peroxide (7.5 mmol) was slowly added to the solution. The ice bath was removed and the solution was stirred at room temperature overnight. After the reaction was completed, the reaction mixture was washed with brine. The organic phase was collected, dried over anhydrous sodium sulfate, filtered and the solvent was evaporated. The crude product was recrystallized from n-hexane/dichloromethane (94:6, vol/vol), filtered, washed with n-hexane and dried under vacuum to give the title compound P077 (2.25 mmol, 90%) by sublimation purification.
Structure of test target product P077: MALDI-TOF MS (m/z) was obtained by matrix assisted laser desorption ionization time-of-flight mass spectrometry: c (C) 27 H 18 N 3 O 2 P calculated 447.1 and tested 447.4.
Elemental analysis: theoretical value C,72.48; h,4.05; n,9.39; test value C,72.54; h,4.02; n,9.35.
1 H-NMR(400MHz，CDCl 3 )：δ(ppm)9.12-9.15(m,2H),8.98-9.02(m,2H),8.74(m,2H),8.07-8.14(m,2H),7.72-7.78(m,4H),7.62-7.66(m,2H),7.51-7.55(m,2H),7.36-7.42(m,2H)。
Example 3
Synthesis of Compound P108
X7 (4 mmol) was weighed and dissolved in THF (80 mL) and the dissolution temperature was reduced to-78℃and t-BuLi (16 mmol) was slowly added dropwise to the solution, after the addition was completed, the temperature was slowly raised to room temperature and stirring was continued for 4h. The solution was then cooled to-196 ℃ with liquid nitrogen. PCl3 (80 mmol) was added, slowly warmed to room temperature, stirring continued for 4h, and the solvent was distilled off under reduced pressure to give a white precipitated crude product which was recrystallized from n-hexane/THF to give intermediate X8 (3.16 mmol, 79%).
Structure of test intermediate X6: MALDI-TOF MS (m/z) was obtained by matrix assisted laser desorption ionization time-of-flight mass spectrometry: c (C) 18 H 12 ClP, calculated 294.0 and tested 294.3.
In a 100mL three-necked flask, compound X9 (2.0 mmol) was weighed and dissolved in 50mL THF, and nBuLi (2.4M in n-hexane, 2.5 mmol) was added to the solution at-78℃and stirred for 2h. Compound X8 (2.5 mmol) was weighed and dissolved in THF (20 mL), and a THF solution of X8 was added to the X9 flask with a syringe, stirred for 1h, then slowly warmed to room temperature, and stirred overnight. After the reaction was completed, 45mL of ethyl acetate was added, and 6mL of brine was added for washing, and extraction was performed using a separating funnel, and an organic phase was collected. Anhydrous Na for organic phase 2 SO 4 And (5) drying. The solvent was removed by distillation under the reduced pressure to give a crude product, which was recrystallized from n-hexane/dichloromethane to give intermediate X10 (1.24 mmol, 62%).
Structure of test intermediate X10: MALDI-TOF MS (m/z) was obtained by matrix assisted laser desorption ionization time-of-flight mass spectrometry: c (C) 34 H 23 N 2 P calculated as 490.2 and tested as 490.5.
X6 (4.0 mmol) was dissolved in dichloromethane (80.0 mL) and cooled to 5℃with an ice bath. Hydrogen peroxide (12.0 mmol) was slowly added to the solution. The ice bath was removed and the solution was stirred at room temperature overnight. After the reaction was completed, the reaction mixture was washed with brine. The organic phase was collected, dried over anhydrous sodium sulfate, filtered and the solvent was evaporated. The crude product was recrystallized from n-hexane/dichloromethane (95:5, vol/vol), filtered, washed with n-hexane and dried under vacuum, and purified by sublimation to give the title compound P108 (3.52 mmol, 88%).
Structure of test target product P108: MALDI-TOF MS (m/z) was obtained by matrix assisted laser desorption ionization time-of-flight mass spectrometry: c (C) 34 H 23 N 2 OP, calculated 506.2 and tested 506.4.
Elemental analysis: theoretical value C,80.62; h,4.58; n,5.53; test value C,80.66; h,4.56; n,5.50.
1 H-NMR(400MHz，CDCl 3 )：δ(ppm)9.22(s,1H),9.09-9.15(m,2H),9.00(d,1H),8.16(m,1H),8.00-8.04(m,6H),7.84(m,1H),7.68-7.73(m,8H),7.42-7.50(m,3H).
Example 4
Synthesis of Compound P082
In a 250mL three-necked flask, compound X11 (4.0 mmol) was weighed and dissolved in 100mL THF, and nBuLi (2.4M in n-hexane, 4.5 mmol) was added to the solution at-78℃and stirred for 2h. Compound X5 (4.5 mmol) was weighed and dissolved in THF (40 mL), and a THF solution of X5 was added to the X11 flask with a syringe, stirred for 1h, then slowly warmed to room temperature, and stirred overnight. After the reaction was completed, 100mL of ethyl acetate was added, and 10mL of brine was added for washing, and the organic phase was collected by extraction using a separating funnel. Anhydrous Na for organic phase 2 SO 4 And (5) drying. The solvent was removed by distillation under the reduced pressure to give a crude product, which was recrystallized from n-hexane/dichloromethane to give intermediate X12 (3.0 mmol, 75%).
Structure of test intermediate X12: MALDI-TOF MS (m/z) was obtained by matrix assisted laser desorption ionization time-of-flight mass spectrometry: c (C) 29 H 18 N 3 OP, calculated 455.1 and tested 455.2.
X12 (1.0 mmol) was dissolved in dichloromethane (10.0 mL) and cooled to 5℃with an ice bath. Hydrogen peroxide (3 mmol) was slowly added to the solution. The ice bath was removed and the solution was stirred at room temperature overnight. After the reaction was completed, the reaction mixture was washed with brine. The organic phase was collected, dried over anhydrous sodium sulfate, filtered and the solvent was evaporated. The crude product was recrystallized from n-hexane/dichloromethane (94:6, vol/vol), filtered, washed with n-hexane and dried under vacuum, and purified by sublimation to give the title compound P082 (0.93 mmol, 93%).
Structure of test target product P082: MALDI-TOF MS (m/z) was obtained by matrix assisted laser desorption ionization time-of-flight mass spectrometry: c (C) 29 H 18 N 3 O 2 P calculated 471.1 and tested 471.4.
Elemental analysis: theoretical value C,73.88; h,3.85; n,8.91; test value C,73.93; h,3.83; n,8.87.
1 H-NMR(400MHz，CDCl 3 )：δ(ppm)9.31(d,1H),9.20(d,1H),8.56-8.60(m,3H),8.50(m,1H),8.18(m,1H),7.98(d,1H),7.93(m,1H),7.70-7.76(m,5H),7.42-7.50(m,4H)。
Example 5
Synthesis of Compound P133
X13 (5.0 mmol) was weighed and dissolved in THF (100 mL) and the dissolution temperature was reduced to-78deg.C, t-BuLi (20.0 mmol) was slowly added dropwise to the solution, after the addition was completed, the temperature was slowly raised to room temperature and stirring was continued for 4h. The solution was then cooled to-196 ℃ with liquid nitrogen. PCl3 (100 mmol) was added, slowly warmed to room temperature, stirring continued for 4h, and the solvent was distilled off under reduced pressure to give a white precipitated crude product which was recrystallized from n-hexane/THF to give intermediate X14 (3.0 mmol, 60%).
Structure of test intermediate X14: MALDI-TOF MS (m/z) was obtained by matrix assisted laser desorption ionization time-of-flight mass spectrometry: c (C) 26 H 16 ClP calculated as 394.1 and tested as 394.3.
In a 250mL three-necked flask, compound X15 (2.0 mmol) was weighed and dissolved in 50mL THF, and nBuLi (2.4M in n-hexane, 2.2 mmol) was added to the solution at-78℃and stirred for 2h. Compound X14 (2.2 mmol) was weighed and dissolved in THF (20 mL) and the T of X14 was injected using a syringeThe HF solution was added to the X15 flask and stirred for 1h, then slowly warmed to room temperature and stirred overnight. After the reaction was completed, 50mL of ethyl acetate was added, and 6mL of brine was added for washing, and extraction was performed using a separating funnel, and an organic phase was collected. Anhydrous Na for organic phase 2 SO 4 And (5) drying. The solvent was removed by distillation under the reduced pressure to give a crude product, which was recrystallized from n-hexane/dichloromethane to give intermediate X16 (1.46 mmol, 73%).
Structure of test intermediate X16: MALDI-TOF MS (m/z) was obtained by matrix assisted laser desorption ionization time-of-flight mass spectrometry: c (C) 44 H 27 N 2 P calculated 614.2 and tested 614.3.
X16 (3.2 mmol) was dissolved in dichloromethane (30.0 mL) and cooled to 5℃with an ice bath. Hydrogen peroxide (10.0 mmol) was slowly added to the solution. The ice bath was removed and the solution was stirred at room temperature overnight. After the reaction was completed, the reaction mixture was washed with brine. The organic phase was collected, dried over anhydrous sodium sulfate, filtered and the solvent was evaporated. The crude product was recrystallized from n-hexane/dichloromethane (93:7, vol/vol), filtered, washed with n-hexane and dried under vacuum, and purified by sublimation to give the title compound P133 (2.72 mmol, 85%).
Structure of test target product P0133: MALDI-TOF MS (m/z) was obtained by matrix assisted laser desorption ionization time-of-flight mass spectrometry: c (C) 44 H 27 N 2 OP, calculated 630.2 and tested 630.5.
Elemental analysis: theoretical value C,83.79; h,4.32; n,4.44; test value C,83.84; h,4.29; n,4.42.
1 H-NMR(400MHz,CDCl 3 )δ(ppm)9.32(d,1H),8.52-8.56(m,3H),8.20-8.22(m,3H),8.12-8.16(m,4H),8.06-8.08(m,2H),8.00-8.02(m,1H),7.80-7.82(m,3H),7.71-7.73(m,2H),7.32-7.38(m,3H),7.07-7.13(m,3H),6.86-6.92(m,1H),6.72-6.76(m,1H)。
Application example 1
The application example provides an OLED device, the OLED device includes in proper order: the device comprises a substrate, an ITO anode, a hole injection layer, a first hole transport layer, a second hole transport layer, a light emitting layer, a first electron transport layer, a second electron transport layer and a cathode (silver electrode).
The OLED device was prepared as follows:
(1) Cutting a glass substrate into sizes of 50mm×50mm×0.7mm, respectively performing ultrasonic treatment in acetone, isopropanol and deionized water for 30 minutes, and then cleaning in ozone for 10 minutes; mounting the obtained glass substrate with the ITO anode on vacuum deposition equipment;
(2) At a vacuum degree of 2X 10 -6 Under Pa, vacuum evaporating a hole injection layer material compound 1 on the ITO anode layer, wherein the thickness is 5nm;
(3) Evaporating a compound 2 on the hole injection layer to form a first hole transport layer with the thickness of 90nm;
(4) Vacuum evaporating a compound 3 on the first hole transport layer to form a second hole transport layer, wherein the thickness of the second hole transport layer is 10nm;
(5) Vacuum evaporating a luminescent layer on the second hole transport layer, wherein the compound 4 is used as a main material of the luminescent layer, the compound 5 is used as a doping material of the luminescent layer, the doping proportion is 3%, and the thickness is 30nm;
(6) Vacuum evaporating a compound 6 on the light-emitting layer as a first electron transport layer, wherein the thickness is 5nm;
(7) Vacuum evaporating an organic compound P001 and doped ytterbium (the mass ratio of the organic compound P001 to the doped ytterbium is 97:3) provided by the application on the first electron transport layer to serve as a second electron transport layer, wherein the thickness of the second electron transport layer is 30nm;
(8) And vacuum evaporating silver electrode as cathode on the second electron transport layer with thickness of 100nm.
Application example 2
The present application example differs from application example 1 in that P001 in step (7) is replaced with an equal amount of P002.
Application example 3
The present application example differs from application example 1 in that P001 in step (7) is replaced with an equal amount of P049.
Application example 4
The present application example differs from application example 1 in that P001 in step (7) is replaced with an equal amount of P077.
Application example 5
The present application example differs from application example 1 in that P001 in step (7) is replaced with an equal amount of P082.
Application example 6
The present application example differs from application example 1 in that P001 in step (7) is replaced with an equal amount of P108.
Application example 7
The present application example differs from application example 1 in that P001 in step (7) is replaced with an equal amount of P112.
Application example 8
The present application example differs from application example 1 in that P001 in step (7) is replaced with an equal amount of P133.
Application example 9
The present application example differs from application example 1 in that P001 in step (7) is replaced with an equal amount of P144.
Application example 10
The present application example differs from application example 1 in that P001 in step (7) is replaced with an equal amount of P148.
Comparative example 1
The present comparative example differs from application example 1 in that M16 in step (7) was used in an equivalent amount of comparative compound 1And (5) replacing.
Comparative example 2
The present comparative example differs from application example 1 in that M16 in step (7) was used with an equal amount of comparative compound 2And (5) replacing.
Performance test:
(1) Simulation calculation of the compound:
by applying Density Functional Theory (DFT), the organic compound provided by the application optimizes and calculates the distribution condition of the molecular front-line orbitals HOMO and LUMO under the calculated level of B3LYP/6-31G (d) through a Guassian09 program package (Guassian Inc.), and simultaneously calculates the singlet energy level S of the compound molecule based on the time-dependent density functional theory (TDDFT) simulation 1 And triplet energy level T 1 The results are shown in Table 1.
TABLE 1
As can be seen from the data in Table 1, the organic compounds S provided in examples 1 to 10 of the present application 1 No absorption in the visible light field exists, and the LUMO (eV) value is between 1.4 and 2.0eV, so that the material is suitable for being used as a common layer material for electron transmission.
(2) Performance evaluation of OLED device:
testing the currents of the OLED device under different voltages by using a Keithley 2365A digital nano-volt meter, and dividing the currents by the light emitting areas to obtain the current densities of the OLED device under different voltages; testing the brightness and radiant energy density of the OLED device under different voltages by using a Konicaminolta CS-2000 spectroradiometer; according to the current density and brightness of the OLED device under different voltages, the OLED device with the same current density (10 mA/cm 2 ) Operating voltage V and current efficiency (cd/A), V on For a luminance of 1cd/m 2 A lower turn-on voltage; lifetime T95 (at 50 mA/cm) was obtained by measuring the time when the luminance of the OLED device reached 95% of the initial luminance 2 Under test conditions; the test data are shown in table 2.
TABLE 2
As can be seen from the data in table 2, the OLED devices prepared based on the organic compounds provided in examples 1 to 10 according to the present application as electron transport layer materials have lower turn-on voltage and operating voltage, higher current efficiency and longer operating life than the comparative compounds 1, 2, 3 and 4, and thus the compounds provided according to the present application can complex with Yb metal, and thus, the heat and electric field generated during the driving of the devices can be alleviated, which can lead to metal movement; in addition, the specific nitrogen-containing heterocyclic skeleton structure and the cyclic structure containing P=O double bond are mutually matched, so that the phenomenon of evaporation coating blocking caused by molecular accumulation is avoided in the processing process of the obtained compound; the application selects specific compound to be used as the electron luminescent layer of the organic electroluminescent device, and the obtained device has low starting voltage and working voltage, high efficiency and long service life.
A further embodiment of the present application provides an organic light emitting display device including an organic light emitting display panel as described above.
The above description of the embodiments is only for aiding in the understanding of the method of the present application and its core ideas. It should be noted that it will be apparent to those skilled in the art that various modifications and adaptations of the application can be made without departing from the principles of the application and these modifications and adaptations are intended to be within the scope of the application as defined in the following claims.
Claims (12)
1. A compound having a structure represented by the formula (I),
wherein Ar is of formula (Ar-3),
wherein A is 5 Ring, A 6 Ring, A 7 The ring is selected from C6-C30 aromatic rings;
# represents the connection position with L;
l is an aryl group of C6-C30;
R 5 、R 6 、R 7 independently selected from hydrogen, C1-C30 alkyl, C1-C30 alkoxy, C6-C30 aromatic ring group or C3-C30 aromatic heterocyclic group;
said n 5 、n 6 、n 7 Independently selected from 0, 1, 2 or 3;
X 1 、X 2 、X 3 、X 4 、X 5 、X 6 independently selected from CH or N; and X is 1 And X 2 At least one of which is N, X 4 And X 5 At least one of which is N;
alternatively, X 1 And X 5 Forms a 5-7 membered ring with the carbon in which they are located, and X 1 And X 2 At least one of which is N, X 4 And X 5 At least one of which is N;
alternatively, X 2 And X 4 Forms a 5-7 membered ring with the carbon in which they are located, and X 1 And X 2 At least one of which is N, X 4 And X 5 At least one of which is N;
the R is 1 、R 2 Independently selected from C1-C30 alkyl, C1-C30 alkoxy, C6-C30 aromatic ring group or C3-C30 aromatic heterocyclic group;
the n, n 1 、n 2 Independently selected from 0, 1, 2, 3 or 4.
2. The compound according to claim 1, wherein the compound has a structure represented by the formula (I-1) or the formula (I-2),
X 1 、X 2 、X 3 、X 4 、X 5 、X 6 independently selected from CH or N; and X is 1 And X 2 At least one of which is N, X 4 And X 5 At least one of which is N;
the R is 1 、R 2 Independently selected from C1-C30 alkyl, C1-C30 alkoxy, C6-C30 aromatic ring group or C3-C30 aromatic heterocyclic group;
l is an aryl group of C6-C30;
the n, n 1 、n 2 Independently selected from 0, 1, 2, 3 or 4.
3. The compound of claim 1, wherein a is 5 Ring, A 6 Ring, A 7 The rings are independently selected from benzene, naphthalene, anthracene, or phenanthrene.
4. A compound having a structure represented by the formula (I),
wherein Ar is
Wherein R is 21 ’、R 22 ’、R 23 ’、R 24 ’、R 25 ’、R 26 ’、R 27 ’、R 28 ’、R 29 ’、R 30 ’、R 31 ’、R 32 ' independently selected from hydrogen or C1-C6 alkyl; or R is 21 ’、R 22 ’、R 23 ’、R 24 ’、R 25 ’、R 26 ’、R 27 ’、R 28 ’、R 29 ’、R 30 ’、R 31 ’、R 32 Any two adjacent substituents of' together with the carbon on which they are located form a C6-C18 aryl group.
5. The compound of claim 1, wherein L is phenyl, naphthyl, biphenyl, terphenyl, anthracenyl, or phenanthryl.
6. The electron transport layer material of claim 1, wherein R 1 Or R is 2 The heteroatoms in the C3-C30 aromatic heterocyclic groups defined in (a) are nitrogen, oxygen or sulfur.
7. The compound of claim 1, wherein R 1 、R 2 Independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, isopentyl, t-pentyl, n-hexyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, t-butoxy, n-pentoxy, isopentoxy, t-pentoxy, n-hexoxy, phenyl, diphenyl, naphthyl, anthracenyl, phenanthryl, furyl, pyranyl, pyridyl, piperidinyl or thienyl.
8. The compound of claim 1, wherein the compound has the structure:
9. a process for the preparation of a compound as claimed in claim 1 comprising:
combining a compound of formula (II) with Ar-Y 1 The compound with the structure of the formula (I) is obtained by reaction,
X 1 、X 2 、X 3 、X 4 、X 5 、X 6 independently selected from CH or N; and X is 1 And X 2 At least one of which is N, X 4 And X 5 At least one of which is N;
alternatively, X 1 And X 5 Forms a 5-7 membered ring with the carbon in which they are located, and X 1 And X 2 At least one of which is N, X 4 And X 5 At least one of which is N;
alternatively, X 2 And X 4 Forms a 5-7 membered ring with the carbon in which they are located, and X 1 And X 2 At least one of which is N, X 4 And X 5 At least one of which is N;
the R is 1 、R 2 Independently selected from C1-C30 alkyl, C1-C30 alkoxy, C6-C30 aromatic ring group or C3-C30 aromatic heterocyclic group;
l is an aryl group of C6-C30;
the n, n 1 、n 2 Independently selected from 0, 1, 2, 3 or 4;
and Y1 and Y2 are independently selected from halogen.
10. A display panel comprising an organic light-emitting device comprising an anode, a cathode, at least one organic compound layer between the anode and the cathode, the organic compound of the organic compound layer comprising at least one of the compounds of any one of claims 1 to 8.
11. The display panel according to claim 10, wherein the organic compound layer includes an electron transport layer containing at least one of the compounds according to any one of claims 1 to 8.
12. A display device comprising the display panel of claim 10.
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