CN106854218B - A kind of silicon anthracene derivative and preparation method thereof and organic luminescent device - Google Patents
A kind of silicon anthracene derivative and preparation method thereof and organic luminescent device Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- SCUHZRDUDKPOPM-UHFFFAOYSA-N anthracene;silicon Chemical class [Si].C1=CC=CC2=CC3=CC=CC=C3C=C21 SCUHZRDUDKPOPM-UHFFFAOYSA-N 0.000 title abstract description 9
- -1 formula (1):Wherein Chemical class 0.000 claims abstract description 37
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
- 239000000543 intermediate Substances 0.000 claims description 20
- 239000012044 organic layer Substances 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 6
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 239000005708 Sodium hypochlorite Substances 0.000 claims description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 239000005457 ice water Substances 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 4
- 238000000967 suction filtration Methods 0.000 claims description 4
- 238000005303 weighing Methods 0.000 claims description 4
- 238000007259 addition reaction Methods 0.000 claims description 3
- 239000007806 chemical reaction intermediate Substances 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 3
- 239000000463 material Substances 0.000 abstract description 20
- 239000000376 reactant Substances 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 61
- 238000002347 injection Methods 0.000 description 17
- 239000007924 injection Substances 0.000 description 17
- 230000005525 hole transport Effects 0.000 description 13
- 239000000243 solution Substances 0.000 description 9
- 230000000903 blocking effect Effects 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 239000000758 substrate Substances 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 238000010345 tape casting Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 108091008695 photoreceptors Proteins 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 238000004506 ultrasonic cleaning Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 238000005566 electron beam evaporation Methods 0.000 description 2
- 238000005328 electron beam physical vapour deposition Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
- 238000007650 screen-printing Methods 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000001931 thermography Methods 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [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 2
- 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
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
- C07F7/0807—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms comprising Si as a ring atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
Abstract
The present invention relates to a kind of silicon anthracene derivative and preparation method thereof and organic luminescent devices, belong to electroluminescent material technical field.Shown in described its structural formula of silicon anthracene derivative such as formula (1):Wherein, R is substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C6~C60Aryl, substituted or non-substituted C5~C60Condensed ring radical or substituted or non-substituted C5~C60Heterocycle.It is to react reactant by addition and cyclization silicon anthracene derivative is made the present invention also provides a kind of preparation method of silicon anthracene derivative.Have the advantages that luminous efficiency is high and the service life is long with organic luminescent device prepared by silicon anthracene derivative provided by the invention.The preparation method of silicon anthracene derivative provided by the invention, raw material are easy to get, and preparation method is simple, is easy to industrialization.
Description
Technical Field
The invention relates to the technical field of electroluminescent materials, in particular to a silanthracene derivative, a preparation method thereof and an organic light-emitting device.
Background
The organic electroluminescent device has attracted extensive attention due to its advantages of thin shape, large area, full curing, flexibility and the like, and the organic electroluminescent device has also become a hot spot of research by people due to its great potential in the aspects of solid-state lighting sources, liquid crystal backlight sources and the like.
As early as the fifty years bernanose.a et al began the study of organic electroluminescent devices (OLEDs). The material initially studied was an anthracene single crystal sheet. The required driving voltage is high due to the problem of large thickness of the single wafer. The structures reported by dungeon (c.w.tang) and Vanslyke of Eastman Kodak company in the united states until 1987 were: ITO/Diamine/Alq3Ag, the brightness of the device reaches 100cd/m under the working voltage of 10V2And the external quantum efficiency reaches 1.0 percent. The research on electroluminescence has attracted much attention by scientists, and they have seen the possibility of applying organic electroluminescent devices to displays. The research and industrialization of organic electroluminescent devices have been revealed.
The organic electroluminescent device has important significance for industrialization, such as high efficiency, high brightness, high color stability and the like. Currently, the luminous efficiency and lifetime have become bottleneck problems that restrict the performance of organic electroluminescent devices. Therefore, it is important to develop a luminescent material with good performance in terms of luminous efficiency and lifetime, which can be used for preparing an organic light emitting device.
Disclosure of Invention
The invention aims to provide a silanthracene derivative, a preparation method thereof and an organic light-emitting device.
In order to achieve the above purpose, the technical scheme of the invention is as follows:
a silanthracene derivative has a structural formula shown as a formula (1):
wherein R is substituted or unsubstituted C1～C60Alkyl, substituted or unsubstituted C6～C60Aryl, substituted or unsubstituted C5～C60Condensed ring group of (A) or substituted or unsubstituted C5～C60The heterocyclic group of (1).
In the above technical scheme, R is phenyl, p-methylphenyl, 4-biphenyl, p-pyridylphenyl, 2-naphthyl, 6-methyl-2-naphthyl, heptalkyl, 1-phenyl-6-hexyl, 4-pyridyl, 2-phenyl-4-pyrimidyl or 2, 6-diphenyl-4-triazinyl.
Namely, the silanthracene derivative has any structure shown in a formula 001-012:
a preparation method of a silanthracene derivative comprises the following steps:
carrying out addition and cyclization reaction on a compound with a structure shown in a formula I and an intermediate with a structure shown in a formula II to obtain a silanthracene derivative with a structure shown in a formula (1);
the synthetic route is as follows:
wherein R is substituted or unsubstituted C1～C60Alkyl, substituted or unsubstituted C6～C60Aryl, substituted or unsubstituted C5～C60Condensed ring group of (A) or substituted or unsubstituted C5～C60The heterocyclic group of (1).
In the technical scheme, the structural intermediate shown in the formula II is prepared by the following method:
adding a compound shown as a formula 1-1, a compound shown as a formula 1-2 and aluminum trichloride into a reaction bottle, adding a benzene solvent, adding ice water after the reaction is finished, stirring, carrying out suction filtration, adding sodium carbonate for neutralization until the pH value is 6.5-7, adding a sodium hypochlorite solution, stirring, filtering to obtain an intermediate shown as a formula 1-3, adding concentrated sulfuric acid for cyclization reaction to obtain a structural intermediate shown as a formula II;
the synthetic route is as follows:
in the technical scheme, the silanthracene derivative is prepared by the following method:
weighing a compound shown in the formula I under a nitrogen protection system, adding a tetrahydrofuran solution, dropwise adding n-butyllithium at-78 ℃, reacting for 2 hours, then dropwise adding a tetrahydrofuran solution containing a structural intermediate shown in the formula II, reacting for 8 hours at room temperature under the nitrogen protection condition after dropwise adding, adding dilute hydrochloric acid, extracting with diethyl ether, separating liquid, concentrating, and adding dichloromethane with the volume ratio of 1: 3: recrystallizing petroleum ether to obtain a reaction intermediate, adding concentrated sulfuric acid, reacting at room temperature for 9 hours, and hydrolyzing, extracting, separating liquid, and recrystallizing to obtain the silanthracene derivative with the structure shown in the formula (1);
the synthetic route is as follows:
whereinR is substituted or unsubstituted C1～C60Alkyl, substituted or unsubstituted C6～C60Aryl, substituted or unsubstituted C5～C60Condensed ring group of (A) or substituted or unsubstituted C5～C60The heterocyclic group of (1).
An organic light emitting device comprising a first electrode, a second electrode, and an organic layer disposed between the first and second electrodes; the organic layer comprises the silanthracene derivative.
The invention has the beneficial effects that:
the organic light-emitting device prepared from the silanthracene derivative provided by the invention has the advantages of high light-emitting efficiency and long service life.
The preparation method of the silanthracene derivative provided by the invention has the advantages of easily available raw materials, simple preparation method and easy industrialization.
Detailed Description
The structural formula of the silanthracene derivative provided by the invention is shown as the formula (1):
wherein R is substituted or unsubstituted C1～C60Alkyl, substituted or unsubstituted C6～C60Aryl, substituted or unsubstituted C5～C60Condensed ring group of (A) or substituted or unsubstituted C5～C60The heterocyclic group of (1). Preferably, R is phenyl, p-methylphenyl, 4-biphenyl, p-pyridylphenyl, 2-naphthyl, 6-methyl-2-naphthyl, heptanyl, 1-phenyl-6-hexyl, 4-pyridyl, 2-phenyl-4-pyrimidinyl, or 2, 6-diphenyl-4-triazinyl. Namely, the silanthracene derivative has any structure shown in a formula 001-012:
the invention also provides a preparation method of the silanthracene derivative, which is characterized in that the silanthracene derivative with the structure shown in the formula (1) is obtained by carrying out addition and cyclization reactions on the compound with the structure shown in the formula I and the intermediate with the structure shown in the formula II. The method specifically comprises the following steps:
step 1, preparation of intermediate
Adding a compound shown as a formula 1-1, a compound shown as a formula 1-2 and aluminum trichloride into a reaction bottle, adding a benzene solvent, adding ice water after the reaction is finished, stirring, carrying out suction filtration, adding sodium carbonate for neutralization until the pH value is 6.5-7, adding a sodium hypochlorite solution, stirring, filtering to obtain an intermediate shown as a formula 1-3, adding concentrated sulfuric acid for cyclization reaction to obtain a structural intermediate shown as a formula II;
the synthetic route is as follows:
step 2, preparation of silanthracene derivatives
Weighing a compound shown in the formula I under a nitrogen protection system, adding a tetrahydrofuran solution, dropwise adding n-butyllithium at-78 ℃, reacting for 2 hours, then dropwise adding a tetrahydrofuran solution containing a structural intermediate shown in the formula II, reacting for 8 hours at room temperature under the nitrogen protection condition after dropwise adding, adding dilute hydrochloric acid, extracting with diethyl ether, separating liquid, concentrating, and adding dichloromethane with the volume ratio of 1: 3: recrystallizing petroleum ether to obtain a reaction intermediate, adding concentrated sulfuric acid, reacting at room temperature for 9 hours, and hydrolyzing, extracting, separating liquid, and recrystallizing to obtain the silanthracene derivative with the structure shown in the formula (1);
the synthetic route is as follows:
wherein R is substituted or unsubstituted C1～C60Alkyl, substituted or unsubstituted C6～C60Aryl, substituted or unsubstituted C5～C60Condensed ring group of (A) or substituted or unsubstituted C5～C60The heterocyclic group of (1). Preferably, R is phenyl, p-methylphenyl, 4-biphenyl, p-pyridylphenyl, 2-naphthyl, 6-methyl-2-naphthyl, heptanyl, 1-phenyl-6-hexyl, 4-pyridyl, 2-phenyl-4-pyrimidinyl, or 2, 6-diphenyl-4-triazinyl.
The invention also provides an organic light-emitting device which comprises the silanthracene derivative with the structure shown in the formula (1).
The organic light emitting device is well known to those skilled in the art, and the present invention preferably includes a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode; the organic layer comprises a silanthracene derivative with a structure shown in formula (1). The silanthracene derivative may be contained in the organic layer in a single form or in a mixture with other substances.
In the present invention, the organic layer refers to all layers between the first electrode and the second electrode of the organic light emitting device. At least one of the organic layers is a light-emitting layer.
According to the present invention, the organic layer preferably includes one or more layers selected from a hole injection layer, a hole transport layer, a layer having both hole injection and hole transport functions, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a layer having both electron transport and electron injection functions, and more preferably includes a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, which are provided in this order, or a layer having both hole injection and hole transport functions, an electron blocking layer, a light emitting layer, a hole blocking layer, and a layer having both electron transport and electron injection functions, which are provided in this order.
When the organic layer of the present invention includes a hole injection layer, a hole transport layer, or a layer having both hole injection and hole transport properties, it is preferable that at least one of the hole injection layer, the hole transport layer, or the layer having both hole injection and hole transport properties includes a hole injection material, a hole transport material, or a material having both hole injection and hole transport properties.
When the organic layer is of a single-layer structure, the organic layer is a light-emitting layer, and when the organic layer is of a multilayer structure, the organic layer comprises a light-emitting layer; the light-emitting layer preferably comprises one or more of a phosphorescent host, a fluorescent host, a phosphorescent doped material and a fluorescent doped material; one or more of the phosphorescent host, the fluorescent host, the phosphorescent doped material and the fluorescent doped material is a silanthracene derivative with a structure shown in a formula (1).
The light emitting layer can also be a red, yellow or cyan light emitting layer, and the silicon anthracene derivative is a main body or a doping substance of the red, yellow or cyan light emitting layer. For example, when the light emitting layer is a cyan light emitting layer, the silicon anthracene derivative having the structure of formula (1) can provide an organic light emitting device having high efficiency, high luminance, high resolution, and long lifetime when used for a cyan host or cyan dopant.
When the organic layer includes an electron transport layer, the electron transport layer may include a silanthracene derivative and/or a metal compound having a structure represented by formula (1). The metal compound is not particularly limited as long as it is a substance for electron transport, which is well known to those skilled in the art.
When the organic layer comprises the light-emitting layer and the electron transport layer at the same time, the light-emitting layer and the electron transport layer can respectively comprise the silanthracene derivative with the structure shown in the formula (1) and the structure of the silanthracene derivative is the same or different.
The organic light-emitting device provided by the invention is prepared by using the silanthracene derivative with the structure shown in the formula (1) and conventional materials, the preparation method of the organic light-emitting device is not limited, the conventional method in the field can be used, and the invention preferably uses the methods of thin film evaporation, electron beam evaporation, physical vapor deposition and the like to evaporate metal, oxide with conductivity and alloy thereof on a substrate to form an anode, and then forms an organic layer and an evaporation cathode on the anode to obtain the organic light-emitting device.
The organic material layer and the anode material are sequentially evaporated on the cathode material layer on the outer substrate to manufacture the organic light-emitting device.
The organic layer may include a multi-layer structure of the hole injection layer, the hole transport layer, the light emitting layer, the hole blocking layer and the electron transport layer, and the multi-layer structure may be formed by evaporation using the above-mentioned thin film evaporation, electron beam evaporation or physical vapor deposition, or various polymer solvent engineering techniques may be used instead of the evaporation method, such as spin-coating (spin-coating), tape-casting (tape-casting), doctor-blading (doctor-blading), Screen-Printing (Screen-Printing), inkjet Printing or Thermal-Imaging (Thermal-Imaging) to reduce the number of layers.
The organic light-emitting device provided by the invention can be divided into front light-emitting, back light-emitting or double-sided light-emitting according to the used materials; and the organic light emitting device may be applied to an Organic Light Emitting Device (OLED), an Organic Solar Cell (OSC), an electronic paper (e-paper), an Organic Photoreceptor (OPC), or an Organic Thin Film Transistor (OTFT) in the same principle.
The silanthracene derivative having the structure represented by formula (1) provided by the present invention is applicable to organic devices such as organic solar cells, lighting OLEDs, flexible OLEDs, organic photoreceptors, and organic transistors, according to the principle of applying organic light-emitting devices.
The invention also provides an organic photoelectric material, which comprises the silanthracene derivative with the structure shown in the formula (1); the organic photoelectric material comprises an organic solar cell, electronic paper, an organic photoreceptor or an organic transistor.
In order to further illustrate the present invention, the following examples are provided to describe the silanthracene derivatives, the preparation method thereof, and the organic light emitting device in detail.
Example 1
Synthesis of intermediate of structure shown as formula II
Adding 0.10mol of a compound shown as a formula 1-1, 0.24mol of a compound shown as a formula 1-2 and 0.24mol of aluminum trichloride into a reaction bottle, wherein the volume of benzene as a solvent is 300mL, adding 50mL of ice water after the reaction is finished, stirring, performing suction filtration, adding soda ash for neutralizing until the pH value is 6.5-7, adding a sodium hypochlorite solution, stirring, filtering to obtain an intermediate 1-3, adding concentrated sulfuric acid for cyclization reaction to obtain a structural intermediate shown as a formula II, wherein the yield is 80%.
Example 2
Synthesis of target product 001
Weighing 0.44mol of bromobenzene under a nitrogen protection system, adding 300mL of freshly distilled tetrahydrofuran solution, dropwise adding 7.19g of n-butyllithium at-78 ℃ for reacting for 2 hours, then dropwise adding 200mL of tetrahydrofuran solution containing 0.15mol of intermediate, reacting for 8 hours at room temperature under the nitrogen protection condition after dropwise adding, adding 100mL of 1M dilute hydrochloric acid, extracting with 100mL of diethyl ether for 3 times, separating liquid, concentrating, and adding dichloromethane with a volume ratio of 1: 3: recrystallizing with petroleum ether to obtain intermediate 2-1. And (2) continuously adding the mixture into 300mL of concentrated sulfuric acid, reacting for 9 hours at room temperature, and obtaining a target product 001(0.075mol) with a yield of 50% through hydrolysis, extraction, liquid separation and recrystallization, wherein the mass spectrum is as follows: 926.38.
examples 3 to 13
The target product 002-012 was synthesized by the above method for preparing the target product 001, the amount of the reactant and the reaction conditions were the same as those of example 2, and the reactant, the product, the yield and the mass spectrum data are shown in Table 1.
TABLE 1 examples 3-13 reactants, products, yields, Mass Spectrometry data
Organic light emitting device production examples
Coating thickness of Fisher company ofThe ITO glass substrate is placed in distilled water for cleaning for 2 times, ultrasonic cleaning is carried out for 30 minutes, the ITO glass substrate is repeatedly cleaned for 2 times by distilled water and ultrasonic cleaning is carried out for 10 minutes, after the cleaning by distilled water is finished, solvents such as isopropanol, acetone, methanol and the like are sequentially subjected to ultrasonic cleaning and drying, the ITO glass substrate is transferred into a plasma cleaning machine, and the substrate is cleaned for 5 minutesAnd the clock is sent to the evaporator.
The compound a is a luminescent layer material, the compound b is a hole injection layer material, the compound C is a hole transport layer material, and the specific device structure is ITO/2-TNATA (80nm)/α -NPD (30 nm)/compound a (30nm)/Alq3(30nm)/LiF(0.5nm)/Al(60nm)。
Evaporating a hole injection layer 2-TNATA on the prepared ITO transparent electrodeEvaporation of hole transport layer a-NPD (N, N '-di (1-naphthyl) -N, N' -diphenyl- (1, 1 '-biphenyl) -4, 4' -diamine)Vapor deposition of Compound 001 or Compound 002 or Compound a 9, 10-bis (Naphthalen-2-yl) Anthracene in Table 1 Hole blocking layer and electron transport layer Alq3 Cathode LiFAlThe organic evaporation speed is maintained in the above processLiF isAl is
The luminescent device prepared by the invention is tested by adopting a KEITHLEY Giaxle 2400 type source measuring unit and a CS-2000 spectral radiance luminance meter so as to evaluate the driving voltage, the luminance, the luminous efficiency and the luminous color of the luminescent device; the performance and light-emitting characteristics of the obtained devices were measured, and the results are shown in table 2, and table 2 shows the results of the light-emitting characteristics of the light-emitting devices prepared from some of the compounds prepared in the examples of the present invention and the comparative materials.
TABLE 2
From the results in table 1, it can be seen that the organic light emitting device made of the blue light host material prepared from the silanthracene derivative provided by the invention has significantly improved luminous efficiency and lifetime characteristics.
The above description of the embodiments is only intended to facilitate the understanding of the method of the invention and its core idea. It should be noted that, for those skilled in the art, it is possible to make various improvements and modifications to the present invention without departing from the principle of the present invention, and those improvements and modifications also fall within the scope of the claims of the present invention.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (5)
1. A silanthracene derivative is characterized by having a structural formula shown as a formula (1):
wherein,
r is phenyl, p-methylphenyl, 4-biphenyl, p-pyridylphenyl, 2-naphthyl, 6-methyl-2-naphthyl, heptanyl, 1-phenyl-6-hexyl, 4-pyridyl, 2-phenyl-4-pyrimidinyl or 2, 6-diphenyl-4-triazinyl.
2. A process for the preparation of a silanthracene derivative according to claim 1, comprising the steps of:
carrying out addition and cyclization reaction on a compound with a structure shown in a formula I and an intermediate with a structure shown in a formula II to obtain a silanthracene derivative with a structure shown in a formula (1);
the synthetic route is as follows:
wherein R is phenyl, p-methylphenyl, 4-biphenyl, p-pyridylphenyl, 2-naphthyl, 6-methyl-2-naphthyl, heptanyl, 1-phenyl-6-hexyl, 4-pyridyl, 2-phenyl-4-pyrimidinyl, or 2, 6-diphenyl-4-triazinyl.
3. The method for preparing silanthracene derivatives according to claim 2, wherein the structural intermediate represented by formula ii is prepared by the following method:
adding a compound shown as a formula 1-1, a compound shown as a formula 1-2 and aluminum trichloride into a reaction bottle, adding a benzene solvent, adding ice water after the reaction is finished, stirring, carrying out suction filtration, adding sodium carbonate for neutralization until the pH value is 6.5-7, adding a sodium hypochlorite solution, stirring, filtering to obtain an intermediate shown as a formula 1-3, adding concentrated sulfuric acid for cyclization reaction to obtain a structural intermediate shown as a formula II;
the synthetic route is as follows:
4. the method for preparing a silanthracene derivative according to claim 2, characterized in that it is prepared in particular by:
weighing a compound shown in the formula I under a nitrogen protection system, adding a tetrahydrofuran solution, dropwise adding n-butyllithium at-78 ℃, reacting for 2 hours, then dropwise adding a tetrahydrofuran solution containing a structural intermediate shown in the formula II, reacting for 8 hours at room temperature under the nitrogen protection condition after dropwise adding, adding dilute hydrochloric acid, extracting with diethyl ether, separating liquid, concentrating, and adding dichloromethane with the volume ratio of 1: 3: recrystallizing petroleum ether to obtain a reaction intermediate, adding concentrated sulfuric acid, reacting at room temperature for 9 hours, and hydrolyzing, extracting, separating liquid, and recrystallizing to obtain the silanthracene derivative with the structure shown in the formula (1);
the synthetic route is as follows:
wherein R is phenyl, p-methylphenyl, 4-biphenyl, p-pyridylphenyl, 2-naphthyl, 6-methyl-2-naphthyl, heptanyl, 1-phenyl-6-hexyl, 4-pyridyl, 2-phenyl-4-pyrimidinyl, or 2, 6-diphenyl-4-triazinyl.
5. An organic light emitting device comprising a first electrode, a second electrode, and an organic layer disposed between the first and second electrodes; wherein the organic layer comprises the silanthracene derivative according to claim 1.
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