CN117820346A - Blue light material based on dibenzofuran and preparation method and application thereof - Google Patents
Blue light material based on dibenzofuran and preparation method and application thereof Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 56
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 75
- 150000001875 compounds Chemical class 0.000 claims description 66
- 239000002904 solvent Substances 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 23
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- 239000003153 chemical reaction reagent Substances 0.000 claims description 16
- 238000002156 mixing Methods 0.000 claims description 14
- 239000003495 polar organic solvent Substances 0.000 claims description 14
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 claims description 12
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 230000035484 reaction time Effects 0.000 claims description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 5
- 239000003999 initiator Substances 0.000 claims description 5
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 5
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical group C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 101150003085 Pdcl gene Proteins 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 13
- 230000021615 conjugation Effects 0.000 abstract description 9
- -1 diaryl boron derivative Chemical class 0.000 abstract description 9
- 125000001624 naphthyl group Chemical group 0.000 abstract description 5
- 238000006862 quantum yield reaction Methods 0.000 abstract description 5
- 230000009286 beneficial effect Effects 0.000 abstract description 3
- 230000009878 intermolecular interaction Effects 0.000 abstract description 2
- 230000007704 transition Effects 0.000 abstract description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 230000008569 process Effects 0.000 description 8
- 239000000370 acceptor Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 230000002194 synthesizing effect Effects 0.000 description 6
- 238000012512 characterization method Methods 0.000 description 5
- 150000001793 charged compounds Chemical class 0.000 description 5
- 238000004020 luminiscence type Methods 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000010791 quenching Methods 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- IPCPCJMAMZSXTE-UHFFFAOYSA-N bis(2,4,6-trimethylphenyl)borane Chemical compound CC1=CC(C)=CC(C)=C1BC1=C(C)C=C(C)C=C1C IPCPCJMAMZSXTE-UHFFFAOYSA-N 0.000 description 3
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 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 3
- 239000011734 sodium Substances 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- PPCDVMPJPKWGEG-UHFFFAOYSA-N chloro-bis(2,4,6-trimethylphenyl)borane Chemical compound CC1=CC(C)=CC(C)=C1B(Cl)C1=C(C)C=C(C)C=C1C PPCDVMPJPKWGEG-UHFFFAOYSA-N 0.000 description 2
- 229960001701 chloroform Drugs 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001194 electroluminescence spectrum Methods 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- IBGUDZMIAZLJNY-UHFFFAOYSA-N 1,4-dibromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=C(Br)C2=C1 IBGUDZMIAZLJNY-UHFFFAOYSA-N 0.000 description 1
- FLLZCZIHURYEQP-UHFFFAOYSA-N 4-chlorobutylbenzene Chemical compound ClCCCCC1=CC=CC=C1 FLLZCZIHURYEQP-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical group [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- ZXHUJRZYLRVVNP-UHFFFAOYSA-N dibenzofuran-4-ylboronic acid Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2B(O)O ZXHUJRZYLRVVNP-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Classifications
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- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
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- 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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Abstract
The invention provides a dibenzofuran-based blue light material, and a preparation method and application thereof, and belongs to the technical field of organic electroluminescent materials. The blue light material provided by the invention takes naphthalene groups as pi bridges, and dibenzofuran electron donor and spiroboron pyridine or diaryl boron derivative electron acceptor structures are introduced into naphthalene rings to form D-pi-A type molecular structures. In the blue light material, the naphthalene group center core has a plane symmetrical structure, the electron acceptor has a non-plane rigid structure, the electron acceptor and the electron acceptor provide electron-withdrawing effect, conjugation effect and steric hindrance effect, and the electron acceptor and the conjugation effect are matched with dibenzofuranyl to form a D-pi-A molecular structure with a twisted structure, so that the blue light emission of the material is realized. Meanwhile, the conjugation effect is beneficial to reducing the energy of the system and improving the thermal stability of the material; the conjugation effect and the steric hindrance effect can improve the rigidity of the molecular structure, inhibit non-radiative transition caused by intermolecular interaction, and improve the fluorescence quantum yield of the material, thereby improving the luminous efficiency of the material.
Description
Technical Field
The invention relates to the technical field of electroluminescent materials, in particular to a dibenzofuran-based blue light material, and a preparation method and application thereof.
Background
Organic light-emitting diodes (OLEDs) have been developed over 30 years and have entered a stage of large-scale application in the display and lighting fields. Compared with the traditional display, the display has the advantages of quick response, low energy consumption, self-luminescence, wide color gamut, ultra-thin, foldable and flexible performance, capability of manufacturing large-size panels and the like, and is a novel display technology which is optimal in the future and has the application prospect.
In OLEDs devices, the properties of the emissive material are important parameters that determine the performance of the device. At present, blue light materials have the problems of low luminous efficiency, concentration quenching and poor stability, and blue light OLEDs with high efficiency and high stability are difficult to obtain, so that commercial application is difficult to meet. From the material molecular structure perspective, there are generally two design strategies for blue light molecules that make up a wide band gap. One is that the materials are connected through aromatic conjugated groups such as phenyl, fluorenyl, naphthyl, aralkyl and the like, and the luminescence wavelength is regulated and controlled through the conjugation length of the regulating groups, but the materials are easy to accumulate in an aggregation state to generate fluorescence quenching. The other is that the D-pi-A type molecule is formed by connecting a weak electron donor and a receptor through a proper conjugated pi bridge group. To realize blue light emission, it is necessary to control electron donating and electron withdrawing capabilities of electron donating and acceptor structures and conjugation degree of pi bridge groups, and improper matching of electron donors, acceptors and pi bridge groups is easy to cause red shift of luminescence and reduction of quantum yield, so that blue light materials with high luminous efficiency and good thermal stability are currently existing difficulties.
Disclosure of Invention
The invention aims to provide a dibenzofuran-based blue light material, a preparation method and application thereof.
In order to achieve the above object, the present invention provides the following technical solutions.
The invention provides a dibenzofuran-based blue light material, which has a structure shown in a formula I:
r in the formula I is* Representing the position of the radical attachment.
A specific synthetic route for dibenzofuran-based blue-light materials is shown below:
wherein, in the process of synthesizing C from A and B, the alkaline reagent is Na 2 CO 3 、K 2 CO 3 Or Cs 2 CO 3 Any one of them; the palladium catalyst is Pd (PPh) 3 ) 4 、PdCl 2 Or Pd 2 (dba) 3 Any one of them; the polar organic solvent M is any one of tetrahydrofuran, toluene and N, N-dimethylformamide; the alcohol solvent is low-carbon alcohol with the carbon number less than 4; the volume ratio of the polar organic solvent M to the alcohol solvent is 20-10:1.
In the process of synthesizing E from D, a polar solvent added with a strong base reagent is adopted as a solvent, the polar solvent is tetrahydrofuran, the strong base reagent is bis (trimethylsilyl) aminopotassium, and the dosage ratio of the strong base reagent, the structural compound shown as D and the solvent is 3-10 mmol:1-2 mmol:20-100 mL. In the process, the reaction temperature is 60-70 ℃ and the reaction time is 6-10 h.
In the synthesis of F from E, a chlorinated alkane solvent is used as the solvent, preferably dichloromethane, chloroform, carbon tetrachloride, dichloroethane, more preferably dichloromethane. The dosage of the reaction materials and the reagents is as follows: a compound of the structure shown in formula E: boron trichloride: dichloromethane solvent = 4-6 mol: 0.5-1 mL: 40-80 mL. The initial temperature of the reaction was-78 ℃, and then the reaction mixture was slowly heated to room temperature for 3-5 hours.
In the process of synthesizing I-1 from C and F, the ratio of the compound with the structure shown in the formula C to the compound with the structure shown in the formula F to the dosage of the tert-butyl lithium initiator is 1 to 1.5mol:1 to 5mol:1.5 to 10mol, the reaction temperature is-78 to room temperature, and the reaction time is 4 to 8 hours.
Another specific synthetic route for dibenzofuran-based blue materials is shown below:
wherein, in the process of synthesizing C from A and B, the alkaline reagent is Na 2 CO 3 、K 2 CO 3 Or Cs 2 CO 3 Any one of them; the palladium catalyst is Pd (PPh) 3 ) 4 、PdCl 2 Or Pd 2 (dba) 3 Any one of them; the polar organic solvent M is any one of tetrahydrofuran, toluene and N, N-dimethylformamide; the alcohol solvent is low-carbon alcohol with the carbon number less than 4; the volume ratio of the polar organic solvent M to the alcohol solvent is 20-10:1.
In the process of synthesizing I-2 from C and G, the ratio of the compound with the structure shown in the formula C to the compound with the structure shown in the formula G to the dosage of the tert-butyl lithium initiator is 1 to 1.5mol:1 to 5mol:1.5 to 10mol, the reaction temperature is-78 to room temperature, and the reaction time is 4 to 8 hours.
The dibenzofuran-based blue light material provided by the invention can be used as a luminescent layer material to be applied to an organic electroluminescent device and a preparation process thereof.
The dibenzofuran-based blue light material, and the preparation method and the application thereof provided by the invention have the technical progress compared with the prior art:
(1) Compared with the existing blue light material, the dibenzofuran-based blue light material provided by the invention takes naphthalene groups as pi-bridges and spiroboron or diaryl boron derivatives as electron acceptors. And introducing dibenzofuran electron donor and proper electron acceptor into naphthalene ring to form D-pi-A type molecule with twisted structure. The naphthalene group center core provided by the invention has a plane symmetrical structure and proper conjugation degree, and the electron acceptor has a non-plane rigid structure and weak electron withdrawing capability. The naphthalene center core and the electron acceptor form a large electron-deficient conjugated system, a weak electron-withdrawing effect, a conjugated effect and a steric hindrance effect are provided, and the naphthalene center core and the electron acceptor are matched with a weak electron donor dibenzofuran, so that blue light emission of the material is realized; meanwhile, the conjugation effect is beneficial to reducing the energy of the system and improving the thermal stability of the material; the conjugation effect and the steric hindrance effect can improve the rigidity of the molecular structure, inhibit non-radiative transition caused by intermolecular interaction, and improve the fluorescence quantum yield of the material, thereby improving the luminous efficiency of the material and being beneficial to improving the performance of the material in electroluminescent devices.
(2) The preparation method of the blue light material provided by the invention has the advantages of easily obtained starting materials, proper reaction conditions, simple operation steps, contribution to reducing the preparation cost and realization of commercial application.
Drawings
FIG. 1 is a fluorescence spectrum in toluene solution of example 1;
FIG. 2 is a graph showing fluorescence spectrum in toluene solution of example 2;
FIG. 3 is a thermogravimetric curve and a differential scanning calorimetry curve of example 1;
FIG. 4 is a thermogravimetric curve and a differential scanning calorimetry curve of example 2;
FIG. 5 is an electroluminescence spectrum of the undoped organic electroluminescent device of example 1;
FIG. 6 is an electroluminescence spectrum of the undoped organic electroluminescent device of example 2;
fig. 7 is a graph showing the variation of luminance and current density with voltage for the organic electroluminescent device prepared in example 1;
fig. 8 is a graph showing the variation of luminance and current density with voltage for the organic electroluminescent device prepared in example 2;
fig. 9 is a graph showing the current efficiency and external quantum efficiency as a function of luminance for the organic electroluminescent device prepared in example 1;
fig. 10 is a graph showing the current efficiency and external quantum efficiency as a function of luminance for the organic electroluminescent device prepared in example 2.
Detailed Description
The invention provides a dibenzofuran-based blue light material, which has a structure shown in a formula I:
r in the formula I is* Representing the position of the radical attachment.
In the synthetic route of the specific compounds of the present invention, the starting materials used are commercially available products well known in the art, unless specifically stated.
The synthetic route of the present invention is as follows.
And mixing the compound with the structure shown in the formula A, the compound B with the structure shown in the formula, an alkaline reagent, a palladium catalyst, a polar organic solvent and an alcohol solvent, and refluxing to obtain the compound with the structure shown in the formula C.
In a specific embodiment, the alcohol solvent is preferably absolute ethanol; the polar organic solvent is preferably toluene. The usage ratio of the compound with the structure shown in the formula A to the compound with the structure shown in the formula B to the alkaline reagent to the palladium catalyst is 1-2 mol: 1-3 mol: 5-20 mol:0.02 to 0.1mol, more preferably 1mol:1mol:10mol:0.05mol. The ratio of the compound of the structure shown in the formula A to the alcohol solvent is preferably 1-1.3 mmol:2 to 5mL, more preferably 1mmol:3mL. The invention has no special requirement on the mixing process of the compound with the structure shown in the formula A, the alcohol solvent and the polar organic solvent, and can uniformly mix the three.
In a specific embodiment, the temperature of the reflux is preferably 70-90 ℃, more preferably 80 ℃; the time of the reflux reaction is based on monitoring the reaction end by thin layer chromatography.
In the present invention, the equation of the reflux reaction is as follows:
after the completion of the reflux, water was added to quench the reaction. After cooling, the crude product was collected by filtration, washed with water and ethanol. The product was purified with dichloromethane or ethanol.
In the invention, a compound with a structure shown in a formula D, 5-dioxo-dibenzothiophene, a strong base reagent and a polar organic solvent are mixed for nucleophilic substitution reaction to obtain a compound with a structure shown in a formula E.
In a specific embodiment, the strong base reagent comprises potassium bis (trimethylsilyl) amide; the polar organic solvent comprises tetrahydrofuran, and the ratio of the strong alkali reagent to the structural compound shown in the D to the solvent is 3-10 mmol/1-2 mmol/20-100 mL. In the invention, the process of mixing the compound with the structure shown in the formula D, the polar organic solvent and the strong alkali reagent is not particularly required, and the three can be uniformly mixed.
In the invention, in the step (2), the temperature of the mixing reaction is 60-70 ℃ and the reaction time is 6-10 h.
In the present invention, the equation of the mixing reaction is as follows:
after completion of the mixing reaction, the present invention preferably quenches the reaction with a saturated aqueous ammonium chloride solution. The organic phase was extracted with dichloromethane and dried over anhydrous sodium sulfate. Purifying by silica gel column chromatography (eluting solvent is dichloromethane), and recrystallizing with dichloromethane and petroleum ether to obtain compound with structure shown in E.
And after obtaining the compound with the structure shown in the E, mixing the compound with the structure shown in the formula E, boron trichloride and chlorinated alkane solvent to obtain the compound with the structure shown in the formula F.
In a specific embodiment of the present invention, the usage ratio of the compound of the structure shown in formula E, boron trichloride to chloroalkanes is 4 to 6mol: 0.5-1 mL: 40-80 mL, wherein the chlorinated alkane solvent is preferably dichloromethane, trichloromethane, carbon tetrachloride and dichloroethane, and more preferably dichloromethane. The mixing of the boron trichloride and the chlorinated alkane solvent of the compound with the structure shown in the formula E preferably comprises the following steps: adding a compound with a structure shown in a formula E and boron trichloride into a chloralkane solvent.
In a specific embodiment of the invention, the initial temperature of the reaction is preferably-78 ℃, and then slowly raised to room temperature. The reaction time is preferably 3 to 5 hours. During the reaction for synthesizing F from E, it is preferably carried out under stirring.
In the present invention, the equation of the reaction is:
after the reaction is completed, the invention preferably uses vacuum to remove the excess boron trichloride and methylene chloride, then heats the residue to 100 ℃ to remove Me formed 2 SnCl 2 Obtaining the compound with the structure shown as F.
And after obtaining the compound with the structure F, mixing the compound with the structure shown in the formula C and the compound with the structure F with tert-butyllithium and tert-butylbenzene to obtain the target product with the structure shown in the formula I-1.
And mixing the compound with the structure shown in the formula C and the compound with the structure G with tert-butyllithium and tert-butylbenzene to obtain a target product with the structure shown in the formula I-2.
In a specific embodiment of the present invention, the ratio of the amount of the compound of the structure represented by formula C, the compound of the structure represented by formula F or formula G, and the t-butyllithium initiator is 1 to 1.5mol:1 to 5mol:1.5 to 10mol, the initial temperature of the reaction is preferably-78 ℃, and then slowly raised to room temperature. The reaction time is preferably 4 to 6 hours.
In the invention, the reaction equation is:
after completion of the reaction, the solvent is preferably removed under reduced pressure, dichloromethane and water are added to the residue to extract, and the organic phase is dried over anhydrous sodium sulfate. Purifying by silica gel column chromatography (eluting solvent is dichloromethane/petroleum ether mixed solvent) to obtain target product with structure of formula I.
The invention provides an application of the dibenzofuran-based blue light material prepared by the scheme or the preparation method of the dibenzofuran-based blue light material as an organic electroluminescent material.
The invention provides an organic electroluminescent device, at least one functional layer contains the dibenzofuran blue light material or the dibenzofuran-based blue light material prepared by the preparation method.
The luminescent layer preferably contains the dibenzofuran blue light material according to the scheme or the dibenzofuran-based blue light material prepared by the preparation method according to the scheme.
In the present invention, the dibenzofuran blue material is preferably used as an undoped light emitting layer material in an electroluminescent device, or a guest material of a doped light emitting layer.
Specific embodiments of the present invention are described in more detail below.
[ example 1 ]
This example provides a dibenzofuran-based blue-emitting compound having the structure shown in formula I-1:
(1) Synthesis of Compound C:
1, 4-dibromonaphthalene (2.86 g,1.0 mol) and 4-dibenzofuran boronic acid (2.12 g,1 mol), pd (PPh 3 ) 4 (57.8 mg,0.05 mol), sodium carbonate (1.06 g,10.0 mol), ethanol and toluene were mixed in the flask. The mixture was refluxed for 8 hours. After the completion of the reaction, water was added to quench the reaction. After cooling, the crude product was collected by filtration, washed with water and ethanol. The product was purified by recrystallisation from methylene chloride or ethanol. Structural characterization data: 1 H NMR(500MHz,CDCl 3 delta 8.94 (dd, j=7.8, 1.4hz, 1H), 8.08 (dd, j=7.9, 1.4hz, 1H), 8.03 (d, j=8.8 hz, 1H), 7.99 (dd, j=7.8, 1.6hz, 1H), 7.94 (dd, j=7.8, 1.6hz, 1H), 7.78-7.74 (m, 2H), 7.63 (d, j=8.4 hz, 1H), 7.54-7.47 (m, 3H), 7.44-7.35 (m, 2H); the mass spectrum analysis determines the molecular ion mass as follows: 372.75 (calculated: 373.25); theoretical element content (%) C 22 H 13 OBr; c70.80, H3.51; measured element content (%): c70.73, H3.54.
(2) Synthesis of compound E:
potassium bis (trimethylsilyl) amide (KHMDS, 21.5mL,1M THF) was slowly added to a 250mL flask, 5-dimethyl-5, 10-dihydrodibenzostannylamine (2.7 g,8.6 mmol), 5-dioxo-dibenzothiophene (1.85 g,8.6 mmol) and dried tetrahydrofuran (40 mL) were added at room temperature. The mixture was then heated to 65 ℃ and stirred for 8 hours. After cooling to room temperature, the reaction was quenched with saturated aqueous ammonium chloride. The organic phase was extracted with dichloromethane (3X 30 mL). The obtained organic matterThe solution was dried over anhydrous sodium sulfate. Purification by column chromatography on silica gel (eluent dichloromethane), recrystallisation from dichloromethane and petroleum ether afforded compound E (white powder, 2.3g, 58% yield). Structural characterization data: 1 HNMR(400MHz,CDCl 3 delta) 7.80 (dd, j=7.8, 1.8hz, 2H), 7.66 (m, dd, j=8.2, 1.8hz, 2H), 7.39-7.32 (m, 6H), 7.20-7.14 (m, 3H), 7.11 (dd, j=7.8, 2.0hz, 1H), 6.93 (dd, j=8.0, 1.8hz, 2H), 0.55 (s, 6H); the mass spectrum analysis determines the molecular ion mass as follows: 465.26 (calculated: 465.18); theoretical element content (%) C 27 H 22 Sn: c69.71, H4.77; measured element content (%): c69.68, H4.75.
(3) Synthesis of compound F:
a solution of boron trichloride in methylene chloride (1M, 33.4 mL) was slowly added to a solution of compound E (3.1 g,6.7 mmol) in methylene chloride (200 mL) at-78deg.C. The reaction mixture was slowly warmed to room temperature and stirred for 3 hours. Excess boron trichloride and methylene chloride were removed in vacuo, then the residue was heated to 100deg.C and kept in vacuo for 3.5 hours to remove Me formed 2 SnCl 2 . Since the resulting compound F is sensitive to moisture, it can be used without further purification. Structural characterization data: 1 H NMR(400MHz,CDCl 3 delta) 7.85 (dd, j=7.8, 1.8hz, 2H), 7.61 (dd, j=7.8, 1.8hz, 2H), 7.39-7.32 (m, 6H), 7.27 (dd, j=7.8, 2.0hz, 2H), 7.16 (td, j=7.8, 1.8hz, 2H), 6.91 (dd, j=8.0, 1.8hz, 2H), mass spectrometry determines molecular ion masses of: 361.60 (calculated: 362.66); theoretical element content (%) C 25 H 16 BCl: c82.80, H4.45; measured element content (%): c82.71, H4.47.
(4) Synthetic route for dibenzofuranyl blue-light compound I-1 containing spiroborane structure:
tert-butyllithium (8.9 mL,14.2 mmol) was slowly added to a 250mL flask containing Compound C (2.65 g,7.1 mmol) and tert-butylbenzene (40 mL) at-78deg.C. The reaction mixture was then heated at room temperature for 2.5 hours. The temperature was lowered to 0deg.C and the mixture was slowly added to a solution of compound F (1.2 g,3.34 mmol) in t-butylbenzene (30 mL). The resulting mixture was then stirred at room temperature overnight. The solvent was removed in vacuo and methylene chloride (3X 30 mL) and water were added to the residue for extraction. The organic phase was dried over anhydrous sodium sulfate. After purification by silica gel column chromatography (eluent dichloromethane/petroleum ether volume ratio=1/8), dibenzofuranyl blue photochemical compound i-1 (2.7 g, yield 65%) containing a spiral borane structure was obtained. Structural characterization data: 1 H NMR(400MHz,CDCl 3 delta 8.09-8.03 (m, 3H), 7.96 (d, j=7.9 hz, 1H), 7.89 (dd, j=7.7, 1.6hz, 1H), 7.85 (dd, j=7.8, 1.8hz, 2H), 7.75 (dd, j=8.0, 1.6hz, 1H), 7.66-7.61 (m, 3H), 7.51-7.33 (m, 12H), 7.24 (dd, j=7.6, 1.8hz, 1H), 7.17-7.11 (m, 3H), 6.91 (dd, j=8.1, 1.8hz, 2H). The mass spectrum analysis determines the molecular ion mass as follows: 620.81 (calculated: 620.56). Theoretical element content (%) C 47 H 29 BO: c90.97, H4.71; measured element content (%): c90.86, H4.69. FIG. 1 shows the reaction of compound I-1 in toluene (concentration 10 -5 mol/L), the luminescence peak is 463nm, the blue light emission is realized, and the fluorescence quantum yield is 59%. FIG. 3 is a thermogravimetric and differential scanning calorimetric curve of a compound with a thermal decomposition temperature and a glass transition temperature of 365 and 140℃respectively, indicating good thermal stability of the material.
The device structure of the invention is ITO/HATCN (5 nm)/NPB (40 nm)/TCTA (5 nm)/I-1 (20 nm)/TPBi (30 nm)/LiF (1 nm)/Al (100 nm). Wherein ITO glass is used as a substrate, HATCN and NPB are used as hole transport layers, TCTA is used as an electron blocking layer, a compound I-1 is used as a light emitting layer, TPBi is used as an electron transport layer, liF is used as an electron injection layer, and Al is used as a cathode layer. And preparing a hole transport layer, an electron blocking layer, a luminescent layer, an electron transport layer, an electron injection layer and a cathode layer on the surface of the anode layer by vacuum evaporation in sequence to obtain the blue light OLED device.
Examples the results of the tests are shown in figures 5,7 and 9, which show that the electroluminescent spectrum of an organic electroluminescent device using dibenzofuranyl blue light compound I-1 with spiroborane as the second substituent as the light-emitting layer, the light-emitting peak at 466nm, and the device shows blue light emission. The device had a turn-on voltage of 3.3V, a maximum current efficiency of 12.5cd/A, a power efficiency of 11.9lm/W, and an external quantum efficiency of 2.7%.
[ example 2 ]
Synthetic route to bis (2, 4, 6-trimethylphenyl) borane-containing dibenzofuranyl blue-light compound I-2:
the only difference from example 1 is that compound F is replaced by chlorobis (2, 4, 6-trimethylphenyl) borane. Tert-butyllithium (8.9 mL,1.6M in n-hex,14.2 mmol) was slowly added to a flask of compound C (2.65 g,7.1 mmol) and tert-butylbenzene (40 mL) at-78deg.C. Then, the reaction mixture was stirred at room temperature for 2.5 hours. The temperature was reduced to 0deg.C and the mixture was added to a solution of chlorobutyl benzene (30 mL) in chlorobis (2, 4, 6-trimethylphenyl) borane (1.94 g,6.8 mmol). The resulting mixture was then stirred at room temperature overnight. The solvent was removed in vacuo, and methylene chloride (3X 30 mL) and water were added to the residue to extract. Anhydrous Na for organic phase 2 SO 4 Drying, filtering, and evaporating the solvent under reduced pressure. After purification by silica gel column chromatography (eluent dichloromethane/petroleum ether volume ratio=1/10), dibenzofuranyl blue compound i-2 of bis (2, 4, 6-trimethylphenyl) borane was obtained (2.8 g, yield 58%). Structural characterization data: 1 H NMR(400MHz,CDCl 3 8.09-8.06 (m, 2H), 8.03 (d, j=8.0 hz, 1H), 7.96 (d, j=8.0 hz, 1H), 7.88 (dd, j=7.8, 1.8hz, 1H), 7.75 (dd, j=8.0, 1.8hz, 1H), 7.72 (d, j=8.0 hz, 1H), 6.52-6.36 (m, 6H), 6.83 (s, 4H), 2.26 (s, 6H), 2.09 (s, 12H). Mass spectrometry determines molecular ion masses of: 542.81 (calculated: 542.53). Theoretical element content (%) C 40 H 35 BO: c88.56, H6.50; measured element content (%): c88.67, H6.56. FIG. 2 shows the toluene-soluble form of the compound I-2In the liquid (concentration is 10) -5 mol/L), the luminescence peak is at 446nm, belonging to blue light emission, and the fluorescence quantum yield is 41%. FIG. 4 is a thermogravimetric and differential scanning calorimetry curve of compound I-2 with a thermal decomposition temperature and a glass transition temperature of 370 and 147℃respectively, indicating that the material has good thermal stability.
The device structure of the invention is ITO/HATCN (5 nm)/NPB (40 nm)/TCTA (5 nm)/I-2 (20 nm)/TPBi (30 nm)/LiF (1 nm)/Al (100 nm). Wherein ITO glass is used as a substrate, HATCN and NPB are used as hole transport layers, TCTA is used as an electron blocking layer, a compound I-2 is used as a light emitting layer, TPBi is used as an electron transport layer, liF is used as an electron injection layer, and Al is used as a cathode layer. And preparing a hole transport layer, an electron blocking layer, a luminescent layer, an electron transport layer, an electron injection layer and a cathode layer on the surface of the anode layer by vacuum evaporation in sequence to obtain the blue light OLED device.
Examples the results of the tests are shown in fig. 6,8 and 10, for an organic electroluminescent device with dibenzofuranyl blue light compound I-2 as the light emitting layer, with bis (2, 4, 6-trimethylphenyl) borane as the second substituent, the emission peak of the electroluminescent spectrum is at 444nm, showing blue light emission. The device had a turn-on voltage of 3.3V, a maximum current efficiency of 11.80cd/A, a power efficiency of 11.6lm/W, and an external quantum efficiency of 2.6%.
The foregoing is merely a preferred embodiment of the present invention and it should be noted that modifications and adaptations to those skilled in the art may be made without departing from the principles of the present invention, which are intended to be comprehended within the scope of the present invention.
Claims (10)
1. A dibenzofuran-based blue light material characterized by having a structure represented by formula I:
in the formula I, R is* Representing the position of the radical attachment.
2. The method for preparing the blue light material according to claim 1, comprising the steps of:
(1) Mixing a compound with a structure shown in a formula A, a compound with a structure shown in a formula B, an alkaline reagent, a palladium catalyst, a polar organic solvent M and an alcohol solvent, and refluxing to obtain a compound with a structure shown in a formula C;
(2) Mixing a compound with a structure shown in a formula C, tert-butylbenzene, a tert-butyllithium initiator and a compound with a structure shown in a formula F or a formula G, and performing nucleophilic substitution reaction to obtain a blue light material with a structure shown in a formula I;
the structural formula of the compound shown in the formula A, B, C, F, G is as follows:
3. the method of claim 2, wherein in step (1), the alkaline agent is Na 2 CO 3 、K 2 CO 3 Or Cs 2 CO 3 Any one of them; the palladium catalyst is Pd (PPh) 3 ) 4 、PdCl 2 Or Pd 2 (dba) 3 Any one of them; the polar organic solvent M is any one of tetrahydrofuran, toluene and N, N-dimethylformamide; the alcohol solvent is low-carbon alcohol with the carbon number less than 4; the volume ratio of the polar organic solvent M to the alcohol solvent is 20-10:1.
4. The method for preparing a blue light material according to claim 2, wherein in the step (2), the ratio of the amount of the compound having the structure represented by formula C, the compound having the structure represented by formula F or formula G, and the t-butyllithium initiator is 1 to 1.5mol:1 to 5mol:1.5 to 10mol, the reaction temperature of nucleophilic substitution reaction is-78 to room temperature, and the reaction time is 4 to 8 hours.
5. The method for preparing a blue light material according to claim 2, wherein the method for preparing the compound having the structure represented by formula F is as follows:
(1) Mixing a compound with a structure shown in a formula D, 5-dioxo-dibenzothiophene, a strong base reagent and a polar organic solvent, and carrying out nucleophilic substitution reaction to obtain a compound with a structure shown in a formula E;
(2) Mixing a compound with a structure shown in a formula E, boron trichloride and a chlorinated alkane solvent, and reacting to obtain a compound with a structure shown in a formula F;
the structural formula of the compound shown in formula D, E is as follows:
6. the method according to claim 5, wherein in the step (1), the polar solvent is tetrahydrofuran, the strong alkali reagent is bis (trimethylsilyl) aminopotassium, and the ratio of the strong alkali reagent, the structural compound shown as D and the solvent is 3-10 mmol:1-2 mmol:20-100 mL.
7. The method of producing a blue light material according to claim 5, wherein in the step (1), the nucleophilic substitution reaction is carried out at a temperature of 60 to 70℃for a reaction time of 6 to 10 hours.
8. The method of claim 5, wherein in step (2), the chlorinated alkane solvent is dichloromethane, chloroform, carbon tetrachloride, dichloroethane, preferably dichloromethane; the dosage ratio of the compound with the structure shown in the formula E to the boron trichloride to the chlorinated alkane solvent is 4-6 mol: 0.5-1 mL: 40-80 mL.
9. The method of preparing blue light material according to claim 5, wherein in the step (2), the initial temperature of the reaction is-78 ℃, and then the reaction mixture is slowly heated to room temperature for 3 to 5 hours.
10. The dibenzofuran-based blue light material as claimed in claim 1, which is used as a light-emitting layer material for an organic electroluminescent device and a preparation process thereof.
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