CN116120526A - 一种bn化合物及bn化合物的制备方法 - Google Patents
一种bn化合物及bn化合物的制备方法 Download PDFInfo
- Publication number
- CN116120526A CN116120526A CN202211713448.9A CN202211713448A CN116120526A CN 116120526 A CN116120526 A CN 116120526A CN 202211713448 A CN202211713448 A CN 202211713448A CN 116120526 A CN116120526 A CN 116120526A
- Authority
- CN
- China
- Prior art keywords
- groups
- carbon atoms
- compound
- aryl
- heteroaryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 44
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 35
- 125000003118 aryl group Chemical group 0.000 claims abstract description 24
- 125000001424 substituent group Chemical group 0.000 claims abstract description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 8
- 125000004404 heteroalkyl group Chemical group 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 8
- 239000003446 ligand Substances 0.000 claims description 7
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 229910052711 selenium Inorganic materials 0.000 claims description 3
- 239000011669 selenium Substances 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 2
- 230000009471 action Effects 0.000 claims description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical group OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 2
- 239000004327 boric acid Substances 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 claims description 2
- LYRCQNDYYRPFMF-UHFFFAOYSA-N trimethyltin Chemical compound C[Sn](C)C LYRCQNDYYRPFMF-UHFFFAOYSA-N 0.000 claims description 2
- DLQYXUGCCKQSRJ-UHFFFAOYSA-N tris(furan-2-yl)phosphane Chemical compound C1=COC(P(C=2OC=CC=2)C=2OC=CC=2)=C1 DLQYXUGCCKQSRJ-UHFFFAOYSA-N 0.000 claims description 2
- IBXMKLPFLZYRQZ-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 IBXMKLPFLZYRQZ-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 11
- 230000005540 biological transmission Effects 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 239000000463 material Substances 0.000 description 12
- 230000005669 field effect Effects 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000004065 semiconductor Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- -1 2-ethylhexyl Chemical group 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- TZHYBRCGYCPGBQ-UHFFFAOYSA-N [B].[N] Chemical compound [B].[N] TZHYBRCGYCPGBQ-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229920005603 alternating copolymer Polymers 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000002484 cyclic voltammetry Methods 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 3
- 238000010200 validation analysis Methods 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 238000007336 electrophilic substitution reaction Methods 0.000 description 2
- 238000004896 high resolution mass spectrometry Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical group C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000015654 memory Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/124—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one nitrogen atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/12—Copolymers
- C08G2261/124—Copolymers alternating
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
- C08G2261/3221—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more nitrogen atoms as the only heteroatom, e.g. pyrrole, pyridine or triazole
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
- C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
- C08G2261/3229—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing nitrogen and sulfur as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
- C08G2261/3241—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
- C08G2261/3246—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing nitrogen and sulfur as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/40—Polymerisation processes
- C08G2261/41—Organometallic coupling reactions
- C08G2261/414—Stille reactions
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/90—Applications
- C08G2261/92—TFT applications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Thin Film Transistor (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Abstract
本发明公开提供一种BN化合物及BN化合物的制备方法。其结构通式如式I所示，R1和R2均独立的代表：碳原子总数为1‑50的烷基、碳原子总数为1‑50的烷氧基、碳原子总数为7‑50的芳烷基和碳原子总数为5‑50的杂烷基；R均独立的代表：选自芳基、杂芳基、含有取代基的芳基和含有取代基的杂芳基，且基团中的键合方式选自单键、双键和三键中的至少一种碳原子总数为1‑50的烷基、碳原子总数为1‑50的烷氧基、碳原子总数为7‑50的芳烷基和碳原子总数为5‑50的杂烷基；Ar’均独立的代表：选自单环芳基、双环芳基和三环芳基,且基团中的键合方式选自单键、双键和三键。本发明的聚合物具有优良的载流子传输性能以及溶解性能，可应用光电领域如有机场效应晶体管中。
Description
技术领域
本发明涉及BN化合物技术领域，具体为一种BN化合物及BN化合物的制备方法。
背景技术
有机半导体器件主要包括(OLEDs)、有机场效应晶体管(OFETs)及有机太阳能电池(OPVs)等。目前，有机发光二极管已经获得应用，如显示、照明等，而有机场效应晶体管和有机太阳能电池正在向产业化迈进。有机场效应晶体管具有制备工艺简单、成本低、重量轻和柔韧性好等特点，可用于智能卡、电子商务、电子纸、存储器、传感器和有源矩阵显示器等领域，是有机光电子器件和电路的关键元器件。相比于无机太阳能电池，有机太阳能电池具有耗材少、重量轻、易加工、低成本、可制备成柔性器件等特点，目前已经成为世界各国尤为关注的高新技术之一。由此可见，有机太阳能电池和场效应晶体管均具有可商业化应用的前景。目前，该类材料发展重心是有机材料分子的设计与结构优化。
利用电子给体单元与电子受体单元组成的给-受体聚合物是人们的研究热点，最有可能实现商业化。经过二十几年的发展，通过新材料的设计、制备工艺的改进及新器件结构的设计，这类给-受体聚合物材料已经在场效应晶体管及太阳能电池器件中取得了优良的性能。硼原子和氮原子处于碳原子的相邻位置。因此，硼氮配位键(B←N)是碳碳单键(C-C)的等电子体。最近，人们发现硼氮配位键的引入可大幅度降低有机分子材料的LUMO/HOMO能级，因而发展出一类新型的n型有机分子材料，为有机高分子半导体领域开拓出新的研究方向，成为目前的一个研究热点。但是硼氮配位键的引入会使得分子稠环化，虽然可拓展分子的共轭骨架，但是大幅度降低了分子的溶解性，不利于半导体器件的溶液法(低成本)制备。
因此，将硼氮配位键与烷基链结合，获得一端稠环，一端为烷基链的半稠环化结构，有望获得高性能、低成本的新型有机半导体材料。
发明内容
本发明提供了一种BN化合物及BN化合物的制备方法，其具体为含硼氮键半稠环结构的共轭小分子单体及基于该分子的交替共聚物的制备方法与应用。
为实现以上目的，本发明通过以下技术方案予以实现：
本发明提供的基于含硼氮键半稠环结构单元的吡咯并吡咯二酮交替共聚物，其结构通式如式I所示，
作为本发明一种优选的方案，所述式I中，R1和R2均选自碳原子总数为1-50的烷基、碳原子总数为1-50的烷氧基、碳原子总数为7-50的芳烷基和碳原子总数为5-50的杂烷基中的至少一种；
作为本发明一种优选的方案，所述式I中，R选自芳基、杂芳基、含有取代基的芳基和含有取代基的杂芳基中的至少一种，且基团中的键合方式选自单键、双键和三键中的至少一种碳原子总数为1-50的烷基、碳原子总数为1-50的烷氧基、碳原子总数为7-50的芳烷基和碳原子总数为5-50的杂烷基中的至少一种；所述含有取代基的芳基，含有取代基的杂芳基中，取代基的个数为1-4的整数。
作为本发明一种优选的方案，所述R优选如下取代或未取代的基团：
作为本发明一种优选的方案，所述式I中，Ar均选自含氮原子的杂芳基、含氮原子的且含有取代基的杂芳基中的至少一种，且基团中的键合方式选自单键、双键和三键中的至少一种；所述含有取代基的杂芳基中，取代基的个数为1-4的整数。
作为本发明一种优选的方案，所述Ar优选如下取代或未取代的基团：
所述含有取代基的杂芳基中，取代基的个数为1-4的整数。
作为本发明一种优选的方案，所述Ar’中，所述芳基均选自单环芳基、双环芳基和三环芳基中的至少一种，优选噻吩基、二联噻吩基和并噻吩基中的至少一种；所述杂芳基均选自单环杂芳基、双环杂芳基和三环杂芳基中的至少一种，杂原子选自氧、硫和硒中的至少一种；所述Ar优选如下取代或未取代的基团：
上述基团中，X均选自氯原子，氟原子，氢、碳原子总数为1-50的烷基和碳原子总数为1-50的烷氧基中的至少一种；
本发明提供的制备所述式Ⅰ所示化合物的方法，包括下述步骤：
在惰性气氛和催化剂存在下，将所述式Ⅱ所示化合物与所述式Ⅲ所示化合物在催化剂的作用下按一定比例在有机溶剂中进行碳碳偶联反应，得到式Ⅰ所示化合物；
作为本发明一种优选的方案，所述式II中，R、R1、R2、Ar的定义与前述定义相同；
作为本发明一种优选的方案，所述式III中，Ar’的定义与前述定义相同；Y为三烷基锡基或硼酸酯基。
作为本发明一种优选的方案，所述Y中，所述硼酸酯基为1,3,2-二氧杂硼烷-2-基或4,4,5,5-四甲基-1,2,3-二氧杂环戊硼烷-2-基；所述三烷基锡基为三甲基锡或三丁基锡。
作为本发明一种优选的方案，上述制备方法中，所述惰性气氛中的气体具体可为氮气。
作为本发明一种优选的方案，所述催化剂由钯催化剂和膦配体组成，其中，所述钯催化剂选自四(三苯基膦)钯、三(三对甲基苯基膦)钯、三(二亚苄基丙酮)二钯和双(1,4-联苯膦)丁基二氯化钯中的至少一种，具体可为三(二亚苄基丙酮)二钯；所述膦配体选自三苯基膦、邻三甲苯基膦、三(2-呋喃基)膦和2-(二叔丁基磷)联苯中的至少一种，具体可为邻三甲苯基膦；
作为本发明一种优选的方案，所述式Ⅱ所示化合物、所述式III所示化合物、所述钯催化剂和所述膦配体的摩尔比为1：(1-50)：(0.04-1.20)：(0.32-9.6)。
作为本发明一种优选的方案，所述碳碳偶联反应的反应温度为90-110℃，优选100℃，反应时间为24-96h，优选为72h。
作为本发明一种优选的方案，所述有机溶剂选自甲苯、N,N-二甲基甲酰胺和氯苯中的至少一种。
上述制备方法中，还包括对所述反应后所得反应物和甲醇混合，过滤所得固体，并将所述固体依次用甲醇、正己烷和丙酮清洗，最后，用氯仿提取目标产物，并将溶有目标产物的氯仿和甲醇混合，抽滤所得固体，即为式Ⅰ所示聚合物。
作为本发明一种优选的方案，本发明提供的制备式Ⅱ所述化合物的方法，反应路线如图1所示，包括如下步骤：
S1、将图1中化合物1与2混匀，以四氢呋喃作为反应液，碳酸钾为碱，进行亲电取代反应，反应完毕后，得到图1所示化合物3；其中将1与2的摩尔比为1:0.3-1.2，优选1:0.75，所述亲电取代反应步骤中，温度为60-80℃，时间为24-72小时；所述1与所述式Ⅱ中Ar定义相同，所述2与所述式II中R1和R2定义相同，所述3与所述式II中Ar，R1和R2定义相同；
S2、将步骤S1所得的3与4按一定摩尔比在惰性气体氛围中进行反应，以甲苯为溶剂，得到5；所述3与4的摩尔比为1:2-10，优选1:2，所述惰性气氛为氮气或氩气气氛中至少一种，所述反应中，溶剂为甲苯、四氢呋喃中的至少一种，温度为60-100℃，时间为12-20小时；所述3与所述式Ⅱ中Ar，R1和R2定义相同，所述4与所述式II中R定义相同，所述4与所示式Ar，R，R1和R2定义相同。
与现有技术相比，本发明的有益效果是：
本发明的目的在于提供所述式I的化合物在制备柔性和刚性衬底有机场效应晶体管中的应用；所述式I为共聚物材料，具有优良的载流子传输性能以及溶解性能，可应用光电领域如有机场效应晶体管中，同时本发明的有机分子材料，是一类含有π-电子结构，具有特殊光、电、磁性质的有机光电子材料，亦称有机半导体材料。相比于无机材料，本发明的有机半导体材料具有易于调控，且制备方法简单，成本低廉，可以大面积制备有机柔性电路等特点。
附图说明
图1为本发明的所述式Ⅱ所述化合物的反应路线；
图2为本发明的实施例1所述式Ⅱ所示化合物的合成的化学反应流程图；
图3为本发明的实施例2所述式Ⅰ所述化合物的化学反应流程图；
图4为本发明实施例2制备的化合物在薄膜状态下的紫外-可见吸收光谱；
图5为本发明实施例2制备的化合物的循环伏安曲线；
图6为本发明实施例2制备的化合物的转移曲线和输出曲线。
具体实施方式
下面结合具体实施例对本发明作进一步阐述，但本发明并不限于以下实施例。所述方法如无特别说明均为常规方法。所述原材料如无特别说明均能从公开商业途径而得。
在描述本发明的实施方案时，为了清楚起见，使用了特定的术语。然而本发明无意局限于所选择的特定术语。应了解每个特定元件包括类似的方法运行以实现类似目的的所有技术等同物。
本发明的实践可采用本领域技术内的有机化学的常规技术。在以下实施例中，努力确保所用数字(包括量、温度、反应时间等)的准确性，但应考虑一些实验误差和偏差。在以下实施例中所用的温度以℃表示，压力为大气压或接近大气压。所有溶剂都是以HPLC级获得，并且所有反应在氮气惰性气氛下进行。除非另外指出，否则所有试剂都是商业获得的。
定义和命名：
除非另外指出，否则本发明不局限于特定的原料、试剂或者反应条件，而是可以变化。本文所用的术语“烷基”指支化的或未支化的饱和烷基，其通常但并非必需地含有1至50个碳原子，如甲基、乙基、正丙基、异丙基、正丁基、正己基、2-乙基己基、十二烷基等。
“芳基”具有其通常含义。本文所用的术语“杂芳基”指含有一个或更多个“杂原子”(如氮、氧、硫、硒)的芳环、
如“取代的芳基”、“取代的杂亚芳基”等中的术语“取代的”指结合至碳或杂原子的至少一个氢原子被一个或更多个非氢取代的部分，这样的取代基可包括但不限于烷基或芳基以及烷基硫代、烷氧基、烷基羰基、酰氧基、腈基等的官能团。
实施例1：式Ⅱ所示化合物的合成，其中Ar为吡啶，R1和R2为十八烷基，R为苯基。
化学反应流程图如图2所示，具体反应步骤条件如下：
步骤1：将2,5-2溴代二吡啶吡咯并吡咯二酮2.23mmol溶于120mL四氢呋喃中，加入叠氮化钠19-(2溴乙基)三十七烷0.3～1.0mmol，60℃反应12h，停止反应。用旋转蒸发仪除去溶剂，向所得物中加入水100mL稀释反应体系，用200mL二氯甲烷萃取3次，合并有机相，无水硫酸钠干燥，过滤，将所得滤液旋干，用硅胶柱分离得到产物(0.446mmol，产率：20％)。结构确证数据如下：1H NMR(400MHz,氘代氯仿)δ8.98(d,J＝8.4Hz,1H),8.92(d,J＝8.6Hz,1H),8.73(dd,J＝13.2,2.3Hz,2H),8.59(s,1H),8.06-7.98(m,2H),4.37–4.30(m,2H),1.60(d,J＝5.2Hz,1H),0.88(t,J＝6.8Hz,6H)；高分辨质谱分析:计算值为C55H86Br2N4O2:994.5092；实际值:994.5099。由上可知，该产物结构正确。
步骤2：将步骤1所得产物0.1mmol溶于10mL甲苯中，氮气保护下将三苯基硼0.1～10mmol加入反应体系中，100℃反应6h。冷却至室温，向反应体系中加入250mL无水乙醇，抽滤，用10mL乙醇洗3次，用硅胶柱分离得到目标产物(0.021mmol，产率：21％)。结构确证数据如下：1H NMR(600MHz,氘代氯仿)δ9.05(s,1H),8.70(d,J＝2.3Hz,1H),8.57(d,J＝1.9Hz,1H),8.43(d,J＝8.5Hz,1H),8.35-8.32(m,1H),7.91(dd,J＝8.6,2.3Hz,1H),7.36-7.33(m,4H),7.29(q,J＝6.2,5.5Hz,6H),4.31(t,J＝8.1Hz,2H),1.25(d,J＝3.3Hz,68H),0.87(t,J＝6.9Hz,6H)；高分辨质谱分析:计算值为C67H95BBr2N4O2:1158.5889；实际值:1158.5891。由上可知，该产物结构正确。
实施例2：式Ⅰ所示交替共聚物的合成，其中R1和R2为十八烷基，R为苯基，Area为吡啶，定义聚合物为PpyDPPBN。
化学反应流程图如图3所示，以PpyDPPBN为例，具体反应步骤条件如下：
将实施例1中步骤2所得化合物0.086mmol和(3，4-二氟噻吩)二(三甲基锡)0.087mmol溶于无水甲苯中，吹氮气20min，加入催化剂三(二亚苄基丙酮)二钯0.0017mmol和配体邻三甲苯基膦0.0069mmol，继续鼓氮气20min，在氮气保护下，100℃反应72h。冷却至室温，将反应体系倒入100mL甲醇中，析出固体，过滤。将所得固体通过索氏提取器用甲醇、正己烷和丙酮依次除去催化剂、未反应完原料和低聚物，最后用氯仿提出目标产物。再将溶有目标产物的氯仿溶液倒入200mL甲醇中，析出固体，抽滤，得最终产物PpyDPPBN。结构确证数据如下：1H NMR(500MHz,1,1,2,2-四氯乙烷，100℃)δ9.19-8.14(m,br),7.57-6.90(m,br),4.44(m,br),1.74-1.30(m,br),0.96-0.94(m,br)；元素分析:计算值为C71H95BF2N4O2S:C,76.32；H,8.57；N,5.01；实际值:C,76.03；H,8.60；N,4.97。
由上可知，上述产物结构正确，为式I所示化合物。
实施例3：本发明聚合物的可加工型和利用吸收光谱的光学带隙的测量
将实施例2中制得的聚合物溶于各种有机溶剂，所述有机溶剂包括氯仿、邻二氯苯、1,1,2,2-四氯乙烷，以及其他溶剂，如甲醇、甲苯、四氢呋喃。发现化合物在氯化溶剂中具有良好地溶解度。通过将化合物的三氯甲烷溶液旋涂至石英片上而制得高品质薄膜。
实施例2制备的聚合物PpyDPPBN在薄膜状态下测得的吸收光谱见于图4。薄膜最大吸收波长在651左右。根据光学带隙的经验公式(Eg＝1240/λ，其中Eg为光学带隙；λ为吸收光谱在长波方向的起点)，得到聚合物的光学带隙为1.56eV左右。
实施例4：利用电化学循环伏安法测量最低未占用分子轨道(LUMO)
利用电化学工作站对实施例2的聚合物的电化学特性进行了测试，以二茂铁为标准，六氟磷酸四丁基胺为电解质，电解液为乙腈。采用标准的三电极系统进行测试，以铂丝作为对电极、Ag/Ag+作为参比电极。测得循环伏安曲线如图5所示，测得化合物的LUMO能级为-3.86eV。
实施例5：制备聚合物的柔性场效应器件
根据文献(Chem.Rev.2012,112,2208-2267)的方法，在聚对苯二甲酸乙二醇酯上(PET)，蒸镀镀金，宽度1440微米，长度为50微米，然后将在实施例2中制得聚合物(6mg)溶解于1mL三氯甲烷中，在以上薄片上旋涂成膜，通过真空退火100℃后，再在上面旋涂聚甲基丙烯酸甲酯(重均分子量＝996kDa)，厚度为900纳米，再在其上蒸镀金属铝，然后，测试其场效应性质。
实施例6：
基于实施例2的化合物，按照实施例5的程序制造并表征场效应器件。其输出曲线和转移曲线如图6所示，其电子迁移率达到0.03cm2 V-1s-1。
最后应说明的是：以上所述仅为本发明的实施例而已，并不局限于仅仅所述的实施方案和实施例。对于本领域的普通技术人员来说，其依然可以对前述各实施例所记载的技术方案进行修改，或者对其中部分技术特征进行等同替换。
Claims (10)
1.一种BN化合物，其特征在于，所述化合物结构为：
其中，所述式I中R1和R2均选自碳原子总数为1-50的烷基、碳原子总数为1-50的烷氧基、碳原子总数为7-50的芳烷基和碳原子总数为5-50的杂烷基中的至少一种，所述式I中R选自芳基、杂芳基、含有取代基的芳基和含有取代基的杂芳基中的至少一种，且基团中的键合方式选自单键、双键和三键中的至少一种碳原子总数为1-50的烷基、碳原子总数为1-50的烷氧基、碳原子总数为7-50的芳烷基和碳原子总数为5-50的杂烷基中的至少一种。
2.根据权利要求1所述的BN化合物，其特征在于：所述含有取代基的芳基，含有取代基的杂芳基中，取代基的个数为1-4的整数。
3.根据权利要求2所述的BN化合物，其特征在于：所述R选取如下取代或未取代的基团的一种：
4.根据权利要求1所述的BN化合物，其特征在于：所述式I中Ar均选自含氮原子的杂芳基、含氮原子的且含有取代基的杂芳基中的至少一种，且基团中的键合方式选自单键、双键和三键中的至少一种，所述含氮原子的且含有取代基的杂芳基中取代基的个数为1-4的整数。
5.根据权利要求4所述的BN化合物，其特征在于：所述Ar选取如下取代或未取代的基团的一种：
6.根据权利要求5所述的BN化合物，其特征在于：所述Ar’中，所述芳基均选自单环芳基、双环芳基和三环芳基中的至少一种。
7.根据权利要求4所述的BN化合物，其特征在于：所述Ar中的杂芳基均选自单环杂芳基、双环杂芳基和三环杂芳基中的至少一种，杂原子选自氧、硫和硒中的至少一种。
8.一种BN化合物的制备方法，包含下述步骤：
在惰性气氛和催化剂存在下，将所述式Ⅱ所示化合物与所述式Ⅲ所示化合物在催化剂的作用下按一定比例在有机溶剂中进行碳碳偶联反应，得到式Ⅰ所示化合物；
其中R1和R2均选自碳原子总数为1-50的烷基、碳原子总数为1-50的烷氧基、碳原子总数为7-50的芳烷基和碳原子总数为5-50的杂烷基中的至少一种，R选自芳基、杂芳基、含有取代基的芳基和含有取代基的杂芳基中的至少一种，且基团中的键合方式选自单键、双键和三键中的至少一种碳原子总数为1-50的烷基、碳原子总数为1-50的烷氧基、碳原子总数为7-50的芳烷基和碳原子总数为5-50的杂烷基中的至少一种，Ar’中芳基均选自单环芳基、双环芳基和三环芳基中的至少一种，Y为三烷基锡基或硼酸酯基。
9.根据权利要求8所述的一种BN化合物的制备方法，其特征在于：所述Y中硼酸酯基为1,3,2-二氧杂硼烷-2-基或4,4,5,5-四甲基-1,2,3-二氧杂环戊硼烷-2-基；所述三烷基锡基为三甲基锡或三丁基锡。
10.根据权利要求8所述的一种BN化合物的制备方法，其特征在于：所述惰性气氛中的气体具体可为氮气，所述催化剂由钯催化剂和膦配体组成，其中，所述钯催化剂选自四(三苯基膦)钯、三(三对甲基苯基膦)钯、三(二亚苄基丙酮)二钯和双(1,4-联苯膦)丁基二氯化钯中的至少一种，具体可为三(二亚苄基丙酮)二钯；所述膦配体选自三苯基膦、邻三甲苯基膦、三(2-呋喃基)膦和2-(二叔丁基磷)联苯中的至少一种，具体可为邻三甲苯基膦，所述式Ⅱ所示化合物、所述式III所示化合物、所述钯催化剂和所述膦配体的摩尔比为1：(1-50)：(0.04-1.20)：(0.32-9.6)，所述碳碳偶联反应的反应温度为90-110℃，优选100℃，反应时间为24-96h，所述有机溶剂选自甲苯、N,N-二甲基甲酰胺和氯苯中的至少一种。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211713448.9A CN116120526A (zh) | 2022-12-27 | 2022-12-27 | 一种bn化合物及bn化合物的制备方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211713448.9A CN116120526A (zh) | 2022-12-27 | 2022-12-27 | 一种bn化合物及bn化合物的制备方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116120526A true CN116120526A (zh) | 2023-05-16 |
Family
ID=86305805
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211713448.9A Withdrawn CN116120526A (zh) | 2022-12-27 | 2022-12-27 | 一种bn化合物及bn化合物的制备方法 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116120526A (zh) |
-
2022
- 2022-12-27 CN CN202211713448.9A patent/CN116120526A/zh not_active Withdrawn
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101601362B1 (ko) | 분지형 알킬 쇄를 갖는 화합물, 그 제조 방법, 및 광전 소자에서의 그의 용도 | |
| CN108546267B (zh) | 一种端基含环烷基链的有机共轭小分子材料及其制备方法与在太阳能电池中的应用 | |
| JP5425338B2 (ja) | アントラセンとピアセレノール類とを含有する共重合体、その製造方法及びその応用 | |
| JP2013523931A (ja) | 縮合環系ジチオフェンコポリマー | |
| Zhang et al. | Synthesis of star-shaped small molecules carrying peripheral 1, 8-naphthalimide functional groups and their applications in organic solar cells | |
| CN104672434A (zh) | 一种有机半导体材料及其制备方法与应用 | |
| WO2011047624A1 (zh) | 硫杂环稠合的萘四羧酸二酰亚胺衍生物、制法和应用 | |
| CN108774253B (zh) | 基于一种硼氮杂环的小分子有机太阳能电池材料及其制备方法 | |
| CN111533886A (zh) | 一类含基于喹喔啉并苯并三唑的稠环单元的给体-受体型聚合物及其制备方法与应用 | |
| Li et al. | Synthesis and photovoltaic properties of new conjugated polymers based on two angular-shaped naphthodifuran isomers and isoindigo | |
| CN110041508B (zh) | 一种星型共轭结构聚合物及其制备方法和应用 | |
| WO2013077615A1 (ko) | 팔라듐계 촉매를 사용한 직접적 ch 아릴화 방법 | |
| CN111454435B (zh) | 一类基于菲并咪唑单元的电致发光聚合物及其制备方法与应用 | |
| KR101595919B1 (ko) | 전도성 유기 반도체 화합물 및 이를 포함하는 유기태양전지 | |
| CN114621251B (zh) | 基于喹喔啉衍生物的稠环单元、含该单元的小分子、聚合物及制备方法与应用 | |
| Bathula et al. | Synthesis, characterization and optoelectronic properties of Benzodithiophene based copolymers for application in solar cells | |
| CN114349771B (zh) | 一种六苯并蔻基非富勒烯受体材料及其制备和应用 | |
| CN116120526A (zh) | 一种bn化合物及bn化合物的制备方法 | |
| CN107304218B (zh) | 一种邻位桥联苝二酰亚胺二聚体及其制备方法和在有机光伏器件中的应用 | |
| CN103965210A (zh) | 二噻并[2,3-d:2′,3′-d′]萘并[1,2-b:3,4-b′]二噻吩衍生物及共轭聚合物的制备方法及应用 | |
| CN109942798B (zh) | 末端硅氧烷基燕尾侧链取代吡咯并吡咯二酮基聚合物及其制备方法与应用 | |
| KR20150102559A (ko) | 테트라플루오로페닐렌 작용기를 갖는 고분자 및 이를 이용한 에너지 변환 소자 | |
| CN109354674B (zh) | 半氟烷基燕尾侧链取代萘二酰亚胺基共聚物、制备方法及其应用 | |
| KR20140114712A (ko) | 유기 반도체 화합물 및 제조방법과 이를 포함하는 유기전자소자 | |
| CN109776767B (zh) | 一种含二氟萘并噻吩二酮吸电子单元的共轭聚合物及其合成方法与应用 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WW01 | Invention patent application withdrawn after publication | ||
| WW01 | Invention patent application withdrawn after publication |
Application publication date: 20230516 |