CN103619855B - 用于有机半导体器件的二酮基吡咯并吡咯低聚物 - Google Patents
用于有机半导体器件的二酮基吡咯并吡咯低聚物 Download PDFInfo
- Publication number
- CN103619855B CN103619855B CN201280030124.3A CN201280030124A CN103619855B CN 103619855 B CN103619855 B CN 103619855B CN 201280030124 A CN201280030124 A CN 201280030124A CN 103619855 B CN103619855 B CN 103619855B
- Authority
- CN
- China
- Prior art keywords
- alkyl
- compound
- formula
- independently
- group
- 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.)
- Active
Links
- 239000004065 semiconductor Substances 0.000 title claims abstract description 44
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 230000005669 field effect Effects 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 112
- 239000001257 hydrogen Substances 0.000 claims description 76
- 229910052739 hydrogen Inorganic materials 0.000 claims description 76
- 229910052736 halogen Inorganic materials 0.000 claims description 61
- 150000002367 halogens Chemical class 0.000 claims description 60
- 150000002431 hydrogen Chemical class 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
- 229920000642 polymer Polymers 0.000 claims description 31
- 239000002904 solvent Substances 0.000 claims description 24
- 150000005690 diesters Chemical class 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 9
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 229910015444 B(OH)3 Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- 150000007514 bases Chemical class 0.000 claims 1
- 238000013086 organic photovoltaic Methods 0.000 abstract description 7
- -1 polysiloxanes Polymers 0.000 description 95
- 239000002585 base Substances 0.000 description 72
- 239000010410 layer Substances 0.000 description 59
- 239000000463 material Substances 0.000 description 42
- 125000004093 cyano group Chemical group *C#N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 32
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 27
- 239000000758 substrate Substances 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 229910052760 oxygen Inorganic materials 0.000 description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 19
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 15
- 239000001301 oxygen Substances 0.000 description 15
- 238000006467 substitution reaction Methods 0.000 description 15
- 229960005137 succinic acid Drugs 0.000 description 15
- 125000003342 alkenyl group Chemical group 0.000 description 14
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 13
- 229910003472 fullerene Inorganic materials 0.000 description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 12
- 125000001072 heteroaryl group Chemical group 0.000 description 12
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 0 CCCCCCCCC(CCCCCC)C*(C(C(C(*1CC(CCCCCC)CCCCCCCC)=O)C2=C1c1ccc[o]1)c1ccc(-c3cc(cc4[n]c(-c5ccc[o]5)cc4c4)c4[n]3)[o]1)C2=O Chemical compound CCCCCCCCC(CCCCCC)C*(C(C(C(*1CC(CCCCCC)CCCCCCCC)=O)C2=C1c1ccc[o]1)c1ccc(-c3cc(cc4[n]c(-c5ccc[o]5)cc4c4)c4[n]3)[o]1)C2=O 0.000 description 11
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 11
- 125000001931 aliphatic group Chemical group 0.000 description 11
- 125000003545 alkoxy group Chemical group 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- 229910052708 sodium Inorganic materials 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 10
- 125000000753 cycloalkyl group Chemical group 0.000 description 10
- 239000010408 film Substances 0.000 description 10
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 10
- 238000007639 printing Methods 0.000 description 10
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 9
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 9
- 238000000151 deposition Methods 0.000 description 9
- 230000008021 deposition Effects 0.000 description 9
- 229910052740 iodine Inorganic materials 0.000 description 9
- 239000011591 potassium Substances 0.000 description 9
- 229910052710 silicon Inorganic materials 0.000 description 9
- 239000010703 silicon Substances 0.000 description 9
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 9
- 230000007704 transition Effects 0.000 description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 9
- 229920002554 vinyl polymer Polymers 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 229910052744 lithium Inorganic materials 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 229910052700 potassium Inorganic materials 0.000 description 8
- 238000004528 spin coating Methods 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
- 239000005864 Sulphur Chemical group 0.000 description 7
- MCEWYIDBDVPMES-UHFFFAOYSA-N [60]pcbm Chemical compound C123C(C4=C5C6=C7C8=C9C%10=C%11C%12=C%13C%14=C%15C%16=C%17C%18=C(C=%19C=%20C%18=C%18C%16=C%13C%13=C%11C9=C9C7=C(C=%20C9=C%13%18)C(C7=%19)=C96)C6=C%11C%17=C%15C%13=C%15C%14=C%12C%12=C%10C%10=C85)=C9C7=C6C2=C%11C%13=C2C%15=C%12C%10=C4C23C1(CCCC(=O)OC)C1=CC=CC=C1 MCEWYIDBDVPMES-UHFFFAOYSA-N 0.000 description 7
- 239000000853 adhesive Substances 0.000 description 7
- 230000001070 adhesive effect Effects 0.000 description 7
- 230000008859 change Effects 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 229940126214 compound 3 Drugs 0.000 description 6
- 229920001903 high density polyethylene Polymers 0.000 description 6
- 239000004700 high-density polyethylene Substances 0.000 description 6
- 239000012212 insulator Substances 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 150000002825 nitriles Chemical class 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 125000001544 thienyl group Chemical group 0.000 description 6
- 229910052727 yttrium Inorganic materials 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 229920000144 PEDOT:PSS Polymers 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 125000001118 alkylidene group Chemical group 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 229910052737 gold Inorganic materials 0.000 description 5
- 239000010931 gold Substances 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 4
- 238000006069 Suzuki reaction reaction Methods 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 238000005266 casting Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 229920001940 conductive polymer Polymers 0.000 description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 150000002118 epoxides Chemical group 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 238000007641 inkjet printing Methods 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 150000003333 secondary alcohols Chemical class 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 150000003509 tertiary alcohols Chemical class 0.000 description 4
- 239000010936 titanium Substances 0.000 description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 238000006619 Stille reaction Methods 0.000 description 3
- YQEILISFULMNRR-UHFFFAOYSA-N [1]benzothiolo[6,5-f][1]benzothiole Chemical compound C1=C2C=C(SC=C3)C3=CC2=CC2=C1C=CS2 YQEILISFULMNRR-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 239000004411 aluminium Substances 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000002322 conducting polymer Substances 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 238000003618 dip coating Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 125000000232 haloalkynyl group Chemical group 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 238000000059 patterning Methods 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 125000005259 triarylamine group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- YMMGRPLNZPTZBS-UHFFFAOYSA-N 2,3-dihydrothieno[2,3-b][1,4]dioxine Chemical class O1CCOC2=C1C=CS2 YMMGRPLNZPTZBS-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000004425 Makrolon Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 229910004749 OS(O)2 Inorganic materials 0.000 description 2
- 229920001665 Poly-4-vinylphenol Polymers 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000005466 alkylenyl group Chemical group 0.000 description 2
- 150000007860 aryl ester derivatives Chemical class 0.000 description 2
- 150000004832 aryl thioethers Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- YKYMGFHOJJOSEB-UHFFFAOYSA-N butan-1-ol;potassium Chemical compound [K].CCCCO YKYMGFHOJJOSEB-UHFFFAOYSA-N 0.000 description 2
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 238000007306 functionalization reaction Methods 0.000 description 2
- 150000002240 furans Chemical class 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- RHZWSUVWRRXEJF-UHFFFAOYSA-N indium tin Chemical compound [In].[Sn] RHZWSUVWRRXEJF-UHFFFAOYSA-N 0.000 description 2
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 2
- 239000010954 inorganic particle Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 238000000813 microcontact printing Methods 0.000 description 2
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 2
- 125000003136 n-heptyl 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])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000002105 nanoparticle Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000009527 percussion Methods 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 2
- 238000001259 photo etching Methods 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- GBROPGWFBFCKAG-UHFFFAOYSA-N picene Chemical compound C1=CC2=C3C=CC=CC3=CC=C2C2=C1C1=CC=CC=C1C=C2 GBROPGWFBFCKAG-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920002530 polyetherether ketone Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002096 quantum dot Substances 0.000 description 2
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 2
- 238000007650 screen-printing Methods 0.000 description 2
- 229920006126 semicrystalline polymer Polymers 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 229910052712 strontium Inorganic materials 0.000 description 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- RCHUVCPBWWSUMC-UHFFFAOYSA-N trichloro(octyl)silane Chemical compound CCCCCCCC[Si](Cl)(Cl)Cl RCHUVCPBWWSUMC-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 125000002948 undecyl 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])[H] 0.000 description 2
- OWOHLURDBZHNGG-YFKPBYRVSA-N (8ar)-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione Chemical group O=C1CNC(=O)[C@@H]2CCCN12 OWOHLURDBZHNGG-YFKPBYRVSA-N 0.000 description 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
- 125000006731 (C1-C8) thioalkoxy group Chemical group 0.000 description 1
- PFNQVRZLDWYSCW-UHFFFAOYSA-N (fluoren-9-ylideneamino) n-naphthalen-1-ylcarbamate Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1=NOC(=O)NC1=CC=CC2=CC=CC=C12 PFNQVRZLDWYSCW-UHFFFAOYSA-N 0.000 description 1
- QVLAWKAXOMEXPM-UHFFFAOYSA-N 1,1,1,2-tetrachloroethane Chemical class ClCC(Cl)(Cl)Cl QVLAWKAXOMEXPM-UHFFFAOYSA-N 0.000 description 1
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical class ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- 150000004818 1,2-dichlorobenzenes Chemical class 0.000 description 1
- IBXNCJKFFQIKKY-UHFFFAOYSA-N 1-pentyne Chemical compound CCCC#C IBXNCJKFFQIKKY-UHFFFAOYSA-N 0.000 description 1
- FNWCDKSFAOGZEO-UHFFFAOYSA-N 1-propan-2-ylperoxypropane Chemical compound CCCOOC(C)C FNWCDKSFAOGZEO-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical class O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- WFRBDWRZVBPBDO-UHFFFAOYSA-N 2-methyl-2-pentanol Chemical compound CCCC(C)(C)O WFRBDWRZVBPBDO-UHFFFAOYSA-N 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical class CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- GGIFEFBEDYDOTI-UHFFFAOYSA-N 2-methylbutan-2-ol;potassium Chemical compound [K].CCC(C)(C)O GGIFEFBEDYDOTI-UHFFFAOYSA-N 0.000 description 1
- KRIMXCDMVRMCTC-UHFFFAOYSA-N 2-methylhexan-2-ol Chemical class CCCCC(C)(C)O KRIMXCDMVRMCTC-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GDRVFDDBLLKWRI-UHFFFAOYSA-N 4H-quinolizine Chemical compound C1=CC=CN2CC=CC=C21 GDRVFDDBLLKWRI-UHFFFAOYSA-N 0.000 description 1
- 241001614291 Anoplistes Species 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- MJBPUQUGJNAPAZ-UHFFFAOYSA-N Butine Natural products O1C2=CC(O)=CC=C2C(=O)CC1C1=CC=C(O)C(O)=C1 MJBPUQUGJNAPAZ-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- YXYKIXHQDOQFFJ-UHFFFAOYSA-N C(CCCCCCCCCCC)ON(C1=CC=CC=C1)OCCCCCCCCCCCCCC Chemical compound C(CCCCCCCCCCC)ON(C1=CC=CC=C1)OCCCCCCCCCCCCCC YXYKIXHQDOQFFJ-UHFFFAOYSA-N 0.000 description 1
- QEPCRAGGRXDAIP-UHFFFAOYSA-N CCC(C)[Na] Chemical compound CCC(C)[Na] QEPCRAGGRXDAIP-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- MSIUQOWNDKIKSG-UHFFFAOYSA-N Cc1cc([s]c(C)c2)c2[s]1 Chemical compound Cc1cc([s]c(C)c2)c2[s]1 MSIUQOWNDKIKSG-UHFFFAOYSA-N 0.000 description 1
- YUXIBTJKHLUKBD-UHFFFAOYSA-N Dibutyl succinate Chemical compound CCCCOC(=O)CCC(=O)OCCCC YUXIBTJKHLUKBD-UHFFFAOYSA-N 0.000 description 1
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical group COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229920002430 Fibre-reinforced plastic Polymers 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- NDJKXXJCMXVBJW-UHFFFAOYSA-N Heptadecane Natural products CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 1
- 208000015924 Lithiasis Diseases 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 1
- 229910020696 PbZrxTi1−xO3 Inorganic materials 0.000 description 1
- 239000004696 Poly ether ether ketone Substances 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000007099 Yamamoto allylation reaction Methods 0.000 description 1
- 239000005083 Zinc sulfide Substances 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- JAGRBVUQNWAXFU-UHFFFAOYSA-N [Li].C(CCC)O Chemical compound [Li].C(CCC)O JAGRBVUQNWAXFU-UHFFFAOYSA-N 0.000 description 1
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000004840 adhesive resin Substances 0.000 description 1
- 229920006223 adhesive resin Polymers 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- DCAYPVUWAIABOU-UHFFFAOYSA-N alpha-n-hexadecene Natural products CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 1
- RZJRJXONCZWCBN-UHFFFAOYSA-N alpha-octadecene Natural products CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000005013 aryl ether group Chemical group 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 description 1
- 229910002113 barium titanate Inorganic materials 0.000 description 1
- 229910021523 barium zirconate Inorganic materials 0.000 description 1
- DQBAOWPVHRWLJC-UHFFFAOYSA-N barium(2+);dioxido(oxo)zirconium Chemical compound [Ba+2].[O-][Zr]([O-])=O DQBAOWPVHRWLJC-UHFFFAOYSA-N 0.000 description 1
- 230000037429 base substitution Effects 0.000 description 1
- 125000002511 behenyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JUPQTSLXMOCDHR-UHFFFAOYSA-N benzene-1,4-diol;bis(4-fluorophenyl)methanone Chemical compound OC1=CC=C(O)C=C1.C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 JUPQTSLXMOCDHR-UHFFFAOYSA-N 0.000 description 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- BDFJWKALVSRGSR-UHFFFAOYSA-N butan-1-ol;sodium Chemical compound [Na].CCCCO BDFJWKALVSRGSR-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- NQIZDFMZAXUZCZ-UHFFFAOYSA-N carbifene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCC)C(=O)N(C)CCN(C)CCC1=CC=CC=C1 NQIZDFMZAXUZCZ-UHFFFAOYSA-N 0.000 description 1
- 229950003365 carbifene Drugs 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000000259 cinnolinyl group Chemical class N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000003851 corona treatment Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
- PJZURRKQOJYGAU-UHFFFAOYSA-N dibutan-2-yl butanedioate Chemical compound CCC(C)OC(=O)CCC(=O)OC(C)CC PJZURRKQOJYGAU-UHFFFAOYSA-N 0.000 description 1
- 150000004816 dichlorobenzenes Chemical class 0.000 description 1
- WWQSMJYMCWMODI-UHFFFAOYSA-N dicyclohexyl butanedioate Chemical compound C1CCCCC1OC(=O)CCC(=O)OC1CCCCC1 WWQSMJYMCWMODI-UHFFFAOYSA-N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- PBZAGXRVDLNBCJ-UHFFFAOYSA-N diheptyl butanedioate Chemical compound CCCCCCCOC(=O)CCC(=O)OCCCCCCC PBZAGXRVDLNBCJ-UHFFFAOYSA-N 0.000 description 1
- XEYHWMQDXTVNJW-UHFFFAOYSA-N dihexyl butanedioate Chemical compound CCCCCCOC(=O)CCC(=O)OCCCCCC XEYHWMQDXTVNJW-UHFFFAOYSA-N 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- KWABLUYIOFEZOY-UHFFFAOYSA-N dioctyl butanedioate Chemical compound CCCCCCCCOC(=O)CCC(=O)OCCCCCCCC KWABLUYIOFEZOY-UHFFFAOYSA-N 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- YPLYFEUBZLLLIY-UHFFFAOYSA-N dipropan-2-yl butanedioate Chemical compound CC(C)OC(=O)CCC(=O)OC(C)C YPLYFEUBZLLLIY-UHFFFAOYSA-N 0.000 description 1
- GOORECODRBZTKF-UHFFFAOYSA-N ditert-butyl butanedioate Chemical compound CC(C)(C)OC(=O)CCC(=O)OC(C)(C)C GOORECODRBZTKF-UHFFFAOYSA-N 0.000 description 1
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 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
- 238000010292 electrical insulation Methods 0.000 description 1
- 239000012777 electrically insulating material Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- UHPJWJRERDJHOJ-UHFFFAOYSA-N ethene;naphthalene-1-carboxylic acid Chemical compound C=C.C1=CC=C2C(C(=O)O)=CC=CC2=C1 UHPJWJRERDJHOJ-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000005621 ferroelectricity Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011151 fibre-reinforced plastic Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002425 furfuryl group Chemical group C(C1=CC=CO1)* 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000000755 henicosyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006342 heptafluoro i-propyl group Chemical group FC(F)(F)C(F)(*)C(F)(F)F 0.000 description 1
- 125000006341 heptafluoro n-propyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QSQIGGCOCHABAP-UHFFFAOYSA-N hexacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC6=CC=CC=C6C=C5C=C4C=C3C=C21 QSQIGGCOCHABAP-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000003427 indacenyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- HRHKULZDDYWVBE-UHFFFAOYSA-N indium;oxozinc;tin Chemical compound [In].[Sn].[Zn]=O HRHKULZDDYWVBE-UHFFFAOYSA-N 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 125000002463 lignoceryl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 1
- AZVCGYPLLBEUNV-UHFFFAOYSA-N lithium;ethanolate Chemical compound [Li+].CC[O-] AZVCGYPLLBEUNV-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 125000002960 margaryl 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])[H] 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000005442 molecular electronic Methods 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- 125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- OSSQSXOTMIGBCF-UHFFFAOYSA-N non-1-yne Chemical group CCCCCCCC#C OSSQSXOTMIGBCF-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- UMIPWJGWASORKV-UHFFFAOYSA-N oct-1-yne Chemical compound CCCCCCC#C UMIPWJGWASORKV-UHFFFAOYSA-N 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- ZPIRTVJRHUMMOI-UHFFFAOYSA-N octoxybenzene Chemical compound CCCCCCCCOC1=CC=CC=C1 ZPIRTVJRHUMMOI-UHFFFAOYSA-N 0.000 description 1
- 125000005447 octyloxy 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])O* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-O oxonium Chemical compound [OH3+] XLYOFNOQVPJJNP-UHFFFAOYSA-O 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- 125000002460 pentacosyl 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])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 1
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 230000005622 photoelectricity Effects 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920000636 poly(norbornene) polymer Polymers 0.000 description 1
- 229920000052 poly(p-xylylene) Polymers 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- YKPJEYXZEBLYCI-UHFFFAOYSA-N pyrrolo[3,4-c]pyrrole Chemical class C1=NC=C2C=NC=C21 YKPJEYXZEBLYCI-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- PBCFLUZVCVVTBY-UHFFFAOYSA-N tantalum pentoxide Inorganic materials O=[Ta](=O)O[Ta](=O)=O PBCFLUZVCVVTBY-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical group C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc oxide Inorganic materials [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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
-
- 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
- C08G61/125—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 oxygen 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/101—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an anthracene dye
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/101—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an anthracene dye
- C09B69/102—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an anthracene dye containing a perylene dye
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/109—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing other specific dyes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/124—Intrinsically conductive polymers
- H01B1/127—Intrinsically conductive polymers comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/653—Aromatic compounds comprising a hetero atom comprising only oxygen as heteroatom
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K99/00—Subject matter not provided for in other groups of this subclass
-
- 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
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/141—Side-chains having aliphatic units
- C08G2261/1412—Saturated aliphatic units
-
- 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
- C08G2261/22—Molecular weight
- C08G2261/226—Oligomers, i.e. up to 10 repeat units
-
- 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
- C08G2261/3222—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 oxygen atoms as the only heteroatom, e.g. furan
-
- 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
- C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
- C08G2261/3243—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 sulfur atoms as the only heteroatom, e.g. benzothiophene
-
- 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
- C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain
- C08G2261/344—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing 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
- C08G2261/36—Oligomers, i.e. comprising up to 10 repeat units
- C08G2261/364—Oligomers, i.e. comprising up to 10 repeat units containing hetero atoms
-
- 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
- C08G2261/411—Suzuki 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
- C08G2261/91—Photovoltaic applications
-
- 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
-
- 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
- C08G2261/94—Applications in sensors, e.g. biosensors
-
- 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
- C08G2261/95—Use in organic luminescent diodes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/50—Photovoltaic [PV] devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/50—Photovoltaic [PV] devices
- H10K30/57—Photovoltaic [PV] devices comprising multiple junctions, e.g. tandem PV cells
-
- 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
-
- 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
- H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
- H10K85/211—Fullerenes, e.g. C60
- H10K85/215—Fullerenes, e.g. C60 comprising substituents, e.g. PCBM
-
- 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
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Nanotechnology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Theoretical Computer Science (AREA)
- Mathematical Physics (AREA)
- Photovoltaic Devices (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thin Film Transistor (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
本发明涉及式(I)的低聚物,及其作为有机半导体在有机器件,尤其是在有机光伏器件(太阳能电池)和光电二极管,或在含有二极管和/或有机场效应晶体管的器件中的用途。在将本发明低聚物用于有机场效应晶体管、有机光伏器件(太阳能电池)和光电二极管中时,可观察到高能量转换效率、优异的场效应迁移率、良好的电流开/关比和/或优异稳定性。
Description
本发明涉及式I的1,4-二酮基吡咯并[3,4-c]吡咯(DPP)衍生物,其制造,及其作为有机半导体,例如在半导体器件中,尤其是传感器、二极管、光电二极管、有机场效应晶体管、柔性显示器用晶体管和/或太阳能电池(光伏电池)的用途。
DPP聚合物的实例及其合成例如描述于US6451459B1、WO05/049695、WO2008/000664、EP2034537A2、EP2075274A1、WO2010/049321、WO2010/049323、WO2010/108873、WO2010/115767、WO2010/136353、WO2010/136352和WO2011/144566(PCT/EP2011/057878)。
Matthias Horn等,Eur.Polymer J.38(2002)2197-2205描述了在主链中具有2,5-二氢吡咯并[3,4-c]吡咯单元的热介晶聚硅氧烷的合成和表征。
M.Smet等,Tetrahedron Letters42(2001)6257-6530描述了低聚物,其通过suzuki偶联的逐步顺序使用溴化1,4-二氧代-3,6-二苯基吡咯并[3,4c]吡咯(DPP衍生物)和1,4-二溴-2,5-二正己基苯作为单体制备。所得低聚物分别含有3、5和7个DPP单元。
WO2003048268涉及一种包含苝衍生物和二酮基吡咯并吡咯衍生物的有机电致发光器件,例如
WO06/061343公开下式的荧光二酮基吡咯并吡咯及其在制备油墨、色料、涂料用着色塑料、非冲击印刷材料、滤色器、化妆品、聚合物油墨颗粒、调色剂、作为荧光跟踪剂、在颜色改变介质、固态染料激光、EL激光和电致发光器件中的制备中的用途:
其中
R1和R2可以相同或不同且选自C1-C25烷基,可以被C1-C3烷基取代1-3次的烯丙基,可以任选被C1-C8烷基和/或C1-C8烷氧基取代1-3次的环烷基,可以被可被C1-C4烷基、卤素、硝基或氰基取代1-3次的苯基稠合1或2次的环烷基,链烯基,环烯基,炔基,杂环基,卤代烷基,卤代链烯基,卤代炔基,杂环基团,酮基或醛基,酯基,氨基甲酰基团,甲硅烷基,硅氧烷基团,芳基,杂芳基或-CR3R4-(CH2)m-A3,其中R3和R4相互独立地为氢或C1-C4烷基,或者可以被C1-C3烷基取代1-3次的苯基,A3表示可以被C1-C8烷基和/或C1-C8烷氧基取代1-3次的芳基或杂芳基,尤其是苯基或者1-或2-萘基,并且m表示0、1、2、3或4,A4和A5相互独立地为
其中R101-R123可相同或不同且选自氢、C1-C25烷基、环烷基、芳烷基、链烯基、环烯基、炔基、羟基、巯基、烷氧基、烷硫基、芳基醚基团、芳基硫醚基团、芳基、杂环基团、卤素、卤代烷基、卤代链烯基、卤代炔基、氰基、醛基团、羰基、羧基、酯基、氨基甲酰基团、其中R27和R28如上所定义的基团NR27R28、硝基、甲硅烷基、硅氧烷基、取代或未取代的乙烯基,或至少两个相邻取代基R115-R121形成芳族、杂芳族或脂族稠合环体系,
R124和R125可相同或不同且选自C1-C18烷基;C1-C18烷氧基、A3、C6-C18芳基;C7-C18芳烷基;或R124和R125一起形成环,尤其是5、6或7元环,其可任选被C1-C8烷基取代或其可任选通过可被C1-C8烷基、C1-C8烷氧基、卤素和氰基取代1-3次的苯基稠合1或2次;或
杂芳族基团,尤其是
其中R131-R152可相同或不同且选自氢、C1-C25烷基、环烷基、芳烷基、链烯基、环烯基、炔基、羟基、巯基、烷氧基、烷硫基、芳基醚基、芳基硫醚基团、芳基、杂环基团、卤素、卤代烷基、卤代链烯基、卤代炔基、氰基、醛基团、羰基、羧基、酯基、氨基甲酰基团、其中R27和R28如上所定义的基团NR27R28、硝基、甲硅烷基、硅氧烷基、取代或未取代的乙烯基,
R153为氢原子、可被–O-间隔的C1-C25烷基、环烷基、芳烷基、芳基或杂环基团,和
A6为环烷基、亚芳基或亚杂芳基,其任选被C1-C8烷基或C1-C8烷氧基取代1-3次。
在WO06/061343中明确提及如下化合物:
JP2006310538公开了下式的荧光二酮基吡咯并吡咯及其在发光元件中的用途:
其中Ar6可为芳基或杂芳基。
WO2007/003520涉及荧光化合物如 一种其制备方法及其在油墨、色料、涂料用着色塑料、非冲击印刷材料、滤色器、化妆品、聚合物油墨颗粒、调色剂、作为荧光跟踪剂、在颜色改变介质、染料激光和电致发光器件的制备中的用途。
US2010/0326525涉及光电器件如光伏器件,包括:
a)第一空穴收集电极;
b)任选地空穴传输层;
c)包含电子供体材料和电子受体材料的混合物的层;和
d)第二电子收集电极,
其中电子供体材料包含式(I)化合物:
其中X为氧或硫;
A1和A2独立地选自取代或未取代的芳基或杂芳基,其中(A1)m结构部分中的单独A1可各自独立地选自取代或未取代的芳基或杂芳基且(A2)n结构部分中的单独A2可各自独立地选自取代或未取代的芳基或杂芳基;
B1独立地选自取代和未取代的芳基或杂芳基;
m独立地选自1、2、3、4、5、6、7、8或9;
n独立地选自1、2、3、4、5、6、7、8或9;
p独立地选自0或1;
E1和E2独立地选自不存在、H或取代或未取代的芳基或杂芳基,或C1-C12烷基;和
R1、R2、R3和R4独立地选自H、C1-C12烷基和-C(-O)-O-C1-C12烷基。
明确公开了如下二聚DPP化合物:
Y.Xu等,Synthetic Metals160(2010)2135–2142报道了含DPP的低聚物的合成: 单体与苯并噻二唑、二辛氧基苯和芴通过氟化物介导的Suzuki聚合共聚而得到具有低含量DPP(1mol%)的共聚物。共聚物在发光二极管中用作发光层。
R.A.J.Janssen等,Macromol.Chem.Phys.2011,212,515–520公开了式(R=2-己基癸基;n=1-4)的二酮基吡咯并吡咯基低聚物,其由镍(0)-介导的单-和二溴化单体的混合物的Yamamoto偶联反应制备。单分散低聚物由所得混合物通过使用再循环GPC分离低聚物得到。研究了其光学和电化学性能。对于所有在溶液中测量的性能,在增加链长时观察不到明显变化,得到的结论为在该体系中的共轭仅仅非常有限。
Stephen Loser等,J.Am.Chem.Soc.,DOI:10.1021/ja202791n·公布日期(网络):2011年5月5日描述了萘并[2,3-b:6,7-b’]二噻吩(NDT)基供体分子的合成、表征和在高效有机光伏器件(OPV)中的首次应用。当NDT(TDPP)2(TDPP=噻吩包封的二酮基吡咯并吡咯:
R=2-乙基己基))与电子受体PC61BM组合时,实现4.06±0.06%能量转换效率(PCE)。
Yuning Li等,J.Mater.Chem.21(2011)10829[网上公布:09.06.2011]公开了如下聚合物的合成及其在OFET中的用途:
(R=2-辛基十二烷基)。
C.H.Woo等,J.Am.Chem.Soc.132(2010)15547[网上公布:14.10.2010]公开了如下聚合物的合成及其在太阳能电池中的用途:
R=2-乙基己基,X=S,Y=S;X=O,Y=S;或X=O,Y=O。
R.A.J.Janssen等,J.Mater.Chem.21(2011)1600[网上公布:06.12.2010]公开了如下聚合物的合成及其在OFET和太阳能电池中的用途:
R=2-己基癸基,X=O,Y=S;X=O,Y=O;或X=S,Y=O。
EP2033983A2涉及具有由(IV)表示的结构的DPP聚合物:
其中X各自独立地选自S、Se、O和NR",R"各自独立地选自氢、任选取代的烃和含杂原子基团,Z各自独立地为任选取代的烃、含杂原子基团和卤素之一,d为至少1的数,e为0-2的数;a为至少1的数;b为0-20的数;M各自为任选共轭结构部分且n为至少1的数。
尤其公开了如下聚合物:
其中n为重复单元数且可为约2至约5000,R"'、R’’’’和R’’’’’可为相同或不同取代基且其中取代基独立地选自任选取代的烃基和含杂原子基团。对于n为2,未定义端基。
WO2011025454A1公开了式(Ib)化合物及其在电子器件中的用途。
X为O、S或Se。D可尤其是尤其公开了如下聚合物:
其中n为2-15000。对于n为2,未定义端基。
本发明的目的是提供在用于有机场效应晶体管、有机光伏器件(太阳能电池)和光电二极管中时显示出高能量转换效率、优异的场效应迁移率、良好的电流开/关比和/或优异稳定性的化合物。
令人惊奇地发现某些二聚、三聚和四聚二酮基吡咯并吡咯衍生物可用作有机半导体。所述衍生物在非卤化有机溶剂中具有优异溶解性(允许容易处理)。其可比聚合物易于合成(允许节省成本),且其易于提纯(允许以低成本获得非常纯的产物)。
因此,本发明涉及式(I)化合物,其中
p为0或1,q为0或1,
A1和A2相互独立地为式的基团,
A3、A4和A5相互独立地为式的基团,
a为1或2;b为0、1或2;c为0、1或2;
k为0、1或2;l为1、2或3;r为0或1;z为0、1或2;
R1、R2、R1’、R2’、R1”、R2”、R1*和R2*可相同或不同且选自氢,
C1-C100烷基,其可任选被C1-C12烷基、C1-C12烷氧基、卤素、C5-C12环烷基、硝基、氰基、乙烯基、烯丙基、C6-C24芳基、C2-C20杂芳基、甲硅烷基或硅氧烷基取代一次或多次和/或可任选被–O-、-S-、-NR39-、-COO-、-CO-或–OCO-间隔,
C2-C100链烯基,其可任选被C1-C12烷基、C1-C12烷氧基、卤素、C5-C12环烷基、硝基、氰基、乙烯基、烯丙基、C6-C24芳基、C2-C20杂芳基、甲硅烷基或硅氧烷基取代一次或多次和/或可任选被–O-、-S-、-NR39-、-COO-、-CO-或–OCO-间隔,
C3-C100炔基,其可任选被C1-C12烷基、C1-C12烷氧基、卤素、C5-C12环烷基、硝基、氰基、乙烯基、烯丙基、C6-C24芳基、C2-C20杂芳基、甲硅烷基或硅氧烷基取代一次或多次和/或可任选被–O-、-S-、-NR39-、-COO-、-CO-或–OCO-间隔,
C3-C12环烷基,其可任选被C1-C12烷基、C1-C12烷氧基、卤素、C5-C12环烷基、硝基、氰基、乙烯基、烯丙基、C6-C24芳基、C2-C20杂芳基、甲硅烷基或硅氧烷基取代一次或多次和/或可任选被–O-、-S-、-NR39-、-COO-、-CO-或–OCO-间隔,
C6-C24芳基,其可任选被C1-C12烷基、C1-C12烷氧基、卤素、C5-C12环烷基、硝基、氰基、乙烯基、烯丙基、C6-C24芳基、C2-C20杂芳基、甲硅烷基或硅氧烷基取代一次或多次,
C2-C20杂芳基,其可任选被C1-C12烷基、C1-C12烷氧基、卤素、C5-C12环烷基、硝基、氰基、乙烯基、烯丙基、C6-C24芳基、C2-C20杂芳基、甲硅烷基或硅氧烷基取代一次或多次,
-CO-C1-C18烷基、-CO-C5-C12环烷基、-COO-C1-C18烷基;
R3为氢、卤素、氰基、C1-C25烷基、被E取代一次或多次和/或被D间隔一次或多次C1-C25烷基、COO-C1-C18烷基、C4-C18环烷基、被G取代的C4-C18环烷基、C2-C18链烯基、C2-C18炔基、C1-C18硫代烷氧基、C1-C18烷氧基、被E取代和/或被D间隔的C1-C18烷氧基、C7-C25芳烷基或被G取代的C7-C25芳烷基,或下式的基团:
Ar1、Ar2、Ar3、Ar4、Ar5、Ar6和Ar7相互独立地为下式的二价基团:
X为–O-、-S-、-NR10-、-Si(R18)(R19)-、-Ge(R18)(R19)-、-C(R12)(R13)-、-C(=O)-、-C(=CR14R15)-、
R10和R11相互独立地为氢、C1-C18烷基、C1-C18卤代烷基、C7-C25芳基烷基或C1-C18烷酰基,
R12和R13相互独立地为氢、C1-C18烷基、C1-C18卤代烷基、C7-C25芳基烷基、C6-C24芳基或C2-C20杂芳基,或R12和R13一起为氧代、或形成5或6元环,其未被取代或被C1-C18烷基和/或C1-C18烷氧基取代;
R14和R15相互独立地为氢、C1-C18烷基、C6-C24芳基、C2-C20杂芳基、-CN或COOR50;
R16和R17相互独立地为氢、卤素、C1-C25烷基、C1-C25烷氧基、C7-C25芳基烷基或Rx为C1-C12烷基或三(C1-C8烷基)甲硅烷基,
R18和R19相互独立地为氢、C1-C18烷基、C7-C25芳基烷基或苯基,其任选可被C1-C8烷基和/或C1-C8烷氧基取代1-3次,
R20和R21相互独立地为氢、C1-C25烷基、C2-C25链烯基、被一个或多个–O-或–S-间隔的C2-C25烷基、COOR50、氰基、C1-C18烷氧基、C6-C24芳基、C7-C25芳基烷基、卤素或C2-C20杂芳基,或R20和R21一起为亚烷基或亚烯基,其可经由氧和/或硫键于(杂)芳族残基且可具有至多25个碳原子,
R30-R37相互独立地为氢、C1-C25烷基、C2-C25链烯基、被一个或多个–O-或–S-间隔的C2-C25烷基、COOR50、氰基、C1-C25烷氧基、C6-C24芳基、C7-C25芳基烷基、卤素或C2-C20杂芳基,
R40和R41相互独立地为氢、C1-C25烷基、C2-C25链烯基、被一个或多个–O-或–S-间隔的C2-C25烷基、COOR50、氰基、C1-C18烷氧基、C6-C24芳基、C7-C25芳基烷基、卤素或C2-C20杂芳基,
R50为C1-C25烷基、C1-C25卤代烷基、C7-C25芳基烷基、C6-C24芳基或C2-C20杂芳基;
R60-R68相互独立地为H、卤素、氰基、C1-C25烷基、被E取代和/或被D间隔的C1-C25烷基、C6-C24芳基、被G取代的C6-C24芳基、C2-C20杂芳基、被G取代的C2-C20杂芳基、C4-C18环烷基、被G取代的C4-C18环烷基、C2-C18链烯基、C2-C18炔基、C1-C18烷氧基、被E取代和/或被D间隔的C1-C18烷氧基、C7-C25芳烷基或被G取代的C7-C25芳烷基,
R70和R71相互独立地为氢、C1-C25烷基或C7-C25芳烷基,或R70和R71一起为亚烷基或亚烯基,其可经由氧和/或硫键于噻吩基残基且可具有至多25个碳原子,
D为-CO-、-COO-、-S-、-O-、–NR39-或–C(=O)NR39-,
E为C1-C8硫代烷氧基、COO-C1-C18烷基、C1-C8烷氧基、CN、-NR39R39’、-CONR39R39’或卤素,
G为E或C1-C18烷基,
R39和R39’相互独立地为氢、C1-C18烷基、C1-C18卤代烷基、C7-C25芳基烷基或C1-C18烷酰基,
条件为基团Ar1、Ar2、Ar3、Ar4、Ar5、Ar6和Ar7中至少一个为式基团;并且如果q为0,p为0,k为0,r为0,z为0且l为1,则另一条件为Ar5不为基团
式(I)的分子优选由镜像对称序列的选自Ar1-Ar7的结构嵌段和二酮基吡咯并吡咯基础骨架构成。
式I化合物优选为下式化合物:
其中A1、A2、A3、A4、A5、R1、R2、R1’、R2’、R1”、R2”、R1*和R2*如上所定义。
Ar1、Ar2、Ar3、Ar4、Ar5、Ar6和Ar7中至少一个为基团优选Ar1、Ar4和Ar7中至少一个为基团更优选Ar1为最优选Ar1、Ar4和Ar7为基团
如果Ar1、Ar4或Ar7为呋喃环,则呋喃环优选为单取代的(远离DPP的位置)或未取代的,最优选未取代的
R1、R2、R1’、R2’、R1”、R2”、R1*和R2*可相同或不同且优选选自氢,C1-C100烷基,其可任选被C1-C12烷基、C1-C12烷氧基、卤素、C5-C12环烷基、氰基、C6-C24芳基、C2-C20杂芳基取代一次或多次和/或可任选被–O-、-S-、-COO-或–OCO-间隔,
C2-C100链烯基,其可任选被C1-C12烷基、C1-C12烷氧基、卤素、C5-C12环烷基、氰基、C6-C24芳基、C2-C20杂芳基取代一次或多次和/或可任选被–O-、-S-、-COO-或–OCO-间隔,
C3-C100炔基,其可任选被C1-C12烷基、C1-C12烷氧基、卤素、C5-C12环烷基、氰基、C6-C24芳基、C2-C20杂芳基取代一次或多次和/或可任选被–O-、-S-、-COO-或–OCO-间隔,
C4-C12环烷基,其可任选被C1-C12烷基、C1-C12烷氧基、卤素、C5-C12环烷基、氰基、C6-C24芳基、C2-C20杂芳基取代一次或多次和/或可任选被–O-、-S-、-COO-或–OCO-间隔,
C6-C24芳基,其可任选被C1-C12烷基、C1-C12烷氧基、卤素、C5-C12环烷基、氰基、C6-C24芳基、C2-C20杂芳基取代一次或多次,
C2-C20杂芳基,其可任选被C1-C12烷基、C1-C12烷氧基、卤素、C5-C12环烷基、氰基、C6-C24芳基、C2-C20杂芳基取代一次或多次,
-CO-C1-C18烷基、-CO-C5-C12环烷基和-COO-C1-C18烷基。
更优选R1、R2、R1’、R2’、R1”、R2”、R1*和R2*选自氢、C1-C50烷基、C1-C50卤代烷基、C7-C25芳基烷基、C2-C50链烯基、C2-C50卤代链烯基、烯丙基、C5-C12环烷基、苯基或可任选被C1-C12烷基或C1-C12烷氧基取代一次或多次的萘基、-CO-C1-C18烷基、-CO-C5-C12环烷基和-COO-C1-C18烷基。甚至更优选R1、R2、R1’、R2’、R1”、R2”、R1*和R2*为C1-C50烷基。还更优选R1、R2、R1’、R2’、R1”、R2”、R1*和R2*为C1-C36烷基。最优选R1、R2、R1’、R2’、R1”、R2”、R1*和R2*为C12-C24烷基,非常特别是C16-C24烷基。优选R1为R2、R1’为R2’、R1”为R2”且R1*为R2*。最优选R1、R2、R1’、R2’、R1”、R2”、R1*和R2*具有相同含义。
有利地,基团R1、R2、R1’、R2’、R1”、R2”、R1*和R2*可以由式表示,其中m1=n1+2和m1+n1≤24。手性侧链如R1、R2、R1’、R2’、R1”、R2”、R1*和R2*可为纯手性或外消旋的,其可影响化合物的形态。
优选a为1;b为0、1或2;c为0、1或2;更优选a为1;b为0或1、c为0或1;还更优选a为1;b为0或1;c为0;最优选a为1;b为0;c为0.
优选k+l+r+z为小于5的整数;更优选k+l+r+z为1-4的整数;甚至更优选k+l+r+z为1-3的整数;最优选k+l+r+z为1或3。如果q为0,p为0,k为0,r为0,z为0且l为1,则Ar5优选不为基团在本发明的一个优选实施方案中,两个呋喃基团不经由单键直接链接。
优选式(Ia)、(Ib)和(Ic)化合物中A1和A2相同。优选式(Ib)化合物中的A3和A4相同。优选式(Ic)化合物中的A3和A5相同。更优选式(Ic)化合物中的A3、A4和A5相同。
A1和A2相互独立地为下式的基团其中
a为1,b为0或1,c为0或1,
Ar1、Ar2和Ar3相互独立地为下式基团:
R10为氢、C1-C25烷基或COO-C1-C25烷基,
R16和R17相互独立地为氢、卤素、C1-C25烷基、C1-C25烷氧基、C7-C25芳基烷基或
Rx为C1-C12烷基或三(C1-C8烷基)甲硅烷基,
R20和R21相互独立地为氢或C1-C25烷基,
R30-R35相互独立地为氢或C1-C25烷基,
R42和R43相互独立地为C1-C25烷基;
R3为氢、卤素、氰基、C1-C25烷基或下式的基团: 其中
R60-R68相互独立地为氢或C1-C25烷基,
R70和R71相互独立地为氢或C1-C25烷基,或
R70和R71一起为亚烷基,其可经由氧和/或硫键于噻吩基残基且可具有至多25个碳原子。
优选R70和R71相互独立地为氢或C1-C25烷基。
在本发明的一个优选实施方案中,A1和A2相互独立地为式的基团,其中
a为1,b为0或1,c为0或1,
Ar2和Ar3相互独立地为和
R3为H、C1-C25烷基或苯基。
在本发明的一个优选实施方案中,A3、A4和A5相互独立地为式的基团,
k为0、1或2;l为1、2或3;r为0或1;z为0、1或2;
Ar4、Ar5、Ar6和Ar7相互独立地为下式的基团:
R10为氢、C1-C25烷基或COO-C1-C25烷基,
R16和R17相互独立地为氢、卤素、C1-C25烷基、C1-C25烷氧基、C7-C25芳基烷基或
Rx为C1-C12烷基或三(C1-C8烷基)甲硅烷基,
R20和R21相互独立地为氢或C1-C25烷基,
R30-R35相互独立地为氢或C1-C25烷基,和
R42和R43相互独立地为C1-C25烷基。
更优选A3、A4和A5相互独立地为式的基团,
k和z为0或1;l为1、2或3;r为0;
Ar4和Ar7为式的基团,
Ar5为下式基团:
y为1、2或3,
R10为H或C1-C25烷基,
R16和R17为H或C1-C25烷基,和
R32和R33为H或C1-C25烷氧基。
优选R3为氢、卤素、氰基、C1-C25烷基或下式的基团:
更优选R3为氢、卤素、氰基、C1-C25烷基或还更优选R3为氢或C1-C25烷基。最优选R3为氢。
优选Ar1、Ar2、Ar3、Ar4、Ar5、Ar6和Ar7相互独立地为下式的二价基团: Ar1、Ar4和Ar7优选以使得没有6元环直接连接至二酮基吡咯并吡咯基础骨架的方式选择。
更优选Ar1、Ar2、Ar3、Ar4、Ar5、Ar6和Ar7相互独立地为下式的二价基团: Ar1、Ar4和Ar7优选以使得没有6元环直接连接至二酮基吡咯并吡咯基础骨架的方式选择。
甚至更优选Ar1、Ar2、Ar3、Ar4、Ar5、Ar6和Ar7相互独立地为下式的基团: Ar1、Ar4和Ar7优选以使得没有6元环直接连接至二酮基吡咯并吡咯基础骨架的方式选择。
如果选自Ar1-Ar7的两个结构部分经由单键链接,则位于该链接键的邻位的选自R14、R15、R20、R21、R30、R31、R32、R33、R34、R35、R36、R37、R38、R40、R41的小于4个取代基不为氢。更优选位于该链接键的邻位的选自R14、R15、R20、R21、R30、R31、R32、R33、R34、R35、R36、R37、R38、R40、R41的小于3个取代基不为氢。甚至更优选位于该链接键的邻位的选自R14、R15、R20、R21、R30、R31、R32、R33、R34、R35、R36、R37、R38、R40、R41的仅一个取代基不为氢。最优选位于该链接键的邻位的选自R14、R15、R20、R21、R30、R31、R32、R33、R34、R35、R36、R37、R38、R40、R41的所有取代基均为氢。
如果选自Ar1、Ar4或Ar7的结构部分经由单键链接至DPP基础骨架,则位于该链接键的邻位的选自R14、R15、R20、R21、R30、R31、R32、R33、R34、R35、R36、R37、R38、R40、R41的取代基优选为氢。
在本发明的一个优选实施方案中,A1和A2相互独立地为式的基团,
A3、A4和A5相互独立地为式的基团,
其中k为1,l为1,z为1和r为0,
Ar1、Ar4和Ar7为
Ar2、Ar3、Ar5、Ar6相互独立地为下式基团:
Ar1、Ar4和Ar7优选以使得没有6元环直接连接至二酮基吡咯并吡咯基础骨架的方式选择。
优选X为–O-、-S-、-NR10-、-Si(R18)(R19)-、-C(R12)(R13)-、 更优选X为–O-、-S-、-NR10-、-C(R12)(R13)-、最优选X为-S-、-NR10-或
R10和R11相互独立地为氢、C1-C18烷基、C1-C18卤代烷基、C7-C25芳基烷基或C1-C18烷酰基,优选氢、C1-C18烷基、C1-C18烷酰基;最优选C1-C18烷基。
优选R12和R13相互独立地为氢、C1-C18烷基、C1-C18卤代烷基、C7-C25芳基烷基,或R12和R13一起为氧代或更优选R12和R13相互独立地为氢、C1-C18烷基,或R12和R13一起为氧代。最优选R12和R13相互独立地为C1-C18烷基。
R14和R15相互独立地为氢、C1-C18烷基、C6-C24芳基、C2-C20杂芳基、-CN或COOR50。优选R14和R15相互独立地为氢、C1-C18烷基、-CN或COOR50,其中更优选R14和R15中至少一个为-CN或COOR50,尤其是R14和R15均为–CN。
R16和R17相互独立地为氢、卤素、C1-C25烷基、C1-C25烷氧基、C7-C25芳基烷基或Rx为C1-C10烷基或三(C1-C8烷基)甲硅烷基。
优选R18和R19为C1-C18烷基。
优选R20和R21相互独立地为氢、C1-C25烷基、COOR50、氰基、C1-C18烷氧基或卤素。更优选R20和R21相互独立地为氢、C1-C25烷基、C1-C18烷氧基或卤素。甚至更优选R20和R21相互独立地为氢或C1-C25烷基。最优选R20和R21为氢;
优选R30-R37相互独立地为氢、C1-C25烷基、COOR50、氰基、C1-C18烷氧基或卤素。更优选R30-R38相互独立地为氢、C1-C25烷基、C1-C18烷氧基或卤素。甚至更优选R30-R38相互独立地为氢或C1-C25烷基。最优选R30-R38为氢。
优选R40和R41相互独立地为氢、C1-C25烷基、COOR50或氰基。更优选R40和R41相互独立地为氢、C1-C25烷基或氰基。甚至更优选R40和R41相互独立地为氢或C1-C25烷基。最优选R40和R41相互独立地为C1-C25烷基。
优选R42和R43相互独立地为C1-C18烷基。
R50为C1-C25烷基、C1-C25卤代烷基、C7-C25芳基烷基、C6-C24芳基或C2-C20杂芳基。R50优选为C1-C25烷基、C1-C25卤代烷基、C7-C25芳基烷基,最优选C1-C25烷基。
优选R60-R68相互独立地为氢、C1-C25烷基、C1-C18烷氧基或卤素。更优选R60-R68相互独立地为氢或C1-C25烷基。最优选R60-R68为氢。
在特别优选的实施方案中,本发明涉及下式化合物:
甚至更优选式
的化合物。
在另一特别优选的实施方案中,本发明涉及下式化合物:
。甚至更优选下式化合物:
b为0或1,c为0或1。
A3、A4、Ar5和Ar6相互独立地为下式基团:
y为1、2或3。
Ar2和Ar3相互独立地为
R3为H、C1-C25烷基或苯基。R10为H或C1-C25烷基。R16和R17为H或C1-C25烷基。R32和R33为H或C1-C25烷氧基。
R1、R2、R1’、R2’、R1*和R2*选自氢、C1-C50烷基、C1-C50卤代烷基、C7-C25芳基烷基、C2-C50链烯基、C2-C50卤代链烯基、烯丙基、C5-C12环烷基、苯基或可任选被C1-C12烷基或C1-C12烷氧基取代一次或多次的萘基、-CO-C1-C18烷基、-CO-C5-C12环烷基和-COO-C1-C18烷基。
目前最优选化合物A-1至A-22、B-1和B-2。参考权利要求9。
在另外的实施方案中,本发明涉及下式的化合物:
其中
A1’和A2’相互独立地为下式的基团
R3’每次出现独立地为ZnX12、-SnR207R208R209,其中R207、R208和R209相同或不同且为H或C1-C6烷基,其中两个基团任选形成公共环且这些基团任选支化或未支化,且X12为卤素原子,非常特别是I或Br;-OS(O)2CF3、-OS(O)2-芳基,尤其是-OS(O)2CH3、-B(OH)2、-B(OH)3 -、-BF3、-B(OY1)2、其中Y1每次出现独立地为C1-C12烷基和Y2每次出现独立地为C2-C10亚烷基,如–CY3Y4-CY5Y6-或–CY7Y8-CY9Y10-CY11Y12-,其中Y3、Y4、Y5、Y6、Y7、Y8、Y9、Y10、Y11和Y12相互独立地为氢或C1-C12烷基,尤其是-C(CH3)2C(CH3)2-、-C(CH3)2CH2C(CH3)2-或-CH2C(CH3)2CH2-,和Y13和Y14相互独立地为氢或C1-C12烷基;a、b、c、q、p、R1、R2、R1’、R2’、R1”、R2”、R1*、R2*、Ar1、Ar2、Ar3、A3、A4和A5如上所定义。
式X化合物优选为式 化合物。式X,尤其是Xa、Xb和Xc化合物为制备聚合物的中间体且可以用于制备聚合物。
因此,本发明还涉及包含式的重复单元的聚合物,其中
A1’’和A2’’相互独立地为式的基团,其中a、b、c、p、q、R1、R2、R1’、R2’、R1”、R2”、R1*、R2*、Ar1、Ar2、Ar3、A3、A4和A5如上所定义。本发明聚合物可用于生产半导体器件。因此,本发明还涉及包含本发明聚合物的半导体器件。
制备式(Ia)化合物(R1=R2=R1*=R2*;A1=A2)的方法包括:
(a)(在强碱存在下)使2摩尔琥珀酸二酯与1摩尔式的腈和2摩尔式的腈反应,
(b)使在步骤a)中得到的式(IX’)化合物与式R1-X16的卤化物(X16为卤素,尤其是Br或I)在合适碱如碳酸钾存在下在合适溶剂如N-甲基吡咯烷酮中反应。
另一合成途径例如为单卤化化合物 借助镍配合物在Yamamoto反应条件下的反应,其中得到式(Ia)化合物。X15为卤素原子,尤其是Br或I。l和z相互独立地为1或2。k为0、1或2。r为0或1。R1、R2、R1’、R2’、A1和A2如上所定义。Ar4、Ar5、Ar6、Ar7和A3分别如上所定义。
制备其中R2为R1*的式(Ia)化合物的另一方法包括:
(a)(在强碱存在下)使2摩尔式(XV)和(XV’)化合物(R200和R200’相互独立地为C1-C8烷基或苄基)与1摩尔式的二腈化合物反应;
(b)然后用化合物R2-X16(X16为卤素,尤其是碘或溴)在碱性条件(优选K2CO3)下在干燥溶剂如二甲基甲酰胺中烷基化在步骤a)中得到的式化合物。
式XV和XV’化合物可以例如类似于C.Morton等、Tetrahedron58(2002)5547–5565中所述的方法合成。
制备式(Ib)化合物(R1=R2=R1*=R2*)的另一方法包括:
(a)(在强碱存在下)使2摩尔琥珀酸二酯与1摩尔式的腈和2摩尔式的腈反应,
(b)使在步骤a)中得到的式(IX’’)化合物与式R1-X16的卤化物(X16为卤素,尤其是Br或I)在合适碱如碳酸钾存在下在合适溶剂如N-甲基吡咯烷酮中反应,R1、R1’、R2’、A1、A2、A3和A4如上所定义。
式化合物可以通过使其中X14为卤素如Br或I的与氰化铜(I)反应而制备。与氰化铜(I)的反应在合适的溶剂如二甲基甲酰胺(DMF)中并且在大致室温至约180°C,优选约100°C至约170°C的温度下,例如在130°C下进行。参考WO2012/041849和FrankWürthner等,Chem.Commun.,2011,47,1767-1769。
制备其中R2为R1*的式(Ib)化合物的另一方法包括:
(a)(在强碱存在下)使2摩尔式(XV)化合物和(XV’)(R200和R200’相互独立地为C1-C8烷基或苄基)与1摩尔式的二腈化合物反应;
(b)然后在碱性条件下(优选K2CO3)在干燥溶剂如二甲基甲酰胺中用化合物R2-X16(X16为卤素,尤其是碘或溴)烷基化在步骤(a)中得到的式化合物。
替换地,式(Ia)化合物(R1=R1*;R2=R2*,A3为式基团,Ar4为Ar7,k为1或2,z为1或2)可以通过使式化合物与式化合物反应而制备,其中X16’为-B(OH)2、-B(OH)3 -、-BF3、-B(OY1)2、或且X16为卤素如Br或I。
Suzuki反应通常在约0°C至180°C下在芳族烃溶剂如甲苯、二甲苯中进行。其他溶剂如二甲基甲酰胺、二烷、二甲氧基乙烷和四氢呋喃也可以单独使用或者与芳族烃混合使用。将含水碱,优选碳酸钠或碳酸氢钠、磷酸钾、碳酸钾或碳酸氢钾用作有机硼酸、硼酸酯的活化剂并用作HBr清除剂。缩合反应可进行0.2-100小时。有机碱如四烷基氢氧化铵和相转移催化剂如TBAB可以促进硼的活性(参见例如Leadbeater&Marco;Angew.Chem.Int.Ed.Eng.42(2003)1407及其中所引用的文献)。反应条件的其他变化由T.I.Wallow和B.M.Novak,J.Org.Chem.59(1994)5034-5037;和M.Remmers、M.Schulze和G.Wegner,Macromol.Rapid Commun.17(1996)239-252中给出。
本发明化合物还可以通过Stille偶联合成(参见例如Babudri等,J.Mater.Chem.,2004,14,11-34;J.K.Stille,Angew.Chemie Int.Ed.Engl.1986,25,508)。为了进行该方法,优选将其中X16’为-SnR207R208R209的锡化合物和卤素化合物引入一种或多种惰性有机溶剂中并在0-200°C,优选30-170°C的温度下搅拌1-200小时,优选5-150小时。
就原料和式I化合物的制备而言参考WO2009/047104和WO2012/041849。
在以上Stille和Suzuki偶联反应中,可将卤化反应配对上的卤素X16用X16’结构部分替换,且同时将另一反应配对的X16’结构部分用X16替换。
式Ib化合物可以以类似于式Ia化合物经由Suzuki或Stille反应合成的方式由相应结构嵌段开始制备,例如:
使2当量式化合物与1当量式化合物反应而得到式化合物。
其中R1、R2、R1’、R2’、R1”、R2”、R1*和/或R2*为氢的化合物可以通过使用可以在前体化合物合成之后移除的保护基团得到(参见例如EP-A-0648770、EP-A-0648817、EP-A-0742255、EP-A-0761772、
WO98/32802、WO98/45757、WO98/58027、WO99/01511、WO00/17275、WO00/39221、WO00/63297和EP-A-1086984)。前体化合物向所需最终化合物的转化借助在已知条件如热下任选在额外催化剂如WO00/36210中所述的催化剂存在下的***而进行。
该保护基团的实例为式的基团,其中L为适于赋予溶解性的任何所需基团。
L优选为式 基团,
其中
Z1、Z2和Z3彼此独立地为C1-C6烷基,
Z4和Z8彼此独立地为C1-C6烷基;间隔有氧、硫或N(Z12)2的C1-C6烷基;或未取代或被C1-C6烷基、C1-C6烷氧基、卤素、氰基或硝基取代的苯基或联苯基,
Z5、Z6和Z7彼此独立地为氢或C1-C6烷基,
Z9为氢、C1-C6烷基或式基团,
Z10和Z11彼此独立地为氢,C1-C6烷基,C1-C6烷氧基,卤素,氰基,硝基,N(Z12)2,或未取代或被卤素、氰基、硝基、C1-C6烷基或C1-C6烷氧基取代的苯基,
Z12和Z13为C1-C6烷基,Z14为氢或C1-C6烷基,且Z15为氢、C1-C6烷基或未取代或被C1-C6烷基取代的苯基,
Q为未取代或被C1-C6烷氧基、C1-C6烷硫基或C2-C12二烷基氨基单取代或多取代的p,q-C2-C6亚烷基,其中p和q为表示不同位置的数,
X为选自氮、氧和硫的杂原子,当X为氧或硫时,m'为数0,当X为氮时,m为数1,且
L1和L2彼此独立地为未取代或被单-或多-C1-C12烷氧基-、-C1-C12烷硫基-、-C2-C24二烷基氨基-、-C6-C12芳氧基-、-C6-C12芳硫基-、-C7-C24烷基芳基氨基-或-C12-C24二芳基氨基-取代的C1-C6烷基或[-(p',q'-C2-C6亚烷基)-Z-]n'-C1-C6烷基,n'为1-1000的数,p'和q'为表示不同位置的数,各Z彼此独立地为杂原子氧、硫或C1-C12烷基取代的氮,且重复单元[-C2-C6亚烷基-Z-]中的C2-C6亚烷基可相同或不同,且L1和L2可为饱和的或不饱和1-10次,可未间隔或在任何位置间隔有1-10个选自-(C=O)-和-C6H4-的基团,且可不带有其他取代基或带有1-10个选自卤素、氰基和硝基的其他取代基。最优选L为式基团。
在本发明方法中要使用的琥珀酸二酯包括琥珀酸二烷基酯、琥珀酸二芳基酯、琥珀酸单烷基单芳基酯。琥珀酸二烷基酯和琥珀酸二芳基酯也可以是不对称的。然而,优选使用对称琥珀酸二酯,最优选对称琥珀酸二烷基酯,最优选对称琥珀酸二烷基酯。如果使用琥珀酸二芳基酯或琥珀酸单芳基单烷基酯,则芳基优选为未被取代或被如下基团取代的苯基:卤素如氯,C1-6烷基如乙基、甲基、异丙基或叔丁基,或C1-6烷氧基如甲氧基或乙氧基。芳基的优选含义为未取代的苯基。如果使用琥珀酸二烷基酯或琥珀酸单烷基单芳基酯,则烷基可以为未支化或支化的,优选支化的且可含有优选1-18,尤其是1-12,更特别是1-8,更优选1-5个碳原子。支化烷基优选为仲烷基或叔烷基,例如异丙基、仲丁基、叔丁基、叔戊基和环己基。
琥珀酸二酯的实例为琥珀酸二甲基酯、琥珀酸二乙基酯、琥珀酸二丙基酯、琥珀酸二丁基酯、琥珀酸二戊基酯、琥珀酸二己基酯、琥珀酸二庚基酯、琥珀酸二辛基酯、琥珀酸二异丙基酯、琥珀酸二仲丁基酯、琥珀酸二叔丁基酯、琥珀酸二叔戊基酯、琥珀酸二[1,1-二甲基丁基]酯、琥珀酸二[1,1,3,3-四甲基丁基]酯、琥珀酸二[1,1-二甲基戊基]酯、琥珀酸二[1-甲基-乙基丁基]酯、琥珀酸二[1,1-二乙基丙基]酯、琥珀酸二苯基酯、琥珀酸二[4-甲基苯基]酯、琥珀酸二[4-氯苯基]酯、琥珀酸单乙基单苯基酯和琥珀酸二环己基酯。最优选,起始的琥珀酸二酯为琥珀酸二异丙基酯。
琥珀酸二酯是已知化合物且可以通过已知方法制备。
腈和琥珀酸二酯通常以化学计量比例使用。以大于仅仅化学计量比例使用要与琥珀酸二酯反应的腈可能是有利的。相对于腈过量琥珀酸二酯可通常对产率具有正面影响,在这种情况下,过量可以至多为琥珀酸二酯所需化学计量量的两倍。
琥珀酸二酯与腈的反应在有机溶剂中进行。合适溶剂的实例为具有1-10碳原子的伯醇、仲醇或叔醇,例如甲醇、乙醇、正丙醇、异丙醇、正丁醇、仲丁醇、叔丁醇、正戊醇、2-甲基-2-丁醇、2-甲基-2-戊醇、3-甲基-3-戊醇、2-甲基-2-己醇、3-乙基-3-戊醇、2,4,4-三甲基-2-戊醇或二醇如乙二醇或二甘醇;以及醚如四氢呋喃或二烷,或二醇醚如乙二醇甲基醚、乙二醇乙基醚、二甘醇单甲基醚或二甘醇单乙基醚;以及偶极非质子性溶剂如乙腈、苄腈、二甲基甲酰胺、N,N-二甲基乙酰胺、硝基苯、N-甲基吡咯烷酮;脂族或芳族烃如苯或烷基、烷氧基或卤素取代的苯,例如甲苯、二甲苯、茴香醚或氯苯;或芳族杂环化合物如吡啶、甲基吡啶或喹啉。还可以使用以上溶剂的混合物。每1重量份反应物使用5-20重量份溶剂是有利的。
在本发明方法中,优选使用醇作为溶剂,尤其是仲醇或叔醇。优选的叔醇为叔丁醇和叔戊醇。这些优选的溶剂与芳族烃如甲苯或二甲苯或卤素取代的苯如氯苯的混合物也是有用的。
本发明方法在强碱存在下进行。合适的强碱尤其是碱金属本身如锂、钠或钾,或碱金属氨基化物如氨基化锂、氨基化钠或氨基化钾,或碱金属氢化物如氢化锂、氢化钠或氢化钾,或碱土金属醇盐或碱金属醇盐(其优选由含有1-10个碳原子的脂族伯醇、仲醇或叔醇得到),例如甲醇锂、甲醇钠、甲醇钾,或乙醇锂、乙醇钠或乙醇钾,正丙醇锂、正丙醇钠或正丙醇钾,异丙醇锂、异丙醇钠或异丙醇钾,正丁醇锂、正丁醇钠或正丁醇钾,仲丁醇锂、仲丁基钠或仲丁醇钾,叔丁醇锂、叔丁醇钠或叔丁醇钾,2-甲基-2-丁醇锂、2-甲基-2-丁醇钠或2-甲基-2-丁醇钾,2-甲基-2-戊醇锂、2-甲基-2-戊醇钠或2-甲基-2-戊醇钾,3-甲基-3-戊醇锂、3-甲基-3-戊醇钠或3-甲基-3-戊醇钾,3-乙基-3-戊醇锂、3-乙基-3-戊醇钠或3-乙基-3-戊醇钾,3-乙基-3-戊醇锂、3-乙基-3-戊醇钠或3-乙基-3-戊醇钾。额外地,还可以使用这些碱的混合物。
优选的强碱为碱金属醇盐,其中碱金属优选为钠或钾且醇盐优选衍生自仲醇或叔醇。特别优选的强碱因此例如为异丙醇钠或异丙醇钾、仲丁醇钠或仲丁醇钾、叔丁醇钠或叔丁醇钾和叔戊醇钠或叔戊醇钾。此外,碱金属醇盐可以通过使合适醇与碱金属、碱金属氢化物或碱金属氨基化物反应而原位制备。
强碱基于1摩尔琥珀酸二酯以优选约0.1摩尔至约10摩尔,最优选约1.9摩尔至约4.0摩尔的量使用。尽管碱的化学计量量可能是足够的,但是发现过量碱对产率具有有利影响。
卤素是氟、氯、溴和碘。
C1-C25烷基(C1-C18烷基)可能的话通常为线性或支化的。实例是甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、2-戊基、3-戊基、2,2-二甲基丙基、1,1,3,3-四甲基戊基、正己基、1-甲基己基、1,1,3,3,5,5-六甲基己基、正庚基、异庚基、1,1,3,3-四甲基丁基、1-甲基庚基、3-甲基庚基、正辛基、1,1,3,3-四甲基丁基和2-乙基己基,正壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、二十烷基、二十一烷基、二十二烷基、二十四烷基或二十五烷基。C1-C8烷基通常为甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、2-戊基、3-戊基、2,2-二甲基丙基、正己基、正庚基、正辛基、1,1,3,3-四甲基丁基和2-乙基己基。C1-C4烷基通常为甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基。卤代烷基为其中一个或超过一个氢原子被卤原子替换的烷基。
C2-C25链烯基(C2-C18链烯基)为直链或支化链烯基,如乙烯基、烯丙基、甲代烯丙基、异丙烯基、2-丁烯基、3-丁烯基、异丁烯基、正戊-2,4-二烯基、3-甲基丁-2-烯基、正辛-2-烯基、正十二碳-2-烯基、异十二碳烯基、正十二碳-2-烯基或正十八碳-4-烯基。
C2-25炔基(C2-18炔基)为直链或支化的,优选可以未被取代或被取代的C2-8炔基,例如乙炔基、1-丙炔-3-基、1-丁炔-4-基、1-戊炔-5-基、2-甲基-3-丁炔-2-基、1,4-戊二炔-3-基、1,3-戊二炔-5-基、1-己炔-6-基、顺式-3-甲基-2-戊烯-4-炔-1-基、反式-3-甲基-2-戊烯-4-炔-1-基、1,3-己二炔-5-基、1-辛炔-8-基、1-壬炔-9-基、1-癸炔-10-基或1-二十四炔-24-基。
与脂族烃基相反,脂族基团可以被任何无环取代基取代,但优选未被取代。优选的取代基是下面进一步例举的C1-C8烷氧基或C1-C8烷硫基。术语“脂族基团”还包括其中一些非相邻碳原子被氧替代的烷基,如-CH2-O-CH2-CH2-O-CH3。后一基团可以被认为是被-O-CH2-CH2-O-CH3取代的甲基。
具有至多25个碳原子的脂族烃基是如上所例举的具有至多25个碳原子的线性或支化烷基、链烯基或炔基。
亚烷基是二价烷基,即具有2个(而不是1个)自由价键的烷基,例如三亚甲基或四亚甲基。
亚链烯基是二价链烯基,即具有2个(而不是1个)自由价键的链烯基,例如-CH2-CH=CH-CH2-。
与脂族烃基相反,脂族基团可以被任何无环取代基取代,但优选未被取代。优选的取代基是下面进一步例举的C1-C8烷氧基或C1-C8烷硫基。术语“脂族基团”还包括其中一些非相邻碳原子被氧替代的烷基,如-CH2-O-CH2-CH2-O-CH3。后一基团可以被认为是被-O-CH2-CH2-O-CH3取代的甲基。
脂环族烃基是可以被一个或多个脂族和/或脂环族烃基取代的环烷基或环烯基。
脂环族-脂族基团为被脂环族基团取代的脂族基团,其中术语“脂环族”和“脂族”具有本文所给含义且其中自由价键由脂族结构部分延伸。因此,脂环族-脂族基团例如为环烷基烷基。
环烷基烷基是被环烷基取代的烷基,例如环己基甲基。
“环烯基”是指含有一个或多个双键的不饱和脂环族烃基,如环戊烯基、环戊二烯基、环己烯基等,它们可以未被取代或者被一个或多个脂族和/或脂环族烃基取代和/或与苯基稠合。
其中R70和R71一起表示可以经由氧和/或硫键合于该噻吩基残基且可以具有至多25个碳原子的亚烷基或亚链烯基的式的二价基团例如为下式基团:
其中A表示具有至多25个碳原子的线性或支化亚烷基,优选可以被一个或多个烷基取代的亚乙基或亚丙基,并且Y表示氧或硫。例如,式-Y-A-O-的二价基团表示-O-CH2-CH2-O-或-O-CH2-CH2-CH2-O-。
C1-C25烷氧基(C1-C18烷氧基)是直链或支化烷氧基,例如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、叔丁氧基、戊氧基、异戊氧基或叔戊氧基、庚氧基、辛氧基、异辛氧基、壬氧基、癸氧基、十一烷氧基、十二烷氧基、十四烷氧基、十五烷氧基、十六烷氧基、十七烷氧基和十八烷氧基。C1-C8烷氧基的实例是甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、异丁氧基、叔丁氧基、正戊氧基、2-戊氧基、3-戊氧基、2,2-二甲基丙氧基、正己氧基、正庚氧基、正辛氧基、1,1,3,3-四甲基丁氧基和2-乙基己氧基,优选C1-C4烷氧基,通常如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、异丁氧基、叔丁氧基。术语“烷硫基”是指与烷氧基相同的基团,不同的是醚键的氧原子被硫原子替代。
C1-C18全氟烷基,尤其是C1-C4全氟烷基为支化或未支化的基团,例如-CF3、-CF2CF3、-CF2CF2CF3、-CF(CF3)2、-(CF2)3CF3和-C(CF3)3。
术语“氨基甲酰基团”通常为可以未被取代或被取代的C1-18氨基甲酰基团,优选C1-8氨基甲酰基团,如氨基甲酰基、甲基氨基甲酰基、乙基氨基甲酰基、正丁基氨基甲酰基、叔丁基氨基甲酰基、二甲基氨基甲酰氧基、吗啉代氨基甲酰基或吡咯烷基氨基甲酰基。
术语“烷酰基”表示通过羰基连接至母体分子基团的烷基且例如为甲酰基、乙酰基、丙酰基和丁酰基。
术语“甲硅烷基”意指式–SiR62R63R64的基团,其中R62、R63和R64相互独立地为C1-C8烷基,尤其是C1-C4烷基,C6-C24芳基或C7-C12芳烷基,例如三甲基甲硅烷基。术语“硅氧烷基”意指式-O-SiR62R63R64的基团,其中R62、R63和R64如上所定义,例如三甲基硅氧烷基。
环烷基通常为可以未被取代或被取代的C3-C12环烷基,如环戊基、环己基、环庚基、环辛基、环壬基、环癸基、环十一烷基、环十二烷基,优选环戊基、环己基、环庚基或环辛基。环烷基或环烯基,尤其是环己基,可以被苯基稠合1或2次,所述苯基可以被C1-C4烷基、卤素和氰基取代1-3次。该类稠合环己基的实例是 其中R151、R152、R153、R154、R155和R156相互独立地为C1-C8烷基、C1-C8烷氧基、卤素和氰基,尤其是氢。
C6-C24芳基(C6-C18芳基)通常为苯基、茚基、甘菊环基、萘基、联苯基、as-茚烯基(indacenyl)、s-茚烯基、苊基、芴基、菲基、荧蒽基、苯并[9,10]菲基(triphenlenyl)、基、并四苯基、二萘品并苯基、苝基、五联苯基(pentaphenyl)、并六苯基、芘基或蒽基,优选苯基、1-萘基、2-萘基、4-联苯基、9-菲基、2-或9-芴基、3-或4-联苯基,它们可以未被取代或被取代。C6-C12芳基的实例是苯基、1-萘基、2-萘基、3-或4-联苯基、2-或9-芴基或9-菲基,它们可以未被取代或被取代。
C7-C25芳烷基通常为苄基、2-苄基-2-丙基、β-苯基乙基、α,α-二甲基苄基、ω-苯基丁基、ω,ω-二甲基-ω-苯基丁基、ω-苯基十二烷基、ω-苯基十八烷基、ω-苯基二十烷基或ω-苯基二十二烷基,优选C7-C18芳烷基如苄基、2-苄基-2-丙基、β-苯基乙基、α,α-二甲基苄基、ω-苯基丁基、ω,ω-二甲基-ω-苯基丁基、ω-苯基十二烷基或ω-苯基十八烷基,特别优选C7-C12芳烷基如苄基、2-苄基-2-丙基、β-苯基乙基、α,α-二甲基苄基、ω-苯基丁基或ω,ω-二甲基-ω-苯基丁基,其中脂族烃基和芳族烃基均可以未被取代或被取代。优选的实例是苄基、2-苯基乙基、3-苯基丙基、萘基乙基、萘基甲基和枯基。
杂芳基通常为C2-C20杂芳基,即具有5-7个环原子的环或稠合环体系,其中氮、氧或硫为可能的杂原子,并且通常为具有至少6个共轭π-电子的具有5-30个原子的不饱和杂环基团,如噻吩基、苯并[b]噻吩基、二苯并[b,d]噻吩基、噻蒽基、呋喃基、糠基、2H-吡喃基、苯并呋喃基、异苯并呋喃基、氧芴基、苯氧基噻吩基、吡咯基、咪唑基、吡唑基、吡啶基、联吡啶基、三嗪基、嘧啶基、吡嗪基、哒嗪基、中氮茚基、异氮杂茚基、吲哚基、吲唑基、嘌呤基、喹嗪基、喹啉基、异喹啉基、2,3-二氮杂萘基、1,5-二氮杂萘基、喹喔啉基、喹唑啉基、噌啉基、蝶啶基、咔唑基、咔啉基、苯并***基、苯并唑基、菲啶基、吖啶基、嘧啶基、菲咯啉基、吩嗪基、异噻唑基、吩噻嗪基、异唑基、呋咱基或吩嗪基,它们可以未被取代或被取代。
上述基团的可能取代基是C1-C8烷基、羟基、巯基、C1-C8烷氧基、C1-C8烷硫基、卤素、卤代-C1-C8烷基、氰基、氨基甲酰基团、硝基或甲硅烷基,尤其是C1-C8烷基、C1-C8烷氧基、C1-C8烷硫基、卤素、卤代-C1-C8烷基或氰基。
被一个或多个O间隔的C1-C25烷基(C1-C18烷基)例如为(CH2CH2O)1-9-R44,其中R44为H或C1-C10烷基,CH2-CH(ORy')-CH2-O-Ry,其中Ry为C1-C25烷基(C1-C18烷基)且Ry'包括与Ry相同的定义或者为H。
若取代基如R3在基团中出现不止一次,则它可以在每次出现时不同。
有利地,本发明化合物或包含本发明化合物的有机半导体器材料、层或组件可用于有机光伏器件(太阳能电池)和光电二极管或有机场效应晶体管(OFET)中。
式I化合物可以呈现p型晶体管行为且可以在半导体器件中用作半导体层。因此,本发明还涉及包含式I化合物作为半导体有效装置的半导体器件。
本发明尤其涉及一种包含分别选自权利要求10所示式A-1至A-22、B-1至B-2化合物的实施例所述式I化合物作为半导体有效装置的半导体器件。
优选所述半导体器件为二极管、光电二极管、传感器、有机场效应晶体管(OFET)、柔性显示器用晶体管或太阳能电池,或含有二极管和/或有机场效应晶体管和/或太阳能电池的器件。存在许多类型的半导体器件。对所有这些常见的是存在一种或多种半导体材料。半导体器件例如已经由S.M.Sze描述于Physics of Semiconductor Devices,第2版,JohnWiley and Sons,New York(1981)中。该类器件包括整流器、晶体管(其中有许多类型,包括p-n-p、n-p-n和薄膜晶体管)、发光半导体器件(例如显示器应用中的有机发光二极管或例如液晶显示器中的背光灯)、光电导体、电流限制器、太阳能电池、电热调节器、p-n结、场效应二极管、肖特基二极管等等。在各半导体器件中,将半导体材料与一种或多种金属和/或绝缘体组合以形成该器件。半导体器件可以通过已知方法如Peter Van Zant在MicrochipFabrication,第4版,McGraw-Hill,New York(2000)中所述那些制备或制造。有机电子组件尤其可以如D.R.Gamota等在Printed Organic and Molecular Electronics,KluverAcademic Publ.,Boston,2004所述制造。
特别有用类型的晶体管器件—薄膜晶体管(TFT)通常包括栅电极、在栅电极上的栅电介质、与栅电介质相邻的源电极和漏电极以及与栅电介质相邻并与源电极和漏电极相邻的半导体层(例如参见S.M.Sze,Physics of Semiconductor Devices,第2版,JohnWiley和Sons,第492页,New York(1981))。这些组件可以以各种构造组装。更具体而言,有机薄膜晶体管(OTFT)具有有机半导体层。
衬底通常在制造、测试和/或使用过程中支撑OTFT。任选地,衬底可以为OTFT提供电功能。有用的衬底材料包括有机和无机材料。例如,衬底可以包括硅材料(包括各种合适形式的硅在内),无机玻璃,陶瓷箔,聚合物材料(例如丙烯酸类聚合物,聚酯,环氧化物,聚酰胺,聚碳酸酯,聚酰亚胺,聚酮,聚(氧基-1,4-亚苯氧基-1,4-亚苯基羰基-1,4-亚苯基)(有时称为聚(醚醚酮)或PEEK),聚降冰片烯,聚苯醚,聚(萘二甲酸乙二醇酯)(PEN),聚(对苯二甲酸乙二醇酯)(PET),聚(苯硫醚)(PPS)),填充的聚合物材料(例如纤维增强的塑料(FRP)),以及涂敷的金属箔。衬底可具有任何合适的厚度,优选为10μm至10mm,甚至更优选10μm至1mm。
栅电极可以是任何有用的导电材料。例如,栅电极可以包括掺杂的硅,或金属,如铝、铬、金、银、镍、钯、铂、钽和钛。还可以使用导电性氧化物,如氧化铟锡(ITO),或由碳黑/石墨或胶态银分散体构成的导电性油墨/糊,它们任选含有聚合物粘合剂。还可以使用导电性聚合物,例如聚苯胺或聚(3,4-亚乙二氧基噻吩)/聚(苯乙烯磺酸酯)(PEDOT:PSS)。此外,也可使用这些材料的合金、组合和多层。在一些OTFT中,相同材料可以可以提供栅电极功能并还提供衬底的支撑功能。例如,掺杂的硅可以起栅电极的作用并支撑OTFT。
栅电介质通常提供在栅电极上。该栅电介质将栅电极与OTFT器件的其余部分(balance)电绝缘。对栅电介质有用的材料可以包括例如无机电绝缘材料。
栅电介质(绝缘体)可以是诸如氧化物、氮化物的材料,或者它可以是选自铁电绝缘体(例如有机材料如聚(偏二氟乙烯/三氟乙烯或聚(己二酰间苯二甲胺)(poly(m-xylylene adipamide))的材料,或者它可以是例如如J.Veres等,Chem.Mat.2004,16,4543或A.Facchetti等,Adv.Mat.2005,17,1705中所述的有机聚合物绝缘体(例如聚甲基丙烯酸酯、聚丙烯酸酯、聚酰亚胺、苯并环丁烯(BCB)、聚对亚苯基二甲基、聚乙烯醇、聚乙烯基苯酚(PVP)、聚苯乙烯、聚酯、聚碳酸酯)。可以用于栅电介质的材料的具体实例包括锶酸盐、钽酸盐、钛酸盐、锆酸盐、铝氧化物、硅氧化物、钽氧化物、钛氧化物、硅氮化物、钛酸钡、钛酸锶钡、锆酸钛酸钡、硒化锌和硫化锌,包括但不限于PbZrxTi1-xO3(PZT)、Bi4Ti3O12、BaMgF4、Ba(Zr1-xTix)O3(BZT)。此外,可以将这些材料的合金、混杂材料(例如聚硅氧烷或纳米颗粒填充聚合物)组合和多层用于栅电介质。电介质层的厚度例如为约10-1000nm,更具体的厚度为约100-500nm,提供的电容范围为0.1-100纳法拉(nF)。
源电极和漏电极由栅电介质与栅电极分开,而有机半导体层可以在源电极和漏电极之上或之下。源电极和漏电极可以是任何有利地对该半导体层提供低电阻欧姆接触的有用导电性材料。有用的材料包括上面对栅电极所述那些材料中的大多数,例如铝、钡、钙、铬、金、银、镍、钯、铂、钛、聚苯胺、PEDOT:PSS,其他导电性聚合物、其合金、其组合及其多层。正如本领域已知的那样,这些材料中的一些适合用于n型半导体材料且其他的适合用于p型半导体材料。
薄膜电极(即栅电极、源电极和漏电极)可以通过任何有用的手段如物理气相沉积(例如热蒸发或溅射)或(喷墨)印刷方法提供。这些电极的图案化可以通过已知方法如阴影掩蔽、相加性光刻法、相减性光刻法、印刷、微接触印刷和图案涂敷。
本发明进一步提供了一种薄膜晶体管器件,其包括:
多个设置在衬底上的导电栅电极;
设置在所述导电栅电极上的栅极绝缘层;
设置在所述绝缘层上的多组导电源电极和漏电极,以使所述各组与各所述栅电极对准;
设置在所述绝缘层上的源电极和漏电极之间的通道中的有机半导体层,其基本覆盖所述栅电极;其中所述有机半导体层包含式I化合物。
此外,本发明提供了一种制备薄膜晶体管器件的方法,该方法包括下列步骤:
在衬底上沉积多个导电栅电极;
在所述导电栅电极上沉积栅极绝缘层;
在所述层上沉积多组导电源电极和漏电极,以使所述各组与各所述栅电极对准;
在所述绝缘层上沉积包含式I化合物的层,以使包含式I化合物的所述层基本覆盖所述栅电极,由此生产薄膜晶体管器件。
包含式I化合物的上述层可以额外至少包含其他材料。该其他材料可以为,但不限于,另一式I化合物、半导体聚合物、聚合物粘合剂、不同于式I化合物的有机小分子、碳纳米管、富勒烯衍生物、无机颗粒(量子点、量子棒、量子三脚架(tripod)、TiO2、ZnO等)、导电颗粒(Au、Ag等)以及如对栅电介质所述的那些绝缘体材料(PET、PS等)。如上所述,该半导体层也可以由一种或多种式I的小分子和聚合物粘合剂的混合物构成。式I的小分子与该聚合物粘合剂的比例可以在5-95%内变化。优选该聚合物粘合剂为半结晶聚合物如聚苯乙烯(PS),高密度聚乙烯(HDPE),聚丙烯(PP)和聚甲基丙烯酸甲酯(PMMA)。使用该技术可以避免电性能的变差(参见WO2008/001123A1)。
任何合适的衬底可以用于制备式I化合物的薄膜。优选用于制备上述薄膜的衬底是金属、硅、塑料、纸、涂布纸、织物、玻璃或涂布玻璃。
或者,TFT例如通过式I化合物在用热生长氧化物层覆盖的高度掺杂硅衬底上的溶液沉积或真空沉积以及随后源电极和漏电极的真空沉积和图案化而制造。
在另一方法中,TFT通过源电极和漏电极在用热生长的氧化物覆盖的高度掺杂硅衬底上的沉积以及随后式I化合物的溶液沉积以形成薄膜而制造。
栅电极还可以是在衬底或导电材料如导电聚合物上的图案化金属栅电极,其随后用通过溶液涂敷或真空沉积而施用于图案化栅电极上的绝缘体涂敷。
可以使用任何合适的溶剂来溶解和/或分散式I化合物,条件是它呈惰性且可以通过常规干燥方法(例如施加热、减压、气流等)而从衬底上部分或完全除去。适于加工本发明半导体的有机溶剂包括但不限于芳族或脂族烃类,卤代烃类如氯代或氟代烃类,酯类,醚类,酰胺类,如氯仿、四氯乙烷、四氢呋喃、甲苯、四氢化萘、茴香醚、二甲苯、乙酸乙酯、甲基乙基酮、二甲基甲酰胺、二氯苯、三氯苯、丙二醇单甲醚乙酸酯(PGMEA)及其混合物。然后通过诸如旋涂、浸涂、丝网印刷、微接触印刷、刮刀涂敷的方法或本领域已知的其他溶液施用技术在衬底上施用该溶液和/或分散体而得到半导电材料的薄膜。
术语“分散体”涵盖包含式I化合物的任何组合物,该化合物不完全溶于溶剂中。该分散可以通过选择至少包含式I化合物或含有式I化合物和溶剂的混合物的组合物而进行,其中该聚合物在室温下在该溶剂中呈现较低溶解性,但在升高的温度下在该溶剂中呈现较高溶解性,其中该组合物在不搅拌下由升高的温度降至第一较低温度时胶凝;
-在升高的温度下将至少一部分式I化合物溶于该溶剂中;将该组合物的温度由升高的温度降至第一较低温度;搅拌该组合物以破坏任何胶凝,其中该搅拌在将该组合物的升高的温度降至第一更低温度之前、同时或之后的任何时间开始;沉积一层该组合物,其中该组合物处于比所述升高的温度更低的第二较低温度下;并至少部分干燥该层。
该分散体还可以由(a)包含溶剂、粘合剂树脂和任选的分散剂的连续相以及(b)包含式I化合物或含有式I化合物的本发明混合物的分散相构成。式I化合物在溶剂中的溶解度例如可以在0.5%至约20%溶解度,特别是1%至约5%溶解度范围内变化。
优选有机半导体层的厚度为约5-1000nm,尤其厚度是约10-100nm。
式I化合物可以单独或组合用作半导体器件的有机半导体层。该层可以通过任何有用的措施,如气相沉积和印刷技术提供。可以充分溶于有机溶剂中的式I化合物可以溶液沉积和图案化(例如通过旋涂、浸涂、喷墨印刷、凹版印刷、柔性印刷、胶版印刷、丝网印刷、微接触(微波)印刷、液滴或区域流延(drop或zone casting)或其他已知技术)。
式I化合物可以用于包含多个OTFT的集成电路以及各种电子制品中。这类制品例如包括射频识别(RFID)标签,柔性显示器用背板(例如用于个人计算机、移动电话或手持设备),智能卡,存储器件,传感器(例如光、图象、生物、化学、机械或温度传感器),尤其是光电二极管,或安全装置等。由于其双极性,该材料还可以用于有机发光晶体管(OLET)中。
此外,本发明提供了包含式I化合物的有机光伏(PV)器件(太阳能电池)。有机光伏器件(太阳能电池)的结构例如描述于C.Deibel等Rep.Prog.Phys.73(2010)096401和Christoph Brabec,Energy Environ.Sci2.(2009)347-303中。
PV器件以如下顺序包括:
(a)阴极(电极),
(b)任选的过渡层,如碱金属卤化物,尤其是氟化锂,
(c)感光层,
(d)任选的平滑层,
(e)阳极(电极),
(f)衬底。
该感光层包含式I化合物。优选该感光层由作为电子供体的式I化合物和作为电子受体的受体材料如富勒烯,特别是官能化富勒烯PCBM构成。如上所述,该感光层还可以含有聚合物粘合剂。式I的小分子与聚合物粘合剂的比例可以在5-95%内变化。优选该聚合物粘合剂为半结晶聚合物如聚苯乙烯(PS),高密度聚乙烯(HDPE),聚丙烯(PP)和聚甲基丙烯酸甲酯(PMMA)。
可以用于本发明中的富勒烯可以具有宽范围的尺寸(每分子的碳原子数)。本文所用术语富勒烯包括纯碳的各种笼状分子,包括Buckminster富勒烯(C60)和相关“球形”富勒烯以及碳纳米管。富勒烯可以选自本领域已知的那些,例如C20-C1000。优选富勒烯选自C60-C96。最优选富勒烯为C60或C70,如[60]PCBM或[70]PCBM。还可以利用化学改性的富勒烯,条件是该改性富勒烯保持受体类型和电子迁移率特性。该受体材料也可以是选自另一式I化合物或任何半导体聚合物的材料,条件是该聚合物保持受体类型和电子迁移率特性,有机小分子,碳纳米管,无机颗粒(量子点、量子棒、量子三脚架、TiO2、ZnO等)。
对于异质结太阳能电池(体异质结太阳能电池),该活性层优选以1:1-1:3的重量比包含式I化合物和富勒烯如[60]PCBM(=6,6-苯基-C61-丁酸甲酯)或[70]PCBM的混合物。亚甲基富勒烯(methanofullerene)苯基-C61-丁酸甲酯([60]PCBM),即1-[3-(甲氧羰基)丙基]-1-苯基-[6.6]C61-3'H-环丙并[1,9][5,6]富勒烯-C60-Ih-3'-丁酸3'-苯基甲基酯是有效的可溶液加工的n型有机半导体。将它与含纳米颗粒如C60的共轭聚合物共混。
电极优选由金属或“金属替代物”构成。本文中术语“金属”用于包括由单质纯金属如Mg构成的材料以及还有为由两种或更多种单质纯金属如Mg和Ag一起(表示为Mg:Ag)构成的材料的金属合金。本文中术语“金属替代物”是指不为正常定义内的金属,但具有在某些合适应用中希望的金属状性能的材料。对电极和电荷转移层常用的金属替代物包括掺杂的宽带隙半导体,例如透明导电氧化物,如氧化铟锡(ITO)、氧化镓铟锡(GITO)和氧化锌铟锡(ZITO)。另一合适的金属替代物是透明导电性聚合物聚苯胺(PANI)及其化学相关物,或PEDOT:PSS。金属替代物可以进一步选自宽范围的非金属材料,其中术语“非金属”意欲包括宽范围的材料,条件是该材料不含呈其未化学结合形式的金属。高度透明的非金属低电阻阴极或高度有效的低电阻金属/非金属化合物阴极例如公开于US-B-6,420,031和US-B-5,703,436中。
衬底例如可以为塑料(柔性衬底)或玻璃衬底。
在本发明的另一优选实施方案中,平滑层位于阳极和感光层之间。该平滑层的优选材料包括3,4-聚亚乙二氧基噻吩(PEDOT)或3,4-聚亚乙二氧基噻吩:聚苯乙烯磺酸酯(PEDOT:PSS)的薄膜。
在本发明的优选实施方案中,该光伏电池例如如US-B-6,933,436所述包括透明玻璃载体,其上施加由氧化铟/锡(ITO)构成的电极层。该电极层通常具有较粗糙的表面结构,因而将其用由聚合物,通常是PEDOT构成的平滑层覆盖,后者通过掺杂而导电。该感光层由两种组分构成,层厚取决于施用方法例如为100nm至几个μm且施用于该平滑层上。该感光层由作为电子供体的式I化合物和作为电子受体的富勒烯,特别是官能化富勒烯PCBM构成。将这两种组分与溶剂混合并通过例如旋涂方法、液滴流延(drop casting)方法、Langmuir-Blodgett(“LB”)方法、喷墨印刷方法和浸涂方法作为溶液施加于平滑层上。还可以使用刮板或印刷方法来用该感光层涂敷更大表面。代替常用的甲苯,优选将分散剂如氯苯用作溶剂。考虑到操作容易性和成本,在这些方法中特别优选真空沉积方法、旋涂方法、喷墨印刷方法和流延方法。
在通过使用旋涂方法、流延方法和喷墨印刷方法形成该层的情况下,涂敷可以使用通过将该组合物以0.01-90重量%的浓度溶于或分散于合适有机溶剂如苯、甲苯、二甲苯、四氢呋喃、甲基四氢呋喃、N,N-二甲基甲酰胺、丙酮、乙腈、茴香醚、二氯甲烷、二甲亚砜、氯苯、1,2-二氯苯及其混合物中而制备的溶液和/或分散体进行。
在施用反电极之前,将层厚为例如0.6nm的必须电绝缘的薄过渡层施用于该感光层。在该示例性实施方案中,该过渡层由碱金属卤化物,即氟化锂构成,其以0.2nm/分钟的速率在2·10-6乇的真空中气相沉积。
若将ITO用作空穴收集电极,则将气相沉积于电绝缘过渡层上的铝用作电子收集电极。该过渡层的电绝缘性能显然防止了妨碍载流子通过的影响起作用,特别是在由该感光层到该过渡层的过渡区中。
在本发明的另一实施方案中,这些层中的一个或多个可以在沉积下一层之前用等离子体处理。特别有利的是在沉积PEDOT:PSS层之前将阳极材料进行温和等离子体处理。
作为PEDOT:PSS的替代品,可以使用在Macromol.Rapid Commun.20,224-228(1999)中提到的基于三芳基胺的可交联空穴传输材料。除了三芳基胺材料外,该层还可以包含电子受体以改善电子传输。该类化合物公开于US2004/0004433中。优选该电子受体材料可溶于一种或多种有机溶剂中。通常而言,该电子受体材料以该三芳基胺材料的0.5-20重量%存在。
该光伏(PV)器件还可以由相互重叠地加工以吸收更多太阳光谱的复结(multiplejunction)太阳能电池构成。该类结构例如描述于App.Phys.Let.90,143512(2007),Adv.Funct.Mater.16,1897-1903(2006)和WO2004/112161和Christoph Brabec,EnergyEnviron.Sci2.(2009)347-303中。
所谓的‘串接太阳能电池’以如下顺序包括:
(a)阴极(电极),
(b)任选的过渡层,如碱金属卤化物,尤其是氟化锂,
(c)感光层,
(d)任选的平滑层,
(e)中间电极(如Au、Al、ZnO、TiO2等),
(f)任选的额外电极以匹配能级,
(g)任选的过渡层,如碱金属卤化物,尤其是氟化锂,
(h)感光层,
(i)任选的平滑层,
(j)阳极(电极),
(k)衬底。
PV器件还可以如例如US20070079867和US20060013549中所述在纤维上加工。
由于其优异的自组织性能,包含式I化合物的材料或薄膜还可以单独或与其他材料一起用于LCD或OLED器件中的对准层中或用作该对准层,例如如US2003/0021913所述。
本发明的各种特征和方面在下列实施例中进一步说明。尽管提供这些实施例以向本领域熟练技术人员说明如何在本发明范围内操作,但它们不用来限制本发明范围,该范围仅在权利要求书中定义。除非在下列实施例以及说明书和权利要求书中其他地方另有指明,所有份数和百分数按重量计,温度按摄氏温标计且压力为大气压或接近大气压。
实施例
实施例1
a)使20g[88949-34-2]和25.76g碳酸钾悬浮于300ml干二甲基甲酰胺中并将该混合物在氮气下加热至90°C。然后滴加79g[1044598-79-9]。然后将反应混合物在90°C下搅拌6小时。在冷却至室温后,加入乙酸乙酯并用水洗涤混合物。将有机相在硫酸镁上干燥并使溶剂蒸发。产物通过在二氧化硅上柱层析而提纯以得到化合物1。1H-NMR数据(ppm,CDCl3):8.332H d,7.602H d,6.682H dxd,4.034H d,1.85-1.752H m,1.45-1.1548H m,0.886H t,0.866H t。
b)将26.30g化合物1溶于300ml氯仿中。将该混合物冷却至-10°C,然后加入11.42gN-溴琥珀酰亚胺(NBS)并将混合物在-10°C下搅拌2小时。将反应混合物用水洗涤、用硫酸镁干燥并蒸发溶剂。粗产物通过在二氧化硅上柱层析提纯而得到化合物2。1H-NMR数据(ppm,CDCl3):8.351H d,8.301H d,7.621H d,6.711H dxd,6.621H d,4.032H d,4.002H d,1.87-1.752Hm,1.45-1.2048H m,0.886H t,0.866H t。
c)将232mg化合物2、58mg化合物[1256165-36-2]、2mg Pd(OAc)2和25mg2-(二叔丁基膦基)-1-苯基吲哚在氩气下置于反应器中。然后加入20ml不含氧气的THF并将反应混合物加热至50°C。然后加入37mg一水合氢氧化锂并然后将反应混合物在回流温度下加热2小时。将反应混合物倾于冰/水上,并然后用氯仿萃取。将有机相在MgSO4上干燥并蒸发。然后在粗产物柱层析之后得到化合物3。1H-NMR数据(ppm,CDCl3):8.462H d,8.362H d,7.712Hs,7.622H s,7.592H d,6.892H d,6.702H d,4.134H d,4.034H d,1.962H broad s,1.832Hbroad s,1.45-1.1596H m,0.8912H t,0.8212H t。
实施例2
使2当量化合物2和1当量化合物[175361-81-6]根据实施例1反应而得到化合物4。
实施例3
使2当量化合物2和1当量化合物[239075-02-6]根据实施例1反应而得到化合物5。
实施例4
使2当量化合物2和1当量化合物[476004-84-9]根据实施例1反应而得到化合物6。
实施例5
使2当量化合物2和1当量化合物[849543-98-2]根据实施例1反应而得到化合物7。
应用实施例1
底栅极底接触(BGBC)场效应晶体管(FET):
硅衬底上的晶体管的标准程序:将230nm厚热生长的二氧化硅层且在二氧化硅层顶部上具有氧化铟锡(15nm)/金(30nm)接触的重掺杂的硅晶片(Sin--(425±40μm)用作衬底。衬底通过在丙酮和异丙醇中标准清洁并随后通过氧等离子体处理30分钟制备,然后转移至手套箱并用辛基三氯硅烷(OTS)处理而得到疏水单层。
半导体膜的沉积:将半导体化合物3在升高的温度下以0.75重量%的浓度溶于甲苯中并以1500转/分钟(rpm)旋涂60秒而旋涂于二氧化硅/硅衬底。所有电测量在氮气氛围下在手套箱中用10V至-30V的门电压(Vg)和等于3V和30V的漏极电压(Vd)进行转移表征。为了输出表征,在Vg=0、10、20、30V下Vd为0至-30V。测量的迁移率表示在Vd=-30V下的饱和迁移率。
化合物3在有机溶剂中具有优异的溶解性并具有优异的成膜性能。其中半导体层由化合物3构成的应用实施例1的FET显示出p型特性并具有优异的加工性和再现性。
应用实施例2
有机本体异质结太阳能电池
太阳能电池具有如下结构:Al电极/LiF层/包含化合物3和1-[3-(甲氧基羰基)丙基]-1-苯基-[6.6]C613′H-环丙[1,9][5,6]富勒烯-C60-Ih-3′-丁酸3′-苯基甲基酯([60]PCBM)的有机层/[聚(3,4-亚乙二氧基噻吩)与聚(苯乙烯磺酸)(PSS)的混合物]/ITO电极/玻璃衬底。太阳能电池通过在玻璃衬底上的预图案化的ITO上旋涂PEDOT-PSS层而制备。然后将本发明化合物(1重量%):[60]PCBM(取代的C60富勒烯)的1:2混合物由氯仿中旋涂(有机层)。LiF和Al在高真空下通过遮蔽掩模升华。
太阳能电池性能
太阳能电池在Aescusoft太阳光模拟器下用卤素光源测量。在AM1.5条件下使用外部量子效率(EQE)图估算电流。
其中半导体层由化合物3和[60]PCBM构成的应用实施例1的太阳能电池显示出OPV特性并具有优异的加工性和再现性。
Claims (15)
1.一种式化合物,其中
p为0或1,q为0或1,
A1和A2相互独立地为式的基团,其中
a为1,b为0或1,c为0或1,
Ar1为下式基团:
Ar2和Ar3相互独立地为下式基团:
R3为氢或C1-C25烷基,
A3、A4和A5相互独立地为式的基团,
k为0、1或2;l为1、2或3;r为0或1;z为0、1或2;其中k+l+r+z为1或3;
Ar4、Ar5、Ar6和Ar7相互独立地为下式基团:
R10为氢、C1-C25烷基或COO-C1-C25烷基,
R16和R17相互独立地为氢、卤素、C1-C25烷基、C1-C25烷氧基、C7-C25芳基烷基或
Rx为C1-C12烷基或三(C1-C8烷基)甲硅烷基,
R20和R21相互独立地为氢或C1-C25烷基,
R30-R35相互独立地为氢或C1-C25烷基,和
R42和R43相互独立地为C1-C25烷基,
R1、R2、R1’、R2’、R1”、R2”、R1*和R2*可相同或不同且选自C1-C50烷基,条件为如果q为0,p为0,k为0,r为0,z为0和l为1,则Ar5不为基团
2.根据权利要求1的化合物,其为下式化合物:
其中A1、A2、A3、A4、A5、R1、R2、R1’、R2’、R1”、R2”、R1*和R2*如权利要求1所定义。
3.根据权利要求1的化合物,其中
A1和A2相互独立地为式的基团,其中
a为1,b为0或1,c为0或1,
Ar2和Ar3相互独立地为和
R3为H或C1-C25烷基。
4.根据权利要求1的化合物,其中A3、A4和A5相互独立地为式的基团,
k和z为0或1;l为1、2或3;r为0;
Ar4和Ar7为式的基团,
Ar5为下式基团:
R10为H或C1-C25烷基,
R16和R17为H或C1-C25烷基,和
R32和R33为H或C1-C25烷基。
5.根据权利要求1-4中任一项的化合物,其为下式化合物:
其中
b为0或1,c为0或1,
A3、A4、Ar5和Ar6相互独立地为下式基团:
Ar2和Ar3相互独立地为
R1、R2、R1’、R2’、R1*和R2*选自C1-C50烷基,
R3为H或C1-C25烷基,
R10为H或C1-C25烷基,
R16和R17为H或C1-C25烷基,和
R32和R33为H或C1-C25烷基。
6.根据权利要求5的化合物,其为下式化合物:
其中A3、Ar5、R1、R2、R1*和R2*如权利要求1所定义。
7.根据权利要求5的化合物,其为下式化合物:
其中R1、R2、R1’、R2’、R1*、R2*、A3、A4、Ar5和Ar6如权利要求1所定义。
8.根据权利要求1或2的化合物:
9.一种半导体器件,包含如权利要求1-8中任一项所定义的式I化合物。
10.根据权利要求9的半导体器件,其呈二极管、传感器、有机场效应晶体管、柔性显示器的晶体管或太阳能电池的形式。
11.根据权利要求9的半导体器件,其呈光电二极管的形式。
12.如权利要求1-8中任一项所定义的式I化合物作为p型晶体管的用途。
13.一种制备其中R2为R1*的式化合物的方法,包括:
(a)在强碱存在下使2摩尔式化合物与1摩尔式的二腈化合物反应,其中R200和R200’相互独立地为C1-C8烷基或苄基;
(b)然后用化合物R2-X16在碱性条件下在干燥溶剂中烷基化在步骤a)中得到的式化合物,其中A1、A2、A3、R1和R2*如权利要求1所定义,X16为卤素;或
一种制备其中R1=R2=R1*=R2*的式化合物的方法,包括:
(a)在强碱存在下使2摩尔琥珀酸二酯与1摩尔式的腈和2摩尔式的腈反应,
(b)使在步骤a)中得到的式化合物与式R1-X16的溴化物在合适碱存在下在合适溶剂中反应,R1、R1’、R2’、A1、A3和A4如上所定义,X16为卤素。
14.一种式化合物,其中
A1’和A2’相互独立地为式的基团,
R3’每次出现独立地为ZnX12、-SnR207R208R209,其中R207、R208和R209相同或不同且为H或C1-C6烷基,其中两个基团任选形成公共环且这些基团任选支化或未支化;
X12为卤素原子、-OS(O)2CF3、-OS(O)2-芳基、-OS(O)2CH3、-B(OH)2、-B(OH)3 -、-BF3、-B(OY1)2、其中Y1每次出现独立地为C1-C12烷基和Y2每次出现独立地为C2-C10亚烷基,和Y13和Y14相互独立地为氢或C1-C12烷基;a、b、c、q、p、R1、R2、R1’、R2’、R1”、R2”、R1*、R2*、Ar1、Ar2、Ar3、A3、A4和A5如权利要求1所定义。
15.根据权利要求14的式(X)化合物在制备聚合物中的用途。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161499700P | 2011-06-22 | 2011-06-22 | |
US61/499,700 | 2011-06-22 | ||
EP11170877 | 2011-06-22 | ||
EP11170877.2 | 2011-06-22 | ||
PCT/EP2012/061777 WO2012175530A1 (en) | 2011-06-22 | 2012-06-20 | Diketopyrrolopyrrole oligomers for use in organic semiconductor devices |
Publications (2)
Publication Number | Publication Date |
---|---|
CN103619855A CN103619855A (zh) | 2014-03-05 |
CN103619855B true CN103619855B (zh) | 2017-08-08 |
Family
ID=47422048
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201280030124.3A Active CN103619855B (zh) | 2011-06-22 | 2012-06-20 | 用于有机半导体器件的二酮基吡咯并吡咯低聚物 |
Country Status (7)
Country | Link |
---|---|
US (1) | US9362508B2 (zh) |
EP (1) | EP2723750B1 (zh) |
JP (1) | JP6165135B2 (zh) |
KR (1) | KR102009846B1 (zh) |
CN (1) | CN103619855B (zh) |
TW (1) | TWI609020B (zh) |
WO (1) | WO2012175530A1 (zh) |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013028441A2 (en) * | 2011-08-19 | 2013-02-28 | University Of Washington | New poly(heteroarylene vinylene)s based on diketopyrrolopyrrole |
KR102030859B1 (ko) | 2011-09-02 | 2019-10-10 | 바스프 에스이 | 디케토피롤로피롤 올리고머, 및 디케토피롤로피롤 올리고머를 포함하는 조성물 |
CN103906786B (zh) | 2011-10-04 | 2017-06-09 | 巴斯夫欧洲公司 | 基于苯并二酮的聚合物 |
US9356241B2 (en) * | 2011-10-13 | 2016-05-31 | The Regents Of The University Of California | End-group-directed self-assembly of organic compounds useful for photovoltaic applications |
KR102017358B1 (ko) | 2011-12-07 | 2019-09-26 | 바스프 에스이 | 유기 반도체 장치에 사용하기 위한 디케토피롤로피롤 중합체 |
CN103975453B (zh) | 2011-12-07 | 2018-01-30 | 巴斯夫欧洲公司 | 有机场效应晶体管 |
KR102030867B1 (ko) | 2012-04-02 | 2019-10-10 | 바스프 에스이 | 전자 응용을 위한 페난트로[9,10-b]푸란 중합체 및 소분자 |
WO2013150005A1 (en) | 2012-04-04 | 2013-10-10 | Basf Se | Diketopyrrolopyrrole polymers and small molecules |
WO2014016219A1 (en) | 2012-07-23 | 2014-01-30 | Basf Se | Dithienobenzofuran polymers and small molecules for electronic application |
US9564604B2 (en) * | 2012-10-18 | 2017-02-07 | Nippon Kayaku Kabushiki Kaisha | Fused polycyclic aromatic compounds, organic semiconductor material and thin film including the same, and method for producing an organic semiconductor device |
CN104177381A (zh) * | 2013-05-27 | 2014-12-03 | 海洋王照明科技股份有限公司 | 含二噻吩并吡咯单元的有机半导体材料及其制备方法和太阳能电池器件 |
CN104177382A (zh) * | 2013-05-27 | 2014-12-03 | 海洋王照明科技股份有限公司 | 含萘并二噻吩单元的有机半导体材料及其制备方法和太阳能电池器件 |
GB2530954A (en) * | 2013-06-21 | 2016-04-06 | Merck Patent Gmbh | Conjugated polymers |
KR101702183B1 (ko) * | 2013-10-28 | 2017-02-06 | 주식회사 엘지화학 | 단분자 및 이를 포함하는 유기 태양 전지 |
CN106103436B (zh) * | 2014-03-17 | 2019-07-09 | 默克专利股份有限公司 | 有机半导体化合物 |
US9580556B2 (en) | 2015-01-29 | 2017-02-28 | Corning Incorporated | DPP with branched alkyl-chain or (and) fused thiophene with branched alkyl-chain and the related designing strategy to increase the molecular weight of their semi-conducting copolymers |
US20160362522A1 (en) * | 2015-06-13 | 2016-12-15 | The Pen | True nanoscale one and two-dimensional organometals |
CN106928255B (zh) * | 2017-03-29 | 2019-05-24 | 湖南文理学院 | 一种苯并二呋喃类有机小分子光伏材料及其制备方法和应用 |
EP3762979A1 (en) | 2018-03-07 | 2021-01-13 | Clap Co., Ltd. | Patterning method for preparing top-gate, bottom-contact organic field effect transistors |
EP3762980B1 (en) | 2018-03-08 | 2023-08-09 | Clap Co., Ltd. | Organic field effect transistor comprising semiconducting single-walled carbon nanotubes and organic semiconducting material |
JP2021530577A (ja) | 2018-06-26 | 2021-11-11 | クラップ カンパニー リミテッドClap Co., Ltd. | 誘電体としてのビニルエーテル系高分子 |
US11552250B2 (en) | 2019-07-30 | 2023-01-10 | Samsung Electronics Co., Ltd. | Polymer and organic thin film and thin film transistor and electronic device |
CN110922418B (zh) * | 2019-11-18 | 2021-05-18 | 河北工业大学 | 吡咯并吡咯二酮类共轭寡聚物及基于其的纳米粒子以及它们的制备方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101072842A (zh) * | 2004-12-09 | 2007-11-14 | 西巴特殊化学品控股有限公司 | 荧光二酮基吡咯并吡咯化合物 |
EP2033983A2 (en) * | 2007-09-06 | 2009-03-11 | Xerox Corporation | Diketopyrrolopyrrole-Based Polymers |
WO2011025454A1 (en) * | 2009-08-28 | 2011-03-03 | Agency For Science, Technology And Research | Ambipolar polymeric semiconductor materials and organic electronic devices |
Family Cites Families (48)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE59408909D1 (de) | 1993-10-13 | 1999-12-16 | Ciba Sc Holding Ag | Neue Fluoreszenzfarbstoffe |
EP0648770B1 (de) | 1993-10-13 | 2000-05-17 | Ciba SC Holding AG | Pyrrolo[3,4-c]pyrrole |
US5703436A (en) | 1994-12-13 | 1997-12-30 | The Trustees Of Princeton University | Transparent contacts for organic devices |
EP0742255B1 (en) | 1995-05-12 | 2004-04-14 | Ciba SC Holding AG | Colouration of high molecular weight organic materials in the mass with soluble phthalocyanine precursors |
DE59604654D1 (de) | 1995-07-28 | 2000-04-20 | Ciba Sc Holding Ag | Lösliche Chromophore mit leicht abspaltbaren löslichmachenden Gruppen |
EP0787731B1 (de) * | 1996-01-30 | 2002-08-07 | Ciba SC Holding AG | Polymerisierbare Diketopyrrolopyrrole und damit hergestellte Polymere |
EP0968250B1 (en) | 1997-01-27 | 2001-04-18 | Ciba SC Holding AG | Soluble chromophores having improved solubilising groups |
AU7211498A (en) | 1997-04-09 | 1998-10-30 | Ciba Specialty Chemicals Holding Inc. | Black-pigmented structured high molecular weight material |
US20010012559A1 (en) | 1997-06-17 | 2001-08-09 | John Zambounis | Pigmented porous material |
AU8541098A (en) | 1997-06-30 | 1999-01-25 | Ciba Specialty Chemicals Holding Inc. | Pigment dispersions containing c.i. pigment red 222 |
US5919944A (en) * | 1997-07-30 | 1999-07-06 | Ciba Specialty Chemicals Corporation | Polymerisable diketopyrrolopyrroles |
US6420031B1 (en) | 1997-11-03 | 2002-07-16 | The Trustees Of Princeton University | Highly transparent non-metallic cathodes |
EP1119590B1 (de) | 1998-09-21 | 2003-01-08 | Ciba SC Holding AG | Substituierte phthalocyanine |
US6495250B1 (en) | 1998-12-16 | 2002-12-17 | Ciba Specialty Chemicals Corporation | Pigmented porous material |
ATE225830T1 (de) | 1998-12-29 | 2002-10-15 | Ciba Sc Holding Ag | Verbessertes verfahren zur herstellung thermisch spaltbarer, löslicher pigmentderivate |
US6423839B1 (en) | 1999-04-16 | 2002-07-23 | Ciba Specialty Chemicals Corporation | Mixed color pigment precursors and their use |
TWI290164B (en) | 1999-08-26 | 2007-11-21 | Ciba Sc Holding Ag | DPP-containing conjugated polymers and electroluminescent devices |
US6355783B1 (en) | 1999-09-24 | 2002-03-12 | Ciba Specialty Chemicals Corporation | Compounds for mass coloration of high temperature polymers |
AT411306B (de) | 2000-04-27 | 2003-11-25 | Qsel Quantum Solar Energy Linz | Photovoltaische zelle mit einer photoaktiven schicht aus zwei molekularen organischen komponenten |
US20030021913A1 (en) | 2001-07-03 | 2003-01-30 | O'neill Mary | Liquid crystal alignment layer |
WO2003048268A1 (en) | 2001-12-03 | 2003-06-12 | Toyo Ink Mfg. Co., Ltd. | Composition for organic electroluminescence element and organic electroluminescence element using the same |
US20040004433A1 (en) | 2002-06-26 | 2004-01-08 | 3M Innovative Properties Company | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
DE10326547A1 (de) | 2003-06-12 | 2005-01-05 | Siemens Ag | Tandemsolarzelle mit einer gemeinsamen organischen Elektrode |
EP1682605B1 (en) | 2003-10-28 | 2012-06-20 | Basf Se | Novel diketopyrrolopyrrole polymers |
US7194173B2 (en) | 2004-07-16 | 2007-03-20 | The Trustees Of Princeton University | Organic devices having a fiber structure |
CA2587781A1 (en) | 2004-12-09 | 2006-06-15 | Ciba Specialty Chemicals Holding Inc. | Fluorescent diketopyrrolopyrroles |
JP2006310538A (ja) * | 2005-04-28 | 2006-11-09 | Toray Ind Inc | 発光素子 |
WO2007003520A1 (en) * | 2005-07-05 | 2007-01-11 | Ciba Specialty Chemicals Holding Inc. | Fluorescent diketopyrrolopyrroles and derivatives |
US20070079867A1 (en) | 2005-10-12 | 2007-04-12 | Kethinni Chittibabu | Photovoltaic fibers |
GB0612929D0 (en) | 2006-06-29 | 2006-08-09 | Univ Cambridge Tech | High-performance organic field-effect transistors based on dilute, crystalline-crystalline polymer blends and block copolymers |
US20090302311A1 (en) | 2006-06-30 | 2009-12-10 | Turbiez Mathieu G R | Diketopyrrolopyrrole polymers as organic semiconductors |
US7910684B2 (en) * | 2007-09-06 | 2011-03-22 | Xerox Corporation | Diketopyrrolopyrrole-based derivatives for thin film transistors |
WO2009047104A2 (en) | 2007-10-09 | 2009-04-16 | Basf Se | Pyrrolopyrrole derivatives, their manufacture and use |
EP2075274B1 (en) | 2007-12-27 | 2010-06-02 | Industrial Technology Research Institute | Soluble polythiophene derivatives |
US8912305B2 (en) | 2008-10-31 | 2014-12-16 | Basf Se | Diketopyrrolopyrrole polymers for use in organic field effect transistors |
CN102203160B (zh) | 2008-10-31 | 2013-07-17 | 巴斯夫欧洲公司 | 用于有机半导体器件的二酮吡咯并吡咯聚合物 |
JP5635070B2 (ja) | 2009-03-23 | 2014-12-03 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 有機半導体デバイスでの使用のためのジケトピロロピロールポリマー |
US20100326525A1 (en) * | 2009-03-26 | 2010-12-30 | Thuc-Quyen Nguyen | Molecular semiconductors containing diketopyrrolopyrrole and dithioketopyrrolopyrrole chromophores for small molecule or vapor processed solar cells |
KR20120022879A (ko) | 2009-04-08 | 2012-03-12 | 바스프 에스이 | 피롤로피롤 유도체, 그의 제조법 및 반도체로서의 용도 |
WO2010136352A1 (en) | 2009-05-27 | 2010-12-02 | Basf Se | A process for polymerising (hetero)aromatic compounds |
US8629238B2 (en) * | 2009-05-27 | 2014-01-14 | Basf Se | Diketopyrrolopyrrole polymers for use in organic semiconductor devices |
US8598448B2 (en) * | 2010-03-20 | 2013-12-03 | Polyera Corporation | Pyrrolo[3,2-B]pyrrole semiconducting compounds and devices incorporating same |
EP2571919B1 (en) * | 2010-05-19 | 2018-07-11 | Basf Se | Diketopyrrolopyrrole polymers for use in organic semiconductor devices |
EP2621927B1 (en) | 2010-09-29 | 2020-02-12 | Basf Se | Semiconductors based on diketopyrrolopyrroles |
US8598450B2 (en) * | 2010-11-24 | 2013-12-03 | Polyera Corporation | Conjugated polymers and their use in optoelectronic devices |
KR102030859B1 (ko) * | 2011-09-02 | 2019-10-10 | 바스프 에스이 | 디케토피롤로피롤 올리고머, 및 디케토피롤로피롤 올리고머를 포함하는 조성물 |
US20150028142A1 (en) * | 2012-02-06 | 2015-01-29 | Donhad Pty Ltd | Quickly releasable liner bolt |
KR101374070B1 (ko) * | 2012-03-08 | 2014-03-14 | 한국과학기술연구원 | 트리페닐아민 유도체 및 이를 포함하는 유기 태양 전지 |
-
2012
- 2012-06-20 EP EP12730461.6A patent/EP2723750B1/en active Active
- 2012-06-20 KR KR1020147001338A patent/KR102009846B1/ko active IP Right Grant
- 2012-06-20 WO PCT/EP2012/061777 patent/WO2012175530A1/en active Application Filing
- 2012-06-20 CN CN201280030124.3A patent/CN103619855B/zh active Active
- 2012-06-20 JP JP2014516317A patent/JP6165135B2/ja active Active
- 2012-06-20 US US14/123,975 patent/US9362508B2/en active Active
- 2012-06-22 TW TW101122561A patent/TWI609020B/zh active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101072842A (zh) * | 2004-12-09 | 2007-11-14 | 西巴特殊化学品控股有限公司 | 荧光二酮基吡咯并吡咯化合物 |
EP2033983A2 (en) * | 2007-09-06 | 2009-03-11 | Xerox Corporation | Diketopyrrolopyrrole-Based Polymers |
WO2011025454A1 (en) * | 2009-08-28 | 2011-03-03 | Agency For Science, Technology And Research | Ambipolar polymeric semiconductor materials and organic electronic devices |
Also Published As
Publication number | Publication date |
---|---|
TW201302762A (zh) | 2013-01-16 |
TWI609020B (zh) | 2017-12-21 |
WO2012175530A1 (en) | 2012-12-27 |
EP2723750A1 (en) | 2014-04-30 |
JP6165135B2 (ja) | 2017-07-19 |
CN103619855A (zh) | 2014-03-05 |
KR102009846B1 (ko) | 2019-08-12 |
US9362508B2 (en) | 2016-06-07 |
US20140128618A1 (en) | 2014-05-08 |
KR20140058499A (ko) | 2014-05-14 |
EP2723750B1 (en) | 2022-08-10 |
JP2014528908A (ja) | 2014-10-30 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN103619855B (zh) | 用于有机半导体器件的二酮基吡咯并吡咯低聚物 | |
CN104094435B (zh) | 二酮基吡咯并吡咯低聚物和包含二酮基吡咯并吡咯低聚物的组合物 | |
CN103140492B (zh) | 基于二酮基吡咯并吡咯的半导体 | |
US8723028B2 (en) | Conjugated polymers and their use in optoelectronic devices | |
TWI408154B (zh) | 萘-醯亞胺半導體聚合物 | |
CN102362314B (zh) | 用于有机半导体器件的二酮吡咯并吡咯聚合物 | |
TWI511997B (zh) | 共軛聚合物及其於光電子裝置的用途 | |
TWI534173B (zh) | 稠合無規雙噻吩-乙烯共聚物 | |
CN102388046A (zh) | 吡咯并吡咯衍生物、其制备及作为半导体的用途 | |
Chen et al. | π-Extended naphthalene diimide derivatives for n-Type semiconducting polymers | |
TWI646096B (zh) | N-氟烷基取代之二溴萘二亞胺及彼等做為半導體之用途 | |
TWI614254B (zh) | 新穎之縮合多環芳香族化合物及其用途 | |
KR102365446B1 (ko) | 메톡시아릴 표면 개질제 및 상기 메톡시아릴 표면 개질제를 포함하는 유기 전자 소자 | |
TWI632146B (zh) | 二噻吩噻二唑半導體及其元件 | |
TWI580681B (zh) | 二酮基吡咯并吡咯寡聚物及包含二酮基吡咯并吡咯寡聚物之組合物 | |
Yan et al. | Design, synthesis and photophysical properties of ADADA small molecules for photovoltaic application | |
WO2015124284A1 (en) | Cyclic amine surface modifier and organic electronic devices comprising such cyclic amine surface modifier | |
US8993711B2 (en) | Semiconducting polymers and optoelectronic devices incorporating same | |
Palai et al. | Fluorene-based conjugated poly (arylene ethynylene) s containing heteroaromatic bicycles: preparation and electro-optical properties | |
TW201529580A (zh) | 新穎縮合多環芳香族化合物及其用途 | |
Park et al. | Organic thin-film transistor based on dibenzothiophene | |
TWI602844B (zh) | 用於有機半導體裝置之二酮基吡咯并吡咯聚合物 | |
JP2019065267A (ja) | 共役系化合物、光電変換素子および光電変換素子用材料 | |
윤승희 et al. | Photocrosslinkable Carbazole-based Hole Transport Materials for Blue Phosphorescent Organic Light-Emitting Diode |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right |
Effective date of registration: 20200903 Address after: Han Guoshouer Patentee after: Clap Ltd. Address before: Ludwigshafen, Germany Patentee before: BASF Europe Inc. |
|
TR01 | Transfer of patent right |