CN102639591B - 二噻吩并苯并噻吩并[3,2-b]噻吩共聚物及其作为高性能可溶液加工半导体聚合物的用途 - Google Patents
二噻吩并苯并噻吩并[3,2-b]噻吩共聚物及其作为高性能可溶液加工半导体聚合物的用途 Download PDFInfo
- Publication number
- CN102639591B CN102639591B CN201080054412.3A CN201080054412A CN102639591B CN 102639591 B CN102639591 B CN 102639591B CN 201080054412 A CN201080054412 A CN 201080054412A CN 102639591 B CN102639591 B CN 102639591B
- Authority
- CN
- China
- Prior art keywords
- group
- alkyl
- thin film
- thiophene
- polymkeric substance
- 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
- 229920001577 copolymer Polymers 0.000 title claims abstract description 5
- 229920000642 polymer Polymers 0.000 title claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 150000002367 halogens Chemical class 0.000 claims abstract description 13
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims abstract description 8
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 49
- 239000004065 semiconductor Substances 0.000 claims description 39
- 239000000463 material Substances 0.000 claims description 27
- 229930192474 thiophene Natural products 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 16
- 239000000758 substrate Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 12
- 239000010409 thin film Substances 0.000 claims description 10
- 238000000151 deposition Methods 0.000 claims description 6
- 238000007766 curtain coating Methods 0.000 claims description 5
- 230000008021 deposition Effects 0.000 claims description 5
- 238000004528 spin coating Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 4
- 238000003618 dip coating Methods 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 2
- 238000012546 transfer Methods 0.000 claims description 2
- 239000007772 electrode material Substances 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 abstract description 8
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract description 5
- 125000001188 haloalkyl group Chemical group 0.000 abstract description 5
- 125000003367 polycyclic group Chemical group 0.000 abstract description 5
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 abstract description 3
- 125000001424 substituent group Chemical group 0.000 abstract description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 abstract 2
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 abstract 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 abstract 1
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 abstract 1
- 125000005915 C6-C14 aryl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000003106 haloaryl group Chemical group 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- -1 butadienyl Chemical group 0.000 description 43
- 125000003118 aryl group Chemical group 0.000 description 20
- 238000007639 printing Methods 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 229910052717 sulfur Inorganic materials 0.000 description 15
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 14
- 125000001072 heteroaryl group Chemical group 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 10
- 238000005516 engineering process Methods 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 125000005605 benzo group Chemical group 0.000 description 8
- 230000005669 field effect Effects 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 7
- 229910052710 silicon Inorganic materials 0.000 description 7
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 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 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000010703 silicon Substances 0.000 description 6
- GKTQKQTXHNUFSP-UHFFFAOYSA-N thieno[3,4-c]pyrrole-4,6-dione Chemical compound S1C=C2C(=O)NC(=O)C2=C1 GKTQKQTXHNUFSP-UHFFFAOYSA-N 0.000 description 6
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 238000007641 inkjet printing Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000003990 capacitor Substances 0.000 description 4
- KWTSZCJMWHGPOS-UHFFFAOYSA-M chloro(trimethyl)stannane Chemical compound C[Sn](C)(C)Cl KWTSZCJMWHGPOS-UHFFFAOYSA-M 0.000 description 4
- 229920001940 conductive polymer Polymers 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 239000011669 selenium Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 4
- NMFKEMBATXKZSP-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2.S1C=CC2=C1C=CS2 NMFKEMBATXKZSP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 150000003851 azoles Chemical class 0.000 description 3
- 230000000295 complement effect Effects 0.000 description 3
- 239000002322 conducting polymer Substances 0.000 description 3
- 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 3
- 239000003989 dielectric material Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 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 3
- 238000001459 lithography Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000000813 microcontact printing Methods 0.000 description 3
- 238000007645 offset printing Methods 0.000 description 3
- 125000004043 oxo group Chemical group O=* 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000007650 screen-printing Methods 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical compound CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KHWJHOOMWFKBLE-UHFFFAOYSA-N BrC(C)C#CCCCCCCCCCCCC Chemical compound BrC(C)C#CCCCCCCCCCCCC KHWJHOOMWFKBLE-UHFFFAOYSA-N 0.000 description 2
- 229910020366 ClO 4 Inorganic materials 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229920000144 PEDOT:PSS Polymers 0.000 description 2
- 229910018286 SbF 6 Inorganic materials 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical group CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 238000002508 contact lithography Methods 0.000 description 2
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 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 2
- 239000013530 defoamer Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 229920000128 polypyrrole Polymers 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000010129 solution processing Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 2
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- BLSQLHNBWJLIBQ-OZXSUGGESA-N (2R,4S)-terconazole Chemical compound C1CN(C(C)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2N=CN=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 BLSQLHNBWJLIBQ-OZXSUGGESA-N 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical group C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 125000005955 1H-indazolyl group Chemical group 0.000 description 1
- JCZAVVUIFWZMQI-UHFFFAOYSA-N 1h-thieno[2,3-d]imidazole Chemical compound N1C=NC2=C1C=CS2 JCZAVVUIFWZMQI-UHFFFAOYSA-N 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- GGRLKHMFMUXIOG-UHFFFAOYSA-M 2-acetyloxyethyl(trimethyl)azanium;hydroxide Chemical compound [OH-].CC(=O)OCC[N+](C)(C)C GGRLKHMFMUXIOG-UHFFFAOYSA-M 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 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 1
- KQBVVLOYXDVATK-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1h-indole Chemical compound C1CCCC2=C1C=CN2 KQBVVLOYXDVATK-UHFFFAOYSA-N 0.000 description 1
- OURXRFYZEOUCRM-UHFFFAOYSA-N 4-hydroxymorpholine Chemical compound ON1CCOCC1 OURXRFYZEOUCRM-UHFFFAOYSA-N 0.000 description 1
- 229910017008 AsF 6 Inorganic materials 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 0 Cc1c2c([s]c3c4c(*)cc5c3[s]cc5)c4[s]c2c2[s]ccc2c1 Chemical compound Cc1c2c([s]c3c4c(*)cc5c3[s]cc5)c4[s]c2c2[s]ccc2c1 0.000 description 1
- 241001269238 Data Species 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910019800 NbF 5 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 1
- 229910018287 SbF 5 Inorganic materials 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- AVRWEULSKHQETA-UHFFFAOYSA-N Thiophene-2 Chemical compound S1C=2CCCCCC=2C(C(=O)OC)=C1NC(=O)C1=C(F)C(F)=C(F)C(F)=C1F AVRWEULSKHQETA-UHFFFAOYSA-N 0.000 description 1
- 229910007926 ZrCl Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000000137 annealing Methods 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
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 230000003190 augmentative effect Effects 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- MXMZCLLIUQEKSN-UHFFFAOYSA-N benzimidazoline Chemical compound C1=CC=C2NCNC2=C1 MXMZCLLIUQEKSN-UHFFFAOYSA-N 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 1
- 125000000259 cinnolinyl group Chemical class N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- CHVJITGCYZJHLR-UHFFFAOYSA-N cyclohepta-1,3,5-triene Chemical compound C1C=CC=CC=C1 CHVJITGCYZJHLR-UHFFFAOYSA-N 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 229940089256 fungistat Drugs 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical group [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- HRFPRVYNMNOAQO-UHFFFAOYSA-N hexadec-3-yne Chemical compound CCCCCCCCCCCCC#CCC HRFPRVYNMNOAQO-UHFFFAOYSA-N 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000005945 imidazopyridyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002467 indacenes Chemical class 0.000 description 1
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- WPHGSKGZRAQSGP-UHFFFAOYSA-N methylenecyclohexane Natural products C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 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 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- LQERIDTXQFOHKA-UHFFFAOYSA-N nonadecane Chemical compound CCCCCCCCCCCCCCCCCCC LQERIDTXQFOHKA-UHFFFAOYSA-N 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 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
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001291 polyvinyl halide Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 description 1
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=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
- 238000010992 reflux Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 1
- 229940125670 thienopyridine Drugs 0.000 description 1
- 239000002175 thienopyridine Substances 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
-
- 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
-
- 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
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
-
- 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
- C08G2261/30—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
- C08G2261/40—Polymerisation processes
- C08G2261/41—Organometallic coupling reactions
- C08G2261/414—Stille reactions
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/90—Applications
- C08G2261/92—TFT applications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Thin Film Transistor (AREA)
- Electroluminescent Light Sources (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Paints Or Removers (AREA)
Abstract
式(I)的二噻吩并苯并噻吩并[3,2-b]噻吩共聚物,其中:pi为任选被1-4个Ra基团取代的单环或多环结构部分,其中Ra在每次出现时独立地为氢或a)卤素,b)-CN,c)-NO2,d)氧代,e)-OH,f)=C(Rb)2,g)C1-20烷基,h)C2-20链烯基,i)C2-20炔基,j)C1-20烷氧基,k)C1-20烷硫基,l)C1-20卤代烷基,m)-Y-C3-10环烷基,n)-Y-C6-14芳基,o)-Y-3-12员环杂烷基或p)-Y-5-14员杂芳基,其中所述C1-20烷基、C2-20链烯基、C2-20炔基、C3-10环烷基、C6-14芳基或卤代芳基、3-12员环杂烷基和5-14员杂芳基各自任选被1-4个基团Rb取代;Y在每次出现时独立地为二价C1-6烷基、二价C1-6卤代烷基或共价键;以及R1、R2、R3在每次出现时独立地为H、卤素、CN、C1-30烷基、C2-30链烯基、C1-30卤代烷基、C2-30炔基、C1-30烷氧基、C(O)-C1-20烷基、C(O)-OC1-20烷基、Y-C3-10环烷基、-Y-3-12员环杂烷基,各自任选被1-5个选自卤素、-CN、C1-6烷基、C1-6烷氧基和C1-6卤代烷基的取代基取代,-L-Ar1、-L-Ar1-Ar1、-L-Ar1-R4或-L-Ar1-Ar1-R4;且Y在每次出现时独立地为二价C1-6烷基、二价C1-6卤代烷基或共价键;n=0、1、2;以及o=1-1000。
Description
本发明涉及二噻吩并苯并噻吩并[3,2-b]噻吩共聚物及其作为高性能可溶液加工半导体聚合物的用途。
在二十世纪下半叶用于开发(微)电子器件的惊人结构单元是基于无机电极、绝缘体和半导体的场效应晶体管(FET)。已经证明这些材料可靠、高效且具有根据众所周知的Moore定律周期性地提高的性能。不与常规硅技术竞争,基于分子材料和聚合物材料的有机FET(OFET)可大规模应用于低性能存储元件以及集成光电子器件,如有源阵列有机发光二极管显示器、RFID标签、智能ID标签和传感器中的像素驱动器(pixel drive)和开关元件。
作为开发几种导电性或半导体性有机聚合物的结果,它们在有机薄膜晶体管(OTFT)中作为有源层并因而作为半导体的应用赢得越来越多的关注。
在OTFT中使用有机半导体相比于迄今为止所使用的无机半导体具有一些优点。它们能以从纤维到薄膜的任何形式加工,具有高机械柔韧性,能以低成本生产且重量轻。然而,显著的优点是可通过在大气压力和温度下例如通过印刷技术在聚合物衬底上由溶液沉积各层而生产整个半导体组件,从而得到可廉价生产的FET。
电子器件的性能主要取决于载流子在半导体材料中的迁移率以及开启状态和关闭状态之间的电流比(开/关比)。因此,理想的半导体在关闭状态下具有最小导电性且在开启状态下具有最大载流子迁移率(迁移率大于10-3cm2V-1s-1,开/关比大于102)。此外,半导体材料必须对氧化相对稳定,即必须具有足够高的电离电位,因为其氧化降解降低组件性能。
EP1510535A1描述了迁移率为3×10-3或1.7×10-2cm2V-1s-1且开/关比为约106的聚噻吩并(2,3-b)噻吩。WO2006/094645A1描述了具有一个或多个硒吩-2,5-二基和一个或多个噻吩-2,5-二基的聚合物,而WO2006/131185公开了聚噻吩并(3,4-d)噻唑且US2005/0082525A1公开了苯并(1,2-b,4,5-b’)二噻吩。
WO2007/105386公开了具有以下重复单元且重均分子量为至多105g/mol的取代苯并[2,1-b;3,4-b′]二噻吩的均聚物和共聚物。
所述两种材料显示载流子迁移率为10-5-10-3cm2/Vs。
此外,据报导具有双噻吩的共聚物
的重均分子量仅为4100g/mol。该材料在场效应晶体管中仅显示出非常差的性能(迁移率:1.6×10-5,开关比:100)。
本发明的目的是提供用作有机半导体材料的新化合物,其易于合成,具有高迁移率、良好稳定性且可容易加工。
所述目的通过A-B共聚物实现,其中单体A为任选取代的二噻吩并苯并噻吩并[3,2-b]噻吩,且单体B为任选用一个或多个吸电子基团、给电子基团或加溶基团官能化的π共轭的结构部分,所述共聚物具有式(I):
其中:
pi为任选被1-4个Ra基团取代的单环或多环结构部分,其中
Ra在每次出现时独立地为氢或a)卤素,b)-CN,c)-NO2,d)氧代,e)-OH,f)=C(Rb)2,g)C1-20烷基,h)C2-20链烯基,i)C2-20炔基,j)C1-20烷氧基,k)C1-20烷硫基,l)C1-20卤代烷基,m)-Y-C3-10环烷基,n)-Y-C6-14芳基,o)-Y-3-12员环杂烷基或p)-Y-5-14员杂芳基,其中所述C1-20烷基、C2-20链烯基、C2-20炔基、C3-10环烷基、C6-14芳基或卤代芳基、3-12员环杂烷基和5-14员杂芳基各自任选被1-4个基团Rb取代;
Rb在每次出现时独立地为a)卤素,b)-CN,c)-NO2,d)氧代,e)-OH,f)-NH2,g)-NH(C1-20烷基),h)-N(C1-20烷基)2,i)-N(C1-20烷基)-C6-14芳基,j)-N(C6-14芳基)2,k)-S(O)mH,l)-S(O)m-C1-20烷基,m)-S(O)2OH,n)-S(O)m-OC1-20烷基,o)-S(O)m-OC6-14芳基,p)-CHO,q)-C(O)-C1-20烷基,r)-C(O)-C6-14芳基,s)-C(O)OH,t)-C(O)-OC1-20烷基,u)-C(O)-OC6-14芳基,v)-C(O)NH2,w)-C(O)NH-C1-20烷基,x)-C(O)N(C1-20烷基)2,y)-C(O)NH-C6-14芳基,z)-C(O)N(C1-20烷基)-C6-14芳基,aa)-C(O)N(C6-14芳基)2,ab)-C(S)NH2,ac)-C(S)NH-C1-20烷基,ad)-C(S)N(C1-20烷基)2,ae)-C(S)N(C6-14芳基)2,af)-C(S)N(C1-20烷基)-C6-14芳基,ag)-C(S)NH-C6-14芳基,ah)-S(O)mNH2,ai)-S(O)mNH(C1-20烷基),aj)-S(O)mN(C1-20烷基)2,ak)-S(O)mNH(C6-14芳基),al)-S(O)mN(C1-20烷基)-C6-14芳基,am)-S(O)mN(C6-14芳基)2,an)SiH3,ao)SiH(C1-20烷基)2,ap)SiH2(C1-20烷基),ar)-Si(C1-20烷基)3,as)C1-20烷基,at)C2-20链烯基,au)C2-20炔基,av)C1-20烷氧基,aw)C1-20烷硫基,ax)C1-20卤代烷基,ay)C3-10环烷基,az)C6-14芳基或卤代芳基,ba)3-12员环杂烷基或bb)5-14员杂芳基;
Y在每次出现时独立地为二价C1-6烷基、二价C1-6卤代烷基或共价键;且m在每次出现时独立地为0、1或2;
R1、R2、R3在每次出现时独立地为H、卤素、CN、C1-30烷基、C2-30链烯基、C1-30卤代烷基、C2-30炔基、C1-30烷氧基、C(O)-C1-20烷基、C(O)-OC1-20链烯基、Y-C3-10环烷基、-Y-3-12员环杂烷基,其各自任选被1-5个选自卤素、-CN、C1-6烷基、C1-6烷氧基和C1-6卤代烷基的取代基取代,-L-Ar1、-L-Ar1-Ar1、-L-Ar1-R4或-L-Ar1-Ar1-R4;
其中:
L在每次出现时独立地为-O-、-Y-O-Y-、-S-、-S(O)-、-Y-S-Y-、-C(O)-、-NRcC(O)-、-NRc-、-SiRc 2-、-Y-[SiRc 2]-Y-、二价C2-30烷基、二价C1-30链烯基、二价C1-30卤代烷基或共价键;
其中:
Rc在每次出现时为H、C1-20烷基或-Y-C6-14芳基;
Ar1在每次出现时独立地为C6-14芳基或5-14员杂芳基,各自任选被1-5个选自卤素、-CN、C1-6烷基、C1-6烷氧基和C1-6卤代烷基的取代基取代;
且
R4在每次出现时独立地为C1-20烷基、C2-20链烯基、C1-20卤代烷基、C1-20烷氧基、-L′-Ar2、-L′-Ar2-Ar2、-L′-Ar2-R5或-L′-Ar2-Ar2-R5;
其中:
L′在每次出现时独立地为-O-、-Y-O-Y-、-S-、-S(O)-、-Y-S-Y-、-C(O)-、-NRcC(O)-、-NRc-、-SiRc 2-、-Y-[SiRc 2]-Y-、二价C1-20烷基、二价C1-20链烯基、二价C1-20卤代烷基或共价键;
Ar2在每次出现时独立地为C6-14芳基或5-14员杂芳基,各自任选被1-5个选自卤素、-CN、C1-6烷基、C1-6烷氧基和C1-6卤代烷基的取代基取代;
且
R5在每次出现时为C1-20烷基、C2-20链烯基、C1-20卤代烷基或C1-20烷氧基;
且Y在每次出现时独立地为二价C1-6烷基、二价C1-6卤代烷基或共价键;
n=0、1、2;且
o=1-1000。
在一个实施方案中,n=0。在另一实施方案中,n=1。
优选o=5-1000,更优选o=5-100。
pi通常为平面且高度共轭的环状核,其中环原子以交替单键和双键共价键合。该类核的高度共轭和平面性质可促进π-电子离域(从而提高稳定性和降低LUMO能量),并提供良好的分子间π-堆叠。合适环状核的实例包括苯、萘、蒽、并四苯、并五苯、苝、芘、晕苯、芴、indacene、茚并芴和四联苯,以及其中一个或多个碳原子被杂原子如O、S、Si、Se、N或P替换的其类似物。
优选pi为选自以下的任选取代的单环、杂环或多环结构部分:
其中:
k、k’、l、l’、p、p’、q、u、u’、v和v’独立地选自-S-、-O-、-CH=、=CH-、-CR6=、=CR6-、-C(O)-、-C(C(CN)2)-、-N=、=N-、-NH-、-NR3-、-SiRc=、=SiRc-和-SiR7Rc-;
R6在每次出现时独立地选自a)卤素,b)-CN,c)-NO2,d)N(Rc)2,e)-ORc,f)-C(O)Rc,g)-C(O)ORc,h)-C(O)N(Rc)2,i)C1-40烷基,j)C2-40链烯基,k)C2-40炔基,l)C1-40烷氧基,m)C1-40烷硫基,n)C1-40卤代烷基,o)-Y-C3-14环烷基,p)-Y-C6-14芳基,q)-Y-3-14员环杂烷基和r)-Y-5-14员杂芳基,其中C1-40烷基、C2-40链烯基、C2-40炔基、C3-14环烷基、C6-14芳基和3-14员环杂烷基以及Y和Rc如本文所定义;
Rc如本文处所定义;
r和s独立地可为-CRcRc-或-C(C(CN)2)-;且
b为1、2、3或4。
在特定实施方案中,pi为包含一个或多个噻吩基、噻唑基或苯基的单环、双环或杂环结构部分,其中这些基团各自可任选如本文所公开的那样被取代。例如,pi可选自:
其中Ra和Rc在每次出现时如本文所定义。
在优选的实施方案中,
R1、R2、R3独立地选自C1-20烷基和C1-20烷氧基,其中所述C1-20烷基或C1-20烷氧基可任选被1-4个独立地选自C1-20烷基和C1-20烷氧基的基团取代。
在特别优选的实施方案中,
R1、R2、R3独立地选自C1-20烷基,且所述C1-20烷基各自可任选被1-4个独立地选自C1-20烷基的基团取代。
特别优选的取代基R1、R2、R3为任选被1-4个C1-C6烷基取代的C6-20烷基。
数均分子量Mn优选为1000-200000g/mol,更优选为10000-100000g/mol。
“链烯基”是指具有一个或多个碳-碳双键的直链或支化烷基。实例为乙烯基、丙烯基、丁烯基、戊烯基、己烯基、丁二烯基、戊二烯基和己二烯基。所述一个或多个碳-碳双键可位于内部(例如在2-丁烯中)或末端(例如在1-丁烯中)。在各个实施方案中,链烯基可具有2-20个碳原子。在一些实施方案中,链烯基可如本文所述被取代。链烯基通常不被另一链烯基、烷基或炔基取代。
“炔基”是指具有一个或多个碳-碳三键的直链或支化烷基。实例包括乙炔基、丙炔基、丁炔基、戊炔基。所述一个或多个碳-碳三键可位于内部(例如在2-丁炔中)或末端(例如在1-丁炔中)。在各个实施方案中,炔基可具有2-20个碳原子。在一些实施方案中,炔基可如本文所述被取代。炔基通常不被另一炔基、烷基或链烯基取代。
“环烃基”是指非芳族碳环基团,包括环化烷基、烯基和炔基。优选的环烃基可具有3-10个碳原子。环烃基可为单环的(例如环己基)或多环的(例如含稠环、桥环和/或螺环体系),其中碳原子位于环体系的内部或外部。环烃基的任何合适环位置可共价连接至指定的化学结构。环烃基的实例包括环丙基、环丁基、环戊基、环己基、环庚基、环戊烯基、环己烯基、环己二烯基、环庚三烯基、降冰片基、降蒎烷基、降蒈烷基、金刚烷基和螺[4.5]癸烷基及其同系物、异构体等。环烃基可如本文所述被取代。
“杂原子”是指碳或氢以外的任何元素的原子且包括例如氮、氧、硅、硫、磷和硒。
“环杂烃基”是指含有至少一个选自O、S、Se、N、P和Si(如O、S和N)的环杂原子且任选含有一个或多个双键或叁键的非芳族环烷基。环杂烃基可具有3-12个环原子。环杂烃基环中的一个或多个N、P、S或Se原子(如N或S)可被氧化(例如吗啉N-氧化物、硫吗啉S-氧化物、硫吗啉S,S-二氧化物)。环杂烃基的氮原子或磷原子可具有取代基,尤其为烷基。环杂烃基还可含有一个或多个氧代基团,如哌啶酮基、唑烷酮基、嘧啶-(1H,3H)-二酮基、吡啶-2(1H)-酮基等。环杂烃基的优选实例尤其包括吗啉基、硫吗啉基、吡喃基、咪唑烷基、咪唑啉基、唑烷基、吡唑烷基、吡唑啉基、吡咯烷基、吡咯啉基、四氢呋喃基、四氢噻吩基、哌啶基、哌嗪基。环杂烃基可被取代或未被取代。
“芳基”是指其中两个或更多个芳族烃环稠合在一起(即具有共同的键)或至少一个芳族单环烃环与一个或多个环烷基和/或环杂烷基环稠合的芳族单环烃环体系或多环环体系。芳基可在可包含多个稠合环的其环体系中具有6-14个碳原子。仅具有芳族碳环的优选芳基包括苯基、1-萘基(双环)、2-萘基(双环)、蒽基(三环)、菲基(三环)。其中至少一个芳族碳环与一个或多个环烷基和/或环杂烷基环稠合的优选多环环体系尤其包括环戊烷的苯并衍生物(即为5,6-双环环烷基/芳族环体系的2,3-二氢化茚基),环己烷的苯并衍生物(即为6,6-双环环烷基/芳族环体系的四氢萘基),咪唑啉的苯并衍生物(即为5,6-双环环杂烷基/芳族环体系的苯并咪唑啉基)和吡喃的苯并衍生物(即为6,6-双环环杂烷基/芳族环体系的苯并吡喃基)。其他优选的芳基包括苯并二烷基、苯并间二氧杂环戊烯基(benzodioxolyl)、苯并二氢吡喃基、二氢吲哚基等。在一些实施方案中,芳基可如本文所述被取代。在一些实施方案中,芳基可具有一个或多个卤素取代基并且可称为“卤代芳基”。全卤代芳基,即其中所有氢原子被卤原子替代的芳基(例如-C6F5)涵盖于“卤代芳基”的定义范围内。在某些实施方案中,芳基被另一芳基取代且可称为联芳基。联芳基中的芳基各自可被取代或未被取代。
“杂芳基”是指含有至少一个环杂原子的芳族单环环体系或多环体系。所述杂原子优选选自氧(O)、氮(N)、硫(S)、硅(Si)和硒(Se)或不限于此的多环体系。多环杂芳基包括两个或更多个稠合在一起的杂芳基环和与一个或多个芳族碳环、非芳族碳环和/或非芳族环杂烷基环稠合的单环杂芳基环。杂芳基可具有5-14个环原子且含有1-5个环杂原子。杂芳基的特别实例包括例如如下所示的5或6员单环体系和5-6双环体系:
其中T为O、S、NH、N-烷基、N-芳基、N-(芳基烷基)(例如N-苄基)、SiH2、SiH-(烷基)、Si(烷基)2、SiH-(芳基烷基)、Si-(芳基烷基)2或Si(烷基)(芳基烷基)。这类杂芳基环的实例包括吡咯基、呋喃基、噻吩基、吡啶基、嘧啶基、哒嗪基、吡嗪基、三唑基、四唑基、吡唑基、咪唑基、异噻唑基、噻唑基、噻二唑基、异唑基、唑基、二唑基、吲哚基、异氮杂茚基、苯并呋喃基、苯并噻吩基、喹啉基、2-甲基喹啉基、异喹啉基、喹喔啉基、喹唑啉基、苯并三唑基、苯并咪唑基、苯并噻唑基、苯并异噻唑基、苯并异唑基、苯并二唑基、苯并唑基、噌啉基、1H-吲唑基、2H-吲唑基、中氮茚基、异苯并呋喃基、1,5-二氮杂萘基、2,3-二氮杂萘基、蝶啶基、嘌呤基、唑并吡啶基、噻唑并吡啶基、咪唑并吡啶基、呋喃并吡啶基、噻吩并吡啶基、吡啶并嘧啶基、吡啶并吡嗪基、吡啶并哒嗪基、噻吩并噻唑基、噻吩并唑基、噻吩并咪唑基等。杂芳基的其他实例包括4,5,6,7-四氢吲哚基、四氢喹啉基、苯并噻吩并吡啶基、苯并呋喃并吡啶基等。在一些实施方案中,杂芳基可如本文所述被取代。
R1、R2、R3特别优选为直链或支化C6-C20烷基,如正己基、正庚基、正辛基、正壬基、正癸基、正十一烷基、正十二烷基、正十三烷基、正十四烷基、正十五烷基、正十六烷基、正十七烷基、正十八烷基、正十九烷基、n-isosyl、1-甲基戊基、1-甲基己基、2-甲基戊基、2-乙基己基和2,7-二甲基辛基。尤其优选为2,6-二甲基辛基、1-乙基己基、1-甲基己基、2-乙基戊基、2-甲基己基、正癸基、正十二烷基、正十四烷基和2-乙基己基,最优选正十二烷基。
本发明共聚物可根据以下方案1制备:
方案1:
参见方案1,本发明共聚物的特定实施方案可在三邻甲苯基膦和Pd2(dba)3(dba=二亚苄基丙酮)存在下,通过金属催化的Stille聚合反应合成。
1,3-双(三甲基甲锡烷基)噻吩并[3,2-b]噻吩可通过在无水THF中,将叔丁基锂添加至噻吩并[3,2-b]噻吩中而制备,此时形成沉淀。向该悬浮液中添加呈固体形式的三甲基氯化锡。1,3-双(3-炔-2-基)噻吩并[3,2-b]噻吩通过在无水邻二氯苯中,使1,3-双(三甲基甲锡烷基)噻吩并[3,2-b]噻吩与2-溴-3-十六炔基噻吩在三邻甲苯基膦和Pd2(dba)3存在下反应而制备。4,8-双烷基二噻吩并苯并噻吩并[3,2-b]噻吩可通过将DBU添加至处于NMP中的1,3-双(3-炔-2-基)噻吩并[3,2-b]噻吩中而获得。双烷基二噻吩并苯并噻吩并[3,2-b]噻吩又通过在无水THF中与叔丁基锂反应,然后添加三甲基氯化锡而转化成相应的双三甲基甲锡烷基化合物。有机锡化合物与适当二溴化物在三邻甲苯基膦和Pd2(dba)3存在下发生聚合反应从而获得所需共聚物。
本发明包括本发明聚合物的氧化形式和还原形式二者。电子的缺乏或过量导致形成具有高导电性的离域离子。这可通过用常规掺杂剂掺杂而实现。掺杂剂和掺杂方法是公知常识且例如由EP-A 0528662、US5198153或WO96/21659已知。合适的掺杂方法例如包括用掺杂气体掺杂,在包含掺杂剂的溶液中电化学掺杂,通过热扩散以及通过将掺杂剂离子注入半导体材料中而掺杂。
在使用电子作为载流子的情况下,优选使用卤素(例如I2、Cl2、Br2、ICl、ICl3、IBr和IF),路易斯酸(例如PF5、AsF5、SbF5、BF3、BCl3、SbCl5、BBr3和SO3),无机酸(例如HF、HCl、HNO3、H2SO4、HClO4、FSO3H和ClSO3H),有机酸或氨基酸,过渡金属化合物(例如FeCl3、FeOCl、Fe(ClO4)3、Fe(4-CH3C6H4SO3)3、TiCl4、ZrCl4、HfCl4、NbF5、NbCl5、TaCl5、MoF5、MoCl5、WF5、WCl6、UF6和LnCl3(其中Ln为镧系元素),阴离子(例如Cl-、Br-、I-、I3 -、HSO4 -、SO4 2-、NO3 -、ClO4 -、BF4 -、PF6 -、AsF6 -、SbF6 -、FeCl4 -、Fe(CN)6 3-,以及不同磺酸的阴离子如芳基-SO3 -)。在使用空穴作为载流子的情况下,作为掺杂剂的例如是阳离子(例如H+、Li+、Na+、K+、Rb+和Cs+),碱金属(例如Li、Na、K、Rb和Cs),碱土金属(例如Ca、Sr和Ba),O2,XeOF4,(NO2 +)(SbF6 -),(NO2 +)(SbCl6 -),(NO2 +)(BF4 -),AgClO4,H2IrCl6,La(NO3)3,FSO2OOSO2F,Eu,乙酰胆碱,R4N+,R4P+,R6As+和R3S+,其中R为烷基。
本发明共聚物的导电形式可用作有机导体,例如有机发光二极管(OLED)中的电荷注入层和ITO平面化层,平面屏和触摸屏,抗静电膜,印刷电路和电容器,但不限于此。
本发明共聚物可用于生产光学、电子和半导体材料,尤其是作为场效应晶体管(FET)中的电荷传输材料,例如作为集成电路(IC)、ID标签或TFT的组件。或者它们可用于电致发光显示器中的有机发光二极管(OLED)中或用作背光,例如液晶显示器(LCD),用于光伏应用或传感器,用于电子照相记录和其他半导体应用。
由于本发明共聚物具有良好的溶解性,它们可作为溶液或分散体施涂于衬底上。因此可以用廉价方法,例如旋涂或印刷施涂各层。
合适的溶剂或溶剂混合物例如包括烷烃、芳烃、酯、酮和尤其是其卤代衍生物。
包含半导体材料的FET和其他组件如二极管可有利地用于ID标签或安全标记中以显示有价值物品如钞票、信用卡、身份文件如ID卡或驾驶执照或具有金钱利益的其他文件如橡皮图章、邮票或票券等的真实性和防止伪造。
或者,本发明聚合物可用于有机发光二极管(OLED)中,例如用于显示器中或用作液晶显示器(LCD)用背光。通常而言,OLED具有多层结构。发光层通常嵌入一个或多个电子-和/或空穴传输层之间。当施加电压时,电子或空穴可在发射层的方向迁移,其中它们在发射层中复合而激发并且发光化合物随后发光。该聚合物、材料和层可根据其电学和光学性能用于一个或多个传输层和/或发射层中。当该化合物、材料或层为电致发光的或具有电致发光基团或化合物时,它们特别适合发射层。
类似于用于OLED中的合适聚合物的加工,选择属于公知常识且例如描述于Synthetic Materials,111-112(2000),31-34或J.Appl.Phys.,88(2000)7124-7128中。
对有机半导体已经使用各种沉积技术,包括由各种溶液加工技术沉积。例如,印刷电子技术大多集中在喷墨印刷,主要是因为该技术对特征布置和多层定位提供了更大的控制。喷墨印刷是无接触方法,其提供的益处是不要求预制底版(与接触印刷技术相比),以及对油墨喷出的数字控制,从而提供按需喷墨印刷。微喷为另一非接触印刷方法。然而,接触印刷技术所具有的重要优点是非常适合非常快速的卷绕加工。示例性接触印刷技术包括但不限于丝网印刷、凹版印刷、胶印印刷、柔性版印刷、平版印刷、和移印印刷和微接触印刷。本文所用“印刷”包括非接触方法,如喷墨印刷、微喷印刷等,以及接触方法丝网印刷、凹版印刷、胶印印刷、柔性版印刷、平版印刷、移印印刷和微接触印刷等。其他溶液加工技术例如包括旋涂、液滴流延(drop-casting)、区域流延(zone casting)、浸涂和刮涂或喷涂。
使用本文所公开化合物的各种制造品,包括电子器件、光学器件和光电器件,如场效应晶体管(如薄膜晶体管)、光伏器件、有机发光二极管(OLED)、互补型金属氧化物半导体(CMOS)、互补型逆变器、D触发器、整流器和环形振荡器及其制备方法也处于本教导的范围内。
因此,本教导进一步提供了制备半导体材料的方法。这些方法可包括制备包含溶于或分散于液体介质如溶剂或溶剂混合物中的一种或多种本文所公开的化合物的组合物,将该组合物沉积于衬底上以提供半导体材料前体,并加工(例如加热)该半导体前体而提供包含本文所公开的化合物的半导体材料(例如薄膜半导体)。在各个实施方案中,所述液体介质为有机溶剂、无机溶剂如水或其组合。在一些实施方案中,该组合物可进一步含有一种或多种独立地选自以下物质的添加剂:洗涤剂、分散剂、粘合剂、相容剂、固化剂、引发剂、保湿剂、消泡剂、润湿剂、pH调节剂、生物杀伤剂和抑菌剂。可包含例如表面活性剂和/或其他聚合物(如聚苯乙烯、聚乙烯、聚α-甲基苯乙烯、聚异丁烯、聚丙烯、聚甲基丙烯酸甲酯等)作为分散剂、粘合剂、相容剂和/或消泡剂。在一些实施方案中,沉积步骤可通过印刷,包括喷墨印刷和各种接触印刷技术(如丝网印刷、凹版印刷、胶印印刷、移印印刷、平版印刷、柔性版印刷和微接触印刷)进行。在其他实施方案中,沉积步骤可通过旋涂、液滴流延、区域流延、浸涂和刮涂或喷涂进行。
本教导进一步提供了制造品,例如包括具有本教导半导体材料和衬底组件和/或电介质组件的复合体的本文所述的各种器件。衬底组件可选自掺杂的硅、铟锡氧化物(ITO)、ITO涂敷的玻璃、ITO涂敷的聚酰亚胺或其他塑料、单独或涂敷在聚合物或其他衬底上的铝或其他金属、掺杂的聚噻吩等。电介质组件可由无机介电材料如各种氧化物(例如SiO2、Al2O3、HfO2),有机介电材料如各种聚合物材料(如聚碳酸酯、聚酯、聚苯乙烯、聚卤代乙烯、聚丙烯酸酯)和自组装超晶格/自组装纳米介电(SAS/SAND)材料(例如如Yoon,M-H.等,PNAS,102(13):4678-4682(2005)所述,其全部公开内容在此引作参考)以及有机/无机混杂介电材料(如美国专利申请序列号11/642,504所述,其全部公开内容在此引作参考)制备。在一些实施方案中,电介质组件可含有美国专利申请序列号11/315,076、60/816,952和60/861,308中所述的交联聚合物共混物,它们各自的全部公开内容在此引作参考。该复合体还可以包括一个或多个电触点。源电极、漏电极和栅电极的合适材料包括金属(例如Au、Al、Ni、Cu),透明导电氧化物(例如ITO、IZO、ZITO、GZO、GIO、GITO),以及导电聚合物(例如聚(3,4-亚乙二氧基噻吩)聚苯乙烯磺酸盐(PEDOT:PSS)、聚苯胺(PANI)、聚吡咯(PPy))。一种或多种本文所述复合体可以包括在各种有机电子、光学和光电器件如有机薄膜晶体管(OTFT),具体为有机场效应晶体管(OFET),以及传感器、电容器、单极电路、互补电路(例如反相电路)等中。
其中可以使用本教导材料的其他制造品是光伏器件或太阳能电池。本教导的组件可呈现宽的光学吸收和/或非常正向偏移的还原电位,这使得其是这类应用所需的。因此,本文所述物质可在包括形成p-n结的相邻n型半导体材料的光伏设计中用作p型半导体。该化合物可以呈薄膜半导体形式,其可沉积于衬底上以形成复合体。在该类器件中利用本教导的小分子为本领域技术人员所知晓。
因此,本发明另一方面涉及一种制造掺有本教导半导体材料的有机场效应晶体管的方法。本教导的半导体材料可用于制造各种类型的有机场效应晶体管,包括顶栅极顶接触电容器结构、顶栅极底接触电容器结构、底栅极顶接触电容器结构和底栅极底接触电容器结构。图1示意了4种常见类型的OFET结构:顶接触底栅极结构(a),底接触底栅极结构(b),底接触顶栅极结构(c)和顶接触顶栅极结构(d)。如图1所示,OFET可包括电介质层(例如在图1a、1b、1c和1d中分别示为8、8′、8"和8′"),半导体层(例如在图1a、1b、1c和1d中分别示为6、6′、6"和6′″),栅极触点(例如在图1a、1b、1c和1d中分别示为10、10′、10"和10′"),衬底(例如在图1a、1b、1c和1d中分别示为12、12′、12"和12′″)以及源电极和漏电极触点(例如在图1a、1b、1c和1d中分别示为2、2′、2"、2′″、4、4′、4"和4′″)。
在特定实施方案中,OTFT器件可用本发明化合物在掺杂的硅衬底上制造,其中以顶接触几何结构使用SiO2作为电介质。在具体实施方案中,掺有至少一种本教导材料的有源半导体层可在室温或升高的温度下沉积。在其他实施方案中,掺有至少一种本教导化合物的有源半导体层可通过本文所述的旋涂或印刷施涂。对于顶接触器件,可使用阴影掩模在薄膜顶部对金属触点进行图案化。
除非另有说明,否则所有定量数据(百分比、ppm等)基于重量,基于混合物的总重量。
实施例
实施例1 制备1,3-双(三甲基甲锡烷基)噻吩并[3,2-b]噻吩
在氩气下,将1g(7.1mmol)噻吩并[3,2-b]噻吩溶解于40ml无水THF中并冷却至-78°C。将11ml(17.6mmol)的1.6M叔丁基锂溶液缓慢添加至戊烷中。将该混合物在-78°C下搅拌2小时,然后添加4g(20mmol)固体形式的三甲基氯化锡。将该溶液温热至室温并搅拌1小时。将所述溶液用100ml二乙醚稀释,用碳酸氢钠水溶液萃取,干燥并蒸发。将残留物在-20°C下由乙腈结晶,从而获得1.9g(58%)无色晶体。Mp=130°C;MS(FD,8kV)m/z=465.4g/mol,计算值465.9g/mol,C12H20S2Sn2;1H-NMR(300MHz,CD2Cl2,RT):δ7.28(s,2H),δ0.41(s,2H);13C-NMR(75MHz,CD2Cl2,RT):δ148.0,142.0,16.6,-8.0;元素分析:实测值30.91%,4.48%H,13.61%S,计算值30.94%C,4.33%H,13.77%S。
实施例2 制备1,3-双(3-十六炔基噻吩-2-基)噻吩并[3,2-b]噻吩
在氩气下,将932mg(2mmol)1,3-双(三甲基甲锡烷基)噻吩并[3,2-b]噻吩和843mg(2.2mmol)2-溴-3-十六炔基噻吩溶解于20ml无水邻二氯苯中。添加61mg(0.2mmol)三邻甲苯基膦和47mg(50μmol)Pd2(dba)3。将该溶液加热至120°C达3小时。在高真空下除去溶剂。残留物通过硅胶柱色谱法使用石油醚-二氯甲烷(17:3v/v)作为洗脱液提纯。在0°C下由己烷结晶后,获得950mg(64%)橙黄色粉末。Mp=71°C;MS(FD,8kV)m/z=743.3g/mol,计算值:744.4g/mol,C46H64S4;1H-NMR(250MHz,CD2Cl2,RT):δ7.68(s,2H),δ7.14(d,J=5.3Hz,2H),δ7.02(d,J=5.3Hz,2H),δ2.54(t,J=7.0Hz,4H),δ1.69(quin,J=7.4Hz,4H),δ1.6-1.1(m,48H),δ0.89(t,J=6.5Hz,6H);13C-NMR(62.5MHz,CD2Cl2,RT):δ140.0,138.99,138.94,132.3,123.7,119.2,117.5,97.4,76.6,32.6,30.4-30.2(多重峰),30.0,29.9,29.7,29.1,23.3,14.5;元素分析:实测值74.00%C,8.62%H,17.30%S,计算值74.14%C,8.66%H,17.21%S。
实施例3 制备4,8-双(十四烷基)二噻吩并苯并噻吩并[3,2-b]噻吩
将500mg(0.67mmol)1,3-双(3-十六炔基噻吩-2-基)噻吩并[3,2-b]噻吩溶解于15ml NMP中。在将该溶液脱气后,添加0.11ml(0.74mmol)DBU。将所得溶液回流过夜,冷却至室温,使用20ml甲醇稀释并过滤。将黄色固体由己烷再结晶,获得390mg(78%)淡黄色细针状物。Mp=118°C;MS(FD,8kV)m/z=743.5g/mol,计算值744.4g/mol,C46H64S4;1H-NMR(500MHz,C2D2Cl4,60°C):δ7.65(s,2H),δ7.40(d,J=5.2Hz,2H),δ7.38(d,J=5.2Hz,2H),δ3.20(t,J=7.9Hz,4H),δ1.85(quin,J=7.7Hz,4H),δ1.56(quin,J=7.6Hz,4H),δ1.39(quin,J=7.5Hz,4H),δ1.3-1.1(m,36H),δ0.82(t,J=7.0Hz,6H);13C-NMR(125MHz,C2D2Cl4,60°C):δ138.3,136.5,134.2,132.1,131.8,130.0,125.1,125.0,120.8,34.8,32.2,31.3,29.9(多重峰),29.8,29.6,22.9,14.4;元素分析:实测值74.12%C,8.67%H,17.04%S,计算值74.14%C,8.66%H,17.21%S。
实施例4 制备2,8-双三甲基甲锡烷基-5,12-双(十四烷基)二噻吩并苯并噻吩并[3,2-b]噻吩
在氩气气氛下,将74.5mg(0.1mmol)4,8-双(十四烷基)二噻吩并苯并噻吩并[3,2-b]噻吩悬浮于5ml无水THF中。将所述悬浮液冷却至0°C,缓慢添加0.16ml(0.25mmol)叔丁基锂(1.6M,于戊烷中),所述悬浮液随之由浅黄色变为深棕色。将该混合物在0°C下搅拌2小时,同时颜色再次变亮。缓慢添加处于2ml THF中的50mg(0.25mmol)三甲基氯化锡,将该混合物温热至室温并在该温度下搅拌1小时。添加20ml甲醇,滤除沉淀物并在4°C下由乙酸乙酯重结晶两次,从而获得45mg黄色针状物。Mp=67°C;MS(FD,8kV)m/z=1070.1g/mol,计算值1070.3g/mol,C52H80S4Sn2;1H-NMR(250MHz,CD2Cl2):δ7.67(s,2H),δ7.51(s,2H),δ3.23(t,J=7.7Hz,4H),δ1.87(quin,J=7.6Hz,4H),δ1.59(quin,J=7.4Hz,4H),δ1.4-1.1(m,40H),δ0.87(t,J=6.5Hz,6H),δ0.48(s,18H);13C-NMR(75MHz,CD2Cl2):δ140.2,139.6,136.8,136.2,134.2,133.2,132.1,129.5,120.4,35.3,32.5,31.7,30.3(多重峰),30.2,29.9,23.3,14.5;元素分析:实测值58.84%C,7.66%H,11.38%S,计算值58.33%C,7.53%H,11.98%S。
实施例5a 制备聚(2,8-双-3-十四烷基噻吩-2-基)-5,12-双(十四烷基)二噻吩并苯并噻吩并[3,2-b]噻吩
在氩气下,将32.13mg(30μmol)2,8-双三甲基甲锡烷基-5,12-双(十四烷基)二噻吩并苯并噻吩并[3,2-b]噻吩和21.50mg(30μmol)5,5′-二溴-4,4′-二(十二烷基)-2,2′-二噻吩溶解于2ml无水1,2-二氯苯中。添加1.2mg(4μmol)三邻甲苯基膦和0.9mg(1μmol)Pd2(dba)3。将所得混合物加热至140°C达3天。用1,2-二氯苯稀释并在甲醇中沉淀。过滤后,将所述聚合物在甲醇中再沉淀两次并干燥。获得31mg红色固体(80%)。GPC(1,2,4-三氯苯,135°C)分析给出Mn=8kg/mol且Mw=16kg/mol,相对于聚苯乙烯标样。1H-NMR(500MHz,C2D2Cl4,120°C,δ(ppm)):7.6(br,2H),7.5(br,2H),7.2(br,2H)。
实施例5b 另一种制备方法
在处于微波管中的手套箱中,将107.09mg(0.1mmol)2,8-双三甲基甲锡烷基-5,12-双(十四烷基)二噻吩并苯并噻吩并[3,2-b]噻吩和71.68mg(0.1mmol)5,5′-二溴-4,4′-二(十二烷基)-2,2′-二噻吩溶解于1ml甲苯中。在添加5mg(5μmol)作为催化剂的Pd(PPh3)4后,密封该管并进行微波辐照(330W)。将温度保持在120°C下5分钟,然后在140°C下再次保持5分钟,最后在155°C下保持40分钟。将部分沉淀的聚合物溶解于1,2-二氯苯中,在甲醇中沉淀,再沉淀并用丙酮索格利特萃取12小时。获得110mg红色聚合物(85%)。GPC(1,2,4-三氯苯,135°C)分析给出Mn=17kg/mol且Mw=43kg/mol,相对于聚苯乙烯标样。
实施例6 FET器件的制备和测量
对晶体管而言,使用具有200nm厚的热生长二氧化硅层的重掺杂硅晶片作为衬底。在120°C下,由气相沉积出六甲基二硅氮烷。半导体聚合物膜通过针涂(pin-coating)(3000rpm,60秒)5mg ml-1 1,2-二氯苯溶液(大约47.5nm厚)而制备。退火后,将衬底在100°C下保持5分钟并缓慢冷却(1°Cmin-1),源电极和漏电极通过经由阴影掩膜在所述半导体薄膜上气相沉积金(3×10-6毫巴,~100nm厚)而制造,从而获得沟道长度为25-75μm且宽度为约0.5-1.5mm(W L-1=20)的器件。所有制备和使用Keithley 4200半导体参数分析仪进行的电测量均在氮气气氛下在黄光中进行。
饱和载流子(场效应)迁移率由如下方程计算:
结果如下:
场效应迁移率:
μsat=1.29(±0.28)×10-3cm2/Vs(5次测量结果的平均值)
开关比:
Ion/Ioff=3.8(±0.2)×103(5次测量结果的平均值)
Claims (13)
1.式(I)的二噻吩并苯并噻吩并[3,2-b]噻吩共聚物,
其中:
pi选自下组:
其中
Ra在每次出现时独立地为氢或a)卤素,b)-CN,e)-OH,g)C1-20烷基,h)C2-20链烯基,i)C2-20炔基,j)C1-20烷氧基,k)C1-20烷硫基,l)C1-20卤代烷基;
R1、R2、R3在每次出现时独立地为H、卤素、C1-30烷基、C2-30链烯基、C1-30卤代烷基、C2-30炔基、C1-30烷氧基;
n=1、2;且
o=5-1000。
2.根据权利要求1的聚合物,其中R1、R2、R3独立地选自H、C1-20烷基和C1-20烷氧基,其中所述C1-20烷基或C1-20烷氧基可任选被1-4个独立地选自C1-20烷基和C1-20烷氧基的基团取代。
3.根据权利要求2的聚合物,其中R1、R2、R3独立地选自H和任选被1-4个C1-C6烷基取代的C6-20烷基。
4.根据权利要求1-3中任一项的聚合物,其中o=5-100。
5.根据权利要求1-4中任一项的聚合物作为半导体或电荷传输材料、作为薄膜晶体管(TFT)、或在有机发光二极管(OLED)、光伏组件或传感器用半导体组件中、作为电池组中的电极材料,作为光波导或用于电子照相术应用的用途。
6.一种组合物,其包含溶解或分散于液体介质中的一种根据或多种权利要求1-4中任一项的聚合物。
7.一种薄膜半导体,其包含一种或多种根据权利要求1-4中任一项的聚合物。
8.一种复合体,其包含衬底和沉积于所述衬底上的根据权利要求7的薄膜半导体。
9.一种制备根据权利要求8的复合体的方法,包括将根据权利要求1-4中任一项的聚合物溶解或分散于液体介质中以形成溶液,将所述溶液沉积于衬底上并除去溶剂从而在所述衬底上形成薄膜半导体。
10.根据权利要求9的方法,其中将所述溶液通过旋涂、液滴流延、浸涂或印刷沉积。
11.一种场效应晶体管器件,其包括根据权利要求7的薄膜半导体或根据权利要求8的复合体。
12.一种光伏器件,其包括根据权利要求7的薄膜半导体或根据权利要求8的复合体。
13.一种有机发光二极管器件,其包括根据权利要求7的薄膜半导体或根据权利要求8的复合体。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US26577809P | 2009-12-02 | 2009-12-02 | |
US61/265,778 | 2009-12-02 | ||
PCT/EP2010/068365 WO2011067192A2 (en) | 2009-12-02 | 2010-11-29 | Dithienobenzo-thieno[3,2-b]thiophene-copolymer and its use as high performance solution processable semiconducting polymer |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102639591A CN102639591A (zh) | 2012-08-15 |
CN102639591B true CN102639591B (zh) | 2015-05-13 |
Family
ID=43912750
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201080054412.3A Active CN102639591B (zh) | 2009-12-02 | 2010-11-29 | 二噻吩并苯并噻吩并[3,2-b]噻吩共聚物及其作为高性能可溶液加工半导体聚合物的用途 |
Country Status (6)
Country | Link |
---|---|
US (1) | US8389670B2 (zh) |
EP (1) | EP2507286B1 (zh) |
JP (1) | JP5774599B2 (zh) |
KR (1) | KR101780083B1 (zh) |
CN (1) | CN102639591B (zh) |
WO (1) | WO2011067192A2 (zh) |
Families Citing this family (40)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102149750B (zh) | 2008-07-18 | 2014-04-23 | 芝加哥大学 | 半导体聚合物 |
US9153785B2 (en) | 2011-04-15 | 2015-10-06 | The University Of Chicago | Semiconducting polymers |
JP5742494B2 (ja) * | 2011-06-10 | 2015-07-01 | 住友化学株式会社 | 高分子化合物及びそれを用いた電子素子 |
WO2013116643A1 (en) * | 2012-02-03 | 2013-08-08 | The University Of Chicago | Semiconducting polymers |
US20130247992A1 (en) * | 2012-03-22 | 2013-09-26 | Polyera Corporation | Polymeric Blends and Related Optoelectronic Devices |
US20150295193A1 (en) * | 2012-11-22 | 2015-10-15 | University of Seoul Industry Cooperation Foundatio n | Semiconductor device using paper as a substrate and method of manufacturing the same |
CN104854111A (zh) * | 2012-12-03 | 2015-08-19 | 巴斯夫欧洲公司 | 用于有机电子器件的杂并苯化合物 |
EP2936052B1 (en) | 2012-12-19 | 2021-04-28 | Basf Se | Detector for optically detecting at least one object |
CN104119502A (zh) * | 2013-04-25 | 2014-10-29 | 海洋王照明科技股份有限公司 | 含噻吩并噻吩-二噻吩并苯并噁二唑-苯并噻二唑类共轭聚合物及其制备方法与应用 |
CN104119501A (zh) * | 2013-04-25 | 2014-10-29 | 海洋王照明科技股份有限公司 | 含噻吩并噻吩-二噻吩并苯并噻二唑-苯并噻二唑类共轭聚合物及其制备方法与应用 |
CN104119503A (zh) * | 2013-04-25 | 2014-10-29 | 海洋王照明科技股份有限公司 | 含噻吩并噻吩-二噻吩并苯并三唑-苯并噻二唑类共轭聚合物及其制备方法与应用 |
CN104211921A (zh) * | 2013-05-29 | 2014-12-17 | 海洋王照明科技股份有限公司 | 共轭聚合物及其制备方法与应用 |
CN104211912A (zh) * | 2013-05-29 | 2014-12-17 | 海洋王照明科技股份有限公司 | 共轭聚合物及其制备方法与应用 |
CN104211915A (zh) * | 2013-05-29 | 2014-12-17 | 海洋王照明科技股份有限公司 | 共轭聚合物及其制备方法与应用 |
CN104211913A (zh) * | 2013-05-29 | 2014-12-17 | 海洋王照明科技股份有限公司 | 共轭聚合物及其制备方法与应用 |
EP3008484A1 (en) | 2013-06-13 | 2016-04-20 | Basf Se | Detector for optically detecting at least one object |
KR102252336B1 (ko) | 2013-06-13 | 2021-05-14 | 바스프 에스이 | 광학 검출기 및 그의 제조 방법 |
KR20160019067A (ko) | 2013-06-13 | 2016-02-18 | 바스프 에스이 | 적어도 하나의 물체의 배향을 광학적으로 검출하기 위한 검출기 |
CN103408733B (zh) * | 2013-08-13 | 2015-09-30 | 武汉理工大学 | 二硒吩并苯并二茚类共轭聚合物半导体材料及其应用 |
WO2015024870A1 (en) | 2013-08-19 | 2015-02-26 | Basf Se | Detector for determining a position of at least one object |
AU2014310703B2 (en) | 2013-08-19 | 2018-09-27 | Basf Se | Optical detector |
WO2015097078A2 (en) | 2013-12-24 | 2015-07-02 | Solvay Sa | Small molecule heteroacenes as semiconductors |
JP2015141912A (ja) * | 2014-01-27 | 2015-08-03 | 富士フイルム株式会社 | 有機薄膜トランジスタ、有機半導体薄膜および有機半導体材料 |
EP3167304A4 (en) | 2014-07-08 | 2018-02-21 | Basf Se | Detector for determining a position of at least one object |
JP6243032B2 (ja) * | 2014-07-18 | 2017-12-06 | 富士フイルム株式会社 | 有機半導体膜形成用組成物、並びに、有機半導体素子及びその製造方法 |
WO2016051323A1 (en) | 2014-09-29 | 2016-04-07 | Basf Se | Detector for optically determining a position of at least one object |
WO2016092451A1 (en) | 2014-12-09 | 2016-06-16 | Basf Se | Optical detector |
US10775505B2 (en) | 2015-01-30 | 2020-09-15 | Trinamix Gmbh | Detector for an optical detection of at least one object |
EP3325917B1 (en) | 2015-07-17 | 2020-02-26 | trinamiX GmbH | Detector for optically detecting at least one object |
US10412283B2 (en) | 2015-09-14 | 2019-09-10 | Trinamix Gmbh | Dual aperture 3D camera and method using differing aperture areas |
US11211513B2 (en) | 2016-07-29 | 2021-12-28 | Trinamix Gmbh | Optical sensor and detector for an optical detection |
WO2018077868A1 (en) | 2016-10-25 | 2018-05-03 | Trinamix Gmbh | Detector for an optical detection of at least one object |
KR102575104B1 (ko) | 2016-10-25 | 2023-09-07 | 트리나미엑스 게엠베하 | 집적 필터를 가진 적외선 광학 검출기 |
KR102484739B1 (ko) | 2016-11-17 | 2023-01-05 | 트리나미엑스 게엠베하 | 적어도 하나의 대상체를 광학적으로 검출하기 위한 검출기 |
US11860292B2 (en) | 2016-11-17 | 2024-01-02 | Trinamix Gmbh | Detector and methods for authenticating at least one object |
JP7204667B2 (ja) | 2017-04-20 | 2023-01-16 | トリナミクス ゲゼルシャフト ミット ベシュレンクテル ハフツング | 光検出器 |
CN110998223B (zh) | 2017-06-26 | 2021-10-29 | 特里纳米克斯股份有限公司 | 用于确定至少一个对像的位置的检测器 |
US11296290B2 (en) | 2018-03-07 | 2022-04-05 | Clap Co., Ltd. | Patterning method for preparing top-gate, bottom-contact organic field effect transistors |
US20200411781A1 (en) | 2018-03-08 | 2020-12-31 | Clap Co., Ltd. | Organic field effect transistor comprising semiconducting single-walled carbon nanotubes and organic semiconducting material |
US20210277157A1 (en) | 2018-06-26 | 2021-09-09 | Clap Co., Ltd. | Vinylether-based polymer as dielectric |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008026602A1 (fr) * | 2006-08-28 | 2008-03-06 | Tosoh Corporation | Dérivé hétéroacène, dérivé tétrahalotérphényle, et leurs procédés de production |
CN101170161A (zh) * | 2006-10-25 | 2008-04-30 | 施乐公司 | 电子器件 |
CN101200471A (zh) * | 2006-12-13 | 2008-06-18 | 三星电子株式会社 | 杂并苯化合物及包括它的有机薄膜以及包括该薄膜的电子器件 |
EP2006291A1 (en) * | 2006-03-10 | 2008-12-24 | Osaka University | Fused ring compound and method for producing same, polymer, organic thin film containing those, and organic thin film device and organic thin film transistor comprising such organic thin film |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5198153A (en) | 1989-05-26 | 1993-03-30 | International Business Machines Corporation | Electrically conductive polymeric |
JP3224829B2 (ja) | 1991-08-15 | 2001-11-05 | 株式会社東芝 | 有機電界効果型素子 |
WO1996021659A1 (en) | 1995-01-10 | 1996-07-18 | University Of Technology, Sydney | Organic semiconductor |
AU8991698A (en) * | 1997-09-05 | 1999-03-29 | Cambridge Display Technology Limited | Compounds for electronic devices |
DE602004017550D1 (de) * | 2003-08-28 | 2008-12-18 | Merck Patent Gmbh | Mono-, Oligo- und Polythienoi2,3-b thiophene |
DE602004024629D1 (de) | 2003-10-15 | 2010-01-28 | Merck Patent Gmbh | Polybenzodithiophene |
US20080303000A1 (en) | 2005-03-11 | 2008-12-11 | Martin Heeney | Monomers, Oligomers and Polymers Comprising Thiophene and Selenophene |
EP1891077B1 (en) | 2005-06-09 | 2010-04-21 | Merck Patent GmbH | Monomers , oligomers and polymers of thieno (3, 4-d) thiazole |
JP5164134B2 (ja) * | 2006-03-10 | 2013-03-13 | 住友化学株式会社 | 縮合環化合物及びその製造方法、重合体、これらを含む有機薄膜、並びに、これを備える有機薄膜素子及び有機薄膜トランジスタ |
JP5472874B2 (ja) * | 2006-10-25 | 2014-04-16 | 三星電子株式会社 | 電子デバイス |
JP5138422B2 (ja) * | 2008-02-29 | 2013-02-06 | 株式会社リコー | ベンゾチエノ[3,2−b]ベンゾチオフェン構造を含む重合体 |
WO2010000669A1 (en) | 2008-07-02 | 2010-01-07 | Basf Se | Poly(5,5'bis(thiophen-2-yl)-benzo[2,1-b;3,4-b']dithiophene) and its use as high performance solution processable semiconducting polymer |
TWI471328B (zh) | 2008-07-02 | 2015-02-01 | Basf Se | 以二噻吩并〔2,3-d:2’,3’-d’〕苯并〔1,2-b:4,5-b’〕二噻吩為主之高效能溶液可加工之半導體 |
WO2010018081A1 (en) | 2008-08-11 | 2010-02-18 | Basf Se | Polybenzothiophene polymers and process for their preparation |
-
2010
- 2010-11-29 CN CN201080054412.3A patent/CN102639591B/zh active Active
- 2010-11-29 JP JP2012541429A patent/JP5774599B2/ja active Active
- 2010-11-29 WO PCT/EP2010/068365 patent/WO2011067192A2/en active Application Filing
- 2010-11-29 EP EP10785057.0A patent/EP2507286B1/en active Active
- 2010-11-29 US US13/511,890 patent/US8389670B2/en active Active
- 2010-11-29 KR KR1020127016964A patent/KR101780083B1/ko active IP Right Grant
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2006291A1 (en) * | 2006-03-10 | 2008-12-24 | Osaka University | Fused ring compound and method for producing same, polymer, organic thin film containing those, and organic thin film device and organic thin film transistor comprising such organic thin film |
WO2008026602A1 (fr) * | 2006-08-28 | 2008-03-06 | Tosoh Corporation | Dérivé hétéroacène, dérivé tétrahalotérphényle, et leurs procédés de production |
CN101170161A (zh) * | 2006-10-25 | 2008-04-30 | 施乐公司 | 电子器件 |
CN101200471A (zh) * | 2006-12-13 | 2008-06-18 | 三星电子株式会社 | 杂并苯化合物及包括它的有机薄膜以及包括该薄膜的电子器件 |
Also Published As
Publication number | Publication date |
---|---|
US20120289672A1 (en) | 2012-11-15 |
JP5774599B2 (ja) | 2015-09-09 |
EP2507286A2 (en) | 2012-10-10 |
WO2011067192A3 (en) | 2011-09-15 |
CN102639591A (zh) | 2012-08-15 |
EP2507286B1 (en) | 2017-07-05 |
KR101780083B1 (ko) | 2017-10-10 |
US8389670B2 (en) | 2013-03-05 |
KR20120116427A (ko) | 2012-10-22 |
JP2013512975A (ja) | 2013-04-18 |
WO2011067192A2 (en) | 2011-06-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN102639591B (zh) | 二噻吩并苯并噻吩并[3,2-b]噻吩共聚物及其作为高性能可溶液加工半导体聚合物的用途 | |
CN102084436B (zh) | 聚(5,5′-二(噻吩-2-基)苯并[2,1-b;3,4-b′]二噻吩)及其作为高性能可溶液加工半导体聚合物的用途 | |
CN102083838B (zh) | 基于二噻吩并[2,3-d:2′,3′-d′]苯并[1,2-b:4,5-b′]二噻吩的高性能可溶液加工半导体 | |
CN101977961B (zh) | 取代的低聚-或聚噻吩 | |
CN102317345B (zh) | 由二噻吩基亚乙烯基共聚物制备的半导体材料 | |
CN102459398B (zh) | 稠合的联噻吩-亚乙烯基共聚物 | |
CN103635505B (zh) | 二噻吩并邻苯二甲酰亚胺半导体聚合物 | |
KR20130040830A (ko) | 어닐링된 디티오펜 공중합체 | |
CN102119185A (zh) | 聚苯并噻吩聚合物及其制备方法 | |
CN101160338A (zh) | 包括噻吩和硒吩的单体、低聚物和聚合物 | |
CN103415522B (zh) | 四氮杂靴二蒽化合物及其作为n-型半导体的用途 | |
Shaik et al. | Synthesis of donor–acceptor copolymer using benzoselenadiazole as acceptor for OTFT | |
Zhang et al. | Controlling Morphology of Active Layer by Tuning Coplanarity of the Centrality in Acceptor‐Donor‐Acceptor Small Molecules for Photovoltaic Application |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right |
Effective date of registration: 20211101 Address after: Seoul, South Kerean Patentee after: Clap Ltd. Patentee after: MAX-PLANCK-GESELLSCHAFT ZUR FORDERUNG DER WISSENSCHAFT E.V. Address before: Ludwigshafen, Germany Patentee before: BASF SE Patentee before: MAX-PLANCK-GESELLSCHAFT ZUR FORDERUNG DER WISSENSCHAFT E.V. |
|
TR01 | Transfer of patent right |