JP5505901B2 - ドーパントとしてフッ化イオン交換ポリマーを有するポリチエノチオフェンの水性ディスパージョン - Google Patents
ドーパントとしてフッ化イオン交換ポリマーを有するポリチエノチオフェンの水性ディスパージョン Download PDFInfo
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- JP5505901B2 JP5505901B2 JP2010115219A JP2010115219A JP5505901B2 JP 5505901 B2 JP5505901 B2 JP 5505901B2 JP 2010115219 A JP2010115219 A JP 2010115219A JP 2010115219 A JP2010115219 A JP 2010115219A JP 5505901 B2 JP5505901 B2 JP 5505901B2
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- dispersion
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- polythienothiophene
- colloid
- aqueous dispersion
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- 239000006185 dispersion Substances 0.000 title claims abstract description 179
- 229920003303 ion-exchange polymer Polymers 0.000 title claims description 26
- 239000002019 doping agent Substances 0.000 title description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical group [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 title 1
- 239000002253 acid Substances 0.000 claims abstract description 76
- 229910052751 metal Inorganic materials 0.000 claims abstract description 25
- 239000002184 metal Substances 0.000 claims abstract description 25
- 229920000642 polymer Polymers 0.000 claims description 82
- 238000000034 method Methods 0.000 claims description 56
- 239000000463 material Substances 0.000 claims description 54
- PFZLGKHSYILJTH-UHFFFAOYSA-N thieno[2,3-c]thiophene Chemical compound S1C=C2SC=CC2=C1 PFZLGKHSYILJTH-UHFFFAOYSA-N 0.000 claims description 51
- 239000000178 monomer Substances 0.000 claims description 41
- 239000007800 oxidant agent Substances 0.000 claims description 28
- 239000003456 ion exchange resin Substances 0.000 claims description 24
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 17
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 14
- 230000001590 oxidative effect Effects 0.000 claims description 14
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 239000011734 sodium Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 238000000816 matrix-assisted laser desorption--ionisation Methods 0.000 claims description 8
- 239000012528 membrane Substances 0.000 claims description 8
- 239000004065 semiconductor Substances 0.000 claims description 8
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 6
- 238000005266 casting Methods 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 claims description 6
- 229910000360 iron(III) sulfate Inorganic materials 0.000 claims description 6
- 150000003460 sulfonic acids Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 229910052742 iron Inorganic materials 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 4
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 claims description 3
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 3
- OZECDDHOAMNMQI-UHFFFAOYSA-H cerium(3+);trisulfate Chemical compound [Ce+3].[Ce+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O OZECDDHOAMNMQI-UHFFFAOYSA-H 0.000 claims description 3
- 229910000333 cerium(III) sulfate Inorganic materials 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 claims description 3
- 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 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims 4
- 238000002347 injection Methods 0.000 abstract description 50
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- 239000000203 mixture Substances 0.000 abstract description 35
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- 150000007513 acids Chemical class 0.000 abstract description 13
- 239000010409 thin film Substances 0.000 abstract description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 9
- 230000005669 field effect Effects 0.000 abstract description 9
- 239000002041 carbon nanotube Substances 0.000 abstract description 7
- 229910021393 carbon nanotube Inorganic materials 0.000 abstract description 7
- 239000002070 nanowire Substances 0.000 abstract description 7
- 238000000605 extraction Methods 0.000 abstract description 5
- 230000005693 optoelectronics Effects 0.000 abstract 1
- 238000013086 organic photovoltaic Methods 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 184
- 229920001940 conductive polymer Polymers 0.000 description 32
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 29
- 238000006116 polymerization reaction Methods 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 22
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 21
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- 239000000084 colloidal system Substances 0.000 description 20
- 150000002500 ions Chemical class 0.000 description 18
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- 230000006870 function Effects 0.000 description 16
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
- 239000002245 particle Substances 0.000 description 14
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- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 13
- 239000003957 anion exchange resin Substances 0.000 description 13
- 239000011575 calcium Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 230000002378 acidificating effect Effects 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000000137 annealing Methods 0.000 description 11
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- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 11
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000005342 ion exchange Methods 0.000 description 9
- 238000004528 spin coating Methods 0.000 description 9
- 229910052786 argon Inorganic materials 0.000 description 8
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- 150000002739 metals Chemical class 0.000 description 8
- 239000011368 organic material Substances 0.000 description 8
- 239000002033 PVDF binder Substances 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 229910052788 barium Inorganic materials 0.000 description 7
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 229910052791 calcium Inorganic materials 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 150000007524 organic acids Chemical class 0.000 description 6
- 238000005240 physical vapour deposition Methods 0.000 description 6
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 6
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- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 238000005341 cation exchange Methods 0.000 description 5
- 229940023913 cation exchange resins Drugs 0.000 description 5
- 239000011651 chromium Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000002482 conductive additive Substances 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical group FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
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- 229910052757 nitrogen Inorganic materials 0.000 description 4
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- 229920000301 poly(3-hexylthiophene-2,5-diyl) polymer Polymers 0.000 description 4
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- 239000011701 zinc Substances 0.000 description 4
- RRZIJNVZMJUGTK-UHFFFAOYSA-N 1,1,2-trifluoro-2-(1,2,2-trifluoroethenoxy)ethene Chemical compound FC(F)=C(F)OC(F)=C(F)F RRZIJNVZMJUGTK-UHFFFAOYSA-N 0.000 description 3
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 description 3
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
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- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 2
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- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
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- 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
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- H10K85/10—Organic polymers or oligomers
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Description
本願は、2005年3月24日に出願された仮出願番号60/665,026号および2004年10月13日に出願された仮出願第60/618,471号の利益を主張する。これらの出願の開示を参照することにより本明細書に取り込む。
アノード/正孔注入層/EL層/カソード
正極/正孔引抜き層(hole extraction layer)/光収穫層(複数可)/負極
ディスパージョンA
0.0575グラム(0.111ミリモル)の硫酸鉄(III)水和物(97%、Sigma-Aldrich Chemical Co)および0.135グラム(0.515ミリモル)の過硫酸カリウム(99+%、Fischer Scientific Co.)を、44.53gの脱イオン水とともに60mlのジャケット付き反応フラスコに加えた。固形物が溶解するまで、系を5分間混合した。15.47グラム(1.406ミリ当量)の10%ナフィオン(登録商標)水性ディスパージョン(Aldrich Chemical Co.から入手)を反応器に加えた。反応器を反応混合物で完全に満たした。ジャケット付き反応フラスコを調整し、16℃の反応温度に維持した。0.0807g(0.576ミリモル)のチエノ[3,4−b]チオフェンを反応混合物に加えた。重合の間、反応器の内容物をよく混合し、確実に安定なディスパージョンとした。反応塊(reaction mass)は、20分以内に、急速に明るい緑からエメラルドグリーンに、不透明な濃青色に変わった。モノマーの導入後、重合を4時間進行させた。反応生成物をカチオン樹脂アンバーライト(Amberlite;登録商標)IR−120(プラス)およびアニオンイオン交換樹脂ルワティット(Lewatit;登録商標)MP62により精製した。
15gのディスパージョンAを、連続的に、2.8gのアンバーライト(登録商標)IR−120カチオン交換樹脂(シグマ−アルドリッチ ケミカル社(Sigma-Aldrich Chemical Co))および2.8gのルワティット(登録商標)MP−62アニオン交換樹脂(Fluka, シグマ−アルドリッチ ケミカル社)に通して精製し、不透明な濃青色のポリ(チエノ[3,4−b]チオフェン)/ナフィオン(登録商標)水性ディスパージョンを得た。
別に、15gのディスパージョンAを、5.0gのアンバーライト(登録商標)IR−120および5.0gのルワティット(登録商標)MP−62イオン交換樹脂を加えて精製し、不透明な濃青色のポリ(チエノ[3,4−b]チオフェン)/ナフィオン(登録商標)水性ディスパージョンと樹脂とのスラリーを得た。終夜の交換の後、スラリーを0.45ミクロンフィルターに通して濾過し、精製されたディスパージョンからイオン交換樹脂を分離した。
終夜の交換の後、ディスパージョンAスラリーの残りの30グラムを、5.0μmフィルターに通して濾過し、精製されたディスパージョンからイオン交換樹脂を分離した。
217グラムの脱イオン水を500mlのジャケット付き反応器に加えた。79.87グラム(72.6ミリ当量)の10%ナフィオン(登録商標)水性ディスパージョン(Aldrich Chemical Co.)を反応器に加え、オーバーヘッドスターラーで5分間混合した。ジャケット付き反応フラスコを調整し、16℃の反応温度を維持した。0.7973グラム(5.7ミリモル)のチエノ[3,4−b]チオフェンを、52.3グラムの脱イオン水に溶かした3.3グラム(6.4ミリモル)のFe2(SO4)3 *H2Oとともに、反応器に別に共供給した。反応塊は、20分以内に、明るい緑からエメラルドグリーンに、濃青色に変わった。モノマーおよび酸化剤の導入後、重合を4時間進行させた。次いで、反応器の内容物を、17.5グラムのアンバーライト(登録商標)IR−120カチオン交換樹脂(シグマ−アルドリッチ ケミカル社)および17.5グラムのルワティット(登録商標)MP−62アニオン交換樹脂(Fluka,シグマ−アルドリッチ ケミカル社)を含む500mlのNalgene(登録商標)ボトルに加えることにより、得られたディスパージョンを精製すると、不透明な濃青色のポリ(チエノ[3,4−b]チオフェン)/ナフィオン(登録商標)水性ディスパージョンが得られた。前記ディスパージョンを、連続的に、10、5、0.65および0.45ミクロンの細孔径のフィルターに通して濾過した。
デバイス性能の比較のため、参照することにより本明細書に取り込む米国特許出願公開番号第2005−0151122−A1にしたがい、ポリマー対イオン/ドーパント/分散剤としてポリ(スチレンスルホン酸)を利用してポリ(チエノ[3,4−b]チオフェン)のディスパージョンを作成した。前記ディスパージョンをPTT:PSSAと称する。
ディスパージョンBは、0.45ミクロンの細孔径のPVDFフィルターを用いて濾過可能である。ディスパージョンBのドロップキャスト膜(1インチ×1インチのガラス支持体上に0.5mL)は、窒素雰囲気下180℃で15分間アニーリングした後、導電率が2.56×10-2S/cmの膜を与えた。アニーリング前のドロップしたままの膜の導電率は9.03×10-7S/cmであった。導電率は、4点プローブ法を利用しアルゴンを充満させたグローブボックス中で測定した。
実施例2
19.8mgのMEH−PPV(ポリ(2−メトキシ、5−(2’−エチル−ヘキシルオキシ)−p−フェニレン−ビニレン)、ADS130RE、カナダ国、ケベック州、Baie D’UrfeのAmerican Dye Source製)を60℃のホットプレート上で2時間2.84gのトルエンに溶解させて、発光ポリマーMEH−PPVのトルエン溶液を調製し、次いで、0.45μmPVDFフィルターで濾過した。前記溶液を以下で溶液Aと称する。この実施例により得られたデバイスを図2に示すが、任意の層140はない。
IV CCDカメラを利用して測定し、図3に示す。EL発光のパワーは、較正済みSiフォトダイオードと連結しているNewport 2835−C多機能光学計を利用して測定した。輝度は、EL発光のランバート分布を仮定しELフォワード出力およびデバイスのELスペクトルを利用して計算し、Photo Research PR650比色計により裏付けた。前記デバイスは、約2.4Vで1cd/cm2に達した。最大外部量子効率は0.60%であった。100mA/cm2の電流密度で、前記デバイスは1,290cd/cm2の輝度を示した。1000mA/cm2の電流密度で、輝度は13,400cd/cm2であった。
ディスパージョンCを正孔注入/輸送層として用い、実施例2と同様にOLEDデバイスを作成した。スピンコートの前に、ディスパージョンCを0.45ミクロンの細孔径のPVDFフィルターで濾過した。厚さが約78nmのPTT:ナフィオンの均一な膜が、1500rpmの回転速度で得られた。このデバイスの構造を図2に示すが、任意の層140はない。デバイスは、約2.1Vで1cd/cm2に達し、最大外部量子効率は1.26%であった。100mA/cm2の電流密度で、前記デバイスは3,040cd/cm2の輝度を示した。1000mA/cm2の電流密度で、輝度は26,400cd/cm2であった。この実施例により得られたデバイスを運転した性能結果を図4に示す。
66.2mgのポリ(N−ビニルカルバゾール)(アメリカ合衆国、ウィスコンシン州、ミルウォーキーのアルドリッチ ケミカル社(Aldrich Chemical Company,Inc)製)、38.7mgの2−(4−ビフェニリル)−5−(4−tert−ブチルフェニル)−1,3,4−オキサジアゾール(アルドリッチ ケミカル社.)、24.8mgのN,N’−ビス(3−メチルフェニル)−N,N’−ジフェニルベンジジン(アルドリッチ ケミカル社.)および8.5mgのトリプレットエミッター(triplet emitter)トリス(2−(4−トリル)フェニルピリジン)イリジウム(III)(American Dye Source, Inc.製)を5.38gのクロロベンゼンに溶解させ、溶液を調製した。溶液を、60℃のホットプレート上で2時間加熱し、次いで0.2ミクロンフィルターで濾過し、以下で溶液Bと称する。溶液Cは溶液B1.0mL中に0.5mLのクロロベンゼンを加えて調製し、デバイス製造に用いた。
ディスパージョンCを正孔注入/輸送層として用いて、実施例4と同様にOLEDデバイスを調製した。このデバイスの構造を図2に示すが、任意の層140はない。デバイスは、約5.9Vで1cd/cm2に達し、最大外部量子効率は2.02%であった。100mA/cm2の電流密度で、前記デバイスは6,630cd/cm2の輝度を示した。1000mA/cm2の電流密度で、輝度は48,900cd/cm2であった。
表面抵抗10−15オーム/スクエアの3つのパターニングされたITO支持体を実施例2と同様に洗浄した。次いで、ITO支持体に、1500rpmの回転速度で、それぞれ、ディスパージョンC、ディスパージョンDおよび参照することにより本明細書に取り込む米国特許出願公開番号2005−0151122−A1に開示されている手順にしたがい製造したPTT:PSSAディスパージョンをスピンコートした。次いで、ITO支持体を180から200℃で15分間アニーリングした。アニーリングの後、約80nmの厚さのLUMATION Green 1304(住友化学(株)製)の層をトルエン溶液からスピンコートした。次いで、試料を、窒素ガス保護下で、ホットプレート上で、130℃で20分間ベーキングした。次いで、試料を、アルゴン雰囲気のグローブボックス中に置かれている真空エバポレーターのチャンバー中に移した。5nmの厚さのBa層を、約1.5Å/sの速度でマスクを通して1×10-7トール未満で真空堆積させ、120nmの厚さのAg層を、堆積速度約3.0−4.0Å/sでBa層の上に真空堆積した。次いで、デバイスを、アルゴングローブボックス中でガラスカバー蓋およびUV硬化エポキシで密封した。デバイスをグローブボックスから取りだし、実施例2と同様にIV曲線および輝度に関して測定した。デバイスの効率を図5に示した。キャラクタリゼーションの後、デバイスをCDT Eclipse PLED Lifetime Tester上に置き、初期輝度2000cd/cm2でDC寿命試験を行った。図6は寿命試験結果を示す。ディスパージョンCおよびDを利用したデバイスは、PTT:PSSAを正孔注入層として利用したデバイスに比べ著しく長い寿命を示した。デバイスの半減期は、デバイスの輝度が初期値2000cd/cm2の50%、すなわち1000cd/cm2に達するのにかかる時間として定義される。デバイスの半減期は、PTT:PSSAデバイスでは289時間であるが、PTT:ナフィオン(登録商標)ディスパージョンCおよびディスパージョンDのPTT:ナフィオン(登録商標)系デバイスでは1870時間および1650時間であった。図7に示すとおり、ディスパージョンCおよびDを利用したデバイスの動作電圧は、PTT:PSSAを正孔注入層として利用したデバイスに比べはるかに安定していた。PTT:PSSAデバイスの電圧上昇率は、289時間で0.6Vであった。PTT:ナフィオン(登録商標)ディスパージョンCおよびDに基づくデバイスでは電圧上昇率は1870時間で0.6Vおよび1650時間で0.5Vであった。
表面抵抗10−15オーム/スクエアの3つのパターニングされたITO支持体を実施例2と同様に洗浄した。次いで、ITO支持体に、1500rpmの回転速度で、それぞれ、ディスパージョンB、ディスパージョンCおよび参照することにより本明細書に取り込む米国特許出願公開番号2005−0151122−A1に開示されている手順にしたがい製造したPTT:PSSAディスパージョンをスピンコートした。次いで、ITO支持体を180から200℃で15分間アニーリングした。アニーリングの後、約80nmの厚さのLUMATION Blue LEP発光ポリマー(住友化学(株)製)の層をトルエン溶液からスピンコートした。次いで、試料を、窒素ガス保護下で、ホットプレート上で、130℃で20分間ベーキングした。次いで、試料を、アルゴン雰囲気のグローブボックス中に置かれている真空エバポレーターのチャンバー中に移した。5nmの厚さのBa層を、約1.5Å/sの速度でマスクを通して1×10-7トール未満で真空堆積させ、120nmの厚さのAg層を、堆積速度約3.0−4.0Å/sでBa層の上に真空堆積した。次いで、デバイスを、アルゴングローブボックス中でガラスカバー蓋およびUV硬化エポキシで密封した。デバイスをグローブボックスから取りだし、実施例2と同様にIV曲線および輝度に関して測定した。キャラクタリゼーションの後、デバイスをCDT Eclipse PLED Lifetime Tester上に置き、初期輝度1000cd/cm2でDC寿命試験を行った。図8は寿命試験結果を示す。ディスパージョンCおよびBを利用したデバイスは、PTT:PSSAを正孔注入層として利用したデバイスに比べ著しく長い寿命を示した。デバイスの半減期は、PTT:PSSAデバイスでは42時間であるが、PTT:ナフィオン(登録商標)ディスパージョンBおよびディスパージョンC系デバイスでは122時間および175時間であった。図9に示すとおり、PTT:ナフィオン(登録商標)ディスパージョンCおよびDを利用したデバイスの動作電圧は、PTT:PSSAを正孔注入層として利用したデバイスに比べはるかに安定していた。PTT:PSSAデバイスの電圧上昇率は、42時間で2.3Vであった。PTT:ナフィオン(登録商標)ディスパージョンBおよびディスパージョンCに基づくデバイスでは電圧上昇率は122時間で0.9Vおよび175時間で0.8Vであった。
8.4mgの位置規則性ポリ(3−ヘキシルチオフェン)(P3HT、Riek Metals,Inc製)および8.9mgのN,N’−ビス(2,5−ジ−tert−ブチルフェニル)−3,4,9,10−ペリレンジカルボキシミド(PDCBI、Sigma−Aldrich製)を1.0gのクロロベンゼンに溶解させて、正孔および電子輸送材料としてのP3HTおよびPDCBIの溶液を調製した。溶液を、細孔径0.2ミクロンのPTFEフィルターで濾過した。前記溶液を本願で溶液Eと称する。パターニングされたITO支持体を正極としBaを負極としてPVデバイスを製造した。ITO支持体は、洗剤を含む脱イオン水ならびにメタノールおよびイソプロパノールを用いて超音波洗浄機で洗浄した。溶媒洗浄の後、ITO支持体を、SPI Desktop II酸素プラズマエッチャー中で10分間酸素プラズマで洗浄した。正孔引抜き層(HEL)用に、実施例1で合成したPTT:ナフィオン(登録商標)またはBaytron P Al4083(ポリ(エチレン−3,4−ジオキシチオフェン):ポリ(スチレンスルホン酸)(PEDOT:PSSA、Bayer製)をその水性ディスパージョンから、1500rpmの回転速度でスピンコートし、空気中で180℃で15分間硬化した。PTT:ナフィオン(登録商標)およびPEDOT:PSSAディスパージョンを、0.45ミクロンPVDFフィルターで濾過してから、スピンコートした。アニーリングの後、P3HT:PDCBIブレンドの層を、溶液EからHEL上へ2000rpmの回転速度で1分間スピンコートした。次いで、試料をマスクし、アルゴン雰囲気のドライボックス内に置かれた真空エバポレーターのチャンバーに移した。5nmの厚さのバリウム(Ba)層を、マスクを通して1×10-7トール未満で真空堆積させ、120nmの厚さの銀(Ag)層をBa層の上に真空堆積し、電極抵抗を下げBa層に保護を与えた。次いで、デバイスを、アルゴングローブボックス中でガラスカバー蓋およびUV硬化エポキシ(UV15、Master Bond,Inc製)で密封した。デバイス試験を室温および空気中で実施した。膜の厚さは、KLA Tencor P15表面プロファイラーで測定した。電流−電圧特性は、Keithley 2400 SourceMeterで測定した。Thermal Oriel製の150Wのオゾンレスキセノンランプを、PVデバイスのキャラクタリゼーションのための照明光源として使用した。HELとしてディスパージョンEからスピンコートしたPTT:ナフィオン(登録商標)膜を利用すると、より高い開回路電圧および短絡電流が得られた。
実験1のディスパージョンEに記載の手順にしたがい、ディスパージョンを作成した。3mLのディスパージョンを1インチ×3インチのガラス支持体にドロップキャストした。ディスパージョンを乾燥した後、支持体を、3つの1インチ×1インチ試料に切断し、それらを以下で試料10A、試料10Bおよび試料10Cと称する。次いで、試料10Bおよび10Cを、ホットプレートを用いて空気中で、それぞれ160および180℃で15分間アニーリングした。3試料全てについて、アメリカ合衆国、マサチューセッツ州、ビルリカのBruker Daltonics製のBiflex IIIデバイスで、マトリックス支援レーザー脱離イオン化飛行時間(MALDI−TOF)質量分析法により分子量を分析した。7,7’,8,8’−テトラシアノキノジメタン(TCQN、Aldrich製)をマトリックスとして使用した。試料調製には、試料10A、10Bまたは10Cの薄膜の薄片のいくつかを約3mgのTCNQとMALDIプレート上で混合した。MALDI−TOF質量分析の結果は、高温でのアニーリングの後、より多数の繰り返し単位を持つポリチエノチオフェンがより多くあることを示した。図11は、試料10Aおよび10CのMALDI−TOFマススペクトルを示す。この結果は、導電性ポリマー膜が高温でアニーリングされると、更なる重合が固体状態で起こり、導電性ポリマーの鎖長が増すことを示している。
Claims (16)
- 前記コロイド形成性ポリマー酸が、少なくとも1種のフッ化スルホン酸ポリマーを含む請求項1に記載のディスパージョン。
- 以下の工程を含む、ポリチエノチオフェンを含むディスパージョンを製造する方法:
(a)少なくとも1種の酸化剤および/または少なくとも1種の触媒を含む水性ディスパージョンを提供する工程;
(b)少なくとも1種のコロイド形成性ポリマー酸を含む水性ディスパージョンを提供する工程;
(c)工程(a)の水性ディスパージョンを、工程(b)の水性ディスパージョンと組合せる工程;
(d)工程(c)の組合せした水性ディスパージョンにチエノチオフェンモノマーを加える工程;および
(e)ポリチエノチオフェンを形成する工程;
前記ポリチエノチオフェンが下記の(1)または(2)の構造を含み、
前記少なくとも1種のコロイド形成性ポリマー酸が、以下を含む構造を有するものである水性ディスパージョンを製造する方法。
- 前記の少なくとも1種の酸化剤が、硫酸鉄(III)、塩化鉄(III)、過硫酸ナトリウム、過硫酸カリウムおよび過硫酸アンモニウムからなる群から選択される少なくとも1つのメンバーを含む請求項3に記載の方法。
- 前記の少なくとも1種の触媒が、硫酸鉄(III)、塩化鉄(III)および硫酸セリウム(III)からなる群から選択される少なくとも1つのメンバーを含む請求項3に記載の方法。
- 前記ポリチエノチオフェンディスパージョンを少なくとも2種のイオン交換樹脂と接触させる工程を更に含む請求項3に記載の方法。
- 以下の工程を含む、導電性膜を支持体上に形成する方法:
ポリチエノチオフェンを含むディスパージョンを形成するために、少なくとも1種のフッ化材料の存在下でチエノチオフェンモノマーを重合する工程、
前記ディスパージョンを支持体上に塗布して膜を形成する工程、
前記支持体および膜を加熱する工程;および
膜を塗布された支持体を回収する工程;
前記ポリチエノチオフェンが下記の(1)または(2)の構造を含み、
前記少なくとも1種のフッ化材料が、以下を含む構造を有するものである、導電性膜を支持体上に形成する方法。
- 前記加熱が、膜の導電率を上昇させるに充分な温度および時間である請求項7に記載の方法。
- 前記加熱が、MALDI(マトリックス支援レーザー脱離イオン化)を利用して測定されるポリマー繰り返し単位の数を増加させるに充分である請求項7に記載の方法。
- 前記の少なくとも1種のフッ化材料が、少なくとも1種のフッ化スルホン酸ポリマーを含む請求項7に記載の方法。
- 前記加熱が約130℃を超える温度で実施される請求項7に記載の方法。
- 前記膜が、鉄、カリウムおよびナトリウムからなる群から選択される少なくとも1つの金属を更に含む請求項7に記載の方法。
- 前記金属が鉄を含む請求項12に記載の方法。
- 少なくとも2つの電極、ポリ(チエノ[3,4−b]チオフェン)を含む層および少なくとも1種の半導性材料を含む層を含むデバイスであって;
前記ポリ(チエノ[3,4−b]チオフェン)を含む層が、ポリチエノチオフェンおよび少なくとも1種のコロイド形成性ポリマー酸を含む水性ディスパージョンのキャストにより形成され、
前記ポリチエノチオフェンが下記の(1)または(2)の構造を含み、
前記少なくとも1種のコロイド形成性ポリマー酸が、以下を含む構造を有するものであるデバイス。
- 前記デバイスが光電デバイスを含み、前記半導性材料が光活性である請求項14に記載のデバイス。
- 前記電極の1つがカソードを含み、片方がアノードを含み、前記半導性材料がエレクトロルミネッセンス層を含む請求項14に記載のデバイス。
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KR100839138B1 (ko) | 2008-06-19 |
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SG121978A1 (en) | 2006-05-26 |
EP1647566A2 (en) | 2006-04-19 |
JP5270065B2 (ja) | 2013-08-21 |
SG137861A1 (en) | 2007-12-28 |
CN102174246A (zh) | 2011-09-07 |
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TWI300785B (en) | 2008-09-11 |
ATE430172T1 (de) | 2009-05-15 |
US7569158B2 (en) | 2009-08-04 |
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