JP6591417B2 - チオフェン単位を含む新規の多環式ポリマー、かかるポリマーの製造方法および使用 - Google Patents
チオフェン単位を含む新規の多環式ポリマー、かかるポリマーの製造方法および使用 Download PDFInfo
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- JP6591417B2 JP6591417B2 JP2016534915A JP2016534915A JP6591417B2 JP 6591417 B2 JP6591417 B2 JP 6591417B2 JP 2016534915 A JP2016534915 A JP 2016534915A JP 2016534915 A JP2016534915 A JP 2016534915A JP 6591417 B2 JP6591417 B2 JP 6591417B2
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- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
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- 229920000123 polythiophene Polymers 0.000 description 1
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- 238000002360 preparation method Methods 0.000 description 1
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- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
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- 239000002096 quantum dot Substances 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
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- 230000006798 recombination Effects 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
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- 229910052701 rubidium Inorganic materials 0.000 description 1
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- FPDOSPSUXAVNKK-UHFFFAOYSA-N selenopheno[3,2-b]thiophene Chemical compound [se]1C=CC2=C1C=CS2 FPDOSPSUXAVNKK-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
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- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical group [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
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- 125000003107 substituted aryl group Chemical group 0.000 description 1
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- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
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- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- APBDREXAUGXCCV-UHFFFAOYSA-L tetraethylazanium;carbonate Chemical compound [O-]C([O-])=O.CC[N+](CC)(CC)CC.CC[N+](CC)(CC)CC APBDREXAUGXCCV-UHFFFAOYSA-L 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
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- 230000005619 thermoelectricity Effects 0.000 description 1
- URMVZUQDPPDABD-UHFFFAOYSA-N thieno[2,3-f][1]benzothiole Chemical compound C1=C2SC=CC2=CC2=C1C=CS2 URMVZUQDPPDABD-UHFFFAOYSA-N 0.000 description 1
- ONCNIMLKGZSAJT-UHFFFAOYSA-N thieno[3,2-b]furan Chemical compound S1C=CC2=C1C=CO2 ONCNIMLKGZSAJT-UHFFFAOYSA-N 0.000 description 1
- 125000004862 thiobutyl group Chemical group 0.000 description 1
- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- BOXGRKIAPBPUEN-UHFFFAOYSA-N tri(propan-2-yl)-thieno[3,2-b]thiophen-5-ylsilane Chemical compound S1C=CC2=C1C=C([Si](C(C)C)(C(C)C)C(C)C)S2 BOXGRKIAPBPUEN-UHFFFAOYSA-N 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- GQHWSLKNULCZGI-UHFFFAOYSA-N trifluoromethoxybenzene Chemical compound FC(F)(F)OC1=CC=CC=C1 GQHWSLKNULCZGI-UHFFFAOYSA-N 0.000 description 1
- DOIRPCDOGSNNCS-UHFFFAOYSA-N trimethyl-[5-(5-trimethylstannylthiophen-2-yl)thiophen-2-yl]stannane Chemical compound S1C([Sn](C)(C)C)=CC=C1C1=CC=C([Sn](C)(C)C)S1 DOIRPCDOGSNNCS-UHFFFAOYSA-N 0.000 description 1
- INHYKPMJJAWZKY-UHFFFAOYSA-N trimethyl-[5-[4-(5-trimethylstannylthiophen-2-yl)-2,1,3-benzothiadiazol-7-yl]thiophen-2-yl]stannane Chemical compound S1C([Sn](C)(C)C)=CC=C1C(C1=NSN=C11)=CC=C1C1=CC=C([Sn](C)(C)C)S1 INHYKPMJJAWZKY-UHFFFAOYSA-N 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
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- 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
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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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- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/124—Intrinsically conductive polymers
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Description
からなる群から選択される二価の単位を含む、化合物を提供する。
(a)前記化合物を提供すること、および
(b)前記化合物で、光学、電気光学、電子、熱電気、エレクトロルミネッセンスまたはフォトルミネッセンスのコンポーネントまたはデバイスにおける、電荷輸送、半導体、導電、光伝導または発光材料を製造すること
を含む、前記方法に関する。
本願の目的に対し、用語「縮合」および「アニールされた」は同義的に用いられる。
用語「ヒドロカルビル基」は、さらに1個または2個以上のH原子を含み、任意に1個または2個以上のヘテロ原子を含むカルビル基を意味すると理解されるであろう。
3個または4個以上のC原子の鎖を含むカルビルまたはヒドロカルビル基は、直鎖状、分枝状および/または環状、ならびにスピロおよび/または縮合環であってもよい。
本明細書中で使用する、「ハロゲン」は、F、Cl、BrまたはI、好ましくはF、ClまたはBrを含む。
本明細書中で使用する、−CO−、−C(=O)−および−C(O)−は、カルボニル基、つまり構造
本願の目的に対し、Rsは、それぞれの出現において互いに独立して、F、Br、Cl、−CN、−NC、−NCO、−NCS、−OCN、−SCN、−C(O)NR0R00、−C(O)X0、−C(O)R0、−C(O)OR0、−NH2、−NR0R00、−SH、−SR0、−SO3H、−SO2R0、−OH、−NO2、−CF3、−SF5、任意に置換されているシリル、1〜40個の炭素原子を有し、任意に置換され、1種または2種以上のヘテロ原子を含むカルビルまたはヒドロカルビルからなる群から選択される。
X0は、ハロゲン、好ましくは、F、ClまたはBrを示すために用いられる。
またはその保護された誘導体である。さらに好ましい基Pは、ビニルオキシ、アクリレート、メタクリレート、フッ素化アクリレート、塩化アクリレート、オキセタンおよびエポキシ基からなる群から、極めて好ましくは、アクリレートまたはメタクリレート基から選択される。
Sp’は、非置換であるか、またはF、Cl、Br、IまたはCNによって単置換または多置換されている、30個までの炭素原子を有するアルキレン、1または2以上の非隣接CH2基が、それぞれの場合において互いに独立して−O−、−S−、−NH−、−NR0−、−SiR0R00−、−C(O)−、−C(O)O−、−OC(O)−、−OC(O)−O−、−S−C(O)−、−C(O)−S−、−CH=CH−または−C≡C−によって、Oおよび/またはS原子が互いに直接結合しないように置換され得る、であり、
Y1およびY2は、互いに独立してH、F、ClまたはCNである。
本発明の化合物は、以下の式(I)
で表される二価の単位を含む。
で表される二価の単位を含む。Arが式(D1)〜(132)および(A1)〜(A93)からなる群から選択される場合が特に好ましい。
一側面において、本願は、小分子、すなわち式(I)および(Ia)からなる群から選択される構造単位、および2つの不活性化学基RaおよびRbを含む化合物を提供する。かかる小分子は、例えば式(IIa)で表わされ得る
Ra−M−Rb (IIa)
式中、Mは式(I)および(Ia)からなる群から選択される構造単位を含み、RaおよびRbは不活性化学基である。かかる不活性化学基RaおよびRbは、互いに独立して、例えば、水素、フッ素、1〜10個の炭素原子を有するアルキル、1〜10個の炭素原子を有するフルオロアルキル、6〜30個の炭素原子の芳香族環系および5〜30個の炭素原子の芳香族環系、ここで1個または2個以上の水素原子は、互いに独立してフッ素または1〜10個の炭素原子を有するアルキルによって置換されていてもよい、からなる群から選択される。
Rc−M−Rd (II−b)
式中、Mは式(I)または(Ia)で表される構造単位を含み、ならびにRcおよびRdは、上でRcに対して定義される反応性化学基である、
によって表される。
*−Ua m1−Ara m2−Ub m3−Arb m4−Arc m5−* (III)
式中、
UaおよびUbは、互いに独立して式(I)または(Ia)からなる群選択される二価の単位から選択され;
Ara、ArbおよびArcは、互いに独立して、UaおよびUbとは異なるアリールまたはヘテロアリールであり;
m1、m2、m3およびm4は、互いに独立して0、1または2、但しm1およびm3の少なくとも1つは0ではない、からなる群から選択され;ならびに
m5は、0または1〜10の整数(例えば、2、3、4、5、6、7、8または9)である。
*−Ara m2−Ub−Arb m4−* (III−a−1)
*−Ua m1−Ara m2−Ub m3−* (III−a−2)
ここで、Ara、Arb、Ua、Ub、m1、m2、m3ならびにm4は、上記に定義したとおりである、
の1つから選択されるものである。
*−Ara−Ua−Arb−* (III−b−1)
*−Ua−* (III−b−2)
*−Ara−Ua−* (III−b−3)
*−Ua−Arb−* (III−b−4)
*−Ua−Ara−Ub−* (III−b−5)
ここで、Ara、Arb、UaならびにUbは、上記に定義したとおりである
の1つから選択されるものである。
さらなる側面において、本願は、オリゴマーまたはポリマーを、すなわち、式(I)および(Ia)からなる群から選択される1より多い構造単位を含む化合物を提供する。好ましくは、かかるオリゴマーまたはポリマーは、式(III)、(III−a―1)、(III−a−2)および(III−b−1)〜(III−b−5)のいずれか1つに定義される、1より多い基Mを含む。それぞれの出現において、Mは、同じであっても異なっていてもよい。
*−[−Ard m6−Ara m2−Are m7−Arb m4−Arc m5]−* (IV)
Ara、Arb、Arc、m2、m4ならびにm5は上記に定義したとおりであり;
ArdおよびAreは、互いに独立して、電子供与体特性または電子受容体特性を有するアリールまたはヘテロアリールであり、好ましくは、互いに独立して、式(D1)〜(D132)および(A1)〜(A93)からなる群から選択され;および
m6およびm7は、互いに独立して、0、1または2であり、但しm6およびm7の少なくとも1つは0ではない(例えば、m6が0であり、かつm7が1である、またはm6が1でありかつm7が0である、またはm6が1でありかつm7が1である)
の1つから選択される。
mは、>1の整数であり;
M1、M2およびM3は、互いに独立して、以下に定義するモノマー単位であり、但しM1、M2およびM3は式(I)および(Ia)からなる群から選択される構造単位を含み;
mxは、>0かつ≦1であり;
myは、≧0かつ<1であり;ならびに
mzは、≧0かつ<1であり、
但しmx+my+mz=1であり、好ましくは、M1、M2またはM3のいずれかは式(I)または(Ia)で表される構造単位Mを含み、それぞれmx、myまたはmzは>0である。このように、MがM2に含まれる場合、my>0であり、MがM3に含まれる場合、その場合はmz>0である、
で表されるポリマー鎖を含み得る。
から選択され得る。
a)単位Uaまたは(Ara−Ua)または(Ara−Ua−Arb)または(Ara−Ua−Arc)または(Ua−Arb−Arc)または(Ara−Ua−Arb−Arc)または(Ua−Ara−Ua)のホモポリマー、すなわちすべての繰り返し単位が同一である、からなる、グループ1、
b)同一の単位(Ara−Ua−Arb)または(Ua−Ara−Ua)および同一の単位(Arc)によって形成された、ランダムまたは交互共重合体からなる、グループ2、
c)同一の単位(Ara−Ua−Arb)または(Ua−Ara−Ua)および同一の単位(Ara)によって形成された、ランダムまたは交互共重合体からなる、グループ3、
d)同一の単位(Ara−Ua−Arb)または(Ua−Ara−Ua)および同一の単位(Ara−Ard−Arb)または(Ard−Ara−Are)によって形成された、ランダムまたは交互共重合体からなる、グループ4、
式中、これらすべての基において、Ara、Arb、Arc、Ard、Are、UaおよびUbは、本明細書に定義されるとおりであり、グループ1、2および3において、Ara、Arb、Arcは単結合とは異なり、およびグループ4において、AraおよびArbの1つはまた、単結合を示してもよい。
Re−chain−Rf (VI)
− 0<my<1かつ0<mz<1;
− Mwが少なくとも5,000、好ましくは少なくとも8,000、より好ましくは少なくとも10,000である;
− Mwが、多くても300,000、好ましくは多くても100,000である;
− R1およびR2が、1〜20個の炭素原子を有する直鎖または分枝のアルキル、ここで1つまたは2つ以上のH原子はFにより任意に置換されていてもよい、から選択される置換基で、単置換または多置換、好ましくは、4位(つまり、パラ位)において単置換されている、フェニルである、
− すべての基において、RsがHである;
− 少なくとも1つの基において、RsがHとは異なる;
− Rsが、それぞれの出現において独立して、1〜30個の炭素原子を有する一級アルキル、3〜30個の炭素原子を有する二級アルキル、ならびに4〜30個の炭素原子を有する三級アルキル、ここで1つまたは2つ以上のH原子はFにより任意に置き換えられていてもよい、からなる群から選択される、
− R2が、それぞれの出現において同一であるかまたは異なって、アリールおよびヘテロアリール、これらのそれぞれは任意に、フッ素化またはアルコキシ化されていてもよく、および4〜30個の環原子を有する、からなる群から選択される;
− RSが、それぞれの出現において同一であるかまたは異なって、1〜30個のC原子を有する一級アルコキシまたはスルファニルアルキル、3〜30個のC原子を有する二級アルコキシまたはスルファニルアルキル、および4〜30個のC原子を有する三級アルコキシまたはスルファニルアルキル、ここですべてのこれら基において、1または2以上のH原子は、Fにより任意に置換されている、からなる群から選択される;
− RSは、それぞれの出現において同一であるかまたは異なって、アリールオキシおよびヘテロアリールオキシ、その各々は任意に、アルキル化またはアルコキシル化されており、および4〜30個の環原子を有している、からなる群から選択される;
− RSは、それぞれの出現において同一であるかまたは異なって、アルキルカルボニル、アルコキシカルボニルおよびアルキルカルボニルオキシ、これらのすべては直鎖もしくは分枝であり、任意にフッ素化されており、および1〜30個の炭素原子を有する、からなる群から選択され;
− R0およびR00は、HまたはC1〜C10アルキルから選択され;
− ReおよびRfは、互いに独立して、H、ハロゲン、−CH2Cl、−CHO、−CH=CH2、−SiR’R’’R’’’、−SnR’R’’R’’’、−BR’R’’、−B(OR’)(OR’’)、−B(OH)2、P−Sp、C1〜C20アルキル、C1〜C20アルコキシ、C2〜C20−アルケニル、C1〜C20−フルオロアルキルおよび任意に置換されているアリールまたはヘテロアリールから選択され、好ましくはフェニルであり;
− RcおよびRdは、互いに独立して、Cl、Br、I、O−トシラート、O−トリフラート、O−メシラート、O−ノナフラート、−SiMe2F、−SiMeF2、−O−SO2Z1、−B(OZ2)2、−CZ3=C(Z4)2、−C≡CH、−C≡CSi(Z1)3、−ZnX0および−Sn(Z4)3からなる群から選択され、X0はハロゲンであり、およびZ1、Z2、Z3およびZ4は、アルキルおよびアリール、それぞれは置換されていてもよく、からなる群から選択され、2つの基Z2はまた、環式基を形成していてもよい。
Rc−(Ar3)m2−Ard−(Arb)m4−Rd (VII−1)
Rc−Ar3−Rd (VII−2)
Rc−Ard−Rd (VII−3)
式中、Ara、Arb、Ard、m2、m4、RcおよびRdは、本明細書に定義されるとおりである。
a)式(VII−1)
Rc−Ara−Ua−Arb−Rd
で表されるモノマーを、式(VII−2)
Rc−Ara−Rd (VII−2)
で表されるモノマーとともに、アリール−アリールカップリングでカップリングすることによる、ポリマーの製造方法;または
b)式
Rc−Ua−Rd
で表されるモノマーを、式(VII−1)
Rc−Ara−Ard−Arb−Rd (VII−1)
で表されるモノマーとともに、アリール−アリールカップリングでカップリングすることによる、ポリマーの製造方法;または
c)式
Rc−Ua−Rd
で表されるモノマーを、式(VII−3)
Rc−Ard−Rd (VII−3)
で表されるモノマーとともに、アリール−アリールカップリング反応でカップリングすることによる、ポリマーの製造方法;または
Rc−Ua−Rd
で表されるモノマーを、式(VII−3)
Rc−Ard−Rd (VII−3)
で表されるモノマー、および式(VII−2)
Rc−Ara−Rd (VII−2)
で表されるモノマーとともに、アリール−アリールカップリング反応にでカップリングすることによる、ポリマーの製造方法;または
e)式
Rc−Ua−Ara−Ub−Rd
で表されるモノマーを、式(VII−2)
Rc−Ara−Rd (VII−2)
で表されるモノマーとともに、アリール−アリールカップリングでカップリングすることによる、ポリマーの製造方法;または
f)式
Rc−Ua−Rd
で表されるモノマーを、式(VII−2)
Rc−Ara−Rd (VII−2)
で表されるモノマー、および式(VII−3)
Rc−Ard−Rd (VII−3)
で表されるモノマーと、アリール−アリールカップリング反応でカップリングすることによる、ポリマーの製造方法、
また本発明による化合物およびポリマーは、混合物またはポリマーブレンド中で、例えば小分子またはモノマー化合物とともに、または電荷輸送性、半導体性、導電性、光伝導性および/もしくは発光半導体特性を有する他のポリマーとともに、または例えば、正孔遮断もしくは電子遮断特性を有するポリマーとともに、OLEDデバイスにおける中間層または電荷遮断層としての使用のために、使用することができる。したがって、本発明の他の側面は、本発明による1種または2種以上のポリマーおよび前述の特性の1つまたは2つ以上を有する1種または2種以上のさらなるポリマーを含む、ポリマーブレンドに関する。これらのブレンドを、従来技術に記載されており、当業者に公知の慣用の方法によって、製造することができる。典型的には、ポリマーを、互いと混合するか、または好適な溶媒に溶解し、溶液を合わせる。
− 任意に、基板、
− 高い仕事関数の電極、これは好ましくは金属酸化物、例えばITOを含み、アノードとしての役割をする、
− 任意の導電性ポリマー層または正孔輸送層、これは好ましくは有機ポリマーまたはポリマーブレンド、例えばPEDOT:PSS(ポリ(3,4−エチレンジオキシチオフェン):ポリ(スチレン−スルホネート)、またはTBD(N,N’−ジフェニル−N−N’−ビス(3−メチルフェニル)−1,1’ビフェニル−4,4’−ジアミン)またはNBD(N,N’−ジフェニル−N−N’−ビス(1−ナフチルフェニル)−1,1’ビフェニル−4,4’−ジアミン)を含む、
− 任意に、電子伝達特性を有する層、これは例えばLiFを含む、
− 低い仕事関数の電極、これは好ましくは金属、例えばアルミニウムを含み、カソードとしての役割をする、
ここで、p型半導体は、本発明によるポリマーである。
− 任意に、基板、
− 高い仕事関数の金属または金属酸化物電極、これは例えばITOを含み、カソードとしての役割をする、
− 正孔遮断特性を有する層、これは好ましくは金属酸化物、例えばTiOxまたはZnxを含む、
− 任意の導電性ポリマー層または正孔輸送層、これは好ましくは、有機ポリマーまたはポリマーブレンド、例えばPEDOT:PSSまたはTBDまたはNBDを含む、
− 高い仕事関数の金属、例えば銀を含む電極、これはアノードとしての役割をする、
ここで、p型半導体は、本発明によるポリマーである。
− ソース電極、
− ドレイン電極、
− ゲート電極、
− 半導体層、
− 1つまたは2つ以上のゲート絶縁体層、および、
− 任意に基板、
ここで、半導体層は、好ましくは、本明細書中に記載される化合物、ポリマー、ポリマーブレンドまたは配合物を含む。
この明細書の記載および特許請求の範囲の全体にわたって、語「含む(comprise)」および「含む(contain)」ならびに当該語の変化形、例えば「含む(comprising)」および「含む(comprises)」は、「含むがそれらには限定されない」を意味し、他の成分を除外することを意図しない(かつ除外しない)。
a) 5,5’’−ビス−トリイソプロピルシラニル−[2,2’;5’,2’’]ター[チエノ[3,2−b]チオフェン]−3’,6’−ジカルボン酸ジエチルエステル(3)の合成
a) {6’−[ビス−(4−ヘキサデシル−フェニル)−ヒドロキシ−メチル]−5,5’’−ビス−トリイソプロピルシラニル−[2,2’;5’,2’’]ター[チエノ[3,2−b]チオフェン]−3’−イル}−ビス−(4−ヘキサデシル−フェニル)−メタノール (7)
a) {6’−[ビス−(4−オクタデシル−フェニル)−ヒドロキシ−メチル]−5,5’’−ビス−トリイソプロピルシラニルl−[2,2’;5’,2’’]ター[チエノ[3,2−b]チオフェン]−3’−イル}−ビス−(4−オクタデシル−フェニル)−メタノール (10)
GPC (1,2,4−トリクロロベンゼン、140 ℃) Mn = 166,000 g/mol, Mw= 520,000 g/mol
トップゲート型薄膜有機電界効果トランジスタ(OFET)を、Auフォトリソグラフ的に規定されたソースドレイン電極を有するガラス基板上に作製した。ジクロロベンゼン中の有機半導体の7mg/cm3の溶液をトップにスピンコートし(膜の任意のアニーリングを、1〜5分間、100℃、150℃または200℃で実行した)、次いでフルオロポリマー誘電材料(Lisicon(登録商標)D139、Merck, Germanyから)によってスピンコートした。最後に、フォトリソグラフ的に規定したAuゲート電極を堆積した。トランジスタデバイスの電気的特徴づけをコンピュータ制御Agilent 4155C半導体パラメータ分析器を用いて周囲空気雰囲気中で実行した。飽和領域における電荷キャリア移動度(μsat)を、化合物に対して計算した。飽和領域(Vd>(Vg−V0))において、電界効果移動度を式(eq.1)を用いて計算した。
有機光起電デバイス(OPV)を、LUMTE C Corporationから購入した予めパターン化されたITOガラス基板(13Ω/sq.)上で作製した。基板は、超音波浴中で一般的な溶媒(アセトン、イソプロパノール、脱イオン水)を用いて洗浄した。ポリ(スチレンスルホン酸)でドープされた導電性ポリマー、ポリ(エチレンジオキシチオフェン)(Clevios VPAI 4083、H.C.Starck)を脱イオン水とともに、1:1の比で混合した。この溶液を、0.45μmのフィルターを用いて濾過してからスピンコートし、20nmの厚さを達成した。基板をスピンコーティングプロセスの前にオゾンに曝露し、良好な濡れ性を確保した。次いで膜を窒素雰囲気中で140℃で30分間アニーリングし、ここでそれらは残りのプロセスのために取っておいた。活性材料溶液(すなわち、ポリマー+C60PCBM)を調製し、一晩撹拌し、溶質を十分に溶解させた。薄膜を窒素雰囲気中でスピンコートまたはブレードコートし、粗面計を用いて測定したところ100〜500nmの活性層厚さを達成した。短い乾燥時間が後続して、全ての残留溶媒の除去を確実にした。
Claims (15)
- 以下の式(I)
式中、アスタリスク(“*”)は、隣接する繰り返し単位または当該ポリマー鎖の末端基への結合を示し、さらに、芳香族または芳香族複素環が、他の芳香族または芳香族複素環に縮合される環原子を示すのに用いられる、
を含む群から選択される二価の単位を含む、オリゴマーまたはポリマー。 - 請求項1に記載のオリゴマーまたはポリマーであって、式中、XがCR3R4またはSiR3R4である、前記オリゴマーまたはポリマー。
- 請求項1に記載のオリゴマーまたはポリマーであって、式中、XがCR3R4である、前記オリゴマーまたはポリマー。
- 請求項1〜3のいずれか一項に記載のオリゴマーまたはポリマーであって、以下の式(Ia)
式中、Arは、6〜60個の芳香族炭素原子を含む芳香族環系、または5〜60個の芳香族環原子、少なくともその1つはヘテロ原子である、を含む複素芳香環系を含む、
で表される二価の単位を含む、前記オリゴマーまたはポリマー。 - 請求項4に記載のオリゴマーまたはポリマーであって、式中、Arが、式(D1)〜(D132)、および(A1)〜(A93)、
式中、アスタリスク(“*”)は、隣接する繰り返し単位または当該ポリマー鎖の末端基への結合を示し、さらに、芳香族または芳香族複素環が、他の芳香族または芳香族複素環に縮合される環原子を示すのに用いられ;
式中、R11、R12、R13、R14、R15、R16、R17、およびR18は、互いに独立して、水素、F、Br、Cl、−CN、−NC、−NCO、−NCS、−OCN、−SCN、−C(O)NR0R00、−C(O)X0、−C(O)R0、−NH2、−NR0R00、−SH、−SR0、−SO3H、−SO2R0、−OH、−NO2、−CF3、−SF5、任意に置換されているシリルまたは任意に置換されておりかつ1つまたは2つ以上のヘテロ原子を任意に含む1〜40個のC原子を有するヒドロカルビルからなる群から選択され;
R0およびR00は、それぞれの出現において互いに独立して、Hまたは任意に置換されているC1〜40カルビルまたはヒドロカルビルであり;
X0は、ハロゲンを示すために用いられる、
からなる群から選択される、前記オリゴマーまたはポリマー。 - 請求項5に記載のオリゴマーまたはポリマーであって、式中、Arが、式(D1)、(D10)、(D19)、(A1)および(A19)、ここで、R11およびR12は、互いに独立して、水素またはフッ素である、からなる群から選択される、前記オリゴマーまたはポリマー。
- 請求項1〜6のいずれか一項に記載のオリゴマーまたはポリマーであって、以下
*−Ua m1−Ara m2−Ub m3−Arb m4−Arc m5−* (III)
式中、
UaおよびUbは、互いに独立して、式(I)および(Ia)からなる群から選択される二価の単位から選択され;
Ara、ArbおよびArcは、互いに独立して、UaおよびUbとは異なる、アリールまたはヘテロアリールであり;
m1、m2、m3およびm4は、互いに独立して、0、1および2からなる群から選択され、但しm1およびm3の少なくとも1つは0ではなく;および
m5は、0または1〜10の整数であり、および
式中、アスタリスク(“*”)は、隣接する繰り返し単位または当該ポリマー鎖の末端基への結合を示し、さらに、芳香族または芳香族複素環が、他の芳香族または芳香族複素環に縮合される環原子を示すのに用いられる、
を含む、前記オリゴマーまたはポリマー。 - 請求項7に記載のオリゴマーまたはポリマーであって、式中、Ara、ArbおよびArc−存在する場合−が、互いに独立して、式(D1)〜(D132)および(A1)〜(A93)
式中、アスタリスク(“*”)は、隣接する繰り返し単位または当該ポリマー鎖の末端基への結合を示し、さらに、芳香族または芳香族複素環が、他の芳香族または芳香族複素環に縮合される環原子を示すのに用いられ;
式中、R11、R12、R13、R14、R15、R16、R17、およびR18は、互いに独立して、水素、F、Br、Cl、−CN、−NC、−NCO、−NCS、−OCN、−SCN、−C(O)NR0R00、−C(O)X0、−C(O)R0、−NH2、−NR0R00、−SH、−SR0、−SO3H、−SO2R0、−OH、−NO2、−CF3、−SF5、任意に置換されているシリルまたは任意に置換されておりかつ1つまたは2つ以上のヘテロ原子を任意に含む1〜40個のC原子を有するヒドロカルビルからなる群から選択され;
R0およびR00は、それぞれの出現において互いに独立して、Hまたは任意に置換されているC1〜40カルビルまたはヒドロカルビルであり;
X0は、ハロゲンを示すために用いられる、
からなる群から選択される、前記オリゴマーまたはポリマー。 - 請求項8に記載のオリゴマーまたはポリマーであって、式中、Ara、ArbおよびArc−存在する場合−が、互いに独立して、式(D1)、(D10)、(D19)、(A1)および(A19)、ここで、R11およびR12は、互いに独立して、水素またはフッ素である、からなる群から選択される、前記オリゴマーまたはポリマー。
- 請求項1〜9のいずれか一項に記載の1種または2種以上のオリゴマーまたはポリマー、および1種または2種以上の化合物またはポリマーを含む、混合物またはブレンドであって、半導電性、電荷輸送性、正孔輸送性、電子輸送性、正孔ブロッキング性、電子ブロッキング性、導電性、光伝導性または発光性を有する、前記混合物またはブレンド。
- 請求項1〜9のいずれか一項に記載のオリゴマーまたはポリマーおよび有機溶剤を含む、配合物。
- 請求項1〜9のいずれか一項に記載のオリゴマーまたはポリマーの使用であって、光学、電気光学、電子、エレクトロルミネッセンスまたはフォトルミネッセンス部品またはデバイスにおける電荷輸送、半導体、導電、光伝導または発光材料としての、前記使用。
- 請求項1〜9のいずれか一項に記載のオリゴマーまたはポリマーを含む、電荷輸送、半導体、導電、光伝導または発光材料。
- 請求項1〜9のいずれか一項に記載のオリゴマーまたはポリマーを含む、コンポーネントまたはデバイスであって、有機電界効果トランジスタ(OFET)、薄膜トランジスタ(TFT)、集積回路(IC)、論理回路、キャパシタ、無線周波数認識(RFID)タグ、デバイスまたは部品、有機発光ダイオード(OLED)、有機発光トランジスタ(OLET)、フラットパネルディスプレイ、ディスプレイのバックライト、有機光起電力デバイス(OPV)、有機太陽電池(O−SC)、フォトダイオード、レーザーダイオード、光伝導体、有機光検出器(OPD)、電子写真デバイス、電子写真記録デバイス、有機メモリーデバイス、センサーデバイス、ポリマー発光ダイオード(PLED)における電荷注入層、電荷輸送層または中間層、ショットキーダイオード、平坦化層、帯電防止膜、ポリマー電解質膜(PEM)、導電性基板、導電性パターン、電池における電極材料、配列層、バイオセンサー、バイオチップ、セキュリティマーク、セキュリティデバイス、ならびにDNA配列を検出および識別するためのコンポーネントまたはデバイスからなる群から選択される、前記コンポーネントまたはデバイス。
- 請求項14に記載のコンポーネントまたはデバイスであって、有機電界効果トランジスタ(OFET)、薄膜トランジスタ(TFT)、集積回路(IC)、無線周波数認識(RFID)タグ、有機発光デバイス(OLED)、有機発光トランジスタ(OLET)およびディスプレイのバックライトからなる群から選択される、前記コンポーネントまたはデバイス。
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Publication number | Publication date |
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TW201527347A (zh) | 2015-07-16 |
CN105764957A (zh) | 2016-07-13 |
KR20160091981A (ko) | 2016-08-03 |
CN105764957B (zh) | 2020-04-21 |
EP3074451B1 (en) | 2017-12-27 |
TWI646124B (zh) | 2019-01-01 |
US20160301008A1 (en) | 2016-10-13 |
EP3074451A1 (en) | 2016-10-05 |
WO2015078551A1 (en) | 2015-06-04 |
JP2017508010A (ja) | 2017-03-23 |
US10134994B2 (en) | 2018-11-20 |
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