JP2015513573A - 共役ポリマー - Google Patents
共役ポリマー Download PDFInfo
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- JP2015513573A JP2015513573A JP2014556946A JP2014556946A JP2015513573A JP 2015513573 A JP2015513573 A JP 2015513573A JP 2014556946 A JP2014556946 A JP 2014556946A JP 2014556946 A JP2014556946 A JP 2014556946A JP 2015513573 A JP2015513573 A JP 2015513573A
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- 229920000547 conjugated polymer Polymers 0.000 title abstract description 11
- 229920000642 polymer Polymers 0.000 claims abstract description 132
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- 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
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- 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
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- 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
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- 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
- 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
- IIOSDXGZLBPOHD-UHFFFAOYSA-N tris(2-methoxyphenyl)phosphane Chemical compound COC1=CC=CC=C1P(C=1C(=CC=CC=1)OC)C1=CC=CC=C1OC IIOSDXGZLBPOHD-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
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- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
-
- C—CHEMISTRY; METALLURGY
- 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
-
- 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
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/124—Intrinsically conductive polymers
- H01B1/127—Intrinsically conductive polymers comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- 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
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- 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
-
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Abstract
Description
芳香環の線状縮合は、OSC分子のπ−π共役が広がった最大の平面性を達成する有効な方法である。従って、電荷キャリア移動度の高い既知のポリマーOSCの大部分は、一般に縮合環芳香族系からなり、固体状態で半結晶性である。他方、このような縮合芳香環系は合成が困難な場合が多く、有機溶媒に対して難溶性を示すことも多く、そのため、OEデバイスに使用される薄膜としてそれらを処理するのがより困難になる。また、従来技術で開示されたOSC材料は依然として、それらの電子特性に関してさらなる改善の余地がある。
る良好な溶解性、高い電荷キャリア移動度、及び小さいバンドギャップを示す有機半導体材料として使用される化合物を提供することであった。本発明の別の目的は、専門家が使用可能なOSC材料のプールを拡大することであった。本発明の他の目的は、以下の詳細な説明から専門家には直ぐに明白となる。
Aは、次式、
から選択される、1〜6個のヘテロ原子を含む任意選択により置換されたベンゾ縮合ヘテロアリール部分を示し、
R1及びR2は、互いに独立してH又はハロゲン、好適にはH又はFを示し、
R3〜R6は、互いに独立して、それぞれ同一であるか又は異なり、H、ハロゲン、炭素原子数1〜30の直鎖、分岐鎖もしくは環状のアルキルであって、O原子及び/又はS原子が互いに直接結合しないように、1個又は複数個のCH2基が、−O−、−S−、−C(O)−、−C(S)−、−C(O)−O−、−O−C(O)−、−NR0−、−SiR0R00−、−CF2−、−CHR0=CR00−、−CY1=CY2−もしくは−C≡C−で任意選択により置き換えられており、1個又は複数個のH原子がF、Cl、Br、IもしくはCNで任意選択により置き換えられているアルキルを示すか、又は任意選択により置換されている、好適にはハロゲンでもしくは前述のアルキル基もしくは環状アルキル基の1種又は複数種で任意選択により置換されている、環員数4〜20のアリール、ヘテロアリール、アリールオキシもしくはヘテロアリールオキシを示し、
Y1及びY2は、互いに独立して、H、F、Cl又はCNであり、
R0及びR00は、互いに独立して、H又は任意選択により置換されたC1〜40カルビルもしくはヒドロカルビルであり、好適にはH又は炭素原子数1〜12のアルキルを示す)
の2価の単位を1種又は複数種含む共役ポリマーに関する。
本発明は、さらに、半導体ポリマー中の電子供与体単位としての式Iの単位の使用にも関する。
本発明は、さらに、電子供与体単位として1種又は複数種の式Iの単位を含み、好適には電子受容体特性を有する1種又は複数種の単位をさらに含む半導体ポリマーにも関する。
本発明は、さらに、半導体材料、配合物、ポリマーブレンド、デバイス又はデバイスの構成要素中の電子供与体成分としての本発明によるポリマーの使用にも関する。
本発明は、さらに、本発明によるポリマー、配合物、混合物もしくはポリマーブレンドを含む、又は本発明による電荷輸送材料、半導体材料、導電性材料、光導電性材料もしくは発光材料を含む、光学デバイス、電子光学デバイス、電子デバイス、エレクトロルミネッセンスデバイスもしくは光ルミネッセンスデバイス、又はその構成要素、又はそれを備える組立体にも関する。
電池、レーザーダイオード、ショットキーダイオード、光導電体及び光検出器が挙げられるが、これらに限定されるものではない。
返し単位を有する化合物を意味するものと理解される。
用されるように指定されているモノマー化合物を意味するものと理解される。それと対照的に、「モノマー」という用語は、特記しない限り、ポリマーが生成するようにモノマー化合物を反応させることができる1個又は複数個の反応性官能基を有するモノマー化合物を意味するものと理解される。
Appl.Chem.)、1994年、第66巻、1134頁も参照されたい)。
味するものと理解される。「ヒドロカルビル基」という用語は、1個又は複数個のH原子をさらに含有し、例えば、N,O,S,P,Si,Se,As,Te,Geのような1個又は複数個のヘテロ原子を任意選択により含有するカルビル基を意味するものと理解される。
好適なカルビル基及びヒドロカルビル基としては、それぞれ任意選択により置換されている炭素原子数1〜40、好適には1〜25、非常に好適には1〜18のアルキル、アルコキシ、アルキルカルボニル、アルコキシカルボニル、アルキルカルボニルオキシ及びアルコキシカルボニルオキシ、さらに任意選択により置換されている炭素原子数6〜40、好適には6〜25のアリール又はアリールオキシ、さらに、それぞれ任意選択により置換されている炭素原子数6〜40、好適には7〜40のアルキルアリールオキシ、アリールカルボニル、アリールオキシカルボニル、アリールカルボニルオキシ及びアリールオキシカルボニルオキシが挙げられ、これらの基は全て、1個又は複数個のヘテロ原子、好適にはN,O,S,P,Si,Se,As,Te,Geから選択されるものを任意選択により含有する。
ここで、Lは、ハロゲン、−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、P−Sp−、任意選択により置換されたシリル、又は、任意選択により置換されており、1個又は複数個のヘテロ原子を任意選択により含む炭素原子数1〜40のカルビルもしくはヒドロカルビルから選択され、好適には、任意選択によりフッ素化されて
いる炭素原子数1〜20のアルキル、アルコキシ、チアアルキル、アルキルカルボニル、アルコキシカルボニル又はアルコキシカルボニルオキシであり、R0,R00,X0,P,Spは前述及び後述の意味を有する。
基は、直鎖であっても又は分岐鎖であってもよい。それは、好適には直鎖で、炭素原子数3〜12である。従って、それは、好適にはビスカルボキシメチル、2,2−ビスカルボキシエチル、3,3−ビスカルボキシプロピル、4,4−ビスカルボキシブチル、5,5−ビスカルボキシペンチル、6,6−ビスカルボキシヘキシル、7,7−ビスカルボキシヘプチル、8,8−ビスカルボキシオクチル、9,9−ビスカルボキシノニル、10,10−ビスカルボキシデシル、ビス(メトキシカルボニル)メチル、2,2−ビス(メトキシカルボニル)エチル、3,3−ビス(メトキシカルボニル)プロピル、4,4−ビス(メトキシカルボニル)ブチル、5,5−ビス(メトキシカルボニル)ペンチル、6,6−ビス(メトキシカルボニル)ヘキシル、7,7−ビス(メトキシカルボニル)ヘプチル、8,8−ビス(メトキシカルボニル)オクチル、ビス(エトキシカルボニル)メチル、2,2−ビス(エトキシカルボニル)エチル、3,3−ビス(エトキシカルボニル)プロピル、4,4−ビス(エトキシカルボニル)ブチル、5,5−ビス(エトキシカルボニル)ヘキシルである。
キシ及び3−メチルブトキシである。
からなる群から選択される。これらの基の中でとりわけ好適なのは、全てのALK部分基が同一のものである。
本明細書で使用する場合、「ハロゲン」は、F、Cl、Br又はI、好適にはF、Cl又はBrを示す。
さらに好適には、式I中のR1はFを示し、R2はHを示す。
さらに好適には式I中のR1及びR2はFを示す。
さらに好適には式I中のR3及びR4はHを示す。
から選択される。
式Iの好適な単位は、次式:
から選択される。
Aは、式I又はその好適な部分式Ia〜Inの単位であり、
Bは、Aとは異なり、式Iもしくはその好適な部分式Ia〜Inから選択されるか、又は、任意選択により置換されているアリール基及びヘテロアリール基から選択される単位であり、
xは、>0且つ≦1であり、
yは、≧0且つ<1であり、
x+yは、1であり、
nは、>1の整数である)
から選択される。
から選択される。
R8−鎖−R9
(式中、「鎖」は、式II又は式IIa〜IIrのポリマー鎖を示し、R8及びR9は、互いに独立して前述のR6の意味の1つを有するか、又は互いに独立してH、F、Br、Cl、I、−CH2Cl、−CHO、−CRa=CRb 2、−SiRaRbRc、−SiRaXaXb、−SiRaRbXa、−SnRaRbRc、−BRaRb、−B(ORa)(ORb)、−B(OH)2、−O−SO2−Ra、−C≡CH、−C≡C−SiRa 3、−ZnXa、又はエンドキャップ基を示し、Xa及びXbはハロゲンを示し、Ra、Rb及びRcは互いに独立して式I1に記載のR0の意味の1つを有し、Ra、Rb及びRcの2つは、それらが結合しているヘテロ原子と一緒に環を形成してもよい)
から選択される。
のモノマーに関する。
−nは、少なくとも5、好適には少なくとも10、非常に好適には少なくとも50、且つ最大で2,000、好適には最大で500である。
−R0,R00は、H又はC1〜C10アルキルから選択され、
−R8,R9は、H、ハロゲン、−CH2Cl、−CHO、−CH=CH2−−SiRaRbRc、−SnRaRbRc、−BRaRb、−B(ORa)(ORb)−B(OH)2、C1〜C20アルキル、C1〜C20アルコキシ、C2〜C20アルケニル、C1〜C20フルオロアルキル及び任意選択により置換アリール又はヘテロアリール、好適にはフェニルから選択され、
−R10及びR11は、好適には互いに独立して、H、Cl、Br、I、O−トシレート、O−トリフレート、O−メシレート、O−ノナフレート、−SiMe2F、−SiMeF2、−O−SO2Z1、−B(OZ2)2、−CZ3=C(Z4)2、−C≡CH、C≡CSi(Z1)3、−ZnXa及び−Sn(Z4)3からなる群から選択され、式中、Xaは、ハロゲンであり、Z1−4は、それぞれ任意選択により置換されているアルキル及びアリールからなる群から選択され、2つの基Z2はまた、環状基を形成してもよい。
R10−(Ar)a−R11 VI
(式中、Arは、それぞれ同一であるか又は異なり、アリール基又はヘテロアリール基であり、aは1、2、3、4、5又は6であり、R10及びR11は、式IVの意味の1つ又は前述の好適な意味の1つを有する)
から選択される。
であり、他方のモノマーの反応性基R10及びR11はボロン酸基、ボロン酸誘導体基、C−H活性化結合又はアルキルスタンナンである。統計コポリマー、交互コポリマー及びブロックコポリマーの合成は、例えば、国際公開第03/048225A2号パンフレット又は国際公開第2005/014688A2号パンフレットに詳述されている。
前述及び後述のモノマー及びポリマーの新規な製造方法は、本発明の別の態様である。
本発明による化合物及びポリマーを、例えば、モノマー化合物と一緒に又は電荷輸送性、半導体特性、導電性、光導電性及び/又は発光半導体特性を有する他のポリマーと一緒に使用することもでき、又は、例えば、OLEDデバイス中の中間層もしくは電荷阻止層として使用される正孔阻止性又は電子阻止性を有するポリマーと共に、混合物又はポリマーブレンドとして使用することができる。従って、本発明の別の態様は、本発明による1種又は複数種のポリマーと、前述の特性の1つ又は複数を有する他の1種又は複数種のポリマーとを含むポリマーブレンドに関する。これらのブレンドは、従来技術に記載され、当業者に既知の従来の方法により製造することができる。典型的には、ポリマーを互いに混合するか、又は好適な溶媒に溶解し、その溶液を合わせる。
好適な溶媒は、脂肪族炭化水素、塩素化炭化水素、芳香族炭化水素、ケトン、エーテル及びこれらの混合物である。使用できるその他の溶媒としては、1,2,4−トリメチルベンゼン、1,2,3,4−テトラメチルベンゼン、ペンチルベンゼン、メシチレン、クメン、シメン、シクロヘキシルベンゼン、ジエチルベンゼン、テトラリン、デカリン、2,6−ルチジン、2−フルオロ−m−キシレン、3−フルオロ−o−キシレン、2−クロロベンゾトリフルオライド、N,N−ジメチルホルムアミド、2−クロロ−6−フルオロトルエン、2−フルオロアニソール、アニソール、2,3−ジメチルピラジン、4−フルオロアニソール、3−フルオロアニソール、3−トリフルオロメチルアニソール、2−メチルアニソール、フェネトール、4−メチルアニソール、3−メチルアニソール、4−フルオロ−3−メチルアニソール、2−フルオロベンゾニトリル、4−フルオロベラトロー
ル、2,6−ジメチルアニソール、3−フルオロベンゾニトリル、2,5−ジメチルアニソール、2,4−ジメチルアニソール、ベンゾニトリル、3,5−ジメチルアニソール、N,N−ジメチルアニリン、安息香酸エチル、1−フルオロ−3,5−ジメトキシベンゼン、1−メチルナフタレン、N−メチルピロリドン、3−フルオロベンゾトリフルオライド、ベンゾトリフルオライド、ジオキサン、トリフルオロメトキシベンゼン、4−フルオロベンゾトリフルオライド、3−フルオロピリジン、トルエン、2−フルオロトルエン、2−フルオロベンゾトリフルオライド、3−フルオロトルエン、4−イソプロピルビフェニル、フェニルエーテル、ピリジン、4−フルオロトルエン、2,5−ジフルオロトルエン、1−クロロ−2,4−ジフルオロベンゼン、2−フルオロピリジン、3−クロロフルオロベンゼン、1−クロロ−2,5−ジフルオロベンゼン、4−クロロフルオロベンゼン、クロロベンゼン、o−ジクロロベンゼン、2−クロロフルオロベンゼン、p−キシレン、m−キシレン、o−キシレン又はo−、m−、及びp−異性体の混合物が挙げられる。比較的極性の低い溶媒が一般的に好適である。インクジェット印刷には、高沸点の溶媒及び溶媒混合物が好適である。スピンコートには、キシレン及びトルエンのようなアルキル化ベンゼンが好適である。
る粘度は、好適には1〜100mPa・s、より好適には1〜50mPa・s、最適には1〜30mPa・sである。
えば、C61フラーレン基、C70フラーレン基、もしくはC71フラーレン基を有する構造類似化合物、もしくは有機ポリマー(例えば、コークレー、K.M.(Coakley,K.M.)及びマギー、M.D.(McGehee,M.D.)著、材料化学(Chem.Mater.)、2004年、第16巻、4533頁参照)などの有機材料であってもよい。
ポリマー:フラーレンの比は、好適には重量で5:1〜1:5、より好適には重量で1:1〜1:3、最適には重量で1:1〜1:2である。ポリマー結合剤も、5〜95重量%含むことができる。結合剤の例としては、ポリスチレン(PS)、ポリプロピレン(PP)及びポリメチルメタクリレート(PMMA)が挙げられる。
− 任意選択により基板、
− アノードとして機能する、仕事関数の高い電極、好適には、例えば、ITOのような金属酸化物を含む電極、
− 任意選択による導電性ポリマー層又は正孔輸送層、好適には、例えば、PEDOT:PSS(ポリ(3,4−エチレンジオキシチオフェン):ポリ(スチレンスルホン酸)、又は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)又は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)などの有機ポ
イマー又はポリマーブレンドを含む層、
− 例えば、p型/n型二重層として、又は別個のp型層及びn型層として、又は、BHJを形成するブレンドもしくはp型及びn型半導体として存在し得る、p型及びn型有
機半導体を含む、「能動層」とも称される層、
− 任意選択により電子輸送性を有する層、例えば、LiFを含む層、
− カソードとして機能する、仕事関数の低い電極、好適には、例えば、アルミニウムのような金属を含む電極、
を備え、
電極の少なくとも1つ、アノードは好適には、可視光線透過性であり、
p型半導体は、本発明によるポリマーである。
− 任意選択により基板、
− カソードとして機能する、仕事関数の高い金属電極又は金属酸化物電極、例えば、ITOを含む電極、
− 正孔阻止性を有する層、好適にはTiOx又はZnxのような金属酸化物を含む層
− 例えば、p型/n型二重層として、又は別個のp型層及びn型層として、又は、BHJを形成するブレンドもしくはp型及びn型半導体として存在し得る、電極間に位置するp型及びn型有機半導体を含む能動層、
− 任意選択による導電性ポリマー層又は正孔輸送層、好適には、例えば、PEDOT:PSS又はTBD又はNBDなどの有機ポイマー又はポリマーブレンドを含む層、
− アノードとして機能する、例えば、銀のような仕事関数の高い金属を含む電極、
を備え、
電極の少なくとも1つ、カソードは好適には可視光線透過性であり、
p型半導体は、本発明によるポリマーである。
能動層を基板上に堆積するとき、それは、ナノスケールレベルで相分離するBHJを形成する。ナノスケール相分離に関する考察については、デンラー(Dennler)ら著、IEEE会報(Proceedings of the IEEE)、2005年、第93巻(8号)、1429頁又は(Hoppe)ら著、アドバンスト・ファンクショナル・マテリアルズ(Adv.Func.Mater)、2004年、第14巻(10号)、1005頁を参照されたい。その場合、ブレンドのモルフォロジー及びその結果としてOPVデバイス性能を最適化するために、任意選択によるアニール処理工程が必要となり得る。
− ソース電極、
− ドレイン電極、
− ゲート電極、
− 半導体層、
− 1つ又は複数のゲート絶縁体層、
− 任意選択により基板、
を備え、半導体層は好適には、前述及び後述の化合物、ポリマー、ポリマーブレンド又は配合物を含む。
土類金属(例えば、Ca,Sr,Ba),O2,XeOF4,(NO2 +)(SbF6 −),(NO2 +)(SbCl6 −),(NO2 +)(BF4 −),AgClO4,H2IrCl6,La(NO3)3・6H2O,FSO2OOSO2F,Eu,アセチルコリン,R4N+,(Rはアルキル基である),R4P+(Rはアルキル基である),R6As+(Rはアルキル基である),R3S+(Rはアルキル基である)がある。
本明細書の詳細な説明及び特許請求の範囲全体を通して、「含む(comprise)」及び「含有する(contain)」という用語ならびにそれらの用語の変形、例えば、「含む(comprising)」及び「含む(comprises)」は、「含むが、それらに限定されるものではない」ことを意味し、他の構成要素を排除することを意図していない(及び、排除しない)。
(実施例)
実施例1
ポリマー(1)を次のように製造する(式中、「EH」は2−エチルヘキシルである)。
(Macromolecules)、2004年、第37巻、6299〜6305頁に記載されている。
次のポリマーを実施例1に記載の方法と同様に製造する(式中、「EH」は−2−エチルヘキシルである):
11当量、0.0099mmol)及びトリ−o−トルイルホスフィン(6.0mg、0.12当量、0.010mmol)から、黒色固体をクロロベンゼン可溶性画分として得る(47mg、収率:35%)。GPC(140℃、1,2,4−トリクロロベンゼン):Mn=19.6kg.mol−1;Mw=25.4kg.mol−1、PDI 1.30。
実施例3
次のポリマーを実施例1に記載の方法と同様に製造する(式中、「EH」は−2−エチルヘキシルである):
実施例4
次のポリマーを実施例1に記載の方法と同様に製造する(式中、「EH」は−2−エチルヘキシルである):
実施例5
光活性ポリマー1及び4を使用する光起電力セルの製造。
Claims (18)
- 式I
Aは、次式、
から選択される1〜6個のヘテロ原子を含む任意選択により置換されたベンゾ縮合ヘテロアリール部分を示し、
R1及びR2は、互いに独立してH又はハロゲン、好適にはH又はFを示し、
R3〜R6は、互いに独立して、それぞれ同一であるか又は異なり、H、ハロゲン、炭素原子数1〜30の直鎖、分岐鎖もしくは環状のアルキルであって、O原子及び/又はS原子が互いに直接結合しないように、1個又は複数個の非隣接CH2基が−O−、−S−、−C(O)−、−C(S)−、−C(O)−O−、−O−C(O)−、−NR0−、−SiR0R00−、−CF2−、−CHR0=CR00−、−CY1=CY2−もしくは−C≡C−で任意選択により置き換えられており、1個又は複数個のH原子がF、Cl、Br、IもしくはCNで任意選択により置き換えられているアルキルを示すか、又は任意
選択により置換されている、好適にはハロゲンでもしくは前述のアルキル基もしくは環状アルキル基の1種又は複数種で任意選択により置換されている、環員数4〜20のアリール、ヘテロアリール、アリールオキシもしくはヘテロアリールオキシを示し、
Y1及びY2は、互いに独立してH、F、Cl又はCNであり、
R0及びR00は、互いに独立してH又は任意選択により置換されたC1〜40カルビルもしくはヒドロカルビルであり、好適にはH又は炭素原子数1〜12のアルキルを示す)
の単位を1種又は複数種含むポリマー。 - 前記式Iの単位が、次の部分式:
から選択されることを特徴とする、請求項1に記載のポリマー。 - 前記式Iの単位が、前記部分式B1a、B2b及びB3aから選択されることを特徴とする、請求項2に記載のポリマー。
- 前記式Iの単位が次式:
から選択されることを特徴とする、請求項1〜3のいずれか一項に記載のポリマー。 - 式II:
Aは、請求項1〜4のいずれか一項に記載の式I又はその部分式Ia〜Inの単位であり、
Bは、Aとは異なり、請求項1〜4のいずれか一項に記載の式I又はその部分式Ia〜Inから選択される、又は任意選択により置換されているアリール基及びヘテロアリール基から選択される単位であり、
xは、>0且つ≦1であり、
yは、≧0且つ<1であり、
x+yは、1であり、
nは、>1の整数である)
から選択されることを特徴とする、請求項1〜4のいずれか一項に記載のポリマー。 - 次の部分式:
から選択されることを特徴とする、請求項1〜5のいずれか一項に記載のポリマー。 - 式III
R8−鎖−R9 III
(式中、「鎖」は、請求項5又は6に記載の式II又は式IIa〜式IIrのポリマー鎖を示し、R8及びR9は、互いに独立して、請求項1に記載のR6の意味の1つを有するか、又は、互いに独立してH、F、Br、Cl、I、−CH2Cl、−CHO、−CRa=CRb 2、−SiRaRbRc、−SiRaXaXb、−SiRaRbXa、−SnRaRbRc、−BRaRb、−B(ORa)(ORb)、−B(OH)2、−O−SO2−Ra、−C≡CH、−C≡C−SiRa 3、−ZnXa又はエンドキャップ基を示し、Xa及びXbはハロゲンを示し、Ra、Rb及びR0は互いに独立して請求項1に記載のR0の意味の1つを有し、Ra、Rb及びRcの2つはまた、それらが結合しているヘテロ原子と一緒に環を形成してもよい)
から選択されることを特徴とする、請求項1〜6のいずれか一項に記載のポリマー。 - 請求項1〜7のいずれか一項に記載の1種又は複数種のポリマーと、半導体特性、電荷輸送性、正孔/電子輸送性、正孔/電子阻止性、導電性、光導電性又は発光性を有する1種又は複数種の化合物又はポリマーとを含む混合物又はポリマーブレンド。
- 請求項1〜7のいずれか一項に記載の1種又は複数種のポリマーと、1種又は複数種のn型有機半導体化合物とを含むことを特徴とする、請求項8に記載の混合物又はポリマーブレンド。
- 前記n型有機半導体化合物がフラーレン又は置換フラーレンであることを特徴とする、請求項9に記載の混合物又はポリマーブレンド。
- 請求項1〜10のいずれか一項に記載の1種又は複数種のポリマー、混合物又はポリマーブレンドと、1種又は複数種の溶媒、好適には有機溶媒から選択される溶媒とを含む配合物。
- 光学デバイス、電子光学デバイス、電子デバイス、エレクトロルミネッセンスデバイスもしくは光ルミネッセンスデバイスにおける、又はこのようなデバイスの構成要素における、又はこのようなデバイスもしくは構成要素を備える組立体における、電荷輸送材料、半導体材料、導電性材料、光導電性材料又は発光材料としての請求項1〜12のいずれか一項に記載のポリマー、混合物、ポリマーブレンド又は配合物の使用。
- 請求項1〜11のいずれか一項に記載のポリマー、配合物、混合物又はポリマーブレンドを含む、電荷輸送材料、半導体材料、導電性材料、光導電性材料又は発光材料。
- 電荷輸送材料、半導体材料、導電性材料、光導電性材料もしくは発光材料を含む、又は請求項1〜13のいずれか一項に記載のポリマー、混合物、ポリマーブレンドもしくは配合物を含む、光学デバイス、電子光学デバイス、電子デバイス、エレクトロルミネッセンスデバイスもしくは光ルミネッセンスデバイス、又はその構成要素、又はそれを備える組立体。
- 前記デバイスが有機電界効果トランジスタ(OFET)、薄膜トランジスタ(TFT)、有機発光ダイオード(OLED)、有機発光トランジスタ(OLET)、有機光起電力デバイス(OPV)、有機光検出器(OPD)、有機太陽電池、レーザーダイオード、ショットキーダイオード、及び光導電体から選択され、前記構成要素が電荷注入層、電荷輸送層、中間層、平坦化層、帯電防止膜、高分子電解質膜(PEM)、導電性基板、導電性パ
ターンから選択され、前記組立体が集積回路(IC)、無線認識(RFID)タグ又はセキュリティマーキング又はそれらを含むセキュリティデバイス、フラットパネルディスプレイ又はそのバックライト、電子写真デバイス、電子写真記録デバイス、有機メモリデバイス、センサデバイス、バイオセンサ及びバイオチップから選択される、請求項14に記載のデバイス、その構成要素、又はそれを備える組立体。 - OFET、バルクヘテロ接続(BHJ)OPVデバイス又は逆型BHJ OPVデバイスである、請求項15に記載のデバイス。
- 式IV
のモノマー。 - 請求項17に記載の1種又は複数種のモノマー(式中、R10及びR11は、H、Cl、Br、I、−B(OZ2)2及び−Sn(Z4)3から選択される)を、式V
の1種又は複数種のモノマーと、アリール−アリールカップリング反応で結合させることによる請求項1〜7のいずれか一項に記載のポリマーの製造方法。
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CN (1) | CN104136484B (ja) |
BR (1) | BR112014020228A2 (ja) |
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WO (1) | WO2013120590A1 (ja) |
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WO2017047808A1 (ja) * | 2015-09-18 | 2017-03-23 | 三菱化学株式会社 | コポリマー、光電変換素子、太陽電池及び太陽電池モジュール |
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EP2650938A1 (en) * | 2012-04-13 | 2013-10-16 | Acreo Swedish ICT AB | Organic Field-Effect Transistor Device |
KR20160102534A (ko) * | 2013-12-26 | 2016-08-30 | 메르크 파텐트 게엠베하 | 광기전력 전지 |
JP6677390B2 (ja) | 2015-01-30 | 2020-04-08 | シクパ ホルディング ソシエテ アノニムSicpa Holding Sa | セキュリティ物品及びセキュリティ物品ユーザの識別の同時認証 |
CN107209967B (zh) | 2015-01-30 | 2021-03-16 | 锡克拜控股有限公司 | 同时进行安全制品的验证和安全制品使用者的识别 |
EP3281182B1 (en) | 2015-04-10 | 2022-02-16 | Sicpa Holding Sa | Mobile, portable apparatus for authenticating a security article and method of operating the portable authentication apparatus |
KR102541669B1 (ko) * | 2015-05-12 | 2023-06-08 | 메르크 파텐트 게엠베하 | 티아디아졸로피리딘 중합체, 이의 합성 및 이의 용도 |
EP3151297A1 (de) * | 2015-09-30 | 2017-04-05 | InnovationLab GmbH | Konjugierte polymere mit thermisch abspaltbaren oxalatseitengruppen |
WO2017102058A1 (en) * | 2015-12-18 | 2017-06-22 | Merck Patent Gmbh | Thiadiazolopyridine polymers, their synthesis and their use |
WO2018068725A1 (en) * | 2016-10-11 | 2018-04-19 | He Yan | Difluorobenze-based building blocks and conjugated polymers |
KR102542436B1 (ko) | 2017-06-08 | 2023-06-13 | 코닝 인코포레이티드 | 다른 중합체의 유기 반도체 중합체로의 도핑 |
CN107946463B (zh) * | 2017-10-30 | 2019-10-18 | 华南理工大学 | 基于以萘[1,2-c:5,6-c]二[1,2,5]噻二唑为核的聚合物的光探测器 |
WO2020187867A1 (en) * | 2019-03-19 | 2020-09-24 | Raynergy Tek Inc. | Organic semiconductors |
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EP2814863B1 (en) | 2017-11-15 |
WO2013120590A1 (en) | 2013-08-22 |
TWI568766B (zh) | 2017-02-01 |
BR112014020228A2 (pt) | 2017-07-04 |
CN104136484A (zh) | 2014-11-05 |
EP2814863A1 (en) | 2014-12-24 |
US9178166B2 (en) | 2015-11-03 |
CN104136484B (zh) | 2017-02-22 |
TW201335220A (zh) | 2013-09-01 |
KR20140135748A (ko) | 2014-11-26 |
US20140339477A1 (en) | 2014-11-20 |
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