JP2019503982A - ジチオフェンチアジアゾール半導体および関連デバイス - Google Patents
ジチオフェンチアジアゾール半導体および関連デバイス Download PDFInfo
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- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- KTQYWNARBMKMCX-UHFFFAOYSA-N tetraphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 KTQYWNARBMKMCX-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- UMHFSEWKWORSLP-UHFFFAOYSA-N thiophene 1,1-dioxide Chemical compound O=S1(=O)C=CC=C1 UMHFSEWKWORSLP-UHFFFAOYSA-N 0.000 description 1
- LWRYDHOHXNQTSK-UHFFFAOYSA-N thiophene oxide Chemical compound O=S1C=CC=C1 LWRYDHOHXNQTSK-UHFFFAOYSA-N 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
- 238000000844 transformation Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 230000005428 wave function Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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Abstract
Description
本願は、2016年1月9日に出願された米国仮特許出願第62/276,844号の優先権および利益を主張し、この米国仮特許出願の開示内容は、その全体が参照により組み込まれる。
可撓性である印刷された電子部品は、シリコン製作に必要とされる極めて特化された高価な設備および機器とは明らかに対照的な、可撓性プラスチック箔上での高スループットの安価な溶液プロセス(例えば印刷方法論)を使用して光電子デバイスを製作するための、新たな革新的概念である。適切な材料を使用することにより、これらの技術は、ディスプレイ、携帯電話、医療診断、RFIDタグ、および太陽電池モジュール用の安価で、軽量で、可撓性で、光学的に透明であり、かつ壊れることのない構成要素を可能にし得、これらは次いで、布地、印刷電池、太陽電池、ならびに飛行機および衛星構築物と統合され得る。これら全ての技術の、実現を可能にする材料構成要素(他の必須材料の中で)は、電荷輸送、光吸収、および/または光発生が起きる半導体である。デバイスの機能性および用途を広げるためには、p型(正孔輸送)およびn型(電子輸送)の2種類の半導体が必要である。これらの2種類の半導体の使用および組合せは、ディスプレイの駆動、集光、光発生、論理演算の実行、およびセンサ機能のための基本的な電子的構成単位の製作を可能にする。
上記に照らして、本教示は、上で概説されたものを含む先行技術の様々な欠陥および欠点に対処することができる有機半導体性化合物を提供する。本教示による化合物は、周囲条件下での最適化された光学的吸収、良好な電荷輸送特性および化学的安定性、低温加工性、共通溶媒に対する高い溶解度、ならびに加工多様性(例えば様々な溶液プロセスによる)等の特性を示し得る。その結果、光活性層として本発明の化合物の1種または複数種を組み込んだOPVセル等の光電子デバイスは、周囲条件下において高い性能を示すことができ、例えば、低いバンドギャップ、高い曲線因子、高い開路電圧、および高い電力変換効率の1つまたは複数、好ましくはこれらの基準の全てを示す。同様に、OTFT等の他の有機半導体ベースのデバイスは、本明細書に記載の有機半導体材料を使用して効率的に製作され得る。
により表され得る。一部の実施形態では、本発明の化合物は1つまたはそれより多くの反復単位M1を有するポリマーであり、M1のそれぞれが、少なくとも1つのジチエノ[1,2,3]チアジアゾール部分を含み、ポリマーは、少なくとも3からの範囲の重合度(n)を有する。ある特定の実施形態では、ポリマーは、反復単位M1のみを含むホモポリマーである。他の実施形態では、ポリマーはまた、いかなるジチエノ[1,2,3]チアジアゾール部分も含まない少なくとも1つの他の反復単位M2を含む。そのようなM2単位は、
から選択され得る。一部の実施形態では、本発明の化合物は、化合物が全体としてπ拡張共役系を提供するように、少なくとも1つのジチエノ[1,2,3]チアジアゾール部分ならびに複数の直鎖および/または環式共役部分を含む分子化合物である。
本出願全体を通して、組成物が特定の構成要素を有する(having)、含む(including)、または含む(comprising)と説明されている場合、または、プロセスが特定のプロセスステップを有する(having)、含む(including)、または含む(comprising)と説明されている場合、本教示の組成物はまた、列挙された構成要素から本質的になる、または列挙された構成要素からなること、および本教示のプロセスはまた、列挙されたプロセスステップから本質的になる、または列挙されたプロセスステップからなることが企図される。
FF=(Vmp*Jmp)/(Jsc*Voc)
(式中、JmpおよびVmpは、それぞれ最大出力点(Pm)での電流密度および電圧を表し、この点は、J*Vがその最大値となるまで回路内の抵抗を変動させることにより得られ;JscおよびVocは、それぞれ短絡電流および開路電圧を表す)
を使用して決定され得る。曲線因子は、太陽電池の性能の評価における主要なパラメータである。商業的な太陽電池は、典型的には、約0.60%またはそれを超える曲線因子を有する。
により表され得る。ポリマー化合物は、1種類のみの反復単位を有してもよく、また2種類またはそれを超える種類の異なる反復単位を有してもよい。ポリマー化合物が1種類のみの反復単位を有する場合、これはホモポリマーと呼ぶことができる。ポリマー化合物が2種類またはそれを超える種類の異なる反復単位を有する場合、「コポリマー」または「コポリマー化合物」という用語が代わりに使用され得る。例えば、コポリマー化合物は、反復単位
を含んでもよい。別段に指定されない限り、コポリマー中の反復単位の集合は、頭−尾(head−to−tail)であっても、頭−頭(head−to−head)であっても、尾−尾(tail−to−tail)であってもよい。さらに、別段に指定されない限り、コポリマーは、ランダムコポリマーであっても、交互コポリマーであっても、ブロックコポリマーであってもよい。例えば、一般式:
各R1は、H、ハロゲン、−CN、NO2、R2、−L−R3、OH、OR2、OR3、NH2、NHR2、N(R2)2、NR2R3、N(R3)2、SH、SR2、SR3、S(O)2OH、−S(O)2OR2、−S(O)2OR3、C(O)H、C(O)R2、C(O)R3、C(O)OH、C(O)OR2、C(O)OR3、C(O)NH2、C(O)NHR2、C(O)N(R2)2、C(O)NR2R3、C(O)N(R3)2、SiH3、SiH(R2)2、SiH2(R2)、およびSi(R2)3からなる群から独立して選択され、Lは、二価C1〜40アルキル基、二価C2〜40アルケニル基、二価C1〜40ハロアルキル基、および共有結合からなる群から選択され;各R2は、C1〜40アルキル基、C2〜40アルケニル基、C2〜40アルキニル基、およびC1〜40ハロアルキル基から独立して選択され;各R3は、C3〜10シクロアルキル基、C6〜14アリール基、C6〜14ハロアリール基、3〜12員シクロヘテロアルキル基、および5〜14員ヘテロアリール基からなる群から独立して選択され、それらのそれぞれは、ハロゲン、−CN、NO2、R2、OR2、およびSR2からなる群から独立して選択される1〜5つの置換基で任意選択で置換されている)
により表される1つまたはそれより多くの部分を含む半導体性化合物を提供する。
により表される、任意選択で置換されているジチエノ[1,2,3]チアジアゾール部分である。例えば、R1は、F、Cl、−CN、−NO2、R2、OR2、およびSR2からなる群から選択されてもよく、R2は、直鎖または分岐状C1〜40アルキル基、直鎖または分岐状C2〜40アルケニル基、および直鎖または分岐状C1〜40ハロアルキル基からなる群から選択される。他の実施形態では、R1は、Hであり、式(I)により表される1つまたはそれより多くの部分は、式(III):
π-2は、任意選択で置換されている共役多環式部分であり;
Arは、出現する毎に、独立して、任意選択で置換されている5員または6員のアリールまたはヘテロアリール基であり;
Zは、共役非環式リンカーであり;
mおよびm’は、独立して0、1、2、3、4、5または6であるが、但しmおよびm’の少なくとも一方は0ではなく;
pおよびp’は、独立して0および1であるが、但しpおよびp’の少なくとも一方は1である)
からなる群から選択され得る。
Raは、H、F、Cl、−CN、R、−OR、−SR、−C(O)R、−OC(O)R、および−C(O)ORからなる群から選択され;
Rbは、H、R、および−L−Rfからなる群から選択され;
Rcは、HまたはRであり;
Rdは、H、F、Cl、−CN、R、−OR、−SR、−C(O)R、−OC(O)R、−C(O)OR、および−L−Rfからなる群から選択され;
Reは、H、F、Cl、−CN、R、−OR、−SR、−C(O)R、−OC(O)R、−C(O)OR、およびRfからなる群から選択され;
Rfは、C6〜20アリール基または5〜20員ヘテロアリール基であり、それぞれが、F、Cl、−CN、R、−OR、および−SRからなる群から独立して選択される1〜8つの基で任意選択で置換されており;
Lは、−O−、−S−、−C(O)−、−OC(O)−、−C(O)O−、および共有結合からなる群から選択され;
Rは、C1〜40アルキル基、C1〜40ハロアルキル基、C2〜40アルケニル基、およびC2〜40アルキニル基からなる群から選択される)
からなる群から選択され得る。
により表され得る。さらに例示すると、(Ar)mまたは(Ar)m’は、存在する場合、
からなる群から選択され得る。
から選択され得る。特定の実施形態では、Zは、
からなる群から選択される反復単位M1を含む。
からなる群から選択される。
から選択され得る。
を有し得る。例えば、M2は、
からなる群から選択され得る。
Raは、H、F、Cl、−CN、R、−OR、−SR、−C(O)R、−OC(O)R、および−C(O)ORからなる群から選択され;
Rbは、H、R、および−L−Rfからなる群から選択され;
Rcは、HまたはRであり;
Rdは、H、F、Cl、−CN、R、−OR、−SR、−C(O)R、−OC(O)R、−C(O)OR、および−L−Rfからなる群から選択され;
Reは、H、F、Cl、−CN、R、−OR、−SR、−C(O)R、−OC(O)R、−C(O)OR、およびRfからなる群から選択され;
Rfは、C6〜20アリール基または5〜20員ヘテロアリール基であり、それぞれが、F、Cl、−CN、R、−OR、および−SRからなる群から独立して選択される1〜8つの基で任意選択で置換されており;
Lは、−O−、−S−、−C(O)−、−OC(O)−、−C(O)O−、および共有結合からなる群から選択され;
Rは、C1〜40アルキル基、C1〜40ハロアルキル基、C2〜40アルケニル基、およびC2〜40アルキニル基からなる群から選択される)から選択され得る)
を有し得る。
を有し得る。好ましくは、(Ar)mおよび(Ar)m’は、
から選択され、π-2は、
Raは、H、F、Cl、−CN、R、−OR、−SR、−C(O)R、−OC(O)R、および−C(O)ORからなる群から選択され;
Rbは、H、R、および−L−Rfからなる群から選択され;
Rcは、HまたはRであり;
Rdは、H、F、Cl、−CN、R、−OR、−SR、−C(O)R、−OC(O)R、
−C(O)OR、および−L−Rfからなる群から選択され;
Reは、H、F、Cl、−CN、R、−OR、−SR、−C(O)R、−OC(O)R、
−C(O)OR、およびRfからなる群から選択され;
Rfは、C6〜20アリール基または5〜20員ヘテロアリール基であり、それぞれが、F、Cl、−CN、R、−OR、および−SRからなる群から独立して選択される1〜8つの基で任意選択で置換されており;
Lは、−O−、−S−、−C(O)−、−OC(O)−、−C(O)O−、および共有結合からなる群から選択され;
Rは、C1〜40アルキル基、C1〜40ハロアルキル基、C2〜40アルケニル基、およびC2〜40アルキニル基からなる群から選択される)
から選択される。
から選択される式を有し得る。そのような実施形態において、M2は、
からなる群から選択され得る。
から選択される。
からなる群から選択される式により表され得る。例示すると、M1AおよびM1Bは、
からなる群から選択される異なる単位であってもよい。さらに例示すると、M2AおよびM2Bは、
により表され得る。
からなる群から選択される式により表され得る。
表1 示されたチアジアゾール単位の化学構造、フロンティア分子軌道エネルギーおよび分子軌道トポロジー。
Claims (23)
- 式(I):
Wは、S、Se、およびTeからなる群から選択され;
各R1は、H、ハロゲン、−CN、NO2、R2、−L−R3、OH、OR2、OR3、NH2、NHR2、N(R2)2、NR2R3、N(R3)2、SH、SR2、SR3、S(O)2OH、−S(O)2OR2、−S(O)2OR3、C(O)H、C(O)R2、C(O)R3、C(O)OH、C(O)OR2、C(O)OR3、C(O)NH2、C(O)NHR2、C(O)N(R2)2、C(O)NR2R3、C(O)N(R3)2、SiH3、SiH(R2)2、SiH2(R2)、およびSi(R2)3からなる群から独立して選択され、Lは、二価C1〜40アルキル基、二価C2〜40アルケニル基、二価C1〜40ハロアルキル基、および共有結合からなる群から選択され;各R2は、C1〜40アルキル基、C2〜40アルケニル基、C2〜40アルキニル基、およびC1〜40ハロアルキル基からなる群から独立して選択され;各R3は、C3〜10シクロアルキル基、C6〜14アリール基、C6〜14ハロアリール基、3〜12員シクロヘテロアルキル基、および5〜14員ヘテロアリール基からなる群から独立して選択され、そのそれぞれは、ハロゲン、−CN、NO2、R2、OR2、およびSR2からなる群から独立して選択される1〜5つの置換基で任意選択で置換されている、
半導体性化合物。 - 式(I)により表される前記1つまたはそれより多くの部分が、式(II):
- R1が、F、Cl、−CN、−NO2、R2、OR2、およびSR2からなる群から選択され、R2が、直鎖または分岐状C1〜40アルキル基、直鎖または分岐状C2〜40アルケニル基、および直鎖または分岐状C1〜40ハロアルキル基からなる群から選択される、請求項2に記載の化合物。
- R1が、Hであり、式(I)により表される前記1つまたはそれより多くの部分が、式(III):
- 前記化合物が、式(I)により表される1つまたはそれより多くの二価単位を含む第1の反復単位M1を有するポリマーであり、前記ポリマーが、3から1,000の範囲の重合度(n)を有する、請求項1に記載の化合物。
- M1が、
π-2は、任意選択で置換されている共役多環式部分であり;
Arは、出現する毎に、独立して、任意選択で置換されている5員または6員のアリールまたはヘテロアリール基であり;
Zは、共役非環式リンカーであり;
mおよびm’は、独立して0、1、2、3、4、5または6であるが、但しmおよびm’の少なくとも一方は0ではなく;
pおよびp’は、独立して0および1であるが、但しpおよびp’の少なくとも一方は1である、
請求項5に記載の化合物。 - Wが、Sである、請求項6に記載の化合物。
- π-2が、任意選択で置換されているC8〜26アリール基または8〜26員ヘテロアリール基である、請求項6または7に記載の化合物。
- π-2が、
Raは、H、F、Cl、−CN、R、−OR、−SR、−C(O)R、−OC(O)R、および−C(O)ORからなる群から選択され;
Rbは、H、R、および−L−Rfからなる群から選択され;
Rcは、HまたはRであり;
Rdは、H、F、Cl、−CN、R、−OR、−SR、−C(O)R、−OC(O)R、
−C(O)OR、および−L−Rfからなる群から選択され;
Reは、H、F、Cl、−CN、R、−OR、−SR、−C(O)R、−OC(O)R、−C(O)OR、およびRfからなる群から選択され;
Rfは、C6〜20アリール基または5〜20員ヘテロアリール基であり、それぞれが、F、Cl、−CN、R、−OR、および−SRからなる群から独立して選択される1〜8つの基で任意選択で置換されており;
Lは、−O−、−S−、−C(O)−、−OC(O)−、−C(O)O−、および共有結合からなる群から選択され;
Rは、C1〜40アルキル基、C1〜40ハロアルキル基、C2〜40アルケニル基、およびC2〜40アルキニル基からなる群から選択される、
請求項8に記載の化合物。 - (Ar)mおよび(Ar)m’中のArが、
請求項6または7に記載の化合物。 - (Ar)mおよび(Ar)m’が、
請求項10に記載の化合物。 - Zが、
請求項6または7に記載の化合物。 - M1以外の1つまたはそれより多くの反復単位をさらに含む、請求項6から12のいずれか一項に記載の化合物であって、前記1つまたはそれより多くの他の反復単位(M2)が、
π-2は、任意選択で置換されている共役多環式部分であり;
Arは、出現する毎に、独立して、任意選択で置換されている5員または6員のアリールまたはヘテロアリール基であり;
Zは、共役非環式リンカーであり;
mおよびm’は、独立して、0、1、2、3、4、5または6であるが、但しmおよびm’の少なくとも一方は0ではなく;
m’’は、1、2、3、4、5または6であり;
pおよびp’は、独立して0および1であるが、但しpおよびp’の少なくとも一方は1である、
化合物。 - 前記1つまたはそれより多くのM2反復単位において、
Zが、
(Ar)m、(Ar)m’、および(Ar)m’’が、
π-2が、
Raは、H、F、Cl、−CN、R、−OR、−SR、−C(O)R、−OC(O)R、および−C(O)ORからなる群から選択され;
Rbは、H、R、および−L−Rfからなる群から選択され;
Rcは、HまたはRであり;
Rdは、H、F、Cl、−CN、R、−OR、−SR、−C(O)R、−OC(O)R、−C(O)OR、および−L−Rfからなる群から選択され;
Reは、H、F、Cl、−CN、R、−OR、−SR、−C(O)R、−OC(O)R、−C(O)OR、およびRfからなる群から選択され;
Rfは、C6〜20アリール基または5〜20員ヘテロアリール基であり、それぞれが、F、Cl、−CN、R、−OR、および−SRからなる群から独立して選択される1〜8つの基で任意選択で置換されており;
Lは、−O−、−S−、−C(O)−、−OC(O)−、−C(O)O−、および共有結合からなる群から選択され;Rは、C1〜40アルキル基、C1〜40ハロアルキル基、C2〜40アルケニル基、およびC2〜40アルキニル基からなる群から選択され;
Rは、C1〜40アルキル基、C1〜40ハロアルキル基、C2〜40アルケニル基、およびC2〜40アルキニル基からなる群から選択される、
請求項13に記載の化合物。 - M1が、
M2が、
請求項14に記載の化合物。 - 前記化合物が
請求項13に記載の化合物。 - 前記化合物がランダムコポリマーである、請求項16に記載の化合物。
- 前記化合物が
Q1およびQ2は、H、R2、およびC(O)R2からなる群から独立して選択され、R2は、C1〜40アルキルまたはハロアルキル基であり;
π-2は、任意選択で置換されている共役多環式部分であり;
Arは、出現する毎に、独立して、任意選択で置換されている5員または6員のアリールまたはヘテロアリール基であり;
Zは、共役非環式リンカーであり;
mおよびm’は、独立して、0、1、2、3、4、5または6であるが、但しmおよびm’の少なくとも一方は0ではなく;
m’’は、1、2、3、4、5または6であり;
pおよびp’は、独立して0および1であるが、但しpおよびp’の少なくとも一方は1である、
請求項1から3のいずれか一項に記載の化合物。 - 半導体構成要素を含む電子、光学または光電子デバイスであって、前記半導体構成要素が、請求項1から18のいずれか一項に記載の化合物を含むデバイス。
- アノードと、カソードと、任意選択で1つまたはそれより多くのアノード中間層と、任意選択で1つまたはそれより多くのカソード中間層と、前記アノードおよび前記カソードの間の半導体構成要素であって、ブレンド材料を含む半導体構成要素とを含む有機光起電デバイスであって、前記ブレンド材料が、電子受容体化合物および電子供与体化合物を含み、前記電子供与体化合物が、請求項1から18のいずれか一項に記載の化合物である、有機光起電デバイス。
- 前記電子受容体化合物が、フラーレン化合物である、請求項20に記載のデバイス。
- 前記電子受容体化合物が、電子輸送ポリマーである、請求項20に記載のデバイス。
- 基材と、薄膜半導体と、誘電体層と、ゲート電極と、ソースおよびドレイン電極とを含む有機薄膜トランジスタであって、前記薄膜半導体が、請求項1から18のいずれか一項に記載の化合物を含む、有機薄膜トランジスタ。
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TWI725583B (zh) * | 2019-10-22 | 2021-04-21 | 國立勤益科技大學 | 可撓式可見光檢測器 |
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DE2349064A1 (de) | 1973-09-29 | 1975-04-10 | Basf Ag | 1,3-diazacycloalkeno- eckige klammer auf 1,2-d eckige klammer zu -benzo- eckige klammer auf f eckige klammer zu -1,3,4- thiadiazepine |
WO2010135723A2 (en) * | 2009-05-21 | 2010-11-25 | Polyera Corporation | Conjugated polymers and their use in optoelectronic devices |
DE102010030500A1 (de) * | 2010-06-24 | 2011-12-29 | Heliatek Gmbh | Verdampfbares organisch halbleitendes Material und dessen Verwendung in einem optoelektronischen Bauelement |
US8993711B2 (en) | 2010-10-06 | 2015-03-31 | Polyera Corporation | Semiconducting polymers and optoelectronic devices incorporating same |
US8835598B2 (en) | 2012-03-22 | 2014-09-16 | Polyera Corporation | Conjugated polymers and their use in optoelectronic devices |
WO2014094965A2 (de) | 2012-12-18 | 2014-06-26 | Merck Patent Gmbh | Emitter mit kondensiertem ringsystem |
WO2014204082A1 (ko) | 2013-06-20 | 2014-12-24 | 경상대학교산학협력단 | 유기 반도체 화합물, 이의 제조방법 및 이를 채용한 유기 태양전지 |
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US9666805B2 (en) * | 2014-11-25 | 2017-05-30 | Northwestern University | Bithiophene sulfonamide-based molecular and polymeric semiconductors |
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