CN104302622A - 用于有机电子器件的非那省化合物 - Google Patents
用于有机电子器件的非那省化合物 Download PDFInfo
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- CN104302622A CN104302622A CN201380023973.0A CN201380023973A CN104302622A CN 104302622 A CN104302622 A CN 104302622A CN 201380023973 A CN201380023973 A CN 201380023973A CN 104302622 A CN104302622 A CN 104302622A
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- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
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- 239000002608 ionic liquid Substances 0.000 description 1
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- 230000004001 molecular interaction Effects 0.000 description 1
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- 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
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- 229910052759 nickel Inorganic materials 0.000 description 1
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- 230000003287 optical effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- 125000002460 pentacosyl 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])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
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229920001291 polyvinyl halide Polymers 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007921 spray Substances 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
- 239000000758 substrate Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 230000009466 transformation Effects 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
- 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
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Abstract
本发明公开了式(I)的非那省(phenacene)化合物。式中的所有变量与说明书中定义的相同。还公开了包含以上化合物的薄膜半导体,以及包含该薄膜的场效应晶体管器件、光伏器件、有机发光二极管器件和单极或互补电路器件。
Description
本发明涉及非那省(phenacene)化合物及其用途。
有机半导体材料可用于电子器件如有机光电(OPV)电池、有机场效应晶体管(OFET)和有机发光二极管(OLED)中。
理想的是有机半导体材料适合液体加工技术如旋涂、溶液浇注或印刷。液体加工技术从加工性观点看是方便的,并且也可应用于塑料基质。因此,适合液体加工技术的有机半导体材料容许生产低成本、轻重量且还任选挠性的电子器件,这是这些有机半导体材料与无机半导体材料相比的明显优点。
此外,理想的是有机半导体材料是稳定的,特别是对氧化而言稳定。
当用于有机场效应晶体管(OFET)中时,有机半导体材料应显示出高电荷载流子迁移率和高开/关比。
有机半导体材料在电子器件中,特别是在有机场效应晶体管(OFET)中的使用是本领域中已知的。
Okamoto,K.;Kawasaki,N.;Kaji,Y.;Kubozono,Y.;Fujiwara,A.;Yamaji,M.J.Am.Chem.Soc.2008,130,10470-10471和Kawasaki,N.;Kubozono,Y.;Okamoto,H.Fujiwara,A.;Yamaji,M.Appl.Phys.Lett.2009,94,043310描述了用于真空沉积OFET的二萘品苯:
其中电荷载流子迁移率达到3cm2V-1s-1。
JP2009/063846公开了作为溶液基OFET且具有至多2cm2V-1s-1的电荷载流子迁移率的烷基化二萘品苯。
S.Shinamura等人,K.J.Am.Chem.Soc.2011,133,5024-5035公开了用于真空沉积OFET的下式线性-和有角型萘并二噻吩:
其中R为H、n-C8H17或苯基,其中电荷载流子迁移率达到1.5cm2/V s。
J.Gao等人,Adv.Mater.2007,19,3008-3011公开了用于FET且具有0.5cm2V-1s-1以上的电荷载流子迁移率和大于106的开/关比的二苯并噻吩并二噻吩。
K.Xiao等人,J.Am.Chem.Soc.2005,127,13281-13286公开了用于真空沉积OFET且具有0.045cm2V-1s-1的电荷载流子迁移率和103的开/关比的并五噻吩。
J.Wang等人,Chem.Mater.2009,21,2595-2597描述了用于真空沉积OFET且具有至多0.4cm2/V s的电荷载流子迁移率的以下小分子:
因此,如果给定在可通过高吞吐量卷到卷生产而生产的便宜且大面积有机电子器件中的潜在应用,本领域想要新的有机p型半导体化合物,尤其是具有理想性能如空气稳定性、高电荷输送效率和在常用有机溶剂中的良好溶解度的那些。
鉴于上文,本发明的目的是提供可解决技术发展水平的各种缺陷和短处,包括上述那些的可用作有机半导体的化合物和相关材料、组合物、复合物和/或器件。
该目的通过下式的非那省化合物解决:
其中:
基团a、b和c中的一个为X,且其它两个基团分别为C-R1和C-R2,
基团d、e和f中的一个为X,且其它两个基团分别为C-R5和C-R6,
其中X相互独立地选自NH、O、S和Se,优选选自O、S和Se,更优选选自O和S,特别优选为S,
R1-R10相互独立地为H、卤素、-CN、-NO2或者线性或支化、饱和或不饱和C1-C40烃残基,其可被卤素(F、Cl、Br、I)、-ORa、-NRa 2、-CN和/或-NO2取代1-5次,且其中一个或多个CH2-基团可被-O-、-S-、-NRb-、-OC(O)-或-C(O)-取代,且其中Ra和Rb相互独立地为H、C1-C30烷基、C2-C30烯基、C2-C30炔基、C1-C30卤代烷基、C2-C30卤代烯基、C2-C30卤代炔基或C2-C30酰基。
优选R1、R2、R5和R6选自H、卤素(F、Cl、Br、I)和C1-20烷基。
优选R3、R4选自H、卤素(F、Cl、Br、I)和C1-20烷基。
优选R7、R8、R9、R10选自H、卤原子和C1-20烷基。
发现本发明非那省化合物具有半导体活性。由这些化合物制备的材料证明了出乎意料的性能。发现本发明化合物在场效应器件(如薄膜晶体管)中可具有高载流子迁移率和/或良好电流调制特性。另外,发现本发明化合物可具有与有关典型化合物相比的某些加工优点,例如更好的溶解度以容许溶液加工性和/或在环境条件下的良好稳定性如空气稳定性。另外,化合物中可嵌入其它组分以用于多种半导体基器件中。
优选的非那省化合物选自式Ia-If的化合物:
其中化合物Ia是最优选的。
在一个优选实施方案中,X为硫。硫的存在可借助S-S相互作用而导致其它分子间相互作用并可导致较高迁移率。
R1-R10相互独立地为H、卤素、-CN、-NO2或者线性或支化、饱和或不饱和C1-C40烃残基,其可被卤素(F、Cl、Br、I)、-ORa、-NRa 2、-CN和/或-NO2取代1-5次,且其中一个或多个CH2-基团可被-O-、-S-、-NRb-、-OC(O)-或-C(O)-取代,且其中Ra和Rb相互独立地为H、C1-C30烷基、C2-C30烯基、C2-C30炔基、C1-C30卤代烷基、C2-C30卤代烯基、C2-C30卤代炔基或C2-C30酰基。
优选R1-R10相互独立地为H、卤素、C1-C30烷基、C1-C30烷氧基、C1-C30烷硫基、C2-C30烯基、C2-C30炔基、C1-C30卤代烷基、C2-C30卤代烯基或卤代炔基如C1-C30全氟烷基或C2-C10酰基。更优选R1-R10相互独立地为H、卤素、C1-C30烷基或C1-C30烷氧基。最优选R1-R10相互独立地为H、卤素或C1-C30烷基。
如果可能的话,C1-C30烷基可以为线性或支化的。
实例为甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、2-戊基、3-戊基、2,2-二甲基丙基、1,1,3,3-四甲基戊基、正己基、1-甲基己基、1,1,3,3,5,5-六甲基己基、正庚基、异庚基、1,1,3,3-四甲基丁基、1-甲基庚基、3-甲基庚基、正辛基、1,1,3,3-四甲基丁基和2-乙基己基、正壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、二十烷基、二十一烷基、二十二烷基、二十四烷基或二十五烷基。
C1-C30烷氧基为直链或支化烷氧基,例如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、叔丁氧基、戊氧基、异戊氧基、叔戊氧基、庚氧基、辛氧基、异辛氧基、壬氧基、癸氧基、十一烷氧基、十二烷氧基、十四烷氧基、十五烷氧基、十六烷氧基、十七烷氧基或十八烷氧基。
术语“烷硫基”意指与烷氧基相同的基团,不同之处在于醚键的氧原子被硫原子取代。
C2-C30烯基为直链或支化烯基,例如乙烯基、烯丙基、甲基烯丙基、异丙烯基、2-丁烯基、3-丁烯基、异丁烯基、正-戊-2,4-二烯基、3-甲基-丁-2-烯基、正-辛-2-烯基、正-十二碳-2-烯基、异十二碳烯基、正-十二碳-2-烯基或正-十八碳-4-烯基。
C2-30炔基为直链或支化的且可未被取代或被取代,例如乙炔基、1-丙炔-3-基、1-丁炔-4-基、1-戊炔-5-基、2-甲基-3-丁炔-2-基、1,4-戊二炔-3-基、1,3-戊二炔-5-基、1-己炔-6-基、顺-3-甲基-2-戊烯-4-炔-1-基、反-3-甲基-2-戊烯-4-炔-1-基、1,3-己二炔-5-基、1-辛炔-8-基、1-壬炔-9-基、1-癸炔-10-基或1-二十四炔-24基。
C1-C30全氟烷基为支化或非支化基团,例如-CF3、-CF2CF3、-CF2CF2CF3、-CF(CF3)2、-(CF2)3CF3或-C(CF3)3。
术语“卤代烷基、卤代烯基和卤代炔基”意指通过将上述烷基、烯基和炔基用卤素部分或完全取代而给出的基团。
C2-C30酰基为直链或支化的且可以为饱和或不饱和的,例如乙酰基、丙酰基、异丁酰基、正丁酰基、戊酰基、己酰基、庚酰基、辛酰基、壬酰基、癸酰基或十二烷酰基。
特别优选的基团R1、R2、R5和R6选自H和C1-20烷基。
特别优选的基团R3、R4选自H和C1-20烷基。
特别优选的基团R7-R10选自H和C1-20烷基。
在一个优选实施方案中,R7-R10为氢。
在另一优选实施方案中,R3和R4为氢。
在又一优选实施方案中,R1和R2中的一个为氢,且另一个为C1-20烷基,并且R5和R6中的一个为氢,且另一个为C1-20烷基。
非常优选的C1-20烷基为C10-20烷基。
通式I的化合物可通过下面所示合成路线得到:
由于本文所述化合物可溶于常用溶剂中,本发明可提供在制造电器件如薄膜半导体、场效应器件、有机发光二极管(OLED)、有机光伏器件、光检测器、电容器和传感器中的加工优点。如本文所用,当至少1mg化合物可溶于1mL溶剂中时,可认为化合物可溶于溶剂中。常用有机溶剂的实例包括石油醚;乙腈;芳族烃,例如苯、甲苯、二甲苯和均三甲基苯;酮,例如丙酮和甲乙酮;醚,例如四氢呋喃、二烷、双(2-甲氧基乙基)醚、二乙醚、二异丙醚和叔丁基甲醚;醇,例如甲醇、乙醇、丁醇和异丙醇;脂族烃,例如己烷;乙酸酯,例如乙酸甲酯、乙酸乙酯、甲酸甲酯、甲酸乙酯、乙酸异丙酯和乙酸丁酯;酰胺,例如二甲基甲酰胺和二甲基乙酰胺;亚砜,例如二甲亚砜;卤代脂族和芳族烃,例如二氯甲烷、氯仿、氯乙烯、氯苯、二氯苯和三氯苯;和环状溶剂,例如环戊酮、环己酮和2-甲基吡咯烷酮。常用无机溶剂的实例包括水和离子液体。
因此,本发明进一步提供包含溶于或分散于液体介质如有机溶剂、无机溶剂或其组合(有机溶剂、无机溶剂或有机和无机溶剂的混合物)中的一种或多种本文所述化合物的组合物。在一些实施方案中,组合物可进一步包含一种或多种添加剂,所述添加剂独立地选自清净剂、分散剂、粘合剂、相容剂、固化剂、引发剂、润湿剂、消泡剂、湿润剂、pH改进剂、杀生物剂和抗菌剂。例如,表面活性剂和/或其它聚合物(例如聚苯乙烯、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)可作为分散剂、粘合剂、相容剂和/或消泡剂包含在内。在一些实施方案中,这类组合物可包含一种或多种本文所述化合物,例如可将两种或更多种不同的本发明化合物溶于有机溶剂中以制备用于沉积的组合物。在某些实施方案中,组合物可包含两种或更多种位置异构体。另外,应当理解本文所述器件还可包含一种或多种本发明化合物,例如两种或更多种如本文所述的位置异构体。
各种沉积技术,包括各种溶液加工技术可用于制备有机电子设备中。例如,多种印刷电子技术集中于喷墨印刷,主要是因为该技术提供对特征位置和多层重合的更大控制。喷墨印刷是非接触技术,其提供如下优点:不需要预成型的母版(与接触印刷技术相比),以及对油墨喷射的数字控制,由此提供按需滴落印刷。微分配是另一非接触印刷方法。然而,接触印刷技术具有很好地适于非常快的辊对辊加工的关键优点。典型接触印刷技术包括但不限于丝网印刷、凹版印刷、胶版印刷、柔版印刷、石版印刷、移印和微接触印刷。如本文所用,“印刷”包括非接触方法,例如喷墨印刷、微分配等,和接触方法,例如丝网印刷、凹版印刷、胶版印刷、柔版印刷、石版印刷、移印、微接触印刷等。其它溶液加工技术包括例如旋涂、滴落涂布、区域浇注、浸涂、刮涂或喷雾。另外,沉积步骤可通过真空气相沉积进行。
因此,本发明进一步提供制备半导体材料的方法。该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述化合物的组合物,和使组合物沉积于基质上以提供包含一种或多种本文所述化合物的半导体材料(例如薄膜半导体)。在各个实施方案中,液体介质可以为有机溶剂、无机溶剂如水,或其组合。在一些实施方案中,组合物可进一步包含一种或多种添加剂,所述添加剂独立地选自粘度调节剂、清净剂、分散剂、粘合剂、相容剂、固化剂、引发剂、润湿剂、消泡剂、湿润剂、pH改进剂、杀生物剂和抗菌剂。例如,表面活性剂和/或聚合物(例如聚苯乙烯、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)可作为分散剂、粘合剂、相容剂和/或消泡剂包含在内。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(例如丝网印刷、凹版印刷、胶版印刷、移印、石版印刷、柔版印刷和微接触印刷)进行。在其它实施方案中,沉积步骤可通过旋涂、滴落涂布、区域浇注、浸涂、刮涂或喷雾进行。
使用本文所述化合物和半导体材料的各种生产制品,包括电子器件、光学器件和光电子器件如场效应晶体管(例如薄膜晶体管)、光伏器件、有机发光二极管(OLED)、互补金属氧化物半导体(CMOS)、互补倒相器、D触发器、整流器和环形振荡器以及其制备方法在本发明范围内。
因此,本发明提供包含具有本发明半导体材料的复合物、基质组分和/或介电组分的生产制品如本文所述各种器件。基质组分可选自材料,包括掺杂硅、氧化铟锡(ITO)、ITO涂覆玻璃、ITO涂覆聚酰亚胺或者单独或涂覆于聚合物或其它基质上的其它塑料、铝或其它金属,掺杂聚噻吩或其它聚合物等。介电组分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(例如聚碳酸酯、聚酯、聚苯乙烯、聚卤乙烯、聚丙烯酸酯)、自组装超晶格/自组装纳米介电(SAS/SAND)材料(例如Yoon,M-H.等人,PNAS,102(13):4678-4682(2005)所述,通过引用将其全部公开内容并入本文中)和混杂有机/无机介电材料(例如美国专利申请序列号11/642,504,通过引用将其全部公开内容并入本文中)制备。在一些实施方案中,介电组分可包括美国专利申请序列号11/315,076、60/816,952和60/861,308所述交联聚合物混合物,通过引用将其各自的全部公开内容并入本文中。复合物还可包含一个或多个电触点。用于源、漏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)和导电聚合物(例如聚(3,4-乙烯二氧噻吩)聚(苯乙烯磺酸酯)(PEDOT:PSS)、聚苯胺(PANI)、聚吡咯(PPy)。本文所述复合物中的一种或多种可并入各种有机电子、光学和光电子器件如有机薄膜晶体管(OTFT),尤其是有机场效应晶体管(OFET),以及传感器、电容器、单极电路、互补电路(例如倒相电路)等中。
因此,本发明一方面涉及制造并入本发明半导体材料的有机场效应晶体管的方法。本发明半导体材料可用于制造各类有机场效应晶体管,包括顶栅顶触点电容器结构、顶栅底触点电容器结构、底栅顶触点电容器结构和底栅底触点电容器结构。
在某些实施方案中,OTFT器件可用本发明化合物在掺杂硅基质上,使用SiO2作为电介质,以顶触点几何制造。在特定实施方案中,并入至少一种本发明化合物的活性半导体层可通过在室温下或在高温下真空蒸气沉积而沉积。在其它实施方案中,并入至少一种本发明化合物的活性半导体层可通过溶液基方法如旋涂或喷墨印刷施涂。对于顶触点器件,可使用荫罩板将金属触点图案化在膜上。
在某些实施方案中,OTFT器件可用本发明化合物在塑料箔上,使用聚合物作为电介质,以顶栅底触点几何制造。在特定实施方案中,并入至少一种本发明化合物的活性半导体层可在室温或高温下沉积。在其它实施方案中,并入至少一种本发明化合物的活性半导体层可通过如本文所述旋涂或印刷施涂。栅和源/漏触点可由Au、其它金属或导电聚合物构成并通过蒸气沉积和/或印刷沉积。
本发明化合物用于其中的其它生产制品为光伏器件或太阳能电池。本发明化合物可显示出宽光学吸收和/或非常积极转变的还原电势,使得它们对这类引用而言是理想的。因此,本文所述化合物可作为p型半导体用于光电设计中,所述光电设计包含形成p-n结的相邻n型半导体材料。化合物可以为薄膜半导体的形式,其可以为沉积于基质上的薄膜半导体的复合物。本发明化合物在这类器件中的采用是技术人员已知的。
因此,本发明另一方面涉及制造并入一种或多种本发明半导体材料的有机发光晶体管、有机发光二极管或有机光伏器件的方法。
提供以下实施例以进一步阐述和促进对本发明的理解,且决不意欲限制本发明。
实施例
2,9-二烷基-1,10-二硫杂二环戊[a,i]非那省通过以下合成路线制备:
实施例1
2,3-二溴-1,4-双-三甲基硅烷基-苯的合成
将LDA(2M,70mL,140毫摩尔)在-78℃下逐滴加入1,2-二溴苯(15.0g,64毫摩尔)和氯三甲基硅烷(20mL,153毫摩尔)在THF(90mL)中的溶液中。将所得褐色悬浮液在-78℃下搅拌30分钟,然后逐步加热至室温。将反应混合物搅拌18小时,然后再次冷却至-78℃,并加入氯三甲基硅烷(20mL,153毫摩尔)。逐滴加入LDA(2M,70mL,140毫摩尔),将所得褐色悬浮液在-78℃下搅拌30分钟,然后逐步加热至室温。将反应混合物搅拌另外18小时,然后用1N HCl(100mL)水解。将所得混合物用二乙醚(3×200mL)萃取,并将结合的有机层浓缩以得到褐色油,其不进一步提纯而直接用于下一步骤中。1H NMR(400MHz,CDCl3)δ7.34(s,2H),0.40(18H)。
实施例2
2,3-二溴-1,4-二碘-苯的合成
将一氯化碘(1M,60mL,58毫摩尔)在0℃下加入2,3-二溴-1,4-双-三甲基硅烷基-苯(10.0g,26.3毫摩尔)的二氯甲烷(105mL)溶液中。将所得紫色溶液在室温下搅拌1天。将反应冷却至0℃并加入另外的一氯化碘(1M,60mL,58毫摩尔)。将反应混合物在室温下搅拌另外1天。将饱和硫代硫酸钠溶液(150mL)加入反应混合物中并用二氯甲烷(2×100mL)萃取。将结合有机层浓缩以得到褐色固体,将其通过在硅胶上使用100%己烷柱层析而提纯以得到褐色固体(8g,69%)。收率:69%;褐色固体;1H NMR(400MHz,CDCl3)δ7.47(s,2H)。
实施例3
2-十四烷基-噻吩的合成
将n-BuLi(1.6M,48mL,76毫摩尔)在-78℃下逐滴加入噻吩(7.0g,83毫摩尔)的THF(70mL)溶液中并搅拌45分钟。将在THF(25mL)中的十四烷基溴(23mL,76毫摩尔)逐滴加入所得悬浮液中,然后逐步加热至室温并搅拌18小时。将反应混合物用水(60mL)骤冷并用二乙醚(2×100mL)萃取。将结合的有机萃取物经MgSO4干燥并浓缩以得到褐色油(20.7g,97%),其不进一步提纯而直接用于下一步骤中。1H NMR(400MHz,CDCl3)δ7.10(d,1H,J=5.2Hz),6.91(dd,1H,J=5.7,4.4Hz),6.77(d,1H,J=3.2Hz),2.82(t,2H,J=7.6Hz),1.68(q,2H,J=6.8Hz),1.50-1.20(m,22H),0.88(t,3H,J=6.8Hz)。
实施例4
三甲基-(5-十四烷基-噻吩-2-基)-锡烷的合成
将n-BuLi(1.6M,42mL,67毫摩尔)在-78℃下缓慢地加入2-十四烷基-噻吩(17.0g,237毫摩尔)的THF(150mL)溶液中并搅拌30分钟。将在THF(30mL)中的三甲基氯化锡(13.3g,67毫摩尔)逐滴加入所得悬浮液中,然后逐步加热至室温。将反应混合物搅拌18小时并用饱和氯化铵溶液(100mL)骤冷。将混合物用二乙醚(2×100mL)萃取并将结合的有机萃取物用盐水(100mL)洗涤。将有机相干燥并浓缩以得到褐色油(26.8g,99%),其不进一步提纯而直接用于下一步骤中。1H NMR(400MHz,CDCl3)δ7.02(d,1H,J=3.2Hz),6.90(d,1H,J=3.2Hz),2.85(t,2H,J=8Hz),1.68(q,2H,J=7.6Hz),1.50-1.20(m,22H),0.88(t,3H,J=6.8Hz),0.344(s,9H)。
实施例5
2,3-二溴-1,4-双(三甲基-(5-十四烷基-噻吩-2-基)-锡烷)-苯的合成
将四(三苯基膦)钯(0)(3.55g,3.07毫摩尔)加入2,3-二溴-1,4-二碘-苯(15.0g,30.7毫摩尔)和三甲基-(5-十四烷基-噻吩-2-基)-锡烷(35.0g,78.9毫摩尔)的DMF(100mL)溶液中并在120℃下搅拌6小时。将反应混合物冷却至室温并用水(100mL)稀释。将混合物用二氯甲烷(2×150mL)萃取。将结合的有机相干燥并浓缩以得到褐色油,将其通过柱层析提纯以得到白色固体(15.0g,61%)。1H NMR(400MHz,CDCl3)δ7.37(s,2H),7.07(d,2H,J=3.6Hz),6.77(d,2H,J=3.6Hz),2.83(t,4H,J=7.6Hz),1.71(q,4H,J=6.8Hz,7.6Hz),1.50-1.20(m,44H),0.88(s,6H)。
实施例6
三甲基-三丁基锡烷基乙炔基-硅烷的合成
将n-BuLi(1.6M,24.4mL,39毫摩尔)在-78℃下逐滴加入乙炔基三甲基硅烷(4.0g,41毫摩尔)的THF(40mL)溶液中并经30分钟逐步加热至0℃。将反应混合物再次冷却至-78℃,并将在THF(30mL)中的三丁基氯化锡(11.4mL,39毫摩尔)逐滴加入所得混合物中。将反应混合物在室温下搅拌18小时并用水(20mL)骤冷。将混合物用二乙醚(2×100mL)萃取并将结合的有机萃取物用盐水(50mL)洗涤。将有机相干燥并浓缩以得到黄色油(15.0g,95%),其不进一步提纯而直接用于下一步骤中。1H NMR(400MHz,CDCl3)δ1.67-1.45(m,6H),1.45-1.20(m,6H),0.98(t,6H,J=8.4Hz),0.90(t,9H,J=7.2Hz),0.16(s,9H)。
实施例7
2,3-双(乙炔基三甲基硅烷)-1,4-双(三甲基-(5-十四烷基-噻吩-2-基)-锡烷)-苯的合成
将四(三苯基膦)钯(0)(2.9g,2.52毫摩尔)加入2,3-二溴-1,4-双(三甲基-(5-十四烷基-噻吩-2-基)-锡烷)-苯(10.0g,12.6毫摩尔)和三甲基-三丁基锡烷基乙炔基-硅烷(14.6g,37.8毫摩尔)的甲苯(250mL)溶液中并在120℃下搅拌5小时。将反应混合物冷却至室温并用水(100mL)稀释。将混合物用二氯甲烷(2×100mL)萃取。将结合的有机相干燥并浓缩以得到褐色油,将其通过快速柱层析提纯以得到定量收率的黄色固体(14.5g)作为粗产物。粗产物不进一步提纯而直接用于下一步骤中。1H NMR(400MHz,CDCl3)δ7.49(d,2H,J=3.6Hz),7.42(s,2H),6.74(d,2H,J=3.6Hz),2.82(t,4H,J=7.6Hz),1.80-1.60(m,4H),1.50-1.20(m,44H),0.92(t,6H,J=7.6Hz),0.27(s,18H)。
实施例8
2,3-二乙炔基-1,4-双(三甲基-(5-十四烷基-噻吩-2-基)-锡烷)-苯的合成
将四丁基氟化铵的THF溶液(1M,83mL,83毫摩尔)在室温下逐滴加入2,3-双(乙炔基三甲基硅烷)-1,4-双(三甲基-(5-十四烷基-噻吩-2-基)-锡烷)-苯(20.9g,25毫摩尔)的THF(240mL)溶液中并搅拌3小时。将反应混合物用饱和氯化铵溶液(200mL)骤冷并用THF(3×100mL)萃取。将结合的有机相干燥并浓缩以得到褐色固体,将其通过快速柱层析提纯以得到浅黄色固体(9.5g,55%,经2个步骤)。1H NMR(400MHz,CDCl3)δ7.48(d,2H,J=3.6Hz),7.45(s,2H),6.77(d,2H,J=3.6Hz),3.54(s,2H),2.82(t,4H,J=7.6Hz),1.80-1.60(m,4H),1.50-1.20(m,44H),0.91(t,6H,J=7.6Hz)。
实施例9
2,9-二-十四烷基-1,10-二硫杂-二环戊[a,i]菲的合成
将2,3-二乙炔基-1,4-双(三甲基-(5-十四烷基-噻吩-2-基)-锡烷)-苯(8.9g,13毫摩尔)和二氯化铂(1.4g,5.21毫摩尔)的甲苯(40mL)溶液在90℃下搅拌18小时。将反应混合物冷却至室温并过滤。将滤液浓缩并将残渣用己烷(50mL)处理。将所得褐色悬浮液过滤并作为褐色残渣分离粗产物。将褐色残渣从热己烷中再结晶以得到白色固体(1.6g,18%)。1H NMR(400MHz,CDCl3)δ8.61(d,2H,J=8.8Hz),8.08(s,2H),7.88(d,2H,J=8.8Hz),7.17(s,2H),2.99(t,4H,J=7.2Hz),1.85-1.75(m,4H),1.50-1.20(m,44H),0.87(t,6H,J=7.2Hz)。
实施例10
底栅顶触点OFET的器件制造的一般程序
具有200nm厚热生二氧化硅(SiO2)的高度掺杂p型硅(100)片用作基质。半导体层通过溶液-或真空沉积(<1×10-3Pa)技术制造。然后通过荫罩板将用于源和漏电极的50nm厚Au层沉积以得到顶触点OFET器件。通道宽度(W)为50μm且通道长度(L)通常为1000μm。
在Keithley 4200SCS上测量晶体管的电特征。所有测量在空气中在室温下进行。所有基于非那省衍生物的OFET显示出典型的p型特征。为得到转换曲线,将漏-源电压(Vd)保持在-60V。使用以下方程式在饱和情况下由(Id)1/2相对于Vg和阈电压(Vth)的斜率提取空穴的电荷载流子迁移率(μ):μ=2Id/{(W/L)Ci(Vg-Vth)2}。
OFET的性能汇总于表1以及图1和2中。
图1A和B显示出溶液沉积OFET的输出和转换特征。在图1A中,将漏电流相对于漏电压绘出。在图1B中,将漏电流相对于栅-源电压绘出。
图2显示真空沉积OFET的转换特征。将漏电流相对于栅-源电压绘出。
表1.基于非那省的OFET的典型特征
Claims (13)
1.式I的非那省(phenacene)化合物:
其中:
基团a、b和c中的一个为X,且其它两个基团分别为C-R1和C-R2,
基团d、e和f中的一个为X,且其它两个基团分别为C-R5和C-R6,
其中X相互独立地选自NH、O、S和Se,
R1-R10相互独立地为H、卤素、-CN、-NO2或者线性或支化、饱和或不饱和C1-C40烃残基,其可被卤素(F、Cl、Br、I)、-ORa、-NRa 2、-CN和/或-NO2取代1-5次,且其中一个或多个CH2-基团可被-O-、-S-、-NRb-、-OC(O)-或-C(O)-取代,且其中Ra和Rb相互独立地为H、C1-C30烷基、C2-C30烯基、C2-C30炔基、C1-C30卤代烷基、C2-C30卤代烯基、C2-C30卤代炔基或C2-C30酰基。
2.根据权利要求1的非那省化合物,其具有式Ia-If:
其中:
X和R1-R10如权利要求1中所定义。
3.根据权利要求1或2的非那省化合物,其中X选自O、S和Se。
4.根据权利要求1-3中任一项的非那省化合物,其中X为S。
5.根据权利要求1-4中任一项的非那省化合物,其中R7-R10为氢。
6.根据权利要求1-5中任一项的非那省化合物,其中R3和R4为氢。
7.根据权利要求1-6中任一项的非那省化合物,其中R1、R2、R5和R6各自相互独立地为氢或C1-20烷基。
8.根据权利要求2的非那省化合物,其具有式Ia,其中X为S,R1和R5为C1-20烷基,且R2-R4和R6-R10为氢。
9.包含一种或多种根据权利要求1-8中任一项的化合物的薄膜半导体。
10.包含根据权利要求9的薄膜半导体的场效应晶体管器件。
11.包含根据权利要求9的薄膜半导体的光伏器件。
12.包含根据权利要求9的薄膜半导体的有机发光二极管器件。
13.包含根据权利要求9的薄膜半导体的单极或互补电路器件。
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JP2015122437A (ja) * | 2013-12-24 | 2015-07-02 | 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 |
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