CN101134744B - 杂环的化合物,其用途、有机半导体材料和电子或光电元件 - Google Patents
杂环的化合物,其用途、有机半导体材料和电子或光电元件 Download PDFInfo
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- CN101134744B CN101134744B CN2007100889082A CN200710088908A CN101134744B CN 101134744 B CN101134744 B CN 101134744B CN 2007100889082 A CN2007100889082 A CN 2007100889082A CN 200710088908 A CN200710088908 A CN 200710088908A CN 101134744 B CN101134744 B CN 101134744B
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- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 2
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Classifications
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Abstract
本发明涉及杂环的自由基或双自由基，其二聚物，低聚物，聚合物，二螺化合物和多环，涉及有机半导体材料和电子和光电元件。
Description
技术领域
本发明涉及杂环的自由基或双自由基、其二聚物、低聚物、聚合物、二螺化合物和多环，其用途、有机半导体材料和电子或光电元件。
背景技术
已知通过掺杂来调节有机半导体的电学性质，尤其是它们的导电性，对于无机半导体例如硅半导体亦然。在此，起初非常低的导电性通过在基体材料中产生载荷子而得以提高，并且取决于所用的掺杂剂类型，还可以实现半导体的Fermi级的改变。在这种情况下掺杂导致电荷传递层的传导率提高，由此欧姆损耗减少，接触物和有机层之间载荷子的传递提高。
目前所用的无机掺杂剂，例如碱金属或碱土金属(例如铯)或Lewis酸(例如FeCl3)，由于其高的扩散系数，在有机基体材料的情形下通常是不利的，因为电子元件的功能和稳定性被损坏。这些无机掺杂剂还有生产困难的问题，因为它们在室温下通常具有高的蒸气压，可能在真空工艺中污染生产系统。由于其对空气的高反应性，碱金属或碱土金属的使用更加因难，因此其也就更为不利。也已知通过化学反应在半导体基体材料中释放掺杂剂以提供掺杂剂。但是以这种方式释放的掺杂剂的氧化电势通常不足以用于各种应用，例如尤其是有机发光二极管(OLEDs)。而且，当释放掺杂剂时，也产生了其他化合物和/或原子，例如原子氢，从而使掺杂层和相应的电子元件的性质遭到破坏。
此外，用作掺杂剂的化合物对于相应的应用而言通常不具有足够低的电离势。
发明内容
本发明的目的是提供新型化合物，其可用作n型掺杂剂，用作注入层或用作阻挡层，其中所述化合物还具有足够低的氧化电势用于生产有机发光二极管的电子传递材料，而不会对基体材料有任何破坏性影响，和意欲提供基体材料中载荷子数量的有效增加并且相对容易处理。
本发明的其他目的包括指明这些化合物可能的用途，提供有机半导体材料和其中可以使用所述化合物的电子元件或光电元件，例如光引发存储器。
第一个目的通过权利要求1给出的杂环的自由基或双自由基、其二聚物、低聚物、聚合物、二螺化合物和多环而实现。其他目的通过其他独立权利要求的内容而实现，优选的实施方式在从属权利要求中给出。
更优选具有下列结构的化合物：
结构5e-5o和3h中的R0，R1-R12可从权利要求1中对于R’s的定义中选择。
另外，优选结构5c，其中R1-R16＝H或R1，R4-R16＝H和R2，R3＝CH3。
另外，一种特别优选的化合物是基于结构1a，其中Y＝NR21，其中R21＝烷基，优选甲基；其中R0，R21＝烷基，优选甲基；R1，R2＝芳基，尤其是苯基、甲苯基、二甲苯基、茴香基、噻吩基、呋喃基、烷基，尤其是环己基、环戊基、正烷基；或混合变体，其中R1＝烷基，尤其是甲基、乙基、丙基，和R2＝芳基，尤其是苯基、甲苯基、二甲苯基、茴香基、噻吩基、呋喃基。
在本发明中，术语“二聚物”应理解为通过使两个单自由基或双自由基彼此反应而产生的化合物。
术语“低聚物”应理解为由多个双自由基组成的化合物，其中一个双自由基的第一自由基末端与其他双自由基的第一末端反应，新形成的较大双自由基的第二末端接着与第二其他双自由基反应。这种低聚物的末端可与单自由基反应。
术语“聚合物”应理解为，与低聚物相比，由较大量的双自由基组成的化合物。
根据本发明，“二螺化合物”是双自由基的分子内加成产物，其基团中心由结构单元隔开，该结构单元的类型使得所述结构单元连接载带自由基的碳原子(即彼此反应的碳原子)。
术语“多环”应理解为双自由基的分子内加成产物，其基团中心由结构单元隔开，该结构单元的类型使得所述结构单元连接除载带自由基的碳原子外的至少一个碳原子(例如，至少一个α-位的原子)。
R0-19，R21，R22和R23可优选为取代芳基，其中取代基优选为给电子基团，例如二烷基胺、julolidyl、二芳基胺、烷基芳基氨基、二杂环基胺、二杂烷基胺、烷氧基、芳氧基、烷基巯基、芳基巯基、烷基、甲硅烷基(sililyl)、卤代烷基、环烷基、卤代环烷基、烯基、炔基、三烷基甲硅烷基炔基或苯乙烯基。
所有要求保护的化合物可以是全氟化的或部分氟化的，特别是饱和的桥或柄。
出人意料地发现，如果自由基和双自由基、其二聚物、低聚物、聚合物、二螺化合物和多环以中性形式用作有机半导体基体材料的n型掺杂剂，则得到比从前已知的给体化合物更强和/或更稳定的掺杂剂。特别地，当根据本发明将所述化合物用作n型掺杂剂时，在诸如电子元件等的应用中，电荷传递层的传导率可显著提高，和/或接触物和有机层之间载荷子的传递可以显著提高。本发明的化合物本身也可用作传递材料。因此，在蒸气沉积过程中为产生有机半导体材料，例如自由基(或二聚物)与常规基体材料之间的浓度比可以是10∶1。
不欲被其所限制，认为根据本发明，当所公开的杂环化合物用于掺杂层时，尤其通过从相应的杂环的自由基或双自由基、其二聚物、低聚物、二螺化合物或多环传递至少一个电子到周围的基体材料，而形成与相应的杂环的自由基和双自由基相关的阳离子。在此过程中，也形成基体材料的阴离子，其可以在基体材料上移动。以这种方式，基体材料得到了比未掺杂基体材料更高的传导率。未掺杂基体材料的传导率通常＜10-8S/cm，特别地通常＜10-10S/cm。应确保基体材料具有足够高的纯度。可用常规方法例如梯度升华来获得这种纯度。通过掺杂，该基体材料的传导率可提高至大于10-8S/cm，通常＞10-6S/cm。这尤其适用于还原电势小于-1V vs.Fc/Fc+，优选小于-1.7V vs.Fc/Fc+，特别小于-2.1V vs.Fc/Fc+的基体材料。符号Fc/Fc+涉及氧化还原对二茂铁/铁铈齐(ferrocenium)，其在电化学电势确定例如循环伏安法中用作参照。
在本申请中，掺杂剂一方面理解为混入的材料(“该层用掺杂剂掺杂”)。另一方面，掺杂剂可以是氧化还原活性物质，其导致电荷传递传导率(“该掺杂剂导致n型掺杂”)。认为二聚物等是所述第一类型的掺杂剂，而相应的自由基则是第二类型的掺杂剂。
根据本发明还发现，所述杂环的自由基或双自由基和其衍生物可用作电子元件中的注入层，优选在电极和半导体层之间，其也可以是掺杂的，或用作阻挡层，优选在发光层和传递层之间，或用作电子元件中的半导体层。还发现通过本发明的化合物，有机半导体的光引发(photo-induced)或光引发(light-induced)的不可逆掺杂是可能的，特别是通过电磁辐射裂解它们的二聚物或低聚物或二螺化合物并随后进行n型传导半导体的不可逆掺杂来产生所述的自由基和双自由基。
也可使用本发明的化合物作为食品工业、制药业中的自由基清除剂或抗氧化剂，用于消防或用作杀虫剂，特别用作杀昆虫剂、除草剂、杀真菌剂等等。也可用作自由基反应中的自由基引发剂(优选自由基引发的聚合或活性自由基聚合)。最后，应指出三重态双自由基也可在有机电子和光电元件中以存储器或开关结构的形式用作磁性化合物。
回到本发明的杂环的自由基、双自由基和其衍生物作为掺杂剂的优选用途，可例如通过下列三种机理以光引发的方式进行掺杂：
1.所述二聚物/低聚物/聚合物/二螺化合物或多环本身吸收适当波长的电磁辐射，从而裂解为掺杂自由基或双自由基。电子从自由基/双自由基的HOMO转移到基体材料的LUMO。
2.通过暴露于电磁辐射激发基体材料，从而电子从掺杂剂(二聚物/低聚物/聚合物/二螺化合物/多环)的HOMO转移到前一HOMO，该HOMO现在是单电子占据的(single occupied)。该掺杂剂然后进行不可逆反应。
3.光化学激发掺杂剂(二聚物/低聚物/聚合物/二螺化合物/多环)，然后电子从掺杂剂的单电子占据的LUMO转移到基体材料的LUMO。该掺杂剂然后进行不可逆反应。
但是，各种机理同时发生也是可能的，最终可能通过此处未提及的机理而实现电子转移，例如通过键的热裂解。然而，一旦电磁辐射被关掉，全部的或部分的传导率被不可逆地和永久地保留。
现在基于下列实施例描述本发明的化合物的其他目的和优点，这些实施例仅是说明性的，不是用来限制本发明的范围。
本发明的掺杂剂就其与大气的反应性而言具有出人意料的高稳定性。
具体实施方式
合成方法
可通过已知方法合成本发明的自由基、双自由基和其衍生物。应理解所引用的文献只是以例子的方式提及。
对于所有所述的化合物，以苯并咪唑为例未意性的显示获得自由基/双自由基的完整路径。
苯并咪唑c尤其可由邻苯二胺a和适当的羧酸衍生物(M.R.DeLuca，S.M.Kerwin Tetrahedron 1997，53 457-64)可醛类(M.Curini etal.Synlett 2004，10，1832-4)容易地合成。还参见：M.R.Grimmett“Imidazole and Benzimidazole Synthesis”Academic Press；Harcourt Brace& Company，Publishers，London，San Diego，New York，Boston。邻苯二胺是可商购的或可例如通过Suschitsky et al.的方法得到(J.Chem.Soc.Chem.Comm.1977，189-90)。苯并噻衍生物或噁唑衍生物可通过邻巯基苯胺或邻羟基苯胺以相同的方式获得。在碱的存在下用硫酸二甲酯或硫酸二乙酯(H.Quast，E.Schmitt Chem.Ber.1968，101，4012-14)或用烷基卤化物进行五元杂环c中N原子的烷基化。相应的阳离子产物(杂芳鎓)d可以中性形式分离，例如作为高氯酸盐、四氟硼酸盐、卤化物、四苯基硼酸盐或六氟磷酸盐或与其他适当的反离子。
所述自由基可以通过碱金属化学制备，或通过还原反应由相应的杂芳阳离子电化学或光化学制备(T.Muramatsu et al.Chemistry Letters1996，151-2；Pragst et al.J.Electroanal.Chem.1984，180，141-56，J.Heinze，
Ber.Bunsenges.1972 76/2 94)。
但是，所述自由基通常进一步快速反应形成二聚物f、低聚物、聚合物、二螺化合物i或多环(三环)l。可通过ESR光谱法检测到所述自由基作为中间阶段发生这一事实。
双-[3-甲基-2-烷基-1，2-二氢苯并噻唑基-(2)]和双-[3-甲基-2-芳基-1，2-二氢苯并噻唑基-(2)]化合物可通过苯并噻唑鎓盐和适当的Grignard化合物直接得到(A.Kinya；S，Hiroaki；I.Naoki；Bull.Chem.Soc.Japan 1979 52/1，156-9)。
二螺化合物I可由2，2’-桥接苯并咪唑形成。
获得N-取代的杂芳阳离子
实施例1：
2-甲基巯基-1，3-二甲基苯并咪唑鎓高氯酸盐
在70ml水中悬浮0.1mol的2-巯基苯并咪唑。加入0.3mol的NaHCO3和0.5mol的硫酸二甲酯并在室温下搅拌过夜。向澄清溶液中逐滴加入12ml 50％四氟硼酸，冷却并通过抽吸沉淀，从1，2-二氯乙烷中重结晶。
Fp.＝160-3℃
实施例2：
2-哌啶基-1，3-二甲基苯并咪唑鎓高氯酸盐
将0.01mol的2-甲基巯基-1，3-二甲基苯并咪唑鎓高氯酸盐与0.01mol的哌啶在250ml二噁烷中回流加热4h。通过抽吸除去固体并从乙醇中重结晶。
Fp.179℃
实施例3：
2-二甲基氨基苯并咪唑鎓氯化物
在室温下在100ml二噁烷中搅拌0.05mol的邻苯二铵二氯化物和0.05mol的二氯亚甲基-N，N-二甲基亚铵氯化物2.5-3h，通过抽吸除去固体并用两者之一洗涤。从乙醇中重结晶。
Fp.293℃
实施例4：
1，4-双-1’，1”，3’，3”-四甲基苯并咪唑鎓-2’，2”-丁烷
在30ml由50％的水和50％的乙二醇单甲基醚组成的混合物中悬浮0.01mol的1，4-二苯并咪唑基-2’，2”-丁烷，加入0.06mol的碳酸氢钠和0.05mol的硫酸二甲酯并在室温下搅拌过夜。然后用10mol的浓高氯酸过滤并沉淀。
实施例5：
2，3，5，6-四氢-1H，4H-3a，10b-二氮杂-6a-氮鎓荧蒽
在205ml的DMF中于120℃加热0.1mol的2-氨基苯并咪唑与0.2mol的1，3-二溴丙烷和0.3mol的KCO3 8h。通过抽吸除去固体，充分浓缩溶剂，吸收甲醇，然后加入70％高氯酸。用甲醇、水并再用甲醇洗涤沉淀的白色晶体。
Fp.：242℃
实施例6：
2-异丙基-1，3-二甲基苯并咪唑鎓高氯酸盐
在70ml水中悬浮0.1mol的2-巯基苯并咪唑。加入0.3mol的NaHCO3和0.5mol的硫酸二甲酯并在室温下搅拌过夜。向澄清溶液中逐滴加入10ml 70％高氯酸，冷却并通过抽吸沉淀，从乙醇中重结晶。
Fp.＝346℃
实施例7：
双-(N，N’，2，2’-四甲基-1H-苯并咪唑鎓)-1，3-丙烷二碘化物
在20ml二甲氧基乙烷中在氩气下悬浮0.02mol的NaH，在冰冷却下加入0.02mol的2-甲基苯并咪唑。气体发散结束后，在室温下继续搅拌60min，逐滴加入0.01mol的1，3-二溴丙烷并搅拌10min。在水浴中于60℃加热反应混合物4.5h，在室温下搅拌过夜，倾倒到冰/水上。通过抽吸除去沉淀的粗产物并真空干燥。将0.005mol的该中间产物置于30ml水中，加入0.015mol的NaHCO3和0.015mol的硫酸二甲酯，搅拌过夜并用1-2ml的浓盐酸沉淀。
Fp.：分解＞306℃
实施例8：
1，2，3，5，6，7-六甲基苯并-1，7-二氢苯并[1，2-d，4，5-d’]二咪唑鎓二高氯酸盐
在约40-50ml水中悬浮0.013mol的2，6-二甲基苯并-1，7-二氢苯并[1，2-d，4，5-d’]二咪唑，加入0.078mol的NaHCO3和0.064mol的硫酸二甲酯。在室温下搅拌12h，逐滴加入4-5ml的70％高氯酸。通过抽吸除去白色沉淀，用乙醇、水并再用乙醇洗涤。
Fp.：＞350℃
获得自由基、双自由基，和其二聚物、低聚物以及二螺化合物或多环
实施例a：
双-[1，3-二甲基-2-N-哌啶基-1，2-二氢苯并咪唑基-(2)]
在THF中回流加热0.01mol的2-N-哌啶基-1，3-二甲基苯并咪唑鎓四氟硼酸盐和钾，过滤，浓缩并冷却。通过抽吸除去沉淀晶体并用冷乙腈洗涤。
Fp：195℃
实施例b：
双-[1，3-二甲基-2-异丙基-1，2-二氢苯并咪唑基-(2)]
将1，3-二甲基-2-异丙基苯并咪唑鎓高氯酸盐溶于0.1M的四丁基铵高氯酸盐在乙腈中的溶液中，并在-2.3V下在三室电解槽中利用汞电极沉淀。通过抽吸除去所述白色沉淀，用乙腈洗涤并真空干燥。
Fp：146℃
实施例c：
双-[1，3-二甲基-2-N-吡咯烷基-1，2-二氢苯并咪唑基-(2)]
将1，3-二甲基-2-N-吡咯烷基苯并咪唑鎓高氯酸盐溶于0.1M的四丁基铵高氯酸盐/DMF中，并在-2.3V下在三室电解槽中利用汞电极沉淀。通过抽吸除去所述白色沉淀，用乙腈洗涤并真空干燥。
Fp：120℃
实施例d：
双-[1，3，5，6-四甲基-2-异丙基-1，2-二氢苯并咪唑基-(2)]
在THF中回流加热0.01mol的1，3，5，6-四甲基-2-异丙基苯并咪唑鎓四氟硼酸盐和钾，过滤，浓缩并冷却。通过抽吸除去沉淀晶体并用冷乙腈洗涤。
或者
将1，3，5，6-四甲基-2-异丙基苯并咪唑鎓高氯酸盐溶于0.1M的四丁基铵高氯酸盐/DMF中，并在-2.3V下在三室电解槽中利用汞电极沉淀。通过抽吸除去所述白色沉淀，用乙腈洗涤并真空干燥。
Fp：129-30℃
实施例e：
2-异丙基-1，3-二甲基-2，3，6，7-四氢-1H-5，8-二氧杂-1，3-二氮杂环五[b]萘
溶解0.1M的四丁基铵高氯酸盐/乙腈，并在-2.4V下在三室电解槽中利用汞电极沉淀。通过抽吸除去所述白色沉淀，用乙腈洗涤并真空干燥。
Fp：142℃
实施例f：
1，2，3，5，6，7-六甲基苯并-1，7-二氢苯并[1，2-d，4，5-d’]二咪唑基-(2)低聚双自由基
将0.01mol的1，2，3，5，6，7-六甲基苯并-1，7-二氢苯并[1，2-d，4，5-d’]二咪唑鎓二高氯酸盐溶解在0.1M的四丁基铵高氯酸盐/DMF中，并在-2.3V下在三室电解槽中利用汞电极沉淀。通过抽吸除去所述白色沉淀，用乙腈洗涤并真空干燥。
Fp：＞250℃
实施例g：
双-[1，3-二甲基-2-异丙基-1，2，4，5，6，7-六氢苯并咪唑基-(2)]
将1，3-二甲基-2-异丙基-4，5，6，7-四氢苯并咪唑鎓六氟磷酸盐溶于0.1M的四丁基铵六氟磷酸盐在DMF中的溶液中，并在-2.6V下在三室电解槽中利用汞电极沉淀。通过抽吸除去所述白色沉淀，用乙腈洗涤并真空干燥。
Fp：127-9℃
实施例h：
双-[4，5-二苯基-2-异丙基-1，2-二氢咪唑基-(2)]
将4，5-二苯基-2-异丙基咪唑鎓六氟磷酸盐溶于0.1M的四丁基铵六氟磷酸盐在DMF中的溶液中，并在-2.45V下在三室电解槽中利用汞电极沉淀。通过抽吸除去所述白色沉淀，用乙腈洗涤并真空干燥。
Fp：160-3℃
实施例i：
双-[3-苯基-2-异丙基-1，2-二氢苯并噻唑基-(2)]
将3-苯基-2-异丙基苯并噻唑鎓高氯酸盐溶于0.1M的四丁基铵高氯酸盐在乙腈中的溶液中，并在-2.3V下在三室电解槽中利用汞电极沉淀。通过抽吸除去所述白色沉淀，用乙腈洗涤并真空干燥。
Fp：146℃
基体材料
作为n型掺杂(n-dopable)基体材料，可以使用喹啉络合物，例如铝或其他主族金属，其中所述的喹啉配体也可以被取代。特别地，所述基体材料可以是三(8-羟基喹啉)合铝。还可以任选使用其他带有O和/或N供电子原子的铝络合物。常见的基体材料还有酞菁锌(ZnPc)或四苯基卟啉锌(ZnTPP)，仅列出几个酞菁或卟啉络合物的例子。
Bis-(2-methyl-8-quinolinolato)-4-(phenyl-phenolato)-aluminium-(III)
所述的喹啉络合物可含有例如一个、两个或三个喹啉配位体，其中另外的配位体优选与O和/或N供电子原子络合到中心原子上，如例如上述的Al络合物。
作为基体材料，还可使用菲咯啉，其可是取代或未取代的，特别是芳基取代的。例如苯基或萘基取代的。特别的，可使用Bphen作为基体材料。
作为基体材料，还可使用杂原子，例如特别是三唑，还可以是吡咯，咪唑，三唑，吡啶，嘧啶，哒嗪，喹喔啉，吡嗪并喹喔啉等。所述杂原子优选被取代，特别是芳基取代，例如苯基或萘基取代的。特别的，可使用下面的三唑作为基体材料。其他的基体材料例如可见A.P.Kulkarni et al.，Chem.Mater.16，4556ff.(2004)。
3-(4-Biphenylyl)-4-phenyl-5-tert-butylphenyl-1，2，4-triazole
C30H27N3
所用的基体材料优选完全由金属酞青络合物组成，特别是ZnPc，卟啉络合物，或巴克明斯特·富勒烯，特别是C60富勒烯。
应理解为在本发明的范围内，所述的基体材料还可以用作彼此或与其他材料的混合物。应理解为还可使用适当的具有半导体特性的其他有机基体材料。
掺杂方法
在掺杂工艺中，作为开环的结果，所述的聚合、低聚或二聚化合物或二螺化合物分解得到实际的掺杂自由基。所述聚合物、低聚物和二聚物和二螺化合物的分解还可以在所述混合层的制备之前、其间或之后，以光引发方式进行，并从而将所述半导体层暴露于电磁辐射之下，优选在紫外和/或可见光下，有利地在所述混合汽相淀积(混合物由掺杂剂和基体组成)之前、其间或之后发生。此外，在所述汽相淀积过程中受热可引起所述聚合物、低聚物和二聚物或二螺化合物裂解成具有掺杂性质的自由基。对于某些应用，在生产其间或之后加热所述混合层也是有利的。
用本发明化合物对各基体材料的掺杂可以通过以下方法的一种或组合进行。
a)在真空中用一种用于基体材料和一种用于掺杂剂的源进行混合汽相淀积。
b)依次将所述基体材料和n型掺杂剂沉淀到基材上，随后所述掺杂剂向内扩散，特别是通过热处理。
c)用n型掺杂剂溶液掺杂基体层，随后蒸发溶剂、特别是通过热处理。
d)通过应用到表面上的掺杂剂层而表面掺杂基体材料层。
e)制备基体分子和掺杂剂的溶液，然后通过常规方法，例如溶剂蒸发或旋涂制备一层由该溶液组成的层。
所述掺杂还可以这样进行，即将掺杂剂从前体化合物中蒸发出来，其在加热和/或受辐射时释放出掺杂剂。所述前体化合物可使用例如，羰基化合物，二氮化合物或类似的在释放掺杂剂时释放出CO、氮等的物质，其中还可使用其他适当的前体，例如盐，如卤化物，氢化化合物等。可通过电磁辐射，尤其是可见光、UV光或IR光进行辐射照射，例如激光，或者通过其他类型的辐射。所述辐射照射可基本通过蒸发所需的热，并还可能以靶向方式将辐射引入所述待蒸发的化合物或前体或络合物化合物-例如电荷转移络合物-的特定波段，以通过分离所述络合物促进所述化合物的蒸发，例如通过将它们转移到激发态。然而，所述络合物还可特别是足够稳定的以蒸发而无离解，或者在给定条件下被应用到所述基材上。应理解还可使用其他适当的方法进行所述掺杂。
这样，根据本发明，从而可以制得有机半导体的n型掺杂层，其可以多种方式使用。
掺杂使用实施例
提供了本发明自由基或其低聚物，优选二聚物，和双自由基或二螺化合物和其三环。
实施例I：
与基体材料酞菁锌ZnPc一起使用中性二聚物双-[1，3-二乙基-2-甲基-1，2-二氢苯并咪唑基-(2)]。以ZnPc作为基体材料，通过基体和掺杂剂的混合汽相淀积制备掺杂比为掺杂剂∶基体材料为1∶20的掺杂层。这里的传导率为3×10-4S/cm。
实施例II：
以与实施例I类似的方式，以在实施例I中给出的比例进行双-[1，3-二甲基-2-异丙基-1，2-二氢苯并咪唑基-(2)]和ZnPc的混合汽相淀积。得到的传导率为10-3S/cm。
实施例III：
以与实施例I类似的方式，以在实施例I中给出的比例进行双-[1，3-二甲基-2-异丙基-1，2-二氢苯并咪唑基-(2)]和ZnTTP的混合汽相淀积。得到的传导率为10-8S/cm。
实施例IV：
以与实施例I类似的方式，以在实施例I中给出的比例进行双-[1，3-二甲基-2-乙基-1，2-二氢苯并咪唑基-(2)]和ZnPc的混合汽相淀积。得到的传导率为10-4S/cm。
实施例V：
以与实施例I类似的方式，以在实施例I中给出的比例进行双-[1，3-二甲基-2-N-吡咯烷基-1，2-二氢苯并咪唑-(2)]和ZnTPP的混合汽相淀积。得到的传导率为10-4S/cm。
实施例VI：
以与实施例I类似的方式，以在实施例I中给出的比例进行双-[1，3，5，6-四甲基-2-异丙基-1，2-二氢苯并咪唑基-(2)]和八乙基卟啉锌ZnOEP的混合汽相淀积。得到的传导率为5×10-8S/cm。
实施例VII：
以与实施例I类似的方式，以在实施例I中给出的比例进行2-异丙基-1，3-二甲基-2，3，6，7-四氢-1H-5，8-二氧杂-1，3-二氮杂环五[b]萘和ZnTPP的混合汽相淀积。得到的传导率为1.8×10-4S/cm。
实施例VIII：
以与实施例I类似的方式，以在实施例I中给出的比例进行2-异丙基-1，3-二甲基-2，3，6，7-四氢-1H-5，8-二氧杂-1，3-二氮杂环五[b]萘和ZnOEP的混合汽相淀积。得到的传导率为5×10-8S/cm。
实施例IX：
以与实施例I类似的方式，以在实施例I中给出的比例进行2-异丙基-1，3-二甲基-2，3，6，7-四氢-1H-5，8-二氧杂-1，3-二氮杂环五[b]萘和ZnPc的混合汽相淀积。得到的传导率为2.2×10-8S/cm。
实施例X：
以与实施例I类似的方式，以在实施例I中给出的比例进行双-[1，3-二甲基-2-异丙基-1，2-二氢苯并咪唑基-(2)]和ZnPc的混合汽相淀积。得到的传导率为10-3S/cm。
实施例XI：
以与实施例I类似的方式，以在实施例I中给出的比例进行双-[1，3-二乙基-2-甲基-1，2-二氢苯并噻唑基-(2)]和ZnPc的混合汽相淀积。得到的传导率为3.8×10-7S/cm。
在上述说明书和权利要求书中公开的本发明的特征可以单独或彼此组合方式来完成本发明的不同实施方式。
Claims (12)
1.一种杂环的自由基的二聚物、二螺化合物和三环，特征在于所述自由基具有下式的结构：
其中结构3具有一个或多个环状连接A和/或A1和/或A2，其中A，A1和A2可以是碳环、杂环和/或多环环系；
其中X，Y＝N或NR21；R0、R1、R2和R21独立选自芳基，杂芳基，H，环烷基，杂环烷基，烷基，烯基，炔基，或R0、R1、R2和R21，单独或结合形成脂肪族或杂脂肪族或芳香族环系或杂芳香族环系的部分；
条件是排除以下结构：
结构3a
结构3a
结构1
2.根据权利要求1的二聚物、二螺化合物和三环，其特征在于A，A1和A2选自芳香族和杂芳香族环系，优选苯并、萘并、噻吩、呋喃、噻唑、咪唑、噁唑、噻二唑、吡嗪、噻喃、邻苯二甲酸酰亚胺和二噻唑基，其中可存在一个或多个取代基，其选自R0、R1、R2和R21。
3.根据权利要求1的二聚物、二螺化合物和三环，所述自由基的特征在于以下结构之一：
4.根据权利要求1的二聚物、二螺化合物和三环，其特征在于R0、R1、R2和R21选自苯基，二苯基，萘基，噻吩基，咪唑基，吡咯基，噻唑基，噁唑基，噻二唑基，哌啶基，吡咯烷基，吗啡酚基和硫代吗啡酚基。
5.根据权利要求1的二聚物、二螺化合物和三环，其特征在于R0-19，R21，R22和R23选自烷基，环烷基。
6.根据前述权利要求1-5任一项的二聚物、二螺化合物和三环作为用于掺杂有机半导体基体材料的掺杂剂，作为阻挡层，作为电荷注入层，作为电极材料，作为记忆材料或作为电子和光电元件中的半导体层自身的用途。
7.一种含有至少一种有机基体化合物和掺杂剂的有机半导体材料，其特征在于所述的掺杂剂是权利要求1的至少一种化合物。
8.根据权利要求7的有机半导体材料，其特征在于掺杂剂与基体分子的掺杂摩尔比或掺杂剂与聚合物基体分子的单体单元的掺杂比为1∶1至1∶100000。
9.一种制备含有有机基体分子和掺杂剂的有机半导体材料的方法，其特征在于至少一种根据权利要求1的化合物用作掺杂剂。
10.一种具有电功能活性区域的电子或光电元件，其特征在于所述的电活性区域包括至少一种权利要求1的化合物。
11.根据权利要求10的电子或光电元件，其特征在于所述的电活性区域包括有机半导体基体材料，所述有机半导体基体材料利用根据权利要求1的至少一种化合物，用至少一种掺杂剂掺杂以改性所述半导体基体材料的电子性能。
12.根据权利要求10或11的电子或光电元件，其为有机发光二极管、光电池，有机太阳能电池，有机二极管，有机场效应晶体管或光敏和磁存储器的形式。
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| CN2007100896620A Active CN101093874B (zh) | 2006-03-21 | 2007-03-21 | 由基质和掺杂材料组成的混合物,及由其构成层的方法 |
| CN2007100889082A Active CN101134744B (zh) | 2006-03-21 | 2007-03-21 | 杂环的化合物,其用途、有机半导体材料和电子或光电元件 |
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| CN2007100896620A Active CN101093874B (zh) | 2006-03-21 | 2007-03-21 | 由基质和掺杂材料组成的混合物,及由其构成层的方法 |
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- 2007-03-21 KR KR1020070027688A patent/KR100885582B1/ko active IP Right Grant
- 2007-03-21 CN CN200780009954.7A patent/CN101405884B/zh active Active
- 2007-03-21 CN CN2007100896620A patent/CN101093874B/zh active Active
- 2007-03-21 TW TW096109810A patent/TWI436985B/zh active
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- 2007-03-22 JP JP2007075182A patent/JP4939988B2/ja active Active
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Also Published As
| Publication number | Publication date |
|---|---|
| CN101405884B (zh) | 2014-02-19 |
| ATE394800T1 (de) | 2008-05-15 |
| CN101405884A (zh) | 2009-04-08 |
| KR20070095818A (ko) | 2007-10-01 |
| US20070252140A1 (en) | 2007-11-01 |
| CN101093874B (zh) | 2013-02-13 |
| US8134146B2 (en) | 2012-03-13 |
| EP1837926A1 (de) | 2007-09-26 |
| KR100885582B1 (ko) | 2009-02-24 |
| TW200745050A (en) | 2007-12-16 |
| CN101134744A (zh) | 2008-03-05 |
| US9118019B2 (en) | 2015-08-25 |
| JP2007314513A (ja) | 2007-12-06 |
| JP4939988B2 (ja) | 2012-05-30 |
| TWI436985B (zh) | 2014-05-11 |
| US20120146012A1 (en) | 2012-06-14 |
| EP1837926B1 (de) | 2008-05-07 |
| HK1104677A1 (en) | 2008-01-18 |
| ES2310380T3 (es) | 2009-01-01 |
| CN101093874A (zh) | 2007-12-26 |
| DE502006000749D1 (de) | 2008-06-19 |
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