Substituted 1,2,3-triylidenetris(cyanomethanylylidene)) cyclopropanes for vte, electronic devices and semiconducting materials using themThe present invention relates to a process for preparation of an electrically doped semiconducting material comprising a [3]-radialene p-dopant or for preparation of an electronic device containing a layer comprising a [3]-radialene p-dopant, the process comprising the steps : (i) loading an evaporation source with the [3]-radialene p-dopant; and (ii) evaporating the [3]-radialene p-dopant at an elevated temperature and at a reduced pressure, wherein the [3]-radialene p-dopant is selected from compounds having a structure according to formula (I) wherein A1 and A2 are independently aryl- or heteroaryl- substituted cyanomethylidene groups, the aryl and/or heteroaryl is selected independently in A1 and A2 from 4-cyano-2,3,5,6-tetrafluorphenyl,2,3,5,6-tetrafluorpyridine-4-yl, 4-trifluormethyl-2,3,5,6-tetrafluorphenyl, 2,4-bis(trifluormethyl)-3,5,6-trifluorphenyl, 2,5-bis(trifluormethyl)-3,4,6-trifluorphenyl, 2,4,6-tris(trifluormethyl)-1,3-diazine-5-yl, 3,4-dicyano-2,5,6-trifluorphenyl, 2-cyano-3,5,6-trifluorpyridine-4-yl, 2-trifluormethyl-3,5,6-trifluorpyridine-4-yl, 2,5,6-trifluor-1,3-diazine-4-yl and 3-trifluormethyl-4-cyano-2,5,6-trifluophenyl), and at least one aryl or heteroaryl is 2,3,5,6-tetrafluorpirydine-4-yl, 2,4-bis(trifluormethyl)-3,5,6-trifluorphenyI, 2,5-bis(trifluormethyl)-3,4,6-trifluorphenyl, 2,4,6-tris(trifluormethyl)-1,3-diazine-5-yl, 3,4-dicyano-2,5,6-trifluorphenyl, 2-cyano-3,5,6-trifluorpyridine-4-yl, 2-trifluormethyl-3,5,6-trifluorphenyl, provided that the heteroaryl in both A1 and A2 cannot be 2,3,5,6-tetrafluorpyridine-4-yl at the same time, respective [3]-radialene compounds, and semiconducting materials and layer, and electronic devices comprising said compounds.One kind, which prepares the electrically doped semi-conducting material comprising the alkene p-doping agent of [3]-axle or prepares to contain, includes [3]-axle alkene p- the method of the electronic device of the layer of dopant, methods described comprises the following steps：(i) evaporation source is loaded with the agent of [3]-axle alkene p-doping, and(ii) [3]-axle alkene p-doping agent described in evaporation at elevated temperature and decompression,wherein described [3]-axle alkene p-doping agent is selected from the compound with the structure according to formula (i)wherein a1and a2the cyanomethylene of aryl or heteroaryl substitution independently is,the aryl and/or heteroaryl are in a1and a2in independently selected from 4- cyano group -2,3,5,6- tetrafluoros phenyl, 2,3,5,6- tetra- double (the trifluoromethyl) -3,5,6- trifluorophenyls of fluorine pyridin-4-yl, 4- trifluoromethyl -2,3,5,6- tetrafluoros phenyl, 2,4-, 2,5- double (trifluoromethyl) -3,4,6- trifluorophenyls, 2,4,6- tri- (trifluoromethyl) -1,3- diazine -5- bases, 3,4- dicyano -2,5, 6- trifluorophenyls, 2- cyano group -3,5,6- trifluoromethyl pyridine -4- bases, 2- trifluoromethyl -3,5,6- trifluoromethyl pyridine -4- bases, 2,5,6- tri- fluoro- 1,3-diazines -4- bases and 3- trifluoromethyl -4- cyano group -2,5,6- trifluorophenyls,and at least one aryl or heteroaryl are 2,3,5,6- ptfe pyridine -4- bases, double (the trifluoromethyl) -3,5,6- three of 2,4- double (the trifluoromethyl) -3,4,6- trifluorophenyls of fluorophenyl, 2,5-, 2,4,6- tri- (trifluoromethyl) -1,3- diazine -5- bases, 3,4- dicyano -2,5,6- trifluorophenyls, 2- cyano group -3,5,6- trifluoromethyl pyridine -4- bases, 2- trifluoromethyl -3,5,6- trifluoromethyl pyridines -4- base, 2,5,6- tri- fluoro- 1,3-diazines -4- bases or 3- trifluoromethyl -4- cyano group -2,5,6- trifluorophenyls, precondition is a1with a2 the heteroaryl in both can not be 2,3,5,6- ptfe pyridine -4- bases simultaneously.
VTE를 위한 치환된 1,2,3-트리일리덴트리스(시아노메타닐일리덴)) 사이클로프로판, 이를 사용하는 전자 디바이스 및 반도체 물질(i) [3]-라디알렌 p-도펀트를 증발 소스(evaporation source)에 로딩하는 단계, 및 (ii) 증가된 온도 및 감소된 압력에서 [3]-라디알렌 p-도펀트를 증발시키는 단계를 포함하여, [3]-라디알렌 p-도펀트를 포함하는 전기적으로 도핑된 반도체 물질을 제조하기 위한 또는 [3]-라디알렌 p-도펀트를 포함하는 층을 함유하는 전자 디바이스를 제조하기 위한 방법, 각각의 [3]-라디알렌 화합물, 및 상기 화합물을 포함하는 반도체 물질 및 층, 및 전자 디바이스에 관한 것이며, [3]-라디알렌 p-도펀트가 하기 화학식 (I)에 따른 구조를 갖는다:[이미지] 상기 식에서, A1 및 A2는 독립적으로 아릴- 또는 헤테로아릴-치환된 시아노메틸리덴 기이고, A1 및 A2에서 아릴 및/또는 헤테로아릴은 독립적으로, 4-시아노-2,3,5,6-테트라플루오르페닐, 2,3,5,6-테트라플루오르피리딘-4-일, 4-트리플루오르메틸-2,3,5,6-테트라플루오르페닐, 2,4-비스(트리플루오르메틸)-3,5,6-트리플루오르페닐, 2,5-비스(트리플루오르메틸)-3,4,6-트리플루오르페닐, 2,4,6-트리스(트리플루오르메틸)-1,3-디아진-5-일, 3,4-디시아노-2,5,6-트리플루오르페닐, 2-시아노-3,5,6-트리플루오르피리딘-4-일, 2-트리플루오르메틸-3,5,6-트리플루오르피리딘-4-일, 2,5,6-트리플루오르-1,3-디아진-4-일 및 3-트리플루오르메틸-4-시아노-2,5,6-트리플루오르페닐로부터 선택되고, 적어도 하나의 아릴 또는 헤테로아릴은 2,3,5,6-테트라플루오르피리딘-4-일, 2,4-비스(트리플루오르메틸)-3,5,6-트리플루오르페닐, 2,5-비스(트리플루오르메틸)-3,4,6-트리플루오르페닐, 2,4,6-트리스(트리플루오르메틸)-1,3-디아진-5-일, 3,4-디시아노-2,5,6-트리플루오르페닐, 2-시아노-3,5,6-트리플루오르피리딘-4-일, 2-트리플루오르메틸-3,5,6-트리플루오르피리딘-4-일, 2,5,6-트리플루오르-1,3-디아진-4-일 또는 3-트리플루오르메틸-4-시아노-2,5,6-트리플루오르페닐이며, 단 A1 및 A2 둘 모두에서 헤테로아릴은 동시에 2,3,5,6-테트라플루오르피리딘-4-일일 수 없다.(i) [3]-라디알렌 p-도펀트를 증발 소스(evaporation source)에 로딩하는 단계, 및(ii) 증가된 온도 및 감소된 압력에서 [3]-라디알렌 p-도펀트를 증발시키는 단계를 포함하여, [3]-라디알렌 p-도펀트를 포함하는 전기적으로 도핑된 반도체 물질을 제조하기 위한 또는 [3]-라디알렌 p-도펀트를 포함하는 층을 함유하는 전자 디바이스를 제조하기 위한 방법으로서, [3]-라디알렌 p-도펀트가 하기 화학식 (I)에 따른 구조를 갖는 화합물로부터 선택되는 방법:[이미지]상기 식에서, A1 및 A2는 독립적으로 아릴- 또는 헤테로아릴-치환된 시아노메틸리덴 기이고, A1 및 A2에서 아릴 및/또는 헤테로아릴은 독립적으로, 4-시아노-2,3,5,6-테트라플루오르페닐, 2,3,5,6-테트라플루오르피리딘-4-일, 4-트리플루오르메틸-2,3,5,6-테트라플루오르페닐, 2,4-비스(트리플루오르메틸)-3,5,6-트리플루오르페닐, 2,5-비스(트리플루오르메틸)-3,4,6-트리플루오르페닐, 2,4,6-트리스(트리플루오르메틸)-1,3-디아진-5-일, 3,4-디시아노-2,5,6-트리플루오르페닐, 2-시아노-3,5,6-트리플루오르피리딘-4-일, 2-트리플루오르메틸-3,5,6-트리플루오르피리딘-4-일, 2,5,6-트리플루오르-1,3-디아진-4-일 및 3-트리플루오르메틸-4-시아노-2,5,6-트리플루오르페닐로부터 선택되고,적어도 하나의 아릴 또는 헤테로아릴은 2,3,5,6-테트라플루오르피리딘-4-일, 2,4-비스(트리플루오르메틸)-3,5,6-트리플루오르페닐, 2,5-비스(트리플루오르메틸)-3,4,6-트리플루오르페닐, 2,4,6-트리스(트리플루오르메틸)-1,3-디아진-5-일, 3,4-디시아노-2,5,6-트리플루오르페닐, 2-시아노-3,5,6-트리플루오르피리딘-4-일, 2-트리플루오르메틸-3,5,6-트리플루오르피리딘-4-일, 2,5,6-트리플루오르-1,3-디아진-4-일 또는 3-트리플루오르메틸-4-시아노-2,5,6-트리플루오르페닐이며, 단 A1 및 A2 둘 모두에서 헤테로아릴은 동시에 2,3,5,6-테트라플루오르피리딘-4-일일 수 없다.