[0012] 以下具體地說明本發明。 本發明之有機矽化合物，是以平均結構式(i)所表示。 [0013][0014] 在此，X表示含有聚苯醚結構之n價的有機基，R1
互為獨立地表示非取代或取代之碳原子數1~10的烷基、或是非取代或取代之碳原子數6~10的芳基，R2
互為獨立地表示非取代或取代之碳原子數1~10的烷基、或是非取代或取代之碳原子數6~10的芳基，A1
表示單鍵、或含有異質原子之二價的連結基，A2
表示不含異質原子之非取代或取代之碳原子數1~20的二價烴基，m為1~3之數，n為1~10之數。 [0015] R1
及R2
之碳原子數1~10的烷基，可為直鏈狀、環狀、分枝狀中任一種，該具體例可列舉出甲基、乙基、正丙基、異丙基、正丁基、二級丁基、三級丁基、正戊基、正己基、正庚基、正辛基、正壬基、正癸基等之直鏈或分枝狀烷基；環丙基、環丁基、環戊基、環己基、環庚基、環辛基等之環烷基。 R1
及R2
之碳原子數6~10的芳基的具體例，可列舉出苯、α-萘基、β-萘基等。 此外，此等各基之氫原子的一部分或全部，可經碳原子數1~10的烷基、F、Cl、Br等之鹵素原子、氰基等所取代，該基的具體例，可例示出3-氯丙基、3,3,3-三氟丙基、2-氰乙基、甲苯基、二甲苯基等。 [0016] 此等當中，R1
，從水解性之觀點來看，較佳為碳原子數1~5的直鏈烷基，尤佳為甲基、乙基，更佳為甲基。另一方面，R2
較佳為直鏈烷基，尤佳為甲基、乙基，更佳為甲基。 此外，m為1~3之整數，從反應性之觀點來看，較佳為2~3，尤佳為3。 [0017] 上述A1
之含有異質原子之二價的連結基的具體例，可列舉出醚鍵(-O-)、硫醚鍵(-S-)、胺鍵(-NH-)、磺醯鍵(-S(=O)2
-)、氧膦鍵(-P-(=O)OH-)、氧代鍵(-C(=O)-)、硫酮鍵(-C(=S)-)、酯鍵(-C(=O)O-)、硫酯鍵(-C(=O)S-)、硫羰酯鍵(-C(=S)O-)、二硫酯鍵(-C(=S)S-)、碳酸酯鍵(-OC(=O)O-)、硫碳酸酯鍵(-OC(=S)O-)、醯胺鍵 (-C(=O)NH-)、硫醯胺鍵(-C(=S)NH-)、胺甲酸乙酯鍵(-OC(=O)NH-)、硫胺甲酸乙酯鍵(-SC(=O)NH-)、硫羰胺甲酸乙酯鍵(-OC(=S)NH-)、二硫胺甲酸乙酯鍵 (-SC(=S)NH-)、脲鍵(-NHC(=O)NH-)、硫脲鍵(-NHC(=S)NH-) 等。 此等當中，A1
較佳為醚鍵(-O-)、或胺甲酸乙酯鍵 (-OC(=O)NH-)。 [0018] 另一方面，A2
之不含異質原子之非取代或取代之碳原子數1~20的二價烴基的具體例，可列舉出亞甲基、伸乙基、三亞甲基、伸丙基、伸異丙基、四亞甲基、伸異丁基、五亞甲基、六亞甲基、七亞甲基、八亞甲基、九亞甲基、十亞甲基、十一亞甲基、十二亞甲基、十三亞甲基、十四亞甲基、十五亞甲基、十六亞甲基、十七亞甲基、十八亞甲基、十九亞甲基、二十亞甲基等之伸烷基；伸環戊基、伸環己基等之伸環烷基；伸苯基、α-,β-伸萘基等之伸芳基等。 此等當中，較佳為三亞甲基、八亞甲基，尤佳為三亞甲基。 [0019] 式(i)中的X表示含有聚苯醚結構之n價的有機基，於此當中，可具有直鏈狀結構、分枝狀結構、或交聯結構。 每一分子之n的平均為1~10，較佳為1~5，尤佳為1~2。n未達1時，由於水解性基不足而使反應性劣化。另一方面，n超過10時，由於反應點變得過多，有時使化合物的保存穩定性惡化，或是硬化物容易產生龜裂。 上述X，只要是含有聚苯醚結構之n價的連結基即可，並無特別限定，考量到提高銅箔密著性及介電特性者，本發明中，特佳為以下述式所表示之基。 [0020][0021] 因此，本發明之有機矽化合物，較佳係平均結構式以式(1)或式(2)所表示，藉由使用此等化合物，可發揮更良好的銅箔密著性及介電特性。 [0022][0023] 此等各式中，R1
、R2
、A1
、A2
及m表示與上述相同涵義，R3
互為獨立地表示鹵素原子、非取代或取代之碳原子數1~12的烷基、非取代或取代之碳原子數1~12的烷氧基、非取代或取代之碳原子數1~12的烷硫基、或是非取代或取代之碳原子數1~12的鹵烷氧基，R4
互為獨立地表示氫原子、鹵素原子、非取代或取代之碳原子數1~12的烷基、非取代或取代之碳原子數1~12的烷氧基、非取代或取代之碳原子數1~12的烷硫基、或是非取代或取代之碳原子數1~12的鹵烷氧基，a及b互為獨立地為1~100之數，c為0以上且未達2之數，Z表示以下述式(3)所表示之連結基。 [0024][0025] 上述R4
表示與上述相同涵義，L表示選自下述式(4)~(11)之連結基。 [0026][0027] 上述R5
互為獨立地表示氫原子或碳原子數1~12的烷基，R6
互為獨立地表示碳原子數1~12的烷基，k表示1~12之整數，j表示1~1,000之數。 [0028] R3
及R4
之碳原子數1~12的烷基，可為直鏈狀、環狀、分枝狀中任一種，該具體例可列舉出甲基、乙基、正丙基、異丙基、正丁基、二級丁基、三級丁基、正戊基、正己基、正庚基、正辛基、正壬基、正癸基、正十一基、正十二基等之直鏈或分枝狀烷基；環丙基、環丁基、環戊基、環己基、環庚基、環辛基等之環烷基。 R3
及R4
之碳原子數1~12的烷氧基，可為直鏈狀、環狀、分枝狀中任一種，該具體例可列舉出甲氧基、乙氧基、丙氧基、異丙氧基、正丁氧基、二級丁氧基、三級丁氧基、正戊氧基、正己氧基、正庚氧基、正辛氧基、正壬氧基、正癸氧基、正十一氧基、正十二氧基等之直鏈或分枝狀烷氧基；環戊氧基、環己氧基、環庚氧基、環辛氧基等之環烷氧基。 此外，此等各基之氫原子的一部分或全部，可經F、Cl、Br等之鹵素原子、巰基、氰基等所取代，該基的具體例，可例示出3-氯丙基、3,3,3-三氟丙基、3-巰丙基、2-氰乙基等。 R3
及R4
的鹵素原子，可列舉出F、Cl、Br等。 [0029] 此等當中，R3
，從製造的容易性之觀點來看，較佳為甲基、甲氧基，尤佳為甲基。 另一方面，R4
較佳為氫原子、甲基、甲氧基，尤佳為氫原子。 [0030] 此外，a及b互為獨立地為1~100之數，從有機矽化合物的銅箔密著性及介電特性之觀點來看，較佳為3~50，尤佳為5~20。當a及b小於1時，會有無法得到良好的銅箔密著性及介電特性之疑慮，當a及b大於100時，有機矽化合物往有機樹脂之相溶性有時會惡化。 [0031] 再者，本發明中，-A1
-A2
-基，較佳為具有以式(12)所表示之胺甲酸乙酯鍵(-OC(=O)NH-)之三亞甲基或是具有以式(13)所表示之醚鍵(-O-)之三亞甲基。 [0032][0033] 本發明之有機矽化合物的重量平均分子量並無特別限定，考量到將含有該化合物之硬化性組成物的黏度等調整為適切的範圍以提升作業性，同時將充分的銅箔密著性及介電特性賦予至所得到之硬化物者，重量平均分子量較佳為500~5萬，尤佳為1,000~2萬，更佳為4,000~1萬。本發明中的重量平均分子量，為依據凝膠滲透層析法(GPC: Gel Permeation Chromatography)所測得之聚苯乙烯換算值。 [0034] 本發明之有機矽化合物，可在含有溶劑之狀態下使用。 溶劑，只要是具有以式(i)所表示之有機矽化合物的溶解能者即可，並無特別限定，從溶解性及揮發性等之觀點來看，較佳為甲苯、二甲苯等之芳香族系溶劑；丁酮、甲基異丁酮等之酮系溶劑；四氫呋喃等之醚系溶劑，當中尤佳為甲苯、二甲苯。 溶劑的添加量，相對於以式(i)所表示之有機矽化合物100質量份，較佳為100~20,000質量份，尤佳為200~10,000質量份。 [0035] 上述以式(i)所表示之有機矽化合物中，A1
為胺甲酸乙酯鍵者，可藉由使以平均結構式(14)或式(15)所表示之於1分子中具有含聚苯醚結構之基及羥基之化合物，與以式(16)所表示之具有異氰酸酯基及烷氧矽基之化合物(以下稱為異氰酸酯矽烷)反應而得到。 更具體而言，係進行：於以平均結構式(14)或(15)所表示之化合物的羥基與異氰酸酯矽烷的異氰酸酯基之間形成胺甲酸乙酯鍵之反應。 [0036](式中，R3
、R4
、a、b及Z與上述相同)。 [0037](式中，R1
、R2
、A2
及m與上述相同)。 [0038] 以式(14)或式(15)所表示之化合物，可取得市售品，該市售品例如可列舉出SABIC Innovative Plastics股份有限公司製 PPO(商標)SA120-100、PPO(商標)SA90-100等。 [0039] 另一方面，以式(16)所表示之異氰酸酯矽烷的具體例，可列舉出3-異氰酸酯丙基三甲氧矽烷、3-異氰酸酯丙基甲基二甲氧矽烷、3-異氰酸酯丙基二甲基甲氧矽烷、3-異氰酸酯丙基三乙氧矽烷、3-異氰酸酯丙基甲基二乙氧矽烷、3-異氰酸酯丙基二甲基乙氧矽烷等。 此等當中，從水解性之觀點來看，較佳為3-異氰酸酯丙基三乙氧矽烷、3-異氰酸酯丙基三甲氧矽烷，尤佳為3-異氰酸酯丙基三甲氧矽烷。 [0040] 以平均結構式(14)或式(15)所表示之於1分子中具有含聚苯醚結構之基及羥基之化合物，與以式(16)所表示之異氰酸酯矽烷之反應比率，考量到抑制胺甲酸乙酯化反應時的副產物，同時提高所得到之有機矽化合物的保存穩定性或特性者，相對於以式(14)或式(15)所表示之化合物中的羥基1mol，較佳為以式(16)所表示之異氰酸酯矽烷的異氰酸酯基成為0.01~1.2mol之比率，尤佳成為0.1~1.1mol之比率，更佳成為0.4~1mol之比率。 [0041] 此外，上述胺甲酸乙酯化反應中，為了提升反應速度，可使用觸媒。 觸媒，可適當地選自一般於胺甲酸乙酯化反應中所使用者，該具體例可列舉出氧化二丁基錫、氧化二辛基錫、雙(2-乙基己酸)錫(II)、二月桂酸二丁基錫、二月桂酸二辛基錫等。 觸媒的用量，只要是觸媒量即可，通常相對於以式(14)或式(15)所表示之化合物與以式(16)所表示之異氰酸酯矽烷的合計，為0.001~1質量%。 [0042] 再者，上述胺甲酸乙酯化反應中，可使用不與所使用之原料反應之溶劑。 該具體例可列舉出戊烷、己烷、庚烷、辛烷、癸烷、環己烷等之烴系溶劑；苯、甲苯、二甲苯等之芳香族系溶劑；丙酮、丁酮、甲基異丁酮等之酮系溶劑；甲醯胺、N,N-二甲基甲醯胺、吡咯啶酮、N-甲基吡咯啶酮等之醯胺系溶劑；乙酸乙酯、乙酸丁酯、γ-丁內酯、丙二醇-1-單甲醚-2-乙酸酯等之酯系溶劑；二乙醚、二丁醚、環戊基甲醚、四氫呋喃、1,4-二噁烷等之醚系溶劑等，此等可單獨使用或組合2種以上而使用。 [0043] 胺甲酸乙酯化反應時的反應溫度並無特別限定，考量到使反應速度達到適切，同時抑制脲基甲酸酯化等之副反應者，較佳為25~90℃，尤佳為40~80℃。 反應時間並無特別限制，通常為10分鐘~24小時。 [0044] 此外，以式(i)所表示之有機矽化合物中，A1
為醚鍵者，作為第1階段，在使平均結構式為以上述式(14)或式(15)所表示之於1分子中具有含聚苯醚結構之基及羥基之化合物，與具有可與羥基反應之官能基及烯基之化合物反應而得到烯基化合物後，於第2階段，可使於第1階段中所得到之烯基化合物與以式(17)所表示之矽烷化合物反應而得到。 更具體而言，於第1階段中，使可與羥基反應之官能基與羥基反應，並藉由醚鍵將平均結構式為以式(14)或式(15)所表示之化合物與具有烯基之化合物偶合，於第2階段中，在含鉑化合物觸媒的存在下，使第1階段中所得到之烯基化合物與以式(17)所表示之矽烷化合物矽氫化，以將矽氫基加成於烯基而形成碳-矽鍵。 [0045](式中，R1
、R2
及m與上述相同)。 [0046] 第1階段中所使用之具有可與羥基反應之官能基及烯基之化合物所具有之上述官能基，只要是選擇性地與羥基反應之官能基即可，並無特別限定，可列舉出鹵素原子、甲烷磺酸酯基、三氟甲烷磺酸酯基、對甲苯磺酸酯基等，較佳為鹵素原子，尤佳為氯原子、溴原子、碘原子。 [0047] 具有鹵素原子及烯基之化合物(以下稱為鹵化烯基化合物)的具體例，可列舉出氯化烯丙基、氯化甲基烯丙基、氯化丁烯基、氯化戊烯基、氯化己烯基、氯化庚烯基、氯化辛烯基、氯化壬烯基等之氯化烯基化合物；溴化烯丙基、溴化甲基烯丙基、溴化丁烯基、溴化戊烯基、溴化己烯基、溴化庚烯基、溴化辛烯基、溴化壬烯基等之溴化烯基化合物；碘化烯丙基、碘化甲基烯丙基、碘化丁烯基、碘化戊烯基、碘化己烯基、碘化庚烯基、碘化辛烯基、碘化壬烯基等之碘化烯基化合物等。 此等當中，從反應性及取得容易性之觀點來看，較佳為氯化烯丙基、氯化己烯基、氯化辛烯基、溴化烯丙基、碘化烯丙基，尤佳為氯化烯丙基、氯化辛烯基、溴化烯丙基，更佳為溴化烯丙基。 [0048] 第1階段的反應，可藉由以往所知的一般方法來進行，例如可採用在鹼性化合物的存在下，由羥基與鹵化烯基化合物等之親核取代反應所進行之非對稱醚的合成法(Williamson合成、Williamson醚合成)等。 此時，以式(14)或式(15)所表示之化合物與鹵化烯基化合物之反應比率，並無特別限定，考量到更為減少未反應的原料，並提高所得到之有機矽化合物的保存穩定性或諸項特性者，相對於以式(14)或式(15)所表示之化合物的羥基1mol，較佳係鹵化烯基化合物的鹵素原子成為0.1~10mol之比率，尤佳成為0.2~5mol之比率，更佳成為0.4~1.2mol之比率。 [0049] 此外，上述鹼性化合物，可使用通常於Williamson合成法所使用之各種鹼性化合物，只要是不與以式(14)或式(15)所表示之化合物的羥基以外者反應者即可，可使用任一種。 具體而言，可列舉出金屬鈉、金屬鋰等之鹼金屬；金屬鈣等之鹼土類金屬；氫化鈉、氫化鋰、氫化鉀、氫化銫等之鹼金屬氫化物；氫化鈣等之鹼土類金屬氫化物；氫氧化鋰、氫氧化鈉、氫氧化鉀、氫氧化銫等之鹼金屬氫氧化物及該水溶液，氫氧化鋇、氫氧化鈣等之鹼土類金屬氫氧化物及該水溶液；三級丁氧化鉀、三級丁氧化鈉等之鹼金屬及鹼土類烷氧化物；碳酸鉀、碳酸鈉、碳酸鈣等之鹼金屬及鹼土類金屬碳酸鹽；碳酸氫鈉、碳酸氫鉀等之鹼金屬及鹼土類金屬碳酸氫鹽；三乙胺、三丁胺、N,N-二異丙基乙胺、四甲基乙二胺、吡啶、N,N-二甲基-4-胺基吡啶等之三級胺等。此等當中，從反應效率之觀點來看，較佳為氫氧化鋰、氫氧化鈉、氫氧化鉀、氫氧化銫、氫氧化鋇、氫氧化鈣等之鹼金屬及鹼土類金屬的氫氧化物或此等之水溶液，尤佳為氫氧化鈉的水溶液。 [0050] 鹼性化合物的用量並無特別限定，考量到充分地進行醚化反應以防止原料的殘存，同時防止鹼性化合物的過剩殘存而提高所得到之有機矽化合物的保存穩定性或諸項特性者，相對於以式(14)或式(15)所表示之化合物的羥基1mol，鹼性化合物較佳為0.5~20mol之比率，尤佳為1~10mol之比率，更佳為2~8mol。 [0051] 上述醚化反應，可使用不與所使用之原料反應之溶劑。 該具體例可列舉出水；戊烷、己烷、庚烷、辛烷、癸烷、環己烷等之烴系溶劑；苯、甲苯、二甲苯等之芳香族系溶劑；甲醯胺、N,N-二甲基甲醯胺、吡咯啶酮、N-甲基吡咯啶酮等之醯胺系溶劑；二乙醚、二丁醚、環戊基甲醚、四氫呋喃、1,4-二噁烷等之醚系溶劑；乙腈等之腈系溶劑等，此等可單獨使用或組合2種以上而使用。 此等當中，從反應效率之觀點來看，尤佳為水、甲苯、二甲苯、二甲基甲醯胺、環戊基甲醚、四氫呋喃，尤佳為水與甲苯之混合溶劑、水與二甲苯之混合溶劑。 [0052] 醚化反應時的反應溫度並無特別限定，考量到使反應速度達到適切，同時抑制鹵化烯基化合物的逸散者，較佳為25~90℃，尤佳為40~80℃，更佳為50~70℃。 此外，醚化反應，通常是在大氣壓下進行，但在上述鹵化烯基化合物的逸散抑制、反應速度提升等目的下，可進行加壓。 反應時間並無特別限制，通常為10分鐘~24小時。 [0053] 上述醚化反應中，為了提升反應速度，可使用觸媒。 觸媒，一般是使用Williamson合成法所使用者，所以可適當地選擇不與以式(14)或式(15)所表示之化合物的羥基以外者反應者。 該具體例可列舉出12-冠-4,15-冠-5,18-冠-6、二苯并-18-冠-6等之冠狀醚；氯化四丁基銨、溴化四丁基銨、碘化四丁基銨、四丁基銨硫酸氫鹽等之四級銨鹽；碘化鉀、碘化鈉等之鹼金屬鹵化物等，此等可單獨使用或組合2種以上而使用。 此等當中，從反應性及取得容易性之觀點來看，較佳為18-冠-6、溴化四丁基銨、碘化四丁基銨、四丁基銨硫酸氫鹽、碘化鉀，尤佳為碘化四丁基銨、四丁基銨硫酸氫鹽、碘化鉀，更佳為四丁基銨硫酸氫鹽。 上述觸媒，可作用為相間移動觸媒，或使鹵化烯基化合物活化而提升反應速度。 [0054] 上述觸媒的用量，只要是觸媒量即可，通常相對於以式(14)或式(15)所表示之化合物與鹵化烯基化合物的合計，較佳為0.001~10質量%，尤佳為0.01~1質量%。 [0055] 第2階段中，作為使用在與第1階段中所得到之烯基化合物的反應之以式(17)所表示之矽烷化合物的具體例，可列舉出三甲氧矽烷、甲基二甲氧矽烷、二甲基甲氧矽烷、三乙氧矽烷、甲基二乙氧矽烷、二乙基乙氧矽烷等，從水解性之觀點來看，較佳為三甲氧矽烷、三乙氧矽烷，尤佳為三甲氧矽烷。 [0056] 第2階段的矽氫化所使用之含鉑化合物觸媒並無特別限定，該具體例可列舉出氯鉑酸、氯鉑酸的醇溶液、鉑-1,3-二乙烯基-1,1,3,3-四甲基二矽氧烷錯合物的甲苯或二甲苯溶液、四(三苯基膦)鉑、二氯雙(三苯基膦)鉑、二氯雙乙腈鉑、二氯雙苯甲腈鉑、二氯環辛二烯鉑、鉑-碳、鉑-氧化鋁、鉑-二氧化矽等之載持觸媒等。 此等當中，從選擇性之面向來看，較佳為0價的鉑錯合物，尤佳為鉑-1,3-二乙烯基-1,1,3,3-四甲基二矽氧烷錯合物的甲苯或二甲苯溶液。 [0057] 含鉑化合物觸媒的用量並無特別限定，從反應性、生產性之觀點來看，相對於以式(17)所表示之矽烷化合物1mol，較佳係使所含有之鉑原子成為1×10-7
~1×10-2
mol之量，尤佳成為1×10-7
~1×10-3
mol之量。 [0058] 此外，為了提升矽氫化的反應性，亦可使用輔助觸媒。此輔助觸媒，可使用一般矽氫化所使用之輔助觸媒，本發明中，較佳為無機酸的銨鹽、酸醯胺化合物、羧酸。 無機酸的銨鹽的具體例，可列舉出氯化銨、硫酸銨、醯胺硫酸銨、硝酸銨、磷酸二氫一銨、磷酸氫二銨、磷酸三銨、二亞磷酸銨、碳酸銨、碳酸氫銨、硫化銨、硼酸銨、硼氟化銨等，當中較佳為pKa為2以上之無機酸的銨鹽，尤佳為碳酸銨、碳酸氫銨。 [0059] 酸醯胺化合物的具體例，可列舉出甲醯胺、乙醯胺、N-甲基乙醯胺、N,N-二甲基乙醯胺、丙醯胺、丙烯醯胺、丙二醯胺、琥珀醯胺、順丁烯二醯胺、反丁烯二醯胺、苯并醯胺、鄰苯二甲醯胺、棕櫚醯胺、硬脂醯胺等。 [0060] 羧酸的具體例，可列舉出甲酸、乙酸、丙酸、丁酸、甲氧乙酸、戊酸、己酸、庚酸、辛酸、乳酸、二醇酸等，此等當中，較佳為甲酸、乙酸、乳酸，尤佳為乙酸。 [0061] 輔助觸媒的用量並無特別限定，從反應性、選擇性、成本等觀點來看，相對於以式(17)所表示之矽烷化合物1mol，較佳為1×10-5
~1×10-1
mol，尤佳為1×10-4
~5×10-3
mol。 [0062] 上述矽氫化反應可在無溶劑下進行，亦可使用溶劑。 可使用的溶劑之具體例，可列舉出戊烷、己烷、環己烷、庚烷、異辛烷、苯、甲苯、二甲苯等之烴系溶劑；二乙醚、四氫呋喃、二噁烷等之醚系溶劑；乙酸乙酯、乙酸丁酯等之酯系溶劑；N,N-二甲基甲醯胺等之非質子性極性溶劑；二氯甲烷、三氯甲烷等之氯化烴系溶劑等，此等溶劑可單獨使用1種或混合2種以上而使用。 [0063] 上述矽氫化反應時的反應溫度並無特別限定，可在0℃至加熱下進行，較佳為0~200℃。 為了得到適度的反應速度，較佳是在加熱下反應，從該觀點來看，反應溫度尤佳為40~110℃，更佳為40~ 90℃。 此外，反應時間亦無特別限定，通常為1~60小時，較佳為1~30小時，尤佳為1~20小時。 [0064] 本發明之硬化性組成物，係含有以式(i)所表示之有機矽化合物。 本發明之以式(i)所表示之有機矽化合物，來自該有機矽化合物的結構，且與以往的有機矽化合物相比，可提升使用含有此之硬化性組成物所得到之硬化物的銅箔密著性及介電特性。 本發明之硬化性組成物中，有機矽化合物的含量並無特別限定，於硬化性組成物中，較佳為約0.1~10質量%，尤佳為0.5~5質量%。當有機矽化合物含有溶劑時，上述含量意指扣除溶劑之非揮發份。 [0065] 此外，本發明之硬化性組成物，較佳係含有有機樹脂。 有機樹脂並無特別限定，該具體例，可因應用途等而適當地選自環氧樹脂、酚樹脂、聚碳酸酯類及聚碳酸酯摻合物、丙烯酸樹脂、聚酯樹脂、聚醯胺樹脂、聚醯亞胺樹脂、丙烯腈-苯乙烯共聚物、苯乙烯-丙烯腈-丁二烯共聚物、聚氯乙烯樹脂、聚苯乙烯樹脂、聚苯醚樹脂、聚苯乙烯與聚苯醚之摻合物、纖維素乙酸丁酸酯、聚乙烯樹脂等，考量到用作為應用高頻區域的電訊號之電子機器所具備之印刷電路板的基板材料者，較佳為環氧樹脂、聚苯醚樹脂、或此等之摻合物。 此時，可因應所使用之有機樹脂來調配適當的硬化劑，例如，當使用環氧樹脂時，可調配咪唑化合物等之硬化劑。 此外，可適當地調配例如氰酸酯化合物等作為交聯成分，再者，可因應使用目的，添加接著性改良劑、紫外線吸收劑、保存穩定性改良劑、塑化劑、填充劑、顏料等之各種添加劑。 [實施例] [0066] 以下係列舉實施例及比較例來更具體說明本發明，惟本發明並不限定於此等實施例。 下述中，黏度為依據B型旋轉黏度計所測得之25℃時的測定值，分子量為藉由GPC(凝膠滲透層析法)測定所求取之聚苯乙烯換算的重量平均分子量，非揮發份，為依據於鋁培養皿上以105℃加熱乾燥3小時後之加熱殘量法所測得之測定值。 [0067] [1]有機矽化合物的合成 [實施例1-1]有機矽化合物1的合成 將PPO(商標)SA120-100(SABIC Innovative Plastics股份有限公司製)40g、甲苯110g及二月桂酸二辛基錫0.05g，裝入於具備攪拌器、迴流冷卻器、滴入供料斗及溫度計之200mL可分離式燒瓶，加熱至80℃。將3-異氰酸酯丙基三甲氧矽烷7.6g滴入投入於其中，於80℃加熱攪拌2小時。藉由IR測定來確認來自原料的異氰酸酯基之吸收峰值完全消失，且取而代之的是生成來自胺甲酸乙酯鍵之吸收峰值，並結束反應。 所得到之反應生成物為褐色透明液體，重量平均分子量6,700，黏度23mm2
/s，非揮發份34質量%。 [0068] [實施例1-2]有機矽化合物2的合成 除了將3-異氰酸酯丙基三乙氧矽烷的量變更為9.2g之外，其他以與實施例1-1相同之步驟來合成。 所得到之反應生成物為褐色透明液體，重量平均分子量6,800，黏度30mm2
/s，非揮發份30質量%。 [0069] [實施例1-3]有機矽化合物3的合成 除了將甲苯的量變更為120g，將3-異氰酸酯丙基三甲氧矽烷的量變更為11.1g之外，其他以與實施例1-1相同之步驟來合成。 所得到之反應生成物為褐色透明液體，重量平均分子量5,300，黏度21mm2
/s，非揮發份29質量%。 [0070] [實施例1-4]有機矽化合物4的合成 除了將3-異氰酸酯丙基三甲氧矽烷的量變更為5.6g之外，其他以與實施例1-1相同之步驟來合成。 所得到之反應生成物為褐色透明液體，重量平均分子量4,200，黏度12mm2
/s，非揮發份30質量%。 [0071] [實施例1-5]有機矽化合物5的合成 將PPO(商標)Resin Powder(SABIC Innovative Plastics股份有限公司製)40g、甲苯110g及二月桂酸二辛基錫0.05g，裝入於具備攪拌器、迴流冷卻器、滴入供料斗及溫度計之200mL可分離式燒瓶，加熱至80℃。將3-異氰酸酯丙基三甲氧矽烷0.5g滴入投入於其中，於80℃加熱攪拌2小時。然後藉由IR測定來確認來自原料的異氰酸酯基之吸收峰值完全消失，且取而代之的是生成來自胺甲酸乙酯鍵之吸收峰值，並結束反應。 所得到之反應生成物為褐色透明液體，重量平均分子量102,000，黏度1,200mm2
/s，非揮發份28質量%。 [0072] [實施例1-6]有機矽化合物6的合成 根據日本特開2015-086329號公報的實施例『PPE-3』所記載之方法，藉由noryl640-111(SABIC Innovative Plastics股份有限公司製)的分配重排，而得到分配重排後之聚苯醚。 將上述所得到之分配重排後之聚苯醚40g、甲苯110g及二月桂酸二辛基錫0.05g，裝入於具備攪拌器、迴流冷卻器、滴入供料斗及溫度計之200mL可分離式燒瓶，加熱至80℃。將3-異氰酸酯丙基三甲氧矽烷27.8g滴入投入於其中，於80℃加熱攪拌2小時。然後藉由IR測定來確認來自原料的異氰酸酯基之吸收峰值完全消失，且取而代之的是生成來自胺甲酸乙酯鍵之吸收峰值，並結束反應。 所得到之反應生成物為褐色透明液體，重量平均分子量6,200，黏度49mm2
/s，非揮發份30質量%。 [0073] [實施例1-7]有機矽化合物7的合成 將實施例1-6中分配重排後之聚苯醚40g、甲苯110g及二月桂酸二辛基錫0.05g，裝入於具備攪拌器、迴流冷卻器、滴入供料斗及溫度計之200mL可分離式燒瓶，加熱至80℃。將3-異氰酸酯丙基三甲氧矽烷13.9g滴入投入於其中，於80℃加熱攪拌2小時。然後藉由IR測定來確認來自原料的異氰酸酯基之吸收峰值完全消失，且取而代之的是生成來自胺甲酸乙酯鍵之吸收峰值，並結束反應。 所得到之反應生成物為褐色透明液體，重量平均分子量5,000，黏度35mm2
/s，非揮發份30質量%。 [0074] [實施例1-8]有機矽化合物8的合成 [第1階段] 將PPO(商標)SA120-100(SABIC Innovative Plastics股份有限公司製)50g、甲苯120g、四丁基銨硫酸氫鹽0.56g、及30%氫氧化鈉水溶液37.6g，裝入於具備攪拌器、迴流冷卻器、滴入供料斗及溫度計之300mL可分離式燒瓶，加熱至60℃。將溴化烯丙基5.7g滴入投入於其中，於60℃加熱攪拌6小時。然後靜置，並將分離為兩層之水層分液，水洗有機層直到成為中性為止，接著將有機層減壓濃縮(80℃、5mmHg)並去除揮發成分，而得到褐色固體之相對應的烯基化合物。 [0075] [第2階段] 將上述第1階段中所得到之烯基化合物30g、甲苯70g、鉑-1,3-二乙烯基-1,1,3,3-四甲基二矽氧烷錯合物的甲苯溶液0.08g(相對於三甲氧矽烷1mol，鉑原子為5.0×10-5
mol)，裝入於具備攪拌器、迴流冷卻器、滴入供料斗及溫度計之200mL可分離式燒瓶，於內溫75~85℃投入三甲氧矽烷3.5g後，於80℃攪拌1小時。 所得到之反應生成物為褐色透明液體，重量平均分子量6,000，黏度15mm2
/s，非揮發份31質量%。 [0076] [實施例1-9]有機矽化合物9的合成 [第1階段] 將PPO(商標)SA-120-100(SABIC Innovative Plastics股份有限公司製)50g、甲苯120g、碘化四丁基銨0.56g、及30%氫氧化鈉水溶液37.6g，裝入於具備攪拌器、迴流冷卻器、滴入供料斗及溫度計之300mL可分離式燒瓶，加熱至60℃。將氯化辛烯基6.9g滴入投入於其中，於60℃加熱攪拌6小時。然後靜置，並將分離為兩層之水層分液，水洗有機層直到成為中性為止，接著將有機層減壓濃縮(80℃、5mmHg)並去除揮發成分，而得到褐色固體之相對應的烯基化合物。 [0077] [第2階段] 將上述第1階段中所得到之烯基化合物30g、甲苯70g、鉑-1,3-二乙烯基-1,1,3,3-四甲基二矽氧烷錯合物的甲苯溶液0.08g(相對於三甲氧矽烷1mol，鉑原子為5.0×10-5
mol)、及乙酸0.003g，裝入於具備攪拌器、迴流冷卻器、滴入供料斗及溫度計之200mL可分離式燒瓶，於內溫75~85℃投入三甲氧矽烷3.4g後，於80℃攪拌1小時。 所得到之反應生成物為褐色透明液體，重量平均分子量6,100，黏度17mm2
/s，非揮發份30質量%。 [0078] [實施例1-10]有機矽化合物10的合成 [第1階段] 將PPO(商標)SA90-100(SABIC Innovative Plastics股份有限公司製)50g、甲苯130g、四丁基銨硫酸氫鹽0.58g、及30%氫氧化鈉水溶液54.1g，裝入於具備攪拌器、迴流冷卻器、滴入供料斗及溫度計之300mL可分離式燒瓶，加熱至60℃。將溴化烯丙基8.2g滴入投入於其中，於60℃加熱攪拌6小時。然後靜置，並將分離為兩層之水層分液，水洗有機層直到成為中性為止，接著將有機層減壓濃縮(80℃、5mmHg)並去除揮發成分，而得到褐色固體之相對應的烯基化合物。 [0079] [第2階段] 將上述第1階段中所得到之烯基化合物40g、甲苯60g、鉑-1,3-二乙烯基-1,1,3,3-四甲基二矽氧烷錯合物的甲苯溶液0.10g(相對於三甲氧矽烷1mol，鉑原子為5.0×10-5
mol)，裝入於具備攪拌器、迴流冷卻器、滴入供料斗及溫度計之200mL可分離式燒瓶，於內溫75~85℃投入三甲氧矽烷6.3g後，於80℃攪拌1小時。 所得到之反應生成物為褐色透明液體，重量平均分子量4,800，黏度13mm2
/s，非揮發份31質量%。 [0080] [實施例1-11]有機矽化合物11的合成 [第1階段] 將PPO(商標)SA90-100(SABIC Innovative Plastics股份有限公司製)50g、甲苯130g、四丁基銨硫酸氫鹽0.54g、及30%氫氧化鈉水溶液54.1g，裝入於具備攪拌器、迴流冷卻器、滴入供料斗及溫度計之300mL可分離式燒瓶，加熱至60℃。將溴化烯丙基4.1g滴入投入於其中，於60℃加熱攪拌6小時。然後靜置，並將分離為兩層之水層分液，水洗有機層直到成為中性為止，接著將有機層減壓濃縮(80℃、5mmHg)並去除揮發成分，而得到褐色固體之相對應的烯基化合物。 [0081] [第2階段] 將上述第1階段中所得到之烯基化合物25g、甲苯75g、鉑-1,3-二乙烯基-1,1,3,3-四甲基二矽氧烷錯合物的甲苯溶液0.06g(相對於三甲氧矽烷1mol，鉑原子為5.0×10-5
mol)，裝入於具備攪拌器、迴流冷卻器、滴入供料斗及溫度計之200mL可分離式燒瓶，於內溫75~85℃投入三甲氧矽烷3.7g後，於80℃攪拌1小時。 所得到之反應生成物為褐色透明液體，重量平均分子量6,100，黏度18mm2
/s，非揮發份30質量%。 [0082] [比較例1-1]有機矽化合物12的合成 將2官能性苯醚樹脂(Mitsubishi Gas Chemical股份有限公司製、OPE-1000)500g、聚四甲氧矽烷(多摩化學股份有限公司製、M Silicate 51)447g，裝入於具備攪拌器、迴流冷卻器、滴入供料斗及溫度計之反應裝置，加熱至90℃使其融解混合，而形成均一溶液。將作為觸媒的二月桂酸二丁基錫0.22g加入於其中，於90℃進行15小時脫甲醇反應，藉此得到相對應之有機矽化合物。 [0083] [比較例1-2]有機矽化合物13的合成 將2官能性苯醚樹脂(Mitsubishi Gas Chemical股份有限公司製、OPE-1000)71.8g、聚甲基三甲氧矽烷(多摩化學股份有限公司製、MTMS-A)45.3g，裝入於具備攪拌器、迴流冷卻器、滴入供料斗及溫度計之反應裝置，加熱至90℃使其融解混合，而形成均一溶液。將作為觸媒的二月桂酸二丁基錫0.02g加入於其中，於90℃進行15小時的脫甲醇反應，藉此得到相對應之有機矽化合物。 [0084] [2]硬化性組成物及該硬化物品的調製 以下說明調製硬化性組成物及該硬化物品時所使用之各成分。 [PPE] ‧SABIC Innovative Plastics股份有限公司製 PPO (商標)SA90-100 [環氧樹脂] ‧環氧樹脂1：DIC股份有限公司製Epiclon HP7200(二環戊二烯型環氧化合物) ‧環氧樹脂2：DIC股份有限公司製Epiclon 850S(雙酚A型環氧樹脂) [硬化劑] ‧四國化成工業股份有限公司製 2E4MZ(2-甲基-4-咪唑) [氰酸酯化合物] ‧Lonza Japan股份有限公司製 BADCy(2,2-雙(4-氰酸酯苯基)丙烷) [有機金屬鹽] ‧DIC股份有限公司製 Cu-NAPHTENATE(環烷酸銅) [有機矽化合物] ‧有機矽化合物：上述實施例1-1~1-11、比較例1-1、1-2中所得到之有機矽化合物 [0085] [實施例2-1] 依循第1表、第2表所記載之調配比率(質量份，惟有機矽化合物為非揮發份換算值)，混合PPE、環氧樹脂、硬化劑及上述實施例1-1中所得到之有機矽化合物1，將所得到之混合溶液加熱至60℃。將氰酸酯化合物及有機金屬鹽添加於其中後，攪拌30分鐘使其完全溶解，而得到清漆狀的硬化性組成物(樹脂清漆)。 接著將所得到之樹脂清漆含浸於玻璃布(日東紡績股份有限公司製、#2116型、WEA116E、E玻璃)後，於160℃加熱乾燥10分鐘而得到預浸材。此時，係調整為使樹脂成分的含量成為約55質量%。 重疊6片所得到之各預浸材，夾入於銅箔(Furukawa Circuit Foil股份有限公司製 GT-MP)並層合，以200℃、2小時、壓力3MPa的條件進行加熱加壓，藉此得到硬化物品之評估基板。 [0086] [實施例2-2~2-11、及比較例2-1、2-2] 除了將有機矽化合物1分別變更為實施例1-2~1-11及比較例1-1~1-2中所得到之有機矽化合物2~13之外，其他與實施例2-1以相同方式進行而製作出硬化性組成物及該硬化物品。 [0087] [比較例2-3、2-4] 除了將有機矽化合物1分別變更為γ-環氧丙氧基丙基三甲氧矽烷(KBM-403、信越化學工業股份有限公司製)作為比較例2-3，以及變更為苯基三甲氧矽烷(KBM-103、信越化學工業股份有限公司製)作為比較例2-4之外，其他與實施例2-1以相同方式進行而製作出硬化性組成物及該硬化物品。 [0088] [比較例2-5] 除了不使用有機矽化合物1之外，其他與實施例2-1相同而製作出硬化性組成物及該硬化物品。 [0089] 對於藉由上述步驟所調製之各評估基板，藉由以下所示之方法來進行評估。 [介電特性] 使用關東電子應用開發股份有限公司製的空腔共振「CP461」，來測定2GHz下之覆銅層合板的介電常數及介電正切。結果如下述第1表、第2表所示。 [銅箔密著強度] 以依據JIS C 6481之方法，測定覆銅層合板表面之銅箔的撕離強度(銅箔密著強度)。此時，於寬20mm、長100 mm的試驗片上形成寬10mm、長100mm的圖型，使用拉伸試驗機以50mm/分的速度撕離銅箔，並以此時的撕離強度(kgf/cm)作為銅箔密著強度來進行評估。結果如下述第1表、第2表所示。 [0090][0091][0092] 如第1表、第2表所示，可得知實施例1-1~1-11中所得到之有機矽化合物，與比較例1-1、1-2中所得到之有機矽化合物、γ-環氧丙氧基丙基三甲氧矽烷及苯基三甲氧矽烷相比，可賦予銅箔密著性以及介電常數或介電正切之介電特性優異之硬化物。[0012] The present invention will be specifically described below. The organosilicon compound of the present invention is represented by an average structural formula (i). [0013] [0014] Here, X represents an n-valent organic group containing a polyphenylene ether structure, and R 1 Each independently represents an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted or substituted aryl group having 6 to 10 carbon atoms, R 2 Each independently represents an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted or substituted aryl group having 6 to 10 carbon atoms, A 1 A single bond or a divalent linking group containing a hetero atom, A 2 Represents a non-substituted or substituted divalent hydrocarbon group having 1 to 20 carbon atoms that does not contain a hetero atom, m is a number from 1 to 3, and n is a number from 1 to 10. [0015] R 1 And R 2 The alkyl group having 1 to 10 carbon atoms may be any of linear, cyclic, and branched, and specific examples include methyl, ethyl, n-propyl, isopropyl, and n-butyl. Linear or branched alkyl groups such as 2,2-butyl, tertiary-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, etc .; cyclopropyl, cyclobutyl Cycloalkyl, such as cyclopentyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and the like. R 1 And R 2 Specific examples of the aryl group having 6 to 10 carbon atoms include benzene, α-naphthyl, β-naphthyl and the like. In addition, a part or all of the hydrogen atoms of each of these groups may be substituted with an alkyl group having 1 to 10 carbon atoms, a halogen atom such as F, Cl, Br, or a cyano group. Specific examples of the group may be exemplified. 3-chloropropyl, 3,3,3-trifluoropropyl, 2-cyanoethyl, tolyl, xylyl and the like are produced. [0016] Among these, R 1 From the viewpoint of hydrolyzability, a linear alkyl group having 1 to 5 carbon atoms is preferred, a methyl group and an ethyl group are particularly preferred, and a methyl group is more preferred. On the other hand, R 2 A linear alkyl group is preferred, a methyl group and an ethyl group are particularly preferred, and a methyl group is more preferred. In addition, m is an integer of 1 to 3, and from the viewpoint of reactivity, it is preferably 2 to 3, and more preferably 3. The above-mentioned A 1 Specific examples of the divalent linking group containing a hetero atom include an ether bond (-O-), a thioether bond (-S-), an amine bond (-NH-), and a sulfonium bond (-S (= O) 2 -), Phosphine bond (-P-(= O) OH-), oxo bond (-C (= O)-), thioketone bond (-C (= S)-), ester bond (-C ( = O) O-), thioester bond (-C (= O) S-), thiocarbonyl ester bond (-C (= S) O-), dithioester bond (-C (= S) S-) , Carbonate bond (-OC (= O) O-), thiocarbonate bond (-OC (= S) O-), amide bond (-C (= O) NH-), thioamide bond (- C (= S) NH-), urethane bond (-OC (= O) NH-), thiocarbamate bond (-SC (= O) NH-), thiocarbamate bond ( -OC (= S) NH-), dithiocarbamate bond (-SC (= S) NH-), urea bond (-NHC (= O) NH-), thiourea bond (-NHC (= S ) NH-) and so on. Among these, A 1 An ether bond (-O-) or a urethane bond (-OC (= O) NH-) is preferred. [0018] On the other hand, A 2 Specific examples of the non-substituted or substituted divalent hydrocarbon group having 1 to 20 carbon atoms that do not contain a hetero atom include methylene, ethylene, trimethylene, propyl, isopropyl, and Methylene, isobutylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, nonamethylene, decamethylene, undecymethylene, dodecamethylene , Trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, 19methylene, icosamethylene, etc. Alkyl groups; Cycloalkyl groups such as cyclopentyl, cyclohexyl, etc .; Cyclic groups such as phenyl, α-, β-naphthyl, etc. Among these, trimethylene and octamethylene are preferred, and trimethylene is particularly preferred. [0019] X in formula (i) represents an n-valent organic group containing a polyphenylene ether structure, and among these, it may have a linear structure, a branched structure, or a crosslinked structure. The average n of each molecule is 1 to 10, preferably 1 to 5, and even more preferably 1 to 2. When n is less than 1, the reactivity is deteriorated due to insufficient hydrolyzable groups. On the other hand, when n exceeds 10, there are too many reaction points, and the storage stability of the compound may be deteriorated, or the hardened product may be easily cracked. The X is not particularly limited as long as it is an n-valent linking group containing a polyphenylene ether structure. In consideration of improving copper foil adhesion and dielectric properties, in the present invention, it is particularly preferably represented by the following formula: The base. [0020] [0021] Therefore, the organosilicon compound of the present invention preferably has an average structural formula represented by Formula (1) or Formula (2). By using these compounds, better copper foil adhesion and dielectric properties can be exhibited. Electrical characteristics. [0022] [0023] In these various formulas, R 1 , R 2 , A 1 , A 2 And m represents the same meaning as above, R 3 Each independently represents a halogen atom, an unsubstituted or substituted alkyl group having 1 to 12 carbon atoms, an unsubstituted or substituted alkoxy group having 1 to 12 carbon atoms, and an unsubstituted or substituted carbon atom having 1 to 12 Alkylthio, or unsubstituted or substituted haloalkoxy group having 1 to 12 carbon atoms, R 4 Each independently represents a hydrogen atom, a halogen atom, an unsubstituted or substituted alkyl group having 1 to 12 carbon atoms, an unsubstituted or substituted alkoxy group having 1 to 12 carbon atoms, or an unsubstituted or substituted carbon atom Alkylthio groups of 1 to 12 or unsubstituted or substituted haloalkoxy groups of 1 to 12 carbon atoms, a and b are independently numbers of 1 to 100, and c is 0 or more and less than 2 Z represents a linking group represented by the following formula (3). [0024] The above-mentioned R 4 Represents the same meaning as described above, and L represents a linking group selected from the following formulae (4) to (11). [0026] The above-mentioned R 5 Each independently represent a hydrogen atom or an alkyl group having 1 to 12 carbon atoms, and R 6 Each independently represents an alkyl group having 1 to 12 carbon atoms, k represents an integer of 1 to 12, and j represents a number of 1 to 1,000. R 3 And R 4 The alkyl group having 1 to 12 carbon atoms may be any of linear, cyclic, and branched, and specific examples include methyl, ethyl, n-propyl, isopropyl, and n-butyl. Straight-chain or branched, secondary butyl, tertiary butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, etc. Cycloalkyl; cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc. R 3 And R 4 The alkoxy group having 1 to 12 carbon atoms may be any of linear, cyclic, and branched, and specific examples include methoxy, ethoxy, propoxy, and isopropoxy , N-butoxy, secondary butoxy, tertiary butoxy, n-pentoxy, n-hexyloxy, n-heptyloxy, n-octyloxy, n-nonoxy, n-decoxy, n-undecyl Linear or branched alkoxy groups such as oxy, n-dodecyloxy, etc .; cycloalkoxy groups such as cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, cyclooctyloxy and the like. In addition, some or all of the hydrogen atoms of these groups may be substituted by halogen atoms such as F, Cl, Br, mercapto, cyano, etc. Specific examples of the group include 3-chloropropyl, 3 , 3,3-trifluoropropyl, 3-mercaptopropyl, 2-cyanoethyl, etc. R 3 And R 4 Examples of the halogen atom include F, Cl, and Br. [0029] Among these, R 3 From the viewpoint of ease of production, methyl and methoxy are preferred, and methyl is particularly preferred. On the other hand, R 4 A hydrogen atom, a methyl group and a methoxy group are preferred, and a hydrogen atom is particularly preferred. [0030] In addition, a and b are independently numbers of 1 to 100. From the viewpoint of the copper foil adhesion and dielectric properties of the organic silicon compound, it is preferably 3 to 50, and particularly preferably 5 to 20. When a and b are less than 1, there is a concern that good copper foil adhesion and dielectric properties cannot be obtained. When a and b are more than 100, the compatibility of the organic silicon compound with the organic resin may deteriorate. [0031] Furthermore, in the present invention, -A 1 -A 2 -Is preferably a trimethylene group having an urethane bond (-OC (= O) NH-) represented by formula (12) or an ether bond (-O) represented by formula (13) -) Trimethylene. [0032] [0033] The weight average molecular weight of the organosilicon compound of the present invention is not particularly limited. Considering that the viscosity and the like of the curable composition containing the compound are adjusted to an appropriate range to improve workability, a sufficient copper foil is adhered. Those who impart properties and dielectric properties to the obtained hardened product preferably have a weight average molecular weight of 500 to 50,000, particularly preferably 1,000 to 20,000, and more preferably 4,000 to 10,000. The weight average molecular weight in the present invention is a polystyrene conversion value measured in accordance with Gel Permeation Chromatography (GPC). [0034] The organosilicon compound of the present invention can be used in a state containing a solvent. The solvent is not particularly limited as long as it has the dissolving power of the organosilicon compound represented by the formula (i). From the viewpoints of solubility and volatility, aromatic solvents such as toluene and xylene are preferred. Family solvents; ketone solvents such as methyl ethyl ketone and methyl isobutyl ketone; ether solvents such as tetrahydrofuran; toluene and xylene are particularly preferred. The amount of the solvent to be added is preferably 100 to 20,000 parts by mass, and even more preferably 200 to 10,000 parts by mass based on 100 parts by mass of the organosilicon compound represented by the formula (i). [0035] In the organosilicon compound represented by the formula (i), A 1 For a urethane bond, a compound having a polyphenylene ether-containing group and a hydroxyl group in one molecule represented by the average structural formula (14) or the formula (15) can be used in combination with the formula (16) The compound having an isocyanate group and an alkoxysilyl group (hereinafter referred to as an isocyanate silane) is obtained by reaction. More specifically, a reaction is performed in which a urethane bond is formed between a hydroxyl group of a compound represented by the average structural formula (14) or (15) and an isocyanate group of an isocyanate silane. [0036] (Where, R 3 , R 4 , A, b, and Z are the same as above). [0037] (Where, R 1 , R 2 , A 2 And m are the same as above). [0038] The compound represented by formula (14) or formula (15) can be obtained as a commercially available product. Examples of the commercially available product include PPO (trademark) SA120-100 and PPO (trademark) manufactured by SABIC Innovative Plastics Co., Ltd. ) SA90-100 and so on. [0039] On the other hand, specific examples of the isocyanate silane represented by formula (16) include 3-isocyanatepropyltrimethoxysilane, 3-isocyanatepropylmethyldimethoxysilane, and 3-isocyanatepropyl. Dimethylmethoxysilane, 3-isocyanatepropyltriethoxysilane, 3-isocyanatepropylmethyldiethoxysilane, 3-isocyanatepropyldimethylethoxysilane, etc. Among these, from the viewpoint of hydrolyzability, 3-isocyanatepropyltriethoxysilane and 3-isocyanatepropyltrimethoxysilane are preferred, and 3-isocyanatepropyltrimethoxysilane is particularly preferred. The reaction ratio of a compound having a polyphenylene ether-containing group and a hydroxyl group represented by the average structural formula (14) or the formula (15) with an isocyanate silane represented by the formula (16), Taking into consideration the by-products during the urethane reaction and improving the storage stability or characteristics of the obtained organosilicon compound, it is 1 mol relative to the hydroxyl group in the compound represented by the formula (14) or (15) It is preferable that the isocyanate group of the isocyanate silane represented by Formula (16) becomes a ratio of 0.01 to 1.2 mol, particularly preferably a ratio of 0.1 to 1.1 mol, and more preferably a ratio of 0.4 to 1 mol. [0041] In the urethane reaction, a catalyst may be used in order to increase the reaction speed. The catalyst can be appropriately selected from users generally used in urethane reactions. Specific examples include dibutyltin oxide, dioctyltin oxide, and bis (2-ethylhexanoate) tin (II). , Dibutyltin dilaurate, dioctyltin dilaurate, and the like. The amount of the catalyst used may be the amount of the catalyst, and is generally 0.001 to 1% by mass based on the total of the compound represented by the formula (14) or the formula (15) and the isocyanate silane represented by the formula (16). . [0042] Furthermore, in the aforementioned urethanization reaction, a solvent that does not react with the raw materials used can be used. Specific examples include hydrocarbon solvents such as pentane, hexane, heptane, octane, decane, and cyclohexane; aromatic solvents such as benzene, toluene, and xylene; acetone, methyl ethyl ketone, and methyl Ketone solvents such as isobutyl ketone; acetamide solvents such as formamidine, N, N-dimethylformamide, pyrrolidone, and N-methylpyrrolidone; ethyl acetate, butyl acetate, Ester solvents such as γ-butyrolactone and propylene glycol-1-monomethyl ether-2-acetate; ethers such as diethyl ether, dibutyl ether, cyclopentyl methyl ether, tetrahydrofuran, and 1,4-dioxane These solvents can be used alone or in combination of two or more. [0043] The reaction temperature during the urethane reaction is not particularly limited. Considering that the reaction rate can be adjusted to an appropriate level while inhibiting side reactions such as urethanization, it is preferably 25 to 90 ° C, and particularly preferably It is 40 ~ 80 ℃. The reaction time is not particularly limited, but is usually 10 minutes to 24 hours. In the organosilicon compound represented by formula (i), A 1 For an ether bond, as the first stage, a compound having a polyphenylene ether-containing group and a hydroxyl group in one molecule represented by the above formula (14) or formula (15) is used as the average structural formula, and After reacting with a functional group that reacts with a hydroxyl group and an alkenyl compound to obtain an alkenyl compound, in the second stage, the alkenyl compound obtained in the first stage can be reacted with the silane compound represented by formula (17) to get. More specifically, in the first stage, a functional group capable of reacting with a hydroxyl group is reacted with a hydroxyl group, and the average structural formula is represented by the formula (14) or the formula (15) with an olefin through an ether bond. In the second stage, the alkenyl compound obtained in the first stage and the silane compound represented by the formula (17) are hydrosilated in the presence of a platinum-containing compound catalyst in the second stage, so as to hydrosilicon. The group is added to the alkenyl group to form a carbon-silicon bond. [0045] (Where, R 1 , R 2 And m are the same as above). [0046] The above-mentioned functional group of the compound having a functional group capable of reacting with a hydroxyl group and an alkenyl group used in the first stage is not particularly limited as long as it is a functional group that selectively reacts with a hydroxyl group. Examples include a halogen atom, a methanesulfonate group, a trifluoromethanesulfonate group, a p-toluenesulfonate group, and the like. A halogen atom is preferred, and a chlorine atom, a bromine atom, and an iodine atom are particularly preferred. [0047] Specific examples of the compound having a halogen atom and an alkenyl group (hereinafter referred to as a halogenated alkenyl compound) include allyl chloride, methyl allyl chloride, butenyl chloride, and pentyl chloride. Alkenyl, hexenyl chloride, heptenyl chloride, octenyl chloride, nonenyl chloride and other chlorinated alkenyl compounds; brominated allyl, bromomethylallyl, brominated Brominated alkenyl compounds such as butenyl, pentenyl bromide, hexenyl bromide, heptenyl bromide, octenyl bromide, nonenyl bromide, etc .; allyl iodide, methyl iodide Iodized alkenyl compounds such as allylic allyl, butenyl iodide, pentenyl iodide, hexenyl iodide, heptenyl iodide, octenyl iodide, nonenyl iodide and the like. Among these, from the viewpoints of reactivity and availability, preferred are chlorinated allyl, hexenyl chloride, octenyl chloride, brominated allyl, and iodized allyl, especially Preferred are chlorinated allyl, octenyl chloride, and brominated allyl, and more preferred is brominated allyl. [0048] The reaction in the first stage can be carried out by a conventionally known method. For example, an asymmetric nucleophilic substitution reaction between a hydroxyl group and a halogenated alkenyl compound in the presence of a basic compound can be used. Ether synthesis method (Williamson synthesis, Williamson ether synthesis), etc. At this time, the reaction ratio of the compound represented by the formula (14) or the formula (15) to the halogenated alkenyl compound is not particularly limited. Considering that the unreacted raw materials are further reduced, the organic silicon compound obtained is improved in For storage stability or various characteristics, the halogen atom of the halogenated alkenyl compound is preferably a ratio of 0.1 to 10 mol, and more preferably 0.2 relative to 1 mol of the hydroxyl group of the compound represented by formula (14) or formula (15). A ratio of ~ 5mol is more preferably a ratio of 0.4 ~ 1.2mol. [0049] As the basic compound, various basic compounds commonly used in Williamson synthesis can be used, as long as they do not react with a hydroxyl group other than the compound represented by formula (14) or formula (15). Yes, you can use either. Specific examples include alkali metals such as metallic sodium and metallic lithium; alkaline earth metals such as metallic calcium; alkali metal hydrides such as sodium hydride, lithium hydride, potassium hydride, and cesium hydride; alkaline earth metals such as calcium hydride Hydride; lithium hydroxide, sodium hydroxide, potassium hydroxide, cesium hydroxide and other alkali metal hydroxides and the aqueous solution; barium hydroxide, calcium hydroxide and other alkaline earth metal hydroxides and the aqueous solution; Alkali metals and alkaline earth alkoxides such as potassium butoxide and tertiary sodium butoxide; alkali metals and alkaline earth metal carbonates such as potassium carbonate, sodium carbonate, calcium carbonate; alkali metals such as sodium bicarbonate and potassium bicarbonate And alkaline earth metal bicarbonates; triethylamine, tributylamine, N, N-diisopropylethylamine, tetramethylethylenediamine, pyridine, N, N-dimethyl-4-aminopyridine, etc. Tertiary amines, etc. Among these, from the viewpoint of reaction efficiency, hydroxides of alkali metals and alkaline earth metals such as lithium hydroxide, sodium hydroxide, potassium hydroxide, cesium hydroxide, barium hydroxide, and calcium hydroxide are preferred. Or such an aqueous solution is particularly preferably an aqueous solution of sodium hydroxide. [0050] The amount of the basic compound used is not particularly limited. In consideration of sufficiently performing the etherification reaction to prevent the remaining of the raw materials, while preventing the excessive remaining of the basic compound, the storage stability or various items of the obtained organic silicon compound are improved. For characteristics, the ratio of the basic compound is preferably 0.5 to 20 mol, particularly preferably the ratio of 1 to 10 mol, and more preferably 2 to 8 mol, relative to 1 mol of the hydroxyl group of the compound represented by the formula (14) or the formula (15). . [0051] For the etherification reaction, a solvent that does not react with the raw materials used can be used. Specific examples include water; hydrocarbon solvents such as pentane, hexane, heptane, octane, decane, and cyclohexane; aromatic solvents such as benzene, toluene, and xylene; formamide, N, N-dimethylformamidine, pyrrolidone, N-methylpyrrolidone and other amine solvents; diethyl ether, dibutyl ether, cyclopentyl methyl ether, tetrahydrofuran, 1,4-dioxane, etc. Ether solvents; nitrile solvents such as acetonitrile, etc. These can be used alone or in combination of two or more kinds. Among these, from the viewpoint of reaction efficiency, water, toluene, xylene, dimethylformamide, cyclopentyl methyl ether, and tetrahydrofuran are particularly preferable, and a mixed solvent of water and toluene, and water and two are particularly preferable. Mixed solvent of toluene. [0052] The reaction temperature during the etherification reaction is not particularly limited. Considering that the reaction speed can be adjusted to a suitable level while suppressing the escape of the halogenated alkenyl compound, it is preferably 25 to 90 ° C, and more preferably 40 to 80 ° C. More preferably, it is 50 to 70 ° C. In addition, the etherification reaction is usually carried out under atmospheric pressure, but for the purpose of suppressing the escape of the halogenated alkenyl compound and increasing the reaction speed, the pressure can be increased. The reaction time is not particularly limited, but is usually 10 minutes to 24 hours. [0053] In the etherification reaction, a catalyst may be used in order to increase the reaction speed. The catalyst is generally used by the Williamson synthesis method. Therefore, it is possible to appropriately select a catalyst that does not react with a hydroxyl group other than the compound represented by formula (14) or formula (15). The specific examples include crown ethers of 12-crown-4, 15-crown-5, 18-crown-6, dibenzo-18-crown-6, etc .; tetrabutylammonium chloride, tetrabutyl bromide Tertiary ammonium salts such as ammonium, tetrabutylammonium iodide, and tetrabutylammonium hydrogen sulfate; alkali metal halides such as potassium iodide and sodium iodide, etc. These can be used alone or in combination of two or more. Among these, from the viewpoints of reactivity and availability, 18-crown-6, tetrabutylammonium bromide, tetrabutylammonium iodide, tetrabutylammonium hydrogen sulfate, potassium iodide, and the like are particularly preferred. Tetrabutylammonium iodide, tetrabutylammonium hydrogen sulfate, and potassium iodide are preferred, and tetrabutylammonium hydrogen sulfate is more preferred. The catalyst can act as a catalyst for moving between phases or activate a halogenated alkenyl compound to increase the reaction speed. [0054] The amount of the catalyst used may be the amount of the catalyst, and is generally preferably 0.001 to 10% by mass relative to the total of the compound represented by the formula (14) or the formula (15) and the halogenated alkenyl compound. , Particularly preferably 0.01 to 1% by mass. [0055] In the second stage, as a specific example of the silane compound represented by the formula (17) using a reaction with the alkenyl compound obtained in the first stage, trimethoxysilane and methyldimethylformate can be cited. From the viewpoint of hydrolyzability, oxysilane, dimethylmethoxysilane, triethoxysilane, methylethoxysilane, diethylethoxysilane, and the like are preferably trimethoxysilane, triethoxysilane, etc. Especially preferred is trimethoxysilane. [0056] The platinum-containing compound catalyst used in the second-stage hydrosilylation is not particularly limited, and specific examples thereof include chloroplatinic acid, an alcohol solution of chloroplatinic acid, and platinum-1,3-divinyl-1 , 1,3,3-tetramethyldisilaxane complex in toluene or xylene solution, tetrakis (triphenylphosphine) platinum, dichlorobis (triphenylphosphine) platinum, platinum Supporting catalysts such as platinum dichlorobisbenzonitrile, platinum dichlorocyclooctadiene, platinum-carbon, platinum-alumina, platinum-silicon dioxide, etc. Among these, from the aspect of selectivity, 0-valent platinum complex is preferred, and platinum-1,3-divinyl-1,1,3,3-tetramethyldisilazol is particularly preferred. A solution of an alkane complex in toluene or xylene. [0057] The amount of the platinum-containing compound catalyst used is not particularly limited. From the viewpoints of reactivity and productivity, it is preferable to make the contained platinum atom into 1 mol of the silane compound represented by formula (17). 1 × 10 -7 ~ 1 × 10 -2 The amount of mol, especially preferably becomes 1 × 10 -7 ~ 1 × 10 -3 The amount of mol. [0058] In addition, in order to improve the reactivity of the hydrosilylation, an auxiliary catalyst may also be used. As the auxiliary catalyst, an auxiliary catalyst used in general hydrosilation can be used. In the present invention, an ammonium salt of an inorganic acid, an ammonium acid compound, and a carboxylic acid are preferred. Specific examples of the ammonium salt of the inorganic acid include ammonium chloride, ammonium sulfate, ammonium ammonium sulfate, ammonium nitrate, monoammonium phosphate, diammonium hydrogen phosphate, triammonium phosphate, ammonium diphosphite, ammonium carbonate, Ammonium bicarbonate, ammonium sulfide, ammonium borate, ammonium borofluoride and the like are preferred. Among them, ammonium salts of inorganic acids with a pKa of 2 or more are preferred, and ammonium carbonate and ammonium bicarbonate are particularly preferred. [0059] Specific examples of the acid amide compounds include methylamine, acetamide, N-methylacetamide, N, N-dimethylacetamide, propylamine, acrylamide, and propylamine. Diamine, succinimidine, maleimide, fumarate, benzoamide, phthalamide, palmaramide, stearylamine and the like. [0060] Specific examples of the carboxylic acid include formic acid, acetic acid, propionic acid, butyric acid, methoxyacetic acid, valeric acid, hexanoic acid, heptanoic acid, caprylic acid, lactic acid, and glycolic acid. Among these, preferred are Formic acid, acetic acid and lactic acid, particularly preferred is acetic acid. [0061] The amount of the auxiliary catalyst is not particularly limited. From the viewpoints of reactivity, selectivity, cost, etc., it is preferably 1 × 10 with respect to 1 mol of the silane compound represented by the formula (17). -5 ~ 1 × 10 -1 mol, especially preferably 1 × 10 -4 ~ 5 × 10 -3 mol. [0062] The above hydrosilylation reaction can be performed without a solvent, and a solvent can also be used. Specific examples of usable solvents include hydrocarbon solvents such as pentane, hexane, cyclohexane, heptane, isooctane, benzene, toluene, and xylene; and diethyl ether, tetrahydrofuran, and dioxane. Ether solvents; Ester solvents such as ethyl acetate and butyl acetate; Aprotic polar solvents such as N, N-dimethylformamide; Chlorinated hydrocarbon solvents such as methylene chloride and chloroform; These solvents can be used singly or in combination of two or more. [0063] The reaction temperature in the above-mentioned hydrosilylation reaction is not particularly limited, and it can be carried out from 0 ° C to heating, and preferably from 0 to 200 ° C. In order to obtain a moderate reaction rate, the reaction is preferably performed under heating. From this viewpoint, the reaction temperature is particularly preferably 40 to 110 ° C, and more preferably 40 to 90 ° C. In addition, the reaction time is not particularly limited, but is usually 1 to 60 hours, preferably 1 to 30 hours, and particularly preferably 1 to 20 hours. [0064] The curable composition of the present invention contains an organosilicon compound represented by formula (i). The organosilicon compound represented by the formula (i) of the present invention is derived from the structure of the organosilicon compound, and compared with conventional organosilicon compounds, it is possible to improve the use of copper containing a cured product obtained by using the curable composition. Foil adhesion and dielectric properties. The content of the organosilicon compound in the curable composition of the present invention is not particularly limited, but in the curable composition, it is preferably about 0.1 to 10% by mass, and particularly preferably 0.5 to 5% by mass. When the organosilicon compound contains a solvent, the above-mentioned content means the non-volatile content of the solvent is deducted. [0065] The curable composition of the present invention preferably contains an organic resin. The organic resin is not particularly limited, and this specific example can be appropriately selected from epoxy resins, phenol resins, polycarbonates and polycarbonate blends, acrylic resins, polyester resins, and polyamide resins depending on the application and the like. , Polyimide resin, acrylonitrile-styrene copolymer, styrene-acrylonitrile-butadiene copolymer, polyvinyl chloride resin, polystyrene resin, polyphenylene ether resin, polystyrene and polyphenylene ether Blends, cellulose acetate butyrate, polyethylene resins, etc., taking into consideration substrate materials for printed circuit boards included in electronic equipment that uses electric signals in the high frequency range, preferably epoxy resins, polybenzenes Ether resin, or a blend of these. In this case, an appropriate hardener may be formulated according to the organic resin used. For example, when an epoxy resin is used, a hardener such as an imidazole compound may be formulated. In addition, for example, a cyanate compound or the like can be appropriately blended as a crosslinking component, and further, an adhesive improver, an ultraviolet absorber, a storage stability improver, a plasticizer, a filler, a pigment, etc. can be added depending on the purpose of use. Of various additives. [Examples] [0066] The following series will give examples and comparative examples to explain the present invention in more detail, but the present invention is not limited to these examples. In the following, the viscosity is a value measured at 25 ° C based on a B-type rotary viscometer, and the molecular weight is a weight-average molecular weight in terms of polystyrene obtained by GPC (gel permeation chromatography) measurement. The non-volatile content is a measurement value based on a heating residue method after heating and drying at 105 ° C for 3 hours on an aluminum petri dish. [1] Synthesis of organosilicon compound [Example 1-1] Synthesis of organosilicon compound 1 PPO (trademark) SA120-100 (manufactured by SABIC Innovative Plastics Co., Ltd.) 40 g, toluene 110 g, and dilauric acid di 0.05 g of octyl tin was put into a 200 mL separable flask equipped with a stirrer, a reflux cooler, a dropping hopper and a thermometer, and heated to 80 ° C. 7.6 g of 3-isocyanatepropyltrimethoxysilane was added dropwise thereto, and the mixture was heated and stirred at 80 ° C for 2 hours. By IR measurement, it was confirmed that the absorption peak of the isocyanate group from the raw material completely disappeared, and instead, an absorption peak derived from a urethane bond was generated, and the reaction was completed. The obtained reaction product was a brown transparent liquid with a weight average molecular weight of 6,700 and a viscosity of 23 mm. 2 / s, 34% by mass of non-volatile matter. [Example 1-2] Synthesis of organosilicon compound 2 The synthesis was carried out in the same manner as in Example 1-1, except that the amount of 3-isocyanatepropyltriethoxysilane was changed to 9.2 g. The obtained reaction product was a brown transparent liquid with a weight average molecular weight of 6,800 and a viscosity of 30 mm. 2 / s, 30% by mass of non-volatile matter. [Example 1-3] The synthesis of organosilicon compound 3 was the same as in Example 1 except that the amount of toluene was changed to 120 g and the amount of 3-isocyanatepropyltrimethoxysilane was changed to 11.1 g. 1 The same steps to synthesize. The obtained reaction product was a brown transparent liquid with a weight average molecular weight of 5,300 and a viscosity of 21 mm. 2 / s, 29% by mass of non-volatile matter. [Example 1-4] Synthesis of organosilicon compound 4 The synthesis was carried out in the same manner as in Example 1-1 except that the amount of 3-isocyanatepropyltrimethoxysilane was changed to 5.6 g. The obtained reaction product was a brown transparent liquid with a weight average molecular weight of 4,200 and a viscosity of 12 mm. 2 / s, 30% by mass of non-volatile matter. [Example 1-5] Synthesis of organosilicon compound 5 40 g of PPO (trademark) Resin Powder (manufactured by SABIC Innovative Plastics Co., Ltd.), 110 g of toluene, and 0.05 g of dioctyltin dilaurate were charged in A 200 mL separable flask equipped with a stirrer, a reflux cooler, a dropping hopper and a thermometer, and heated to 80 ° C. 0.5 g of 3-isocyanatepropyltrimethoxysilane was added dropwise thereto, and the mixture was heated and stirred at 80 ° C for 2 hours. Then, by IR measurement, it was confirmed that the absorption peak of the isocyanate group from the raw material completely disappeared, and instead, the absorption peak derived from the urethane bond was generated, and the reaction was completed. The obtained reaction product was a brown transparent liquid with a weight-average molecular weight of 102,000 and a viscosity of 1,200 mm. 2 / s, 28% by mass of non-volatile matter. [Example 1-6] Synthesis of organosilicon compound 6 According to the method described in Example "PPE-3" of Japanese Patent Application Laid-Open No. 2015-086329, noryl640-111 (SABIC Innovative Plastics Co., Ltd.) System) to rearrange the distribution, and obtain the polyphenylene ether after the distribution and rearrangement. 40 g of polyphenylene ether, 110 g of toluene, and 0.05 g of dioctyltin dilaurate obtained after the above-mentioned distribution and rearrangement were charged into a 200 mL separable type equipped with a stirrer, a reflux cooler, a dropping hopper and a thermometer. The flask was heated to 80 ° C. 27.8 g of 3-isocyanatepropyltrimethoxysilane was added dropwise thereto, and the mixture was heated and stirred at 80 ° C for 2 hours. Then, by IR measurement, it was confirmed that the absorption peak of the isocyanate group from the raw material completely disappeared, and instead, the absorption peak derived from the urethane bond was generated, and the reaction was completed. The obtained reaction product was a brown transparent liquid with a weight average molecular weight of 6,200 and a viscosity of 49 mm. 2 / s, 30% by mass of non-volatile matter. [Example 1-7] Synthesis of organosilicon compound 7 40 g of polyphenylene ether, 110 g of toluene, and 0.05 g of dioctyltin dilaurate in Example 1-6 were rearranged, and charged in A 200 mL separable flask with a stirrer, a reflux cooler, a dropping hopper and a thermometer, heated to 80 ° C. 13.9 g of 3-isocyanatepropyltrimethoxysilane was added dropwise thereto, followed by heating and stirring at 80 ° C for 2 hours. Then, by IR measurement, it was confirmed that the absorption peak of the isocyanate group from the raw material completely disappeared, and instead, the absorption peak derived from the urethane bond was generated, and the reaction was completed. The obtained reaction product was a brown transparent liquid with a weight average molecular weight of 5,000 and a viscosity of 35 mm. 2 / s, 30% by mass of non-volatile matter. [Example 1-8] Synthesis of organosilicon compound 8 [First stage] 50 g of PPO (trademark) SA120-100 (manufactured by SABIC Innovative Plastics Co., Ltd.), 120 g of toluene, and tetrabutylammonium hydrogen sulfate 0.56 g and 37.6 g of a 30% sodium hydroxide aqueous solution were put into a 300 mL separable flask equipped with a stirrer, a reflux cooler, a dropping hopper and a thermometer, and heated to 60 ° C. 5.7 g of brominated allyl was added dropwise thereto, and the mixture was heated and stirred at 60 ° C. for 6 hours. Then let it stand and separate the water layer separated into two layers, wash the organic layer with water until it becomes neutral, then concentrate the organic layer under reduced pressure (80 ° C, 5mmHg) and remove the volatile components to obtain the corresponding brown solid. Alkenyl compounds. [Second stage] 30 g of the alkenyl compound obtained in the first stage, 70 g of toluene, and platinum-1,3-divinyl-1,1,3,3-tetramethyldisilaxane 0.08 g of a toluene solution of the complex (relative to 1 mol of trimethoxysilane, the platinum atom is 5.0 × 10 -5 mol), put in a 200 mL separable flask equipped with a stirrer, a reflux cooler, a dropping hopper and a thermometer, put 3.5 g of trimethoxysilane at an internal temperature of 75 to 85 ° C, and stir at 80 ° C for 1 hour. The obtained reaction product was a brown transparent liquid with a weight average molecular weight of 6,000 and a viscosity of 15 mm. 2 / s, 31% by mass of non-volatile matter. [Example 1-9] Synthesis of organosilicon compound 9 [First stage] 50 g of PPO (trademark) SA-120-100 (manufactured by SABIC Innovative Plastics Co., Ltd.), 120 g of toluene, and tetrabutyl iodide 0.56 g of ammonium and 37.6 g of 30% aqueous sodium hydroxide solution were put into a 300 mL separable flask equipped with a stirrer, a reflux cooler, a dropping hopper and a thermometer, and heated to 60 ° C. 6.9 g of octenyl chloride was added dropwise thereto, and the mixture was heated and stirred at 60 ° C. for 6 hours. Then let it stand and separate the water layer separated into two layers, wash the organic layer with water until it becomes neutral, then concentrate the organic layer under reduced pressure (80 ° C, 5mmHg) and remove the volatile components to obtain the corresponding brown solid. Alkenyl compounds. [Second stage] 30 g of the alkenyl compound obtained in the first stage, 70 g of toluene, and platinum-1,3-divinyl-1,1,3,3-tetramethyldisilaxane 0.08 g of a toluene solution of the complex (relative to 1 mol of trimethoxysilane, the platinum atom is 5.0 × 10 -5 mol), and 0.003 g of acetic acid, put into a 200 mL separable flask equipped with a stirrer, a reflux cooler, a dropping hopper and a thermometer, and put 3.4 g of trimethoxysilane at an internal temperature of 75 to 85 ° C, and then at 80 ° C Stir for 1 hour. The obtained reaction product was a brown transparent liquid with a weight average molecular weight of 6,100 and a viscosity of 17 mm. 2 / s, 30% by mass of non-volatile matter. [Example 1-10] Synthesis of organosilicon compound 10 [First stage] 50 g of PPO (trademark) SA90-100 (manufactured by SABIC Innovative Plastics Co., Ltd.), 130 g of toluene, and tetrabutylammonium hydrogen sulfate 0.58 g and 54.1 g of a 30% sodium hydroxide aqueous solution were put into a 300 mL separable flask equipped with a stirrer, a reflux cooler, a dropping hopper and a thermometer, and heated to 60 ° C. 8.2 g of brominated allyl was added dropwise thereto, and the mixture was heated and stirred at 60 ° C. for 6 hours. Then let it stand and separate the water layer separated into two layers, wash the organic layer with water until it becomes neutral, then concentrate the organic layer under reduced pressure (80 ° C, 5mmHg) and remove the volatile components to obtain the corresponding brown solid. Alkenyl compounds. [Second stage] 40 g of the alkenyl compound obtained in the first stage, 60 g of toluene, and platinum-1,3-divinyl-1,1,3,3-tetramethyldisilazane 0.10 g of a toluene solution of the complex (relative to 1 mol of trimethoxysilane, the platinum atom is 5.0 × 10 -5 mol), put in a 200 mL separable flask equipped with a stirrer, a reflux cooler, a dropping hopper and a thermometer, put 6.3 g of trimethoxysilane at an internal temperature of 75 to 85 ° C, and stir at 80 ° C for 1 hour. The obtained reaction product was a brown transparent liquid with a weight average molecular weight of 4,800 and a viscosity of 13 mm. 2 / s, 31% by mass of non-volatile matter. [Example 1-11] Synthesis of organosilicon compound 11 [First stage] 50 g of PPO (trademark) SA90-100 (manufactured by SABIC Innovative Plastics Co., Ltd.), 130 g of toluene, and tetrabutylammonium hydrogen sulfate 0.54 g and 54.1 g of a 30% sodium hydroxide aqueous solution were put into a 300 mL separable flask equipped with a stirrer, a reflux cooler, a dropping hopper and a thermometer, and heated to 60 ° C. 4.1 g of brominated allyl was added dropwise thereto, followed by heating and stirring at 60 ° C for 6 hours. Then let it stand and separate the water layer separated into two layers, wash the organic layer with water until it becomes neutral, then concentrate the organic layer under reduced pressure (80 ° C, 5mmHg) and remove the volatile components to obtain the corresponding brown solid. Alkenyl compounds. [Second stage] 25 g of the alkenyl compound obtained in the first stage described above, 75 g of toluene, and platinum-1,3-divinyl-1,1,3,3-tetramethyldisilaxane 0.06 g of a toluene solution of the complex (relative to 1 mol of trimethoxysilane, the platinum atom is 5.0 × 10 -5 mol), put into a 200 mL separable flask equipped with a stirrer, a reflux cooler, a dropping hopper and a thermometer, put 3.7 g of trimethoxysilane at an internal temperature of 75 to 85 ° C, and stir at 80 ° C for 1 hour. The obtained reaction product was a brown transparent liquid with a weight average molecular weight of 6,100 and a viscosity of 18 mm. 2 / s, 30% by mass of non-volatile matter. [Comparative Example 1-1] Synthesis of organosilicon compound 12 500 g of a bifunctional phenyl ether resin (manufactured by Mitsubishi Gas Chemical Co., Ltd., OPE-1000) and polytetramethoxysilane (manufactured by Tama Chemical Co., Ltd.) (M Silicate 51) 447g, put into a reaction device equipped with a stirrer, a reflux cooler, a dropping hopper and a thermometer, and heat to 90 ° C to melt and mix to form a uniform solution. 0.22 g of dibutyltin dilaurate as a catalyst was added thereto, and a methanol removal reaction was performed at 90 ° C for 15 hours, thereby obtaining a corresponding organosilicon compound. [Comparative Example 1-2] Synthesis of organosilicon compound 13 71.8 g of a bifunctional phenyl ether resin (manufactured by Mitsubishi Gas Chemical Co., Ltd., OPE-1000), polymethyltrimethoxysilane (Tama Chemical Co., Ltd. MTMS-A) (45.3 g, manufactured by the company) was charged into a reaction device equipped with a stirrer, a reflux cooler, a dropping hopper and a thermometer, and heated to 90 ° C to melt and mix to form a uniform solution. 0.02 g of dibutyltin dilaurate as a catalyst was added thereto, and a methanol removal reaction was performed at 90 ° C for 15 hours, thereby obtaining a corresponding organic silicon compound. [2] Preparation of hardenable composition and the hardened article Hereinafter, each component used when preparing the hardenable composition and the hardened article will be described. [PPE] ‧PPO (trademark) SA90-100 made by SABIC Innovative Plastics Co., Ltd. [Epoxy resin] ‧Epoxy resin 1: Epiclon HP7200 (dicyclopentadiene type epoxy compound) made by DIC Corporation Resin 2: Epiclon 850S (bisphenol A type epoxy resin) manufactured by DIC Corporation [Hardener] ‧ 2E4MZ (2-methyl-4-imidazole) [Cyanate Compound] manufactured by Shikoku Chemical Industry Co., Ltd. ‧ BADCy (2,2-bis (4-cyanatephenyl) propane) manufactured by Lonza Japan Co., Ltd. [Organic metal salt] ‧Cu-NAPHTENATE (copper naphthenate) manufactured by DIC Corporation [Organic silicon compound] ‧ Organic silicon compound: The organic silicon compounds obtained in the above Examples 1-1 to 1-11, Comparative Examples 1-1, and 1-2. [0085] [Example 2-1] Follow Table 1 and Table 2. The blending ratio (parts by mass, except that the organic silicon compound is a non-volatile content conversion value) is described. PPE, epoxy resin, hardener, and the organic silicon compound 1 obtained in Example 1-1 are mixed, and the obtained mixture is mixed. The solution was heated to 60 ° C. After adding a cyanate ester compound and an organic metal salt thereto, the mixture was stirred for 30 minutes to completely dissolve it, and a varnish-like curable composition (resin varnish) was obtained. Next, the obtained resin varnish was impregnated with glass cloth (manufactured by Nitto Textile Co., Ltd., # 2116 type, WEA116E, E glass), and then heated and dried at 160 ° C. for 10 minutes to obtain a prepreg. At this time, it adjusted so that content of a resin component might be about 55 mass%. Each of the prepregs obtained by superposing 6 sheets was sandwiched between copper foil (GT-MP manufactured by Furukawa Circuit Foil Co., Ltd.) and laminated, and then heated and pressed under conditions of 200 ° C, 2 hours, and a pressure of 3 MPa. An evaluation substrate of the hardened article was obtained. [Examples 2-2 to 2-11, and Comparative Examples 2-1, 2-2] Except changing the organic silicon compound 1 to Examples 1-2 to 1-11 and Comparative Examples 1-1 to Except for the organosilicon compounds 2 to 13 obtained in 1-2, a hardening composition and the hardened article were produced in the same manner as in Example 2-1. [Comparative Examples 2-3, 2-4] Except changing the organosilicon compound 1 to γ-glycidoxypropyltrimethoxysilane (KBM-403, manufactured by Shin-Etsu Chemical Industry Co., Ltd.) as a comparison Except for Example 2-3 and changing to phenyltrimethoxysilane (KBM-103, manufactured by Shin-Etsu Chemical Industry Co., Ltd.) as Comparative Example 2-4, the rest of the process was performed in the same manner as in Example 2-1 to produce a hardening. Sexual composition and the hardened article. [Comparative Example 2-5] A curable composition and the cured article were produced in the same manner as in Example 2-1 except that the organosilicon compound 1 was not used. [0089] Each evaluation substrate prepared by the above steps was evaluated by the method shown below. [Dielectric Properties] The cavity resonance "CP461" manufactured by Kanto Electronics Application Development Co., Ltd. was used to measure the dielectric constant and dielectric tangent of a copper-clad laminate at 2 GHz. The results are shown in Tables 1 and 2 below. [Copper Foil Adhesion Strength] The tear strength (copper foil adhesion strength) of the copper foil on the surface of the copper-clad laminate was measured in accordance with JIS C 6481. At this time, a pattern with a width of 10 mm and a length of 100 mm was formed on a test piece having a width of 20 mm and a length of 100 mm. The copper foil was peeled off at a speed of 50 mm / min using a tensile tester, and the peel strength at this time (kgf / cm) was evaluated as the copper foil adhesion strength. The results are shown in Tables 1 and 2 below. [0090] [0091] [0092] As shown in Tables 1 and 2, the organosilicon compounds obtained in Examples 1-1 to 1-11 and the organosilicon compounds obtained in Comparative Examples 1-1 and 1-2 are known. Compared with the compound, γ-glycidoxypropyltrimethoxysilane and phenyltrimethoxysilane, the cured product can provide copper foil with excellent adhesion and excellent dielectric properties such as dielectric constant or dielectric tangent.