JP4210751B2 - Dendron compound and method for producing the same - Google Patents
Dendron compound and method for producing the same Download PDFInfo
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- JP4210751B2 JP4210751B2 JP2003319674A JP2003319674A JP4210751B2 JP 4210751 B2 JP4210751 B2 JP 4210751B2 JP 2003319674 A JP2003319674 A JP 2003319674A JP 2003319674 A JP2003319674 A JP 2003319674A JP 4210751 B2 JP4210751 B2 JP 4210751B2
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- 150000001875 compounds Chemical class 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- LGKDIHUXRXRYJV-UHFFFAOYSA-N 9h-carbazole;quinoline Chemical compound N1=CC=CC2=CC=CC=C21.C1=CC=C2C3=CC=CC=C3NC2=C1 LGKDIHUXRXRYJV-UHFFFAOYSA-N 0.000 claims description 3
- GTEMIOZMYHWLSN-UHFFFAOYSA-N IC1=CC=C2C=CC=NC2=C1OC(C)=O Chemical class IC1=CC=C2C=CC=NC2=C1OC(C)=O GTEMIOZMYHWLSN-UHFFFAOYSA-N 0.000 claims description 3
- 150000001716 carbazoles Chemical class 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 238000000034 method Methods 0.000 description 12
- 239000010409 thin film Substances 0.000 description 9
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000004696 coordination complex Chemical class 0.000 description 4
- 239000000412 dendrimer Substances 0.000 description 4
- 229920000736 dendritic polymer Polymers 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 150000004984 aromatic diamines Chemical class 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- RSEDJGQHEVYWOD-UHFFFAOYSA-N (5-chloro-7-iodoquinolin-8-yl) acetate Chemical compound C1=CN=C2C(OC(=O)C)=C(I)C=C(Cl)C2=C1 RSEDJGQHEVYWOD-UHFFFAOYSA-N 0.000 description 1
- CKHGYGVALSENIE-UHFFFAOYSA-N 2-[4,5-bis(2-aminoethyl)oxolan-3-yl]ethanamine Chemical class NCCC1COC(CCN)C1CCN CKHGYGVALSENIE-UHFFFAOYSA-N 0.000 description 1
- JJIQKIUIIVFHAN-UHFFFAOYSA-N 9-(4-ethynylphenyl)carbazole Chemical compound C1=CC(C#C)=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 JJIQKIUIIVFHAN-UHFFFAOYSA-N 0.000 description 1
- HRWRWJJOTOKGHE-UHFFFAOYSA-N 9-ethynyl-1-phenylcarbazole Chemical class C(#C)N1C2=CC=CC=C2C=2C=CC=C(C1=2)C1=CC=CC=C1 HRWRWJJOTOKGHE-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N N,N-Diethylethanamine Substances CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- 238000003477 Sonogashira cross-coupling reaction Methods 0.000 description 1
- 125000005011 alkyl ether group Chemical group 0.000 description 1
- 125000005012 alkyl thioether group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- -1 copper halide Chemical class 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
本発明は、有機エレクトロルミネセンス分野、発光材料分野、有機FET分野等のデバイスへの応用することができる薄膜デバイスを作成するのに適した金属錯体デンドリマーの原料となるデンドロン化合物及びその製造方法に関する。 The present invention relates to a dendron compound as a raw material of a metal complex dendrimer suitable for producing a thin film device that can be applied to devices in the organic electroluminescence field, light emitting material field, organic FET field, and the like, and a method for producing the same. .
トリス(8-キノリノレート)アルミニウム（Alq3）ならびに類縁化合物は、多層型有機ELデバイスにおいて、極めて有用とされる分子であるが、その溶解性の低さ、ならびに結晶性のため、薄膜形成等のデバイス用の加工が困難な分子である。したがって良好な薄膜デバイス作製のために、真空蒸着法などのドライプロセスを用いなければならず、製造コスト低減や効率化をはかるうえで問題が多い。
ITOガラス上に、芳香族ジアミンの第１層（ホール移動層）、Alq3の第２層（発光層）を形成し、Mg/Ag電極で挟みこんだ、二層系ＥＬデバイスが報告されている。二層の有機薄膜のモルホロジーがデバイス性能を左右し、両層ともにスムースで連続的でなければならないが、芳香族ジアミン層がアモルファス性である一方で、Alq3層は５００Åの平均サイズを持った微結晶からなっていることが知られている。（非特許文献１参照）
A two-layer EL device has been reported in which a first layer (hole transfer layer) of aromatic diamine and a second layer (light emitting layer) of Alq3 are formed on ITO glass and sandwiched between Mg / Ag electrodes. . The morphology of the two-layer organic thin film affects the device performance, and both layers must be smooth and continuous, while the aromatic diamine layer is amorphous, while the Alq3 layer has a fine size with an average size of 500 mm. It is known to consist of crystals. (See Non-Patent Document 1)
分子を用いる薄膜デバイスの作製には、真空蒸着などの乾式法と、スピンコートなどによる湿式法とがある。真空蒸着法は作製した蒸着膜の純度や均一性の点で良好であるが、効率性が低く、時間やコストなどに難点がある。一方、スピンコート法は、簡便で、安価、短時間で大面積の薄膜材料が作製できるなどの特長があり、経済性が高い。
薄膜デバイスとして急速に成長しているELに用いられるAlq3ならびに類縁化合物群は、概して溶解性が低いため、湿式法による薄膜形成が困難で、真空蒸着法により製造されてきた。本発明は、これら従来、難溶性とされるAlq３など、デバイス機能を担う分子を、易溶性ならびにアモルファス性としたもので、湿式法による分子デバイス形成を可能にする分子材料を提供するものである。
本発明は、有機溶剤に溶解しやすい金属錯体デンドリマーの原料となるデンドロン化合物及びその製造方法を開発する。
There are two methods for manufacturing a thin film device using molecules: a dry method such as vacuum deposition and a wet method such as spin coating. The vacuum vapor deposition method is good in terms of the purity and uniformity of the produced vapor deposition film, but has low efficiency and has problems in time and cost. On the other hand, the spin coating method has features such as being simple, inexpensive, and capable of producing a thin film material having a large area in a short time, and is highly economical.
Alq3 and related compounds used in EL, which is rapidly growing as a thin film device, generally have low solubility, so that it is difficult to form a thin film by a wet method and has been manufactured by a vacuum deposition method. The present invention provides a molecular material that enables molecular devices to be formed by a wet process, in which molecules having a device function, such as Alq3, which has been conventionally poorly soluble, are easily soluble and amorphous. .
This invention develops the dendron compound used as the raw material of the metal complex dendrimer which is easy to melt | dissolve in an organic solvent, and its manufacturing method.
本発明は、有機溶剤に溶解しやすい金属錯体デンドリマーを形成する化合物であるデンドロン化合物のうち、とくに一般式
本発明は、さらにこのデンドロン化合物の製造方法も見出した。すなわち、
一般式
化合物（Ｎ−エチニルフェニルカルバゾール類）と、一般式
を反応させて、一般式
化合物（カルバゾール−キノリン複合体）を得て、さらに当該化合物を加水分解することにより、一般式
The present invention also found a method for producing this dendron compound. That is,
General formula
To give the general formula
本発明のデンドロン化合物は、Ａｌ，Ｚｎ，Ｂｅ，Ｇｅ，Ｇｅ，Ｍｇなどの金属と錯塩を形成することができること、及びその錯塩が、有機溶剤に溶解しやすいことが判明した。 It has been found that the dendron compound of the present invention can form a complex salt with a metal such as Al, Zn, Be, Ge, Ge, Mg, and the complex salt is easily dissolved in an organic solvent.
本発明で用いる出発原料である化合物（Ｎ−エチニルフェニルカルバゾール類）としては、カルバゾール基を構成するベンゼン環ならびにＮ位に結合したフェニル環上に、それぞれ０〜２個の炭素数１〜８までのアルキル基、アルキルエーテル基、アルキルチオエーテル基を導入した置換体等をあげることができる。また、もう一方の出発原料である化合物（７−ヨード−８−アセトキシキノリン類）としては、５位に、水素、フッ素、塩素、臭素、沃素を導入した置換体等をあげることができる。
また、これらをカップリングしてカルバゾール−キノリン複合体を得る際の反応条件としては、両者の等モル混合物を、脱水テトラヒドロフラン-トリエチルアミン混合溶媒中、ジクロロビス(トリフェニルホスフィン)パラジウムなどのパラジウム錯体ならびに沃化銅を触媒として、不活性ガス雰囲気下で長時間室温付近にて攪拌する方法（所謂Sonogashira反応法）が好適である。
The compounds (N-ethynylphenylcarbazoles) which are starting materials used in the present invention are each composed of 0 to 2 carbon atoms of 1 to 8 on the benzene ring constituting the carbazole group and the phenyl ring bonded to the N position. Substituents into which an alkyl group, an alkyl ether group, or an alkylthioether group is introduced can be used. In addition, examples of the other starting material (7-iodo-8-acetoxyquinolines) include a substituent in which hydrogen, fluorine, chlorine, bromine or iodine is introduced at the 5-position.
In addition, as a reaction condition when these are coupled to obtain a carbazole-quinoline complex, an equimolar mixture of them is mixed with a palladium complex such as dichlorobis (triphenylphosphine) palladium and iodine in a dehydrated tetrahydrofuran-triethylamine mixed solvent. A method (so-called Sonogashira reaction method) in which copper halide is used as a catalyst and stirred for a long time in the vicinity of room temperature in an inert gas atmosphere is suitable.
（8-アセトキシ-7-[4-(9’-カルバゾリル)フェニルエチニル]-5-クロロキノリンの製造）
9-(4-エチニルフェニル)カルバゾール(3.059 g, 11.443 mmol)、8-アセトキシ-5-クロロ-7-ヨードキノリン(3.911 g, 11.222 mmol)、ジクロロビス(トリフェニルホスフィン)パラジウム(0.183 g, 0.261 mmol)及びヨウ化銅(0.094 g, 0.494 mmol)の混合物をテトラヒドロフラン(40 ml)-トリエチルアミン(10 ml)の混合溶媒中、窒素下室温で一晩撹拌した。その溶液をろ過、溶媒を留去して得られた粗製物を、シリカゲルカラムクロマトグラフィーにて、まずクロロホルム、続いてクロロホルム-メタノール(9: 1 v/v)を流出溶媒として展開、主生成物を分離した。ジクロロメタン-メタノールより再結晶し、粉末を得た（収率71.3%）。
1H NMR (400 MHz, CDCl3, TMS): δ (ppm) 2.62 (s, 3H, CH3), 7.32 (t, J 7.2 Hz, 2H, arom. H), 7.42-7.48 (m, 4H, arom. H), 7.565 (dd, J 8.55 and 4.2 Hz, 1H, quinoline H), 7.63 (d, J 8.4 Hz, 2H, arom. H), 7.79 (d, J 8.4 Hz, 2H, arom. H), 7.82 (s, 1H, quinoline H), 8.16 (d, J 7.7 Hz, 2H, arom. H), 8.565 (dd, J 8.6 and 1.5 Hz, 1H, quinoline H), 9.01 (dd, J 4.2 and 1.5 Hz, 1H, quinoline H); ESI-MS : m/z 509.1 [M+Na]+, 997.4 [2M+Na]+.
(Production of 8-acetoxy-7- [4- (9'-carbazolyl) phenylethynyl] -5-chloroquinoline)
9- (4-ethynylphenyl) carbazole (3.059 g, 11.443 mmol), 8-acetoxy-5-chloro-7-iodoquinoline (3.911 g, 11.222 mmol), dichlorobis (triphenylphosphine) palladium (0.183 g, 0.261 mmol) ) And copper iodide (0.094 g, 0.494 mmol) were stirred in a mixed solvent of tetrahydrofuran (40 ml) -triethylamine (10 ml) at room temperature overnight under nitrogen. The crude product obtained by filtering the solution and distilling off the solvent was developed using silica gel column chromatography, first with chloroform and then with chloroform-methanol (9: 1 v / v) as the effluent solvent. Separated. Recrystallization from dichloromethane-methanol gave a powder (yield 71.3%).
1 H NMR (400 MHz, CDCl 3 , TMS): δ (ppm) 2.62 (s, 3H, CH 3 ), 7.32 (t, J 7.2 Hz, 2H, arom.H), 7.42-7.48 (m, 4H, arom.H), 7.565 (dd, J 8.55 and 4.2 Hz, 1H, quinoline H), 7.63 (d, J 8.4 Hz, 2H, arom.H), 7.79 (d, J 8.4 Hz, 2H, arom.H) , 7.82 (s, 1H, quinoline H), 8.16 (d, J 7.7 Hz, 2H, arom.H), 8.565 (dd, J 8.6 and 1.5 Hz, 1H, quinoline H), 9.01 (dd, J 4.2 and 1.5 Hz, 1H, quinoline H); ESI-MS: m / z 509.1 [M + Na] + , 997.4 [2M + Na] + .
（7-[4-(9’-カルバゾリル)フェニルエチニル]-5-クロロ-8-キノリノール ）の製造)
上記8-アセトキシ-7-[4-(9’-カルバゾリル)フェニルエチニル]-5-クロロキノリン(1.510 g, 3.101 mmol)を、テトラヒドロフラン(60 ml)-エタノール(15 ml)混合溶媒に溶解し、水酸化ナトリウム(0.221 g, 5.525 mmol)水溶液5 mlを加え室温で一晩撹拌した。150 mlの水を加えた後、p-トルエンスルホン酸一水和物を用いて中和して得られた沈殿を、ろ集、乾燥することにより目的物を得た（収率100%）
1H NMR (400 MHz, DMSO-d6): δ (ppm) 7.33-7.37 (m, 2H, arom. H), 7.48-7.57 (m, 6H, arom. H), 7.67 (d, J 8.5 Hz, 2H, arom. H), 7.75 (d, J 8.5 Hz, 2H, arom. H), 8.27-8.31 (m, 3H, arom. H), 8.66 (s, 1H, arom. H).
(Production of 7- [4- (9'-carbazolyl) phenylethynyl] -5-chloro-8-quinolinol)
The 8-acetoxy-7- [4- (9′-carbazolyl) phenylethynyl] -5-chloroquinoline (1.510 g, 3.101 mmol) was dissolved in a tetrahydrofuran (60 ml) -ethanol (15 ml) mixed solvent, 5 ml of an aqueous solution of sodium hydroxide (0.221 g, 5.525 mmol) was added and stirred overnight at room temperature. After adding 150 ml of water, the precipitate obtained by neutralization with p-toluenesulfonic acid monohydrate was collected by filtration and dried to obtain the desired product (yield 100%)
1 H NMR (400 MHz, DMSO-d 6 ): δ (ppm) 7.33-7.37 (m, 2H, arom.H), 7.48-7.57 (m, 6H, arom.H), 7.67 (d, J 8.5 Hz , 2H, arom.H), 7.75 (d, J 8.5 Hz, 2H, arom.H), 8.27-8.31 (m, 3H, arom.H), 8.66 (s, 1H, arom.H).
実施例１の製造方法を化学式で示すと、以下のとおりである。
本発明のデンドロン化合物は、有機エレクトロルミネセンス分野、発光材料分野、有機FET分野等のデバイスへの応用することができる薄膜デバイスを作成するのに適した有機溶剤に溶けやすい金属錯体デンドリマーの原料となるデンドロン化合物であることが判明した。
The dendron compound of the present invention is a raw material of a metal complex dendrimer that is easily soluble in an organic solvent suitable for making a thin film device that can be applied to devices in the organic electroluminescence field, light emitting material field, organic FET field, etc. Was found to be a dendron compound.
Claims (2)
で示されるデンドロン化合物。 General formula
A dendron compound represented by:
化合物（Ｎ−エチニルフェニルカルバゾール類）と、一般式
を反応させて、一般式
化合物（カルバゾール−キノリン複合体）を得て、さらに当該化合物を加水分解することにより、一般式
General formula
To give the general formula
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003319674A JP4210751B2 (en) | 2003-09-11 | 2003-09-11 | Dendron compound and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003319674A JP4210751B2 (en) | 2003-09-11 | 2003-09-11 | Dendron compound and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005082573A JP2005082573A (en) | 2005-03-31 |
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