JP2008074917A5 - - Google Patents
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- JP2008074917A5 JP2008074917A5 JP2006253962A JP2006253962A JP2008074917A5 JP 2008074917 A5 JP2008074917 A5 JP 2008074917A5 JP 2006253962 A JP2006253962 A JP 2006253962A JP 2006253962 A JP2006253962 A JP 2006253962A JP 2008074917 A5 JP2008074917 A5 JP 2008074917A5
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- 229920000642 polymer Polymers 0.000 description 15
- -1 triethylsilyl group Chemical group 0.000 description 15
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 238000004770 highest occupied molecular orbital Methods 0.000 description 6
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 229910052697 platinum Inorganic materials 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 230000002194 synthesizing Effects 0.000 description 5
- 125000005103 alkyl silyl group Chemical group 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000005587 bubbling Effects 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- NNZZSJSQYOFZAM-UHFFFAOYSA-N tetrabutylazanium;tetrafluoroborate Chemical compound F[B-](F)(F)F.CCCC[N+](CCCC)(CCCC)CCCC NNZZSJSQYOFZAM-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N AI2O3 Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M Silver chloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000002484 cyclic voltammetry Methods 0.000 description 2
- 229910021397 glassy carbon Inorganic materials 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-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
- FOIXSVOLVBLSDH-UHFFFAOYSA-N silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JRTIUDXYIUKIIE-KZUMESAESA-N (1Z,5Z)-cycloocta-1,5-diene;nickel Chemical compound [Ni].C\1C\C=C/CC\C=C/1.C\1C\C=C/CC\C=C/1 JRTIUDXYIUKIIE-KZUMESAESA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N 2,2'-bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WNEXSUAHKVAPFK-UHFFFAOYSA-N 2,8-dibromodibenzothiophene Chemical compound C1=C(Br)C=C2C3=CC(Br)=CC=C3SC2=C1 WNEXSUAHKVAPFK-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- IMBKASBLAKCLEM-UHFFFAOYSA-L Ammonium iron(II) sulfate Chemical compound [NH4+].[NH4+].[Fe+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O IMBKASBLAKCLEM-UHFFFAOYSA-L 0.000 description 1
- AYHVBQBQROAZHP-UHFFFAOYSA-N Bis(cyclooctadiene)nickel(0) Chemical compound [Ni].[C]1[C]CC[C][C]CC1.[C]1[C]CC[C][C]CC1 AYHVBQBQROAZHP-UHFFFAOYSA-N 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- UQNVLAAMEYKKJO-UHFFFAOYSA-N dimethoxy methyl borate Chemical compound COOB(OC)OOC UQNVLAAMEYKKJO-UHFFFAOYSA-N 0.000 description 1
- 239000008079 hexane Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- QXZGXRIXJAVMTI-UHFFFAOYSA-N tribenzylsilicon Chemical group C=1C=CC=CC=1C[Si](CC=1C=CC=CC=1)CC1=CC=CC=C1 QXZGXRIXJAVMTI-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Description
以下、本発明を説明する。本明細書中において、重合体のHOMO(最高被占準位)のエネルギーレベルは、重合体の酸化電位から求め、重合体のLUMO(最低空準位)のエネルギーレベルは、重合体の還元電位から求める。酸化電位は、サイクリックボルタンメトリー法により、参照電極に銀/塩化銀電極、作用極に白金電極、対極に白金電極を用い、0.1重量%テトラブチルアンモニウムテトラフルオロボレートを含むアセトニトリル溶液中で、該溶液を窒素で1分間バブリングした後に測定して得られる値である。還元電位は、参照電極に銀/銀イオン電極、作用極にグラッシーカーボン電極、対極に白金電極を用い、窒素で置換したグローブボックスにおいて、0.1重量%テトラブチルアンモニウムテトラフルオロボレートを含むアセトニトリル溶液中で測定して得られる値である。また、電位の掃引速度は50mV/sで測定する。 The present invention will be described below. In this specification, the energy level of HOMO (highest occupied level) of a polymer is determined from the oxidation potential of the polymer, and the energy level of LUMO (lowest empty level) of the polymer is the reduction potential of the polymer. Ask from. Oxidation potential by cyclic voltammetry, silver / silver chloride electrode as a reference electrode, a platinum electrode the working electrode, a platinum electrode as a counter electrode, acetonitrile solvent solution containing 0.1 wt% tetrabutyl ammonium tetrafluoroborate, the the solvent solution is a value obtained by measuring after bubbling for 1 minute with nitrogen. Reduction potential, the silver / silver ion electrode as a reference electrode, glassy carbon electrode to the working electrode, a platinum electrode as a counter electrode, in a glove box purged with nitrogen, acetonitrile solvent solution containing 0.1 wt% tetrabutyl ammonium tetrafluoroborate It is a value obtained by measuring with. The potential sweep rate is measured at 50 mV / s.
置換シリル基としては、アルキル基、アリール基、アリールアルキル基及び1価の複素環基から選ばれる1個、2個又は3個の基で置換されたシリル基が挙げられる。置換シリル基の炭素数は、通常、1〜60程度、好ましくは3〜48である。これらのアルキル基、アリール基、アリールアルキル基及び1価の複素環基は置換基を有していてもよい。置換シリル基の具体例としては、トリメチルシリル基、トリエチルシリル基、トリプロピルシリル基、トリ−i−プロピルシリル基、ジメチル−i−プロピルシリル基、ジエチル−i−プロピルシリル基、t−ブチルシリルジメチルシリル基、ペンチルジメチルシリル基、ヘキシルジメチルシリル基、ヘプチルジメチルシリル基、オクチルジメチルシリル基、2−エチルヘキシル−ジメチルシリル基、ノニルジメチルシリル基、デシルジメチルシリル基、3,7−ジメチルオクチル−ジメチルシリル基、ラウリルジメチルシリル基、フェニル−C1〜C12アルキルシリル基、C1〜C12アルコキシフェニル−C1〜C12アルキルシリル基、C1〜C12アルキルフェニル−C1〜C12アルキルシリル基、1−ナフチル−C1〜C12アルキルシリル基、2−ナフチル−C1〜C12アルキルシリル基、フェニル−C1〜C12アルキルジメチルシリル基、トリフェニルシリル基、トリ−p−キシリルシリル基、トリベンジルシリル基、ジフェニルメチルシリル基、t−ブチルジフェニルシリル基、ジメチルフェニルシリル基等が挙げられる。 Examples of the substituted silyl group include silyl groups substituted with one, two, or three groups selected from an alkyl group, an aryl group, an arylalkyl group, and a monovalent heterocyclic group. The carbon number of the substituted silyl group is usually about 1 to 60, preferably 3 to 48. These alkyl group, aryl group, arylalkyl group and monovalent heterocyclic group may have a substituent. Specific examples of the substituted silyl group, a trimethylsilyl group, triethylsilyl group, tripropylsilyl group, tri -i- propyl silyl group, dimethyl -i- propyl Le silyl group, diethyl -i- propyl silyl group, t-butylsilyl Dimethylsilyl group, pentyldimethylsilyl group, hexyldimethylsilyl group, heptyldimethylsilyl group, octyldimethylsilyl group, 2-ethylhexyl-dimethylsilyl group, nonyldimethylsilyl group, decyldimethylsilyl group, 3,7-dimethyloctyl-dimethyl silyl group, lauryl dimethyl silyl group, a phenyl -C 1 -C 12 alkylsilyl group, C 1 -C 12 alkoxyphenyl -C 1 -C 12 alkylsilyl group, C 1 -C 12 alkylphenyl -C 1 -C 12 alkyl silyl group, 1-naphthyl -C 1 -C 12 Arukirushiri Group, 2-naphthyl -C 1 -C 12 alkylsilyl group, a phenyl -C 1 -C 12 alkyldimethylsilyl group, triphenylsilyl group, tri -p- Kishirirushiriru group, tribenzylsilyl group, diphenylmethylsilyl group, t -A butyl diphenylsilyl group, a dimethylphenylsilyl group, etc. are mentioned.
−HOMO及びLUMOのエネルギーレベルの測定−
重合体のHOMOのエネルギーレベルは重合体の酸化電位から求め、重合体のLUMOのエネルギーレベルは重合体の還元電位から求めた。酸化電位及び還元電位の測定には、サイクリックボルタンメトリー(ビー・エー・エス製、商品名:ALS600)を用い、0.1重量%テトラブチルアンモニウムテトラフルオロボレートを含むアセトニトリル溶液中で測定を行った。酸化電位の測定は、参照電極に銀/塩化銀電極、作用極に白金電極、対極に白金電極を用い、溶液を窒素で1分間バブリングした後に測定を行った。一方、還元電位の測定は、参照電極に銀/銀イオン電極、作用極にグラッシーカーボン電極、対極に白金電極を用い、窒素で置換したグローブボックス中で測定を行った。また、電位の掃引速度は共に50mV/sで測定した。
-Measurement of HOMO and LUMO energy levels-
The HOMO energy level of the polymer was determined from the oxidation potential of the polymer, and the LUMO energy level of the polymer was determined from the reduction potential of the polymer. For the measurement of the oxidation potential and reduction potential by cyclic voltammetry (BAS, trade name: ALS600) used, it was measured in acetonitrile solvent solution containing 0.1 wt% tetrabutyl ammonium tetrafluoroborate It was. Measurement of oxidation potential, silver / silver chloride electrode as a reference electrode, a platinum electrode the working electrode, a platinum electrode as a counter electrode, a soluble liquid was measured after bubbling for 1 minute with nitrogen. On the other hand, the reduction potential was measured in a glove box substituted with nitrogen using a silver / silver ion electrode as a reference electrode, a glassy carbon electrode as a working electrode, and a platinum electrode as a counter electrode. Both potential sweep rates were measured at 50 mV / s.
<合成例1>(化合物Aの合成)
(1)化合物A−1の合成
不活性雰囲気下1lの四つ口フラスコに、2,8−ジブロモジベンゾチオフェン7gとTHF 280mlを入れ、室温で撹拌し、溶解させた後、−78℃まで冷却した。n−ブチルリチウム 29ml(1.6Mヘキサン溶液)を滴下した。滴下終了後、温度を保持したまま2時間撹拌し、トリメトキシボロン酸 13gを滴下した。滴下終了後、ゆっくり室温まで戻した。3時間室温で撹拌後、TLCで原料の消失を確認した。5重量%硫酸 100mlを加えて反応を終了させ、室温で12時間撹拌した。水を加えて洗浄し、有機層を抽出した。溶媒を酢酸エチルに置換した後、30重量%過酸化水素水 5mlを加え、40℃で5時間撹拌した。その後、有機層を抽出し、10重量%硫酸アンモニウム鉄(II)水溶液で洗浄後、乾燥し、溶媒を除去することにより、下記式:
A−1
で表される化合物A−1(茶色の固体)を4.43g得た。LC−MS測定結果から、二量体等の副生成物も生成しており、化合物A−1の純度は77%であった(LC面積百分率)。
<Synthesis Example 1> (Synthesis of Compound A)
(1) Synthesis of Compound A-1 In a 1 l four-necked flask under an inert atmosphere, 7 g of 2,8-dibromodibenzothiophene and 280 ml of THF were added, stirred at room temperature, dissolved, and then cooled to −78 ° C. did. 29 ml of n-butyllithium (1.6 M hexane solution) was added dropwise. After completion of dropping, the mixture was stirred for 2 hours while maintaining the temperature, and 13 g of trimethoxyboronic acid was added dropwise. After completion of dropping, the temperature was slowly returned to room temperature. After stirring at room temperature for 3 hours, disappearance of the raw material was confirmed by TLC. The reaction was terminated by adding 100 ml of 5% by weight sulfuric acid and stirred at room temperature for 12 hours. Water was added for washing, and the organic layer was extracted. After replacing the solvent with ethyl acetate, 5 ml of 30 wt% aqueous hydrogen peroxide was added and stirred at 40 ° C. for 5 hours. Thereafter, the organic layer was extracted, washed with a 10% by weight aqueous ammonium iron (II) sulfate solution, dried, and the solvent was removed to obtain the following formula:
A-1
4.43g of compound A-1 (brown solid) represented by this was obtained. From the LC-MS measurement results, by-products such as dimers were also produced, and the purity of Compound A-1 was 77% (LC area percentage).
−HOMO、LUMOのエネルギーレベルの測定−
上述の測定方法に従って、重合体2(26.3量体)のHOMOのエネルギーレベル及びLUMOのエネルギーレベルを測定した。重合体2のHOMOのエネルギーレベルは5.9eVであり、LUMOのエネルギーレベルは2.4eVであった。なお、これらの値を、前記重合体1において、繰り返し単位Aのみからなる重合体のものとみなした。
-Measurement of HOMO and LUMO energy levels-
According to the measurement method described above, the HOMO energy level and LUMO energy level of polymer 2 (26.3-mer) were measured. Polymer 2 had a HOMO energy level of 5.9 eV and a LUMO energy level of 2.4 eV. Note that these values, said have you to polymer 1 was regarded as the polymer consisting of a repeating unit A.
<合成例5>(重合体3の合成)
化合物A 352mg及び2,2’−ビピリジル 274mgを脱水したテトラヒドロフラン20mLに溶解した後、窒素でバブリングして系内を窒素置換した。窒素雰囲気下において、この溶液に、ビス(1、5−シクロオクタジエン)ニッケル(0){Ni(COD)2} 500mg加え、60℃まで昇温し、3時間反応させた。反応後、得られた反応液を室温(約25℃)まで冷却し、25重量%アンモニア水10ml/メタノール120ml/イオン交換水50ml混合溶液中に滴下して1時間攪拌した後、析出した沈殿をろ過して2時間減圧乾燥し、トルエン30mlに溶解させた。その後、1N塩酸30mlを加えて1時間攪拌し、水層を除去して有機層に4重量%アンモニア水30mlを加え、1時間攪拌した後に水層を除去した。有機層はメタノール200mlに滴下して1時間攪拌し、析出した沈殿をろ過して2時間減圧乾燥し、トルエン30mlに溶解させた。その後、アルミナカラム(アルミナ量5g)に通して精製を行い、回収したトルエン溶液をメタノール250mlに滴下して1時間攪拌し、析出した沈殿をろ過して2時間減圧乾燥させて、重合体(以下、この重合体を「重合体3」という)46mgを得た。
<Synthesis Example 5> (Synthesis of Polymer 3)
After 352 mg of Compound A and 274 mg of 2,2′-bipyridyl were dissolved in 20 mL of dehydrated tetrahydrofuran, the system was purged with nitrogen by bubbling with nitrogen. Under a nitrogen atmosphere, 500 mg of bis (1,5-cyclooctadiene) nickel (0) {Ni (COD) 2 } was added to this solution, and the temperature was raised to 60 ° C. and reacted for 3 hours. After the reaction, the resulting reaction solution was cooled to room temperature (about 25 ° C.), dropped into a mixed solution of 25 wt% ammonia water 10 ml / methanol 120 ml / ion-exchanged water 50 ml and stirred for 1 hour, and then the deposited precipitate was removed. The solution was filtered, dried under reduced pressure for 2 hours, and dissolved in 30 ml of toluene. Thereafter, 30 ml of 1N hydrochloric acid was added and stirred for 1 hour, the aqueous layer was removed, 30 ml of 4% by weight aqueous ammonia was added to the organic layer, and the aqueous layer was removed after stirring for 1 hour. The organic layer was dropped into 200 ml of methanol and stirred for 1 hour, the deposited precipitate was filtered, dried under reduced pressure for 2 hours, and dissolved in 30 ml of toluene. Then, it refine | purifies by passing through an alumina column (alumina amount 5g), The collect | recovered toluene solution is dripped at methanol 250ml, it stirs for 1 hour, The depositing precipitate is filtered and dried under reduced pressure for 2 hours. This polymer was referred to as “Polymer 3”).
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US8927978B2 (en) | 2010-07-21 | 2015-01-06 | Sumitomo Chemical Company, Limited | Organic EL element |
US9276237B2 (en) | 2010-07-21 | 2016-03-01 | Sumitomo Chemical Company, Limited | Method for producing organic EL element |
CN103120020B (en) | 2010-07-21 | 2016-03-23 | 住友化学株式会社 | The manufacture method of organic electroluminescent device |
JP5653122B2 (en) | 2010-08-10 | 2015-01-14 | 住友化学株式会社 | Organic electroluminescence device and method for producing the same |
CN103385036B (en) | 2011-02-21 | 2017-02-08 | 住友化学株式会社 | Method for producing organic electroluminescent element |
GB2515909B (en) * | 2012-01-31 | 2020-07-15 | Cambridge Display Tech Ltd | Composition comprising a fluorescent light-emitting material and triplet-accepting polymer and use thereof |
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