JP2011195515A - アントラセン誘導体、樹脂、硬化性組成物及び硬化物 - Google Patents
アントラセン誘導体、樹脂、硬化性組成物及び硬化物 Download PDFInfo
- Publication number
- JP2011195515A JP2011195515A JP2010064569A JP2010064569A JP2011195515A JP 2011195515 A JP2011195515 A JP 2011195515A JP 2010064569 A JP2010064569 A JP 2010064569A JP 2010064569 A JP2010064569 A JP 2010064569A JP 2011195515 A JP2011195515 A JP 2011195515A
- Authority
- JP
- Japan
- Prior art keywords
- group
- anthracene derivative
- resin
- anthracene
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001454 anthracenes Chemical class 0.000 title claims abstract description 102
- 229920005989 resin Polymers 0.000 title claims abstract description 73
- 239000011347 resin Substances 0.000 title claims abstract description 73
- 239000000203 mixture Substances 0.000 title claims abstract description 27
- 125000003118 aryl group Chemical group 0.000 claims abstract description 22
- 125000005027 hydroxyaryl group Chemical group 0.000 claims abstract description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 abstract description 43
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 abstract description 37
- -1 polycyclic aromatic compound Chemical class 0.000 description 71
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 43
- 230000000052 comparative effect Effects 0.000 description 36
- 238000004519 manufacturing process Methods 0.000 description 30
- 239000000047 product Substances 0.000 description 30
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 27
- 239000000463 material Substances 0.000 description 24
- 239000002994 raw material Substances 0.000 description 24
- 238000000034 method Methods 0.000 description 22
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 20
- 125000001424 substituent group Chemical group 0.000 description 20
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 19
- 229910052799 carbon Inorganic materials 0.000 description 19
- 239000013078 crystal Substances 0.000 description 19
- 150000002989 phenols Chemical class 0.000 description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 18
- 230000009257 reactivity Effects 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 16
- 239000003960 organic solvent Substances 0.000 description 16
- 125000005577 anthracene group Chemical group 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 238000000862 absorption spectrum Methods 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- 238000001723 curing Methods 0.000 description 14
- 229920003986 novolac Polymers 0.000 description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
- 229930185605 Bisphenol Natural products 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- 239000003377 acid catalyst Substances 0.000 description 11
- 125000004849 alkoxymethyl group Chemical group 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 238000002189 fluorescence spectrum Methods 0.000 description 10
- 230000009477 glass transition Effects 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- YMNKUHIVVMFOFO-UHFFFAOYSA-N anthracene-9-carbaldehyde Chemical compound C1=CC=C2C(C=O)=C(C=CC=C3)C3=CC2=C1 YMNKUHIVVMFOFO-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000005011 phenolic resin Substances 0.000 description 9
- 229920001187 thermosetting polymer Polymers 0.000 description 9
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 8
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 6
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 5
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 230000018109 developmental process Effects 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 150000005846 sugar alcohols Polymers 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000004566 building material Substances 0.000 description 4
- 239000012776 electronic material Substances 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 230000005284 excitation Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 229920002120 photoresistant polymer Polymers 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 236TMPh Natural products CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 238000005530 etching Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
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- 150000002576 ketones Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- OGRAOKJKVGDSFR-UHFFFAOYSA-N 2,3,5-trimethylphenol Chemical compound CC1=CC(C)=C(C)C(O)=C1 OGRAOKJKVGDSFR-UHFFFAOYSA-N 0.000 description 2
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
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Abstract
【解決手段】本発明は、下記式(1)にて表されるアントラセン誘導体、このアントラセン誘導体から得られる樹脂、これらを含む組成物及びこの組成物の硬化物である。
(式(1)中、X及びYは、それぞれ独立に、芳香環上の1又は2以上の水素原子がCH2OZで置換されているヒドロキシアリール基である。複数のZは、それぞれ独立に、水素原子又は炭素数1〜4のアルキル基である。)
【選択図】なし
Description
下記式(1)にて表されるアントラセン誘導体である。
<アントラセン誘導体>
本発明のアントラセン誘導体は、上記式(1)で示される。
本発明のアントラセン誘導体は、非反応性含酸素有機溶媒及び酸触媒の存在下にて、フェノール類とアントラセン−9−カルボアルデヒドとを反応させ、ビスフェノールアントラセン化合物を得る第一工程、及び、得られたビスフェノールアントラセン化合物を塩基性触媒の存在下でホルムアルデヒドと反応させる第二工程により製造される。また、第三工程として、酸触媒存在下にて、第二工程にて得られたアントラセン誘導体と、炭素数1〜4の飽和脂肪族アルコールとを反応させ、メチロール基をアルコキシメチル基に変えることも出来る。
この製造方法の第一工程におけるフェノール類とは芳香環上にヒドロキシル基を有する化合物をいい、フェノール系化合物、ナフトール系化合物等が挙げられる。上記フェノール系化合物とは、フェノール及び芳香環上の水素が他の置換基に置換されたフェノールをいう。上記置換基としては、アルキル基やヒドロキシル基等が挙げられる。この置換基の数としては、アントラセン−9−カルボアルデヒドとの反応性から、4以下が好ましく、2以下が更に好ましく、0が特に好ましい。また、アントラセン−9−カルボアルデヒドとの反応性から、ヒドロキシル基のパラ位に置換基が配置されていないことが好ましい。
本製造方法の第二工程においては、塩基性触媒及び水等の溶媒の存在下にて、第一工程で得られたビスフェノールアントラセン化合物とホルムアルデヒドと反応させることにより行われる。
本製造方法の第三工程は、必ずしも必要ではないが、第二工程で得られたアントラセン誘導体の安定性を高めたい場合や、硬化剤として用いる場合に硬化開始温度を高めたい場合に行う工程である。本製造方法の第三工程では、酸触媒下にて、第二工程で得られたアントラセン誘導体と炭素数1〜4の飽和脂肪族アルコールとを反応させることによって製造される。
本発明の樹脂は、当該アントラセン誘導体を用いて得られる樹脂であり、例えば、当該アントラセン誘導体とフェノール類又はビスフェノール類とを含む混合物を加熱し、縮合させたノボラック型フェノール樹脂等である。当該アントラセン誘導体は、CH2OZ(メチロール基又はアルコキシメチル基)を有するため、一般的なアントラセン誘導体とフェノール類又はビスフェノール類とをホルムアルデヒド等の縮合剤を利用して縮合する場合と比べ、反応性が高い。従って、本発明のアントラセン誘導体をモノマーとして用いることで、未反応及び低分子量のアントラセン骨格が残りがたく、容易に高分子量の樹脂を得ることができる。
当該硬化性組成物は、本発明のアントラセン誘導体又はこのアントラセン誘導体から得られる重合体を含むものである。
本発明の硬化物は、上記硬化性組成物を加熱することで硬化して得られるものである。当該硬化物は各種樹脂として使用することができる。当該硬化物は、アントラセン骨格に由来する高屈折率、高炭素密度、蛍光性能といった広範の用途に有用な各特性を付与する他、耐エッチング性のような電子材料用途特有の特性も付与する事ができ、高汎用性の材料として様々な用途に用いることができる。
GPC純度は、東ソー製HLC−8220型GPC、RI検出器、TSK−Gel SuperHZ2000+HZ1000+HZ1000(4.6mmφ×150mm)カラムを用い、展開溶媒としてテトラヒドロフランを0.35ml/分で送液し、目的物ピークの面積比によって求めた。
HPLC純度及び反応の終点確認は、島津製作所製HPLC Promineceシリーズ、UV検出器SPD−20A(246nm)、GLサイエンス製ODS−3(4.6mmφ×250mm)カラムを用い、展開溶媒として水/アセトニトリル=40/60を1.0ml/分で送液し、目的物ピークの面積比によって求めた。
分子量は、東ソー製HLC−8220型GPC、検出器(UV254nm)、TSK−Gel G4000HXL+G2000HXL(7.8mmφ×300mm)カラムを用い、展開溶媒としてテトラヒドロフランを1.00ml/分で送液して測定し、標準ポリスチレン換算の重量平均分子量(Mw)を求めた。
融点は、リガク製DSC8230型示差走査熱量計にて、窒素雰囲気下5℃/分の昇温速度によるピークトップ法にて求めた。また、ガラス転移温度は同様の条件で測定し、中点ガラス転移温度を求めた。
残炭率は、リガク製TG8230型示差熱天秤にて、窒素雰囲気下10℃/分の昇温速度で830℃までの測定を行い、重量減少率を100%から除した数値で求めた。
1H−NMR及び13C−NMRは、バリアン社製UNITY−INOVA 400MHzを用い、TMSを基準物質としてDMSO−d6溶媒で測定した。
屈折率は、京都電子工業製RA−520N型屈折率計を用い、25℃にて1、5及び10質量%の各濃度でプロピレングリコールモノメチルエーテルアセテート(PGMEA)に溶解して測定し、検量線を作成して100質量%時の換算屈折率を求めた。
吸収スペクトルは、日本分光製分光光度計V−570を用いて1×10−5mol/L濃度でDMSOに溶解して測定を行い、蛍光スペクトルは、日立ハイテクノロジーズ社製蛍光分光光度計F−4010を用い、1×10−5mol/L濃度でDMSOに溶解して極大波長で励起させて測定を行った。また、アズワン製ハンディーUVランプSLUV−4を用いて、365nmの紫外線を照射し、発光の有無を観察した。
300mlの還流管付き反応容器にフェノール(112.8g,1.20mol)、アントラセン−9−カルボアルデヒド(49.4g,0.24mol)及びメタノール(11.3g)を入れ、40℃にて溶解した。濃硫酸(5.6g)を投入し、40℃で24時間反応を行った。次いで、反応液をメチルイソブチルケトン(169.2g)に溶解し、蒸留水(56.4g)にて水洗を数回行って触媒を除去した。減圧下にて、メチルイソブチルケトン及びフェノールを留去した後、キシレン(169.2g)及び蒸留水(11.3g)投入して10℃で攪拌した。析出した結晶を濾別後、減圧乾燥を行って、淡黄色の9−(4−ヒドロキシベンジル)−10−(4−ヒドロキシフェニル)アントラセン48.3g(収率53.3%)を得た。
300mlの還流管付き反応容器に合成例1で得られた結晶(26.3g,0.07mol)、純水263.2g、48%苛性ソーダ(23.4g,0.28mol)を入れ、40℃で溶解した。37%ホルムアルデヒド水溶液(45.4g,0.56mol)を投入し、40℃で24時間反応を行った。次いで、反応液をメチルエチルケトン(263.2g)に溶解した後、20%硫酸で中和した。撹拌を止めて静置し、水層を除去した。減圧下にてメチルエチルケトンを留去した後、メチルイソブチルケトン(263.5g)及びトルエン(525.0g)を加え、10℃で撹拌した。析出した結晶を濾別し、粗結晶43.6gを得た。得られた粗結晶を、メタノール(43.6g)、トルエン(43.6g)に溶解した後10℃で撹拌し、析出した結晶を濾別し、減圧乾燥を行って、実施例1のアントラセン誘導体である淡黄色結晶25.4g(収率73.0%)を得た。
300mlの還流管付き反応容器にm−クレゾール(27.0g,0.25mol)及び実施例1で得られた結晶(24.8g,0.05mol)を入れ、撹拌しながら昇温した。80℃で蓚酸(0.08g)を投入し、内温約105℃で還流反応を3時間行った。次いで、還流管を外して170℃まで常圧脱水を行った後、減圧下に未反応のm−クレゾールを除去し、実施例2のノボラック樹脂(35.5g)を得た。
実施例2において、実施例1で得られた結晶(24.8g,0.05mol)の代わりに合成例1で得られた結晶(18.8g,0.05mol)及びパラホルムアルデヒド(6.9g,0.21mol)を用いたこと以外は、実施例2と同様の操作を行い、比較例1のノボラック樹脂(44.0g)を得た。
実施例1において、合成例1で得られた結晶(26.3g,0.07mol)の代わりにビスフェノール−A(16.0g,0.07mol)を用いたこと以外は、実施例1と同様の操作を行い、12.9g(収率53.0%)の2,2−ビス(4−ヒドロキシ−3,5−ジヒドロキシメチルフェニル)プロパン(比較例2の化合物)を得た。
実施例1において、合成例1で得られた結晶(26.3g,0.07mol)の代わりにビスフェノールフルオレンの市販品であるBPAF[商品名:JFEケミカル製/9,9−ビス(4−ヒドロキシフェニル)フルオレン](24.5g,0.07mol)を用いたこと以外は実施例1と同様の操作を行い21.8g(収率66.3%)の9,9−ビス(4−ヒドロキシ−3,5−ジヒドロキシメチルフェニル)フルオレン(比較例3の化合物)を得た。
実施例2において、実施例1で得られた結晶(24.8g,0.05mol)の代わりに比較例2で得られた結晶(17.4g,0.05mol)を用いたこと以外は、実施例2と同様の操作を行い、比較例4のノボラック樹脂(29.7g)を得た。
実施例2において、実施例1で得られた結晶(24.8g,0.05mol)の代わりに比較例3で得られた結晶(14.1g,0.05mol)を用いたこと以外は、実施例2と同様の操作を行い、比較例5のノボラック樹脂(20.7g)を得た。
Claims (6)
- 下記式(1)にて表されるアントラセン誘導体。
- 上記X及びYは、それぞれ独立に、芳香環上の1又は2の水素原子が*−CH2OZで置換されているヒドロキシフェニル基である請求項1に記載のアントラセン誘導体。
- 上記Zが、水素原子である請求項1又は請求項2に記載のアントラセン誘導体。
- 請求項1、請求項2又は請求項3に記載のアントラセン誘導体を用いて得られる樹脂。
- 請求項1、請求項2又は請求項3に記載のアントラセン誘導体及び請求項4に記載の樹脂からなる群より選ばれる少なくとも1種を含む硬化性組成物。
- 請求項5に記載の硬化性組成物を硬化して得られる硬化物。
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JP2012224723A (ja) * | 2011-04-18 | 2012-11-15 | Asahi Organic Chemicals Industry Co Ltd | フェノール樹脂、これを含む硬化性組成物及び硬化物 |
JP2013140203A (ja) * | 2011-12-28 | 2013-07-18 | Mitsubishi Gas Chemical Co Inc | 感放射線性組成物及びレジストパターン形成方法 |
JP2016029160A (ja) * | 2014-07-15 | 2016-03-03 | ローム アンド ハース エレクトロニック マテリアルズ エルエルシーRohm and Haas Electronic Materials LLC | 下地層用の樹脂 |
JP2016108297A (ja) * | 2014-12-09 | 2016-06-20 | 旭有機材工業株式会社 | アントラセン誘導体、その製造方法、フェノール樹脂、フォトレジスト用組成物及び発光剤 |
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JP2016108297A (ja) * | 2014-12-09 | 2016-06-20 | 旭有機材工業株式会社 | アントラセン誘導体、その製造方法、フェノール樹脂、フォトレジスト用組成物及び発光剤 |
WO2020039708A1 (ja) | 2018-08-23 | 2020-02-27 | 国立大学法人九州大学 | 有機エレクトロルミネッセンス素子 |
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