JP6451140B2 - トリアジン化合物、その製造方法、およびその用途 - Google Patents
トリアジン化合物、その製造方法、およびその用途 Download PDFInfo
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- JP6451140B2 JP6451140B2 JP2014163920A JP2014163920A JP6451140B2 JP 6451140 B2 JP6451140 B2 JP 6451140B2 JP 2014163920 A JP2014163920 A JP 2014163920A JP 2014163920 A JP2014163920 A JP 2014163920A JP 6451140 B2 JP6451140 B2 JP 6451140B2
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- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 4
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- 229910052976 metal sulfide Inorganic materials 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000004492 methyl ester group Chemical group 0.000 description 1
- XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical compound COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- MESMXXUBQDBBSR-UHFFFAOYSA-N n,9-diphenyl-n-[4-[4-(n-(9-phenylcarbazol-3-yl)anilino)phenyl]phenyl]carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)C=C1 MESMXXUBQDBBSR-UHFFFAOYSA-N 0.000 description 1
- 229940078494 nickel acetate Drugs 0.000 description 1
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 1
- GAIQJSWQJOZOMI-UHFFFAOYSA-L nickel(2+);dibenzoate Chemical compound [Ni+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 GAIQJSWQJOZOMI-UHFFFAOYSA-L 0.000 description 1
- UQPSGBZICXWIAG-UHFFFAOYSA-L nickel(2+);dibromide;trihydrate Chemical compound O.O.O.Br[Ni]Br UQPSGBZICXWIAG-UHFFFAOYSA-L 0.000 description 1
- HZPNKQREYVVATQ-UHFFFAOYSA-L nickel(2+);diformate Chemical compound [Ni+2].[O-]C=O.[O-]C=O HZPNKQREYVVATQ-UHFFFAOYSA-L 0.000 description 1
- ZLQBNKOPBDZKDP-UHFFFAOYSA-L nickel(2+);diperchlorate Chemical compound [Ni+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O ZLQBNKOPBDZKDP-UHFFFAOYSA-L 0.000 description 1
- DOLZKNFSRCEOFV-UHFFFAOYSA-L nickel(2+);oxalate Chemical compound [Ni+2].[O-]C(=O)C([O-])=O DOLZKNFSRCEOFV-UHFFFAOYSA-L 0.000 description 1
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
- DBJLJFTWODWSOF-UHFFFAOYSA-L nickel(ii) fluoride Chemical compound F[Ni]F DBJLJFTWODWSOF-UHFFFAOYSA-L 0.000 description 1
- BFSQJYRFLQUZKX-UHFFFAOYSA-L nickel(ii) iodide Chemical compound I[Ni]I BFSQJYRFLQUZKX-UHFFFAOYSA-L 0.000 description 1
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 1
- USPVIMZDBBWXGM-UHFFFAOYSA-N nickel;oxotungsten Chemical compound [Ni].[W]=O USPVIMZDBBWXGM-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- PBDBXAQKXCXZCJ-UHFFFAOYSA-L palladium(2+);2,2,2-trifluoroacetate Chemical compound [Pd+2].[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F PBDBXAQKXCXZCJ-UHFFFAOYSA-L 0.000 description 1
- PENAXHPKEVTBLF-UHFFFAOYSA-L palladium(2+);prop-1-ene;dichloride Chemical class [Pd+]Cl.[Pd+]Cl.[CH2-]C=C.[CH2-]C=C PENAXHPKEVTBLF-UHFFFAOYSA-L 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 description 1
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000005062 perfluorophenyl group Chemical group FC1=C(C(=C(C(=C1F)F)F)F)* 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 229910001404 rare earth metal oxide Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003346 selenoethers Chemical class 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 150000004882 thiopyrans Chemical class 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 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 1
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- KAAYGTMPJQOOGY-UHFFFAOYSA-N tris(2,5-dimethylphenyl)phosphane Chemical compound CC1=CC=C(C)C(P(C=2C(=CC=C(C)C=2)C)C=2C(=CC=C(C)C=2)C)=C1 KAAYGTMPJQOOGY-UHFFFAOYSA-N 0.000 description 1
- DLQYXUGCCKQSRJ-UHFFFAOYSA-N tris(furan-2-yl)phosphane Chemical compound C1=COC(P(C=2OC=CC=2)C=2OC=CC=2)=C1 DLQYXUGCCKQSRJ-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Ar1およびAr2は、各々独立に、炭素数6〜12の芳香族炭化水素基(該基は、メチル基、メトキシ基、ピリジル基、ピリミジル基、フッ素原子、または炭素数2〜10のアルキル基、アルコキシ基、アルコキシアルキル基、エステル基もしくはエステルアルキル基で置換されていてもよい)を表す。
Ar3は、連結及び/又は縮環していてもよい炭素数10〜26の芳香族炭化水素基または連結及び/又は縮環していてもよい炭素数8〜25の含窒素へテロ芳香族基(これらの基は、メチル基、メトキシ基、フッ素原子、または炭素数2〜10のアルキル基、アルコキシ基、アルコキシアルキル基、エステル基もしくはエステルアルキル基で置換されていてもよい)を表す。
Xは酸素原子もしくは硫黄原子を表す。
R1、R2、R3、R4、R5、R6およびR7は、各々独立に、水素原子、メチル基、メトキシ基、フェニル基、フッ素原子、または炭素数2〜10のアルキル基、アルコキシ基、アルコキシアルキル基、エステル基もしくはエステルアルキル基を表す。
また、式中の各水素原子は各々独立に重水素原子であってもよい。)
反応系中で調製することもできる。
で示される方法で製造することができる。
アルゴン気流下、4−(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)−10H−フェノチアジン 3.42g(8.30mmol)、1−クロロ−3,5−ジフェニルトリアジン 2.44g(9.13mmol)、テトラキス(トリフェニルホスフィノ)パラジウム 192mg(0.166mmol)、および炭酸カリウム 2.28g(16.5mmol)をジオキサン 80mLおよび水 5.5mLの混合溶媒に添加し、95℃で20時間加熱撹拌した。室温まで放冷後、クロロホルムおよび水を加えて分液抽出を行い、有機層をあつめて減圧留去した。得られた粗生成物をシリカゲルクロマトグラフィー(展開溶媒クロロホルム:ヘキサン=1:1)で精製することで、目的の4−(4,6−ジフェニル−1,3,5−トリアジン−2−イル)−10H−フェノチアジンの薄黄粉末(収量2.02g,収率56%)を得た。
実験例−2(実施例)
実験例−3(実施例)
実験例−4(実施例)
試験例−1(実施例)
有機電界発光素子の作製および評価を以下の様にして行った。基板には、2mm幅の酸化インジウム−スズ(ITO)膜がストライプ状にパターンされたITO透明電極付きガラス基板を用いた。この基板をイソプロピルアルコールで洗浄した後、酸素プラズマ洗浄にて表面処理を行った。洗浄後の基板に、真空蒸着法で各層の真空蒸着を行い、断面図を図1に示すような、発光面積4mm2の有機電界発光素子を作製した。
正孔注入層2としては、昇華精製したHILを65nmの膜厚で真空蒸着した。
正孔輸送層3としては、HATとHTLをそれぞれ5nm、10nmの膜厚で真空蒸着した。
発光層4としては、EML−1とEML−2を954:46(質量%)の割合で25nmの膜厚で真空蒸着した。
電子輸送層5としては、本発明の実験例−2で合成した4−(4,6−ジフェニル−1,3,5−トリアジン−2−イル)−10−{3,5−ビス(2−ピリジル)フェニル}フェノチアジン(化合物 C84)を30nmの膜厚で真空蒸着した。
最後に、ITOストライプと直交するようにメタルマスクを配し、陰極層6を成膜した。陰極層6としては、Liqと銀マグネシウム、銀をそれぞれ0.5nm、80nmと20nmの膜厚で真空蒸着し、三層構造とした。
試験例−1の電子輸送層5の4−(4,6−ジフェニル−1,3,5−トリアジン−2−イル)−10−{3,5−ビス(2−ピリジル)フェニル}フェノチアジン(化合物 C84)に変えて、実験例−3で得られた4−(4,6−ジフェニル−1,3,5−トリアジン−2−イル)−10−{3−(2−ピリジル)フェニル}フェノチアジン(化合物 C69)を用いた以外は、試験例−1と同様にして有機電界発光素子を作製し、試験例−1と同様に評価した。測定結果を表1に示す。
試験例−1の電子輸送層5の4−(4,6−ジフェニル−1,3,5−トリアジン−2−イル)−10−{3,5−ビス(2−ピリジル)フェニル}フェノチアジン(化合物 C84)に変えて、実験例−4で得られた4−(4,6−ジフェニル−1,3,5−トリアジン−2−イル)−10−(8−キノリル)フェノチアジン(化合物 C35)を用いた以外は、試験例−1と同様にして有機電界発光素子を作製し、試験例−1と同様に評価した。測定結果を表1に示す。
作製した素子の測定値は、それぞれ454cd/m2、4.54cd/Aであった。また、この素子の連続点灯時の輝度25%劣化時間は、343時間であった。
試験例−1の電子輸送層5の4−(4,6−ジフェニル−1,3,5−トリアジン−2−イル)−10−{3,5−ビス(2−ピリジル)フェニル}フェノチアジン(化合物 C84)に変えて、特許番号WO2008129912に記載の2,4−ジフェニル−6−[4,4’’−ジ(2−ピリジル)−1,1’:3’,1’’−テルフェニル−5’−イル]−1,3,5−トリアジン(下記式で表される)を真空蒸着した有機電界発光素子を、試験例−1と同様に作製、測定した。測定結果を表1に示す。
2.正孔注入層
3.正孔輸送層
4.発光層
5.電子輸送層
6.陰極層
Claims (14)
- 一般式(1)で示されるトリアジン化合物。
Ar1およびAr2は、各々独立に、炭素数6〜12の芳香族炭化水素基(該基は、メチル基、メトキシ基、ピリジル基、ピリミジル基、フッ素原子、または炭素数2〜10のアルキル基、アルコキシ基、アルコキシアルキル基、−COOR 8 基もしくは−R 9 COOR 10 基で置換されていてもよい)を表す。
Ar3は、連結及び/又は縮環していてもよい炭素数10〜26の芳香族炭化水素基または連結及び/又は縮環していてもよい炭素数8〜25の含窒素へテロ芳香族基(これらの基は、メチル基、メトキシ基、フッ素原子、または炭素数2〜10のアルキル基、アルコキシ基、アルコキシアルキル基、−COOR 8 基もしくは−R 9 COOR 10 基で置換されていてもよい)を表す。
Xは酸素原子もしくは硫黄原子を表す。
R1、R2、R3、R4、R5、R6およびR7は、各々独立に、水素原子、メチル基、メトキシ基、フェニル基、フッ素原子、または炭素数2〜10のアルキル基、アルコキシ基、アルコキシアルキル基、−COOR8基もしくは−R9COOR10基を表す。
R8、R9およびR10は、各々独立に、任意の炭化水素基である。
また、式中の各水素原子は各々独立に重水素原子であってもよい。) - Ar3が、連結および/または縮環していてもよい炭素数10〜22の芳香族炭化水素基、もしくは連結および/または縮環していてもよい炭素数8〜21の含窒素へテロ芳香族基(これらの基は、メチル基、メトキシ基、フッ素原子、炭素数2〜10のアルキル基、または炭素数2〜10のアルコキシ基で置換されていてもよい)である請求項1に記載のトリアジン化合物。
- Ar3が、ベンゼン環を2〜5つ連結および/または縮環して形成される炭素数10〜26の芳香族炭化水素基、ベンゼン環、ピリジン環、およびピリミジン環からなる群より選ばれる環を2〜5つ連結および/または縮環して形成される炭素数8〜25の含窒素へテロ芳香族基(これらの基は、メチル基、メトキシ基、フッ素原子、炭素数2〜10のアルキル基、または炭素数2〜10のアルコキシ基で置換されていてもよい)である請求項1に記載のトリアジン化合物。
- Ar3が、ベンゼン環を2〜4つ連結および/または縮環して形成される炭素数10〜22の芳香族炭化水素基、ベンゼン環、ピリジン環、およびピリミジン環からなる群より選ばれる環を2〜4つ連結および/または縮環して形成される炭素数8〜21の含窒素へテロ芳香族基(これらの基は、メチル基、メトキシ基、フッ素原子、炭素数2〜10のアルキル基、または炭素数2〜10のアルコキシ基で置換されていてもよい)である請求項3に記載のトリアジン化合物。
- R1、R2、R3、R4、R5、R6およびR7が、各々独立に、水素原子、メチル基、またはフェニル基である請求項1〜4のいずれか一項に記載のトリアジン化合物。
- R1、R2、R3、R4、R5、R6およびR7が、水素原子である請求項1〜5のいずれか一項に記載のトリアジン化合物。
- Ar1およびAr2が、各々独立に、フェニル基、ナフチル基、またはビフェニル基(これらの基は、メチル基、メトキシ基、ピリジル基、ピリミジル基、またはフッ素原子で置換されていてもよい)である請求項1〜6のいずれか一項に記載のトリアジン化合物。
- Ar1およびAr2が、フェニル基である請求項1〜7のいずれか一項に記載のトリアジン化合物。
- 金属触媒の存在下、一般式(2)で表される化合物と一般式(3)で表される化合物をカップリング反応させることを特徴とする、請求項1に記載のトリアジン化合物の製造方法。
Ar1およびAr2は、各々独立に、炭素数6〜12の芳香族炭化水素基(該基は、メチル基、メトキシ基、ピリジル基、ピリミジル基、フッ素原子、または炭素数2〜10のアルキル基、アルコキシ基、アルコキシアルキル基、−COOR 8 基もしくは−R 9 COOR 10 基で置換されていてもよい)を表す。
Ar3は、連結及び/又は縮環していてもよい炭素数10〜26の芳香族炭化水素基または連結及び/又は縮環していてもよい炭素数8〜25の含窒素へテロ芳香族基(これらの基は、メチル基、メトキシ基、フッ素原子、または炭素数2〜10のアルキル基、アルコキシ基、アルコキシアルキル基、−COOR 8 基もしくは−R 9 COOR 10 基で置換されていてもよい)を表す。
Xは酸素原子もしくは硫黄原子を表す。
R1、R2、R3、R4、R5、R6およびR7は、各々独立に、水素原子、メチル基、メトキシ基、フェニル基、フッ素原子、または炭素数2〜10のアルキル基、アルコキシ基、アルコキシアルキル基、−COOR8基もしくは−R9COOR10基を表す。
R8、R9およびR10は、各々独立に、任意の炭化水素基である。
また、式中の各水素原子は各々独立に重水素原子であってもよい。
M1は脱離基を表す。) - 一般式(2)で表されるトリアジン化合物。
Ar1およびAr2は、各々独立に、炭素数6〜12の芳香族炭化水素基(該基は、メチル基、メトキシ基、ピリジル基、ピリミジル基、フッ素原子、または炭素数2〜10のアルキル基、アルコキシ基、アルコキシアルキル基、−COOR 8 基もしくは−R 9 COOR 10 基で置換されていてもよい)を表す。
Xは酸素原子もしくは硫黄原子を表す。
R1、R2、R3、R4、R5、R6およびR7は、各々独立に、水素原子、メチル基、メトキシ基、フェニル基、フッ素原子、または炭素数2〜10のアルキル基、アルコキシ基、アルコキシアルキル基、−COOR8基もしくは−R9COOR10基を表す。
R8、R9およびR10は、各々独立に、任意の炭化水素基である。
また、式中の各水素原子は各々独立に重水素原子であってもよい。) - 金属触媒の存在下、一般式(4)で示される化合物と一般式(5)で表される化合物をカップリング反応させることを特徴とする、請求項10に記載の一般式(2)で表されるトリアジン化合物の製造方法。
Ar1およびAr2は、各々独立に、炭素数6〜12の芳香族炭化水素基(該基は、メチル基、メトキシ基、ピリジル基、ピリミジル基、フッ素原子、または炭素数2〜10のアルキル基、アルコキシ基、アルコキシアルキル基、−COOR 8 基もしくは−R 9 COOR 10 基で置換されていてもよい)を表す。
Xは酸素原子もしくは硫黄原子を表す。
R1、R2、R3、R4、R5、R6およびR7は、各々独立に、水素原子、メチル基、メトキシ基、フェニル基、フッ素原子、または炭素数2〜10のアルキル基、アルコキシ基、アルコキシアルキル基、−COOR8基もしくは−R9COOR10基を表す。
R8、R9およびR10は、各々独立に、任意の炭化水素基である。
また、式中の各水素原子は各々独立に重水素原子であってもよい。
Zは金属基、ボロン酸基、またはボロン酸エステル基を表し、M2は脱離基を表す。) - 請求項1〜8のいずれか一項に記載のトリアジン化合物を含む有機電界発光素子用材料。
- 請求項1〜8のいずれか一項に記載のトリアジン化合物を含む発光層ホスト材料、電子注入材料または電子輸送材料。
- 請求項1〜8のいずれか一項に記載のトリアジン化合物を含む電子注入材料または電子輸送材料。
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