JP2020164518A - フルオレン化合物およびその製造方法 - Google Patents
フルオレン化合物およびその製造方法 Download PDFInfo
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- -1 Fluorene compound Chemical class 0.000 title abstract description 147
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 title abstract description 112
- 125000001424 substituent group Chemical group 0.000 claims abstract description 20
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 14
- 239000011248 coating agent Substances 0.000 claims description 73
- 238000000576 coating method Methods 0.000 claims description 63
- 238000000295 emission spectrum Methods 0.000 claims description 61
- 239000000463 material Substances 0.000 claims description 47
- 239000007787 solid Substances 0.000 claims description 47
- 239000000203 mixture Substances 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 25
- 238000005859 coupling reaction Methods 0.000 claims description 24
- 125000001624 naphthyl group Chemical group 0.000 claims description 18
- 235000010290 biphenyl Nutrition 0.000 claims description 15
- 239000004305 biphenyl Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 6
- 238000001514 detection method Methods 0.000 claims description 6
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- 150000004945 aromatic hydrocarbons Chemical group 0.000 abstract description 10
- 238000006862 quantum yield reaction Methods 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
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- 125000003118 aryl group Chemical group 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
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- 125000000217 alkyl group Chemical group 0.000 description 29
- 239000002904 solvent Substances 0.000 description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
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- 125000003710 aryl alkyl group Chemical group 0.000 description 20
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- 125000003545 alkoxy group Chemical group 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 19
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- 125000003367 polycyclic group Chemical group 0.000 description 19
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 125000005027 hydroxyaryl group Chemical group 0.000 description 17
- 239000004793 Polystyrene Substances 0.000 description 16
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- 239000012044 organic layer Substances 0.000 description 16
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- 125000001246 bromo group Chemical group Br* 0.000 description 13
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- 239000000126 substance Substances 0.000 description 13
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- 239000010703 silicon Substances 0.000 description 12
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- 238000001228 spectrum Methods 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 238000010791 quenching Methods 0.000 description 11
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 9
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 9
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
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- 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 7
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- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 229930185605 Bisphenol Natural products 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 150000002220 fluorenes Chemical class 0.000 description 6
- 239000000976 ink Substances 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
- 229920000734 polysilsesquioxane polymer Polymers 0.000 description 6
- 238000012916 structural analysis Methods 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 5
- 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 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- 101150003085 Pdcl gene Proteins 0.000 description 5
- 238000006161 Suzuki-Miyaura coupling reaction Methods 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
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- 229910052749 magnesium Inorganic materials 0.000 description 5
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
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- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
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- XPEIJWZLPWNNOK-UHFFFAOYSA-N (4-phenylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC=C1 XPEIJWZLPWNNOK-UHFFFAOYSA-N 0.000 description 3
- 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 3
- AVXFJPFSWLMKSG-UHFFFAOYSA-N 2,7-dibromo-9h-fluorene Chemical compound BrC1=CC=C2C3=CC=C(Br)C=C3CC2=C1 AVXFJPFSWLMKSG-UHFFFAOYSA-N 0.000 description 3
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- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 2
- 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 2
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- 239000004973 liquid crystal related substance Substances 0.000 description 1
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- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
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- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
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- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
【解決手段】本発明のフルオレン化合物は、下記式(1)で表される。
(式中、Z1a、Z1b、Z2aおよびZ2bはアレーン環を示し、R1a、R1b、R2a、R2b、R3aおよびR3bは置換基を示し、A1aおよびA1bはアルキレン基を示し、k1、k2、p1およびp2は0以上の整数を示し、m1、m2、n1およびn2は0〜4の整数を示し、m1+n1およびm2+n2はそれぞれ独立して0〜4の整数を示し、m1およびm2のうち、少なくとも一方は1以上の整数である)
【選択図】なし
Description
本発明の新規なフルオレン化合物は、下記式(1)で表される。
前記式(1)で表されるフルオレン化合物の製造方法は、特に制限されず、慣用の方法、例えば、下記反応式に従って、下記式(2)で表される化合物と下記式(3)で表される化合物とをカップリング反応(またはクロスカップリング反応)させることで製造してもよい(以下、第1の方法ともいう)。
本発明のフルオレン化合物は、所定の分子構造を有するため、光エネルギーや電気エネルギーなどの外部エネルギーにより励起すると、極めて高い発光量子効率で紫外光または可視光などの短波長な光、例えば、波長350〜400nm程度の紫外光、波長400〜450nm程度の可視光などを発光できる。特に、従来は低かった固体状態における発光量子効率を顕著に向上できる。
本発明の発光性組成物(または紫外光発光性組成物)は、発光材料および/または増感剤として、前記式(1)で表されるフルオレン化合物を少なくとも含んでいる。なお、前記式(1)で表されるフルオレン化合物を増感剤として含む場合、通常、他の発光材料を含むことが多い。前記式(1)で表されるフルオレン化合物は、単独でまたは二種以上組み合わせて使用することもできる。このような発光性組成物は、種々の形態または用途において利用でき、例えば、塗料またはインク組成物などのコーティング剤などが挙げられる。
本発明の発光素子(または光電変換素子)は、発光材料および/または増感剤として少なくとも前記式(1)で表されるフルオレン化合物を含んでいる。なお、前記式(1)で表されるフルオレン化合物を増感剤として含む場合、通常、他の発光材料を含むことが多い。
(NMR)
BRUKER社製「ULTRASHIELD300」を用いて測定した。
(株)リガク製「RAXIS−rapid II」を用いて測定した。
(株)島津製作所製「LC−20A」を用いて測定した。
分光蛍光光度計((株)日立ハイテクノロジーズ製「F−4500」、光源:キセノンランプ、検出器:光電子増倍管、分光器:回折格子)を用いて、試料の励起スペクトルおよび発光(蛍光またはりん光)スペクトルを室温下(25℃)で測定し、励起スペクトルの極大波長λex,max、発光スペクトルの極大波長λem,maxおよびλem,maxを含むピーク(または吸収帯)の半値幅を求めた。
蛍光積分球ユニット(日本分光(株)製「ILF−533」、直径100mmφ)を取り付けた蛍光分光光度計(日本分光(株)製「FP−6500」、光源:キセノンランプ、検出器:光電子増倍管、分光器:回折格子)を、付属の校正用標準光源を用いて得た装置関数によりスペクトル補正を行い、スペクトル面積とフォトン数が比例する状態にした後に、絶対法により発光量子効率を算出した。試料を設置しない状態で励起光を測定して照射する励起光のスペクトル面積を求め、次に試料を設置した状態で励起光を測定して試料に吸収されなかった照射励起光のスペクトル面積を求め、これらの差を求めることで試料に吸収されたフォトン数を算出した。同時に試料の発光スペクトルも観測し、そのスペクトル面積から発光したフォトン数を算出した。最後に吸収されたフォトン数に対する発光したフォトン数から発光量子効率を算出した。
(合成例1)BEPF−Brの調製
(固体状態における発光特性)
実施例および参考例で調製したフルオレン化合物の固体状態における励起スペクトルおよび発光スペクトル、並びに発光量子効率を測定した。表1に試料と得られたスペクトルとの対応関係およびスペクトル測定条件を示し、表2ならびに図1〜7および15〜16に測定結果を示す。なお、表1中、「発光波長」は、励起スペクトルにおいて発光強度をモニターした波長を示し、「励起波長」は、発光スペクトルにおける励起光の波長を示す(以下、表3も同じ)。
実施例および参考例で調製したフルオレン化合物をジクロロメタンに表3に記載の濃度で溶解し、溶液状態における励起スペクトルおよび発光スペクトル、並びに発光量子効率を測定した。表3に試料と得られたスペクトルとの対応関係およびスペクトル測定条件を示し、表4ならびに図8〜14および17〜18に測定結果を示す。
実施例1〜4で調製したフルオレン化合物0.01gまたは0.001gと、後述のバインダー成分0.01gとを、クロロホルムに固形分濃度が5質量%となるように混合して混合液(コーティング剤)を調製した。詳しくは、表5に示すように、各フルオレン化合物および各バインダー成分はそれぞれ単独で用いて混合して、両者の割合がフルオレン化合物/バインダー成分(質量比)=1/1または1/10となる合計24種類のコーティング剤を調製した。
PC:ポリカーボネート、三菱エンジニアリングプラスチックス(株)製
PMMA:ポリメチルメタクリレート、三菱レイヨン(株)製
PPSQ:ポリフェニルシルセスキオキサン、下記記載の方法により調製したもの
トリメトキシフェニルシラン1mmolと、溶媒としてのテトラヒドロフラン1.5mLと、酸触媒としてのギ酸(60μL)と、水(60μL)とを混合し、90℃で3時間加熱攪拌して加水分解反応及び縮合反応を行い乾固させた。放冷後、純水で残留する酸を洗い流し、次いでテトラヒドロフラン1.5mLを加えて再度溶液とし、110℃で2時間、加熱攪拌し、乾固することでポリフェニルシルセスキオキサン(PPSQ、下記式で表される化合物)を合成した。
Claims (11)
- 下記式(1)
で表される化合物。 - 前記式(1)において、Z1aおよびZ1bがC6−12アレーン環であり、Z2aおよびZ2bがC6−12アレーン環であり、A1aおよびA1bが直鎖状または分岐鎖状C1−6アルキレン基であり、m1およびm2が0〜2の整数である請求項1記載の化合物。
- 前記式(1)において、Z1aおよびZ1bがベンゼン環、ナフタレン環またはビフェニル環であり、Z2aおよびZ2bがベンゼン環、ナフタレン環またはビフェニル環であり、A1aおよびA1bが直鎖状または分岐鎖状C1−4アルキレン基であり、m1およびm2が1である請求項1または2記載の化合物。
- 固体状態での発光スペクトルにおいて、極大波長λem,maxが350〜450nm、半値幅が60nm以下である発光ピークを少なくとも1つ含み、発光量子効率が40%以上である請求項1〜3のいずれか1項に記載の化合物。
- 発光材料および/または増感剤である請求項1〜4のいずれか1項に記載の化合物。
- 下記式(2)
で表される化合物と、下記式(3)
で表される化合物とをカップリング反応させる工程;または、下記式(4)
で表される化合物と、下記式(5)
で表される化合物を反応させる工程を含む、請求項1〜5のいずれか1項に記載の化合物の製造方法。 - 請求項1〜5のいずれか1項に記載の化合物を励起して、発光させる方法。
- 請求項1〜5のいずれか1項に記載の化合物を含む発光性組成物。
- コーティング剤である請求項8記載の発光性組成物。
- 請求項8または9に記載の発光性組成物で形成された塗膜に光を照射して、塗膜から放出される光を少なくとも検出器を備えた検出装置により検出する方法。
- 請求項1〜5のいずれか1項に記載の化合物を含む発光素子。
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