JP4644802B2 - Fluorescent diazaanthracenes and method for synthesizing fluorescent diazaanthracenes - Google Patents
Fluorescent diazaanthracenes and method for synthesizing fluorescent diazaanthracenes Download PDFInfo
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- 230000002194 synthesizing effect Effects 0.000 title claims description 4
- BMWYMEQOMFGKSN-UHFFFAOYSA-N benzo[g]cinnoline Chemical class N1=NC=CC2=CC3=CC=CC=C3C=C21 BMWYMEQOMFGKSN-UHFFFAOYSA-N 0.000 title description 13
- 239000000126 substance Substances 0.000 claims description 12
- JOLZWIIAYQNMSJ-UHFFFAOYSA-N phenyl-(2,4,5-tribenzoylphenyl)methanone Chemical compound C=1C(C(=O)C=2C=CC=CC=2)=C(C(=O)C=2C=CC=CC=2)C=C(C(=O)C=2C=CC=CC=2)C=1C(=O)C1=CC=CC=C1 JOLZWIIAYQNMSJ-UHFFFAOYSA-N 0.000 claims description 11
- 238000001308 synthesis method Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- HHSMIVJMVWYXKX-UHFFFAOYSA-N 1,3,4,6,7,9-hexakis-phenylpyrido[4,3-g]isoquinoline Chemical compound c1ccc(cc1)-c1nc(-c2ccccc2)c2cc3c(nc(-c4ccccc4)c(-c4ccccc4)c3cc2c1-c1ccccc1)-c1ccccc1 HHSMIVJMVWYXKX-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- TZKFDCQLDUXMBS-UHFFFAOYSA-N 1,2,4,5-tetrabenzylbenzene Chemical compound C=1C(CC=2C=CC=CC=2)=C(CC=2C=CC=CC=2)C=C(CC=2C=CC=CC=2)C=1CC1=CC=CC=C1 TZKFDCQLDUXMBS-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- UTXIKCCNBUIWPT-UHFFFAOYSA-N 1,2,4,5-tetrakis(bromomethyl)benzene Chemical compound BrCC1=CC(CBr)=C(CBr)C=C1CBr UTXIKCCNBUIWPT-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- FLCLHVZXQPXMME-UHFFFAOYSA-N 1,3,4,6,8,9-hexakis-phenylpyrido[3,4-g]isoquinoline Chemical compound C1(=CC=CC=C1)C1=NC(=C(C2=CC3=C(N=C(C(=C3C=C12)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 FLCLHVZXQPXMME-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 108010043121 Green Fluorescent Proteins Proteins 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000013076 target substance Substances 0.000 description 2
- TXTWXQXDMWILOF-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl)azanium;chloride Chemical compound [Cl-].CCOC(=O)C[NH3+] TXTWXQXDMWILOF-UHFFFAOYSA-N 0.000 description 1
- 0 *c(c(cc1c(-c2ccccc2)nc(*)c(-c2ccccc2)c1c1)c1c(-c1ccccc1)n1)c1O Chemical compound *c(c(cc1c(-c2ccccc2)nc(*)c(-c2ccccc2)c1c1)c1c(-c1ccccc1)n1)c1O 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- SWKLATFJEZTLSR-UHFFFAOYSA-N C1=CC=C2C=C3C=C4C(=CC3=CC2=C1)C=CC5=C4C=C6C(=C5)C=CC=C6C7=NC=CC8=C7C=C9C=NC=CC9=C8 Chemical compound C1=CC=C2C=C3C=C4C(=CC3=CC2=C1)C=CC5=C4C=C6C(=C5)C=CC=C6C7=NC=CC8=C7C=C9C=NC=CC9=C8 SWKLATFJEZTLSR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- BGLGAKMTYHWWKW-UHFFFAOYSA-N acridine yellow Chemical compound [H+].[Cl-].CC1=C(N)C=C2N=C(C=C(C(C)=C3)N)C3=CC2=C1 BGLGAKMTYHWWKW-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- GTGIXCPOLMWQTC-UHFFFAOYSA-N cyanomethylazanium;hydrogen sulfate Chemical compound NCC#N.OS(O)(=O)=O GTGIXCPOLMWQTC-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- -1 monocyclic compound Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
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- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
本発明は、新規蛍光物質およびその合成方法に関する。 The present invention relates to a novel fluorescent material and a synthesis method thereof.
アントラセンは色素または蛍光物質として利用され、このような複素環化合物は単素環化合物に比べて著しい濃色性を示す。 Anthracene is used as a dye or a fluorescent substance, and such a heterocyclic compound exhibits a remarkable dark color as compared with a monocyclic compound.
近年は、液晶ディスプレイに代えてＥＬディスプレイの開発が進行しており、特に、有機ＥＬ材料は無機材料に比べて駆動電圧や素材設計の多様性の観点から期待されている。この中でも低分子有機ＥＬ材料は、高分子有機ＥＬ材料と比べて寿命や発光効率の点で優れている。 In recent years, an EL display has been developed in place of a liquid crystal display. In particular, an organic EL material is expected from the viewpoint of driving voltage and diversity of material design as compared with an inorganic material. Among these, the low molecular organic EL material is superior in terms of lifetime and luminous efficiency as compared with the high molecular organic EL material.
本発明は上記に鑑みてなされたものであって、緑色系の新規蛍光物質を提供することを目的とする。 The present invention has been made in view of the above, and an object of the present invention is to provide a new green fluorescent substance.
請求項１に記載の発明は、式（１）
で表される蛍光物質である。
The invention according to claim 1 has the formula (1)
It is a fluorescent substance represented by
請求項２に記載の発明は、式（２）
で表される蛍光物質である。
The invention according to
It is a fluorescent substance represented by
請求項３に記載の発明は、１，２，４，５−テトラベンゾイルベンゼンを用いて請求項１または請求項２の蛍光物質を合成することを特徴とする蛍光物質合成方法である。
The invention described in claim 3 is a fluorescent substance synthesis method characterized in that the fluorescent substance of claim 1 or
なお、式（１）および式（２）で表される物質は、異性体の関係にあるので以降では総称として便宜的にジアザアントラセン類と適宜称することとする。また、置換基Ｒのうち、アリール基としては、例えば、フェニル基、チエニル基、ピリジル基、ナフチル基を挙げることができ、また、低級アルキル基としては、例えば、Ｃ＝１〜４のアルキル基を挙げることができる。 In addition, since the substances represented by the formulas (1) and (2) are in an isomer relationship, they will be appropriately referred to as diazaanthracenes as a general term for convenience hereinafter. Among the substituents R, examples of the aryl group include a phenyl group, a thienyl group, a pyridyl group, and a naphthyl group. Examples of the lower alkyl group include a C = 1-4 alkyl group. Can be mentioned.
本発明によれば、緑色系の新規蛍光物質を提供することが可能となる。 According to the present invention, it is possible to provide a new green fluorescent material.
試験例１．
試験例１では、まず、Ｒをフェニル基としたジアザアントラセン類の合成方法を説明し、次に、その物性について説明する。
Test Example 1
In Test Example 1, first, a synthesis method of diazaanthracenes in which R is a phenyl group will be described, and then the physical properties thereof will be described.
〔合成方法〕
次の反応式は、１，２，４，５−テトラキス（ブロモメチル）ベンゼンを出発物質として、Ｒをフェニル基としたジアザアントラセン類を合成するスキームを示した図である。但し、ここでは、Ｒとして他の置換基も併せて表記した。
Ｒをフェニル基としたジアザアントラセン類を合成するスキームとしては、まず、１，２，４，５−テトラキス（ブロモメチル）ベンゼンから１，２，４，５−テトラベンジルベンゼンを合成し（ステップ１）、次に、１，２，４，５−テトラベンジルベンゼンから１，２，４，５−テトラベンゾイルベンゼンを合成し（ステップ２）、最後に１，２，４，５−テトラベンゾイルベンゼンから目的物質のジアザアントラセン類である１，３，４，５，６，８−ヘキサフェニル−２，７−ジアザアントラセンおよび１，３，４，５，７，８−ヘキサフェニル−２，６−ジアザアントラセンを得た（ステップ３）。
(Synthesis method)
The following reaction formula shows a scheme for synthesizing diazaanthracenes using 1,2,4,5-tetrakis (bromomethyl) benzene as a starting material and R as a phenyl group. However, here, other substituents are also represented as R.
As a scheme for synthesizing diazaanthracenes having R as a phenyl group, first, 1,2,4,5-tetrabenzylbenzene is synthesized from 1,2,4,5-tetrakis (bromomethyl) benzene (Step 1). Next, 1,2,4,5-tetrabenzoylbenzene is synthesized from 1,2,4,5-tetrabenzylbenzene (step 2), and finally from 1,2,4,5-tetrabenzoylbenzene. 1,3,4,5,6,8-hexaphenyl-2,7-diazaanthracene and 1,3,4,5,7,8-hexaphenyl-2,6 which are diazaanthracenes of the target substance -Diazaanthracene was obtained (step 3).
次に各ステップについて説明する。
（ステップ１）１，２，４，５−テトラベンジルベンゼンの合成：
まず、１，２，４，５−テトラキス（ブロモメチル）ベンゼンと無水塩化鉄をベンゼン中で一晩加熱環流させた。希塩酸を少量加えた水にこの反応混合物を注いだ。これをベンゼンで抽出し、ＭｇＳＯ４で乾燥させた後、減圧下で溶媒を留去した。残渣をメタノールで熱抽出し、減圧下で溶媒を留去して、略無色の結晶である１，２，４，５−テトラベンジルベンゼンを得た。
Next, each step will be described.
(Step 1) Synthesis of 1,2,4,5-tetrabenzylbenzene:
First, 1,2,4,5-tetrakis (bromomethyl) benzene and anhydrous iron chloride were heated and refluxed overnight in benzene. The reaction mixture was poured into water with a small amount of diluted hydrochloric acid added. This was extracted with benzene, dried over MgSO 4 , and then the solvent was distilled off under reduced pressure. The residue was subjected to hot extraction with methanol, and the solvent was distilled off under reduced pressure to obtain 1,2,4,5-tetrabenzylbenzene as substantially colorless crystals.
なお、最初の反応として、ベンゼンにＡｌＣｌ３とＣＨ３ＮＯ２を溶かし、１，２，４，５−テトラキス（ブロモメチル）ベンゼンを加えて５時間撹拌し、その後は、上述したのと同様にしても１，２，４，５−テトラベンジルベンゼンを得ることが出来る。 As the first reaction, AlCl 3 and CH 3 NO 2 are dissolved in benzene, 1,2,4,5-tetrakis (bromomethyl) benzene is added and stirred for 5 hours, and then the same as described above. Can also obtain 1,2,4,5-tetrabenzylbenzene.
表１に、反応の結果を示す。
表に示したように、収率は後者の反応の方が優れていることが確認できた。なお、文献（ｌｉｔ．）はＪ．Ｏｒｇ．Ｃｈｅｍ．，３８，３９７７（１９７３）による。
Table 1 shows the results of the reaction.
As shown in the table, it was confirmed that the latter reaction was superior in yield. Note that the literature (lit.) is J.I. Org. Chem. 38, 3977 (1973).
（ステップ２）１，２，４，５−テトラベンゾイルベンゼンの合成：
ステップ１で得られた１，２，４，５−テトラベンジルベンゼンとＣｒＯ３を酢酸中で２時間加熱環流させた。反応混合液を水に注いで生じた粉末をろ取した。この粉末を酢酸を用いて再結晶させ１，２，４，５−テトラベンゾイルベンゼンを得た。
(Step 2) Synthesis of 1,2,4,5-tetrabenzoylbenzene:
The 1,2,4,5-tetrabenzylbenzene and CrO 3 obtained in Step 1 were heated to reflux in acetic acid for 2 hours. The reaction mixture was poured into water and the resulting powder was collected by filtration. This powder was recrystallized using acetic acid to obtain 1,2,4,5-tetrabenzoylbenzene.
表２に、反応の結果を示す。
表に示したように、収率は５４％であった。
Table 2 shows the results of the reaction.
As shown in the table, the yield was 54%.
（ステップ３）１，３，４，５，６，８−ヘキサフェニル−２，７−ジアザアントラセンおよび１，３，４，５，７，８−ヘキサフェニル−２，６−ジアザアントラセンの合成：
ステップ２で得られた１，２，４，５−テトラベンゾイルベンゼンとＰｈＣＨ２ＮＨ２をＫＯＨのエタノール溶液中で１時間加熱環流した。反応混合物に水を加えて生じた固体をろ取した。ろ取した固体をシクロヘキサンでソックスレー抽出をし、減圧下で溶媒を留去して目的物質である１，３，４，５，６，８−ヘキサフェニル−２，７−ジアザアントラセン（式（３））および１，３，４，５，７，８−ヘキサフェニル−２，６−ジアザアントラセン（式（４））の黄色結晶を得た。
(Step 3) 1,3,4,5,6,8-hexaphenyl-2,7-diazaanthracene and 1,3,4,5,7,8-hexaphenyl-2,6-diazaanthracene Synthesis:
The 1,2,4,5-tetrabenzoylbenzene and PhCH 2 NH 2 obtained in
（ステップ３’）１，３，４，５，６，８−ヘキサフェニル−２，７−ジアザアントラセンの単離：
正常に合成できたか確認するため、ステップ３で得られた黄色結晶をシリカゲルカラムクロマトグラフ処理し、ヘキサン−ベンゼンで再結晶を行った。得られた結晶も黄色結晶であり、元素分析の値も合致した（化９参照）。さらに、この結晶の１Ｈ−ＮＭＲを測定したところ９．２３（ｓ，１Ｈ），８．０７（ｓ，１Ｈ）にシグナル値があり、この結晶は、１，３，４，５，６，８−ヘキサフェニル−２，７−ジアザアントラセンであることが確認できた。
(Step 3 ') Isolation of 1,3,4,5,6,8-hexaphenyl-2,7-diazaanthracene:
In order to confirm whether the synthesis was successful, the yellow crystals obtained in Step 3 were subjected to silica gel column chromatography and recrystallized from hexane-benzene. The obtained crystal was also a yellow crystal, and the value of elemental analysis also agreed (see chemical formula 9). Furthermore, when 1 H-NMR of this crystal was measured, there were signal values at 9.23 (s, 1H) and 8.07 (s, 1H). It was confirmed to be 8-hexaphenyl-2,7-diazaanthracene.
表３に、反応の結果を示す。
表に示したように、収率は１５％であった。
Table 3 shows the results of the reaction.
As shown in the table, the yield was 15%.
〔物性〕
ステップ３’で単離した１，３，４，５，６，８−ヘキサフェニル−２，７−ジアザアントラセンの特徴量ないし物性を測定した結果を示す。
上記したように、吸収極大波長は４２３ｎｍであり、吸光強度ｌｏｇεは３．８８であった。なお、吸光スペクトルを図１に示す。また、発光極大波長は５１５ｎｍであった。なお、発光スペクトルを図２に示す。標準物資としてアクリジンイエローを用いた相対的量子収率は０．０４であった。
[Physical properties]
The result of having measured the characteristic quantity thru | or physical property of 1,3,4,5,6,8-hexaphenyl-2,7-diazaanthracene isolated at step 3 'is shown.
As described above, the absorption maximum wavelength was 423 nm, and the absorbance intensity log ε was 3.88. The absorption spectrum is shown in FIG. The emission maximum wavelength was 515 nm. The emission spectrum is shown in FIG. The relative quantum yield using acridine yellow as a standard material was 0.04.
次に、安定性について確認した。まず、このジアザアントラセン類は、室温で空気中に放置しておいても少なくとも１ヶ月は変化しないことを確認した。さらに、水には溶けず、アルコール類には少量しか溶けないことも確認した。なお、クロロホルムには溶解することを確認した。また、アルカリに対しても安定である。熱耐性については、３００℃までは分解しないことを確認した。 Next, stability was confirmed. First, it was confirmed that the diazaanthracenes did not change for at least one month even when left in the air at room temperature. Furthermore, it was confirmed that it was insoluble in water and only a small amount in alcohols. In addition, it confirmed that it melt | dissolved in chloroform. It is also stable against alkali. About heat resistance, it confirmed that it did not decompose | disassemble up to 300 degreeC.
試験例２．
試験例２では、Ｒをカルボキシル基としたジアザアントラセン類の合成方法について説明する。試験例１の合成スキームから分かるように、本発明のジアザアントラセン類を得るための直近の出発物質は１，２，４，５−テトラベンゾイルベンゼンである。試験例２では、これを用いて合成を試みた。
まず、１，２，４，５−テトラベンゾイルベンゼンとグリシンエチルエステル塩酸塩（ＮＨ２ＣＨ２ＣＯＯＣ２Ｈ５・ＨＣｌ）をＫＯＨのエタノール溶液中で２０時間加熱環流させた。反応溶液を水（２００ｍｌ）に注ぎ沈殿物を溶解した。塩酸を加えてｐＨを２〜３の間に調整し、式（５）および式（６）で表される化合物をろ取した。このジアザアントラセン類も蛍光性を示すことを確認した。
Test Example 2
In Test Example 2, a synthesis method of diazaanthracenes in which R is a carboxyl group will be described. As can be seen from the synthesis scheme of Test Example 1, the immediate starting material for obtaining the diazaanthracenes of the present invention is 1,2,4,5-tetrabenzoylbenzene. In Test Example 2, synthesis was attempted using this.
First, 1,2,4,5-tetrabenzoylbenzene and glycine ethyl ester hydrochloride (NH 2 CH 2 COOC 2 H 5 .HCl) were heated to reflux in an ethanol solution of KOH for 20 hours. The reaction solution was poured into water (200 ml) to dissolve the precipitate. Hydrochloric acid was added to adjust the pH between 2 and 3, and the compounds represented by formula (5) and formula (6) were collected by filtration. It was confirmed that these diazaanthracenes also showed fluorescence.
表４に、反応の結果を示す。
試験例３．
試験例３では、Ｒをシアノ基としたジアザアントラセン類の合成方法について説明する。
まず、１，２，４，５−テトラベンゾイルベンゼンと硫酸アミノアセトニトリルをｎ−ブタノール中で加熱環流させた。加熱環流１時間後に紫外線ランプを照射したところ青色蛍光を示すことを確認した。加熱環流後、ｎ−ブタノールを減圧下に留去した。残渣をＩＲ測定したところ、２２４０ｃｍ−１にシアノ基に由来する吸収ピークを確認し、式（７）および式（８）で表される化合物の合成が確認できた。
Test Example 3
In Test Example 3, a synthesis method of diazaanthracenes in which R is a cyano group will be described.
First, 1,2,4,5-tetrabenzoylbenzene and aminoacetonitrile sulfate were heated to reflux in n-butanol. When an ultraviolet lamp was irradiated after 1 hour of heating reflux, it was confirmed to show blue fluorescence. After heating to reflux, n-butanol was distilled off under reduced pressure. When the residue was subjected to IR measurement, an absorption peak derived from a cyano group was confirmed at 2240 cm −1 , and synthesis of the compounds represented by formula (7) and formula (8) could be confirmed.
式（７）
式（８）
Formula (8)
本発明のジアザアントラセン類は、低分子有機ＥＬ材料に適用可能である。なお、出発物質を１，２，４，５−テトラベンゾイルベンゼンとすれば、種々に置換基を変更でき、所望の特性に応じたバリエーションのある蛍光材料を合成可能となる。 The diazaanthracenes of the present invention can be applied to low molecular organic EL materials. If the starting material is 1,2,4,5-tetrabenzoylbenzene, the substituents can be variously changed, and a fluorescent material having variations according to desired characteristics can be synthesized.
Claims (3)
で表される蛍光物質。
Formula (1)
A fluorescent substance represented by
で表される蛍光物質。
Formula (2)
A fluorescent substance represented by
3. A fluorescent substance synthesis method comprising synthesizing the fluorescent substance according to claim 1 or 2, using 1,2,4,5-tetrabenzoylbenzene.
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| JP2002515502A (en) * | 1998-05-21 | 2002-05-28 | ユニベルシダド コムプルテンセ デ マドリッド | Antitumor 1,5-diazaanthraquinone |
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