JPH03202386A - Fluorene compound, its manufacture and recording material using same compound - Google Patents
Fluorene compound, its manufacture and recording material using same compoundInfo
- Publication number
- JPH03202386A JPH03202386A JP2018433A JP1843390A JPH03202386A JP H03202386 A JPH03202386 A JP H03202386A JP 2018433 A JP2018433 A JP 2018433A JP 1843390 A JP1843390 A JP 1843390A JP H03202386 A JPH03202386 A JP H03202386A
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- Japan
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- formulas
- carbon atoms
- formula
- chemical formulas
- 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.)
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- -1 Fluorene compound Chemical class 0.000 title claims abstract description 22
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 239000000463 material Substances 0.000 title claims abstract description 10
- 150000001875 compounds Chemical class 0.000 title claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 239000003086 colorant Substances 0.000 claims abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims 1
- 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 abstract description 6
- 239000013078 crystal Substances 0.000 abstract description 5
- 238000001454 recorded image Methods 0.000 abstract description 2
- 239000002253 acid Substances 0.000 abstract 1
- 239000004927 clay Substances 0.000 abstract 1
- 239000005011 phenolic resin Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000012015 optical character recognition Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
Landscapes
- Heat Sensitive Colour Forming Recording (AREA)
- Color Printing (AREA)
- Furan Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
【発明の詳細な説明】
〔発明の目的〕
本発明は、近赤外領域に吸収を有する新規なフルオレン
化合物、その製造法、および該フルオレン化合物を電子
供与性発色剤として用いる記録材料に関する。DETAILED DESCRIPTION OF THE INVENTION [Object of the Invention] The present invention relates to a novel fluorene compound having absorption in the near-infrared region, a method for producing the same, and a recording material using the fluorene compound as an electron-donating coloring agent.
更に詳しくは、本発明は一般式（１）
み得る）を形成するものとする。）
で示されるフルオレン化合物および該フルオレン化合物
を電子供与性発色剤として用いる記録材料に関する。More specifically, the present invention is intended to form general formula (1). ) and a recording material using the fluorene compound as an electron-donating coloring agent.
また本発明は、−形式（ＩＩ）
（式中Ｅは、
Ｒｓ Ｒｂ
であり、Ｒ＋、 Ｒ２＋ Ｒ３，Ｒａ、 ＲｓおよびＲ
６はいずれも水素、炭素数１〜４のアルキル基、炭素数
５〜７のシクロアルキル基、ヘンシル基を表わす。但し
、Ｒ＋、 Ｒｚ、 Ｒ３，Ｒａ、ＲｓおよびＲ，は全て
が同時には炭素数１〜４のアルキル基を示すことがなく
、又Ｒ１とＲ２、又はＲ８とＲ４は場合によりそれらが
それぞれ結合する窒素原子（アミノ基の窒素原子）とと
もに炭素数４〜６の複素環（第２の窒素原子をも含（式
中Ｅ１およびＲ＋、 Ｒｉ、 ＲｓおよびＲ４は一般式
（Ｉ）中のＥ、およびＲ，、Ｉｌｌ、 ＬおよびＲ４と
同じ意味を表わす。）
で示される化合物をジアゾ化後閉環させることを特徴と
する一般式（Ｉ）で示されるフルオレン化合物の製造法
に関する。The present invention also provides -form (II) (wherein E is Rs Rb , R+, R2+ R3, Ra, Rs and R
Each of 6 represents hydrogen, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, or a Hensyl group. However, R+, Rz, R3, Ra, Rs, and R do not all represent an alkyl group having 1 to 4 carbon atoms at the same time, and R1 and R2, or R8 and R4 may be bonded to each other in some cases. A heterocyclic ring having 4 to 6 carbon atoms (including a second nitrogen atom) together with a nitrogen atom (nitrogen atom of an amino group) (where E1 and R+, Ri, Rs and R4 are E in general formula (I), The present invention relates to a method for producing a fluorene compound represented by the general formula (I), which comprises diazotizing the compound represented by R, , Ill, L and R4 and then ring-closing the compound.
従来より、電子供与性発色剤を用いる記録材料としては
感圧記録紙、感熱記録紙、通電感熱記録紙など種々の形
態のものが知られており、情報化時代と共に、これらの
記録材料の需要が増大している。更に最近は、事務の合
理化にコンピューターが多用されており、その際コンピ
ューターへの情報入力に光学文字読取機が用いられてい
る。この光学文字読取機は、近赤外光を用いて情報を読
取ることが読取りの正確さ、早さなどにおいて有利であ
る。従って、近赤外光で情報を読取るためには、情報が
近赤外領域の光を吸収する物質で記録されていることが
必要である。Recording materials using electron-donating color formers have been known in various forms, such as pressure-sensitive recording paper, heat-sensitive recording paper, and current-carrying heat-sensitive recording paper.With the advent of the information age, demand for these recording materials has increased. is increasing. Furthermore, recently, computers have been widely used to streamline office work, and optical character readers are used to input information into the computers. In this optical character reader, reading information using near-infrared light is advantageous in terms of accuracy and speed of reading. Therefore, in order to read information using near-infrared light, it is necessary that the information be recorded with a substance that absorbs light in the near-infrared region.
しかしながら、従来の電子供与性発色剤を用いる記録材
料による記録像は、近赤外部に吸収を有しないため近赤
外光を用いる光学文字読取機では読取ることができない
と云う大きな欠点があった。However, images recorded by conventional recording materials using electron-donating coloring agents have a major drawback in that they cannot be read by optical character readers that use near-infrared light because they do not absorb near-infrared light.
本発明者らは、従来の記録材料における前記の欠点を克
服すべき鋭意研究を重ねた結果、フルオレン化合物を電
子供与性発色剤として用いた記録材料の記録像が近赤外
部に吸収を有することを見出し既に特開昭５９−１９９
７５７号で出願しているが、本発明はこの特開昭５９−
１９９７５７号の発明を更に発展させた発明に関する。As a result of intensive research to overcome the above-mentioned drawbacks of conventional recording materials, the present inventors have discovered that a recorded image of a recording material using a fluorene compound as an electron-donating coloring agent has absorption in the near-infrared region. Already in the headline JP-A-59-199
No. 757, but the present invention is based on this patent application.
This invention relates to an invention that further develops the invention of No. 199757.
即ち、本発明の一般式（１）で示されるフルオレン化合
物は新規な化合物であり、それ自体は、実質的に無色の
結晶で近赤外部に吸収を有しないが、酸性白土、フェノ
ール樹脂、ヒドロキシ安息香酸エステル、ビスフェノー
ルＡ等の電子受容性顕色剤と反応した状態では図−１に
示すごとく、近赤外部に吸収を有するという優れた性質
を有するものである。That is, the fluorene compound represented by the general formula (1) of the present invention is a new compound, which itself is a substantially colorless crystal and has no absorption in the near-infrared region, but it is a compound that has no absorption in the near-infrared region. When reacted with an electron-accepting color developer such as benzoic acid ester or bisphenol A, it has an excellent property of absorbing in the near-infrared region, as shown in Figure 1.
本発明の一般式（１）で示されるフルオレン化合物は次
のようにして合成される。The fluorene compound represented by the general formula (1) of the present invention is synthesized as follows.
−形式（ＩＩ）で示される化合物を硫酸中−５〜１０°
Ｃ位でジアゾ化し、次いで約１０〜１００°Ｃにおいて
数時間乃至数十時間反応させて閉環させる。尚、銅粉あ
るいは銅化合物の存在下に閉環させることが収率向上に
有効である。次いで反応生成物をアルカリで中和し、析
出物を公知の方法によって溶剤精製すると、一般式（Ｉ
）で示されるフルオレン化合物が実質的に無色の結晶と
して得られる。- Compound of form (II) in sulfuric acid at -5 to 10°
Diazotization is carried out at the C position, followed by reaction at about 10 to 100°C for several hours to several tens of hours to effect ring closure. Note that ring closure in the presence of copper powder or a copper compound is effective for improving the yield. Next, the reaction product is neutralized with an alkali, and the precipitate is purified with a solvent by a known method to obtain the general formula (I
) is obtained as substantially colorless crystals.
（発明の具体例、並びに実施例）
次に本発明の一般式（■・）で示されるフルオレン化合
物の具体例とその融点を次表に示す。但し、本発明の化
合物はこれらに限定されるものではない。(Specific Examples and Examples of the Invention) Next, specific examples of the fluorene compound represented by the general formula (■.) of the present invention and their melting points are shown in the following table. However, the compounds of the present invention are not limited to these.
弘３
２５９−２６１
ｌ憑」］弓召し鉦宣
阻１
Ｌ且−仁（ヒ
２３８−２４Ｏ
ＣＬ４
２７８．５−２７９．５
Ｎα２
２２９、５−２３１
Ｎ（ＣＨｓ）ｚ
Ｎα６
１３１−１３２
Ｎｏ、 ７
２２８−２２９．５
Ｎα８
１６２−１６４
一般式（１）で示されるフルオレン化合物を感圧記録紙
に適用するには感圧記録紙を製造する方法として周知の
従来方法例えば特公昭４６−４６１４号に記載されてい
る方法によればよく、又感熱記録紙に適用するにはその
ための慣用方法例えば特公昭４５−１４０３９号に記載
されている方法によればよい。Hiroshi 3 259-261 l possession''] Bow summoning gong transmission 1 L and - Ren (hi 238-24O CL4 278.5-279.5 Nα2 229, 5-231 N(CHs)z Nα6 131-132 No, 7 228-229.5 Nα8 162-164 To apply the fluorene compound represented by the general formula (1) to pressure-sensitive recording paper, a well-known conventional method for producing pressure-sensitive recording paper is used, for example, as described in Japanese Patent Publication No. 46-4614. The described method may be used, and for application to heat-sensitive recording paper, a commonly used method therefor may be used, such as the method described in Japanese Patent Publication No. 14039/1983.
以下実施例により本発明を更に詳細に説明する。The present invention will be explained in more detail with reference to Examples below.
なお、文中、部は重量部を表わす。In addition, parts in the text represent parts by weight.
実施班上＝フルオレン 八 Ｎα１のＡ３−（２−アミ
ノ−４−ジメチルアミノフェニル）−３−（４−ジベン
ジルアミノフェニル）６−シメチルアミノフタリド５．
８部を濃硫酸１８．５部と水６部の混合物中に溶解し、
０℃に冷却する。Working group top = Fluorene 8 Nα1 A3-(2-amino-4-dimethylaminophenyl)-3-(4-dibenzylaminophenyl)6-dimethylaminophthalide5.
8 parts dissolved in a mixture of 18.5 parts concentrated sulfuric acid and 6 parts water,
Cool to 0°C.
次いでこれに亜硝酸ナトリウム０．８部を濃硫酸１８．
５部に溶解した溶液を０〜５°Ｃで３０分を要して滴下
し、同温度で２時間反応してジアゾ化を完了する。Next, add 0.8 parts of sodium nitrite to this and add 18 parts of concentrated sulfuric acid.
5 parts of the solution was added dropwise over 30 minutes at 0 to 5°C, and reacted at the same temperature for 2 hours to complete diazotization.
次いで銅粉０．４部を添加した後徐々に３０゛Ｃ迄加熱
し、３０〜３５°Ｃで１時間攪拌して閉環を完了する。Next, after adding 0.4 part of copper powder, the mixture was gradually heated to 30°C and stirred at 30-35°C for 1 hour to complete ring closure.
反応生成物を氷水２００部に注入し、２０％カセイソー
ダ溶液でアルカリ性とする。これをトルエン８０部と還
流すること１時間の後、分層し、トルエン層を５０部の
温湯で洗い次いでトルエンを溜置した後これにメタノー
ル２０部を加えて更に１時間還流し、冷却すると結晶が
析出する。析出物を濾取し乾燥するとＮｏ、１のフルオ
レン化合物が、白色結晶として得られる。収量２．２部
（収率３９．１％）、ｍ、ｐ、２３Ｂ−２４０’Ｃであ
った。The reaction product is poured into 200 parts of ice water and made alkaline with 20% caustic soda solution. After refluxing this with 80 parts of toluene for 1 hour, the layers were separated, the toluene layer was washed with 50 parts of hot water, the toluene was distilled, 20 parts of methanol was added thereto, and the mixture was further refluxed for 1 hour and cooled. Crystals precipitate. When the precipitate is filtered and dried, fluorene compound No. 1 is obtained as white crystals. The yield was 2.2 parts (yield 39.1%), m, p, 23B-240'C.
元素分析値より、この化合物の分子式がＣ１１ＩＨ３ｓ
Ｎ３Ｃｈであることを確認した。From the elemental analysis value, the molecular formula of this compound is C11IH3s
It was confirmed that it was N3Ch.
ＣＨＮ
理論値 ８０．６７％ ６．２５＄ ７．４
３χ実測値 ８０．６１χ ６．２０！ ７．
３８χ夫施班之：感且五４０動克塾造
実施例１によって合成したフルオレン化合物をアルキル
ナフタリン等の溶剤に溶解し、公知の方法によりカプセ
ルに封入する。これを支持体の下面に塗布、乾燥して上
用紙（ＣＢシート）を得る。CHN Theoretical value 80.67% 6.25$ 7.4
3χ actual value 80.61χ 6.20! 7.
The fluorene compound synthesized in Example 1 was dissolved in a solvent such as alkylnaphthalene and encapsulated in a capsule by a known method. This is applied to the lower surface of the support and dried to obtain a top paper (CB sheet).
一方、フェノール化合物等の固体酸を支持体の上面に塗
布し下用紙（ＣＦシート）を得る。上用紙と下用紙を塗
布面が相対向するように重ね、筆記等により加圧すると
、下用紙上に青緑色の複写像を得る。この複写像は耐光
性が良く、且つ近赤外部に吸収を有する。On the other hand, a solid acid such as a phenol compound is applied to the upper surface of the support to obtain a lower paper (CF sheet). When the upper paper and the lower paper are stacked so that the coated surfaces face each other and pressure is applied by writing or the like, a blue-green copy image is obtained on the lower paper. This copied image has good light resistance and absorbs near infrared light.
夫施拠主：感光五４０動１４遣
実施例１によって合成したフルオレン化合物Ｎα１の４
部を１０％ポリビニルアルコール水溶液ｌＯ部および水
６部と摩砕し分散液を得る（成分Ａとする）。一方、ビ
スフェノールＡの４部をｌＯ％ポリ威分Ａ１部と成分８
６部を混合し、これを支持体上に塗布、乾燥して感熱記
録紙を得る。この感熱記録紙は、熱ペン等により加熱す
ると緑色に発色する。この発色像は近赤外部に吸収を有
し、且つ耐光性が良い。Owner: Fluorene compound Nα1-4 synthesized according to Example 1
One part was triturated with 10 parts of a 10% aqueous polyvinyl alcohol solution and 6 parts of water to obtain a dispersion (referred to as component A). On the other hand, 4 parts of bisphenol A, 1 part of polyphenol A and 8 parts of 1O% polyphenol A were added.
6 parts of the mixture are mixed, coated on a support, and dried to obtain heat-sensitive recording paper. This thermosensitive recording paper develops a green color when heated with a thermal pen or the like. This colored image has absorption in the near-infrared region and has good light resistance.
図−１は、青色の電子供与性発色剤として用いられるＣ
ＶＬ （クリスタル バイオレット ラクトン）と、本
発明のフルオレン化合物阻２、および弘８のビスフェノ
ールＡ上の発色像のスペクトルを示す。
本発明のフルオレン化合物は近赤外領域（７００〜＋０
００ｎｍ）に吸収を有するが、これに反しＣＶＬは近赤
外部に吸収を有しない。Figure 1 shows C used as a blue electron-donating coloring agent.
1 shows spectra of color images of VL (crystal violet lactone), the fluorene compounds of the present invention, and Hiroshi 8 on bisphenol A. The fluorene compound of the present invention can be used in the near-infrared region (700 to +0
CVL, on the other hand, has no absorption in the near-infrared region.
Claims (1)
表等があります▼、▲数式、化学式、表等があります▼
又は▲数式、化学式、表等があります▼ であり、Ｒ＿１、Ｒ＿２、Ｒ＿３、Ｒ＿４、Ｒ＿５およ
びＲ＿６はいずれも水素、炭素数１〜４のアルキル基、
炭素数５〜７のシクロアルキル基、ベンジル基を表わす
。但し、Ｒ＿１、Ｒ＿２、Ｒ＿３、Ｒ＿４、Ｒ＿５およ
びＲ＿６は全てが同時には炭素数１〜４のアルキル基を
示すことがなく、又Ｒ＿１とＲ＿２、又はＲ＿３とＲ＿
４は場合によりそれらがそれぞれ結合する窒素原子（ア
ミノ基の窒素原子）とともに炭素数４〜６の複素環（第
２の窒素原子をも含み得る）を形成するものとする。 ２、一般式（II） ▲数式、化学式、表等があります▼（II） （式中Ｅは、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、▲数式、化学式、表等があります▼
又は▲数式、化学式、表等があります▼ であり、Ｒ＿１、Ｒ＿２、Ｒ＿３、Ｒ＿４、Ｒ＿５およ
びＲ＿６はいずれも水素、炭素数１〜４のアルキル基、
炭素数５〜７のシクロアルキル基、ベンジル基を表わす
。但し、Ｒ＿１、Ｒ＿２、Ｒ＿３、Ｒ＿４、Ｒ＿５およ
びＲ＿６は全てが同時には炭素数１〜４のアルキル基を
示すことがなく、又Ｒ＿１とＲ＿＿２、又はＲ＿＿３と
Ｒ＿＿４は場合によりそれらがそれぞれ結合する窒素原
子（アミノ基の窒素原子）とともに炭素数４〜６の複素
環（第２の窒素原子をも含み得る）を形成するものとす
る。｝ で表わされる化合物をジアゾ化後閉環させることを特徴
とする一般式（ I ） ▲数式、化学式、表等があります▼（ I ） （式中Ｅ、およびＲ＿１、Ｒ＿２、Ｒ＿３およびＲ＿４
は一般式（II）中のＥ、およびＲ＿１、Ｒ＿２、Ｒ＿３
およびＲ＿４と同じ意味を表わす。） で示されるフルオレン化合物の製造法。 ３、次の一般式（ I ） ▲数式、化学式、表等があります▼（ I ） ｛式中Ｅは、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、▲数式、化学式、表等があります▼
又は▲数式、化学式、表等があります▼ であり、Ｒ＿１、Ｒ＿２、Ｒ＿３、Ｒ＿４、Ｒ＿５およ
びＲ＿６はいずれも水素、炭素数１〜４のアルキル基、
炭素数５〜７のシクロアルキル基、ベンジル基を表わす
。但し、Ｒ＿１、Ｒ＿２、Ｒ＿３、Ｒ＿４、Ｒ＿５およ
びＲ＿６は全てが同時には炭素数１〜４のアルキル基を
示すことがなく、又Ｒ＿１とＲ＿２、又はＲ＿３とＲ＿
４は場合によりそれらがそれぞれ結合する窒素原子（ア
ミノ基の窒素原子）とともに炭素数４〜６の複素環（第
２の窒素原子をも含み得る）を形成するものとする。｝ で表わされるフルオレン化合物を電子供与性発色剤とし
て用いることを特徴とする記録材料。[Claims] 1. A fluorene compound represented by the general formula (I), ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) In the formula, E is: ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas ,Chemical formula,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and R_1, R_2, R_3, R_4, R_5 and R_6 are all hydrogen, an alkyl group having 1 to 4 carbon atoms,
Represents a cycloalkyl group or benzyl group having 5 to 7 carbon atoms. However, R_1, R_2, R_3, R_4, R_5 and R_6 do not all represent an alkyl group having 1 to 4 carbon atoms at the same time, and R_1 and R_2, or R_3 and R_
4 forms a heterocycle having 4 to 6 carbon atoms (which may also contain a second nitrogen atom) together with the nitrogen atom to which they are bonded (the nitrogen atom of the amino group). 2. General formula (II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) (E in the formula is, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and R_1, R_2, R_3, R_4, R_5 and R_6 are all hydrogen, an alkyl group having 1 to 4 carbon atoms,
Represents a cycloalkyl group or benzyl group having 5 to 7 carbon atoms. However, R_1, R_2, R_3, R_4, R_5, and R_6 do not all represent an alkyl group having 1 to 4 carbon atoms at the same time, and R_1 and R__2, or R__3 and R__4 may be nitrogen atoms to which they are bonded, respectively. Together with the atom (nitrogen atom of the amino group), a heterocycle having 4 to 6 carbon atoms (which may also include a second nitrogen atom) is formed. } General formula (I) characterized by diazotizing and ring-closing a compound represented by
is E in general formula (II), and R_1, R_2, R_3
and R_4. ) A method for producing a fluorene compound. 3. The following general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) {E in the formula is ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and R_1, R_2, R_3, R_4, R_5 and R_6 are all hydrogen, an alkyl group having 1 to 4 carbon atoms,
Represents a cycloalkyl group or benzyl group having 5 to 7 carbon atoms. However, R_1, R_2, R_3, R_4, R_5 and R_6 do not all represent an alkyl group having 1 to 4 carbon atoms at the same time, and R_1 and R_2, or R_3 and R_
4 forms a heterocycle having 4 to 6 carbon atoms (which may also contain a second nitrogen atom) together with the nitrogen atom to which they are bonded (the nitrogen atom of the amino group). } A recording material characterized in that a fluorene compound represented by the following is used as an electron-donating coloring agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2018433A JPH0633246B2 (en) | 1990-01-29 | 1990-01-29 | Fluorene compound, method for producing the same and recording material using the compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2018433A JPH0633246B2 (en) | 1990-01-29 | 1990-01-29 | Fluorene compound, method for producing the same and recording material using the compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03202386A true JPH03202386A (en) | 1991-09-04 |
| JPH0633246B2 JPH0633246B2 (en) | 1994-05-02 |
Family
ID=11971515
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018433A Expired - Lifetime JPH0633246B2 (en) | 1990-01-29 | 1990-01-29 | Fluorene compound, method for producing the same and recording material using the compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0633246B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0757287A1 (en) | 1995-07-19 | 1997-02-05 | Fuji Photo Film Co., Ltd. | Image formation method |
-
1990
- 1990-01-29 JP JP2018433A patent/JPH0633246B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0757287A1 (en) | 1995-07-19 | 1997-02-05 | Fuji Photo Film Co., Ltd. | Image formation method |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0633246B2 (en) | 1994-05-02 |
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