Aromatic imide compound and method for producing same
View Patent ↗[Problem] to provide an aromatic imide compound wherein the sensitivity for visible light such as g-line, h-line etc. is increased and solubility is also improved. [Means for solving problem] The aromatic imide compound of the invention is a compound represented by the formula (1) below (in the formula, R 1 represents a haloalkyl group having 1 to 7 carbon atoms or a haloaryl group, R 2 represents a group containing a substituted or unsubstituted, aliphatic or aromatic group which may have a heteroatom, and adjacent R 2 s may form an imido group by connecting each other, R 3 represent a halogen atom or a hydrocarbon group, m is zero or an integer of 1 or more, n is zero or an integer of 1 or more, and a sum of n and m is 1 to 6). These compounds are obtained by following processes. A halogenated naphtharic anhydride is reacted with an aromatic group-containing hydrocarbon such as ethynylbenzene to prepare a naphthalic anhydride substituted by an aromatic group-containing group. The obtained compound is then reacted with hydroxylamine hydrochloride to be made N-hydoxyimidization. Finally, the resultant compound is reacted with a sulfonyl halide such as trifluoromethylsulfonyl chloride to obtain the objective compound.
1. An aromatic imide compound represented by the formula (1):
wherein in R 1 represents a haloalkyl group having 1 to 7 carbon atoms or a haloaryl group, R 3 represents a halogen atom or a hydrocarbon group n is zero or an integer of 1 or more, m is at least 1 and a sum of n and m is 1 to 6, and R 2 is the group R 4 -R 5 — wherein R 4 is selected from the group consisting of
and where R 5 is an alkenylene group or an alkynylene group.
2. The aromatic imide compound according to claim 1 , which can absorb light of g-line (436 nm) and/or h-line (405 nm) as measured using ultraviolet absorption spectroscopy of a solution of this aromatic imide compound in solution in methylene chloride, and where the addition of bromocresolgreen imparts a dark blue color to this solution, and further where upon irradiation with this light, the solution shows both a discoloration of the dark blue color indicating of a decreasing pH, and an attenuation of an absorption maximum measured by ultraviolet spectroscopy at the g-line (436 nm) and/or h-line (405 nm).
3. The aromatic imide compound represented by the formula (1) of claim 1 wherein R 1 represents a haloalkyl group having 1 to 7 carbon atoms.
4. The aromatic imide compound represented by the formula (1) of claim 3 , where R 5 is an alkynylene group.
5. An aromatic imide compound represented by formula (2):
wherein, R 1 represents a haloalkyl group having 1 to 7 carbon atoms or a haloaryl group, R 4 is selected from the group consisting of
6. The aromatic imide compound of claim 5 wherein, R 1 represents a haloalkyl group having 1 to 7 carbon atoms.
7. The aromatic imide compound of claim 5 wherein, R 1 represents a haloalkyl group having 1 to 7 carbon atoms and R 4 is selected from the group consisting of
8. The aromatic imide compound of claim 5 wherein the haloalkyl group having 1 to 7 carbon atoms or the haloaryl in one where the halo moiety is a fluorine atom and further where, respectively, a part or all of hydrogen atoms in the alkyl group of the haloalkyl or the aryl of the haloaryl group are substituted by a fluorine atoms, and further where the alkyl group of the haloalkyl is selected from the group consisting of a linear alkyl, a branched alkyl and a cyclic alkyl groups.
9. The aromatic imide compound of claim 5 wherein the haloalkyl group having 1 to 7 carbon atoms or the haloaryl in one where the halo moiety is a fluorine atom and further where, respectively, a part or all of hydrogen atoms in the alkyl group of the haloalkyl or the aryl of the haloaryl group are substituted by a fluorine atoms, and further where the alkyl group of the haloalkyl is selected from the groups consisting of a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, and a heptyl group and further where the aryl group of the haloaryl is selected from phenyl or tolyl.
10. The aromatic imide compound of claim 5 wherein R 1 is a haloalkyl group having 1 to 7 carbon atoms, and this haloalkyl is in one where the halo moiety is a fluorine atom and further where a part or all of hydrogen atoms in the alkyl group of the haloalkyl are substituted by a fluorine atoms, and further where the alkyl group of the haloalkyl is selected from the groups consisting of a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, and a heptyl group.
11. The aromatic imide compound of claim 5 wherein the aromatic imide compound is selected from the compounds having structure (1 ra ),
and further wherein R 1 represents a haloalkyl group having 1 to 7 carbon atoms or a haloaryl group, and where R 4 is selected from the group consisting
and where the haloalkyl or the haloaryl in one where the halo moiety is a fluorine atom and further where, respectively, a part or all of hydrogen atoms in the alkyl group of the haloalkyl or the aryl of the haloaryl group are substituted by a fluorine atoms.
12. The aromatic imide compound of claim 11 wherein the haloalkyl group having 1 to 7 carbon atoms, where the halo moiety is a fluorine atom and further where, respectively, a part or all of hydrogen atoms in the alkyl group of the haloalkyl or the aryl of the haloaryl group are substituted by a fluorine atoms and further where the alkyl group in the haloalkyl is selected from the groups consisting of a linear alkyl, a branched alkyl and a cyclic alkyl groups.
13. The aromatic imide compound of claim 11 wherein the haloalkyl group having 1 to 7 carbon atoms, where the halo moiety is a fluorine atom and further wherein, respectively, a part or all of hydrogen atoms in the alkyl group of the haloalkyl, or the aryl of the haloaryl group are substituted by a fluorine atoms and further where the alkyl group of the haloalkyl is selected from the groups consisting of a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, and a heptyl group and further where the aryl group of the haloaryl is selected from phenyl or tolyl.
14. The aromatic imide compound of claim 11 wherein R 1 is a haloalkyl group having 1 to 7 carbon atoms, where the halo moiety is a fluorine atom and further where, respectively, a part or all of hydrogen atoms in the alkyl group of the haloalkyl are substituted by a fluorine atom and further where the alkyl group of the haloalkyl is selected from the groups consisting of a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, and a heptyl group.
15. The aromatic imide compound of claim 14 wherein R 4 is selected from the group consisting of