Halogenoacetoxyadamantane derivatives and process for production thereof
View Patent ↗Provided are a novel halogenoacetoxyadamantane derivative which is useful as a modifying agent for a resin for a photoresist and a dry etching resistance-improving agent in the photolithography field, agricultural and medical intermediates and a compound for other various industrial products and a process for producing the same. To be specific, provided are a halogenoacetoxyadamantane derivative having a halogenoacetoxy group in an adamantane skeleton and a process for producing a halogenoacetoxyadamantane derivative, comprising the step of reacting a hydroxyl group of an adamantane skeleton with halogenoacetic halide or reacting the above hydroxyl group with a lithiation agent to derive it into a lithiumoxy group and then reacting halogenoacetic halide to introduce a halogenoacetoxy group.
1. A halogenoacetoxyadamantane derivative which is 1-halogenoacetoxyperfluoroadamantane.
2. A halogenoacetoxyadamantane derivative which is 2-alkyl-2-halogenoacetoxyadamantane.
3. A halogenoacetoxyadamantane which is 1-halogenoacetoxy-3-hydroxyadamantane.
4. A process for producing a halogenoacetoxyadamantane derivative, comprising:
reacting a hydroxyl group of an adamantane skeleton directly with halogenoacetic halide or reacting said hydroxyl group with a lithiation agent to obtain a lithiumoxy group and then reacting halogenoacetic halide therewith to introduce a halogenoacetoxy group;
wherein said halogenoacetoxyadamantane derivative is 2-alkyl-2-halogenoacetoxyadamantane, 1-halogenoacetoxy-3-hydroxyadamantane or 1-halogenoacetoxyperfluoroadamantane.
5. The process of claim 4 , wherein said lithiating agent is lithium metal, n-butyllithium, sec-butyllithium or tert-butyllithium.
6. A photoresist composition, comprising:
the halogenoacetoxyadamantane derivative of claim 1 .
7. A photoresist composition, comprising:
the halogenoacetoxyadamantane derivative of claim 2 .
8. A photoresist composition, comprising:
the halogenoacetoxyadamantane derivative of claim 3 .
9. A dry-etching resistance improving agent, comprising:
the halogenoacetoxyadamantane derivative of claim 1 .
10. A dry-etching resistance improving agent, comprising:
the halogenoacetoxyadamantane derivative of claim 2 .
11. A dry-etching resistance improving agent, comprising:
the halogenoacetoxyadamantane derivative of claim 3 .