Preparation of asymmetric anthracene derivatives and organic electroluminescent device using same
Provided is a method of preparing asymmetric anthracene derivative, more particularly, a method for high-yield production of an anthracene derivative in which an alkyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group or a heteroaryl group is introduced at position 2 of anthracene, and an aryl group or a heteroaryl group is introduced at each of positions 9 and 10 of the anthracene.
1. A method of preparing an anthracene derivative represented by Formula 5 below, the method comprising:
(a) reacting a compound of Formula 1 below with a compound of Formula 2 below to obtain a compound of Formula 3 below;
(b) cyclizing the compound of Formula 3 to obtain a compound of Formula 4 below; and
(c) introducing an aryl group at position 10 of anthracene of the compound of Formula 4,
wherein Z is MgX where X is halogen, Li, or Na; R 2 is an alkyl group of C 1 ˜C 30 , a cycloalkyl group of C 5 ˜C 30 , a heterocycloalkyl group of C 5 ˜C 30 , an aryl group of C 5 ˜C 30 , or a heteroaryl group of C 5 ˜C 30 ; Ar 2 is an aryl group of C 5 ˜C 30 or a heteroaryl group of C 5 ˜C 30 ; and
wherein the alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group and heteroaryl group are each independently unsubstituted or substituted by at least one selected from the group consisting of C 1 -C 30 alkyl, C 2 -C 30 alkenyl, C 2 -C 30 alkynyl, C 5 -C 30 aryl, C 5 -C 30 heteroaryl, C 5 -C 30 aryloxy, C 1 -C 30 alkyloxy, C 5 -C 30 arylamino, C 5 -C 30 diarylamino, C 5 -C 30 arylalkyl, C 5 -C 30 cycloalkyl, C 5 -C 30 heterocycloalkyl and a halogen atom.
2. The method of claim 1 , wherein in step (b), the compound of Formula 3 is acetylated and cyclized.
3. The method of claim 1 , wherein in step (c), a halogen is introduced at position 10 of the anthracene of the compound of Formula 4 and the resultant compound is subjected to Suzuki coupling reaction with Ar 2 —B(OH) 2 to obtain the compound of Formula 5.