Compound of quinacridones-carbazole group and application in organic electroluminescence device

[0027] Example 1: Synthesis of TMDCzBQA

[0028] Compound 2,5-dihydroxy-1,4-cyclohexadiene-1,4-dicarboxylic acid diethyl ester 5.0g, 3,5-dimethylaniline 10ml, hydrochloric acid 0.5ml, heated to reflux with ethanol as solvent 6 hours. Cool and filter, wash the precipitation with ethanol to obtain 8.2 g of pink product 2,5-bis(3,5-dimethylanilino)-1,4-cyclohexadiene-1,4-dicarboxylate diethyl ester, Yield 90.3%.

[0029] The compound 2,5-bis(3,5-dimethylanilino)-1,4-cyclohexadiene-1,4-dicarboxylic acid diethyl ester 5.0 g and 1-chloronaphthalene were heated to reflux at 260°C for 2 hours, filtered and washed with chloroform to obtain 3.2 g of the product 1,3,8,10-tetramethyl-6,13-dihydro-quinacridone with a yield of 81.2%.

[0030] 2.5 g of compound 1,3,8,10-tetramethyl-6,13-dihydro-quinacridone was added to nitrobenzene, potassium hydroxide, ethylene glycol monomethyl ether, heated to reflux for 2 hours, and then added 100 ml of ethanol and 150 ml of acetic acid were heated to reflux for 2 hours, and the product was filtered by washing with water, ethanol and chloroform to obtain a red product. 1,3,8,10-Tetramethylquinacridone (TMQA) 2.1 g Yield 84.5%.

[0031]

[0032] 1,3,8,10-Tetramethyl-5,12-bis-(4-N-carbazolyl-butyl)quinacridone

[0033] TMDCzBQA

[0034] The above TMQA was added to the tetrahydrofuran solvent, 2.0 ml of 1,4-dibromobutane and a little sodium hydride were added, and the reaction was heated under reflux for 12 h. Cool, add appropriate amount of methanol and let stand. After filtration, an orange-red solid, 1,3,8,10-tetramethyl-5,12-bis(4-bromobutyl)quinacridone, was precipitated with petroleum ether, the product was 2.0 g, and the yield was 50%.

[0035] 1.05 g of carbazole was reacted with the above 1,3,8,10-tetramethyl-5,12-bis(4-bromobutyl)quinacridone in the presence of a little KOH in butanone under reflux for 12h . Cool, wash with water, and extract with dichloromethane. with Al 2 O 3 As the stationary phase, cyclohexane is used as the developing solvent to run the chromatographic column to obtain a red powdery solid product 1,3,8,10-tetramethyl-5,12-bis{4-N-carbazolyl)butyl}quinoline Acridone (TMDCzBQA) 0.76 g, 30% yield. Mass spectrum molecular ion peak: 830.5. Elemental analysis according to formula C 57 H 58 N 4 O 2 Calculated: C: 82.4%; H: 7.0%; N: 6.7%; Experiment: C: 82.6%; H: 7.2%; N: 6.5%.

[0036] Example 2: Synthesis of TMDCzHQA

[0037] The synthesis of TMDCzHQA is the same as in Example 1, except that 1,6-dibromohexane is used instead of 1,4-dibromobutane to obtain the product 1,3,8,10-tetramethyl-5,12-bis{4 -N-carbazolyl)hexyl}quinacridone (TMDCzHQA). Mass spectrum molecular ion peak: 886.5. Elemental analysis according to formula C 61 H 66 N 4 O 2 Calculated: C: 82.6%; H: 7.5%; N: 6.3%; Experiment: C: 82.6%; H: 7.2%; N: 6.5%.

[0038] Example 3: Synthesis of TMDCzOQA

[0039] The synthesis of TMDCzOQA is the same as in Example 1, except that 1,8-dibromooctane is used instead of 1,4-dibromobutane to obtain the product 1,3,8,10-tetramethyl-5,12-bis{4 -N-carbazolyl)octyl}quinacridone (TMDCzOQA). Mass spectrum molecular ion peak: 942.6. Elemental analysis according to formula C 65 H 74 N 4 O 2 Calculated: C: 82.8%; H: 7.9%; N: 5.9%; Experiment: C: 82.6%; H: 7.8%; N: 6.0%.

[0040]

[0041] 1,3,8,10-Tetramethyl-5,12-bis- 1,3,8,10-Tetramethyl-5,12-bis-(4-N-carbazolyl)-hexyl)quinacridone (4-N-carbazolyl- octyl)quinacridone

[0042] TMDCzHQA TMDCzOQA