Organic electroluminescent material of dendritic macromolecular naphthalene imide
An electroluminescent material, naphthalimide technology, applied in the direction of luminescent materials, naphthalene dicarboxamide dyes/phthalimide dyes, chemical instruments and methods, etc., can solve problems such as recrystallization
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Embodiment 1
[0058] Synthesis of dendrimer with carrier transport function group (compound NPOXZ1)
[0059]
[0060] (1) Synthesis of substituted 1,8-naphthimide (compound NP1):
[0061]
[0062] Add 4-N,N'-dimethyl-1,8-naphthalene anhydride (1.0g, 4.15mmol) and 5-amino-isotitanic acid (1.5g, 8.2mmol) dry DMF (20ml) into a 50ml single-mouth bottle ), heating to 100°C under nitrogen protection, after stirring for 24 hours, stop heating and cool to normal temperature. Pour the reaction solution into 100ml water, a large amount of orange-yellow solid precipitated, filtered, washed with plenty of water, dried, and then recrystallized with dichloromethane to obtain 0.9g orange-red solid (compound NP1), the yield was 54%, mp>250 ℃.
[0063] 1 H-NMR(500MHz, DMSO-d 6 , Ppm)δ=3.1(s, 6H, N(CH 3 ) 2 ), 7.25(d, 1H, naphthene-H, J=8.3Hz), 7.8(t, 1H, naphthene-H, J=7.9Hz), 8.2(s, Ph-H, 2H), 8.37(d, 1H , Naphthene-H, J = 8.2 Hz), 8.45 (d, lH, naphthene-H, J = 7.2 Hz), 8.52 (s, 1H, Ph-H), 8.57 (d, 1H, nap...
Embodiment 2
[0074] Synthesis of dendrimers with carrier transport functional groups (compound NPOXZ2).
[0075]
[0076] (1) Synthesis of substituted 1,8-naphthimide (compound NP2)
[0077]
[0078] Add 4-piperidinyl-1,8-naphthalene (1.0g, 3.56mmol), 5-amino-isotitanic acid (1.29g, 7.12mmol) and dry DMF (20ml) into a 50ml single-necked flask. Reaction and treatment The method was the same as that of compound NP1, and 0.88 g of yellow solid (compound NP2) was obtained, the yield was 56.1%, and the mp>250°C.
[0079] 1 H-NMR(500MHz, DMSO-d 6 , Ppm)δ=1.65(m, 2H, -CH 2 -), 1.85(m, 4H, -CH 2 -), 3.2(t, 4H, N-CH 2 ), 7.25 (d, 1H, naphthene-H, J = 8.2 Hz), 7.8 (t, l H, naphthene-H, J = 7.9 Hz), 8.2 (s, Ph-H, 2H), 8.37 (d, 1H, naphthene-H, J = 8.2 Hz), 8.45 (d, 1H, naphthene-H, J = 7.1 Hz), 8.47 (s, 1H, Ph-H), 8.53 (d, 1H, naphthene-H, J = 8.1 Hz).
[0080] (2) Synthesis of dendrimer with carrier transport function group (compound NPOXZ2):
[0081]Compound NP2 (0.1g, 0.225mmol), compound 2 (0.38g...
Embodiment 3
[0084] Synthesis of dendrimers (NPOXZ3) with carrier transport functional groups:
[0085]
[0086] (1) Synthesis of substituted 1,8-naphthimide (NP3):
[0087]
[0088] Add 4-morpholinyl-1,8-naphthalene anhydride (1.0g, 3.53mmol) and 5-amino-isotitanic acid (1.27g, 7.06mmol) and dry DMF (20ml) into a 50ml single-necked flask. The treatment method is the same as the preparation of compound NP1 to obtain 0.83 g of yellow solid (compound NP3) with a yield of 52.7%. m.p.>250°C.
[0089] 1 H-NMR(500MHz, DMSO-d 6 , Ppm)δ=3.2(t, 4H, N-CH 2 ), 4.0(t, 4H, O-CH 2 -), 7.4(d, 1H, naphthene-H, J=8.2Hz), 7.85(t, 1H, naphthene-H, J=7.9Hz), 8.2(s, Ph-H, 2H), 8.42(d, 1H, naphthene-H, J = 8.1 Hz), 8.47 (d, 1H, naphthene-H, J = 7.2 Hz), 8.52 (s, 1H, Ph-H), 8.55 (d, 1H, naphthene-H, J =8.4Hz).
[0090] (2) Synthesis of compound NPOXZ3:
[0091] Compound NP3 (0.1g, 0.224mmol), compound 2 (0.38g, 0.473mmol) obtained from step (3) in Example 1, potassium carbonate (0.1g, 0.72mmol) and dry DMF ( 10m...
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