2,3,6,7-tetrabromonaphthalene tetracarboxylic acid imidodicarbonic diamide compound, manufacturing method and application of 2,3,6,7-tetrabromonaphthalene tetracarboxylic acid imidodicarbonic diamide compound
A technology of tetrabromonaphthalene tetracarboxylic acid diimide and compound, which is applied in the field of 2,3,6,7-tetrabromonaphthalenetetracarboxylic acid diimide compound and can solve the problem of low electron mobility of OTFT devices , difficult to form, poor film formation and other problems, to achieve the effect of easy synthesis, high purity and low synthesis cost
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Embodiment 1
[0049] Example 1: N,N'-Dioctyl-[2,3-d:6,7-d']-bis[1,3-dithia-2-yrcene-propanedicyano]-naphthalene - Synthesis of 1,4,5,8-tetracarboxylic diimide (1).
[0050] Concrete synthetic steps are:
[0051] 1. Synthesis of 12,3,6,7-tetrabromonaphthalene tetracarboxylic dianhydride (TBNDA)
[0052] Mix 450mL of 20% oleum into a 1L three-necked flask, and then add naphthalene tetracarboxylic dianhydride (NDA) (16g, 59.7mmol), liquid bromine (16mL, 320mmol) and 0.8g of iodine (catalyst). Raise the temperature of the reaction mixture to 130°C, heat the reaction for 78 hours, then lower it to room temperature, remove unreacted liquid bromine with nitrogen flow, pour the reaction solution into 1Kg of crushed ice, filter, and wash the precipitate with a large amount of water until the filtrate is neutral. Drying in vacuo afforded 28 g of a yellow powdery solid (TBNDA), with a yield of 81%.
[0053] Mass Spectrum (MS-EI)) m / z584 (M + ,95%)
[0054] 1.2 Synthesis of N,N′-dioctyl-2,3,6,7-t...
Embodiment 2
[0067] Example 2: N,N'-bis(2-ethyl-hexyl)-[2,3-d:6,7-d']-bis[1,3-dithia-2-yrylene- Synthesis of malondicyano]-naphthalene-1,4,5,8-tetracarboxylic diimide (2).
[0068] Concrete synthetic steps are:
[0069] 2.1 Synthesis of N,N′-bis(2-ethyl-hexyl)-2,3,6,7-tetrabromo-naphthalene tetracarboxylic acid diimide
[0070] Using 2-ethyl-hexylamine instead of n-octylamine, the synthesis method is the same as step 1.2 in Example 1, and the yield is 33%.
[0071] Mass Spectrum: [MS(TOF)]m / z:806.8(M + ),884.3(M+2K) + .
[0072] H NMR spectrum: 1 H-NMR (300MHz, CDCl 3 )δ(ppm):0.859-0.969(m,6H),1.287-1.409(m,8H),1.923-1.967(m,1H),4.169-4.194(d,J=7.50Hz,2H).
[0073] 2.2 Synthesis of example compound 2
[0074] Replace N,N'- Dioctyl-2,3,6,7-tetrabromonaphthalene-1,4,5,8-tetracarboxylic diimide, the synthetic method is the same as step 1.4 in Example 1, and dark brown solid (2 ), yield 51%.
[0075] Mass Spectrum: [MS(TOF)]m / z:767.5(M + ).
[0076] Elemental analysis: Molecular f...
Embodiment 3
[0078] Example 3: N,N'-bis(2-octyl-dodecyl)-[2,3-d:6,7-d']-bis[1,3-dithia-2-phyllo Synthesis of butene-propanedicyano]-naphthalene-1,4,5,8-tetracarboxylic diimide (3).
[0079] Concrete synthetic steps are:
[0080] 3.1. Synthesis of N,N′-bis(2-octyl-dodecyl)-2,3,6,7-tetrabromonaphthalene-1,4,5,8-tetracarboxylic acid diimide
[0081] Using 2-octyl-dodecylamine instead of n-octylamine, the synthesis method is the same as step 1.2 in Example 1, and the yield is 33%.
[0082] Mass Spectrum: [MS(TOF)]m / z:1144.8(M + ).
[0083] H NMR spectrum: 1 H-NMR (300MHz, CDCl 3 )δ(ppm):0.863-0.888(m,6H),1.235(b,32H),1.966-2.008(m,1H),4.159-4.183(d,J=7.20Hz,2H).
[0084] 3.2 Synthesis of example compound 3
[0085] Replace N with N,N′-bis(2-octyl-dodecyl)-2,3,6,7-tetrabromonaphthalene-1,4,5,8-tetracarboxylic diimide, N'-dioctyl-2,3,6,7-tetrabromonaphthalene-1,4,5,8-tetracarboxylic acid diimide, the synthesis method is the same as step 1.4 in Example 1, and reddish-brown Solid (3), 53% y...
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