Hybrid materials and light-emitting diodes

A hybrid light-emitting diode (HLED), the HLED comprising:

• an anode;
• a cathode;
• a metal oxide layer having a first surface and an opposite second surface;
• a self-assembled monolayer attached to the first surface of the metal oxide layer, wherein the opposite second surface of the metal oxide layer is positioned on the anode and the self-assembled monolayer comprises:
• a moiety of formula (I-a):
• wherein:
• X1, at each occurrence, is independently O, S, or NH;
• R1, at each occurrence, is independently hydrogen, C1-4alkyl, —OR10, —SR10, or —N(R10)2;
• and
• R10, at each occurrence, is independently hydrogen or C1-4alkyl;
• an emissive layer positioned on the self-assembled monolayer, the emissive layer comprising a hybrid material of formula Cu4X8(L)4, wherein:
• Cu is copper (I);
• X is bromide (Br) or iodide (I);
• and
• L is a 1,4-diazabicyclo[2.2.2]octan-1-ium of formula:
• wherein:
• R′, at each occurrence, is independently C1-4alkyl, —Br, —Cl, —CN, —OC1-4alkyl, —C1-4alkylOH, —C1-2alkylNH2;
• R″ is phenyl or —CH2-phenyl;
• n is 0, 1, 2, 3, 4, 5, or 6;
• and
• m is 0 or 1;
• wherein each Cu is coordinated to a positively charged nitrogen atom (N+) of the 1,4-diazabicyclo[2.2.2]octan-1-ium and 3 halides;
• an electron transport layer;
• and
• an electron injection layer positioned on the electron transport layer, wherein the cathode is positioned on the electron injection layer.

A method of manufacturing a hybrid light-emitting diode (HLED), the method comprising:

• preparing a self-assembled monolayer solution comprising a first solvent and a compound of formula (I):
• wherein:
• X1, at each occurrence, is independently O, S, or NH;
• R1, at each occurrence, is independently hydrogen, C1-4alkyl, —OR10, —SR10, or —N(R10)2;
• and
• R10, at each occurrence, is independently hydrogen or C1-4alkyl;
• providing a metal oxide layer positioned on an anode;
• spin coating the self-assembled monolayer solution onto a first surface of the metal oxide layer to provide a self-assembled monolayer attached to the first surface of the metal oxide layer, the self-assembled monolayer comprising:
• a moiety of formula (I-a):
• wherein:
• X1, at each occurrence, is independently O, S, or NH;
• R1, at each occurrence, is independently hydrogen, C1-4alkyl, —OR10, —SR10, or —N(R10)2;
• and
• R10, at each occurrence, is independently hydrogen or C1-4alkyl;
• annealing the self-assembled monolayer;
• preparing a hybrid material solution comprising a second solvent and a hybrid material of formula Cu4X8(L)4, wherein:
• Cu is copper (I);
• X is bromide (Br) or iodide (I);
• and
• L is a 1,4-diazabicyclo[2.2.2]octan-1-ium of formula:
• wherein:
• R′, at each occurrence, is independently C1-4alkyl, —Br, —Cl, —CN, —OC1-4alkyl, —C1-4alkylOH, —C1-2alkylNH2;
• R″ is phenyl or —CH2-phenyl;
• n is 0, 1, 2, 3, 4, 5, or 6;
• and
• m is 0 or 1;
• wherein each Cu is coordinated to a positively charged nitrogen atom (N+) of the 1,4-diazabicyclo[2.2.2]octan-1-ium and 3 halides;
• providing the self-assembled monolayer positioned on the anode;
• spin coating the hybrid material solution onto the self-assembled monolayer to provide an emissive layer;
• and
• recrystallizing the emissive layer.