High mobility periodic structured organic films
View Patent ↗An high mobility structured organic film comprising a plurality of segments and a plurality of linkers arranged as a covalent organic framework, wherein the structured organic film may be a multi-segment thick structured organic film.
1. A high mobility structured organic film (SOF) comprising a plurality of segments and a plurality of linkers arranged as a covalent organic framework (COF), wherein
at least a portion of the SOF is periodic,
the SOF is a defect-free film having fewer than 10 pinholes, pores or gaps greater than about 250 nanometers in diameter per cm 2 , and
the SOF possesses a mobility ranging from about 0.1 to about 3.0 cm 2 /Vs.
2. The SOF of claim 1 , wherein at least one segment is derived from aryl, arylamine, or thiophene building blocks.
3. The SOF of claim 2 , wherein the at least one segment derived from aryl, arylamine, or thiophene building blocks contains at least one core selected from the group consisting of triarylamines, hydrazones, and enamines, arene, heteroarene, nitrofluorenones, 9-fluorenylidenes, malonitriles, diphenoquinones, and naphthalenetetracarboxylic diimides, thiophenes, oligothiophenes, fused thiophenes, perylene bisimides, tetrathiofulvalenes, melamine, porphyrin, and phthalocyanine.
4. The SOF of claim 1 , wherein the plurality of linkers are selected from the group consisting of covalent bond linkers, ester linkers, ketone linkers, amide linkers, amine linkers, imine linkers, ether linkers, urethane linkers, and carbonates linkers.
5. The SOF of claim 1 , wherein the high mobility SOF comprises a plurality of mono-segment thick SOFs and the plurality of mono-segment thick SOFs form a layered structure.
6. The SOF of claim 1 , wherein from about 30% by weight to about 99% by weight of the SOF is periodic.
7. The SOF of claim 1 , wherein the portion of the SOF that is periodic is uniformly distributed in the SOF.
8. The SOF of claim 1 , wherein the portion of the SOF that is periodic is not uniformly distributed in the SOF.
9. The SOF of claim 1 , wherein the periodic portion of the SOF comprises at least one atom of an element that is not carbon.
10. The SOF of claim 1 , wherein the SOF is 1 to about 50 segments thick.
11. The SOF of claim 1 , wherein the plurality of segments consists of segments having an identical structure and the plurality of linkers consists of linkers having an identical structure.
12. The SOF of claim 1 , wherein the SOF is a composite SOF.
13. An electronic device comprising the high mobility SOF of claim 1 .
14. The electronic device of claim 13 , wherein the electronic device is selected from the group consisting of radio frequency identification tags, photoreceptors, organic light emitting diodes, and thin film transistors, solar cells.
15. The electronic device of claim 13 , wherein the electronic device is a electrophotographic imaging member, the electrophotographic imaging member comprising: a supporting substrate, an electrically conductive ground plane, a charge blocking layer, a charge generating layer, a charge transport layer, an overcoat layer, and a ground strip.
16. A process for preparing a structured organic film (SOF) comprising:
(a) performing a computer simulation and/or materials modeling to formulate a molecular-level structure of a SOF and based on a metric of the computer simulation and/or materials modeling;
(b) preparing a liquid-containing reaction mixture comprising: a solvent, and
a plurality of molecular building blocks each comprising a segment and functional groups, wherein the plurality of molecular building blocks is selected based on results obtained from the computer simulation and/or materials modeling;
(c) depositing the reaction mixture as a wet film; and
(d) promoting a change of the wet film and forming a dry SOF that substantially replicates the formulated molecular-level structure of the SOF; wherein
the formulated molecular-level structure of a SOF is a high mobility SOF that possesses a mobility ranging from about 0.1 to about 3.0 cm 2 /Vs, and
the SOF is a defect-free film having fewer than 10 pinholes, pores or gaps greater than about 250 nanometers in diameter per cm 2 .
17. The SOF of claim 1 , wherein the mobility of the SOF is in the range of from about 0.2 to about 2.0 cm 2 /Vs.
18. The SOF of claim 1 , wherein the SOF possess a thermal stability higher than 400° C. under atmospheric conditions.