An Efficient Diazirine‐Based Four‐Armed Cross‐linker for Photo‐patterning of Polymeric Semiconductors

Abstract

A diazirine‐based four‐armed cross‐linker (4CNN) with a tetrahedron geometry is presented for efficient patterning of polymeric semiconductors by photo‐induced carbene insertion. After blending of 4CNN with no more than 3 % (w/w), photo‐patterning of p‐, n‐, and ambipolar semiconducting polymers with side alkyl chains was achieved; regular patterns with size as small as 5 μm were prepared with appropriate photomasks after 365 nm irradiation for just 40 s. The interchain packing order and the thin film morphology were nearly unaltered after the cross‐linking and the semiconducting properties of the patterned thin films were mostly retained. A complementary‐like inverter with a gain value of 112 was constructed easily by two steps of photo‐patterning of the p‐type and n‐type semiconducting polymers. The results show that 4CNN is a new generation of cross‐linker for the photo‐patterning of polymeric semiconductors for all‐solution‐processible flexible electronic devices.

Electronically optimized diazirine-based polymer crosslinkers

“…For example, Burgoon and co-workers reported the use of bis-(benzyl) ether 2 for photopatterning of cycloolefin polymers, 11 while the Anzenbacher group developed bis-(aryl) ether 3 for crosslinking the components of organic light-emitting diodes, 12 and the Zhang lab used tetrakis-diazirine 4 for photopatterning polymeric semiconductors. 13 Meanwhile the Bao group reported compound 5 (linked with an aliphatic tether) for use in patterning wearable elastic circuits, 14 while our lab developed 6 (linked with flexible perfluoroalkyl chains) for adhesion of commodity plastics. 15 Polymeric analogues ( e.g.…”

An Efficient Diazirine‐Based Four‐Armed Cross‐linker for Photo‐patterning of Polymeric Semiconductors

“…Moreover, the crystal structure of 2CNN was determined (see the Supporting Information). [21] As shown in Figure S4a, 4CNN and 2CNN show absorptions around 243/356 nm and 267/ 360 nm, respectively.T he samples of 4CNN and 2CNN are stable at ambient condition, and moreover 4CNN and 2CNN are thermally stable below 128 8 8Cand 106 8 8C, respectively,on the basis of their TGA data (see Figure S4b).…”

Beyond a Linker: The Role of Photochemistry of Crosslinkers in the Direct Optical Patterning of Colloidal Nanocrystals

“…One possible solution to the air‐sensitivity of phenyl carbene‐based crosslinkers is to switch their ground state to singlet (unreactive to 3 O 2 ) by substitution of the aromatic ring, as predicted by Wulff and co‐workers [16b] . It is also important to note recent studies on the patterning of functional polymers with carbene‐based crosslinkers did not specify the required atmosphere for patterning [13a,b] …”