Silicon-containing compounds for forming a patterning coating and devices incorporating same
A layered semiconductor device comprising a compound, the compound comprising a silicon-oxygen backbone and at least one fluorine-containing moiety attached to the silicon-oxygen backbone. The compound may comprise a unit represented by: formula (I) wherein R and R′ each independently represents at least one of: substituted or unsubstituted alkyl, substituted or unsubstituted fluoroalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted fluoroalkoxy, substituted or unsubstituted siloxy, or substituted or unsubstituted fluoroalkylsiloxy, substituted or unsubstituted cycloalkyl, substituted or unsubstituted fluorocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted fluoroaryl, or substituted or unsubstituted heteroaryl; and wherein at least one of R and R′ is the fluorine-containing moiety.
1 . A layered semiconductor device comprising:
at least one first electrode;
at least one second electrode;
at least one semiconducting layer disposed between the first and second electrodes, and
a compound comprising a silicon-oxygen backbone and at least one fluorine-containing moiety attached to the silicon-oxygen backbone.
2 . The device of claim 1 , wherein the compound comprises a unit represented by the following formula:
wherein:
R and R′ each independently represents at least one of: a substituted alkyl, an unsubstituted alkyl, a substituted fluoroalkyl, an unsubstituted fluoroalkyl, a substituted alkoxy, an unsubstituted alkoxy, a substituted fluoroalkoxy, an unsubstituted fluoroalkoxy, a substituted siloxy, an unsubstituted siloxy, a substituted fluoroalkylsiloxy, an unsubstituted fluoroalkylsiloxy, a substituted cycloalkyl, an unsubstituted cycloalkyl, a substituted fluorocycloalkyl, an unsubstituted fluorocycloalkyl, a substituted aryl, an unsubstituted aryl, a substituted fluoroaryl, an unsubstituted fluoroaryl, a substituted heteroaryl, and an unsubstituted heteroaryl; and
at least one of R and R′ is the fluorine-containing moiety.
3 . The device of claim 1 , wherein the compound is represented by the following formula:
wherein:
R and R′ each independently represents at least one of: a substituted alkyl, an unsubstituted alkyl, a substituted fluoroalkyl, an unsubstituted fluoroalkyl, a substituted alkoxy, an unsubstituted alkoxy, a substituted fluoroalkoxy, an unsubstituted fluoroalkoxy, a substituted siloxy, an unsubstituted siloxy, a substituted fluoroalkylsiloxy, an unsubstituted fluoroalkylsiloxy, a substituted cycloalkyl, an unsubstituted cycloalkyl, a substituted fluorocycloalkyl, an unsubstituted fluorocycloalkyl, a substituted aryl, an unsubstituted aryl, a substituted fluoroaryl, an unsubstituted fluoroaryl, a substituted heteroaryl, and an unsubstituted heteroaryl;
at least one of R and R′ is the fluorine-containing moiety; and
n is an integer of at least 3.
4 . The device of claim 3 , wherein n is an integer of between about 6-30.
5 . The device of claim 1 , wherein the silicon-oxygen backbone comprises a branching moiety.
6 . The device of claim 1 , wherein the silicon-oxygen backbone comprises a cyclic structure.
7 . The device of claim 1 , wherein the compound is represented by the following formula:
wherein:
T 1 and T 2 each independently represents at least one of: a substituted alkyl, an unsubstituted alkyl, a substituted fluoroalkyl, an unsubstituted fluoroalkyl, a substituted alkoxy, an unsubstituted alkoxy, a substituted fluoroalkoxy, an unsubstituted fluoroalkoxy, a substituted siloxy, an unsubstituted siloxy, a substituted fluoroalkylsiloxy, an unsubstituted fluoroalkylsiloxy, a substituted cycloalkyl, an unsubstituted cycloalkyl, a substituted fluorocycloalkyl, an unsubstituted fluorocycloalkyl, a substituted aryl, an unsubstituted aryl, a substituted heteroaryl, and an unsubstituted heteroaryl;
R and R′ each independently represents: at least one of a substituted alkyl, an unsubstituted alkyl, a substituted fluoroalkyl, an unsubstituted fluoroalkyl, a substituted alkoxy, an unsubstituted alkoxy, a substituted fluoroalkoxy, an unsubstituted fluoroalkoxy, a substituted siloxy, an unsubstituted siloxy, a substituted fluoroalkylsiloxy, an unsubstituted fluoroalkylsiloxy, a substituted cycloalkyl, an unsubstituted cycloalkyl, a substituted fluorocycloalkyl, an unsubstituted fluorocycloalkyl, a substituted aryl, an unsubstituted aryl, a substituted fluoroaryl, an unsubstituted fluoroaryl, a substituted heteroaryl, and an unsubstituted heteroaryl;
at least one of R and R′ is the fluorine-containing moiety; and
n is an integer of at least 3.
8 . The device of claim 7 , wherein T 1 and T 2 each independently represents at least one of: H, CF 3 , CF 2 H, and CH 3 .
9 . The device of claim 1 , wherein the silicon-oxygen backbone forms a caged structure.
10 . The device of claim 9 , wherein the compound is a silsesquioxane compound.
11 . The device of claim 9 , wherein the compound is represented by the formula (RSiO 1.5 ) v wherein:
v is an integer of between about 6-12; and
R represents, upon each occurrence, at least one of: a substituted alkyl, an unsubstituted alkyl, a substituted fluoroalkyl, an unsubstituted fluoroalkyl, a substituted alkoxy, an unsubstituted alkoxy, a substituted fluoroalkoxy, an unsubstituted fluoroalkoxy, a substituted siloxy, an unsubstituted siloxy, a substituted fluoroalkylsiloxy, and an unsubstituted fluoroalkylsiloxy; and
R, at least on one occurrence, is the fluorine-containing moiety.
12 . The device of claim 11 , wherein v is at least one of 6, 8, 10, or 12.
13 . The device of claim 9 , wherein the compound is represented by at least one of: Formula (PO-1), (PO-2), and (PO-3):
wherein in each formula, R represents, independently upon each occurrence, at least one of: a substituted alkyl, an unsubstituted alkyl, a substituted fluoroalkyl, an unsubstituted fluoroalkyl, a substituted alkoxy, an unsubstituted alkoxy, a substituted fluoroalkoxy, an unsubstituted fluoroalkoxy, a substituted siloxy, an unsubstituted siloxy, a substituted fluoroalkylsiloxy, an unsubstituted fluoroalkylsiloxy, a substituted cycloalkyl, an unsubstituted cycloalkyl, a substituted fluorocycloalkyl, an unsubstituted fluorocycloalkyl, a substituted aryl, an unsubstituted aryl, a substituted fluoroaryl, an unsubstituted fluoroaryl, a substituted heteroaryl, and an unsubstituted heteroaryl; and
at least one R is the fluorine-containing moiety.
14 . The device of claim 1 , wherein the fluorine-containing moiety is at least one of: a substituted fluoroalkyl, an unsubstituted fluoroalkyl, a substituted fluoroalkoxy, an unsubstituted fluoroalkoxy, a substituted fluoroalkylsiloxy, an unsubstituted fluoroalkylsiloxy, a substituted fluorocycloalkyl, an unsubstituted fluorocycloalkyl, a substituted fluoroaryl, an unsubstituted fluoroaryl, and a heteroaryl containing a fluorinated substituent.
15 . The device of claim 1 , wherein the fluorine-containing moiety is represented by the following formula:
wherein x is an integer of between about 1-6; y is an integer of between about 1-12; and A is H or F.
16 . The device of claim 15 , wherein y is 1, and A is F.
17 . The device of claim 1 , wherein the fluorine-containing moiety comprises a CH 2 CF 3 terminal group.
18 . The device of claim 1 , wherein the fluorine-containing moiety comprises a fluoroalkyl moiety comprising no more than 6 continuous fluorinated carbon atoms.
19 . The device of claim 1 , wherein the compound comprises a non-fluorinated moiety.
20 . The device of claim 19 , wherein the non-fluorinated moiety is at least one of: a substituted alkyl, an unsubstituted alkyl, a substituted alkoxy, an unsubstituted alkoxy, a substituted siloxy, an unsubstituted siloxy, a substituted cycloalkyl, an unsubstituted cycloalkyl, a substituted aryl, an unsubstituted aryl, a substituted heteroaryl, and an unsubstituted heteroaryl.
21 . The device of claim 1 , wherein the compound has a molecular weight of between about 1,000-5,000 g/mol.
22 . The device of claim 1 , comprising a patterning coating disposed on a first layer surface in a first portion of a lateral aspect of the device, and wherein the patterning coating comprises the compound.
23 . The device of claim 22 , wherein the surface energy of the patterning coating is no more than about 20 dynes/cm.
24 . The device of claim 22 , wherein a refractive index of the patterning coating is no more than about 1.4.
25 . The device of claim 1 , comprising an electrode coating disposed on a second layer surface in a second portion of the lateral aspect of the device.
26 . The device of claim 25 , wherein the electrode coating comprises silver (Ag), ytterbium (Yb), or magnesium (Mg).
27 . The device of claim 1 , comprising a plurality of layers disposed on a surface of a substrate and configured such that at least one of the plurality of layers lies: (i) between the substrate and the patterning coating in the first portion, and (ii) between the substrate and the electrode coating in the second portion.
28 . The device of claim 27 , wherein the at least one of the plurality of layers comprises at least one semiconducting layer.
29 . The device of claim 28 , wherein the at least one semiconducting layer comprises an electron transport layer (ETL).
30 . The device of claim 27 , wherein the at least one semiconducting layer comprises an emissive layer (EML).
31 . The device of claim 30 , wherein the EML lies between the ETL and the substrate.
32 . The device of claim 29 , wherein the plurality of layers comprises the at least one first electrode, which is disposed between the ETL and the substrate.
33 . The device of claim 32 , wherein the at least one first electrode is an anode.
34 . The device of claim 25 , wherein the at least one second electrode comprises the electrode coating.
35 . The device of claim 34 , wherein the at least one second electrode lies between the ETL and the patterning coating in the first portion.
36 . The device of claim 1 , wherein the at least one second electrode is a cathode.
37 . The device of claim 25 , wherein the second portion comprises at least one emissive region.
38 . The device of claim 22 , wherein the first portion comprises at least a part of a non-emissive region.
39 . The device of claim 22 , further comprising a discontinuous coating disposed on the patterning coating.
40 . The device of claim 39 , wherein the discontinuous coating comprises a plurality of islands.
41 . The device of claim 39 , wherein the electrode coating and the discontinuous coating comprise at least one material in common.
42 . The device of claim 41 , wherein the discontinuous coating covers less than about 25% of a surface of the patterning coating in the first portion.