Planarization layer for organic electronic devices
View Patent ↗The invention relates to organic electronic devices containing polycycloolefin planarization layers between the substrate and a functional layer such as a semiconducting layer, dielectric layer, or electrode; to the use of polycycloolefins as a planarization layer on the substrate of an organic electronic device; and to processes for preparing such polycycloolefin planarization layers and organic electronic devices.
1. An organic electronic device comprising a substrate having a planarization layer disposed directly on the substrate, and provided on said substrate a functional layer selected from semiconducting layers, dielectric layers, and electrodes, wherein the planarization layer is positioned between the substrate and the functional layer, wherein said planarization layer comprises a polycycloolefinic polymer.
2. The organic electronic device of claim 1 , wherein the polycycloolefinic polymer is a norbornene-type polymer.
3. The organic electronic device of claim 1 , wherein the polycycloolefinic polymer comprises two or more distinct types of repeating units.
4. The organic electronic device of claim 3 , wherein one of the two or more distinct repeating units includes a pendant crosslinkable group.
5. The organic electronic device of claim 4 , wherein the pendant crosslinkable group is a latent crosslinkable group.
6. The organic electronic device of claim 5 , wherein the pendant crosslinkable group comprises a substituted or unsubstituted maleimide portion, an epoxide portion, a vinyl portion, an acetylene portion, an indenyl portion, a cinnamate portion or a coumarin portion.
7. The organic electronic device of claim 6 , wherein the repeating unit having a pendant crosslinkable group is derived during polymerization from one of the following monomers:
where n is an integer from 1 to 8, Q 1 and Q 2 are each independently selected from —H or —CH 3 , and R′ in P4 is —H or —OCH 3 .
8. The organic electronic device of claim 4 , wherein the polycycloolefinic polymer comprises a second type of repeating unit having a pendant silyl group.
9. The organic electronic device of claim 1 , wherein the polycycloolefinic polymer comprises one or more distinct types of repeating units represented by formula I
wherein Z is selected from —CH 2 —, —CH 2 —CH 2 — or —O—, m is an integer from 0 to 5, each of R 1 , R 2 , R 3 and R 4 are independently selected from H, a C 1 to C 25 hydrocarbyl, a C 1 to C 25 halohydrocarbyl or a C 1 to C 25 perhalocarbyl group.
10. The organic electronic device of claim 9 , wherein the one or more distinct types of repeating units is formed from norbornene-type monomers independently selected from the following formulae:
wherein b is an integer from 1 to 6.
11. The organic electronic device of claim 9 , wherein the one or more distinct types of repeating units is formed from norbornene-type monomers independently selected from the following formulae:
12. The organic electronic device of claim 9 , wherein the one or more distinct types of repeating units is formed from norbornene-type monomers independently selected from the following formulae:
13. The organic electronic device of claim 1 , wherein the planarization layer comprises two or more polycycloolefinic polymers having one or more distinct types of repeating units of formula I
wherein Z is selected from —CH 2 —, —CH 2 —CH 2 — or —O—, m is an integer from 0 to 5, each of R 1 , R 2 , R 3 and R 4 are independently selected from H, a C 1 to C 25 hydrocarbyl, a C 1 to C 25 halohydrocarbyl or a C 1 to C 25 perhalocarbyl group.
14. The organic electronic device of claim 1 , wherein the planarization layer is derived from a polymer composition, said composition comprising one or more of a solvent, a crosslinking agent, an optional reactive solvent, a stabilizer, a UV sensitizer, an adhesion promoter, and a thermal sensitizer.
15. The organic electronic device of claim 14 , wherein the polymer composition comprises a compound selected of formula III1 or III2
P-A″-X′-A″-P III1
H 4-c C(A″-P) c III2
wherein X′ is O, S, NH or a single bond, A″ is a single bond or a connecting, spacer or bridging group selected from (CZ 2 ) n , (CH 2 ) n —(CH═CH) p —(CH 2 ) n , (CH 2 ) n —O—(CH 2 ) n , (CH 2 ) n —C 6 Q 10 -(CH 2 ) n , and C(O), where each n is independently an integer from 0 to 12, p is an integer from 1-6, Z is independently H or F, C 6 Q 10 is cyclohexyl that is substituted with Q, Q is independently H, F, CH 3 , CF 3 or OCH 3 , P is a latent crosslinkable group, and c is 2, 3 or 4, and where in formula III1 at least one of X′ and the two groups A″ is not a single bond.
16. The organic electronic device of claim 15 , wherein the compound of formula III1 is selected of formula C1:
wherein R 10 and R 11 are independently of each other H or a C 1 -C 6 alkyl group and A″ is as defined in claim 15 .
17. The organic electronic device of claim 14 , wherein the polymer composition comprises a compound of formula IV
G-A″-P IV
wherein G is a surface-active group of the formula —SiR 12 R 13 R 14 , or a group of the formula —NH—SiR 12 R 13 R 14 , wherein R 12 , R 13 and R 14 are each independently selected from halogen, silazane, C 1 -C 12 -alkoxy, C 1 -C 12 -alkylamino, optionally substituted C 5 -C 20 -aryloxy and optionally substituted C 2 -C 20 -heteroaryloxy, and wherein one or two of R 12 , R 13 and R 14 may also denote C 1 -C 12 -alkyl, optionally substituted C 5 -C 20 -aryl or optionally substituted C 2 -C 20 -heteroaryl,
P is a crosslinkable group selected from a maleimide, a 3-monoalkyl-maleimide, a 3,4-dialkylmaleimide, an epoxy, a vinyl, an acetylene, an indenyl, a cinnamate or a coumarin group, or comprises a substituted or unsubstituted maleimide portion, an epoxide portion, a vinyl portion, an acetylene portion, an indenyl portion, a cinnamate portion or a coumarin portion, and
A″ is a single bond or a connecting, spacer or bridging group selected from (CZ 2 ) n , (CH 2 ) n —(CH═CH) p —(CH 2 ) n , (CH 2 ) n —O, (CH 2 ) n —O—(CH 2 ) n , (CH 2 ) n —C 6 Q 4 -(CH 2 ) n , (CH 2 ) n —C 6 Q 10 -(CH 2 ) n and C(O)—O, where each n is independently an integer from 0 to 12, p is an integer from 1-6, Z is independently H or F, C 6 Q 4 is phenyl that is substituted with Q, C 6 Q 10 is cyclohexyl that is substituted with Q, Q is independently H, F, CH 3 , CF 3 or OCH 3 .
18. The organic electronic device of claim 17 , wherein the compound of formula IV is selected of formula A1:
where R 12 , R 13 , R 14 , and A″ are as defined in claim 17 , and R 10 and R 11 are each independently H or a C 1 -C 6 alkyl group.
19. The organic electronic device of claim 1 , wherein the substrate is a polyester film.
20. The organic electronic device of claim 19 , wherein the substrate is a polyethyleneterephthalate (PET) or polyethylenenaphthalate (PEN) film.
21. The organic electronic device of claim 1 , wherein an electrode is formed on the planarization layer.
22. The organic electronic device of claim 1 , wherein an organic semiconductor layer is formed on the planarization layer.
23. The organic electronic device of claim 1 , wherein a dielectric layer is formed on the planarization layer.
24. The organic electronic device of claim 1 , which is an Organic Field Effect Transistor (OFET), Organic Photovoltaic (OPV) Device, or Organic Sensor.
25. The organic electronic device of claim 24 , which is a top gate OFET or a bottom gate OFET.
26. A product or assembly comprising an organic electronic device of claim 1 , which is an Integrated Circuit (IC), a Radio Frequency Identification (RFID) tag, a security marking or security device containing an RFID tag, a Flat Panel Display (FPD), a backplane of an FPD, or a sensor.
27. A process for preparing a top gate OFET, the process comprising:
a) depositing a layer of planarization material, which comprises a polycycloolefinic polymer on a substrate,
b) forming source and drain electrodes on at least a portion of the planarization layer,
c) depositing a layer of organic semiconductor material over said planarization layer and the source and drain electrodes,
d) depositing a layer of dielectric material on the organic semiconductor layer,
e) forming a gate electrode on at least a portion of the dielectric layer and
f) optionally depositing a layer selected from an insulating, protection, stabilizing, and/or adhesive layer, on the gate electrode and portions of the dielectric layer.
28. A process for preparing a bottom gate OFET, the process comprising:
a) depositing a layer of planarization material, which comprises a polycycloolefinic polymer on a substrate,
b) forming a gate electrode on at least a portion of the planarization layer,
c) depositing a layer of dielectric material over said planarization layer and the gate electrode,
d) depositing a layer of organic semiconductor material) on dielectric layer,
e) forming source and drain electrodes on at least a portion of organic semiconductor layers as depicted, and
f) optionally depositing a layer selected from an insulating, protection, stabilizing, and/or adhesive layer, on the source and drain electrodes and portions of the organic semiconductor layer.