Planarization layer for organic electronic devices

Abstract

The invention relates to organic electronic devices containing polycycloolefin planarization layers between the substrate and a functional layer like a semiconducting layer, dielectric layer or electrode, to the use of polycycloolefins as 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, and provided on said substrate a functional layer selected from semiconducting layers, dielectric layers and electrodes, wherein a planarization layer is provided 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 1 , wherein the polycycloolefinic polymer comprises a first type of repeating unit having 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 first type of 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 units 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 polycycloolefinic polymer comprises one or more distinct types of repeating units 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 polycycloolefinic polymer comprises one or more distinct types of repeating units formed from norbornene-type monomers independently selected from the following formulae: 
       
         
           
           
               
               
           
         
       
     
     
         12 . The organic electronic device of  claim 9 , wherein the polycycloolefinic polymer comprises one or more distinct types of repeating units 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 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 the top gate OFET of  claim 25 , comprising:
 a) depositing a layer of planarization material, which comprises a polycycloolefinic polymer or a polymer composition on a substrate,   b) forming source and drain electrodes on at least a portion of planarization layer,   c) depositing a layer of organic semiconductor material over said planarization layer and source and drain electrodes,   d) depositing a layer of dielectric material on organic semiconductor layer,   e) forming gate electrode on at least a portion of dielectric layer and   f) optionally depositing layer, which is an insulating and/or protection and/or stabilizing and/or adhesive layer, on the gate electrode and portions of dielectric layer.   
     
     
         28 . A process for preparing the bottom gate OFET of  claim 25 , comprising:
 a) depositing a layer of planarization material, which comprises a polycycloolefinic polymer or a polymer composition on a substrate,   b) forming gate electrode on at least a portion of planarization layer as depicted,   c) depositing a layer of dielectric material over said planarization layer and 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 layer as depicted, and   f) optionally depositing layer, which is an insulating and/or protection and/or stabilizing and/or adhesive layer, on the source and drain electrodes and portions of organic semiconductor layer.