Bank structures for organic electronic devices

• US 9,331,281 B2
• Filed: 04/24/2013
• Issued: 05/03/2016
• Est. Priority Date: 04/25/2012
• Status: Active Grant

• Current Assignee: Flexenable Technology Limited, Merck Patent GmbH (Merck & Co., Inc.), Promerus, LLC (Sumitomo Bakelite Company Limited)
• Original Assignee: Merck Patent GmbH (Merck & Co., Inc.), Promerus, LLC (Sumitomo Bakelite Company Limited)
• Inventors: Miskiewicz, Pawel, Backlund, Tomas, May, Philip Edward, Cull, Toby, Rhodes, Larry F., Elce, Edmund, Bell, Andrew
• Primary Examiner(s): Nguyen, Dao H
• Application Number:
  US13/869,436
• Publication Number:
  US 20130285026A1
• Time in Patent Office: 1,105 Days
• Field of Search: 257/40, 257/57, 257/618, 257/737, 257/E51.001, 257/E51.002, 257/E29.003, 257/E29.022, 257/E21.511, 257/E21.615, 438/22, 438/99, 438/197, 526/266, 526/273, 526/281, 252/500, 430/281.1, 430/319, 430/323
• US Class Current: 1/1
• CPC Class Codes: C08G 2261/418 Ring opening metathesis polymerisation [ROMP]
• CPC Class Codes: C08G 61/08 of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
• CPC Class Codes: C08L 65/00 Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain C08L7/00 - C08L57/00, C08L61/00 take precedence; Compositions of derivatives of such polymers
• CPC Class Codes: H10K 10/466 Lateral bottom-gate IGFETs comprising only a single gate
• CPC Class Codes: H10K 59/122 Pixel-defining structures or layers, e.g. banks
• CPC Class Codes: H10K 59/173 comprising banks or shadow masks
• CPC Class Codes: H10K 85/10 Organic polymers or oligomers
• CPC Class Codes: H10K 85/111 comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
• CPC Class Codes: Y02E 10/549 Organic PV cells

Abstract

Embodiments in accordance with the present invention relate generally to the use of polycycloolefinic polymers as a structure defining material in organic electronic devices, and more specifically to separators, insulating structures or bank structures of such devices and to organic electronic devices comprising such structures, to processes for preparing such structures and to organic electronic devices encompassing such structures.

Claims

1. An organic electronic device comprising a substrate in contact with one or more bank structures, wherein said bank structures comprise a polycycloolefinic polymer that includes one or more distinct types of repeating units of formula I

2. The organic electronic device of claim 1, wherein the polycycloolefinic polymer is a copolymer comprising two or more distinct types of repeating units.

3. The organic electronic device of claim 1, wherein the polycycloolefinic polymer comprises a repeating unit having a pendent crosslinkable group.

4. The organic electronic device of claim 3, wherein the pendent 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.

5. The organic electronic device of claim 4, wherein the repeating unit having a pendent crosslinkable group is derived during polymerization from one of the following monomers:

6. The organic electronic device of claim 1, wherein the polycycloolefinic polymer comprises one or more repeating units from norbornene-type monomers independently selected from the following formulae:

7. The organic electronic device of claim 6, wherein the polycycloolefinic copolymer further comprises one or more repeating units from norbornene-type monomers independently selected from the following formulae:

8. The organic electronic device of claim 7, wherein the polycycloolefinic copolymer comprises units of the formula 15

9. The organic electronic device of claim 1, wherein the polycycloolefinic polymer comprises one or more repeating units from norbornene-type monomers independently selected from the following formulae:

10. The organic electronic device of claim 1, wherein the bank structures are 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.

11. The organic electronic device of claim 1, wherein the polymer composition comprises a crosslinking agent selected of formula III1 or III2

P-A″

-X′

-A″

-P 

 

III1

H<sub>4−

c</sub>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 (CZ₂)_n, (CH₂)_n—

(CH═

CH)_p—

(CH₂)_n, (CH₂)_n—

O—

(CH₂)_n, (CH₂)_n—

C₆Q₁₀-(CH₂)_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, C₆Q₁₀ is cyclohexyl that is substituted with Q, Q is independently H, F, CH₃, CF₃ or OCH₃, 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.

12. The organic electronic device of claim 11, wherein the compound of formula III1 is selected of formula C1

13. The organic electronic device of claim 1, wherein the polymer composition comprises a crosslinking agent of formula IV

G¹-A″

-G² 

 

IV

wherein G¹ is a surface active group, A″

is a single bond or a connecting, spacer or bridging group, and G² is a crosslinkable group or a non-reactive compatibilizing group.

14. The organic electronic device of claim 13, wherein G¹ is a surface-active group of the formula —

SiR¹²R¹³R¹⁴, or a group of the formula —

NH—

SiR¹²R¹³R¹⁴, wherein R¹², R¹³ and R¹⁴ are each independently selected from halogen, silazane, C₁-C₁₂-alkoxy, C₁-C₁₂-alkylamino, optionally substituted C₅-C₂₀-aryloxy and optionally substituted C₂-C₂₀-heteroaryloxy, and wherein one or two of R¹², R¹³ and R¹⁴ may also denote C₁-C₁₂-alkyl, optionally substituted C₅-C₂₀-aryl or optionally substituted C₂-C₂₀-heteroaryl,

G² is a crosslinkable group selected from a maleimide, a 3-monoalkyl-maleimide, a 3,4-dialkylmaleimide, an epoxy, a vinyl, an acetyl, 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 (CZ₂)_n, (CH₂)_n—

(CH═

CH)_p—

(CH₂)_n, (CH₂)_n—

O, (CH₂)_n—

O—

(CH₂)_n, (CH₂)_n—

C₆Q₄-(CH₂)_n, (CH₂)_n—

C₆Q₁₀-(CH₂)_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, C₆Q₄ is phenyl that is substituted with Q, C₆Q₁₀ is cyclohexyl that is substituted with Q, Q is independently H, F, CH₃, CF₃ or OCH₃.

15. The organic electronic device of claim 14, wherein the compound of formula IV is selected of formula A1:

16. The organic electronic device of claim 1, which is an Organic Field Effect Transistor (OFET), Organic Thin Film Transistor (OTFT), Organic Light Emitting Diode (OLED) or Organic Photovoltaic (OPV) device.

17. The organic electronic device of claim 16, which is a top gate OFET or bottom gate OFET.

18. The organic electronic device of claim 17, which comprises a substrate, a gate electrode, a dielectric layer serving as gate insulator, source and drain electrodes that are spaced apart with a channel region located therebetween, first and second bank structures that are patterned such that they define a well that extends over the channel region, and an OSC layer provided in the channel region, wherein the bank structures are derived from a polycycloolefinic polymer or said polymer composition.

19. A process for preparing the organic electronic device of claim 18, which comprise:

a) forming gate electrode on a substrate,

b) depositing a layer of dielectric material on the gate electrode,

c) forming source and drain electrodes on the dielectric layer such that they are spaced apart with a channel region located therebetween,

d) forming bank structures by depositing a bank structure material comprising a polycycloolefinic polymer or said polymer composition on the source and drain electrodes, thereby defining a well that extends over the channel region, and

e) depositing a layer of semiconductor material in the well formed by the bank structures and onto the source and drain electrodes.

20. The organic electronic device of claim 17, which comprises a substrate, source and drain electrodes that are spaced apart with a channel region located therebetween, first and second bank structures that are patterned such that they define a well that extends over the channel region, an OSC layer provided in the channel region, a dielectric layer serving as gate insulator, and gate electrode, wherein the bank structures are derived from a polycycloolefinic polymer or said polymer composition.

21. A process for preparing the organic electronic device of claim 20, which comprise:

a) forming source and drain electrodes on a substrate such that they are spaced apart with a channel region located therebetween,

b) forming bank structures by depositing a bank structure material comprising a polycycloolefinic polymer or said polymer composition on the source and drain electrode, thereby defining a well that extends over the channel region,

c) depositing a layer of semiconductor material in the well formed by the bank structures and onto the source and drain electrodes,

d) depositing a layer of dielectric material on the semiconductor layer, and

e) forming gate electrode on the dielectric layer.

22. The organic electronic device according to claim 16, which comprises one or more electrodes that are spaced apart to define a channel region located therebetween, and the bank structures are provided such that they are overlying said electrodes and define a well or a pattern of wells into which an organic semiconducting layer is deposited, so that the bank structures are contacting said electrodes and said organic semiconducting layer.

23. The organic electronic device of claim 1, wherein the bank structures are formed as single layers comprising a polycycloolefinic polymer.

24. A product or assembly comprising the organic electronic device according to 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, a backlight of an FPD, an electrophotographic device, an electrophotographic recording device, an organic memory device, a sensor, a biosensor or a biochip.

25. A bank structure in an organic electronic device comprising a polycycloolefinic polymer that includes one or more distinct types of repeating units of formula I

26. The bank structure of claim 25 wherein the organic electronic device is an Organic Field Effect Transistor (OFET), Organic Thin Film Transistor (OTFT), Organic Light Emitting Diode (OLED) or Organic Photovoltaic (OPV) device.

27. The bank structure of claim 25, wherein the polycycloolefinic polymer is a polycycloolefinic copolymer comprising one or more repeating units from norbornene-type monomers independently selected from the following formulae: