Adhesion promoter, electroactive layer and electroactive device comprising same, and method

• US 20060127562A1
• Filed: 12/15/2004
• Published: 06/15/2006
• Est. Priority Date: 12/15/2004
• Status: Active Grant

• Current Assignee: General Electric Company
• Original Assignee: General Electric Company
• Inventors: Liu, Jie, Manivannan, Venkatesan, Lewis, Larry, Cella, James, Faircloth, Tami
• Granted Patent: US 7,625,596 B2
• Time in Patent Office: Days
• US Class Current: 427/58
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 71/50 Forming devices by joining two substrates together, e.g. lamination techniques
• CPC Class Codes: H10K 85/115 Polyfluorene; Derivatives thereof
• CPC Class Codes: Y02E 10/549 Organic PV cells
• CPC Class Codes: Y02P 70/50 Manufacturing or production processes characterised by the final manufactured product
• CPC Class Codes: Y10S 428/917 Electroluminescent

Abstract

In one embodiment the present invention discloses a method for making a first layer in an electroactive device comprising the steps of (i) preparing a composition by mixing at least one adhesion promoter material and at least one electroactive material; and (ii) depositing said composition onto a second electroactive layer of said electroactive device; and (iii) optionally further depositing a third electroactive layer onto the surface of said first layer opposite the second layer, wherein said composition enables adhesion between said first layer and said second layer or between said first layer and said third layer, or between said first layer and both said second layer and said third layer. In another embodiment the present invention discloses a method for improving adhesion between layers in an electroactive device comprising the steps of (i) depositing a surface treatment composition comprising at least one adhesion promoter material on at least one surface of a first electroactive layer, and (ii) depositing a second electroactive layer onto the surface of said first layer comprising said adhesion promoter; wherein said composition enables adhesion between said first layer and said second layer of said electroactive device. Electroactive layers and electroactive devices comprising said layers are also disclosed, as well as methods to make said electroactive devices. In another embodiment adhesion promoters comprising 9,9-disubstituted fluorenyl compounds are disclosed, as well as methods for making the same.

Claims

1. A method for making a first layer in an electroactive device comprising the steps of (i) preparing a first layer composition by mixing at least one adhesion promoter material and at least one electroactive material;

and (ii) depositing said composition on a second electroactive layer of said electroactive device to form said first layer; and

(iii) optionally further depositing a third layer of electroactive material onto the surface of said first layer opposite the second layer, wherein said first layer composition enables adhesion between said first layer and said second layer or between said first layer and said third layer, or between said first layer and both said second layer and said third layer.

2. The method of claim 1, wherein said depositing is selected from the group consisting of reverse roll coating, wire-wound or Mayer rod coating, direct and offset gravure coating, slot die coating, blade coating, hot melt coating, curtain coating, knife over roll coating, extrusion, air knife coating, spray, rotary screen coating, multilayer slide coating, coextrusion, meniscus coating, comma and microgravure coating, spin coating, dip coating, lithographic process, langmuir process and flash evaporation, vapor deposition, plasma-enhanced chemical-vapor deposition, radio-frequency plasma-enhanced chemical-vapor deposition, expanding thermal-plasma chemical-vapor deposition, sputtering, reactive sputtering, electron-cyclotron-resonance plasma-enhanced chemical-vapor deposition, inductively coupled plasma-enhanced-chemical-vapor deposition, and combinations thereof.

3. The method of claim 1 wherein the adhesion promoter material comprises at least one compound selected from the group consisting of metal compounds, 9,9-disubstituted fluorenyl compounds, alpha-(1-naphthyl)-omega-trialkoxysilyl alkanes, copolymers of styrene and vinyl naphthalene, methacryloxyalkyl trialkoxysilanes and glycidoxyalkyl trialkoxysilanes.

4. The method of claim 3, wherein the metal compound further comprises at least one moiety selected from the group consisting of acetoxy, acetylacetonate, acryloxy, alkoxy, amino propyl, carbinol, carboxylate, silanol, siloxy, phosphite, phosphate, glycidoxy, mercaptopropyl, halides, chloride, bromide and oxides;

and wherein said metal is selected from the group consisting of silicon, tin, zirconium, hafnium, aluminum, antimony and titanium.

5. The method of claim 1 wherein the electroactive material is selected from the group consisting of an anode material, a cathode material, an organic light emitting material, a hole transport material, a hole injection material, a hole blocking material, an electron injection material, an electron transport material and combinations thereof.

6. The method of claim 5 wherein the light emitting material is selected from the group consisting of poly(N-vinylcarbazole), polyfluorene, poly(alkylfluorene), poly(para-phenylene), poly(p-phenylene vinylene), polythiophene, poly(pyridine vinylene), polyquinoxaline, polyquinoline, polysilanes, 1,3,5-tris{n-(4-diphenylaminophenyl)phenylamino}benzene, phenylanthracene, tetraarylethene, coumarin, rubrene, tetraphenylbutadiene, anthracene, perylene, coronene, tris(8-quinolinolato)aluminum;

derivatives of the foregoing, 8-hydroxyquinoline aluminum acetylacetonate, gallium acetylacetonate, indium acetylacetonate, aluminum-(picolylmethylketone)-bis{2,6-di(t-butyl)phenoxide}, scandium-(4-methoxy-picolylmethylketone)-bis(acetylacetonate), and combinations thereof.

7. The method of claim 5 wherein the cathode material is selected from the group consisting of K, Li, Na, Mg, Ca, Sr, Ba, Al, Ag, Au, In, Sn, Zn, Zr, Sc, Y, Mn, Pb, elements of the lanthanide series, and alloys thereof, indium tin oxide, tin oxide, indium oxide, zinc oxide, indium zinc oxide, zinc indium tin oxide, antimony oxide, carbon nanotubes, alkali metal fluorides, alkaline earth fluorides and combinations thereof.

8. The method of claim 5 wherein the anode material is selected indium tin oxide, tin oxide, indium oxide, zinc oxide, indium zinc oxide, zinc indium tin oxide, antimony oxide, nickel, gold, and combinations thereof.

9. The method of claim 5 wherein the hole injection and hole transport material is selected from the group consisting of poly(3,4-ethylenedioxythiophene), polyaniline, triaryldiamine, tetraphenyldiamine, aromatic tertiary amines, hydrazone derivatives, carbazole derivatives, triazole derivatives, imidazole derivatives, oxadiazole derivatives having an amino group, polythiophenes and combinations thereof.

10. The method of claim 5 wherein the electron injection and hole transport material is selected from the group consisting of tris(8-quinolinolato)aluminum, oxadiazole derivatives, perylene derivatives, pyridine derivatives, pyrimidine derivatives, quinoline derivatives, quinoxaline derivatives, diphenylquinone derivatives, nitro-substituted fluorene derivatives and combinations thereof.

11. The method of claim 5 wherein the hole blocking material is selected from the group consisting of poly(N-vinyl carbazole), bathocurpoine, bis(2-methyl-8-quinolinato)triphenylsilanolate aluminum (III), bis(2-methyl-8-quinolinato)4-phenolate aluminum (III), bis(2-methyl-8-quinolinato)4-phenylphenolate aluminum (III) and combinations thereof.

12. The composition comprising at least one adhesion promoter material and at least one electroactive material of claim 1.

13. The first layer made by the method of claim 1.

14. The first layer of claim 13, comprising a material selected from the group consisting of an anode material, a cathode material, an organic light emitting material, a hole transport material, a hole injection material, a hole blocking material, an electron injection material, an electron transport material and combinations thereof.

15. An electroactive device comprising the layer of claim 13.

16. The electroactive device of claim 15, wherein the device comprises a light emitting device, an organic light emitting device, a photovoltaic device, a photconductor, a photodetector, a liquid crystal display, an organic transistor or molecular electronic device component, or combinations thereof.

17. A method for making a first layer in an electroactive device comprising the steps of

(a) preparing a first layer composition by mixing at least one adhesion promoter material and at least one electroactive material, wherein the adhesion promoter material comprises at least one compound selected from the group consisting of mixtures of titanium tetraalkoxide with tetraalkyl orthosilicate, mixtures of titanium tetrabutoxide with tetraethylorthosilicate;

9,9-disubstituted fluorenyl compounds, alpha-(1-naphthyl)-omega-trialkoxysilyl alkanes, copolymers of styrene with vinyl naphthalene, methacryloxyalkyl trialkoxysilanes, methacryloxypropyltrimethoxysilanes, glycidoxyalkyl trialkoxysilanes, glycidoxypropyl trimethoxysilane, and combinations thereof; and

(b) depositing said composition on a second electroactive layer of said electroactive device to form said first layer, and optionally further depositing a third electroactive layer onto the surface of said first layer opposite the second layer, wherein said first layer composition enables adhesion between said first layer and said second layer or between said first layer and said third layer, or between said first layer and both said second layer and said third layer.

18. An electroactive layer comprising an intimate mixture of at least one adhesion promoter material and one electroactive organic material.

19. An electroactive device comprising a layer comprising an intimate mixture of at least one adhesion promoter material and one electroactive organic material.

20. A method for improving adhesion between layers in an electroactive device comprising the steps of (i) depositing a surface treatment composition comprising at least one adhesion promoter material on at least one surface of a first electroactive layer, and (ii) depositing a second electroactive layer onto the surface of said surface treatment composition comprising said adhesion promoter;

wherein said composition enables adhesion between said first layer and said second layer of said electroactive device.

21. The method of claim 20, wherein said depositing is selected from the group consisting of reverse roll coating, wire-wound or Mayer rod coating, direct and offset gravure coating, slot die coating, blade coating, hot melt coating, curtain coating, knife over roll coating, extrusion, air knife coating, spray, rotary screen coating, multilayer slide coating, coextrusion, meniscus coating, comma and microgravure coating, spin coating, dip coating, lithographic process, langmuir process and flash evaporation, vapor deposition, plasma-enhanced chemical-vapor deposition, radio-frequency plasma-enhanced chemical-vapor deposition, expanding thermal-plasma chemical-vapor deposition, sputtering, reactive sputtering, electron-cyclotron-resonance plasma-enhanced chemical-vapor deposition, inductively coupled plasma-enhanced chemical-vapor deposition, and combinations thereof.

22. The method of claim 20 wherein the adhesion promoter material comprises at least one compound selected from the group consisting of metal compounds, 9,9-disubstituted fluorenyl compounds, alpha-(1-naphthyl)-omega-trialkoxysilyl alkanes, copolymers of styrene and vinyl naphthalene, methacryloxyalkyl trialkoxysilanes and glycidoxyalkyl trialkoxysilanes.

23. The method of claim 22, wherein the metal compound further comprises at least one moiety selected from the group consisting of acetoxy, acetylacetonate, acryloxy, alkoxy, amino propyl, carbinol, carboxylate, silanol, siloxy, phosphite, phosphate, glycidoxy, mercaptopropyl, halides, chloride, bromide and oxides;

and wherein said metal is selected from the group consisting of silicon, tin, zirconium, hafnium, aluminum, antimony and titanium.

24. The method of claim 20 wherein the first or second electroactive layer comprises a material selected from the group consisting of an anode material, a cathode material, an organic light emitting material, a hole transport material, a hole injection material, a hole blocking material, an electron injection material, an electron transport material and combinations thereof.

25. The method of claim 24 wherein the light emitting material is selected from the group consisting of poly(N-vinylcarbazole), polyfluorene, poly(alkylfluorene), poly(para-phenylene), poly(p-phenylene vinylene), polythiophene, poly(pyridine vinylene), polyquinoxaline, polyquinoline, polysilanes, 1,3,5-tris{n-(4-diphenylaminophenyl)phenylamino}benzene, phenylanthracene, tetraarylethene, coumarin, rubrene, tetraphenylbutadiene, anthracene, perylene, coronene, tris(8-quinolinolato) aluminum;

derivatives of the foregoing, 8-hydroxyquinoline aluminum acetylacetonate, gallium acetylacetonate, indium acetylacetonate, aluminum-(picolylmethylketone)-bis{2,6-di(t-butyl)phenoxide}, scandium-(4-methoxy-picolylmethylketone)-bis(acetylacetonate), and combinations thereof.

26. The method of claim 24 wherein the cathode material is selected from the group consisting of K, Li, Na, Mg, Ca, Sr, Ba, Al, Ag, Au, In, Sn, Zn, Zr, Sc, Y, Mn, Pb, elements of the lanthanide series, and alloys thereof, indium tin oxide, tin oxide, indium oxide, zinc oxide, indium zinc oxide, zinc indium tin oxide, antimony oxide, carbon nanotubes, alkali metal fluorides, alkaline earth fluorides and combinations thereof.

27. The method of claim 24 wherein the anode material is selected indium tin oxide, tin oxide, indium oxide, zinc oxide, indium zinc oxide, zinc indium tin oxide, antimony oxide, nickel, gold, and combinations thereof.

28. The method of claim 24 wherein the hole injection and hole transport material is selected from the group consisting of poly(3,4-ethylenedioxythiophene), polyaniline, triaryldiamine, tetraphenyldiamine, aromatic tertiary amines, hydrazone derivatives, carbazole derivatives, triazole derivatives, imidazole derivatives, oxadiazole derivatives having an amino group, polythiophenes and combinations thereof.

29. The method of claim 24 wherein the electron injection and hole transport material is selected from the group consisting of tris(8-quinolinolato)aluminum, oxadiazole derivatives, perylene derivatives, pyridine derivatives, pyrimidine derivatives, quinoline derivatives, quinoxaline derivatives, diphenylquinone derivatives, nitro-substituted fluorene derivatives and combinations thereof.

30. The method of claim 24 wherein the hole blocking material is selected from the group consisting of poly(N-vinyl carbazole), bathocurpoine, bis(2-methyl-8-quinolinato)triphenylsilanolate aluminum (III), bis(2-methyl-8-quinolinato)4-phenolate aluminum (III), bis(2-methyl-8-quinolinato)4-phenylphenolate aluminum (III), and combinations thereof.

31. The first layer made by the method of claim 20.

32. The first layer of claim 31, comprising a material selected from the group consisting of an anode material, a cathode material, an organic light emitting material, a hole transport material, a hole injection material, a hole blocking material, an electron injection material, an electron transport material and combinations thereof.

33. An electroactive device comprising the layer of claim 31.

34. The electroactive device of claim 33, wherein the device comprises a light emitting device, an organic light emitting device, a photovoltaic device, a photconductor, a photodetector, a liquid crystal display, an organic transistor or molecular electronic device component, or combinations thereof.

35. A method for improving adhesion between layers in an electroactive device comprising the steps of (i) depositing a surface treatment composition comprising at least one adhesion promoter material on at least one surface of an electroactive layer;

and (ii) depositing a second electroactive layer onto the surface of said surface treatment composition comprising said adhesion promoter;

wherein the adhesion promoter material comprises at least one compound selected from the group consisting of mixtures of titanium tetraalkoxides with tetraalkylorthosilicates, mixtures of titanium tetrabutoxide with tetraethyl orthosilicate, 9,9-disubstituted fluorenyl compounds, alpha-(1-naphthyl)-omega-trialkoxysilyl alkanes, copolymers of styrene with vinyl naphthalene, methacryloxyalkyl trialkoxysilanes, methacryloxypropyltrimethoxysilanes, glycidoxyalkyl trialkoxysilanes, glycidoxypropyl trimethoxysilanes and combinations thereof, and wherein said composition enables adhesion between said first layer and said second layer of said electroactive device.

36. An electroactive layer with a surface treatment, wherein the surface treatment comprises a composition comprising at least one adhesion promoter material on at least one surface of the electroactive layer, wherein said composition enables adhesion between said layer and at least one other layer in an electroactive device;

and wherein the adhesion promoter material comprises at least one compound selected from the group consisting of mixtures of titanium tetraalkoxides with tetraalkylorthosilicates, mixtures of titanium tetrabutoxide with tetraethyl orthosilicate, 9,9-disubstituted fluorenyl compounds, alpha-(1-naphthyl)-omega-trialkoxysilyl alkanes, copolymers of styrene with vinyl naphthalene, methacryloxyalkyl trialkoxysilanes, methacryloxypropyltrimethoxysilanes, glycidoxyalkyl trialkoxysilanes, glycidoxypropyl trimethoxysilanes and combinations thereof.

37. An electroactive device comprising at least one electroactive layer with a surface treatment, wherein the surface treatment comprises a composition comprising at least one adhesion promoter material on at least one surface of the electroactive layer, wherein said composition enables adhesion between said layer and at least one other electroactive layer of said electroactive device;

wherein the adhesion promoter material comprises at least one compound selected from the group consisting of mixtures of titanium tetraalkoxides with tetraalkylorthosilicates, mixtures of titanium tetrabutoxide with tetraethyl orthosilicate, 9,9-disubstituted fluorenyl compounds, alpha-(1-naphthyl)-omega-trialkoxysilyl alkanes, copolymers of styrene with vinyl naphthalene, methacryloxyalkyl trialkoxysilanes, methacryloxypropyltrimethoxysilanes, glycidoxyalkyl trialkoxysilanes, glycidoxypropyl trimethoxysilanes and combinations thereof.

38. A method of making an electroactive device comprising (A) an anode layer, (B) a cathode layer, (C) a layer derived from a composition comprising an adhesion promoter and a first electroactive organic material, and (D) at least one other layer comprising an electroactive organic material different from the first electroactive organic material, comprising the steps of:

(i) providing a first and a second electrode layer different from each other;

(ii) forming a first composite structure comprising (a) the first electrode layer and (b) optionally one or more layers each comprising a different electroactive organic material,

(iii) forming a second composite structure comprising (c) the second electrode layer;

(d) a layer comprising the intimate mixture of the adhesion promoter material and the first electroactive organic material, and (e) optionally one or more layers each comprising a different electroactive organic material; and

(iv) forming the device by laminating the first composite structure and the second composite structure, wherein the layer comprising the adhesion promoter is in contact with and provides adhesion between an electrode layer and at least one other layer of electroactive organic material different from said first electroactive organic material.

39. A method of making an electroactive device comprising (A) an anode layer, (B) a cathode layer, (C) a layer derived from a first electroactive organic material, and (D) at least one other layer comprising an electroactive organic material different from the first electroactive organic material, comprising the steps of:

(i) providing a first and a second electrode layer different from each other;

(ii) forming a first composite structure comprising (a) the first electrode layer;

(b) an adhesion promoter material deposited on one surface of the first electrode layer and (c) optionally one or more layers each comprising a different electroactive organic material,

(iii) forming a second composite structure comprising (d) the second electrode layer; and

(e) one or more layers each comprising a different electroactive organic material; and

(iv) forming the device by laminating the first composite structure and the second composite structure, wherein the adhesion promoter is in contact with and provides adhesion between an electrode layer and a layer of electroactive organic material.

40. A method of making an electroactive device comprising (A) an anode layer, (B) a cathode layer, (C) a layer derived from a first electroactive organic material, and (D) at least one other layer comprising an electroactive organic material different from the first electroactive organic material, comprising the steps of:

(i) providing a first and a second electrode layer different from each other;

(ii) forming a first composite structure comprising (a) the first electrode layer;

(b) one or more layers each comprising a different electroactive organic material, and (c) an adhesion promoter material deposited on at least one surface of at least one electroactive organic layer;

(iii) forming a second composite structure comprising (d) the second electrode layer;

(e) one or more layers each comprising a different electroactive organic material; and

optionally (f) an adhesion promoter material deposited on at least one surface of at least one electroactive organic layer; and

(iv) orming the device by laminating the first composite structure and the second composite structure, wherein the adhesion promoter is in contact with and provides adhesion between a first layer comprising a first electroactive organic material and a second layer comprising an electroactive organic material different from said first electroactive organic material.

41. A 9,9-disubstituted fluorenyl compound of the formula (I):

42. The 9,9-disubstituted fluorenyl compound of claim 41, wherein x is zero;

each R¹ is the same and is a C₁-C₁₆ alkyl group; and

each R² is the same.

43. The 9,9-disubstituted fluorenyl compound of claim 41, wherein x is zero;

each R¹ is the same and is selected from the group consisting of methyl, ethyl, and n-propyl; and

each R² is the same and is selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, n-pentyl, iso-pentyl, methylpentyl, n-hexyl, and iso-hexyl.

44. A 9,9-bis(alkynyl) fluorenyl compound of the formula (IV):

45. The 9,9-bis(alkynyl) fluorenyl compound of claim 44, wherein x is zero;

and each R is the same.

46. The 9,9-bis(alkynyl) fluorenyl compound of claim 44, wherein x is zero;

and each R² is the same and is selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, n-pentyl, iso-pentyl, methylpentyl, n-hexyl, and iso-hexyl.

47. A method for preparing a 9,9-disubstituted fluorenyl compound of the formula (I):

48. The method of claim 47, wherein the solvent is a dipolar aprotic solvent and Z is selected from the group consisting of halide, bromide, and chloride.

49. The method of claim 47, wherein the solvent is a non-polar solvent;

Z is selected from the group consisting of halide, bromide, and chloride; and

the reaction mixture further comprises a phase transfer catalyst.

50. The method of claim 47, wherein Z is bromide;

x is zero;

each R¹ is the same and is a C₁-C₁₆ alkyl group; and

each R² is the same.

51. The method of claim 47, wherein Z is bromide;

x is zero;

each R¹ is the same and is selected from the group consisting of methyl, ethyl, and n-propyl; and

each R² is the same and is selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, n-pentyl, iso-pentyl, methylpentyl, n-hexyl, and iso-hexyl.