Laminated structure, method for producing same, and electronic element comprising same

Patent metadata

Field	Value
Publication number	US-9318706-B2
Application number	US-200913056475-A
Country	US
Kind code	B2
Filing date	Jul 29, 2009
Priority date	Jul 30, 2008
Publication date	Apr 19, 2016
Grant date	Apr 19, 2016

Abstract

A laminated structure comprising an electrode, a polymer binding layer arranged on the electrode, and an electrically conductive organic material layer arranged on the polymer binding layer, wherein the polymer binding layer comprises an aromatic polymeric compound which has a structure represented by formula (I) [wherein Ar represents a conjugated divalent group which may have a substituent, provided that when there are multiple Ar's, the Ar's may be the same as or different from each other; and n represents an integer of 1 or greater] and has a number average molecular weight of 1×10 3 to 1×10 8 inclusive in terms of polystyrene content, the polymer binding layer is bonded to the electrode via a chemical bond between the aromatic polymeric compound and the surface of the electrode, and an electrically conductive organic material that composes a layer included in the electrically conductive organic material layer and arranged adjacent to the polymer binding layer has a number average molecular weight of 3×10 2 to 1×10 8 inclusive in terms of polystyrene content.

First claim

The invention claimed is:

1. A laminated structure comprising an electrode, a polymer binding layer disposed on the electrode, and a conductive organic material layer disposed on the polymer binding layer, wherein the polymer binding layer is composed of an aromatic polymer compound having a structure represented by the following formula (V):

wherein G is an r+p valent group having an aromatic ring; X 1 is a terminal group; r is an integer of 1 or greater and 10 or smaller, n and p are each independently an integer of 1 or greater, and if r is 2 or greater, the plurality of E present may be identical to or different from one another, and if n is 2 or greater, the plurality of Ar 1 present may be identical to or different from one another, and if p is 2 or greater, the plurality of X 1 present may be identical to or different from one another, wherein E is a binding group formed by a chemical bond between a monovalent group selected from the group consisting of a mercapto group, a hydroxy group, a carboxyl group, a sulfonic acid group, a phosphonic acid group, a trialkoxysilyl group, a trihydroxysilyl group, a chlorocarbonyl group, a chlorophosphonic acid group, a chlorosulfonic acid group, a cyanate group, an isocyanate group, an amino group, a substituted amino group and a substituted disulfide group, and a reactive group which is present on an Electrode Surface,
wherein Ar 1 comprises a repeating unit represented by the following formula (VI):

wherein R 5 is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group or a monovalent heterocyclic group, wherein the alkyl group, the aryl group, the arylalkyl group and the monovalent heterocyclic group each may optionally have a substituent, and R 6 is a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an arylalkenyl group, an arylalkynyl group, an amino group, a substituted amino group, a silyl group, a substituted silyl group, a halogen atom, an acyl group, an acyloxy group, a carbamoyl group, an imide residue, a monovalent heterocyclic group, a carboxyl group, a substituted carboxyl group or a cyano group, wherein the alkyl group, the alkoxy group, the alkylthio group, the aryl group, the aryloxy group, the arylthio group, the arylalkyl group, the arylalkoxy group, the arylalkylthio group, the arylalkenyl group, the arylalkynyl group, the acyl group, the acyloxy group, the carbamoyl group and the monovalent heterocyclic group each may optionally have a substituent, wherein the plurality of R 5 and R 6 present may be identical to or different from one another, and if R 5 and R 6 , which are alkyl groups optionally having a substituent, are each present in a plural number, they may be bonded to each other to form a ring
in an amount of 0.1% by mass or more with respect to the total mass of the number of all repeating units in the aromatic polymer compound which constitutes the polymer binding layer, and/or comprises a repeating unit represented by the following formula (VII):

wherein R 6 has the same definitions as in the formula (VI):
in an amount of 0.1% by mass or more with respect to the total mass of the number of all repeating units in the aromatic polymer compound which constitutes the polymer binding layer, and having a polystyrene equivalent number average molecular weight of 1 ×10 3 or more and 1 ×10 8 or less,
the polymer binding layer is connected to the electrode via a chemical bond between the aromatic polymer compound and the Electrode Surface.

2. The laminated structure according to claim 1 , wherein a film thickness of the polymer binding layer is from 0.1 nm to 100 μm, and a film thickness of the layer in the conductive organic material layer adjacent to the polymer binding layer is from 0.1 nm to 1 cm.

3. The laminated structure according to claim 1 , wherein an orbital energy of the lowest unoccupied molecular orbital (LUMO) of the aromatic polymer compound is −4.0 eV or more and −0.5 eV or less, and/or an orbital energy of the highest occupied molecular orbital (HOMO) of the aromatic polymer compound is −6.0 eV or more and −4.0 eV or less.

4. The laminated structure according to claim 1 , wherein a difference between the orbital energy of the LUMO of the aromatic polymer compound and an orbital energy of the LUMO of the conductive organic material which constitutes the layer in the conductive organic material layer adjacent to the polymer binding layer is −2.5 eV or more and +2.5 eV or less, and/or a difference between the orbital energy of the HOMO of the aromatic polymer compound and an orbital energy of the HOMO of the conductive organic material which constitutes the layer in the conductive organic material layer adjacent to the polymer binding layer is −1.5 eV or more and +1.5 eV or less.

5. The laminated structure according to claim 1 , wherein the electrode comprises at least one electroconductive compound selected from the group consisting of a base metal, a noble metal and an oxide thereof.

6. The laminated structure according to claim 1 , wherein the polymer binding layer is formed by immersing the electrode in a solution containing a conjugated polymer represented by the following formula (II) at a concentration of 0.0001% by mass or more, and/or by coating the electrode with the solution:

wherein Ar 1 , G, X 1 , r, n, p, and r are as defined previously, wherein if r is 2 or greater, the plurality of E a present may be identical to or different from one another, and wherein E a is a monovalent group selected from the group consisting of a mercapto group, a hydroxy group, a carboxyl group, a sulfonic acid group, a phosphonic acid group, a trialkoxysilyl group, a trihydroxysilyl group, a chlorocarbonyl group, a chlorophosphonic acid group, a chlorosulfonic acid group, a cyanate group, an isocyanate group, an amino group, a substituted amino group, and a substituted disulfide group.

7. The laminated structure according to claim 1 , wherein the binding group E in the formula (V) is a binding group formed by at least one selected from the group consisting of a covalent bond, a coordinate bond, a hydrogen bond and an ionic bond, which are formed between the monovalent group and the reactive group which is present on the Electrode Surface.

8. The laminated structure according to claim 1 , wherein the monovalent group is a monovalent group selected from the group consisting of a mercapto group, a carboxyl group, a sulfonic acid group, a phosphonic acid group, a chlorocarbonyl group, a chlorophosphonic acid group and a chlorosulfonic acid group.

9. The laminated structure according to claim 1 , wherein r in the formula (V) is an integer of 1 or greater and 3 or smaller (provided that if G in the formula (V) is a monocyclic aromatic ring structure and the number of carbon atoms that constitute the ring structure is 2, r is 1, and if the number of the carbon atoms is 3, r is 1 or 2).

10. The laminated structure according to claim 1 , wherein a total of the molar percentage of the repeating unit represented by the formula (VI) and the molar percentage

Assignees

• Tanaka Kenta
• Ishikawa Rui
• Temma Tomohisa
• Higashimura Hideyuki
• Sumitomo Chemical Co

Inventors

• Tanaka Kenta
• Ishikawa Rui
• Temma Tomohisa
• Higashimura Hideyuki

Classifications

• H10K50/805

  Electrodes · CPC title

• H10K50/18

  Carrier blocking layers · CPC title

• H10K50/17

  Carrier injection layers · CPC title

• H10K59/805

  Electrodes · CPC title

• H10K59/131

  Interconnections, e.g. wiring lines or terminals · CPC title