Treatment liquid containing ionic compound, organic electronic element, and method for producing organic electronic element

• US 10,665,786 B2
• Filed: 03/06/2014
• Issued: 05/26/2020
• Est. Priority Date: 03/08/2013
• Status: Active Grant

• Current Assignee: Resonac Corp. (Resonac Holdings Corp.)
• Original Assignee: Hitachi Chemical Company Limited (Resonac Holdings Corp.)
• Inventors: Funyuu, Shigeaki, Asano, Naoki, Ishitsuka, Kenichi
• Primary Examiner(s): Yang, Jay
• Application Number:
  US14/773,490
• Publication Number:
  US 20160020395A1
• Time in Patent Office: 2,273 Days
• Field of Search: None
• CPC Class Codes: C08G 2261/135 Cross-linked structures
• CPC Class Codes: C08G 2261/312 Non-condensed aromatic systems, e.g. benzene
• CPC Class Codes: C08G 2261/3142 fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
• CPC Class Codes: C08G 2261/3162 Arylamines
• CPC Class Codes: C08G 2261/3223 containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
• CPC Class Codes: C08G 2261/3241 containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole
• CPC Class Codes: C08G 2261/3246 containing nitrogen and sulfur as heteroatoms
• CPC Class Codes: C08G 2261/411 Suzuki reactions
• CPC Class Codes: C08G 2261/512 Hole transport
• CPC Class Codes: C08G 2261/5222 electrofluorescent
• CPC Class Codes: C08G 2261/76 crosslinking
• CPC Class Codes: C08G 2261/794 with polymeric dopants
• CPC Class Codes: C08G 2261/95 Use in organic luminescent diodes
• CPC Class Codes: C08G 61/12 Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
• CPC Class Codes: C08G 65/18 Oxetanes
• CPC Class Codes: C08G 65/22 Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
• CPC Class Codes: H10K 30/00 Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation integrated devices or assemblies of multiple devices H10K39/00, H10K65/00; electrolytic light-sensitive devices H01G9/20
• CPC Class Codes: H10K 50/15 Hole transporting layers
• CPC Class Codes: H10K 50/17 Carrier injection layers
• CPC Class Codes: H10K 71/12 using liquid deposition, e.g. spin coating
• CPC Class Codes: H10K 85/151 : Copolymers
• CPC Class Codes: H10K 85/60 : Organic compounds having low molecular weight H10K85/10 - H10K85/50 take precedence
• CPC Class Codes: H10K 85/653 : comprising only oxygen as heteroatom
• 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

Abstract

An embodiment of the present invention relates to a treatment liquid which contains an ionic compound and a solvent, and is used for adhering the ionic compound to at least one surface selected from the group consisting of a surface on which a layer having hole transport properties is to be formed, and a surface of a layer having hole transport properties.

Claims

1. A method for producing an organic electronic element comprising:

a step of forming an anode,

a step of forming a layer (A) having hole transport properties, and

a step of forming a cathode,

the method further comprising at least one step selected from the group consisting of;

a step of adhering a material comprising an ionic compound to a surface on which the layer (A) having hole transport properties is to be formed, and

a step of adhering a material comprising an ionic compound to a surface of the layer (A) having hole transport properties,

wherein the material comprising the ionic compound does not contain more than 0.1 part by mass of a compound having hole transport properties relative to 1 part by mass of the ionic compound, and wherein the ionic compound has at least one anion selected from the group consisting of anions represented by any one of the following formulae (1A), (2A), (3A), and (5A);

2. The method for producing an organic electronic element according to claim 1, wherein the material comprising the ionic compound does not contain more than 0.01 parts by mass of a compound having hole transport properties relative to 1 part by mass of the ionic compound.

3. The method for producing an organic electronic element according to claim 1, wherein the material comprising the ionic compound does not contain a compound having hole transport properties.

4. A method for producing an organic electronic element comprising the following set of steps (1) in order, or set of steps (2) in order:

(1) a step of forming an anode,

a step of adhering a material comprising an ionic compound to a surface of the anode by applying a treatment liquid comprising the ionic compound and a solvent to the surface of the anode,

a step of forming a layer (A) having hole transport properties on the surface of the anode to which the treatment liquid has been applied, and

a step of forming a cathode, or

(2) a step of forming an anode,

a step of forming a layer (B) having hole transport properties,

a step of adhering a material comprising an ionic compound to a surface of the layer (B) having hole transport properties by applying a treatment liquid comprising the ionic compound and a solvent to the surface of the layer (B) having hole transport properties,

a step of forming a layer (A) having hole transport properties on the surface of the layer (B) having hole transport properties to which the treatment liquid has been applied, and

a step of forming a cathode,

wherein the material comprising the ionic compound does not contain more than 0.1 part by mass of a compound having hole transport properties relative to 1 part by mass of the ionic compound, wherein the treatment liquid does not contain more than 0.1 part by mass of a compound having hole transport properties relative to 1 part by mass of the ionic compound, and wherein the ionic compound comprises at least one selected from the group consisting of;

anions represented by any one of the following formulae (1A), (2A), (3A), and (5A);

5. The method for producing an organic electronic element according to claim 4, wherein the ionic compound has at least one cation selected from the group consisting of cations of elements belonging to group 1 or group 2 of the IUPAC Periodic Table of Elements, and cations represented by any one of of the formulae (1B), (2B) and (3B).

6. The method for producing an organic electronic element according to claim 4, further comprising a step of forming a light-emitting layer.

7. An organic electronic element prepared using the method for producing an organic electronic element according to claim 4.

8. The method for producing an organic electronic element according to claim 4, wherein the treatment liquid comprising the ionic compound and a solvent does not contain more than 0.01 parts by mass of a compound having hole transport properties relative to 1 part by mass of the ionic compound.

9. The method for producing an organic electronic element according to claim 4, wherein the treatment liquid comprising the ionic compound and a solvent does not contain a compound having hole transport properties.

10. A method for producing an organic electronic element comprising:

a step of forming an anode,

a step of forming a layer (A) having hole transport properties, and

a step of forming a cathode,

the method further comprising at least one step selected from the group consisting of;

a step of adhering a material comprising an ionic compound to a surface on which the layer (A) having hole transport properties is to be formed, and

a step of adhering a material comprising an ionic compound to a surface of the layer (A) having hole transport properties,

wherein the step of adhering the material comprising the ionic compound is a step of applying a treatment liquid comprising the ionic compound, a compound having a polymerizable substituent and a solvent, wherein the treatment liquid does not contain more than 0.1 part by mass of a compound having hole transport properties relative to 1 part by mass of the ionic compound,

wherein the material comprising the ionic compound does not contain more than 0.1 part by mass of a compound having hole transport properties relative to 1 part by mass of the ionic compound, and wherein the ionic compound comprises at least one selected from the group consisting of;

anions represented by any one of the following formulae (1A), (2A), (3A), and (5A);

11. The method for producing an organic electronic element according to claim 10, wherein the treatment liquid comprising the ionic compound and a solvent does not contain more than 0.01 parts by mass of a compound having hole transport properties relative to 1 part by mass of the ionic compound.

12. The method for producing an organic electronic element according to claim 10, wherein the treatment liquid comprising the ionic compound and a solvent does not contain a compound having hole transport properties.

13. A method for producing an organic electronic element comprising:

a step of forming an anode,

a step of forming a layer (A) having hole transport properties, and

a step of forming a cathode,

the method further comprising at least one step selected from the group consisting of;

a step of adhering a material comprising an ionic compound to a surface on which the layer (A) having hole transport properties is to be formed, and

a step of adhering a material comprising an ionic compound to a surface of the layer (A) having hole transport properties,

wherein the material comprising the ionic compound does not contain more than 0.1 part by mass of a compound having hole transport properties relative to 1 part by mass of the ionic compound, and wherein the ionic compound comprises;

at least one anion selected from the group consisting of anions represented by any one of the following formulae (1A), (2A), (3A), (4A) and (5A);

14. The method for producing an organic electronic element according to claim 13, wherein the material comprising the ionic compound does not contain more than 0.01 parts by mass of a compound having hole transport properties relative to 1 part by mass of the ionic compound.

15. The method for producing an organic electronic element according to claim 13, wherein the material comprising the ionic compound does not contain a compound having hole transport properties.