阅读说明：本技术 有机功能材料的制剂 (Preparation of organic functional material ) 是由 安雅·雅提斯奇 埃德加·克吕热 曾信荣 伊里娜·马丁诺娃 萨比恩·科尼派尔 于 2019-02-25 设计创作，主要内容包括：本发明涉及含有至少一种有机功能材料和至少第一有机溶剂和第二有机溶剂的制剂,其中所述第一有机溶剂是金刚烷衍生物；以及通过使用这些制剂制备的电子器件。(The present invention relates to a formulation comprising at least one organic functional material and at least a first organic solvent and a second organic solvent, wherein the first organic solvent is an adamantane derivative; and electronic devices prepared by using these formulations.)

1. A formulation comprising at least one organic functional material and at least a first organic solvent and a second organic solvent, wherein the first organic solvent is an adamantane derivative.

2. The formulation of claim 1, wherein the first organic solvent is an adamantane derivative according to general formula (I)

Wherein

X is CR or N, preferably CR;

r is identical or different on each occurrence and is H, D, F, CN, NO₂，N(R¹)₂，Si(R¹)₃A linear alkyl, alkoxy or thioalkoxy group having 1 to 20 carbon atoms, a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, a linear alkenyl or alkynyl group having 2 to 20 carbon atoms, or a branched or cyclic alkenyl or alkynyl group having 3 to 20 carbon atoms, wherein one or more non-adjacent CH's are present₂The radicals being optionally substituted by-O-, -S-, -NR-¹-、-CONR¹-、-S(O)₂-O-、-Si(R¹)₂-、-CO-O-、-C＝O-、-CR¹＝CR¹-or-C.ident.C-and wherein one or more hydrogen atoms may be replaced by D, F, CN or NO₂Instead of, or as aryl or heteroaryl groups having from 5 to 60 ring atoms, or as aryloxy or heteroaryloxy groups having from 5 to 40 ring atoms, or as aralkyl or heteroaralkyl groups having from 5 to 40 ring atoms, said groups may be substituted by one or more non-aromatic R¹Are substituted by radicals and two substituents R on the same ring may in turn together form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system which may be substituted by a plurality of substituents R¹Substitution; and is

R¹In each case identical or different and are straight-chain alkyl or alkoxy groups having from 1 to 20 carbon atoms or branched or cyclic alkyl or alkoxy groups having from 3 to 20 carbon atoms, in which one or more non-adjacent CH' s₂The radicals may be replaced by-O-, -S-, -CO-O-, -C ═ O-, -CH ═ CH-, or-C ≡ C-, and in which one or more hydrogen atoms may be replaced by F, or have 4 to 14 carbon atoms and may be substituted by one or more non-aromatic R' S¹A group-substituted aryl or heteroaryl group.

3. The formulation according to claim 1 or 2, wherein the first organic solvent is an adamantane derivative according to general formula (I) where R and R¹As defined in claim 1, and X is CR.

4. The formulation of claim 1 or 2, wherein the firstThe organic solvent is an adamantane derivative according to the general formula (I) wherein R and R¹As defined in claim 1, and X is N.

5. The formulation according to one or more of claims 1 to 3, wherein the first organic solvent is an adamantane derivative according to general formula (II),

wherein R and R¹As defined in claim 1.

6. The formulation according to one or more of claims 1 to 5, wherein said first organic solvent has a surface tension ≥ 20 mN/m.

7. The formulation according to one or more of claims 1 to 6, wherein the content of the first organic solvent is in the range of 0.1 to 30 wt. -%, based on the total amount of solvents in the formulation.

8. The formulation according to one or more of claims 1 to 7, wherein the first organic solvent has a boiling point in the range of 100 ℃ to 400 ℃.

9. The formulation according to one or more of claims 1 to 8, wherein said formulation comprises at least one second organic solvent different from said first organic solvent.

10. The formulation according to one or more of claims 1 to 9, wherein the second organic solvent has a boiling point in the range of 100 ℃ to 400 ℃.

11. The formulation according to one or more of claims 1 to 10, wherein the solubility of the at least one organic functional material in the first organic solvent and in the second organic solvent is in the range of 1g/l to 250 g/l.

12. The formulation according to one or more of claims 1 to 11, wherein said formulation has a surface tension in the range of 10mN/m to 50 mN/m.

13. The formulation according to one or more of claims 1 to 12, wherein the formulation has a mPa of 1mPa^.s to 50mPa^.Viscosity in the s range.

14. The formulation according to one or more of claims 1 to 13, wherein the content of the at least one organic functional material in the formulation is in the range of 0.001 to 20 wt. -%, based on the total weight of the formulation.

15. The formulation according to one or more of claims 1 to 14, wherein the at least one organic functional material is selected from organic conductors, organic semiconductors, organic fluorescent compounds, organic phosphorescent compounds, organic light absorbing compounds, organic photoactive compounds, organic photosensitizers and other organic photoactive compounds, such as organometallic complexes of transition metals, rare earth elements, lanthanides and actinides.

16. The formulation according to claim 15, wherein the at least one organic functional material is selected from fluorescent emitters, phosphorescent emitters, host materials, exciton blocking materials, electron transporting materials, electron injecting materials, hole transporting materials, hole injecting materials, n-type dopants, p-type dopants, wide band gap materials, electron blocking materials and hole blocking materials.

17. A formulation according to claim 15, wherein the at least one organic functional material is an organic semiconductor selected from hole injecting materials, hole transporting materials, light emitting materials, electron transporting materials and electron injecting materials.

18. A formulation according to claim 17, wherein at least one organic semiconductor is selected from hole injection materials and hole transport materials.

19. A formulation according to claim 18, wherein the hole injection material and hole transport material are polymeric compounds or blends of polymeric compounds with non-polymeric compounds.

20. A method of preparing a formulation according to one or more of claims 1 to 19, wherein the at least one organic functional material is mixed with the at least first and second organic solvents.

21. A method of making an electroluminescent device, wherein at least one layer of the electroluminescent device is made by: deposition, preferably printing, of a formulation according to one or more of claims 1 to 19 on a surface and subsequent drying.

22. An electroluminescent device in which at least one layer is prepared as follows: deposition, preferably printing, of a formulation according to one or more of claims 1 to 19 on a surface and subsequent drying.

Technical Field

The present invention relates to a formulation comprising at least one organic functional material and at least a first organic solvent and a second organic solvent, wherein the first organic solvent is an adamantane derivative; and electroluminescent devices prepared by using these formulations.

Background

Organic Light Emitting Devices (OLEDs) have long been manufactured by vacuum deposition methods. Other techniques such as inkjet printing have been studied extensively recently because they have advantages such as cost savings and the possibility of scale-up. One of the main challenges of multi-layer printing is to determine relevant parameters to obtain uniform ink deposition on the substrate. To trigger such parameters as surface tension, viscosity or boiling point, additives may be added to the formulation.

Technical problem and object of the invention

Many solvents have been proposed in organic electronic devices for ink jet printing. However, the number of important parameters that play a role during the deposition and drying process makes solvent selection very challenging. Thus, there remains a need for improved formulations containing organic semiconductors for deposition by inkjet printing. It is an object of the present invention to provide a formulation for organic semiconductors which enables controlled deposition to form organic semiconductor layers with good layer properties and efficiency performance. It is another object of the present invention to provide a formulation of an organic semiconductor which, when used, for example, in an inkjet printing process, enables uniform application of ink droplets on a substrate, thereby providing good layer properties and efficiency performance.

Solution to the problem

The above object of the present invention is solved by providing a formulation comprising at least one organic functional material and at least a first organic solvent and a second organic material, wherein the first organic solvent is an adamantane derivative.

Advantageous effects of the invention

The present inventors have surprisingly found that the use of an adamantane derivative organic solvent as the first solvent enables complete control of surface tension and induces efficient ink deposition to form uniform and clearly distinguishable organic layers of functional materials, which have good layer properties and performance.

Drawings

Fig. 1 shows a typical layer structure of a device comprising a substrate, an ITO anode, a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), a green emitting layer (G-EML), a Hole Blocking Layer (HBL), an Electron Transport Layer (ETL), and an Al cathode.

Fig. 2 to 10 show the film profiles of comparative example 1 and examples 1 to 8.

Detailed Description

The invention relates to a formulation comprising at least one organic functional material and at least a first organic solvent and a second organic solvent, wherein the first organic solvent is an adamantane derivative.