Esters containing non-aromatic cycles as solvents for OLED formulations

Patent metadata

Field	Value
Publication number	US-10808170-B2
Application number	US-201615735013-A
Country	US
Kind code	B2
Filing date	May 13, 2016
Priority date	Jun 12, 2015
Publication date	Oct 20, 2020
Grant date	Oct 20, 2020

Abstract

The present invention relates to formulations for the preparation of organic electronic devices (OLEDs) which comprise at least one specific ester solvent containing a non aromatic cycle and at least one organic functional material selected from organic conductors, organic semiconductors, organic fluorescent compounds, organic phosphorescent compounds, organic light-absorbent compounds, organic light-sensitive compounds, organic photosensitisation agents and other organic photoactive compounds, selected from organometallic complexes of transition metals, rare earths, lanthanides and actinides.

First claim

The invention claimed is:

1. A formulation comprising
at least one ester solvent according to General Formula (II):

wherein

is a non-aromatic cyclic alkyl or alkenyl group having from 3 to 20 carbon atoms, to which the substituents R 2 , R 3 and —[CH 2 ] m —O—CO—R 1 or —[CH 2 ] m —CO—O—R 1 are bound as shown in General Formulae (I) and (II), respectively, in which one or more hydrogen atoms may be optionally replaced by F and in which one or more non-adjacent CH 2 groups may be optionally replaced by —O—;
R 1 and R 2 are the same or different from each other and are independently selected from the group consisting of hydrogen, straight-chain alkyl or alkenyl groups having from 1 to 20 carbon atoms, branched-chain alkyl or alkenyl groups having from 3 to 20 carbon atoms, cyclic alkyl or alkenyl groups having from 3 to 20 carbon atoms, and aryl or heteroaryl groups having from 4 to 6 carbon atoms, wherein one or more hydrogen atom may be optionally replaced by F and wherein one or more non-adjacent CH 2 groups may be optionally replaced by —O— or —Si(R 4 ) 2 —;
R 3 is identical or different at each occurrence and is selected from the group consisting of straight-chain alkyl or alkenyl groups having from 1 to 20 carbon atoms, branched-chain alkyl or alkenyl groups having from 3 to 20 carbon atoms, cyclic alkyl or alkenyl groups having from 3 to 20 carbon atoms, and aryl or heteroaryl groups having from 4 to 6 carbon atoms, wherein one or more hydrogen atoms may be optionally replaced by F and wherein one or more non-adjacent CH 2 groups may be optionally replaced by —O— or —Si(R 4 ) 2 — and/or a plurality of R 3 may together form a mono- or polycyclic aliphatic ring system;
R 4 is identical or different at each occurrence and is selected from the group consisting of hydrogen, straight-chain alkyl or alkenyl groups having from 1 to 20 carbon atoms, branched-chain alkyl or alkenyl groups having from 3 to 20 carbon atoms, cyclic alkyl or alkenyl groups having from 3 to 20 carbon atoms, and aryl or heteroaryl groups having from 4 to 6 carbon atoms, wherein one or more hydrogen atoms may be optionally replaced by F and wherein one or more non-adjacent CH 2 groups may be optionally replaced by —O—, —(C═O)—O— or —(C═O)—;
m is an integer from 0 to 5; and
n is an integer from 0 to 2x-2, wherein x is the number of carbon atoms in the non-aromatic cyclic alkyl or alkenyl group

and at least one organic functional material selected from the group consisting of organic conductors, organic semiconductors, organic fluorescent compounds, organic phosphorescent compounds, organic light-absorbent compounds, organic light-sensitive compounds, organic photosensitisation agents and other organic photoactive compounds, selected from organometallic complexes of transition metals, rare earths, lanthanides and actinides.

2. The formulation according to claim 1 ,
wherein

is a non-aromatic cyclic alkyl or alkenyl group having from 4 to 12 carbon atoms, to which the substituents R 2 , R 3 and —[CH 2 ] m —O—CO—R 1 or —[CH 2 ] m —CO—O—R 1 are bound as shown in General Formulae (I) and (II), respectively, in which one or more hydrogen atoms may be optionally replaced by F and in which one or more non-adjacent CH 2 groups may be optionally replaced by —O—.

3. The formulation according to claim 1 ,
wherein

to which the substituents R 2 , R 3 and —[CH 2 ] m —O—CO—R 1 or —[CH 2 ] m —CO—O—R 1 are bound as shown in General Formula (II).

4. The formulation according to claim 1 , wherein R 1 , R 2 and each of R 3 are independently selected from the group consisting of hydrogen and alkyl having from 1 to 10 carbon atoms with the provision that R 3 is not hydrogen.

5. The formulation according to claim 4 , wherein R 1 , R 2 and each of R 3 are independently selected from the group consisting of hydrogen, methyl, ethyl, 1-propyl, 2-propyl, n-butyl, iso-butyl, sec-butyl, t-butyl, n-pentyl, 2-pentyl, 3-pentyl, 2-methylbutyl, 3-methylbutyl, 3-methylbut-2-yl, 2-methylbut-2-yl, 2,2-dimethylpropyl, n-hexyl, 2-hexyl, 3-hexyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 2-methylpent-2-yl, 3-methylpent-2-yl, 2-methylpent-3-yl, 3-methylpent-3-yl, 2-ethylbutyl, 3-ethylbutyl, 2,3-dimethylbutyl, 2,3-dimethylbut-2-yl, 2,2-dimethylbutyl, n-heptyl, n-octyl, n-nonyl and n-decyl with the provision that R 3 is not hydrogen.

6. The formulation according to claim 1 , wherein R 4 is identical or different at each occurrence and is selected from the group consisting of hydrogen, straight-chain alkyl or alkenyl groups having from 1 to 10 carbon atoms, branched-chain alkyl or alkenyl groups having from 3 to 10 carbon atoms, cyclic alkyl or alkenyl groups having from 3 to 10 carbon atoms, and aryl or heteroaryl groups having from 4 to 6 carbon atoms, wherein one or more hydrogen atoms may be optionally replaced by F and wherein one or more non-adjacent CH 2 groups may be optionally replaced by —O—, —(C═O)—O— or —(C═O)—.

7. The formulation according to claim 1 , wherein the ester solvent is selected from the group consisting of:

8. The formulation according to claim 1 , wherein the ester solvent is liquid at room temperature.

9. The formulation according to claim 1 , wherein the ester solvent has a boiling point of 400° C. or below, wherein the boiling point is given at 760 mm Hg.

10. The formulation according to claim 1 , wherein the formulation has a surface tension in the range from 1 to 70 mN/m.

11. The formulation according to claim 1 , wherein the formulation has a viscosity in the range from 0.8 to 50 mPas.

12. The formulation according to claim 1 , wherein the content of the ester solvent is in the range from 0.01 to 99.99 vol.-% based on the total amount of solvents in the formulation.

13. The formulation according to claim 1 , wherein the formulation contains at least one further solvent selected from the group consisting of substituted and non-substituted aromatic or linear esters; substituted and non-substituted aromatic or linear ethers; substituted or non-substituted arene derivatives; indane derivatives; substituted and non-substituted aromatic or linear ketones; substituted and non-substituted heterocycles, pyridines; fluorinated or chlorinated hydrocarbons; and linear or cyclic siloxanes.

14. The formulation according to claim 1 , wherein the content of the organic functional material in the formulation is in the range from 0.001 to 20 weight-% based on the total weight of the formulation.

15. The formulation according to claim 1 , wherein at least one organic functional material is selected from the group consisting of fluorescent emitters, phosphorescent emitters, host materials, matrix materials, exciton-blocking materials, electron-transport materials, electron-injection materials, hole-conductor materials, hole-injection materials, n-dopants, p-dopants, wide-band-gap materials, electron-blocking materials or hole-blocking materials.

16. The formulation according to cla

Assignees

• Merck Patent Gmbh

Inventors

• Béalle Gaëlle
• Leonhard Christoph
• Tseng Hsin-Rong
• Martynova Irina
• Ludemann Aurélie

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• H10K71/15 Primary

  characterised by the solvent used · CPC title

• C09D11/36

  based on non-aqueous solvents · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• C07C69/013

  Esters of alcohols having the esterified hydroxy group bound to a carbon atom of a ring other than a six-membered aromatic ring · CPC title