Printing ink and electronic device manufactured by printing with same

Patent metadata

Field	Value
Publication number	US-2018237691-A1
Application number	US-201615751370-A
Country	US
Kind code	A1
Filing date	Jul 5, 2016
Priority date	Aug 14, 2015
Publication date	Aug 23, 2018
Grant date	—

Abstract

A printing ink comprising inorganic nano-materials. The provided printing ink comprises at least one inorganic nano-material, in particular, quantum dots, and at least one aryl ketone-based or aryl ether-based organic solvent. Also provided is an electronic device manufactured by printing with the printing ink, in particular, an electroluminescent device.

First claim

What is claimed is:

1 . A printing ink, comprising an inorganic nano-material, and at least one aryl ketone-based or aryl ether-based organic solvent, wherein, the aryl ketone-based or aryl ether-based organic solvent has a boiling point over 200° C., and a viscosity in a range of 1 cPs to 100 cPs at 25° C., the aryl ketone-based or aryl ether-based organic solvent is able to be evaporated from a solvent system and forming an inorganic nano-material film.

2 . The printing ink according to claim 1 , wherein the aryl ketone-based or aryl ether-based organic solvent has a surface tension in a range of 19 dyne/cm to 50 dyne/cm at 25° C.

3 . The printing ink according to claim 1 , wherein the aryl ketone-based or aryl ether-based organic solvent has a structure shown as a general formula (I) and (II), respectively:

wherein, an Ar 1 and an Ar 2 may be identical or different, and each is a substituted or unsubstituted aryl or heteroaryl ring system having 5 to 40 ring atoms;
the Ar 1 and the Ar 2 may be different, and one of them is a substituted or unsubstituted aryl or heteroaryl ring system having 5 to 40 ring atoms, another is a linear alkyl, alkoxy or thioalkoxy group having 1 to 20 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group or a silyl group having 3 to 20 carbon atoms, or a substituted keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, a cyano group (—CN), a carbamoyl group (—C(═O)NH 2 ), a haloformyl group (—C(═O)—X, wherein X represents a halogen atom), a formyl group (—C(═O)—H), an isocyano group, an isocyanate group, a thiocyanate group or an isothiocyanate group, a hydroxyl group, a nitro group, a CF 3 group, a Cl, a Br, a F, a crosslinkable group, or a combination thereof.

4 . The printing ink according to claim 1 , wherein the substituted or unsubstituted aryl or heteroaryl group, that both the Ar 1 and the Ar 2 in the general formulas (I) and (II) are selected from, has a structure shown as a general formula below:

wherein,
X is CR 1 or N;
Y is selected from CR 2 R 3 , SiR 2 R 3 , NR 2 or, C(═0), S, or O;
R 1 , R 2 , R 3 is a H, a D, or a linear alkyl, alkoxy or thioalkoxy group having 1 to 20 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group or a silyl group having 3 to 20 carbon atoms, or a substituted keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, a cyano group (—CN), a carbamoyl group (—C(═O)NH 2 ), a haloformyl group (—C(═O)—X, wherein X represents a halogen atom), a formyl group (—C(═O)—H), an isocyano group, an isocyanate group, a thiocyanate group or an isothiocyanate group, a hydroxyl group, a nitro group, a CF 3 group, a Cl, a Br, a F, a crosslinkable group or a substituted or unsubstituted aryl or heteroaryl ring system having 5 to 40 ring atoms, or an aryloxy or a heteroaryloxy group having 5 to 40 ring atoms, or a combination thereof, wherein one or more groups of R 1 , R 2 , R 3 may form a mono or polycyclic aliphatic or aryl ring system by themselves or rings bonded with the groups.

5 . The printing ink according to claim 1 , wherein the organic solvent is a single aryl ketone solvent or a mixture of a plurality of aryl ketone solvents or a mixture of aryl ketone solvents and other solvents; or the organic solvent is a single aryl ether solvent, or a mixture of a plurality of aryl ether solvents, or a mixture of aryl ether solvents and other solvents; or the organic solvent is a mixture of aryl ketone solvents and aryl ether solvents or a mixture further mixed with other solvents.

6 . The printing ink according to claim 1 , wherein the organic solvent of the aryl ketone is 1-tetralone, 2-tetralone, acetophenone, propiophenone, benzophenone and a plurality of derivatives thereof.

7 . The printing ink according to claim 1 , wherein the organic solvent of the aryl ether is 3-phenoxytoluene, butoxybenzene, benzylbutylbenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl) benzene, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, dibenzyl ether, 1,2-dimethoxybenzene, glycidic phenyl ether.

8 . The printing ink according to claim 1 , wherein the aryl ketone-based organic solvent is a tetralone or a solvent comprising at least 50% by weight of the tetralone and at least one other additional solvent.

9 . The printing ink according to claim 1 , wherein the aryl ether-based organic solvent is a 3-phenoxytoluene or a solvent comprising at least 50% by weight of the 3-phenoxytoluene and at least one other additional solvent.

10 . The printing ink according to claim 1 , wherein the inorganic nano-material is a quantum dot material, that is, the particle diameter thereof has a monodisperse size distribution, and a shape thereof may be selected from a plurality of different forms, including a sphere, a cube, a rod or a branched structure.

11 . The printing ink according to claim 10 , wherein at least one luminescent quantum dot material is comprised, with a luminescence wavelength between 380 nm and 2500 nm.

12 . The printing ink according to claim 1 , wherein the at least one inorganic nano-material is a binary or multiple semiconductor compound or a mixture thereof in Group IV, Group II-VI, Group II-V, Group III-V, Group III-VI, Group IV-VI, Group I-III-VI, Group II-IV-VI, Group II-IV-V of the Periodic Table.

13 . The printing ink according to claim 1 , wherein the at least one inorganic nano-material is a perovskite nanoparticle material, specifically, a perovskite nanoparticle material, a metal nanoparticle material or a metal oxide nanoparticle material having a luminescent property, or a mixture thereof.

14 . The printing ink according to claim 1 , wherein at least one organic functional material is further comprised, the organic functional material may be selected from a hole injection material (HIM), a hole transport material (HTM), an electron transport materials (ETM), an electron injection material (EIM), an electrons blocking material (EBM), a hole blocking material (HBM), a light emitter (Emitter) and a host material (Host).

15 . The printing ink according to claim 1 , wherein a weight ratio of the inorganic nano-material is 0.3%˜70%, a weight ratio of the organic solvent comprised based on aryl ketone or aryl ether is 30%˜99.7%.

16 . An electronic device comprises a functional layer printed by the printing ink according to claim 1 , wherein the aryl ketone-based or aryl ether-based organic solvent may be evaporated from the solvent system, and forming a film comprising the inorganic nano-material.

17 . The electronic device according to claim 16 , wherein the electronic device is selected from a quantum dot light emitting diode (QLED), a quantum dot photovoltaic cell (QPV), a quantum dot light emitting electrochemical cell (QLEEC), a quantum dot field-effect transistor (QFET), a quantum dot light emitting field-effect transistor, a quantum dot Laser, a quantum dot sensor.

Assignees

• Guangzhou Chinaray Optoelectronic Mat Ltd

Inventors

• Pan Junyou
• Yang Xi

Classifications

• C01B17/20

  Methods for preparing sulfides or polysulfides, in general (ammonium sulfides or polysulfides C01C; sulfides or polysulfides of metals, other than alkali metals, magnesium, calcium, strontium and barium, see the relevant groups of subclasses C01F or C01G, according to the metal) · CPC title

• C30B7/14

  the crystallising materials being formed by chemical reactions in the solution · CPC title

• G01N33/533

  with fluorescent label · CPC title

• C01B19/007

  Tellurides or selenides of metals (C01B19/002 takes precedence) · CPC title

• C09K11/883 Primary

  with zinc or cadmium · CPC title