Multi-component composition

Patent metadata

Field	Value
Publication number	US-12167682-B2
Application number	US-202017638867-A
Country	US
Kind code	B2
Filing date	Sep 15, 2020
Priority date	Sep 20, 2019
Publication date	Dec 10, 2024
Grant date	Dec 10, 2024

Abstract

A composition for manufacturing an organic electronic device includes at least three organic functional materials H1, H2, and H3, and at least one organic solvent. The organic functional materials H1 and H2 can form a type II semiconductor heterojunction structure. A LUMO value of the organic functional material H3 is greater than or equal to that of the organic functional materials H1 and H2, and a HOMO value thereof is less than or equal to that of the organic functional materials H1 and H2.

First claim

What is claimed is:

1. A composition, comprising at least three organic functional materials H1, H2, and H3, and at least one organic solvent;
wherein 1) H1 and H2 form a type II semiconductor heterojunction structure, and min (LUMO(H1)-HOMO(H2), LUMO(H2)-HOMO(H1))≤min(E T (H1), E T (H2))+0.1 eV; and 2) LUMO(H3)≥max(LUMO(H1), LUMO(H2)) and HOMO(H3)≤min (HOMO(H1), HOMO(H2));
wherein LUMO(H1) represents a lowest unoccupied molecular orbital energy level of H1, HOMO(H1) represents a highest occupied molecular orbital energy level of H1, and E T (H1) represents a triplet state energy level of H1; LUMO(H2) represents a lowest unoccupied molecular orbital energy level of H2, HOMO(H2) represents a highest occupied molecular orbital energy level of H2, and E T (H2) represents a triplet state energy level of H2; and LUMO(H3) represents a lowest unoccupied molecular orbital energy level of H3, and HOMO(H3) represents a highest occupied molecular orbital energy level of H3.

2. The composition according to claim 1 , wherein H1 is an electron transport material, and H2 is a hole transport material.

3. The composition according to claim 2 , wherein H1 has a structure of a general formula (1):

wherein Ar 1 to Ar 3 are independently selected from a substituted or unsubstituted aromatic group with 6 to 60 carbon atoms, a substituted or unsubstituted heteroaromatic group with 5 to 60 ring atoms, or a substituted or unsubstituted non-aromatic ring group with 3 to 30 ring atoms;
each Z 1 to Z 3 is same or different and independently represents CR 1 or N, and at least one of Z 1 to Z 3 is N; and
each R 1 is independently selected from the group consisting of H, D, a linear alkyl group with 1 to 20 carbon atoms, an alkoxy group with 1 to 20 carbon atoms, a thioalkoxy group with 1 to 20 carbon atoms, a branched alkyl group with 3 to 20 carbon atoms, a cyclic alkyl group with 3 to 20 carbon atoms, a silyl group, a keto group with 1 to 20 carbon atoms, an alkoxycarbonyl group with 2 to 20 carbon atoms, an aryloxycarbonyl group with 7 to 20 carbon atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF 3 , Cl, Br, F, I, a crosslinkable group, a substituted or unsubstituted aromatic group with 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group with 5 to 60 ring atoms, an aryloxy group with 5 to 60 ring atoms, a heteroaryloxy group with 5 to 60 ring atoms, or a combination thereof.

4. The composition according to claim 3 , wherein H1 has a structure selected from general formulas (1-1) to (1-4):

wherein each X independently represents CR 2 or N;
each Y independently represents CR 3 R 4 , NR 3 , BR 3 , O, S, SiR 3 R 4 , PR 3 , P(═O)R 3 , S═O, S(═O) 2 , or C═O;
Ar 4 is independently a substituted or unsubstituted phenyl group;
Ar 5 and Ar 6 are independently selected from a substituted or unsubstituted aromatic group with 6 to 60 carbon atoms, a substituted or unsubstituted heteroaromatic group with 5 to 60 ring atoms, or a substituted or unsubstituted non-aromatic ring group with 3 to 30 ring atoms;
wherein L 1 and L 2 are each independently selected from a single bond, a substituted or unsubstituted aromatic group with 6 to 60 carbon atoms, a substituted or unsubstituted heteroaromatic group with 5 to 60 ring atoms, or a substituted or unsubstituted non-aromatic ring group with 3 to 30 ring atoms; and
R 2 to R 4 are each independently selected from the group consisting of H, D, a linear alkyl group with 1 to 20 carbon atoms, an alkoxy group with 1 to 20 carbon atoms, a thioalkoxy group with 1 to 20 carbon atoms, a branched alkyl group with 3 to 20 carbon atoms, a cyclic alkyl group with 3 to 20 carbon atoms, a silyl group, a keto group with 1 to 20 carbon atoms, an alkoxycarbonyl group with 2 to 20 carbon atoms, an aryloxycarbonyl group with 7 to 20 carbon atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF 3 , Cl, Br, F, I, a crosslinkable group, a substituted or unsubstituted aromatic group with 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group with 5 to 60 ring atoms, an aryloxy group with 5 to 60 ring atoms, a heteroaryloxy group with 5 to 60 ring atoms, or a combination thereof.

5. The composition according to claim 3 , wherein H2 has a structure selected from general formulas (2-1) to (2-4):

wherein X 1 to X 9 each independently represent a single bond, CR 5 R 6 , NR 5 , O, S, SiR 5 R 6 , PR 5 , P(═O)R 5 , S═O, S(═O) 2 , or C═O, X 2 and X 3 are not a single bond at a same time, X 4 and X 5 are not a single bond at a same time, X 6 and X 7 are not a single bond at a same time, and X 8 and X 9 are not a single bond at a same time;
Ar 7 to Ar 12 are independently selected from a substituted or unsubstituted aromatic group with 6 to 60 carbon atoms, a substituted or unsubstituted heteroaromatic group with 5 to 60 ring atoms, or a substituted or unsubstituted non-aromatic ring group with 3 to 30 ring atoms;
wherein L 3 and L 4 are each independently selected from a single bond, a triarylamino group, a substituted or unsubstituted aromatic group with 6 to 60 carbon atoms, a substituted or unsubstituted heteroaromatic group with 5 to 60 ring atoms, or a substituted or unsubstituted non-aromatic ring group with 3 to 30 ring atoms;
n is an integer ranging from 1 to 4; and
R 5 and R 6 are each independently selected from the group consisting of H, D, a linear alkyl group with 1 to 20 carbon atoms, an alkoxy group with 1 to 20 carbon atoms, a thioalkoxy group with 1 to 20 carbon atoms, a branched alkyl group with 3 to 20 carbon atoms, a cyclic alkyl group with 3 to 20 carbon atoms, a silyl group, a keto group with 1 to 20 carbon atoms, an alkoxycarbonyl group with 2 to 20 carbon atoms, an aryloxycarbonyl group with 7 to 20 carbon atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF 3 , Cl, Br, F, I, a crosslinkable group, a substituted or unsubstituted aromatic group with 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group with 5 to 60 ring atoms, an aryloxy group with 5 to 60 ring atoms, a heteroaryloxy group with 5 to 60 ring atoms, or a combination thereof; and
H3 has a structure of a general formula (4):

wherein each Y 1 independently represents nonexistence, a single bond, CR 9 R 10 , NR 9 , O, S, SiR 9 R 10 , PR 9 , P(═O)R 9 , S═O, S(═O) 2 , or C═O;
each Ar 13 is independently selected from a substituted or unsubstituted aromatic group with 6 to 60 carbon atoms, a substituted or unsubstituted heteroaromatic group with 5 to 60 ring atoms, or a substituted or unsubstituted non-aromatic ring group with 3 to 30 ring atoms; and
R 9 to R 10 are each independently selected from the group consisting of H, D, a linear alkyl group with 1 to 20 carbon atoms, an alkoxy group with 1 to 20 carbon atoms, a thioalkoxy group with 1 to 20 carbon atoms, a branched alkyl group with 3 to 20 ca

Assignees

• Guangzhou Chinaray Optoelectronic Mat Ltd

Inventors

• Tan Jiahui
• Chen Yusheng
• Pan Junyou

Classifications

• H10K85/624 Primary

  containing six or more rings · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H10K2101/90

  Multiple hosts in the emissive layer · CPC title

• H10K2101/30

  Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values · CPC title

• H10K50/16

  Electron transporting layers · CPC title