IP Library Granted Patent US 10,544,361
Granted Patent B2
US 10,544,361 · App. 15/544,556 · Granted Jan 28, 2020

Pyridines and derivatives thereof as components for use in optoelectronic components

Inventors: David Ambrosek (Berlin, DE); Michael Danz (Eggenstein-Leopoldshafen, DE); Harald Flügge (Karlsruhe, DE); Jana Friedrichs (Karlsruhe, DE); Tobias Grab (Karlsruhe, DE); Andreas Jacob (Hannover, DE); Stefan Seifermann (Brühl, DE); Daniel Volz (Karlsruhe, DE)
Assignee: CYNORA GMBH
C09K11/06H01L51/0059H01L51/0061H01L51/0067H01L51/0071H01L51/0072H01L51/5072H01L51/5096C09K2211/1007C09K2211/1014C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1044H01L51/5012Y02E10/549Y02P70/521
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,544,361
App. No.
15/544,556
Granted
Jan 28, 2020
Kind
B2
Abstract

The invention relates to an organic molecule comprising a structure of formula 1 and to the use thereof in optoelectronic components. wherein: X is SO2, CO or a C—C single bond; m is 0 or 1; n is 1, 2 or 3; r is 0 or 1; s is 0 or 1; LG is a divalent linker group, selected from: or LG is an element-element single bond.

Claims (80)

1. An optoelectronic device comprising:

a substrate,

an anode and

a cathode, wherein the anode or the cathode is applied to the substrate, and at least one light-emitting layer is disposed between the anode and the cathode, wherein the light-emitting layer comprises at least one host material, wherein an activated singlet state (S 1 ) and/or an activated triplet state (T 1 ) of the at least one host material is higher than an activated singlet state (S 1 ) and/or activated triplet state (T 1 ) of the organic molecule, and wherein the light-emitting layer further comprises an organic molecule comprising a structure of formula 3b:

wherein:

m is 0 or 1;

n is 1, 2 or 3;

LG is a divalent linker group, selected from

or LG is an element-element single bond;

wherein AF2 comprises a structure of formula 2:

wherein:

x is 1;

y is 0;

o is 0 or 1;

p is 0 or 1;

A is CR*** when o=0, otherwise C;

VG1 is a bridging group and is selected from the group consisting of

NR**, CR** 2 , O, S, a C—C single bond, BR**, AsR**, SiR** 2 , GeR** 2 ,

when x=1 and at the same time y=0;

VG2=bridging group at each occurrence independently of one another is selected from the group consisting of CR** 2 , NR**, O, S and a C—C single bond, wherein two units VG2 are not equal to a C—C single bond at the same time;

E is NR**,

O or S;

G is C when o=1 and at the same time x=1; G is CR** when o=0 and at the same time x=1;

J is C when x=1;

L is CR*** when y=0;

R*** is R** or is selected from the following units, wherein a maximum of two of the radicals R*** are simultaneously one of the following units:

R** at each occurrence independently of one another is a radical R* and/or marks the linking site to the linker group LG or in case m=0, to the pyridine unit of formula 3b;

R* at each occurrence independently of one another is selected from the group consisting of H, deuterium, phenyl, naphthyl, N(R 2 ) 2 —, —SCN, —NO 2 , a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms, each of which may be substituted with one or more radicals R 9 , wherein an adjacent CH 2 group may be replaced by —Si(R 4 ) 2 —, —Ge(R 4 ) 2 —, —Sn(R 4 ) 2 , —NR 2 —, —O—, or —S— and wherein one or more H atoms may be replaced by deuterium, F, Cl, Br, I, CF 3 or NO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which in each case may be substituted with one or more radicals R 2 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which with one or more radicals R 9 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which with one or more radicals R 9 , or a combination of these systems;

R 2 at each occurrence independently of one another is selected from the group consisting of H, deuterium, phenyl, naphthyl, CF 3 , a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms, each of which may be substituted with one or more radicals R 9 , wherein an adjacent CH 2 group is replaced by a —Si(R 4 ) 2 —, —Ge(R 4 ) 2 —, —Sn(R 4 ) 2 —NR 2 —, —O—, or —S— and wherein one or more H atoms may be replaced by deuterium, F, Cl, Br, I, CF 3 or NO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which in each case may be substituted with one or more radicals R 9 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted with one or more radicals R 9 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which with one or more radicals R 9 , or a combination of these systems;

R 4 at each occurrence independently of one another is selected from the group consisting of H, deuterium, phenyl, naphthyl, N(R 2 ) 2 , CF 3 , OH, a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms each of which may be substituted with one or more radicals R 9 , wherein or an adjacent CH 2 group may be replaced by —Si(R 4 ) 2 —, —Ge(R 4 ) 2 —, —Sn(R 4 ), —NR 2 —, —O—, or —S— and wherein one or more H atoms may be replaced by deuterium, F, Cl, Br, I, CF3 or NO2, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which in each case may be substituted with one or more radicals R 8 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted with one or more radicals R 9 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which may be substituted with one or more radicals R 9 , or a combination of these systems;

R 8 at each occurrence independently of one another is selected from the group consisting of H, deuterium, phenyl, naphthyl, F, CF 3 or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical with 1 to 20 C atoms, in which also one or more H atoms may be replaced by F or CF 3 ;

R 9 at each occurrence independently of one another is selected from the group consisting of H, deuterium, phenyl, naphthyl, N(R 2 ) 2 —, CF 3 , NO 2 , a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms, each of which may be substituted with one or more radicals R 8 , wherein an adjacent CH 2 group may be replaced by —Si(R 4 ) 2 —, —Ge(R 4 ) 2 —, —Sn(R 4 ) 2 —NR 2 —, —O—, or —S— and wherein one or more H atoms may be replaced by deuterium, F, Cl, Br, I, CF 3 or NO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which in each case may be substituted with one or more radicals R 8 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted with one or more radicals R 3 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which may be substituted with one or more radicals R 8 , or a combination of these systems.

2. The optoelectronic device according to claim 1 , comprising at least one host material comprising the organic molecule.

3. The optoelectronic device according to claim 1 , wherein the light-emitting layer comprises one or more of a fluorescent material or a phosphorescent material and wherein the fluorescent material or the phosphorescent material are an organic molecule.

4. The optoelectronic device according to claim 3 , in which the organic molecule together with a functional material forms an exciplex.

5. An optoelectronic device comprising:

a substrate,

an anode and

a cathode, wherein the anode or the cathode is applied to the substrate, and at least one light-emitting layer is disposed between the anode and the cathode, wherein the light-emitting layer comprises one or more of a fluorescent material or a phosphorescent material and wherein the fluorescent material or the phosphorescent material are an organic molecule, and wherein the light-emitting layer further comprises an organic molecule comprising a structure of formula 3b:

wherein:

m is 0 or 1;

n is 1, 2 or 3;

LG is a divalent linker group, selected from

or LG is an element-element single bond;

wherein AF2 comprises a structure of formula 2:

wherein:

x is 1;

y is 0;

o is 0 or 1;

p is 0 or 1;

A is CR*** when o=0, otherwise C;

VG1 is a bridging group and is selected from the group consisting of

NR**, CR** 2 , O, S, a C—C single bond, BR**, AsR**, SiR** 2 , GeR** 2 ,

when x=1 and at the same time y=0;

VG2=bridging group at each occurrence independently of one another is selected from the group consisting of CR**, NR**, O, S and a C—C single bond, wherein two units VG2 are not equal to a C—C single bond at the same time;

E is NR**,

O or S:

G is C when o=1 and at the same time x=1; G is CR** when o=0 and at the same time x=1;

J is C when x=1;

L is CR*** when y=0;

R*** is R** or is selected from the following units, wherein a maximum of two of the radicals

R*** are simultaneously one of the following units:

R** at each occurrence independently of one another is a radical R* and/or marks the linking site to the linker group LG or in case m=0, to the pyridine unit of formula 3b;

R* at each occurrence independently of one another is selected from the group consisting of H, deuterium, phenyl, naphthyl, N(R 2 ) 2 , —SCN, —CF 3 , —NO 2 , a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms, each of which may be substituted with one or more radicals R 9 , wherein an adjacent CH 2 group may be replaced by —Si(R 4 ) 2 —, —Ge(R 4 ) 2 —, —Sn(R 4 ), —O—, or —S— and wherein one or more H atoms may be replaced by deuterium, F, Cl, Br, I, CF 3 or NO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which in each case may be substituted with one or more radicals R 2 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which with one or more radicals R 9 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which with one or more radicals R 9 , or a combination of these systems;

R 2 at each occurrence independently of one another is selected from the group consisting of H, deuterium, phenyl, naphthyl, CF 3 , a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms, each of which may be substituted with one or more radicals R 9 , wherein an adjacent CH 2 group is replaced by a —Si(R 4 ) 2 —, —Ge(R 4 ) 2 —, —Sn(R 4 ) 2 —NR 2 —, —O—, or —S— and wherein one or more H atoms may be replaced by deuterium, F, Cl, Br, I, CF 3 or NO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which in each case may be substituted with one or more radicals R 9 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted with one or more radicals R 9 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which with one or more radicals R 9 , or a combination of these systems;

R 4 at each occurrence independently of one another is selected from the group consisting of H, deuterium, phenyl, naphthyl, N(R 2 ) 2 , CF 3 , OH, a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms each of which may be substituted with one or more radicals R 9 , wherein or an adjacent CH 2 group may be replaced by —Si(R 4 ) 2 —, —Ge(R 4 ) 2 —, —Sn(R 4 ), —NR 2 —, —O—, or —S— and wherein one or more H atoms may be replaced by deuterium, F, Cl, Br, I, CF 3 or NO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which in each case may be substituted with one or more radicals R 8 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted with one or more radicals R 9 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which may be substituted with one or more radicals R 9 , or a combination of these systems;

R 8 at each occurrence independently of one another is selected from the group consisting of H, deuterium, phenyl, naphthyl, F, CF 3 or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical with 1 to 20 C atoms, in which also one or more H atoms may be replaced by F or CF 3 ;

R 9 at each occurrence independently of one another is selected from the group consisting of H, deuterium, phenyl, naphthyl, N(R 2 ) 2 , CF 3 , NO 2 , a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms, each of which may be substituted with one or more radicals R 8 , wherein an adjacent CH 2 group may be replaced by —Si(R 4 ) 2 —, —Ge(R 4 ) 2 —, —Sn(R 4 ) 2 —NR 2 —, —O—, or —S— and wherein one or more H atoms may be replaced by deuterium, F, Cl, Br, I, CF 3 or NO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which in each case may be substituted with one or more radicals R 8 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted with one or more radicals R 3 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which may be substituted with one or more radicals R 8 , or a combination of these systems, wherein the organic molecule is a charge transport layer.

6. The optoelectronic component device according to claim 1 , wherein in the organic molecule m is 0.

7. The optoelectronic component device according to claim 1 , wherein the organic molecule comprises one of the structures 3.1, 3.2, 3.5, 3.6, 3.11 or 3.12, wherein optionally all C sp2 —H groups may also be C sp2 —R* groups and otherwise the definitions given in claim 1 apply:

8. The optoelectronic component device according to claim 1 , wherein in the organic molecule at least one chemically substitutable position comprises at least one radical R, wherein:

R at each occurrence independently of one another is selected from the group consisting of H, deuterium, phenyl, naphthyl, F, Cl, Br, I, N(R 2 ) 2 , —SCN, —CF 3 , —NO 2 , —OH, a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms, each of which may be substituted with one or more radicals R 9 , wherein an adjacent CH 2 group may be replaced by —Si(R 4 ) 2 —, —Ge(R 4 ) 2 —, —Sn(R 4 ) 2 —NR 2 —, —O—, or —S— and wherein one or more H atoms may be replaced by deuterium, F, Cl, Br, I, CF 3 or NO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which in each case may be substituted with one or more radicals R 2 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted with one or more radicals R 9 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which may be substituted with one or more radicals R 9 , or a combination of these systems; wherein R 2 to R 9 have the aforestated meanings.

9. The optoelectronic device according to claim 1 , wherein the organic molecule is one or more of a luminescent emitter, a host material, an electron transport material, a hole injection material and a hole blocking material in the optoelectronic component.

10. The optoelectronic device according to claim 1 , wherein the optoelectronic device is an organic light-emitting diode, a light-emitting electrochemical cell, an organic light-emitting sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, and an organic laser or a down-conversion element.

11. The optoelectronic device according to claim 1 , wherein the proportion of the organic molecule in the emitter is in the range of 1% to 99%.

12. The optoelectronic device according to claim 1 , wherein the proportion of the organic molecule in the emitter is in the range of 5% to 80%.

13. The optoelectronic component device according to claim 5 , wherein in the organic molecule m is 0.

14. The optoelectronic component device according to claim 5 , wherein the organic molecule comprises one of the structures 3.1, 3.2, 3.5, 3.6, 3.11 or 3.12, wherein optionally all C sp2 —H groups may also be C sp2 —R* groups and otherwise the definitions given in claim 5 apply:

15. The optoelectronic component device according to claim 5 , wherein in the organic molecule at least one chemically substitutable position comprises at least one radical R, wherein:

R at each occurrence independently of one another is selected from the group consisting of H, deuterium, phenyl, naphthyl, F, Cl, Br, I, N(R 2 ) 2 , —SCN, —CF 3 , —NO 2 , —OH, a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms, each of which may be substituted with one or more radicals R 9 , wherein an adjacent CH 2 group may be replaced by —Si(R 4 ) 2 —, —Ge(R 4 ) 2 —, —Sn(R 4 ) 2 —NR 2 —, —O—, or —S— and wherein one or more H atoms may be replaced by deuterium, F, Cl, Br, I, CF 3 or NO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which in each case may be substituted with one or more radicals R 2 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted with one or more radicals R 9 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which may be substituted with one or more radicals R 9 , or a combination of these systems; wherein R 2 to R 9 have the aforestated meanings.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 10, 2022
From: CYNORA GMBH
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 060329/0712 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 19, 2019
From: AMBROSEK, DAVID; DANZ, MICHAEL; FLÜGGE, HARALD; FRIEDRICHS, JANA; GRAB, TOBIAS; JACOB, ANDREAS; SEIFERMANN, STEFAN; VOLZ, DANIEL
To: CYNORA GMBH
Reel/Frame 051050/0027 →
Priority Claims (2)
EP 15151870 · Jan 20, 2015 · regional
DE 10 2015 107 994 · May 20, 2015 · national
Continuity (1)
Related Publication 20180265776A1 · Sep 20, 2018