IP Library Granted Patent US 11,845,889
Granted Patent B2
US 11,845,889 · App. 17/285,242 · Granted Dec 19, 2023

Nanoparticle

Inventor: Itai Lieberman (Dreieich, DE)
Assignee: Merck Patent GmbH
C09K11/70C09K11/025C09K11/565C09K11/883B82Y20/00B82Y30/00B82Y40/00H10K50/115
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Quick Facts
Patent No.
US 11,845,889
App. No.
17/285,242
Granted
Dec 19, 2023
Kind
B2
Abstract

The present invention relates to a nanoparticle and a composition comprising a nanoparticle.

Claims (79)

1. A semiconducting light emitting nanoparticle comprising at least

i) a first semiconducting material;

ii) optionally at least one shell layer;

iii) a chemical compound of formula (I)

wherein

X and Y are each independently of each other, O, S, P or N;

n is 0 if Y is O or S, or n is 1 if Y is N or P;

m is 0 if X is O or S, or m is 1 if Y is N or P;

R 1 is an attaching group,

R 2 is a linear alkyl group or alkoxyl group having 1 to 40 carbon atoms, a branched alkyl group or alkoxyl group having 3 to 40 carbon atoms, a cycloalkane group having 3 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an aryl group having 3 to 40 carbon atoms, a hetero aryl group having 3 to 40 carbon atoms, and or an aralkyl group having 4 to 40 carbon atoms, which may in each case be substituted by one or more radicals R a , where one or more non-adjacent CH 2 groups may be replaced by R a C═CR a , C═C, Si(R a ) 2 , Ge(R a ) 2 , Sn(R a ) 2 , C═O, C═S, C═NR a , SO, SO 2 , NR a , or CONR a and where one or more H atoms may be replaced by F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R a ,

R a is at each occurrence, identically or different D, or an alkyl group having 1 to 20 carbon atoms, or a cyclic alkyl or alkoxy group having 3 to 40 carbon atoms, an aromatic ring system having 5 to 60 carbon ring atoms, or a hetero aromatic ring system having 5 to 60 carbon atoms, wherein H atoms may be replaced by D, F, Cl, Br, or I; and wherein two or more adjacent substituents R a here may form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another;

R 3 is a divalent bond,

R 4 is an H atom, D atom, or R 2 ,

R 5 is an H atom, D atom, or R 2 .

2. The nanoparticle of claim 1 , comprising at least

i) the first semiconducting material;

ii) optionally at least one shell layer;

iii) the chemical compound represented by following chemical formula (I) in this sequence.

3. The nanoparticle of claim 1 , comprising at least one shell layer represented by formula (II)

ZnS x Se (1-x-z) Te z, —  (II)

wherein 0≤x≤1, 0≤z≤1.

4. The nanoparticle of claim 1 , wherein the first semiconducting material comprises at least one element of group 13 elements or group 12 elements of the periodic table and one element of group 16 elements of the periodic table.

5. A composition comprising at least

a) one semiconducting light emitting nanoparticle comprising a core, optionally at least one shell layer,

b) one chemical compound of formula (I)

wherein

X and Y are each independently or dependently of each other, 0, S, P or N;

n is 0 if Y is O or S, n is 1 if Y is N or P;

m is 0 if X is O or S, m is 1 if Y is N or P;

R 1 is an attaching group;

R 2 is a linear alkyl group or alkoxyl group having 1 to 40 carbon atoms, a branched alkyl group or alkoxyl group having 3 to 40 carbon atoms, a cycloalkane group having 3 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an aryl group having 3 to 40 carbon atoms, a hetero aryl group having 3 to 40 carbon atoms, or an aralkyl group having 4 to 40 carbon atoms, which may in each case be substituted by one or more radicals R a , where one or more non-adjacent CH 2 groups may be replaced by R a C═CR a , C═C, Si(R a ) 2 , Ge(R a ) 2 , Sn(R a ) 2 , C═O, C═S, C═NR a , SO, SO 2 , NR a , or CONR a and where one or more H atoms may be replaced by F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R a ,

R a is at each occurrence, identically or different D, or an alkyl group having 1 to 20 carbon atoms, or a cyclic alkyl or alkoxy group having 3 to 40 carbon atoms, an aromatic ring system having 5 to 60 carbon ring atoms, or a hetero aromatic ring system having 5 to 60 carbon atoms, wherein H atoms may be replaced by D, F, Cl, Br, or I; and wherein two or more adjacent substituents R a here may form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another;

R 3 is of a linear alkylene group or alkoxylene group having 1 to 25 carbon atoms, where one or more non-adjacent CH 2 groups may be replaced by R a C═CR a , C═C, Si(R a ) 2 , Ge(R a ) 2 , Sn(R a ) 2 , C═O, C═S, C═NR a , SO, SO 2 , NR a , or CONR a and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R a ,

R 4 is an H atom, D atom, or R 2 ,

R 5 is an H atom, D atom or R 2 ,

and

c) another compound.

6. A composition comprising at least

A) one semiconducting light emitting nanoparticle according to claim 1 , and

B) another compound.

7. The composition of claim 6 , wherein the composition comprises a plurality of semiconducting light emitting nanoparticles.

8. The composition according to claim 6 , wherein said another compound is an organic light emitting material, inorganic light emitting material, charge transporting material, scattering particle, host material, nanosized plasmonic particle, photo initiator or a matrix material.

9. A formulation comprising at least one semiconducting light emitting nanoparticle according to claim 1 ,

and

at least one solvent.

10. The formulation of claim 9 , wherein the total amount of the compound of formula (I) is 0.001 wt. % to 50 wt. % based on the total amount of the formulation.

11. The formulation according to claim 9 , wherein the total amount of the nanoparticle is 0.01 wt. % to 90 wt. % based on the total amount of the formulation.

12. An optical device or biomedical device comprising the semiconducting light emitting nanoparticle according to claim 1 .

13. An optical medium comprising at least one semiconducting light emitting nanoparticle according to claim 1 .

14. An optical medium, comprising an anode and a cathode, and at least one organic layer comprising the at least one semiconducting light emitting nanoparticle according to claim 1 , and optionally the medium further comprises one or more layers selected from the group consisting of hole injection layers, hole transporting layers, electron blocking layers, hole blocking layers, electron blocking layers, and electron injection layers.

15. The optical medium of claim 14 , wherein the organic layer comprises the at least one semiconducting light emitting nanoparticle and a host material.

16. An optical device comprising at least said optical medium according to claim 13 .

17. The nanoparticle of claim 1 , wherein

R 1 is an attaching group of one of the following formulae

where “#” represents the connecting point to group R 3 , and “*” represents the connecting point to the surface of the core or the outermost surface of the shell layer of the semiconducting light emitting nanoparticle; and

R 3 is a linear alkylene group or alkoxylene group having 1 to 25 carbon atoms, where one or more non-adjacent CH 2 groups may be replaced by R a C═CR a , C═C, Si(R a ) 2 , Ge(R a ) 2 , Sn(R a ) 2 , C═O, C═S, C═NR a , SO, SO 2 , NR a , or CONR a and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R a .

18. The composition of claim 5 , wherein

R 1 is an attaching croup of one of the following formulae

where “#” represents the connecting point to group Y, and “*” represents the connecting point to the surface of the core or the outermost surface of the shell layer of the semiconducting light emitting nanoparticle; and

R 3 is a linear alkylene group or alkoxylene group having 1 to 25 carbon atoms, where one or more non-adjacent CH 2 groups may be replaced by R a C═CR a , C═C, Si(R a ) 2 , Ge(R a ) 2 , Sn(R a ) 2 , C═O, C═S, C═NR a , SO, SO 2 , NR a , or CONR a and where one or more H atoms may be replaced by D, F, CI, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R a .

19. The nanoparticle of claim 1 , wherein the first semiconducting material is of formula (III),

In (1-x-y) Ga1.5 x Zn y P  (III)

wherein 0≤x≤1, 0≤x+y<1,

or

is selected from the group consisting of InP, InP:Zn, InP:ZnS, InP:ZnSe, InP:ZnSSe and InP:Ga.

20. A semiconducting light emitting nanoparticle comprising at least

i) a first semiconducting material;

ii) optionally at least one shell layer;

iii) a chemical compound of formula (I)

wherein

X and Y are each independently of each other, 0, S, P or N;

n is 0 if Y is O or S, or n is 1 if Y is N or P;

m is 0 if X is O or S, or m is 1 if Y is N or P;

R 1 is an attaching group,

R 2 is a branched alkyl group or alkoxyl group having 3 to 40 carbon atoms, a cycloalkane group having 3 to 40 carbon atoms, an aryl group having 3 to 40 carbon atoms, a hetero aryl group having 3 to 40 carbon atoms, or an aralkyl group having 4 to 40 carbon atoms, which may in each case be substituted by one or more radicals R a , where one or more non-adjacent CH 2 groups may be replaced by R a C═CR a , C═C, Si(R a ) 2 , Ge(R a ) 2 , Sn(R a ) 2 , C═O, C═S, C═NR a , SO, SO 2 , NR a , or CONR a and where one or more H atoms may be replaced by F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R a ,

R a is at each occurrence, identically or differently D, or an alkyl group having 1 to 20 carbon atoms, or a cyclic alkyl or alkoxy group having 3 to 40 carbon atoms, an aromatic ring system having 5 to 60 carbon ring atoms, or a hetero aromatic ring system having 5 to 60 carbon atoms, wherein H atoms may be replaced by D, F, Cl, Br, or I; and wherein two or more adjacent substituents R a here may form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another;

R 3 is a divalent bond,

R 4 is an H atom, D atom, or R 2 ,

R 5 is an H atom, D atom, or R 2 .

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 7, 2025
From: MERCK PATENT GMBH
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 071620/0512 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 30, 2021
From: LIEBERMAN, ITAI
To: MERCK KGAA
Reel/Frame 057657/0434 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 30, 2021
From: MERCK KGAA
To: MERCK PERFORMANCE MATERIALS GERMANY GMBH
Reel/Frame 057657/0570 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 30, 2021
From: MERCK PERFORMANCE MATERIALS GERMANY GMBH
To: MERCK PATENT GMBH
Reel/Frame 057657/0657 →
Priority Claims (1)
EP 18200551 · Oct 15, 2018 · regional
Continuity (1)
Related Publication 20210380882A1 · Dec 9, 2021