Semiconducting nanoparticle
A semiconducting light emitting nanoparticle includes a core, optionally one or more shell layers, and a compound represented by chemical formula (I) wherein the variables in chemical formula (I) are as described in the specification. A composition includes the aforementioned nanoparticle and at least one further functional material. A formulation includes the aforementioned nanoparticle and at least one solvent. An optical medium and an optical device include the aforementioned nanoparticle.
1 . A semiconducting light emitting nanoparticle comprising a core, optionally one or more shell layers, and a compound (I′),
wherein the compound (I′) represents:
(i) a compound of the following chemical formula (III):
(ii) a compound of the following chemical formulae (IV), (V-a) or (V-b):
or
(iii) a compound of one of the following chemical formulae (IV-1) to (IV-6) and (V-1) to (V-6):
wherein
R 1 is H, D, CN, a straight chain alkyl or alkoxy group having 1 to 40 carbon atoms, a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more groups R a , where in each case one or more CH 2 groups may each 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═Se, C═NR a , P(═O)(R a ), SO, SO 2 , —O—, NR a , —C(═O)O, or —C(═O)NR a —, and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 ; an aromatic ring system or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, each of which may be substituted by one or more groups R a , and where one or more H atoms may each be replaced by D, F, Cl, Br, I, CN or NO 2 ;
R 2 , R 3 are, independently of each other, H, D, CN, a straight chain alkyl or alkoxy group having 1 to 40 carbon atoms, a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more groups R a , where in each case one or more CH 2 groups may each 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═Se, C═NR a , P(═O)(R a ), SO, SO 2 , —O—, NR a , —C(═O)O—, or —C(═O)NR a —, and where one or more H atoms may each be replaced by D, F, Cl, Br, I, CN, or NO 2 ; or an aromatic ring system or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, each of which may be substituted by one or more groups R a , and where one or more H atoms may each be replaced by D, F, Cl, Br, I, CN, or NO 2 ;
Y is O, NH, or S;
R a is at each occurrence, identically or differently, H, D, a straight chain alkyl or alkoxy group having 1 to 40 carbon atoms, a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms, a straight-chain alkenyl or alkynyl group having 2 to 40 carbon atoms, a branched alkenyl group or alkynyl group having 3 to 40 carbon atoms, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, wherein in each of the above-mentioned groups one or more H atoms may each be replaced by D, F, Cl, Br, I, and where two or more adjacent substituents R a here may optionally form a mono- or polycyclic, aliphatic ring system with one another;
L is a divalent group selected from a straight-chain alkylene group having 1 to 40 carbon atoms, a branched or cyclic alkylene group having 3 to 40 carbon atoms, a straight-chain alkenylene or alkynylene group having 2 to 40 carbon atoms, or a branched alkenylene group or alkynylene group having 3 to 40 carbon atoms, each of which each may be substituted by one or more groups R a , where in each case one or more CH 2 groups may each be replaced by an arylene group or heteroarylene group having 5 to 40 aromatic ring atoms, Si(R a ) 2 , Ge(R a ) 2 , Sn(R a ) 2 , C═O, C═S, C═Se, C═NR a , P(═O)(R a ), SO, SO 2 , —O—, NR a , —C(═O)O—, or —C(═O)NR a —, and where one or more H atoms may each be replaced by D, F, Cl, Br, I, CN or NO 2 ; an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, an aralkylene group, a heteroaralkylene group, an alkylarylene group or an alkylheteroarylene group, each of which may be substituted by one or more groups R a , and where in each case one or more H atoms may each be replaced by D, F, Cl, Br, I, CN, NO 2 ; or a group represented by the following chemical formula (II):
wherein
m is an integer of 1 to 50;
l is an integer of 1 to 25;
L 1 is
L 2 is
wherein a dashed line indicates a bond to the remainder of the compound and the symbol “*” marks the bond between groups L 1 and L 2 , and wherein each of L 1 and L 2 may be substituted by one or more groups R a , where one or more CH 2 groups of L 1 and L 2 may each 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═Se, C═NR a , P(═O)(R a ), SO, SO 2 , NR a , or —C(═O)NR a —, and where one or more H atoms in L 1 and L 2 may each be replaced by D, F, Cl, Br, I, CN or NO 2 ;
A 3 is a divalent group selected from a straight-chain alkylene group having 1 to 40 carbon atoms, a branched or cyclic alkylene group having 3 to 40 carbon atoms, each of which may be substituted by one or more groups R a , where in each case one or more CH 2 groups may each be replaced by, Si(R a ) 2 , Ge(R a ) 2 , Sn(R a ) 2 , C═O, C═S, C═Se, C═NR a , P(═O)(R a ), SO, SO 2 , —O—, NR a , —C(═O)O—, or —C(═O)NR a —, and where one or more H atoms may each be replaced by D, F, Cl, Br, I, CN, or NO 2 ; an aromatic or heteroaromatic ring system having 5 to 25 aromatic ring atoms, each of which may be substituted by one or more groups R a , and where one or more H atoms of the aromatic or heteroaromatic ring system may each be replaced by D, F, Cl, Br, I, CN, or NO 2 ;
M 1 denotes a hydrogen atom, or a metal cation selected from ½ Mg 2+ , ½ Cu 2+ , ½ Zn 2+ , ½ Pb 2+ , ½ Sn 2+ , ½ Cd 2+ , ⅓ Bi 3+ or ¼ Sn 4+ ;
Z is NH or O;
j is an integer of 1 to 40; and
indices g and f are identically or differently an integer of 1 to 40.
2 . The semiconducting light emitting nanoparticle according to claim 1 , wherein the compound (I′) represents a compound of the following chemical formula (III):
wherein the symbols occurring are as defined in claim 1 .
3 . The semiconducting light emitting nanoparticle according to claim 1 , wherein the compound (I′) represents a compound of the following chemical formulae (IV), (V-a) or (V-b):
wherein the symbols and indices occurring are as defined in claim 1 .
4 . The semiconducting light emitting nanoparticle according to claim 1 , wherein the compound (I′) represents a compound of one of the following chemical formulae (IV-1) to (IV-6) and (V-1) to (V-6):
wherein the symbols and indices occurring have the meaning as in claim 1 .
5 . A composition comprising a nanoparticle according to claim 1 and at least one further functional material selected from the group consisting of organic light emitting materials, inorganic light emitting materials, charge transporting materials, host or matrix materials, optically transparent polymers, anti-oxidants or stabilizers, radical quenchers, photo initiators or polymerization initiators, wetting and dispersing agents, scattering particles, reflective index adjusting materials, developer-dissolution promoters, scum removers, adhesion enhancers, polymerization inhibitors, defoaming agents, surfactants and sensitizers.
6 . The composition according to claim 5 , wherein the at least one further functional material is a host or matrix material selected from (meth)acrylate monomers or polymers.
7 . A composition comprising a semiconducting light emitting nanoparticle having at least a core, and optionally one or more shell layers, a compound (I′) represented by chemical formula (III):
wherein
R 1 is H, D, CN a straight chain alkyl or alkoxy group having 1 to 40 carbon atoms, a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more groups R a , where in each case one or more CH 2 groups may each 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═Se, C═NR a , P(═O)(R a ), SO, SO 2 , —O—, NR a , C(═O)O, or C(═O)NR a —, and where one or more H atoms may each be replaced by D, F, Cl, Br, I, CN, or NO 2 ; an aromatic ring system or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, each of which may be substituted by one or more groups R a , and where one or more H atoms may each be replaced by D, F, Cl, Br, I, CN, or NO 2 ;
R 2 , R 3 are, independently of each other, H, D, CN, a straight chain alkyl or alkoxy group having 1 to 40 carbon atoms, a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more groups R a , where in each case one or more CH 2 groups may each 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═Se, C═NR a , P(═O)(R a ), SO, SO 2 , —O—, NR a , —C(═O)O—, or —C(═O)NR a —, and where one or more H atoms may each be replaced by D, F, Cl, Br, I, CN, or NO 2 ; or an aromatic ring system or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, each of which may be substituted by one or more groups R a , and where one or more H atoms may each be replaced by D, F, Cl, Br, I, CN, or NO 2 ;
Y is O, NH, or S;
R a is at each occurrence, identically or differently, H, D, a straight chain alkyl or alkoxy group having 1 to 40 carbon atoms, a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms, a straight-chain alkenyl or alkynyl group having 2 to 40 carbon atoms, a branched alkenyl group or alkynyl group having 3 to 40 carbon atoms, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, wherein in each of the above-mentioned groups one or more H atoms may each be replaced by D, F, Cl, Br, or I, and where two or more adjacent substituents R a here may optionally form a mono- or polycyclic, aliphatic ring system with one another;
L is a divalent group selected from a straight-chain alkylene group having 1 to 40 carbon atoms, a branched or cyclic alkylene group having 3 to 40 carbon atoms, a straight-chain alkenylene or alkynylene group having 2 to 40 carbon atoms, or a branched alkenylene group or alkynylene group having 3 to 40 carbon atoms, each of which each may be substituted by one or more groups R a , where in each case one or more CH 2 groups may each be replaced by an arylene group or heteroarylene group having 5 to 40 aromatic ring atoms, Si(R a ) 2 , Ge(R a ) 2 , Sn(R a ) 2 , C═O, C═S, C═Se, C═NR a , P(═O)(R a ), SO, SO 2 , —O—, NR a , —C(═O)O—, or —C(═O)NR a —, and where one or more H atoms may each be replaced by D, F, Cl, Br, I, CN, or NO 2 ; an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, an aralkylene group, a heteroaralkylene group, an alkylarylene group or an alkylheteroarylene group, each of which may be substituted by one or more groups R a , and where in each case one or more H atoms may each be replaced by D, F, Cl, Br, I, CN, or NO 2 ; or a group represented by the following chemical formula (II)
wherein
m is an integer of 1 to 50;
l is an integer of 1 to 25;
L 1 is
L 2 is
wherein a dashed line indicates a bond to the remainder of the compound and the symbol “*” marks the bond between groups L 1 and L 2 , and wherein each of L 1 and L 2 may be substituted by one or more groups R a , where one or more CH 2 groups of L 1 and L 2 may each 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═Se, C═NR a , P(═O)(R a ), SO, SO 2 , NR a , or —C(═O)NR a —, and where one or more H atoms in L 1 and L 2 may each be replaced by D, F, Cl, Br, I, CN, or NO 2 ;
A 3 is a divalent group selected from a straight-chain alkylene group having 1 to 40 carbon atoms, a branched or cyclic alkylene group having 3 to 40 carbon atoms, each of which may be substituted by one or more groups R a , where in each case one or more CH 2 groups may each be replaced by, Si(R a ) 2 , Ge(R a ) 2 , Sn(R a ) 2 , C═O, C═S, C═Se, C═NR a , P(═O)(R a ), SO, SO 2 , —O—, NR a , —C(═O)O—, or —C(═O)NR a —, and where one or more H atoms may each be replaced by D, F, Cl, Br, I, CN, or NO 2 ; an aromatic or heteroaromatic ring system having 5 to 25 aromatic ring atoms, each of which may be substituted by one or more groups R a , and where one or more H atoms of the aromatic or heteroaromatic ring system may each be replaced by D, F, Cl, Br, I, CN, or NO 2 ; and
M 1 denotes a hydrogen atom; and
Z is NH or O;
and at least one further functional material selected from the group consisting of organic light emitting materials, inorganic light emitting materials, charge transporting materials, host or matrix materials, optically transparent polymers, anti-oxidants or stabilizers, radical quenchers, photo initiators or polymerization initiators, wetting and dispersing agents, scattering particles, reflective index adjusting materials, developer-dissolution promoters, scum removers, adhesion enhancers, polymerization inhibitors, defoaming agents, surfactants and sensitizers.
8 . The composition according to claim 7 , wherein the at least one further functional material is a host or matrix material, selected from (meth)acrylate monomers or polymers.
9 . A formulation comprising a nanoparticle according to claim 1 and at least one solvent selected from the group consisting of esters, ketones, glycols, ethers, and aromatic, halogenated and aliphatic hydrocarbons.
10 . An optical medium comprising a nanoparticle according to claim 1 .
11 . An optical device comprising a nanoparticle according to claim 1 .
12 . A process for the preparation of an optical device according to claim 11 , comprising:
a) preparing a mixture by mixing a semiconducting light emitting nanoparticle having at least a core and optionally one or more shell layers, at least one further functional material, a compound (I′) defined below and, optionally, at least one solvent;
b) providing the mixture onto a substrate; and
c) subjecting the mixture obtained to a photo irradiation having a peak light wavelength in the range from 300 to 650 nm;
wherein the compound (I′) represents:
(i) a compound of the following chemical formula (III):
(ii) a compound of the following chemical formulae (IV), (V-a) or (V-b):
(iii) a compound of one of the following chemical formulae (IV-1) to (IV-6) and (V-1) to (V-6):
wherein
R 1 is H, D, CN, a straight chain alkyl or alkoxy group having 1 to 40 carbon atoms, a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more groups R a , where in each case one or more CH 2 groups may each 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═Se, C═NR a , P(═O)(R a ), SO, SO 2 , —O—, NR a , —C(═O)O—, or —C(═O)NR a —, and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 ; an aromatic ring system or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, each of which may be substituted by one or more groups R a , and where one or more H atoms may each be replaced by D, F, Cl, Br, I, CN or NO 2 ;
R 2 , R 3 are, independently of each other, H, D, CN, a straight chain alkyl or alkoxy group having 1 to 40 carbon atoms, a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more groups R a , where in each case one or more CH 2 groups may each 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═Se, C═NR a , P(═O)(R a ), SO, SO 2 , —O—, NR a , —C(═O)O—, or —C(═O)NR a —, and where one or more H atoms may each be replaced by D, F, Cl, Br, I, CN, or NO 2 ; or an aromatic ring system or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, each of which may be substituted by one or more groups R a , and where one or more H atoms may each be replaced by D, F, Cl, Br, I, CN, or NO 2 ;
Y is O, NH, or S;
R a is at each occurrence, identically or differently, H, D, a straight chain alkyl or alkoxy group having 1 to 40 carbon atoms, a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms, a straight-chain alkenyl or alkynyl group having 2 to 40 carbon atoms, a branched alkenyl group or alkynyl group having 3 to 40 carbon atoms, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, wherein in each of the above-mentioned groups one or more H atoms may each be replaced by D, F, Cl, Br, I, and where two or more adjacent substituents R a here may optionally form a mono- or polycyclic, aliphatic ring system with one another;
L is a divalent group selected from a straight-chain alkylene group having 1 to 40 carbon atoms, a branched or cyclic alkylene group having 3 to 40 carbon atoms, a straight-chain alkenylene or alkynylene group having 2 to 40 carbon atoms, or a branched alkenylene group or alkynylene group having 3 to 40 carbon atoms, each of which each may be substituted by one or more groups R a , where in each case one or more CH 2 groups may each be replaced by an arylene group or heteroarylene group having 5 to 40 aromatic ring atoms, Si(R a ) 2 , Ge(R a ) 2 , Sn(R a ) 2 , C═O, C═S, C═Se, C═NR a , P(═O)(R a ), SO, SO 2 , —O—, NR a , —C(═O)O—, or —C(═O)NR a —, and where one or more H atoms may each be replaced by D, F, Cl, Br, I, CN or NO 2 ; an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, an aralkylene group, a heteroaralkylene group, an alkylarylene group or an alkylheteroarylene group, each of which may be substituted by one or more groups R a , and where in each case one or more H atoms may each be replaced by D, F, Cl, Br, I, CN, NO 2 ; or a group represented by the following chemical formula (II):
wherein
m is an integer of 1 to 50;
l is an integer of 1 to 25;
L 1 is
L 2 is
wherein a dashed line indicates a bond to the remainder of the compound and the symbol “*” marks the bond between groups L 1 and L 2 , and wherein each of L 1 and L 2 may be substituted by one or more groups R a , where one or more CH 2 groups of L 1 and L 2 may each 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═Se, C═NR a , P(═O)(R a ), SO, SO 2 , NR a , or —C(═O)NR a —, and where one or more H atoms in L 1 and L 2 may each be replaced by D, F, Cl, Br, I, CN or NO 2 ;
A 3 is a divalent group selected from a straight-chain alkylene group having 1 to 40 carbon atoms, a branched or cyclic alkylene group having 3 to 40 carbon atoms, each of which may be substituted by one or more groups R a , where in each case one or more CH 2 groups may each be replaced by, Si(R a ) 2 , Ge(R a ) 2 , Sn(R a ) 2 , C═O, C═S, C═Se, C═NR a , P(═O)(R a ), SO, SO 2 , —O—, NR a , —C(═O)O—, or —C(═O)NR a —, and where one or more H atoms may each be replaced by D, F, Cl, Br, I, CN, or NO 2 ; an aromatic or heteroaromatic ring system having 5 to 25 aromatic ring atoms, each of which may be substituted by one or more groups R a , and where one or more H atoms of the aromatic or heteroaromatic ring system may each be replaced by D, F, Cl, Br, I, CN, or NO 2 ;
M 1 denotes a hydrogen atom, or a metal cation selected from ½ Mg 2+ , ½ Cu 2+ , ½ Zn 2+ , ½ Pb 2+ , ½ Sn 2+ , ½ Cd 2+ , ⅓ Bi 3+ or ¼ Sn 4+ ;
Z is NH or O;
j is an integer of 1 to 40; and
indices g and f are identically or differently an integer of 1 to 40.