US 2005/0033040 A1Published application

Self-dispersible bipyridine-based metal complex and ink composition comprising the same

AssigneeSamsung Electronics Co., Ltd.

InventorsJong-in Lee, Seung-min Ryu, Su-aa Jung

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Abstract

A self-dispersible bipyridine-based metal complex includes a bipyridine-based ligand and a metal, and an ink composition including the metal complex. The bipyridine-based metal complex may be self-dispersed without requiring a dispersing agent and may be used as a colorant per se. Furthermore, the metal complex, when binding with a common colorant, may produce various colors and exhibit enhanced durability including light resistance. In addition, the metal complex includes a hydrophilic group-containing ligand coordinating with the metal, in addition to the bipyridine-based ligand, and thus, has a bulky structure. Therefore, dispersion stability is enhanced by a self-dispersion system based on a steric hindrance due to the bulky structure of the metal complex and an electrostatic repulsive force between the charged metal and the hydrophilic group-containing ligand, thus enhancing a long-term storage stability.

Claims28

Dependent claims

A bipyridine-based metal complex represented by the following Formula I:

wherein W1, W2, and W4 are each independently atoms required to form a 4- to 8-membered heteroaryl group or heterocycloalkenyl group;
W3 refers to atoms required to form one of a 0- to 8-membered cycloalkyl group, a cycloalkenyl group, an aryl group, a heteroaryl group, a heterocycloalkyl group, and a heterocycloalkenyl group;
n is an integer of 0 to 100;
R1, R2, R3, and R4 are mono-substituents or a same or different multi-substituents, and are each independently one of a hydrogen atom, a halogen atom, a nitro group, —SO3H, —COOH, a substituted or unsubstituted alkyl group of C1-C20, a substituted or unsubstituted heteroalkyl group of C1-C20, a hydroxy group, an amino group, a cyano group, a substituted or unsubstituted alkenyl group of C2-C20, a substituted or unsubstituted alkoxy group of C1-C20, a substituted or unsubstituted alkylsulfonamide group of C1-C20, a substituted or unsubstituted arylsulfonamide group of C6-C20, a substituted or unsubstituted acylamino group of C1-C20, an alkylureido group of C1-C20, an arylureido group of C6-C20, an alkoxycarbonyl group of C2-C20, an alkoxycarbonylamino group of C2-C20, a carbamoyl group, a sulfamoyl group, a sulfo group or its salt, a carboxyl group or its salt, a substituted or unsubstituted hydroxyalkyloxyalkyl group of C1-C20, a substituted or unsubstituted dialkylaminoalkyl group of C1-C20, a substituted or unsubstituted pyridylalkyl group of C6-C20, a substituted or unsubstituted pyridyl group of C5-C20, a substituted or unsubstituted imidazolyl group of C6-C20, a hydrazine group, a hydrazone group, a substituted or unsubstituted pyridylalkyl group of C1-C20, a substituted or unsubstituted aryl group of C6-C20, a substituted or unsubstituted arylalkyl group of C6-C20, a substituted or unsubstituted heteroaryl group of C6-C20, a heteroarylalkyl group of C6-C20, a substituted or unsubstituted heteroarylalkenyl group of C6-C20, and a substituted or unsubstituted heterocycloalkyl group of C3-C20;
R5 and R6 are each independently a hydrophilic mono-substituent or a same or different hydrophilic multi-substituent;
M is a metal atom selected from Groups III through XIV;
X is an anionic moiety;
Y is a neutral moiety;
Z is a counterion;
o, p, and q are each independently an integer of 0 to 10, wherein a sum of o and p is not equal to zero.

7 more elements

A bipyridine-based metal complex represented by the following Formula II:

wherein W1, W2, and W4 are each independently atoms required to form a 4- to 8-membered heteroaryl group or heterocycloalkenyl group;
W3 refers to atoms required to form one of a 0- to 8-membered cycloalkyl group, a cycloalkenyl group, an aryl group, a heteroaryl group, a heterocycloalkyl group, and a heterocycloalkenyl group;
n is an integer of 0 to 100;
A1, A2, A3, and A4 are each independently a same or different colorant and respectively bind with the ring compounds, W1, W2, W3, and W4;
i, j, k, and m are each independently 0 or 1, wherein a sum of i, j, k, and m is not equal to zero;
where all of i, j, k, and m are 1, R1, R2, R3, and R4 are each a linker;
where i is 0, R1 is a mono-substituent or a same or different multi-substituent and is one of:
a hydrogen atom, a halogen atom, a nitro group, —SO3H, —COOH, a substituted or unsubstituted alkyl group of C1-C20, a substituted or unsubstituted heteroalkyl group of C1-C20, a hydroxy group, an amino group, a cyano group, a substituted or unsubstituted alkenyl group of C2-C20, a substituted or unsubstituted alkoxy group of C1-C20, a substituted or unsubstituted alkylsulfonamide group of C1-C20, a substituted or unsubstituted arylsulfonamide group of C6-C20, a substituted or unsubstituted acylamino group of C1-C20, an alkylureido group of C1-C20, an arylureido group of C6-C20, an alkoxycarbonyl group of C2-C20, an alkoxycarbonylamino group of C2-C20, a carbamoyl group, a sulfamoyl group, a sulfo group or its salt, a carboxyl group or its salt, a substituted or unsubstituted hydroxyalkyloxyalkyl group of C1-C20, a substituted or unsubstituted dialkylaminoalkyl group of C1-C20, a substituted or unsubstituted pyridylalkyl group of C6-C20, a substituted or unsubstituted pyridyl group of C5-C20, a substituted or unsubstituted imidazolyl group of C6-C20, a hydrazine group, a hydrazone group, a substituted or unsubstituted pyridylalkyl group of C1-C20, a substituted or unsubstituted aryl group of C6-C20, a substituted or unsubstituted arylalkyl group of C6-C20, a substituted or unsubstituted heteroaryl group of C6-C20, a heteroarylalkyl group of C6-C20, a substituted or unsubstituted heteroarylalkenyl group of C6-C20, and a substituted or unsubstituted heterocycloalkyl group of C3-C20;
where j is 0, R2 is referred to in a description of R1 where i is 0;
where k is 0, R3 is referred to in a description of R1 where i is 0;
where m is 0, R4 is referred to in a description of R1 where i is 0;
R5 and R6 are each independently a hydrophilic mono-substituent or a same or different hydrophilic multi-substituent;
M is a metal atom selected from Groups III through XIV;
X is an anionic ligand;
Y is a neutral ligand;
Z is a counterion;
o, p, and q are each independently an integer of 0 to 10, wherein a sum of o and p is not equal to zero.

14 more elements

An ink composition comprising an aqueous liquid medium, a colorant and at least one of a bipyridine-based metal complex represented by the following Formula I and a bipyridine-based metal complex represented by the following Formula II:

wherein W1, W2, and W4 are each independently atoms required to form a 4- to 8-membered heteroaryl group or heterocycloalkenyl group;
W3 refers to atoms required to form one of a 0- to 8-membered cycloalkyl group, a cycloalkenyl group, an aryl group, a heteroaryl group, a heterocycloalkyl group, and a heterocycloalkenyl group;
n is an integer of 0 to 100;
R1, R2, R3, and R4 are mono-substituents or a same or different multi-substituents, and are each independently one of a hydrogen atom, a halogen atom, a nitro group, —SO3H, —COOH, a substituted or unsubstituted alkyl group of C1-C20, a substituted or unsubstituted heteroalkyl group of C1-C20, a hydroxy group, an amino group, a cyano group, a substituted or unsubstituted alkenyl group of C2-C20, a substituted or unsubstituted alkoxy group of C1-C20, a substituted or unsubstituted alkylsulfonamide group of C1-C20, a substituted or unsubstituted arylsulfonamide group of C6-C20, a substituted or unsubstituted acylamino group of C1-C20, an alkylureido group of C1-C20, an arylureido group of C6-C20, an alkoxycarbonyl group of C2-C20, an alkoxycarbonylamino group of C2-C20, a carbamoyl group, a sulfamoyl group, a sulfo group or its salt, a carboxyl group or its salt, a substituted or unsubstituted hydroxyalkyloxyalkyl group of C1-C20, a substituted or unsubstituted dialkylaminoalkyl group of C1-C20, a substituted or unsubstituted pyridylalkyl group of C6-C20, a substituted or unsubstituted pyridyl group of C5-C20, a substituted or unsubstituted imidazolyl group of C6-C20, a hydrazine group, a hydrazone group, a substituted or unsubstituted pyridylalkyl group of C1-C20, a substituted or unsubstituted aryl group of C6-C20, a substituted or unsubstituted arylalkyl group of C6-C20, a substituted or unsubstituted heteroaryl group of C6-C20, a heteroarylalkyl group of C6-C20, a substituted or unsubstituted heteroarylalkenyl group of C6-C20, and a substituted or unsubstituted heterocycloalkyl group of C3-C20;
R5 and R6 are each independently a hydrophilic mono-substituent or a same or different hydrophilic multi-substituent;
M is a metal atom selected from Groups III through XIV;
X is an anionic moiety;
Y is a neutral moiety;
Z is a counterion;
o, p, and q are each independently an integer of 0 to 10, wherein a sum of o and p is not equal to zero;
and
wherein A1, A2, A3, and A4 are each independently a same or different colorant and respectively bind with the ring compounds, W1, W2, W3, and W4;
i, j, k, and m are each independently 0 or 1, wherein a sum of i, j, k, and m is not equal to zero;
where all of i, j, k, and m are 1, R1, R2, R3, and R4 are each a linker;
where i is 0, R1, is a mono-substituent or a same or different multi-substituent and is one of:
a hydrogen atom, a halogen atom, a nitro group, —SO3H, —COOH, a substituted or unsubstituted alkyl group of C1-C20, a substituted or unsubstituted heteroalkyl group of C1-C20, a hydroxy group, an amino group, a cyano group, a substituted or unsubstituted alkenyl group of C2-C20, a substituted or unsubstituted alkoxy group of C1-C20, a substituted or unsubstituted alkylsulfonamide group of C1-C20, a substituted or unsubstituted arylsulfonamide group of C6-C20, a substituted or unsubstituted acylamino group of C1-C20, an alkylureido group of C1-C20, an arylureido group of C6-C20, an alkoxycarbonyl group of C2-C20, an alkoxycarbonylamino group of C2-C20, a carbamoyl group, a sulfamoyl group, a sulfo group or its salt, a carboxyl group or its salt, a substituted or unsubstituted hydroxyalkyloxyalkyl group of C1-C20, a substituted or unsubstituted dialkylaminoalkyl group of C1-C20, a substituted or unsubstituted pyridylalkyl group of C6-C20, a substituted or unsubstituted pyridyl group of C5-C20, a substituted or unsubstituted imidazolyl group of C6-C20, a hydrazine group, a hydrazone group, a substituted or unsubstituted pyridylalkyl group of C1-C20, a substituted or unsubstituted aryl group of C6-C20, a substituted or unsubstituted arylalkyl group of C6-C20, a substituted or unsubstituted heteroaryl group of C6-C20, a heteroarylalkyl group of C6-C20, a substituted or unsubstituted heteroarylalkenyl group of C6-C20, and a substituted or unsubstituted heterocycloalkyl group of C3-C20;
where j is 0, R2 is referred to in a description of R1 where i is 0;
where k is 0, R3 is referred to in a description of R1 where i is 0;
where m is 0, R4 is referred to in a description of R1 where i is 0.

16 more elements

Dependencies are inferred from the claim text.