US 11,066,351 B2 · Organic compound, three-dimensional organic framework formed by using organic compound, separation sieve and optical layer, which comprise organic framework, and optical device comprising optical layer as optical amplification layer

Abstract

An organic compound, a three-dimensional organic structure formed by using the organic compound, a separation sieve and an optical layer having the organic structure, and an optical device having the optical layer as an optical amplification layer are provided. The organic structure includes a plurality of organic molecules self-assembled by non-covalent bonding. Each of the unit organic molecules has an aromatic ring, a first pair of substituents being connected to immediately adjacent positions of substitutable positions of the aromatic ring, and a second pair of substituents being connected to immediately adjacent positions of remaining substitutable positions of the aromatic ring. The unit organic molecules are self-assembled by van der Waals interaction, London dispersion interaction or hydrogen bonding between the first and the second pairs of the substituents and by pi-pi interactions between the aromatic rings.

A three-dimensional organic structure comprising a plurality of unit organic molecules which are self-assembled to form the three-dimensional organic structure,

wherein each of the unit organic molecules has at least one aromatic ring, a first pair of substituents being connected to immediately adjacent positions of substitutable positions of the aromatic ring, and a second pair of substituents being connected to immediately adjacent positions of substitutable positions of the aromatic ring,
wherein the substituents have terminal groups, respective of which is independently selected from the group consisting of —CRcRdRe, —OH, —COOH, —CHO, —SH, —COCRcRdRe, —COOCRcRdRe, —CRc═CRdRe, —CN, —N═C═O, —C═N═N—CRcRdRe, —C≡CRa, —NHCRcRdRe, and —NH2, wherein Rc, Rd, and Re are, independently of each other, H, F, Cl, Br, or I,
wherein the unit organic molecules contained in one layer of the three-dimensional structure are self-assembled by physical interaction between the terminal groups of the first pair of the substituents included in one unit organic molecule and the terminal groups of the second pair of the substituent groups included in another unit organic molecule among the unit organic molecules,
wherein the unit organic molecules contained in one layer and the unit organic molecules contained in another adjacent layer of the three-dimensional structure are self-assembled by pi-pi interactions between the aromatic rings,
wherein the three-dimensional organic structure is an organic crystal,
wherein the unit organic molecules has an organic compound of the following Chemical Formula 1:
in Chemical-Formula 1,
-A1-(L1)n1-Y1—X1 and -A2-(L2)n2-Y2—X2 form one of the pairs of substituents being connected immediately adjacent positions among substitution positions of Ar,
X1 and X2 are the terminal groups,
A1 and A2 are, independently of each other, —O— or —S—,
L1 and L2 are, independently of each other, -E-,
E, E1, and E2 are, independently of each other, O or S, n1 and n2 are, independently of each other, 0 or 1,
Y1 and Y2 are, independently of each other,
a1, a2, a3, b1, and b2 are, independently of each other, integers of 0 to 30, and a1+a2+a3+b1+b2 is an integer of 3 to 30,
P1, P2, and P3 are, independently of each other, —CRaRb— or —(CRaRb)rO—, r is an integer of 1 to 3,
Q1 and Q2 are, independently of each other, q1-(p1)c1-q2-(p2)c2-q3, q1 and q3 are, independently of each other, —O— or —S—, q2 is —CH═CH—, —C≡C—, —N═N—,
in which the hydrogen group bonded to the carbon is substituted with F, Cl, Br, or I, or unsubstituted, p1 and p2 are, independently of each other, —CRaRb—, c1 and c2 are, independently of each other, an integer of 0 to 2,
Ra and Rb are, independently of each other, H, F, Cl, Br, or I,
Rc, Rd, and Re are, independently of each other, H, F, Cl, Br, or I,
U is one selected from the group consisting of a hydroxyl group, fluorine, chlorine, iodine, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 15 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 15 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 15 carbon atoms, and a substituted or unsubstituted alkynyl group having 2 to 15 carbon atoms,
o is an integer between 0 and 16,
m is an integer of 2 to 8, and
the aromatic ring (Ar) is selected from the group consisting of an aromatic ring of the following Structural Formula 3, an aromatic ring of the following Structural Formula 6, an aromatic ring of the following Structural Formula 8, an aromatic ring of the following Structural Formula 10 and an aromatic ring of the following Structural Formula 12:
in Structural Formula 3, T1 to T14 are all C;
or some of T1 to T14 are N, P, B or Si independently of each other and remainders are C,
G1, G3, G5, G6, G7, G8, G10, G12, G13, and G14 represent substitution positions of the aromatic ring,
a first pair of -A1-(L1)n1-Y1—X1 and -A2-(L2)n2-Y2—X2 are bonded to G6 and G7 positions,
a second pair of -A1-(L1)n1-Y1—X1 and -A2-(L2)n2-Y2—X2 are bonded to G13 and G14 positions,
U is bonded to any one of remaining G1, G3, G5, G8, G10, and G12 positions or not, and
o is an integer of 0 to 6;
in Structural Formula 6, T1 to T13 are all C;
or some of T1 to T13 are N, P, B or Si independently of each other and remainders are C,
G1, G2, G4, G5, G7, G8, G10, and G11 represent substitution positions of the aromatic ring,
a first pair of -A1-(L1)n1-Y1—X1 and -A2-(L2)n2-Y2—X2 are bonded to G4 and G5 positions,
a second pair of -A1-(L1)n1-Y1—X1 and -A2-(L2)n2-Y2—X2 are bonded to G10 and G11 positions,
U is bonded to any one of remaining G1, G2, G7, and G8 positions or not, and
o is an integer of 0 to 4;
in Structural Formula 8, T1 to T14, T16 and T17 are all C;
or some of T1 to T14, T16 and T17 are N, P, B or Si independently of each other and remainders are C,
G1, G2, G4, G5, G7, G8, G9, G11, G12, and G14 represent substitution positions of the aromatic ring,
a first pair of -A1-(L1)n1-Y1—X1 and -A2-(L2)n2-Y2—X2 are bonded to G4 and G5 positions,
a second pair of -A1-(L1)n1-Y1—X1 and -A2-(L2)n2-Y2—X2 are bonded to G11 and G12 positions,
U is bonded to any one of remaining G1, G2, G7, G8, G9, and G14 positions or not, and
o is an integer of 0 to 6;
in Structural Formula 10, T1 to T18 are all C;
or some of T1 to T18 are N, P, B or Si independently of each other and remainders are C,
G1, G2, G3, G6, G7, G8, G9, G12, G13, G14, G15, and G18 represent substitution positions of the aromatic ring,
a first pair of -A1-(L1)n1-Y1—X1 and -A2-(L2)n2-Y2—X2 are bonded to G1 and G2 positions,
a second pair of -A1-(L1)n1-Y1—X1 and -A2-(L2)n2-Y2—X2 are bonded to G7 and G8 positions,
a third pair of -A1-(L1)n1-Y1—X1 and -A2-(L2)n2-Y2—X2 are bonded to G13 and G14 positions,
U is bonded to any one of remaining G3, G6, G9, G12, G15, and G18 positions or not, and
o is an integer of 0 to 6;
in Structural Formula 12, T1 to T24 are all C;
or some of T1 to T24 are N, P, B or Si independently of each other and remainders are C,
G1, G3, G4, G6, G7, G9, G10, G12, G13, G15, G16, and G18 represent substitution positions of the aromatic ring,
a first pair of -A1-(L1)n1-Y1—X1 and -A2-(L2)n2-Y2—X2 are bonded to G6 and G7 positions,
a second pair of -A1-(L1)n1-Y1—X1 and -A2-(L2)n2-Y2—X2 are bonded to G15 and G16 positions,
U is bonded to any one of remaining G1, G3, G4, G9, G10, G12, G13, and G18 positions or not, and
o is an integer of 0 to 8.

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Organic compound, three-dimensional organic framework formed by using organic compound, separation sieve and optical layer, which comprise organic framework, and optical device comprising optical layer as optical amplification layer

Life of this patent

Organic compound, three-dimensional organic framework formed by using organic compound, separation sieve and optical layer, which comprise organic framework, and optical device comprising optical layer as optical amplification layer

Life of this patent

Abstract

Claims12