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

Patent metadata

Field	Value
Publication number	US-11066351-B2
Application number	US-201716072986-A
Country	US
Kind code	B2
Filing date	Jan 24, 2017
Priority date	Jan 28, 2016
Publication date	Jul 20, 2021
Grant date	Jul 20, 2021

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.

First claim

The invention claimed is:

1. 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 —CR c R d R e , —OH, —COOH, —CHO, —SH, —COCR c R d R e , —COOCR c R d R e , —CR c ═CR d R e , —CN, —N═C═O, —C═N═N—CR c R d R e , —C≡CR a , —NHCR c R d R e , and —NH 2 , wherein R c , R d , and R e 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,
-A 1 -(L 1 ) n1 -Y 1 —X 1 and -A 2 -(L 2 ) n2 -Y 2 —X 2 form one of the pairs of substituents being connected immediately adjacent positions among substitution positions of Ar,
X 1 and X 2 are the terminal groups,
A 1 and A 2 are, independently of each other, —O— or —S—,
L 1 and L 2 are, independently of each other, -E-,

E, E 1 , and E 2 are, independently of each other, O or S, n 1 and n 2 are, independently of each other, 0 or 1,
Y 1 and Y 2 are, independently of each other,

a 1 , a 2 , a 3 , b 1 , and b 2 are, independently of each other, integers of 0 to 30, and a 1 +a 2 +a 3 +b 1 +b 2 is an integer of 3 to 30,
P 1 , P 2 , and P 3 are, independently of each other, —CR a R b — or —(CR a R b ) r O—, r is an integer of 1 to 3,
Q 1 and Q 2 are, independently of each other, q 1 -(p 1 ) c1 -q 2 -(p 2 ) c2 -q 3 , q 1 and q 3 are, independently of each other, —O— or —S—, q 2 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, p 1 and p 2 are, independently of each other, —CR a R b —, c 1 and c 2 are, independently of each other, an integer of 0 to 2,
R a and R b are, independently of each other, H, F, Cl, Br, or I,
R c , R d , and R e 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, T 1 to T 14 are all C; or some of T 1 to T 14 are N, P, B or Si independently of each other and remainders are C,
G 1 , G 3 , G 5 , G 6 , G 7 , G 8 , G 10 , G 12 , G 13 , and G 14 represent substitution positions of the aromatic ring,
a first pair of -A 1 -(L 1 ) n1 -Y 1 —X 1 and -A 2 -(L 2 ) n2 -Y 2 —X 2 are bonded to G 6 and G 7 positions,
a second pair of -A 1 -(L 1 ) n1 -Y 1 —X 1 and -A 2 -(L 2 ) n2 -Y 2 —X 2 are bonded to G 13 and G 14 positions,
U is bonded to any one of remaining G 1 , G 3 , G 5 , G 8 , G 10 , and G 12 positions or not, and
o is an integer of 0 to 6;

in Structural Formula 6, T 1 to T 13 are all C; or some of T 1 to T 13 are N, P, B or Si independently of each other and remainders are C,
G 1 , G 2 , G 4 , G 5 , G 7 , G 8 , G 10 , and G 11 represent substitution positions of the aromatic ring,
a first pair of -A 1 -(L 1 ) n1 -Y 1 —X 1 and -A 2 -(L 2 ) n2 -Y 2 —X 2 are bonded to G 4 and G 5 positions,
a second pair of -A 1 -(L 1 ) n1 -Y 1 —X 1 and -A 2 -(L 2 ) n2 -Y 2 —X 2 are bonded to G 10 and G 11 positions,
U is bonded to any one of remaining G 1 , G 2 , G 7 , and G 8 positions or not, and
o is an integer of 0 to 4;

in Structural Formula 8, T 1 to T 14 , T 16 and T 17 are all C; or some of T 1 to T 14 , T 16 and T 17 are N, P, B or Si independently of each other and remainders are C,
G 1 , G 2 , G 4 , G 5 , G 7 , G 8 , G 9 , G 11 , G 12 , and G 14 represent substitution positions of the aromatic ring,
a first pair of -A 1 -(L 1 ) n1 -Y 1 —X 1 and -A 2 -(L 2 ) n2 -Y 2 —X 2 are bonded to G 4 and G 5 positions,
a second pair of -A 1 -(L 1 ) n1 -Y 1 —X 1 and -A 2 -(L 2 ) n2 -Y 2 —X 2 are bonded to G 11 and G 12 positions,
U is bonded to any one of remaining G 1 , G 2 , G 7 , G 8 , G 9 , and G 14 positions or not, and
o is an integer of 0 to 6;

in Structural Formula 10, T 1 to T 18 are all C; or some of T 1 to T 18 are N, P, B or Si independently of each other and remainders are C,
G 1 , G 2 , G 3 , G 6 , G 7 , G 8 , G 9 , G 12 , G 13 , G 14 , G 15 , and G 18 represent substitution positions of the aromatic ring,
a first pair of -A 1 -(L 1 ) n1 -Y 1 —X 1 and -A 2 -(L 2 ) n2 -Y 2 —X 2 are bonded to G 1 and G 2 positions,
a second pair of -A 1 -(L 1 ) n1 -Y 1 —X 1 and -A 2 -(L 2 ) n2 -Y 2 —X 2 are bonded to G 7 and G 8 positions,
a third pair of -A 1 -(L 1 ) n1 -Y 1 —X 1 and -A 2 -(L 2 ) n2 -Y 2 —X 2 are bonded to G 13 and G 14 positions,
U is bonded to any one of remaining G 3 , G 6 , G 9 , G 12 , G 15 , and G 18 positions or not, and
o is an integer of 0 to 6;

in Structural Formula 12, T 1 to T 24 are all C; or some of T 1 to T 24 are N, P, B or Si independently of each other and remainders are C,
G 1 , G 3 , G 4 , G 6 , G 7 ,

Assignees

• Univ Hanyang Ind Univ Coop Found
• Iucf Hyu

Inventors

• Suh Donghack
• Choi Kyounghwan

Classifications

• C07C43/257 Primary

  having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings · CPC title

• H10K59/875

  Arrangements for extracting light from the devices · CPC title

• B01J20/22 Primary

  comprising organic material · CPC title

• H10H20/855

  Optical field-shaping means, e.g. lenses · CPC title

• H10F77/42

  directly associated or integrated with photovoltaic cells, e.g. light-reflecting means or light-concentrating means · CPC title