KR101796859B1 - Light amplifying layer comprising 3-dimensional organic framework and optical device having the layer - Google Patents

Abstract

The present invention relates to an optical layer having a 3D organic structure, and an optical element having the same as an optical amplification layer. The 3D organic structure includes a plurality of organic molecules which are self-assembled by non-covalent bonding. Each of the organic molecules includes: an aromatic ring; a first pair of substituents combined with adjacent positions among substituent positions of the aromatic ring, respectively; and a second pair of substituents combined with adjacent positions among remaining substituent positions, respectively. The plurality of organic molecules are self-assembled by a Van Der Waals interaction, a London dispersion interaction, and hydrogen bonding between the first pair and the second pair of the substituents; and a Pi-pi interaction between aromatic rings. The optical layer is transparent; exhibits a dielectric constant close to zero; and facilitates light amplification through plasmon by Dirac electrons as a topological insulator.

Description

[0001] The present invention relates to an optical element having a three-dimensional organic structure and an optical element having the three-dimensional organic structure as an optical amplification layer,

The present invention relates to an optical amplification layer, and more particularly to an optical amplification layer using a three-dimensional porous organic structure.

As science and technology develops, nanoscale materials can be controlled and materials with periodicity and regularity of nanoparticles or nano units can be designed and implemented relatively freely. Nano-optics, which deals with existing optical phenomena and other phenomena using such nanoparticles or nanometer unit periodicity, is attracting new attention in the field of optics, and many studies have been made.

In the early days of nano-optics, photonic crystal research has been actively carried out, beginning with controlling the band gap using nanoparticles and reflecting structural color characteristics according to periodic and regular arrangement. Since then metamaterials have been announced that have a much smaller periodicity and regularity than applicable wavelengths.

Meta-materials with various new properties resulting from regular and periodic structural properties were first proposed by Victor Veselago, a physicist in Russia in 1968 [SOV PHYS USPEKHI, 1968, 10 (4), 509- 514] Through a variety of experiments, a meta-material with a negative permittivity and negative transmittance against the gigahertz band [Phys. Rev. Lett., 4, 4184, (2000)] and a meta-material having a negative refractive index for electromagnetic waves in the gigahertz band have been experimentally reported [Science, 2001, 292, 5514, 77-79]

In order to solve various problems such as a large loss and opaque state of a meta material having a negative refractive index thereafter, studies have been actively conducted on materials having a dielectric constant near zero, A material having a dielectric constant could be formed. Plasmonics originating from nanoparticles is also an axis that leads to nano-optics. Recently, as materials with topological insulator properties are arranged regularly and periodically, plasmonic phenomena caused by Dirac electrons, which have a massless Fermion behavior ≪ / RTI >

The above-described material having a dielectric constant close to zero and a plasmon phenomenon due to dirac electrons commonly have a characteristic capable of amplifying a photon. However, since the conventional topological insulator having a dielectric constant close to zero and a dirac electron is formed on the basis of a metal or an inorganic semiconductor, a large reflection loss due to the inherent negative dielectric constant of the material of a metal or an inorganic semiconductor, The problem of ohmnic loss due to electrons has not been solved yet

The object of the present invention is to provide a layer which is transparent and has a dielectric constant close to zero using organic materials other than metals or inorganic semiconductors and capable of optical amplification through plasmon by Dirac electrons as a topological insulator.

According to one aspect of the present invention, an optical layer is provided. The optical layer has a plurality of unit organic molecules represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

Ar is a 6- to 46-membered homocyclic aromatic ring or a heterocyclic aromatic ring,

-A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to immediately adjacent ones of the substitution positions of Ar However,

m is an integer of 1 to 8,

또는

이고,A ₁ and A ₂ , independently of each other,

or

ego,

,

,

,

,

,

,

,

, 또는

이고, E, E₁, 및 E₂는 서로에 관계없이 O 또는 S이고, n₁과 n₂는 서로에 관계없이 0 또는 1이고,L ₁ and L ₂ , independently of each other,

,

,

,

,

,

,

,

, or

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

이고, a₁, a₂, a₃, b₁, 및 b₂는 서로에 관계없이 0내지 30의 정수이며, a₁+a₂+a₃+b₁+b₂는 3 내지 30의 정수이고,Y < ₁ > and Y < ₂ >

And a ₁ , a ₂ , a ₃ , b ₁ , and b ₂ are independently an integer 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 independently of one another are -CR _a R _b - or - (CR _a R _b ) _r O-, r is an integer of 1 to 3,

또는

이고, q₂는 탄소에 결합된 수소기가 F, Cl, Br, 또는 I로 치환되거나 혹은 비치환된

,

,

,

,

,

,

,

, 또는

이고, p₁과 p₂는 서로에 관계없이 -CR_aR_b- 이고, c₁과 c₂는 서로에 관계없이 0 내지 2의 정수이고,Q ₁ and Q ₂ are independently of each other q ₁ - (p ₁ ) _{c 1} -q ₂ - (p ₂ ) _{c 2} -q ₃ , and q ₁ and q ₃ independently of each other

or

, Q < ₂ > is hydrogen or a group in which the hydrogen group bonded to the carbon is substituted by F, Cl, Br, or I,

,

,

,

,

,

,

,

, or

, P ₁ and p ₂ are independently of each other -CR _a R _b -, c ₁ and c ₂ are integers of 0 to 2,

X ₁ and X ₂ are independently selected _{-CR c R d R e, -OH} , -COOH, -CHO, -SH, -COCR c R d R e, -COOCR c R d R e, -CR c = and _{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, or -NH _2,

R _a and R _b are independently H, F, Cl, Br, or I,

R _c , R _d , and R _e are independently H, F, Cl, Br, or I,

U represents 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 carbon number of 3 to 15 A substituted or unsubstituted C2-C15 alkenyl group, a substituted or unsubstituted C2-C15 alkynyl group, a substituted or unsubstituted C6-C15 aryl group, a substituted or unsubstituted C2-C20 alkynyl group, A substituted or unsubstituted arylalkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted arylalkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted alkylsulfone group having 1 to 15 carbon atoms, a substituted or unsubstituted alkylmercapto group having 1 to 15 carbon atoms, Or a substituted or unsubstituted alkylthio group having 1 to 15 carbon atoms, a substituted or unsubstituted alkylphosphoryl group having 1 or 15 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 15 carbon atoms, a substituted or unsubstituted carbon number 1 A substituted or unsubstituted C1-C15 alkylthio group, a substituted or unsubstituted C1-C15 alkylthryl group, a substituted or unsubstituted C1-C15 alkyl isothiocyanic group, a substituted or unsubstituted C1- A substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, A substituted or unsubstituted aliphatic hydrocarbon group having 1 to 15 carbon atoms, a ketimine group having 1 to 15 carbon atoms, an aldimine group having 1 to 15 carbon atoms, a substituted or unsubstituted amido group having 1 to 15 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, , An arylamino group having 3 to 24 carbon atoms, an arylsilyl group having 3 to 24 carbon atoms, an aryloxy group having 3 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, and an alkylamino group having 1 to 24 carbon atoms Which is selected,

o is an integer between 0 and 16;

The three-dimensional organic structure may include a pair of unit organic molecules adjacent to each other in the same layer, a pair of unit organic molecules, X ₁ and X _2, and a unit organic molecule, X ₁ and X ₂ , A pair of unit organic molecules that are self-assembled by Van Der Waals interaction, London dispersion interaction or hydrogen bonding, and are located in different layers and are adjacent to each other, - self-assembly by pi interaction.

According to an aspect of the present invention, there is provided another embodiment of the optical layer. The optical layer includes a plurality of unit organic molecules forming a three-dimensional structure. Each unit organic molecule has a first pair of substituents respectively bonded to immediately adjacent positions of the aromatic ring and substitution positions of the aromatic ring and a second pair of substituents respectively bonded to immediately adjacent positions of the remaining substitution positions do. The terminal groups of the substituents contained in the first pair of unit organic molecules of one of the unit organic molecules contained in one layer of the three-dimensional structure and the terminal groups of the substituents contained in the second pair of another unit organic molecule The terminal groups of the substituents are self-assembled by van der Waals interaction, London dispersion interaction or hydrogen bonding. The unit organic molecules contained in one layer of the three-dimensional structure and the unit organic molecules contained in another adjacent layer are self-assembled by pi-pi interactions between aromatic rings.

The optical layer may be provided in the optical element as an optical amplification layer, and may be disposed on the optical path of the optical element. The optical element may be a light emitting element having a light emitting layer, and the optical amplifying layer may be disposed between the light emitting layer and the outside. The optical element may be a solar cell having a light absorbing layer, and the optical amplifying layer may be disposed between the light absorbing layer and the outside. The optical element may be a display having a light emitting layer or a light emitting element, and the optical amplifying layer may be disposed between the light emitting layer or the light emitting element and the outside. The optical element may be an illuminating device having a light emitting layer or a light emitting element, and the optical amplifying layer may be disposed between the light emitting layer or the light emitting element and the outside.

The optical layer may be included on the optical path of the super lens or the variable wavelength optical amplifier.

Such a porous three-dimensional organic structure, that is, an optical layer containing a porous organic crystal, is transparent using an organic material that is not a metal or an inorganic semiconductor and exhibits a dielectric constant close to 0, and optical amplification through a plasmon It can be possible.

It should be understood that the effects of the present invention are not limited to the above effects and include all effects that can be deduced from the detailed description of the present invention or the configuration of the invention described in the claims.

1 is a schematic view of a self-assembled three-dimensional organic structure according to an embodiment of the present invention.
2 is a cross-sectional view illustrating a light emitting diode having an optical amplification layer according to an embodiment of the present invention.
3 is a cross-sectional view illustrating an organic light emitting diode panel having an optical amplification layer according to an embodiment of the present invention.
4 is a cross-sectional view illustrating a liquid crystal display having an optical amplification layer according to an embodiment of the present invention.
5 is a cross-sectional view of a solar cell having an optical amplification layer according to an embodiment of the present invention.
6 is a cross-sectional view illustrating a dye-sensitized solar cell having an optical amplification layer according to an embodiment of the present invention.
7 is a ¹ H-NMR spectrum of 4,5,9,10-tetrakis (dodecyloxy) -pyrrole according to Production Example 1A measured in a CDCl ₃ solvent.
8 is a ¹ H-NMR spectrum of 4,5,9,10-tetrakis (tetradecyloxy) -pyran according to Preparation Example 1B measured in a CDCl ₃ solvent.
9 is a ¹ H-NMR spectrum of 4,5,9,10-tetrakis (octadecyloxy) -pyran according to Production Example 1C measured in a CDCl ₃ solvent.
10 is a ¹ H-NMR spectrum of 4,5-bis (dodecyloxy) -pyrane according to Production Example 1D measured in a CDCl ₃ solvent.
FIG. 11 is a ¹ H-NMR spectrum of the 4,5-bis (dodecyloxy) -pyrene-9,10-polyion according to Production Example 1E measured in a DMSO-d6 solvent.
12 is a ¹ H-NMR spectrum of 2,3,6,7-tetrakis (dodecyloxy) anthracene according to Production Example 2A measured in a CDCl ₃ solvent.
13 is a ¹ H-NMR spectrum of 2,3-bis (dodecyloxy) anthracene according to Production Example 2B measured in a CDCl ₃ solvent.
14 is a ¹ H-NMR spectrum of 2,3-bis (dodecyloxy) anthracene-6,7-dione according to Production Example 2B measured in a CDCl ₃ solvent.
15 is a ¹ H-NMR spectrum of 1,2,7,8-tetrakis (dodecyloxy) coronene according to Production Example 3A measured in a CDCl ₃ solvent.
16 is a ¹ H-NMR spectrum of 1,2-bis (dodecyloxy) coronene according to Production Example 3B measured in a CDCl ₃ solvent.
17 is a ¹ H-NMR spectrum of 7,8-bis (dodecyloxy) coronene-1,2-dione according to Production Example 3C in a CDCl ₃ solvent.
18 is a ¹ H-NMR spectrum of 1,2,5,6-tetrakis (dodecyloxy) cyclopenta [fg] acenaphthylene according to Production Example 4A measured in a CDCl ₃ solvent.
19 is a ¹ H-NMR spectrum of 1,2, -bis (dodecyloxy) cyclopenta [fg] Ace naphthalene according to Production Example 4B measured in a CDCl ₃ solvent.
20 is a ¹ H-NMR spectrum of 5,6-bis (dodecyloxy) cyclopenta [fg] acenaphthylene-1,2-dione according to Production Example 4C in a CDCl ₃ solvent.
21 is a ¹ H-NMR spectrum of 2,3,6,7,10,11-hexakis (dodecyloxy) triphenylene measured in a CDCl ₃ solvent according to Production Example 5A.
22 is a ¹ H-NMR spectrum of Compound 151 according to Production Example 15A measured in a CDCl ₃ solvent.
23 is a ¹ H-NMR spectrum of Compound 152 according to Production Example 15B measured in a CDCl ₃ solvent.
24 is a ¹ H-NMR spectrum of Compound 153 according to Production Example 15C measured in a CDCl ₃ solvent.
25A and 25B are optical photographs of 4,5,9,10-tetrakis (dodecyloxy) -pyrene (compound 11) crystals according to the preparation example of the compound.
26 shows the X-ray spectrum of a three-dimensional structure crystal by 4,5,9,10-tetrakis (dodecyloxy) -pyran (compound 11) according to the preparation example of the compound.
27 shows an X-ray spectrum of a three-dimensional structure crystal by 2,3,6,7-tetrakis (dodecyloxy) anthracene (Compound 21) according to a preparation example of the compound.
28 shows X-ray spectra of crystals of a three-dimensional structure formed by 1,2,7,8-tetrakis (dodecyloxy) coronene (Compound 31) according to the compound preparation example.
29 shows the X-ray spectrum of a three-dimensional structure crystal by 1,2,5,6-tetrakis (dodecyloxy) cyclopenta [f, g] acenaphthalene (Compound 41) according to the preparation example of the compound.
30 shows an X-ray spectrum of a three-dimensional structure crystal by 2,3,6,7,10,11-hexakis (dodecyloxy) triphenylene (compound 51) according to the compound preparation example.
31A and 31B are a perspective view and a top view, respectively, of the crystal structure of 4,5,9,10-tetrakis (dodecyloxy) -pyran deduced from the X-ray spectrum of FIG.
FIG. 32 is a graph showing the crystal structure of 4,5,9,10-tetrakis (dodecyloxy) -pyrene crystal, 4,5,9,10-tetrakis (tetradecyloxy) , 10-tetrakis (octadecyloxy) - pyrene crystal.
FIG. 33 shows photographs of 4,5,9,10-tetrakis (dodecyloxy) -pyrene (compound 11) crystals according to the preparation example of the compound by irradiating light.
34 shows an X-ray spectrum of the optical amplification layer obtained in Production Example 1 of the light-emitting element into which the optical amplification layer is introduced.
FIG. 35A is a graph showing a refractive index and a permittivity at an ordinary axis of the optical amplification layer according to an embodiment of the present invention, and FIG. 35B is a graph showing the refractive index and the permittivity at an extra-ordinary axis and the refractive index and the permittivity thereof.
36 is a graph showing light transmittance of an optical amplification layer according to an embodiment of the present invention.
37 is a graph showing the relationship between the normalized Fermi level of the optical amplification layer and the normalized plasmon frequency in the optical amplification layer production example.
38 is a graph showing photoluminescence intensity of an optical amplification layer according to an embodiment of the present invention.
39 is a graph showing amplification degree according to incident energy of the laser.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, the present invention will be described with reference to the accompanying drawings. The present invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Like parts are designated by like reference numerals throughout the specification.

In the specification, the expression "integer of N to N + X" includes all integers between N and N + X, that is, N, N + 1, N + 2 ... N + X-1, and N + X, where N and X are arbitrary integers.

As used herein, unless otherwise defined, the term "alkyl group" means an aliphatic hydrocarbon group. The alkyl group may be a "saturated alkyl group" which does not contain any double or triple bonds. The alkyl group may be an "unsaturated alkyl group" comprising at least one double bond or triple bond. The alkyl group, whether saturated or unsaturated, can be branched, straight chain or cyclic.

Hereinafter, embodiments of the present invention will be described in detail.

The optical layer according to this embodiment may contain a three-dimensional organic structure formed by self-assembly of an organic compound represented by the following formula (1), that is, an organic crystal.

Organic compounds constituting the three-dimensional organic structure

In one embodiment, the organic compound constituting the three-dimensional organic structure formed by self-assembly may be represented by the following formula (1).

[Chemical Formula 1]

Wherein Ar is a 6- to 46-member aromatic ring, which is a homocyclic aromatic ring in which all members are carbon or a heterocyclic aromatic ring having any one or more selected from N, P, B or Si have. Ar is a monocyclic aromatic ring of one member, for example, of 6 members, or a member of 10 to 46 members, in which two or more aromatic rings are bonded to each other to form a condensed ring, Lt; / RTI > may be a polycyclic aromatic ring having 14 rings.

Specifically, Ar may be any one of the following aromatic rings, but is not limited thereto. Specifically, a benzene group of Ar 1 to Ar 16 comprising a benzene which is a monocyclic aromatic or a heteroatom containing aromatic analogues of benzene containing a hetero atom; A naphthalene group of Ar17 to Ar30 comprising an aromatic analogue of naphthalene having two rings or of naphthalene containing a heteroatom; An anthracene group of Ar 31 to Ar 45 comprising an anthracene or an aromatic analog of an anthracene containing a heteroatom having three rings, an anthracene group of Ar 31 to Ar 45 of phenylene or an aromatic analog of a phenalene containing a hetero atom phenalene group, and a phenanthrene group of Ar 52 to Ar 69 comprising a phenanthracene or an aromatic analog of a phenanthracene containing a heteroatom; Cyclopenta [fg] acenaphthylene having four rings, or cyclopenta [fg] acenaphthylene of Ar70 to Ar71 containing an aromatic analog of cyclopenta [fg] acenaphthylene containing heteroatoms (cyclopenta [fg] acenaphthylene group, a tetracene group of Ar 72 to Ar 86 comprising an aromatic analogue of tetracene containing a tetraene or a heteroatom, Ar 87 to Ar 27 comprising an aromatic analog of pyrene containing a pyrene or heteroatom, Benz [de] anthracene group of Ar101 to Ar115 comprising a pyrene group of Ar100, a benz [de] anthracene or an aromatic analog of a benz [de] anthracene containing a heteroatom, and A triphenylene group of Ar116 to Ar130 comprising an aromatic analog of triphenylene or a tripehenylene containing heteroatom; A pentacene group of Ar131 to Ar140 comprising an aromatic analog of a pentacene or a heteroatom containing pentacene, having five rings; A coronene group of Ar141 to Ar148 comprising a coronene or an aromatic analogue of coronene containing a heteroatom, having 6 peri-fused rings; Or Ar149 to Ar152 having 7 or more rings.

In one embodiment, the Ar is a C _n (n is an integer from 2 to 6), as an example C ₂ (180 ° symmetry), C ₃ (120 ° symmetry), C ₄ (90 ° symmetry), or C ₆ ( 60 ° symmetry) molecular symmetry axis. At this time, it is assumed that all members of Ar are carbon.

Specifically, the benzene group of Ar1 to Ar16, the naphthalene group of Ar17 to Ar30, the anthracene group of Ar31 to Ar45, the cyclopenta [fg] acenaphthylene group of Ar70 to Ar71, the tetracene of Ar72 to Ar86 Group, the pyrene group of Ar87 to Ar100, the pentacene group of Ar131 to Ar140, the coronene group of Ar141 to Ar148, and Ar149 to Ar159 have C ₂ (180 °) symmetry; The benzene group of Ar1 to Ar16, the phenalene group of A46 to A51, the triphenylene group of Ar116 to Ar130, and the coronene group of Ar141 to Ar148 have C ₃ (120 °) symmetry; The benzene group of Ar1 to Ar16 and the coronene group of Ar141 to Ar148 have C ₆ (60 °) symmetry.

또는

일 수 있고, 서로 같거나 다를 수 있다. A₁과 A₂는 비공유 전자쌍을 가지고 있어 이들이 결합된 방향족 고리(Ar)에 전자를 공여(electron donating)할 수 있다. 이에 따라 방향족 고리(Ar)의 파이(π)-전자 구조 내 전자 밀도의 편재화가 유도될 수 있다. 구체적으로, A₁과 A₂가 결합된 위치에 인접한 영역의 전자 밀도가 다른 영역에 비해 상대적으로 높을 수 있으며, 그 외 부분은 상대적으로 낮을 수 있다.In Formula 1, A ₁ and A ₂ are chalcogen elements,

or

And may be the same or different from each other. A ₁ and A ₂ have a non-covalent electron pair and can donate electrons to the aromatic ring (Ar) to which they are bonded. This can lead to the localization of the electron density in the pi-electron structure of the aromatic ring (Ar). Specifically, the electron density of the region adjacent to the position where A ₁ and A ₂ are bonded may be relatively higher than that of the other regions, and the other portions may be relatively low.

,

,

,

,

,

,

,

, 또는

일 수 있다. 이 때, E, E₁, 및 E₂는 서로에 관계없이 O 또는 S일 수 있고, E₁ 및 E₂는 서로 같거나 다를 수 있다. n₁과 n₂는 서로 같거나 다를 수 있고, 0 또는 1일 수 있다.L ₁ and L ₂ may be the same or different from each other,

,

,

,

,

,

,

,

, or

Lt; / RTI > In this case, E, E ₁ , and E ₂ may be O or S, and E ₁ and E ₂ may be the same or different from each other. n ₁ and n ₂ may be the same or different from each other and may be 0 or 1.

일 수 있다. Y₁과 Y₂는 서로 같거나 다를 수 있다. a₁, a₂, a₃, b₁, 및 b₂는 서로에 관계없이 0내지 30의 정수이며, a₁+a₂+a₃+b₁+b₂는 3 내지 30의 정수일 수 있다. a₁, a₂, a₃, b₁, 및 b₂의 각각 그리고 a₁+a₂+a₃+b₁+b₂는 P₁, P₂, P₃, Q₁ 및 Q₂를 구성하는 작용기의 종류에 따라 달라질 수 있다. 다만, Y₁과 Y₂ 사이에 충분한 물리적 상호작용이 미칠 수 있도록, Y₁과 Y₂ 각각의 주쇄를 구성하는 원소의 수가 6 내지 30일 수 있다.Y ₁ and Y ₂ are organic groups, for example linear organic groups, irrespective of each other

Lt; / RTI > Y ₁ and Y ₂ may be the same or different from each other. _{a 1, a 2, a 3} , b 1, and b ₂ is from 0 to 30 constant irrespective of each _{other, a 1 + a 2 + a} 3 + b 1 + b 2 is a number of 3 to 30 integer. each of a ₁ , a ₂ , a ₃ , b ₁ , and b ₂ and a ₁ + a ₂ + a ₃ + b ₁ + b ₂ constitute P ₁ , P ₂ , P ₃ , Q ₁ and Q ₂ And may vary depending on the kind of the functional group. However, to have sufficient physical interaction between Y ₁ and Y ₂ have, Y may be a number of elements constituting the main chain ₁ and Y ₂ each from 6 to 30.

P ₁ , P ₂ , and P ₃ , independently of each other, may be -CR _a R _b - or - (CR _a R _b ) _r O-. Here, R _a and R _b may independently be H, F, Cl, Br, or I, and r may be an integer of 1 to 3. Specifically, P ₁ , P ₂ and P ₃ independently represent - (CH ₂ ) -, - (CF ₂ ) -, - (CH ₂ O) -, - (CH ₂ CH ₂ O) - (CH ₂ CH ₂ CH ₂ O) -.

또는

일 수 있고, 서로 같거나 다를 수 있다. q₂는 탄소에 결합된 수소기가 다른 작용기 예를 들어, F, Cl, Br, 또는 I로 치환되거나 혹은 비치환된

,

,

,

,

,

,

,

, 또는

일 수 있다. p₁과 p₂는 서로에 관계없이 -CR_aR_b- 일 수 있고, R_a와 R_b는 서로에 관계없이 H, F, Cl, Br, 또는 I일 수 있고, c₁과 c₂는 0 내지 2의 정수일 수 있다. 일 예로서, Q₁ 및 Q₂는 서로에 관계없이

,

,

,

,

, 또는

일 수 있다.Q ₁ and Q ₂ may be q ₁ - (p ₁ ) _{c 1} -q ₂ - (p ₂ ) _{c 2} -q ₃ and may be the same or different from each other. q ₁ and q ₃ independently of each other

or

And may be the same or different from each other. q < ₂ > is a group in which the hydrogen group bonded to the carbon is substituted with another functional group, for example, F, Cl, Br, or I,

,

,

,

,

,

,

,

, or

Lt; / RTI > p ₁ and p ₂ may be independently of each other -CR _a R _b -, R _a and R _b may be independently of each other H, F, Cl, Br, or I, and c ₁ and c ₂ And may be an integer of 0 to 2. As an example, Q ₁ and Q ₂ , independently of one another

,

,

,

,

, or

Lt; / RTI >

(즉, 위에서 a₂, a₃, b₁, 및 b₂는 모두 0), 더 구체적으로는 -(CH₂)_a1-(a1은 6 내지 30의 정수) 또는 -(CH₂CH₂O)_a1-(a1은 3 내지 10의 정수)일 수 있다.In one embodiment, Y < ₁ > and Y < ₂ >

(I.e., above a _2, a _3, b _1, and b ₂ are both 0), more specifically, the _{- (CH 2) a1 - (} a1 is an integer of 6 to 30) or - (CH ₂ CH ₂ O) _a1 - (a1 is an integer of 3 to 10).

(즉, 위에서 a₃ 및 b₂는 모두 0)이고, 더 구체적으로는 P₁은 -(CH₂)-이고, a1은 3 내지 15의 정수이고, Q₁은

,

,

,

,

, 또는

이고, b1은 1이고, P₂은 -(CH₂)-이고, a2은 1 내지 3의 정수일 수 있다.In another embodiment, Y < ₁ > and Y < _{2 &}

(I.e., above a ₃ and b ₂ are both 0), more specifically, a P ₁ is - (CH ₂₎ - and, a1 is an integer of 3 to 15, Q ₁ is

,

,

,

,

, or

, B 1 is 1, P ₂ is - (CH ₂ ) -, and a 2 is an integer of 1 to 3.

X ₁ and X ₂ are each a terminal group independently of each other, -H, -F, -Cl, -Br, -I, -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 , or -NH ₂ , and may be the same or different from each other. Here, R _c , R _d , and R _e may independently be H, F, Cl, Br, or I. As an example, -CR _c R _d R _e is -CH ₃ or -CF ₃ days may be, -COCR _c R _d R _e may be a _{-COCH 3, -COOCR c R d R} e is -COOCH ₃ days number and, -CR _c = CR _d R _e is _{-CH = CH 2, -CH = CF} 2, -CF = CH 2, -CF = CF 2, -CF = CH 2, -CF = CFH, or -CF = CF ₂ , -C = N = N-CR _c R _d R _e can be -C═N═N-CH ₃ , -C≡CR _a can be -C≡CH, -NHCR _c R _d R _e can be -NHCH ₃ .

In the present specification, each of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ may be referred to as a strain. The pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _n2 -Y ₂ -X ₂ may be substituted at the substitution positions of the aromatic ring (Ar) (E. G., G ₄ and G ₅ positions in structure 2 below) or peri positions (e. G., In the following structure 2) G ₁ and G ₃ positions). More specifically, the pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to each other to form an aromatic ring (Ar) And may be coupled to ortho positions. In this case, the _{-A 1 - (L 1) n1} -Y 1 -X 1 and _{-A 2 - (L 2) n2} -Y 2 -X 2, specifically, the Y ₁ and Y ₂ are included in between these There may be a physical interaction, such as an interaction by Van Der Waals interaction, which can be stabilized to increase the rigidity of the strains.

A pair of strains, that is, pairs of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ is one (m = 1) 8 (m = 2 to 8). That is, in Formula 1, m may be an integer of 1 to 8. The maximum value of the number of pairs of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ that can be bonded to one aromatic ring (Ar) May vary depending on the number and type of members of Ar.

When two or more pairs of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are present, that is, when m is 2 or more, The positions at which the pairs of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are connected are C _n (n is 2 to 6 (Symmetry-equivalent positions) of symmetrical positions among the substitution positions of the Ar, i.e., symmetry-equivalent positions. When the Ar is symmetrical with respect to C _n (n is an integer of 2 to 6), the -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ The number m of pairs of " m " Specifically, when Ar is symmetrical with C ₂ (180 °), a pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ The number m may be 2, and the positions at which two pairs of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are connected to Ar And may be positions that maintain the C ₂ (180 °) symmetry of Ar. In another example, when Ar is symmetrical to C ₃ (120 °), the -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ The number m of pairs may be 3 and three pairs of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are connected to Ar Positions may be positions that maintain the C ₃ (120 °) symmetry of Ar. In another example, when Ar is symmetrical with C ₄ (90 °), the -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ The number m of pairs of the pair of atoms A and B may be 4 and four pairs of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are connected to Ar which positions may be a position for holding a C ₄ (90 °) the symmetry of the Ar. In other words, when the number of pairs of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ is two or more, The angle formed by these pairs with respect to the center of Ar may be the same.

In _{addition, -A 1 - (L 1)} n1 -Y 1 -X 1 and -A ₂ - (L ₂₎ between pairs of _n2 -Y ₂ -X ₂ is _{-A 1 - (L 1) n1} -Y 1 A substitution position where -X ₁ or -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ is not bonded can be located, which can enhance the localization of the electron density in the aromatic ring. Further, U may be bonded to at least some of the substitutable positions in which -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ or -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are not bonded have.

U represents 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 carbon number of 3 to 15 A substituted or unsubstituted C2-C15 alkenyl group, a substituted or unsubstituted C2-C15 alkynyl group, a substituted or unsubstituted C6-C15 aryl group, a substituted or unsubstituted C2-C20 alkynyl group, A substituted or unsubstituted arylalkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted arylalkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted alkylsulfone group having 1 to 15 carbon atoms, a substituted or unsubstituted alkylmercapto group having 1 to 15 carbon atoms, Or a substituted or unsubstituted alkylthio group having 1 to 15 carbon atoms, a substituted or unsubstituted alkylphosphoryl group having 1 or 15 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 15 carbon atoms, a substituted or unsubstituted carbon number 1 A substituted or unsubstituted C1-C15 alkylthio group, a substituted or unsubstituted C1-C15 alkylthryl group, a substituted or unsubstituted C1-C15 alkyl isothiocyanic group, a substituted or unsubstituted C1- A substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, A substituted or unsubstituted aliphatic hydrocarbon group having 1 to 15 carbon atoms, a ketimine group having 1 to 15 carbon atoms, an aldimine group having 1 to 15 carbon atoms, a substituted or unsubstituted amido group having 1 to 15 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, , An arylamino group having 3 to 24 carbon atoms, an arylsilyl group having 3 to 24 carbon atoms, an aryloxy group having 3 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, and an alkylamino group having 1 to 24 carbon atoms And can be any one selected. o may be an integer between 0 and x, where x is an integer less than 2m from the number of replaceable positions of Ar. As an example, x may be a maximum of 16.

The compound represented by Formula 1 may be any one selected from the following Structural Formulas 1 to 15, but is not limited to the following structural formulas.

[Structural formula 1]

[Structural formula 2]

[Structural Formula 3]

[Structural Formula 4]

[Structural Formula 5]

[Structural Formula 6]

[Structural Formula 7]

[Structural formula 8]

[Structural Formula 9]

[Structural Formula 10]

[Structural Formula 11]

[Structural Formula 12]

[Structural Formula 13]

In Structural Formulas 1 to 13, T ₁ to T ₄₀ are all C; Some of T ₁ to T ₄₀ may be N, P, B or Si, and the remainder may be C, regardless of each other. In addition, Gn represents substitution positions of an aromatic ring (Ar of the above formula (1)).

The compound represented by the formula (1) may be a compound represented by any of the following formulas (1a) to (1e).

[Formula 1a]

[Chemical Formula 1b]

[Chemical Formula 1c]

≪ RTI ID = 0.0 &

[Formula 1e]

In Formula 1a to _{1e, Ar, A 1, A} 2, L 1, L 2, n1, n2, Y 1, Y 2, X 1, X 2, m, U and o Ar explained in the above-mentioned general formula (1) , A _1, A _2, may be equal to L _1, L _2, and _{n1, n2, Y 1, Y} 2, X 1, X 2, m, U and o, respectively. A plurality of A _{1 s} may be the same or different from each other, a plurality of A _{2 s} may be the same or different from each other, a plurality of L _{1 s} may be the same or different from each other, and a plurality of L _{2 s} may be the same or different from each other and, a plurality of _n1 they may be the same as or different from each other, and a plurality of _n2 are may be the same as or different from each other, and a plurality of Y ₁ are may be the same as or different from each other, and a plurality of Y ₂ may be the same or different from each other, a plurality of X _{1 s} may be the same or different from each other, and the plurality of X _{2 s} may be the same or different from each other, and the plurality of U s may be the same or different from each other.

In particular, the compound represented by Formula 1 may be a compound of any of Formula 1c to 1e.

Specifically, the compound of formula (1c) has a pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ , (M = 2 in formula (1)). In the formula (1c), Ar may have a C ₂ (180 °) symmetry. Specifically, Ar may be a benzene group of the Ar 1 to Ar 16, a naphthalene group of Ar 17 to Ar 30, an anthracene group of Ar 31 to Ar 45, Penta [fg] acenaphthylene group, tetracene group of Ar72 to Ar86, pyrene group of Ar87 to Ar100, pentacene group of Ar131 to Ar140, coronene group of Ar141 to Ar148, and Ar149 to Ar159 Lt; / RTI > In addition, the positions at which the strains are connected to the Ar may be positions at which C ₂ (180 °) symmetry is maintained, that is, positions having equivalent symmetry among the substitution positions of Ar. Further, the positions at which the pair of strains are connected to the Ar may be orthogonal to each other. Also, a replacement position where the strain is not connected may be located between the pairs.

Specifically, when Ar is a benzene group of the formula 1, a pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ to _{(L 2) n2 -Y 2 -X} 2 is G ₄ and G ₅ position - the other pair of the G ₁ and G ₂ -A ₁ where _{- (L 1) n1 -Y 1} -X 1 -A ₂ and And the remaining G ₃ or G ₆ may be bonded to U or not. In this case, o may be an integer of 0 to 2.

When Ar is a naphthalene group of the above formula 2, a pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are G ₄ and the other pair of -A ₁ to G ₅ where _{- (L 1) n1 -Y 1} -X 1 and _{-A 2 - (L 2) n2} -Y 2 -X 2 may be bonded to G ₉ and G ₁₀ position And the remainder of G ₁ , G ₃ , G ₆ , or G ₈ may or may not be bound to U. In this case, o may be an integer of 0 to 4.

A pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ is a group represented by G ₆ and the other pair in the position G ₇ -A ₁ - may be _{(L 2) n2 -Y 2 -X} 2 is coupled to a G ₁₃ and G ₁₄ where _{- (L 1) n1 -Y 1} -X 1 -A ₂ and And U may or may not be bonded to the remaining G ₁ , G ₃ , G ₅ , G ₈ , G ₁₀ , or G ₁₂ . In this case, o may be an integer of 0 to 6.

When Ar is a cyclopenta [fg] acenaphthylene group of the above formula 6, a pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ is a pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ different from G ₁ and G _{2 at} positions G ₇ and G ₈ position, and the remaining G ₄ , G ₅ , G ₁₀ , or G ₁₁ may be bonded to U or not. In this case, o may be an integer of 0 to 4. In another example in which Ar is the cyclopenta [fg] acenaphthylene group of the above formula 6, a pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _n2 -Y ₂ -X _2, G ₄ and G _5, the other pair to position _{-A 1 - (L 1) n1} -Y 1 -X 1 and _{-A 2 - (L 2) n2} -Y 2 -X 2 May be bonded to the G ₁₀ and G ₁₁ positions, and the remaining G ₁ , G ₂ , G ₇ , or G ₈ may or may not be bound to U. In this case, o may be an integer of 0 to 4.

A pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ is a group represented by G ₈ and G ₉ located on the other pair of _{-A 1 - (L 1) n1} -Y 1 -X 1 and _{-A 2 - (L 2) n2} -Y 2 -X 2 can be coupled to a G ₁₇ and G ₁₈ position And U may or may not be bonded to the remaining G ₁ , G ₃ , G ₅ , G ₇ , G ₁₀ , G ₁₂ , G ₁₄ , or G ₁₆ . In this case, o may be an integer of 0 to 8.

When Ar is a pyrene group of the structural formula 8, a pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ is G ₄ G and the other pair on the _{5-position -A 1 - (L 1) n1} -Y 1 -X 1 and _{-A 2 - (L 2) n2} -Y 2 -X 2 can be coupled to a G ₁₁ and G ₁₂ position And U may or may not be bonded to the remaining G ₁ , G ₂ , G ₇ , G ₈ , G ₉ , or G ₁₄ . In this case, o may be an integer of 0 to 6.

A pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ in the case where Ar is the pentacene group of the structural formula 11 is G ₁₀ and the other pair in the position G _{11 -A 1 - (L 1) n1} -Y 1 -X 1 and _{-A 2 - (L 2) n2} -Y 2 -X 2 can be coupled to a G ₂₁ and G ₂₂ position And U may or may not be bonded to the rest of G ₁ , G ₃ , G ₅ , G ₇ , G ₉ , G ₁₂ , G ₁₄ , G ₁₆ , G ₁₈ or G ₂₀ . In this case, o may be an integer of 0 to 10.

A pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ is a group represented by G ₆ G ₇ and the other pair to position _{-A 1 - (L 1) n1} -Y 1 -X 1 and _{-A 2 - (L 2) n2} -Y 2 -X 2 can be coupled to a G ₁₅ and G ₁₆ position And U may or may not be bonded to the remaining G ₁ , G ₃ , G ₄ , G ₉ , G ₁₀ , G ₁₂ , G ₁₃ , or G ₁₈ . In this case, o may be an integer of 0 to 8.

A pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ is an aromatic ring of G ₈ and the other pair in the position G ₉ -A ₁ - may be _{(L 2) n2 -Y 2 -X} 2 is coupled to a G ₂₁ and G ₂₂ where _{- (L 1) n1 -Y 1} -X 1 -A ₂ and And U may or may not be bonded to the remaining G ₁ , G ₃ , G ₄ , G ₆ , G ₁₁ , G ₁₃ , G ₁₄ , G ₁₆ , G ₁₇ , G ₁₉ , G ₂₄ or G ₂₆ . In this case, o may be an integer of 0 to 12.

The compound of the formula (1d) has three pairs of strains (-A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ m = 3). In the formula (1d), Ar may have C ₃ (120 °) symmetry. Specifically, Ar may be a phenalene group of A46 to A51, a triphenylene group of Ar116 to Ar130, And n is an integer of 1 to 3, In addition, the positions at which the strains are connected to the Ar may be positions at which C ₃ (120 °) symmetry is maintained, that is, positions having equivalent symmetry among the substitution positions of Ar. Further, the positions at which the pair of strains are connected to the Ar may be orthogonal to each other. Also, a replacement position where the strain is not connected may be located between the pairs.

A pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ is a group represented by G ₁ and G ₂ in position, the other pair of _{-A 1 - (L 1) n1} -Y 1 -X 1 and _{-A 2 - (L 2) n2} -Y 2 -X 2 are coupled to G ₅ and G ₆ position And another pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ may be bonded to G ₉ and G ₁₀ positions And in the remaining G ₄ , G ₈ , or G ₁₃ , U may be bonded or not. In this case, o may be an integer of 0 to 3.

When Ar is a triphenylene group of the formula 10, a pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _n2 -Y ₂ -X ₂ is G ₁ and G ₂ in position, the other pair of _{-A 1 - (L 1) n1} -Y 1 -X 1 and _{-A 2 - (L 2) n2} -Y 2 -X 2 is a G ₇ and G ₈ position And another pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ may be bonded to G ₁₃ and G ₁₄ And U may or may not be bonded to the remaining G ₃ , G ₆ , G ₉ , G ₁₂ , G ₁₅ , or G ₁₈ . In this case, o may be an integer of 0 to 6.

A pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ is a group represented by G ₆ G ₇ and the other pair to position _{-A 1 - (L 1) n1} -Y 1 -X 1 and _{-A 2 - (L 2) n2} -Y 2 -X 2 can be coupled to a G ₁₂ and G ₁₃ position And another pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _n2 -Y ₂ -X ₂ can be attached to the G ₁ and G ₁₈ positions And U may or may not be bonded to the remaining G ₃ , G ₄ , G ₉ , G ₁₀ , G ₁₅ , or G ₁₆ . In this case, o may be an integer of 0 to 6.

The compound of the formula (1e) has three pairs of strains (-A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ m = 4). In the formula (1e), Ar may have a C ₄ (90 °) symmetry. In addition, the positions at which the strains are connected to the Ar may be positions at which C ₄ (90 °) symmetry is maintained, that is, positions having equivalent symmetry among the substitution positions of Ar. Further, the positions at which the pair of strains are connected to the Ar may be orthogonal to each other. Also, a replacement position where the strain is not connected may be located between the pairs.

In another embodiment, the organic compound constituting the self-assembled three-dimensional structure may be represented by the following formula (2).

(2)

In Formula _{2, Ar, A 1, A} 2, L 1, L 2, n1, n2, Y 1, Y 2, X 1, X 2, U and o are as described in formula ₁ Ar, A 1, A _2, may be the same as L _1, L _2, and _{n1, n2,} Y _1, Y _2, X _1, X _2, and U o, respectively. A plurality of A _{1 s} may be the same or different from each other, a plurality of A _{2 s} may be the same or different from each other, a plurality of L _{1 s} may be the same or different from each other, and a plurality of L _{2 s} may be the same or different from each other and, a plurality of _n1 they may be the same as or different from each other, and a plurality of _n2 are may be the same as or different from each other, and a plurality of Y ₁ are may be the same as or different from each other, and a plurality of Y ₂ may be the same or different from each other, a plurality of X _{1 s} may be the same or different from each other, and the plurality of X _{2 s} may be the same or different from each other, the plurality of U s may be the same or different from each other, and the plurality of o s may be the same or different from each other.

In Formula 2, Z ₁ and Z ₂ independently represent 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 An alkyl group, a substituted or unsubstituted alkenyl group having 2 to 15 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 15 carbon atoms, a substituted or unsubstituted aryl group having 5 to 15 carbon atoms, a substituted or unsubstituted C2 to C15 A substituted or unsubstituted arylalkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted alkylsulfone group having 1 to 15 carbon atoms, a substituted or unsubstituted alkylmercapto group having 1 to 15 carbon atoms, A substituted or unsubstituted C1 to C15 alkylphosphoric acid group, a substituted or unsubstituted C1 to C15 alkylthio group, a substituted or unsubstituted C1 to C15 alkylthio group, A substituted or unsubstituted C1-C15 alkylthio group, a substituted or unsubstituted C1-C15 alkylthryl group, a substituted or unsubstituted C1-C15 alkyl isothiocyanic group, a substituted or unsubstituted C1- A substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, A substituted or unsubstituted aliphatic hydrocarbon group having 1 to 15 carbon atoms, a ketimine group having 1 to 15 carbon atoms, an aldimine group having 1 to 15 carbon atoms, a substituted or unsubstituted amido group having 1 to 15 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, , An arylamino group having 3 to 24 carbon atoms, an arylsilyl group having 3 to 24 carbon atoms, an aryloxy group having 3 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, and an alkylamino group having 1 to 24 carbon atoms. May be any one selected.

In Formula 2, L may be an integer of 1 to 4.

In another embodiment, the organic compound constituting the self-assembled three-dimensional structure may be represented by the following formula (3).

 (3)

In Formula _{3 Ar, A 1, A 2} , L 1, L 2, n1, n2, Y 1, Y 2, X 1, X 2, U and o Ar, A _1, A ₂ mentioned in the above formula (1) , may be equal to L _1, L _2, and _{n1, n2,} Y _1, Y _2, X _1, X _2, and U o, respectively. A plurality of A _{1 s} may be the same or different from each other, a plurality of A _{2 s} may be the same or different from each other, a plurality of L _{1 s} may be the same or different from each other, and a plurality of L _{2 s} may be the same or different from each other and, a plurality of _n1 they may be the same as or different from each other, and a plurality of _n2 are may be the same as or different from each other, and a plurality of Y ₁ are may be the same as or different from each other, and a plurality of Y ₂ may be the same or different from each other, a plurality of X _{1 s} may be the same or different from each other, and the plurality of X _{2 s} may be the same or different from each other, the plurality of U s may be the same or different from each other, and the plurality of o s may be the same or different from each other.

,

,

,

,

,

, 또는

이고,A′ 및 A″는 서로에 관계없이 O 또는 S이고, R_f, R_g, R_h, R_i, R_j, R_f′, 및 R_g′는 서로에 관계없이 H 또는 C1 내지 C3의 알킬기일 수 있다.In the above formula (3), X ₁ 'and X ₂ '

,

,

,

,

,

, or

And, A 'and A "is O or S, regardless of each _{other, R f, R g, R} h, R i, R j, R f', and R _g 'is H or a C1 to C3 independently selected Lt; / RTI >

In addition, l may be an integer of 1 to 4.

Self-assembled three-dimensional organic structure

1 is a schematic view of a self-assembled three-dimensional organic structure according to an embodiment of the present invention.

Referring to FIG. 1, the compounds represented by Chemical Formulas 1 to 3, that is, unit organic molecules (UM), can be self-assembled to form a three-dimensional organic structure, that is, an organic crystal. 1 shows an organic structure using the unit organic molecules shown in Chemical Formula 1c, but is not limited thereto.

-A- (L) _n -YX, which are a pair of substituents connected to an aromatic ring in a unit organic molecule (UM), are directly adjacent positions of substitutable positions of the aromatic ring, for example ortho, Position or a peri position. In this case, a pair of -A- (L) _n -YX, specifically the Y groups contained in each of them, are specifically referred to as a Van Der Waals interaction by a physical interaction (PIa) ≪ / RTI > As a result, a pair of -A- (L) _n -YXs, ie, a pair of strains, is less rigid than a strain of -A- (L) _n -YX, ).

On the other hand, A has a non-covalent electron pair and can electron donate to the bonded aromatic ring (Ar). As a result, the electron density of the pi (pi) -electronic structure in the aromatic ring (Ar) is uniformalized, so that a region having a relatively high electron density and a region having a relatively low electron density can be arranged. In other words, A bonded to the aromatic ring (Ar) can induce the localization of electron density in the aromatic ring (Ar).

Specifically, the electric multipole self-strengthening corresponding to twice the number of -A- (L) _n -YX (strain) pairs (m in Formula (1)) can be enhanced. For example, in the case of 1-coordinate organic molecules represented by the general formulas (1a) and (1b), a quadrupole can be intensified in the aromatic ring (Ar) , The quadrupole in the aromatic ring (Ar) can be further strengthened. In the case of the 3 coordination type organic molecule represented by the formula (1d), hexapole can be strengthened in the aromatic ring (Ar), and in the case of the tetrahedral organic molecule represented by the formula (1e) Octapole can be strengthened.

When a plurality of such unit organic molecules (UM) are located, X groups between unit organic molecules (UM) adjacent to each other in one direction (for example, X direction) have physical interactions, specifically, Van Der Waals interaction, London dispersion interaction, or hydrogen bonding (PIb). As one example, among the X groups, -CF ₃ , -SH, -F, -Cl, -Br, -I, -CH = CF ₂ , -CF═CH ₂ , -CF═CF ₂ , -CF═CH ₂ , -CF = CFH, -CF = CF ₂ , -COCH ₃ , -COOCH ₃ , -CHO, -CN, -N═C═O, and -C═N═N-CH ₃ can be obtained by van der Waals interaction may be bonded _{to, -H, -CH 3, -CH =} CH 2, -C≡CH, and may be bonded by the London dispersion forces, -OH, -COOH, -NH _2, or -NHCH ₃ is a hydrogen bond . ≪ / RTI >

In addition, the aromatic ring groups included in each of the unit organic molecules (UM) adjacent to one another (F ₁ ) and another layer (F ₂ ) in another direction (for example, the Z direction) Can be self-assembled or laminated by interaction (PIc). Specifically, as described above, an electron-rich region (? -) and an electron-deficient region (? +) Induced in the aromatic ring group (Ar) Compared to the direction X in which the compound of the first layer (F ₁ ) extends due to attraction between the electron rich region (delta-) and the electron deficient region (delta +) between adjacent aromatic ring groups in the Y direction The direction in which the unit organic molecules (UM) of the two layers (F ₂ ) extend can be changed by a predetermined angle. As an example, the direction in which the first layer (F ₁₎ unit of the organic molecules (UM) the direction (X) a second layer (F ₂₎ unit of the organic molecules (UM) compared to extending the extension 90 also turn be And thus the direction in which the unit organic molecules (UM) of the second layer (F ₂ ) extend can be in the Y direction.

In addition, the X groups between the unit organic molecules (UM) of the second layer (F ₂ ) may also exhibit physical interactions, specifically Van Der Waals interaction, London dispersion interaction, (PIb) by being pulled by hydrogen bonding.

As described above, the porous three-dimensional organic structure according to the present embodiment, that is, the porous organic crystal, can exhibit a physical interaction, specifically, a pi-pi interaction, a dipole- The unit organic molecules can be self-assembled through induced dipole-dipole interactions and induced dipole-induced dipole interactions.

In addition, these organic crystals have regularity and periodicity, and thus have a basic lattice of triclinic, monoclinic, orthorhombic, tetragonal, hexagonal, or cubic Structure. Specifically, in the case of linear coordination organic molecules represented by Chemical Formulas 1a and 1b and 2 coordination types represented by Chemical Formula 1c, that is, linear organic molecules, triclinic, orthorhombic, tetragonal, cubic The cubic organic molecules represented by formula (1d) can be hexagonal or monoclinic.

Specifically, Fig. 1 shows a lattice structure of an orthorhombic system.

Such a porous three-dimensional organic structure, that is, a porous organic crystal, is formed by self-assembly based on weak organic-organic interaction, specifically, non-covalent bonding between unit organic molecules, so that a structure is easily and simply formed, Because they are formed using physical bonding between pure compounds without bonding, melting and dissolving are possible at all times, and a wide void volume and fully regular and periodic structure can be secured. Unlike the metal organic framework (MOF), the use of no metal makes it possible to maintain structural characteristics even in the water and atmospheric environment. In addition, the compound according to the present invention has an advantage of self-assembling process of forming a structure, but it produces an elaborate and orderly complex and hierarchical structure despite its rapid speed.

Organic compound manufacturing method for self-assembled three-dimensional organic structure

Method for preparing a compound according to formula (1)

In one embodiment, the compound according to Formula 1 can be prepared by the following Reaction Schemes 1 to 2. However, the present invention is not limited thereto.

[Reaction Scheme 1]

(1) Synthesis of Sub 1-1, Sub 1-2, and Sub 1-3

The aromatic ring (Ar) was dissolved in dichloromethane and acetonitrile solution and dissolved in distilled water together with ruthenium (Ⅲ) chloride hydrate and sodium metapelidate (NaIO ₄ ) To obtain Sub1-1, Sub1-2, and Sub1-3. At this time, Sub1-1, Sub1-2, and Sub1-3 can be obtained in accordance with the reflux temperature.

(2) Synthesis of Products 1 to 4

Sub1-1, bromo any of Sub1-2, and Sub1-3 parent tetrabutylammonium (Bu ₄ NBr), with sodium hydrosulfite _{(Na 2 S 2 O 4)} , distilled water, tetrahydrofuran (THF) And then refluxed at a predetermined temperature for a predetermined period of time, X'-R (wherein X 'is Br as an example of halide and -R is - (L ₁ ) _n1 -Y ₁ -X ₁ . L ₁ , n ₁ , Y ₁ , X ₁ may be as defined in the description of formula (1). Specifically, X ₁ may be CR _c R _d R _e or -OH, wherein R _c , R _d , And R _e may independently be H, F, Cl, Br, or I) and an aqueous solution prepared by dissolving KOH in distilled water, and then refluxing at a predetermined temperature for a predetermined time, You can get either one. At this time, any one of Products 1 to 4 can be obtained by adjusting the molar ratio of X'-R to each of Sub1-1, Sub1-2, and Sub1-3.

[Reaction Scheme 2]

(1) Synthesis of Product 2-1

In the above Reaction Scheme 1, X'-R ₁ -X "wherein X 'and X" are Br as an example of halide and -R ₁ - is -L ₁ - (P ₁ ) _a1 -, wherein L ₁ , P ₁ , a ₁ can be as defined in the description of formula (1), the same method as the synthesis of product 2 is carried out to obtain product 2-1 Can be obtained.

(2) Synthesis of Product 2-2

product 2-1 and HO-R ₁ '-OH (in this case, -R ₁ ' - may be -q ₂ - described in Formula 1) are dissolved in dimethylformamide, refluxed at a predetermined temperature, After the reaction, the product is extracted with chloroform, the water is removed with magnesium sulfite, and the product 2-2 can be obtained through column chromatography.

(3) Synthesis of Product 2-3

(2) and X'-R ₁ ", where X 'is Br as an example of a halide and -R ₁ " is - (P ₂ ) a ₂ -CH ₃ , wherein P ₂ and a 2 are May be as defined in the description of Chemical Formula 1) into tetrahydrofuran, refluxing at a predetermined temperature for a predetermined period of time, reacting, and subjecting to column chromatography using chloroform as a developing solution.

Method for preparing compound of formula (2)

In one embodiment, the compound according to Formula 2 can be prepared in the same manner as in Reaction Scheme 3 below. However, the present invention is not limited thereto.

[Reaction Scheme 3]

(Bu ₄ NBr) and sodium hydrosulfite (Na ₂ S ₂ O ₄ ) were mixed with Sub 1-2 and Product 3 (molar ratio of Sub 1-2 and Product 3 = 1: 2) , R 'is - (L ₁ ) _{n 1} -Y ₁ (R ₁ ), and R ₁ is a halogen such as chlorine, bromine or iodine, dissolved in distilled water or tetrahydrofuran (THF) can be -X _1. wherein, L _1, n _1, Y _1, X ₁ may be the same as defined in the description of formula (I), specifically, X ₁ may be a CR _c R _d R _e or -OH , R _c , R _d , and R _e may independently be H, F, Cl, Br, or I) and an aqueous solution prepared by dissolving KOH in distilled water, Yielding the final product, product 5.

Method for preparing compound of formula (3)

In one embodiment, the compound according to Formula 3 can be prepared by the same method as in Reaction Scheme 4 below. However, the present invention is not limited thereto.

[Reaction Scheme 4]

Two or more compounds (compounds A and B) in which the terminal groups (X ₁ , X ₂ ) of the compounds represented by the formula (1c) can react with each other are selected and dissolved in distilled water and chlorobenzene to dissolve the KOH in distilled water And then refluxing the solution at a predetermined temperature for a predetermined time, compound 3 can be obtained as a final product.

In the above reaction scheme 4 Ar, A, L, n , Y, l, and X 'is _{Ar, A 1, L 1,} n 1, Y 1, l, and X ₁ is mentioned in the formula (3)' may be respectively the same as the . On the other hand, X ₁ and X ₂ can be appropriately selected from the examples of X _{1 in} the formula (1) so as to form X 'by a reaction therebetween.

Manufacturing method of self assembled 3D structure

The above-described organic compound or organic molecule is dissolved in an appropriate organic solvent, and then recrystallized and dried to obtain a three-dimensional structure by self-assembly of the organic molecules. The drying may be vacuum drying. Specifically, a powder containing self-assembled three-dimensional structure particles can be obtained through the following first to fourth methods. The self-assembled three-dimensional structure particles may have a nano-rod shape.

First Method: Powder Formation Method Containing a Three-Dimensional Structure Using an Organic Solvent Evaporation Method

 1) dissolving the organic molecules in an organic solvent having a medium solubility to form a homogeneous solution

 2) gradually evaporating the solvent in the solution to gradually change to a homogenous solution with a thick concentration

 3) forming a three-dimensional structure according to self-assembly of the organic molecules at a critical concentration

 4) filtering the structure and removing residual organic solvent in vacuum

Second Method: Powder Formation Method Containing Three-Dimensional Structure Using Cooling Method

 1) dissolving the organic molecules in a heated insoluble organic solvent to make a homogeneous solution at a low concentration

 2) cooling the homogeneous solution in a state of blocking the movement of the substance from the outside

 3) forming a three-dimensional structure according to self-assembly of the organic molecules at a critical temperature

 4) filtering the structure and removing residual organic solvent in vacuum

Third method: Powder forming method containing three-dimensional structure using multi-solvent having different solubility

 1) Two different systems in an enclosed space are provided. In one system, a homogeneous solution in which the organic molecules are dissolved is placed in a first organic solvent having high solubility for the organic molecules, and the other system is evaporated A step of disposing a second organic solvent which has good solubility in the organic molecules but has good mixing with the first organic solvent

 2) the second organic solvent is evaporated and the evaporated second organic solvent is mixed into the homogeneous solution to lower the solubility of the organic molecules

3) a step of forming a three-dimensional structure according to self-assembly of the organic molecules in the critical solubility

4) filtering the structure and removing residual organic solvents in vacuo

Fourth method: Powder forming method containing three-dimensional structure using multi-solvent having different solubility

 1) dissolving the organic molecules in a first organic solvent having a high solubility by saturation solubility to obtain a homogeneous solution

2) dropping the homogeneous solution into a second organic solvent in which the organic molecules exhibit a very low solubility to lower the solubility of the organic molecules

3) a step of forming a three-dimensional structure according to self-assembly of the organic molecules in the critical solubility

4) filtering the structure and removing residual organic solvents in vacuo

In addition, when the nuclei for self-assembly of the organic molecules are generated in the first to fourth methods, specifically, step 3), and at the time of subsequent growth, Compounds to be displayed may be added. As a result, a structure having different kinds of organic molecules in one structure can be formed.

Method for manufacturing an optical layer having a three-dimensional organic structure

The optical layer can be manufactured using the three-dimensional organic structure obtained by the above-described three-dimensional organic structure manufacturing method. A specific method of manufacturing the optical layer may be as follows.

The optical layer manufacturing method according to the first embodiment

A powder containing the three-dimensional structure is put into a mixed solvent of a first solvent capable of dissolving a powder containing the three-dimensional structure and a second solvent capable of mixing with the first solvent to prepare a solution, The optical layer can be formed by coating on a support. In this case, the first solvent and the second solvent may be mixed in a volume ratio of 1: 1 to 7: 1, specifically 1: 1 to 4: 1, for example, 1.5: 1 to 2.5: The solution may have a concentration of 5 mM to 50 mM, as an example, 5 mM to 40 mM, and as another example, 1 mM to 30 mM. The coating may also be spin coating, dip coating, bar coating, slot die coating, spray coating, roll to roll coating, or inverse roll coating. The first solvent may be, for example, chloroform, and the second solvent may be, for example, ethyl acetate.

The optical layer manufacturing method according to the second embodiment

In another example, a selected polymer having compatibility with the three-dimensional structure is placed in a mixed solvent of a first solvent capable of dissolving a powder containing the three-dimensional structure and a second solvent capable of mixing with the first solvent, After forming the first solution, a powder containing the three-dimensional structure is placed in the first solution to form a second solution, and the second solution is coated on the support to form an optical layer. The first solvent may be, for example, chloroform, and the second solvent may be, for example, ethyl acetate. Such a separator may be finely phase-separated into a region containing the three-dimensional structure and a region containing the polymer within the three-dimensional structure. In this case, the first solvent and the second solvent may be mixed in a volume ratio of 1: 1 to 7: 1, specifically 1: 1 to 4: 1, for example, 1.5: 1 to 2.5: The first solution may have a concentration of 1 mM to 20 mM, and the second solution may have a concentration of 5 mM to 50 mM, for example, 5 mM to 40 mM. The coating may also be spin coating, dip coating, bar coating, slot die coating, spray coating, roll to roll coating, or inverse roll coating. The polymer may be selected from the group consisting of polyvinyl chloride (PVC), polyamide (PA), polyethylene (PE), polyethersulfone (PTFE), polydimethylsiloxane (PDMS), polymethyl methacrylate (PMMA) density polyethylene, LDPE, PP, polystyrene, PVAC, polyethylene oxide, NYLON, polyethylene terephthalate (PI), polyimide It can be a combination of two or more.

The optical layer manufacturing method according to the third embodiment

In the first and second embodiments, instead of using a mixed solvent of the first solvent and the first solvent, a single solvent capable of dissolving or dispersing the powder containing the three-dimensional structure may be used.

The optical layer manufacturing method according to the fourth embodiment

The solutions or dispersions of the first, second, and third embodiments may further contain an antioxidant. The antioxidant may be contained in the solution in an amount of 0.5 to 3% by weight, for example, 1 to 2% by weight. The antioxidant may be a primary antioxidant and a secondary antioxidant. At this time, the primary antioxidant may be a radical scavenger, and the secondary antioxidant may be a hydroperoxide decomposer. The primary antioxidant and the secondary antioxidant may be contained in a weight ratio of 1: 1 to 1: 3.

The primary antioxidant may be selected from the group consisting of phenolics, monophenolics, bisphenolics, polymeric phenol antioxidants, amine-based antioxidants, Or a combination thereof. The secondary antioxidant may also be phosphoric-based antioxidants, phosphates-based antioxidants, or a combination thereof.

The phenolic antioxidants may be phenolic, monophenolic, biphenolic, polyphenolic and thiobisphenolic or hindered phenolics. The polymer polyphenol system was synthesized from tetrakis (methylene-3,5-di-t-butyl-4-hydroxyphenyl) hydrocinnamate) methane Octadecy-3- (3,5-di-tert-butyl-4-hydroxyphenyl) - propionate propionate. The amine-based antioxidant plays a role of hydrogen donation similar to the phenol-based antioxidant, and also acts as a peroxide decomposer at a high temperature. Such amine-based antioxidants include N-substituents of amines of p-phenylene such as alkyl-substituted phenylamines, diaryl-p-phenylene amines or their substituents, Substituted phenol such as 6-ethoxy-2,2'-4-trimethyl-1,2-dihydroxynorine, 2,2 ', 6,6'-tetralkylpiperazine, and the like.

The sulfur-based antioxidant is useful as a release agent for peroxidation which is effective for long-term exposure to heat, such as dirauryl 3,3'-thio-dipropionate or dimyristyl 3,3'- Dimyristyl 3, 3 ' -dipropionate (DMTP). The phosphorus antioxidant may be converted into phosphates after converting hydrogen peroxide to alcohol. Examples of such phosphorus antioxidants include trialkylphosphite (alkyl: isodecyl-, tridecyl-), phenylalkyl-di-phosphite (alkyl: isodecyl, isooctyl isooctyl), diphenylalkylphosphite (alkyl: isodecyl, isooctyl), triphenylphosphite, phosphaparaside (1,1-biphenyl-4,4'- Bis (1,1'-dimethylethyl) phenyl) ester, bis-tetra (bis (1,1'-dimethylethyl) 3,5-di-t-butyl-hydroxybenzylphosphate diethylester, 9,10-dihydro-9-xy-10-phospho 10-phosphonaltrene-10-oxide, sodium (4-t-butylphenyl) phosphite, Sodium-2,2-methylene-bis (4,6-di-t-butylphenyl) phosphate is (4,6-di-t-butylphenyl) phosphate, 1,3-bis (diphenoxyphosphonyloxy) benzene, bis Bis (2,6-di-t-butyl-4-methylphenyl) pentaerythritol phodphite), tris (2,4-di-t-butylphenyl) phosphite 2,4-di-t-butylphenyl) phosphite), or 2,2-methylene bis- (4,6- di-t-butylphenyl) octylphosphite).

In addition, the solution may be selected from the group consisting of butylhydroxyanilide, dibutylhydroxytoluene, vitamin c, tocopherol, lecithin, propyl gallate, tertiary butyl hydroquinone, erythorbinic acid, ascorbyl palmitate, L-ascorbyl And at least one biostable antioxidant selected from the group of biostability-proven biosynthetic antioxidants consisting of bosdecylate and bosderate.

The optical layer manufacturing method according to the fifth embodiment

In another example, 20 to 75% by weight of the powder containing the three-dimensional structure, 5 to 75% of the miscible polymer with the three-dimensional structure, and the remaining amount of the antioxidant are mixed to form a mixture, To form an optical layer. The coating may also be spin coating, dip coating, bar coating, slot die coating, spray coating, roll to roll coating, or inverse roll coating. The polymer may be as described in the optical amplification layer manufacturing method according to the second embodiment, and the antioxidant may be as described in the optical layer manufacturing method according to the fourth embodiment.

The optical layer may have a thickness of 50 to 500 nm, and more specifically, may have a thickness of 100 to 200 nm.

Such an optical layer is a periodic and regular three-dimensional organic structure layer. The optical layer is mixed with a material having a near-zero dielectric constant and a topological insulator, thereby exhibiting excellent properties as an optical amplifying material.

의 각 구성요소들의 설정에 의해 조절될 수 있다. 일 예로서, 주기적이고 규칙적인 3차원 구조체를 형성하는 화합물이 4,5,9,10-테트라키스(도데실옥시)-파이렌(화합물 11)인 경우, 격자 간격은 약 3.4 nm일 수 있고 이에 따라 약 300nm 이하의 범위에서 유전율이 1보다 작은 구체적으로는 0에 가까운 메타물질로서의 특성을 나타낼 수 있다.Specifically, the characteristic of the optical layer as a meta material is attributed to a periodic and regular three-dimensional structure. Within the wavelength range defined by the lattice spacing of the three-dimensional structure, the optical layer exhibits a dielectric constant of less than 1, in particular close to zero, and the resulting elliptic dispersion ), The optical amplification characteristic can be exhibited. The lattice spacing is such that -A- (L) nYX shown in FIG. 1, that is, the compounds represented by Formula 1 are -A1- (L1) n1-Y1-X1 or -A2- (L2) Can be controlled by the length. More specifically, Y1 and Y2. Specifically,

As shown in FIG. As an example, if the compound forming the periodic and ordered three-dimensional structure is 4,5,9,10-tetrakis (dodecyloxy) -pyran (compound 11), the lattice spacing can be about 3.4 nm As a result, the material can exhibit a dielectric constant of less than 1 in the range of about 300 nm or less, specifically, a material close to zero.

In addition to optical amplification characteristics, the optical layer exhibiting properties as a meta-material can not exceed the resolution limit of a general medium due to the absence of a disarray in the optical layer as in a general medium. Further, as there is no loss of electromagnetic wave in the optical layer, the electromagnetic wave can be guided or amplified with respect to the region where the dielectric constant is lower than 1. Using these properties, a novel magnetic resonance image, a novel optical circuit for a new near-infrared, visible, or ultraviolet region, a super-lens beyond the diffraction limit, an adjustable metamaterial capable of switching and modulating electromagnetic waves metamaterials). As well as more practical areas such as invisible cloacks, illusion optics, optical black holes, bean shifters, field rotators, light concentrators, ), Lossless waveguide bends, and the like.

On the other hand, topological insulators can be realized by 1) lattice symmetry and 2) spin-orbital coupling. The periodic and regular three-dimensional structure according to the present embodiment can exhibit lattice symmetry. In addition, spin-orbit coupling may occur due to periodic and regularly arranged aromatic rings in the structure. Accordingly, the optical layer having a periodic and regular three-dimensional structure can have a feature as a topological insulator. Therefore, the optical layer according to the present embodiment can have a dirac band structure, and dirac plasmons generated by the periodic and regular arrangement of aromatic ring groups cause local surface plasmon resonance. Therefore, Effect can be obtained. The optical layer exhibiting characteristics of such a topological insulator is extended to a topological insulator having a magnetic property and a topological insulator having an electrical property, and is used as a quantum computer, a terahertz band detector, a device of a spintronic device, (tunable amplifier).

In addition, the optical layer may exhibit various linear or nonlinear optical properties, which are caused by the anisotropic properties of the electrical multipoles of the quadrupole of aromatic rings in a regular, periodic three-dimensional organic structure. By using this, the optical layer can be classified into an optical parametric amplifying material, an optical parametric generating material, an optical parametric vibrating material, and an electromagnetic coupling due to n-harmonic generation by n-order polarization, It can be used in a wide range of materials, such as electromagnetic wave magnetic focusing material. When these anisotropic properties are synergistic with metamaterial properties, they function as linear or non-linear metamaterials. In this case, the giant local field amplifiers, hysteretic transient materials transition waves, unusual wave mixers, solitary wave propagations, backward phase matching materials using second harmonics, and optical parametric amplifiers. It is possible.

As described above, the optical layer secures both the properties originating from the meta-material and the properties originating from the topological insulator. The properties as a meta-material are super lenses exceeding the diffraction limit [Nature materials, 7.6, 435-441 (2008) (Nature photonics, 1.4, 224-227 (2007)), Antennas and Wireless Propagation Letter, IEEE, 8, 295-298 (2008)] . In addition to recent structural changes in meta-materials, as well as the view of basic unit materials of meta-materials, various bandgap materials (physical review B 70.23 235109 (2004)), nano-lasers (Physical Review B 75.8 085436 2007), electromagnetic wave shielding materials capable of blocking electromagnetic waves for a specific band gap [Microwave Theory and Techniques, IEEE Transactions 58.1, 195-202 (2010)] have been proposed, and furthermore, an absorber for the terahertz band [Applied Physics Letter, 100.11, 111104 (2012)], gradient refractive lens material (GRIN) [US Patent No. (Science 325, 5947, 1518-1521 (2009)) which can be used as a memory and can be used as a memory.

An optical element including an optical amplification layer

An example in which the optical layer having the above-described three-dimensional organic structure is applied to the optical amplification layer in the optical element will be described below.

2 is a cross-sectional view illustrating a light emitting diode having an optical amplification layer according to an embodiment of the present invention.

Referring to FIG. 2, a base substrate 101 having an element region and a peripheral region surrounding the element region is provided. The base substrate 101 may be a silicon substrate, a metal substrate, or a ceramic substrate. The device region is a region in which a light emitting diode semiconductor chip to be described later is mounted, and the peripheral region may be another region. The base substrate 101 may have bonding pads 102 and 103 on its element region. The housing 105 having the cavity 105a can be disposed on the peripheral region of the base substrate 101. [ Portions of the bonding pads 102 and 103 may be exposed in the cavity 105a. The housing 105 may be formed of silicon, metal, ceramics or resin. The base substrate 101 and the housing 105 may be integrally formed without being separated from each other.

The light emitting diode chip (C) is disposed on one of the bonding pads (102) exposed in the cavity (105a). The light emitting diode chip (C) includes an n-type semiconductor layer, a p-type semiconductor layer, and a photoactive layer interposed therebetween. The photoactive layer may be a depletion region between the n-type semiconductor layer and the p-type semiconductor layer or may be a separately introduced layer. When the electric field is applied between the n-type semiconductor layer and the p-type semiconductor layer, the light emitting diode chip (C) emits light while recombining electrons and holes in the photoactive layer. The light emitting diode chip (C) may be any one of GaAlAs type, AlGaIn type, AlGaInP type, AlGaInPAs type, and GaN type. Further, the light emitting diode chip (C) may be a device that emits visible light, ultraviolet light, or infrared light. The n-electrode and the p-electrode of the light emitting diode chip C may be electrically connected to the bonding pads 102 and 103 through the wires W, respectively.

An organic encapsulation layer 110 filling the cavity 105a may be disposed in the cavity 105a. The organic sealing layer 110 may contain a light-transmitting resin and a light-converting resin. The light converter converts the light generated from the light emitting diode chip (C) into light having a lower wavelength, and may be a phosphor or a quantum dot. At this time, a white element can be realized.

The glass encapsulation layer 120 may be formed on the organic encapsulation layer 110. The glass sealing layer 120 may have a lens portion 120a corresponding to the position of the light emitting diode chip C. The anti-reflection film 130 may be disposed on the organic sealing layer 120.

An optical amplification layer (LAL) may be disposed on the path of light generated from the photoactive layer of the light emitting diode, that is, between the photoactive layer and the exterior. Specifically, an optical amplification layer (LAL) may be disposed on the anti-reflection layer 130. However, the present invention is not limited to this, and the optical amplification layer LAL may be formed between the glass encapsulation layer 120 and the anti-reflective layer 130, between the glass encapsulation layer 120 and the organic encapsulation layer 110, And may be disposed between the sealing layer 110 and the light emitting diode chip (C).

The light emitting diode shown in FIG. 2 may be a light emitting diode module. However, the present invention is not limited thereto, and the light emitting diode chip (C) or the light emitting diode array having a plurality of the light emitting diode modules may be implemented.

3 is a cross-sectional view illustrating an organic light emitting diode or a quantum dot light emitting diode panel having an optical amplification layer according to an embodiment of the present invention. The organic light emitting diode or the quantum dot light emitting diode panel may be a display panel or an illumination panel. In the case of the display panel, the unit pixels shown in FIG. 3 may be arranged in a matrix form. In the case of the illumination panel, the unit module may be the unit module shown in FIG. 3, or may be an array in which a plurality of unit modules are arranged.

3, the organic light emitting diode or quantum dot light emitting diode panel 200 includes a pixel electrode 230 disposed on an element substrate 210, a light emitting functional layer 250 disposed on the pixel electrode 230, A common electrode 270 disposed on the light emitting functional layer 250 and an encapsulation substrate 290 disposed on the common electrode 270. An encapsulant 280 may be disposed between the common electrode 270 and the encapsulation substrate 290 to block or absorb moisture and oxygen.

In the case of a display panel, a thin film transistor 220 electrically connected to the pixel electrode 230 and supplying or blocking an electric signal to the pixel electrode 230 may be disposed on the device substrate 210. Specifically, the buffer layer 215 may be disposed on the device substrate 210. A semiconductor layer 221 having source and drain regions and a channel region disposed therebetween may be disposed on the buffer layer 215 and a gate insulating layer 223 may be disposed on the semiconductor layer 221 And a gate electrode 225 may be disposed on the gate insulating layer 223 and the semiconductor layer 221 may cross the upper portion. A first interlayer insulating film 226 may be disposed on the gate electrode 225 to cover the gate electrode 225. The first interlayer insulating film 226 and the gate electrode 225 may be formed on the first interlayer insulating film 226, And source / drain electrodes 227 which penetrate the insulating film 223 and connect to the source / drain regions, respectively. A second interlayer insulating film 229 covering the source / drain electrodes 227 may be disposed on the source / drain electrodes 227. The pixel electrode 230 may be formed on the second interlayer insulating film 229, May be disposed. The pixel electrode 230 may be a transparent conductive film such as indium tin oxide (ITO) or indium zinc oxide (IZO).

A pixel defining layer 235 having an opening for exposing the pixel electrode 230 may be disposed on the pixel electrode 230. The opening may define the light emitting region ER. The light emitting functional layer 250 may be disposed on the pixel electrode 230 exposed in the opening. The light emitting function layer 250 may include a photoactive layer that is a light emitting layer. The light emitting layer may be an organic light emitting layer or a quantum dot light emitting layer. The light emitting functional layer 250 may further include at least one of a hole injection layer, a hole transport layer, an electron transport layer, and an electron injection layer. The common electrode 270 may be formed of a metal such as aluminum, magnesium, calcium, sodium, potassium, indium, yttrium, lithium, silver, lead or cesium as a light transmitting or transparent electrode or a combination of two or more thereof . ≪ / RTI >

Holes injected from the pixel electrode 230 and electrons injected from the common electrode 270 are injected into the light emitting functional layer 250 when an electric field is applied between the pixel electrode 230 and the common electrode 270. [ In the light emitting layer of the light emitting layer. At least one of the element substrate 210 and the sealing substrate 290 may be a light transmitting substrate, a glass substrate, or a resin substrate. For example, the element substrate 210 may be a light transmitting substrate, and the sealing substrate 290 may be a light reflecting substrate. In this case, the light emitted from the light emitting layer may be emitted to the outside through the device substrate 210. This case is referred to as a back-light-emitting type panel. As another example, the element substrate 210 may be a light reflecting substrate and the sealing substrate 290 may be a light transmitting substrate. In this case, the light emitted from the light emitting layer may be emitted to the outside through the sealing substrate 290. This case is referred to as a top emission type panel. As another example, both the element substrate 210 and the encapsulation substrate 290 may be a light transmission substrate. In this case, the light emitted from the light emitting layer may be emitted to the outside through both the element substrate 210 and the sealing substrate 290. This case is referred to as a double-sided emission type panel. When both the element substrate 210 and the sealing substrate 290 are resin substrates, a flexible element may be present.

An optical amplification layer (LAL) may be disposed in a path along which light generated from the light emitting layer of the organic light emitting diode panel travels. Specifically, in the case of a bottom emission type panel, an optical amplification layer (LAL) may be disposed on the lower surface of the element substrate 210. However, the present invention is not limited to this, and it is also possible to use the thin film transistor 220 and the first interlayer insulating film 226 between the element substrate 210 and the buffer layer 215, between the buffer layer 215 and the thin film transistor 220, Or between the first interlayer insulating layer 226 and the pixel electrode 230 may be disposed between the first interlayer insulating layer 226 and the pixel electrode 230. On the other hand, in the case of a front emission type panel, an optical amplification layer (LAL) may be disposed on the sealing substrate 290. However, the present invention is not limited to this, and the optical amplification layer LAL may be disposed between the sealing substrate 290 and the sealing material 280, or between the sealing material 280 and the common electrode 270. On the other hand, in the case of a double-sided emission type panel, the position of the optical amplification layer (LAL) in the case of the front emission type panel can be combined with the case of the back emission type panel.

On the other hand, the light layered layer according to an embodiment of the present invention can be used in various illumination devices. Specifically, the optical amplification layer can be disposed in a path along which light travels in each illumination device. The illumination device may be a light emitting diode module, a light emitting diode array, an organic light emitting diode lighting module, a quantum dot light emitting diode lighting module, an organic light emitting diode array, a quantum dot light emitting diode array, a fluorescent lamp, an incandescent lamp and the like.

4 is a cross-sectional view illustrating a liquid crystal display having an optical amplification layer according to an embodiment of the present invention.

4, the liquid crystal display includes a lower substrate 310, an upper substrate 320, and a liquid crystal layer 330 positioned between the upper and lower substrates 310 and 320.

The lower substrate 100 includes a lower base substrate 311. The lower base substrate 311 may be a light-transmitting substrate and a glass substrate. A thin film transistor (not shown) may be formed on the upper surface of the lower base substrate 311. An interlayer insulating film 313 covering the thin film transistor can be formed on the thin film transistor. The interlayer insulating film 313 may be an inorganic insulating film such as a silicon nitride film or a silicon oxide film, an organic insulating film such as a resin, or a multilayer thereof. A pixel electrode 315 can be formed on the interlayer insulating film 313. [ The pixel electrode 315 may be electrically connected to the thin film transistor through the interlayer insulating layer 313. The pixel electrode 315 may be a transparent conductive film such as indium tin oxide (ITO) or indium zinc oxide (IZO). The lower alignment layer 317 may be formed on the pixel electrode 315.

The upper substrate 320 includes an upper base substrate 321. The upper base substrate 321 may be a light-transmitting substrate and a glass substrate. Shielding patterns (not shown) and color filters (not shown) may be formed on the lower surface of the upper base substrate 321. A protective film 323 may be formed on the color filters. The protective film 323 may be an inorganic insulating film such as a silicon nitride film or a silicon oxide film, an organic insulating film such as a resin, or a multilayer thereof. The counter electrode 325 may be formed on the protective film 323. The counter electrode 325 may also be a transparent conductive film such as indium tin oxide (ITO) or indium zinc oxide (IZO). An upper alignment layer 327 may be formed on the counter electrode 325. The upper alignment layer 327 and the lower alignment layer 317 may be formed of poly-amic acid, polyimide, lecithin, nylon, or PVA polyvinylalcohol). The liquid crystal in the liquid crystal layer 330 is initially oriented by the alignment layers and can perform light interception or light transmission operation by an electric field applied between the first and second electrodes 315 and 325.

A lower polarizing film 341 may be disposed adjacent to a lower surface of the lower base substrate 311 and an upper polarizing film 342 may be disposed adjacent to an upper surface of the upper base substrate 321. The lower polarizing film 341 and the upper polarizing film 342 may be arranged such that the transmission axes thereof are orthogonal to each other.

A backlight unit 350 may be disposed below the lower polarizing film 341. The backlight unit 350 may include a reflective sheet 351, a light guide plate 352, a diffusion sheet 355, a prism sheet 356, and a protective sheet 357 sequentially stacked. Further, the light emitting device 353 and the light emitting device mounting portion 354 for mounting the light emitting device 353 may be disposed at the edge portions of the light guide plate 352. The light emitting device 353 may be a cold cathode fluorescent lamp or the light emitting diode described with reference to FIG. The illustrated backlight unit 350 may be an edge type in which the light emitting element is located at an edge, but it may be a direct type, not limited thereto. In this case, the light emitting device 353 is positioned between the reflective sheet 351 and the diffusion sheet 355, and the light guide plate 352 may be omitted.

An optical amplification layer (LAL) may be disposed in a path along which light generated from the light emitting device 353 of the liquid crystal display panel proceeds. Specifically, an optical amplification layer (LAL) may be disposed on the upper polarizing film 342. However, the present invention is not limited thereto. The optical amplification layer LAL may be disposed between the upper polarizer film 342 and the upper base substrate 321, between the upper base substrate 321 and the color filters (not shown) The lower alignment layer 317 is formed between the color filters (not shown) and the protective layer 323, between the protective layer 323 and the counter electrode 325, between the counter electrode 325 and the upper alignment layer 327, Between the pixel electrode 315 and the interlayer insulating layer 313 and between the interlayer insulating layer 313 and the thin film transistor (not shown), between the pixel electrode 315 and the interlayer insulating layer 313, The lower polarizing film 341 and the backlight unit 350 or between the lower base plate 311 and the lower polarizer film 341, between the lower polarizer film 341 and the backlight unit 350, . Specifically, the backlight unit 350 is disposed between the protective sheet 357 and the prism sheet 356, between the prism sheet 356 and the diffusion sheet 355, or between the diffusion sheet 355 and the light- And may be disposed between the light guide plates 352. Or between the light guide plate 352 and the light emitting device 353.

5 is a cross-sectional view of a solar cell having an optical amplification layer according to an embodiment of the present invention.

Referring to FIG. 5, a second conductivity type semiconductor layer 413 is disposed on the first conductivity type semiconductor layer 411. The first and second conductivity type semiconductor layers 411 and 413 may be inorganic semiconductor layers that are silicon semiconductor layers, germanium semiconductor layers, silicon germanium semiconductor layers, or compound semiconductor layers. In this case, a PN junction where excitons are generated by light absorption may be formed between the first and second conductivity type semiconductor layers 411 and 413. The compound semiconductor layer is a III-V semiconductor layer, and may be a GaAs-based, an AlAs-based, a GaP-based, or an InP-layer, specifically, AlXGa1-XAs (0? X? 1), GaXIn1- .

Meanwhile, the first conductivity type semiconductor layer 411 may be an I-III-VI ₂ compound semiconductor layer or a II-VI compound semiconductor layer as an example of a chalcogenide-based material layer. The compound semiconductor layer of I-III-VI ₂ is formed of CuInS ₂ (CIS), CuGaS ₂ (CGS), CuInSe ₂ (CISe), CuGaSe ₂ (CGSe), CuAlSe ₂ (CASe), CuInTe ₂ (CITe), CuGaTe ₂ , Cu (In, Ga) S ₂ (CIGS), Cu (In, Ga) Se ₂ (CIGSe), Cu ₂ ZnSnS ₄ (CZTS) or Cu (In, Ga) Se ₂ The II-VI compound semiconductor layer may be a CdTe layer. In this case, the second conductive semiconductor layer 413 may be a CdS, Zn (O, S, OH) x, In (OH) xSy, ZnInxSey, or ZnSe layer and may be referred to as a buffer layer.

These semiconductor layers 411 and 413 may be crystalline semiconductor layers, polycrystalline semiconductor layers or amorphous semiconductor layers. Further, these semiconductor layers 411 and 413 may be polycrystalline semiconductor layers or amorphous semiconductor layers which can realize a thin film solar cell.

Alternatively, the first and second conductive semiconductor layers 411 and 413 may be organic semiconductor layers. In this case, a photoactive layer (not shown) in which excitons are generated by light irradiation may be further formed between the first and second conductivity type semiconductor layers 411 and 413. The photoactive layer may be a bulk heterojunction (BHJ) layer in which an electron donor material and an electron acceptor material are mixed with each other. Or the photoactive layer has the formula RMX ₃ wherein R is C _n H _{2n + 1} NH ₃ ⁺ (n is an integer of 1 to 0), NH ₄ ⁺ , HC (NH ₂ ) ₂ ⁺ , CS ⁺ , NF ₄ ⁺ , NCl ₄ ⁺ , PF ₄ ⁺ , PCl ₄ ⁺ , CH ₃ PH ₃ ⁺ , CH ₃ ASH ₃ ⁺ . PH ₄ ⁺ , ASH ₄ ⁺ , SbH ₄ ^+, and combinations thereof, wherein M is selected from the group consisting of Pb ₂ ⁺ , Sn ₂ ⁺ , Ge ₂ ^+, and combinations thereof , And X may be a halogen anion. At this time, the first conductive semiconductor layer 411 may be referred to as a dense TiO ₂ layer as an anti-recombination layer.

A reflective layer may be formed under the first conductive semiconductor layer 411. The reflective layer may serve as the first electrode 401. The second electrode 420 may be formed on the second-type semiconductor layer 413. The second electrode 420 may be a light-transmitting electrode. The light-transmitting electrode may be a carbon nanotube layer, a graphene layer, a transparent conductive oxide layer, or a metal layer, and may be formed using coating, thermal evaporation, electron beam evaporation, or sputtering.

An anti-reflection layer 430 may be additionally disposed on the second electrode 420. The antireflection film 430 may be a silicon nitride film (SiN x layer). When the second electrode 420 or the anti-reflection film 430 is formed, a glass substrate 440 may be formed on the anti-reflection film 430. The glass substrate 440 may be a silica (SiO2) layer or a silicate layer having a refractive index of 1.4 to about 1.6, for example, borosilicate glass, soda-lime glass, Aluminum silicate glass, or spin on glass (SOG). However, the present invention is not limited thereto.

A protective film 450 may be disposed on the glass substrate 440. The protective film 450 may be PDMS (Polydimethylsiloxane), PMMA (polymethyl methacrylate), or EVA (Ethylene Vinyl Acetate) having a refractive index of about 1.4 to about 1.5.

When the solar cell is irradiated with light, for example, solar light, the PN junction or the photoactive layer between the first and second conductive type semiconductor layers 411 and 413 absorbs photons, - hole pairs are generated, and the electron-hole pairs are separated so that electrons are transferred to the second electrode 420 and holes are transferred to the first electrode 401 to produce electricity.

An optical amplification layer (LAL) may be disposed in a path where the light of the solar cell, for example, sunlight, propagates into the solar cell. Specifically, an optical amplification layer (LAL) may be disposed on the protective film 450. However, the present invention is not limited to this, and the optical amplification layer LAL may be formed between the protective film 450 and the glass substrate 440, between the glass substrate 440 and the antireflection film 430, ) And the second electrode (420).

6 is a cross-sectional view of a dye-sensitized solar cell having an optical amplification layer according to an embodiment of the present invention.

Referring to FIG. 6, a lower substrate 510 is provided. The lower substrate 510 is a light-transmitting substrate, and the material thereof may be glass or a light-transmitting polymer. A first electrode 520 may be formed on the lower substrate 510. The first electrode 520 may be a light-permeable electrode. The first electrode 520 may be a conductive polymer film such as polyaniline and may be formed of ITO (indium tin oxide), FTO (F-doped SnO 2), or ITO with antimony tin oxide Conductive oxide thin film. A semiconductor layer may be formed on the first electrode 520.

The semiconductor layer may have stacked metal oxide particles 530. Although the metal oxide particles 530 are illustrated as being spherical, the metal oxide particles 530 may be tubular, wire or rod-shaped, and may be nanomaterials having a length in at least one direction of less than 1000 nm . The metal oxide may be selected from the group consisting of titanium oxide (e.g., TiO2), tin oxide (e.g., SnO2), tungsten oxide (e.g. WO3), zinc oxide (e.g. ZnO), zirconium oxide , ZrO2), strontium oxide (e.g., SrO), or niobium oxide (e.g., Nb2O5). The dye 535 particles can be adsorbed on the surface of the metal oxide particles 530. The dye 535 can be an organic dye or a quantum dot inorganic dye, for example, as a material capable of absorbing sunlight to generate electron-hole pairs. The organic dye may be a ruthenium-based organometallic compound or an organic compound, and the quantum dot inorganic dye may be InP or CdSe. The dual ruthenium-based organometallic compound may be a pyridine-based ligand, or a dye in which pyridine-based ligands / SCN ligands are coordinated around the central metal ruthenium.

After the dye 535 is adsorbed on the surface of the metal oxide particles 530, an encapsulating material 570 may be formed on the edge of the substrate 510 at a height greater than a height of the semiconductor layer. An upper substrate 560 having a second electrode 550 formed on one surface thereof may be prepared and an upper substrate 560 may be disposed such that the second electrode 550 faces the metal oxide particles 530. have. The edge portions of the upper substrate 560 are closely contacted with the sealing material 570 and the second electrodes 550 and the semiconductor layers are spaced apart from each other by a predetermined distance. At this time, the upper substrate 560 may be a light-transmitting substrate like the lower substrate 510, and the material thereof may be glass or a light-transmitting polymer.

The upper substrate 560 and the lower substrate 510 are formed by injecting an electrolyte 540 through an electrolyte injection port (not shown in the figure) formed in advance on one side of the sealing material 570, And then the electrolyte injection hole is sealed to manufacture the dye-sensitized solar cell 500 according to an embodiment of the present invention.

At this time, the electrolyte 540 may be introduced into the porous semiconductor layer, and may be a liquid electrolyte to facilitate diffusion in the porous semiconductor layer. The liquid electrolyte may contain a liquid such as acetonitrile as a medium and may contain I ^- / I ₃ ^- as a redox species. The source of I ^- may be LiI, NaI, or imidazolium iodide, and I ₃ ^- may be generated by dissolving I ₂ in the medium.

A specific wavelength band of the entire wavelength band of the solar light Li incident through the lower substrate 510 is absorbed by the dye 535 and the dye 535 absorbing the light energy is absorbed by the MLCT (Metal to Ligand Charge Transfer) to generate electron-hole pairs. The generated electrons are transmitted to the first electrode 520 through the metal oxide particles 530. I ^- in the electrolyte transfers electrons to the oxidized dye 535 while being oxidized to I ₃ ^- , and the dye 535 is reduced again. I ₃ ^- may receive electrons from the second electrode 550 and be reduced back to I ^- .

An optical amplification layer (LAL) may be disposed in the path of the light of the dye-sensitized solar cell, for example, the sunlight traveling into the dye-sensitized solar cell. Specifically, an optical amplification layer (LAL) may be disposed on the upper substrate 560. However, the present invention is not limited to this, and the optical amplification layer LAL may be disposed between the upper substrate 560 and the second electrode 550.

As described with reference to Figs. 2 to 6, the optical amplification layer (LAL) can be disposed on the optical path of the optical element. Specifically, in the case of the light emitting device described with reference to FIGS. 2 and 3, an optical amplification layer (LAL) may be disposed on an optical path where light generated from the light emitting layer is extracted to the outside, that is, between the light emitting layer and the outside . In addition, in the case of the liquid crystal display device described with reference to FIG. 4, the optical amplification layer (LAL) may be disposed on the optical path from which light emitted from the light emitting device is extracted to the outside. 5 and 6, an optical amplification layer (LAL) may be disposed between the outside and the light absorption layer, in other words, an optical path in which external light is introduced into the light absorption layer .

Such an optical amplification layer (LAL) is a periodic and regular three-dimensional organic structure as described above. Particularly, by forming a regular periodic three-dimensional structure having nanometer periodicity, a meta material having a dielectric constant close to zero in a specific wavelength region can be realized. Thus, an optical amplification shape can be shown. The particular wavelength region may be in the near infrared, visible or ultraviolet region, which can be controlled by adjusting the lattice spacing of the three-dimensional structure. In addition, the optical amplification layer (LAL) may exhibit characteristics as a topological insulator. In particular, the optical amplification layer (LAL) having the periodic and regular structure may be a topological Light can be amplified by surface plasmon resonance.

The periodic and regular three-dimensional organic structure described above can mix the characteristics of a meta material having a dielectric constant close to zero and the characteristics of a topological insulator, and particularly, it can exhibit excellent characteristics as an optical amplifying material. An optical element having high efficiency can be realized.

Hereinafter, the present invention will be described in detail with reference to experimental examples. However, the following experimental examples illustrate the present invention, and the present invention is not limited thereto.

Compound Preparation Examples 1A to 3A: Preparation of tetrakis (alkyloxy) -pyrene

[Reaction Scheme 5]

Compound Preparation Example 1A: Preparation of 4,5,9,10-tetrakis (dodecyloxy) -pyrene

1A-1. Preparation of pyrene-4,5,9,10-tetra

(10 mmol) was dissolved in a solution of dichloromethane (40.0 ml) and acetonitrile (40 ml), and then ruthenium (Ⅲ) chloride hydrate (0.25 g, 1.2 mmol) Was refluxed with sodium metaperiodate (NaIO ₄ ) (17.5 g, 81.8 mmol) in distilled water (50.0 mL) at 40 ° C for 16 hours to produce pyrene-4,5,9,10-tetraone.

Pyrene -4,5,9,10- ^{tetrahydro-on: 1 H NMR (600MHz, DMSO} -d6) δ8.32 (d, 4H), 7.71 (t, 2H)

1A-2. Preparation of 4,5,9,10-tetrakis (dodecyloxy) -pyrene

(10 mmol) of bromo tetrabutylammonium (Bu ₄ NBr) (13 mmol) and sodium hydrosulfite (Na ₂ S ₂ O ₄ ) obtained in 1A- (115 mmol) were dissolved in distilled water (50 ml) and tetrahydrofuran (THF) and refluxed at 65 ° C for 5 minutes. An aqueous solution prepared by dissolving bromododecyl (60 mmol) and KOH (306 mmol) in distilled water (50 ml) was added to the reaction solution and refluxed at 65 ° C for 16 hours to obtain 4,5,9,10-tetra Keto (dodecyloxy) -pyrene (R = C ₁₂ H ₂₅ in Scheme 5, compound 11) (yield: 72%).

4,5,9,10- tetrakis (dodecyloxy City) ^{pyrene: 1 H NMR (600MHz, CDCl} 3) δ 8.32 (d, 4H), 7.71 (t, 2H), 4,21 (t, 8H , 1.91 (m, 8H), 1.57 (m, 8H), 1.40-1.27 (m, 64H), 0.88

7 is 4,5,9,10- tetrakis (dodecyloxy City) according to Preparation Example 1A - is a 1H-NMR spectrum measured under the CDCl ₃ solvent of the pyrene.

Compound Preparation Example 1B: Preparation of 4,5,9,10-tetrakis (tetradecyloxy) -pyrrole

The same procedure as in Preparation Example 1A was conducted except that bromotetradecyl was used instead of bromododecyl in the above 1A-2 to prepare 4,5,9,10-tetrakis (tetra decyloxy) the pyrene (Scheme 5 R = C ₁₄ H _29, compound 12) was prepared (yield: 70%).

4,5,9,10- tetrakis (tetra-decyloxy) ^{pyrene: 1 H NMR (600MHz, CDCl} 3) δ 8.32 (d, 4H), 7.71 (t, 2H), 4,21 (t, 8H), 1.91 (m, 8H), 1.57 (m, 8H), 1.40-1.27 (m, 64H), 0.88

8 is 4,5,9,10- tetrakis (tetra-decyloxy) according to Preparation Example 1B - is a 1H-NMR spectrum measured under the CDCl ₃ solvent of the pyrene.

Compound Preparation Example 1C: Preparation of 4,5,9,10-tetrakis (octadecyloxy) -pyrene

The same procedure as in PREPARATION 1A was carried out except that bromododecyl was used instead of bromododecyl in the above 1A-2 to obtain 4,5,9,10-tetrakis (octa Decyloxy) -pyrene (R = C ₁₈ H ₃₇ , compound 13 in Scheme 5) (yield: 72%).

4,5,9,10- tetrakis (octa-decyloxy) ^{pyrene: 1 H NMR (600MHz, CDCl} 3) δ 8.32 (d, 4H), 7.71 (t, 2H), 4,21 (t, 8H), 1.91 (m, 8H), 1.57 (m, 8H), 1.40-1.27 (m, 64H), 0.88

9 is 4,5,9,10- tetrakis (octa-decyloxy) according to Preparation Example 1C - is a 1H-NMR spectrum measured under the CDCl ₃ solvent of the pyrene.

Compound Preparation Example 1D: Preparation of 4,5-bis (dodecyloxy) -pyrene

[Reaction Scheme 6]

1D-1. Production of pyrene-4,5-dione

The same procedure was followed except that the reaction temperature was changed from 40 占 폚 to 30 占 폚 in Step 1A-1 of Preparation Example 1A to obtain pyrene-4,5-dione.

1D-2. Preparation of 4,5-bis (dodecyloxy) -pyrene

The same procedure was followed except that the pyrene-4,5-dione obtained in Step 1D-1 was used instead of the pyrene-4,5,9,10-tetraone in Step 1A-2 of Preparation Example 1A (Yield: 68%) of 4,5-bis (dodecyloxy) -pyrrole (R = C ₁₂ H ₂₅ in Scheme 6, compound 14).

4,5-bis (dodecyloxy City) ^{pyrene: 1 H NMR (600MHz, CDCl} 3) δ 8.12 (d, 2H), 7.83 (m, 4H), 7.71 (s, 2H), 4.21 (t, 4H , 1.91 (m, 4H), 1.57 (m, 4H), 1.40-1.27 (m, 36H), 0.88

10 is a ¹ H-NMR spectrum of 4,5-bis (dodecyloxy) -pyrane according to Production Example 1D measured in a CDCl ₃ solvent.

Compound Preparation Example 1E: Preparation of 4,5-bis (dodecyloxy) -pyrene-9,10-dione

[Reaction Scheme 7]

(Dodecyloxy) -pyrene-9, 5-bis (dodecyloxy) -pyran-9-one was obtained in the same manner as in Preparation Example 1A except that the equivalent amount of bromododecyl was changed to 20 mmol in Step 1A- 10-dione (R = C ₁₂ H ₂₅ in Scheme 7, compound 15) was prepared (yield: 63%).

4,5-bis (dodecyloxy City) ^{pyrene-9,10-dione: 1 H NMR (600MHz, DMSO} -d6) δ 8.40 (m, 4H), 8.01 (t, 2H), 4.21 (t, (M, 4H), 1.91 (m, 4H), 1.57 (m, 4H), 1.40-1.27

FIG. 11 is a ¹ H-NMR spectrum of the 4,5-bis (dodecyloxy) -pyrene-9,10-polyion according to Production Example 1E measured in a DMSO-d6 solvent.

compound
Manufacturing example compound
number Compound structure Compound name yield(%) 1A 11

4,5,9,10-tetrakis (dodecyloxy) -pyrene 72 1B 12

4,5,9,10-tetrakis (tetradecyloxy) -pyrene 70 1C 13

4,5,9,10-tetrakis (octadecyloxy) -pyrene 72 1D 14

4,5-bis (dodecyloxy) -pyrene 68 1E 15

4,5-bis (dodecyloxy) -pyrene-9,10-dione 63

Compound Preparation Example 2A: Preparation of 2,3,6,7-tetrakis (dodecyloxy) anthracene

[Reaction Scheme 8]

In the above Reaction Scheme 8, R is C ₁₂ H ₂₅ .

2A-1. Preparation of 2,3,6,7-tetrakis (methoxy) -9,10-dimethyl anthracene (1)

The cooled solution of veratrol (32 mL) and acetic acid (125 mL) was slowly added to a cooled solution of methanol (20 mL) and acetaldehyde (21 mL). The mixed solution was thoroughly stirred for 1 hour, then concentrated sulfuric acid (95%, 125 ml) was added over 2 hours and reacted with stirring for 20 hours. After the reaction was completed, the reaction mixture was poured into ice water to terminate the reaction. The reaction mixture was filtered, washed with water and subjected to column chromatography using chloroform as a developing solution to obtain 2,3,6,7-tetrakis (methoxy) -9, 10-Dimethylanthracene (1) was isolated.

2A-2. Preparation of 2,3,6,7-tetrakis (methoxy) anthracene-9,10-dione (2)

(10.0 g), sodium dichromate (50 g), and acetic acid (500 mL), which were the result of Step 2A-1, To give 2,3,6,7-tetrakis (methoxy) anthracene-9,10-dione (2).

2,3,6,7-tetrakis (methoxymethyl) ^{anthracene-9,10-dione: 1 H NMR (600MHz, CDCl} 3) δ 7.32 (s, 4H), 4.06 (t, 8H), 1.76 (m , 8H), 1.57 (m, 8H), 1.43-1.26 (m, 72H), 0.88 (t, 12H)

2A-3. Preparation of 2,3,6,7-tetrakis (dodecyloxy) anthracene-9,10-dione (4)

The resulting 2,3,6,7-tetrakis (methoxy) anthracene-9,10-dione (2) (470 mg, 1.6 mmol) and tetra-n-butyl- ammonium bromide Mg) was added to concentrated hydrochloric acid (30 mg). The resultant was refluxed for 12 hours, and the reaction was terminated by filtering in ice water to obtain a brown precipitate (3). Dimethylformamide (100 ml) and potassium carbonate (17.64 g) were added to the brown precipitate (5 g, 18.3 mmol), followed by addition of 1-bromododecane (183 mmol) Then, the temperature was gradually raised to 60 DEG C and the reaction was carried out for 12 hours. Thereafter, distilled water (80 ml) was added to dissolve the unreacted potassium carbonate to dissolve the entangled product, and the resulting product was poured into ice water to complete the reaction and then filtered to obtain 2,3,6,7-tetrakis (dodecyloxy) anthracene- , 10-dione ion (4) were prepared.

¹ H NMR (600 MHz, CDCl ₃ )? 8.11 (s, 2H), 7.14 (s, 4H), 4.16 (s, t, 8H), 1.76 (m, 8H), 1.43-1.26 (m, 72H), 0.88 (t,

2A-4. Preparation of 2,3,6,7-tetrakis (dodecyloxy) anthracene-9-one (5)

The zinc powder (16.9 g) was added to a solution of copper sulfide (0.4 g) in distilled water (250 ml) and activated with stirring for 10 minutes. The activated zinc powder solution was decanted and a solution of 10% sodium hydroxide solution (160 ml) and the resultant product of step 2A-2,3,6,7-tetrakis (dodecyloxy) anthracene-9,10-dione (4) (9.82 g, 10.4 mmol) in toluene (150 ml) was added to the activated zinc powder solution. The resultant flame was stirred at 120 ° C. for 15 hours. After completion of the reaction, the flask was washed with water to remove unreacted zinc powder, recrystallized at -5 ° C., filtered, and dried in a vacuum oven. , 6,7-tetrakis (dodecyloxy) anthracene-9-one (5).

2A-5. Preparation of 2,3,6,7-tetrakis (dodecyloxy) anthracene (6)

The resulting 2,3,6,7-tetrakis (dodecyloxy) anthracene-9-one (5) (8.38 g, 8.98 mmol) obtained in step 2A-4 was dissolved in dichloromethane (200 mL) Was added sodium borohydride (5.25 g, 135 mmol), and the mixture was stirred at room temperature while methanol (30 mL) was added. Sodium borohydride (15 g, 385 mmol) was added after 90 minutes with stirring. After 7 hours, acetic acid (10 mL) was slowly added and the reaction was further continued for 12 hours, followed by the addition of concentrated sulfuric acid (10 mL) and successively adding distilled water (50 mL). After the reaction was completed, the dichloromethane layer was extracted, washed thoroughly with water, recrystallized at -5 DEG C, filtered, and stored in a vacuum oven for one day to obtain 2,3,6,7-tetrakis (dodecyloxy) anthracene (6, compound 21) (yield: 53%).

12 is a 1H-NMR spectrum measured under the 2,3,6,7-tetrakis CDCl ₃ solvent (dodecyloxy City) anthracene according to Preparation Example 2A.

Compound Preparation Examples 2B and 2C: Preparation of 2,3-bis (dodecyloxy) anthracene and 6,7-bis (dodecyloxy) anthracene-2,3-

[Reaction Scheme 9]

In the above reaction scheme 9, R is C ₁₂ H ₂₅ .

Compound Preparation Example 2B: Preparation of 2,3-bis (dodecyloxy) anthracene

2B-1. Preparation of 1,2-bis (dodecyloxy) benzene (1)

Catechol (0.1 mol) was added to dimethylformamide (20 ml), and the temperature was raised to 100 ° C. Then, 1-bromododecyl (0.3 mol) was added and reacted for 18 hours. After completion of the reaction, the reaction mixture was slowly cooled to room temperature, and the reaction was terminated by adding water to the reaction mixture. The mixture was extracted with chloroform, evaporated, and clean 1,2-bis (dodecyloxy) benzene (1) was obtained through flash column.

1,2-bis (dodecyloxy) ^{benzene: 1 H NMR (600MHz, CDCl} 3) δ 6.88 (s, 4H), 4.06 (t, 2H), 1.76 (m, 4H), 1.43 (m, 4H), 1.43-1.26 (m, 36H), 0.88 (t, 6H)

2B-2. Preparation of 2,3-bis (dodecyloxy) -9,10-dimethyl anthracene (2)

Benzene (12.8 mL, 0.1 mol), benzene (9 mL, 0.1 mmol), and propaldehyde (7.4 mL, 0.1 mol), which is the product of step 2B-1, were dissolved in acetonitrile (Dodecyloxy) -9,10-dimethylanthracene (2 ml, 0.1 mol) was dissolved in 50 ml of concentrated sulfuric acid, and the mixture was stirred for 2 hours. ).

2,3-bis (dodecyloxy City) ^{anthracene-9,10-dimethyl-: 1 H NMR (600MHz, CDCl} 3) δ 7.98 (d, 2H), 7.35 (d, 2H), 7.14 (s, 2H), 4H), 1.43-1.26 (m, 36H), 0.88 (t, 6H), 4.16 (m,

2B-3. Preparation of 2,3-bis (dodecyloxy) anthracene-9,10-dione (3)

The resultant product of step 2B-2, 2,3-bis (dodecyloxy) -9,10-dimethyl anthracene (10.0 g), sodium dichromate (50 g) and acetic acid (500 ml) 2,3,6,7-tetrakis (dodecyloxy) anthracene-9,10-dione (3).

(3,3): ¹ H NMR (600 MHz, CDCl ₃ )? 8.05 (s, 4H), 4.73 (s, 2H) , 4.18 (d, 2H), 4.01 (t, 4H), 1.76 (m, 4H), 1.43-1.26

2B-4. Preparation of 2,3-bis (dodecyloxy) anthracene (4)

(10 g, 41.3 mmol) and active zinc powder (167 g, 2.6 mol), which is the result of Step 2B-3, were dissolved in sodium hydroxide (50 g, 1.25 mol) was dissolved in distilled water (670 ml), and the mixture was reacted at 100 ° C for 48 hours while replacing with nitrogen to obtain 2,3-bis (dodecyloxy) anthracene (4, compound 22) : 63%)

2,3-bis (dodecyloxy City) ^{anthracene: 1 H NMR (600MHz, CDCl} 3) δ 8.21 (s, 2H), 7.91 (t, 2H), 7.36 (d, 2H) 7.14 (s, 2H), 4.16 (t, 4H), 1.76 (m, 4H), 1.43-1.26 (m, 36H), 0.88

13 is a ¹ H-NMR spectrum of 2,3-bis (dodecyloxy) anthracene according to Production Example 2B measured in a CDCl ₃ solvent.

Compound Preparation Example 2C: Preparation of 2,3-bis (dodecyloxy) anthracene-6,7-dione (5)

2,3-bis (dodecyloxy) anthracene (10 mmol) obtained in Production Example 2B was dissolved in a solution of dichloromethane (40.0 mL) and acetonitrile (40 mL), and then ruthenium (III) chloride hydrate was refluxed in distilled water (50.0 ml) at 25 ° C for 16 hours with ruthenium (Ⅲ) chloride hydrate (0.25 g, 1.2 mmol) and sodium metapeliodate (NaIO ₄ ) (17.5 g, 81.8 mmol) -Bis (dodecyloxy) anthracene-6,7-dione (5, compound 23) (yield: 58%).

2,3-bis (dodecyloxy City) ^{anthracene-6,7-dione: 1 H NMR (600MHz, DMSO} -d6) δ6.46 (s, 2H), 6.28 (s, 2H), 6.24 (s, 2H ), 4.16 (t, 4H), 1.76 (m, 4H), 1.43-1.26 (m, 36H), 0.88

14 is a ¹ H-NMR spectrum of 2,3-bis (dodecyloxy) anthracene-6,7-dione according to Production Example 2B measured in a CDCl ₃ solvent.

compound
Manufacturing example compound
number Compound structure Compound name yield(%) 2A 21

2,3,6,7-tetrakis (dodecyloxy) anthracene 53 2B 22

2,3-bis (dodecyloxy) anthracene 63 2C 23

2,3-bis (dodecyloxy) anthracene-5,6-dione 58

Compound Preparation Example 3A. Preparation of 1,2,7,8-tetrakis (dodecyloxy) coronene

[Reaction Scheme 10]

3A-1. Preparation of 1- (2,2-diethoxyethyl) perylene (2)

Perylene (4.00 g, 15.9 mmol), tetrahydrofuran (THF) (250 mL) and sodium (0.80 g) were placed in a reactor substituted with argon and ultrasonicated at 30 ° C for 3 hours. And bromoacetaldehyde diethyl acetal (3.13 g, 15.9 mmol) was added together with stirring. Then, iodine (6.05 g, 23.8 mmol) was added and sodium thiosulfate (100 ml) was added to obtain 1- (2,2-diethoxyethyl) perylene (2).

1- (2,2-diethoxy-ethyl) ^{perylene: 1 H NMR (600MHz, CDCl} 3) δ 7.91 (s, 3H), 7.39 (s, 6H), 7.26 (s, 1H), 7.17 (s, 1H), 4.58 (t, IH), 3.50 (m, 4H), 3.28 (d, 2H), 1.10

3A-2. Preparation of benzo [ghi] perylene (3)

(4.2 mL, 11.6 mmol) was added dropwise to a stirred solution of the resulting 1- (2,2-diethoxyethyl) perylene (4.29 g, 11.6 mmol) with methanol (8 mL) ] Perylene (3).

Benzo [ghi] ^{perylene: 1 H NMR (600MHz, CDCl} 3) δ 7.91 (d, 2H), 7.71 (s, 2H), 7.39 (s, 8H)

3A-3. Preparation of 7- (2,2-diethoxyethyl) benzo [ghi] perylene (4)

(2,2-diethoxyethyl) benzoate was obtained in the same manner as in the step 3A-1 except that benzo [ghi] perylene (3) as the result of Step 3A-2 was used instead of perylene [ghi] perylene (4) was obtained.

7- (2,2-ethoxyethyl) benzo [ghi] ^{perylene: 1 H NMR (600MHz, CDCl} 3) δ 7.91 (d, 1H), 7.71 (s, 2H), 7.39 (s, 6H), 2H), 1.10 (t, 6H), 7.28 (s, 1H), 7.17 (s,

3A-4. Preparation of coronene (5)

Except that 7- (2,2-diethoxyethyl) benzo [ghi] perylene was used instead of 1- (2,2-diethoxyethyl) perylene as a result of Step 3A-3. Coronene (5) was obtained in the same manner as in Step 2.

Coronene: ¹ H NMR (600 MHz, CDCl ₃ )? 7.39 (s, 12H)

3A-5. Production of coronene-1,2,7,8-tetraon (6)

2,6,7,8-tetraone (6) was prepared in the same manner as in PREPARATION EXAMPLE 1A-1, except that coronene as a result of Step 3A-4 was added instead of pyrene .

Nene nose -1,2,7,8- ^{tetrahydro-on: 1 H NMR (600MHz, DMSO} -d6) δ 7.83 (d, 4H), 7.49 (d, 4H)

3A-6. Preparation of 1,2,7,8-tetrakis (dodecyloxy) coronene (7)

2-one was obtained in the same manner as in Production Example 1A-2 except that the resultant product of Step 3A-5 was replaced by coronene-1,2,7,8-tetraone in place of the pyrene-4,5,9,10- 1,2,7,8-tetrakis (dodecyloxy) coronene (7, compound 31) was prepared in the same manner (Yield: 61%).

¹ H NMR (600 MHz, CDCl ₃ )? 7.39 (s, 4H), 4.16 (t, 8H), 1.76 (m, 8H), 1.43 -1.26 (m, 72H), 0.88 (t, 12H)

15 is a ¹ H-NMR spectrum of 1,2,7,8-tetrakis (dodecyloxy) coronene according to Production Example 3A measured in a CDCl ₃ solvent.

Compound Preparation Examples 3B and 3C: Preparation of 1,2-bis (dodecyloxy) coronene and 7,8-bis (dodecyloxy) coronene-1,2-dione

[Reaction Scheme 11]

Compound Preparation Example 3B: Preparation of 1,2-bis (dodecyloxy) coronene

In the same manner as in Production Example 1A except that the reaction temperature was changed from 40 ° C to 30 ° C by adding coronene instead of pyrene in Step 1A-1 of Production Example 1A, 1,2-bis ), Coronene (3, compound 32) was obtained (yield: 63%).

¹ H NMR (600 MHz, CDCl ₃ )? 7.39 (s, 10H), 4.16 (t, 4H), 1.76 (m, 4H), 1.43-1.26 (m, 36H), 0.88 (t, 6H)

16 is a ¹ H-NMR spectrum of 1,2-bis (dodecyloxy) coronene according to Production Example 3B measured in a CDCl ₃ solvent.

Compound Preparation Example 3C: Preparation of 7,8-bis (dodecyloxy) coronene-1,2-dione

Except that 1,2-bis (dodecyloxy) coronene of Production Example 3B was used instead of 2,3-bis (dodecyloxy) anthracene, 7,8-bis Dodecyloxy) -1,2-dione (4, compound 33) (yield: 62%).

7,8-bis (dodecyloxy) coronene-1,2-dione: ¹ H NMR (600 MHz, CDCl ₃ )? 7.88 (d, 2H), 7.53 , 4.16 (t, 4H), 1.76 (m, 4H), 1.43-1.26 (m, 36H), 0.88

17 is a ¹ H-NMR spectrum of 7,8-bis (dodecyloxy) coronene-1,2-dione according to Production Example 3C in a CDCl ₃ solvent.

compound
Manufacturing example compound
number Compound structure Compound name yield(%) 3A 31

1,2,7,8-tetrakis (dodecyloxy) coronene 61 3B 32

1,2-bis (dodecyloxy) coronene 63 3C 33

7,8-bis (dodecyloxy) coronene-1,2-dione 62

Compound Preparation Example 4A: Preparation of 1,2,5,6-tetrakis (dodecyloxy) cyclopenta [fg] acenaphthylene

[Reaction Scheme 12]

4A-1. Production of Daiketo Pyrrhene (2)

Acenaphthene (17.60 g, 0.114 mol) was dissolved in carbon disulfide (1500 mL) and then oxalyl bromide (25.00 g, 0.116 mol) was added at -5 [deg.] C. Aluminum bromide (62.50 g, 0.234 mol) was added to the resultant over 10-15 minutes with vigorous stirring, and the reactor was reacted overnight at room temperature to obtain diketopyrarcine (2).

The pond Sat pie ^{Larsen: 1 H NMR (600MHz, CDCl} 3) δ 8.36 (d, 2H), 7.64 (d, 2H), 3.52 (s, 4H)

4A-2. Preparation of 5,6-dibromo-1,2-dicetaparasene (3)

N-bromosuccinimide (2.60 g, 15.0 mmol) and dibenzoyl peroxide (100 mg, 0.25 mmol) were added to a solution of the diketoparacene (1.00 g, 4.8 mmol) obtained in step 4A-1 in carbon tetrachloride ) Was added, and the mixture was refluxed for 5 hours to obtain 5,6-dibromo-1,2-diketopalacene (3).

5,6-dibromo-1,2-ike is topa in ^{Larsen: 1 H NMR (600MHz, CDCl} 3) δ 8.36 (d, 2H), 7.64 (d, 2H), 5.69 (s, 2H)

4A-3. Preparation of cyclopenta [fg] acenaphthylene-1,2,5,6-tetraone (4)

Dibromo-1,2-diketopalacene (0.832 g, 4.0 mmol) and anhydrous benzene selenium (2.88 g, 8.0 mmol) obtained in step 4A-2 were dissolved in chlorobenzene , And the mixture was refluxed at 125 ° C for 72 hours to obtain cyclopenta [fg] acenaphthylene-1,2,5,6-tetraone (4).

Cyclopenta [fg] acenaphthylene-1,2,5,6-tetraene: ¹ H NMR (600 MHz, CDCl ₃ )? 8.65 (s, 4H)

4A-4. Preparation of 1,2,5,6-tetrakis (dodecyloxy) cyclopenta [fg] acenaphthylene (5)

Except that cyclopenta [fg] acenaphthylene-1,2,5,6-tetraone, which is the result of step 4A-3, was used instead of 4,6-dihydro-pyrene-4,5,9,10- (Yield: 59%) of 1,2,5,6-tetrakis (dodecyloxy) cyclopenta [fg] acenaphthylene (5, compound 41) was obtained in the same manner as in step 1A-

¹ H NMR (600 MHz, CDCl ₃ )? 7.34 (s, 4H), 4.16 (t, 8H), 1.76 (t, m, 8H), 1.43-1.26 (m, 72H), 0.88 (t, 12H)

18 is a ¹ H-NMR spectrum of 1,2,5,6-tetrakis (dodecyloxy) cyclopenta [fg] acenaphthylene according to Production Example 4A measured in a CDCl ₃ solvent.

Compound Preparation Examples 4B and 4C: Synthesis of 1,2-bis (dodecyloxy) cyclopenta [fg] acenaphthylene and 5,6-bis (dodecyloxy) cyclopenta [fg] acenaphthylene- Ion production

[Reaction Scheme 13]

Compound Preparation Example 4B: Preparation of 1,2-bis (dodecyloxy) cyclopenta [fg] acenaphthylene

4B-1. Preparation of cyclopenta [fg] acenaphthalene-1,2, -dione (4)

5,6-Dibromo-1,2-diketopalacene (3, 10 mmol) prepared in Preparation Example 4A-2 was dissolved in acetone together with excess potassium iodide and refluxed overnight to obtain cyclopenta [fg] acenaphthalene-1,2, -dion (4).

Cyclopenta [fg] acetate naphthalene-1,2-dione ^{(4): 1 H NMR (} 600MHz, CDCl 3) δ 7.90 (d, 2H), 7.58 (d, 2H), 7.15 (s, 2H)

4B-2. Preparation of 1,2, -bis (dodecyloxy) cyclopenta [fg] acenaphthalene (5)

Except that cyclopenta [fg] acenaphthalene-1,2, -dion, which is the result of step 4B-1, was used in place of phylene-4,5-dione in Example 1D, , 2, -bis (dodecyloxy) cyclopenta [fg] acenaphthalene (5, compound 42) (yield: 62%).

1,2-bis (dodecyloxy City) cyclopenta [fg] naphthalene ^{acetate: 1 H NMR (600MHz, CDCl} 3) δ 7.90 (d, 2H), 7.58 (d, 2H), 7.15 (s, 2H), 4H), 1.76 (m, 4H), 1.43-1.26 (m, 36H), 0.88 (t, 6H)

19 is a ¹ H-NMR spectrum of 1,2, -bis (dodecyloxy) cyclopenta [fg] Ace naphthalene according to Production Example 4B measured in a CDCl ₃ solvent.

Compound Preparation Example 4C: Preparation of 5,6-bis (dodecyloxy) cyclopenta [fg] acenaphthylene-1,2-dione (6)

Except that 1,2,2-bis (dodecyloxy) cyclopenta [fg] acenaphthalene (5) obtained in Production Example 4B was used instead of 2,3-bis (dodecyloxy) anthracene in Production Example 2C (Yield: 60%) of 5,6-bis (dodecyloxy) cyclopenta [fg] acenaphthylene-1,2-dione (6, 43)

5,6-bis (dodecyloxy City) cyclopenta [fg] ^{acenaphthylene-1,2-dione: 1 H NMR (600MHz, CDCl} 3) δ 8.25 (d, 2H), 8.14 (d, 2H), 4H), 1.76 (m, 4H), 1.43-1.26 (m, 36H), 0.88 (t, 6H)

20 is a ¹ H-NMR spectrum of 5,6-bis (dodecyloxy) cyclopenta [fg] acenaphthylene-1,2-dione according to Production Example 4C in a CDCl ₃ solvent.

compound
Manufacturing example compound
number Compound structure Compound name yield(%) 4A 41

1,2,5,6-tetrakis (dodecyloxy) cyclopenta [fg] acenaphthylene 59 4B 42

1,2, -bis (dodecyloxy) cyclopenta [fg] acenaphthylene 62 4C 43

5,6-bis (dodecyloxy) cyclopenta [fg] acenaphthylene-l, 2-dione 60

Compound Preparation Example 5A: Preparation of 2,3,6,7,10,11-hexakis (dodecyloxy) triphenylene

[Reaction Scheme 14]

5A-1. Preparation of triphenylen-2,3,6,7,10,11-hexanol (2)

Catechol (20 g, 0.182 mol) and hexahydrate (III) (196.8 g, 0.728 mol) were reacted for 24 hours using ultrasonic waves. The reaction mixture was washed with dilute hydrochloric acid and water, and extracted with heated cyclopentanone to obtain a major amount of triphenylen-2,3,6,7,10,11-hexanol (2).

Tri-phenylene -2,3,6,7,10,11- ^{hexanol: 1 H NMR (600MHz, CDCl} 3) δ 7.82 (s, 6H), 5.35 (s, 6H)

5A-2. Preparation of 2,3,6,7,10,11-hexakis (dodecyloxy) triphenylene (3)

Bromododecyl (60 mmol) and potassium hydroxide (306 mmol) were dissolved in distilled water (10 mmol), and the resultant product of step 5A-1, triphenylen- 50 ml), and the mixture was refluxed at 65 ° C for 16 hours to obtain 2,3,6,7,10,11-hexakis (dodecyloxy) triphenylene (3, 51) : 74%)

¹ H NMR (600 MHz, CDCl ₃ )? 7.92 (s, 6H), 4.16 (t, 8H), 1.76 (m , 8H), 1.43-1.26 (m, 72H), 0.88 (t, 12H)

21 is a ¹ H-NMR spectrum of 2,3,6,7,10,11-hexakis (dodecyloxy) triphenylene measured in a CDCl ₃ solvent according to Production Example 5A.

compound
Manufacturing example compound
number Compound structure Compound name yield(%) 5A 51

2,3,6,7,10,11-hexakis (dodecyloxy) triphenylene 74

Compound Preparation Example 6A: Preparation of pyrene-4,5,9,10-tetrayl tetraundecanoate

In the same manner as in PREPARATION 1A except that undecanoyl bromide was used instead of bromododecyl in Step 1A-2 of Production Example 1A, pyrene-4,5,9,10-tetrayltetraundecano (Compound 61).

Compound Preparation Example 6B: Preparation of pyrene-4,5-diyldytridecanoate

5-dylidododecanoate (Compound 62 (a)) was obtained in the same manner as in Preparation Example 1D, except that dodecanoyl bromide was used instead of bromododecyl in Step 1D-2 of Preparation Example 1D. ).

Compound Preparation Example 6C: Preparation of pyrene-4,5-diyl ditridecanoate

The same method as Preparation Example 1E was used, except that dodecanoyl bromide was used instead of bromododecyl in Production Example 1E to obtain 9,10-dioxo-9,10-dihydropyran-4,5-diyl (Compound 63) was obtained.

compound
Manufacturing example compound
number Compound structure Compound name Replacement reagent yield
(%) 6A 61

Pyrene-4,5,9,10-tetrayl tetraundecanoate Undecanoyl bromide 72 6A 61-1

Pyrene-4,5,9,10-tetrayltetradodecanoate Dodecanoyl bromide 74 6A 61-2

Pyrene-4,5,9,10-tetralayetrakis (dodecane-1-sulfonate) Dodecylsulfinyl bromide 20 6A 61-3

Pyrene-4,5,9,10-tetrayltetradecyltetracarbonate Carbornurobromic acid, undecyl ester
45 6A 61-4

4,5,9,10-tetrakis ((dodecylthio) oxy) pyrene Dodecylthio bromide 78 6A 61-5

12, 12 ', 12 ", 12"' - (pyrene-4,5,9,10-tetrayltetrakis (oxy) tetrakis (dodecan- 12-bromododecan-1-ol 73 6A 61-6

12, 12 ', 12 ", 12"' - (pyrene-4,5,9,10-tetraisetetrakis (oxy)) tetradodecanoic acid 12-bromododecanoic acid
(cas number 73367-80-3) 56 6B 62

Pyrene-4,5-di one also decanoate Dodecanoyl bromide
54 6B
62-1

Pyrene-4,5-diylbis (undecane-1-sulfinate) Undecylsulfinyl bromide 33 6B 62-2

Pyrene-4,5-diylbis (dodecane-1-sulfinate) Dodecylsulfinyl bromide 22 6B 62-3

Pyrene-4,5-diallyldecylbis (carbonate) Carbornurobromic acid, undecyl ester 85 6B 62-4

4,5-bis ((undecylthio) oxy) pyrene Undecylthio bromide 59 6B 62-5

12,12'- (Pyrane-4,5-diylbis (oxy)) bis (dodecan-1-ol) 12-bromododecan-1-ol 47 6C 63

9,10-dioxo-9,10-dihydropylylene-4,5-dyldidodecanoate Dodecanoyl bromide 71 6C 63-1

9,10-dioxo-9,10-dihydropyrene-4,5-dylidoundecyl dicarbonate Carbornurobromic acid, undecyl ester 76 6C 63-2

9,10-bis ((dodecylthio) oxy) pyrene-4,5-dione Dodecylthio bromide 47

Compound Preparation Example 7A: Preparation of anthracene-2,3,6,7-tetrayltetradodecanoate

In the same manner as in PREPARATION 2A, except that dodecanoyl bromide was used instead of 1-bromododecane in Step 2A-3 of Production Example 2A, anthracene-2,3,6,7-tetrayl tetradodde (Compound 71) was obtained.

Compound Preparation Example 7B: Preparation of anthracene-2,3-diyldidodecanoate

In the same manner as in Preparation Example 2B, except that dodecanoyl bromide was used instead of 1-bromododecyl in 2B-1 of Production Example 2B, anthracene-2,3-diyl dicyclohexyl dicarbonate (compound 72).

Compound Preparation Example 7C: Preparation of 6,7-dioxo-6,7-dihydroanthracene-2,3-diyldidodecanoate

In the same manner as in Preparation Example 2B and Preparation Example 2C, except that dodecanoyl bromide was used in place of 1-bromododecyl in 2B-1 of Production Example 2B, 6,7-dioxo-6, 7-dihydroanthracene-2,3-diyldidodecanoate (Compound 73).

compound
Manufacturing example compound
number Compound structure Compound name Replacement reagent yield(%) 7A 71

Anthracene-2,3,6,7-tetrayltetradodecanoate Dodecanoyl bromide 71 7A 71-1

Anthracene-2,3,6,7-tetrayl tetraundecane peroxoate 1- (bromooxy) -1-oxo-undecane 64 7A 71-2

N, N ', N ", N'" - (anthracene-2,3,6,7-tetrayltetrakis (oxy)) tetraundecanamide N-bromododecanamide 67 7A 71-3

2,3,6,7-tetrakis ((undecylsioo) oxy) anthracene Undecylthio bromide 38 7A 71-4

Anthracene-2,3,6,7-tetrayltetrakis (dodecane-1-sulfinate) Dodecylsulfinyl bromide 59 7A 71-5

(Anthracene-2,3,6,7-tetrayltetrakis (oxy)) tetrakis (dodecan-1-ol), 12 ' 12-bromododecan-1-ol 33 7A 71-6

Anthracene-2,3,6,7-tetrayl) tetrakis (oxy)) tetradodecanoic acid 12-bromododecanoic acid
(cas number 73367-80-3) 56 7B 72

Anthracene-2,3-diyldidecanoate Dodecanoyl bromide 42 7B 72-1

Anthracene-2,3-diallyldecyl dicarbonate Carbornurobromic acid, undecyl ester 33 7B 72-2

N, N '- (anthracene-2,3-diybis (oxy)) dione decanamide N-bromododecanamide 58 7B 72-3

2,3-bis ((undecylthio) oxy) anthracene Undecylthio bromide 37 7B 72-4

Anthracene-2,3-diylbis (undecane-1-sulfinate) Undecylsulfinyl bromide 40 7B 72-5

12,12 '- (Anthracene-2,3-diylbis (oxy)) bis (dodecan-1-ol) 12-bromododecan-1-ol 32 7C 73

6,7-dioxo-6,7-dihydroanthracene-2,3-diallyldodecanoate Dodecanoyl bromide 49 7C 73-1

(6,7-dioxo-6,7-dihydroanthracene-2,3-diyl) dicarbonate Carbornurobromic acid, undecyl ester 38 7C 73-2

N, N '- ((6,7-dioxo-6,7-dihydroanthracene-2,3-dile) bis (oxy)) dione decanamine N-bromododecanamide 62 7C 73-3

7,8-bis ((undecylthio) oxy) coronene-1,2-dione Undecylthio bromide 59 7C 73-4

7,8-Dioxo-7,8-dihydrocholone-1,2-diylbis (undecane-1-sulfonate) Undecylsulfonyl bromide 83

Compound Preparation Example 8A: Preparation of coronene-1,2,7,8-tetrayltetradodecanoate

In the same manner as in Preparation Example 3A except that dodecanoyl bromide was used instead of bromododecyl in Step 3A-6 of Preparation Example 3A, a solution of coronene-1,2,7,8-tetrayltetradodecano (Compound 81).

Compound Preparation Example 8B: Preparation of coronene-1,2-diyldidodecanoate

(Compound 82) was obtained using the same method as Preparation Example 3B, except that dodecanoyl bromide was used instead of bromododecyl in Production Example 3B.

Compound Preparation Example 8C: Preparation of 7,8-dioxo-7,8-dihydrocholone-1,2-dyldidodecanoate

In the same manner as in Preparation Example 3B and Preparation Example 3C, except that dodecanoyl bromide was used in place of bromododecyl in Production Example 3B, 7,8-dioxo-7,8-dihydrochlorone -1,2-diallyldodecanoate (Compound 83).

compound
Manufacturing example compound
number Compound structure Compound name Replacement reagent yield(%) 8A 81

Coronene-1,2,7,8-tetrayltetradodecanoate Dodecanoyl bromide 28 8A 81-1

Coronene-1,2,7,8-tetrayltetrakis (undecyl) tetracarbonate Carbornurobromic acid, undecyl ester 66 8A 81-2

N, N ', N' ', N' '' - (coronene-1,2,7,8-tetrayltetrakis (oxy)) tetraundecanamide N-bromododecanamide 49 8A 81-3

1,2,7,8-tetrakis ((undecylthio) oxy) coronene Undecylthio bromide 47 8A 81-4

Coronene-1,2,7,8-tetrayltetrakis (undecane-1-sulfinate) Undecylsulfinyl bromide 56 8A 81-5

(Coronene-1,2,7,8-tetrayltetrakis (oxy)) tetrakis (dodecan-1-ol), 12 ' 12-bromododecan-1-ol 49 8A 81-6

(Coronate Nene -1,2,7,8- tetrayl tetrakis (oxy)) tetra deca FIG ohnik acid 12-bromododecanoic acid
(cas number 73367-80-3) 51 8B 82

Coronene-1,2-diyldidodecanoate Dodecanoyl bromide 61 8B 82-1

N, N '- (coronene-1,2-diybis (oxy)) dideecanamide N-bromododecanamide 79 8B 82-2

1,2-bis ((undecylthio) oxy) coronene Undecylthio bromide 79 8B 82-3

Coronene-1,2-diyl bis (undecane-1-sulfinate) Undecylsulfinyl bromide 75 8B 82-4

12, 12 '- (coronene-1,2-diylbis (oxy)) bis (dodecan- 12-bromododecan-1-ol 31 8B 82-5

Bis (ethane-3, 1 -diyl)) bis (oxy)) bis (ethane-2, 1 -dicyclohexyl) Bis (ethane-1-yl) bis (oxy)) bis (ethane-1-ol) Bromo-2- (2- (2- (2-hydroxyethoxy) ethoxy) ethoxy) ethane 59 8C 83

7,8-Dioxo-7,8-dihydrocholornene-l, 2-dyldidodecanoate Dodecanoyl bromide 35 8C 83-1

Diene undecyl (7,8-dioxo-7,8-dihydrocholornene-1,2-diyl) Carbornurobromic acid, undecyl ester 51 8C 83-2

N, N '- ((7,8-dioxo-7,8-dihydrocholornene-1,2-diyl) bis (oxy)) dione decanamide N-bromododecanamide 45

Compound Preparation Example 9A: Preparation of cyclopenta [fg] acenaphthylene-1,2,5,6-tetrayltetradodecanoate

In the same manner as in Preparation Example 4A, except for using dodecanoyl bromide instead of bromododecyl in Step 4A-4 of Preparation Example 4A, cyclopenta [fg] acenaphthylene-1,2,5,6 -Tetrayl tetradodecanoate (Compound 91) was obtained.

Compound Preparation Example 9B: Preparation of cyclopenta [fg] acenaphthylene-1,2-diallyldodecanoate

Synthesis of cyclopenta [fg] acenaphthylene-1,2-diallyldodecanoate (prepared in Example 4B-2) in the same manner as in Production Example 4B, except that dodecanoyl bromide was used instead of bromododecyl in Production Example 4B-2 Compound 92).

Compound Preparation Example 9C: Preparation of 5,6-bis ((12-hydroxydodecyl) oxy) cyclopenta [fg] acenaphthylene-1,2-

Bis ((12-hydroxydodecyl) oxy) -2-methylpropionic acid was prepared by using the same method as Preparation Example 4C, but using 12-bromododecan-1-ol instead of bromododecyl in Production Example 4C. Cyclopenta [fg] acenaphthylene-1,2-dione (Compound 93).

compound
Manufacturing example compound
number Compound structure Compound name Replacement reagent yield(%) 9A 91

Cyclopenta [fg] acenaphthylene-1,2,5,6-tetrayltetradodecanoate Dodecanoyl bromide 39 9A 91-1

Cyclopenta [fg] acenaphthylene-1,2,5,6-tetrayltetrakis (undecyl) tetracarbonate Carbornurobromic acid, undecyl ester 54 9A 91-2

N, N ', N ", N'" - (cyclopenta [fg] acenaphthylene-1,2,5,6-tetrayltetrakis (oxy)) tetraundecanamide N-bromododecanamide 31 9A 91-3

1,2,5,6-tetrakis ((undecylthio) oxy) cyclopenta [fg] acenaphthylene Undecylthio bromide 80 9A 91-4

Cyclopenta [fg] acenaphthylene-1,2,5,6-tetrayltetrakis (undecane-1-sulfinate) Undecylsulfinyl bromide 28 9A 91-5

12, 12 ', 12 ", 12"' - (1,2,5,6-cyclopenta [fg] acenaphthylene-1,2,5,6-tetrayltetrakis (oxy) tetrakis Dodecan-1-ol) 12-bromododecan-1-ol 76 9A 91-6

12, 12 ', 12 ", 12' '' - (cyclopenta [fg] acenaphthylene-1,2,5,6-tetrayltetrakis (oxy)) tetradodecanoic acid 12-bromododecanoic acid
(cas number 73367-80-3) 70 9B 92

Cyclopenta [fg] acenaphthylene-1,2-diallyldodecanoate Dodecanoyl bromide 85 9B 92-1

Cyclopenta [fg] acenaphthylene-l, 2-diallyldecyl dicarbonate Carbornurobromic acid, undecyl ester 80 9B 92-2

12,12'- (cyclopenta [fg] acenaphthylene-1,2-diylbis (oxy)) bis (dodecan-1-ol) 12-bromododecan-1-ol 63 9C 93

5,6-bis ((12-hydroxydodecyl) oxy) cyclopenta [fg] acenaphthylene- 12-bromododecan-1-ol 37

Compound Preparation Example 10A:

12, 12 ', 12' ', 12' '', 12 '' '', 12 '' '' - (triphenylen-2,3,6,7,10,11-hexaylhexakis )) Preparation of hexakis (dodecan-1-ol)

12 '', 12 '', 12 '', 12 '', 12 ', 12' 'and 12' 'were prepared in the same manner as in Production Example 5A, except that 12-bromododecan-1-ol was used instead of bromododecyl in Production Example 5A- 12 '' '', 12 '' '' - (triphenylen-2,3,6,7,10,11-hexaylhexakis (oxy)) hexakis (dodecan-1-ol) 101).

compound
Manufacturing example compound
number Compound structure Compound name Replacement reagent yield
(%) 10A 101

12, 12 ', 12' ', 12' '', 12 '' '', 12 '' '' - (triphenylen-2,3,6,7,10,11-hexaylhexakis )) Hexakis (dodecan-1-ol) 12-bromododecan-1-ol 50 10A 101-1

2 '' ', 2' '', 2 '' '' - ((((((((triphenyl- (Hexane) hexakis (oxy)) hexakis (ethane-2,1-diyl)) hexakis (oxy)) hexakis (ethane- Diyl)) hexakis (oxy)) hexaethanol Bromo-2- (2- (2- (2-hydroxyethoxy) ethoxy) ethoxy) ethane 56

Compound Preparation Example 11A: Preparation of 4,5,9,10-tetrakis ((6 - ((2-ethoxyvinyl) oxy) hexyl) oxy)

[Reaction Scheme 15]

11A-1. Preparation of 4,5,9,10-tetrakis ((6-bromohexyl) oxy) pyrene (1)

The same procedure as in Step 1A-2 of Preparation Example 1A was repeated except that 1,6-dibromoheaxnae was used instead of bromododecyl, -Tetrakis ((6-bromohexyl) oxy) pyrene (1) was prepared.

(D, 4H), 7.82 (m, 2H), 4.16 (d, 8H (CDCl3) ), 3.51 (t, 8H), 1.73 (m, 16H), 1.43-1.29 (m, 8H)

11A-2. (Pyrene-4,5,9,10-tetrayltetrakis (oxy)) tetrakis (hexane-6,1-dile)) tetrakis (Oxy)) Preparation of tetraethanol (2)

The resulting 4,5,9,10-tetrakis (6-bromohexyl) oxy) pyrene (1 mmol) and 1,2-ethanediol (5 mmol) were dissolved in dimethylformamide 20 ml), and the mixture was reacted at reflux at 80 ° C for 14 hours. Thereafter, the reaction mixture was extracted with chloroform, and water was removed with magnesium sulfite. The residue was purified by column chromatography to obtain 2,2 ', 2' ', 2' '' - (((pyrene-4,5,9,10- Keto (oxy)) tetrakis (hexane-6,1-dile)) tetrakis (oxy)) tetraethanol (2).

(Pyrene-4,5,9,10-tetrayltetrakis (oxy)) tetrakis (hexane-6,1-dile)) tetrakis (D, 4H), 7.82 (m, 2H), 6.44 (d, 4H), 4.15 (m, 12H) 1.71 (m, 16H), 1.43 (m, 16H)

11A-3. Preparation of 4,5,9,10-tetrakis ((6 - ((2-ethoxyvinyl) oxy) hexyl) oxy) pyrene (3)

The result of 11A-2, 2,2 ', 2 ", 2' '' - (((pyrene-4,5,9,10-tetrayltetrakis (oxy)) tetrakis -Dialyl) tetrakis (oxy) tetraethanol (1 mmol) and 1-bromoethane (6 mmol) were dissolved in tetrahydrofuran (30 ml) and refluxed at 70 ° C for 12 hours. To obtain 9,10-tetrakis ((6 - ((2-ethoxyvinyl) oxy) hexyl) oxy) pyrene (3, compound 111).

(D, 4H), 7.82 (m, < RTI ID = 0.0 > 2H), 5.40 (s, 4H), 4.49 (t, 4H), 4.16 (t, 8H), 4.01 (t, )

Compound Preparation Example 11B: Preparation of 2,3,6,7-tetrakis ((7 - ((2-ethoxyvinyl) oxy) heptyl) oxy)

11B-1. Preparation of 2,3,6,7-tetrakis ((7-bromoheptyl) oxy) anthracene

In the same manner as in PREPARATION 2A except that 1,7-dibromodecane was used instead of 1-bromododecane in Step 2A-3 of Preparation 2A, 2,3,6,7-tetrakis ((7 -Bromoheptyl) oxy) anthracene.

11B-2. Preparation of 2,3,6,7-tetrakis ((7 - ((2-ethoxyvinyl) oxy) heptyl) oxy) anthracene

(7-bromoheptyl) thiophene instead of 4,5,9,10-tetrakis ((6-bromohexyl) oxy) pyrene in the step 11A-2 of Preparation Example 11A. ) 11a-2 and 11A-3 of Preparative Example 11A were followed except that 2,3,6,7-tetrakis ((7 - ((2-ethoxyvinyl) oxy ) Heptyl) oxy) anthracene (Compound 112).

Compound Preparation Example 11C: Preparation of 1,2,7,8-tetrakis ((7 - ((2-ethoxyvinyl) oxy) heptyl) oxy) coronene

11C-1. Preparation of 1,2,7,8-tetrakis ((7-bromoheptyl) oxy) coronene

The same procedure as in Preparation Example 3A was repeated except that 1,7-dibromoheptane was used instead of bromododecyl in Step 3A-6 of Preparation Example 3A to prepare 1,2,7,8-tetrakis ((7-bromo Morpholyl) oxy) coronene.

11C-2. Preparation of 1,2,7,8-tetrakis ((7 - ((2-ethoxyvinyl) oxy) heptyl) oxy) coronene

((7-bromoheptyl) oxy) pyrene instead of 4,5,9,10-tetrakis (6-bromohexyl) oxy) pyrene in the step 11A- ) (11- (2-ethoxyvinyl) oxy) coronene was added to give 1,2,7,8-tetrakis ((7 - Oxy) heptyl) oxy) coronene (Compound 113).

Compound Preparation Example 11D Preparation of 1,2,5,6-tetrakis ((7 - ((2-ethoxyvinyl) oxy) heptyl) oxy) cyclopenta [fg] acenaphthylene

11D-1. Preparation of 1,2,5,6-tetrakis ((7-bromoheptyl) oxy) cyclopenta [fg] acenaphthylene

4,4'-bipyridinyl was prepared in the same manner as in Production Example 4A, except that 1,6-dibromoheptane was used instead of bromododecyl in the step 4A-4 of Production Example 4A. Morpholyl) oxy) cyclopenta [fg] acenaphthylene.

11D-2. Preparation of 1,2,5,6-tetrakis ((7 - ((2-ethoxyvinyl) oxy) heptyl) oxy) cyclopenta [fg] acenaphthylene

In the same manner as in Production Example 11A except for using 1,2,5,6-tetrakis ((7-bromoheptyl) oxy) pyrene instead of 4,5,9,10-tetrakis Step 11A-2 and 11A-3 of Preparation 11A were followed except that 1,2,5,6-tetrakis ((7 - (( 2-ethoxyvinyl) oxy) heptyl) oxy) cyclopenta [fg] acenaphthylene (Compound 114).

compound
Manufacturing example compound
number Compound structure Compound name Replacement reagent yield(%) 11A 111

4,5,9,10-tetrakis ((6 - ((2-ethoxyvinyl) oxy) hexyl) oxy) 1,2-ethenediol 11A 111-1

4,5,9,10-tetrakis ((6 - ((ethoxyethynyl) oxy) hexyl) oxy) pyrene 1,2-ethynediol 71 11A 111-2

4,5,9,10-tetrakis ((6 - ((ethoxydiazenyl) oxy) hexyl) oxy) pyrene Hypophony trussan acid
(Hyponitrous acid) 37 11B 112

2,3,6,7-tetrakis ((7 - ((2-ethoxyvinyl) oxy) heptyl) oxy) anthracene 1,2-ethenediol 44 11B 112-1

2,3,6,7-tetrakis ((7 - ((ethoxyethynyl) oxy) heptyl) oxy) anthracene 1,2-ethynediol 58 11B 112-2

2,3,6,7-tetrakis ((7 - ((ethoxydiazenyl) oxy) heptyl) oxy) anthracene Hypophony trussan acid
(Hyponitrous acid) 25 11C 113

1,2,7,8-tetrakis ((7 - ((2-ethoxyvinyl) oxy) heptyl) oxy) coronene 1,2-ethenediol 79 11C 113-1

1,2,7,8-tetrakis ((7 - ((ethoxyethynyl) oxy) heptyl) oxy) coronene 1,2-ethynediol 42 11C 113-2

1,2,7,8-tetrakis ((7 - ((ethoxydiazenyl) oxy) heptyl) oxy) coronene Hypophony trussan acid
(Hyponitrous acid) 53 11D 114

1,2,5,6-tetrakis ((7 - ((2-ethoxyvinyl) oxy) heptyl) oxy) -1,2,5,6-tetrahydrocyclopenta [fg] acenaphthylene 1,2-ethenediol 71 11D 114-1

1,2,5,6-tetrakis ((7 - ((ethoxyethynyl) oxy) heptyl) oxy) -1,2,5,6-tetrahydroxacyclopenta [fg] acenaphthylene 1,2-ethynediol 32 11D 114-2

1,2,5,6-tetrakis ((7 - ((ethoxydiazenyl) oxy) heptyl) oxy) -1,2,5,6-tetrahydrocyclopenta [fg] acenaphthylene Hypophony trussan acid
(Hyponitrous acid) 34

Compound Preparation Example 12A: Preparation of 4,5,9,10-tetrakis ((6 - ((3-ethoxyoxylan) -2-yl) oxy)

After dissolving iron chloride (0.001 mmol) in toluene (2 ml) and sufficiently replacing with nitrogen, the 4,5,9,10-tetrakis ((6 - ((2- ethoxyvinyl) oxy) ) Oxy) pyrene (compound 111, 1 mmol) was added, and the mixture was refluxed and reacted for 10 hours. Thereafter, the reaction mixture was extracted with chloroform and subjected to flash column chromatography using chloroform and hexane as developing solutions to obtain 4,5,9,10-tetrakis ((6 - ((3-ethoxyoxylan- Oxy) hexyl) oxy) pyrene (Compound 121) (yield: 68%).

Compound Preparation Example 12B: 2,2 ', 2 ", 2"' - (((pyrene-4,5,9,10-tetrayltetrakis (oxy)) tetrakis (hex- Dile)) tetrakis (oxy)) tetrakis (1-ethoxyethan-1,2-diol)

2 mmol of 4,5,9,10-tetrakis ((6 - ((3-ethoxyoxylan-2-yl) oxy) hexyl) oxy) pyrene (Compound 121) (III) porphyrin complex meso-tetrakis (2,3,5,6-tetrafluoro-4-N, N, N-trimethylaniline The reaction mixture was stirred at room temperature for 12 hours to obtain a final product, 2,2 ', 2' ', 2' '' - (((pyrene-4,5,9,10-tetrayltetrakis (Yield: 37%) of tetrakis (hexane-6,1-diallyl) tetrakis (oxy)) tetrakis (1-ethoxyethan-1,2-diol)

Compound Preparation Example 12C: Synthesis of 1,1 ', 1 ", 1"' - (((pyrene-4,5,9,10-tetrayltetrakis (oxy)) tetrakis (hex- Dile)) tetrakis (oxy)) tetrakis (2-ethoxyethanol)

1 mmol of 4,5,9,10-tetrakis ((6- ((3-ethoxyoxylan-2-yl) oxy) hexyl) oxy) pyrene (Compound 121) and NaBH ₄ 1 mmol) were added to 1 ml of urea / chlorine chloride eutectic salt and reacted at 60 ° C for 30 minutes to obtain final products 1,1 ', 1 ", 1"' - (((pyrene- Tetraquis (oxy)) tetrakis (hexane-6,1-dile)) tetrakis (oxy)) tetrakis (2-ethoxyethanol) )

compound
Manufacturing example compound
number Compound structure Compound name Replacement reagent yield(%) 12A 121

4,5,9,10-tetrakis ((6 - ((3-ethoxyoxylan-2-yl) oxy) hexyl) oxy) Compound 101 68 12A 121-1

2,3,6,7-tetrakis ((7 - ((3-ethoxyoxiran-2-yl) oxy) heptyl) oxy) anthracene Compound 102 79 12A 121-2

1,2,7,8-tetrakis ((7 - ((3-ethoxyoxiran-2-yl) oxy) heptyl) oxy) coronene Compound 103 63 12A 121-3

Tetrakis ((7 - ((3-ethoxyoxiran-2-yl) oxy) heptyl) oxy) -1,2,5,6-tetrahydrocyclopenta [fg] Naphthylene Compound 104 65 12B 122

(Pyrene-4,5,9,10-tetrayltetrakis (oxy)) tetrakis (hexane-6,1-dile)) tetrakis (Oxy)) tetrakis (1-ethoxyethane-1,2-diol) Compound 111 37 12B 122-1

((Anthracene-2,3,6,7-tetrayltetrakis (oxy)) tetrakis (heptane-7,1-diyl)) tetrakis (Oxy)) tetrakis (1-ethoxyethane-1,2-diol) Compound 111-1 45 12B 122-2

Tetrakis (heptane-7,1-diyl)) tetra (2,2 ', 2 ", 2" Kiss (oxy)) tetrakis (1-ethoxyethane-l, 2-diol) Compound 111-2 25 12B 122-3

2,2 ', 2 ", 2"' - ((((1,2,5,6-tetrahydrocyclopenta [fg] acenaphthylene-1,2,5,6-tetrayl) tetrakis (Oxy)) tetrakis (heptane-7,1-dile)) tetrakis (oxy)) tetrakis (1-ethoxyethan- Compound 111-3 24 12C 123

(Pyrene-4,5,9,10-tetrayltetrakis (oxy)) tetrakis (hexane-6,1-dile)) tetrakis (Oxy)) tetrakis (2-ethoxyethanol) Compound 111 76 12C 123-1

Tetrakis (heptane-7,1-dile)) tetrakis ((anthracene-2,3,6,7-tetrayltetrakis (oxy) Oxy)) tetrakis (2-ethoxyethanol) Compound 111-1 57 12C 123-2

Tetrakis (heptane-7, 1-dile)) tetrakis (triphenylphosphine) palladium (II) (Oxy)) tetrakis (2-ethoxyethanol) Compound 111-2 52 12C 123-3

1,1 ', 1 ", 1"' - ((((1,2,5,6-tetrahydrocyclopenta [fg] acenaphthylene-1,2,5,6-tetrayl) tetra Tetrakis (oxy)) tetrakis (heptane-7,1-dile)) tetrakis (oxy)) tetrakis (2-ethoxyethanol) Compound 111-3 65

Compound Preparation Example 13A. 13, 13 ', 13 ", 13"' - (pyrene-4,5,9,10-tetraisetetrakis (oxy)) tetra triadecanal

To a solution of 12,12 ', 12 ", 12"' - (pyrene-4,5,9,10-tetrayltetrakis (oxy) tetrakis (dodecane- -Ol) (Compound 61-5) (0.8 mmol) was added thereto, and 0.5M of KBr (0.16 ml) was added thereto, and 0.35 M of sodium hypochlorite (2.86 ml) was added to the solution at pH 8.6 for 3 hours. After the completion of the reaction, only the organic layer was extracted, and the water was removed with magnesium sulfate and evaporated. The resulting product was further purified by column chromatography to obtain the final products 13, 13 ', 13 ", 13'" - (pyrene-4,5,9,10- Tetrakis (oxy)) tetra-tricarboxylate (Compound 131) (yield: 38%).

compound
Manufacturing example compound
number Compound structure Compound name Replacement reagent yield(%) 13A 131

13,13 ', 13 ", 13"' - (pyrene-4,5,9,10-tetraisetetrakis (oxy)) tetra-tricarboxylate Compound 61-5 38 13A 131-1

13,13 ', 13 ", 13"' - ((tetradecahydroanthracene-2,3,6,7-tetrayl) tetrakis (oxy) Compound 71-5 39 13A 131-2

13, 13 ', 13 ", 13"' - (coronene-1,2,7,8-tetrayltetrakis (oxy) Compound 81-5 38 13A 131-3

13,13 ', 13 ", 13"' - (cyclopenta [fg] acenaphthylene-1,2,5,6-tetrayltetrakis (oxy) Compound 91-5 30

Compound Preparation Example 14A: 12,12 ', 12 ", 12"' - (pyrene-4,5,9,10-tetrayltetrakis (oxy)) tetrakis (dodecane- Manufacturing

12, 12 ', 12 "' - (pyrene-4,5,9,10-tetrayltetrakis (oxy) tetrakis (dodecan-1-ol) 15 mmol of hydrosene sulfide, 4 mmol of disodium carbonate and 3 mmol of calcium carbonate hydroxide were stirred and reacted at 250 ° C for 12 hr, 12 ', 12' ', 12' '- (pyrene- , 5,9,10-tetrayltetrakis (oxy)) tetrakis (dodecane-1-sial) (Compound 141) (yield: 47%).

Compound Preparation Example 14B: Preparation of 12,12 ', 12 ", 12"' - (pyrene-4,5,9,10-tetrayltetrakis (oxy) tetrakis (dodecane-1 -amine)

12, 12 ", 12 '''- (pyrene-4,5,9,10-tetrayltetrakis (oxy)) tetrakis (dodecane- (Compound 141) was fed with 7.5 bar of NH ₃ and 0.01 mmol of RuHCl (a-iPr-PNP) (CO) was refluxed for 12 hours in an argon atmosphere using toluene as a solvent. (Yield: 73%) of 12 '''- (pyrene-4,5,9,10-tetrayltetrakis (oxy) tetrakis (dodecane-1 -amine)

Compound Preparation Example 14C: Preparation of 11,11 '- (pyrene-4,5-diylbis (oxy)) di (dodecane-1-amine)

12, 12 ', 12 "' - (pyrene-4,5,9,10-tetrayltetrakis (oxy) tetrakis (dodecan-1-ol) except that 20 mmol of 12,12 '- (anthracene-2,3-diylbis (oxy)) bis (dodecan-1-ol) (Compound 72-5) (Pyrene-4,5-diylbis (oxy)) di (dodecane-1-thiol) was obtained through the same procedure as in Example 1,

Thereafter, 12,12 ', 12 ", 12"' - (pyrene-4,5,9,10-tetrayltetrakis (oxy)) tetrakis (dodecane- Except that 20 mmol of the above obtained 11,11 '- (pyrene-4,5-diylbis (oxy)) diester (dodecane-1-diol) (Compound 143) (yield: 57%) was obtained in the same manner as in step (1) of Example 1, except that 11,11'- (pyrene-4,5-diylbis (oxy)) di (dodecan-1 -amine)

Compound Preparation Example 14D: Synthesis of 11,11 ', 11 ", 11"' - (pyrene-4,5,9,10-tetrayltetrakis (oxy)) tetrakis (undecane- Produce

11 ", 11 ", 11 ", 11 ', 11 ', and < RTI ID = 0.0 > (Pyrene-4,5,9,10-tetrayltetrakis (oxy) tetrakis (undecan-1-ol).

(Compound 61-5) instead of 12, 12 ', 12 ", 12' '' - (pyrene-4,5,9,10-tetrayltetrakis (oxy) tetrakis (dodecan- Except that 11, 11 ', 11 "and 11"' - (pyrene-4,5,9,10-tetrayltetrakis (oxy) tetrakis (undecan-1-ol) (11), 11 '' - (pyrene-4,5,9,10-tetrayltetrakis (oxy) tetrakis (undecane- 1-thiol).

Thereafter, 12,12 ', 12 ", 12"' - (pyrene-4,5,9,10-tetrayltetrakis (oxy)) tetrakis (dodecane- 141) instead of the above obtained 11,11 ', 11 ", 11"' - (pyrene-4,5,9,10-tetrayltetrakis (oxy) tetrakis (undecane- ), 11 '', 11 "'- (pyrene-4,5,9,10-tetrayltetrakis (oxy) tetra Kiss (undecane-1-amine) (Compound 144) (yield 70%).

compound
Manufacturing example compound
number Compound structure Compound name Replacement reagent yield(%) 14A 141

12, 12 ', 12 ", 12"' - (pyrene-4,5,9,10-tetrayltetrakis (oxy)) tetrakis (dodecane- Compound 61-5 47 14A 141-1

(Tetrahexahydroanthracene-2,3,6,7-tetrayltetrakis (oxy)) tetrakis (dodecane-1-sial), 12 ' Compound 71-5 43 14A 141-2

(Coronene-1,2,7,8-tetranyltetrakis (oxy)) tetrakis (dodecane-1-sial), 12 " Compound 81-5 77 14A 141-3

(Cyclopenta [fg] acenaphthylene-1,2,5,6-tetranyltetrakis (oxy)) tetrakis (dodecane-1-sialyl) ) Compound 91-5 59 14B 142

12, 12 ', 12 ", 12"' - (pyrene-4,5,9,10-tetrayltetrakis (oxy) tetrakis (dodecane- Compound 141 73 14B 142-1

(Tetrahexahydroanthracene-2,3,6,7-tetrayl) tetrakis (oxy)) tetrakis (dodecan-l-amine) Compound 141-1 45 14B 142-2

(Coronene-1,2,7,8-tetranyltetrakis (oxy)) tetrakis (dodecan-1-amine), 12 ' Compound 141-2 35 14B 142-3

Tetrakis (dodecan-1-amine), 12 ', 12' ', 12' '' - (cyclopenta [fg] acenaphthylene-1,2,5,6- tetranyltetrakis Compound 141-3 50 14C 143

11, 11 '- (pyrene-4,5-diylbis (oxy)) di (dodecan- 57 14D 144

(Pyrene-4,5,9,10-tetrayltetrakis (oxy)) tetrakis (undecane-1-amine), 11 ' 70

Compound Preparation Example 15A: Preparation of Compound 151

[Compound 151]

(Pyrene-4,5,9,10-tetrayltetrakis (oxy)) tetradodecanoic acid (compound 61-6) (10 mmol (Compound 142) and 12,12 ', 12 ", 12"' - (pyrene-4,5,9,10-tetrayltetrakis (oxy)) tetrakis (dodecan- (10 mmol) were dissolved in distilled water (70 ml) and tetrahydrofuran (THF) and refluxed at 65 ° C for 5 hours to obtain the final product, Compound 151.

22 is a ¹ H-NMR spectrum of Compound 151 according to Production Example 15A measured in a CDCl ₃ solvent.

Compound Preparation Example 15B: Preparation of Compound 152

[Compound 152]

Production Example 1E The obtained 4,5-bis (dodecyloxy) -pyrylene-9,10-dione (compound 15, 20 mmol) and pyrene-4,5,9,10-tetraone (10 mmol) Was dissolved in distilled water (70 ml) and tetrahydrofuran (THF) together with bromotetrabutylammonium (Bu4NBr) (26 mmol) and sodium hydrosulfite (Na2S2O4) (230 mmol) and refluxed at 65 ° C for 5 minutes. (bromomododecyl) (60 mmol) and KOH (306 mmol) in distilled water (50 ml) was added to the solution, and the mixture was refluxed at 65 ° C for 16 hours to obtain compound 152.

23 is a ¹ H-NMR spectrum of Compound 152 according to Production Example 15B measured in a CDCl ₃ solvent.

Compound Preparation Example 15C: Preparation of Compound 153

[Compound 153]

The obtained 12, 12 ', 12 ", 12' '' - (pyrene-4,5,9,10-tetrayltetrakis (oxy)) tetradodecanoic acid (compound 61-6) (phenyl) -4,5,9,10-tetrayltetrakis (oxy)) tetrakis (undecane-1 -amine) (Compound 144 ) (10 mmol) were dissolved in distilled water (70 ml) and tetrahydrofuran (THF) and refluxed at 65 ° C for 5 minutes to obtain compound 153.

24 is a ¹ H-NMR spectrum of Compound 153 according to Production Example 15C measured in a CDCl ₃ solvent.

25A and 25B are optical photographs of 4,5,9,10-tetrakis (dodecyloxy) -pyrene (compound 11) crystals according to the preparation example of the compound.

Referring to FIGS. 25A and 25B, it can be seen that the organic crystals exhibit the shape of a rod having a width of several micrometers and a length of several tens to several hundreds of micrometers.

Evaluation of three-dimensional structure Example 1: Identification of three-dimensional structure by X-ray diffraction analysis

X-ray diffraction was carried out using Cu-Kα (λ = 0.15418 nm) radiation at 40 kV and 100 mA using D8 advance (Brucker) and D / MAX RINT 2000 (Rikaku) 45 °. In addition, the program EXPO2013 [Altomare A, et al. EXPO2013: a kit of tools for phasing crystal structures from powder data. Journal of Applied Crystallography, 2013 46, 1231-1235].

The X-ray diffraction spectrum results of the compound obtained in the Preparation Example of Compound using the measurement method are as follows.

26 shows the X-ray spectrum of a three-dimensional structure crystal by 4,5,9,10-tetrakis (dodecyloxy) -pyran (compound 11) according to the preparation example of the compound.

26, a = 37.523 A, b = 34.476 A and c = 9.340 A (residuals: Rp = 8.532, Rwp = 11.747) with an orthorhombic unit lattice.

27 shows an X-ray spectrum of a three-dimensional structure crystal by 2,3,6,7-tetrakis (dodecyloxy) anthracene (Compound 21) according to a preparation example of the compound.

28 shows X-ray spectra of crystals of a three-dimensional structure formed by 1,2,7,8-tetrakis (dodecyloxy) coronene (Compound 31) according to the compound preparation example.

29 shows the X-ray spectrum of a three-dimensional structure crystal by 1,2,5,6-tetrakis (dodecyloxy) cyclopenta [f, g] acenaphthalene (Compound 41) according to the preparation example of the compound.

30 shows an X-ray spectrum of a three-dimensional structure crystal by 2,3,6,7,10,11-hexakis (dodecyloxy) triphenylene (compound 51) according to the compound preparation example.

31A and 31B are a perspective view and a top view, respectively, of the crystal structure of 4,5,9,10-tetrakis (dodecyloxy) -pyran deduced from the X-ray spectrum of FIG.

31A, four oxides (A) in 4,5,9,10-tetrakis (dodecyloxy) -pyrene, which is a unit organic molecule (UM) forming a three-dimensional organic structure, The electron structure can be generated in an electron-rich region (δ-) and an electron-deficient region (δ +) within a group, ie, pyrene (Ar).

In addition, the dodecyl groups (Y) adjacent to each other in the unit organic molecule 4,5,9,10-tetrakis (dodecyloxy) -pyrane are separated by a Van Der Waals interaction (PIa) It can be stabilized and rigid as the flexibility decreases compared to the dodecyl group of one strain.

In addition, the terminal portions (X) of the dodecyl groups between adjacent unit organic molecules in each layer can also be bonded by a physical interaction (PIb). At this time, the terminal portions of adjacent dodecyl groups may interdigit with each other.

On the other hand, the unit organic molecules are stacked in the Z direction by pi-interactions (PIc). In this case, the electron-rich region (δ-) An attracting force PIc between the electron rich region delta- and the electron deficient region delta + is generated between the pyrene arrays Ar adjacent in the Y direction due to the electron-deficient region, , Whereby the direction in which the compound of the second layer (F ₂ ) extends relative to the direction X in which the compound of the first layer (F ₁ ) extends is shifted by 90 degrees in the Y direction, and the direction of the third layer (F ₃ ) can be turned 90 degrees again to be in the X direction.

Referring to FIG. 31B, it can be seen that a large number of pores V are formed in the three-dimensional organic structure.

3-Dimensional Structure Evaluation Example 2: Determination of Porous Structure by Nitrogen Adsorption Experiment

Nitrogen adsorption experiments were carried out using an Autosorb-iQ2ST / MP analyzer (Quantachrome Instruments), and 4,5,9,10-tetrakis (dodecyloxy) -pyrrole crystals, 4,5,9,10-tetra After the kiss (tetradecyloxy) -pyrene crystal and the 4,5,9,10-tetrakis (octadecyloxy) -pyrene crystal were respectively degassed at room temperature for 16 hours, Nitrogen was used.

FIG. 32 is a graph showing the crystal structure of 4,5,9,10-tetrakis (dodecyloxy) -pyrene crystal, 4,5,9,10-tetrakis (tetradecyloxy) , 10-tetrakis (octadecyloxy) - pyrene crystal.

Referring to FIG. 32, it can be seen that hysteresis curves appear that the nitrogen isothermal adsorption process and the nitrogen isothermal desorption process do not coincide with each other. In addition, all of the organic crystals showed mesoporous (2-50 nm) isothermal adsorption characteristics of type 4 according to IUPAC classification. This can be confirmed only by crystals having a porous structure, and it can be confirmed that the organic crystals effectively and clearly form a porous structure.

On the other hand, when 4,5,9,10-tetrakis (dodecyloxy) -pyrene crystals, 4,5,9,10-tetrakis (tetradecyloxy) It is known that the amount of nitrogen adsorption increases with 10-tetrakis (octadecyloxy) -pyrene crystals, which is presumed to be due to an increase in the pore area due to the length of the substituent bonded to pyrene.

Evaluation of three-dimensional structure Example 3: Confirmation of optical characteristics of three-dimensional structure crystal

FIG. 33 shows photographs of 4,5,9,10-tetrakis (dodecyloxy) -pyrene (compound 11) crystals according to the preparation example of the compound by irradiating light. Specifically, a direct irradiation light source using a BX-51 fluorescence polarization microscope (Olympus) and a U-RFL-T source was used, but a light source of 400 nm or less was irradiated to the crystal using an ultraviolet filter.

Referring to FIG. 33, it can be confirmed that the light inside the structure is prevented from diffusing to a specific part due to the characteristics of the photonic crystal material, and the light is strongly emitted only at the end of the structure.

Optical amplification layer production example 1

4,5,9,10-tetrakis (dodecyloxy) -pyrrole (Compound 11) according to Compound Preparation Example 1A was added to a mixed solvent of chloroform and ethyl acetate having a volume ratio of 1: 1 to prepare a homogeneous solution having a concentration of 12.5 mM And the homogeneous solution was spin-coated on soda lime glass to form an optical amplification layer.

Light-emitting element production example 1 in which an optical amplification layer was introduced

4,5,9,10-tetrakis (dodecyloxy) -pyrrole (Compound 11) according to Compound Preparation Example 1A was added to a mixed solvent of chloroform and ethyl acetate having a volume ratio of 5: 1 to prepare a homogeneous solution having a concentration of 27.5 mM And an optical amplification layer was formed on the light emitting device by using a dip coating method in which the red LED bulb, the blue LED bulb, the green LED bulb, or the white LED bulb was immersed in the homogeneous solution and then dried.

Light Emitting Device Production Example 2 Incorporating an Optical Amplification Layer

4,5,9,10-tetrakis (dodecyloxy) -pyrrole (Compound 11) according to Compound Preparation Example 1A was added to a mixed solvent of chloroform and ethyl acetate having a volume ratio of 1: 1 to prepare a homogeneous solution having a concentration of 12.5 mM And this homogeneous solution is spin-coated on a red LED array panel, a blue LED array panel, a green LED array panel, a white LED array panel, a red LED module, a blue LED module, a green LED module, An optical amplification layer was formed.

Organic Light-Emitting Element Production Example 1 into which an Optical Amplification Layer Was Incorporated

4,5,9,10-tetrakis (dodecyloxy) -pyrrole (Compound 11) according to Compound Preparation Example 1A was added to a mixed solvent of chloroform and ethyl acetate having a volume ratio of 5: 1 to prepare a homogeneous solution having a concentration of 27.5 mM And a red OLED bulb, a blue OLED bulb, a green OLED bulb, or a white OLED bulb were immersed in the homogeneous solution, and the resultant was taken out and dried, thereby forming an optical amplification layer on the organic light emitting device.

Production Example 2 of Organic Light Emitting Device Incorporating an Optical Amplification Layer

4,5,9,10-tetrakis (dodecyloxy) -pyrrole (Compound 11) according to Compound Preparation Example 1A was added to a mixed solvent of chloroform and ethyl acetate having a volume ratio of 1: 1 to prepare a homogeneous solution having a concentration of 12.5 mM And this homogeneous solution is spin-coated on a red LED array panel, a blue LED array panel, a green LED array panel, a white LED array panel, a red LED module, a blue LED module, a green LED module, An optical amplification layer was formed.

Production Example of Fluorescent Lamp Incorporating an Optical Amplification Layer

4,5,9,10-tetrakis (dodecyloxy) -pyrrole (Compound 11) according to Compound Preparation Example 1A was added to a mixed solvent of chloroform and ethyl acetate having a volume ratio of 5: 1 to prepare a homogeneous solution having a concentration of 27.5 mM And this homogeneous solution was dip-coated on a fluorescent lamp to form an optical amplification layer on a fluorescent lamp.

Production example of an incandescent lamp into which an optical amplification layer was introduced

4,5,9,10-tetrakis (dodecyloxy) -pyrrole (Compound 11) according to Compound Preparation Example 1A was added to a mixed solvent of chloroform and ethyl acetate having a volume ratio of 5: 1 to prepare a homogeneous solution having a concentration of 27.5 mM And this homogeneous solution was dip-coated on a fluorescent lamp to form an optical amplification layer on the incandescent lamp.

Optical amplification layer evaluation example 1: X-ray diffraction analysis

The X-ray diffraction analysis was performed on the optical amplification layer of the light emitting device or the organic light emitting device having the optical amplification layer, and the X-ray diffraction analysis was performed on the three-dimensional structure.

34 shows an X-ray spectrum of the optical amplification layer obtained in Production Example 1 of the light-emitting element into which the optical amplification layer is introduced.

34, the X-ray spectrum of the optical amplification layer obtained in the light-emitting element production example 1 in which the optical amplification layer is introduced shows the X-ray spectrum of 4,5,9,10-tetrakis (dodecyloxy) - Ray spectrum (Fig. 21) of the three-dimensional structure crystal by pyrene (compound 11). It can be seen that the optical amplification layer maintains the three-dimensional structure crystal.

Examples 1 and 2 of the light emitting device in which the optical amplifying layer is introduced, Examples 1 and 2 of the organic light emitting device in which the optical amplifying layer is introduced, the fluorescent light producing example in which the optical amplifying layer is introduced, and the incandescent lamp manufacturing example The X-ray spectrum of the optical amplification layer obtained in the same manner as in Fig. 34 was also shown.

Optical amplification layer evaluation example 2: Confirmation of refractive index and permittivity

The refractive index and the dielectric constant were measured by irradiating the optical amplification layer according to the optical amplification layer production example with light of 200 to 1800 nm.

FIG. 35A is a graph showing a refractive index and a permittivity at an ordinary axis of the optical amplification layer according to an embodiment of the present invention, and FIG. 35B is a graph showing the refractive index and the permittivity at an extra-ordinary axis and the refractive index and the permittivity thereof.

Referring to FIGS. 35A and 35B, it can be seen that the dielectric constant and the refractive index are both lower than or equal to 1 in both the normal axis and the abnormal axis in the wavelength region of about 300 nm or less, specifically, the dielectric constant and refractive index close to zero.

Optical amplification layer evaluation example 3: Confirmation of optical amplification by ultraviolet / visible light spectrometer

Light transmittance was measured by irradiating light from 200 to 800 nm with an ultraviolet / visible light spectrophotometer (Jasco 500) to the optical amplification layer according to the production example of the optical amplification layer.

36 is a graph showing light transmittance of an optical amplification layer according to an embodiment of the present invention.

Referring to FIG. 36, it can be seen that the transmittance ranging from 200 to about 300 nm is about 2750%. Considering that the transmittance of a general material is maximally 100%, it can be seen that the optical amplification layer exhibits optical amplification due to physical properties having a dielectric constant close to zero, which is generated by periodic and regular characteristics.

Optical amplification layer evaluation example 4: Confirmation of the relationship between the normalized Fermi level and the normalized plasmon frequency

37 is a graph showing the relationship between the normalized Fermi level of the optical amplification layer and the normalized plasmon frequency in the optical amplification layer production example.

Referring to FIG. 37, when the normalized Fermi level is denoted by Ef0 and the normalized plasmon frequency is denoted by Ef, DELTA Ef / DELTA Ef0 represents a value of 1 when electrons have an effective mass, (Ef / [Delta] Ef0) 1/2 is smaller than 1, specifically, 1/2 in the case where it is smaller than 1. [Nature Nanotechnology 7, 330-334 (2012)] According to the production example of the optical amplification layer It can be seen that fitting the data points obtained in the optical amplification layer (? Ef /? Ef0) 1/2 completely overlaps the graph representing 1/2. Thus, in this embodiment It can be seen that electrons in the optical amplification layer can have an effective mass of zero. This means that the optical amplification layer according to this embodiment is a topological insulator having a dirac band structure.

Optical amplification layer evaluation example 5: Confirmation of optical amplification through ultraviolet / visible light photoluminescence spectrometer

The optical amplification layer according to Production Example of the optical amplification layer was irradiated with light of 200 nm to 800 nm in a unit of 25 nm by using an ultraviolet / visible light emission spectrometer (Varian Cary Eclipse Fluorescence Spectrometer) The photoluminescence intensity was measured.

38 is a graph showing photoluminescence intensity of an optical amplification layer according to an embodiment of the present invention. 38, when 300 nm light is irradiated onto the optical amplification layer to excite the optical amplification layer, it is preferable that 300 nm (A1) equal to the excitation wavelength, 600 nm (A2) which is twice the excitation wavelength, Luminescence was observed at three times of 900 nm (A3). Similar phenomena were observed at different wavelengths (B1, C1, D1, E1, F1, G1, H1, I1, J1, and K1).

On the other hand, the light emission intensity at the same wavelength as the excitation wavelength was found to be 1000 au. This optical amplification is a phenomenon due to the local surface plasmon resonance of dirac plasmon caused by the characteristic of the optical amplification layer having a periodic and regular structure as a meta material having a near zero dielectric constant and as a topological insulator. This shows that the optical layer according to this embodiment can also be used as a tunable amplifier. Further, luminescent light having a wavelength corresponding to an integral multiple of the excitation wavelength was detected, which is caused by the anisotropy of the molecules themselves and the quadrupole characteristic.

Optical amplification layer evaluation example 6: Confirmation of degree of optical amplification according to the energy of incident light

According to the optical amplification layer production example, optical amplification layers were formed on soda lime glass at 120 nm, 135 nm, or 150 nm, and optical amplification layers having different thicknesses and 266 nm Was irradiated.

39 is a graph showing amplification degree according to incident energy of the laser.

Referring to FIG. 39, the optical amplification performance according to the amount of incident light can be confirmed.

Production Example 1 of solar cell into which an optical amplification layer was introduced

(Dodecyloxy) -pyrrole (Compound 11) according to Compound Preparation Example 1A was added to a mixed solution of chloroform and ethyl acetate (2: 1% v) to prepare a homogeneous solution of 27.5 mM concentration And the homogeneous solution was spin-coated on a silicon solar cell to form an optical amplification layer.

Production Example 2 of solar cell into which an optical amplification layer was introduced

A solution in which 25 ml of a solution of 4,5,9,10-tetrakis (dodecyloxy) -pyrene (Compound 11) according to Preparation Example 1A was dissolved in chloroform with 1 wt% of PMMA dissolved therein was used as a solvent Then, 0.1 wt% of catechol was mixed with PMMA to form a mixture, and the mixture was spin-coated on a silicon solar cell to form an optical amplification layer.

Production Example 3 of Solar Cell Incorporating an Optical Amplifying Layer

An optical amplification layer was formed in the same manner as in the solar cell production example 1 except that a cadmium telluride alloy solar cell was used instead of the silicon solar cell.

Production Example 4 of solar cell into which an optical amplification layer was introduced

An optical amplification layer was formed in the same manner as in Production Example 1 of solar cell except that a copper indium gallium-selenium alloy solar cell was used in place of the silicon solar cell.

Production Example 5 of solar cell into which an optical amplification layer was introduced

An optical amplification layer was formed in the same manner as in the solar cell production example 1 except that an organic solar cell was used instead of the silicon solar cell.

A solar cell production example 6 in which an optical amplification layer was introduced

An optical amplification layer was formed in the same manner as in Production Example 1 of Solar Cell, except that an organic / inorganic hybrid solar cell was used instead of the silicon solar cell.

Production Example 7 of Solar Cell Incorporating an Optical Amplification Layer

An optical amplification layer was formed in the same manner as in Production Example 1 of solar cell except that a dye-sensitized solar cell was used instead of the silicon solar cell.

Production Example 8 of solar cell into which an optical amplification layer was introduced

An optical amplification layer was formed in the same manner as in the solar cell production example 1 except that a gallium arsenide solar cell was used in place of the silicon solar cell.

Production Example 9 of Solar Cell Incorporating an Optical Amplification Layer

An optical amplification layer was formed in the same manner as in the solar cell production example 1 except that a transparent solar cell was used in place of the silicon solar cell.

Evaluation example of a solar cell into which an optical amplification layer is introduced

The open circuit voltage (Voc), the short circuit current (Jsc), and the fill factor (FF) of the solar cells into which the optical amplification layer obtained in the solar cell production examples 1 to 9 are introduced The results are summarized in Table 15 below. On the other hand, the ratio of the power conversion efficiency of the photovoltaic cells in which the optical amplification layer is introduced to the power conversion efficiency (PCE) of the solar cells to which the optical amplification layer is not introduced is expressed as a relative efficiency.

division Voc (V) Isc (A) Filling Factor (FF) Relative Efficiency (%) Example 1 0.5994 0.963 57.3 186 Comparative Example 1 0.5979 0.666 44.69 100 Example 2 0.577 0.839 55.94 152 Comparative Example 2 0.5984 0.666 44.67 100 Example 3 0.5994 0.963 57.3 186 Comparative Example 3 0.5979 0.666 44.69 100 Example 4 0.577 0.839 55.94 152 Comparative Example 4 0.5984 0.666 44.67 100 Example 5 0.5994 0.963 57.3 186 Comparative Example 5 0.5979 0.666 44.69 100 Example 6 0.577 0.839 55.94 152 Comparative Example 6 0.5984 0.666 44.67 100 Example 7 0.5994 0.963 57.3 186 Comparative Example 7 0.5979 0.666 44.69 100 Example 8 0.577 0.839 55.94 152 Comparative Example 8 0.5984 0.666 44.67 100 Example 9 0.5994 0.963 57.3 186 Comparative Example 9 0.5979 0.666 44.69 100

Referring to the above table, it was found that the solar cells into which the optical amplification layer was introduced exhibited an improvement of the strategy conversion efficiency, indicating a relative efficiency of 152% or 186% as compared with the solar cells without the optical amplification layer.

The scope of the present invention is defined by the appended claims, and all changes or modifications derived from the meaning and scope of the claims and their equivalents should be construed as being included within the scope of the present invention.

Claims (38)

An optical layer comprising a three-dimensional organic structure having a plurality of unit organic molecules represented by Formula 1:
[Chemical Formula 1]

In Formula 1,
Ar is a 6- to 46-membered homocyclic aromatic ring or a heterocyclic aromatic ring,
-A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to immediately adjacent ones of the substitution positions of Ar However,
m is an integer of 1 to 8,
A ₁ and A ₂ , independently of each other,

or

ego,
L ₁ and L ₂ , independently of each other,

,

,

,

,

,

,

,

, or

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

And a ₁ , a ₂ , a ₃ , b ₁ , and b ₂ are independently an integer 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 independently of one another are -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 ) _{c 1} -q ₂ - (p ₂ ) _{c 2} -q ₃ , and q ₁ and q ₃ independently of each other

or

, Q < ₂ > is hydrogen or a group in which the hydrogen group bonded to the carbon is substituted by F, Cl, Br, or I,

,

,

,

,

,

,

,

, or

, P ₁ and p ₂ are independently of each other -CR _a R _b -, c ₁ and c ₂ are integers of 0 to 2,
X ₁ and X ₂ are independently selected _{-CR c R d R e, -OH} , -COOH, -CHO, -SH, -COCR c R d R e, -COOCR c R d R e, -CR c = and _{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, or -NH _2,
R _a and R _b are independently H, F, Cl, Br, or I,
R _c , R _d , and R _e are independently H, F, Cl, Br, or I,
U represents 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 carbon number of 3 to 15 A substituted or unsubstituted C2-C15 alkenyl group, a substituted or unsubstituted C2-C15 alkynyl group, a substituted or unsubstituted C6-C15 aryl group, a substituted or unsubstituted C2-C20 alkynyl group, A substituted or unsubstituted arylalkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted arylalkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted alkylsulfone group having 1 to 15 carbon atoms, a substituted or unsubstituted alkylmercapto group having 1 to 15 carbon atoms, Or a substituted or unsubstituted alkylthio group having 1 to 15 carbon atoms, a substituted or unsubstituted alkylphosphoryl group having 1 or 15 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 15 carbon atoms, a substituted or unsubstituted carbon number 1 A substituted or unsubstituted C1-C15 alkylthio group, a substituted or unsubstituted C1-C15 alkylthryl group, a substituted or unsubstituted C1-C15 alkyl isothiocyanic group, a substituted or unsubstituted C1- A substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, A substituted or unsubstituted aliphatic hydrocarbon group having 1 to 15 carbon atoms, a ketimine group having 1 to 15 carbon atoms, an aldimine group having 1 to 15 carbon atoms, a substituted or unsubstituted amido group having 1 to 15 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, , An arylamino group having 3 to 24 carbon atoms, an arylsilyl group having 3 to 24 carbon atoms, an aryloxy group having 3 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, and an alkylamino group having 1 to 24 carbon atoms Which is selected,
o is an integer between 0 and 16; The method according to claim 1,
The three-dimensional organic structure
The van der Waals mutual interaction between X ₁ and X ₂ of one unit organic molecule and X ₁ and X ₂ of another unit organic molecule among a pair of unit organic molecules adjacent to each other in the same layer Self-assembly by action, London dispersion interaction or hydrogen bonding,
A pair of unit organic molecules positioned in different layers and adjacent to each other are self-assembled by pi-pi interactions between aromatic rings. The method according to claim 1,
Wherein Ar is selected from the group consisting of benzene, heteroatom containing aromatic analogues of benzene, naphthalene, aromatic analogs of naphthalene containing heteroatoms, anthracene, aromatic analogues of anthracene containing heteroatoms, phenalene, an aromatic analog of a phenalene containing a heteroatom, phenanthrene, an aromatic analog of a phenanthracene containing a heteroatom, cyclopenta [fg] acenaphthylene, Aromatic analogs of cyclopenta [fg] acenaphthylene containing atoms, tetracene, aromatic analogs of tetracene containing heteroatoms, pyrene, aromatic analogs of pyrene containing heteroatoms, Benz [de] anthracene, aromatic analogues of benz [de] anthracene containing heteroatoms, triphenylene, hetero Tri-phenylenediamine of an aromatic analogs containing from, pentacene (pentacene), an aromatic analog of pentacene containing a hetero atom, a nose Nene (coronene), or through the nose Nene aromatic analogue optical layer containing a hetero atom. The method according to claim 1,
Wherein Ar is an aromatic ring having C _n (n is an integer of 2 to 6) symmetry. The method according to claim 1,
Wherein -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to ortho positions of Ar Optical layer. The method according to claim 1,
M is at least 2,
Between the -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and the -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ pairs,
Wherein at least one substitution position of Ar in which -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ or -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ is not bonded, . The method according to claim 1,
Wherein Ar has C _n (n is an integer of 2 to 6) symmetry,
Wherein m is the same as n. 8. The method of claim 7,
Wherein the -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are positions symmetry- equivalent positions. The method according to claim 1,
Wherein the compound is an optical layer represented by the following formula (1c):
[Chemical Formula 1c]

In the above formula _{1c, Ar, A 1, A} 2, L 1, L 2, n1, n2, Y 1, Y 2, X 1, X 2, U and o are Ar, A _1, A ₂ of the general formula (1) _{, L 1, L 2, n1} , n2, Y 1, Y 2, X 1, X 2, the same each and U and o. 10. The method of claim 9,
Wherein Ar is an aromatic ring of the following structural formula 1:
[Structural formula 1]

In the above formula 1,
T ₁ to T ₆ are both C; Some of T &_lt; ₁ > to T &_lt; _{6 & gt} ; are independently N, P, B or Si,
G ₁ to G ₆ are substitution positions,
The pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to the G ₁ and G ₂ positions,
Another pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to G ₄ and G ₅ positions,
U is not bonded or bonded to the remaining G ₃ or G ₆ ,
The o may be an integer of 0 to 2. 10. The method of claim 9,
Wherein Ar is an aromatic ring of the following structural formula 2:
[Structural formula 2]

In the above formula 2,
T ₁ to T ₁₀ are both C; Some of T ₁ to T ₁₀ are N, P, B or Si independently of each other and the others are C,
G ₁ , G ₃ , G ₄ , G ₅ , G ₆ , G ₈ , G ₉ , and G ₁₀ are substitution positions,
The pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to G ₄ and G ₅ positions,
Another pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to G ₉ and G ₁₀ positions,
U is not bonded or bonded to the rest G ₁ , G ₃ , G ₆ , or G ₈ ,
And o may be an integer of 0 to 4. 10. The method of claim 9,
Wherein Ar is an aromatic ring of the following structural formula 3:
[Structural Formula 3]

In the above formula 3,
T ₁ to T ₁₄ are both C; Some of T &_lt; ₁ > to T &_lt; _{14 & gt} ; are independently N, P, B or Si,
G ₁ , G ₃ , G ₅ , G ₆ , G ₇ , G ₈ , G ₁₀ , G ₁₂ , G ₁₃ and G ₁₄ are substitution positions,
The pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to G ₆ and G ₇ positions,
Another pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to the G ₁₃ and G ₁₄ positions,
U is not bonded or bonded to the rest G ₁ , G ₃ , G ₅ , G ₈ , G ₁₀ , or G ₁₂ ,
And o is an integer of 0 to 6. 10. The method of claim 9,
Wherein Ar is an aromatic ring of the following structural formula 6:
[Structural Formula 6]

In the above formula 6,
T ₁ to T ₁₃ are both C; Some of T ₁ to T ₁₃ are N, P, B or Si independently of each other and the others are C,
G ₁ , G ₂ , G ₄ , G ₅ , G ₇ , G ₈ , G ₁₀ , and G ₁₁ are substitution positions,
The pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to the G ₁ and G ₂ positions,
Another pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded at G ₇ and G ₈ positions,
And the remaining G ₄ , G ₅ , G ₁₀ , or G ₁₁ is not bonded or bonded to U,
And o is an integer of 0 to 4. 10. The method of claim 9,
Wherein Ar is an aromatic ring of the following structural formula 6:
[Structural Formula 6]

In the above formula 6,
T ₁ to T ₁₃ are both C; Some of T ₁ to T ₁₃ are N, P, B or Si independently of each other and the others are C,
G ₁ , G ₂ , G ₄ , G ₅ , G ₇ , G ₈ , G ₁₀ , and G ₁₁ are substitution positions,
A pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to G ₄ and G ₅ positions,
Another pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to the G ₁₀ and G ₁₁ positions,
U is not bonded or bonded to the rest G ₁ , G ₂ , G ₇ , or G ₈ ,
And o is an integer of 0 to 4. 10. The method of claim 9,
Wherein Ar is an aromatic ring of the following structural formula 7:
[Structural Formula 7]

In Formula 7,
T ₁ to T ₁₈ are both C; Some of T ₁ to T ₁₈ are N, P, B or Si independently of each other and the others are C,
G ₁ , G ₃ , G ₅ , G ₇ , G ₈ , G ₉ , G ₁₀ , G ₁₂ , G ₁₄ , G ₁₆ , G ₁₇ and G ₁₈ are substitution positions,
The pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to G ₈ and G ₉ positions,
Another pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to G ₁₇ and G ₁₈ positions,
U is not bonded or bonded to the rest G ₁ , G ₃ , G ₅ , G ₇ , G ₁₀ , G ₁₂ , G ₁₄ , or G ₁₆ ,
And o is an integer of 0 to 8. 10. The method of claim 9,
Wherein Ar is an aromatic ring of the following structural formula 8:
[Structural formula 8]

In the above formula 8,
T ₁ to T ₁₄ , T ₁₆ , and T ₁₇ are both C; T ₁ to T ₁₄ , T ₁₆ , and T ₁₇ are independently N, P, B, or Si, with the remainder being C,
G ₁ , G ₂ , G ₄ , G ₅ , G ₇ , G ₈ , G ₉ , G ₁₁ , G ₁₂ , and G ₁₄ are substitution positions,
A pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to G ₄ and G ₅ positions,
Another pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded at the positions of G ₁₁ and G ₁₂ ,
U is not bonded or bonded to the rest G ₁ , G ₂ , G ₇ , G ₈ , G ₉ , or G ₁₄ ,
And o is an integer of 0 to 6. 10. The method of claim 9,
Wherein Ar is an aromatic ring of the following structural formula 11:
[Structural Formula 11]

In Formula 11,
T ₁ to T ₂₂ are both C; Some of T ₁ to T ₂₂ are independently of each other N, P, B or Si and the remainder is C,
G ₁ , G ₃ , G ₅ , G ₇ , G ₉ , G ₁₀ , G ₁₁ , G ₁₂ , G ₁₄ , G ₁₆ , G ₁₈ , G ₂₀ , G ₂₁ and G ₂₂ are substitution positions,
The pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to the G ₁₀ and G ₁₁ positions,
Another pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to G ₂₁ and G ₂₂ positions,
The remaining _{G 1, G 3, G 5} , G 7, G 9, G 12, G 14, G 16, G 18, G ₂₀ or is U is not bonded or coupled,
And o is an integer of 0 to 10. 10. The method of claim 9,
Wherein Ar is an aromatic ring of the following structural formula 12:
[Structural Formula 12]

In Formula 12,
T ₁ to T ₂₄ are both C; Some of T ₁ to T ₂₄ are N, P, B or Si independently of each other and the others are C,
G ₁ , G ₃ , G ₄ , G ₆ , G ₇ , G ₉ , G ₁₀ , G ₁₂ , G ₁₃ , G ₁₅ , G ₁₆ and G ₁₈ are substitution positions,
The pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to G ₆ and G ₇ positions,
Another pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to G ₁₅ and G ₁₆ positions,
U is not bonded or bonded to the rest G ₁ , G ₃ , G ₄ , G ₉ , G ₁₀ , G ₁₂ , G ₁₃ , or G ₁₈ ,
And o is an integer of 0 to 8. 10. The method of claim 9,
Wherein Ar is an aromatic ring of the following structural formula 13:
[Structural Formula 13]

In Formula 13,
T ₁ to T ₄₀ are both C; Some of T &_lt; ₁ > to T &_lt; _{40 & gt} ; independently of each other are N, P, B or Si,
_{G 1, G 3, G 4} , G 6, G 8, G 9, G 11, G 13, G 14, G 16, G 17, G 19, G 21, G 22, G 24, and G ₂₆ is a substituted Location,
The pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to G ₈ and G ₉ positions,
Another pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to G ₂₁ and G ₂₂ positions,
The remaining _{G 1, G 3, G 4} , G 6, G 11, G 13, G 14, G 16, G 17, G 19, G 24, G ₂₆ or is U is not bonded or coupled,
And o is an integer of 0 to 12. The method according to claim 1,
Wherein the compound is a compound represented by the following formula (1d):
≪ RTI ID = 0.0 &

In formula _{1d, Ar, A 1, A} 2, L 1, L 2, n1, n2, Y 1, Y 2, X 1, X 2, U and o are Ar, A _1, A ₂ of the general formula (1) _{, L 1, L 2, n1} , n2, Y 1, Y 2, X 1, X 2, the same each and U and o. 21. The method of claim 20,
Wherein Ar is an aromatic ring of the following structural formula 4:
[Structural Formula 4]

In the above formula 4,
T ₁ to T ₁₃ are both C; Some of T ₁ to T ₁₃ are N, P, B or Si independently of each other and the others are C,
G ₁ , G ₂ , G ₄ , G ₅ , G ₆ , G ₈ , G ₉ , G ₁₀ , and G ₁₃ are substitution positions,
The pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to the G ₁ and G ₂ positions,
Another pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to the G ₅ and G ₆ positions,
Another pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to G ₉ and G ₁₀ positions,
The remaining G ₄ , G ₈ , or G ₁₃ is not bonded or bonded to U,
And o is an integer of 0 to 3. 21. The method of claim 20,
Wherein Ar is an aromatic ring of the following structural formula 10:
[Structural Formula 10]

In the above formula 10,
T ₁ to T ₁₈ are both C; Some of T ₁ to T ₁₈ are N, P, B or Si independently of each other and the others 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 are substitution positions,
The pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to the G ₁ and G ₂ positions,
Another pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded at G ₇ and G ₈ positions,
Another pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to G ₁₃ and G ₁₄ positions,
U is not bonded or bonded to the remaining G ₃ , G ₆ , G ₉ , G ₁₂ , G ₁₅ , or G ₁₈ ,
And o is an integer of 0 to 6. 21. The method of claim 20,
Wherein Ar is an aromatic ring of the following structural formula 12:
[Structural Formula 12]

In Formula 12,
T ₁ to T ₂₄ are both C; Some of T ₁ to T ₂₄ are N, P, B or Si independently of each other and the others are C,
G ₁ , G ₃ , G ₄ , G ₆ , G ₇ , G ₉ , G ₁₀ , G ₁₂ , G ₁₃ , G ₁₅ , G ₁₆ and G ₁₈ are substitution positions,
The pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to G ₆ and G ₇ positions,
Another pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to G ₁₂ and G ₁₃ positions,
Another pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ are bonded to G ₁ and G ₁₈ positions,
U is not bonded or bonded to the remaining G ₃ , G ₄ , G ₉ , G ₁₀ , G ₁₅ , or G ₁₆ ,
And o is an integer of 0 to 6. The method according to claim 1,
Wherein the compound is an optical layer represented by the following formula
[Formula 1e]

In Formula _{1e, Ar, A 1, A} 2, L 1, L 2, n1, n2, Y 1, Y 2, X 1, X 2, U and o are Ar, A _1, A ₂ of the general formula (1) _{, L 1, L 2, n1} , n2, Y 1, Y 2, X 1, X 2, the same each and U and o. The method according to claim 1,
m is 2 or more,
The angle formed by the pair of -A ₁ - (L ₁ ) _{n 1} -Y ₁ -X ₁ and -A ₂ - (L ₂ ) _{n 2} -Y ₂ -X ₂ with respect to the center of Ar is the same optical layer. The method according to claim 1,
Wherein P ₁ , P ₂ and P ₃ are independently - (CH ₂ ) -, - (CF ₂ ) -, - (CH ₂ O) -, - (CH ₂ CH ₂ O) CH ₂ CH ₂ CH ₂ O) -. The method according to claim 1,
Wherein Q < ₁ > and Q < ₂ &

,

,

,

,

, or

/ RTI > The method according to claim 1,
Wherein Y ₁ and Y ₂ are independently selected _{- (CH 2) a1 - (} a1 is an integer of 6 to 30) or _{- (CH 2 CH 2 O)} a1 - (a1 is an integer of 3 to 10) of the optical layer . The method according to claim 1,
Y ₁ and Y ₂ are each independently of one another

, P ₁ is - (CH ₂ ) -, a ₁ is an integer of 3 to 15, Q ₁ is

,

,

,

,

, or

A, b1 is 1, P ₂ is - (CH ₂₎ - a, a2 is an integer from 1 to 3 of the optical layer. The method according to claim 1,
In Formula _1, A 1 and A _2, L ₁ and L _{2, n1} and _n2, Y ₁ and Y _2, X ₁ and X ₂ are both the same optical layer. A plurality of unit organic molecules forming a three-dimensional structure
Each unit organic molecule has a first pair of substituents respectively bonded to immediately adjacent positions of the aromatic ring and substitution positions of the aromatic ring and a second pair of substituents respectively bonded to immediately adjacent positions of the remaining substitution positions and,
The terminal groups of the substituents contained in the first pair of unit organic molecules of one of the unit organic molecules contained in one layer of the three-dimensional structure and the terminal groups of the substituents contained in the second pair of another unit organic molecule The terminal groups of the substituents are self-assembled by van der Waals interaction, London dispersion interaction or hydrogen bonding,
Wherein the unit organic molecules contained in one layer of the three-dimensional structure and the unit organic molecules contained in another layer adjacent thereto are self-assembled by pi-pi interactions between aromatic rings. An optical element comprising the optical layer of any one of claims 1 to 31 on an optical path. 33. The method of claim 32,
The optical element is a light emitting element having a light emitting layer,
Wherein the optical layer is an optical amplification layer disposed between the light emitting layer and the outside. 33. The method of claim 32,
Wherein the optical element is a solar cell having a light absorbing layer,
And the optical layer is an optical amplification layer disposed between the light absorption layer and the outside. 33. The method of claim 32,
The optical element is a display having a light emitting layer or a light emitting element,
Wherein the optical layer is an optical layer thick layer disposed between the light emitting layer or the light emitting element and the outside. 33. The method of claim 32,
The optical element is an illuminating device having a light emitting layer or a light emitting element,
Wherein the optical layer is an optical layer thick layer disposed between the light emitting layer or the light emitting element and the outside. 33. The method of claim 32,
Wherein the optical element is a super lens. 33. The method of claim 32,
Wherein the optical element is a tunable amplifier.

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