KR102435048B1 - Topological superconductor comprising organic crystal and electrical device having the same - Google Patents

Abstract

Provided are a topological superconductor having an organic crystal and an electronic device having the same. The topological superconductor includes an organic crystal in which a plurality of unit layers having aromatic ring groups regularly arranged in a plane are stacked, and the stacking of the unit layers is between aromatic ring groups disposed in the unit layers adjacent to each other. It is an active layer implemented by the pi-pi interaction of

Description

Topological superconductor comprising organic crystal and electrical device having the same

The present invention relates to superconductors, and specifically to topological superconductors.

Recently, the demand for a computer that calculates complex data, such as a supercomputer, is rapidly increasing. Quantum computers have been proposed as an alternative to this. A quantum computer is a new concept computer that is implemented and operated according to the main principles of quantum mechanics and quantum phenomena. do. A qubit is a superposition phenomenon that can be both '0' and '1' at the same time, which is a state that cannot be realized in conventional computers. It works based on the entanglement phenomenon that the state is also determined instantaneously. In this way, while the existing computer generates only a unique result corresponding to a specific input, the quantum computer can not only express a large number of cases simultaneously even when the number of qubits composed by using such quantum properties is small, but also , it has the advantage of being able to generate multiple results simultaneously using the non-deterministic properties of qubits.

Among the various ways to implement a quantum computer, the superconductor method uses the phenomenon of superconductivity in which resistance disappears near absolute 0°C, and uses an electronic device called a Josephson junction. A Josephson junction is a device with a thin insulator sandwiched between two superconductors. Although the original insulator does not allow current to flow, a current flows in the superconductor due to quantum mechanical tunneling effect. Pair), this Cooper pair maintains and transmits quantum information, and this information can be manipulated with microwaves to be used as qubits. However, as described above, the superconductivity phenomenon occurs only around an absolute temperature of 0° C., so it is difficult to apply it to an actual device.

Recently, a topological superconductor has been successfully implemented through the Josephson junction of a topological insulator and a superconductor, but it still has many limitations such as a cryogenic environment and an external magnetic field.

Accordingly, the present invention has been devised to solve the above problems, and an object of the present invention is to provide an intrinsic topological superconductor having superconductivity even at room temperature and an electronic device using the same.

In order to solve the above problems, one aspect of the present invention provides a topological superconductor. The topological superconductor includes an organic crystal in which a plurality of unit layers having aromatic ring groups regularly arranged in a plane are stacked, and the stacking of the unit layers is between aromatic ring groups disposed in the unit layers adjacent to each other. It is an active layer implemented by the pi-pi interaction of

The unit layer of the organic crystal includes a plurality of unit organic molecules including the aromatic ring, and each unit organic molecule includes a first pair of substituents bonded to immediately adjacent positions among substitution positions of the aromatic ring and the remainder. terminal groups of substituents included in the first pair of unit organic molecules among the unit organic molecules included in the unit layer, each having a second pair of substituents bonded to positions immediately adjacent among the substitution positions and the terminal groups of the substituents included in the second pair of the other unit organic molecule self-assemble by Van Der Waals interaction, London dispersion interaction, or hydrogen bonding can be A pair of substituents each bonded to immediately adjacent positions among substitution positions of the aromatic ring may have increased rigidity compared to a single substituent due to a Van Der Waals interaction therebetween. A pair of substituents each bonded to immediately adjacent positions among substitution positions of the aromatic ring may be bonded to ortho positions of the aromatic ring with respect to each other.

Each of the substituents may have a chalcogen element having a lone pair of electrons directly connected to the aromatic ring. The aromatic ring may be a 6 to 46 membered homocyclic aromatic ring or a heterocyclic aromatic ring. The substituents may be bonded to symmetry-equivalent positions among the substitution positions of the aromatic ring. The organic crystal may have a basic lattice structure of triclinic, monoclinic, orthorhombic, tetragonal, hexagonal, or cubic.

In order to solve the above problems, an aspect of the present invention provides an electronic device including the topological superconductor. The electronic device includes an organic crystal in which a plurality of unit layers having aromatic ring groups regularly arranged in a plane are stacked, wherein the stacking of the unit layers is between aromatic ring groups disposed in the unit layers adjacent to each other. It has an active layer realized by the pi-pi interaction of At least two edge electrodes spaced apart from each other are connected to an edge of one side of the active layer. At this time, the active layer is a topological superconductor that implements a zero bias current flowing along the edge even when no bias is applied.

The active layer may have a single crystal layer or a polycrystalline structure including a plurality of the organic crystals. The corner electrodes may be four. It may further include gate electrodes connected to the active layer on a surface opposite to the surface on which the corner electrodes are formed.

According to the present invention described above, it is possible to provide an intrinsic topological superconductor having superconductivity even at room temperature and an electronic device using the same.

1 is a schematic view showing an organic crystal (a) and its unit layer (b) according to an embodiment of the present invention.
FIG. 2 is a schematic diagram specifically illustrating a partial region of an organic crystal described with reference to FIG. 1 .
3 is a schematic view showing a method for manufacturing a self-assembled three-dimensional structure.
4 is a conceptual diagram illustrating an edge state of an aromatic ring included in a unit organic molecule of an organic crystal according to an embodiment of the present invention.
5 is a schematic diagram showing the state of a unit layer of an organic crystal according to an embodiment of the present invention.
6 and 7 are schematic views showing the state of the organic crystal according to an embodiment of the present invention.
8 is a schematic diagram showing the state of an active layer in a polycrystalline state.
9 is a schematic diagram illustrating an electronic device using an active layer including an organic crystal according to an embodiment of the present invention.
10A is a plan view illustrating an electronic device using an active layer including organic crystals according to another embodiment of the present invention, and FIG. 10B is a cross-sectional view taken along the cut line I-I' of FIG. 10A.
11 shows an X-ray spectrum of 4,5,9,10-tetrakis(dodecyloxy)-pyrene 3D organic crystal according to Preparation Example of 3D organic crystal.
12 is a photograph of an active layer in the form of pellets obtained during the manufacturing method of Superconducting Electronic Device Manufacturing Example 1. FIG.
13 shows an X-ray spectrum of an active layer in the form of a pellet obtained during the manufacturing method of Superconducting Electronic Device Preparation Example 1. FIG.
14 is a photograph of an electronic device obtained according to the manufacturing method of Superconducting Electronic Device Manufacturing Example 2;
15 is a graph showing current characteristics according to voltage of an electronic device according to Preparation Example 1 of a superconducting electronic device.
16 is a graph illustrating current characteristics with time when a voltage of 0V is applied to an electronic device according to Superconducting Electronic Device Manufacturing Example 1;
17 is a graph showing current characteristics according to voltage of an electronic device according to Preparation Example 1 of a superconducting electronic device.
18 is a graph showing current characteristics according to voltage of an electronic device according to Manufacturing Example 3 of a superconducting electronic device.
19 is a graph illustrating current characteristics according to time when a voltage of 0V is applied to an electronic device according to Manufacturing Example 3 of a superconducting electronic device.

Since the present invention can have various changes and can have various forms, specific embodiments are illustrated in the drawings and described in detail in the text. However, this is not intended to limit the present invention to the specific disclosed form, it should be understood to include all modifications, equivalents and substitutes included in the spirit and scope of the present invention. In describing each figure, like reference numerals have been used for like elements.

Unless defined otherwise, all terms used herein, including technical or scientific terms, have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Terms such as those defined in a commonly used dictionary should be interpreted as having a meaning consistent with the meaning in the context of the related art, and should not be interpreted in an ideal or excessively formal meaning unless explicitly defined in the present application. does not

Hereinafter, preferred embodiments of the present invention will be described in more detail with reference to the accompanying drawings.

self-assembled organic crystals

1 is a schematic view showing an organic crystal (a) and its unit layer (b) according to an embodiment of the present invention.

Referring to FIG. 1 , a unit layer (Ln) of an organic crystal according to an embodiment of the present invention may include aromatic ring groups (Ar) regularly arranged in a plane (b). The unit layers (L ₁ , L ₂ , L ₃ , and L ₄ ) of the organic crystal are stacked between aromatic ring groups (Ar) disposed in the unit layers adjacent to each other by pi-pi interaction to form a three-dimensional (3D) layer. An organic structure, that is, the organic crystal 100 may be formed (a). In addition, the organic crystal 100 may have pores V that are regularly arranged in the crystal.

FIG. 2 is a schematic diagram specifically illustrating a partial region of an organic crystal described with reference to FIG. 1 .

Referring to FIG. 2 , unit organic molecules UM shown with reference to Formula 1 below are regularly arranged in the unit layers L ₁ , L ₂ .

[Formula 1]

In Formula 1, Ar is a 6 to 46 membered aromatic ring, and may be a homocyclic aromatic ring in which all members are carbon or a heterocyclic aromatic ring having at least one selected from N, P, B, or Si. have. In addition, Ar is a single ring, for example, a 6-membered, monocyclic aromatic ring, or two or more aromatic rings joined to each other to form a condensed ring, for example, a 10- to 46-membered, 2- to It 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 represented by Ar1 to Ar16, including monocyclic aromatic benzene or heteroatom containing aromatic analogues of benzene; a naphthalene group of Ar17 to Ar30, including naphthalene having two rings or an aromatic analog of naphthalene containing a hetero atom; The anthracene group of Ar31 to Ar45, including an aromatic analog of anthracene containing anthracene or hetero atom, having three rings, phenalene of Ar46 to Ar51, including aromatic analog of phenalene containing phenalene or hetero atom ( phenalene) group, and a phenanthrene group of Ar52 to Ar69 including phenanthracene or an aromatic analog of phenanthracene containing a hetero atom; Cyclopenta[fg]acenaphthylene of Ar70 to Ar71 containing aromatic analogs of cyclopenta[fg]acenaphthylene having four rings or cyclopenta[fg]acenaphthylene containing heteroatoms (cyclopenta[fg] ]acenaphthylene) group; A pyrene group of Ar100, a benz[de]anthracene or a benz[de]anthracene group of Ar101 to Ar115, including aromatic analogs of benz[de]anthracene containing a hetero atom, and a triphenylene group of Ar116 to Ar130, including triphenylene or an aromatic analog of triphenylene containing a hetero atom; a pentacene group of Ar131 to Ar140, including aromatic analogs of pentacene or pentacene containing heteroatoms, having 5 rings; a coronene group of Ar141 to Ar148, including an aromatic analog of coronene or coronene containing a hetero atom, having six peri-fused rings; or Ar149 to Ar152 having 7 or more rings.

As an example, the Ar is C _n (n is an integer of 2 to 6), for example C ₂ (180° symmetry), C ₃ (120° symmetry), C ₄ (90° symmetry), or C ₆ ( 60° symmetry) may be an aromatic ring having an axis of molecular symmetry. In this case, it is assumed that all members of Ar are carbon.

Specifically, among the exemplified Ars, Ar1 to Ar16 benzene group, Ar17 to Ar30 naphthalene group, Ar31 to Ar45 anthracene group, Ar70 to Ar71 cyclopenta[fg]acenaphthylene group, Ar72 to Ar86 tetracene The 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

may be, and may be the same as or different from each other. A ₁ and A ₂ have a lone pair of electrons, so they can donate electrons to the aromatic ring (Ar) to which they are attached. Accordingly, localization of electron density in the pi (π)-electron structure of the aromatic ring (Ar) may be induced. Specifically, the electron density of the region adjacent to the position where A ₁ and A ₂ are bonded may be relatively high compared to other regions, and the other regions 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 are a linking group, and may be the same as or different from each other,

,

,

,

,

,

,

,

, or

can be In this case, E, E ₁ , and E ₂ may be O or S regardless of each other, and E ₁ and E ₂ may be the same as or different from each other. n ₁ and n ₂ may be the same as 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 an organic group, for example, a linear organic group, regardless of each other

can be Y ₁ and Y ₂ may be the same as or different from each other. a ₁ , a ₂ , a ₃ , b ₁ , and b ₂ may be an integer of 0 to 30 regardless of each other, and a ₁ +a ₂ +a ₃ +b ₁ +b ₂ may be an integer of 3 to 30. 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 . It may vary depending on the type of functional group. However, the number of elements constituting the main chain of each of Y ₁ and Y ₂ may be 6 to 30 so that a sufficient physical interaction may occur between Y ₁ and Y ₂ .

The P ₁ , P ₂ , and P ₃ may be -CR _a R _b - or -(CR _a R _b ) _r O- regardless of each other. In this case, R _a and R _b may be H, F, Cl, Br, or I regardless of each other, and r may be an integer of 1 to 3. Specifically, P ₁ , P ₂ , and P ₃ independently of each other are -(CH ₂ )-, -(CF ₂ )-, -(CH ₂ O)-, -(CH ₂ CH ₂ O)-, or -(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 ) _c1 -q ₂ -(p ₂ ) _c2 -q ₃ , and may be the same as or different from each other. q ₁ and q ₃ are independent of each other

or

may be, and may be the same as or different from each other. q ₂ is an unsubstituted or substituted hydrogen group bonded to carbon with another functional group, for example, F, Cl, Br, or I.

,

,

,

,

,

,

,

, or

can be p ₁ and p ₂ can be -CR _a R _b - independently of each other, R _a and R _b can be independently of each other H, F, Cl, Br, or I, c ₁ and c ₂ are It may be an integer from 0 to 2. As an example, Q ₁ and Q ₂ are independent of each other

,

,

,

,

, or

can be

(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 are independent of each other

(ie, in the above, a ₂ , a ₃ , b ₁ , and b ₂ are all 0), more specifically -(CH ₂ ) _a1 -(a1 is an integer from 6 to 30) or -(CH ₂ CH ₂ O) _a1 - (a1 is an integer from 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 other embodiments, Y ₁ and Y ₂ are independent of each other

(ie, in the above, a ₃ and b ₂ are both 0), more specifically, P ₁ is -(CH ₂ )-, a1 is an integer from 3 to 15, and Q ₁ is

,

,

,

,

, or

, b1 may be 1, P ₂ may be -(CH ₂ )-, and a2 may be an integer of 1 to 3.

X ₁ and X ₂ are terminal groups, 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 as or different from each other. In this case, R _c , R _d , and R _e may be H, F, Cl, Br, or I regardless of each other. As an example, -CR _{c R d R e may be -CH 3 or -CF 3 , -COCR c R d R e may be -COCH 3 , -COOCR c} R _d R _e may be -COOCH ₃ can be, -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 may be -C=N=N-CH ₃ , -C≡CR _a may be -C≡CH, -NHCR _c R _d R _e may be -NHCH ₃ .

In the present specification, each of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ may be referred to as a strain. The pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ are substitution positions of the aromatic ring (Ar) of immediately adjacent positions, i.e., ortho positions with respect to each other (eg, G ₄ and G ₅ positions of Structural Formula 2 below) or peri positions (eg, of Structural Formula 2 below) G ₁ and G ₃ positions). More specifically, the pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ are the aromatic rings (Ar) with respect to each other. may be bound 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, Y ₁ and Y ₂ included therein are between There may be an attractive force due to a physical interaction, for example, a Van Der Waals interaction, thereby stabilizing and increasing the stiffness of the strains.

The -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ pair, that is, a pair of strains is one (m=1) or two to It may be 8 pieces (m=2-8). That is, in Formula 1, m may be an integer of 1 to 8. Maximum number of pairs of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ that can be bonded to one aromatic ring (Ar) may vary depending on the number and form of Ar members.

When there are two or more pairs of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ , that is, when m is 2 or more, in the Ar The positions at which the -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ pairs are connected are C _n of Ar (n is 2 to 6 ) may be positions maintaining symmetry, that is, positions having equal symmetry among the substitution positions of Ar. When Ar is C _n (n is an integer of 2 to 6) symmetrical, -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ The number of pairs of m may be equal to n. Specifically, when Ar is C ₂ (180°) symmetric, the pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ The number m may be 2, and the positions where two pairs of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ are connected to Ar are C ₂ (180°) symmetry of Ar may be maintained. In another example, when Ar is C ₃ (120°) symmetrical, -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ The number of pairs m may be 3, and three pairs of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ are connected to Ar The positions may be positions that maintain the C ₃ (120°) symmetry of Ar. In another example, when Ar is C ₄ (90°) symmetric, the -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ The number of pairs of m may be 4, and four pairs of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ are connected to Ar. The positions used may be positions that maintain the C ₄ (90°) symmetry of Ar. In other words, if the number of pairs of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ is two or more, the spacing between these pairs, that is, The angles 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 ) _n2 -Y ₂ -X ₂ between pairs of -A ₁ -(L ₁ ) _n1 -Y ₁ A substitution position where -X ₁ or -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ is not bonded may be positioned to enhance localization of electron density in the aromatic ring. Further, U may be bonded to at least some of the substitutable positions to which -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ or -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ is not bonded. have.

U is a cyano group, a hydroxyl group, fluorine, chlorine, iodine, a substituted or unsubstituted C 1 to C 15 alkyl group, a substituted or unsubstituted C 1 to C 15 alkoxy group, a substituted or unsubstituted C 3 to C 15 of a cycloalkyl group, a substituted or unsubstituted C2 to C15 alkenyl group, a substituted or unsubstituted C2 to C15 alkynyl group, a substituted or unsubstituted C5 to C15 aryl group, a substituted or unsubstituted C2 to 15 heteroaryl group, substituted or unsubstituted C 1 to C 15 arylalkyl group, substituted or unsubstituted C 1 to C 15 alkylsulfone group, substituted or unsubstituted C 1 to C 15 alkyl mercapto group, substituted Or an unsubstituted C 1 to C 15 alkylthiocyan group, a substituted or unsubstituted C 1 or C 15 alkyl phosphate group, a substituted or unsubstituted C 1 to C 15 alkylnitro group, a substituted or unsubstituted C 1 to C 15 of an alkylnitroso group, a substituted or unsubstituted C1 to C15 alkylnitrile group, a substituted or unsubstituted C1 to C15 alkylisothiocyanate group, a substituted or unsubstituted C1 to C15 alkylisocyanic acid group , A substituted or unsubstituted C 1 to C 15 alkylcyanic acid group, a substituted or unsubstituted C 1 to C 15 alkylazo group, a substituted or unsubstituted C 1 to C 15 alkylazide group, a substituted or unsubstituted C 1 to 15 ketimine group, substituted or unsubstituted aldimine group having 1 to 15 carbon atoms, substituted or unsubstituted amide group having 1 to 15 carbon atoms, arylalkyl group having 6 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, carbon number It may be any one selected from 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. . o may be an integer between 0 and x, where x is an integer obtained by subtracting 2m from the number of substitutable positions of Ar. As an example, x may be at most 16.

A plurality of A ₁ may be the same as or different from each other, a plurality of A ₂ may be the same as or different from each other, a plurality of L ₁ may be the same as or different from each other, a plurality of L ₂ may be the same as or different from each other, a plurality of _n1s may be the same as or different from each other, a plurality of _n2s may be the same as or different from each other, a plurality of Y _1s may be the same as or different from each other, a plurality of Y _2s may be the same as or different from each other, and a plurality of X _1s may be different from each other. may be the same or different, a plurality of X _2s may be the same as or different from each other, and a plurality of Us may be the same or different from each other.

The compound represented by Formula 1 may be any one selected from the following Structural Formulas 1 to 13, but is not limited thereto.

[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 independently of each other, and others may be C. In addition, Gn is a substitution position of the aromatic ring (Ar of Formula 1), and some of them are -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 of Formula 1 -Y ₂ -X ₂ strains and U may be substituted.

The compound represented by Chemical Formula 1 may be any one of the following Chemical Formulas 1a to 1e.

[Formula 1a]

[Formula 1b]

[Formula 1c]

[Formula 1d]

[Formula 1e]

In Formulas 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 are Ar described in Formula 1 , A ₁ , A ₂ , L ₁ , L ₂ , _n1 , _n2 , Y ₁ , Y ₂ , X ₁ , X ₂ , m, U and o, respectively. In each formula, a plurality of A _1s may be the same as or different from each other, a plurality of A ₂ may be the same as or different from each other, a plurality of L ₁ may be the same as or different from each other, and a plurality of L ₂ may be the same as or different from each other. and a plurality of _n1s may be the same or different from each other, a plurality of _n2 may be the same as or different from each other, a plurality of Y ₁ may be the same as or different from each other, a plurality of Y ₂ may be the same as or different from each other, and a plurality of X _1s may be the same as or different from each other, a plurality of X _2s may be the same as or different from each other, and a plurality of Us may be the same or different from each other.

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

Specifically, the compound of Formula 1c is a pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ , that is, a compound having two pairs of strains. Thus, in Formula 1c, Ar may have C ₂ (180°) symmetry, and specifically, Ar is a benzene group of Ar1 to Ar16, a naphthalene group of Ar17 to Ar30, an anthracene group of Ar31 to Ar45, Ar70 to Ar71 of cyclopenta[fg]acenaphthylene group, Ar72 to Ar86 tetracene group, Ar87 to Ar100 pyrene group, Ar131 to Ar140 pentacene group, Ar141 to Ar148 coronene group, and Ar149 to Ar159 It may be any one aromatic ring selected from. Also, positions at which the strains are connected to Ar may be positions at which C ₂ (180°) symmetry is maintained, that is, positions having equal symmetry among substitution positions of Ar. Furthermore, positions at which the pair of strains are connected to Ar may be in an ortho position to each other. In addition, a substitution position to which the strain is not connected may be located between the pairs.

Specifically, when Ar is a benzene group of Structural Formula 1, a pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ are Another pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ at positions G ₁ and G ₂ is at positions G ₄ and G ₅ may be bonded, and U may or may not be bonded to the remaining G ₃ or G ₆ . In this case, o may be an integer of 0 to 2.

When Ar is a naphthalene group of Structural Formula 2, a pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ is G ₄ and Another pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ at the G ₅ position can be bonded at the G ₉ and G ₁₀ positions. and U may or may not be bonded to the remaining G ₁ , G ₃ , G ₆ , or G ₈ . In this case, o may be an integer of 0 to 4.

When Ar is an anthracene group of Structural Formula 3, a pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ is G ₆ and Another pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ at the G ₇ position can be bonded at the G ₁₃ and G ₁₄ positions. 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 Structural Formula 6, a pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ is a pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ with G ₇ in positions G ₁ and G ₂ It may be bonded to the G ₈ position, and U may or may not be bonded to the remaining G ₄ , G ₅ , G ₁₀ , or G ₁₁ . In this case, o may be an integer of 0 to 4. In another example when Ar is a cyclopenta[fg]acenaphthylene group of Structural Formula 6, a pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ is another pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ in positions G ₄ and G ₅ may be bonded to G ₁₀ and G ₁₁ positions, and U may or may not be bonded to the remaining G ₁ , G ₂ , G ₇ , or G ₈ . In this case, o may be an integer of 0 to 4.

When Ar is a tetracene group of Structural Formula 7, a pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ is G ₈ and another pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ at positions G ₉ and G ₁₇ and G ₁₈ 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 from 0 to 8.

When Ar is a pyrene group of Structural Formula 8, a pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ is G ₄ and another pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ at positions G ₅ and G 11 are bound to positions G ₁₁ and G ₁₂ 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.

When Ar is a pentacene group of Structural Formula 11, a pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ is G ₁₀ and another pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ at positions G ₁₁ and G 21 are bound to positions G ₂₁ and G ₂₂ and U may or may not be bonded to the remaining 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 from 0 to 10.

When Ar is a coronene group of Structural Formula 12, a pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ is G ₆ and another pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ at positions G ₇ and G ₁₅ and G ₁₆ 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 from 0 to 8.

When Ar is the aromatic ring of Structural Formula 13, a pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ is G ₈ and Another pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ at position G ₉ can be bonded at position G ₂₁ and G ₂₂ 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 from 0 to 12.

The compound of Formula 1d has a pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ , that is, three pairs of strains (in Formula 1) m=3). In Formula 1d, Ar may have C ₃ (120°) symmetry, and specifically, Ar is a phenalene group of A46 to A51, a triphenylene group of Ar116 to Ar130, and a co of Ar141 to Ar148. It may be any one aromatic ring selected from the group consisting of four groups. Also, positions at which the strains are connected to Ar may be positions at which C ₃ (120°) symmetry is maintained, that is, positions having equal symmetry among substitution positions of Ar. Furthermore, positions at which the pair of strains are connected to Ar may be in an ortho position to each other. In addition, a substitution position to which the strain is not connected may be located between the pairs.

When Ar is a phenalene group of Structural Formula 4, a pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ is G ₁ and at the G ₂ position, another pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ bonds at the G ₅ and G ₆ positions and another pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ may be bonded at positions G ₉ and G ₁₀ . and U may or may not be bonded to the remaining G ₄ , G ₈ , or G ₁₃ . In this case, o may be an integer of 0 to 3.

When Ar is a triphenylene group of Structural Formula 10, a pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ is G At positions ₁ and G ₂ , another pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ at positions G ₇ and G ₈ may be bonded, and another pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ is bonded at the G ₁₃ and G ₁₄ positions 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.

When Ar is a coronene group of Structural Formula 12, a pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ is G ₆ and another pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ at positions G ₇ and G 12 are bound to positions G ₁₂ and G ₁₃ and another pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ may be bonded at positions G ₁ and G ₁₈ 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 Formula 1e is a pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ , that is, three pairs of strains (in Formula 1) m=4). In Formula 1e, Ar may have C ₄ (90°) symmetry. Also, positions at which the strains are connected to Ar may be positions at which C ₄ (90°) symmetry is maintained, that is, positions having equal symmetry among substitution positions of Ar. Furthermore, positions at which the pair of strains are connected to Ar may be in an ortho position to each other. In addition, a substitution position to which the strain is not connected may be located between the pairs.

In another embodiment, the organic compound constituting the organic crystal may be represented by Formula 2 below.

[Formula 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 Ar, A ₁ , A described in Formula 1 above. ₂ , L ₁ , L ₂ , _n1 , _n2 , Y ₁ , Y ₂ , X ₁ , X ₂ , U and o, respectively. In each formula, a plurality of A _1s may be the same as or different from each other, a plurality of A ₂ may be the same as or different from each other, a plurality of L ₁ may be the same as or different from each other, and a plurality of L ₂ may be the same as or different from each other. and a plurality of _n1s may be the same or different from each other, a plurality of _n2 may be the same as or different from each other, a plurality of Y ₁ may be the same as or different from each other, a plurality of Y ₂ may be the same as or different from each other, and a plurality of X _1s may be the same as or different from each other, a plurality of X _2s may be the same as or different from each other, a plurality of Us may be the same as or different from each other, and a plurality of o may be the same or different from each other.

In Formula 2, Z ₁ and Z ₂ are independently of each other a substituted or unsubstituted C 1 to C 15 alkyl group, a substituted or unsubstituted C 1 to C 15 alkoxy group, or a substituted or unsubstituted C 3 to C 15 cyclo Alkyl group, a substituted or unsubstituted C2 to C15 alkenyl group, a substituted or unsubstituted C2 to C15 alkynyl group, a substituted or unsubstituted C5 to C15 aryl group, a substituted or unsubstituted C2 to C15 of a heteroaryl group, 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, substituted or unsubstituted A substituted or unsubstituted C1 to C15 alkylthiocyan group, a substituted or unsubstituted C1 or C15 alkylphosphoric acid group, a substituted or unsubstituted C1 to C15 alkylnitro group, or a substituted or unsubstituted C1 to C15 alkyl A nitroso group, a substituted or unsubstituted C 1 to C 15 alkylnitrile group, a substituted or unsubstituted C 1 to C 15 alkyl isothiocyanate group, a substituted or unsubstituted C 1 to C 15 alkyl isocyanate group, substituted or an unsubstituted C 1 to C 15 alkylcyanic acid group, a substituted or unsubstituted C 1 to C 15 alkylazo group, a substituted or unsubstituted C 1 to C 15 alkylazide group, a substituted or unsubstituted C 1 to C 15 of a ketimine group, a substituted or unsubstituted aldimine group having 1 to 15 carbon atoms, a substituted or unsubstituted amide group having 1 to 15 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, a carbon number 3 to It may be any one selected from an arylamino group having 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.

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

In another embodiment, the organic compound constituting the organic crystal may be represented by the following formula (3).

[Formula 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 are Ar, A ₁ , A ₂ described in Formula 1 above. , L ₁ , L ₂ , _n1 , _n2 , Y ₁ , Y ₂ , X ₁ , X ₂ , U and o, respectively. In each formula, a plurality of A _1s may be the same as or different from each other, a plurality of A ₂ may be the same as or different from each other, a plurality of L ₁ may be the same as or different from each other, and a plurality of L ₂ may be the same as or different from each other. and a plurality of _n1s may be the same or different from each other, a plurality of _n2 may be the same as or different from each other, a plurality of Y ₁ may be the same as or different from each other, a plurality of Y ₂ may be the same as or different from each other, and a plurality of X _1s may be the same as or different from each other, a plurality of X _2s may be the same as or different from each other, a plurality of Us may be the same as or different from each other, and a plurality of o 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 Formula 3, X ₁ ' and X ₂ ' are independent of each other.

,

,

,

,

,

, or

, A′ and A″ independently of each other are O or S, and R _f , R _g , R _h , R _i , R _j , R _f ′, and R _g ′ independently of each other are H or C1 to C3 may be an alkyl group of

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

Specifically, the compounds represented by Chemical Formulas 1c to 1e, that is, unit organic molecules (UM) may self-assemble to form a three-dimensional organic structure, that is, an organic crystal. 2 shows an organic structure using the unit organic molecule shown in Formula 1c, but is not limited thereto.

A pair of substituents -A-(L) _n -YX connected to an aromatic ring in one unit organic molecule (UM) are immediately adjacent to substitutable positions of the aromatic ring, for example, ortho It may be bound to a location or a peri location. In this case, a pair of -A-(L) _n -YXs specifically, the Y groups included in each of them, are specifically involved in the Van Der Waals interaction by physical interaction (PIa). can be stabilized by As a result, a pair of -A-(L) _n -YXs, that is, a pair of strains, has reduced flexibility compared to a pair of -A-(L) _n -YX of a strain and becomes more rigid (rigid). ) can be

On the other hand, A has a lone pair of electrons, so it can donate electrons to the bonded aromatic ring (Ar). As a result, the electron density of the pi (π)-electron structure is localized in the aromatic ring (Ar), so that a region having a relatively high electron density and a region having a relatively low electron density may be disposed. In other words, A bonded to the aromatic ring (Ar) may induce localization of electron density in the aromatic ring (Ar).

Specifically, an electric multipole corresponding to twice the number of -A-(L) _n -YXs (strain) pairs (m in Formula 1) may be strengthened. As an example, in the case of one-coordinated organic molecules represented by Chemical Formulas 1a and 1b, a quadrupole may be reinforced in the aromatic ring (Ar), and in the case of a bi-coordinated organic molecule represented by Chemical Formula 1c, that is, a linear organic molecule. , a quadrupole in the aromatic ring (Ar) may be further strengthened. In addition, in the case of a three-coordinated organic molecule represented by Formula 1d, a hexapole may be reinforced in the aromatic ring (Ar), and in the case of a tetracoordinated organic molecule represented by Formula 1e, in the aromatic ring (Ar) The octapole may be enhanced.

When a plurality of these unit organic molecules (UM) are located, the X groups between the unit organic molecules (UM) adjacent in one direction (for example, the X direction) have physical interactions, specifically, van der Waals (Van der Waals) (Van der Waals). Der Waals) interaction, London dispersion interaction, or hydrogen bonding may be non-covalently bonded (PIb). As an 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 by van der Waals interaction can bind, -H, -CH ₃ , -CH=CH ₂ , and -C≡CH can bind by London dispersion force, and -OH, -COOH, -NH ₂ , or -NHCH ₃ is a hydrogen bond can be combined by

In addition, the aromatic ring groups included in each of the unit organic molecules (UM) adjacent in another direction (eg, the Z direction) or included in one layer (L ₁ ) and the other layer (L ₂ ) are pi-pi It can be self-assembled or laminated by interaction (PIc). Specifically, as described above, an electron-rich region (δ-) and an electron-deficient region (δ+) induced by group A in the aromatic ring group (Ar) may occur, Compared to the direction (X) in which the compound of the first layer (L ₁ ) is extended due to the attractive force between the electron-rich region (δ-) and the electron-deprived region (δ+) between adjacent aromatic ring groups in the Y direction, A direction in which the unit organic molecules UM of the second layer L ₂ extend may be deviated by a predetermined angle. As an example, the direction in which the unit organic molecules UM of the second layer L ₂ extend may be rotated by 90 degrees compared to the direction X in which the unit organic molecules UM of the first layer F ₁ extend. Therefore, the direction in which the unit organic molecules UM of the second layer L ₂ extend may be the Y direction.

In addition, the X groups between the unit organic molecules (UM) of the second layer (L ₂ ) also have physical interactions, specifically Van Der Waals interactions, London dispersion interactions or hydrogen bonding. It can be attracted and non-covalently bonded (PIb) by hydrogen bonding.

As such, the organic crystal 100 is a non-covalent bond, specifically physical interaction, more specifically pi-pi interaction (π-π interaction), dipole-dipole interaction, induced dipole-dipole interaction and induced dipole- Unit organic molecules may be formed by self-assembly through induced dipole interactions. In addition, the organic crystal according to the present embodiment may be referred to as a porous organic crystal by having regularly arranged pores (V) between regularly arranged unit organic molecules (UM).

In addition, these organic crystals have regularity and periodicity, so the basic lattice of triclinic, monoclinic, orthorhombic, tetragonal, hexagonal, or cubic system It is characterized by having a structure. Specifically, in the case of the one-coordinated organic molecule represented by Chemical Formulas 1a and 1b and the two-coordinated organic molecule represented by Chemical Formula 1c, that is, linear organic molecules, triclinic, orthorhombic, tetragonal, and cubic A cubic system may be formed, and in the case of a tricoordinated organic molecule represented by Chemical Formula 1d, a hexagonal system and a monoclinic system are possible.

Specifically, in the case of FIG. 2, an orthorhombic lattice structure is shown.

Such a porous three-dimensional organic structure, that is, a porous organic crystal, is formed by self-assembly based on non-covalent bonds between unit organic molecules, specifically weak organic-organic interactions, and thus forms a structure easily and simply, and chemical cross-linking. Since it is formed using physical bonding between pure compounds without bonding, melting and dissolution are possible at any time, and a large pore volume and a completely regular and periodic structure can be secured. In addition, unlike a metal organic framework (MOF), since a metal is not used, structural characteristics can be maintained even in moisture and atmospheric environments. In addition, although the self-assembly process for forming the structure proceeds fairly quickly, the compound according to the present embodiment has the advantage of creating sophisticated and ordered complex and hierarchical structures despite the high speed.

Method for producing organic crystals

3 is a schematic view showing a method for manufacturing a self-assembled three-dimensional structure.

3 and 2, when the organic compound or organic molecule (UM) of Formula 1 is dissolved in an appropriate organic solvent and recrystallized, first, pi-pi between the aromatic rings (Ar) in the organic molecules (UM) Dimers are first generated by interaction (PIc), and then these dimers are further pi-pi interaction between aromatic rings (Ar) and physical interaction by X groups between unit organic molecules (UM). The organic molecules (UM) are self-assembled due to non-covalent bonding (PIb) attracted by action, specifically Van Der Waals interaction, London dispersion interaction, or hydrogen bonding. A three-dimensional structure can be obtained.

Specifically, a powder containing self-assembled organic crystal particles may be obtained through the following first to fourth methods. The self-assembled organic crystal particles may have a nanorod shape.

Method 1: Forming Powder Containing Organic Crystals Using Organic Solvent Evaporation Method

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

2) slowly evaporating only the solvent from the solution to gradually change to a homogeneous solution with a thick concentration

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

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

Method 2: Forming Powder Containing Organic Crystals Using Cooling Method

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

2) Cooling the homogeneous solution in a state in which the movement of the outside and the material is blocked

3) Forming organic crystals as the organic molecules self-assemble at a critical temperature

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

3rd method: powder formation method containing organic crystals using multi-solvents having different solubility

1) Two different systems are prepared in a closed space, and a homogeneous solution in which the organic molecules are dissolved in a first organic solvent having high solubility for the organic molecules is placed in one system, and evaporated in the other system disposing a second organic solvent that is well-formulated and has very low solubility in the organic molecules but good miscibility with the first organic solvent

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

3) forming organic crystals as the organic molecules self-assemble at critical solubility

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

Fourth method: powder forming method containing organic crystals using multi-solvents having different solubility

1) obtaining a homogeneous solution by dissolving the organic molecules at a saturated solubility in a first organic solvent having high solubility

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

3) forming organic crystals as the organic molecules self-assemble at critical solubility

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

An active layer in the form of pellets or a film can be obtained by using the powder containing the obtained self-assembled organic crystal particles. In one example, the powder containing the organic crystal particles may be pressed to prepare pellets or films. The pressurization may be performed within a pressure range of 100 to 5,000 kgf/cm ² , and the organic crystals may be additionally self-assembled during the pressurization process and the crystals may be enlarged. Specifically, the pellet form can be prepared by pressing in a state in which the powder is filled in the pellet die, and the film form can be prepared by pressing the powder evenly on the support.

In a mixed solvent of a first solvent capable of dissolving the powder containing organic crystals and a second solvent miscible with the first solvent, the powder containing the organic crystals is added to make a solution, and then the solution is placed on a support. It can be coated to form an active layer in the form of a thin film. At this time, 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 2.5:1, The solution may have a concentration of 5 mM to 40 mM. In addition, the coating may be spin coating, bar coating, slot die coating, spray coating, roll-to-roll coating, or inverse roll coating.

In another example, in a mixed solvent of a first solvent capable of dissolving the powder containing organic crystals and a second solvent miscible with the first solvent, a selected polymer miscible with the organic crystals is added to the first After forming the solution, a second solution may be formed by putting the powder containing the three-dimensional structure in the first solution, and the second solution may be coated on a support to form an active layer in the form of a thin film. The active layer may be finely phase-separated into a region containing the organic crystal and a region containing the polymer therein. At this time, 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 2.5:1, 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 40 mM. In addition, the coating may be spin coating, bar coating, slot die coating, spray coating, roll-to-roll coating, or inverse roll coating. The polymer is PVC (Polyvinyl chloride), PA (Polyamide), PE (polyethylene), PES (Polyethersulfone), PTFE (Polytetrafluoroethylene), PMMA (Poly (methyl methacrylate)), HDPE (high-density polyethylene), LDPE (low- density polyethylene), PP (polypropylene), PS (polystyrene), PVAC (polyvinyl acetate), PEO (polyethylene oxide), NYLON, PET (polyethylene terephthalate), PI (polyimide), or a combination of two or more thereof. The active layer may have a thickness of 50 to 500 nm, specifically, may have a thickness of 100 to 200 nm.

4 is a conceptual diagram illustrating an edge state of an aromatic ring included in a unit organic molecule of an organic crystal according to an embodiment of the present invention. Although pyrene is described as an example of the aromatic ring in FIG. 4 , the boundary state may be represented in all the aromatic rings described above without being limited thereto.

Referring to FIG. 4 , as the aromatic ring has a structure in which single bonds and double bonds are repeated between members constituting the ring, the aromatic ring has an up (↑) spin electron in the p orbital and down (↓) ) may have a structure in which members with spin electrons are repeated. According to the SSH (Su-Schrieffer-Heeger) model, in the non-trivial topological state of an aromatic ring having this structure, up (↑) spin and down (↓) through intercell pairing (CP) When the spins are linearly coupled, it is possible to implement an edge state in which unpaired up (↑) spins (MF ₁ ) and down (↓) spins (MF ₂ ) remain at both edges of the aromatic ring. These up (↑) and down (↓) spins can be referred to as marjoram or fermions. In other words, in a specific phase state, the aromatic ring has an up (↑) spin and a down (↓) spin on both edges, and as a result, the aromatic ring forms a majorana bound state (MBS), It can be defined as a topological superconductor.

5 is a schematic diagram showing the state of a unit layer of an organic crystal according to an embodiment of the present invention.

Referring to FIG. 5 , the unit layer (Ln) of the organic crystal may include aromatic ring groups (Ar) regularly arranged in a plane as described in FIG. 1(b). Each aromatic ring group (Ar) may have ↑ spin and ↓ spin at both edges of the ring, as described with reference to FIG. 4 . Between the aromatic ring groups (Ar) regularly arranged in the plane of the unit layer (Ln), ↑ spin and ↓ spin can be linearly coupled while forming a pair (CP), as a result, the unit layer (Ln) of the organic crystal ), ↑ spin (MF ₁ ) and ↓ spin (MF ₂ ) may be repeatedly arranged at corners of the unit layer Ln. The ↑ spin (MF ₁ ) and ↓ spin (MF ₂ ) located at the corners of the unit layer Ln may also be referred to as Majorana fermions.

6 and 7 are schematic views showing the state of the organic crystal according to an embodiment of the present invention.

Referring to FIG. 6 , as described in FIG. 1( a ), the organic crystal 100 is formed between the aromatic ring groups (Ar) disposed in the unit layers adjacent to each other by pi-pi interaction in the unit layers ( L ₁ , L ₂ , L ₃ , L ₄ , L ₅ , L ₆ ) may be sequentially stacked. As described with reference to FIG. 5 , each unit layer L _n may be arranged such that ↑ spin and ↓ spin are repeated at the boundary, that is, at the corners. The ↑ spin and the ↓ spin may be linearly coupled to form a pair (CP) with the ↑ spin and the ↓ spin located at corners in another adjacent unit layer (L _n ).

As a result, referring to FIGS. 6 and 7 , in the organic crystal 100 , the ↑ spin (MF ₁ ) and the ↓ spin (MF ₂ ) that do not form a pair at the corners of the organic crystal 100 are repeatedly arranged can be The ↑ spin (MF ₁ ) and ↓ spin (MF ₂ ) located at the corners of the organic crystal 100 may also be referred to as marjoram or fermions.

As such, the organic crystal 100 may implement a Majorana corner mode as it is arranged so that the ↑ spin (MF ₁ ) and the ↓ spin (MF ₂ ) are repeated at its corners. As a result, the organic crystal 100 forms a majorana bound state (MBS) and may be defined as a topological superconductor. Majorana fermions have the characteristics of being a particle and an anti-particle by themselves due to the nature of the real solution in which mass exists. In addition, the organic crystal 100 can implement a Majorana fermion at room temperature, and based on this, a single electron nanodevice can be implemented, which can be used as a core device of a quantum computer using a quantum effect. The single electron nanodevice may be a single electron spin control nanodevice by spin dependence in which spin is polarized at room temperature and bound to quantum dots.

The organic crystal 100 described above with reference to FIG. 7 may be a structure having a single crystal, and may be referred to as an active layer below.

8 is a schematic diagram showing the state of an active layer in a polycrystalline state.

Referring to FIG. 8 , the active layer may be implemented in the form of pellets or a film. Pellets or films can be prepared in the same manner as described above. In the active layer 100 ′, the organic crystal particles described with reference to FIGS. 1 to 7 , that is, the grains G may be disposed to face a grain boundary GB. As described above, the organic crystal particles G may have ↑ spin and ↓ spin at the edge, and ↑ provided in the organic crystal particles G adjacent to each other disposed facing the grain boundary GB. Spin and ↓ spin can be linearly coupled to form a pair (CP). As a result, as the ↑ spin (MF ₁ ) and the ↓ spin (MF ₂ ) are disposed at the edge of the active layer 100 in the polycrystalline state, the Marjoram corner mode can also be implemented.

9 is a schematic diagram illustrating an electronic device using an active layer including an organic crystal according to an embodiment of the present invention.

Referring to FIG. 9 , at least two edge electrodes connected to an edge of one side of the active layer 101 and spaced apart from each other are disposed. The active layer 101 may have an organic crystal having a single crystal structure described with reference to FIGS. 1 to 7 or a polycrystalline structure having a plurality of organic crystal particles described with reference to FIG. 8 . As an example, the edge electrodes T ₁ , T ₂ , T ₃ , and T ₄ are disposed on the upper surface of the active layer 101 to be spaced apart from each other so as to be connected to the upper surface of the active layer 101 . In the drawing, the corner electrodes T ₁ , T ₂ , T ₃ , and T ₄ are disposed to be connected to the corner portion of the active layer 101 , but the present invention is not limited thereto.

In addition, the gate electrode G may be connected on a surface opposite to a surface to which the edge electrodes T ₁ , T ₂ , T ₃ , and T ₄ of the active layer 101 are connected, for example, on a lower surface of the active layer 101 . . However, an insulating layer I may be disposed between the gate electrode G and a corner of the lower surface of the active layer 101 so that the gate electrode G is not connected to the corner of the lower surface. However, the gate electrode G may be omitted.

Above, the upper surface and the lower surface are relative and only mean surfaces facing each other and should not be construed in a limiting sense.

10A is a plan view illustrating an electronic device using an active layer including organic crystals according to another embodiment of the present invention, and FIG. 10B is a cross-sectional view taken along the cutting line I-I' of FIG. 10A.

10A and 10B , an insulating layer 201 may be formed on the substrate 200 . The substrate 100 may be a semiconductor, a polymer, or a glass substrate, but is not limited thereto. At least two corner electrodes T ₁ , T ₂ , T ₃ , and T ₄ may be formed on the insulating layer 201 . The corner electrodes T ₁ , T ₂ , T ₃ , and T ₄ may be, for example, metal electrodes having excellent conductivity, and may be aluminum, tungsten, or copper electrodes, but is not limited thereto. Thereafter, an active layer 101 including an organic crystal that covers some portions of each of the corner electrodes T ₁ , T ₂ , T ₃ , and T ₄ and exposes other portions may be formed. The active layer 101 is formed by coating a solution obtained by dissolving or dispersing the organic crystalline powder described above in a solvent on the substrate on which the corner electrodes T ₁ , T ₂ , T ₃ , T ₄ are formed, and then volatilizing the solvent. After forming, it can be formed by patterning using a patterning method through electron beam lithography or the like. A polymer serving as a binder may also be included in the solution. As a result, the corner electrodes T ₁ , T ₂ , T ₃ , and T ₄ may be respectively connected to the corners of the lower surface of the active layer 101 and disposed to be spaced apart from each other. Thereafter, the gate electrode G may be connected to the upper surface of the active layer 101 . In this case, the gate electrode G may be formed to be spaced apart so as not to be connected to the edge of the active layer 101 . However, the gate electrode G may be omitted.

In the electronic device described with reference to FIGS. 9, 10A, and 10B , when an external circuit is connected to at least two of the corner electrodes T ₁ , T ₂ , T ₃ , and T ₄ , the corner electrodes are A current, that is, a zero bias current, may flow along the edge of the active layer 101 even when no voltage is applied therebetween. This is presumed to be because the active layer 101 can implement the Majorana corner mode as the active layer 101 is arranged so that ↑ spin (MF ₁ ) and ↓ spin (MF ₂ ) are repeated at corners or edges as described above, The active layer 101 through which a zero bias current can also flow may be referred to as a topological superconductor.

An electronic circuit may be provided in which a plurality of electronic devices described with reference to FIGS. 9, 10A, and 10B are provided, and the plurality of electronic devices are electrically connected to each other. In this case, the electronic circuit may be referred to as a quantum circuit or a braided circuit.

Hereinafter, in order to explain the present invention in more detail, preferred experimental examples according to the present invention will be described in more detail with reference to the accompanying drawings. However, the present invention is not limited to the embodiments described herein and may be embodied in other forms.

Preparation example of three-dimensional organic crystal: Preparation of 4,5,9,10-tetrakis(dodecyloxy)-pyrene

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

After dissolving pyrene (10 mmol) in dichloromethane (40.0 mL) and acetonitrile (40 mL) solution, ruthenium (III) chloride hydrate (0.25 g, 1.2 mmol) and Sodium metaperiodate (NaIO ₄ ) (17.5 g, 81.8 mmol) was refluxed in distilled water (50.0 mL) at 40° C. for 16 hours to prepare pyrene-4,5,9,10-tetraone.

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

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

Pyrene-4,5,9,10-tetraone (10 mmol) obtained in 1A-1 was mixed with bromotetrabutylammonium (Bu ₄ NBr) (13 mmol) and sodium hydrosulfite (Na ₂ S ₂ O ₄ ) (115 mmol) and dissolved in distilled water (50 mL) and tetrahydrofuran (THF), and refluxed at 65° C. for 5 minutes. To the reaction solution, an aqueous solution prepared by dissolving bromododecyl (60 mmol) and KOH (306 mmol) in distilled water (50 mL) was added, followed by refluxing at 65° C. for 16 hours to 4,5,9,10-tetra Kis(dodecyloxy)-pyrene (R=C ₁₂ H ₂₅ , compound 11 in Scheme 5) was obtained (yield: 72%).

4,5,9,10-tetrakis(dodecyloxy)-pyrene: ¹ H NMR (600 MHz, 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(t,12H)

11 shows an X-ray spectrum of 4,5,9,10-tetrakis(dodecyloxy)-pyrene 3D organic crystal according to Preparation Example of 3D organic crystal.

11 , for 4,5,9,10-tetrakis(dodecyloxy)-pyrene, a=37.523 Å, b=34.476 Å, and c=9.340 Å (residuals: Rp=8.532, Rwp= 11.747), it was confirmed to form a crystal having an orthorhombic unit lattice.

Superconductor Electronic Device Manufacturing Example 1

The 4,5,9,10-tetrakis(dodecyloxy)-pyrene organic crystal obtained in the three-dimensional organic crystal preparation example was dissolved in ethyl acetate, an organic solvent, and only the organic solvent was slowly evaporated to the critical concentration. The 4,5,9,10-tetrakis(dodecyloxy)-pyrene was self-assembled to obtain a three-dimensional organic crystal, and the organic crystal was filtered and the residual organic solvent was removed in a vacuum. The self-assembled three-dimensional organic crystalline powder thus obtained was prepared as an active layer in the form of pellets having a diameter of 13 mm and a thickness of 5 mm by applying a pressure of 1 bar using an Evacuable pellet press of PIKE. The edge electrodes, which are four Al strips, were connected to the upper surface of the active layer in the form of pellets obtained using carbon tape or silver paste, and the van der pauw method was used so that the corner electrodes were connected to the upper surface of the active layer.

Superconductor Electronic Device Manufacturing Example 2

In the superconducting electronic device obtained in Superconducting Electronic Device Manufacturing Example 1, the gate electrode, which is an Al strip, on the lower surface of the active layer in the form of a pellet is connected using carbon tape or silver paste, but is connected so as to be insulated from the edge of the pellet. was prepared.

Superconductor Electronic Device Manufacturing Example 3

The 4,5,9,10-tetrakis(dodecyloxy)-pyrene organic crystal obtained in the three-dimensional organic crystal preparation example was dissolved in an organic solvent ethyl acetate, and only the organic solvent was slowly evaporated to obtain a critical concentration. Three-dimensional organic crystals were obtained by self-assembly of the 4,5,9,10-tetrakis(dodecyloxy)-pyrene, and the organic crystals were filtered and the residual organic solvent was removed in a vacuum. The self-assembled three-dimensional organic crystal powder thus obtained was subjected to a pressure of 1 bar using an evacuable pellet press from PIKE to prepare pellets having a diameter of 13 mm and a thickness of 5 mm. After the formed pellets were pulverized to obtain 93 mg of three-dimensional organic crystal powder, 5 mg of polyvinylpyrrolidone was mixed with a solution of 2 mg of ethanol. The mixture was bar-coated on a substrate to form an active layer in the form of a film. The edge electrodes, which are four Al strips, were connected to the upper surface of the obtained film-type active layer using carbon tape or silver paste, and the van der pauw method was used in which the corner electrodes were connected to the upper surface edge of the film-type active layer.

Superconductor Electronic Device Manufacturing Example 4

In the superconducting electronic device obtained in Superconducting Electronic Device Manufacturing Example 3, the gate electrode, which is an Al strip, is connected to the lower surface of the active layer in the form of a film using carbon tape or silver paste. was prepared.

12 is a photograph of an active layer in the form of a pellet obtained during the manufacturing method of Superconducting Electronic Device Manufacturing Example 1. FIG.

Referring to FIG. 12 , it can be seen that the active layer 101 in the form of a pellet has a thickness of about 13 mm and is manufactured in a circular shape.

13 shows an X-ray spectrum of an active layer in the form of pellets obtained during the manufacturing method of Superconducting Electronic Device Preparation Example 1. FIG.

Referring to FIG. 13 , the pellet shows a strong main peak indicating the (100) plane in which 2theta is between 0 and 2, and it can be seen from this X-ray spectrum that the pellet is a polycrystal having a plurality of orthorhombic crystal grains.

14 is a photograph of an electronic device obtained according to the manufacturing method of Superconducting Electronic Device Manufacturing Example 2;

Referring to FIG. 14 , four Al strip edge electrodes ( T ₁ , T ₂ , T ₃ , T ₄ ) connected to the top edge are formed on the top surface of the active layer 101 in the form of a pallet, and the bottom surface It can be seen that the Al strip gate electrode (G) insulated from the lower surface edge is formed thereon. Meanwhile, the electronic device according to Superconductor Electronic Device Manufacturing Example 1 has the same shape as the electronic device according to Superconductor Electronic Device Manufacturing Example 2 except that the gate electrode G is not provided.

15 is a graph showing current characteristics according to voltage of an electronic device according to Preparation Example 1 of a superconducting electronic device. To this end, in a state in which a voltage is applied to the two opposite corner electrodes T ₁ , T ₃ among the corner electrodes T ₁ , T ₂ , T ₃ , and T ₄ , the other two corner electrodes T ₂ , T ₄ ) by connecting an external circuit to measure the flowing current. This process was carried out at room temperature and no artificial magnetic field was applied from the outside.

Referring to FIG. 15 , the same voltage is applied to the two corner electrodes T ₁ , T ₃ , that is, a current flows through the other two corner electrodes T ₂ , T ₄ even when a voltage of 0V is applied. can be observed This means that a zero bias current exists, and this zero bias current flows along the edge of the active layer 101 in the form of a pallet. Also, it shows that phase locking is achieved regardless of the magnitude of the voltage. These characteristics indicate that the active layer in the form of pellets used in Preparation Example 1 of the superconducting electronic device is a topological superconductor.

16 is a graph illustrating current characteristics with time when a voltage of 0 V is applied to an electronic device according to Superconducting Electronic Device Manufacturing Example 1; This process was carried out at room temperature and no artificial magnetic field was applied from the outside.

Referring to FIG. 16 , the same voltage is applied to the two corner electrodes T ₁ , T ₃ , that is, a current flows through the other two corner electrodes T ₂ , T ₄ even in a state where a voltage of 0V is applied. , and that this current appears as a constant alternating current with time is a result of the Josephson junction. Also, it can be seen that this alternating current exhibits periodicity of pi, which is evidence confirming that the active layer in the form of a pellet used in Preparation Example 3 of the superconducting electronic device is a topological superconductor.

17 is a graph showing current characteristics according to voltage of an electronic device according to Preparation Example 1 of a superconducting electronic device. In this case, unlike the case shown in FIG. 15 , in a state in which a voltage is applied to two adjacent corner electrodes T ₁ , T ₄ among the corner electrodes T ₁ , T ₂ , T ₃ , and T ₄ . By connecting an external circuit to the other two adjacent edge electrodes (T ₂ , T ₃ ), the conductivity between the edge electrodes (T ₂ , T ₃ ) was measured. This process was carried out at room temperature and no artificial magnetic field was applied from the outside.

Referring to FIG. 17 , it can be seen that the conductivity exhibits a negative value close to -0.5 in a voltage range between -0.7V and 0.7V. This is evidence confirming that the active layer in the form of a pellet used in Preparation Example 1 of the superconducting electronic device is a topological superconductor.

18 is a graph showing current characteristics according to voltage of an electronic device according to Manufacturing Example 3 of a superconducting electronic device. To this end, current flowing through the other two upper electrodes was measured while voltage was applied to the two upper electrodes facing each other among the upper electrodes. This process was carried out at room temperature and no artificial magnetic field was applied from the outside.

Referring to FIG. 18 , it can be observed that current flows through the other two upper electrodes even when the same voltage is applied to the two upper electrodes, that is, a voltage of 0V is applied. This means that there is a zero bias current. In addition, it shows that phase locking is achieved regardless of the magnitude of the voltage. These characteristics indicate that the active layer in the form of a film used in Preparation Example 3 of the superconducting electronic device is a topological superconductor.

19 is a graph illustrating current characteristics according to time when a voltage of 0V is applied to an electronic device according to Manufacturing Example 3 of a superconducting electronic device.

Referring to FIG. 19 , even when the same voltage is applied to the two upper electrodes, that is, a voltage of 0V is applied, current flows through the other two upper electrodes, and this current appears as a constant alternating current with time. It is the result of a Josephson junction. In addition, it can be seen that the alternating current exhibits periodicity of pi, which is evidence confirming that the active layer in the form of a film used in Preparation Example 3 of the superconducting electronic device is a topological superconductor.

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

Claims (25)

An organic crystal comprising an organic crystal in which a plurality of unit layers having a plurality of aromatic ring groups regularly arranged in a plane are stacked, wherein the stacking of the unit layers is a pi between aromatic ring groups disposed in the unit layers adjacent to each other. -The active layer implemented by pi interaction,
The active layer is a topological superconductor that implements a zero bias current flowing along the edge even in a non-biased state. According to claim 1,
The unit layer of the organic crystal includes a plurality of unit organic molecules including the aromatic ring,
Each unit organic molecule has a first pair of substituents each bonded to immediately adjacent positions among the substitution positions of the aromatic ring and a second pair of substituents respectively bonded to immediately adjacent positions among the remaining substitution positions,
The terminal groups of the substituents included in the first pair of one unit organic molecule among the unit organic molecules included in the unit layer and the terminal groups of the substituents included in the second pair of the other unit organic molecules are Topological superconductors self-assembled by Van Der Waals interactions, London dispersion interactions or hydrogen bonding. 3. The method of claim 2,
A topological superconductor in which a pair of substituents each bonded to immediately adjacent positions among substitution positions of the aromatic ring has increased rigidity compared to a single substituent by a Van Der Waals interaction between them. 3. The method of claim 2,
A topological superconductor in which a pair of substituents each bonded to immediately adjacent positions among substitution positions of the aromatic ring are bonded to ortho positions of the aromatic ring with respect to each other. 3. The method of claim 2,
Each of the substituents is a topological superconductor having a chalcogen element having an unshared pair of electrons directly connected to the aromatic ring. 3. The method of claim 2,
The aromatic ring is a 6 to 46 membered homocyclic aromatic ring or a heterocyclic aromatic ring topological superconductor. 3. The method of claim 2,
wherein the substituents are bonded to symmetry-equivalent positions among the substitution positions of the aromatic ring. According to claim 1,
The organic crystal is a topological superconductor having a basic lattice structure of triclinic, monoclinic, orthorhombic, tetragonal, hexagonal, or cubic. 3. The method of claim 2,
The unit organic molecules are topological superconductors which are organic compounds represented by the following formula (1):
[Formula 1]

In Formula 1,
Ar is a 6 to 46 membered homocyclic aromatic ring or heterocyclic aromatic ring,
-A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ are bonded to immediately adjacent positions among the substitution positions of Ar, there is,
m is an integer from 1 to 8,
A ₁ and A ₂ are independent of each other,

or

ego,
L ₁ and L ₂ are independent of each other,

,

,

,

,

,

,

,

, or

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

, a ₁ , a ₂ , a ₃ , b ₁ , and b ₂ are integers from 0 to 30 regardless of each other, and a ₁ +a ₂ +a ₃ +b ₁ +b ₂ is an integer from 3 to 30 ,
P ₁ , P ₂ , and P ₃ independently of each other are -CR _a R _b - or -(CR _a R _b ) _r O-, r is an integer from 1 to 3;
Q ₁ and Q ₂ are q ₁ -(p ₁ ) _c1 -q ₂ -(p ₂ ) _c2 -q ₃ independent of each other, and q ₁ and q ₃ are independent of each other

or

and q ₂ is a hydrogen group bonded to carbon is substituted or unsubstituted with F, Cl, Br, or I

,

,

,

,

,

,

,

, or

, p ₁ and p ₂ are -CR _a R _b - regardless of each other, c ₁ and c ₂ are integers from 0 to 2 regardless of each other,
X ₁ and X ₂ are independent of each other -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 ,
R _a and R _b independently of each other are H, F, Cl, Br, or I,
R _c , R _d , and R _e independently of each other are H, F, Cl, Br, or I;
U is a cyano group, a hydroxyl group, fluorine, chlorine, iodine, a substituted or unsubstituted C 1 to C 15 alkyl group, a substituted or unsubstituted C 1 to C 15 alkoxy group, a substituted or unsubstituted C 3 to C 15 of a cycloalkyl group, a substituted or unsubstituted C2 to C15 alkenyl group, a substituted or unsubstituted C2 to C15 alkynyl group, a substituted or unsubstituted C5 to C15 aryl group, a substituted or unsubstituted C2 to 15 heteroaryl group, substituted or unsubstituted C 1 to C 15 arylalkyl group, substituted or unsubstituted C 1 to C 15 alkylsulfone group, substituted or unsubstituted C 1 to C 15 alkyl mercapto group, substituted Or an unsubstituted C 1 to C 15 alkylthiocyan group, a substituted or unsubstituted C 1 or C 15 alkyl phosphate group, a substituted or unsubstituted C 1 to C 15 alkylnitro group, a substituted or unsubstituted C 1 to C 15 of an alkylnitroso group, a substituted or unsubstituted C1 to C15 alkylnitrile group, a substituted or unsubstituted C1 to C15 alkylisothiocyanate group, a substituted or unsubstituted C1 to C15 alkylisocyanic acid group , A substituted or unsubstituted C 1 to C 15 alkylcyanic acid group, a substituted or unsubstituted C 1 to C 15 alkylazo group, a substituted or unsubstituted C 1 to C 15 alkylazide group, a substituted or unsubstituted C 1 to 15 ketimine group, substituted or unsubstituted aldimine group having 1 to 15 carbon atoms, substituted or unsubstituted amide group having 1 to 15 carbon atoms, arylalkyl group having 6 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, carbon number Any one selected from 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,
o is an integer between 0 and 16; 10. The method of claim 9,
Ar is benzene, aromatic analogues of benzene containing heteroatoms (heteroatom containing aromatic analogues of benzene), naphthalene, aromatic analogues of naphthalene containing heteroatoms, anthracene, aromatic analogues of anthracene containing heteroatoms, phenalene ( phenalene), aromatic analogues of phenalene containing heteroatoms, phenanthrene, aromatic analogues of phenanthracene containing heteroatoms, cyclopenta[fg]acenaphthylene, hetero Aromatic analogues of cyclopenta[fg]acenaphthylene containing atoms, tetracene, aromatic analogues of tetracene containing heteroatoms, pyrene, aromatic analogues of pyrene containing heteroatoms, benz[de]anthracene, aromatic analogues of benz[de]anthracene containing heteroatoms, triphenylene, aromatic analogues of triphenylene containing heteroatoms, pentacene, aromatic analogues of benz[de]anthracene containing heteroatoms A topological superconductor that is an aromatic analog of pentacene, coronene, or an aromatic analog of coronene containing heteroatoms. 10. The method of claim 9,
Wherein Ar is C _n (n is an integer of 2 to 6) A topological superconductor having an aromatic ring having symmetry. 10. The method of claim 9,
The -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and the -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ are bonded to ortho positions of the Ar with respect to each other. Topological superconductors. 10. The method of claim 9,
Wherein m is 2 or more,
Between the pairs of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and the -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ ,
The -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ or the -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ Topology in which at least one substitution position of Ar is not bonded superconductor. 10. The method of claim 9,
Wherein Ar has C _n (n is an integer of 2 to 6) symmetry,
Wherein m is the same topological superconductor as n. 15. The method of claim 14,
The -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and the -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ are positions having equal symmetry among the substitution positions of Ar. topological superconductors bonded to equivalent positions). 10. The method of claim 9,
The compound is a topological superconductor, which is a compound represented by the following formula (1c):
[Formula 1c]

In 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 in Formula 1 , L ₁ , L ₂ , _n1 , _n2 , Y ₁ , Y ₂ , X ₁ , X ₂ , U and o, respectively. 17. The method of claim 16,
A topological superconductor wherein Ar is an aromatic ring of the following Structural Formula 8:
[Structural Formula 8]

In Structural Formula 8,
T ₁ to T ₁₇ are all C; Some of T ₁ to T ₁₇ may be N, P, B or Si independently of each other, others are 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 ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ are bonded at the G ₄ and G ₅ positions,
the other pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ are bonded at positions G ₁₁ and G ₁₂ ,
U is bonded or unbonded to the remaining G ₁ , G ₂ , G ₇ , G ₈ , G ₉ , or G ₁₄ ,
o is an integer of 0 to 6. 10. The method of claim 9,
The compound is a topological superconductor, which is a compound represented by the following formula 1d:
[Formula 1d]

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 in Formula 1 , L ₁ , L ₂ , _n1 , _n2 , Y ₁ , Y ₂ , X ₁ , X ₂ , U and o, respectively. 10. The method of claim 9,
The compound is a topological superconductor, which is a compound represented by Formula 1e:
[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 in Formula 1 , L ₁ , L ₂ , _n1 , _n2 , Y ₁ , Y ₂ , X ₁ , X ₂ , U and o, respectively. 10. The method of claim 9,
m is greater than or equal to 2,
The angle formed by the pair of -A ₁ -(L ₁ ) _n1 -Y ₁ -X ₁ and -A ₂ -(L ₂ ) _n2 -Y ₂ -X ₂ with respect to the center of Ar is the same topological superconductor. An organic crystal including an organic crystal in which a plurality of unit layers having aromatic ring groups regularly arranged in a plane are stacked, wherein the stacking of the unit layers is pi-pi between aromatic ring groups disposed in the unit layers adjacent to each other. an active layer implemented by interaction; and
At least two edge electrodes connected to an edge of one side of the active layer and spaced apart from each other,
The active layer is an electronic device that is a topological superconductor that implements a zero bias current flowing along the edge even in a state in which no bias is applied. 22. The method of claim 21,
The active layer is a single crystal layer or an electronic device having a polycrystalline structure including a plurality of organic crystals. 22. The method of claim 21,
The corner electrodes are four electronic devices. 22. The method of claim 21,
The electronic device further comprising gate electrodes connected to the active layer on a surface opposite to the surface on which the corner electrodes are formed. An electronic circuit comprising a plurality of electronic devices according to any one of claims 21 to 24, wherein the plurality of electronic devices are electrically connected.

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