Compounds for organic electronic devices, organic electronic devices using the same, and electronic devices using the same

Abstract

The present invention provides a fluorinated material for metal or electrode (cathode) patterning that enables the formation of precise electrode patterns in display devices while reducing the time and cost required for the patterning method. [Solution] Disclosed are a fluorinated compound represented by any one of formulas (2-1) to (2-5), a metal patterning composition containing the same, and an organic electronic element and an electronic device containing the same.

Description

[Technical Field]

[0001] This invention relates to a fluorine-containing metal or a compound for electrode (cathode) patterning, and a transparent display device using the same. [Background technology]

[0002] The continuous advancement of display technology has led to increased user demands for display devices, and terminal display devices (especially smartphones) are required to evolve toward flexibility, full screen, and high integration.

[0003] In particular, with smartphone displays, as technology advances, efforts are being made to maximize screen size even for smartphones of the same size. As a result, development has focused on minimizing the base size of smartphones as much as possible as the screen size increases. In this process, the physical buttons that were on the front of smartphones have disappeared into the screen, and the position of the smartphone camera has also been continuously changed using methods such as notches, holes, and slides.

[0004] Recently, the development of base-less under-display technology has been progressing rapidly, which in turn has led to a rapid advancement in transparent display technology.

[0005] With the development of such display devices, there has recently been growing interest in the implementation of next-generation smartphone display technologies such as UDC (Under Display Camera) and UPS (Under Panel Sensor).

[0006] In particular, UDC cameras cannot function properly unless the display has high transparency; therefore, precise patterning of the cathode is essential to increase transparency.

[0007] Generally, there are two main methods used for electrode patterning. First, a shadow mask is used to pattern the electrodes in the desired area, or second, a laser is used to irradiate the cathode to create a pattern.

[0008] However, electrode patterning methods using shadow masks are susceptible to warping during the high-temperature deposition process due to the typical material properties of metal masks, resulting in distortion of the mask shape and electrode pattern. Consequently, the time and cost required for mask maintenance make this method commercially unsuitable for mass production of devices.

[0009] Furthermore, the electrode patterning method using a laser presents the challenge of having to determine the type and intensity of the laser to avoid damaging the substrate, as the electrodes are patterned in a way that depends on the inherent properties of the laser.

[0010] On the other hand, fluorinated organic compound materials are used in various applications in organic electronic devices. For example, Patent Document 1 discloses an organic EL device having a laminated structure in which a light-emitting layer made of a fluorescent organic solid is interposed between two electrodes facing each other, wherein at least one polymer from the group consisting of chlorotrifluoroethylene homopolymer, dichlorofluoroethylene homopolymer, and copolymer of chlorotrifluoroethylene and dichlorodifluoreneethylene is deposited to further adequately prevent the intrusion of moisture and oxygen into the light-emitting layer, and the compound plays the role of a encapsulant.

[0011] Furthermore, Patent Document 2 and Non-Patent Document 1 disclose that fluorine-containing materials have high chemical and thermal stability and can improve electron transport characteristics, so they can be used as electron transport layers in organic EL devices. They also exhibit hole shielding functionality, so they can be used not only as hole shielding layers but also as protective films, thereby improving the lifespan of the device.

[0012] Patent Document 3 also discloses that fluorine-containing substances can be used as materials for the light-emitting layer in addition to the electron transport layer, and that Patent Document 3 discloses a green light-emitting polymer in which the electroluminescence efficiency is improved by introducing a fluorinated aryl group with strong electron affinity, i.e., a pentafluoroaryl or octafluorobiphenyl group, into poly(p-phenylenevinylene) to induce a balanced encounter between electrons and holes. Furthermore, Patent Document 4 discloses a light-emitting compound containing a fluorine-based branch that has particularly excellent AIEE (Aggregation Induced Enhanced Emission) properties in the solid state. Patent Document 5 discloses an organic light-emitting element comprising a first electrode; a hole transport layer; a light-emitting layer; and a second electrode, wherein a fluorine-substituted C is placed between the first electrode and the hole transport layer. 6y F 6y-2n This document describes an aromatic fluorinated carbon compound and an organic light-emitting device characterized by further inclusion of the compound between the light-emitting layer and the second electrode. This discloses the provision of a low-power organic light-emitting device by enhancing the driving voltage, through the insertion of a thin film containing a fluorine-containing compound at the interface between the first electrode (positive electrode) and the hole injection (hole transport layer) to adjust the interface of the organic light-emitting device using an aromatic fluorinated carbon compound. [Prior art documents] [Patent Documents]

[0013] [Patent Document 1] Japanese Patent Publication No. 1992-206386 [Patent Document 2] Japanese Patent Publication No. 2001-247498 [Patent Document 3] South Korea JP 10-2000-0000628 [Patent Document 4] South Korea JP 10-2005-0115069 [Patent Document 5] Korean Patent No. 10-0846597 [Non-patent literature]

[0014] [Non-Patent Document 1] J. Am. Chem. Soc., 2000, Vol.122, 1832. [Overview of the Initiative] [Problems that the invention aims to solve]

[0015] The present invention aims to provide a fluorinated material for metal or electrode (cathode) patterning that can form precise electrode patterns in display devices and reduce the time and cost required for the patterning method. [Means for solving the problem]

[0016] The present invention provides a fluorine-containing compound represented by the following formula (1), a metal patterning composition containing the same, and an organic electronic device containing the same.

[0017] [ka] [Effects of the Invention]

[0018] The present invention makes it possible to form fine patterns on electrodes without using a shadow mask by using the compound represented by formula (1) as a metal or electrode (cathode) patterning material, facilitating the fabrication of transparent displays with high light transmittance and making UDC applications easier. [Brief explanation of the drawing]

[0019] [Figure 1] This is an illustrative diagram of a display layer structure containing a fluorine compound. [Figure 2] This is an illustrative diagram of a display layer structure containing a fluorine compound. [Figure 3] This is an illustrative diagram of a display layer structure containing a fluorine compound. [Figure 4A] This is a cross-sectional view of Comparative Example 1 using SEM. [Figure 4B]This is a cross-sectional view taken by SEM of Example 3. [Figure 5A] This graph shows the measurement results of the light transmittance for Comparative Example 1 and Example 1. [Figure 5B] This graph shows the measurement results of light transmittance for Comparative Example 1 and Example 2. [Figure 5C] This graph shows the measurement results of light transmittance for Comparative Example 1 and Example 3. [Figure 5D] This graph shows the measurement results of light transmittance for Comparative Example 1 and Example 4. [Figure 5E] This graph shows the measurement results of the light transmittance for Comparative Example 1 and Example 5. [Figure 5F] This graph shows the measurement results of light transmittance for Comparative Example 1 and Example 6. [Figure 5G] This graph shows the measurement results of light transmittance for Comparative Example 1 and Example 7. [Figure 5H] This graph shows the measurement results of light transmittance for Comparative Example 1 and Example 8. [Figure 5I] This graph shows the measurement results of the light transmittance for Comparative Example 1 and Example 9. [Figure 5J] This graph shows the measurement results of light transmittance for Comparative Example 1 and Example 10. [Figure 6A] This graph shows the measurement results of the light transmittance for Comparative Example 3 and Example 11. [Figure 6B] This graph shows the measurement results of light transmittance for Comparative Example 4 and Example 12. [Figure 6C] This graph shows the measurement results of light transmittance for Comparative Example 5 and Example 13. [Figure 7A] This graph shows the measurement results of light transmittance for Comparative Example 6 and Examples 14 to 16. [Figure 7B] This graph shows the measurement results of light transmittance for Comparative Example 6 and Examples 17 to 19. [Figure 7C] This graph shows the measurement results of light transmittance for Comparative Example 6 and Examples 20 to 22. [Figure 7D] This graph shows the measurement results of light transmittance for Comparative Example 6 and Examples 23 to 25. [Figure 8A]This figure shows the measurement results of the contact angle for Comparative Example 7. [Figure 8B] This figure shows the measurement results of the contact angle in Example 26. [Figure 8C] This figure shows the measurement results of the contact angle in Example 27. [Figure 8D] This figure shows the measurement results of the contact angle in Example 28. [Figure 8E] This figure shows the measurement results of the contact angle in Example 29. [Figure 8F] This figure shows the measurement results of the contact angle in Example 30. [Figure 8G] This figure shows the measurement results of the contact angle in Example 31. [Figure 8H] This figure shows the measurement results of the contact angle in Example 32. [Figure 8I] This figure shows the measurement results of the contact angle in Example 33. [Figure 8J] This figure shows the measurement results of the contact angle in Example 34. [Modes for carrying out the invention]

[0020] As used in this specification and the appended claims, unless otherwise specified, the following terms have the meanings set forth below.

[0021] As used herein, the terms "halo" or "halogen" refer to fluorine (F), bromine (Br), chlorine (Cl), or iodine (I), unless otherwise specified.

[0022] As used in this invention, the terms "alkyl" or "alkyl group" refer to a radical of a saturated aliphatic functional group having a single bond with 1 to 60 carbon atoms, including linear alkyl groups, branched alkyl groups, cycloalkyl (alicyclic) groups, alkyl-substituted cycloalkyl groups, and cycloalkyl-substituted alkyl groups, unless otherwise specified.

[0023] As used in this invention, the terms "alkenyl group" or "alkynyl group" refer to, unless otherwise specified, oily, linear, or branched groups containing double or triple bonds with 2 to 60 carbon atoms.

[0024] As used in this invention, the term "cycloalkyl" means, unless otherwise specified, an alkyl group that forms a ring having 3 to 60 carbon atoms, and is not limited thereto.

[0025] As used in this invention, the terms "alkoxyl group," "alkoxy group," or "alkyloxy group" refer to an alkyl group to which an oxygen radical is bonded, and unless otherwise specified, have 1 to 60 carbon atoms, but are not limited thereto.

[0026] As used in this invention, the terms "aryloxyl group" or "aryloxy group" refer to an aryl group to which an oxygen radical is bonded, and unless otherwise specified, have 6 to 60 carbon atoms, but are not limited thereto.

[0027] As used herein, the term "alkylthio group" means an alkyl group to which a sulfur radical is bonded, and unless otherwise specified, has between 1 and 60 carbon atoms, but is not limited thereto.

[0028] As used herein, the term "arylthio group" means an aryl group to which a sulfur radical is bonded, and unless otherwise specified, has 1 to 60 carbon atoms, but is not limited thereto.

[0029] As used herein, the terms "aryl group" and "arylene group" each have 6 to 60 carbon atoms, unless otherwise specified. In the present invention, an aryl group or arylene group means a monocyclic or polycyclic aromatic group, and includes an aromatic ring formed by the bonding or reaction of adjacent substituents. For example, an aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

[0030] The prefix "aryl" or "-ar" signifies a radical substituted with an aryl group. For example, an arylalkyl group is an alkyl group substituted with an aryl group, an arylalkenyl group is an alkenyl group substituted with an aryl group, and an aryl-substituted radical has the number of carbon atoms specified herein. When prefixes are used consecutively, it means that the substituents are listed in the order listed above. For example, an arylalkoxy group means an alkoxy group substituted with an aryl group, an alkoxylcarbonyl group means a carbonyl group substituted with an alkoxyl group, and an arylcarbonylalkenyl group means an alkenyl group substituted with an arylcarbonyl group, where an arylcarbonyl group is a carbonyl group substituted with an aryl group.

[0031] As used herein, the term "heterocyclic group" means, unless otherwise specified, a group comprising one or more heteroatoms, having 2 to 60 carbon atoms, comprising at least one monocyclic and polycyclic ring, and including heteroaliphatic and heteroaromatic rings. It may be formed by the bonding of adjacent functional groups.

[0032] As used herein, the term "heteroatom" refers to N, O, S, P, or Si unless otherwise specified.

[0033] Furthermore, "heterocyclic group" refers to monocyclic structures, ring assemblies, various joined ring systems, and spiro compounds containing heteroatoms. Compounds containing heteroatom groups such as SO2 and P=O instead of the carbon atoms forming the ring, as shown in the compounds below, can also be included in the definition of heterocyclic group.

[0034] [ka]

[0035] As used in this invention, the term "aliphatic ring group" refers to cyclic hydrocarbons excluding aromatic hydrocarbons, and includes monocyclic rings, ring aggregates, various joined ring systems, spiro compounds, etc. Unless otherwise specified, it refers to rings with 3 to 60 carbon atoms, but is not limited thereto. For example, when an aromatic ring such as benzene and a non-aromatic ring such as cyclohexane are condensed, it also falls under the category of an aliphatic ring.

[0036] In this invention, the terms "fluorenyl group," "fluorenylene group," and "fluorentryyl group" refer to monovalent, divalent, or trivalent functional groups in the following structures where R, R', and R'' are all hydrogen atoms, unless otherwise specified. "Substituted fluorenyl group," "substituted fluorenylene group," or "substituted fluorentryyl group" means that at least one of the substituents R, R', and R'' is a substituent other than hydrogen, and includes cases where R and R' are bonded to each other and form a spiro compound with the carbon atom to which they are bonded. In this specification, regardless of valency, fluorenyl groups, fluorenylene groups, and fluorentryyl groups may all be referred to as fluorene groups.

[0037] [ka]

[0038] In this specification, the "group names" corresponding to aryl groups, arylene groups, heterocyclic groups, etc., as exemplified by each symbol and its substituents, may be the names of the groups that reflect their valency, or they may be the names of the parent compounds. For example, in the case of "phenanthrene," a type of aryl group, the monovalent group can be named "phenanthryl" and the divalent group "phenanthrylene," distinguishing the group names by valency, or it can be named "phenanthrene," the name of the parent compound, regardless of valency. Similarly, in the case of pyrimidines, they can be named "pyrimidine" regardless of valency, or they can be named with the corresponding "group name," such as pyrimidinyl for monovalent groups and pyrimidinylene for divalent groups. Furthermore, in this specification, numbers and letters indicating position may be omitted when listing compound names and substituent names. For example, pyrido[4,3-d]pyrimidine can be written as pyridopyrimidine, benzoflo[2,3-d]pyrimidine as benzoflopyrimidine, and 9,9-dimethyl-9H-fluorene as dimethylfluorene. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be written as benzoquinoxaline.

[0039] Furthermore, unless otherwise explicitly stated, the formulas used in this invention are applied in the same way as the definition of substituents by the definition of the exponents in the following formulas.

[0040] [ka]

[0041] In the formula, if a is an integer of 0, the substituent R 1 It is absent, and if a is an integer of 1, there is one substituent R 1 It is bonded to any of the carbon atoms forming the benzene ring, and when a is an integer of 2 or 3, it is bonded as follows, and in this case, R 1 These may be the same or different from each other, and when a is an integer between 4 and 6, they are similarly bonded to the carbon atoms of the benzene ring, while the hydrogen atoms bonded to the carbon atoms forming the benzene ring are omitted from the notation.

[0042]

Chem.

[0043] Also, unless otherwise specified in this specification, when representing a condensed ring, in "number-condensed ring", the numerical value represents the number of condensed rings. For example, a form in which three rings are condensed with each other, such as anthracene, phenanthrene, benzoxazoline, etc., can be represented as 3-condensed ring.

[0044] Also, unless otherwise specified in this specification, when representing a ring in the form of "number atoms", such as a 5-membered ring, a 6-membered ring, etc., the number in "number - atom" represents the number of elements forming the ring. For example, thiophene, furan, etc. correspond to 5-membered rings, and benzene, pyridine, etc. may correspond to 6-membered rings.

[0045] Also, unless otherwise specified in this specification, a ring formed by bonding adjacent groups to each other is an aromatic ring group of C6~C 60 ; a fluorenyl group; a heterocyclic group of C2~C containing at least one heteroatom of O, N, S, Si, and P 60 ; and an aliphatic ring group of C3~C 60 ; and can be selected from the group consisting of.

[0046] At this time, unless otherwise specified in this specification, "adjacent groups" means, taking the following formula as an example, R 1 and R 2 ; R 2 and R 3 ; R 3 and R 4 ; R 5 and R 6 not only; but also includes R 7 and R 8 sharing one carbon, and also includes R 1 and R 7 ; R 1 and R 8 ; or R 4 and R 5This may include substituents bonded to ring constituent elements (such as carbon and nitrogen) that are not immediately adjacent, such as two or more substituents. In other words, if there are substituents on immediately adjacent ring constituent elements such as carbon or nitrogen, these can become adjacent groups. However, if there are no substituents bonded to the immediately adjacent ring constituent element, the substituent bonded to the next ring constituent element can become an adjacent group. Furthermore, substituents bonded to the same ring constituent carbon can also become adjacent groups.

[0047] In the following equation, R 7 and R 8 When substituents bonded to the same carbon atom bond to each other to form a ring, as in the example above, a compound containing a spiro moiety can be formed.

[0048] [ka]

[0049] Furthermore, in this specification, the expression "adjacent groups can bond with each other to form a ring" is used interchangeably with "adjacent groups can bond with each other to selectively form a ring," meaning that at least one pair of adjacent groups can bond with each other to form a ring.

[0050] The following describes compounds according to one aspect of the present invention.

[0051] According to one aspect of the present invention, a fluorinated compound represented by the following formula (1) is provided.

[0052] [ka]

[0053] [In the formula, each symbol can be defined as follows: 1) Ar 1 and Ar 2 These are independent of each other, C6~C 60An aryl group; containing at least one heteroatom of O, N, S, Si, and P (C2-C2). 60 heterocyclic group; and C3~C 60 aliphatic ring and C6~C 60 Selected from the group consisting of fused ring groups of aromatic rings. The aforementioned Ar 1 and Ar 2 If the group is an aryl group, preferably C6-C 30 The aryl group, more preferably C6-C 20 The aryl group, more preferably C6-C 18 The aryl group may be, for example, phenyl, biphenyl, naphthyl, or terphenyl. The aforementioned Ar 1 and Ar 2 If it is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2-C 20 A heterocyclic group, more preferably C2-C 16 The heterocyclic group may be, for example, pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, dibenzofuran, dibenzothiophene, naphthobenzothiophene, naphthobenzofuran, benzofuran, benzothiophene, etc. 2) A, B, C, and D are independent of each other, -CR a R b -;-NR c -;-O-;-S-;-SiR d R e -;C6~C 60 Allerene group; fluorenylene group; and C2-C containing at least one heteroatom of O, N, S, Si and P. 60 Selected from the group consisting of heterocyclic groups. When A, B, C and D are allylene groups, preferably C6 to C 30 Arylene group, more preferably C6~C 20 Arylene groups, more preferably C6-C 18 The allerene group may be, for example, phenylene, biphenylene, naphthylene, terphenylene, etc. When A, B, C, and D are fluorenylene groups, they may be 9,9-dimethyl-9H-fluorenylene, 9,9-diphenyl-9H-fluorenylene, 9,9'-spirobifluorenylene, etc. When A, B, C, and D are heterocyclic groups, preferably C2 to C 30 A heterocyclic group, more preferably C2-C 20 A heterocyclic group, more preferably C2-C 16 The heterocyclic group may be, for example, pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, dibenzofuran, dibenzothiophene, naphthobenzothiophene, naphthobenzofuran, benzofuran, benzothiophene, etc. However, if m is 0, A is C6~C 60 An aryl group of; or a C2-C containing at least one heteroatom of O, N, S, Si, and P. 60 It is a heterocyclic group. If A is an aryl group, preferably C6~C 30 The aryl group, more preferably C6-C 20 The aryl group, more preferably C6-C 18 The aryl group may be, for example, phenyl, biphenyl, naphthyl, or terphenyl. When A is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2-C 20 A heterocyclic group, more preferably C2-C 16 The heterocyclic group may be, for example, pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, dibenzofuran, dibenzothiophene, naphthobenzothiophene, naphthobenzofuran, benzofuran, benzothiophene, etc. 3) R 1 , R 2 and R 3 They are either the same or different, and are independent of each other, C6~C 60 aryl group; fluorenyl group; C2-C containing at least one heteroatom of O, N, S, Si and P 60 heterocyclic group; C3~C 60 aliphatic ring and C6~C60 The condensed ring group of the aromatic ring; C1-C 50 The alkyl group; C1-C 50 The alkoxyl group; C6-C 60 The aryloxy group; -L-NR’R’’; the substituent represented by the formula (1-1); and the substituent represented by the formula (1-2); selected from the group consisting of, or adjacent groups may be bonded to each other to form a ring. When the R 1 ~R 3 is an aryl group, preferably a C6-C 30 aryl group, more preferably a C6-C 20 aryl group, still more preferably a C6-C 18 aryl group, for example, phenyl, biphenyl, naphthyl, terphenyl may be used. When the R 1 ~R 3 is a fluorenyl group, 9,9-dimethyl-9H-fluorenyl, 9,9-diphenyl-9H-fluorenyl, 9,9'-spirobifluorenyl, etc. may be used. When the R 1 ~R 3 is a heterocyclic group, preferably a C2-C 30 heterocyclic group, more preferably a C2-C 20 heterocyclic group, still more preferably a C2-C 16 heterocyclic group, for example, pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, dibenzofuran, dibenzothiophene, naphthobenzothiophene, naphthobenzofuran, benzofuran, benzothiophene, etc. may be used. When the R 1 ~R 3 is an alkyl group, preferably a C1-C 20 alkyl group, more preferably a C1-C 10 alkyl group may be used, for example, methyl, t-butyl, etc. may be used. When the R 1 ~R 3 is an alkoxy group, preferably a C1-C 20 alkoxyl group, more preferably a C1-C 10The alkoxyl group may be, for example, methoxy, t-butoxy, etc. Said R 1 ~R 3 When it is an aryloxy group, it is preferably a C6-C 30 aryloxy group, more preferably a C6-C 20 aryloxy group may also be used. However, at least one of R 1 , R 2 and R 3 is a substituent represented by the formula (1-1) or a substituent represented by the formula (1-2). 4) a, b, and c are each independently an integer from 0 to 10, provided that a + b + c is 1 or more. 5) m and n are each independently an integer from 0 to 50. Here, when n is 0, R 2 is absent, and at this time, A + c is 1 or more. When m is 0, R 3 is absent, and at this time, A + b is 1 or more. When both n and m are 0, R 2 and R 3 are absent, and at this time, a is an integer from 1 to 10. 6) X 1 , X 2 , X 3 and X 4 are each independently CR f R g , NR h , O, S or SiR i R j is. 7) R’ and R'' are each independently a C6-C 60 aryl group; a C2-C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; and a condensed ring group of a C3-C 60 aliphatic ring and a C6-C 60 aromatic ring; selected from the group consisting of, or adjacent groups may be bonded to each other to form a ring. When said R’ and R'' are aryl groups, preferably a C6-C 30 aryl group, more preferably a C6-C 20The aryl group, more preferably C6-C 18 The aryl group may be, for example, phenyl, biphenyl, naphthyl, or terphenyl. When R' and R'' are heterocyclic groups, preferably C2~C 30 A heterocyclic group, more preferably C2-C 20 A heterocyclic group, more preferably C2-C 16 The heterocyclic group may be, for example, pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, dibenzofuran, dibenzothiophene, naphthobenzothiophene, naphthobenzofuran, benzofuran, benzothiophene, etc. 8)R a , R b , R c , R d , R e , R f , R g , R h , R i and R j These are, independently of each other: hydrogen; deuterium; halogens; C6~C 60 An aryl group; containing at least one heteroatom of O, N, S, Si, and P (C2-C2). 60 heterocyclic group; C3~C 60 aliphatic ring and C6~C 60 A fused ring group of an aromatic ring; C1~C 50 A substituent is selected from the group consisting of an alkyl group; a substituent represented by formula (1-1); and a substituent represented by formula (1-2); or adjacent groups may bond to each other to form a ring. The aforementioned R a ~R j If the group is an aryl group, preferably C6-C 30 The aryl group, more preferably C6-C 20 The aryl group, more preferably C6-C 18 The aryl group may be, for example, phenyl, biphenyl, naphthyl, or terphenyl. The aforementioned R a ~R j If it is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2-C 20A heterocyclic group, more preferably C2-C 16 The heterocyclic group may be, for example, pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, dibenzofuran, dibenzothiophene, naphthobenzothiophene, naphthobenzofuran, benzofuran, benzothiophene, etc. The aforementioned R a ~R j If the alkyl group is C1-C 20 Alkyl alkyl groups, more preferably C1-C 10 It may also be an alkyl group, such as methyl or t-butyl. 9) o, p, q, and r are independent integers of 0 or 1. In this case, if o is 0, X 1 If p is absent and p is 0, X 2 If is absent and the above q is 0, X 3 If X is absent and r is 0, 4 He will be absent. 10) x is an integer between 3 and 50. Also, y+z is an integer of 2x+1, 2x, or 2x-2. For example, y may be 0 and z may be 2x+1, 2x, or 2x-2. In this case, x is preferably an integer between 3 and 20, more preferably an integer between 5 and 15, and even more preferably an integer between 5 and 12. If x exceeds the above range, there is a problem that Td will be high during vacuum deposition, and if it is below the above range, there is a high possibility that the compound will become liquid. 11) i, t, and v are independent integers between 0 and 20, and s, u, and w are independent integers between 1 and 20. Here, if i or t is 0, B and C are simple combinations, in which case s or u is 1. 12) L is a single bond; C6~C 60 Arylene group; fluorenylene group; C2-C containing at least one heteroatom of O, N, S, Si and P. 60 heterocyclic group; C1~C 50 alkylene group; and C3~C 60 aliphatic ring and C6~C 60 Selected from the group consisting of fused ring groups of aromatic rings. When L is an arylene group, preferably C6~C 30 Arylene group, more preferably C6~C 20 Arylene groups, more preferably C6-C 18 The allerene group may be, for example, phenylene, biphenylene, naphthylene, terphenylene, etc. When L is a fluorenylene group, it may be 9,9-dimethyl-9H-fluorenylene, 9,9-diphenyl-9H-fluorenylene, 9,9'-spirobifluorenylene, etc. When L is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2-C 20 A heterocyclic group, more preferably C2-C 16 The heterocyclic group may be, for example, pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, dibenzofuran, dibenzothiophene, naphthobenzothiophene, naphthobenzofuran, benzofuran, benzothiophene, etc. When L is an alkylene group, preferably C1 to C 20 an alkylene group, more preferably C1~C 10 It may also be an alkylene group, such as methylene or butylene. 13) Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, condensed ring group, alkyl group, alkoxy group, aryloxy group, and rings formed by the bonding of adjacent groups to each other are, respectively, deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1~C 20 alkylthio group; C1~C 20 Alkoxyl group of C6~C 20 aryloxy group; C1~C 20 alkyl groups; C2~C 20 alkenyl group; C2~C 20 Alkynyl group of C6~C 20 aryl group; deuterium-substituted C6-C 20 aryl group; halogen-substituted C6-C 20 aryl group; fluorenyl group; C2~C20 heterocyclic group; C3~C 20 Cycloalkyl groups; C7~C 20 Arylalkyl groups; and C8-C 20 The arylalkenyl group of the arylalkenyl group may be further substituted with one or more substituents selected from the group consisting of the arylalkenyl group 60 aliphatic ring or C6~C 60 Aromatic ring or C2~C 60 This refers to a fused ring consisting of a heterocycle or a combination thereof, including saturated or unsaturated rings.

[0054] The above equation (1) is given by the following equation (2).

[0055] [ka]

[0056] (In the formula, Ar 1 Ar 2 , R 1 , R 2 , R 3 A, a, b, c, m, and n are the same as the definitions given in formula (1) above.

[0057] Preferably, formula (1) is represented by one of the following formulas (2-1) to (2-5).

[0058] [ka]

[0059] (In the formula, Ar 1 Ar 2 , R 1 , R 3 , R a , R b , R c , R d , R e (a and c have the same meanings as those defined in formula (1) above.)

[0060] Preferably, formula (1) is represented by the following formulas (2-6).

[0061] [ka]

[0062] [In the formula, each symbol can be defined as follows: 1) Ar 1 Ar 2 , R 1 , R 2 , R 3 a, b, and c are the same as the definitions described in formula (1) above, 2) A' is C6~C 60 an arylene group; or a C2-C containing at least one heteroatom of O, N, S, Si, and P. 60 It is a heterocyclic group. When A' is an arylene group, preferably C6~C 30 Arylene group, more preferably C6~C 20 Arylene groups, more preferably C6-C 18 The allerene group may be, for example, phenylene, biphenylene, naphthylene, terphenylene, triphenylenylene, etc. When A' is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2-C 20 A heterocyclic group, more preferably C2-C 16 The heterocyclic group may be pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, benzofuran, benzothiophene, etc.

[0063] Preferably, formula (1) is represented by the following formula (2-12).

[0064] [ka]

[0065] [In the formula, each symbol can be defined as follows: 1) b, c, x, y, z and Ar 2 This is equivalent to the definition described in formula (1) above, 2) A' is equivalent to the definition described in formula (2-6) above, 3) R 4 C6~C 60 aryl group; fluorenyl group; C2-C containing at least one heteroatom of O, N, S, Si and P 60 heterocyclic group; C3~C 60 aliphatic ring and C6~C 60 A fused ring group of an aromatic ring; C1~C 50 alkyl groups; C1~C 50 Alkoxyl group of C6~C 60 A group selected from the group consisting of aryloxy groups; and -L-NR'R''; or adjacent groups may bond to each other to form a ring. The terms L, R', and R'' above have the same meaning as those defined in formula (1) above. The aforementioned R 4 If the group is an aryl group, preferably C6-C 30 The aryl group, more preferably C6-C 20 The aryl group, more preferably C6-C 18 The aryl group may be, for example, phenyl, biphenyl, naphthyl, or terphenyl. The aforementioned R 4 If the group is a fluorenyl group, it may be 9,9-dimethyl-9H-fluorenyl, 9,9-diphenyl-9H-fluorenyl, 9,9'-spirobaifluorenyl, etc. The aforementioned R 4 If it is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2-C 20 A heterocyclic group, more preferably C2-C 16 The heterocyclic group may be, for example, pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, dibenzofuran, dibenzothiophene, naphthobenzothiophene, naphthobenzofuran, benzofuran, benzothiophene, etc. The aforementioned R 4If the alkyl group is C1-C 20 Alkyl alkyl groups, more preferably C1-C 10 It may also be an alkyl group, such as methyl or t-butyl. The aforementioned R 4 If the group is an alkoxy group, preferably C1-C 20 Alkoxyl groups, more preferably C1-C 10 The alkoxy group may be, for example, methoxy, t-butoxy, etc. The aforementioned R 4 If the group is an aryloxy group, preferably C6-C 30 an aryloxy group, more preferably C6-C 20 It may also be an aryloxy group. 4) R 3 ' is hydrogen; deuterium; C6~C 60 aryl group; fluorenyl group; C2-C containing at least one heteroatom of O, N, S, Si, or P 60 heterocyclic group; C3~C 60 aliphatic ring and C6~C 60 A fused ring group of an aromatic ring; C1~C 50 alkyl groups; C1~C 50 Alkoxyl group of C6~C 60 A group selected from the group consisting of aryloxy groups and -L-NR'R'' may be formed by adjacent groups bonding to each other to form a ring. The aforementioned R 3 If ' is an aryl group, preferably C6~C 30 The aryl group, more preferably C6-C 20 The aryl group, more preferably C6-C 18 The aryl group may be, for example, phenyl, biphenyl, naphthyl, or terphenyl. The aforementioned R 3 If ' is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2-C 20 A heterocyclic group, more preferably C2-C 16The heterocyclic group may be, for example, pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, dibenzofuran, dibenzothiophene, naphthobenzothiophene, naphthobenzofuran, benzofuran, benzothiophene, etc. The aforementioned R 3 If ' is an alkyl group, preferably C1-C 20 Alkyl alkyl groups, more preferably C1-C 10 It may also be an alkyl group, such as methyl or t-butyl. The aforementioned R 3 If ' is an alkoxy group, preferably C1~C 20 Alkoxyl groups, more preferably C1-C 10 The alkoxy group may be, for example, methoxy, t-butoxy, etc. The aforementioned R 3 If ' is an aryloxy group, preferably C6~C 30 an aryloxy group, more preferably C6-C 20 It may also be an aryloxy group.

[0066] More preferably, formula (1) is represented by the following formulas (2-7).

[0067] [ka]

[0068] [In the formula, 1)R 1 , R 2 , R 3 and b are equivalent to the definitions described in formula (1) above, 2) A' is equivalent to the definition described in formula (2-6) above, 3) a' and c' are independent integers between 0 and 5.

[0069] More preferably, formula (1) is represented by the following formulas (2-8) or (2-9).

[0070] [ka]

[0071] [In the formula, each symbol can be defined as follows: 1) b, B, i, x, y, z, and s are the same as the definitions described in formula (1) above, 2) A' is equivalent to the definition described in formula (2-6) above, 3) R 4 This is equivalent to the definition given in formula (2-12) above.

[0072] Most preferably, formula (1) is represented by the following formula (2-10) or formula (2-11).

[0073] [ka]

[0074] [In the formula, 1) b, x, y, and z have the same meanings as those defined in formula (1) above, 2) A' is equivalent to the definition described in formula (2-6) above, 3) R 4 This is equivalent to the definition given in formula (2-12) above.

[0075] Furthermore, equation (1) is represented by equation (3) below.

[0076] [ka]

[0077] (In the formula, Ar 1 Ar 2 , R 1 , R 3 A, c, and m have the same meanings as those defined in formula (1) above.

[0078] Preferably, formula (1) is represented by the following formula (3-1).

[0079] [ka]

[0080] [In the formula, 1)R 1 , R 3 1) a' and c' are defined as in the same way as in formula (1) above, and 2) a' and c' are independent integers between 0 and 5.

[0081] Furthermore, equation (1) above is represented by equation (4) below.

[0082] [ka]

[0083] [In the formula, 1) Ar 1 , X 1 , X 3 , R 1 , R 2 a and b are the same as the definitions described in formula (1) above, 2) o' and p' are independent of each other, either 0 or 1, provided that o'+p' is 1 or greater. 3) A'' is C6~C 60 An aryl group of; or a C2-C containing at least one heteroatom of O, N, S, Si, and P. 60 It is a heterocyclic group.

[0084] If A'' is an aryl group, preferably C6~C 30 The aryl group, more preferably C6-C 20 The aryl group, more preferably C6-C 18 The aryl group may be, for example, phenyl, biphenyl, naphthyl, or terphenyl.

[0085] If A'' is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2-C 20 A heterocyclic group, more preferably C2-C 16 The heterocyclic group may be, for example, pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, benzofuran, benzothiophene, etc.

[0086] Preferably, formula (1) is represented by the following formula (4-1).

[0087] [ka]

[0088] [In the formula, 1) Ar 1 , R 1 , R 2 ,X1, a, and b are the same as the definitions described in formula (1) above, and 2)A'' is the same as the definition described in formula (4) above.

[0089] More preferably, formula (1) is represented by any one of the following formulas (4-2) to (4-6).

[0090] [ka]

[0091] [In the formula, 1) Ar 1 , R 1 , R 2 , R f , R g , R h , R i , R j , a and b are the same as the definitions described in formula (1) above, and 2) A'' is the same as the definition described in formula (4) above.

[0092] Furthermore, more preferably, formula (1) is represented by the following formulas (4-7).

[0093] [ka]

[0094] [In the formula, 1)X 1 , R 1 and R 2is synonymous with the definition described in the above formula (1), and 2) a'' and b' are each independently an integer from 0 to 4.

[0095] Further, the above formula (1) is represented by the following formula (5) or formula (6).

[0096]

Chemical formula

[0097] [In the formula, 1) Ar 1 , Ar 2 , X 1 , X 2 , X 4 , R 1 , R 2 , R 3 , a, b and c are synonymous with the definition described in the above formula (1), and 2) A' is synonymous with the definition described in the above formula (2-6).

[0098] Preferably, the above formula (1) is represented by any one of the following formulas (5-1) to (5-3).

[0099]

Chemical formula

[0100] [In the formula, 1) X 1 , X 2 , R 1 , R 2 and R 3 are synonymous with the definition described in the above formula (1), and 2) a'' and c'' are each independently an integer from 0 to 4, and b'' is an integer from 0 to 2.

[0101] Further, preferably, the above formula (1) is represented by the following formula (6-1) or formula (6-2).

[0102]

Chemical formula

[0103] [In the formula, 1)X 1 , X 4 , R 1 , R 2 and R 3 is equivalent to the definition described in formula (1) above, and 2) a'' and c'' are independent integers between 0 and 4, and b'' is an integer between 0 and 2.

[0104] Furthermore, equation (1-1) is represented by the following equation (1-1-a) or equation (1-1-b).

[0105] [ka]

[0106] [In the formula, 1) x, y, z, s, and B are the same as defined in formula (1), and 2) i' is an integer between 1 and 20.]

[0107] On the other hand, the above formula (1-1-b) may also be the following formula (1-1-c).

[0108] [ka]

[0109] [In the formula, 1) x, y, z, and s are the same as the definitions described in formula (1) above, 2) i' is an integer from 1 to 20, d is an integer from 0 to 4, and 3) R 5 Deuterium; halogen; C6~C 20 An aryl group; containing at least one heteroatom of O, N, S, Si, and P (C2-C2). 20 heterocyclic group; C3~C 20 A fused ring group of an aliphatic ring and a C6-C aromatic ring; C1-C 20 A group consisting of alkyl groups; or adjacent groups may bond to each other to form a ring.

[0110] Furthermore, equation (1-2) can be represented by the following equations (1-2-a) or (1-2-b).

[0111]

Chem.

[0112] [In the formula, 1) x, y, z, C, D, u, v, and w have the same meanings as defined in formula (1), and 2) t' is an integer from 1 to 20.]

[0113] Specifically, the formula (1-1) and formula (1-2) may be any one of the following compounds, but are not limited thereto.

[0114]

Chem.

[0115]

Chem.

[0116] On the other hand, specifically, the compound represented by the formula (1) may be any one of the following compounds, but is not limited thereto.

[0117]

Chem.

[0118]

Chem.

[0119]

Chem.

[0120]

Chem.

[0121]

Chem.

[0122]

change

[0123]

change

[0124]

change

[0125]

change

[0126]

change

[0127]

change

[0128]

change

[0129]

change

[0130]

change

[0131]

change

[0132] [ka]

[0133] [ka]

[0134] Here, the fluorine content of the compound represented by formula (1) may be 20% or more. Preferably it may be 20% to 80%, and more preferably 30% to 60%.

[0135] The fluorine content of the compounds described herein is given by the following formula (A). Fluorine content = Number of fluorine atoms in the compound / Total number of atoms in the compound × 100 (A) Here, the number of fluorine atoms in a compound refers to the number of fluorine atoms contained in the compound, while the total number of atoms in a compound refers to the total number of atoms in the compound that contains fluorine.

[0136] In another aspect of the present invention, the present invention provides an organic electronic element comprising a positive electrode, an organic layer formed on the positive electrode, and a metal patterning layer formed on the organic layer, wherein the metal patterning layer comprises one single compound or two or more compounds represented by formula (1).

[0137] The organic layer may include at least one of the following layers: a hole injection layer, a hole transport layer, a light emission auxiliary layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer.

[0138] In yet another aspect of the present invention, the present invention provides an electronic device comprising a display device including an organic electronic element represented by formula (1), and a control unit for driving the display device.

[0139] The stacked structure of an organic electronic device containing the compound of the present invention will be described below with reference to Figures 1 to 3.

[0140] When assigning reference numerals to the components of each drawing, identical components should, as far as possible, have the same reference numeral when shown in other drawings. Furthermore, in the description of the present invention, if it is determined that a specific description of a related known configuration or function would obscure the gist of the invention, such detailed description will be omitted.

[0141] Wherever "includes," "possesses," "becomes," etc., are used as referred to herein, other parts may be added unless "only" is used. When a component is expressed singularly, it includes cases where it includes multiple components unless otherwise explicitly stated.

[0142] Furthermore, when describing the components of the present invention, terms such as First, Second, A, B, (a), (b), etc., may be used. These terms are used to distinguish a component from other components, and the terms do not limit the nature, order, sequence, etc., of that component. When it is stated that a component is “connected,” “joined,” or “connected” to another component, it should be understood that the component may be directly connected or connected to the other components, but further components may be “connected,” “joined,” or “connected” between each component.

[0143] Furthermore, when a component such as a layer, membrane, region, or plate is said to be "on top of" another component, this should be understood to include not only the case where it is "directly above" the other component, but also the case where there is another component in between. Conversely, when a component is said to be "directly above" another part, this should be understood to mean that there is no other part in between.

[0144] Figures 1, 2, and 3 are illustrative diagrams of organic electronic devices according to embodiments of the present invention.

[0145] Referring to Figure 1, an organic electronic element 100 according to one embodiment of the present invention includes a first electrode 110 formed on a substrate (not shown), organic material layers 120, 130, 140, and 150 formed on the first electrode 110, and a metal patterning layer 170 formed on the organic material layers.

[0146] The organic layer may sequentially include a hole injection layer 120, a hole transport layer 130, a light-emitting layer 140, and an electron transport layer 150 on the first electrode 110. It may further include a hole blocking layer, an electron blocking layer, a light-emitting auxiliary layer 220, a buffer layer 210, an electron injection layer, etc., and the electron transport layer 150 may act as a hole blocking layer. An electron injection layer may be formed on the electron transport layer 150, and may be excluded if necessary, but is not limited thereto.

[0147] The metal patterning layer 190 containing the compound represented by formula (1) is formed on the organic layer, and the second electrode 170 is not formed in the portion where the metal patterning layer is formed. That is, by using the compound represented by formula (1) according to the present invention as the material for the metal patterning layer 170, it is possible to form only the portion or selective portion where the second electrode material is to be formed. Alternatively, by forming the metal patterning layer on the organic layer as shown in Figure 3, the formation of the second electrode can be suppressed.

[0148] When a metal patterning layer is coated, the formation of a negative electrode on the metal patterning layer is suppressed depending on the structure of the compound and the fluorine content of the compound entering the metal patterning layer, ultimately resulting in only a very small amount of negative electrode being formed, or no negative electrode being formed at all.

[0149] In this context, when considering the coating of electrodes (electrically conductive materials), light transmittance is used to determine the amount of electrode material present on a given surface. This is because electrode materials contain metals, and electrically conductive materials such as metals attenuate and / or absorb light. Therefore, a surface with a light transmittance exceeding 90% in the visible light region of the electromagnetic spectrum is considered to contain substantially no electrically conductive material.

[0150] As a result, the pixels of organic electronic elements containing metal patterning have high transmittance and do not emit light, acting as blanks. This high transmittance allows them to transmit light to various wide-angle sensors (optical sensors) on the substrate (TFT substrate) without optical noise.

[0151] Therefore, in an organic electronic device containing a metal patterning layer (see Figure 3), when forming the organic layer on the substrate (ITO), the light-emitting layer 140 may or may not be present, and since there is no second electrode (negative electrode) on the metal patterning layer, electricity does not pass through and no light is emitted.

[0152] On the other hand, the present invention provides a metal patterning composition comprising two or more compounds of the same type or structurally different from the compound represented by formula (1).

[0153] Furthermore, the present invention provides an organic electronic element comprising a metal patterning layer containing the compound represented by formula (1).

[0154] Furthermore, the organic layer can be manufactured in fewer layers by solution processes or solvent processes, such as spin coating, nozzle printing, inkjet printing, slot coating, dip coating, roll-to-roll, doctor blade, screen printing, or thermal transfer, rather than by vapor deposition using various polymer materials. Since the organic layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the method of formation.

[0155] Furthermore, an organic electronic element according to one embodiment of the present invention can be selected from the group consisting of organic electron light-emitting devices, organic solar cells, organic photoreceptors, organic transistors, monochromatic lighting elements, and quantum dot display elements.

[0156] Other embodiments of the present invention may include an electronic device that includes a display device comprising the organic electronic element of the present invention described above, and a control unit for controlling the display device. In this case, the electronic device may be a current or future wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation systems, game consoles, various TVs, and various computers.

[0157] The following examples will specifically describe the synthesis of the compound represented by formula (1) of the present invention and the production of the organic electronic device of the present invention, but the present invention is not limited to the following examples.

[0158] Example of synthesis The compound represented by formula (1) according to the present invention (Final Product) is synthesized as shown in reaction scheme 1 below, but is not limited thereto.

[0159] <Reaction Scheme 1>

[0160] [ka]

[0161] [In the formula, 1)Hal 1 Hal 2 Hal 3 and Hal 4 These are, independently of each other, Cl, Br, or I. 2) a'+a'' is a, b'+b'' is b, and c'+c'' is c, where at least one of a'', b'', and c'' is 1 or greater. 3) Y is -[C x H y F z ] or -[C x H y F z ]-[D] v -[C x H y F z ] w And, 4) Y' is -[B]i’ -[C x H y F z ] s or -[C] t’ -[C x H y F z ] u -[D] v -[C x H y F z ] w And, 5)X 1 , X 2 , X 3 , X 4 o, p, q, r, R 1 , R 2 , R 3 a, b, c, Ar 1 Ar 2 A, D, m, n, i', t', u, v, w, x, y, and z are synonymous with the above definitions.

[0162] I. Synthesis of Sub1

[0163] 1. Example of Sub1-9 synthesis

[0164] [ka]

[0165] In a round-bottom flask, 1,4-dibromo-2-iodobenzene (10.0 g, 27.6 mmol) was dissolved in THF (138 mL), then naphthalene-1-ylboronic acid (5.2 g, 30.4 mmol), K2CO3 (11.5 g, 82.9 mmol), Pd(PPh3)4 (1.92 g, 1.66 mmol), and water (69 mL) were added, and the mixture was stirred at 80°C. After the reaction was complete, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. Subsequently, the resulting compound was subjected to silica gel column chromatography and recrystallized to obtain 7.5 g of product (yield: 75%).

[0166] 2. Example of Sub1-12 synthesis

[0167] [ka]

[0168] 4-Bromo-1-chloro-2-iodobenzene (5.0 g, 15.8 mmol), THF (79 mL), naphtho[2,3-b]benzofuran-3-ylboronic acid (4.5 g, 17.3 mmol), K2CO3 (6.5 g, 47.3 mmol), Pd(PPh3)4 (1.09 g, 0.95 mmol), and water (39 mL) were combined using the synthesis method described in Sub1-9 to obtain 4.9 g of product (yield: 77%).

[0169] 3. Example of Sub1-46 synthesis

[0170] [ka]

[0171] 3-Bromo-1-iodonaphthalene (5.0 g, 15.0 mmol), THF (75 mL), (3-bromophenyl)boronic acid (3.3 g, 16.5 mmol), K2CO3 (6.2 g, 45.0 mmol), Pd(PPh3)4 (1.04 g, 0.90 mmol), and water (38 mL) were combined using the synthesis method described in Sub1-9 to obtain 4.4 g of product (yield: 81%).

[0172] 4. Example of Sub1-58 synthesis

[0173] [ka]

[0174] In a round-bottom flask, dibenzo[b,d]thiophene-3-amine (5.0 g, 25.1 mmol), toluene (250 mL), 1-bromo-4-chlorobenzene (10.6 g, 55.2 mmol), Pd2(dba)3 (1.38 g, 1.51 mmol), P(t-Bu)3 (0.61 g, 3.01 mmol), and NaOt-Bu (9.6 g, 100 mmol) were added and the mixture was stirred at 100°C. After the reaction was complete, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. Subsequently, the resulting compound was subjected to silica gel column chromatography and recrystallized to obtain 7.5 g of product (yield: 71%).

[0175] 5. Example of Sub1-63 synthesis

[0176] [ka]

[0177] In a round-bottom flask, 4-bromonaphthalene-1-ol (5.0 g, 22.4 mmol), 1-bromo-4-iodobenzene (12.7 g, 44.8 mmol), and DMSO (22 mL) were added and the mixture was stirred for 5 minutes. Subsequently, t-BuOK (6.29 g, 56.0 mmol) was slowly added dropwise, and the mixture was stirred at 45°C for 8 hours. After the reaction was complete, the mixture was extracted with EA (ethyl acetate) and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was then subjected to silica gel column chromatography and recrystallized to obtain 4.9 g of product (yield: 58%).

[0178] 6. Example of Sub1-69 synthesis

[0179] [ka]

[0180] (2-bromo-4-chlorophenyl)(4-chlorophenyl)sulfan (6.0 g, 18.0 mmol), THF (90 mL), phenylboronic acid (2.4 g, 19.8 mmol), K2CO3 (7.4 g, 53.9 mmol), Pd(PPh3)4 (1.25 g, 1.08 mmol), and water (45 mL) were combined using the synthesis method described in Sub1-9 to obtain 4.4 g of product (yield: 74%).

[0181] 7. Example of Sub1-78 synthesis

[0182] [ka]

[0183] 3,6-dibromo-9H-carbazole (5.0 g, 15.4 mmol), toluene (154 mL), 4'-bromo-2,3,4,5,6-pentafluoro-1,1'-biphenyl (10.9 g, 33.8 mmol), Pd2(dba)3 (0.85 g, 0.92 mmol), P(t-Bu)3 (0.37 g, 1.85 mmol), and NaOt-Bu (5.9 g, 61.5 mmol) were synthesized using the synthesis method described in Sub1-58 to obtain 6.8 g of product (yield: 78%).

[0184] 8. Example of Sub1-83 synthesis

[0185] [ka]

[0186] 7-Bromo-2-chlorodibenzo[b,d]furan (5.0 g, 17.8 mmol), THF (89 mL), Sub3-2 (10.2 g, 19.5 mmol), K2CO3 (7.4 g, 53.3 mmol), Pd(PPh3)4 (1.23 g, 1.07 mmol), and water (44 mL) were combined using the synthesis method for Sub1-9 to obtain 8.3 g of product (yield: 78%).

[0187] 9. Example of Sub1-112 synthesis

[0188] [ka]

[0189] 2-Chloro-8,8-dimethyl-5,8-dihydroindeno[2,1-c]carbazole (5.0 g, 15.7 mmol, CAS #: 2376527-04-5), toluene (79 mL), bromobenzene (2.7 g, 17.3 mmol), Pd2(dba)3 (0.43 g, 0.47 mmol), P(t-Bu)3 (0.19 g, 0.94 mmol), and NaOt-Bu (3.0 g, 31.5 mmol) were synthesized using the synthesis method of Sub1-58 to obtain 4.7 g of product (yield: 76%).

[0190] On the other hand, compounds belonging to Sub1 may be, but are not limited to, the following compounds. Table 1 below shows the FD-MS (Field Desorption-Mass Spectrometry) values ​​or CAS numbers (hereinafter referred to as 'CAS#') of the following compounds. In Table 1 below, known compounds are indicated by CAS#, and unknown compounds are indicated by FD-MS.

[0191] [ka]

[0192] [ka]

[0193] [ka]

[0194] [ka]

[0195] [ka]

[0196] [ka]

[0197] [ka]

[0198] [Table 1-1]

[0199] [Table 1-2]

[0200] [Table 1-3]

[0201] II. Synthesis of Sub2

[0202] 1. Example of Sub2-12 synthesis

[0203] [ka]

[0204] (1) Example of Sub2-12-a synthesis

[0205] In a round-bottom flask, 4-iodoaniline (30.0 g, 137 mmol), Cu (34.8 g, 548 mmol), and DMSO (274 mL) were added and dissolved at 70°C, followed by stirring for 30 minutes. Then, 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-hexadecafluoro-1-iodo-8-((perfluoropropan-2-yl)oxy)octane (117 g, 164 mmol) was slowly added dropwise for 1 hour, followed by stirring at 120°C for 24 hours. After the reaction was complete, distilled water was added, and the resulting solid was filtered under reduced pressure. The filtrate was then extracted with ethyl acetate, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was then separated by silica gel column to obtain 63.0 g of product (yield: 68%).

[0206] (2)Sub2-12-b synthesis example

[0207] In a round-bottom flask, the Sub2-12-a (50.0 g, 73.8 mmol) synthesized above and 35% HCl (6.84 mL, 222 mmol) were added and the mixture was stirred for 1 hour. Subsequently, the mixture was cooled in an ice bath, and an aqueous solution of NaNO2 (7.13 g, 103 mmol) was added dropwise for 30 minutes. Then, KI (17.2 g, 103 mmol) dissolved in distilled water (60 mL) was added dropwise. Next, THF (80 mL) was added, and the mixture was stirred overnight at room temperature. Once the reaction was complete, the mixture was neutralized with aqueous NaOH solution, extracted with diethyl ether, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was separated by silica gel column chromatography to obtain 47.0 g of product (yield: 81%).

[0208] (3) Example of Sub2-12 synthesis

[0209] In a round-bottom flask, the synthesized Sub2-12-b (40.0 g, 50.8 mmol), Cu (7.10 g, 112 mmol), and DMSO (102 mL) were added and dissolved at 70°C, followed by stirring for 30 minutes. Then, 1,1,2,2,3,3,4,4,5,5,6,6-dodecafluoro-1,6-diiodohexane (33.7 g, 60.9 mmol) was slowly added dropwise for 1 hour, followed by stirring at 120°C for 24 hours. Once the reaction was complete, distilled water was added, and the resulting solid was filtered under reduced pressure. The filtrate was then extracted with ethyl acetate, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was separated by silica gel column to obtain 11.0 g of product (yield: 20%).

[0210] 2. Examples of Sub2-13 combination

[0211] [ka]

[0212] 1-iodo-4-(trifluoromethyl)benzene (40.0 g, 147 mmol), Cu (20.6 g, 324 mmol), 1,1,2,2-tetrafluoro-1,2-diiodoethane (62.4 g, 176 mmol), and DMSO (294 mL) were combined using the synthesis method of Sub2-12 to obtain 9.3 g of product (yield: 17%).

[0213] 3. Example of Sub2-15 synthesis

[0214] [ka]

[0215] 1-iodo-4-(perfluorohexyl)benzene (40.0 g, 76.6 mmol), Cu (10.7 g, 169 mmol), 1,1,2,2-tetrafluoro-1,2-diiodoethane (32.5 g, 92.0 mmol), and DMSO (153 mL) were combined using the synthesis method of Sub2-12 to obtain 9.1 g of product (yield: 19%).

[0216] 4. Example of Sub2-16 synthesis

[0217] 1-iodo-4-(perfluorohexyl)benzene (40.0 g, 76.6 mmol), Cu (10.7 g, 169 mmol), 1,1,2,2,3,3,4,4,5,5,6,6-dodecafluoro-1,6-diiodohexane (50.9 g, 92.0 mmol), and DMSO (153 mL) were synthesized using the method described in Sub2-12 to obtain 13.2 g of product (yield: 21%).

[0218] On the other hand, compounds belonging to Sub2 may be, but are not limited to, the following compounds. Table 2 below shows the FD-MS values ​​or CAS# of the following compounds. In Table 2 below, known compounds are shown by CAS#, and unknown compounds are shown by FD-MS.

[0219] [ka]

[0220] [Table 2]

[0221] III. Sub3 Synthesis

[0222] 1. Example of Sub3-1 synthesis

[0223] [ka]

[0224] In a round-bottom flask, 1-iodo-4-(trifluoromethyl)benzene (5.0 g, 18.4 mmol) was added, followed by bis(pinacolate)diborone (4.9 g, 19.3 mmol), Pd2(dba)3 (0.51 g, 0.55 mmol), x-phos (0.53 g, 1.10 mmol), KOAc (3.6 g, 36.8 mmol), and toluene (61 mL). The mixture was refluxed at 120°C. After the reaction was complete, the reaction solution was concentrated and separated by silica gel column to obtain 3.9 g of product (yield: 79%).

[0225] 2. Example of Sub3-2 synthesis

[0226] (1) Example of Sub3-2-a synthesis

[0227] [ka]

[0228] In a round-bottom flask, the previously synthesized 1-bromo-4-chlorobenzene (30.0 g, 157 mmol), Cu (39.8 g, 627 mmol), and DMSO (313 mL) were added and dissolved at 70°C, followed by stirring for 30 minutes. Then, Sub2-1 (76.9 g, 172 mmol) was slowly added dropwise for 1 hour, followed by stirring at 120°C for 24 hours. Once the reaction was complete, distilled water was added, and the resulting solid was filtered under reduced pressure. The filtrate was then extracted with ethyl acetate, the organic layer was dried over MgSO4 and concentrated, and the resulting compound was separated by silica gel column chromatography and recrystallized to obtain 50.7 g of product (yield: 75%).

[0229] (2) Example of Sub3-2 synthesis

[0230] Sub3-2-a (50.7 g, 118 mmol), bis(pinacolate)diborone (31.4 g, 124 mmol), Pd2(dba)3 (3.24 g, 3.54 mmol), x-phos (3.37 g, 7.07 mmol), KOAc (23.1 g, 236 mmol), and toluene (393 mL) synthesized as described above were combined using the synthesis method for Sub3-1 to obtain 49.9 g of product (yield: 81%).

[0231] 3. Example of Sub3-7 synthesis

[0232] [ka]

[0233] (1) Example of Sub3-7-a synthesis

[0234] 3-Bromo-3'-chloro-1,1'-biphenyl (10.0 g, 37.4 mmol), Cu (9.5 g, 145 mmol), DMSO (75 mL), and Sub2-1 (18.3 g, 41.1 mmol) were combined using the synthesis method for Sub3-2-a to obtain 14.6 g of product (yield: 77%).

[0235] (2) Example of Sub3-7 synthesis

[0236] Sub3-7-a (14.6 g, 28.9 mmol), bis(pinacolate)diborone (7.7 g, 30.3 mmol), Pd2(dba)3 (0.79 g, 0.87 mmol), x-phos (0.83 g, 1.73 mmol), KOAc (5.7 g, 57.7 mmol), and toluene (96 mL), synthesized as described above, were used with the synthesis method of Sub3-1 to obtain 13.8 g of product (yield: 80%).

[0237] 4. Example of Sub3-15 synthesis

[0238] [ka]

[0239] (1) Example of Sub3-15-a synthesis

[0240] In a round-bottom flask, add (3-chlorophenyl)boronic acid (8.0 g, 51.2 mmol), 1,1,1,1,1,1,1,1,1,1,1,1,1-tridecafluoro-8-iodo-1λ 16 Octa-1,3,5-triyne (26.7 g, 56.3 mmol) was added and dissolved in DME (ethylene glycol dimethyl ether) (256 mL) and 1N NaHCO3 aqueous solution (128 mL). Then Pd(PPh3)4 (3.55 g, 3.07 mmol) was added and the mixture was stirred under reflux for 5 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with diethyl ether and brine. The resulting organic layer was then dehydrated with MgSO4 to remove any remaining water. Subsequently, the resulting organic layer was filtered under reduced pressure and passed through a silica gel column to obtain 17.7 g of the product (yield: 76%).

[0241] (2) Example of Sub3-15 synthesis

[0242] Sub3-15-a (17.7 g, 38.7 mmol), bis(pinacolate)diborone (10.3 g, 40.6 mmol), Pd2(dba)3 (1.06 g, 1.16 mmol), x-phos (1.11 g, 2.32 mmol), KOAc (7.6 g, 77.3 mmol), and toluene (129 mL), synthesized as described above, were used with the synthesis method of Sub3-1 to obtain 16.9 g of product (yield: 79%).

[0243] 5. Example of Sub3-23 synthesis

[0244] [ka]

[0245] (1) Example of Sub3-23-a synthesis

[0246] 1,3-Dibromo-5-chlorobenzene (30.0 g, 111 mmol), Cu (56.4 g, 888 mmol), DMSO (222 mL), and Sub2-4 (158 g, 244 mmol) were used in the synthesis of Sub3-2-a to obtain 99.8 g of product (yield: 78%).

[0247] (2) Example of Sub3-23 synthesis

[0248] Sub3-23-a (99.8 g, 86.9 mmol), bis(pinacolate)diborone (23.2 g, 91.2 mmol), Pd2(dba)3 (2.39 g, 2.61 mmol), x-phos (2.49 g, 5.21 mmol), KOAc (17.1 g, 174 mmol), and toluene (290 mL), synthesized as described above, were used with the synthesis method of Sub3-1 to obtain 84.5 g of product (yield: 78%).

[0249] On the other hand, compounds belonging to Sub3 may be, but are not limited to, the following compounds. Table 3 below shows the FD-MS values ​​of the following compounds.

[0250] [ka]

[0251] [ka]

[0252] [Table 3]

[0253] IV. Synthesis of the Final Product

[0254] 1. Example of P1-1 synthesis

[0255] [ka]

[0256] In a round-bottom flask, Sub1-52 (3.0 g, 7.77 mmol), Cu (4.0 g, 62.2 mmol), and DMSO (16 mL) were added and dissolved at 70°C, followed by stirring for 30 minutes. Then, Sub2-3 (9.3 g, 17.1 mmol) was slowly added dropwise over 1 hour, followed by stirring at 120°C for 24 hours. Once the reaction was complete, distilled water was added, and the resulting solid was filtered under reduced pressure. The filtrate was then extracted with ethyl acetate, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was separated by silica gel column chromatography and recrystallized to obtain 6.6 g of product (yield: 80%).

[0257] 2. Example of synthesis of P1-22

[0258] [ka]

[0259] (1) Example of Inter1-22 synthesis

[0260] Sub1-1 (1.0 g, 5.22 mmol) was dissolved in toluene (17 mL) in a round flask, then Sub3-20 (4.39 g, 5.22 mmol), K2CO3 (2.17 g, 15.7 mmol), and Pd(PPh3)4 (0.12 g, 0.10 mmol) were added, and the mixture was stirred at 120 °C. After the reaction was complete, the product was separated by silica gel column chromatography and recrystallized to obtain 3.53 g of product (yield: 82%).

[0261] (2) Example of P1-22 synthesis

[0262] In a round flask, the Inter1-22 (3.0 g, 3.64 mmol) synthesized above was dissolved in toluene (12 mL), then Sub3-2 (1.9 g, 3.64 mmol), K2CO3 (1.5 g, 10.9 mmol), and Pd(PPh3)4 (0.08 g, 0.07 mmol) were added, and the mixture was stirred at 120 °C. After the reaction was complete, the product was separated by silica gel column chromatography and recrystallized to obtain 3.41 g of product (yield: 79%).

[0263] 3. Examples of synthesis of P1-23

[0264] [ka]

[0265] (1) Example of Inter1-23 synthesis

[0266] Sub1-1 (1.0 g, 5.22 mmol), Sub3-23 (7.1 g, 5.75 mmol), K2CO3 (2.2 g, 15.7 mmol), Pd(PPh3)4 (0.12 g, 0.10 mmol), and toluene (17.4 mL) were combined using the synthesis method of Inter1-22 to obtain 4.4 g of product (yield: 69%).

[0267] (2) Example of synthesis of P1-23

[0268] Inter1-23 (4.4g, 3.60 mmol), Sub3-5 (2.86g, 3.96 mmol), K2CO3 (1.49g, 10.8 mmol), Pd(PPh3)4 (0.08g, 0.07 mmol), and toluene (12 mL) synthesized as described above were used to obtain 4.9 g of product (yield: 76%) using the synthesis method of P1-22.

[0269] 4. Examples of synthesis of P1-34

[0270] [ka]

[0271] Sub1-2 (1.0 g, 4.24 mmol), Sub3-20 (7.8 g, 9.33 mmol), K2CO3 (1.76 g, 12.72 mmol), Pd(PPh3)4 (0.10 g, 0.08 mmol), and toluene (14 mL) were used in the synthesis of P1-22 to obtain 5.0 g of product (yield: 78%).

[0272] 5. Examples of synthesis of P1-44

[0273] [ka]

[0274] (1) Example of Inter1-44 synthesis

[0275] Sub1-22 (1.0 g, 3.74 mmol), Sub3-23 (5.1 g, 4.11 mmol), K2CO3 (1.6 g, 11.21 mmol), Pd(PPh3)4 (0.09 g, 0.07 mmol), and toluene (13 mL) were combined using the synthesis method for Inter1-22 to obtain 3.3 g of product (yield: 67%).

[0276] (2) Example of synthesis of P1-44

[0277] Inter1-44 (3.3g, 2.51 mmol), Sub3-5 (2.0g, 2.76 mmol), K2CO3 (1.0g, 7.52 mmol), Pd(PPh3)4 (0.06g, 0.05 mmol), and toluene (8.4 mL) synthesized as described above were used to obtain 3.6 g of product (yield: 77%) using the synthesis method described in P1-22.

[0278] 6. Examples of synthesis using P1-46

[0279] [ka]

[0280] Sub1-23 (1.0 g, 3.21 mmol), Sub3-20 (5.9 g, 7.05 mmol), K2CO3 (1.3 g, 9.62 mmol), Pd(PPh3)4 (0.07 g, 0.06 mmol), and toluene (11 mL) were combined using the synthesis method of P1-22 to obtain 4.6 g of product (yield: 79%).

[0281] 7. Examples of synthesis of P1-50

[0282] [ka]

[0283] Sub1-24 (1.0g, 3.21 mmol), Sub3-23 (8.8g, 7.05 mmol), K2CO3 (1.3g, 9.62 mmol), Pd(PPh3)4 (0.07g, 0.06 mmol), and toluene (11 mL) were combined using the synthesis method of P1-22 to obtain 5.3 g of product (yield: 70%).

[0284] 8. Examples of synthesis using P1-52

[0285] [ka]

[0286] Sub1-36 (1.0 g, 2.58 mmol), Sub3-20 (4.8 g, 5.67 mmol), K2CO3 (1.1 g, 7.73 mmol), Pd(PPh3)4 (0.06 g, 0.05 mmol), and toluene (8.6 mL) were combined using the synthesis method of P1-22 to obtain 3.1 g of product (yield: 73%).

[0287] 9. Examples of synthesis using P1-55

[0288] [ka]

[0289] Sub1-26 (1.0g, 3.21 mmol), Sub3-23 (8.8g, 7.05 mmol), K2CO3 (1.3g, 9.62 mmol), Pd(PPh3)4 (0.07g, 0.06 mmol), and toluene (11 mL) were combined using the synthesis method of P1-22 to obtain 5.5 g of product (yield: 72%).

[0290] 10. Examples of synthesis using P1-61

[0291] [ka]

[0292] Sub1-38 (2.0 g, 3.66 mmol), Sub3-2 (8.4 g, 16.1 mmol), K2CO3 (3.0 g, 22.0 mmol), Pd(PPh3)4 (0.08 g, 0.07 mmol), and toluene (12 mL) were combined using the synthesis method described in P1-22 to obtain 3.8 g of product (yield: 58%).

[0293] 11. Synthesis examples of P1-63

[0294] [ka]

[0295] Sub1-41 (2.0 g, 6.99 mmol), Sub3-2 (8.0 g, 15.4 mmol), K2CO3 (2.90 g, 21.0 mmol), Pd(PPh3)4 (0.16 g, 0.14 mmol), and toluene (23 mL) were combined using the synthesis method described in P1-22 to obtain 4.8 g of product (yield: 75%).

[0296] 12. Examples of synthesis using P1-65

[0297] [ka]

[0298] Sub1-44 (1.0 g, 3.50 mmol), Sub3-20 (6.5 g, 7.69 mmol), K2CO3 (1.45 g, 10.5 mmol), Pd(PPh3)4 (0.08 g, 0.07 mmol), and toluene (12 mL) were combined using the synthesis method of P1-22 to obtain 4.1 g of product (yield: 76%).

[0299] 13. Synthesis example of P1-67

[0300] [ka]

[0301] Sub1-47 (2.0 g, 5.95 mmol), Sub3-2 (6.8 g, 13.1 mmol), K2CO3 (2.5 g, 17.9 mmol), Pd(PPh3)4 (0.14 g, 0.12 mmol), and toluene (20 mL) were combined using the synthesis method of P1-22 to obtain 4.4 g of product (yield: 77%).

[0302] 14. Synthesis examples of P1-69

[0303] [ka]

[0304] Sub1-45 (1.0 g, 2.76 mmol), Sub3-23 (7.6 g, 6.08 mmol), K2CO3 (1.2 g, 8.29 mmol), Pd(PPh3)4 (0.06 g, 0.06 mmol), and toluene (9.2 mL) were used with the synthesis method of P1-22 to obtain 4.8 g of product (yield: 71%).

[0305] 15. Synthesis example of P1-71

[0306] [ka]

[0307] Sub1-42 (2.0g, 6.99 mmol), Sub3-2 (8.0g, 15.4 mmol), K2CO3 (2.9g, 21.0 mmol), Pd(PPh3)4 (0.16g, 0.14 mmol), and toluene (23 mL) were combined using the synthesis method of P1-22 to obtain 4.7 g of product (yield: 74%).

[0308] 16. Synthesis example of P1-73

[0309] [ka]

[0310] Sub1-52 (0.8g, 2.07mmol), Sub3-23 (5.7g, 4.56mmol), K2CO3 (0.86g, 6.22mmol), Pd(PPh3)4 (0.05g, 0.04mmol), and Luen (6.9mL) were synthesized using the synthesis method for P1-22 to obtain 3.9g of product (yield: 76%).

[0311] 17. Example of P2-1 synthesis

[0312] [ka]

[0313] Sub1-54 (2.0 g, 6.33 mmol), Sub3-2 (10.9 g, 20.9 mmol), K2CO3 (5.3 g, 38.0 mmol), Pd(PPh3)4 (0.15 g, 0.13 mmol), and toluene (21 mL) were combined using the synthesis method described in P1-22 to obtain 4.9 g of product (yield: 61%).

[0314] 18. Example of P2-2 synthesis

[0315] [ka]

[0316] Sub1-55 (1.0 g, 3.15 mmol), Sub3-2 (5.42 g, 10.4 mmol), K2CO3 (1.3 g, 9.44 mmol), Pd(PPh3)4 (0.07 g, 0.06 mmol), and toluene (11 mL) were combined using the synthesis method of P1-22 to obtain 3.1 g of product (yield: 78%).

[0317] 19. Example of P3-2 synthesis

[0318] [ka]

[0319] Sub1-56 (2.0 g, 4.15 mmol), Sub3-2 (7.2 g, 13.7 mmol), K2CO3 (3.4 g, 24.9 mmol), Pd(PPh3)4 (0.10 g, 0.08 mmol), and toluene (14 mL) were combined using the synthesis method of P1-22 to obtain 3.6 g of product (yield: 61%).

[0320] 20. Example of P3-4 synthesis

[0321] [ka]

[0322] Sub1-58 (1.5g, 3.58 mmol), Cu (1.8g, 28.6 mmol), Sub2-4 (5.1g, 7.88 mmol), and DMSO (7 mL) synthesized as described above were used with the synthesis method of P1-1 to obtain 3.8 g of product (yield: 76%).

[0323] 21. Example of P3-5 synthesis

[0324] [ka]

[0325] Sub1-59 (2.0 g, 3.23 mmol), Sub3-20 (6.0 g, 7.10 mmol), K2CO3 (1.34 g, 9.69 mmol), Pd(PPh3)4 (0.07 g, 0.06 mmol), and toluene (11 mL) were combined using the synthesis method of P1-22 to obtain 4.1 g of product (yield: 68%).

[0326] 22. Example of P4-2 synthesis

[0327] [ka]

[0328] Sub1-63 (1.5 g, 3.97 mmol), Cu (2.0 g, 31.7 mmol), Sub2-4 (5.6 g, 8.73 mmol), and DMSO (8 mL) synthesized as described above were used with the synthesis method of P1-1 to obtain 3.6 g of product (yield: 72%).

[0329] 23. Example of P4-4 synthesis

[0330] [ka]

[0331] Sub1-62 (2.0 g, 6.10 mmol), Sub3-3 (8.4 g, 13.4 mmol), K2CO3 (2.5 g, 18.3 mmol), Pd(PPh3)4 (0.14 g, 0.12 mmol), and toluene (20 mL) were combined using the synthesis method of P1-22 to obtain 5.2 g of product (yield: 73%).

[0332] 24. Example of P5-3 synthesis

[0333] [ka]

[0334] Sub1-67 (2.0 g, 5.81 mmol), Sub3-2 (6.7 g, 12.8 mmol), K2CO3 (2.4 g, 17.4 mmol), Pd(PPh3)4 (0.13 g, 0.12 mmol), and toluene (19 mL) were combined using the synthesis method described in P1-22 to obtain 4.5 g of product (yield: 79%).

[0335] 25. Example of synthesis of P5-6

[0336] [ka]

[0337] Sub1-69 (2.0 g, 6.04 mmol), Sub3-2 (6.9 g, 13.3 mmol), K2CO3 (2.5 g, 18.1 mmol), Pd(PPh3)4 (0.14 g, 0.12 mmol), and toluene (20 mL) were synthesized using the method described in P1-22 to obtain 4.8 g of product (yield: 75%).

[0338] 26. Example of P6-1 synthesis

[0339] [ka]

[0340] Sub1-70 (3.0 g, 6.27 mmol), Cu (3.2 g, 50.2 mmol), Sub2-1 (6.2 g, 13.8 mmol), and DMSO (13 mL) were combined using the synthesis method of P1-1 to obtain 4.9 g of product (yield: 81%).

[0341] 27. Example of synthesis of P6-4

[0342] [ka]

[0343] Sub1-70 (2.0 g, 4.18 mmol), Sub3-2 (4.8 g, 9.20 mmol), K2CO3 (1.7 g, 12.6 mmol), Pd(PPh3)4 (0.10 g, 0.08 mmol), and toluene (14 mL) were synthesized using the method described in P1-22 to obtain 3.3 g of product (yield: 72%).

[0344] 28. Example of synthesis of P7-1

[0345] [ka]

[0346] Sub1-73 (3.0 g, 6.07 mmol), Cu (3.1 g, 48.6 mmol), Sub2-1 (6.0 g, 13.4 mmol), and DMSO (12 mL) were combined using the synthesis method of P1-1 to obtain 4.4 g of product (yield: 75%).

[0347] 29. Example of synthesis on page 7-4

[0348] [ka]

[0349] Sub1-73 (2.0g, 4.05 mmol), Sub3-2 (4.7g, 8.90 mmol), K2CO3 (1.68g, 12.1 mmol), Pd(PPh3)4 (0.09g, 0.08 mmol), and toluene (14 mL) were combined using the synthesis method described in P1-22 to obtain 3.5 g of product (yield: 76%).

[0350] 30. Example of synthesis of P8-2

[0351] [ka]

[0352] Sub1-77 (3.0 g, 3.75 mmol), Cu (2.9 g, 45.0 mmol), Sub2-1 (7.4 g, 16.5 mmol), and DMSO (7 mL) were combined using the synthesis method of P1-1 to obtain 3.4 g of product (yield: 52%).

[0353] 31. Example of synthesis of P8-3

[0354] [ka]

[0355] Sub1-78 (2.0 g, 3.53 mmol), Cu (1.8 g, 28.2 mmol), Sub2-4 (5.0 g, 7.76 mmol), and DMSO (7 mL) synthesized as described above were used with the synthesis method of P1-1 to obtain 3.9 g of product (yield: 77%).

[0356] 32. Example of synthesis of P9-3

[0357] [ka]

[0358] Sub1-81 (2.0 g, 6.14 mmol), Sub3-2 (7.1 g, 13.5 mmol), K2CO3 (2.5 g, 18.4 mmol), Pd(PPh3)4 (0.14 g, 0.12 mmol), and toluene (21 mL) were synthesized using the method described in P1-22 to obtain 4.3 g of product (yield: 73%).

[0359] 33. Example of synthesis on page 9-4

[0360] [ka]

[0361] Sub1-83 (3.0 g, 5.03 mmol), Cu (2.6 g, 40.2 mmol), Sub2-1 (2.3 g, 5.03 mmol), and DMSO (10 mL) synthesized as described above were used with the synthesis method of P1-1 to obtain 3.6 g of product (yield: 82%).

[0362] 34. Synthesis example of P9-6

[0363] [ka]

[0364] Sub1-82 (1.0g, 3.07mmol), Sub3-24 (6.2g, 6.75mmol), K2CO3 (1.3g, 9.20mmol), Pd(PPh3)4 (0.07g, 0.06mmol), and toluene (10mL) were synthesized using the synthesis method for P1-22 to obtain 3.8g of product (yield: 71%).

[0365] 35. Example of synthesis of P10-1

[0366] [ka]

[0367] Sub1-81 (3.0 g, 8.77 mmol), Cu (4.5 g, 70.2 mmol), Sub2-4 (12.5 g, 19.3 mmol), and DMSO (18 mL) were combined using the synthesis method described in P1-1 to obtain 8.2 g of product (yield: 77%).

[0368] 36. Example of synthesis on page 10-5

[0369] [ka]

[0370] Sub1-85 (1.0g, 2.92 mmol), Sub3-24 (5.9g, 6.43 mmol), K2CO3 (1.2g, 8.77 mmol), Pd(PPh3)4 (0.07g, 0.06 mmol), and toluene (10 mL) were combined using the synthesis method of P1-22 to obtain 3.6 g of product (yield: 70%).

[0371] 37. Example of synthesis on page 11-2

[0372] [ka]

[0373] Sub1-90 (1.0g, 2.84 mmol), Sub3-20 (5.3g, 6.25 mmol), K2CO3 (1.2g, 8.52 mmol), Pd(PPh3)4 (0.07g, 0.06 mmol), and toluene (10 mL) were combined using the synthesis method of P1-22 to obtain 3.4 g of product (yield: 73%).

[0374] 38. Synthesis example of P11-4

[0375] [ka]

[0376] Sub1-91 (3.0 g, 6.30 mmol), Cu (3.2 g, 50.4 mmol), Sub2-1 (6.2 g, 13.9 mmol), and DMSO (13 mL) were combined using the synthesis method of P1-1 to obtain 4.8 g of product (yield: 80%).

[0377] 39. Synthesis example of P11-6

[0378] [ka]

[0379] Sub1-91 (2.0 g, 4.20 mmol), Sub3-20 (7.8 g, 9.24 mmol), K2CO3 (1.7 g, 12.6 mmol), Pd(PPh3)4 (0.10 g, 0.08 mmol), and toluene (14 mL) were combined using the synthesis method of P1-22 to obtain 5.2 g of product (yield: 71%).

[0380] 40. Synthesis example of P11-10

[0381] [ka]

[0382] Sub1-95 (2.0g, 4.08 mmol), Sub3-20 (7.5g, 8.98 mmol), K2CO3 (1.7g, 12.2 mmol), Pd(PPh3)4 (0.09g, 0.08 mmol), and toluene (14 mL) were synthesized using the method described in P1-22 to obtain 4.9 g of product (yield: 68%).

[0383] 41. Example of synthesis on page 12-1

[0384] [ka]

[0385] Sub1-98 (2.0 g, 5.43 mmol), Sub3-2 (6.2 g, 12.0 mmol), K2CO3 (2.3 g, 16.3 mmol), Pd(PPh3)4 (0.13 g, 0.11 mmol), and toluene (18 mL) were combined using the synthesis method described in P1-22 to obtain 4.0 g of product (yield: 73%).

[0386] 42. Example of synthesis on page 13-3

[0387] [ka]

[0388] In a round-bottom flask, Sub1-103 (2.0 g, 6.5 mmol), toluene (33 mL), Sub3-2-a (6.2 g, 14.4 mmol), Pd2(dba)3 (0.18 g, 0.20 mmol), P(t-Bu)3 (0.08 g, 0.39 mmol), and NaOt-Bu (2.5 g, 26.1 mmol) were added and stirred at 120°C. After the reaction was complete, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. Subsequently, the resulting compound was subjected to silica gel column chromatography and recrystallized to obtain 5.1 g of product (yield: 72%).

[0389] 43. Synthesis example of P14-4

[0390] [ka]

[0391] Sub1-108 (2.0 g, 4.52 mmol), Sub3-20 (4.2 g, 4.97 mmol), K2CO3 (1.9 g, 13.6 mmol), Pd(PPh3)4 (0.10 g, 0.09 mmol), and toluene (15 mL) were combined using the synthesis method of P1-22 to obtain 4.0 g of product (yield: 79%).

[0392] 44. Synthesis example of P15-2

[0393] [ka]

[0394] Sub1-110 (3.0 g, 9.41 mmol), Cu (4.8 g, 75.3 mmol), Sub2-4 (13.4 g, 20.7 mmol), and DMSO (19 mL) were combined using the synthesis method described in P1-1 to obtain 5.8 g of product (yield: 77%).

[0395] 45. Synthesis example of P16-2

[0396] [ka]

[0397] Sub1-114 (3.0 g, 8.26 mmol), Cu (4.2 g, 66.1 mmol), Sub2-1 (11.7 g, 18.2 mmol), and DMSO (17 mL) were combined using the synthesis method of P1-1 to obtain 3.7 g of product (yield: 75%).

[0398] 46. ​​Example of synthesis on page 17-1

[0399] [ka]

[0400] Sub1-117 (2.0 g, 7.80 mmol), Sub3-32 (9.3 g, 17.2 mmol), Pd2(dba)3 (0.21 g, 0.23 mmol), P(t-Bu)3 (0.09 g, 0.47 mmol), NaOt-Bu (3.0 g, 31.2 mmol), and toluene (39 mL) were used with the synthesis method of P13-3 to obtain 7.3 g of product (yield: 74%).

[0401] The FD-MS values ​​of compounds P1-1 to P17-4 of the present invention, produced by the synthesis examples described above, are shown in Table 4 below.

[0402] [Table 4-1]

[0403] [Table 4-2]

[0404] [Table 4-3]

[0405] Light transmittance measurement

[0406] Example 1: Comparison of light transmittance according to the type of metal patterning layer First, an organic layer of N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluoren-2-amine (hereinafter abbreviated as 'C-1') was formed on a glass substrate by vacuum deposition to a thickness of 100 nm. On the organic layer, compound P1-22 of the present invention was vacuum deposited to a thickness of 10 nm to form an electrode patterning layer. Subsequently, Yb was vacuum deposited on the electrode patterning layer as an electron injection layer, and then Mg and Ag were deposited as a negative electrode in a 1:9 weight ratio. Subsequently, N4,N4'-diphenyl-N4,N4'-bis(9-phenyl-9H-carbazole-3-yl)-[1,1'-biphenyl]-4,4'-diamine (hereinafter abbreviated as 'D-1') was deposited to a thickness of 70 nm as a capping layer to prepare a sample necessary for light transmittance measurement.

[0407] Examples 2 to 10 A light transmittance sample was prepared in the same manner as in Example 1, except that the compounds of the present invention listed in Table 5 below were used as the metal (electrode) patterning layer material instead of compound P1-22 of the present invention.

[0408] Comparative Example 1 A light transmittance sample was prepared in the same manner as in Example 1, except that a metal (electrode) patterning layer was not used.

[0409] Comparative Example 2 A light transmittance sample was prepared in the same manner as in Example 1, except that comparative compound A was used instead of compound P1-22 of the present invention as the metal (electrode) patterning layer material.

[0410] Comparative compound A

[0411] [ka]

[0412] The light transmittance samples of the examples and comparative examples prepared in this manner were measured at 550 nm in the visible light region using a Lambda 365 UV / VIS spectrometer (Perkinelmer). The measurement results are shown in Table 5 below. The fluorine content of the metal (electrode) patterning layer material is also shown in Table 5 below. The results in Table 5 below were created based on the graph of the light transmittance measurement results in Figure 5.

[0413] [Table 5]

[0414] As can be seen from the results in Table 5 above, in Comparative Example 1, which did not use a metal patterning layer, and in Comparative Compound A, which is a compound with a low intramolecular fluorine content, it was confirmed that the light transmittance was less than 90%, while in Examples 1 to 10, which used the present invention compound with an intramolecular fluorine content of 30% or more, it was confirmed that the light transmittance was 90% or more.

[0415] In particular, in the case of Comparative Example 1, comparative evaluations with Comparative Example 2 and Examples 1 to 10 confirmed that each lot exhibited a light transmittance of 69.13% to 72.38%. Furthermore, in the case of comparative compound A, which has an intramolecular fluorine content of 13.16%, it was confirmed that it had a lower light transmittance than Comparative Example 1, which does not contain intramolecular fluorine.

[0416] Comparative Example 1 showed slight differences in light transmittance from lot to lot. To correct for this, we calculated the difference in light transmittance between the compound of the present invention and the compound of the present invention by setting the light transmittance of Comparative Example 1 to 100% for each lot. The results showed that when using the compound of the present invention compared to Comparative Example 1, the light transmittance increased by 28% to 39%.

[0417] Regarding electrode (electrically conductive material) coatings, light transmittance is used to determine the amount of electrode material present on a given surface. This is because electrode materials contain metals, and electrically conductive materials such as metals attenuate and / or absorb light. Therefore, a surface with a light transmittance exceeding 90% in the visible light region of the electromagnetic spectrum is considered to contain substantially no electrically conductive material.

[0418] Therefore, as a result of measuring the light transmittance of the samples prepared according to the present invention, it was found that when using the compound of the present invention with an intramolecular fluorine content of 20% or more, as shown in Table 5 above, the metal Yb used as the electron injection layer and Ag and Mg used as the negative electrode were not deposited on the compound of the present invention.

[0419] To confirm the above, the end faces of the samples from Comparative Example 1 and Example 3 were examined using a scanning electron microscope (SEM), an analytical instrument capable of observing the surface of various metal types. The results are shown in Figure 4 (FE-SEM: JMS6701F manufactured by JEOL).

[0420] As shown in Figure 4(a), it was confirmed that a thin white film was formed between the organic layer (lower end) and the capping layer (upper end), and as shown in Figure 4(b), it was confirmed that no thin film was formed between the organic layer and the metal patterning layer (lower end) and the capping layer (upper end).

[0421] Example 11: Comparison of light transmittance with and without electron injection layer metal and with different types of electrode metals. First, a C-1 film was vacuum-deposited as an organic layer onto a glass substrate to a thickness of 100 nm. On the organic layer, compound P1-46 of the present invention was vacuum-deposited to a thickness of 10 nm to form a metal patterning layer. Next, Yb was vacuum-deposited as an electron injection layer onto the metal patterning layer, and then Mg and Ag were deposited as a negative electrode in a 1:9 weight ratio. After that, D-1 was deposited as a capping layer to a thickness of 70 nm to prepare the sample.

[0422] Comparative Example 3 An organic electronic device was manufactured in the same manner as in Example 11, except that a metal patterning layer was not used.

[0423] Example 12: Sample with no Yb as the electron injection layer metal. First, a C-1 film was vacuum-deposited onto a glass substrate to form an organic layer with a thickness of 100 nm. A metal patterning layer was then formed on the organic layer by vacuum-depositing compound P1-46 to a thickness of 10 nm. Next, Mg and Ag were deposited on the metal patterning layer in a 1:9 weight ratio as a negative electrode. Finally, a D-1 capping layer was deposited to a thickness of 70 nm to fabricate an organic electronic device.

[0424] Comparative Example 4: Sample without Yb, the electron injection layer metal. An organic electronic device was manufactured in the same manner as in Example 12, except that a metal patterning layer was not used.

[0425] Example 13: Sample using only Ag as the electrode (negative electrode) First, a C-1 film was vacuum-deposited onto a glass substrate to form an organic layer with a thickness of 100 nm. On the organic layer, the compound P1-46 of the present invention was vacuum-deposited to a thickness of 10 nm to form a metal patterning layer. Next, Yb was vacuum-deposited onto the metal patterning layer as an electron injection layer, followed by Ag being deposited as a negative electrode. After that, D-1 was deposited to a thickness of 70 nm as a capping layer to fabricate an organic electronic device.

[0426] Comparative Example 5: Sample using only Ag as the electrode (negative electrode) An organic electronic device was manufactured in the same manner as in Example 13, except that a metal patterning layer was not used.

[0427] The light transmittance samples of the examples and comparative examples prepared in this manner were measured at 550 nm in the visible light region using a Lambda 365 UV / VIS spectrometer (Perkinelmer). The measurement results are shown in Table 6 below.

[0428] [Table 6]

[0429] The results in Table 6 were prepared based on the graph of the light transmittance measurement results in Figure 6. Table 6 compares the light transmittance of Comparative Examples 3, 4, and 5, which did not use a metal patterning layer, with that of Examples 11, 12, and 13, which used the inventive compound P1-46 with an intramolecular fluorine content of 30% or more, to investigate the feasibility of electrode patterning with or without an electron injection layer metal and the change in electrode patterning depending on the type of metal used for the negative electrode. Comparative Examples 3 and 11 were evaluated as a comparison group in which Yb, the electron injection layer metal, and Mg, the negative electrode metal, were not used, and it was confirmed that when the inventive compound P1-46, which has an intramolecular fluorine content of 30% or more, was used as the metal patterning layer, it showed a light transmittance of 95.63%.

[0430] Excluding Yb, the metal used as the electron injection layer, Comparative Example 4 and Example 12 were performed to confirm the patterning performance for the negative electrode metal. The results showed that in the absence of Yb, the electron injection layer metal, the light transmittance of Example 12 using the compound of the present invention was 96.68% (T%: 146%), which is higher than that of Example 11, where the electron injection layer is present (a 16% increase in T%).

[0431] Furthermore, in order to investigate the patterning performance according to the type of metal used for the negative electrode, we compared Comparative Example 5 and Example 13, which used only Ag for the negative electrode, with Comparative Example 3 and Example 11, which were comparison groups. The results showed that when only Ag was used for the negative electrode, and the compound of the present invention was used in the metal patterning layer, the light transmittance increased by 135% (T%), which is 5% higher than that of Example 11.

[0432] Example 14 First, a C-1 film was vacuum-deposited as an organic layer onto a glass substrate to a thickness of 100 nm. On the organic layer, compound P1-22 of the present invention was vacuum-deposited to a thickness of 3 nm to form a metal patterning layer. Next, Yb was vacuum-deposited as an electron injection layer onto the metal patterning layer, and then Mg and Ag were deposited as a negative electrode in a 1:9 weight ratio. After that, D-1 was deposited as a capping layer to a thickness of 70 nm to prepare a sample.

[0433] Examples 15 to 25 Samples were prepared in the same manner as in Example 14, except that the compounds of the present invention listed in Table 7 and the thicknesses listed in Table 7 below were used as the metal patterning layer material, instead of compound P1-22 of the present invention.

[0434] Comparative Example 6 Samples were prepared in the same manner as in Example 14, except that a metal patterning layer was not used.

[0435] The light transmittance samples of the examples and comparative examples prepared in this manner were measured at 550 nm in the visible light region using a Lambda 365 UV / VIS spectrometer (Perkinelmer). The measurement results are shown in Table 7 below.

[0436] [Table 7]

[0437] The results in Table 7 were prepared based on the graph of the light transmittance measurement results in Figure 7. Table 7 was prepared to confirm the change in light transmittance with respect to the thickness of the metal patterning layer using the compound of the present invention. In the case of Comparative Example 6, the light transmittance results for each lot of the comparative example used during the evaluation of each material described in Examples 14 to 25 are listed as a range (69.13% to 72.38%), the light transmittance measured for each lot is calculated as 100% (T%), and the light transmittance of the example is listed as T%.

[0438] In Examples 14 to 25, when the compounds of the present invention were used as metal patterning layers with thicknesses of 3 nm, 5 nm, and 10 nm, respectively, it was confirmed that there was no significant difference in light transmittance, ranging from 95.01% to 96.47% (T% 132% to 140%). This indicates that when the compounds of the present invention are used as a material for metal patterning, problems such as performance degradation due to variations in deposition thickness that may occur during the deposition process can be prevented.

[0439] Example 26 To measure the contact angle, a sample was prepared by vacuum-depositing the compound P1-34 of the present invention to a thickness of 50 nm onto a glass substrate.

[0440] Examples 27-34 Samples were prepared in the same manner as in Example 26, except that the compounds of the present invention listed in Table 8 were used on a glass substrate instead of compound P1-34 of the present invention.

[0441] Comparative Example 7 The procedure was carried out in the same manner as in Example 26, but C-1 was used instead of the compound P1-34 of the present invention.

[0442] The contact angles of the comparative example 7 and examples 26 to 34 samples prepared in this manner were measured using a DSA25 (KRUSS) contact angle measuring device, and the evaluation results are shown in Table 8 below.

[0443] [Table 8]

[0444] As shown in Table 8 above, it was confirmed that the contact angle of the C-1 material, which does not contain fluorine and has low light transmittance, is 83.2°, while the contact angles of all the compounds of the present invention, which have a light transmittance of 90% or more, were confirmed to be 100° or more (103.6~118.2°). The results in Table 8 above are judged to indicate the reason why the compounds of the present invention, which have high light transmittance (90% or more), are suitable for metal patterning. Generally, adhesion is explained by the solid surface energy through the contact angle (wetting angle or contact angle) and wettability. Generally, the larger the contact angle, the smaller the wettability, and as a result, the lower the adhesion, the lower the solid surface energy. This is because if the surface tension of a liquid is large, the force pulling them together becomes large, making it difficult to spread on a solid surface.

[0445] The above can be confirmed by Young's equation below.

[0446] The following relationship holds between interfacial tension and contact angle: gLVcosθ=gSV-gSL (1) gSL: Interfacial tension between a solid and a liquid. gSV: Interfacial tension between a solid surface and liquid vapor. gLV: Interfacial tension between liquid and liquid vapor

[0447] The formula for the work of adhesion Wa presented by Dupre, as shown in formula (1) above, is as follows: Wa=gS+gLV-gSL=gS+gLV+(gLVcosθ-gSV)=(gS-gSV)+gLV(1+cosθ) (2) In equation (2) above, gS is the surface tension of the solid itself, and since gS and gSV can generally be considered equal at small surface energies, equation (2) above can be summarized as follows. Wa = gLV(1 + cosθ) (3) From equation (3) above, if the contact angle is 0°, cos0°=1, so it is completely wetted. On the other hand, if the contact angle is 180°, cos180°=-1, so it is not wetted at all.

[0448] Therefore, as the contact angle decreases from 90° to 0°, cosθ approaches 1, which increases wettability and adhesion. Conversely, as the contact angle increases from 90° to 180°, cosθ approaches -1, wettability and adhesion decrease.

[0449] When the compound of the present invention is used as a metal patterning material, it is determined that the low surface energy of the compound reduces the adhesion to the metal (electrode) and increases the light transmittance.

[0450] The above description is merely illustrative, and various modifications are possible without departing from the essential characteristics of the present invention for those with ordinary skill in the art relating to the present invention. Therefore, the examples disclosed herein are for illustrative purposes only, not to limit the present invention, and the spirit and scope of the invention are not limited by such examples. The scope of protection of the present invention should be interpreted by the following claims, and all art of an equivalent scope should be interpreted as being included within the scope of the present invention.

[0451] (Potential for industrial use) According to the present invention, it is possible to manufacture organic elements having excellent element characteristics such as high brightness, high light emission, and long lifespan, and these elements have potential for industrial application. [Explanation of symbols]

[0452] 100, 200, 300: Organic electronic devices 110: 1st electrode 120: Hole injection layer 130: Hole transport layer 140: Emitting layer 150: Electron transport layer 170:Second electrode 180: Light efficiency improvement layer 190: Metal patterning layer

Claims

1. An organic electronic element having a positive electrode, at least one organic layer on the positive electrode, a non-luminescent region including a metal patterning layer on the organic layer, and a luminescent region including a metal; a metal electrode; or a metal and a metal electrode on the organic layer, An organic electronic device characterized in that the metal patterning layer contains a fluorinated compound represented by the following formula (2-5): 【Chemistry 1】 [In the formula, 1) Ar １ and Ar ２ They are independent of each other, C ６ ~C １８ The aryl group of; and C containing at least one heteroatom of O, N, S, Si, and P. ２ ~C １６ From the group consisting of heterocyclic groups; 2) B is, independently of one another, -CR ａ R ｂ -; -O-; and C ６ ~C １８ an arylene group; and is selected from the group consisting of: 3) R １ and R ３ Each of them is either the same or different, and is independent of the others, C ６ ~C １８ aryl group; fluorenyl group; C containing at least one heteroatom of O, N, S, Si and P. ２ ~C １６ heterocyclic group; C １ ~C １０ Selected from the group consisting of alkyl groups; -L-NR'R''; and substituents represented by the above formula (1-1), However, R １ and R ３ At least one of them is a substituent represented by formula (1-1), 4) a and c are independent integers between 1 and 10. 7) R' and R'' are independent of each other, C ６ ~C １８ Selected from the group consisting of aryl groups, 8) R ａ , R ｂ , R ｄ , and R ｅ These are, independently of each other: hydrogen; deuterium; halogen; C ６ ~C １８ The aryl group of; and C containing at least one heteroatom of O, N, S, Si, and P. ２ ~C １６ heterocyclic group; C １ ~C ５０ Selected from the group consisting of alkyl groups; 10) x is an integer between 6 and 50, and y + z is an integer of 2x + 1, 2x, or 2x - 2. 11) i are mutually independent integers between 0 and 20, and s are mutually independent integers between 1 and 20. However, if i is 0, then s is 1, 12) L is a single bond; and C ６ ~C １８ Selected from the group consisting of the arylene group; 13) Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, and alkyl group are deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C １ ~C ２０ alkylthio group; C １ ~C ２０ alkoxyl group of; C ６ ~C ２０ aryloxy group; C １ ~C ２０ alkyl group; C ２ ~C ２０ alkenyl group of C ２ ~C ２０ The alkynyl group of C ６ ~C ２０ aryl group; deuterium-substituted C ６ ~C ２０ aryl group of; halogen-substituted C ６ ~C ２０ aryl group; fluorenyl group; C ２ ~C ２０ heterocyclic group; C ３ ~C ２０ cycloalkyl groups; C ７ ~C ２０ arylalkyl groups; and C ８ ~C ２０ The arylalkenyl group of ; may be further substituted with one or more substituents selected from the group consisting of , and these substituents may be bonded to each other to form a ring, where 'ring' means C ３ ~C ６０ aliphatic ring or C ６ ~C ６０ The aromatic ring or C ２ ~C ６０ This refers to a fused ring consisting of a heterocycle or a combination thereof, including saturated or unsaturated rings.

2. Ar １ and Ar ２ These are, independently of each other, C ６ ~C １８ The organic electronic device according to claim 1, wherein the aryl group is...

3. The above formula (1-1) is either formula (1-1-a) or formula (1-1-b) 【Chemistry 2】 [In the formula, 1) x, y, z, s and B are the same as the definitions in claim 1, and 2) i' The organic electronic element according to claim 1, characterized by being an integer from 1 to 20.

4. The above equation (1-1) is the following equation (1-1-c) 【Transformation 3】 [In the formula, 1) x, y, z, and s are the same as the definitions in claim 1, 2) i' is an integer between 1 and 20, and d is an integer between 0 and 4. 3) R ５ is deuterium; halogen; C ６ ~C ２０ aryl group of; C １ ~C ２０ The organic electronic element according to claim 1, characterized by being represented by: an alkyl group selected from the group consisting of; or adjacent groups bond to each other to form a ring.

5. Fluorinated compounds that are any one of the following compounds: 【Chemistry 4】 。

6. The organic electronic element according to claim 1, characterized in that the metal contains Ag when metal patterning is performed using the compound represented by formula (2-5).

7. The organic electronic element according to claim 1, characterized in that the metal contains Ag or Mg when metal patterning is performed using the compound represented by formula (2-5).

8. The organic electronic device according to claim 1, wherein the fluorinated compound is a mixture of two or more different compounds represented by formula (2-5).

9. A display device comprising an organic electronic element as described in claim 1; and A control unit for driving the display device; Electronic devices including

10. The electronic device according to claim 9, characterized in that the organic electronic element is selected from the group consisting of an organic electron light-emitting element, an organic transistor, a monochromatic illumination element, and a quantum dot display element.

11. A composition for metal patterning of organic electronic devices, comprising one of the fluorinated compounds according to formula (2-5) described in claim 1, or two or more compounds having structures different from each other.

12. Fluorinated compounds represented by the following formula (2-5): 【Transformation 5】 [In the formula, 1) Ar １ and Ar ２ They are independent of each other, C ６ ~C １８ The aryl group of; and C containing at least one heteroatom of O, N, S, Si, and P. ２ ~C １６ From the group consisting of heterocyclic groups; 2) B is independent of each other, -CR ａ R ｂ -; -O-; and C ６ ~C １８ Selected from the group consisting of the arylene group; 3) R １ and R ３ are each the same or different and are independent of each other, and are C ６ -C １８ aryl group; fluorenyl group; C containing at least one heteroatom of O, N, S, Si and P ２ -C １６ heterocyclic group; C １ -C １０ alkyl group; -L-NR'R''; and the substituent represented by the formula (1-1); and is selected from the group consisting of However, R １ and R ３ At least one of them is a substituent represented by formula (1-1), 4) a and c are independent integers between 1 and 10. 7) R' and R'' are each independently selected from the group consisting of aryl groups of C ６ to C １８ and 8) R ａ , R ｂ , R ｄ , and R ｅ These are, independently of each other: hydrogen; deuterium; halogen; C ６ ~C １８ The aryl group of; and C containing at least one heteroatom of O, N, S, Si, and P. ２ ~C １６ heterocyclic group; C １ ~C ５０ Selected from the group consisting of alkyl groups; 10) x is an integer between 6 and 50, and y + z is an integer of 2x + 1, 2x, or 2x - 2. 11) i are mutually independent integers between 0 and 20, and s are mutually independent integers between 1 and 20. However, if i is 0, then s is 1, 12) L is a single bond; and C ６ ~C １８ Selected from the group consisting of the arylene group; 13) Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, and alkyl group are deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C １ ~C ２０ alkylthio group; C １ ~C ２０ alkoxyl group of; C ６ ~C ２０ aryloxy group; C １ ~C ２０ alkyl group; C ２ ~C ２０ alkenyl group of C ２ ~C ２０ The alkynyl group of C ６ ~C ２０ aryl group; deuterium-substituted C ６ ~C ２０ aryl group of; halogen-substituted C ６ ~C ２０ aryl group; fluorenyl group; C ２ ~C ２０ heterocyclic group; C ３ ~C ２０ cycloalkyl groups; C ７ ~C ２０ arylalkyl groups; and C ８ ~C ２０ The arylalkenyl group of ; may be further substituted with one or more substituents selected from the group consisting of , and these substituents may be bonded to each other to form a ring, where 'ring' means C ３ ~C ６０ aliphatic ring or C ６ ~C ６０ The aromatic ring or C ２ ~C ６０ This refers to a fused ring consisting of a heterocycle or a combination thereof, including saturated or unsaturated rings.

13. Ar １ and Ar ２ These are, independently of each other, C ６ ~C １８ The fluorinated compound according to claim 12, wherein the aryl group is...

14. The above formula (1-1) is either formula (1-1-a) or formula (1-1-b) 【Transformation 6】 The fluorinated compound according to claim 12, characterized by being represented by [wherein 1) x, y, z, s, and B are the same as defined in claim 12, and 2) i' is an integer from 1 to 20.]

15. The above equation (1-1) is the following equation (1-1-c) 【Transformation 7】 [In the formula, 1) x, y, z, and s are the same as the definitions in claim 12, 2) i' is an integer between 1 and 20, and d is an integer between 0 and 4. 3) R ５ is deuterium; halogen; C ６ ~C ２０ aryl group of; C １ ~C ２０ A fluorinated compound according to claim 12, characterized by being represented by: an alkyl group selected from the group consisting of; or adjacent groups bond to each other to form a ring.

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