Compound for organic electronic element, organic electronic element using the same, and electronic device therefor

Abstract

To provide a fluorinated material for patterning a metal or an electrode (cathode) that can reduce time and cost required for a patterning process while forming a precise electrode pattern in a display device.SOLUTION: A fluorinated compound represented by formula (2), an organic electronic element including the same, and an electronic device are disclosed. [In the formula, Ar1, Ar2, and A are independently selected from the group consisting of phenyl, biphenyl, naphthyl, and terphenyl, R1, R2, and R3 are independently substituents represented by formula (1-1), and B is phenyl, biphenyl, naphthyl, or terphenyl].SELECTED DRAWING: Figure 1

Description

Technical Field

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

Background Art

[0002] With the continuous development of display technology, the requirements of users for display devices are increasing. Terminal display devices (especially smartphones) are required to develop in the directions of flexibility, full screen, and high integration.

[0003] Especially in the case of smartphone displays, with the development of technology, efforts are being made to maximize the screen size of smartphones of the same size. As a result, the bezel size of smartphones has been developed to be minimized as much as possible with the increase in screen size. In the process, the physical buttons on the front of the smartphone have disappeared into the screen, and the position of the camera of the smartphone has also been continuously changed in ways such as notches, holes, and slides.

[0004] Recently, the development of bezel-less under-display has been rapidly progressing, and accordingly, the development of transparent display technology has also been rapidly progressing.

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

[0006] In particular, for UDC, precise patterning of the cathode is essential to increase the transmittance because the UDC camera cannot operate normally unless the high transmittance of the display is ensured.

[0007] Generally, as the electrode patterning method, there are roughly two methods used. First, electrodes are patterned on desired portions using a shadow mask, or second, a method of creating a pattern by irradiating a cathode with a laser.

[0008] However, in the electrode patterning method via a shadow mask, due to the typical material properties of the metal mask, a warping phenomenon occurs during the high-temperature evaporation process, and thus problems such as distortion of the mask shape and electrode pattern occur. Therefore, since it is inevitably necessary to incur time and costs for mask maintenance, it is not commercially suitable for mass production of devices.

[0009] Also, in the electrode patterning method via a laser, due to the inherent properties of the laser, the type and intensity of the laser must be determined so that the substrate is not damaged in the method where the electrodes are patterned. This causes a nuisance that must be determined.

[0010] On the other hand, fluorinated organic compound materials are used in various applications in organic electronic devices. For example, in Patent Document 1, in 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, at least one polymer selected from the group consisting of chlorotrifluoroethylene homopolymer, dichlorofluoroethylene homopolymer, and a copolymer of chlorotrifluoroethylene and dichlorodifluoroethylene is vapor-deposited to further sufficiently prevent the intrusion of moisture and oxygen into the light-emitting layer, and a compound that serves as a sealing material is disclosed.

[0011] Also, Patent Document 2 and Non-Patent Document 1 disclose that substances containing fluorine have high chemical and thermal stability and can improve the electron transport characteristics, so they can be used as the electron transport layer of an organic EL device, and since they exhibit a hole blocking function, they can also be used as a hole blocking layer and can also be used as a protective film, and the lifetime of the device can be improved.

[0012] Patent Document 3 also discloses that a substance containing fluorine can be used as a material for the light-emitting layer in addition to the electron transport layer, and discloses a green light-emitting polymer in which a fluorinated aryl with strong electron affinity, i.e., a pentafluoroaryl or octafluorobiphenyl group, is introduced into poly(p-phenylenevinylene) to induce a balanced encounter between electrons and holes, thereby improving the electroluminescence efficiency. Patent Document 4 also discloses a fluorine-based compound having AIEE (Aggregation Induced Enhanced Emission) properties that are particularly excellent in luminescence efficiency in the solid state. Patent Document 5 discloses an organic light-emitting device having a first electrode, a hole transport layer, a light-emitting layer, and a second electrode, in which a fluorine-substituted C is placed between the first electrode and the hole transport layer. 6y F 6y-2n Also, an organic light-emitting device characterized in that the aromatic fluorocarbon compound is further contained between the light-emitting layer and the second electrode is described. This discloses that in order to adjust the interface of the organic light-emitting device, a thin film containing a fluorine-containing compound is inserted at the interface between the first electrode (positive electrode) and the hole injection (hole transport layer), and an organic light-emitting device with low power consumption is provided by strengthening the driving voltage. [Prior art documents] [Patent documents]

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

[0014]

Non-Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0015] An object of the present invention is to provide a fluorinated material for metal or electrode (cathode) patterning that can form a precise electrode pattern in a display device and reduce the time and cost required for the patterning method.

Means for Solving the Problems

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

[0017]

Chemical Formula

Effects of the Invention

[0018] By using the compound represented by the formula (1) as a metal or electrode (cathode) patterning material, the present invention can form a fine pattern of the electrode without using a shadow mask, facilitate the production of a transparent display having a high light transmittance, and make it easier to apply UDC.

Brief Description of the Drawings

[0019]

Figure 1

Figure 2

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Figure 5B

Figure 5C

Figure 5D

Figure 5E

Figure 5F

Figure 5G

Figure 5H

Figure 5I

Figure 5J

Figure 6A

Figure 6B

Figure 6C

Figure 7A

Figure 7B

Figure 7C

Figure 7D

Figure 8A

Figure 8B

Figure 8C

Figure 8D

Figure 8E

Figure 8F

Figure 8G

Figure 8H

Figure 8I

Figure 8J

Modes for Carrying Out the Invention

[0020] As used in this specification and the appended claims, unless otherwise specified, the meanings of the following terms are as follows.

[0021] As used in this specification, the term "halo" or "halogen" means fluorine (F), bromine (Br), chlorine (Cl), or iodine (I) unless otherwise specified.

[0022] As used in the present invention, the term "alkyl" or "alkyl group" means a radical of a saturated aliphatic functional group having a single bond with 1 to 60 carbon atoms, including a linear alkyl group, a branched-chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cycloalkyl group, a cycloalkyl-substituted alkyl group, etc., unless otherwise specified.

[0023] As used herein, the terms "alkenyl group" or "alkynyl group" each contain a double bond or triple bond having 2 to 60 carbon atoms and a straight-chain or branched-chain group in the oil or fat, unless otherwise specified, and are not limited thereto.

[0024] As used herein, the term "cycloalkyl" means an alkyl forming a ring having 3 to 60 carbon atoms, unless otherwise specified, and is not limited thereto.

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

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

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

[0028] As used herein, the term "arylthio group" means an aryl group to which a sulfur radical is bonded, and has 1 to 60 carbon atoms, unless otherwise specified, and 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, and are not limited thereto. In the present invention, the aryl group or arylene group means a monocyclic or polycyclic aromatic group and includes an aromatic ring formed by adjacent substituents participating in a bond or reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

[0030] The prefix "aryl" or "ar" means a radical substituted with an aryl group. For example, an arylalkyl group is an alkyl group substituted with an aryl group, and an ar lkenyl group is an alkenyl group substituted with an aryl group, and a radical substituted with an aryl group has the number of carbon atoms described herein. Also, when prefixes are named consecutively, it means that substituents are enumerated in the order described above. For example, in the case of an aryloxy group, it means an alkoxy group substituted with an aryl group, in the case of an alkoxylcarbonyl group, it means a carbonyl group substituted with an alkoxyl group, and in the case of an arylcarbonylalkenyl group, it means an alkenyl group substituted with an arylcarbonyl group, where the arylcarbonyl group is a carbonyl group substituted with an aryl group.

[0031] As used herein, the term "heterocyclic group" includes one or more heteroatoms, has 2 to 60 carbon atoms, includes at least one of monocyclic and polycyclic rings, and includes heteroaliphatic rings and heteroaromatic rings, unless otherwise specified. Adjacent functional groups may be joined to form a ring.

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

[0033] Also, "heterocyclic group" means a monocyclic, ring assembly, various joined ring systems, spiro compounds, etc. containing heteroatoms. Also, compounds containing heteroatomic groups such as SO2, P=O, etc. like the following compounds instead of carbon forming the ring can also be included in the heterocyclic group.

[0034]

Chemical formula

[0035] The term "aliphatic cyclic group" used in the present invention means a cyclic hydrocarbon excluding aromatic hydrocarbons, including monocyclic, ring aggregates, various joined ring systems, spiro compounds, etc., and means a ring having 3 to 60 carbon atoms, but is not limited thereto, unless otherwise specified. For example, when benzene, which is an aromatic ring, and cyclohexane, which is a non-aromatic ring, are condensed, it also corresponds to an aliphatic ring.

[0036] The terms "fluorenyl group", "fluorenylene group", and "fluorenetriyl group" used in the present invention, unless otherwise specified, in the following structures, R, R' and R'' are all monovalent, divalent or trivalent functional groups that are hydrogen, and "substituted fluorenyl group", "substituted fluorenylene group" or "substituted fluorenetriyl group" mean that at least one of the substituents R, R' and R'' is a substituent other than hydrogen, and includes the case where R and R' are bonded to each other to form a spiro compound together with the carbon to which they are bonded. In this specification, regardless of the valence number, all of the fluorenyl group, fluorenylene group, and fluorenetriyl group can be called fluorenyl group.

[0037]

Chemical formula

[0038] In this specification, for "group names" corresponding to aryl groups, arylene groups, heterocyclic groups, etc. exemplified by each symbol and examples of its substituents, it is possible to describe the "group name reflecting the valence", but it is also possible to describe it as the "parent compound name". For example, in the case of "phenanthrene", which is a kind of aryl group, the monovalent group can be described as "phenanthryl", and the divalent group can be described with the group name differentiated by valence such as "phenanthrylene", but it can also be described as "phenanthrene", which is the parent compound name regardless of the valence. Similarly, in the case of pyrimidine, it can be described as "pyrimidine" regardless of the valence, or it can be described with the "group name" of the corresponding valence such as pyrimidinyl group in the monovalent case and pyrimidinylene in the divalent case. In addition, in this specification, when describing compound names and substituent names, numbers, alphabets, etc. indicating positions can also be omitted. For example, pyrido[4,3-d]pyrimidine can be described as pyridopyrimidine, benzofuro[2,3-d]pyrimidine can be described as benzofuropyrimidine, 9,9-dimethyl-9H-fluorene can be described as dimethylfluorene, etc. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be described as benzoquinoxaline.

[0039] Also, unless otherwise explicitly stated, the formulas used in the present invention are applied in the same way as the definitions of substituents according to the definitions of the exponents of the following formulas.

[0040]

Chemical formula

[0041] In the formula, when a is an integer of 0, the substituent R 1 is absent, and when a is an integer of 1, one substituent R 1 is bonded to any carbon forming the benzene ring. When a is an integer of 2 or 3, they are bonded as follows, respectively. At this time, R 1 may be the same as or different from each other. When a is an integer of 4 to 6, it is bonded to the carbon of the benzene ring in the same way, while the representation of hydrogen bonded to the carbon forming the benzene ring is omitted.

[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 rings that are condensed. For example, a form in which three rings are condensed with each other, such as anthracene, phenanthrene, benzoxazoline, etc., can be denoted 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 - atom ring, a 6 - atom ring, etc., the number in "number - atoms" represents the number of elements forming the ring. For example, thiophene, furan, etc. correspond to 5 - atom rings, and benzene, pyridine, etc. may correspond to 6 - atom rings.

[0045] Also, unless otherwise specified in this specification, a ring formed by the bonding of 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 to each other, R 2 and R 3 to each other, R 3 and R 4 to each other, R 5 and R 6 not only to each other, but also R 7 and R 8 sharing one carbon atom with each other are included, and R 1 and R 7 to each other, R 1 and R 8 to each other or R 4 and R 5Substituents bonded to ring-constituting elements (such as carbon and nitrogen) that are not immediately adjacent, such as to each other, may also be included. That is, when there are substituents on ring-constituting elements such as carbon or nitrogen that are immediately adjacent, these may be adjacent groups, but when there are no substituents bonded to the ring-constituting elements at immediately adjacent positions, the substituents bonded to the next ring-constituting element may be taken as the adjacent groups, and substituents bonded to the same ring-constituting carbon may also be taken as adjacent groups.

[0047] In the following formula, R 7 and R 8 When substituents bonded to the same carbon, such as, bond to each other to form a ring, a compound containing a spiro moiety may be formed.

[0048]

Chemical formula

[0049] Also, in this specification, the expression "adjacent groups can bond to each other to form a ring" is used in the same meaning as "adjacent groups can bond to each other to selectively form a ring", and means the case where at least one pair of adjacent groups bond to each other to form a ring.

[0050] Hereinafter, the compound according to one aspect of the present invention will be described.

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

[0052]

Chemical formula

[0053] [In the formula, each symbol can be defined as follows. 1) Ar 1 and Ar 2 are, independently of each other, C6 - C 60an aryl group; a C2-C heterocyclic group containing at least one heteroatom of O, N, S, Si and P 60 ; and a condensed ring group of an aliphatic ring of C3-C 60 and an aromatic ring of C6-C 60 ; selected from the group consisting of. When the said Ar 1 and Ar 2 are aryl groups, 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 sufficient. When the said Ar 1 and Ar 2 are heterocyclic groups, 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 and the like may be sufficient. 2) A, B, C and D are, independently of one another, -CR a R b -; -NR c -; -O-; -S-; -SiR d R e -; a C6-C arylene group; a fluorenylene group; and a C2-C heterocyclic group containing at least one heteroatom of O, N, S, Si and P 60 ; selected from the group consisting of. 60 When the said A, B, C and D are arylene groups, preferably a C6-C arylene group, more preferably a C6-C 30 arylene group, still more preferably a C6-C 20 arylene group, for example, phenylene, biphenylene, naphthylene, terphenylen may be sufficient. 18 ​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 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. However, when m is 0, A is an aryl group of C6-C 60 ; or a C2-C heterocyclic group containing at least one heteroatom of O, N, S, Si, and P 60 ; is. When A is an aryl group, preferably an aryl group of C6-C 30 , more preferably an aryl group of C6-C 20 , still more preferably an aryl group of C6-C 18 , for example, phenyl, biphenyl, naphthyl, terphenyl may be used. When A 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. 3) R 1 , R 2 and R 3 are each the same or different and are independent of each other, an aryl group of C6-C 60 ; a fluorenyl group; a C2-C heterocyclic group containing at least one heteroatom of O, N, S, Si, and P 60 ; a C3-C 60 aliphatic ring and a 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); are selected from the group consisting of, or adjacent groups may be bonded to each other to form a ring. When the said 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 said 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 said 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 said 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 said 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 or the like. 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, R 1 , R 2 and R 3 At least one of them is a substituent represented by the formula (1-1) or a substituent represented by the formula (1-2). 4) a, b and c are, independently of one another, integers from 0 to 10, provided that a + b + c is 1 or more. 5) m and n are, independently of one another, integers 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, independently of one another, CR f R g , NR h , O, S or SiR i R j is. 7) R’ and R'' are, independently of one another, an aryl group having 6 to C 60 ; a heterocyclic group having 2 to C 60 containing at least one heteroatom of O, N, S, Si and P; and a condensed ring group of an aliphatic ring having 3 to C 60 and an aromatic ring having 6 to C 60 ; 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 an aryl group having 6 to C 30 , more preferably an aryl group having 6 to C 20The aryl group, more preferably a C6-C 18 aryl group, for example, phenyl, biphenyl, naphthyl, terphenyl may be sufficient. When the R' and R'' are hetero ring groups, preferably a C2-C 30 hetero ring group, more preferably a C2-C 20 hetero ring group, still more preferably a C2-C 16 hetero ring group, for example, pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, dibenzofuran, dibenzothiophene, naphthobenzothiophene, naphthobenzofuran, benzofuran, benzothiophene and the like may be sufficient. 8)R a 、R b 、R c 、R d 、R e 、R f 、R g 、R h 、R i and R j are each independently hydrogen; deuterium; halogen; C6-C 60 aryl group; a C2-C containing at least one hetero atom of O, N, S, Si and P 60 hetero ring group; a condensed ring group of a C3-C 60 aliphatic ring and a C6-C 60 aromatic ring; a C1-C 50 alkyl group; the substituent represented by the formula (1-1); and the substituent represented by the formula (1-2); and may be selected from the group consisting of, or adjacent groups may be bonded to each other to form a ring. Said R a ~R j When 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 sufficient. Said R a ~R j When is a hetero ring group, preferably a C2-C 30 hetero ring group, more preferably a C2-C 20The heterocyclic group, more preferably C2-C 16 The heterocyclic group, for example, pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, dibenzofuran, dibenzothiophene, naphthobenzothiophene, naphthobenzofuran, benzofuran, benzothiophene, etc. may be used. When the said R a ~R j is an alkyl group, preferably a C1-C 20 alkyl group, more preferably a C1-C 10 alkyl group, and may be, for example, methyl, t-butyl, etc. 9) o, p, q, and r are each independently an integer of 0 or 1. At this time, when the said o is 0, X 1 is absent. When the said p is 0, X 2 is absent. When the said q is 0, X 3 is absent. When the said r is 0, X 4 is absent. 10) x is an integer of 3 to 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. At this time, x is preferably an integer of 3 to 20, more preferably an integer of 5 to 15, and even more preferably an integer of 5 to 12. If x exceeds the said range, there is a problem that Td becomes high during vacuum deposition. If it is less than the said range, the compound is likely to become a liquid. 11) i, t, and v are each independently an integer of 0 to 20, and s, u, and w are each independently an integer of 1 to 20. Here, when i or t is 0, B and C mean a single bond, and at this time, s or u is 1. 12) L is a single bond; a C6-C 60 arylene group; a fluorenylene group; a C2-C containing at least one heteroatom of O, N, S, Si, and P 60 heterocyclic group; a C1-C 50 alkylene group; 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. When the said L is an arylene group, it is preferably an arylene group of C6-C 30 and more preferably an arylene group of C6-C 20 and even more preferably an arylene group of C6-C 18 such as, for example, phenylene, biphenylene, naphthylene, terphenylene, etc. may be used. When the said L is a fluorenylene group, 9,9-dimethyl-9H-fluorenylene, 9,9-diphenyl-9H-fluorenylene, 9,9'-spirobifluorenylene, etc. may be used. When the said L is a heterocyclic group, it is preferably a heterocyclic group of C2-C and more preferably a heterocyclic group of C2-C 30 and even more preferably a heterocyclic group of C2-C 20 such as, for example, pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, dibenzofuran, dibenzothiophene, naphthobenzothiophene, naphthobenzofuran, benzofuran, benzothiophene, etc. may be used. 16 When the said L is an alkylene group, it is preferably an alkylene group of C1-C and more preferably an alkylene group of C1-C 20 and may be, for example, methylene, butylene, etc. 10 13) Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, condensed ring group, alkyl group, alkoxyl group, aryloxy group, and the ring formed by the adjacent groups bonding to each other are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1-C 20 alkylthio group; C1-C 20 alkoxyl group; C6-C 20 aryloxy group; C1-C 20 alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C6-C 20 aryl group; C6-C 20 aryl group substituted with deuterium; C6-C 20 aryl group substituted with halogen;an aryl group; a fluorenyl group; C2-C 20 heterocyclic group; C3-C 20 cycloalkyl group; C7-C 20 arylalkyl group; and C8-C 20 arylalkenyl group; 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 an aliphatic ring of C3-C 60 or an aromatic ring of C6-C 60 or a heterocycle of C2-C 60 or a condensed ring consisting of a combination thereof, including saturated or unsaturated rings.]

[0054] The formula (1) is represented by the following formula (2).

[0055]

Chemical formula

[0056] (In the formula, Ar 1 , Ar 2 , R 1 , R 2 , R 3 , A, a, b, c, m and n have the same meanings as defined in the formula (1).)

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

[0058]

Chemical formula

[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 defined in the formula (1).)

[0060] Also preferably, the said formula (1) is represented by the following formula (2-6).

[0061] [Chemical formula]

[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 have the same meanings as defined in the said formula (1), and 2) A' is an arylene group having 6 to 60 carbon atoms; or a heterocyclic group having 2 to 60 carbon atoms containing at least one hetero atom selected from O, N, S, Si and P. When the said A' is an arylene group, preferably it is an arylene group having 6 to 30 carbon atoms, more preferably an arylene group having 6 to 20 carbon atoms, still more preferably an arylene group having 6 to 18 carbon atoms, and for example, it may be phenylene, biphenylene, naphthylene, terphenylene, triphenylenylene or the like. When the said A' is a heterocyclic group, preferably it is a heterocyclic group having 2 to 30 carbon atoms, more preferably a heterocyclic group having 2 to 20 carbon atoms, still more preferably a heterocyclic group having 2 to 16 carbon atoms, and for example, it may be pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, benzofuran, benzothiophene or the like.]

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

[0064] [Chemical formula]

[0065] [In the formula, each symbol can be defined as follows. 1) b, c, x, y, z, and Ar 2 are synonymous with the definitions described in the above formula (1), 2) A' is synonymous with the definition described in the above formula (2-6), 3) R 4 is an aryl group having 6 to 60 carbon atoms; a fluorenyl group; a heterocyclic group having 2 to 60 carbon atoms containing at least one heteroatom selected from O, N, S, Si, and P; a condensed ring group of an aliphatic ring having 3 to 60 carbon atoms and an aromatic ring having 6 to 60 carbon atoms; an alkyl group having 1 to 50 carbon atoms; an alkoxyl group having 1 to 50 carbon atoms; an aryloxy group having 6 to 60 carbon atoms; and -L-NR'R''; selected from the group consisting of, or adjacent groups may be bonded to each other to form a ring, wherein L, R', and R'' are synonymous with the definitions described in the above formula (1). When the above R 4 is an aryl group, it is preferably an aryl group having 6 to 30 carbon atoms, more preferably an aryl group having 6 to 20 carbon atoms, still more preferably an aryl group having 6 to 18 carbon atoms, for example, phenyl, biphenyl, naphthyl, or terphenyl. When the above R 4 is a fluorenyl group, it may be 9,9-dimethyl-9H-fluorenyl, 9,9-diphenyl-9H-fluorenyl, 9,9'-spirobifluorenyl, or the like. When the above R 4 is a heterocyclic group, it is preferably a heterocyclic group having 2 to 30 carbon atoms, more preferably a heterocyclic group having 2 to 20 carbon atoms, still more preferably a heterocyclic group having 2 to 16 carbon atoms, for example, pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, dibenzofuran, dibenzothiophene, naphthobenzothiophene, naphthobenzofuran, benzofuran, benzothiophene, or the like. R 4 When is an alkyl group, it is preferably C1 to C 20 More preferably, the alkyl group is C1 to C 10 For example, it may be an alkyl group such as methyl or t-butyl. R 4 When is an alkoxy group, it is preferably a C1 to C 20 Alkoxyl groups, more preferably C1 to C 10 The alkyl group may be an alkoxy group, such as methoxy, t-butoxy, and the like. R 4 When is an aryloxy group, it is preferably a C6 to C 30 Aryloxy groups of the formula C6 to C 20 It may also be an aryloxy group of the formula: 4) R 3 ' is hydrogen; deuterium; C6-C 60 Aryl groups; fluorenyl groups; O, N, C2-C containing at least one heteroatom of S, Si, or P 60 Heterocyclic group; C3-C 60 Aliphatic rings and C6-C 60 Aromatic ring condensed group; C1-C 50 Alkyl group; C1-C 50 Alkoxy group; C6-C 60 and -L-NR'R''; and adjacent groups may be bonded to each other to form a ring. R 3 When ' is an aryl group, it is preferably a C6-C 30 Aryl groups of the formula Or C6~C 20 Aryl groups of C6 to C 18 The aryl group may be, for example, phenyl, biphenyl, naphthyl, terphenyl. R 3 When ' is a heterocyclic group, it is preferably a C2-C 30 Heterocyclic groups, more preferably Or C2~C 20 Heterocyclic groups of the formula (I) are preferably C2 to C16 The heterocyclic group may be, for example, pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, dibenzofuran, dibenzothiophene, naphthobenzothiophene, naphthobenzofuran, benzofuran, benzothiophene, etc. When the above R 3 ' is an alkyl group, it is preferably a C1-C 20 alkyl group, more preferably a C1-C 10 alkyl group, and may be, for example, methyl, t-butyl, etc. When the above R 3 ' is an alkoxy group, it is preferably a C1-C 20 alkoxyl group, more preferably a C1-C 10 alkoxyl group, such as methoxy, t-butoxy, etc. may be. When the above R 3 ' is an aryloxy group, it is preferably a C6-C 30 aryloxy group, more preferably a C6-C 20 aryloxy group, and may be.

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

[0067] [Chemical formula]

[0068] [In the formula, 1) R 1 , R 2 , R 3 and b are synonymous with the definitions described in the formula (1), 2) A’ is synonymous with the definition described in the formula (2-6), 3) a’ and c’ are independently integers from 0 to 5.

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

[0070]

Chemical formula

[0071] [In the formula, each symbol can be defined as follows. 1) b, B, i, x, y, z, and s have the same meaning as the definitions described in the formula (1), 2) A' has the same meaning as the definition described in the formula (2-6), 3) R 4 has the same meaning as the definition described in the formula (2-12).]

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

[0073]

Chemical formula

[0074] [In the formula, 1) b, x, y, and z have the same meaning as the definitions described in the formula (1), 2) A' has the same meaning as the definition described in the formula (2-6), 3) R 4 has the same meaning as the definition described in the formula (2-12).]

[0075] Also, the formula (1) is represented by the following formula (3).

[0076]

Chemical formula

[0077] (In the formula, Ar 1 , Ar 2 , R 1 , R 3 , A, c, and m have the same meaning as the definitions described in the formula (1).)

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

[0079] [Chemical formula]

[0080] [In the formula, 1) R 1 , R 3 and m are synonymous with the definitions described in the above formula (1), and 2) a' and c' are, independently of each other, integers from 0 to 5.]

[0081] Further, the above formula (1) is represented by the following formula (4).

[0082] [Chemical formula]

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

[0084] When the said A'' is an aryl group, preferably an aryl group of C6 - C 30 , more preferably an aryl group of C6 - C 20 , still more preferably an aryl group of C6 - C 18 , for example, it may be phenyl, biphenyl, naphthyl, terphenyl.

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

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

[0087]

Chemical formula

[0088] [In the formula, 1) Ar 1 , R 1 , R 2 , X1, a and b have the same meanings as defined in the said formula (1), and 2) A’’ has the same meaning as defined in the said formula (4).]

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

[0090]

Chemical formula

[0091] [In the formula, 1) Ar 1 , R 1 , R 2 , R f , R g , R h , R i , R j , a and b have the same meanings as defined in the said formula (1), and 2) A’’ has the same meaning as defined in the said formula (4).}

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

[0093]

Chemical formula

[0094] [In the formula, 1) X 1 , R1 and R 2 is synonymous with the definition described in the formula (1), and 2) a'' and b' are independently integers from 0 to 4.]

[0095] Further, the 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 formula (1), and 2) A' is the definition described in the formula (2-6) is synonymous with it.]

[0098] Preferably, the 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 formula (1) and 2) a'' and c'' are independently integers from 0 to 4, and b'' is an integer from 0 to 2.]

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

[0102]

Chemical formula

[0103] [wherein, 1) X 1 , X 4 , R 1 , R 2 and R 3 have the same meanings as defined in the said formula (1); 2) a'' and c'' are each independently an integer of 0 to 4, and b'' is an integer of 0 to 2.]

[0104] Further, the said formula (1-1) is represented by the following formula (1-1-a) or formula (1-1-b).

[0105]

Chemical formula

[0106] [wherein, 1) x, y, z, s and B have the same meanings as defined in formula (1); 2) i' is an integer of 1 to 20.]

[0107]

[0108]

Chemical formula

[0109] [wherein, 1) x, y, z and s have the same meanings as defined in the said formula (1); 2) i' is an integer of 1 to 20, d is an integer of 0 to 4, and 3) R 5 is deuterium; halogen; an aryl group of C6~C 20 ; a heterocyclic group of C2~C containing at least one heteroatom of O, N, S, Si and P 20 ; a condensed ring group of an aliphatic ring of C3~C and an aromatic ring of C6~C; an alkyl group of C1~C 20 ; selected from the group consisting of, or adjacent groups may be bonded to each other to form a ring.] 20 is selected from the group consisting of, or adjacent groups may be bonded to each other to form a ring.]

[0110] Further, the formula (1-2) can be represented by the following formula (1-2-a) or formula (1-2-b).

[0111]

Chemical formula

[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]

Chemical formula

[0115]

Chemical formula

[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]

Chemical formula

[0118]

Chemical formula

[0119]

Chemical formula

[0120]

Chemical formula

[0121] [Chemical]

[0122] [Chemical]

[0123] [Chemical]

[0124] [Chemical]

[0125] [Chemical]

[0126] [Chemical]

[0127] [Chemical]

[0128] [Chemical]

[0129] [Chemical]

[0130] [Chemical]

[0131] [Chemical]

[0132] [Chemical formula]

[0133] [Chemical formula]

[0134] Here, the fluorine content of the compound represented by the 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 compound described in this specification is represented by the following mathematical 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 the compound means the number of fluorine atoms contained in the compound, and the total number of atoms in the compound means the total number of atoms of the compound containing fluorine.

[0136] In another aspect of the present invention, the present invention provides an organic electronic device including a positive electrode, an organic layer formed on the positive electrode, and a metal patterning layer formed on the organic layer. At this time, the metal patterning layer contains one kind of single compound or two or more compounds represented by the formula (1).

[0137] The organic layer may include at least one layer of 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 still another aspect of the present invention, the present invention provides an electronic device including a display device including the organic electronic device represented by the formula (1) and a control unit for driving the display device.

[0139] Hereinafter, the laminated structure of the organic electronic device containing the compound of the present invention will be described with reference to FIGS. 1 to 3.

[0140] When adding reference numerals to the components of each drawing, for the same components, even if they are shown in other drawings, they should preferably have the same numerals as much as possible. Further, in the description of the present invention, when it is determined that a specific description of a related known configuration or function obscures the gist of the present invention, the detailed description thereof will be omitted.

[0141] When terms such as "comprising", "having", "becoming" and the like referred to in this specification are used, other parts can be added unless "only" is used. When a component is expressed in the singular, it includes the case of including a plurality unless there are particularly explicit descriptions.

[0142] Also, when describing the components of the present invention, terms such as first, second, A, B, (a), (b), etc. can be used. This term is for distinguishing the component from other components, and the nature, order, sequence, etc. of the component are not limited by the term. When a component is described as being "connected", "coupled" or "connected" to another component, it should be understood that the component may be directly connected or connected to the other component, but another component may be further "connected", "coupled" or "connected" between the components.

[0143] Also, when a component such as a layer, film, region, plate, etc. is said to be "on" another component, it should be understood that this includes 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, it should be understood to mean that there is no other part in between.

[0144] FIGS. 1, 2 and 3 are exemplary views of the organic electronic device according to the embodiment of the present invention.

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

[0146] The organic layers 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 etc. may serve as a hole blocking layer. An electron injection layer may be formed on the electron transport layer 150, and although it may be excluded as necessary, it is not limited thereto.

[0147] The metal patterning layer 190 containing the compound represented by the formula (1) is formed on the organic layers, and the second electrode 170 is not formed on the portion where the metal patterning layer is formed. That is, by using the compound represented by the formula (1) according to the present invention as the material of the metal patterning layer 170, only the portion or the selected site where the second electrode material is to be formed can be formed. Or by forming a metal patterning layer on the organic layers as shown in FIG. 3, the formation of the second electrode can be suppressed.

[0148] When the metal patterning layer is coated, depending on the structure of the compound entering the metal patterning layer and the fluorine content, the deposition of the negative electrode on the metal patterning layer is suppressed, and finally, the negative electrode is deposited in an extremely small amount or not deposited at all.

[0149] At this time, for the coating of the electrode (electrically conductive substance), the light transmittance is used to examine the amount of the electrode substance present on a certain surface. The reason is that the electrode substance contains metal, and electrically conductive substances such as metal 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 have substantially no electrically conductive substance.

[0150] As a result, the pixels of the organic electronic device including the metal patterning are highly transparent and do not emit light, acting as blanks, and due to the high transparency, it becomes possible to transmit without light noise to various wide-angle sensors (optical sensors) such as (TFT substrates) under the substrate.

[0151] Therefore, in the organic electronic device including the metal patterning layer (see FIG. 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 and light is not emitted.

[0152] On the other hand, the present invention provides a composition for metal patterning containing two or more compounds of the same kind as the compound represented by the formula (1) or compounds having different structures from each other.

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

[0154] Further, the organic layer can be manufactured with a smaller number of layers by methods such as a solution process or a solvent process, for example, a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll-to-roll process, a doctor blade process, a screen printing process, or a thermal transfer method, rather than a vapor deposition method using various polymer materials. Since the organic layer according to the present invention can be formed by various methods, the scope of the right of the present invention is not limited by the formation method.

[0155] Further, the organic electronic device according to an embodiment of the present invention can be selected from the group consisting of an organic light-emitting device, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting element, and a quantum dot display element.

[0156] Other embodiments of the present invention can include a display device including the organic electronic device of the present invention described above, and an electronic device including a control unit for controlling the display device. At this time, the electronic device may be a current or future wired or wireless communication terminal, such as a mobile communication terminal like a mobile phone including all electronic devices such as machines, PDAs, electronic dictionaries, PMPs, remote controls, navigations, game machines, various TVs, and various computers.

[0157] Hereinafter, synthesis examples of the compound represented by the above formula (1) of the present invention and manufacturing examples of the organic electronic device of the present invention will be specifically described with examples, but the present invention is not limited to the following examples.

[0158] Synthesis Example The compound (Final Product) represented by formula (1) according to the present invention is synthesized as shown in the following Reaction Scheme 1, but is not limited thereto.

[0159] <Reaction Scheme 1>

[0160]

Chemical formula

[0161] [In the formula, 1) Hal 1 , Hal 2 , Hal 3 and Hal 4 are each independently Cl, Br or I, 2) a'+a'' is a, b'+b'' is b, c'+c'' is c, provided that at least one of a'', b'' and c'' is 1 or more, 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, z have the same meaning as the above definitions.]

[0162] Synthesis of I.Sub1

[0163] Synthesis Examples of 1.Sub1-9

[0164]

Chemical Formula

[0165] In a round-bottom flask, 1,4-dibromo-2-iodobenzene (10.0 g, 27.6 mmol) was dissolved in THF (138 mL), and 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 completed, it was extracted with CH2Cl2 and water, and then the organic layer was dried over MgSO4 and concentrated. Subsequently, the resulting compound was applied to a silica gel column and then recrystallized to obtain 7.5 g of the product (yield: 75%).

[0166] Synthesis Examples of 2.Sub1-12​​​

[0167]

Chem.

[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 used in the synthesis method of Sub1-9 above to obtain 4.9 g of the product (yield: 77%).

[0169] 3. Synthesis Example of Sub1-46

[0170]

Chem.

[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 used in the synthesis method of Sub1-9 above, and 4.4 g of the product (yield: 81%) was obtained.

[0172] 4. Synthesis Example of Sub1-58

[0173]

Chem.

[0174] To a round-bottom flask were added dibenzo[b,d]thiophen-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), and the mixture was stirred at 100 °C. After the reaction was completed, it was extracted with CH2Cl2 and water, and then the organic layer was dried over MgSO4 and concentrated. Subsequently, the resulting compound was applied to a silica gel column and then recrystallized to obtain 7.5 g of the product (yield: 71%).

[0175] Synthesis Example of 5.Sub1-63

[0176]

Chemical Structure

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

[0178] Synthesis Example of 6.Sub1-69

[0179]

Chemical Structure

[0180] (2-Bromo-4-chlorophenyl)(4-chlorophenyl)sulfane (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 used according to the synthesis method of Sub1-9 to obtain 4.4 g of the product (yield: 74%).

[0181] 7. Synthesis Example of Sub1-78

[0182]

Chemical formula

[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 used according to the synthesis method of Sub1-58 to obtain 6.8 g of the product (yield: 78%).

[0184] 8. Synthesis Example of Sub1-83

[0185]

Chemical formula

[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 used according to the synthesis method of Sub1-9 to obtain 8.3 g of the product (yield: 78%).

[0187] 9. Synthesis Example of Sub1-112

[0188]

Chem.

[0189] 2-Chloro-8,8-dimethyl-5,8-dihydroinden[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 used according to the synthesis method of Sub1-58 to obtain 4.7 g of the product (yield: 76%).

[0190] On the other hand, the 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. For compounds known in Table 1 below, they are indicated by CAS♯, and for compounds not known, they are indicated by FD-MS.

[0191]

Chem.

[0192]

Chem.

[0193]

Chem.

[0194]

Chem.

[0195]

Chem.

[0196]

Chem.

[0197]

Chem.

[0198]

Table 1-1

[0199]

Table 1-2

[0200]

Table 1-3

[0201] II. Synthesis of Sub2

[0202] 1. Synthesis Example of Sub2-12

[0203]

Chem.

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

[0205] To 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, then for 30 minutes It was stirred intermittently. 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 over 1 hour, and then stirred at 120 °C for 24 hours. After the reaction was completed, distilled water was added, and the resulting solid was filtered under reduced pressure. Then, the filtrate was extracted with ethyl acetate, the organic layer was dried over MgSO4 and concentrated, and the resulting compound was separated by silica gel column to obtain 63.0 g of the product (yield: 68%).

[0206] (2) Synthesis example of Sub2 - 12 - b

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

[0208] (3) Synthesis example of Sub2 - 12

[0209] To a round - bottom flask, the Sub2 - 12 - b synthesized above (40.0 g, 50.8 mmo l), Cu (7.10 g, 112 mmol) and DMSO (102 mL) were added, dissolved at 70 °C, and then stirred 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 over 1 hour, and then stirred at 120 °C for 24 hours. After the reaction was completed, distilled water was added, and the resulting solid was filtered under reduced pressure. Then, the filtrate was extracted with ethyl acetate, the organic layer was dried over MgSO4 and concentrated, and the resulting compound was separated by silica gel column to obtain 11.0 g of the product (yield: 20%).

[0210] 2. Synthesis Example of Sub2-13

[0211]

Chemical Structure

[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 used according to the synthesis method of Sub2-12 to obtain 9.3 g of the product (yield: 17%).

[0213] 3. Synthesis Example of Sub2-15

[0214]

Chemical Structure

[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 used according to the synthesis method of Sub2-12 to obtain 9.1 g of the product (yield: 19%).

[0216] 4. Synthesis Example of Sub2-16

[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 used in the synthesis method of Sub2-12 to obtain 13.2 g of the product (yield: 21%).

[0218] On the other hand, the 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, for known compounds, they are shown by CAS#, and for unknown compounds, they are shown by FD-MS.

[0219] [Chemical formula]

[0220] [Table 2]

[0221] III. Synthesis of Sub3

[0222] 1. Synthesis example of Sub3-1

[0223] [Chemical formula]

[0224] To a round-bottom flask, 1-iodo-4-(trifluoromethyl)benzene (5.0 g, 18.4 mmol) was added, followed by bis(pinacolato)diboron (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 completed, the reaction solution was concentrated and then separated by silica gel column to obtain 3.9 g of the product (yield: 79%).

[0225] 2. Synthesis Example of Sub3-2

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

[0227]

Chemical Structure

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

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

[0230] Sub3-2-a (50.7 g, 118 mmol) synthesized above, bis(pinacol -Boronic acid (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) were used in the synthesis method of Sub3-1 to obtain 49.9 g of the product (yield: 81%).

[0231] 3. Synthesis Example of Sub3-7

[0232]

Chemical Structure

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

[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 used in the synthesis method of Sub3-2-a to obtain 14. 6 g of the product (yield: 77%).

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

[0236] The previously synthesized Sub3-7-a (14.6 g, 28.9 mmol), bis(pinacolato )diboron (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) were used in the synthesis method of Sub3-1 to obtain 13.8 g of the product (yield: 80%).

[0237] 4. Synthesis Example of Sub3-15

[0238]

Chemical Structure

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

[0240] Into a round-bottom flask, (3-chlorophenyl)boronic acid (8.0 g, 51.2 mmol) and 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) were added. After dissolving in DME (ethylene glycol dimethyl ether) (256 mL) and 1N aqueous NaHCO3 solution (128 mL), Pd(PPh3)4 (3.55 g, 3.07 mmol) was added, and the mixture was refluxed and stirred for 5 hours. After the reaction was completed, it was cooled to room temperature, extracted with diethyl ether and brine, and the obtained organic layer was dried over MgSO4 to remove the remaining moisture. Then, the obtained organic layer was filtered under reduced pressure, and 17.7 g of the product (yield: 76%) was obtained through a silica gel column.

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

[0242] The Sub3-15-a (17.7 g, 38.7 mmol) synthesized above, bis(pina colato)diboron (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) were used according to the synthesis method of Sub3-1 to obtain 16.9 g of the product (yield: 79%).

[0243] 5. Synthesis Example of Sub3-23

[0244]

Chemical Structure

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

[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 method of Sub3-2-a above to obtain 99.8 g of the product (yield: 78%).

[0247] (2) Synthesis example of Sub3-23

[0248] The synthesized Sub3-23-a (99.8 g, 86.9 mmol), bis(pina colate) diboron (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) were used in the synthesis method of Sub3-1 above to obtain 84.5 g of the product (yield: 78%).

[0249] On the other hand, the 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] [Chemical formula]

[0251] [Chemical formula]

[0252] [Table 3]

[0253] IV. Synthesis of Final product

[0254] 1. Synthesis example of P1-1

[0255] [Chemical formula]

[0256] To a round 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, and then stirred at 120 °C for 24 hours. After the reaction was completed, distilled water was added, and the resulting solid was filtered under reduced pressure. Then, the filtrate was extracted with ethyl acetate, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was separated by silica gel column and recrystallized to obtain 6.6 g of the product (yield: 80%).

[0257] 2. Synthesis Example of P1-22

[0258]

Chemical Formula

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

[0260] Sub1-1 (1.0 g, 5.22 mmol) was dissolved in toluene (17 mL) in a round flask, and 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 stirred at 120 °C. After the reaction was completed, it was separated by silica gel column and recrystallized to obtain 3.53 g of the product (yield: 82%).

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

[0262] Inter1-22 (3.0 g, 3.64 mmol) synthesized above was dissolved in toluene (12 mL) in a round-bottomed flask, and 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, followed by stirring at 120 °C. After the reaction was completed, it was separated by silica gel column and then recrystallized to obtain 3.41 g of the product (yield: 79%).

[0263] 3. Synthesis Example of P1-23

[0264]

Chemical formula

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

[0266] Using the same synthesis method as that of Inter1-22 above, 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 used to obtain 4.4 g of the product (yield: 69%).

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

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

[0269] 4. Synthesis Example of P1-34

[0270]

Chemical formula

[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 with the synthesis method of P1-22 to obtain 5.0 g of the product (yield: 78%).

[0272] 5. Synthesis Example of P1-44

[0273]

Chemical formula

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

[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 used with the synthesis method of Inter1-22 to obtain 3.3 g of the product (yield: 67%).

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

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

[0278] 6. Synthesis Example of P1-46

[0279]

Chemical formula

[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 used in the synthesis method of P1-22 to obtain 4.6 g of the product (yield: 79%).

[0281] 7. Synthesis Example of P1-50

[0282]

Chemical formula

[0283] Sub1-24 (1.0 g, 3.21 mmol), Sub3-23 (8.8 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 used in the synthesis method of P1-22 to obtain 5.3 g of the product (yield: 70%).

[0284] 8. Synthesis Example of P1-52

[0285]

Chemical formula

[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 used in the synthesis method of P1-22 to obtain 3.1 g of the product (yield: 73%).

[0287] 9. Synthesis Example of P1-55

[0288]

Chemical formula

[0289] Sub1-26 (1.0 g, 3.21 mmol), Sub3-23 (8.8 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 used in the synthesis method of P1-22 to obtain 5.5 g of the product (yield: 72%).

[0290] 10. Synthesis Example of P1-61

[0291]

Chemical Structure

[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 used in the synthesis method of P1-22 to obtain 3.8 g of the product (yield: 58%).

[0293] 11. Synthesis Example of P1-63

[0294]

Chemical Structure

[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 used in the synthesis method of P1-22 to obtain 4.8 g of the product (yield: 75%).

[0296] 12. Synthesis Example of P1-65

[0297]

Chemical Structure

[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 used in the synthesis method of P1-22 to obtain 4.1 g of the product (yield: 76%).

[0299] 13. Synthesis Example of P1-67

[0300]

Chemical formula

[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 used in the synthesis method of P1-22 to obtain 4.4 g of the product (yield: 77%).

[0302] 14. Synthesis Example of P1-69

[0303]

Chemical formula

[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 in the synthesis method of P1-22 to obtain 4.8 g of the product (yield: 71%).

[0305] 15. Synthesis Example of P1-71

[0306]

Chemical formula

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

[0308] 16. Synthesis Example of P1-73

[0309]

Chemical Structure

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

[0311] 17. Synthesis Example of P2-1

[0312]

Chemical Structure

[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 used in the synthesis method of P1-22 to obtain 4.9 g of the product (yield: 61%).

[0314] 18. Synthesis Example of P2-2

[0315]

Chemical Structure

[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 used in the synthesis method of P1-22 to obtain 3.1 g of the product (yield: 78%).

[0317] 19. Synthesis Example of P3-2

[0318]

Chemical formula

[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 used in the synthesis method of P1-22 to obtain 3.6 g of the product (yield: 61%).

[0320] 20. Synthesis Example of P3-4

[0321]

Chemical formula

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

[0323] 21. Synthesis Example of P3-5

[0324]

Chemical formula

[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 used in the synthesis method of P1-22 to obtain 4.1 g of the product (yield: 68%).

[0326] 22. Synthesis Example of P4-2

[0327]

Chemical formula

[0328] The synthesized 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) were used in the synthesis method of P1-1 to obtain 3.6 g of the product (yield: 72%).

[0329] 23. Synthesis Example of P4-4

[0330]

Chemical formula

[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 used in the synthesis method of P1-22 to obtain 5.2 g of the product (yield: 73%).

[0332] 24. Synthesis Example of P5-3

[0333]

Chemical formula

[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 used in the synthesis method of P1-22 to obtain 4.5 g of the product (yield: 79%).

[0335] 25. Synthesis example of P5-6

[0336]

Chemical formula

[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 used in the synthesis method of P1-22 to obtain 4.8 g of the product (yield: 75%).

[0338] 26. Synthesis example of P6-1

[0339]

Chemical formula

[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 used in the synthesis method of P1-1 to obtain 4.9 g of the product (yield: 81%).

[0341] 27. Synthesis example of P6-4

[0342]

Chemical formula

[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 used in the synthesis method of P1-22 to obtain 3.3 g of the product (yield: 72%).

[0344] 28. Synthesis example of P7-1

[0345]

Chemical formula

[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 used in the synthesis method of P1-1 to obtain 4.4 g of the product (yield: 75%).

[0347] 29. Synthesis example of P7-4

[0348]

Chemical formula

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

[0350] 30. Synthesis example of P8-2

[0351]

Chemical formula

[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 used with the synthesis method of P1-1 to obtain 3.4 g of the product (yield: 52%).

[0353] 31. Synthesis Example of P8-3

[0354]

Chemical formula

[0355] The synthesized 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) were used with the synthesis method of P1-1 to obtain 3.9 g of the product (yield: 77%).

[0356] 32. Synthesis Example of P9-3

[0357]

Chemical formula

[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 used with the synthesis method of P1-22 to obtain 4.3 g of the product (yield: 73%).

[0359] 33. Synthesis Example of P9-4

[0360]

Chemical formula

[0361] The synthesized 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) were used with the synthesis method of P1-1 to obtain 3.6 g of the product (yield: 82%).

[0362] 34. Synthesis Example of P9-6

[0363]

Chemical formula

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

[0365] 35. Synthesis Example of P10-1

[0366]

Chemical formula

[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 used with the synthesis method of P1-1 to obtain 8.2 g of the product (yield: 77%).

[0368] 36. Synthesis Example of P10-5

[0369]

Chemical formula

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

[0371] 37. Synthesis Example of P11-2

[0372]

Chemical formula

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

[0374] 38. Synthesis Example of P11-4

[0375]

Chemical formula

[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 used with the synthesis method of P1-1 to obtain 4.8 g of the product (yield: 80%).

[0377] 39. Synthesis Example of P11-6

[0378]

Chemical formula

[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 used with the synthesis method of P1-22 to obtain 5.2 g of the product (yield: 71%).

[0380] 40. Synthesis Example of P11-10

[0381]

Chemical formula

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

[0383] 41. Synthesis Example of P12-1

[0384]

Chemical formula

[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 used with the synthesis method of P1-22 to obtain 4.0 g of the product (yield: 73%).

[0386] 42. Synthesis Example of P13-3

[0387]

Chemical formula

[0388] To 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 (0.1 8 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 completed, it was extracted with CH2Cl2 and water, and then the organic layer was dried over MgSO4 and concentrated. Thereafter, the resulting compound was applied to a silica gel column and then recrystallized to obtain 5.1 g of the product (yield: 72%).

[0389] 43. Synthesis Example of P14-4

[0390]

Chemical formula

[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 used according to the synthesis method of P1-22 to obtain 4.0 g of the product (yield: 79%).

[0392] 44. Synthesis Example of P15-2

[0393]

Chemical formula

[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 used according to the synthesis method of P1-1 to obtain 5.8 g of the product (yield: 77%).

[0395] 45. Synthesis Example of P16-2

[0396] [Chemical]

[0397] Using the synthesis method of P1-1 above, 3.7 g (yield: 75%) of the product was obtained from 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).

[0398] 46. Synthesis Example of P17-1

[0399] [Chemical]

[0400] Using the synthesis method of P13-3 above, 7.3 g (yield: 74%) of the product was obtained from 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).

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

[0402] [Table 4-1]

[0403] [Table 4-2]

[0404] [Table 4-3]

[0405] Measurement of Light Transmittance

[0406] Example 1: Comparison of Light Transmittance According to the Type of Metal Patterning Layer First, an N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine (hereinafter abbreviated as 'C-1') film was vacuum-deposited on a glass substrate to form a 100-nm-thick film. On the organic layer, the 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 as an electron injection layer on the electrode patterning layer, and then Mg and Ag were deposited at a weight ratio of 1:9 to form a negative electrode. Thereafter, 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 to prepare a sample necessary for measuring the light transmittance.

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

[0408] Comparative Example 1 A light transmittance sample was prepared in the same manner as in Example 1, except that no metal (electrode) patterning layer was 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 the compound P1-22 of the present invention as the metal (electrode) patterning layer material.

[0410] Comparative Compound A

[0411]

Chemical Formula

[0412] The light transmittance samples of the examples and comparative examples prepared as described above were measured for their light transmittance at 550 nm in the visible light region using a Lambda 365 UV / VIS spectrometer (manufactured by Perkinelmer), and the measurement results are shown in the evaluation results in Table 5 below. Also, the fluorine content of the metal (electrode) patterning layer material is shown in Table 5 below. The results in Table 5 below were created based on the graph of the light transmittance measurement results in FIG. 5.

[0413]

Table 5

[0414] Looking at the results in Table 5 above, it was confirmed that when Comparative Example 1 without using a metal patterning layer and Comparative Compound A, which is a compound with a low fluorine content in the molecule, were used, the light transmittance was less than 90%. In the case of Examples 1 to 10 using the compound of the present invention with a fluorine content in the molecule of 30% or more, it was confirmed that the light transmittance was 90% or more.

[0415] Particularly in the case of Comparative Example 1, as a result of comparative evaluation with Comparative Example 2 and Examples 1 to 10 respectively, it was confirmed that the light transmittance showed 69.13% to 72.38% for each lot. Also, in the case of Comparative Compound A with a fluorine content in the molecule of 13.16%, it was confirmed that it had a lower light transmittance than Comparative Example 1 without a material containing fluorine in the molecule.

[0416] The light transmittance showed a slight difference for each lot in Comparative Example 1. After calculating the light transmittance of Comparative Example 1 for each lot as 100% and showing the difference in light transmittance with the compound of the present invention as T% (corrected), it was found that when the compound of the present invention was used instead of Comparative Example 1, the light transmittance increased by 28% to 39%.

[0417] Regarding the coating of an electrode (an electrically conductive material), the light transmittance is used to examine the amount of the electrode material present on a certain surface. The reason is that the electrode material contains a metal, and an electrically conductive material such as a metal attenuates and / or absorbs light. Therefore, a surface with a light transmittance exceeding 90% in the visible light region of the electromagnetic spectrum is considered to have substantially no electrically conductive material.

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

[0419] To confirm the above content, the end faces of the Comparative Example 1 and Example 3 samples were confirmed using a scanning electron microscope (SEM: Scanning Electron Microscope), which is an analytical device capable of observing the surface of the metal type. The results were as shown in FIG. 4 (FE-SEM: JMS6701F manufactured by JEOL).

[0420] As shown in FIG. 4(a), it was confirmed that a white and thin film was formed between the organic layer (lower end) and the capping layer (upper end). As shown in FIG. 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 Depending on the Presence or Absence of the Metal in the Electron Injection Layer and the Metal Type of the Electrode On a glass substrate, first, a C-1 film was vacuum-deposited as an organic layer to form a thickness of 100 nm. The compound P1-46 of the present invention was vacuum-deposited on the organic layer to a thickness of 10 nm to form a metal patterning layer. Then, Yb was vacuum-deposited as an electron injection layer on the metal patterning layer, and then Mg and Ag were vapor-deposited as a negative electrode at a weight ratio of 1:9. Thereafter, D-1 was vapor-deposited as a capping layer to a thickness of 70 nm to manufacture a 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 without using Yb which is a metal for the electron injection layer First, a C-1 film was vacuum-deposited on a glass substrate as an organic layer to form a film with 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, Mg and Ag were deposited at a weight ratio of 1:9 as a negative electrode on the metal patterning layer. Then, D-1 was deposited as a capping layer to a thickness of 70 nm to manufacture an organic electronic device.

[0424] Comparative Example 4: Sample without using Yb which is a metal for the electron injection layer 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 an electrode (negative electrode) First, a C-1 film was vacuum-deposited on a glass substrate as an organic layer to form a film with 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 on the metal patterning layer, and then Ag was deposited as a negative electrode. Then, D-1 was deposited as a capping layer to a thickness of 70 nm to manufacture an organic electronic device.

[0426] Comparative Example 5: Sample using only Ag as an 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 thus manufactured Examples and Comparative Examples were measured for the light transmittance at 550 nm in the visible light region using a Lambda 365 UV / VIS spectrometer (manufactured by Perkinelmer), and the measurement results are shown in the evaluation results in Table 6 below.

[0428]

Table 6

[0429] The results in Table 6 were created based on the graph of the light transmittance measurement results in Figure 6. Table 6 compared the light transmittances of Comparative Example 3, Comparative Example 4, and Comparative Example 5 without using a metal patterning layer with Example 11, Example 12, and Example 13 using the inventive compound P1-46 with an intramolecular fluorine content of 30% or more, to examine the feasibility of electrode patterning depending on the presence or absence of metal in the electron injection layer and the change in electrode patterning depending on the metal type of the negative electrode. Comparative Example 3 and Example 11 were evaluated as a comparison group when Yb, the metal in the electron injection layer, and Mg, the negative electrode metal, were not used. When the inventive compound P1-46 with an intramolecular fluorine content of 30% or more was used in the metal patterning layer, it was confirmed that a light transmittance of 95.63% was shown.

[0430] To confirm the patterning performance with respect to the metal of the negative electrode, excluding Yb, the metal used as the electron injection layer, Comparative Example 4 and Example 12 were conducted. As a result, when there was no Yb, the metal in the electron injection layer, the light transmittance of Example 12 using the inventive compound was 96.68% (T%: 146%), which was confirmed to be higher than that of Example 11 when there was an electron injection layer (a 16% increase in T%).

[0431] Also, to examine the patterning performance according to the metal type of the negative electrode, the results of comparing Comparative Example 5 using only Ag as the negative electrode, Example 13, with Comparative Example 3 and Example 11, which were the comparison groups, showed that when only Ag was used as the negative electrode and the inventive compound was used in the metal patterning layer, it was confirmed that the light transmittance increased by 5% compared to Example 11 at 135% (T%).

[0432] Example 14 First, a C-1 film was vacuum-deposited as an organic layer on a glass substrate to form a layer with a thickness of 100 nm. Then, Compound P1-22 of the present invention was vacuum-deposited on the organic layer to a thickness of 3 nm to form a metal patterning layer. Next, Yb was vacuum-deposited as an electron injection layer on the metal patterning layer, and then Mg and Ag were co-evaporated at a weight ratio of 1:9 to form a cathode. Thereafter, D-1 was deposited as a capping layer to a thickness of 70 nm to fabricate a sample.

[0433] Examples 15 to 25 Samples were fabricated 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 instead of Compound P1-22 of the present invention as the metal patterning layer material.

[0434] Comparative Example 6 Samples were fabricated in the same manner as in Example 14, except that no metal patterning layer was used.

[0435] The light transmittance samples of the examples and comparative examples thus produced were measured for the light transmittance at 550 nm in the visible light region using a Lambda 365 UV / VIS spectrometer (manufactured by Perkinelmer), and the measurement results are shown in the evaluation results in Table 7 below.

[0436] [Table 7]

[0437] The results in Table 7 above were created based on the graph of the light transmittance measurement results in Figure 7. Table 7 was conducted to confirm the change in light transmittance according 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 examples used during the evaluation of each material described in Examples 14 to 25 are described in the range (69.13% to 72.38%), the measured light transmittance for each lot was calculated as 100% (T%), and the light transmittance of the examples relative thereto was described as T%.

[0438] In Examples 14 to 25, when the compound of the present invention was used as a metal patterning layer having a thickness of 3 nm, 5 nm, or 10 nm, it was confirmed that there was no significant difference in the light transmittance, which was 95.01% to 96.47% (T% 132% to 140%). This indicates that when the compound of the present invention is used as a material for metal patterning, problems such as performance degradation due to variations in the 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 on a glass substrate to a thickness of 50 nm.

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

[0441] Comparative Example 7 The same method as in Example 26 was used, except that C-1 was used instead of the compound P1-34 of the present invention.

[0442] The contact angles of the samples of Comparative Example 7 and Examples 26 to 34 prepared in this way were measured with a DSA2 5 (manufactured by KRUSS) contact angle measuring device, and the measurement results are shown in the evaluation results in Table 8 below. shown.

[0443]

Table 8

[0444] As shown in Table 8 above, it was confirmed that the contact angle of the C-1 substance without fluorine and with low light transmittance was 83.2°, while the contact angles of the compounds of the present invention with a light transmittance of 90% or more were all confirmed to be 100° or more (103.6 to 118.2). The results in Table 8 above are judged to show the reason why the compounds of the present invention having a high light transmittance (90% or more) are suitable for metal patterning. Generally, adhesiveness 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 thus, when the adhesiveness becomes smaller, it has a low solid surface energy. This is because when the surface tension of the liquid is large, the force pulling itself together becomes large, making it difficult to spread on the solid surface.

[0445] The above content can be confirmed by the following Young's equation.

[0446] The following relationship holds between the interfacial tension and the contact angle. γLVcosθ = γSV - γSL (1) γSL: Interfacial tension between solid and liquid γSV: Interfacial tension between solid surface and liquid vapor γLV: Interfacial tension between liquid and liquid vapor

[0447] The formula of the above formula (1) for the work of adhesion Wa presented by Dupre is shown as follows. Wa = γS + γLV - γSL = γS + γLV + (γLVcosθ - γSV) = (γS - γSV) + γLV(1 + cosθ) (2) γS in the above formula (2) is the surface tension of the solid itself. Generally, at a low surface energy, γS and γSV are considered equal. Therefore, the above formula (2) is summarized as follows. Wa = γLV(1 + cosθ) (3) From the above formula (3), if the contact angle is 0°, then cos0° = 1, indicating complete wetting. On the other hand, if the contact angle is 180°, then cos180° = -1, meaning no wetting at all.

[0448] Therefore, as the contact angle decreases from 90° to 0°, cosθ approaches 1, resulting in increased wettability and adhesiveness. Conversely, as the contact angle increases from 90° to 180°, cosθ approaches -1, leading to decreased wettability and adhesiveness.

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

[0450] The above description is merely illustrative of the present invention. Those with ordinary knowledge in the technical field to which the present invention pertains can make various modifications without departing from the essential characteristics of the present invention. Therefore, the examples disclosed in this specification are for the purpose of explaining rather than limiting the present invention, and the spirit and scope of the present invention are not limited by such examples. The protection scope of the present invention should be interpreted by the following claims, and all technologies within the equivalent scope should be construed as being included in the scope of the rights of the present invention.

[0451] (Industrial Applicability) According to the present invention, an organic device having excellent device characteristics of high brightness, high emission, and long life can be manufactured, and it has industrial applicability.

Explanation of Reference Numerals

[0452] 100, 200, 300: Organic electronic device 110: First electrode 120: Hole injection layer 130: Hole transport layer 140: Light-emitting layer 150: Electron transport layer 170: Second electrode 180: Light efficiency improvement layer 190: Metal patterning layer

Claims

1. A fluorinated compound represented by the following formula (2): 【Chemical 1】 [wherein, 1) Ar １ , Ar ２ , and A are each independently selected from the group consisting of phenyl, biphenyl, naphthyl, and terphenyl, 2) R １ , R ２ , and R ３ are, independently of one another, substituents represented by the formula (1-1), 3) a and c are each independently an integer of 2 to 10, b is an integer of 0 to 10, 4) B is phenyl, biphenyl, naphthyl, or terphenyl, 5) i is an integer of 0 or 1, s is an integer of 1 to 5, provided that when i is 0, s is 1, 6) x is an integer of 1 to 5, y + z is an integer of 2x + 1, 7) m and n are each independently an integer of 0 or 1, wherein the phenyl, biphenyl, naphthyl, and terphenyl may each be further substituted with one or more substituents selected from the group consisting of deuterium, halogen, and cyano groups.]]

2. The fluorinated compound according to claim 1, wherein the formula (2) is represented by the following formula (2-6) 【Chemical 2】 [wherein, 1) Ar １ , Ar ２ , R １ , R ２ , R ３ , a, b, and c are synonymous with the definitions described in claim 1, 2) A' is phenyl, biphenyl, or terphenyl.]]

3. The fluorinated compound according to claim 2, wherein the formula (2) is represented by the following formula (2-7) [Chemical Formula 3] [wherein, 1) R １ , R ２ , R ３ , and b have the same meanings as defined in claim 1, 2) A' is phenyl, biphenyl, or terphenyl, 3) a' and c' are each independently an integer of 2 to 5.]]

4. The formula (2) is represented by the following formula (2-8) or formula (2-9) 【Chemical Formula 4】 [wherein, 1) b, B, i, x, y, z, and s have the same meanings as defined in the formula (2), 2) A' is phenyl, biphenyl, or terphenyl, 3) R ４ is synonymous with R in the formula (2).] The fluorinated compound according to claim 2, characterized in that it is represented by ２ .

5. In an organic electronic device having a positive electrode, at least one organic layer on the positive electrode, a non-light-emitting region including a metal patterning layer on the organic layer, and a light-emitting region including a metal; a metal electrode; or a metal and a metal electrode on the organic layer, the organic electronic device, wherein the metal patterning layer contains a fluorinated compound represented by the following formula (2). [Chemical Formula 5] [wherein, 1) Ar １ , Ar ２ , and A are each independently selected from the group consisting of phenyl, biphenyl, naphthyl, and terphenyl, 2) R １ 、R ２ 、and R ３ are, independently of each other, substituents represented by the formula (1-1), 3) a and c are each independently an integer of 2 to 10, b is an integer of 0 to 10, 4) B is phenyl, biphenyl, naphthyl, or terphenyl, 5) i is an integer of 0 or 1, s is an integer of 1 to 5, provided that when i is 0, s is 1, 6) x is an integer of 1 to 5, y + z is an integer of 2x + 1, 7) m and n are each independently an integer of 0 or 1, wherein the phenyl, biphenyl, naphthyl, and terphenyl may each be further substituted with one or more substituents selected from the group consisting of deuterium, halogen, and cyano groups.]]

6. The organic electronic device according to claim 5, wherein the metal contains Ag when patterning the metal using the compound represented by the formula (2).

7. The organic electronic device according to claim 5, wherein the metal contains Ag or Mg when patterning the metal using the compound represented by the formula (2).

8. The organic electronic device according to claim 5, wherein the metal patterning layer contains a mixture of two or more different compounds represented by the formula (2).

9. A display device including the organic electronic device according to claim 5; and A control unit for driving the display device; An electronic device including the above.

10. The electronic device according to claim 9, wherein the organic electronic device is selected from the group consisting of an organic electroluminescent element, an organic transistor, a monochromatic lighting element, and a quantum dot display element.

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