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: Disclosed is a fluorinated compound of formula (4), a composition for patterning metals comprising the same, and an organic electronic element comprising the same, as well as an electronic device thereof.SELECTED DRAWING: Figure 1

Description

[Technical Field]

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

[0002] 2. Description of the Related Art With the continuous development of display technology, user demands for display devices are increasing, and terminal display devices (especially smartphones) are being required to develop in the direction of flexibility, full screen, and high integration.

[0003] In particular, in the case of smartphone displays, efforts are being made to maximize the screen size of smartphones of the same size as technology advances, and as a result, development has been underway to minimize the bazel size of smartphones as screen size increases. In the process, the physical buttons on the front of smartphones have disappeared into the screen, and the position of smartphone cameras has been continually changed using methods such as notches, holes, and slides.

[0004] Recently, the development of bazel-less under-display This has led to rapid progress in the development of transparent display technology.

[0005] With the development of such display devices, the implementation of next-generation smartphone display technologies such as UDC (Under Display Camera) and UPS (Under Panel Sensor) has recently attracted a lot of attention.

[0006] In particular, UDC requires high transparency for the display in order for the UDC camera to function properly, so precise patterning of the cathode is essential to increase transparency.

[0007] Generally, there are two main methods used for electrode patterning: the first is to pattern the electrode in the desired area using a shadow mask, and the second is to create a pattern by irradiating the cathode with a laser.

[0008] However, the electrode patterning method using a shadow mask has a problem that warping occurs during a high-temperature deposition process due to the typical material properties of the metal mask, which causes distortion of the mask shape and electrode pattern. Therefore, time and costs are inevitably required for mask maintenance, making this method commercially unsuitable for mass production of devices.

[0009] In addition, the electrode patterning method using a laser is a method in which the electrode is patterned using the inherent properties of the laser, and the type and strength of the laser must be determined so as not to damage the substrate. This creates the hassle of having to make decisions.

[0010] Meanwhile, fluorinated organic compound materials are used in a variety of applications in organic electronic elements. For example, Patent Document 1 discloses a compound that functions as a sealant 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 opposing electrodes, and that further prevents moisture and oxygen from entering the light-emitting layer by vapor-depositing at least one polymer selected from the group consisting of chlorotrifluoroethylene homopolymer, dichlorofluoroethylene homopolymer, and copolymer of chlorotrifluoroethylene and dichlorodifluoreneethylene.

[0011] Furthermore, Patent Document 2 and Non-Patent Document 1 disclose that fluorine-containing substances have high chemical and thermal stability and can improve the electron transport properties, and therefore can be used as an electron transport layer of an organic EL device, and can also be used as a hole blocking layer as well as a protective film because they exhibit a hole blocking function, thereby improving the life of the device.

[0012] Patent Document 3 also discloses that fluorine-containing substances can be used as materials for the light-emitting layer in addition to the electron transport layer, and that a green light-emitting polymer is disclosed in which a fluorinated aryl with strong electron affinity, i.e., a pentafluoroaryl or octafluorobiphenyl group, is introduced into poly(p-phenylene vinylene) to induce a balanced encounter between electrons and holes, thereby improving the electroluminescence efficiency. Furthermore, Patent Document 4 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 compound is placed between the first electrode and the hole transport layer. 6y F 6y-2n The article also describes an organic light-emitting device characterized by further including the aromatic fluorocarbon compound between the light-emitting layer and the second electrode. This article discloses that the aromatic fluorocarbon compound is used to adjust the interface of the organic light-emitting device, by inserting a thin film containing a fluorine-containing compound at the interface between the first electrode (anode) and the hole injection (hole transport layer), thereby providing an organic light-emitting device with low power consumption due to enhanced driving voltage. [Prior art documents] [Patent documents]

[0013] [Patent Document 1] Japan Patent 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] J. Am. Chem. Soc., 2000, Vol.122, 1832. Summary of the Invention [Problem to be solved by the invention]

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

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

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

[0018] In the present invention, by using the compound represented by the formula (1) as a metal or electrode (cathode) patterning material, it is possible to form a fine pattern of an electrode without using a shadow mask, which makes it easy to produce a transparent display with high light transmittance and makes it easier to apply UDC. [Brief explanation of the drawings]

[0019] [Figure 1] 1 is an illustration of a display layer structure including a fluorine compound. [Figure 2] 1 is an illustration of a display layer structure including a fluorine compound. [Figure 3] 1 is an illustration of a display layer structure including a fluorine compound. [Figure 4A] FIG. 1 is a SEM cross-sectional view of Comparative Example 1. [Figure 4B] FIG. 10 is a SEM cross-sectional view of Example 3. [Figure 5A] 1 is a graph showing the measurement results of light transmittance in Comparative Example 1 and Example 1. [Figure 5B] 1 is a graph showing the measurement results of light transmittance in Comparative Example 1 and Example 2. [Figure 5C] 1 is a graph showing the measurement results of light transmittance in Comparative Example 1 and Example 3. [Figure 5D] 1 is a graph showing the measurement results of light transmittance in Comparative Example 1 and Example 4. [Figure 5E] 1 is a graph showing the measurement results of light transmittance in Comparative Example 1 and Example 5. [Figure 5F] 1 is a graph showing the measurement results of light transmittance of Comparative Example 1 and Example 6. [Figure 5G] 1 is a graph showing the measurement results of light transmittance in Comparative Example 1 and Example 7. [Figure 5H] 1 is a graph showing the measurement results of light transmittance of Comparative Example 1 and Example 8. [Figure 5I] 1 is a graph showing the measurement results of light transmittance of Comparative Example 1 and Example 9. [Figure 5J] 1 is a graph showing the measurement results of light transmittance in Comparative Example 1 and Example 10. [Figure 6A] 1 is a graph showing the measurement results of light transmittance in Comparative Example 3 and Example 11. [Figure 6B] 1 is a graph showing the measurement results of light transmittance in Comparative Example 4 and Example 12. [Figure 6C] 1 is a graph showing the measurement results of light transmittance in Comparative Example 5 and Example 13. [Figure 7A] 1 is a graph showing the results of measuring the light transmittance of Comparative Example 6 and Examples 14 to 16. [Figure 7B] 1 is a graph showing the results of measuring the light transmittance of Comparative Example 6 and Examples 17 to 19. [Figure 7C] 1 is a graph showing the results of measuring the light transmittance of Comparative Example 6 and Examples 20 to 22. [Figure 7D] 1 is a graph showing the results of measuring the light transmittance of Comparative Example 6 and Examples 23 to 25. [Figure 8A]FIG. 10 is a diagram showing the results of contact angle measurement in Comparative Example 7. [Figure 8B] FIG. 10 is a diagram showing the contact angle measurement results of Example 26. [Figure 8C] FIG. 10 is a diagram showing the contact angle measurement results of Example 27. [Figure 8D] FIG. 10 is a diagram showing the contact angle measurement results of Example 28. [Figure 8E] FIG. 10 is a diagram showing the contact angle measurement results of Example 29. [Figure 8F] FIG. 10 is a diagram showing the contact angle measurement results of Example 30. [Figure 8G] FIG. 10 is a diagram showing the contact angle measurement results of Example 31. [Figure 8H] FIG. 10 is a diagram showing the contact angle measurement results of Example 32. [Figure 8I] FIG. 10 is a diagram showing the contact angle measurement results of Example 33. [Figure 8J] FIG. 10 is a diagram showing the contact angle measurement results of Example 34. DETAILED DESCRIPTION OF THE INVENTION

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

[0021] The term "halo" or "halogen," as used herein, unless otherwise stated, refers to fluorine (F), bromine (Br), chlorine (Cl), or iodine (I).

[0022] The term "alkyl" or "alkyl group," as used herein, unless otherwise specified, refers to a single-bonded saturated aliphatic functional group having 1 to 60 carbon atoms, including a straight-chain alkyl group, a branched-chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cycloalkyl group, or a cycloalkyl-substituted alkyl group.

[0023] As used herein, unless otherwise specified, the terms "alkenyl group" or "alkynyl group" include, but are not limited to, double- or triple-bonded, straight- or branched-chain groups having 2 to 60 carbon atoms, respectively.

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

[0025] The terms "alkoxyl group," "alkoxy group," or "alkyloxy group" as used herein refer to an alkyl group having an oxygen radical bonded thereto, and unless otherwise specified, has from 1 to 60 carbon atoms, but is not limited thereto.

[0026] The term "aryloxyl group" or "aryloxy group" as used herein means an aryl group having an oxygen radical bonded thereto, and unless otherwise specified, has 6 to 60 carbon atoms, but is not limited thereto.

[0027] The term "alkylthio group," as used herein, means an alkyl group having a sulfur radical attached thereto, and unless otherwise specified, has from 1 to 60 carbon atoms, but is not limited to such.

[0028] The term "arylthio group," as used herein, means an aryl group having a sulfur radical attached thereto, and unless otherwise specified, has from 1 to 60 carbon atoms, but is not limited to such.

[0029] The terms "aryl group" and "arylene group" used herein each have 6 to 60 carbon atoms, but are not limited thereto, unless otherwise specified. In the present invention, an aryl group or an arylene group refers to a monocyclic or polycyclic aromatic ring, and includes an aromatic ring formed by bonding or reaction of adjacent substituents. 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" refers to a radical that is substituted with an aryl group. For example, an arylalkyl group is an alkyl group substituted with an aryl group; An alkenyl group is an alkenyl group substituted with an aryl group, and the aryl-substituted radical has the number of carbon atoms described herein. In addition, when prefixes are consecutively named, it means that the substituents are listed in the order described above. For example, an arylalkoxy group means an alkoxy group substituted with an aryl group, an alkoxylcarbonyl group means a carbonyl group substituted with an alkoxyl group, and an arylcarbonylalkenyl group means an alkenyl group substituted with an arylcarbonyl group, where the arylcarbonyl group is a carbonyl group substituted with an aryl group.

[0031] As used herein, unless otherwise specified, the term "heterocyclic group" refers to a group containing one or more heteroatoms, having 2 to 60 carbon atoms, and including at least one of a monocycle and a polycycle, including a heteroaliphatic ring and a heteroaromatic ring, which may be formed by bonding adjacent functional groups.

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

[0033] The term "heterocyclic group" refers to a monocyclic ring, a ring assembly, various fused ring systems, spiro compounds, etc., containing heteroatoms. Compounds containing heteroatom groups such as SO2, P=O, etc., instead of carbon atoms forming a ring, as in the following compounds, are also included in the heterocyclic group.

[0034] [ka]

[0035] The term "aliphatic cyclic group" as used in the present invention refers to cyclic hydrocarbons excluding aromatic hydrocarbons, including monocyclic rings, ring aggregates, various fused ring systems, spiro compounds, etc., and unless otherwise specified, refers to a ring having 3 to 60 carbon atoms, but is not limited thereto. For example, the condensation of benzene, an aromatic ring, with cyclohexane, a non-aromatic ring, also falls under the category of an aliphatic ring.

[0036] The terms "fluorenyl group", "fluorenylene group", and "fluorenetriyl group" used in the present invention mean, unless otherwise specified, that R, R', and R'' are each in the following structure. The term "substituted fluorenyl group," "substituted fluorenylene group," or "substituted fluorenetriyl group" refers to a monovalent, divalent, or trivalent functional group in which all substituents are hydrogen. The terms "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 include cases in which 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, fluorenyl groups, fluorenylene groups, and fluorenetriyl groups can all be referred to as fluorene groups, regardless of valence.

[0037] [ka]

[0038] In this specification, the "group names" corresponding to the aryl groups, arylene groups, heterocyclic groups, etc. exemplified in the examples of each symbol and its substituent can be written as "group names reflecting the valence" or as "parent compound names." For example, in the case of "phenanthrene," a type of aryl group, the group names can be written by distinguishing the valence, such as "phenanthryl" for a monovalent group and "phenanthrylene" for a divalent group, or they can be written as the parent compound name "phenanthrene" regardless of the valence. Similarly, in the case of pyrimidine, it can be written as "pyrimidine" regardless of the valence, or it can be written as the "group name" of the valence, such as pyrimidinyl group for a monovalent group and pyrimidinylene for a divalent group. Furthermore, in this specification, numbers and letters indicating positions can be omitted when writing compound names and substituent names. For example, pyrido[4,3-d]pyrimidine can be written as pyridopyrimidine, benzofuro[2,3-d]pyrimidine as benzofuropyrimidine, 9,9-dimethyl-9H-fluorene as dimethylfluorene, etc. Thus, both benzo[g]quinoxaline and benzo[f]quinoxaline can be written as benzoquinoxaline.

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

[0040] [ka]

[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 of the carbon atoms forming the benzene ring, and when a is an integer of 2 or 3, it is bonded as follows, and in this case, R 1 may be the same or different, and when a is an integer of 4 to 6, they are bonded to carbon atoms of the benzene ring in the same manner, while the hydrogen atoms bonded to carbon atoms forming the benzene ring are omitted.

[0042] [ka]

[0043] Unless otherwise specified in this specification, when a fused ring is represented by "number-fused ring", the number represents the number of fused rings. For example, a form in which three rings are fused to each other, such as anthracene, phenanthrene, or benzoquinazoline, can be represented as a 3-fused ring.

[0044] Unless otherwise specified herein, when a ring is expressed in the "number-atoms" format, such as a five-atom ring, a six-atom ring, etc., the number in "number-atoms" represents the number of elements forming the ring. For example, thiophene and furan may correspond to five-atom rings, while benzene and pyridine may correspond to six-atom rings.

[0045] Unless otherwise specified in this specification, the ring formed by bonding adjacent groups to each other is a ring having C6 to C 60 an aromatic ring group; a fluorenyl group; a C2-C group containing at least one heteroatom selected from O, N, S, Si, and P 60 Heterocyclic groups; and C3-C 60 an aliphatic cyclic group;

[0046] In this case, unless otherwise specified in the present specification, "adjacent groups" refers to groups adjacent to each other, for example, R 1 and R 2 Comrade, R 2 and R 3 Comrade, R 3 and R 4 Comrade, R 5 and R 6 R that share one carbon atom, not just with each other 7 and R 8 This includes friends and family. 1 and R 7 Comrade, R 1 and R 8 Comrades or R 4 and R 5This also includes substituents bonded to ring-constituting elements (carbon, nitrogen, etc.) that are not immediately adjacent to each other, such as when two ring-constituting elements are bonded to the same carbon or nitrogen. That is, when there are substituents on ring-constituting elements such as immediately adjacent carbon or nitrogen, these may form adjacent groups, but when no substituent is bonded to the ring-constituting element at the immediately adjacent position, the substituent bonded to the next ring-constituting element may form adjacent groups, and substituents bonded to the same ring-constituting carbon may also form adjacent groups.

[0047] In the following formula, R 7 and R 8 When substituents attached to the same carbon atom are joined together to form a ring, such as: a compound containing a spiro moiety can be formed.

[0048] [ka]

[0049] In addition, in this specification, the expression "adjacent groups can be bonded to each other to form a ring" is used in the same sense as "adjacent groups are bonded to each other to selectively form a ring", and means that at least one pair of adjacent groups are bonded to each other to form a ring.

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

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

[0052] [ka]

[0053] [In the formula, each symbol can be defined as follows.] 1) Ar 1 and Ar 2 are independent of each other, C6 to C 60aryl groups; C2-C containing at least one heteroatom selected from O, N, S, Si and P; 60 Heterocyclic groups; and C3-C 60 Aliphatic rings and C6-C 60 a fused ring group of aromatic rings; The Ar 1 and Ar 2 When is an aryl group, it is preferably a C6 to C 30 an aryl group of, more preferably, C6 to C 20 aryl groups, more preferably C6 to C 18 The alkyl group may be an aryl group such as phenyl, biphenyl, naphthyl, or terphenyl. The Ar 1 and Ar 2 When is a heterocyclic group, it is preferably a C2 to C 30 Heterocyclic groups of the formula (I), more preferably C2 to C 20 Heterocyclic groups of the formula (I), more preferably C2 to C 16 and the like, for example, pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, dibenzofuran, dibenzothiophene, naphthobenzothiophene, naphthobenzofuran, benzofuran, benzothiophene, and the like. 2) A, B, C and D are each independently -CR a R b -;-NR c -;-O-;-S-;-SiR d R e -;C6~C 60 arylene groups; fluorenylene groups; and C2-C groups containing at least one heteroatom selected from O, N, S, Si, and P. 60 heterocyclic groups; When A, B, C and D are arylene groups, they are preferably C6 to C 30 an arylene group, more preferably a C6-C 20 an arylene group of C6 to C 18 and the like, for example, phenylene, biphenylene, naphthylene, terphenylene, etc. When A, B, C and D are fluorenylene groups, they may be 9,9-dimethyl-9H-fluorenylene, 9,9-diphenyl-9H-fluorenylene, 9,9'-spirobifluorenylene or the like. When A, B, C, and D are heterocyclic groups, they are preferably C2 to C 30 Heterocyclic groups of the formula (I), more preferably C2 to C 20 Heterocyclic groups of the formula (I), more preferably C2 to C 16 and the like, for example, pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, dibenzofuran, dibenzothiophene, naphthobenzothiophene, naphthobenzofuran, benzofuran, benzothiophene, and the like. However, if m is 0, A is C6~C 60 or a C2-C group containing at least one heteroatom selected from O, N, S, Si, and P. 60 a heterocyclic group; When A is an aryl group, it is preferably a C6 to C 30 an aryl group of, more preferably, C6 to C 20 aryl groups, more preferably C6 to C 18 The alkyl group may be an aryl group such as phenyl, biphenyl, naphthyl, or terphenyl. When A is a heterocyclic group, it is preferably a C2 to C 30 Heterocyclic groups of the formula (I), more preferably C2 to C 20 Heterocyclic groups of the formula (I), more preferably C2 to C 16 and the like, for example, pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, dibenzofuran, dibenzothiophene, naphthobenzothiophene, naphthobenzofuran, benzofuran, benzothiophene, and the like. 3) R 1 , R 2 and R 3 are the same or different, and are independent of each other, C6 to C 60 an aryl group; a fluorenyl group; a C2-C group containing at least one heteroatom selected from O, N, S, Si, and P; 60 Heterocyclic group; C3-C 60 Aliphatic rings and C6-C60 Aromatic condensed ring group; C1-C 50 Alkyl groups of C1-C 50 Alkoxyl group; C6-C 60 -L-NR'R''; a substituent represented by the formula (1-1); and a substituent represented by the formula (1-2); or adjacent groups may be bonded to each other to form a ring. R 1 ~R 3 When is an aryl group, it is preferably a C6 to C 30 an aryl group of, more preferably, C6 to C 20 aryl groups, more preferably C6 to C 18 The alkyl group may be an aryl group such as phenyl, biphenyl, naphthyl, or terphenyl. R 1 ~R 3 When is a fluorenyl group, it may be 9,9-dimethyl-9H-fluorenyl, 9,9-diphenyl-9H-fluorenyl, 9,9'-spirobifluorenyl, or the like. R 1 ~R 3 When is a heterocyclic group, it is preferably a C2 to C 30 Heterocyclic groups of the formula (I), more preferably C2 to C 20 Heterocyclic groups of the formula (I), more preferably C2 to C 16 and the like, for example, pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, dibenzofuran, dibenzothiophene, naphthobenzothiophene, naphthobenzofuran, benzofuran, benzothiophene, and the like. R 1 ~R 3 When is an alkyl group, it is preferably C1 to C 20 alkyl groups, more preferably C1 to C 10 It may be an alkyl group such as methyl, t-butyl, etc. R 1 ~R 3 When is an alkoxy group, it is preferably a C1 to C 20 Alkoxyl groups, more preferably C1 to C 10and the like. The alkyl group may be an alkoxyl group such as methoxy, t-butoxy, etc. R 1 ~R 3 When is an aryloxy group, it is preferably a C6 to C 30 an aryloxy group, more preferably a C6 to C 20 It may also be an aryloxy group of the formula: However, R 1 , R 2 and R 3 At least one of the groups is a substituent represented by the formula (1-1) or a substituent represented by the formula (1-2). 4) a, b, and c are each independently an integer of 0 to 10, provided that a+b+c is 1 or greater. 5) m and n are each independently an integer of 0 to 50. When n is 0, R 2 is absent, then A+c is 1 or more, and if m is 0, then R 3 was absent, and at this time , when A+b is 1 or more and n and m are both 0, R 2 and R 3 is absent, and a is an integer from 1 to 10. 6) X 1 , X 2 , X 3 and X 4 are independent of each other, CR f R g , N.R. h , O, S or SiR i R j is. 7) R' and R'' are each independently C6 to C 60 aryl groups; C2-C containing at least one heteroatom selected from O, N, S, Si and P; 60 Heterocyclic groups; and C3-C 60 Aliphatic rings and C6-C 60 or adjacent groups may be bonded to each other to form a ring. When R' and R'' are aryl groups, they are preferably C6 to C 30 an aryl group of, more preferably, C6 to C 20aryl groups, more preferably C6 to C 18 The alkyl group may be an aryl group such as phenyl, biphenyl, naphthyl, or terphenyl. When R' and R'' are heterocyclic groups, they are preferably C2 to C 30 Heterocyclic groups of the formula (I), more preferably C2 to C 20 Heterocyclic groups of the formula (I), more preferably C2 to C 16 and the like, for example, pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, dibenzofuran, dibenzothiophene, naphthobenzothiophene, naphthobenzofuran, benzofuran, benzothiophene, and the like. 8)R a , R b , R c , R d , R e , R f , R g , R h , R i and R j are, independently of each other, hydrogen; deuterium; halogen; C6-C 60 aryl groups of C2-C containing at least one heteroatom selected from O, N, S, Si and P; 60 Heterocyclic group; C3-C 60 Aliphatic rings and C6-C 60 Aromatic condensed ring group; C1-C 50 or adjacent groups may be bonded to each other to form a ring. R a ~R j When is an aryl group, it is preferably a C6 to C 30 an aryl group of, more preferably, C6 to C 20 aryl groups, more preferably C6 to C 18 The alkyl group may be an aryl group such as phenyl, biphenyl, naphthyl, or terphenyl. R a ~R j When is a heterocyclic group, it is preferably a C2 to C 30 Heterocyclic groups of the formula (I), more preferably C2 to C 20Heterocyclic groups of the formula (I), more preferably C2 to C 16 and the like, for example, pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, dibenzofuran, dibenzothiophene, naphthobenzothiophene, naphthobenzofuran, benzofuran, benzothiophene, and the like. R a ~R j When is an alkyl group, it is preferably C1 to C 20 alkyl groups, more preferably C1 to C 10 It may be an alkyl group such as methyl, t-butyl, etc. 9) o, p, q and r are each independently an integer of 0 or 1. If is 0, then X 1 is absent, and if p is 0, then X 2 is absent, and if q is 0, then X 3 is absent and r is 0, then X 4 is absent. 10) x is an integer of 3 to 50. Furthermore, y+z is an integer of 2x+1, 2x, or 2x-2. For example, y may be 0, and z may be 2x+1, 2x, or 2x-2. In this case, x is preferably an integer 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 above range, there is a problem that Td becomes high during vacuum deposition, and if x is less than the above range, there is a high possibility that the compound will 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 represent a single bond, and in this case, s or u is 1. 12) L is a single bond; C6-C 60 an arylene group; a fluorenylene group; a C2-C group containing at least one heteroatom selected from O, N, S, Si, and P; 60 Heterocyclic group; C1-C 50 alkylene groups; and C3-C 60 Aliphatic rings and C6-C 60 a fused ring group of aromatic rings; When the L is an arylene group, it is preferably a C6 to C 30 an arylene group, more preferably a C6-C 20 an arylene group of C6 to C 18 Arylene groups, e.g. For example, it may be phenylene, biphenylene, naphthylene, terphenylene, or the like. When L is a fluorenylene group, it may be 9,9-dimethyl-9H-fluorenylene, 9,9-diphenyl-9H-fluorenylene, 9,9'-spirobifluorenylene, or the like. When L is a heterocyclic group, it is preferably a C2 to C 30 Heterocyclic groups of the formula (I), more preferably C2 to C 20 Heterocyclic groups of the formula (I), more preferably C2 to C 16 and the like, for example, pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, dibenzofuran, dibenzothiophene, naphthobenzothiophene, naphthobenzofuran, benzofuran, benzothiophene, and the like. When the L is an alkylene group, it is preferably a C1 to C 20 alkylene groups, more preferably C1 to C 10 It may be an alkylene group such as methylene, butylene, etc. 13) Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, fused ring group, alkyl group, alkoxyl group, aryloxy group, and rings formed by bonding adjacent groups to each other are each selected from the group consisting of deuterium, halogen, silane group, siloxane group, boron group, germanium group, cyano group, nitro group, C1 to C6 20 Alkylthio group; C1-C 20 Alkoxyl group; C6-C 20 Aryloxy groups of C1-C 20 Alkyl groups of C2 to C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 20 Aryl groups; deuterium-substituted C6-C 20 aryl groups; halogen-substituted C6-C 20Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl groups of C7-C 20 aryl alkyl groups; and C8-C 20 and these substituents may be bonded to each other to form a ring, where 'ring' means a C3 to C6 alkyl group. 60 Aliphatic ring or C6-C 60 Aromatic ring or C2-C 60 or a fused ring consisting of a combination thereof, and includes saturated or unsaturated rings.]

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

[0055] [ka]

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

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

[0058] [ka]

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

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

[0061] [ka]

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

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

[0064] [ka]

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

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

[0067] [ka]

[0068] [In the formula, 1)R 1 , R 2 , R 3 and b are defined as defined in the formula (1), 2) A' is defined as defined in formula (2-6) above, 3) a' and c' are each independently an integer of 0 to 5.

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

[0070] [ka]

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

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

[0073] [ka]

[0074] [In the formula, 1) b, x, y, and z are defined as defined in the formula (1), 2) A' is defined as defined in formula (2-6) above, 3) R 4 has the same definition as in formula (2-12).

[0075] Moreover, the above formula (1) is expressed by the following formula (3).

[0076] [ka]

[0077] (In the formula, Ar 1 , Ar 2 , R 1 , R 3 , A, c, and m are defined as in the formula (1).

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

[0079] [ka]

[0080] [In the formula, 1)R 1 , R 3 and m are defined as defined in the formula (1), and 2) a' and c' are each independently an integer of 0 to 5.]

[0081] Moreover, the above formula (1) is expressed by the following formula (4).

[0082] [ka]

[0083] [In the formula, 1) Ar 1 , X 1 , X 3 , R 1 , R 2 , a and b are defined as defined in the formula (1), 2) o' and p' are each independently 0 or 1, provided that o' + p' is 1 or greater; 3) A'' is C6~C 60 or a C2-C group containing at least one heteroatom selected from O, N, S, Si, and P. 60 a heterocyclic group;

[0084] When A″ is an aryl group, it is preferably a C6 to C 30 an aryl group of, more preferably, C6 to C 20 aryl groups, more preferably C6 to C 18 The alkyl group may be an aryl group such as phenyl, biphenyl, naphthyl, or terphenyl.

[0085] When A″ is a heterocyclic group, it is preferably a C2 to C 30 Heterocyclic groups of the formula (I), more preferably C2 to C 20 Heterocyclic groups of the formula (I), more preferably C2 to C 16and the like, for example, pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, benzofuran, benzothiophene, etc.

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

[0087] [ka]

[0088] [In the formula, 1) Ar 1 , R 1 , R 2 , X1, a, and b are defined as in the formula (1), and 2) A″ is defined as in the formula (4).

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

[0090] [ka]

[0091] [In the formula, 1) Ar 1 , R 1 , R 2 , R f , R g , R h , R i , R j 1) a and b have the same definitions as those in formula (1), and 2) A″ has the same definition as those in formula (4).

[0092] More preferably, the formula (1) is represented by the following formula (4-7):

[0093] [ka]

[0094] [In the formula, 1)X 1 , R1 and R 2 has the same definition as defined in the formula (1), and 2) a'' and b' each independently represent an integer of 0 to 4.

[0095] Moreover, the formula (1) is expressed by the following formula (5) or formula (6).

[0096] [ka]

[0097] [In the formula, 1)Ar 1 , Ar 2 , X 1 , X 2 , X 4 , R 1 , R 2 , R 3 2) a, b, and c are defined as in the formula (1), and 2) A' is defined as in the formula (2-6). is equivalent to.]

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

[0099] [ka]

[0100] [In the formula, 1)X 1 , X 2 , R 1 , R 2 and R 3 is defined as in the formula (1) above. 2) a'' and c'' are each independently an integer of 0 to 4, and b'' is an integer of 0 to 2.

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

[0102] [ka]

[0103] [In the formula, 1)X 1 , X 4 , R 1 , R 2 and R 3 has the same definition as defined in the 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] Moreover, the formula (1-1) is expressed by the following formula (1-1-a) or formula (1-1-b).

[0105] [ka]

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

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

[0108] [ka]

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

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

[0111] [ka]

[0112] [In the formula, 1) x, y, z, C, D, u, v, and w are defined as defined in formula (1), and 2) t′ is an integer of 1 to 20.]

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

[0114] [ka]

[0115] [ka]

[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] [ka]

[0118] [ka]

[0119] [ka]

[0120] [ka]

[0121]

change

[0122]

change

[0123]

change

[0124]

change

[0125]

change

[0126]

change

[0127]

change

[0128]

change

[0129]

change

[0130]

change

[0131]

change

[0132] [ka]

[0133] [ka]

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

[0135] The fluorine content of the compounds described herein is shown by the following mathematical formula (A): Fluorine content = number of fluorine atoms in compound / total number of atoms in compound × 100 (A) Here, the number of fluorine atoms in a compound means the number of fluorine atoms contained in the compound, and the total number of atoms in a compound means the total number of atoms in the compound including fluorine.

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

[0137] The organic layer may include at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer.

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

[0139] The laminate structure of an organic electronic device containing the compound of the present invention will be described below with reference to FIGS.

[0140] When assigning reference numerals to components in each drawing, the same components should be assigned the same numerals as much as possible even when they are shown in different drawings. Furthermore, in the description of the present invention, if a detailed description of related known structures or functions is deemed to obscure the gist of the present invention, the detailed description thereof will be omitted.

[0141] When the terms "comprise," "have," "constitute," etc. are used herein, other parts may be added unless "only" is used. When an element is expressed in the singular, it also includes the plural unless otherwise expressly stated.

[0142] Furthermore, when describing components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used. These terms are used to distinguish the component from other components, and do not limit the nature, order, sequence, etc. of the components. When a component is described as being "coupled," "coupled," or "connected" to another component, it should be understood that the component may be directly coupled or connected to the other component, but that additional components may also be "coupled," "coupled," or "connected" between the components.

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

[0144] 1, 2 and 3 are diagrams illustrating an organic electronic device according to an 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 material layers 120, 130, 140, and 150 formed on the first electrode 110, and a metal patterning layer 170 formed on the organic material layers.

[0146] The organic layer may include a hole injection layer 120, a hole transport layer 130, an emitting layer 140, and an electron transport layer 150, which are arranged in this order on the first electrode 110. A hole blocking layer, an electron blocking layer, an emitting auxiliary layer 220, a buffer layer 210, an electron injection layer, etc. may also be included. An electron injection layer may be formed on the electron transport layer 150, but may be omitted if necessary, but is not limited thereto.

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

[0148] When the metal patterning layer is coated, depending on the structure and fluorine content of the compound contained in the metal patterning layer, the negative electrode is prevented from being laid on the metal patterning layer, and ultimately only a small amount of the negative electrode is laid on the metal patterning layer, or none at all.

[0149] In this regard, for electrode (electrically conductive) coatings, light transmittance is used to determine the amount of electrode material present on a surface. This is because electrode materials contain metals, and electrically conductive materials such as metals attenuate and / or absorb light. Therefore, a surface with a light transmittance of greater than 90% in the visible light region of the electromagnetic spectrum is considered to be substantially free of electrically conductive material.

[0150] As a result, the pixels of the organic electronic device containing metal patterning have high transmittance and act as blanks, preventing light from emitting. The high transmittance allows light to be transmitted to various wide-angle sensors (optical sensors) located underneath the substrate (TFT substrate) without optical noise.

[0151] Therefore, in an organic electronic device including a metal patterning layer (see FIG. 3), when forming an organic layer on a 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 flow and no light is emitted.

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

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

[0154] Furthermore, the organic material layer can be manufactured with fewer layers by a solution or solvent process, such as 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 process, rather than by a deposition process using various polymer materials. The organic material layer according to the present invention can be formed by various methods, and the method of formation does not limit the scope of the present invention.

[0155] The organic electronic device according to an embodiment of the present invention may be selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a device for monochrome lighting, and a device for quantum dot display.

[0156] Another embodiment of the present invention may include an electronic device including a display device including the organic electronic device of the present invention and a controller for controlling the display device. In this case, the electronic device may be a current or future wired or wireless communication terminal, such as a mobile communication terminal, for example, a mobile phone. This includes all electronic devices such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation systems, game consoles, various TVs, and various computers.

[0157] Examples of synthesis of the compound represented by formula (1) of the present invention and examples of production of the organic electronic device of the present invention will be specifically described below with reference to 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 can be synthesized as shown in the following Reaction Scheme 1, but is not limited thereto.

[0159] <Reaction Scheme 1>

[0160] [ka]

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

[0162] I. Synthesis of Sub1

[0163] 1.Synthesis example of Sub1-9

[0164] [ka]

[0165] 1,4-Dibromo-2-iodobenzene (10.0 g, 27.6 mmol) was dissolved in THF (138 mL) in a round-bottom flask, and then naphthalen-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 stirred at 80 °C. Upon completion of the reaction, the mixture was extracted with CHCl2 and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was then recrystallized through a silica gel column to give 7.5 g of product (75% yield).

[0166] 2.Synthesis example of Sub1-12

[0167] [ka]

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

[0169] 3.Synthesis example of Sub1-46

[0170] [ka]

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

[0172] 4. Synthesis example of Sub1-58

[0173] [ka]

[0174] Dibenzo[b,d]thiophene-3-amine (5.0 g, 25.1 mmol), toluene (250 mL), 1-bromo-4-chlorobenzene (10.6 g, 55.2 mmol), Pd(dba) (1.38 g, 1.51 mmol), P(t-Bu) (0.61 g, 3.01 mmol), and NaOt-Bu (9.6 g, 100 mmol) were added to a round-bottom flask and stirred at 100 °C. Upon completion of the reaction, the mixture was extracted with CHCl and water, and the organic layer was dried over MgSO and concentrated. The resulting compound was then recrystallized through a silica gel column to give 7.5 g of product (71% yield).

[0175] 5. Synthesis example of Sub1-63

[0176] [ka]

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

[0178] 6.Synthesis example of Sub1-69

[0179] [ka]

[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 to obtain 4.4 g of product (74% yield) using the synthesis method for Sub1-9.

[0181] 7.Synthesis example of Sub1-78

[0182] [ka]

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

[0184] 8.Synthesis example of Sub1-83

[0185] [ka]

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

[0187] 9.Synthesis example of Sub1-112

[0188] [ka]

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

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

[0191] [ka]

[0192] [ka]

[0193] [ka]

[0194] [ka]

[0195] [ka]

[0196] [ka]

[0197] [ka]

[0198] [Table 1-1]

[0199] [Table 1-2]

[0200] [Table 1-3]

[0201] II. Synthesis of Sub2

[0202] 1. Synthesis example of Sub2-12

[0203] [ka]

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

[0205] 4-Iodoaniline (30.0 g, 137 mmol), Cu (34.8 g, 548 mmol), and DMSO (274 mL) were added to a round-bottom flask, dissolved at 70°C, and then stirred for 30 minutes. The mixture was stirred for 1 hour. 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 the mixture was stirred at 120°C for 24 hours. Upon completion of the reaction, distilled water was added and the resulting solid was filtered under reduced pressure. The filtrate was then extracted with ethyl acetate, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was then separated using a silica gel column to obtain 63.0 g of product (yield: 68%).

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

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

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

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

[0210] 2. Example of Sub2-13 conjunction

[0211] [ka]

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

[0213] 3. Synthesis example of Sub2-15

[0214] [ka]

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

[0216] 4. Sub2-16 synthesis example

[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 to obtain 13.2 g of product (21% yield) using the synthesis method for Sub2-12.

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

[0219] [ka]

[0220] [Table 2]

[0221] III. Synthesis of Sub3

[0222] 1. Sub3-1 synthesis example

[0223] [ka]

[0224] A round-bottom flask was charged with 1-iodo-4-(trifluoromethyl)benzene (5.0 g, 18.4 mmol), 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), and the mixture was refluxed at 120 °C. Upon completion of the reaction, the reaction solution was concentrated and separated on a silica gel column to obtain 3.9 g of product (yield: 79%).

[0225] 2. Sub3-2 synthesis example

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

[0227] [ka]

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

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

[0230] Sub3-2-a (50.7 g, 118 mmol) synthesized above, bis(pinacola Using the synthesis method for Sub3-1, 49.9 g (81% yield) of product was obtained using (31.4 g, 124 mmol), Pd(dba) (3.24 g, 3.54 mmol), x-phos (3.37 g, 7.07 mmol), KOAc (23.1 g, 236 mmol), and toluene (393 mL).

[0231] 3. Synthesis example of Sub3-7

[0232] [ka]

[0233] (1) Synthesis 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 reacted using the synthesis method for Sub3-2-a to obtain product 14. 6 g (yield: 77%) was obtained.

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

[0236] Sub3-7-a (14.6 g, 28.9 mmol) synthesized above, bis(pinaco) Using the synthesis method for Sub3-1, 13.8 g (yield: 80%) of product was obtained using (methyl)-diboron (7.7 g, 30.3 mmol), Pd(dba) (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).

[0237] 4. Synthesis example of Sub3-15

[0238] [ka]

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

[0240] In a round-bottom flask, (3-chlorophenyl)boronic acid (8.0 g, 51.2 mmol), 1,1,1,1,1,1,1,1,1,1,1,1,1,1-tridecafluoro-8-iodo-1λ 16 The resulting mixture was cooled to room temperature and extracted with diethyl ether and brine. The resulting organic layer was then dehydrated with MgSO4. The organic layer was then filtered under reduced pressure and passed through a silica gel column to obtain 17.7 g of product (76% yield).

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

[0242] Sub3-15-a (17.7 g, 38.7 mmol), bis(pina Using the synthesis method for Sub3-1 described above, 16.9 g (yield: 79%) of product was obtained from (cholato)diboron (10.3 g, 40.6 mmol), Pd(dba) (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).

[0243] 5. Synthesis example of Sub3-23

[0244] [ka]

[0245] (1) Synthesis 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 mixed together to give 99.8 g of product (yield: 78%).

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

[0248] Sub3-23-a (99.8 g, 86.9 mmol), bis(pina Using the synthesis method for Sub3-1 described above, 84.5 g (yield: 78%) of product was obtained from (cholato)diboron (23.2 g, 91.2 mmol), Pd(dba) (2.39 g, 2.61 mmol), x-phos (2.49 g, 5.21 mmol), KOAc (17.1 g, 174 mmol), and toluene (290 mL).

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

[0250] [ka]

[0251] [ka]

[0252] [Table 3]

[0253] IV. Synthesis of the Final Product

[0254] 1. Synthesis example of P1-1

[0255] [ka]

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

[0257] 2. Synthesis example of P1-22

[0258] [ka]

[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, the product was separated on a silica gel column and recrystallized. As a result, 3.53 g of product was obtained (yield: 82%).

[0261] (2) P1-22 synthesis example

[0262] Inter1-22 (3.0 g, 3.64 mmol) synthesized above was dissolved in toluene (12 mL) in a round 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 and stirred at 120 °C. Upon completion of the reaction, the product was separated on a silica gel column and recrystallized to obtain 3.41 g of product (yield: 79%).

[0263] 3. Synthesis example of P1-23

[0264] [ka]

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

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

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

[0268] Inter1-23 (4.4 g, 3.60 mmol), Sub3-5 (2.86 g, 3.96 mmol), K2CO3 (1.49 g, 10.8 mmol), and P Using the synthesis method for P1-22, d(PPh3)4 (0.08 g, 0.07 mmol) and toluene (12 mL) gave 4.9 g of product (yield: 76%).

[0269] 4. Synthesis example of P1-34

[0270] [ka]

[0271] Using the synthesis method for P1-22 described above, 5.0 g of product (78% yield) was obtained using 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).

[0272] 5. Synthesis example of P1-44

[0273] [ka]

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

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

[0277] The synthesis of P1-22 was carried out using the above-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) to give 3.6 g of product (77% yield).

[0278] 6. Synthesis example of P1-46

[0279] [ka]

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

[0281] 7. Synthesis example of P1-50

[0282] [ka]

[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 to obtain 5.3 g of product (70% yield) using the synthesis method for P1-22.

[0284] 8.Synthesis example of P1-52

[0285] [ka]

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

[0287] 9.Synthesis example of P1-55

[0288] [ka]

[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 to obtain 5.5 g of product (72% yield) using the synthesis method for P1-22.

[0290] 10.Synthesis example of P1-61

[0291] [ka]

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

[0293] 11.Synthesis example of P1-63

[0294] [ka]

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

[0296] 12.Synthesis example of P1-65

[0297] [ka]

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

[0299] 13.Synthesis example of P1-67

[0300] [ka]

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

[0302] 14.Synthesis example of P1-69

[0303] [ka]

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

[0305] 15.Synthesis example of P1-71

[0306] [ka]

[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 to obtain 4.7 g of product (74% yield) using the synthesis method for P1-22.

[0308] 16.Synthesis example of P1-73

[0309] [ka]

[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 toluene (6.9 mL) were used to obtain 3.9 g of product (76% yield) using the synthesis method for P1-22.

[0311] 17.Synthesis example of P2-1

[0312] [ka]

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

[0314] 18.Synthesis example of P2-2

[0315] [ka]

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

[0317] 19.Synthesis example of P3-2

[0318] [ka]

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

[0320] 20.Synthesis example of P3-4

[0321] [ka]

[0322] 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 of P1-1 to obtain 3.8 g of product (yield: 76%).

[0323] 21.Synthesis example of P3-5

[0324] [ka]

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

[0326] 22.Synthesis example of P4-2

[0327] [ka]

[0328] The synthesis of P1-1 was carried out using the above-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) to obtain 3.6 g of product (yield: 72%).

[0329] 23.Synthesis example of P4-4

[0330] [ka]

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

[0332] 24.Synthesis example of P5-3

[0333] [ka]

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

[0335] 25.Synthesis example of P5-6

[0336] [ka]

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

[0338] 26.Synthesis example of P6-1

[0339] [ka]

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

[0341] 27.Synthesis example of P6-4

[0342] [ka]

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

[0344] 28.Synthesis example of P7-1

[0345] [ka]

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

[0347] 29.Synthesis example of P7-4

[0348] [ka]

[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 to obtain 3.5 g of product (76% yield) using the synthesis method for P1-22.

[0350] 30.Synthesis example of P8-2

[0351] [ka]

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

[0353] 31.Synthesis example of P8-3

[0354] [ka]

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

[0356] 32.Synthesis example of P9-3

[0357] [ka]

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

[0359] 33.Synthesis example of P9-4

[0360] [ka]

[0361] The above-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 in the synthesis of P1-1 to obtain 3.6 g of product (yield: 82%).

[0362] 34.Synthesis example of P9-6

[0363] [ka]

[0364] Sub1-82 (1.0 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 to obtain 3.8 g of product (71% yield) using the synthesis method for P1-22.

[0365] 35.Synthesis example of P10-1

[0366] [ka]

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

[0368] 36.Synthesis example of P10-5

[0369] [ka]

[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 to obtain 3.6 g of product (70% yield) using the synthesis method for P1-22.

[0371] 37.Synthesis example of P11-2

[0372] [ka]

[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 to obtain 3.4 g of product (73% yield) using the synthesis method for P1-22.

[0374] 38.Synthesis example of P11-4

[0375] [ka]

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

[0377] 39.Synthesis example of P11-6

[0378] [ka]

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

[0380] 40.Synthesis example of P11-10

[0381] [ka]

[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 in the synthesis of P1-22 to afford 4.9 g of product (yield: 68%).

[0383] 41.Synthesis example of P12-1

[0384] [ka]

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

[0386] 42.Synthesis example of P13-3

[0387] [ka]

[0388] In a round-bottom flask, Sub1-103 (2.0 g, 6.5 mmol), toluene (33 mL), Sub3-2-a (6.2 g, 14.4 mmol), Pd2(dba)3 (0.1 The mixture was stirred at 120 °C with P(t-Bu) (0.8 g, 0.20 mmol), P(t-Bu) (0.08 g, 0.39 mmol), and NaOt-Bu (2.5 g, 26.1 mmol). After the reaction was completed, the mixture was extracted with CHCl and water, and the organic layer was dried over MgSO and concentrated. The resulting compound was then recrystallized through a silica gel column to obtain 5.1 g of product (yield: 72%).

[0389] 43.Synthesis example of P14-4

[0390] [ka]

[0391] Sub1-108 (2.0g, 4.52mmol), Sub3-20 (4.2g, 4. Using the synthesis method for P1-22, 4.0 g of product (yield: 79%) was obtained by adding Pd(PPh) (0.97 mmol), K2CO3 (1.9 g, 13.6 mmol), Pd(PPh3)4 (0.10 g, 0.09 mmol), and toluene (15 mL).

[0392] 44.Synthesis example of P15-2

[0393] [ka]

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

[0395] 45.Synthesis example of P16-2

[0396] [ka]

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

[0398] 46.Synthesis example of P17-1

[0399] [ka]

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

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

[0402] [Table 4-1]

[0403] [Table 4-2]

[0404] [Table 4-3]

[0405] Light transmittance measurement

[0406] Example 1: Comparison of light transmittance depending on the type of metal patterning layer First, a film of N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine (hereinafter abbreviated as 'C-1') was vacuum-deposited on a glass substrate to a thickness of 100 nm as an organic layer. Compound P1-22 of the present invention was vacuum-deposited on the organic layer to a thickness of 10 nm to form an electrode patterning layer. Subsequently, Yb was vacuum-deposited on the electrode patterning layer as an electron injection layer, and then Mg and Ag were vacuum-deposited in a ratio of 1:9 by weight to form a negative electrode. Thereafter, N4,N4'-diphenyl-N4,N4'-bis(9-phenyl- 9H-carbazol-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 required for measuring 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 listed in Table 5 below was used as the metal (electrode) patterning layer material instead of compound P1-22 of the present invention.

[0408] Comparative Example 1 A light transmittance sample was prepared in the same manner as in Example 1, except that 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 the 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] [ka]

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

[0413] [Table 5]

[0414] The results in Table 5 confirm that the light transmittance was less than 90% in Comparative Example 1, which did not use a metal patterning layer, and in Comparative Compound A, which is a compound with a small intramolecular fluorine content, while the light transmittance was 90% or more in Examples 1 to 10, which used compounds of the present invention with an intramolecular fluorine content of 30% or more.

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

[0416] The light transmittance varied slightly between the lots of Comparative Example 1, and in an attempt to correct this, the light transmittance was expressed in T% (the light transmittance of Comparative Example 1 for each lot was calculated as 100%, and the difference in light transmittance from the compound of the present invention was shown). As a result, it was found that the light transmittance increased by 28% to 39% when the compound of the present invention was used compared to Comparative Example 1.

[0417] With respect to electrode (electrically conductive) coatings, light transmittance is used to determine the amount of electrode material present on a surface. This is because electrode materials contain metals, and electrically conductive materials such as metals attenuate and / or absorb light. Thus, a surface with a light transmittance greater than 90% in the visible region of the electromagnetic spectrum is considered to be substantially free of electrically conductive material.

[0418] Therefore, when the light transmittance of the samples prepared in the present invention was measured, it was found that when the compound of the present invention having an intramolecular fluorine content of 20% or more was used as shown in Table 5, the metal Yb used as the electron injection layer and Ag and Mg used as the anode were not vapor-deposited on the compound of the present invention.

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

[0420] As shown in Figure 4(a), it was confirmed that a thin white film was formed between the organic layer (lower end) and the capping layer (upper end), and as shown in Figure 4(b), it was confirmed that no thin film was formed between the organic layer and 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 a metal in the electron injection layer and the type of metal in the electrode First, a C-1 film was vacuum-deposited on a glass substrate to form a 100 nm thick organic layer. Compound P1-46 of the present invention was vacuum-deposited on the organic layer to form a 10 nm thick metal patterned layer. Next, Yb was vacuum-deposited on the metal patterned layer to form an electron injection layer, and then a negative electrode was deposited using a 1:9 ratio of Mg and Ag by weight. Finally, D-1 was vacuum-deposited on the metal patterned layer to form a 70 nm thick capping layer, producing a sample.

[0422] Comparative Example 3 An organic electronic device was manufactured in the same manner as in Example 11, except that no metal patterning layer was used.

[0423] Example 12: Sample without using Yb as an electron injection layer metal First, a C-1 film was vacuum-deposited on a glass substrate to form a 100 nm thick organic layer. Compound P1-46 of the present invention was vacuum-deposited on the organic layer to form a 10 nm thick metal patterned layer. Next, Mg and Ag were vapor-deposited in a ratio of 1:9 by weight onto the metal patterned layer to form a negative electrode. Finally, D-1 was vapor-deposited to a thickness of 70 nm as a capping layer to fabricate an organic electronic device.

[0424] Comparative Example 4: Sample without Yb, the electron injection layer metal An organic electronic device was manufactured in the same manner as in Example 12, except that no metal patterning layer was used.

[0425] Example 13: Sample using only Ag as electrode (negative electrode) First, a C-1 film was vacuum-deposited on a glass substrate to form a 100 nm thick organic layer. Compound P1-46 of the present invention was vacuum-deposited on the organic layer to form a 10 nm thick metal patterned layer. Next, Yb was vacuum-deposited on the metal patterned layer to form an electron injection layer, followed by Ag deposition as a negative electrode. Finally, D-1 was vacuum-deposited to a thickness of 70 nm to form a capping layer, thereby producing an organic electronic device.

[0426] Comparative Example 5: Sample using only Ag as electrode (negative electrode) An organic electronic device was manufactured in the same manner as in Example 13, except that no metal patterning layer was used.

[0427] The light transmittance of the thus prepared samples of the Examples and Comparative Examples was measured at 550 nm, which is the visible light region, using a Lambda 365 UV / VIS spectrometer (manufactured by PerkinElmer), and the measurement results are shown in Table 6 below.

[0428] [Table 6]

[0429] The results in Table 6 were compiled based on the graph of light transmittance measurement results in Figure 6. Table 6 compares the light transmittance of Comparative Examples 3, 4, and 5, which did not use a metal patterning layer, with that of Examples 11, 12, and 13, which used compound P1-46 of the present invention with an intramolecular fluorine content of 30% or more, to examine whether electrode patterning is possible depending on the presence or absence of an electron injection layer metal and the change in electrode patterning depending on the type of negative electrode metal. Comparative Example 3 and Example 11 are considered comparisons in which the electron injection layer metal Yb and the negative electrode metal Mg were not used. It was confirmed that when compound P1-46 of the present invention with an intramolecular fluorine content of 30% or more was used in the metal patterning layer, a light transmittance of 95.63% was observed.

[0430] In order to confirm the patterning performance for the negative electrode metals excluding Yb, which was the metal used as the electron injection layer, Comparative Example 4 and Example 12 were carried out. As a result, it was confirmed that in the absence of Yb, which was the metal for the electron injection layer, the light transmittance of Example 12, which used the compound of the present invention, was 96.68% (T%: 146%), which was higher than that of Example 11, which had an electron injection layer (a 16% increase in T%).

[0431] Furthermore, in order to investigate the patterning performance depending on the type of metal in the negative electrode, Comparative Example 5 and Example 13, which used only Ag in the negative electrode, were compared with Comparative Example 3 and Example 11, which were comparative groups. As a result, it was confirmed that when only Ag was used in the negative electrode and the compound of the present invention was used in the metal patterning layer, the light transmittance increased by 5% to 135% (T%) compared to Example 11.

[0432] Example 14 First, a C-1 film was vacuum-deposited on a glass substrate to form a 100 nm thick organic layer. Compound P1-22 of the present invention was vacuum-deposited on the organic layer to form a 3 nm thick metal patterned layer. Next, Yb was vacuum-deposited on the metal patterned layer as an electron injection layer, and then a negative electrode was deposited by vapor-depositing Mg and Ag in a 1:9 ratio by weight. Then, D-1 was vapor-deposited to a 70 nm thick capping layer to prepare a sample.

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

[0434] Comparative Example 6 A sample was prepared 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 prepared were measured using Lambda 365 The light transmittance at 550 nm in the visible light region was measured using a UV / VIS spectrometer (manufactured by PerkinElmer), and the measurement results were evaluated and shown in Table 7 below.

[0436] [Table 7]

[0437] The results in Table 7 were prepared based on the graph of the light transmittance measurement results in Figure 7. Table 7 was prepared to confirm the change in light transmittance depending on the thickness of the metal patterning layer using the compound of the present invention. In the case of Comparative Example 6, the light transmittance results for each lot of the Comparative Example used in the evaluation of each material described in Examples 14 to 25 are shown as a range (69.13% to 72.38%), and the light transmittance measured for each lot was calculated as 100% (T%), and the light transmittance of the Examples relative to this was shown 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, respectively, it was confirmed that the light transmittance was 95.01% to 96.47% (T% 132% to 140%), and there was no significant difference. This indicates that when the compound of the present invention is used as a metal patterning material, problems such as performance degradation due to variations in deposition thickness that may occur during the deposition process can be prevented.

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

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

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

[0442] The contact angles of the samples of Comparative Example 7 and Examples 26 to 34 thus prepared were measured using DSA2 The measurement results were evaluated using a contact angle measuring device (KRUSS Co., Ltd.) and are shown in Table 8 below. showed.

[0443] [Table 8]

[0444] As shown in Table 8, the contact angle of the C-1 material, which does not contain fluorine and has low light transmittance, was 83.2°, while the contact angles of the compounds of the present invention, which have a light transmittance of 90% or more, were all 100° or more (103.6 to 118.2°). The results in Table 8 are considered to show the reason why the compounds of the present invention, which have high light transmittance (90% or more), are suitable for metal patterning. Generally, adhesion is explained by the solid surface energy through the contact angle (wetting angle or contact angle) and wettability. Generally, The larger the contact angle, the lower the wettability, and therefore the lower the adhesiveness, and the lower the solid surface energy. This is because when the surface tension of a liquid is high, the force of attraction between itself becomes strong, 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: gLVcosθ=gSV-gSL (1) gSL: Interfacial tension between solid and liquid, gSV: Interfacial tension between a solid surface and a liquid vapor, gLV: Interfacial tension between liquid and liquid vapor

[0447] The formula for the work of adhesion Wa proposed by Dupre based on the formula (1) is as follows: Wa=gS+gLV-gSL=gS+gLV+(gLVcosθ-gSV)=(gS- gSV)+gLV(1+cosθ) (2) In the formula (2), gS is the surface tension of the solid itself, and since gS and gSV are generally considered to be equal at a small surface energy, the formula (2) can be summarized as follows: Wa=gLV(1+cosθ) (3) From the formula (3), if the contact angle is 0°, cos 0° = 1, meaning complete wetting; on the other hand, if the contact angle is 180°, cos 180° = -1, meaning no wetting at all.

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

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

[0450] The above description is merely illustrative of the present invention, and those skilled in the art will appreciate that various modifications may be made without departing from the essential characteristics of the present invention. Therefore, the embodiments disclosed herein are for illustrative purposes only and do not limit the present invention, and the spirit and scope of the present invention should not be limited by such embodiments. The scope of the present invention should be interpreted by the following claims, and all technologies within the scope equivalent thereto should be interpreted as being within the scope of the present invention.

[0451] (Possibility of Industrial Applicability) According to the present invention, an organic element having excellent element characteristics such as high brightness, high light emission, and long life can be produced, and the present invention has industrial applicability. [Explanation of symbols]

[0452] 100, 200, 300: Organic electronic devices 110: 1st 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. The following formula (5) or formula (6) 【Chemical 1】 [In the formula, 1) Ar １ and Ar ２ are, independently of each other, C ６ ~C ６０ an aryl group of the formula: 2) A' is C ６ ~C ６０ an arylene group of the formula: 3) R １ , R ２ , and R ３ are the same or different, and independently of each other, C ６ ~C ６０ an aryl group; a fluorenyl group; a C group containing at least one heteroatom selected from O, N, S, Si, and P; ２ ~C ６０ a heterocyclic group represented by the formula C ３ ~C ６０ and the aliphatic ring C ６ ~C ６０ A fused ring group of an aromatic ring represented by the formula C １ ~C ５０ an alkyl group of C １ ~C ５０ an alkoxyl group of C ６ ~C ６０ -L-NR'R''; a substituent represented by the formula (1-1); and a substituent represented by the formula (1-2); or adjacent groups may be bonded to each other to form a ring, However, R １ , R ２ and R ３ at least one of is a substituent represented by the formula (1-1) or a substituent represented by the formula (1-2), 4) a, b, and c are each independently an integer from 0 to 10, provided that a+b+c is 1 or greater; 5) X １ , X ２ , and X ４ are, independently of each other, CR ｆ R ｇ , N.R. ｈ , O, S or SiR ｉ R ｊ and 6) R′ and R″ are each independently C ６ ~C ６０ aryl groups of the formula: C, containing at least one heteroatom of O, N, S, Si and P; ２ ~C ６０ Heterocyclic groups of the formula: ３ ~C ６０ and the aliphatic ring C ６ ~C ６０ or adjacent groups may be bonded to each other to form a ring, 7) R ｆ , R ｇ , R ｈ , R ｉ and R ｊ are each independently hydrogen; deuterium; halogen; C ６ ~C ６０ aryl groups of the formula: C, containing at least one heteroatom of O, N, S, Si and P; ２ ~C ６０ a heterocyclic group represented by the formula C ３ ~C ６０ and the aliphatic ring C ６ ~C ６０ A condensed ring group of an aromatic ring represented by the formula C １ ~C ５０ a substituent represented by the formula (1-1); and a substituent represented by the formula (1-2); or adjacent groups may be bonded to each other to form a ring, 8) B, C and D are, independently of each other, C ６ ~C ６０ arylene groups; fluorenylene groups; and C containing at least one heteroatom of O, N, S, Si, and P ２ ~C ６０ heterocyclic groups; 9) x is an integer from 1 to 50, and y+z is an integer of 2x+1, 2x, or 2x-2; i, t, and v are each independently an integer from 0 to 20; s, u, and w are each independently an integer from 1 to 20; provided that when i or t is 0, s or u is 1; 10) L is a single bond; C ６ ~C ６０ an arylene group; a fluorenylene group; a C group containing at least one heteroatom selected from O, N, S, Si, and P; ２ ~C ６０ a heterocyclic group represented by the formula C １ ~C ５０ an alkylene group of the formula: ３ ~C ６０ and the aliphatic ring C ６ ~C ６０ a fused ring group of an aromatic ring of the formula: 11) Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, fused ring group, alkyl group, alkoxyl group, aryloxy group, and rings formed by bonding adjacent groups to each other are each selected from the group consisting of deuterium, halogen, silane group, siloxane group, boron group, germanium group, cyano group, nitro group, C １ ~C ２０ an alkylthio group represented by C １ ~C ２０ an alkoxyl group of C ６ ~C ２０ an aryloxy group represented by C １ ~C ２０ an alkyl group of C ２ ~C ２０ an alkenyl group of C ２ ~C ２０ an alkynyl group represented by C ６ ~C ２０ aryl groups of the formula: ６ ~C ２０ an aryl group of the formula: ６ ~C ２０ an aryl group; a fluorenyl group; ２ ~C ２０ a heterocyclic group represented by the formula C ３ ~C ２０ a cycloalkyl group represented by the formula C ７ ~C ２０ arylalkyl groups of the formula: ８ ~C ２０ and these substituents may be linked together to form a ring, where 'ring' refers to an arylalkenyl group selected from the group consisting of C ３ ~C ６０ an aliphatic ring of C ６ ~C ６０ or C ２ ~C ６０ or a fused ring consisting of a heterocycle or a combination thereof, and includes a saturated or unsaturated ring.

2. The compound represented by the formula (5) is represented by the following formulas (5-1) to (5-3): 【Chemistry 2】 [In the formula, 1) １ , X ２ , R １ , R ２ and R ３ is as defined in claim 1, and 2) a'' and c'' are each independently an integer of 0 to 4, and b'' is an integer of 0 to 2.

3. The compound represented by formula (6) is represented by the following formula (6-1) or formula (6-2): 【Chemistry 3】 [In the formula, 1) １ , X ４ , R １ , R ２ and R ３ is as defined in claim 1, and 2) a'' and c'' are each independently an integer of 0 to 4, and b'' is an integer of 0 to 2.

4. A fluorinated compound that is any one of the following compounds: 【Chemistry 4】 【change】 【Chemistry 5】 【Chemistry 6】 。

5. An organic electronic device having a non-light-emitting region including a positive electrode, at least one organic material layer on the positive electrode, and a metal patterning layer on the organic material layer, and a light-emitting region including a metal on the organic material layer; a metal electrode; or a metal and a metal electrode; 10. An organic electronic device, wherein the metal patterning layer is a fluorine compound represented by formula (5) or (6) according to claim 1, the fluorine content in the molecule being 30% or more.

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

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

8. 6. The organic electronic device according to claim 5, wherein a mixture of two or more different compounds represented by formula (5) or (6) is used.

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 comprising:

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

11. A metal patterning composition comprising one or more fluorinated compounds according to formula (5) or formula (6) of claim 1, each of which has a different structure.

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