Compound, coating composition containing the same, organic light-emitting device using the same, and method for producing the same

Abstract

The present invention relates to a compound represented by Chemical Formula 1, a coating composition containing the compound represented by Chemical Formula 1, an organic light-emitting device using the same, and a method for manufacturing the same.

Description

Technical Field

[0001] This specification claims the benefit of the filing date of Korean Patent Application No. 10-2021-0038765, filed with the Korean Intellectual Property Office on March 25, 2021, and all of its contents are incorporated herein by reference.

[0002] This specification relates to a compound, a coating composition containing the compound, an organic light-emitting device formed using the coating composition, and a method for manufacturing the same.

Background Art

[0003] The organic light-emitting phenomenon is an example in which current is converted into visible light by an internal process of specific organic molecules. The principle of the organic light-emitting phenomenon is as follows. When an organic layer is positioned between an anode and a cathode and a current is applied between the two electrodes, electrons and holes are injected into the organic layer from the cathode and the anode, respectively. The electrons and holes injected into the organic layer recombine to form an exciton, and light is emitted when this exciton falls back to the ground state again. An organic light-emitting device using such a principle can generally be composed of a cathode, an anode, and an organic layer positioned therebetween, for example, an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and the like.

[0004] Conventionally, a deposition process has been mainly used to manufacture organic light-emitting devices. However, there is a problem in that a large amount of material loss occurs during the manufacture of organic light-emitting devices in the deposition process. To solve this problem, a technique for manufacturing an element through a solution process with less material loss and increased production efficiency has been developed, and the development of substances that can be used during the solution process is required.

[0005] Substances used in organic light-emitting devices for the solution process must have the following properties.

[0006] First, a storable homogeneous solution must be formed. In the case of commercially available substances for the vapor deposition process, they have good crystallinity and do not dissolve well in the solution, or even if a solution is formed, crystals are easily formed. As a result, the concentration gradient of the solution may change depending on the storage period, or there is a high possibility of forming defective elements.

[0007] Second, the substance used in the solution process must have excellent coating properties so that no pores or aggregation phenomena occur during the formation of the thin film and a thin film of uniform thickness can be formed.

[0008] Third, the layer where the solution process is performed should have resistance to the solvents and substances used in the processes for forming other layers, and is required to have excellent current efficiency and excellent lifetime characteristics during the manufacture of the organic light-emitting device.

[0009] Therefore, in this technical field, the development of new organic substances is required.

SUMMARY OF THE INVENTION

PROBLEMS TO BE SOLVED BY THE INVENTION

[0010] An object of the present invention is to provide a compound for a solution process and an organic light-emitting device formed using the same.

MEANS FOR SOLVING THE PROBLEMS

[0011] One embodiment of the present invention provides a compound represented by the following Chemical Formula 1.

CHEM.

[0012] In the above Chemical Formula 1, R1 to R19 are the same as or different from each other, and each independently is hydrogen, deuterium, a fluoro group, a fluoroalkyl group, a cyano group, or a substituted or unsubstituted alkyl group, Ar is a substituted or unsubstituted (n1 + 1)-valent aryl group, X is a curing group, m1 is an integer from 1 to 3. When m1 is 2 or more, the substituents within the two or more parentheses are the same as or different from each other. n1 is an integer from 1 to 5. When n1 is 2 or more, the substituents within the two or more parentheses are the same as or different from each other.

[0013] Another embodiment of the present invention provides a coating composition containing the above compound.

[0014] Another embodiment of the present invention provides an organic light-emitting device including a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain the above coating composition or a cured product thereof.

[0015] Finally, another embodiment of the present invention provides a method for manufacturing an organic light-emitting device, including the steps of preparing a substrate; forming a first electrode on the substrate; forming one or more organic layers on the first electrode; and forming a second electrode on the organic layers, wherein the step of forming the organic layers includes the step of forming one or more organic layers using the above coating composition.

Advantages of the Invention

[0016] The compound according to one embodiment of the present invention can be used as a material for a solution process when manufacturing an organic layer of an organic light-emitting device, enabling large-areaization of the device, and can provide a device having a low driving voltage, high luminous efficiency, and high lifetime characteristics.

[0017] The compound of the present invention has an asymmetric structure in which one or more of the four substituents bonded around the boron anion have a structure different from that of the other substituents. Therefore, the compound has a higher solubility in a solvent than a compound having a symmetric structure in which all four substituents have the same structure, and is more suitable as a material for a solution process.

[0018] In addition, while the compound of the present invention has an asymmetric structure, when X, which is a substituent containing a vinyl group, is bonded to Ar, the probability that X, which is a substituent containing a vinyl group, is located on the outer periphery in a single molecule and meets and bonds with the vinyl group of another single molecule increases, which is advantageous for curing.

Brief Description of Drawings

[0019]

Figure 1

Figure 2

Figure 3

Figure 4

Figure 5

Figure 6

Figure 7

Figure 8

Figure 9

Figure 10

Figure 11

Modes for Carrying Out the Invention

[0020] Hereinafter, the present invention will be described in more detail.

[0021] One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.

Chem.

[0022] In the above Chemical Formula 1, R1 to R19 are the same as or different from each other, and each independently is hydrogen, deuterium, a fluoro group, a fluoroalkyl group, a cyano group, or a substituted or unsubstituted alkyl group. Ar is a substituted or unsubstituted (n1 + 1)-valent aryl group. X is a curing group. m1 is an integer from 1 to 3. When m1 is 2 or more, the substituents in the two or more parentheses are the same as or different from each other. n1 is an integer from 1 to 5. When n1 is 2 or more, the substituents in the two or more parentheses are the same as or different from each other.

[0023] In this specification, when a member is located "above" another member, this includes not only the case where a member is in contact with another member, but also the case where there are other members between the two members.

[0024] In this specification, when a certain part "includes" a certain component, this means that, unless otherwise stated to the contrary, it does not exclude other components, but can further include other components.

[0025] In one embodiment of this specification, in the compound of Chemical Formula 1 above, a phenyl group to which a fluoro group and / or a fluoroalkyl group is bonded around a boron anion is bonded, so that electrons in the compound become deficient and electrons are taken from substances used together. As a result, there is an effect that the generation of holes becomes smooth in the substances used together with the compound of Chemical Formula 1 above.

[0026] One embodiment of this specification is that the compound of Chemical Formula 1 above is preferably a compound having solubility in an appropriate organic solvent.

[0027] The compound according to one embodiment of this specification has an asymmetric structure in which one or more of the four substituents bonded around a boron anion have a structure different from other substituents. Thus, the solubility in a solvent is higher than that of a compound having a symmetric structure in which all four substituents have the same structure, and it is suitable as a material for a solution process.

[0028] In addition, in the case of the compound according to one embodiment of the present specification, an organic light-emitting device can be manufactured by a solution coating method, and the area of the device can be increased.

[0029] In addition, the compound of the present invention has an asymmetric structure, and by bonding X, which is a substituent containing a vinyl group, to Ar, the probability that X, which is a substituent containing a vinyl group, is located on the outer periphery in a single molecule and meets and bonds with the vinyl group of another single molecule increases, which is advantageous for curing.

[0030] Hereinafter, the substituents in the present specification will be described in detail.

[0031] In the present specification,

Chemical formula

[0032] In the present specification, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent, and the position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted. When two or more substitutions occur, the two or more substituents may be the same as or different from each other.

[0033] In the present specification, the term "substituted or unsubstituted" means being substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a nitrile group; an alkyl group; a cycloalkyl group; an alkoxy group; an aryloxy group; an aryl group; and a heterocyclic group, or being unsubstituted, or being substituted with a substituent in which two or more of the above-exemplified substituents are linked, or being unsubstituted. For example, the "substituent in which two or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group and can be interpreted as a substituent in which two phenyl groups are linked.

[0034] In this specification, the halogen group is a fluoro group (-F), a chloro group (-Cl), a bromo group (-Br), or an iodo group (-I).

[0035] In this specification, the above alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but may be 1 to 60, and according to one embodiment, the number of carbon atoms of the above alkyl group may be 1 to 40. According to other embodiments, the number of carbon atoms of the above alkyl group is 1 to 20. Specific examples of the above alkyl group include, but are not limited to, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, etc.

[0036] In this specification, the above alkylene group can cite the description of the above alkyl group except that it is a divalent alkyl group.

[0037] In this specification, the fluoroalkyl group means an alkyl group substituted with a fluoro group, and specific examples include, but are not limited to, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, etc.

[0038] In this specification, the cycloalkyl group is not particularly limited, but may have 3 to 60 carbon atoms, and according to one embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 40. According to other embodiments, the number of carbon atoms of the above cycloalkyl group is 3 to 20. Specific examples of the above cycloalkyl group include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, etc.

[0039] In this specification, the above alkoxy group may be linear or branched. The number of carbon atoms of the above alkoxy group is not particularly limited, but may be 1 to 20. Specific examples of the above alkoxy group include, but are not limited to, methoxy group, ethoxy group, n-propoxy group, n-butoxy group, tert-butoxy group, n-pentyloxy group, n-hexyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group, etc.

[0040] In this specification, the above aryl group is not particularly limited, but may have 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the above aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the above aryl group is 6 to 20. When the above aryl group is a monocyclic aryl group, it may be, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, etc. Examples of the above polycyclic aryl group include, but are not limited to, naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, etc.

[0041] In this specification, the fluorenyl group can be substituted, and two substituents can be bonded to each other to form a spiro structure.

[0042] When the above fluorenyl group is substituted,

Chemical formula

Chemical formula

Chemical formula

[0043] In the present specification, for the above arylene group, except that it is a divalent aryl group, the description of the above aryl group can be cited.

[0044] In the present specification, the heterocyclic group is a heterocyclic group containing one or more of N, O, P, S, Si, and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but may be 2 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the above heterocyclic group is 2 to 30. According to another embodiment, the number of carbon atoms of the above heterocyclic group is 2 to 20. Examples of the heterocyclic group include a pyridyl group, a pyrrole group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophene group, a benzothiophene group, a benzofuran group, a dibenzothiophene group, a dibenzofuran group, etc., but is not limited thereto.

[0045] In the present specification, for the heteroaryl group, except that it is aromatic, the description regarding the above heterocyclic group can be applied.

[0046] In the present specification, for the aryl group in the above aryloxy group, the description regarding the above aryl group is applicable.

[0047] In one embodiment of the present specification, R1 to R19 are the same as or different from each other, and each independently is hydrogen, deuterium, a fluoro group, a fluoroalkyl group, a cyano group, or a substituted or unsubstituted alkyl group.

[0048] In one embodiment of the present specification, R1 to R19 are the same as or different from each other, and each independently is hydrogen, deuterium, a fluoro group, a fluoroalkyl group having 1 to 10 carbon atoms, a cyano group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0049] In one embodiment of the present specification, the above R1 to R19 are the same as or different from each other, and each independently is a fluoro group or a fluoroalkyl group.

[0050] In other embodiments, the above R1 to R19 are the same as or different from each other, and each independently is a fluoro group or a fluoroalkyl group having 1 to 10 carbon atoms.

[0051] According to other embodiments, the above R1 to R19 are the same as or different from each other, and each independently is a fluoro group or a trifluoromethyl group.

[0052] According to other embodiments, the above R1 to R15 are the same as or different from each other, and each independently is a fluoro group or a trifluoromethyl group.

[0053] According to other embodiments, the above R3, R8, and R13 are trifluoromethyl groups.

[0054] According to other embodiments, the above R1, R2, R4 to R7, R9 to R12, R14, and R15 are fluoro groups.

[0055] In one embodiment of the present specification, the above m1 is an integer from 1 to 3. When m1 is 2 or more, the substituents within two or more parentheses are the same as or different from each other.

[0056] According to other embodiments, the above m1 is 1 or 2. When m1 is 2, the two substituents within the parentheses are the same as or different from each other.

[0057] According to one embodiment of the present specification, the above Chemical Formula 1 is represented by the following Chemical Formula 2 or 3.

Chemical Formula

Chemical Formula

[0058] In the above Chemical Formulas 2 and 3, R1 to R15, Ar, X and n1 are as defined in Chemical Formula 1, R21 to R28 are the same as or different from each other and are each independently hydrogen, deuterium, a fluoro group, a fluoroalkyl group, a cyano group, or a substituted or unsubstituted alkyl group.

[0059] According to one embodiment of the present specification, the above R21 to R28 are the same as or different from each other and are each independently a fluoro group or a fluoroalkyl group.

[0060] According to another embodiment, the above R21 to R28 are the same as or different from each other and are each independently a fluoro group or a fluoroalkyl group having 1 to 10 carbon atoms.

[0061] In another embodiment, the above R21 to R28 are the same as or different from each other and are each independently a fluoro group or a trifluoromethyl group.

[0062] In another embodiment, the above R21 to R28 are fluoro groups.

[0063] In one embodiment of the present specification, the above Ar is a substituted or unsubstituted (n1 + 1)-valent aryl group.

[0064] According to another embodiment, the above Ar is a substituted or unsubstituted (n1 + 1)-valent aryl group having 6 to 30 carbon atoms. In another embodiment, the above Ar is a (n1 + 1)-valent aryl group having 6 to 30 carbon atoms.

[0065] According to another embodiment, the above Ar is a substituted or unsubstituted (n1 + 1)-valent phenyl group.

[0066] In another embodiment, the above Ar is a (n1 + 1)-valent phenyl group.

[0067] In one embodiment of the present specification, the above Chemical Formula 1 is represented by the following Chemical Formula 4. [Chemical Formula] In the above Chemical Formula 4, R1 to R19, X, n1 and m1 are as defined in Chemical Formula 1, R101 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, n2 is an integer from 0 to 4, and when n2 is 2 or more, two or more R101s are the same as or different from each other, and n1 + n2 is from 1 to 5.

[0068] According to one embodiment of the present specification, the above R101 is hydrogen or deuterium.

[0069] In one embodiment of the present specification, the above n2 is an integer from 0 to 3.

[0070] According to one embodiment of the present specification, the above Chemical Formula 2 is represented by the following Chemical Formula 5 or 6. [Chemical Formula] [Chemical Formula]

[0071] In the above Chemical Formulas 5 and 6, R1 to R15, X and n1 are as defined in Chemical Formula 1, R21 to R28 are the same as or different from each other, and each independently is a fluoro group or a fluoroalkyl group, R101 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, n2 is an integer from 0 to 4. When n2 is 2 or more, two or more R101s are the same as or different from each other, and n1 + n2 is from 1 to 5.

[0072] According to one embodiment of the present specification, the above X is a curing group. At this time, the curing group means a substituent in which the curing groups of adjacent compounds chemically react with each other to form a bond, whereby the molecule can grow and the curing can proceed. This can also be called an addition-reaction-capable group capable of addition reaction or a crosslinking-forming group in which adjacent compounds form a crosslink.

[0073] In one embodiment of the present specification, the above curing group is not particularly limited as long as the curing groups of adjacent compounds can chemically react with each other, and can include at least one of an aliphatic ring group capable of ring-opening reaction and an ethylenically unsaturated group.

[0074] In one embodiment of the present specification, the above curing group is any one of the following chemical formulas 7-1 to 7-5, compound:

Chemical formula

Chemical formula

[0075] In one embodiment of the present specification, when k1 is 2 or more, except that L1 forms -O - O - by continuous bonding of O, or forms -S - S - by continuous bonding of S, or forms -O - S -.

[0076] In one embodiment of the present specification, when k2 is 2 or more, except that L2 forms -O - O - by continuous bonding of O, or forms -S - S - by continuous bonding of S, or forms -O - S -.

[0077] In one embodiment of the present specification, when k3 is 2 or more, except that L3 forms -O - O - by continuous bonding of O, or forms -S - S - by continuous bonding of S, or forms -O - S -.

[0078] In one embodiment of the present specification, when k4 is 2 or more, except that L4 forms -O - O - by continuous bonding of O, or forms -S - S - by continuous bonding of S, or forms -O - S -.

[0079] In one embodiment of the present specification, when k5 is 2 or more, L5 excludes forming -O-O- by continuous bonding of O, forming -S-S- by continuous bonding of S, or forming -O-S-.

[0080] According to one embodiment of the present specification, the above X is a substituted or unsubstituted alkenyl group; or an aryl group substituted with a substituted or unsubstituted alkenyl group.

[0081] According to one embodiment of the present specification, the above X is a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms; or an aryl group substituted with a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms.

[0082] According to one embodiment of the present specification, the above X is a substituted or unsubstituted alkenyl group having 2 to 5 carbon atoms; or an aryl group substituted with a substituted or unsubstituted alkenyl group having 2 to 5 carbon atoms.

[0083] According to one embodiment of the present specification, the above X is a substituted or unsubstituted ethenyl group; a substituted or unsubstituted propenyl group; or a substituted or unsubstituted butenyl group; or an aryl group substituted with a substituted or unsubstituted ethenyl group, a substituted or unsubstituted propenyl group, or a substituted or unsubstituted butenyl group.

[0084] According to another embodiment of the present specification, the above X is a vinyl group (-CH=CH2) or an aryl group substituted with a vinyl group (-CH=CH2).

[0085] In another embodiment, the above X is a vinyl group (-CH=CH2), or an aryl group having 6 to 30 carbon atoms substituted with one or more vinyl groups (-CH=CH2).

[0086] According to another embodiment, the above X is a vinyl group (-CH=CH2), a phenyl group substituted with one or more vinyl groups (-CH=CH2), or a naphthyl group substituted with one or more vinyl groups (-CH=CH2).

[0087] According to another embodiment, the above X is a vinyl group (-CH=CH2), a phenyl group substituted with one vinyl group (-CH=CH2), a phenyl group substituted with two vinyl groups (-CH=CH2), or a naphthyl group substituted with a vinyl group (-CH=CH2).

[0088] In another embodiment, the above X is selected from the following structures.

Chemical formula

Chemical formula

[0089] In this specification, the compound of the above chemical formula 1 is a boron compound in which one of the four substituents bonded to boron has a terminal group of -Ar-(X)n1 (X = curing group), and is characterized by having an asymmetric structure due to the above terminal group. Compared with a symmetric compound, in the compound of the above chemical formula 1, X which is a curing group is located more on the outer periphery and has a lower curing temperature, making curing easier and advantageous for maintaining curing. In particular, when X which is a curing group is a vinyl group or an aryl group substituted with a vinyl group, there is an advantage that curing is relatively easy. In particular, a vinyl group substituted with a methyl group

Chemical formula

[0090] According to one embodiment of this specification, the above n1 is an integer from 1 to 5. When n1 is 2 or more, the substituents within the two or more parentheses are the same as or different from each other.

[0091] In other embodiments, n1 is 1 or 2. When n1 is 2, the two Xs are the same as or different from each other.

[0092] In one embodiment of the present specification, the above chemical formula 1 is represented by any one of the following compounds. [Chemical formula] [Chemical formula]

[0093] According to one embodiment of the present specification, the above compound further contains a counter ion. At this time, the type of the counter ion is not particularly limited, and it can contain any one of the cations of the following structural formulas. [Chemical formula]

[0094] In the above structural formula, X1 to X 32 are the same as or different from each other, and each independently is hydrogen; deuterium; cyano group; nitro group; halogen group; -COOR 104 ; substituted or unsubstituted alkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted fluoroalkyl group; or substituted or unsubstituted aryl group, or a curing group selected from the following curing group groups, R 104 is hydrogen; deuterium; or substituted or unsubstituted alkyl group, a is 1 or 2, b is 0 or 1, and a + b = 2, X 100 ~X 124 are the same as or different from each other, and each independently is hydrogen; deuterium; cyano group; nitro group; halogen group; -COOR 105; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted fluoroalkyl group; or a substituted or unsubstituted aryl group, or a curing group selected from the following curing group group, the above R 105 is a substituted or unsubstituted alkyl group, [Curing group group]

Chemical formula

[0095] The above R30 to R32 are the same as or different from each other, and each independently is a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,

Chemical formula

[0096] According to one embodiment of the present specification, the above R30 to R32 are a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted heterocycle.

[0097] According to one embodiment of the present specification, when adjacent groups among the above R30 to R32 are bonded to each other, they form a heterocycle containing a central S as a hetero element, and the above heterocycle can be substituted or unsubstituted.

[0098] According to one embodiment of the present specification, when adjacent groups among the above R30 to R32 are bonded to each other, they can form tetrahydrothiophene, thiophene, benzothiophene or dibenzothiophene, and the above ring can be substituted or unsubstituted.

[0099] According to one embodiment of the present specification, the above cation can contain any one of the cations of the following structural formulas.

Chemical formula

[0100] According to one embodiment of the present specification, the structural formula of the above cation may be any one of the following cations.

Chemical formula

Chemical formula

Chemical formula

[0101] According to one embodiment of the present specification, the above compound is represented by any one of the following structures.

Chemical formula

Chemical formula

Chemical formula

[0102] The compound according to an embodiment of the present specification can be produced as described in the production method below. In the production method described below, the substituents can be bonded by methods known in the art, and the type, position, or number of substituents can be changed according to the techniques known in the art.

[0103] In one embodiment of the present specification, a coating composition containing the above-described compound is provided.

[0104] In one embodiment of the present specification, the above coating composition contains the compound of Chemical Formula 1 and a solvent.

[0105] In one embodiment of the present specification, the above coating composition may be liquid. The above "liquid" means a liquid state at normal temperature and normal pressure.

[0106] In one embodiment of the present specification, the solvent may be, for example, chlorinated solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o-dichlorobenzene; ether solvents such as tetrahydrofuran, dioxane; aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, mesitylene; aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane; ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone, isophorone, tetralone, decalone, acetylacetone; ester solvents such as ethyl acetate, butyl acetate, ethyl cellosolve acetate; polyhydric alcohols and their derivatives such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol; alcohol solvents such as methanol, ethanol, propanol, isopropanol, cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; and amide solvents such as N-methyl-2-pyrrolidone, N,N-dimethylformamide; solvents such as tetralin are exemplified, but any solvent that can dissolve or disperse the compound of Chemical Formula 1 according to one embodiment of the present invention may be used, and the solvents are not limited thereto.

[0107] In other embodiments, the solvent can be used alone or in combination of two or more solvents.

[0108] In one embodiment of the present specification, the coating composition may further include an additional compound together with the compound of Chemical Formula 1.

[0109] According to another embodiment, the coating composition contains the compound of Chemical Formula 1 as a dopant and contains the additional compound as a host. At this time, the mass ratio of the compound of Chemical Formula 1 to the additional compound (Compound of Chemical Formula 1: Additional compound) may be 1:9 to 5:5.

[0110] In another embodiment, the additional compound may be an arylamine compound or an arylamine compound substituted with a vinyl group. When the compound of Chemical Formula 1 and the arylamine compound substituted with a vinyl group are used together, there is an advantage that their curing temperatures are similar to each other and the reactivity is good.

[0111] As an example of the additional compound, the following compounds are included, but not limited thereto.

Chemical Formula

[0112] The viscosity of the coating composition is 2 cP to 15 cP at room temperature (about 25 °C). When the viscosity is satisfied, it is easy to manufacture the device.

[0113] This specification also provides an organic light-emitting device formed using the coating composition.

[0114] The organic light-emitting device according to this specification can be included and used in various electronic devices. For example, the electronic device may be, but is not limited to, a display panel, a touch panel, a solar module, a lighting device, etc.

[0115] In one embodiment of this specification, it includes a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, and one or more of the organic layers include the coating composition or a cured product thereof, and the cured product of the coating composition is a state in which the coating composition is cured by heat treatment or light treatment.

[0116] In one embodiment of the present specification, the organic layer containing the coating composition or its cured product is a hole transport layer or a hole injection layer.

[0117] In one embodiment of the present specification, the organic layer containing the coating composition or its cured product is an electron transport layer or an electron injection layer.

[0118] In other embodiments, the organic layer containing the coating composition or its cured product is a light-emitting layer.

[0119] In other embodiments, the organic layer containing the coating composition or its cured product is a light-emitting layer, and the light-emitting layer contains the compound as a host of the light-emitting layer.

[0120] In other embodiments, the organic layer containing the coating composition or its cured product is a light-emitting layer, and the light-emitting layer contains the compound as a dopant of the light-emitting layer.

[0121] In one embodiment of the present specification, the organic light-emitting device further includes one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, a layer that simultaneously performs hole transport and hole injection, and a layer that simultaneously performs electron transport and electron injection.

[0122] In one embodiment of the present specification, the first electrode is an anode and the second electrode is a cathode.

[0123] According to other embodiments, the first electrode is a cathode and the second electrode is an anode.

[0124] In other embodiments, the organic light-emitting device may be an organic light-emitting device having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

[0125] In other embodiments, the organic light-emitting device may be an inverted type organic light-emitting device in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0126] The organic layer of the organic light-emitting device described in this specification can be a single-layer structure, but can also be a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention can have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, a layer that simultaneously performs hole transport and hole injection, a layer that simultaneously performs electron transport and electron injection, and the like as the organic layer. However, the structure of the organic light-emitting device is not limited thereto, and it can include a smaller number of organic layers.

[0127] For example, the structure of the organic light-emitting device according to an embodiment of this specification is illustrated in FIG. 1.

[0128] FIG. 1 illustrates the structure of an organic light-emitting device in which an anode 201, a hole injection layer 301, a hole transport layer 401, a light-emitting layer 501, a layer 601 that simultaneously performs electron transport and electron injection, and a cathode 701 are sequentially stacked on a substrate 101.

[0129] The above FIG. 1 illustrates an organic light-emitting device and is not limited thereto.

[0130] When the above organic light-emitting device includes a plurality of organic layers, the above organic layers can be formed of the same substance or different substances.

[0131] The organic light-emitting device described in this specification can be manufactured by materials and methods known in the art, except that one or more of the organic layers are formed using a coating composition containing the compound of Chemical Formula 1 above.

[0132] For example, the organic light-emitting device of this specification can be manufactured by sequentially laminating an anode, an organic layer, and a cathode on a substrate. At this time, a PVD (physical vapor deposition) method such as a sputtering method or an e-beam evaporation method is used to deposit a metal, a metal oxide having conductivity, or an alloy thereof on the substrate to form an anode, and a hole injection layer, a hole transport layer, a light-emitting layer, and an organic layer including a layer that simultaneously performs electron transport and electron injection are formed through a solution process, a vapor deposition process, etc., and then a substance that can be used as a cathode is deposited thereon to be manufactured. In addition to such a method, an organic light-emitting device can be manufactured by sequentially depositing an organic layer and an anode substance from a cathode substance on a substrate.

[0133] This specification also provides a method for manufacturing an organic light-emitting device formed using the above coating composition.

[0134] Specifically, in one embodiment of this specification, it includes the steps of preparing a substrate; forming a first electrode on the substrate; forming one or more organic layers on the first electrode; and forming a second electrode on the organic layer, and the step of forming the organic layer includes the step of forming one or more organic layers using the coating composition.

[0135] In one embodiment of this specification, the step of forming one or more organic layers using the coating composition uses a spin coating method.

[0136] In other embodiments, the step of forming one or more organic layers using the coating composition uses a printing method.

[0137] In the embodiments of this specification, the printing method includes, for example, inkjet printing, nozzle printing, offset printing, transfer printing, or screen printing, etc., but is not limited thereto.

[0138] The coating composition according to an embodiment of the present specification is suitable for a solution process due to its structural characteristics and can be formed by a printing method, so it has the effect of being economical in terms of time and cost during the manufacture of the device.

[0139] In one embodiment of the present specification, the step of forming one or more organic layers using the coating composition includes: coating the coating composition on the first electrode or one or more organic layers; and heat-treating or light-treating the coated coating composition.

[0140] In one embodiment of the present specification, the step of heat-treating can be performed through heat treatment, and the heat treatment temperature in the step of heat-treating is 85°C to 250°C. According to one embodiment, it may be 100°C to 250°C, and in other embodiments, it may be 150°C to 250°C.

[0141] In other embodiments, the heat treatment time in the step of heat-treating is 1 minute to 2 hours. According to one embodiment, it may be 10 to 2 hours, and in other embodiments, it may be 10 minutes to 90 minutes.

[0142] In the step of forming an organic layer formed using the coating composition, when the heat treatment or light treatment step is included, an organic layer including a structure in which a plurality of the compounds included in the coating composition form crosslinks and are thinned can be provided. In this case, when another layer is laminated on the surface of the organic layer formed using the coating composition, it is possible to prevent dissolution, morphological influence, or decomposition by a solvent.

[0143] Therefore, when the organic layer formed using the coating composition is formed including the heat treatment or light treatment step, the resistance to a solvent increases, and solution deposition and crosslinking methods can be repeatedly performed to form multiple layers, and the stability increases, thereby increasing the lifetime characteristics of the device.

[0144] As the anode material, usually, a material with a large work function is preferred so that hole injection into the organic layer becomes smooth. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SNO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0145] As the cathode material, usually, a material with a small work function is preferably used so that electron injection into the organic layer becomes easy. Specific examples of cathode materials include metals such as barium, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structured materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0146] The above hole injection layer is a layer for injecting holes from an electrode. As the hole injection material, a compound having the ability to transport holes, excellent hole injection effects from the anode and to the light-emitting layer or light-emitting material, preventing the transfer of excitons generated in the light-emitting layer to the electron injection layer or electron injection material, and excellent in thin film forming ability is preferable. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include the compound of Chemical Formula 1 described above, metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, and conductive polymers such as polyaniline and polythiophene, but are not limited thereto only.

[0147] The above hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. As the hole transport material, a material that can transport holes from the anode or the hole injection layer and transfer them to the light-emitting layer, and a material having a high mobility with respect to holes is suitable. Specific examples include arylamine-based organic substances, conductive polymers, and block copolymers having both a conjugated part and a non-conjugated part, but are not limited thereto only.

[0148] The layer that simultaneously performs hole transport and hole injection can contain the materials of the above-described hole transport layer and hole injection layer.

[0149] As the above-mentioned luminescent substance, it is a substance that can emit light in the visible light region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer respectively, and a substance with good quantum efficiency for fluorescence and phosphorescence is preferred. Specific examples include 8-hydroxyquinoline aluminum complex (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole, benzothiazole and benzimidazole-based compounds; polymers of poly(p-phenylene vinylene) (PPV); spiro compounds; polyfluorene, rubrene, etc., but are not limited thereto.

[0150] The above-mentioned light-emitting layer can contain a host material and a dopant material. Examples of the host material include condensed aromatic ring derivatives or heterocyclic ring-containing compounds. Specifically, examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and examples of the heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder-shaped furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

[0151] Examples of the above-mentioned dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, examples of the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, periflanthene having an arylamino group, etc., and examples of the styrylamine compounds include compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and a substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc., but are not limited thereto. Also, examples of the metal complexes include iridium complexes, platinum complexes, etc., but are not limited thereto.

[0152] The above-mentioned electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. As the electron transport material, a material that can be well injected with electrons from the cathode and transferred to the light-emitting layer, and has a high mobility for electrons, is preferred. Specific examples include Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; hydroxyflavone-metal complexes, etc., but are not limited thereto. The electron transport layer can be used together with any desired cathode material as used in the prior art. In particular, examples of suitable cathode materials are those having a low work function and are ordinary materials such as an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium, and samarium, and in each case, it is the same as an aluminum layer or a silver layer.

[0153] The above-mentioned electron injection layer is a layer that injects electrons from the electrode. As the electron injection material, a compound that has the ability to transport electrons, has an excellent effect of electron injection from the cathode, has an excellent effect of electron injection on the light-emitting layer or the light-emitting material, prevents the transfer of excitons generated in the light-emitting layer to the hole injection layer, and has excellent thin film forming ability is preferred. Specifically, they include fluorenone, anthraquinodimethane, diphenoquinone, thiopyrandioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthrone, etc. and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives, etc., but are not limited thereto.

[0154] The layer that performs electron transport and electron injection simultaneously can contain the materials of the above-mentioned electron transport layer and electron injection layer.

[0155] Examples of the metal complex compound include, but are not limited to, lithium 8-hydroxyquinolinate, zinc bis(8-hydroxyquinolinate), copper bis(8-hydroxyquinolinate), manganese bis(8-hydroxyquinolinate), aluminum tris(8-hydroxyquinolinate), aluminum tris(2-methyl-8-hydroxyquinolinate), gallium tris(8-hydroxyquinolinate), beryllium bis(10-hydroxybenzo[h]quinolinate), zinc bis(10-hydroxybenzo[h]quinolinate), gallium bis(2-methyl-8-quinolinato)chloride, gallium bis(2-methyl-8-quinolinato)(o-cresolate), aluminum bis(2-methyl-8-quinolinato)(1-naphtholate), gallium bis(2-methyl-8-quinolinato)(2-naphtholate).

[0156] The hole blocking layer is a layer that blocks the holes from reaching the cathode, and generally can be formed under the same conditions as the hole injection layer. Specifically, examples include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.

[0157] The electron blocking layer is a layer that inhibits the electrons from reaching the anode, and substances known in the art can be used.

[0158] The organic light-emitting device according to this specification may be a front emission type, a back emission type, or a double-sided emission type depending on the materials used.

Examples

[0159] Hereinafter, in order to specifically describe the present invention, examples will be given for detailed description. However, the examples according to the present invention can be deformed into various other forms, and the scope of the present invention is not construed as being limited to the examples described below. The examples in this specification are provided to more fully explain the present invention to those having average knowledge in the art.

[0160] <Synthesis Example>

[0161] Synthesis Example 1. Synthesis of Compound 1 1) Synthesis Example 1-1

Chem.

[0162] 5 g (16.2406 mmol) of 1,4-dibromotetrafluorobenzene, 1,201 mg (8.1203 mmol) of 4-vinylphenylboronic acid, 4,137 mg (19.4487 mmol, in 10 mL of distilled water) of tripotassium phosphate (K3PO4), and 40 mL of 1,2-dimethoxyethane were charged into a flask and purged with nitrogen for 30 minutes. 375 mg (0.3248 mmol) of tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) was charged into the flask and stirred at 80 °C for 8 hours. After cooling to room temperature, 40 mL of water was added, and the mixture was extracted three times with 30 mL of ethyl acetate to obtain an organic layer. The obtained organic layer was dried over magnesium sulfate and filtered to obtain a filtrate. The organic solvent was removed, and column purification was performed with 100% hexane to obtain 1.7 g of the target compound (4-bromo-2,3,5,6-tetrafluoro-4'-vinyl-1,1'-biphenyl).

[0163] 2) Synthesis Example 1-2

Chem.

[0164] 4,574 mg (15.4026 mmol) of 1-bromo-2,3,5,6-tetrafluoro-4-(trifluoromethyl)benzene and 50 mL of diethyl ether were charged into a flask and stirred under the condition of -78 °C for 1 hour. 6.16 mL (15.4206 mmol, 2.5 M) of n-butyllithium (n-BuLi) was slowly charged into the flask and stirred under the condition of -78 °C for 1 hour. 5.13 mL (5.1342 mmol, 1 M heptane) of trichloroborane was slowly added at -78 °C and stirred for 1 hour to obtain a solution of tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borane. This solution was used for the next reaction at -78 °C without a purification process immediately.

[0165] 3) Synthesis Example 1-3

Chemical formula

[0166] 1.7 g (5.1342 mmol) of 4-bromo-2,3,5,6-tetrafluoro-4'-vinyl-1,1'-biphenyl and 17 mL of diethyl ether were charged into a flask and stirred under the condition of -78 °C for 30 minutes. 2.05 mL (5.1342 mmol, 2.5 M) of n-butyllithium was added at -78 °C and stirred under the condition of -78 °C for 1 hour. This solution was added to the previously prepared solution of tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borane at -78 °C. It was stirred overnight while slowly warming to room temperature naturally. 50 mL of water was added to terminate the reaction, and the organic layer was obtained by extracting 3 times with 50 mL of dichloromethane. The organic layer was dried and column-purified while changing the eluent to 50%, 100% ethyl acetate / hexane, and 100% dichloromethane to obtain 2.6 g of the target compound (lithium (2,3,5,6-tetrafluoro-4'-vinyl-[1,1'-biphenyl]-4-yl)tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borate).

[0167] 4) Synthesis Example 1-4

Chemical formula

[0168] 2.6 g (2.8256 mmol) of lithium (2,3,5,6-tetrafluoro-4'-vinyl-[1,1'-biphenyl]-4-yl)tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borate), 15 mL of acetone (Act), and 15 mL of water were charged into a flask and stirred for 30 minutes. 1,180 mg (2.8256 mmol) of (4-isopropylphenyl)(p-tolyl)iodonium bromide was charged into the flask and stirred strongly for 2 hours. The mixture was extracted three times with 15 mL of dichloromethane to obtain an organic layer, and the organic solvent was removed. Column purification was sequentially performed with 50%, 100% ethyl acetate / hexane, and 100% dichloromethane to obtain 2.5 g of Compound 1 {(4-isopropylphenyl)(p-tolyl)iodonium (2,3,5,6-tetrafluoro-4'-vinyl-[1,1'-biphenyl]-4-yl)tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borate)}.

[0169] The Mass measurement chart of the cation of the above Compound 1 is shown in Figure 2 below, and the Mass measurement chart of the anion is shown in Figure 3 below.

[0170] Synthesis Example 2. Synthesis of Compound 2 1) Synthesis Example 2-1

Chemical formula

[0171] 5 g (10.9666 mmol) of 4,4'-dibromooctafluorobiphenyl, 1,623 mg (10.9666 mmol) of 4-vinylphenylboronic acid, 2,793 mg (13.1599 mmol, 7 mL of distilled water) of tripotassium phosphate, and 30 mL of 1,2-dimethoxyethane were charged into a flask and purged with nitrogen for 30 minutes. 253 mg (0.2193 mmol) of tetrakis(triphenylphosphine)palladium(0) was charged into the flask and stirred at 80 °C for 8 hours. After cooling to room temperature, 30 mL of water was added, and the mixture was extracted three times with 30 mL of ethyl acetate to obtain an organic layer. The obtained organic layer was dried over magnesium sulfate and filtered to obtain a filtrate. The organic solvent was removed, and column purification was performed with 100% hexane to obtain 3 g of the target compound (4-bromo-2,2',3,3',5,5',6,6'-octafluoro-4''-vinyl-1,1':4',1''-terphenyl).

[0172] 2) Synthesis Example 2-2

Chemical formula

[0173] The solution of tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borane was prepared in the same manner as in Synthesis Example 1-2 described above.

[0174] (4-Bromo-2,2’,3,3’,5,5’,6,6’-octafluoro-4’’-vinyl-1,1’:4’,1’’-terphenyl) 3 g (6.2608 mmol) and 20 mL of diethyl ether were placed in a flask and stirred at -78 °C for 30 minutes. 2.50 mL (6.2608 mmol, 2.5 M) of n-butyllithium was added to the flask at -78 °C and stirred for 1 hour. The solution in the flask was gradually added to a solution of tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borane prepared in another flask at -78 °C. The mixture was stirred overnight while slowly warming to room temperature naturally. 20 mL of water was added to terminate the reaction, and the mixture was extracted 3 times with 20 mL of dichloromethane to obtain an organic layer. The organic layer was dried and purified by column chromatography while changing the eluent to 50%, 100% ethyl acetate / hexane, and 100% dichloromethane to obtain 4.1 g of the target compound (lithium (2,2’,3,3’,5,5’,6,6’-octafluoro-4’’-vinyl-[1,1’:4’,1’’-terphenyl]-4-yl)tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borate).

[0175] 3) Synthesis Example 2-3

Chemical formula

[0176] 4.1 g (3.8382 mmol) of lithium (2,2′,3,3′,5,5′,6,6′-octafluoro-4″-vinyl-[1,1′:4′,1″-terphenyl]-4-yl)tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borate, 30 mL of acetone and 30 mL of water were charged into a flask and stirred for 30 minutes. 1,430 mg (3.8382 mmol) of (4-isopropylphenyl)(p-tolyl)iodonium bromide was charged into the flask and stirred strongly for 2 hours. The mixture was extracted three times with 30 mL of dichloromethane to obtain an organic layer, and the organic solvent was removed. Column purification was sequentially performed with 50%, 100% ethyl acetate / hexane, and 100% dichloromethane to obtain 4.2 g of Compound 2 {(4-isopropylphenyl)(p-tolyl)iodonium (2,2′,3,3′,5,5′,6,6′-octafluoro-4″-vinyl-[1,1′:4′,1″-terphenyl]-4-yl)tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borate}.

[0177] The NMR measurement diagram of the above Compound 2 is shown in Figure 4. m / z: 1061.02 (100.0%), 1062.02 (44.3%), 1060.02 (24.8%), 1061.03 (11.0%), 1063.03 (5.0%), 1063.03 (4.6%), 1062.03 (1.8%), 1064.03 (1.3%)

[0178] Synthesis Example 3. Synthesis of Compound 3 1) Synthesis Example 3-1

Chemical Structure

[0179] The above 5′-bromo-[1,1′:3′,1″-terphenyl]-4,4″-dicarbaldehyde compound was synthesized with reference to the literature "Nature Communications, 10(1), 1-9, 2019".

[0180] 2) Synthesis Example 3-2 [Chemistry]

[0181] 11,248 mg (31.4870 mmol) of methyltriphenylphosphonium bromide (CH3PPh3Br) and 80 mL of tetrahydrofuran (THF) were charged into a flask and stirred at 0 °C for 30 minutes. 12.05 mL (30.118 mmol, 2.5 M) of n-butyllithium was slowly added to the flask and stirred at 0 °C for 1 hour. 5 g (13.6900 mmol) of the prepared 5'-bromo-[1,1':3',1''-terphenyl]-4,4''-dicarbaldehyde and 50 mL of an aqueous solution of tetrahydrofuran were slowly added to the flask and stirred at 0 °C for 30 minutes. The flask was stirred for 2 hours while gradually raising the temperature to room temperature. 100 mL of water was added to terminate the reaction, and the mixture was extracted 3 times with 100 mL of ethyl acetate. It was dried over sodium sulfate and filtered. The organic solvent was removed, and purification by silica column with 10% ethyl acetate / hexane gave 4,580 mg of the target compound (5'-bromo-4,4''-divinyl-1,1':3',1''-terphenyl).

[0182] 3) Synthesis Example 3-3 [Chemistry]

[0183] 5'-Bromo-4,4''-divinyl-1,1':3',1''-terphenyl 4,580 mg (12.6771 mmol), bis(pinacolato)diboron (B2Pin2) 4,185 mg (16.4803 mmol), potassium acetate (KOAc) 3,732 mg (38.0138 mmol) and 42 mL of dioxane were charged into a flask and filled with nitrogen. [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (Pd(dppf)Cl2) 311 mg (0.3803 mmol) was charged into the flask and stirred at 80 °C for 16 hours. The flask was cooled to room temperature and 40 mL of water was added. The mixture was extracted three times with 40 mL of ethyl acetate. The organic layer was dried over sodium sulfate and filtered. The organic solvent was removed and the residue was purified by silica column chromatography with 20% ethyl acetate / hexane to obtain 4,600 mg of the target compound (2-(4,4''-divinyl-[1,1':3',1''-terphenyl]-5'-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane).

[0184] 4) Synthesis Example 3-4

Chemical formula

[0185] The solution of tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borane was prepared in the same manner as in Synthesis Example 1-2 described above.

[0186] 2-(4,4’’-Divinyl-[1,1’:3’,1’’-terphenyl]-5’-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 4,600 mg (11.2648 mmol) and 38 mL of diethyl ether were charged into a flask and stirred at -78 °C for 30 minutes. 4.51 mL (11.2648 mmol, 2.5 M) of n-butyllithium was charged into the flask at -78 °C and stirred for 1 hour. The solution in the flask was gradually added to a solution of tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borane prepared in another flask at -78 °C. The mixture was stirred overnight while slowly warming to room temperature naturally. 38 mL of water was added to terminate the reaction, and the mixture was extracted three times with 30 mL of dichloromethane to obtain an organic layer. The organic layer was dried and purified by column chromatography while changing the eluent to 50%, 100% ethyl acetate / hexane, and 100% dichloromethane to obtain 8.2 g of the target compound (lithium (2’’,2’’’,3’’,3’’’,5’’,5’’’,6’’,6’’’-octafluoro-4-vinyl-5’-(4-vinylphenyl)-[1,1’:3’,1’’:4’’,1’’’-quarterphenyl]-4’’’-yl)tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borate).

[0187] 5) Synthesis Example 3-5

Chemical Structure

[0188] 8.2 g (6.5787 mmol) of lithium (2’’,2’’’,3’’,3’’’,5’’,5’’’,6’’,6’’’-octafluoro-4-vinyl-5’-(4-vinylphenyl)-[1,1’:3’,1’’:4’’,1’’’-quarterphenyl]-4’’’-yl) tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl) borate, 33 mL of dichloromethane (MC) and 33 mL of water were charged into a flask and stirred for 30 minutes. 2,748 mg (6.5787 mmol) of (4-isopropylphenyl)(p-tolyl)iodonium bromide was charged into the flask and stirred strongly for 2 hours. The mixture was extracted three times with 30 mL of dichloromethane to obtain an organic layer, and the organic solvent was removed. Column purification was sequentially performed with 50%, 100% ethyl acetate / hexane, and 100% dichloromethane to obtain 6.7 g of Compound 3 ((4-isopropylphenyl)(p-tolyl)iodonium (2’’,2’’’,3’’,3’’’,5’’,5’’’,6’’,6’’’-octafluoro-4-vinyl-5’-(4-vinylphenyl)-[1,1’:3’,1’’:4’’,1’’’-quarterphenyl]-4’’’-yl) tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl) borate).

[0189] The NMR measurement diagram of the above Compound 3 is shown in Figure 5. m / z: 1239.10 (100.0%), 1240.10 (59.5%), 1238.10 (24.8%), 1241.10 (17.4%), 1239.10 (14.8%), 1242.11 (3.3%), 1240.11 (2.9%), 1240.11 (1.4%)

[0190] Synthesis Example 4. Synthesis of Compound 4 1) Synthesis Example 4-1

Chemical Structure

[0191] 5-Bromoisophthalaldehyde (5 g, 23.4709 mmol) and CH3BrPPh3 (30.75 g, 70.4126 mmol) were placed in tetrahydrofuran [THF], and then potassium tert-butoxide [t-BuOK] (8.0 g, 70.4126 mmol) was added at 0 °C and stirred for 1 hour. The reaction was quenched with water and extracted with ethyl acetate [EA]. Magnesium sulfate [MgSO4] was added to the collected organic solution for drying and filtration, and then the organic solvent was removed by a rotary evaporator under vacuum. The residue was purified by column chromatography to obtain 4.1 g of the target compound.

[0192] 2) Synthesis Example 4-2

Chemical formula

[0193] 1-Bromo-3,5-divinylbenzene (4.1 g, 19.6088 mmol) was placed in dioxane, and potassium acetate [KOAc] (5.8 g, 58.8264 mmol) and bis(pinacolato)diboron (6.5 g, 25.4914 mmol) were added. After that, nitrogen bubbling was carried out at room temperature for 30 minutes. [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (717 mg, 0.9804 mmol) was added thereto, and the mixture was stirred under the condition of 80 °C for 16 hours. The reaction was quenched with water and extracted with ethyl acetate. Magnesium sulfate was added to the collected organic solution for drying and filtration, and then the organic solvent was removed by a rotary evaporator under vacuum. The residue was purified by column chromatography to obtain 3.9 g of the target compound.

[0194] 3) Synthesis Example 4-3

Chemical formula

[0195] 2-(3,5-Divinylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.9 g, 15.2255 mmol) was placed in 1,2-dimethoxyethane, potassium phosphate tribasic (K3PO4, 8.2 g, 38.6727 mmol) and 1,4-dibromo-2,3,5,6-tetrafluorobenzene (9.4 g, 30.4509 mmol) were additionally added, and then nitrogen bubbling was carried out for 30 minutes. Tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4, 704 mg, 0.6090 mmol) was added, and the mixture was stirred at 80 °C for 9 hours. The reaction was terminated with water and extracted with ethyl acetate. Magnesium sulfate was added to the collected organic solution for drying and filtration, and then the organic solvent was removed by a rotary evaporator under vacuum. The residue was purified by column chromatography to obtain 3.4 g of the target compound.

[0196] 4) Synthesis Example 4-4

Chemical formula

[0197] The solution of tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borane was prepared in the same manner as in Synthesis Example 1-2 described above.

[0198] 4-Bromo-2,3,5,6-tetrafluoro-3’,5’-divinyl-1,1’-biphenyl (2 g, 5.5999 mmol) was placed in diethyl ether and stirred at -78 °C for 1 hour. n-Butyllithium (2.35 mL, 5.8799 mmol, 2.5 M) was slowly added and stirred at -78 °C for 1 hour. The prepared solution was slowly added to the prepared solution of tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borane, and the mixture was stirred overnight while slowly warming from -78 °C to room temperature. The reaction was terminated with water and extracted with ethyl acetate. The solvent of the collected organic solution was removed by a rotary evaporator under vacuum. Column purification was carried out in the order of 50% ethyl acetate, 100% ethyl acetate, and 100% dichloromethane to obtain 3.2 g of the target compound.

[0199] 5) Synthesis Example 4-5

Chem.

[0200] Lithium (2,3,5,6-tetrafluoro-3’,5’-divinyl-[1,1’-biphenyl]-4-yl)tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borate (3.2 g, 3.3820 mmol) was placed in 36 ml of a mixed solvent of dichloromethane and water (volume ratio = 1:1) and stirred for 30 minutes. (4-Isopropylphenyl)(p-tolyl)iodonium chloride (1260 mg, 3.3820 mmol) was added and stirred strongly for 1 hour. The reaction was quenched with water and extracted with dichloromethane. The solvent of the collected organic solution was removed by a rotary evaporator under vacuum. Column purification was performed in the order of 50% ethyl acetate, 100% ethyl acetate, and 100% dichloromethane to obtain 3 g of the final compound.

[0201] The NMR measurement chart of the above Compound 4 is shown in Fig. 6. m / z: 939.04 (100.0%), 940.04 (30.3%), 938.04 (24.8%), 940.04 (9.7%), 939.05 (5.6%), 939.05 (4.3%), 941.05 (4.1%), 941.05 (3.6%), 940.05 (1.6%)

[0202] Synthesis Example 5. Synthesis of Comparative Compound 1 1) Synthesis Example 5-1

Chem.

[0203] (The solution of tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borane was prepared in the same manner as in Synthesis Example 1-2 described above.) 5 g (27.3149 mmol) of 4-bromostyrene and 90 mL of diethyl ether were placed in a flask and stirred at -78°C for 30 minutes. 10.9 mL (27.3149 mmol, 2.5 M) of n-butyllithium was added to the flask at -78°C and stirred for 1 hour. The solution in the flask was gradually added to the solution of tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borane prepared at -78°C in another flask. The mixture was stirred overnight while slowly warming to room temperature naturally. 90 mL of water was added to terminate the reaction, and the organic layer was obtained by extracting three times with 90 mL of dichloromethane. The organic layer was dried and purified by column chromatography while changing the eluent to 50%, 100% ethyl acetate / hexane, and 100% dichloromethane to obtain 7.5 g of the target compound (lithium tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)(4-vinylphenyl)borate).

[0204] 2) Synthesis Example 5-2

Chemical formula

[0205] 7.5 g (9.7139 mmol) of lithium tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)(4-vinylphenyl)borate, 50 mL of dichloromethane, and 50 mL of water were placed in a flask and stirred for 30 minutes. 4,508 mg (9.7139 mmol) of (4-isopropylphenyl)(p-tolyl)iodonium bromide was added to the flask and stirred strongly for 2 hours. The organic layer was obtained by extracting three times with 50 mL of dichloromethane, and the organic solvent was removed. The product was purified by column chromatography successively with 50%, 100% ethyl acetate / hexane, and 100% dichloromethane to obtain 7.3 g of Comparative Compound 1 (((4-isopropylphenyl)(p-tolyl)iodonium tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)(4-vinylphenyl)borate).

[0206] Synthesis Example 6. Synthesis of Comparative Compound 2 1) Synthesis Example 6-1

Chemical formula

[0207] (The solution of tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borane was prepared in the same manner as in Synthesis Example 1-2 described above.) 5 g (19.6071 mmol) of 1-bromo-2,3,5,6-tetrafluoro-4-vinylbenzene and 65 mL of diethyl ether were charged into a flask and stirred at -78°C for 30 minutes. 7.84 mL (19.6071 mmol, 2.5 M) of n-butyllithium was added to the flask at -78°C and stirred for 1 hour. The solution in the flask was gradually added to the solution of tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borane prepared in another flask at -78°C. It was stirred overnight while slowly warming to room temperature naturally. 60 mL of water was added to terminate the reaction, and the organic layer was obtained by extracting 3 times with 60 mL of dichloromethane. The organic layer was dried and purified by column chromatography while changing the eluent to 50% ethyl acetate / hexane, 100% ethyl acetate / hexane, and 100% dichloromethane to obtain 10 g of the target compound (lithium tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)(2,3,5,6-tetrafluoro-4-vinylphenyl)borate).

[0208] 2) Synthesis Example 6-2

Chemical formula

[0209] 10 g (8.6488 mmol) of lithium tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)(2,3,5,6-tetrafluoro-4-vinylphenyl)borate, 43 mL of dichloromethane, and 43 mL of water were charged into a flask and stirred for 30 minutes. 3,613 mg (8.6488 mmol) of (4-isopropylphenyl)(p-tolyl)iodonium bromide was charged into the flask and stirred strongly for 2 hours. The mixture was extracted three times with 40 mL of dichloromethane to obtain an organic layer, and the organic solvent was removed. Column purification was sequentially performed with 50%, 100% ethyl acetate / hexane, and 100% dichloromethane to obtain 6.5 g of Comparative Compound 2 ((4-isopropylphenyl)(p-tolyl)iodonium tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)(2,3,5,6-tetrafluoro-4-vinylphenyl)borate).

[0210] Synthesis Example 7. Synthesis of Comparative Compound 3 1) Synthesis Example 7-1 [Chemical formula]

[0211] (The solution of tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borane was prepared in the same manner as in Synthesis Example 1-2 described above.) 5 g (15.1007 mmol) of 3-(4-bromo-2,3,5,6-tetrafluorophenyl)bicyclo[4.2.0]octa-1,3,5-triene and 50 mL of diethyl ether were charged into a flask and stirred at -78°C for 30 minutes. 6.04 mL (15.1007 mmol, 2.5 M) of n-butyllithium was added to the flask at -78°C and stirred for 1 hour. The solution in the flask was gradually added to the solution of tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borane prepared in another flask at -78°C. The mixture was stirred overnight while slowly warming to room temperature naturally. 50 mL of water was added to terminate the reaction, and the organic layer was obtained by extracting three times with 50 mL of dichloromethane. The organic layer was dried and purified by column chromatography while changing the eluent to 50%, 100% ethyl acetate / hexane, and 100% dichloromethane to obtain 9.8 g of the target compound (lithium (4-(bicyclo[4.2.0]octa-1,3,5-triene-3-yl)-2,3,5,6-tetrafluorophenyl)tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borate).

[0212] 2) Synthesis Example 7-2

Chemical formula

[0213] 9.8 g (10.6504 mmol) of lithium (4-(bicyclo[4.2.0]octa-1,3,5-trien-3-yl)-2,3,5,6-tetrafluorophenyl)tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borate, 50 mL of dichloromethane, and 50 mL of water were charged into a flask and stirred for 30 minutes. 4,449 mg (10.6504 mmol) of (4-isopropylphenyl)(p-tolyl)iodonium bromide was charged into the flask and stirred vigorously for 2 hours. The mixture was extracted three times with 50 mL of dichloromethane to obtain an organic layer, and the organic solvent was removed. Column purification was sequentially performed with 50%, 100% ethyl acetate / hexane, and 100% dichloromethane to obtain 7.2 g of Comparative Compound 3 ((4-isopropylphenyl)(p-tolyl)iodonium (4-(bicyclo[4.2.0]octa-1,3,5-trien-3-yl)-2,3,5,6-tetrafluorophenyl)tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borate).

[0214] Synthesis Example 8. Synthesis of Comparative Compound 4 1) Synthesis Example 8-1

Chemical Formula

[0215] 10 g (30.2014 mmol) of 4-bromo-2,3,5,6,-tetrafluoro-4'-vinyl-1,1'-biphenyl and 100 mL of diethyl ether were charged into a flask and stirred at -78 °C for 30 minutes. 12.08 mL (30.2014 mmol) of n-butyllithium was slowly added to the flask and stirred at -78 °C for 1 hour. 6.95 mL (6.9463 mmol, 1 M) of boron trichloride was slowly added and stirred overnight while slowly warming from -78 °C to room temperature. 100 mL of water was added to the flask and extracted three times with 100 mL of ethyl acetate to obtain an organic layer. The organic solvent was removed and column purification was performed while changing the eluent to 50%, 100% ethyl acetate / hexane, and 100% dichloromethane to obtain 6.3 g of the target compound (lithium tetrakis(2,3,5,6-tetrafluoro-4'-vinyl-[1,1'-biphenyl]-4-yl)borate).

[0216] 2) Synthesis Example 8-2

Chemical formula

[0217] 6.3 g (6.1610 mmol) of lithium tetrakis(2,3,5,6-tetrafluoro-4'-vinyl-[1,1'-biphenyl]-4-yl)borate, 30 mL of dichloromethane, and 30 mL of water were charged into a flask and stirred for 30 minutes. 2,574 mg (6.1610 mmol) of (4-isopropylphenyl)(p-tolyl)iodonium bromide was added to the flask and strongly stirred for 2 hours. The mixture was extracted three times with 30 mL of dichloromethane to obtain an organic layer, and the organic solvent was removed. Column purification was performed successively with 50%, 100% ethyl acetate / hexane, and 100% dichloromethane to obtain 7.2 g of Comparative Compound 4 ((4-isopropylphenyl)(p-tolyl)iodonium tetrakis(2,3,5,6-tetrafluoro-4'-vinyl-[1,1'-biphenyl]-4-yl)borate).

[0218] Synthesis Example 9. Synthesis of Compound A

Chemical formula

[0219] 1) Preparation of Chemical Formula A-B Chemical formula A-A (9 g, 27.9 mmol) and 4-formylbenzeneboronic acid (4.18 g, 27.9 mmol) were dissolved in anhydrous tetrahydrofuran (THF) (100 mL). Then, Pd(PPh3)4 (0.32 g, 0.28 mmol) and 70 mL of 2M aqueous potassium carbonate (K2CO3 / H2O) solution were added, and the mixture was refluxed for 6 hours. After the reaction solution was cooled to room temperature, the organic layer was extracted. The reaction solution was concentrated and recrystallized with ethyl alcohol (EtOH) to obtain chemical formula A-B (8.9 g, yield 92%). MS: [M+H] + =348

[0220] 2) Preparation of Chemical Formula A-C Chemical formula A-B (8.2 g, 23.6 mmol) prepared in step 1) above was dissolved in chloroform (200 mL). After adding N-bromosuccinimide (4.15 g, 23.6 mmol), the mixture was stirred at room temperature for 5 hours. Distilled water was added to the reaction solution to terminate the reaction, and the organic layer was extracted. The reaction solution was concentrated and recrystallized with ethyl alcohol (EtOH) to obtain chemical formula A-C (8.25 g, yield 82%). MS: [M+H] + =427

[0221] Figure 8 is a diagram showing the MS spectrum of the above chemical formula A-C.

[0222] 3) Preparation of Chemical Formula A-D Dihydroxyethene (1.1 g, 17.7 mmol) was dissolved in 50 mL of toluene with chemical formula A-C (3.1 g, 8.85 mmol) prepared in step 2) above, and then the mixture was stirred at 150 °C for 48 hours. Ethanol was added to the reaction solution, and a precipitate was formed. The formed ivory solid was filtered, washed with ethanol, and then dried under vacuum to obtain chemical formula A-D (2.8 g, yield 80.2%). MS: [M+H] + =469

[0223] 4) Preparation of Chemical Formula A-E In the above step 3), the produced chemical formula A-D (3 g, 7.04 mmol) and N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (0.99 g, 2.93 mmol) were dissolved in 40 ml of xylene. After adding sodium tert-butoxide (0.68 g, 7.04 mmol), bis(dibenzylideneacetone)palladium(0) 0.13 g (0.23 mmol), and 0.11 ml (0.23 mmol) of 50 wt% tri-tert-butylphosphine toluene solution, the mixture was refluxed under a nitrogen stream for 5 hours. Distilled water was added to the reaction solution to terminate the reaction, and the organic layer was extracted. After column separation with an n-hexane / tetrahydrofuran = 6 / 1 solvent, it was stirred in ethyl alcohol (EtOH), filtered, and then dried under vacuum to obtain chemical formula A-E (2.92 g, yield 48%). MS: [M+H] + =1027

[0224] 5) Production of Chemical Formula A (Bromomethyl)triphenylphosphonium Bromide (2.55 g, 5.85 mmol) was dissolved in 100 mL of tetrahydrofuran (THF). After adding 1 eq. of n-butyllithium (n-BuLi) (2.5 M in hexane, 2.34 mL, 5.85 mmol) at -78 °C, the mixture was stirred for 20 minutes. After raising the reaction temperature to 0 °C, the chemical formula A-E (2 g, 1.95 mmol) produced in the above step 4) was added to the reactant and stirred at the same temperature for 1 hour. Distilled water was added to the reaction solution to terminate the reaction, and the organic layer was extracted. The reaction solution was concentrated, dissolved in methylene chloride (MC), and then recrystallized with ethyl alcohol (EtOH) to obtain chemical formula A (1.28 g, yield 64%). MS: [M+H] + =1023

[0225] Figure 9 is a diagram showing the MS spectrum of chemical formula A.

[0226] Synthesis Example 10. Synthesis of Compound 5 1) Synthesis Example 10-1

Chem.

[0227] 5-Bromoisophthalaldehyde (5 g, 23.4709 mmol) and CH3BrPPh3 (30.75 g, 70.4126 mmol) were placed in tetrahydrofuran [THF], and then potassium tert-butoxide [t-BuOK, potassium tert-butoxide] (8.0 g, 70.4126 mmol) was added at 0 °C and stirred for 1 hour. The reaction was quenched with water and extracted with ethyl acetate [EA]. Magnesium sulfate (magnesium sulfate) was added to the collected organic solution for drying and filtration, and then the organic solvent was removed by a rotary evaporator under vacuum. The residue was purified by column chromatography to obtain 4.1 g of the target compound.

[0228] 2) Synthesis Example 10-2

Chem.

[0229] 1-Bromo-3,5-divinylbenzene (4.1 g, 19.6088 mmol) was placed in dioxane, and potassium acetate (KOAc) (5.8 g, 58.8264 mmol) and bis(pinacolato)diboron (6.5 g, 25.4914 mmol) were added. After that, nitrogen bubbling was carried out at room temperature for 30 minutes. [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (717 mg, 0.9804 mmol) was added thereto, and the mixture was stirred at 80 °C for 16 hours. The reaction was quenched with water and extracted with ethyl acetate. Magnesium sulfate was added to the collected organic solution for drying and filtration, and then the organic solvent was removed by a rotary evaporator under vacuum. The residue was purified by column chromatography to obtain 3.9 g of the target compound.

[0230] 3) Synthesis Example 10-3

Chem.

[0231] 4) Synthesis Example 10-4

Chemical formula

[0232] The solution of tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borane was prepared in the same manner as in Synthesis Example 1-2 described above.

[0233] 4-Bromo-2,2’,3,3’,5,5’,6,6’-octafluoro-3’’,5’’-divinyl-1,1’:4’,1’’-terphenyl (2.829 g, 5.5999 mmol) was placed in diethyl ether and stirred at -78 °C for 1 hour. n-Butyllithium (2.35 mL, 5.8799 mmol, 2.5 M) was slowly added and stirred at -78 °C for 1 hour. The resulting solution was slowly added to a prepared solution of tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borane and stirred overnight while slowly warming from -78 °C to room temperature. The reaction was quenched with water and extracted with ethyl acetate. The solvent of the collected organic solution was removed by a rotary evaporator under vacuum. Column purification was performed in the order of 50% ethyl acetate, 100% ethyl acetate, and 100% dichloromethane to obtain 3.0 g of the target compound.

[0234] 5) Synthesis Example 10-5

Chemical Formula

[0235] Lithium (2,2’,3,3’,5,5’,6,6’-octafluoro-3’’,5’’-divinyl-[1,1’:4’,1’’-terphenyl]-4-yl)tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borate (3.0 g, 2.7416 mmol) was placed in 36 ml of a mixed solvent of dichloromethane and water (volume ratio = 1:1) and stirred for 30 minutes. (4-Isopropylphenyl)(p-tolyl)iodonium chloride (1022 mg, 2.7416 mmol) was added and stirred strongly for 1 hour. The reaction was quenched with water and extracted with dichloromethane. The solvent of the collected organic solution was removed by a rotary evaporator under vacuum. Column purification was performed in the order of 50% ethyl acetate, 100% ethyl acetate, and 100% dichloromethane to obtain 3.4 g of [Compound 5].

[0236] The NMR measurement chart of the above Compound 5 is shown in Figure 10. m / z: 1424.08 (100.0%), 1425.08 (63.8%), 1423.08 (24.8%), 1426.09 (17.1%), 1424.09 (15.9%), 1427.09 (4.1%), 1425.09 (3.3%), 1426.09 (2.9%), 1425.09 (1.7%), 1426.09 (1.0%)

[0237] Synthesis Example 11. Synthesis of Compound 6 1) Synthesis Example 11-1

Chemical Structure

[0238] (E)-1-Bromo-4-(prop-1-en-1-yl)benzene (5.0 g, 25.3704 mmol) was placed in dioxane, and potassium acetate (KOAc) (7.47 g, 76.1112 mmol) and bis(pinacolato)diboron (8.38 g, 32.9815 mmol) were added. After that, nitrogen bubbling was carried out at room temperature for 30 minutes. [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1035 mg, 1.2685 mmol) was added thereto, and the mixture was stirred at 80 °C for 16 hours. The reaction was terminated with water and extracted with ethyl acetate. Magnesium sulfate was added to the collected organic solution for drying and then filtered, and the organic solvent was removed by a rotary evaporator under vacuum. The residue was purified by column chromatography to obtain 4.5 g of the target compound.

[0239] 2) Synthesis Example 11-2

Chemical Structure

[0240] (E)-4,4,5,5-Tetramethyl-2-(4-(prop-1-en-1-yl)phenyl)-1,3,2-dioxaborolane (4.5 g, 18.4320 mmol) was placed in 1,2-dimethoxyethane, potassium phosphate tribasic (K3PO4, 9.9 g, 46.8174 mmol) and 4,4'-dibromo-2,2',3,3',5,5',6,6'-octafluoro-1,1'-biphenyl (16.807 g, 36.8640 mmol) were added, and then nitrogen bubbling was carried out for 30 minutes. Tetrakis(triphenylphosphine)palladium(0) (852 mg, 0.7373 mmol) was added and stirred at 80 °C for 9 hours. The reaction was interrupted with water and extracted with ethyl acetate. Magnesium sulfate was added to the collected organic solution for drying and filtration, and then the organic solvent was removed by a rotary evaporator under vacuum. The residue was purified by column chromatography to obtain 5.6 g of (E)-4-bromo-2,2',3,3',5,5',6,6'-octafluoro-4''-(prop-1-en-1-yl)-1,1':4',1''-terphenyl.

[0241] 3) Synthesis Example 11-3

Chemical formula

[0242] The solution of tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borane was prepared in the same manner as in Synthesis Example 1-2 described above.

[0243] (E)-4-Bromo-2,2’,3,3’,5,5’,6,6’-octafluoro-4’’-(prop-1-en-1-yl)-1,1’:4’,1’’-terphenyl (5.6 g, 11.3547 mmol) was placed in diethyl ether and stirred at -78 °C for 1 hour. n-Butyllithium (4.77 mL, 11.9224 mmol, 2.5 M) was slowly added and stirred at -78 °C for 1 hour. The resulting solution was slowly added to a pre-prepared solution of tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borane and stirred overnight while slowly warming from -78 °C to room temperature. The reaction was quenched with water and extracted with ethyl acetate. The solvent of the collected organic solution was removed by a rotary evaporator under vacuum. Column purification was carried out in the order of 50% ethyl acetate, 100% ethyl acetate, and 100% dichloromethane to obtain 7.4 g of the target compound.

[0244] 4) Synthesis Example 11-4

Chemical formula

[0245] Lithium (E)-(2,2’,3,3’,5,5’,6,6’-octafluoro-4’’-(prop-1-en-1-yl)-[1,1’:4’,1’’-terphenyl]-4-yl)tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borate (7.4 g, 6.8377 mmol) was placed in 36 ml of a mixed solvent of dichloromethane (MC) and water (volume ratio = 1:1) and stirred for 30 minutes. (4-Isopropylphenyl)(p-tolyl)iodonium chloride (2548 mg, 6.8377 mmol) was added and stirred vigorously for 1 hour. The reaction was quenched with water and extracted with dichloromethane. The solvent of the collected organic solution was removed by a rotary evaporator under vacuum. Column purification was carried out in the order of 50% ethyl acetate, 100% ethyl acetate, and 100% dichloromethane to obtain 5.4 g of [Compound 6].

[0246] The NMR measurement diagram of the above Compound 6 is shown in Figure 11. m / z: 1412.08 (100.0%), 1413.08 (62.7%), 1411.08 (24.8%), 1414.09 (16.5%), 1412.09 (15.6%), 1415.09 (3.9%), 1413.09 (3.2%), 1414.09 (2.8%), 1413.09 (1.6%)

[0247] <Example> Example 1 The coating composition was prepared by mixing the coating composition as described in Table 1 below. Specifically, Coating Composition 1 was prepared by mixing the p-doping substance represented by the following Compound 1 of the present invention, the host compound [Compound A], and cyclohexanone. At this time, the weight ratio of Compound 1, Compound A, and the organic solvent was mixed at a weight ratio of 2:8:490 to produce a coating composition.

[0248] The above Coating Composition 1 was spin-coated to form a coating layer, and the film was baked at 250 °C or lower.

[0249] Example 2 Coating Composition 2 was produced in the same manner as Coating Composition 1 above, except that Compound 2 was used instead of Compound 1 of the present invention. The above Coating Composition 2 was spin-coated to form a coating layer, and the film was baked at 250 °C or lower.

[0250] Example 3 Coating Composition 3 was produced in the same manner as Coating Composition 1 above, except that Compound 3 was used instead of Compound 1 of the present invention. The above Coating Composition 3 was spin-coated to form a coating layer, and the film was baked at 250 °C or lower.

[0251] Example 4 Coating Composition 4 was produced in the same manner as Coating Composition 1 above, except that Compound 4 was used instead of Compound 1 of the present invention. The above Coating Composition 4 was spin-coated to form a coating layer, and the film was baked at 250 °C or lower.

[0252] Example 5 Coating composition 5 was produced in the same manner as the above coating composition 1, except that compound 5 was used instead of compound 1 of the present invention. The above coating composition 5 was spin-coated to form a coating layer, and the film was baked at 250°C or lower.

[0253] Comparative Example 1 Coating composition 6 was produced in the same manner as the above coating composition 1, except that comparative compound 1 was used instead of compound 1 of the present invention. The above coating composition 6 was spin-coated to form a coating layer, and the film was baked at 250°C or lower.

[0254] Comparative Example 2 Coating composition 7 was produced in the same manner as the above coating composition 1, except that comparative compound 2 was used instead of compound 1 of the present invention. The above coating composition 7 was spin-coated to form a coating layer, and the film was baked at 250°C or lower.

[0255] Comparative Example 3 Coating composition 8 was produced in the same manner as the above coating composition 1, except that comparative compound 3 was used instead of compound 1 of the present invention. The above coating composition 8 was spin-coated to form a coating layer, and the film was baked at 250°C or lower.

[0256] Comparative Example 4 Coating composition 9 was produced in the same manner as the above coating composition 1, except that comparative compound 4 was used instead of compound 1 of the present invention. The above coating composition 9 was spin-coated to form a coating layer, and the film was baked at 250°C or lower.

[0257] Example 6 Coating composition 10 was produced in the same manner as the above coating composition 1, except that compound 6 was used instead of compound 1 of the present invention. The above coating composition 10 was spin-coated to form a coating layer, and the film was baked at 250°C or lower.

[0258]

Chemical formula

[0259] Example 7 Coating composition 11 was produced in the same manner as the above coating composition 1, except that compound 7 was used instead of compound 1 of the present invention. The above coating composition 11 was spin-coated to form a coating layer, and the film was baked at 250°C or lower.

[0260]

Chemical formula

[0261] Example 8 Coating composition 12 was produced in the same manner as the above coating composition 1, except that compound 8 was used instead of compound 1 of the present invention. The above coating composition 12 was spin-coated to form a coating layer, and the film was baked at 250°C or lower.

[0262]

Table 1

[0263] Through Examples 1 to 8 and Comparative Examples 1 to 4, it was confirmed that films were formed.

[0264] <Experimental Example 1> To confirm the film retention rates for compound 1, compound 3, compound 5, compound 6, compound 7, compound 8, and comparative compounds 1 to 4, the ultraviolet-visible absorption spectra (UV-vis absorption spectrum) of the films formed by the following method were measured.

[0265] The film retention rate was evaluated for the solvent resistance of Compound 1, Compound 3, Compound 5, Compound 6, Compound 7, Compound 8, and Comparative Compounds 1-4 using cyclohexanone. Specifically, after preparing solutions by dissolving the above-prepared Compound 1, Compound 3, Compound 5, Compound 6, Compound 7, Compound 8, and Comparative Compounds 1-4 in cyclohexanone at 4 wt% each, these were spin-coated onto a quartz substrate to a thickness of 100 nm. Then, after heat treatment in a nitrogen atmosphere at a temperature between 190 °C and 200 °C for 30 minutes, the ultraviolet-visible absorption spectrum (UV-vis absorption spectrum) was measured. Next, the same sample was immersed in cyclohexanone for 10 minutes, taken out, the solvent was dried, and again the ultraviolet-visible absorption spectrum (UV-vis absorption spectrum) was measured.

[0266] At this time, the ultraviolet-visible absorption spectra (UV-vis absorption spectra) for Compound 1 and Comparative Compounds 1-4 after solvent immersion, from which the film retention rate can be confirmed, are shown in Fig. 7, and the absorbances at 350 nm, which is the maximum absorption wavelength for Compound 1, Compound 3, Compound 5, Compound 6, Compound 7, Compound 8, and Comparative Compounds 1-4, are compared in Table 2 below.

[0267]

Table 2

[0268] During the device fabrication process, the film is retained while being cured during heat treatment. A higher absorbance means that relatively more remains in the film. Through Fig. 7 and Table 2, it can be confirmed that in the case of Comparative Examples 1-4 using the comparative compounds, the absorbance is relatively low because the film is not retained and is washed out, as compared with Example 1 using Compound 1.

[0269] <Experimental Example 2> Compounds 1 to 3, compound 5 synthesized as a P-doping substance, and comparative compound 4 were dissolved at a weight ratio of 5 wt% in each of the solvents described in Table 3 below to confirm the solubility.

[0270]

Table 3

[0271] Through the above experimental results, it can be confirmed that the compounds in this specification having asymmetry have the characteristic of being relatively well soluble in non-polar solvents compared to comparative compound 4. In an organic light-emitting device in a solution process, when selecting an ink solvent in the process, both the host and the dopant must be soluble. In this regard, the solubility of the dopant is important, but in the case of the compounds of the present invention, there is an advantage that they have solubility in a wider variety of solvents, and the range of solvent selection becomes wider.

Explanation of symbols

[0272] 101: Substrate 201: Anode 301: Hole injection layer 401: Hole transport layer 501: Light-emitting layer 601: Layer for simultaneously performing electron transport and electron injection 701: Cathode

Claims

1. A compound comprising a tetraarylborate anion represented by the following chemical formula 4 and the following counterion: 【Chemical 1】 In the above chemical formula 4, R1 to R19 are the same as or different from each other, and each independently is hydrogen, deuterium, a fluoro group, a fluoroalkyl group, a cyano group, or a substituted or unsubstituted alkyl group, X is a curing group selected from the following structures, 【Chemical Formula 2】 In the above formula, 【Chemical Formula 3】 is the bonding site; m1 is an integer from 1 to 3. When m1 is 2 or more, the substituents in two or more parentheses are the same as or different from each other, n1 is an integer from 1 to 5. When n1 is 2 or more, the substituents in two or more parentheses are the same as or different from each other, R101 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, n2 is an integer from 0 to 4. When n2 is 2 or more, two or more R101s are the same as or different from each other, and n1 + n2 is from 1 to 5; and The counterion is represented by any one of the following structural formulas, 【Chemical Formula 4】 In the above structural formula, X1 to X32 are the same as or different from each other, and each independently is hydrogen; deuterium; a cyano group; a nitro group; a halogen group; -COOR104; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted fluoroalkyl group; or a substituted or unsubstituted aryl group, or a curing group selected from the following curing group group, R104 is hydrogen; deuterium; or a substituted or unsubstituted alkyl group, a is 1 or 2, b is 0 or 1, and a + b = 2, X100 to X124 are the same as or different from each other, and each independently is hydrogen; deuterium; a cyano group; a nitro group; a halogen group; -COOR105; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted fluoroalkyl group; or a substituted or unsubstituted aryl group, or a curing group selected from the following curing group group, The above R105 is a substituted or unsubstituted alkyl group, [Curing Group Group] 【Chemical Formula 5】 R30 to R32 are the same as or different from each other, and each independently is a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring. In the above formula, ​ is the site where bonding occurs.

2. The chemical formula 4 is represented by the following chemical formula 5 or 6, and the compound according to claim 1: [Chemical Formula 7] [Chemical 8] In the above chemical formulas 5 and 6, R1 to R15, X and n1 are as defined in chemical formula 4, R21 to R28 are the same as or different from each other, and each independently is hydrogen, deuterium, a fluoro group, a fluoroalkyl group, a cyano group, or a substituted or unsubstituted alkyl group, R101 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, n2 is an integer from 0 to 4. When n2 is 2 or more, two or more R101 are the same as or different from each other, and n1 + n2 is from 1 to 5.

3. R1 to R19 are the same as or different from each other, and each independently is a fluoro group or a fluoroalkyl group, and the compound according to claim 1.

4. A compound composed of a tetraarylborate anion and a counter ion, wherein the tetraarylborate anion is represented by any one of the following chemical formulas, 【Chemical Formula 9】 【Chemical Formula 10】 、 The compound, wherein the counter ion is represented by any one of the following structural formulas: 【Chemical 11】 In the above structural formula, X1 to X32 are the same as or different from each other, and each independently is hydrogen; deuterium; a cyano group; a nitro group; a halogen group; -COOR104; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted fluoroalkyl group; or a substituted or unsubstituted aryl group, or a curing group selected from the following curing group group, R104 is hydrogen; deuterium; or a substituted or unsubstituted alkyl group, a is 1 or 2, b is 0 or 1, and a + b = 2. X100 to X124 are the same as or different from each other, and each independently is hydrogen; deuterium; a cyano group; a nitro group; a halogen group; -COOR105; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted fluoroalkyl group; or a substituted or unsubstituted aryl group, or a curing group selected from the following curing group group, wherein R105 is a substituted or unsubstituted alkyl group, [Curing group group] 【Chemical Formula 12】 R30 to R32 are the same as or different from each other, and each independently is a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring, in the above formula, 【Chemical 13】 is the bonding site.

5. A coating composition comprising the compound according to any one of Claims 1 to 4.

6. A first electrode; A second electrode; and One or more organic layers provided between the first electrode and the second electrode, An organic light-emitting device, wherein one or more of the organic layers contain the coating composition according to Claim 5 or a cured product thereof.

7. The organic light-emitting device according to Claim 6, wherein the organic layer containing the coating composition or a cured product thereof is a hole transport layer or a hole injection layer.

8. A step of preparing a substrate; A step of forming a first electrode on the substrate; A step of forming one or more organic layers on the first electrode; and A step of forming a second electrode on the organic layer, The method for manufacturing an organic light-emitting device, wherein the step of forming the organic layer includes a step of forming one or more organic layers using the coating composition according to Claim 5.

9. The step of forming one or more organic layers using the coating composition includes A step of coating the coating composition on the first electrode; and A step of heat-treating or light-treating the coated coating composition, The method for manufacturing an organic light-emitting device according to Claim 8.

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