Organic light emitting device

Abstract

The present disclosure relates to an organic light emitting device including: an anode; a cathode; an emitting layer disposed between the anode and the cathode; a first organic material layer disposed between the emitting layer and the anode, the first organic material layer including a composition including a compound of Chemical Formula 1 or a cured material thereof; and a second organic material layer disposed between the first organic material layer and the emitting layer, the second organic material layer including a copolymer of Chemical Formula 3 or a cured material thereof.

Description

Technical Field

[0001] This disclosure claims priority and benefit to Korean Patent Application No. 10-2020-0102660, filed with the Korean Intellectual Property Office on August 14, 2020, the entire contents of which are incorporated herein by reference.

[0002] This disclosure relates to organic light-emitting devices. Background Technology

[0003] Organic light emission (OLED) is one example of converting electric current into visible light through internal processes of specific organic molecules. The principle of OLED is as follows: When an organic material layer is placed between an anode and a cathode, and a current is applied between the two electrodes, electrons and holes are injected into the organic material layer from the cathode and anode, respectively. The injected holes and electrons recombine to form excitons, and light is emitted when these excitons return to their ground state. OLED devices utilizing this principle typically consist of a cathode, an anode, and an organic material layer disposed therebetween (e.g., a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer, and an electron transport layer).

[0004] In this field, deposition methods are primarily used to fabricate organic light-emitting devices. However, the deposition method for fabricating organic light-emitting devices has the following problems: it causes significant material loss and makes it difficult to fabricate large-area devices. To address these issues, devices using solution methods have been developed.

[0005] Therefore, there is a need to develop materials and material combinations for organic material layers prepared using solution methods. Summary of the Invention

[0006] Technical issues

[0007] This disclosure aims to provide organic light-emitting devices with excellent efficiency and / or lifetime characteristics.

[0008] Technical solution

[0009] One embodiment of this disclosure provides an organic light-emitting device, comprising: an anode; a cathode; a light-emitting layer disposed between the anode and the cathode; a first organic material layer disposed between the light-emitting layer and the anode, the first organic material layer comprising a composition containing a compound of formula 1 or a cured material thereof; and a second organic material layer disposed between the first organic material layer and the light-emitting layer, the second organic material layer comprising a copolymer of formula 3 or a cured material thereof.

[0010] [Chemical Formula 1]

[0011]

[0012] In chemical formula 1,

[0013] L represents C, whether substituted or unsubstituted. 6-60 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S. 2-60 Hybrid aryl,

[0014] R1 and R3 may be the same as or different from each other, and each is an independent halogen group.

[0015] R2 and R4 may be the same as or different from each other, and each is independently hydrogen; deuterium; or C. 1-10 alkyl,

[0016] L1 and L2 may be the same or different from each other, and each is an independent direct bond; or methylene.

[0017] X1 and X2 may be the same as or different from each other, and each is an independent curing group.

[0018] R'1, R'2, R'3, R”1, R”2, and R”3 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted C. 1-60 Alkyl; substituted or unsubstituted C 1-60 Alkoxy; substituted or unsubstituted C 6-60 aryl; or C containing one or more heteroatoms selected from N, O and S. 2-60 Mixed aromatics,

[0019] n and n' are each integers from 1 to 5, m and m' are 0 or 1, n+m is 5 or less, and n'+m' is 5 or less.

[0020] n1 and m1 are integers from 0 to 5, n2 and m2 are integers from 0 to 4, and n3 and m3 are integers from 0 to 3.

[0021] When n, n', n1 to n3 and m1 to m3 are each 2 or greater, the substituents in two or more parentheses are either the same or different from each other.

[0022] [Chemical Formula 3]

[0023]

[0024] In chemical formula 3,

[0025] A is a monomer unit containing at least one triarylamine group.

[0026] B' is a monomer unit having at least three bonding sites in the copolymer.

[0027] C' is an aromatic monomer unit or its deuterated analogue.

[0028] E may be the same as or different from each other, and each is independently selected from hydrogen; deuterium; halogen groups; substituted or unsubstituted alkyl groups; substituted or unsubstituted silyl groups; substituted or unsubstituted germanyl groups; substituted or unsubstituted aryl groups; substituted or unsubstituted arylamino groups; substituted or unsubstituted siloxane groups; and substituted or unsubstituted curing groups, and

[0029] a, b, and c are mole fractions, a + b + c = 1, a ≠ 0, and b ≠ 0.

[0030] Beneficial effects

[0031] In an organic light-emitting device comprising a compound of formula 1 in the first organic material layer according to one embodiment of the present disclosure, the curing and film retention properties during the formation of the first organic material layer are excellent, and the hole injection capability to the second organic material layer is enhanced.

[0032] Furthermore, by forming a second organic material layer comprising a copolymer of chemical formula 3 on the first organic material layer as described above, the organic light-emitting device according to one embodiment of the present disclosure has improved device efficiency and / or lifetime. Attached Figure Description

[0033] Figure 1 An example of an organic light-emitting device according to one embodiment of the present disclosure is shown.

[0034] Figures 2 to 6 NMR data of the compounds prepared in the preparation examples of this disclosure are shown.

[0035] Figure 7 The NMR spectrum of lithium (perfluorophenyl)tris(2,3,5,6-tetrafluoro-4-vinylphenyl)borate (compound 3.3') is shown.

[0036] Figure 8 Mass spectra of lithium tris(2,3,5,6-tetrafluoro-4-vinylphenyl)borate (compound 3.3') are shown.

[0037] [Figure Labels]

[0038] 101: Base

[0039] 201: Anode

[0040] 301: Hole Injection Layer

[0041] 401: Hole Transport Layer

[0042] 501: Emissive layer

[0043] 601: Electron Injection and Transport Layer

[0044] 701: Cathode Detailed Implementation

[0045] The contents of this disclosure will be described in detail below.

[0046] In this disclosure, the description of a component (layer) being disposed "on" another component (layer) includes not only the case where one component (layer) is in contact with another component, but also the case where there is another component (layer) between the two components (layers).

[0047] In this specification, unless otherwise stated to the contrary, a description in which a part "includes" certain constituent elements means that it may also include other constituent elements, and does not exclude other constituent elements.

[0048] In this disclosure, the term "layer" has the same meaning as "film" primarily used in the art, and refers to a coating covering a target area. There is no limitation on the size of a "layer," and layers can have the same or different dimensions. According to one embodiment, the size of a "layer" can be the same as the entire device, can correspond to the size of a specific functional region, or can be as small as a single subpixel.

[0049] Unless otherwise defined in this specification, all technical and scientific terms used in this disclosure have the same meaning as commonly understood by one of ordinary skill in the art. While similar or equivalent methods and materials to those described in this disclosure may be used in implementing or experimenting with embodiments of this disclosure, suitable methods and materials are described later. All publications, patent applications, patents, and other references mentioned in this disclosure are incorporated herein by reference in their entirety, and in the event of conflict, the definition in this disclosure takes precedence unless a specific paragraph is cited. Furthermore, materials, methods, and examples are for illustrative purposes only and do not limit the scope of this disclosure.

[0050] In this disclosure, "curing group" means a group capable of crosslinking through heat treatment and / or exposure to light. Crosslinking can be generated by free radicals produced when carbon-carbon multiple bonds or cyclic structures are decomposed by heat treatment or light irradiation.

[0051] In one embodiment of this disclosure, the curing group may be selected from the following structures.

[0052]

[0053] In the structure,

[0054] L11 represents a direct bond; -O-; -S-; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group.

[0055] k is 1 or 2,

[0056] When k is 2, L11 are either the same or different from each other, and

[0057] R21 is a substituted or unsubstituted alkyl group.

[0058] According to one embodiment of this disclosure, L11 is a direct bond; methylene; or ethylene.

[0059] In another implementation, L11 is a direct key.

[0060] According to one embodiment of this disclosure, R21 is methyl; or ethyl.

[0061] According to another embodiment, R21 is methyl.

[0062] In this disclosure, the term "deuterated" is intended to mean that at least one available H is replaced by D. In an X% deuterated compound or group, X% of the available H is replaced by D. In the deuterated compound or group, deuterium is present at 100 times or more of its natural abundance level.

[0063] According to one embodiment of this disclosure, one or more of the compound of Formula 1 and the copolymer of Formula 3 may be deuterated. Hereinafter, the deuterated compound may be prepared in a similar manner using a deuterated precursor material, or more generally, by treating the undeuterated compound with a deuterating solvent such as benzene-d6 in the presence of a Lewis acid H / D exchange catalyst such as trifluoromethanesulfonic acid, aluminum trichloride, or ethylaluminum dichloride.

[0064] In this disclosure, the “deuteration rate” or “deuteration substitution rate” can be determined using known methods such as nuclear magnetic resonance (1H NMR), TLC / MS (thin-layer chromatography / mass spectrometry) or GC / MS (gas chromatography / mass spectrometry).

[0065] In this disclosure, "deuterated analog" refers to a structural analog in which one or more of the available hydrogen atoms of a compound or group are replaced by deuterium.

[0066] In one embodiment of this disclosure, at least one of the compound of formula 1 and the copolymer of formula 3 may be 10% to 100% deuterated.

[0067] In one embodiment of this disclosure, the copolymer of formula 3 is 5% to 100% deuterated.

[0068] In one embodiment of this disclosure, the copolymer of formula 3 is 40% to 100% deuterated.

[0069] In one embodiment of this disclosure, the copolymer of formula 3 is 50% to 100% deuterated.

[0070] According to one embodiment of this disclosure, one or more of the compound of Formula 1 and the copolymer of Formula 3 can be deuterated. When hydrogen positions are replaced by deuterium, the chemical properties of the compound remain almost unchanged. However, the physical properties of the deuterated compound change because the atomic weight of deuterium is twice that of hydrogen. For example, the deuterated compound has a lower vibrational energy, and the reduction in vibrational energy level can prevent a decrease in intermolecular van der Waals forces or a decrease in quantum efficiency due to collisions caused by intermolecular vibrations. Therefore, devices containing deuterated compounds have improved efficiency and lifetime.

[0071] Throughout the disclosure of this application, the term "combination thereof" included in the Markush-type representation means a mixture or combination of one or more of the constituent elements described in the Markush-type representation, and means to include one or more of the constituent elements.

[0072] Examples of substituents in this disclosure are described below; however, substituents are not limited thereto.

[0073] In this public disclosure, "-----" and "*" each refer to a connection point.

[0074] In this disclosure, the term “substitution” means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent, and there is no limitation on the position of substitution, as long as the position is where the hydrogen atom is substituted (i.e., the position where the substituent can be substituted), and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

[0075] In this disclosure, the term "substituted or unsubstituted" means substituted with one or more substituents selected from: deuterium; halogen group; cyano; alkyl; cycloalkyl; alkoxy; silyl; aryl; germanyl; methyl group; and heteroaryl, or substituted with two or more substituents linked together from the substituents exemplified above, or without substituents.

[0076] In this disclosure, the halogen group is a fluorine group (-F), a chlorine group (-Cl), a bromine group (-Br), or an iodine group (-I).

[0077] In this disclosure, the alkyl group can be linear or branched, and although not particularly limited thereto, the number of carbon atoms can be from 1 to 20. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of alkyl groups may include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, etc.

[0078] In this disclosure, cycloalkyl groups are not particularly limited, but may have 3 to 60 carbon atoms, and according to one embodiment, the number of carbon atoms in a cycloalkyl group is 3 to 30. According to another embodiment, the number of carbon atoms in a cycloalkyl group is 3 to 20. Specific examples of cycloalkyl groups may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc.

[0079] In this disclosure, alkoxy groups can be linear or branched. There is no particular limitation on the number of carbon atoms in an alkoxy group, but it can be from 1 to 20. Specific examples of alkoxy groups may include, but are not limited to, methoxy, ethoxy, n-propoxy, n-butoxy, tert-butoxy, n-pentoxy, n-hexoxy, n-octoxy, n-nonoxy, n-decoxy, etc.

[0080] In this disclosure, amino means -NRR', and R and R' may be the same as or different from each other, and may each be an alkyl, aryl, or deuterated analogue thereof independently.

[0081] In this disclosure, aryloxy means -OR, and R means aryl.

[0082] In this disclosure, germanium-based means -GeRR'R", and R, R' and R" are the same as or different from each other, and each is independently hydrogen, deuterium, alkyl, deuterated alkyl, fluoroalkyl, deuterated partially fluorinated alkyl, aryl, or deuterated aryl.

[0083] In this disclosure, silyl means -SiRR'R", and R, R', and R" may be the same as or different from each other, and each is independently hydrogen, deuterium, alkyl, deuterated alkyl, fluoroalkyl, aryl, or deuterated aryl. In some embodiments, when R, R', and R" are each alkyl, one or more carbons of the alkyl group are replaced by Si.

[0084] In this disclosure, siloxane is defined as -SiR2OSiR3, and R may be the same as or different from each other, and each is independently hydrogen, deuterium, alkyl, deuterated alkyl, fluoroalkyl, aryl, or deuterated aryl. In some embodiments, when R is alkyl, one or more carbons of the alkyl group are replaced by Si.

[0085] In this disclosure, siloxy means -OSiR3, and R is the same or different from each other, and each is independently hydrogen, deuterium, alkyl, deuterated alkyl, fluoroalkyl, aryl, or deuterated aryl.

[0086] In this disclosure, the aryl group is not particularly limited, but may have 6 to 60 carbon atoms, and the aryl group may be monocyclic or polycyclic. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to another embodiment, the aryl group has 6 to 20 carbon atoms. When the aryl group is monocyclic, examples may include, but are not limited to, phenyl, biphenyl, terphenyl, etc. When the aryl group is polycyclic, examples may include naphthyl, anthraceneyl, phenanthryl, pyrene, etc. Benzyl, phenylenetriene It includes, but is not limited to, methyl, fluorene, etc.

[0087] In this disclosure, the fluorene group may be substituted, and the two substituents may bond together to form a spirocyclic structure.

[0088] When the fluorene group is substituted, it may include a spirofluorene group, for example... and And substituted fluorene groups, for example (9,9-dimethylfluorene) and (9,9-Diphenylfluorenyl). However, the structure is not limited to this.

[0089] In this disclosure, a heteroaryl group is an aromatic cyclic group comprising one or more of N, O, P, S, Si, and Se as heteroatoms, and although not particularly limited thereto, the number of carbon atoms can be from 2 to 60. According to one embodiment, the heteroaryl group has 2 to 30 carbon atoms. Examples of heteroaryl groups may include, but are not limited to, pyridyl, pyrroloyl, pyrimidinyl, pyridazinyl, furanyl, thiopheneyl, benzothiopheneyl, benzofuranyl, dibenzothiopheneyl, dibenzofuranyl, etc.

[0090] In this disclosure, the above description of aryl groups can be applied to arylene groups, except that arylene groups are divalent.

[0091] In this disclosure, the above description of heteroaryl groups can be applied to hypoaryl groups, except that hypoaryl groups are divalent.

[0092] In this disclosure, an aliphatic ring is a non-aromatic hydrocarbon ring, and examples of aliphatic rings may include examples of the above-described cycloalkyl groups, adamantyl groups, etc.

[0093] In this disclosure, the above description of aryl groups can be applied to aromatic rings.

[0094] In this disclosure, "adjacent" groups can mean a substituent that replaces an atom directly bonded to the atom substituted by the corresponding substituent, a substituent spatially closest to the corresponding substituent, or another substituent that replaces the atom substituted by the corresponding substituent. For example, two substituents in an ortho position of a benzene ring and two substituents in the same carbon atom of an aliphatic ring can be interpreted as groups that are "adjacent" to each other. In Formula 1 of this disclosure, Ra and Rb can be adjacent groups, and Rc and Rd can be adjacent groups.

[0095] In this disclosure, the term "ring" in substituted or unsubstituted rings formed by bonding together refers to a hydrocarbon ring; or a heterocycle. The hydrocarbon ring can be aromatic, aliphatic, or a fused ring of both aromatic and aliphatic compounds. Regarding heterocycles, the description of heterocyclic groups can be applied, except that the heterocycle is divalent.

[0096] In this disclosure, the above description of aryl groups can be applied to aromatic hydrocarbon rings, except that the aromatic hydrocarbon rings are divalent.

[0097] In this disclosure, the above description of cycloalkyl groups can be applied to aliphatic hydrocarbon rings, except that the aliphatic hydrocarbon rings are divalent.

[0098] In this disclosure, mole fraction means the ratio of the number of moles of a given component to the total number of moles of all components.

[0099] In this disclosure, "monomer unit" is intended to mean a repeating unit in a polymer or copolymer.

[0100] Chemical Formula 1 will be described below.

[0101] [Chemical Formula 1]

[0102]

[0103] In chemical formula 1,

[0104] L represents C, whether substituted or unsubstituted. 6-60 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S. 2-60 Hybrid aryl,

[0105] R1 and R3 may be the same as or different from each other, and each is an independent halogen group.

[0106] R2 and R4 may be the same as or different from each other, and each is independently hydrogen; deuterium; or C. 1-10 alkyl,

[0107] L1 and L2 may be the same or different from each other, and each is an independent direct bond; or methylene.

[0108] X1 and X2 may be the same as or different from each other, and each is an independent curing group.

[0109] R'1, R'2, R'3, R”1, R”2, and R”3 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted C. 1-60 Alkyl; substituted or unsubstituted C 1-60 Alkoxy; substituted or unsubstituted C 6-60 aryl; or C containing one or more heteroatoms selected from N, O and S. 2-60 Mixed aromatics,

[0110] n and n' are each integers from 1 to 5, m and m' are 0 or 1, n+m is 5 or less, and n'+m' is 5 or less.

[0111] n1 and m1 are integers from 0 to 5, n2 and m2 are integers from 0 to 4, and n3 and m3 are integers from 0 to 3.

[0112] When n, n', n1 to n3 and m1 to m3 are each 2 or greater, the substituents in two or more parentheses are the same or different from each other.

[0113] According to one embodiment of this disclosure, L is C, whether substituted or unsubstituted. 6-30 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S. 2-30 Hybrid aryl.

[0114] According to one embodiment of this disclosure, L is a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; or a substituted or unsubstituted spirofluorene group.

[0115] In one embodiment of this disclosure, L is any of the following structures.

[0116]

[0117] According to one embodiment of this disclosure, R1 and R3 are each fluorine-based (-F).

[0118] In one embodiment of this disclosure, R2 and R4 may be the same as or different from each other, and each is independently hydrogen; deuterium; or methyl.

[0119] According to one embodiment of this disclosure, R1 and R3 are each fluorinated, and R2 and R4 are the same as or different from each other, and are each independently hydrogen; deuterium; or methyl.

[0120] In one embodiment of this disclosure, L1 and L2 may be the same as or different from each other, and each is independently a direct bond or a methylene group.

[0121] According to one embodiment of this disclosure, X1 and X2 may be the same as or different from each other, and each is an independent curing group. Here, the curing group may include the structure described above.

[0122] In another implementation, X1 and X2 are each

[0123] According to one embodiment of this disclosure, R'1, R'2, R'3, R”1, R”2, and R”3 are the same as or different from each other, and each is independently hydrogen; deuterium; or substituted or unsubstituted C. 1-60 alkyl.

[0124] According to another implementation, R'1 and R”1 are hydrogen; deuterium; or methyl.

[0125] According to one embodiment of this disclosure, R'2, R'3, R”2 and R”3 are each hydrogen.

[0126] In another embodiment, R'1 and R”1 are methyl groups, and n1 and m1 are each integers from 0 to 2.

[0127] According to one embodiment of this disclosure, n2, n3, m2, and m3 are each 0 or 1.

[0128] In one embodiment of this disclosure, chemical formula 1 is selected from any of the following structures.

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136] According to one embodiment of this disclosure, the first organic material layer may further comprise an ionic compound containing an anionic group of the following chemical formula 2.

[0137] [Chemical Formula 2]

[0138]

[0139] In chemical formula 2,

[0140] At least one of R101 to R120 is a curing group.

[0141] At least one of the remaining groups in R101 to R120 that are not curing groups is F; cyano; or a substituted or unsubstituted fluoroalkyl group.

[0142] The remaining groups in R101 to R120 that are not curing groups, F, cyano, or substituted or unsubstituted fluoroalkyl groups are the same as or different from each other, and are each independently hydrogen; deuterium; nitro; -C(O)R 201 ;-OR 202 ;-SR 203 ;-SO3R 204 ;-COOR 205 ;-OC(O)R 206 ;-C(O)NR 207 R 208 ; substituted or unsubstituted alkyl groups; substituted or unsubstituted alkenyl groups; substituted or unsubstituted amino groups; substituted or unsubstituted aryl groups; or substituted or unsubstituted heterocyclic groups, and

[0143] R 201 To R 208 They may be the same as or different from each other, and each is independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group.

[0144] The following text describes ionic compounds containing anionic groups of chemical formula 2.

[0145] According to one embodiment of this disclosure, the anionic group represented by chemical formula 2 includes a curing group in at least one of R101 to R120.

[0146] According to one embodiment of this disclosure, the anionic group represented by chemical formula 2 has one to four curing groups.

[0147] In another embodiment, the anionic group represented by chemical formula 2 has a curing group.

[0148] According to another embodiment, the anionic group represented by chemical formula 2 has two curing groups.

[0149] In another embodiment, the anionic group represented by Formula 2 has four curing groups. The anionic group represented by Formula 2 will not cure without the curing groups, and the device characteristics degrade due to the movement of the cationic and anionic groups of this disclosure between the electrode layers. Furthermore, as the number of curing groups increases, the curing rate of the coating composition increases and the film retention improves; therefore, compounds having four curing groups are more preferred.

[0150] In one embodiment of this disclosure, the anionic group represented by Formula 2 has 8 to 19 F, cyano, or substituted or unsubstituted fluoroalkyl groups.

[0151] According to one embodiment of this disclosure, the amount of F in the anionic group represented by chemical formula 2 is from 15 to 50 parts by weight relative to 100 parts by weight of the anionic group.

[0152] According to one embodiment of this disclosure, the anionic group represented by chemical formula 2 has 8 to 19 F atoms.

[0153] In one embodiment of this disclosure, the first organic material layer may be a hole injection layer, and the ionic compound may be used as a dopant. Here, as the F content in the anionic group increases, the force attracting electrons from other compounds (the host compound) increases, which is more conducive to the generation of holes in the host, and therefore, the performance of the hole injection layer is enhanced.

[0154] According to one embodiment of this disclosure, the content of F can be analyzed using a COSA AQF-100 combustion furnace connected to a Dionex ICS2000 ion chromatograph, or determined by 19F NMR (a method commonly used for the analysis of F).

[0155] In one embodiment of this disclosure, at least one benzene ring selected from the following structural formulas is one of the benzene rings bonded by R101 to R105, R106 to R110, R111 to R115, and R116 to R120 in Formula 2.

[0156]

[0157] According to one embodiment of this disclosure, the ionic compound comprises a cationic group, and the cationic group is selected from monovalent cationic groups. Compounds or the following structural formulas.

[0158]

[0159] In the structural formula,

[0160] Y1 to Y 89 They may be the same as or different from each other, and each is independently hydrogen; cyano; nitro; halogen group; hydroxyl group; -COOR 305 ; substituted or unsubstituted alkyl groups; substituted or unsubstituted alkoxy groups; substituted or unsubstituted aryloxy groups; substituted or unsubstituted cycloalkyl groups; substituted or unsubstituted fluoroalkyl groups; substituted or unsubstituted aryl groups; or fixed groups,

[0161] R 305 It is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0162] p is an integer from 0 to 10, and

[0163] r is 1 or 2, s is 0 or 1, and r + s = 2.

[0164] In this public disclosure, A compound is a compound formed by the coordination bonding of hydrogen ions or other free radicals with non-shared electron pairs of iodine, oxygen, sulfur, nitrogen, phosphorus, etc.

[0165] According to one implementation of this disclosure, Y1 to Y 89 They may be the same as or different from each other, and each is independently hydrogen; cyano; nitro; F; Cl; hydroxyl; -COOR 305 ; methyl; methyl substituted with phenylmethoxy; ethyl; propyl; butyl; pentyl; hexyl; methoxy; methoxy substituted with phenyl; phenoxy; cyclopropyl; ethoxyethoxy; phenyl; naphthyl; or a fixed group, and R 305 It is methyl.

[0166] According to one embodiment of this disclosure, examples of monovalent cationic groups may include Na. + Li + K + And so on, but not limited to these.

[0167] In one embodiment of this disclosure, the cationic group is selected from the following structural formulas.

[0168]

[0169]

[0170]

[0171]

[0172] According to one embodiment of this disclosure, the ionic compound is selected from the following structural formulas.

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180] In one embodiment of this disclosure, a composition comprising a compound of formula 1 and an ionic compound containing an anionic group of formula 2 comprises 5 to 50 parts by weight of the ionic compound containing an anionic group of formula 2, relative to 100 parts by weight of the compound of formula 1.

[0181] The copolymer of chemical formula 3 will be described below.

[0182] According to one embodiment of this disclosure, the copolymer of chemical formula 3 is represented as follows.

[0183] [Chemical Formula 3]

[0184]

[0185] In chemical formula 3,

[0186] A is a monomer unit containing at least one triarylamine group.

[0187] B' is a monomer unit having at least three bonding sites in the copolymer.

[0188] C' is an aromatic monomer unit or its deuterated analogue.

[0189] E may be the same as or different from each other, and each is independently selected from hydrogen; deuterium; halogen groups; substituted or unsubstituted alkyl groups; substituted or unsubstituted silyl groups; substituted or unsubstituted germanyl groups; substituted or unsubstituted aryl groups; substituted or unsubstituted arylamino groups; substituted or unsubstituted siloxane groups; and substituted or unsubstituted curing groups, and

[0190] a, b, and c are mole fractions, a + b + c = 1, a ≠ 0, and b ≠ 0.

[0191] a, b, and c may be the same as or different from each other.

[0192] According to another embodiment, chemical formula 3 can be represented by the following chemical formula 3'.

[0193] [Chemical Formula 3']

[0194]

[0195] In chemical formula 3',

[0196] A is a monomer unit containing at least one triarylamine group.

[0197] B' is a monomer unit having at least three bonding sites in the copolymer.

[0198] C' is an aromatic monomer unit or its deuterated analogue.

[0199] E' may be the same as or different from each other, and each is independently selected from hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted arylamino group; substituted or unsubstituted siloxane group; and substituted or unsubstituted curing group.

[0200] a1, b1, c1, and e1 are mole fractions, a1 + b1 + c1 + e1 = 1, a1 ≠ 0, and b1 ≠ 0.

[0201] z1 is an integer of 3 or greater, and

[0202] * indicates a connection point in the copolymer.

[0203] a1, b1, c1, and e1 may be the same as or different from each other.

[0204] According to one embodiment of this disclosure, all embodiments of A, B', C' and E described below for chemical formula 3 are equivalently applied to chemical formula 3'.

[0205] In one embodiment of this disclosure, unit A, unit B', and optional unit C' are arranged in a regular alternation pattern.

[0206] In one embodiment of this disclosure, unit A, unit B', and optional unit C' are arranged in a block format.

[0207] In one embodiment of this disclosure, unit A, unit B', and optional unit C' are arranged randomly.

[0208] According to one embodiment of this disclosure, the copolymer of Formula 3 can be deuterated. Here, deuteration can be present on one or more of monomer unit A, monomer unit B', and monomer unit C'. Furthermore, deuteration can be present on the copolymer backbone, on side groups (substituents), or both.

[0209] According to one embodiment of this disclosure, the weight-average molecular weight (Mw) of the copolymer of formula 3 can be from 10,000 g / mol to 5,000,000 g / mol, from 10,000 g / mol to 2,000,000 g / mol, or from 10,000 g / mol to 500,000 g / mol.

[0210] In this disclosure, the term weight-average molecular weight (Mw) refers to the molecular weight relative to standard polystyrene as measured using GPC (gel permeation chromatography).

[0211] In this disclosure, monomer unit A is a monomer unit containing at least one triarylamine group. Monomer unit A has two bonding sites in the copolymer.

[0212] According to one embodiment of this disclosure, A is represented by the following chemical formula A-1.

[0213] [Chemical Formula A-1]

[0214]

[0215] In chemical formula A-1,

[0216] Ar1 is a substituted or unsubstituted arylene or a deuterated arylene.

[0217] Ar2 is a substituted or unsubstituted aryl or deuterated aryl group.

[0218] T is selected from direct bonds; substituted or unsubstituted aryl groups; and deuterated aryl groups, as well as

[0219] * indicates a bonding point in the copolymer.

[0220] In one embodiment of this disclosure, A is represented by the following chemical formula A-2.

[0221] [Chemical Formula A-2]

[0222]

[0223] In chemical formula A-2,

[0224] Ar1 may be the same as or different from each other, and each is independently a substituted or unsubstituted arylene or a deuterated arylene.

[0225] Ar2 groups may be identical or different from each other, and each is independently a substituted or unsubstituted aryl or deuterated aryl group.

[0226] Ar3 is a substituted or unsubstituted arylene or a deuterated arylene.

[0227] q is an integer of 0 or greater, and

[0228] * indicates a bonding point in the copolymer.

[0229] According to one embodiment of this disclosure, chemical formula A-2 is represented by the following chemical formula A-2-1.

[0230] [Chemical Formula A-2-1]

[0231]

[0232] In chemical formula A-2-1, the substituents have the same limitations as in chemical formula A-2.

[0233] According to one embodiment of this disclosure, chemical formula A-2 is represented by the following chemical formula A-2-2.

[0234] [Chemical Formula A-2-2]

[0235]

[0236] In chemical formula A-2-2,

[0237] Ar2 groups may be identical or different from each other, and each is independently a substituted or unsubstituted aryl or deuterated aryl group.

[0238] T21 to T25 may be the same as or different from each other, and each is independently selected from hydrogen; F; cyano; alkyl; fluoroalkyl; aryl; heteroaryl; amino; silyl; germanyl; alkoxy; aryloxy; fluoroalkoxy; siloxane; siloxy; deuterated alkyl; deuterated partially fluorinated alkyl; deuterated aryl; deuterated heteroaryl; deuterated amino; deuterated silyl; deuterated germanyl; deuterated alkoxy; deuterated aryloxy; deuterated fluoroalkoxy; deuterated siloxane; deuterated siloxy; and fixed groups, and herein, adjacent groups selected from T21 to T25 may be bonded to each other to form a 5- or 6-membered aromatic ring.

[0239] k are integers from 0 to 4, g are integers from 0 to 3, and h and h1 are either 1 or 2.

[0240] * indicates a bonding point in the copolymer.

[0241] In one embodiment of this disclosure, A is represented by the following chemical formula A-3.

[0242] [Chemical Formula A-3]

[0243]

[0244] In chemical formula A-3,

[0245] Ar2 groups may be identical or different from each other, and each is independently a substituted or unsubstituted aryl or deuterated aryl group.

[0246] Ar4 groups may be identical or different from each other, and each is independently selected from substituted or unsubstituted phenylene groups; substituted or unsubstituted naphthylene groups; and their deuterated analogs.

[0247] T1 and T2 may be the same as or different from each other, and each is independently a conjugate part or its deuterated analogue connected by a non-planar structure.

[0248] d represents an integer from 1 to 6.

[0249] e are integers from 1 to 6, and

[0250] * indicates a bonding point in the copolymer.

[0251] In one embodiment of this disclosure, A is represented by the following chemical formula A-4 or A-5.

[0252] [Chemical Formula A-4]

[0253]

[0254] [Chemical Formula A-5]

[0255]

[0256] In chemical formulas A-4 and A-5,

[0257] Ar2 groups may be identical or different from each other, and each is independently a substituted or unsubstituted aryl or deuterated aryl group.

[0258] Ar5, Ar6, and Ar7 may be identical or different from each other, and each is independently a substituted or unsubstituted arylene or a deuterated arylene.

[0259] T3 to T5 may be the same as or different from each other, and each is independently selected from hydrogen; deuterium; F; cyano; alkyl; fluoroalkyl; aryl; heteroaryl; amino; silyl; germanyl; alkoxy; aryloxy; fluoroalkoxy; siloxane; siloxy; deuterated alkyl; deuterated partially fluorinated alkyl; deuterated aryl; deuterated heteroaryl; deuterated amino; deuterated silyl; deuterated germanyl; deuterated alkoxy; deuterated aryloxy; deuterated fluoroalkoxy; deuterated siloxane; deuterated siloxy; and fixed groups, and hereby, adjacent groups selected from T3, T4, and T5 may bond to each other to form a ring.

[0260] k3 is an integer from 0 to 4, and k4 and k5 are each an integer from 0 to 3.

[0261] * indicates a bonding point in the copolymer.

[0262] According to one embodiment of this disclosure, Ar1 is selected from naphthylene, anthraceneylene, divalent naphthylphenyl, divalent phenylnaphthyl, divalent fluorenyl, their substituted derivatives, and their deuterated analogs.

[0263] According to one embodiment of this disclosure, Ar1 is an aryl group substituted with one or more of the following substituents: deuterium; F; cyano; alkyl; fluoroalkyl; aryl; heteroaryl; amino; silyl; germanyl; alkoxy; aryloxy; fluoroalkoxy; siloxane; siloxy; a fixed group; a deuterated alkyl group; a deuterated partially fluorinated alkyl group; a deuterated aryl group; a deuterated heteroaryl group; a deuterated amino group; a deuterated silyl group; a deuterated germanyl group; a deuterated alkoxy group; a deuterated aryloxy group; a deuterated fluoroalkoxy group; a deuterated siloxane group; a deuterated siloxy group; and a deuterated fixed group. According to another embodiment, the substituent is selected from deuterium, alkyl, arylamino, aryl, deuterated alkyl, deuterated arylamino, and deuterated aryl.

[0264] According to one embodiment of this disclosure, Ar1 is a aryl group.

[0265] According to one embodiment of this disclosure, Ar1 is selected from phenylene; biphenylene; terphenylene; 1-naphthylene; 2-naphthylene; anthraceneylene; divalent fluorene; its deuterated analogs; and derivatives thereof having one or more substituents. According to another embodiment, the one or more substituents are selected from fluorinated, alkyl, alkoxy, silyl, germanyl, siloxy, substituents having a curing group, and their deuterated analogs.

[0266] According to one embodiment of this disclosure, Ar1 is an unsubstituted or aryl group having 6 to 30 carbon atoms substituted with an alkyl group having 1 to 20 carbon atoms or an arylamine group having 6 to 30 carbon atoms.

[0267] In another embodiment, Ar1 is an unsubstituted or substituted phenylene with an alkyl group having 1 to 20 carbon atoms or an arylamine group having 6 to 30 carbon atoms; an unsubstituted or substituted biphenylene with an alkyl group having 1 to 20 carbon atoms or an arylamine group having 6 to 30 carbon atoms; an unsubstituted or substituted terphenylene with an alkyl group having 1 to 20 carbon atoms or an arylamine group having 6 to 30 carbon atoms; or an unsubstituted or substituted naphthylene with an alkyl group having 1 to 20 carbon atoms or an arylamine group having 6 to 30 carbon atoms.

[0268] The description of the implementation scheme for Ar1 applies equally to Ar3, Ar5, Ar6, and Ar7.

[0269] According to one embodiment of this disclosure, Ar2 is selected from naphthyl, anthraceneyl, naphthylphenyl, phenylnaphthyl, fluorenyl, their substituted derivatives, and their deuterated analogs.

[0270] According to one embodiment of this disclosure, Ar2 is aryl.

[0271] According to one embodiment of this disclosure, Ar2 is selected from phenyl; biphenyl; terphenyl; 1-naphthyl; 2-naphthyl; anthraceneyl; fluorenyl; their deuterated analogs; and their derivatives having one or more substituents. According to another embodiment, the one or more substituents are selected from fluorinyl, alkyl, alkoxy, silyl, germanyl, siloxy, substituents having a curing group, and their deuterated analogs.

[0272] According to one embodiment of this disclosure, Ar2 is an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms or an arylamine group having 6 to 30 carbon atoms.

[0273] In another embodiment, Ar2 is an unsubstituted phenyl or a phenyl substituted with an alkyl group having 1 to 20 carbon atoms or an arylamine group having 6 to 30 carbon atoms; an unsubstituted biphenyl or a biphenyl substituted with an alkyl group having 1 to 20 carbon atoms or an arylamine group having 6 to 30 carbon atoms; a terphenyl or a triphenyl or a terphenyl substituted with an alkyl group having 1 to 20 carbon atoms or an arylamine group having 6 to 30 carbon atoms; or an unsubstituted naphthyl or a naphthyl substituted with an alkyl group having 1 to 20 carbon atoms or an arylamine group having 6 to 30 carbon atoms.

[0274] According to one embodiment of this disclosure, T is a direct bond; or an arylene group having 6 to 30 carbon atoms.

[0275] In one embodiment of this disclosure, T3 to T5 may be the same as or different from each other, and each is independently hydrogen or deuterium.

[0276] According to one embodiment of this disclosure, when d is 2 or greater, the substituents in two or more brackets are the same or different from each other.

[0277] According to one embodiment of this disclosure, d is 1 or 2.

[0278] According to one embodiment of this disclosure, when e is 2 or greater, the substituents in two or more brackets are the same or different from each other.

[0279] According to one embodiment of this disclosure, e is 1 or 2.

[0280] According to one embodiment of this disclosure, when k3 to k5 are each 2 or greater, the substituents in two or more brackets are the same or different from each other.

[0281] According to one embodiment of this disclosure, when q is 2 or greater, the substituents in two or more brackets are the same or different from each other.

[0282] According to one embodiment of this disclosure, q is an integer from 0 to 2.

[0283] According to another implementation, q is 0 or 1.

[0284] According to one embodiment of this disclosure, T21 to T25 may be the same as or different from each other, and each is independently hydrogen; deuterium; C. 1-10 Alkyl; or C 1-10 Deuterated alkyl groups.

[0285] According to another implementation, T21 to T25 may be the same as or different from each other, and each is independently C. 1-10 Silyl alkyl; or deuterated C 1-10 Silicylates.

[0286] In another implementation, T21 to T25 may be the same as or different from each other, and each is independently C. 6-20 Aryl; C 6-20 Deuterated aryl; or C 3-20 Mixed aromatic compounds.

[0287] In another embodiment, T21 to T25 may be the same as or different from each other, and each is independently an amino group; or a deuterated amino group.

[0288] According to one embodiment of this disclosure, when k, g, h, and h1 are 2 or greater, the substituents in two or more brackets are the same or different from each other.

[0289] According to one embodiment of this disclosure, k is an integer from 0 to 2.

[0290] According to one embodiment of this disclosure, g is an integer from 0 to 2.

[0291] In one embodiment of this disclosure, g is 1.

[0292] According to one embodiment of this disclosure, T1 and T2 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0293] According to another embodiment, T1 and T2 may be the same as or different from each other, and each is independently an arylene group having 6 to 30 carbon atoms that is either unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms.

[0294] According to another embodiment, T1 and T2 may be the same as or different from each other, and each is independently an unsubstituted or alkyl-substituted naphthylene group having 1 to 20 carbon atoms.

[0295] According to one embodiment of this disclosure, the single-unit A can be any of the following structures.

[0296]

[0297]

[0298]

[0299] In one embodiment of this disclosure, monomer unit B' is a multifunctional monomer unit having at least three bonding sites in the copolymer.

[0300] According to another implementation, the monomer unit B' has three to six bonding sites.

[0301] In another embodiment, the monomer unit B' has three bonding sites.

[0302] In another embodiment, the monomer unit B' has four bonding sites.

[0303] In another embodiment, the monomer unit B' has five bonding sites.

[0304] In another embodiment, the monomer unit B' has six bonding sites.

[0305] According to one embodiment of this disclosure, the monomer unit B' is represented by the following chemical formula B'-A.

[0306] [Chemical formula B'-A]

[0307] Cy1-(Cy2-*)s

[0308] In the chemical formula B'-A,

[0309] Cyl is selected from C, Si, Ge, N, aliphatic cyclic groups, aromatic cyclic groups, deuterated aliphatic cyclic groups, or deuterated aromatic cyclic groups having at least three bonding positions.

[0310] Cy2 groups may be identical or different from each other, and each is independently a direct bond; alkylene; arylene; deuterated alkylene; or deuterated arylene.

[0311] However, when Cy2 is a direct bond, alkylene, or deuterated alkylene, Cy1 is an aromatic cyclic group or a deuterated aromatic cyclic group.

[0312] s is an integer representing the maximum number of available bonding positions from 3 to Cy1, and

[0313] * indicates a bonding point in the copolymer.

[0314] According to one embodiment of this disclosure, Cy1 is C, Si, N, an aliphatic cyclic group having 3 to 30 carbon atoms, or an aromatic cyclic group having 6 to 30 carbon atoms.

[0315] According to one embodiment of this disclosure, s is an integer from 3 to 5, and the substituents in parentheses are the same or different from each other.

[0316] In another implementation, s is 3 or 4.

[0317] According to one embodiment of this disclosure, Cy2 atoms may be the same as or different from each other and are each independently a direct bond; or an arylene group having 6 to 30 carbon atoms.

[0318] In another embodiment, Cy2 may be the same as or different from each other, and each is independently a direct bond; phenylene; or biphenylene.

[0319] In one embodiment of this disclosure, the monomer unit B' is represented by any one of the following chemical formulas B'-1 to B'-9.

[0320] [Chemical formula B'-1]

[0321]

[0322] [Chemical formula B'-2]

[0323]

[0324] [Chemical formula B'-3]

[0325]

[0326] [Chemical formula B'-4]

[0327]

[0328] [Chemical formula B'-5]

[0329]

[0330] [Chemical formula B'-6]

[0331]

[0332] [Chemical formula B'-7]

[0333]

[0334] [Chemical formula B'-8]

[0335]

[0336] [Chemical formula B'-9]

[0337]

[0338] In chemical formulas B'-1 to B'-9,

[0339] Ar8 is an aromatic cyclic group or a deuterated aromatic cyclic group having at least three bonding sites.

[0340] T31 to T61 may be the same as or different from each other, and each is independently selected from deuterium; F; cyano; alkyl; fluoroalkyl; aryl; heteroaryl; amino; silyl; germanyl; alkoxy; aryloxy; fluoroalkoxy; siloxane; siloxy; deuterated alkyl; deuterated partially fluorinated alkyl; deuterated aryl; deuterated heteroaryl; deuterated amino; deuterated silyl; deuterated germanyl; deuterated alkoxy; deuterated aryloxy; deuterated fluoroalkoxy; deuterated siloxane; deuterated siloxy; and fixed groups, and herein, adjacent groups selected from T31 to T61 may be bonded to each other to form a 5- or 6-membered aromatic ring.

[0341] k6 to k19, k21 to k25, and k27 to k35 are each integers from 0 to 4; k20 and k26 are integers from 0 to 5; and k36 is an integer from 0 to 3.

[0342] * indicates a bonding point in the copolymer.

[0343] According to one embodiment of this disclosure, when k6 to k36 are each 2 or greater, the substituents in two or more brackets are the same or different from each other.

[0344] According to one embodiment of this disclosure, Ar8 is benzene having at least three bonding sites.

[0345] According to one embodiment of this disclosure, T31 to T61 are each hydrogen or deuterium.

[0346] According to one embodiment of this disclosure, the single-unit B' can be any of the following structures.

[0347]

[0348]

[0349] According to one embodiment of this disclosure, the monomer unit C' is an aromatic monomer unit or its deuterated analogue.

[0350] In one embodiment of this disclosure, the monomer unit C' is a bifunctional monomer unit having two bonding sites.

[0351] According to one embodiment of this disclosure, the monomer unit C' comprises a curing group or a deuterated curing group.

[0352] In one embodiment of this disclosure, the monomer unit C' can be one of the following chemical formulas.

[0353]

[0354]

[0355]

[0356] In chemical formulas M1 to M20

[0357] R 12 They may be the same as or different from each other, and each is independently selected from deuterium; alkyl; silyl; germanyl; aryl; deuterated alkyl; deuterated silyl; deuterated germanyl; and deuterated aryl.

[0358] R 13 They may be the same as or different from each other, and each is independently selected from hydrogen; deuterium; alkyl; and deuterated alkyl.

[0359] R 14 They may be the same as or different from each other, and each is independently selected from alkyl; aryl; and their deuterated analogues.

[0360] R 15 Selected from aryl and deuterated aryl,

[0361] R represents hydrogen; deuterium; or an alkyl group.

[0362] f is an integer representing the maximum number of available bonding positions from 0 to the substituent.

[0363] t is an integer from 0 to 20, and

[0364] **Refers to the bonding point.

[0365] In one embodiment of this disclosure, when f and t are each 2 or greater, the substituents in two or more brackets are the same or different from each other.

[0366] According to one embodiment of this disclosure, f is an integer from 0 to 2.

[0367] In one embodiment of this disclosure, t is an integer from 1 to 3.

[0368] In one embodiment of this disclosure, R 12 They may be the same as or different from each other, and each is independently deuterium; alkyl groups having 1 to 20 carbon atoms; or aryl groups having 6 to 30 carbon atoms.

[0369] In one embodiment of this disclosure, R 13 They may be the same as or different from each other, and each is independently hydrogen; deuterium; alkyl group having 1 to 20 carbon atoms; or deuterated alkyl group having 1 to 20 carbon atoms.

[0370] In one embodiment of this disclosure, R 15 It is an aryl group having 6 to 30 carbon atoms; or a deuterated aryl group having 6 to 30 carbon atoms.

[0371] In one embodiment of this disclosure, R 14 They may be the same as or different from each other, and each independently is an alkyl group having 1 to 20 carbon atoms; or an aryl group having 6 to 30 carbon atoms.

[0372] According to one embodiment of this disclosure, R is hydrogen; deuterium; or an alkyl group having 1 to 20 carbon atoms.

[0373] According to one embodiment of this disclosure, the single-unit C' may be selected from the following structures.

[0374]

[0375] According to one embodiment of this disclosure, unit E is a capping unit of the copolymer.

[0376] In one embodiment of this disclosure, unit E is a monofunctional unit having a single bond point.

[0377] According to one embodiment of this disclosure, unit E is hydrogen or deuterium.

[0378] According to one embodiment of this disclosure, unit E is a monofunctional monomer unit.

[0379] According to one embodiment of this disclosure, unit E is a curing group or a deuterated curing group.

[0380] According to one embodiment of this disclosure, unit E is aryl or deuterated aryl.

[0381] According to one embodiment of this disclosure, unit E is selected from aryl; arylamino; fixed group; and deuterated analogues thereof.

[0382] According to one embodiment of this disclosure, unit E is selected from phenyl; biphenyl; diphenylamino; its substituted derivatives; and its deuterated analogs. Here, the substituent is C. 1-10 Alkyl groups, curing groups, or their deuterated analogs.

[0383] According to one embodiment of this disclosure, unit E can be any of the following structures.

[0384]

[0385]

[0386] Here, * indicates a bonding point in the copolymer.

[0387] According to one embodiment of this disclosure, a in chemical formula 3 is 0.50 or greater.

[0388] According to one embodiment of this disclosure, a in chemical formula 3 is 0.50 to 0.99.

[0389] According to one embodiment of this disclosure, a in chemical formula 3 is 0.60 to 0.90.

[0390] According to one embodiment of this disclosure, a in chemical formula 3 is 0.65 to 0.80.

[0391] According to one embodiment of this disclosure, b in chemical formula 3 is 0.05 or greater, and according to some embodiments, b is 0.10 or greater.

[0392] According to one embodiment of this disclosure, b in chemical formula 3 is from 0.01 to 0.50.

[0393] According to one embodiment of this disclosure, b in chemical formula 3 is from 0.05 to 0.45.

[0394] According to one embodiment of this disclosure, b in chemical formula 3 is 0.10 to 0.40.

[0395] According to one embodiment of this disclosure, b in chemical formula 3 is 0.20 to 0.35.

[0396] According to one embodiment of this disclosure, the c of chemical formula 3 is 0.

[0397] According to one embodiment of this disclosure, the c of chemical formula 3 is 0 to 0.20.

[0398] According to one embodiment of this disclosure, the c of chemical formula 3 is from 0.01 to 0.20.

[0399] According to one embodiment of this disclosure, the c of chemical formula 3 is from 0.05 to 0.15.

[0400] In one embodiment of this disclosure, the molar ratio of A+B' to E is in the range of 40:60 to 98:2, 50:50 to 90:10, or 60:40 to 80:20.

[0401] According to one embodiment of this disclosure, a1 in chemical formula 3' is 0.30 to 0.90.

[0402] According to one embodiment of this disclosure, a1 in chemical formula 3' is 0.40 to 0.80.

[0403] According to one embodiment of this disclosure, a1 in chemical formula 3' is 0.50 to 0.80.

[0404] According to one embodiment of this disclosure, b1 in chemical formula 3' is 0.05 to 0.40.

[0405] According to one embodiment of this disclosure, b1 in chemical formula 3' is 0.10 to 0.30.

[0406] According to one embodiment of this disclosure, b1 in chemical formula 3' is 0.10 to 0.20.

[0407] According to one embodiment of this disclosure, c1 in chemical formula 3' is 0.

[0408] According to one embodiment of this disclosure, c1 in chemical formula 3' is 0 to 0.15.

[0409] According to one embodiment of this disclosure, c1 in chemical formula 3' is from 0.01 to 0.15.

[0410] According to one embodiment of this disclosure, c1 in chemical formula 3' is 0.05 to 0.12.

[0411] According to one embodiment of this disclosure, the c1 in chemical formula 3' is from 0.05 to 0.60.

[0412] According to one embodiment of this disclosure, c1 in chemical formula 3' is from 0.10 to 0.50.

[0413] According to one embodiment of this disclosure, the c1 in chemical formula 3' is 0.15 to 0.35.

[0414] According to one embodiment of this disclosure, e1 in chemical formula 3' is from 0.05 to 0.60.

[0415] According to one embodiment of this disclosure, e1 in chemical formula 3' is 0.10 to 0.50.

[0416] According to one embodiment of this disclosure, e1 in chemical formula 3' is 0.15 to 0.35.

[0417] According to one embodiment of this disclosure, examples of copolymers of formula 3 are shown below using the form of formula 3'.

[0418] [Copolymer Type 1]

[0419]

[0420] In copolymer type 1, c1 is 0 and there is no monomer unit C'. The end-capping unit E is a curing group.

[0421] [Copolymer Type 2]

[0422]

[0423] In copolymer type 2, c1 is 0 and there is no monomer unit C'. The end-capping unit E is aryl.

[0424] [Copolymer Type 3]

[0425]

[0426] In copolymer type 3, c1 is 0 and there is no monomer unit C'. The end-capping unit E is a curing group.

[0427] [Copolymer Type 4]

[0428]

[0429] In copolymer type 4, monomer unit C' is present and contains a curing group. The end-capping unit E is aryl.

[0430] [Copolymer Type 5]

[0431]

[0432] In copolymer type 5, c1 is 0 and there is no monomer unit C'. The end-capping unit E is a curing group.

[0433] [Copolymer Type 6]

[0434]

[0435] In copolymer type 6, c1 is 0 and there is no monomer unit C'. The end-capping unit E is a curing group.

[0436] [Copolymer Type 7]

[0437]

[0438] In copolymer type 7, c1 is 0 and there is no monomer unit C'. The end-capping unit E is aryl.

[0439] [Copolymer Type 8]

[0440]

[0441] In copolymer type 8, c1 is 0 and there is no monomer unit C'. The end-capping unit E is a curing group.

[0442] [Copolymer Type 9]

[0443]

[0444] In copolymer type 9, c1 is 0 and there is no monomer unit C'. The end-capping unit E is aryl.

[0445] [Copolymer Type 10]

[0446]

[0447] In copolymer type 10, monomer unit C' is present and contains a curing group. End-capping unit E is a curing group.

[0448] [Copolymer Type 11]

[0449]

[0450] In copolymer type 11, c1 is 0 and there is no monomer unit C'. The end-capping unit E is a curing group.

[0451] [Copolymer Type 12]

[0452]

[0453] In copolymer type 12, c1 is 0 and there is no monomer unit C'. The end-capping unit E contains a curing group.

[0454] [Copolymer Type 13]

[0455]

[0456] In copolymer type 13, c1 is 0 and there is no monomer unit C'. The end-capping unit E is aryl.

[0457] [Copolymer Type 14]

[0458]

[0459] In copolymer type 14, c1 is 0 and monomer unit C' is absent. Monomer unit B' is tetrafunctional. End-capping unit E is aryl.

[0460] [Copolymer Type 15]

[0461]

[0462] In copolymer type 15, c1 is 0 and there is no monomer unit C'. The end-capping unit E is a curing group.

[0463] [Copolymer Type 16]

[0464]

[0465] In copolymer type 16, c1 is 0 and there is no monomer unit C'. The end-capping unit E is a curing group.

[0466] [Copolymer Type 17]

[0467]

[0468] In copolymer type 17, c1 is 0 and there is no monomer unit C'. The end-capping unit E is aryl.

[0469] [Copolymer Type 18]

[0470]

[0471] In copolymer type 18, c1 is 0 and there is no monomer unit C'. The end-capping unit E is a curing group.

[0472] [Copolymer Type 19]

[0473]

[0474] In copolymer type 19, c1 is 0 and there is no monomer unit C'. The end-capping unit E is aryl.

[0475] [Copolymer type 20]

[0476]

[0477] In copolymer type 20, c1 is 0 and there is no monomer unit C'. The end-capping unit E is a curing group.

[0478] [Copolymer Type 21]

[0479]

[0480] In copolymer type 21, c1 is 0 and there is no monomer unit C'. The end-capping unit E is a curing group.

[0481] Copolymers of Formula 3 can be prepared using any technique that generates C-C or CN bonds and known polymerization techniques. Several such techniques are known, such as metal-catalyzed direct arylation and Suzuki, Yamamoto, Stille, and metal-catalyzed CN coupling.

[0482] Techniques for controlling the molecular weight of the copolymers of this disclosure are well known in the art. The molecular weight of the copolymers described in this disclosure can generally be controlled by the ratio of monomers in the polymerization reaction. According to another embodiment, the molecular weight can be controlled using a quenching reaction.

[0483] In one embodiment of this disclosure, the composition may be a liquid phase. "Liquid phase" means liquid at room temperature and atmospheric pressure.

[0484] In one embodiment of this disclosure, the composition comprising a compound of formula 1 further comprises a solvent.

[0485] According to one embodiment of this disclosure, a composition comprising a compound of formula 1 may further comprise an ionic compound containing an anionic group of formula 2, and the composition further comprises a solvent.

[0486] According to one embodiment of this disclosure, the composition comprising the copolymer of formula 3 further comprises a solvent.

[0487] In one embodiment of this disclosure, examples of solvents may include: chlorine-based solvents, such as chloroform, dichloromethane, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, or o-dichlorobenzene; and ether-based solvents, such as tetrahydrofuran or dichlorobenzene. Alkanes; solvents based on aromatic hydrocarbons, such as toluene, xylene, trimethylbenzene, or mesitylene; solvents based on aliphatic hydrocarbons, such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, or n-decane; solvents based on ketones, such as acetone, methyl ethyl ketone, cyclohexanone, isophorone, tetrahydronaphthone, naphthyl ketone, or acetylacetone; solvents based on esters, such as ethyl acetate, butyl acetate, or ethyl cellosolve acetate; polyols, such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, etc. Dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerol or 1,2-hexanediol, and derivatives thereof; alcohol-based solvents, such as methanol, ethanol, propanol, isopropanol or cyclohexanol; sulfoxide-based solvents, such as dimethyl sulfoxide; amide-based solvents, such as N-methyl-2-pyrrolidone or N,N-dimethylformamide; tetrahydronaphthalene; etc., however, the solvent is not limited to these, as long as it is a solvent capable of dissolving or dispersing a compound of formula 1 according to one embodiment of this disclosure.

[0488] In another embodiment, the solvent may be used as a single type or as a mixture of two or more solvent types.

[0489] In another embodiment, the boiling point of the solvent is preferably from 40°C to 250°C, more preferably from 60°C to 230°C, however, the boiling point is not limited to this.

[0490] In another embodiment, the composition comprising a compound of formula 1 and an ionic compound containing an anionic group of formula 2 has a viscosity of 2 cP to 15 cP at room temperature.

[0491] In another embodiment, the composition comprising the copolymer of formula 3 has a viscosity of 2 cP to 15 cP at room temperature.

[0492] In one embodiment of this disclosure, the concentration of the composition comprising a compound of Formula 1 and an ionic compound containing an anionic group of Formula 2 is from 0.5 wt% to 10 wt%.

[0493] In one embodiment of this disclosure, the concentration of the composition comprising the copolymer of formula 3 is from 0.1 wt% to 10 wt%.

[0494] In one embodiment of this disclosure, the composition may further comprise one, two or more types of additives selected from thermal polymerization initiators and photopolymerization initiators.

[0495] Examples of thermal polymerization initiators can include peroxides, such as methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, acetylacetone peroxide, methyl cyclohexanone peroxide, cyclohexanone peroxide, isobutyryl peroxide, 2,4-dichlorobenzoyl peroxide, bis-3,5,5-trimethylhexanoyl peroxide, lauryl peroxide, benzoyl peroxide, p-chlorobenzoyl peroxide, dicumyl peroxide, 2,5-dimethyl-2,5-(tert-butoxy)hexane, 1,3-bis(tert-butylperoxy-isopropyl)benzene, tert-butylcumyl peroxide, di-tert-butyl peroxide, 2,5-dimethyl-2,5-(di-tert-butylperoxy-isopropyl)benzene, tert-butylcumyl peroxide, di-tert-butyl peroxide, 2,5-dimethyl-2,5-(di-tert-butylperoxy)hexane, etc. (3,3,5-trimethyl)hexane, tris(tert-butylperoxy)triazine, 1,1-di-tert-butylperoxy-3,3,5-trimethylcyclohexane, 1,1-di-tert-butylperoxycyclohexane, 2,2-di(tert-butylperoxy)butane, 4,4-di-tert-butylperoxyvalerate n-butyl ester, 2,2-bis(4,4-tert-butylperoxycyclohexyl)propane, tert-butylperoxyisobutyrate, di-tert-butylperoxyhexahydroterephthalate, tert-butylperoxy-3,5,5-trimethylhexanoate, tert-butylperoxybenzoate, or di-tert-butylperoxytrimethyl adipate; or azo compounds, such as azobisisobutyronitrile, azobisdimethylvalerate, or azobiscyclohexanenitrile, but not limited thereto.

[0496] Examples of photopolymerization initiators may include acetophenone-based or ketal-based photopolymerization initiators, such as diethoxyacetophenone, 2,2-dimethoxy-1,2-diphenylethyl-1-one, 1-hydroxy-cyclohexyl-phenyl-one, 4-(2-hydroxyethoxy)phenyl-(2-hydroxy-2-propyl)one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butanone-1,2-hydroxy-2-methyl-1 -Phenylacet-1-one, 2-methyl-2-morpholino(4-methylthiophenyl)prop-1-one or 1-phenyl-1,2-propanedione-2-(o-ethoxycarbonyl)oxime; benzoin-based photopolymerization initiators, such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether or benzoin isopropyl ether; benzophenone-based photopolymerization initiators, such as benzophenone, 4-hydroxybenzophenone, 2-benzoylnaphthalene, 4- Benzoylbiphenyl, 4-benzoylphenyl ether, acrylated benzophenone, or 1,4-benzoylbenzene; and thioxanthone-based photopolymerization initiators, such as 2-isopropylthioxanthone, 2-chlorothioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, or 2,4-dichlorothioxanthone; and other photopolymerization initiators such as ethylanthraquinone, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,4,6-trimethylbenzoylphenylethoxyphosphine oxide, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, bis(2,4-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide, methylphenylglyoxyester, 9,10-phenanthrene, acridine-based compounds, triazine-based compounds, imidazole-based compounds; and so on, but not limited to these.

[0497] Furthermore, materials with photopolymerization promoting effects can be used alone or in combination with photopolymerization initiators. Examples include, but are not limited to, triethanolamine, methyldiethanolamine, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, ethyl (2-dimethylamino)benzoate, and 4,4'-dimethylaminobenzophenone.

[0498] According to one embodiment of this disclosure, the first organic material layer is a hole injection layer, and the second organic material layer is a hole transport layer.

[0499] According to one embodiment of this disclosure, a first organic material layer is configured to contact the anode, and a second organic material layer is configured to contact the first organic material layer.

[0500] In one embodiment of this disclosure, a third organic material layer may be included between the second organic material layer and the light-emitting layer.

[0501] According to one embodiment of this disclosure, in addition to the first organic material layer, the second organic material layer, and the light-emitting layer, the organic light-emitting device may also include one, two, or more layers selected from the following: a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a light-emitting layer, an electron injection and transport layer, a hole injection and transport layer, an electron blocking layer, and a hole blocking layer.

[0502] In another embodiment, the organic light-emitting device can be an organic light-emitting device (normal type) having a structure in which an anode, one or more layers of organic material and a cathode are sequentially laminated on a substrate.

[0503] In another embodiment, the organic light-emitting device can be an inverted organic light-emitting device having a reverse structure in which a cathode, one or more layers of organic material and an anode are sequentially laminated on a substrate.

[0504] The organic material layer of the organic light-emitting device disclosed herein can be formed as a single-layer structure, or it can be formed as a multilayer structure in which two or more organic material layers are laminated. For example, the organic light-emitting device of this disclosure 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 injection and transport layer, and an electron injection and transport layer as organic material layers. However, the structure of the organic light-emitting device is not limited to this, and it can include fewer organic layers.

[0505] For example, the structure of an organic light-emitting device according to one embodiment of this disclosure is shown in... Figure 1 middle.

[0506] Figure 1 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, an electron injection and transport layer 601, and a cathode 701 are sequentially laminated on a substrate 101 is shown. In this document, the electron injection and transport layer refers to a layer in which electron injection and electron transport occur simultaneously. Figure 1 The hole injection layer 301 may contain a composition of a compound of formula 1 and an ionic compound or a cured material thereof, and the hole transport layer 401 may contain a composition of a copolymer of formula 3 or a cured material thereof.

[0507] Figure 1 Organic light-emitting devices are shown; however, organic light-emitting devices are not limited to this.

[0508] When an organic light-emitting device comprises a plurality of organic material layers, the organic material layers can be formed of the same or different materials.

[0509] The organic light-emitting device disclosed herein can be manufactured using materials and methods known in the art, except that in the organic material layer, the first organic material layer is formed using a composition comprising a compound of formula 1 and an ionic compound, and the second organic material layer is formed using a composition comprising a copolymer of formula 3.

[0510] For example, the organic light-emitting device of this disclosure can be fabricated by sequentially laminating an anode, an organic material layer, and a cathode on a substrate. In this document, the organic light-emitting device can be fabricated by depositing a metal, a conductive metal oxide, or an alloy thereof on a substrate using physical vapor deposition (PVD) methods such as sputtering or electron beam evaporation to form an anode; forming an organic material layer on the anode using solution methods, deposition methods, etc., including one or more of a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer, an electron transport layer, a hole injection and transport layer, and an electron injection and transport layer; and then depositing a material suitable for use as a cathode on the organic material layer. Besides this method, the organic light-emitting device can also be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0511] Furthermore, one embodiment of this disclosure provides a method for manufacturing an organic light-emitting device formed using the composition.

[0512] Specifically, one embodiment of the method disclosed herein includes: preparing a substrate; forming an anode on the substrate; forming a first organic material layer on the anode; forming a second organic material layer on the first organic material layer; forming a light-emitting layer on the second organic material layer; and forming a cathode on the light-emitting layer.

[0513] In one embodiment of this disclosure, the first organic material layer and / or the second organic material layer are formed using spin coating or inkjet printing.

[0514] In one embodiment of this disclosure, the first organic material layer and / or the second organic material layer are formed using a printing method.

[0515] In one embodiment of this disclosure, the printing method may include, for example, inkjet printing, nozzle printing, offset printing, transfer printing, screen printing, etc., but is not limited thereto.

[0516] According to one embodiment of this disclosure, the solution method is suitable as a method for forming a first organic material layer and a second organic material layer, and spin coating, inkjet coating or printing can be used in the manufacturing of the device, which is economical in terms of time and cost.

[0517] In one embodiment of this disclosure, the formation of the first organic material layer includes: coating the first organic material layer with a composition; and subjecting the coated composition to heat treatment or light treatment.

[0518] In one embodiment of this disclosure, the formation of the second organic material layer includes: coating the composition with the second organic material layer; and subjecting the coated composition to heat treatment or light treatment.

[0519] In one embodiment of this disclosure, heat treatment can be performed by heat treatment, and the heat treatment temperature can be from 85°C to 250°C, from 100°C to 250°C according to one embodiment, and from 150°C to 250°C according to another embodiment.

[0520] In another embodiment, the heat treatment time can be from 1 minute to 2 hours, according to one embodiment it can be from 1 minute to 1 hour, and in another embodiment it can be from 20 minutes to 1 hour.

[0521] According to one embodiment of this disclosure, the atmosphere for heat treatment during the formation of the first organic material layer and / or the second organic material layer can be an inert gas atmosphere such as argon or nitrogen, or air, but is not limited thereto.

[0522] When heat treatment or light treatment is included in the formation of the first organic material layer and / or the second organic material layer, the plurality of compounds contained in the composition form crosslinks, and an organic material layer comprising a thin film structure can be provided. This prevents the organic material layer formed using the composition from being dissolved by solvents, morphologically affected, or decomposed when other layers are laminated onto the surface of the organic material layer.

[0523] Therefore, when heat treatment or light treatment is included to form an organic material layer using the composition, solvent resistance is improved, and multilayers can be formed by repeated solution deposition and crosslinking, and the lifespan characteristics of the device can be improved by increasing stability.

[0524] In one embodiment of this disclosure, a composition comprising a compound of formula 1 and an ionic compound, or a composition comprising a copolymer of formula 3, may be a composition mixed into and dispersed in a polymer binder.

[0525] In one embodiment of this disclosure, polymeric binders are preferably those that do not severely inhibit charge transport, and preferably those that do not strongly absorb visible light. Examples of polymeric binders may include poly(N-vinylcarbazole), polyaniline and its derivatives, polythiophene and its derivatives, poly(p-phenylenevinylene) and its derivatives, poly(2,5-thiopheneylenevinylene) and its derivatives, polycarbonate, polyacrylate, polymethyl acrylate, polymethyl methacrylate, polystyrene, polyvinyl chloride, polysiloxane, etc.

[0526] In addition to compounds of Formula 1, the composition of the first organic material layer according to one embodiment of this disclosure may also contain ionic compounds or other monomers (compounds) containing anionic groups of Formula 2.

[0527] The composition of the second organic material layer according to one embodiment of this disclosure may use a copolymer of Formula 3 alone, or may contain other monomers or other copolymers.

[0528] As an anode material, materials with a large work function are generally preferred, which facilitates hole injection into the organic material layer. Specific examples of anode materials that can be used in this disclosure 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; conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; and so on, but are not limited thereto.

[0529] As cathode materials, materials with a small work function are generally preferred, which facilitates electron injection into the organic material layer. 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 materials, such as LiF / Al or LiO2 / Al; and so on, but are not limited to these.

[0530] The hole injection layer is a layer that injects holes from the electrode, and the hole injection material is preferably a compound that has the ability to transfer holes and thus has the effect of injecting holes into the anode, exhibits excellent hole injection effect on the light-emitting layer or light-emitting material, prevents excitons generated in the light-emitting layer from moving to the electron injection layer or electron injection material, and, in addition, has excellent thin film forming ability. The highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include compounds of the above-mentioned chemical formula 1, metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, and so on. Organic materials, anthraquinones, and conductive polymers based on polyaniline and polythiophene, etc., but not limited to these.

[0531] A hole transport layer is a layer that receives holes from a hole injection layer and transports them to a light-emitting layer. Suitable hole transport materials are those capable of receiving holes from the anode or hole injection layer, enabling the holes to move to the light-emitting layer, and possessing high hole mobility. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers possessing both conjugated and non-conjugated portions.

[0532] The hole injection and transport layer may contain the materials of the aforementioned hole transport layer and hole injection layer.

[0533] Luminescent materials are materials capable of emitting light in the visible light region by receiving holes and electrons from the hole transport layer and electron transport layer, respectively, and by combining the holes and electrons. Preferably, they are materials with favorable quantum efficiencies for fluorescence or phosphorescence. Specific examples include: 8-hydroxyquinoline aluminum complexes (Alq3); carbazole-based compounds; dipolystyrene-based compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; and benzo[…]. Zyrazoles, benzothiazole-based and benzimidazole-based compounds; polymers based on poly(p-phenylenevinylene) (PPV); spirocyclic compounds; polyfluorene; red fluorene; etc., but not limited to these.

[0534] The luminescent layer may comprise a host material and dopant materials. Host materials include fused aromatic ring derivatives, heterocyclic compounds, etc. Specifically, fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., however, the materials are not limited to these.

[0535] Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives are fused aromatic ring derivatives having substituted or unsubstituted aryl amino groups, and include pyrene, anthracene, etc., containing aryl amino groups. Diindrone pyrene, etc., and styrylamine compounds are compounds in which at least one aryl vinyl group is substituted with a substituted or unsubstituted aryl amine, and one, two or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamino groups are substituted or unsubstituted. Specifically, this includes styrylamines, styryldiamines, styryltriamines, styryltetraamines, etc., however, styrylamine compounds are not limited thereto. In addition, metal complexes include iridium complexes, platinum complexes, etc., but are not limited thereto.

[0536] An electron transport layer is a layer that receives electrons from an electron injection layer and transports them to a light-emitting layer. Suitable electron transport materials are those that can advantageously receive electrons from the cathode, enabling electrons to move to the light-emitting layer, and possess high electron mobility. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; hydroxyflavonoid-metal complexes, etc. The electron transport layer can be used with any desired cathode material as used in the art. In particular, examples of suitable cathode materials include common materials with small work functions, followed by an aluminum or silver layer. Specifically, cathode materials include cesium, barium, calcium, ytterbium, and samarium, and in each case, followed by an aluminum or silver layer.

[0537] An electron injection layer is a layer that injects electrons from the electrode. Preferably, the electron injection material is a compound that possesses the ability to transport electrons, has the effect of injecting electrons from the cathode, exhibits excellent electron injection effects on the light-emitting layer or light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the hole injection layer, and also possesses excellent thin film forming capabilities. Specific examples include fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiamethoxam dioxide, etc. azole, diazole, triazole, imidazole, Tetracarboxylic acids, fluorenemethane, anthrone, and their derivatives; metal complexes; nitrogen-containing 5-membered ring derivatives; and so on, but not limited to these.

[0538] The electron injection and transport layer may contain the materials of the aforementioned electron transport layer and electron injection layer.

[0539] Metal complex compounds include lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)chlorogallium, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, bis(2-methyl-8-quinoline)(2-naphthol)gallium, etc., but are not limited to these.

[0540] A hole blocking layer is a layer that prevents holes from reaching the cathode, and it can typically be formed under the same conditions as a hole injection layer. Specific examples may include... Diazole or triazole derivatives, phenanthrene-rhein derivatives, BCP, aluminum complexes, etc., but not limited to these.

[0541] An electron blocking layer is a layer that blocks electrons from reaching the anode, and can be made of materials known in the art.

[0542] Depending on the materials used, the organic light-emitting devices according to this disclosure can be top-emitting, bottom-emitting, or dual-emitting.

[0543] Invention Embodiments

[0544] In the following description, this disclosure will be described in detail with reference to embodiments to specifically illustrate this disclosure. However, embodiments based on this disclosure can be modified in various different forms, and the scope of this disclosure should not be construed as limited to the embodiments described below. Embodiments of this disclosure are provided to more fully describe this disclosure to those skilled in the art.

[0545] <Examples of preparation of compounds with chemical formula 1>

[0546] Preparation Example 1. Preparation of Compound 1

[0547] Step 1) Preparation of compound 1-1

[0548]

[0549] 4,4'-Dibromobiphenyl (2 g, 6.4 mmol), Pd(tBu3P)2 (163.5 mg), and NaOtBu (2.46 g, 25.6 mmol) were introduced into a reactor, which was then purged with N2. Toluene (32 mL) and 3-fluoro-4-methylaniline (1.6 mL, 14 mmol) were introduced into the reactor, and the product was stirred overnight at 90 °C. The product was then treated with ethyl acetate and brine, and purified by column chromatography to prepare compound 1-1. The NMR results (¹H NMR (300 Hz, CD2Cl2)) are shown in [Figure number missing]. Figure 2 middle.

[0550] Step 2) Preparation of Compound 1

[0551]

[0552] Compound 1-1 (0.6 g, 1.5 mmol), Pd(tBu3P)2 (54 mg), and NaOtBu (0.432 g, 4.5 mmol) were introduced into a reactor, which was then purged with N2. Toluene (7.5 mL) and compound 1-2 (1.386 g, 3.07 mmol) were introduced into the reactor, and the mixture was stirred overnight at 90 °C. The mixture was then treated with ethyl acetate and water, and the resulting product was purified by column chromatography to prepare compound 1. The NMR results (¹H NMR (300 Hz, CDCl3)) are shown in [Figure number missing]. Figure 3 middle.

[0553] Preparation Example 2. Preparation of Compound 2

[0554] Step 1) Preparation of compound 2-1

[0555]

[0556] 4,4'-Dibromobiphenyl (2 g, 6.4 mmol), Pd(tBu3P)2 (163.5 mg), and NaOtBu (2.46 g, 25.6 mmol) were introduced into a reactor, which was then purged with N2. Toluene (32 mL) and 3,4-difluoroaniline (1.4 mL, 14.1 mmol) were introduced into the reactor, and the product was stirred overnight at 90 °C. The product was then treated with ethyl acetate and brine, and purified by column chromatography to prepare compound 2-1. The NMR results (1H NMR (300 Hz, CDCl3)) are shown in [Figure number missing]. Figure 4 middle.

[0557] Step 2) Preparation of Compound 2

[0558]

[0559] Compound 2-1 (1 g, 2.45 mmol), Pd(tBu3P)2 (87.6 mg, 0.17 mmol), and NaOtBu (0.706 g, 7.35 mmol) were introduced into a reactor, which was then purged with N2. Toluene (12 mL) and compound 1-2 (2.27 g, 5 mmol) were introduced into the reactor, and the mixture was stirred overnight at 90 °C. The mixture was then treated with ethyl acetate and water, and the resulting product was purified by MPLC (medium-pressure liquid chromatography) and recrystallized from DCM (dichloromethane) to prepare compound 2. The NMR results (1H NMR (300 Hz, CD2Cl2)) are shown in [image missing]. Figure 5 middle.

[0560] Preparation Example 3. Preparation of Compound 3

[0561] Step 1) Preparation of compound 3-1

[0562]

[0563] 4,4'-Dibromobiphenyl (0.5 g, 1.6 mmol), Pd(tBu3P)2 (40.9 mg), and NaOtBu (615 mg) were introduced into a reactor, which was then purged with N2. Toluene (8 mL) and 4-fluoroaniline (0.337 mL, 3.52 mmol) were introduced, and the product was stirred overnight at 90 °C. The product was then treated with ethyl acetate and brine, and purified by column chromatography to prepare compound 3-1.

[0564] Step 2) Preparation of Compound 3

[0565]

[0566] Compound 3-1 (0.32 g, 0.86 mmol), Pd(tBu3P)2 (31 mg), and NaOtBu (0.248 g, 2.58 mmol) were introduced into a reactor, which was then purged with N2. Toluene (6 mL) and compound 1-2 (900 mg, 1.76 mmol) were introduced into the reactor, and the mixture was stirred overnight at 90 °C. The mixture was then treated with ethyl acetate and water, and the resulting product was purified by column chromatography to prepare compound 3. The NMR results (1H NMR (300 Hz, CDCl3)) are shown in [Figure number missing]. Figure 6 middle.

[0567] Preparation Example 4. Preparation of Compound 4

[0568]

[0569] Diiodobiphenyl (5.00 g, 1.0 equivalent), NaOtBu (7.10 g, 6.0 equivalent), toluene (200 mL), and 3-fluoroaniline (2.39 mL, 2.02 equivalent) were introduced into a round-bottom flask, and the temperature was raised to 90 °C after purging with N2. Pd(tBu3P)2 (0.250 g, 4 mol%) was then introduced, and the mixture was stirred at 90 °C for 1.5 hours. The mixture was then treated with ethyl acetate and brine, and the resulting product was purified by column chromatography to prepare compound 4-1.

[0570] Compound 4-1 (1.0 equivalent) and compound 1-2 (11.4 g, 2.05 equivalent) were introduced into a round-bottom flask, and after introducing NaOtBu (7.10 g, 6.0 equivalent), toluene (200 mL), and Pd(tBu3P)2 (0.25 g, 4 mol%), the mixture was stirred at 90 °C for 1.5 h. The mixture was then purified by column chromatography to prepare compound 4.

[0571] MS:[M+H] + =1113

[0572] Preparation Example 5. Preparation of Compound 5

[0573]

[0574] Diiodobiphenyl (5.00 g, 1.0 equivalent), NaOtBu (7.10 g, 6.0 equivalent), toluene (200 mL), and 2-fluoroaniline (2.40 mL, 2.02 equivalent) were introduced into a round-bottom flask, and the temperature was raised to 90 °C after purging with N2. Pd(tBu3P)2 (0.250 g, 4 mol%) was then introduced, and the mixture was stirred at 90 °C for 1 hour. The mixture was then treated with ethyl acetate and brine, and the resulting product was purified by column chromatography to prepare compound 5-1.

[0575] Compound 5-1 (1.0 equivalent) and compound 1-2 (11.4 g, 2.05 equivalent) were introduced into a round-bottom flask, and after introducing NaOtBu (7.10 g, 6.0 equivalent), toluene (200 mL), and Pd(tBu3P)2 (0.25 g, 4 mol%), the mixture was stirred at 90 °C for 1 hour. The mixture was then purified by column chromatography to prepare compound 5.

[0576] MS:[M+H] + =1113

[0577] Preparation Example 6. Preparation of Compound 6

[0578] Step 1) Preparation of compound 6-1

[0579]

[0580] Diiodobiphenyl (6.00 g, 1.0 equivalent), 2,6-difluoroaniline (4.20 g, 2.2 equivalent), NaOtBu (4.26 g, 3.0 equivalent), and toluene (85 mL) were introduced into a round-bottom flask, and after introducing N2, the temperature was raised to 90 °C. Pd(tBu3P)2 was then introduced into the flask, and the resulting mixture was stirred overnight at 90 °C.

[0581] Step 2) Preparation of Compound 6

[0582]

[0583] Compound 6-1 (1.30 g, 1.0 equivalent), compound 1-2 (3.02 g, 2.1 equivalent), NaOtBu (0.918 g, 3.0 equivalent), and toluene (30 mL) were introduced into a round-bottom flask, and the temperature was raised to 90 °C after introducing N2. Pd(tBu3P)2 (0.114 g, 7 mol%) was then introduced, and the result was stirred at 90 °C for 1 hour. The result was then purified by column chromatography to prepare compound 6.

[0584] MS:[M+H] + =1149

[0585] Preparation Example 7. Preparation of Compound 7

[0586]

[0587] Compound 7-1 (1.0 equivalent), NaOtBu (7.10 g, 6.0 equivalent), toluene (200 mL), and 4-fluoroaniline (2.40 mL, 2.02 equivalent) were introduced into a round-bottom flask, and the temperature was raised to 60 °C after purging with N2. Pd(tBu3P)2 (0.250 g, 4 mol%) was introduced, and the mixture was stirred at 60 °C for 1 hour. Compound 7-2 was prepared by treating the mixture with ethyl acetate and brine, and then purified by column chromatography.

[0588] Compound 7-2 (1.0 equivalent) and compounds 1-2 (11.4 g, 2.05 equivalent) were introduced into a round-bottom flask, and after introducing NaOtBu (7.10 g, 6.0 equivalent), toluene (200 mL), and Pd(tBu3P)2 (0.25 g, 4 mol%), the mixture was stirred at 60 °C for 1 hour. The mixture was then purified by column chromatography to prepare compound 7.

[0589] MS:[M+H]+ =1276

[0590] Preparation Example 8. Preparation of Compound 8

[0591]

[0592] Compound 7-1 (1.0 equivalent), NaOtBu (7.10 g, 6.0 equivalent), toluene (200 mL), and 3-fluoro-4-methylaniline (2.02 equivalent) were introduced into a round-bottom flask, and the temperature was raised to 60 °C after purging with N2. Pd(tBu3P)2 (0.250 g, 4 mol%) was introduced, and the result was stirred at 60 °C for 1 hour. The mixture was then treated with ethyl acetate and brine, and the result was purified by column chromatography to prepare compound 8-1.

[0593] Compound 8-1 (1.0 equivalent) and compound 1-2 (11.4 g, 2.05 equivalent) were introduced into a round-bottom flask, and after introducing NaOtBu (7.10 g, 6.0 equivalent), toluene (200 mL), and Pd(tBu3P)2 (0.25 g, 4 mol%), the mixture was stirred at 60 °C for 1 hour. The mixture was then purified by column chromatography to prepare compound 8.

[0594] MS:[M+H] + =1304

[0595] Preparation Example 9. Preparation of Compound 9

[0596]

[0597] Compound 7-1 (1.0 equivalent), NaOtBu (7.10 g, 6.0 equivalent), toluene (200 ml), and 3,4-difluoroaniline (2.02 equivalent) were introduced into a round-bottom flask, and the temperature was raised to 60 °C after purging with N2. Pd(tBu3P)2 (0.250 g, 4 mol%) was introduced, and the mixture was stirred at 60 °C for 1 hour. Compound 9-1 was prepared by treating the mixture with ethyl acetate and brine, and then purified by column chromatography.

[0598] Compound 9-1 (1.0 equivalent) and compound 1-2 (11.4 g, 2.05 equivalent) were introduced into a round-bottom flask, and after introducing NaOtBu (7.10 g, 6.0 equivalent), toluene (200 mL), and Pd(tBu3P)2 (0.25 g, 4 mol%), the mixture was stirred at 60 °C for 1 hour. The mixture was then purified by column chromatography to prepare compound 9.

[0599] MS:[M+H] + =1312

[0600] Preparation Example 10. Preparation of Compound 10

[0601]

[0602] Diiodobiphenyl (4.00 g, 1.0 equivalent), 2,4,6-trifluoroaniline (2.2 equivalent), NaOtBu (3.79 g, 4.0 equivalent), and toluene (100 mL) were introduced into a round-bottom flask, and the temperature was raised to 90 °C after purging with N2. Pd(tBu3P)2 (0.25 g, 5 mol%) was then introduced, and the mixture was stirred overnight at 90 °C. The mixture was then treated with ethyl acetate and brine, and the resulting product was purified by column chromatography to prepare compound 10-1.

[0603] Compound 10-1 (1.0 equivalent) and compound 1-2 (2.05 equivalent) were introduced into a round-bottom flask, and after introducing NaOtBu (6.0 equivalent), toluene (100 mL), and Pd(tBu3P)2 (0.25 g, 5 mol%), the mixture was stirred at 90 °C for 1 hour. The mixture was then purified by column chromatography to prepare compound 10.

[0604] MS:[M+H] + =1185

[0605] Preparation Example 11. Preparation of Compound 11

[0606]

[0607] Diiodobiphenyl (4.00 g, 1.0 equivalent), 3,4,5-trifluoroaniline (2.2 equivalent), NaOtBu (3.79 g, 4.0 equivalent), and toluene (100 mL) were introduced into a round-bottom flask, and the temperature was raised to 90 °C after purging with N2. Pd(tBu3P)2 (0.25 g, 5 mol%) was then introduced, and the mixture was stirred overnight at 90 °C. Compound 11-1 was prepared by treating the mixture with ethyl acetate and brine, and then purified by column chromatography.

[0608] Compound 11-1 (1.0 equivalent) and compound 1-2 (2.05 equivalent) were introduced into a round-bottom flask, and after introducing NaOtBu (6.0 equivalent), toluene (100 mL), and Pd(tBu3P)2 (0.25 g, 5 mol%), the mixture was stirred at 90 °C for 1 hour. The mixture was then purified by column chromatography to prepare compound 11.

[0609] MS:[M+H] + =1185

[0610] Preparation Example 12. Preparation of Compound 12

[0611]

[0612] Compound 7-1 (1.0 equivalent), NaOtBu (7.10 g, 6.0 equivalent), toluene (200 mL), and 2,4,6-trifluoroaniline (2.02 equivalent) were introduced into a round-bottom flask, and the temperature was raised to 60 °C after purging with N2. Pd(tBu3P)2 (5 mol%) was introduced, and the result was stirred at 60 °C for 1 hour. The mixture was then treated with ethyl acetate and brine, and the result was purified by column chromatography to prepare compound 12-1.

[0613] Compound 12-1 (1.0 equivalent) and compound 1-2 (2.05 equivalent) were introduced into a round-bottom flask, and after introducing NaOtBu (6.0 equivalent), toluene (100 mL), and Pd(tBu3P)2 (5 mol%), the mixture was stirred at 60 °C for 1 hour. The mixture was then purified by column chromatography to prepare compound 12.

[0614] MS:[M+H] + =1348

[0615] Preparation Example 13. Preparation of Compound 13

[0616]

[0617] Compound 7-1 (1.0 equivalent), NaOtBu (7.10 g, 6.0 equivalent), toluene (200 mL), and 3,4,5-trifluoroaniline (2.02 equivalent) were introduced into a round-bottom flask, and the temperature was raised to 60 °C after purging with N2. Pd(tBu3P)2 (4 mol%) was introduced, and the result was stirred at 60 °C for 1 hour. The mixture was then treated with ethyl acetate and brine, and the result was purified by column chromatography to prepare compound 13-1.

[0618] Compound 13-1 (1.0 equivalent) and compound 1-2 (2.05 equivalent) were introduced into a round-bottom flask, and after introducing NaOtBu (6.0 equivalent), toluene (100 mL), and Pd(tBu3P)2 (5 mol%), the mixture was stirred at 60 °C for 1 hour. The mixture was then purified by column chromatography to prepare compound 13.

[0619] MS:[M+H] + =1348

[0620] Preparation Example 14. Preparation of Compound 14

[0621]

[0622] Diiodobiphenyl (6.00 g, 1.0 equivalent), 2,3,4,5,6-pentafluoroaniline (2.2 equivalent), NaOtBu (4.26 g, 3.0 equivalent), and toluene (120 mL) were introduced into a round-bottom flask, and the temperature was raised to 90 °C after purging with N2. Pd(tBu3P)2 (4 mol%) was introduced into the flask, and the mixture was stirred at 90 °C for 1 hour. The mixture was then treated with ethyl acetate and brine, and the resulting product was purified by column chromatography to prepare compound 14-1.

[0623] Compound 14-1 (1.0 equivalent) and compound 1-2 (2.05 equivalent) were introduced into a round-bottom flask, and after introducing NaOtBu (6.0 equivalent), toluene (100 mL), and Pd(tBu3P)2 (5 mol%), the mixture was stirred at 90 °C for 1 hour. The mixture was then purified by column chromatography to prepare compound 14.

[0624] MS:[M+H] + =1257

[0625] Preparation Example 15. Preparation of Compound 15

[0626]

[0627] Compound 7-1 (1.0 equivalent), NaOtBu (7.10 g, 6.0 equivalent), toluene (200 mL), and 2,3,4,5,6-pentafluoroaniline (2.02 equivalent) were introduced into a round-bottom flask, and the temperature was raised to 60 °C after purging with N2. Pd(tBu3P)2 (4 mol%) was introduced, and the result was stirred at 60 °C for 1 hour. The mixture was then treated with ethyl acetate and brine, and the result was purified by column chromatography to prepare compound 15-1.

[0628] Compound 15-1 (1.0 equivalent) and compound 1-2 (2.05 equivalent) were introduced into a round-bottom flask, and after introducing NaOtBu (6.0 equivalent), toluene (100 mL), and Pd(tBu3P)2 (5 mol%), the mixture was stirred at 60 °C for 1 hour. The mixture was then purified by column chromatography to prepare compound 15.

[0629] MS:[M+H] + =1419

[0630] Preparation Examples 1 to 15 illustrate methods for synthesizing compounds of Formula 1, and compounds of Formula 1 can be synthesized by adjusting the type, bonding position, and number of substituents.

[0631] <Examples of the preparation of ionic compounds>

[0632] Preparation Example 1. Preparation of Compound 3-1

[0633] Step 1) Preparation of compound 3-1'

[0634]

[0635] Mg (193 mg, 7.92 mmol), I₂ (4 mg), and THF (10 mL) were introduced into a 100 mL round-bottom flask under a nitrogen atmosphere and stirred for 30 minutes. 4-Bromostyrene (1.04 mL, 7.92 mmol) was then introduced, and the mixture was stirred for one day after placing a 30°C water bath under the round-bottom flask. The dissolution of Mg was confirmed as the reaction solution turned black. Ether (5 mL) was added to dilute the reaction solution. Tris(pentafluorophenyl)borane (1 g, 3.96 mmol) dissolved in ether (5 mL) was slowly added to the reaction solution over 30 minutes. The solution was stirred for one day. Na₂CO₃ (0.1 M, 80 mL, 8.0 mmol) was slowly added to the reaction solution. The organic solvent was extracted with ethyl acetate (20 mL × 3), and residual water was removed with MgSO₄. To further remove residual water and impurities, the mixture was distilled with benzene using Dean-Stark distillation. When approximately 10 mL of solvent remained, the solution was cooled and filtered to prepare compound 3-1' (1.6 g, yield 64%).

[0636] Step 2) Preparation of compound 3-1

[0637]

[0638] Compound 3-1' (100 mg, 0.16 mmol), distilled water (10 mL), and Ph2ICl (60 mg, 0.19 mmol) were introduced into a 25 mL round-bottom flask and stirred for 1 hour. Acetone (15 mL) was added to the reaction solution to produce a precipitate, which was then filtered and dried to prepare compound 3-1 (140 mg, 100% yield).

[0639] MS:[MH] - =615 (negative mode)

[0640] MS:[M+H] + =281 (positive pattern)

[0641] Preparation Example 2. Preparation of Compound 3-2

[0642] Step 1) Preparation of compound 3-2'

[0643]

[0644] Methyltriphenyl potassium bromide (13.90 g, 38.91 mmol) and THF (100 mL) were introduced into a 250 mL round-bottom flask and stirred at 0 °C for 30 min. n-BuLi (15.6 mL, 38.91 mmol, in 2.5 M hexane) was slowly added to the reaction solution, and the result was stirred at 0 °C for 30 min. At 0 °C, 4-formyl-2,3,5,6-tetrafluoro-1-bromobenzene (5.0 g, 19.47 mmol, in 30 mL THF) was slowly added to the reaction solution. The reaction solution was stirred while slowly raising the temperature to room temperature. After 3 h, ether (100 mL) and saturated NH4Cl solution (400 mL) were added to the reaction solution. The organic solvent was extracted with ether (200 mL × 2), and residual water was removed with MgSO4. The result was subjected to column chromatography with ethyl acetate:hexane = 1:9 (volume:volume) to prepare compound 3-2' (1.29 g, yield 26%).

[0645] Step 2) Preparation of compound 3-2”

[0646]

[0647] Mg (95 mg, 3.92 mmol), THF (10 mL), and I₂ (4 mg) were introduced into a 25 mL round-bottom flask and stirred. Compound 3-2' (1.0 g, 3.92 mmol) was introduced into the reaction solution, and the result was stirred at room temperature. After 10 hours, as the solution darkened to confirm complete dissolution of Mg, ether (10 mL) and BCl₃ (1.3 mL, 1.3 mmol, 1 M in hexane solution) were added over 30 minutes. The reaction solution was stirred for one day, and Na₂CO₃ (30 mL, 3.0 mmol, 0.1 M in H₂O) was added. The synthesized material was extracted with ethyl acetate (10 mL × 3), and residual water was removed with MgSO₄. After complete removal of the solvent, water was completely removed using benzene via Dean-Stark solvent, and the solid was filtered to prepare compound 3-2'' (340 mg, 28% yield).

[0648] Step 3) Preparation of compound 3-2

[0649]

[0650] Compound 3-2” (200 mg, 0.27 mmol), 1-(4-vinylbenzyl)pyridine-1- Chloride (69 mg, 0.30 mmol), H₂O (10 mL), and dichloromethane (10 mL) were introduced into a 25 mL round-bottom flask and stirred vigorously for 30 minutes. The organic solvent was extracted with ether (10 mL × 3), and residual water was removed with MgSO₄. The solvent was removed, and the result was dried under vacuum to prepare compound 3-2 (247 mg, 100% yield).

[0651] MS:[MH] - =711 (Negative Mode)

[0652] MS:[M+H] + =196 (positive pattern)

[0653] Preparation Example 3. Preparation of Compound 3-3

[0654] Step 1) Preparation of compound 3-3'

[0655]

[0656] In a 50 mL round-bottom flask, 1-bromo-2,3,5,6-tetrafluoro-4-vinylbenzene (2 g, 7.84 mmol) was introduced into THF (20 mL) and stirred at -78 °C for 30 min. n-BuLi (3.45 mL, 8.63 mmol, 2.5 M) in hexane was slowly introduced into the solution, and the result was stirred at -78 °C for 30 min. BCl3 (2.6 mL, 2.61 mmol, 1 M in hexane solution) was added to the reaction solution over 15 min at -78 °C. The reaction solution was stirred for one day while slowly raising the temperature to room temperature, and water (30 mL) was added. The synthesized material was extracted with ethyl acetate (10 mL × 3) to remove all solvent. Water was completely removed using benzene via Dean-Stark extraction, and the solid was filtered to prepare compound 3-3' (800 mg, 43% yield).

[0657] The NMR spectrum of compound 3-3' is shown in Figure 7 The mass spectrum of compound 3-3' is shown in the figure. Figure 8 middle.

[0658] Step 2) Preparation of compound 3-3

[0659]

[0660] Compound 3-3' (400 mg, 0.56 mmol) and diphenyliodine chloride were added. 176 mg (0.56 mmol), water (10 mL), and acetone (10 mL) were introduced into a 25 mL round-bottom flask and stirred vigorously for 30 minutes. The product was extracted with dichloromethane (10 mL × 3) and dried after solvent removal to prepare compound 3-3 (552 mg, 100% yield).

[0661] MS:[MH] - =711 (Negative Mode)

[0662] MS:[M+H] + =281 (positive pattern)

[0663] Preparation Example 4. Preparation of Compounds 3-4

[0664] Step 1) Preparation of compounds 3-4'

[0665]

[0666] Potassium carbonate (10.4 g, 75.3 mmol) was introduced into a 500 mL round-bottom flask, and dimethylformamide (DMF) (200 mL) was introduced into the flask. 2,3,5,6-Tetrafluorophenol (10.0 g, 60.22 mmol) was introduced into the flask, and the mixture was stirred at 60 °C for 30 min. 4-Vinylbenzyl chloride (7.66 g, 50.18 mmol) was slowly added to the reaction solution, and the mixture was stirred at 60 °C for 16 h. Then, water (300 mL) and ethyl acetate (200 mL) were added. The organic layer was extracted with ethyl acetate (200 mL × 2), and residual water was removed with MgSO4. The mixture was then subjected to column chromatography using ethyl acetate:hexane = 1:9 (v:v) to prepare compound 3-4' (11.2 g, 79% yield).

[0667] Step 2) Preparation of compounds 3-4

[0668]

[0669] Compound 3-4' (10 g, 35.43 mmol) was introduced into a 250 mL round-bottom flask, and the mixture was stirred after the addition of ether (130 mL). The reaction solution was cooled to -78 °C and stirred for 30 min. n-BuLi (17 mL, 42.52 mmol, 2.5 M in hexane) was slowly added over 30 min. The result was then stirred for 1 h. BCl3 (8.15 mL, 8.15 mmol, 1 M in hexane) was slowly added over 30 min. The temperature of the reaction solution was slowly raised to room temperature. The reaction solution was stirred for one day, and water (200 mL) was added. The synthesized material was extracted with ether (100 mL × 3) to remove all solvent. The water was then completely removed using Dean-Stark solvent with benzene, and the solid was filtered to prepare compound 3-4' (6.2 g, 66% yield).

[0670] Step 3) Preparation of compounds 3-4

[0671]

[0672] Compound 3-4” (6.2 g, 5.42 mmol) and diphenyliodine chloride were added. (2.57 g, 8.13 mmol), water (50 mL), and acetone (10 mL) were introduced into a 25 mL round-bottom flask and stirred vigorously for 30 minutes. The organic solvent was extracted with dichloromethane (20 mL × 3) and the solvent was removed. The result was subjected to column chromatography with dichloromethane:acetone = 9:1 (v:v) to prepare compound 3-4 (5.0 g, 65% yield).

[0673] MS:[MH] - =1135 (Negative Mode)

[0674] MS:[M+H] + =281 (positive pattern)

[0675] Preparation Examples 1 to 4 illustrate methods for synthesizing ionic compounds containing anionic groups of Formula 2, and ionic compounds can be synthesized by adjusting the type, bonding position and number of substituents.

[0676] <Example of preparation of copolymers of chemical formula 3>

[0677] Preparation Example 1. Copolymer Type 5 (a1:b1:e1 = 58:12:30)

[0678] Step 1) Preparation of intermediate A

[0679]

[0680] 1,4-Dibromobenzene (55.84 g, 236.71 mmol) and anhydrous THF (400 mL) were added to a dried 1 L three-necked round-bottom flask under nitrogen atmosphere. After all starting materials dissolved, the solution was cooled to -67 °C (internal temperature). Slight dibromobenzene precipitation was observed. After cooling, n-butyllithium (15.16 g, 236.71 mmol) was added to the solution via a sleeve. The solution was stirred at -67 °C for 15 minutes, and careful observation was required during stirring due to lithium salt precipitation. 1,6-Diiodohexane (40.00 g, 118.35 mmol) was added, and the bath was slowly heated to room temperature to produce a clear solution. The solution was stirred at room temperature for 16 hours. The solution was slowly quenched with 1 N HCl (200 mL). Slight heat generation was observed. The layers were separated, and the organic layer was dried with NaSO4 and concentrated by rotary evaporation. The water bath temperature was increased to 55 °C to distill off low molecular weight impurities. The remaining product (crude) was purified using rapid chromatography (silica, 100% hexane isocratic). A second purification was performed using rapid chromatography (C18, 10% H2O: 90% ACN isocratic). ACN was removed to precipitate the product, which was then collected by filtration. Intermediate A was given as a white solid in 19% yield (8.871 g).

[0681] Step 2) Preparation of intermediate XL1

[0682]

[0683] Compound A (8.871 g, 22.39 mmol), benzocyclobutene-4-boronic acid (3.313 g, 22.39 mmol), sodium carbonate (7.12 g, 67.17 mmol), and 1:1 m-xylene:water (80 mL) were added to a dried 500 mL 3-necked flask under nitrogen. The solution was degassed. Tetra(triphenylphosphine)Pd(0) (7.12 g, 67.17 mmol) was added to the solution. The resulting mixture was heated to 100 °C for 4 hours. Toluene (100 mL) and water (50 mL) were added to the reaction mixture. The layers were separated, and the organic layer was dried with NaSO4 and filtered through diatomaceous earth, Florisil, and silica gel. The crude material was concentrated to obtain a yellow oil. The yellow oil was purified by rapid chromatography (silica, hexane:DCM 0% to 10%). The pure fraction was concentrated to obtain a white solid. The resulting material was dissolved in acetonitrile (400 mL). Add water (50 mL). Remove ACN by rotary evaporation to precipitate the product, filter it and collect it as a white solid (2.854 g, 30% yield).

[0684] Step 3) Preparation of monomer M1

[0685]

[0686] The synthesis of M1 and other monomers is described in International Patent Publication No. WO 2011 / 159872.

[0687] The synthesis can be carried out according to the following scheme.

[0688]

[0689]

[0690] Step 4) Preparation of copolymer type 5 (a1:b1:e1 = 58:12:30)

[0691]

[0692] Compounds M1 (0.765 mmol), M2 (0.158 mmol), and XL1 (0.396 mmol) were added to a scintillation flask and dissolved in toluene (11 mL). Bis(1,5-cyclooctadiene)nickel (0) (2.42 mmol) was loaded into a clean, dry 50 mL Schlenk tube. 2,2'-Bipyridine (2.42 mmol) and 1,5-cyclooctadiene (2.42 mmol) were weighed and introduced into a scintillation flask and dissolved in N,N'-dimethylformamide (5.5 mL) and toluene (11 mL). The solution was added to the Schlenk tube, which was then inserted into an aluminum block and heated to an internal temperature of 50 °C. The catalytic system was maintained at 50 °C for 30 minutes. The monomer solution in toluene was added to the Schlenk tube, and the tube was sealed.

[0693] The polymerization mixture was stirred at 50°C for 180 minutes. The Schlenk tube was then removed from the block and allowed to cool to room temperature. The contents were poured into HCl / methanol (5% v / v, concentrated HCl). After stirring for 45 minutes, the polymer was collected by vacuum filtration and dried under high vacuum. The polymer was dissolved in toluene (1% w / v) and passed through a column containing basic alumina (6 g) layered on silica gel (6 g). The polymer / toluene filtrate was concentrated (2.5% w / v toluene) and milled with 3-pentanone. The toluene / 3-pentanone solution was gradient-separated from the semi-solid polymer, then dissolved in toluene (15 mL) and poured into stirred methanol to obtain copolymer type 5 (a1:b1:e1 = 58:12:30) (Mw: 32,000) in 60% yield.

[0694] Using the method described above for preparing copolymer type 5 (a1:b1:e1 = 58:12:30), other copolymer types can be prepared in a similar manner.

[0695] The copolymers were characterized by gel permeation chromatography (“GPC”) using a multi-angle light scattering detector and an online viscometer, and by using THF as a solvent.

[0696] Preparation Example 2. Copolymer Type 17 (a1:b1:e1 = 47:21:32)

[0697] Copolymer type 17 was prepared via Suzuki coupling as shown in the following scheme. In the Suzuki method, after the monomers of unit A and unit B' are converted into polymers, the end-capping monomers are finally filled. This is done to consume all remaining residual functional groups on the polymer.

[0698]

[0699]

[0700] Under inert gas conditions, compound M1 (0.207 mmol), compound B30 (0.092 mmol), Aliquat 336 (0.041 mmol), potassium carbonate aqueous solution (0.5 M, 1.24 mL), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.1 mmol), and toluene (total 6.0 mL) were added to a scintillation flask equipped with a magnetic stir bar. The flask was sealed with a diaphragm-sealed cap, inserted into an aluminum block, and heated to an external temperature of 105 °C for 30 minutes, and stirred at this temperature under gentle reflux for 5 hours. Then, bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.05 μmol), pinacol phenylborate E30 (0.138 mmol), and toluene (0.9 mL) were introduced into the reaction mixture. The reaction mixture was then heated at the above temperature for 1.5 hours. Then, iodobenzene (0.092 mmol) and toluene (0.6 mL) were added. The reaction mixture was heated further for 1.5 hours, then cooled to room temperature. The aqueous layer was removed, and the organic layer was washed twice with deionized water (20 mL each time). The toluene layer was dried by passing it through silica gel (10 g) as a drying agent, and the silica was rinsed with toluene. The solvent was removed to obtain the product (250 mg). The toluene solution was then passed through alumina, silica gel, and... The crude product was further purified. After concentration, the solvent-soaked product was diluted with toluene (approximately 14 mL) and then added to ethyl acetate (150 mL) to obtain the polymer (approximately 200 mg). The toluene solution of the product was then reprecipitated in 3-pentanone to obtain the final copolymer type 17 (a1:b1:e1 = 47:21:32) (145 mg) (Mw: 232, 350).

[0701] Preparation Example 3. Copolymer Type 9 (a1:b1:e1 = 42:17:41)

[0702] Copolymer type 9 was prepared by Suzuki coupling as shown in the following scheme.

[0703] Step 1) Preparation of monomer M3

[0704]

[0705] A 1L jacketed reactor equipped with a top-mounted mechanical stirrer and a reflux condenser was loaded with compound M1 (27.81 g, 21.3 mmol), bis(pinacol)diboron (16.2 g, 63.8 mmol), potassium acetate (8.35 g, 85.1 mmol), and 1,4-dioxanone. Alkane (280 mL) was added and inertized. Then, under an inert atmosphere, the reactor was loaded with a complex of [1,1'-bis(diphenyl-phosphino)ferrocene]dichloropalladium(II) (0.70 g) and dichloromethane, and the reaction mixture was heated to an external temperature of approximately 97 °C for 1 hour. After heating for 10 hours, the reaction was considered complete, and the result was cooled to 25 °C. The reaction mixture was passed through a diatomaceous earth layer and then washed with a mixture of dichloromethane / hexane (1:1 v / v) (250 mL). The solvent was removed, and the residue was diluted with dichloromethane / hexane (1:1 v / v) (50 mL), with the addition of dichloromethane to facilitate loading the crude mixture onto a column containing silica gel (150 g) pre-embedded with boric acid. The collected product fractions were combined and purified by repeated column purification using silica gel (300 g) pre-embedded with boric acid. After solvent removal, a bright monomer (19.1 g) was obtained. Further purification was performed using dichloromethane / hexane, passing the monomer through a column packed with Florisil (190 g). Finally, the monomer was dissolved in toluene / hexane and precipitated in methanol to separate solid monomer M3 (15.4 g) in 52% yield.

[0706] Step 2) Preparation of copolymer type 9 (a1:b1:e1 = 42:17:41)

[0707] The synthesis was carried out in a similar manner to that in Preparation Example 2 (Mw: 461,000). In the devices of the following examples, the copolymers described in Table 1 below were used.

[0708] [Table 1]

[0709]

[0710] <Experimental Example>

[0711] Example 1

[0712] A thickness of [thickness] was deposited on it. The ITO glass substrate used as the thin film was ultrasonically cleaned with acetone for 10 minutes. Afterward, the substrate was immersed in distilled water containing a cleaning agent, and ultrasonically cleaned for 10 minutes, followed by two more 10-minute ultrasonic cleaning sessions with distilled water. Following the distilled water cleaning, the substrate was ultrasonically cleaned with isopropanol for 10 minutes and then dried. The substrate was then transferred to a glove box.

[0713] On the transparent ITO electrode prepared above, a 2 wt% cyclohexanone solution containing compounds 1 and 3-1 prepared above in a weight ratio of 8:2 is spin-coated, and the electrode is heat-treated at 230°C for 30 minutes to form a hole injection layer with a thickness of 60 nm. On the hole injection layer, a 0.8 wt% toluene solution containing the copolymer HTL1-1 prepared above is spin-coated, and the electrode is heat-treated at 230°C for 25 minutes to form a hole transport layer with a thickness of 140 nm.

[0714] The resulting material was transferred to a vacuum deposition apparatus, and compounds A and B were vacuum deposited on the hole transport layer at a weight ratio of 9:1 to form a 30 nm thick emitting layer. Compound C was then vacuum deposited on the emitting layer to form a 40 nm thick electron injection and transport layer. LiF with a thickness of 0.5 nm and aluminum with a thickness of 100 nm were sequentially deposited on the electron injection and transport layer to form a cathode.

[0715]

[0716] In the above process, the deposition rate of organic materials is maintained at to The deposition rates of LiF and aluminum at the cathode were maintained at... and And the vacuum level during deposition was maintained at 2×10⁻⁶. -8 Up to 5×10 -6 Entrust.

[0717] Examples 2 to 21 and Comparative Examples 1 to 4.

[0718] The organic light-emitting device was manufactured in the same manner as in Example 1, except that the following method was used.

[0719] The materials described in Table 2 replace compound 1, compound 3-1 and copolymer HTL1-1.

[0720]

[0721]

[0722]

[0723] [Table 2]

[0724]

[0725] For the organic light-emitting devices manufactured in Examples 1 to 21, at 10 mA / cm 2 The values ​​of drive voltage, current efficiency, and power efficiency were measured at a given current density. The results are shown in Table 3 below.

[0726] [Table 3]

[0727] Experimental Example Drive voltage (V) Current efficiency (cd / A) Power efficiency (1m / W) Example 1 4.23 4.46 3.31 Example 2 4.38 4.31 3.09 Example 3 4.24 4.34 3.21 Example 4 4.19 4.19 3.14 Example 5 4.11 4.23 3.20 Example 6 4.14 4.25 3.22 Example 7 4.38 4.31 3.09 Example 8 4.25 4.22 3.12 Example 9 4.22 4.25 3.16 Example 10 4.17 4.28 3.22 Example 11 4.20 4.23 3.16 Example 12 4.29 4.29 3.14 Example 13 4.24 4.46 3.30 Example 14 4.25 4.34 3.21 Example 15 4.19 4.22 3.16 Example 16 4.27 4.35 3.20 Example 17 4.13 4.29 3.26 Example 18 4.22 4.18 3.11 Example 19 4.24 4.25 3.15 Example 20 4.41 4.33 3.08 Example 21 4.37 4.31 3.10 Comparative Example 1 4.82 3.25 2.12 Comparative Example 2 6.82 1.72 0.79 Comparative Example 3 5.49 2.81 1.61 Comparative Example 4 5.87 3.14 1.68

[0728] Based on the experimental results in Table 3, it was determined that compared with Comparative Examples 1 to 3, which used materials different from those of the compound of Formula 1 or the copolymer of Formula 3 of this application, the organic light-emitting devices of this disclosure 1 to 21 have superior driving voltage and efficiency.

[0729] Specifically, Comparative Example 1 uses a compound in which R1 and R3 of Formula 1 of this application are hydrogen (Comparative Compound 1), and Comparative Example 2 uses a monomer compound (a-NPD) that is different from the copolymer of Formula 3 of this application. Comparative Example 3 uses a compound in which naphthyl groups are bonded instead of fluorene in Formula 1 of this application (Comparative Compound 2). Furthermore, Comparative Example 4 uses a compound in which L1 and L2 of Formula 1 of this application are replaced by hexane groups (Comparative Compound 3).

[0730] As an example, when comparing Example 10 of this application with Comparative Example 4, Example 10 of this application uses a compound according to Formula 1, specifically compound 2, instead of comparative compound 3 used in Comparative Example 4, and all other materials are the same. Compound 2 and comparative compound 3 have different structures depending on whether L1 and L2 are bonds, and it is determined that in Example 10 of this application, which uses compound 2 in which L1 and L2 are bonds, the organic light-emitting device has a low driving voltage and high efficiency compared to Comparative Example 4, which uses comparative compound 3 having a structure in which L1 and L2 are hexanediol groups instead of bonds.

Claims

1. An organic light-emitting device, comprising: anode; cathode; A light-emitting layer disposed between the anode and the cathode; A first organic material layer disposed between the light-emitting layer and the anode, the first organic material layer comprising a composition or cured material thereof containing a compound of formula 1, wherein the first organic material layer further comprises an ionic compound containing an anionic group of formula 2; and A second organic material layer is disposed between the first organic material layer and the light-emitting layer, the second organic material layer comprising a copolymer of the following chemical formula 3 or a cured material thereof: [Chemical Formula 1] In chemical formula 1, L represents C, whether substituted or unsubstituted. 6-60 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S. 2-60 heteroaryl; R1 and R3 may be the same as or different from each other, and each is an independent halogen group; R2 and R4 may be the same as or different from each other, and each is independently hydrogen; deuterium; or C. 1-10 alkyl; L1 and L2 may be the same as or different from each other, and each is an independent direct bond; or a methylene group; X1 and X2 may be the same as or different from each other, and each is independently a curing group selected from the following structures; In the structure, L11 represents a direct bond; -O-; -S-; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group. k is 1 or 2, When k is 2, L11 are either the same or different from each other, and R21 is a substituted or unsubstituted alkyl group. R'1, R'2, R'3, R”1, R”2, and R”3 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted C. 1-60 Alkyl; substituted or unsubstituted C 1-60 Alkoxy; substituted or unsubstituted C 6-60 aryl; or C containing one or more heteroatoms selected from N, O and S. 2-60 Mixed aromatics; n and n' are each integers from 1 to 5, m and m' are 0 or 1, n+m is 5 or less, and n'+m' is 5 or less; n1 and m1 are integers from 0 to 5, n2 and m2 are integers from 0 to 4, and n3 and m3 are integers from 0 to 3; and When n, n', n1 to n3 and m1 to m3 are each 2 or greater, the substituents in two or more parentheses are either the same or different from each other. [Chemical Formula 2] In chemical formula 2, At least one of R101 to R120 is a curing group. At least one of the remaining groups in R101 to R120 that are not curing groups is F; cyano; or a substituted or unsubstituted fluoroalkyl group. The remaining groups in R101 to R120 that are not curing groups, F, cyano, or substituted or unsubstituted fluoroalkyl groups are the same as or different from each other, and are each independently hydrogen; deuterium; nitro; -C(O)R 201 ;-OR 202 ;-SR 203 ;-SO3R 204 ;-COOR 205 ;-OC(O)R 206 ;-C(O)NR 207 R 208 ; substituted or unsubstituted alkyl groups; substituted or unsubstituted alkenyl groups; substituted or unsubstituted amino groups; substituted or unsubstituted aryl groups; or substituted or unsubstituted heterocyclic groups, and R 201 To R 208 They may be the same as or different from each other, and each is independently hydrogen, deuterium, or substituted or unsubstituted alkyl groups. [Chemical Formula 3] In chemical formula 3, A is a monomer unit containing at least one triarylamine group; B' is a monomer unit having at least three bonding sites in the copolymer; C' is an aromatic monomer unit or its deuterated analogue; E may be the same as or different from each other, and each is independently selected from hydrogen; deuterium; halogen groups; substituted or unsubstituted alkyl groups; substituted or unsubstituted silyl groups; substituted or unsubstituted germanyl groups; substituted or unsubstituted aryl groups; substituted or unsubstituted arylamino groups; substituted or unsubstituted siloxane groups; and substituted or unsubstituted curing groups; and a, b, and c are mole fractions, a + b + c = 1, a ≠ 0, and b ≠ 0.

2. The organic light-emitting device according to claim 1, wherein at least one of the compound of formula 1 and the copolymer of formula 3 is 10% to 100% deuterated.

3. The organic light-emitting device according to claim 1, wherein the copolymer of chemical formula 3 is 5% to 100% deuterated.

4. The organic light-emitting device according to claim 1, wherein L is any of the following structures: 。 5. The organic light-emitting device according to claim 1, wherein the monomer unit A is represented by any one of the following chemical formulas A-1 to A-5: [Chemical Formula A-1] [Chemical Formula A-2] [Chemical Formula A-3] [Chemical Formula A-4] [Chemical Formula A-5] In chemical formulas A-1 to A-5, Ar1 may be the same as or different from each other, and each is independently a substituted or unsubstituted arylene or a deuterated arylene; Ar2 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl or deuterated aryl; Ar3 is a substituted or unsubstituted arylene or a deuterated arylene; Ar4 may be the same as or different from each other, and each is independently selected from substituted or unsubstituted phenylene; substituted or unsubstituted naphthylene; and their deuterated analogs; Ar5, Ar6, and Ar7 may be the same as or different from each other, and each is independently a substituted or unsubstituted arylene or a deuterated arylene; T1 and T2 may be the same or different from each other, and each is independently a conjugate part or its deuterated analogue connected by a non-planar structure; T is selected from substituted or unsubstituted arylene groups; and deuterated arylene groups. T3 to T5 may be the same as or different from each other, and each is independently selected from hydrogen; F; cyano; alkyl; fluoroalkyl; aryl; heteroaryl; amino; silyl; germanyl; alkoxy; aryloxy; fluoroalkoxy; siloxane; siloxy; deuterated alkyl; deuterated partially fluorinated alkyl; deuterated aryl; deuterated heteroaryl; deuterated amino; deuterated silyl; deuterated germanyl; deuterated alkoxy; deuterated aryloxy; deuterated fluoroalkoxy; deuterated siloxane; deuterated siloxy; and fixed groups, and herein, adjacent groups selected from T3, T4 and T5 are bonded to each other to form a ring; d represents an integer from 1 to 6; e are integers from 1 to 6; k3 is an integer from 0 to 4, k4 and k5 are each integers from 0 to 3, and q is an integer of 0 or greater; and * indicates a bonding point in the copolymer.

6. The organic light-emitting device according to claim 1, wherein the monomer unit B' is represented by any one of the following chemical formulas B'-1 to B'-9: [Chemical formula B'-1] [Chemical formula B'-2] [Chemical formula B'-3] [Chemical formula B'-4] [Chemical formula B'-5] [Chemical formula B'-6] [Chemical formula B'-7] [Chemical formula B'-8] [Chemical formula B'-9] In chemical formulas B'-1 to B'-9, Ar8 is an aromatic cyclic group or a deuterated aromatic cyclic group having at least three bonding sites; T31 to T61 may be the same as or different from each other, and each is independently selected from deuterium; F; cyano; alkyl; fluoroalkyl; aryl; heteroaryl; amino; silyl; germanyl; alkoxy; aryloxy; fluoroalkoxy; siloxane; siloxy; deuterated alkyl; deuterated partially fluorinated alkyl; deuterated aryl; deuterated heteroaryl; deuterated amino; deuterated silyl; deuterated germanyl; deuterated alkoxy; deuterated aryloxy; deuterated fluoroalkoxy; deuterated siloxane; deuterated siloxy; and fixed groups, and herein, adjacent groups selected from T31 to T61 are bonded to each other to form a 5- or 6-membered aromatic ring; k6 to k19, k21 to k25, and k27 to k35 are each integers from 0 to 4; k20 and k26 are integers from 0 to 5; and k36 is an integer from 0 to 3; and * indicates a bonding point in the copolymer.

7. The organic light-emitting device according to claim 1, wherein the copolymer of chemical formula 3 is represented by the following chemical formula 3': [Chemical Formula 3'] In chemical formula 3', A is a monomer unit containing at least one triarylamine group; B' is a monomer unit having at least three bonding sites in the copolymer; C' is an aromatic monomer unit or its deuterated analogue; E' may be the same as or different from each other, and each is independently selected from hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; substituted or unsubstituted arylamino; substituted or unsubstituted siloxane; and substituted or unsubstituted curing group; a1, b1, c1, and e1 are mole fractions, a1 + b1 + c1 + e1 = 1, a1 ≠ 0, and b1 ≠ 0; z1 is an integer of 3 or greater; and * indicates a connection point in the copolymer.

8. The organic light-emitting device according to claim 1, wherein the copolymer of formula 3 has a weight-average molecular weight of 10,000 g / mol to 5,000,000 g / mol.

9. The organic light-emitting device according to claim 1, wherein the first organic material layer is a hole injection layer and the second organic material layer is a hole transport layer.

10. The organic light-emitting device according to claim 1, wherein the first organic material layer is configured to contact the anode, and the second organic material layer is configured to contact the first organic material layer.

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