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

Abstract

This specification relates to a compound of Chemical Formula 1, a coating composition containing the same, an organic light-emitting device containing the same, and a method for manufacturing the same.

Description

Technical Field

[0001] This application claims the benefit of the filing date of Korean Patent Application No. 10-2022-0059693, filed with the Korean Intellectual Property Office on May 16, 2022, and all of its content is incorporated herein by reference.

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

Background Art

[0003] The organic light-emitting phenomenon is an example in which an electric current is switched to visible light by an internal process of a specific organic molecule. The principle of the organic light-emitting phenomenon is as follows. When an organic layer is disposed between an anode and a cathode and a current is passed between both electrodes, electrons and holes are injected into the organic layer from the cathode and the anode, respectively. The electrons and holes injected into the organic layer recombine to form an exciton, and this exciton falls back to the ground state again to emit light. An organic light-emitting device utilizing such a principle can generally be composed of a cathode, an anode, and an organic layer located therebetween, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer, and an electron transport layer.

[0004] Conventionally, an evaporation process has been mainly used to manufacture an organic light-emitting device. However, when manufacturing an organic light-emitting device by an evaporation process, there are problems such as a large amount of material loss and difficulty in manufacturing a large-area device. To solve this problem, devices using a solution process are being developed. Therefore, the development of materials for the solution process is required.

Summary of the Invention

Problems to be Solved by the Invention

[0005] The present invention provides a compound, a coating composition containing the same, an organic light-emitting device containing the same, and a method for manufacturing the same.

Means for Solving the Problems

[0006] One embodiment of the present invention provides a compound of the following Chemical Formula 1.

Chemical formula

Chemical formula

[0007] Another embodiment of the present invention provides a coating composition containing the aforementioned compound.

[0008] Another embodiment of the present invention provides an organic light-emitting device including a first electrode, a second electrode, and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers contains the aforementioned coating composition or a cured product thereof.

[0009] Another embodiment of the present invention provides a method for manufacturing an organic light-emitting device, including the steps of preparing a first electrode, forming at least one organic layer on the first electrode, and forming a second electrode on the organic layer, wherein the step of forming the organic layer includes forming at least one organic layer using the aforementioned coating composition.

[0010] Another embodiment of the present invention provides a method for manufacturing an organic light-emitting device, including the steps of preparing a first electrode, forming at least one organic layer on the first electrode, and forming a second electrode on the organic layer, wherein the step of forming the organic layer includes forming at least one organic layer by vapor-depositing the aforementioned compound.

Advantages of the Invention

[0011] Due to the excellent solubility of the compound according to one embodiment of the present invention, there is an advantage that various solvents can be selected during the manufacture of the coating composition.

[0012] In addition, the compound according to one embodiment of the present invention can be used as a material for the organic layer of an organic light-emitting device, and when applied to an organic light-emitting device, an element having a low driving voltage, excellent efficiency characteristics, and / or excellent lifetime characteristics can be obtained.

[0013] Furthermore, the compound according to one embodiment of the present invention enables a solution process, thereby enabling the enlargement of the area of the element.

Brief Description of the Drawings

[0014]

Figure 1

BEST MODE FOR CARRYING OUT THE INVENTION

[0015] Hereinafter, the present invention will be described in detail. One embodiment of the present invention provides a compound of the following Chemical Formula 1.

Chem.

Chem.

[0016] In one embodiment of the present invention, at least one of X1 to X4 and X11 to X14 contains deuterium. That is, the compound of Chemical Formula 1 contains at least one deuterium.

[0017] When a compound contains deuterium, since the bond energy of a C-D bond is greater than that of a C-H bond, it will have a strong intramolecular bond energy, thereby enabling the substance stability to be increased. Therefore, when the compound of Chemical Formula 1 is applied to an organic light-emitting device, it has the effect of improving the efficiency and lifespan.

[0018] In this specification, when a member is located "on" another member, this includes not only the case where a member is in contact with another member, but also the case where there is another member between the two members.

[0019] In this specification, when a certain part "includes" a certain component, this means that, unless otherwise stated to the contrary, it does not exclude other components, but may further include other components.

[0020] In this specification, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent, and the position to be substituted is not limited as long as it is the position where a hydrogen atom is substituted, that is, the position where a substituent can be substituted. When two or more substitutions occur, the two or more substituents may be the same or different from each other.

[0021] As used herein, the term "substituted or unsubstituted" means being substituted with one or more substituents selected from the group consisting of deuterium; halogen groups; alkyl groups; cycloalkyl groups; alkoxy groups; aryloxy groups; amine groups; aryl groups; and heteroaryl groups, being substituted with a substituent in which two or more of the exemplified substituents are linked, or having no substituents. For example, the "substituent in which two or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group and may also be interpreted as a substituent in which two phenyl groups are linked.

[0022] As used herein, [Chemical formula] and * means a site for bonding to another substituent or a bonding site.

[0023] Examples of the substituents are described below, but are not limited thereto.

[0024] As used herein, examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

[0025] As used herein, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. Specific examples of the alkyl group include, but are not limited to, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, etc.

[0026] As used herein, the alkylene group means a group having two bonding positions to an alkyl group, that is, a divalent group. The descriptions of the aforementioned alkyl groups can be applied to these, except that they are each divalent groups.

[0027] In this specification, the number of carbon atoms of the cycloalkyl group is not particularly limited, but is preferably 3 to 60. According to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. Specific examples of the cycloalkyl group include, but are not limited to, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, etc.

[0028] In this specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30. Specific examples of the alkoxy group include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc.

[0029] In this specification, the amine group is a group represented by -NRaRb, where Ra and Rb are the same as or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group. Specifically, the amine group is -NH 2 ; an alkylamine group; an arylalkylamine group; an arylamine group; an arylheteroarylamine group; an alkylheteroarylamine group and a heteroarylamine group, and can be selected from the group consisting of, but not limited to, these. The number of carbon atoms of the amine group is not particularly limited, but is preferably 1 to 60.

[0030] In this specification, the aryl group is not particularly limited and may have 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. Examples of the monocyclic aryl group include, but are not limited to, phenyl group, biphenyl group, terphenyl group, etc. Examples of the polycyclic aryl group include, but are not limited to, naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, ferrenyl group, triphenylenyl group, chrysenyl group, fluorenyl group, etc.

[0031] In this specification, the fluorenyl group may be substituted, or two substituents may be bonded to each other to form a spiro structure.

[0032] When the fluorenyl group is substituted, [Chemical formula] etc. are included, and the exemplified structures may be substituted with additional substituents. However, the structure is not limited thereto.

[0033] In this specification, the arylene group means a group having two bonding positions on the aryl group, that is, a divalent group. The descriptions of the above-mentioned aryl groups can be applied to these, except that they are each divalent groups.

[0034] In this specification, the heteroaryl group is a heteroaryl group containing at least one of N, O, P, S, Si, and Se, which are heteroatoms, and the number of carbon atoms is not particularly limited, but may be 2 to 60. According to the above-mentioned embodiment, the number of carbon atoms of the heteroaryl group is 2 to 30. According to another embodiment, the number of carbon atoms of the heteroaryl group is 2 to 20. Examples of the heteroaryl group include, but are not limited to, a pyridyl group, a pyrrole group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophene group, a benzothiophene group, a benzofuran group, a dibenzothiophene group, a dibenzofuran group, and the like.

[0035] In this specification, the heteroarylene group means a group having two bonding positions to the heteroaryl group, that is, a divalent group. The above description of the heteroaryl group can be applied to these, except that they are each divalent groups.

[0036] In this specification, the statement that X# (#: an integer from 1 to 4) contains deuterium means that X# is Chemical Formula 2, and at least one of R1, R2, and L1 in Chemical Formula 2 contains deuterium.

[0037] Hereinafter, the compound of Chemical Formula 1 will be described in detail.

[0038] In one embodiment of the present invention, a11 is an integer from 1 to 4. In one embodiment of the present invention, a12 is an integer from 1 to 4. In one embodiment of the present invention, a13 is an integer from 1 to 4. In one embodiment of the present invention, a14 is an integer from 1 to 4.

[0039] In one embodiment of the present invention, a1 + a11 is an integer from 1 to 4. In one embodiment of the present invention, a2 + a12 is an integer from 1 to 4. In one embodiment of the present invention, a3 + a13 is an integer from 1 to 4. In one embodiment of the present invention, a4 + a14 is an integer from 1 to 4.

[0040] In one embodiment of the present invention, a1 to a4 are each an integer of 0 or 1, and a1 + a2 + a3 + a4 is an integer from 2 to 4. In one embodiment of the present invention, a1 to a4 are each an integer of 0 or 1, and a1 + a2 + a3 + a4 is 2.

[0041] In one embodiment of the present invention, a1 and a2 are 0, and a3 and a4 are 1.

[0042] In one embodiment of the present invention, a1 and a3 are 1, and a2 and a4 are 0.

[0043] In one embodiment of the present invention, Chemical Formula 1 is represented by the following Chemical Formula 1-1 or 1-2.

Chemical Formula

[0044] In Chemical Formulas 1-1 and 1-2, X1, X3, X4, X11 to X14, a11, a12 and a14 are the same as those defined in Chemical Formula 1, a11’, a13’, and a14’ are each an integer from 1 to 3. When a11’, a13’, and a14’ are each 2 or more, the substituents in parentheses are the same as or different from each other.

[0045] In one embodiment of the present invention, Chemical Formula 1 is represented by the following Chemical Formula 1-1-1 or 1-2-1.

Chemical Formula

[0046] In Chemical Formulas 1-1-1 and 1-2-1, X11 to X14, a11, a12 and a14 are the same as those defined in Chemical Formula 1 above, Y1 and Y2 are the same as or different from each other, and each independently is O, S or Se, L1 and L2 are the same as or different from each other, and each independently is a direct bond; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, R1 to R4 are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, a11’, a13’, and a14’ are each an integer from 1 to 3, and when a11’, a13’, and a14’ are each 2 or more, the substituents in parentheses are the same as or different from each other.

[0047] In one embodiment of the present invention, R1 to R4 are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group.

[0048] In one embodiment of the present invention, R1 to R4 are the same as or different from each other, and each independently is an aryl group substituted or unsubstituted with deuterium.

[0049] In one embodiment of the present invention, R1 to R4 are the same as or different from each other, and each independently is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted fluorenyl group; or a substituted or unsubstituted naphthyl group.

[0050] In one embodiment of the present invention, R1 to R4 are the same as or different from each other, and each independently is a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a phenanthrenyl group substituted or unsubstituted with deuterium; a fluorenyl group substituted or unsubstituted with deuterium; or a naphthyl group substituted or unsubstituted with deuterium.

[0051] In one embodiment of the present invention, X11 to X14 are the same as or different from each other, and each independently is hydrogen; deuterium; or a substituted or unsubstituted alkyl group, or combines with an adjacent group to form a substituted or unsubstituted ring.

[0052] In one embodiment of the present invention, X11 to X14 are the same as or different from each other, and each independently is hydrogen; deuterium; or a substituted or unsubstituted alkyl group with deuterium, or combines with an adjacent group to form a substituted or unsubstituted ring with deuterium.

[0053] In one embodiment of the present invention, when a12 is 2 or more, Chemical Formula 1 can be represented by the following Chemical Formula 1-a.

Chemical formula

[0054] In Chemical Formula 1-a, X1, X3, X4, X11, X13, X14, a1, a3, a4, a11, a13, and a14 are the same as those defined in Chemical Formula 1, X12a to X12d are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group, or a group (X2) represented by Chemical Formula 2, or combines with an adjacent group to form a substituted or unsubstituted ring.

[0055] In one embodiment of the present invention, a12 is 2 or more, and adjacent X12s are bonded to each other to form a substituted or unsubstituted ring. Specifically, X12a and X12b are bonded to form a substituted or unsubstituted ring, X12b and X12c are bonded to form a substituted or unsubstituted ring, and / or X12c and X12d are bonded to form a substituted or unsubstituted ring. In this case, they can be represented by the following Chemical Formulas 1-4 to 1-6, respectively.

[0056] In one embodiment of the present invention, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-4 to 1-6.

Chemical Formula

Chemical Formula

[0057] In Chemical Formulas 1-4 to 1-6, X1 to X4, X11, X13, X14, a1 to a4, a11, a13, and a14 are the same as those defined in Chemical Formula 1, X15 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, at least one of X1 to X4, X11, and X13 to X15 contains deuterium, a15 is an integer from 1 to 6, and when a15 is an integer of 2 or more, the structures in the parentheses are the same as or different from each other.

[0058] In one embodiment of the present invention, a15 + a2 is an integer of 6 or less. In one embodiment of the present invention, a15 + a2 is an integer from 1 to 6.

[0059] The exemplification for the case where a12 is 2 or more is similarly applicable when a11 is 2 or more, a13 is 2 or more, and a14 is 2 or more.

[0060] In one embodiment of the present invention, a1 to a4 in Chemical Formulas 1-4 to 1-6 are each an integer of 0 or 1, and a1 + a2 + a3 + a4 is an integer of 2 to 4. In one embodiment of the present invention, a1 to a4 in Chemical Formulas 1-4 to 1-6 are each an integer of 0 or 1, and a1 + a2 + a3 + a4 is 2.

[0061] In one embodiment of the present invention, a1 and a2 in Chemical Formulas 1-4 to 1-6 are 0, and a3 and a4 are 1.

[0062] In one embodiment of the present invention, a1 and a3 in Chemical Formulas 1-4 to 1-6 are 0, and a2 and a4 are 1.

[0063] In one embodiment of the present invention, a1 and a4 in Chemical Formulas 1-4 to 1-6 are 0, and a2 and a3 are 1.

[0064] In one embodiment of the present invention, a2 and a3 in Chemical Formulas 1-4 to 1-6 are 0, and a1 and a4 are 1.

[0065] In one embodiment of the present invention, a2 and a4 in Chemical Formulas 1-4 to 1-6 are 0, and a1 and a3 are 1.

[0066] In one embodiment of the present invention, a3 and a4 in Chemical Formulas 1-4 to 1-6 are 0, and a1 and a2 are 1.

[0067] In one embodiment of the present invention, X11, X13, X14, and X15 in Chemical Formulas 1-4 to 1-6 are the same as or different from each other, and each independently is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0068] In one embodiment of the present invention, X11, X13, X14, and X15 in Chemical Formulas 1-4 to 1-6 are the same as or different from each other, and each independently is hydrogen; deuterium; or a substituted or unsubstituted alkyl group substituted with deuterium.

[0069] In this specification, the * in Chemical Formula 2 is the site bonded to Chemical Formula 1.

[0070] In one embodiment of the present invention, R1 and R2 are the same as or different from each other, and each independently is hydrogen; deuterium; or a substituted or unsubstituted aryl group.

[0071] In one embodiment of the present invention, R1 and R2 are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group.

[0072] In one embodiment of the present invention, R1 and R2 are the same as or different from each other, and each independently is an aryl group substituted or unsubstituted with deuterium.

[0073] In one embodiment of the present invention, R1 and R2 are the same as or different from each other, and each independently is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted fluorenyl group; or a substituted or unsubstituted naphthyl group.

[0074] In one embodiment of the present invention, R1 and R2 are the same as or different from each other, and each independently is a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a phenanthrenyl group substituted or unsubstituted with deuterium; a fluorenyl group substituted or unsubstituted with deuterium; or a naphthyl group substituted or unsubstituted with deuterium.

[0075] In one embodiment of the present invention, L1 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0076] In one embodiment of the present invention, L1 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and substituted or unsubstituted with deuterium.

[0077] In one embodiment of the present invention, the L1 is a direct bond; or a substituted or unsubstituted phenylene group.

[0078] In one embodiment of the present invention, the L1 is a direct bond; or a phenylene group substituted or unsubstituted with deuterium.

[0079] In one embodiment of the present invention, the Y1 is O. In one embodiment of the present invention, the Y1 is S. In one embodiment of the present invention, the Y1 is Se.

[0080] In one embodiment of the present invention, 1 to 8 of X1 to X4 and X11 to X14 contain deuterium.

[0081] In one embodiment of the present invention, the X1 contains deuterium.

[0082] In one embodiment of the present invention, at least one of R1 and R2 of the X1 contains deuterium.

[0083] In one embodiment of the present invention, at least one of R1 and R2 of the X1 is deuterium; an alkyl group substituted with deuterium; a cycloalkyl group substituted with deuterium; an aryl group substituted with deuterium; or a heteroaryl group substituted with deuterium.

[0084] In one embodiment of the present invention, R1 and R2 of the X1 contain deuterium.

[0085] In one embodiment of the present invention, R1 and R2 of the X1 are the same as or different from each other, and each independently is deuterium; an alkyl group substituted with deuterium; a cycloalkyl group substituted with deuterium; an aryl group substituted with deuterium; or a heteroaryl group substituted with deuterium.

[0086] In one embodiment of the present invention, R1 and R2 of X1 are the same as or different from each other, and each independently is an aryl group substituted with deuterium.

[0087] In one embodiment of the present invention, L1 of X1 contains deuterium.

[0088] In one embodiment of the present invention, X2 contains deuterium.

[0089] In one embodiment of the present invention, at least one of R1 and R2 of X2 contains deuterium.

[0090] In one embodiment of the present invention, at least one of R1 and R2 of X2 is deuterium; an alkyl group substituted with deuterium; a cycloalkyl group substituted with deuterium; an aryl group substituted with deuterium; or a heteroaryl group substituted with deuterium.

[0091] In one embodiment of the present invention, R1 and R2 of X2 contain deuterium.

[0092] In one embodiment of the present invention, R1 and R2 of X2 are the same as or different from each other, and each independently is deuterium; an alkyl group substituted with deuterium; a cycloalkyl group substituted with deuterium; an aryl group substituted with deuterium; or a heteroaryl group substituted with deuterium.

[0093] In one embodiment of the present invention, R1 and R2 of X2 are the same as or different from each other, and each independently is an aryl group substituted with deuterium.

[0094] In one embodiment of the present invention, L1 of X2 contains deuterium.

[0095] In one embodiment of the present invention, X3 contains deuterium.

[0096] In one embodiment of the present invention, at least one of R1 and R2 of X3 contains deuterium.

[0097] In one embodiment of the present invention, at least one of R1 and R2 of X3 is deuterium; an alkyl group substituted with deuterium; a cycloalkyl group substituted with deuterium; an aryl group substituted with deuterium; or a heteroaryl group substituted with deuterium.

[0098] In one embodiment of the present invention, R1 and R2 of X3 contain deuterium.

[0099] In one embodiment of the present invention, R1 and R2 of X3 are the same as or different from each other, and each independently is deuterium; an alkyl group substituted with deuterium; a cycloalkyl group substituted with deuterium; an aryl group substituted with deuterium; or a heteroaryl group substituted with deuterium.

[0100] In one embodiment of the present invention, R1 and R2 of X3 are the same as or different from each other, and each independently is an aryl group substituted with deuterium.

[0101] In one embodiment of the present invention, L1 of X3 contains deuterium.

[0102] In one embodiment of the present invention, X4 contains deuterium.

[0103] In one embodiment of the present invention, at least one of R1 and R2 of X4 contains deuterium.

[0104] In one embodiment of the present invention, at least one of R1 and R2 of X4 is deuterium; an alkyl group substituted with deuterium; a cycloalkyl group substituted with deuterium; an aryl group substituted with deuterium; or a heteroaryl group substituted with deuterium.

[0105] In one embodiment of the present invention, R1 and R2 of X4 contain deuterium.

[0106] In one embodiment of the present invention, R1 and R2 of X4 are the same as or different from each other, and each independently is deuterium; an alkyl group substituted with deuterium; a cycloalkyl group substituted with deuterium; an aryl group substituted with deuterium; or a heteroaryl group substituted with deuterium.

[0107] In one embodiment of the present invention, R1 and R2 of X4 are the same as or different from each other, and each independently is an aryl group substituted with deuterium.

[0108] In one embodiment of the present invention, L1 of X4 contains deuterium.

[0109] In one embodiment of the present invention, X11 contains deuterium.

[0110] In one embodiment of the present specification, X11 is deuterium; an alkyl group substituted or unsubstituted with deuterium; a cycloalkyl group substituted or unsubstituted with deuterium; an aryl group substituted or unsubstituted with deuterium; or a heteroaryl group substituted or unsubstituted with deuterium, or combines with an adjacent group to form a ring substituted with deuterium.

[0111] In one embodiment of the present invention, X11 is deuterium; or an alkyl group substituted with deuterium, or combines with an adjacent group to form a ring substituted with deuterium.

[0112] In one embodiment of the present invention, X12 contains deuterium.

[0113] In one embodiment of the present invention, X12 is deuterium; an alkyl group substituted or unsubstituted with deuterium; a cycloalkyl group substituted or unsubstituted with deuterium; an aryl group substituted or unsubstituted with deuterium; or a heteroaryl group substituted or unsubstituted with deuterium, or combines with an adjacent group to form a ring substituted with deuterium.

[0114] In one embodiment of the present invention, X12 is deuterium; or an alkyl group substituted with deuterium, or combines with an adjacent group to form a ring substituted with deuterium.

[0115] In one embodiment of the present invention, X13 contains deuterium.

[0116] In one embodiment of the present invention, X13 is deuterium; an alkyl group substituted or unsubstituted with deuterium; a cycloalkyl group substituted or unsubstituted with deuterium; an aryl group substituted or unsubstituted with deuterium; or a heteroaryl group substituted or unsubstituted with deuterium, or combines with an adjacent group to form a ring substituted with deuterium.

[0117] In one embodiment of the present invention, X13 is deuterium; or an alkyl group substituted with deuterium.

[0118] In one embodiment of the present invention, X14 contains deuterium.

[0119] In one embodiment of the present invention, X14 is deuterium; an alkyl group substituted or unsubstituted with deuterium; a cycloalkyl group substituted or unsubstituted with deuterium; an aryl group substituted or unsubstituted with deuterium; or a heteroaryl group substituted or unsubstituted with deuterium, or combines with an adjacent group to form a ring substituted with deuterium.

[0120] In one embodiment of the present invention, X14 is deuterium; or an alkyl group substituted with deuterium.

[0121] In one embodiment of the present invention, X1 and X3 contain deuterium.

[0122] In one embodiment of the present invention, at least one of R1 and R2 of X1, and at least one of R1 and R2 of X3 contain deuterium.

[0123] In one embodiment of the present invention, at least one of R1 and R2 of X1 and at least one of R1 and R2 of X3 are deuterium; an alkyl group substituted with deuterium; a cycloalkyl group substituted with deuterium; an aryl group substituted with deuterium; or a heteroaryl group substituted with deuterium.

[0124] In one embodiment of the present invention, R1 of X1, R2 of X1, R1 of X3, and R2 of X3 each contain deuterium.

[0125] In one embodiment of the present invention, R1 of X1, R2 of X1, R1 of X3, and R2 of X3 are the same as or different from each other, and each independently is deuterium; an alkyl group substituted with deuterium; a cycloalkyl group substituted with deuterium; an aryl group substituted with deuterium; or a heteroaryl group substituted with deuterium.

[0126] In one embodiment of the present invention, R1 of X1, R2 of X1, R1 of X3, and R2 of X3 are the same as or different from each other, and each independently is an aryl group substituted with deuterium.

[0127] In one embodiment of the present invention, L1 of X1 and L1 of X3 contain deuterium.

[0128] In one embodiment of the present invention, X1 and X4 contain deuterium.

[0129] In one embodiment of the present invention, at least one of R1 and R2 of X1 and at least one of R1 and R2 of X4 contain deuterium.

[0130] In one embodiment of the present invention, at least one of R1 and R2 of X1 and at least one of R1 and R2 of X4 are deuterium; an alkyl group substituted with deuterium; a cycloalkyl group substituted with deuterium; an aryl group substituted with deuterium; or a heteroaryl group substituted with deuterium.

[0131] In one embodiment of the present invention, R1 of X1, R2 of X1, R1 of X4, and R2 of X4 each contain deuterium.

[0132] In one embodiment of the present invention, R1 of X1, R2 of X1, R1 of X4, and R2 of X4 are the same as or different from each other, and each independently is deuterium; an alkyl group substituted with deuterium; a cycloalkyl group substituted with deuterium; an aryl group substituted with deuterium; or a heteroaryl group substituted with deuterium.

[0133] In one embodiment of the present invention, R1 of X1, R2 of X1, R1 of X4, and R2 of X4 are the same as or different from each other, and each independently is an aryl group substituted with deuterium.

[0134] In one embodiment of the present invention, L1 of X1 and L1 of X4 contain deuterium.

[0135] In one embodiment of the present invention, X2 and X3 contain deuterium.

[0136] In one embodiment of the present invention, at least one of R1 and R2 of X2 and at least one of R1 and R2 of X3 contain deuterium.

[0137] In one embodiment of the present invention, at least one of R1 and R2 of X2 and at least one of R1 and R2 of X3 are deuterium; an alkyl group substituted with deuterium; a cycloalkyl group substituted with deuterium; an aryl group substituted with deuterium; or a heteroaryl group substituted with deuterium.

[0138] In one embodiment of the present invention, R1 of X2, R2 of X2, R1 of X3, and R2 of X3 each contain deuterium.

[0139] In one embodiment of the present invention, R1 of X2, R2 of X2, R1 of X3, and R2 of X3 are the same as or different from each other, and each independently is deuterium; an alkyl group substituted with deuterium; a cycloalkyl group substituted with deuterium; an aryl group substituted with deuterium; or a heteroaryl group substituted with deuterium.

[0140] In one embodiment of the present invention, R1 of X2, R2 of X2, R1 of X3, and R2 of X3 are the same as or different from each other, and each independently is an aryl group substituted with deuterium.

[0141] In one embodiment of the present invention, L1 of X2 and L1 of X3 contain deuterium.

[0142] In one embodiment of the present invention, X2 and X4 contain deuterium.

[0143] In one embodiment of the present invention, at least one of R1 and R2 of X2 and at least one of R1 and R2 of X4 contain deuterium.

[0144] In one embodiment of the present invention, at least one of R1 and R2 of X2 and at least one of R1 and R2 of X4 are deuterium; an alkyl group substituted with deuterium; a cycloalkyl group substituted with deuterium; an aryl group substituted with deuterium; or a heteroaryl group substituted with deuterium.

[0145] In one embodiment of the present invention, R1 of X2, R2 of X2, R1 of X4, and R2 of X4 each contain deuterium.

[0146] In one embodiment of the present invention, R1 of X2, R2 of X2, R1 of X4, and R2 of X4 are the same as or different from each other, and each independently is deuterium; an alkyl group substituted with deuterium; a cycloalkyl group substituted with deuterium; an aryl group substituted with deuterium; or a heteroaryl group substituted with deuterium.

[0147] In one embodiment of the present invention, R1 of X2, R2 of X2, R1 of X4, and R2 of X4 are the same as or different from each other, and each independently is an aryl group substituted with deuterium.

[0148] In one embodiment of the present invention, L1 of X2 and L1 of X4 contain deuterium.

[0149] In one embodiment of the present invention, X3 and X4 contain deuterium.

[0150] In one embodiment of the present invention, at least one of R1 and R2 of X3 and at least one of R1 and R2 of X4 contain deuterium.

[0151] In one embodiment of the present invention, at least one of R1 and R2 of X3 and at least one of R1 and R2 of X4 is deuterium; an alkyl group substituted with deuterium; a cycloalkyl group substituted with deuterium; an aryl group substituted with deuterium; or a heteroaryl group substituted with deuterium.

[0152] In one embodiment of the present invention, R1 of X3, R2 of X3, R1 of X4, and R2 of X4 each contain deuterium.

[0153] In one embodiment of the present invention, R1 of X3, R2 of X3, R1 of X4, and R2 of X4 are the same as or different from each other, and each independently is deuterium; an alkyl group substituted with deuterium; a cycloalkyl group substituted with deuterium; an aryl group substituted with deuterium; or a heteroaryl group substituted with deuterium.

[0154] In one embodiment of the present invention, R1 of X3, R2 of X3, R1 of X4, and R2 of X4 are the same as or different from each other, and each independently is an aryl group substituted with deuterium.

[0155] In one embodiment of the present invention, L1 of X3 and L1 of X4 contain deuterium.

[0156] In one embodiment of the present invention, two of X1 to X4 contain deuterium, and X11 to X14 do not contain deuterium.

[0157] In one embodiment of the present invention, two of X1 to X4 are groups represented by Chemical Formula 2, R1 and R2 in Chemical Formula 2 are aryl groups substituted with deuterium, and X11 to X14 are the same as or different from each other and are each independently hydrogen; a halogen group; an alkyl group substituted or unsubstituted with a substituent other than deuterium; a cycloalkyl group substituted or unsubstituted with a substituent other than deuterium; an aryl group substituted or unsubstituted with a substituent other than deuterium; or a heteroaryl group substituted or unsubstituted with a substituent other than deuterium, or combine with adjacent groups to form a ring substituted or unsubstituted with a substituent other than deuterium.

[0158] In one embodiment of the present invention, two of X1 to X4 are groups represented by Chemical Formula 2, R1 and R2 in Chemical Formula 2 are aryl groups substituted with deuterium, and X11 to X14 are the same as or different from each other and are each independently hydrogen; a halogen group; an alkyl group; a cycloalkyl group; an aryl group; or a heteroaryl group, or combine with adjacent groups to form a ring.

[0159] In one embodiment of the present invention, X11 and X12 contain deuterium.

[0160] In one embodiment of the present invention, X11 and X12 are the same as or different from each other and are each independently deuterium; an alkyl group substituted or unsubstituted with deuterium; a cycloalkyl group substituted or unsubstituted with deuterium; an aryl group substituted or unsubstituted with deuterium; or a heteroaryl group substituted or unsubstituted with deuterium, or combine with adjacent groups to form a ring substituted with deuterium.

[0161] In one embodiment of the present invention, X11 and X12 are the same as or different from each other, and each independently is deuterium; or an alkyl group substituted with deuterium, or combines with an adjacent group to form a ring substituted with deuterium.

[0162] In one embodiment of the present invention, X11 and X13 contain deuterium.

[0163] In one embodiment of the present invention, X11 and X13 are the same as or different from each other, and each independently is deuterium; an alkyl group substituted or unsubstituted with deuterium; a cycloalkyl group substituted or unsubstituted with deuterium; an aryl group substituted or unsubstituted with deuterium; or a heteroaryl group substituted or unsubstituted with deuterium, or combines with an adjacent group to form a ring substituted with deuterium.

[0164] In one embodiment of the present invention, X11 and X13 are the same as or different from each other, and each independently is deuterium; or an alkyl group substituted with deuterium, or combines with an adjacent group to form a ring substituted with deuterium.

[0165] In one embodiment of the present invention, X11 and X14 contain deuterium.

[0166] In one embodiment of the present invention, X11 and X14 are the same as or different from each other, and each independently is deuterium; an alkyl group substituted or unsubstituted with deuterium; a cycloalkyl group substituted or unsubstituted with deuterium; an aryl group substituted or unsubstituted with deuterium, or a heteroaryl group substituted or unsubstituted with deuterium, or combines with an adjacent group to form a ring substituted with deuterium.

[0167] In one embodiment of the present invention, X11 and X14 are the same as or different from each other, and each independently is deuterium; or an alkyl group substituted with deuterium, or combines with an adjacent group to form a ring substituted with deuterium.

[0168] In one embodiment of the present invention, X12 and X13 contain deuterium.

[0169] In one embodiment of the present invention, X12 and X13 are the same as or different from each other, and each independently is deuterium; an alkyl group substituted or unsubstituted with deuterium; a cycloalkyl group substituted or unsubstituted with deuterium; an aryl group substituted or unsubstituted with deuterium; or a heteroaryl group substituted or unsubstituted with deuterium, or combines with an adjacent group to form a ring substituted with deuterium.

[0170] In one embodiment of the present invention, X12 and X13 are the same as or different from each other, and each independently is deuterium; or an alkyl group substituted with deuterium, or combines with an adjacent group to form a ring substituted with deuterium.

[0171] In one embodiment of the present invention, X12 and X14 contain deuterium.

[0172] In one embodiment of the present invention, X12 and X14 are the same as or different from each other, and each independently is deuterium; an alkyl group substituted or unsubstituted with deuterium; a cycloalkyl group substituted or unsubstituted with deuterium; an aryl group substituted or unsubstituted with deuterium, or a heteroaryl group substituted or unsubstituted with deuterium, or combines with an adjacent group to form a ring substituted with deuterium.

[0173] In one embodiment of the present invention, X12 and X14 are the same as or different from each other, and each independently is deuterium; or an alkyl group substituted with deuterium, or combines with an adjacent group to form a ring substituted with deuterium.

[0174] In one embodiment of the present invention, X13 and X14 contain deuterium.

[0175] In one embodiment of the present invention, X13 and X14 are the same as or different from each other, and each independently is deuterium; an alkyl group substituted or unsubstituted with deuterium; a cycloalkyl group substituted or unsubstituted with deuterium; an aryl group substituted or unsubstituted with deuterium, or a heteroaryl group substituted or unsubstituted with deuterium, or combines with an adjacent group to form a ring substituted with deuterium.

[0176] In one embodiment of the present invention, X13 and X14 are the same as or different from each other, and each independently is deuterium; or an alkyl group substituted with deuterium, or combines with an adjacent group to form a ring substituted with deuterium.

[0177] In one embodiment of the present invention, X11, X12 and X13 contain deuterium.

[0178] In one embodiment of the present invention, X11, X12, and X13 are the same as or different from each other, and each independently is deuterium; an alkyl group substituted or unsubstituted with deuterium; a cycloalkyl group substituted or unsubstituted with deuterium; an aryl group substituted or unsubstituted with deuterium; or a heteroaryl group substituted or unsubstituted with deuterium, or combines with an adjacent group to form a ring substituted with deuterium.

[0179] In one embodiment of the present invention, X11, X12, and X13 are the same as or different from each other, and each independently is deuterium; or an alkyl group substituted with deuterium, or combines with an adjacent group to form a ring substituted with deuterium.

[0180] In one embodiment of the present invention, X11, X12 and X14 contain deuterium.

[0181] In one embodiment of the present invention, X11, X12, and X14 are the same as or different from each other, and each independently is deuterium; an alkyl group substituted or unsubstituted with deuterium; a cycloalkyl group substituted or unsubstituted with deuterium; an aryl group substituted or unsubstituted with deuterium; or a heteroaryl group substituted or unsubstituted with deuterium, or combines with an adjacent group to form a ring substituted with deuterium.

[0182] In one embodiment of the present invention, X11, X12, and X14 are the same as or different from each other, and each independently is deuterium; or an alkyl group substituted with deuterium, or combines with an adjacent group to form a ring substituted with deuterium.

[0183] In one embodiment of the present invention, X12, X13, and X14 contain deuterium.

[0184] In one embodiment of the present invention, X12, X13, and X14 are the same as or different from each other, and each independently is deuterium; an alkyl group substituted or unsubstituted with deuterium; a cycloalkyl group substituted or unsubstituted with deuterium; an aryl group substituted or unsubstituted with deuterium; or a heteroaryl group substituted or unsubstituted with deuterium, or combines with an adjacent group to form a ring substituted with deuterium.

[0185] In one embodiment of the present invention, X12, X13, and X14 are the same as or different from each other, and each independently is deuterium; or an alkyl group substituted with deuterium, or combines with an adjacent group to form a ring substituted with deuterium.

[0186] In one embodiment of the present invention, X11 to X14 contain deuterium.

[0187] In one embodiment of the present invention, X11 to X14 are the same as or different from each other, and each independently is deuterium; an alkyl group substituted or unsubstituted with deuterium; a cycloalkyl group substituted or unsubstituted with deuterium; an aryl group substituted or unsubstituted with deuterium; or a heteroaryl group substituted or unsubstituted with deuterium, or combines with an adjacent group to form a ring substituted with deuterium.

[0188] In one embodiment of the present invention, X11 to X14 are the same as or different from each other, and each independently is deuterium; or an alkyl group substituted with deuterium, or combines with an adjacent group to form a ring substituted with deuterium.

[0189] In one embodiment of the present invention, one or more of X11 to X14 contain deuterium, and X1 to X4 do not contain deuterium.

[0190] In one embodiment of the present invention, two of X1 to X4 and one or more of X11 to X14 contain deuterium.

[0191] In one embodiment of the present invention, two of X1 to X4 and one of X11 to X14 contain deuterium.

[0192] In one embodiment of the present invention, two of X1 to X4 and two of X11 to X14 contain deuterium.

[0193] In one embodiment of the present invention, two of X1 to X4 and three of X11 to X14 contain deuterium.

[0194] In one embodiment of the present invention, two of X1 to X4 and X11 to X14 contain deuterium.

[0195] In one embodiment of the present invention, X1, X2 and X11 to X14 contain deuterium. In one embodiment of the present invention, X1, X3 and X11 to X14 contain deuterium. In one embodiment of the present invention, X1, X4, and X11 to X14 contain deuterium. In one embodiment of the present invention, X2, X3, and X11 to X14 contain deuterium. In one embodiment of the present invention, X2, X4, and X11 to X14 contain deuterium. In one embodiment of the present invention, X3, X4, and X11 to X14 contain deuterium.

[0196] In one embodiment of the present invention, two of X1 to X4 are groups represented by Chemical Formula 2, R1 and R2 in Chemical Formula 2 are unsubstituted aryl groups, and X11 to X14 are the same as or different from each other and are each independently deuterium; or an alkyl group substituted with deuterium, or combine with adjacent groups to form a ring substituted with deuterium.

[0197] In one embodiment of the present invention, two of X1 to X4 are groups represented by Chemical Formula 2, R1 and R2 in Chemical Formula 2 are aryl groups substituted with deuterium, and X11 to X14 are the same as or different from each other and are each independently deuterium; or an alkyl group substituted with deuterium, or combine with adjacent groups to form a ring substituted with deuterium.

[0198] In one embodiment of the present invention, the deuterium substitution rate of the compound is 20% or more. Specifically, the deuterium substitution rate of the compound is 25% or more, 30% or more, 35% or more, 40% or more, 45% or more, or 50% or more. The upper limit of the deuterium substitution rate is 100%.

[0199] In the present invention, the deuterium substitution rate means the substitution ratio of deuterium in the molecule. To grasp the substitution distribution of deuterium in the molecule, the following two methods are followed. Among the following two methods, TLC-MS is a method for adjusting the substitution ratio of deuterium in the synthesis process of the compound.

[0200] 1. Utilization of TLC-MS (Thin-Layer Chromatography / Mass Spectrometry) (Synthesis process confirmation method) The substitution rate can be calculated based on the maximum value (max. value) of the molecular weight distribution formed at the end of the reaction.

[0201] 2. Quantitative analysis using NMR By adding DMF (dimethylformamide) as an internal standard and using the integration ratio of the 1H NMR phase, the deuterium substitution rate can be calculated from the integrated value of the total peaks.

[0202] In one embodiment of the present invention, the deuterium substitution rate of a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a phenanthrenyl group substituted or unsubstituted with deuterium; a fluorenyl group substituted or unsubstituted with deuterium; and a naphthyl group substituted or unsubstituted with deuterium is 20% - 100%. Specifically, it is 40% - 100%, or 60% - 99%, and more specifically, it is 70% - 99%.

[0203] As an example, a phenyl group substituted with deuterium is

Chemical formula

Chemical formula

[0204] In one embodiment of the present invention, when the fluorenyl group is further substituted with other substituents in addition to deuterium, the deuterium substitution rate of the portion of the fluorenyl group excluding the portion substituted with other substituents is 20% to 100%. For example, a fluorenyl group substituted with a methyl group and deuterium can be represented by the following structure. In the following structure, the portion represented by deuterium may be replaced with hydrogen, and the deuterium substitution rate of the following structure is 20% to 100%. More specifically, the deuterium substitution rate of the following structure is 40% to 100%.

Chemical formula

[0205] In one embodiment of the present invention, the deuterium substitution rate of the phenylene group substituted with deuterium; and the naphthylene group substituted with deuterium is 20% to 100%.

[0206] As an example, the phenylene group substituted with deuterium is

Chemical formula

[0207] As another example, the naphthylene group substituted with deuterium can be represented by any of the following structures. In the following structures, the portion represented by deuterium can be replaced with hydrogen, and the deuterium substitution rate of the following structures is 20% to 100%. More specifically, the deuterium substitution rate of the following structures is 40% to 100%.

Chemical formula

[0208] In one embodiment of the present invention, the compound of Chemical Formula 1 is any of the following structures.

[0209] [Chemistry]

[0210] [Chemistry]

[0211] [Chemistry]

[0212] [Chemistry]

[0213] The compound of Chemical Formula 1 according to one embodiment of the present invention can be bonded by a method known in the art such as a coupling reaction under a palladium catalyst of two aryl groups each having a bromine and a boronic acid functional group, and the type, position, or number of substituents can be changed by a technique known in the art.

[0214] For example, the compound of Chemical Formula 1 may be produced with a core structure as shown in the following reaction formula. The substituents can be bonded by a method known in the art, and the type, position, or number of substituents can be changed according to a technique known in the art.

[0215] [Chemistry]

[0216] In the above reaction formula, Step 1-1 is a step of reacting Compound A1 and Compound A2 to produce Intermediate Compound A3 into which a phosphine group is introduced, and Step 1-2 is a step of oxidizing Intermediate Compound A3 to produce Final Compound A4.

[0217] In the above reaction formula, X is Br, and each substituent has the same definition as the substituent of Chemical Formula 1.

[0218] In the above reaction formula, Y can be used without limitation as long as it is a group used in the art, for example, Cl.

[0219] Hereinafter, the coating composition containing the aforementioned compound will be described in detail.

[0220] One embodiment of the present invention provides a coating composition containing the compound of Chemical Formula 1 described above.

[0221] In one embodiment of the present invention, the coating composition contains the compound of Chemical Formula 1 and a solvent.

[0222] In one embodiment of the present invention, the coating composition may be liquid.

[0223] In one embodiment of the present invention, the solvent is a solvent that dissolves the compound. Examples of the solvent include chlorinated solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, and o-dichlorobenzene; ether solvents such as tetrahydrofuran and dioxane; aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; ketone solvents such as acetone, methyl ethyl ketone, and cyclohexanone; ester solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; polyhydric alcohols and their derivatives such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, and 1,2-hexanediol; alcohol solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; benzoate solvents such as methyl benzoate, butyl benzoate, and 3-phenoxybenzoate; and tetralin. The solvent may be any solvent that can dissolve or disperse the compound according to one embodiment of the present invention, and is not limited thereto.

[0224] In one embodiment of the present invention, the solvent may be used alone or in combination of two or more solvents.

[0225] In one embodiment of the present invention, the coating composition may further contain a dopant substance. At this time, the dopant substance may be a dopant substance for an electron injection layer, a dopant substance for an electron transport layer, or a dopant substance for an electron injection and transport layer. The dopant substance may contain at least one selected from the group consisting of an organic-inorganic mixture, a metal, and an organic salt.

[0226] In one embodiment of the present invention, the dopant substance may be an organic substance containing a substituent containing CN and / or F.

[0227] In one embodiment of the present invention, the dopant substance may contain at least one selected from the group consisting of alkali metals, alkaline earth metals, lanthanide metals, Se, Ru, and their compounds. Specifically, the alkali metal may be Li. Also, the alkaline earth metal may be Ca and Mg. Further, the compounds may be LiF, Liq, and RuCO 3 and may be. Also, the lanthanide metal may be Yb.

[0228] In one embodiment of the present invention, the dopant substance may contain fullerene. Specifically, the fullerene may be fullerene having 60 carbon atoms or fullerene having 70 carbon atoms.

[0229] In one embodiment of the present invention, the dopant substance may contain a halogenated salt. Specifically, the halogenated salt may be LiF.

[0230] According to one embodiment of the present invention, the content of the dopant substance may be 1% by weight or more and 50% by weight or less based on the total weight of the layer containing the dopant substance.

[0231] In one embodiment of the present invention, the coating composition further contains a single molecule containing a photocurable group and / or a thermosettable group; or a single molecule containing an end group capable of forming a polymer by heat. The molecular weight of the single molecule containing a photocurable group and / or a thermosettable group; or a single molecule containing an end group capable of forming a polymer by heat as described above may be a compound having a molecular weight of 3,000 g / mol or less, but is not limited to the exemplified molecular weights.

[0232] A single molecule containing the photocurable group and / or thermosetting group; or a single molecule containing a terminal group capable of polymer formation by heat means an aryl such as phenyl, biphenyl, fluorene, naphthalene; arylamine; or a single molecule in which a photocurable group, thermosetting group and / or terminal group capable of polymer formation by heat is substituted for fluorene.

[0233] In one embodiment of the present invention, the viscosity of the coating composition is 2 cP to 15 cP at room temperature. When the viscosity is satisfied, the manufacturing of the device is easy. Specifically, when forming an organic layer in an organic light-emitting device, a uniform film can be formed.

[0234] One embodiment of the present invention provides an organic light-emitting device including the compound of Chemical Formula 1, the coating composition or a cured product thereof.

[0235] Hereinafter, the organic light-emitting device will be described in detail.

[0236] One embodiment of the present invention provides an organic light-emitting device formed using the compound of Chemical Formula 1.

[0237] One embodiment of the present invention provides an organic light-emitting device including a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one layer of the organic layers contains the aforementioned compound.

[0238] In one embodiment of the present invention, the organic layer includes a light-emitting layer. As an example, the light-emitting layer contains the aforementioned compound. As a specific example, the light-emitting layer contains the aforementioned compound as a host of the light-emitting layer. As another specific example, the light-emitting layer contains the aforementioned compound as a dopant of the light-emitting layer.

[0239] In one embodiment of the present invention, the organic layer includes at least one layer selected from the group consisting of an electron injection layer, an electron transport layer, and an electron injection and transport layer. As an example, at least one layer selected from the group consisting of the electron injection layer, the electron transport layer, and the electron injection and transport layer contains the aforementioned compound.

[0240] In one embodiment of the present invention, the organic layer includes an electron transport layer. As an example, the electron transport layer contains the aforementioned compound.

[0241] In one embodiment of the present invention, the organic layer includes at least one layer selected from the group consisting of an electron blocking layer, a hole blocking layer, a hole injection layer, a hole transport layer, and a hole injection and transport layer. As an example, at least one layer selected from the group consisting of the electron blocking layer, the hole blocking layer, the hole injection layer, the hole transport layer, and the hole injection and transport layer contains the aforementioned compound.

[0242] In one embodiment of the present invention, the organic light-emitting device includes a single layer of an organic layer, and the organic layer contains the aforementioned compound.

[0243] In one embodiment of the present invention, the organic light-emitting device includes two or more layers (multilayer) of an organic layer, and the two or more layers of the organic layer contain the aforementioned compound. For example, one of the two or more layers of the organic layer contains the aforementioned compound, and further includes at least one of the remaining organic layers. The remaining at least one layer of the organic layer according to one embodiment does not contain the aforementioned compound. The remaining at least one layer of the organic layer according to another embodiment contains the aforementioned compound. However, it is not limited to the above examples.

[0244] The above two or more organic layers include, for example, two or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, and the like. At this time, the hole injection and transport layer means a layer that simultaneously performs hole injection and hole transport, and the electron injection and transport layer means a layer that simultaneously performs electron injection and electron transport. However, the organic layers forming the group are merely examples and are not limited to the above examples. Further, the above two or more organic layers may include two or more layers that perform the same role as necessary. An organic light emitting device according to an example includes a first electron transport layer and a second electron transport layer. However, it is not limited to the above example.

[0245] In one embodiment of the present invention, the above two or more organic layers include a light emitting layer and an organic layer other than the light emitting layer. As an example, the light emitting layer is provided between the first electrode and the second electrode, and the organic layer other than the light emitting layer is provided between the first electrode and the light emitting layer. As another example, the light emitting layer is provided between the first electrode and the second electrode, and the organic layer other than the light emitting layer is provided between the light emitting layer and the second electrode. As still another example, the light emitting layer is provided between the first electrode and the second electrode, and one organic layer other than the light emitting layer is provided between the first electrode and the light emitting layer, and the other organic layer other than the light emitting layer is provided between the light emitting layer and the second electrode. However, the above configuration is merely an example and is not limited to the above configuration. Further, the organic layer other than the light emitting layer may be, for example, at least one layer selected from the group consisting of a hole injection and transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, and the like, but is not limited thereto.

[0246] In one embodiment of the present invention, the organic layer includes a light emitting layer and a first organic layer, and the first organic layer contains the aforementioned compound.

[0247] In one embodiment of the present invention, the first organic layer has a single-layer (one layer) or multilayer (two or more layers) structure. When there are two or more first organic layers, the two or more first organic layers are the same as or different from each other.

[0248] In one embodiment of the present invention, the first organic layer is provided between the light-emitting layer and the cathode.

[0249] In one embodiment of the present invention, the second electrode is a cathode, and the first organic layer is provided between the light-emitting layer and the cathode.

[0250] In one embodiment of the present invention, the first organic layer is at least one of an electron injection layer; an electron transport layer; and an electron injection and transport layer.

[0251] In one embodiment of the present invention, the organic layers of the multilayer structure included in the organic light-emitting device include a light-emitting layer; and a first organic layer selected from the group consisting of a hole injection and transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer. The light-emitting layer is provided between the first electrode and the second electrode, and the first organic layer is provided between the light-emitting layer and the second electrode, or between the first electrode and the light-emitting layer. As an example, the first organic layer contains the aforementioned compound.

[0252] According to a preferred embodiment of the present invention, the first organic layer is at least one of an electron injection layer; an electron transport layer; and an electron injection and transport layer. More preferably, the first organic layer is an electron transport layer.

[0253] The above has illustrated the case where the organic layer of the organic light-emitting device contains the aforementioned compound. In one embodiment of the present invention, the organic layer containing the aforementioned compound may contain a coating composition containing the aforementioned compound or a cured product thereof instead of the aforementioned compound.

[0254] As an example, one embodiment of the present invention provides an organic light-emitting device including a first electrode, a second electrode, and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers includes the aforementioned coating composition or a cured product thereof. As another example, the aforementioned organic layer includes a light-emitting layer and a first organic layer, and the aforementioned first organic layer includes the coating composition or a cured product thereof.

[0255] In one embodiment of the present invention, the cured product is a state in which the coating composition is cured by heat treatment or light treatment.

[0256] The structure of an organic light-emitting device according to one embodiment of the present invention is shown in FIG. 1. FIG. 1 illustrates the structure of an organic light-emitting device in which a first electrode 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 second electrode 701 are sequentially stacked on a substrate 101. However, FIG. 1 illustrates an organic light-emitting device according to one embodiment of the present invention, and the structure of the organic light-emitting device of the present invention is not limited thereto.

[0257] In one embodiment of the present invention, the first electrode is an anode and the second electrode is a cathode.

[0258] In another embodiment of the present invention, the first electrode is a cathode and the second electrode is an anode.

[0259] Generally, in an organic light-emitting device, a hole injection layer, a hole transport layer, or an electron blocking layer is provided between the anode and the light-emitting layer. As a specific example, the hole injection layer is provided on the anode, the hole transport layer is provided on the hole injection layer, and the electron blocking layer is provided on the hole transport layer, but is not limited to the above examples.

[0260] In general, in an organic light-emitting device, an electron injection layer, an electron transport layer, or a hole blocking layer is provided between the cathode and the light-emitting layer. As a specific example, the hole blocking layer is provided above the light-emitting layer, the electron transport layer is provided above the hole blocking layer, and the electron injection layer is provided above the electron transport layer, but is not limited to the above examples.

[0261] As described above, an organic light-emitting device having a single-layer or multi-layer organic layer can have, for example, the following laminated structures, but is not limited thereto. (1) Anode / Hole Transport Layer / Light-Emitting Layer / Cathode (2) Anode / Hole Injection Layer / Hole Transport Layer / Light-Emitting Layer / Cathode (3) Anode / Hole Injection Layer / Hole Buffer Layer / Hole Transport Layer / Light-Emitting Layer / Cathode (4) Anode / Hole Transport Layer / Light-Emitting Layer / Electron Transport Layer / Cathode (5) Anode / Hole Transport Layer / Light-Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode (6) Anode / Hole Injection Layer / Hole Transport Layer / Light-Emitting Layer / Electron Transport Layer / Cathode (7) Anode / Hole Injection Layer / Hole Transport Layer / Light-Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode (8) Anode / Hole Injection Layer / Hole Buffer Layer / Hole Transport Layer / Light-Emitting Layer / Electron Transport Layer / Cathode (9) Anode / Hole Injection Layer / Hole Buffer Layer / Hole Transport Layer / Light-Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode (10) Anode / Hole Transport Layer / Electron Blocking Layer / Light-Emitting Layer / Electron Transport Layer / Cathode (11) Anode / Hole Transport Layer / Electron Blocking Layer / Light-Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode (12) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light-Emitting Layer / Electron Transport Layer / Cathode (13) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light-Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode (14) Anode / Hole Transport Layer / Light-Emitting Layer / Hole Blocking Layer / Electron Transport Layer / Cathode (15) Anode / Hole Transport Layer / Light-Emitting Layer / Hole Blocking Layer / Electron Transport Layer / Electron Injection Layer / Cathode (16) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Hole Blocking Layer / Electron Transport Layer / Cathode (17) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Hole Blocking Layer / Electron Transport Layer / Electron Injection Layer / Cathode (18) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Hole Blocking Layer / Electron Transport Layer / Electron Injection Layer / Cathode / Capsule (19) Anode / Hole Injection Layer / First Hole Transport Layer / Second Hole Transport Layer / Light Emitting Layer / Hole Blocking Layer / Electron Transport Layer / Electron Injection Layer / Cathode / Capsule In the above configuration, "Electron Transport Layer / Electron Injection Layer" can be replaced with "Electron Injection and Transport Layer" or "Layer that simultaneously performs electron transport and electron injection".

[0262] Also, in the above configuration, "Hole Injection Layer / Hole Transport Layer" can be replaced with "Hole Injection and Transport Layer" or "Layer that simultaneously performs hole injection and hole transport".

[0263] In one embodiment of the present invention, the organic light-emitting device may be a normal type organic light-emitting device in which an anode, at least one organic layer, and a cathode are sequentially stacked on a substrate.

[0264] In another embodiment of the present invention, the organic light-emitting device may be an inverted type organic light-emitting device in which a cathode, at least one organic layer, and an anode are sequentially stacked on a substrate.

[0265] One embodiment of the present invention also provides a method for manufacturing an organic light-emitting device formed using the aforementioned compound or the aforementioned coating composition.

[0266] The organic light-emitting device according to one embodiment of the present invention may be manufactured by materials and methods known in the art, except that at least one of the organic layers is formed using the aforementioned compound or the aforementioned coating composition.

[0267] For example, the organic light-emitting device of the present invention can be manufactured by sequentially laminating an anode, an organic layer, and a cathode on a substrate. At this time, a metal, a metal oxide having conductivity, or an alloy thereof is deposited on the substrate using a PVD (Physical Vapor Deposition) method such as sputtering or e-beam evaporation to form an anode, and a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer, an electron transport layer, a hole transport and injection layer, and an organic layer solution process including at least one layer of an electron injection and transport layer, After forming through a deposition process or the like, it can be manufactured by depositing a substance that can be used as a cathode thereon. In addition to such a method, an organic light-emitting device can be manufactured by sequentially depositing an organic layer and an anode substance from a cathode substance on a substrate.

[0268] Specifically, one embodiment of the present invention includes a step of preparing a first electrode; a step of forming an organic layer on the first electrode; and a step of forming a second electrode on the organic layer, and the step of forming the organic layer includes a step of forming at least one organic layer using the aforementioned coating composition.

[0269] In one embodiment of the present invention, the step of forming at least one organic layer using the coating composition uses a spin coating method.

[0270] In another embodiment of the present invention, the step of forming at least one organic layer using the coating composition uses a printing method.

[0271] In one embodiment of the present invention, the printing method includes, for example, coating jet printing, nozzle printing, offset printing, transfer printing, or screen printing, but is not limited to the listed printing methods.

[0272] According to one embodiment of the present invention, the coating composition is suitable for solution processes in terms of structural properties and can be formed by printing methods, which is economically effective in terms of time and cost during the manufacture of devices.

[0273] In one embodiment of the present invention, the step of forming an organic layer using the coating composition includes the step of coating the coating composition; and the coated coating composition includes a drying step, a heat treatment step, and / or a light treatment step.

[0274] In one embodiment of the present invention, the step of forming at least one organic layer using the coating composition includes the step of coating the coating composition on the first electrode; and the step of heat-treating or light-treating the coated coating composition. Preferably, the step of forming at least one organic layer using the coating composition includes the step of coating the coating composition on the first electrode or another organic layer; and the step of heat-treating the coated coating composition.

[0275] In one embodiment of the present invention, the heat treatment step includes a drying step.

[0276] In one embodiment of the present invention, the other organic layer means an organic layer formed previously before forming an organic layer using the coating composition. The other organic layer at this time may be an organic layer formed previously using the aforementioned coating composition, or may be an organic layer formed previously using other substances without using the aforementioned coating composition.

[0277] In one embodiment of the present invention, the heat treatment step can be performed through heat treatment. The heat treatment temperature in the heat treatment step is 85°C to 250°C, and according to one embodiment, it may be 100°C to 250°C, and in another embodiment, it may be 150°C to 250°C.

[0278] In one embodiment of the present invention, the heat treatment time in the heat treatment step is from 1 minute to 2 hours. According to one embodiment, it is from 1 minute to 1 hour, and in another embodiment, it may be from 10 minutes to 1 hour. As a preferred example, the heat treatment time in the heat treatment step is from 20 minutes to 40 minutes.

[0279] In the step of forming at least one organic layer using the coating composition, when the coating composition further contains a single molecule containing a photocurable group and / or a thermosettable group; or a single molecule containing a terminal group capable of forming a polymer by heat, it is possible to provide an organic layer including a structure in which crosslinking between the components contained in the coating composition is formed through the heat treatment or light treatment step to form a thin film. At this time, when another layer is laminated on the surface of the organic layer formed using the coating composition, it is possible to prevent dissolution, morphological influence, or decomposition by a solvent. Therefore, when an organic layer is formed by the manufacturing method, the resistance to a solvent increases, and a multilayer can be formed by repeatedly performing a solution deposition and crosslinking method, and the stability increases and the lifetime characteristics of the element can be increased.

[0280] In another embodiment of the present invention, the step of forming at least one organic layer using the coating composition utilizes vapor deposition.

[0281] One embodiment of the present invention also includes a step of preparing a first electrode; a step of forming at least one organic layer on the first electrode; and a step of forming a second electrode on the organic layer, and the step of forming the organic layer includes a step of vapor depositing the compound to form at least one organic layer, and provides a method for manufacturing an organic light-emitting device.

[0282] In one embodiment of the present invention, the vapor deposition step may be performed under vacuum conditions. Specifically, it can be performed at a degree of vacuum of 5×10 -8 torr to 2×10 -7 torr.

[0283] In one embodiment of the present invention, the vapor deposition step may be performed at a rate of 0.01 Å / sec to 10 Å / sec. Specifically, it can be performed at a rate of 0.05 Å / sec to 8 Å / sec, or 0.1 Å / sec to 6 Å / sec.

[0284] Hereinafter, the substances contained in the organic light-emitting element will be described.

[0285] As the anode material, usually, a material having a large work function is preferable so that hole injection into the organic layer becomes smooth. For example, metals such as vanadium, chromium, copper, zinc, gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0286] As the cathode material, usually, a material having a small work function is preferably used so that electron injection into the organic layer becomes easy. For example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or their alloys; multilayer structured materials such as LiF / Al or LiO 2 / Al, but is not limited thereto.

[0287] The light-emitting layer may contain a host material for the light-emitting layer and / or a dopant material for the light-emitting layer.

[0288] Examples of the host material for the light-emitting layer include condensed aromatic ring derivatives and heterocyclic compounds. Specifically, examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and examples of the heterocyclic compounds include dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto. Specifically, the host material for the light-emitting layer is an anthracene derivative.

[0289] In one embodiment of the present invention, as the host material, two or more host materials selected from the above-described host materials can be mixed and used. As an example, an anthracene derivative and a pyrene derivative can be mixed and used at a weight ratio of 1:99 to 99:1. As a more specific example, an anthracene derivative and a pyrene derivative can be mixed and used at a weight ratio of 92:8.

[0290] In one embodiment of the present invention, the host of the light-emitting layer contains the following compound EH-1. [Chemical formula]

[0291] In the chemical formula EH-1, L401 and L402 are the same as or different from each other, and each independently is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, Ar401 and Ar402 are the same as or different from each other, and each independently is hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, R401 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, l401 and l402 are the same as or different from each other, and each independently is an integer from 1 to 10. When l401 and l402 are each 2 or more, the structures within each pair of parentheses are the same as or different from each other. r401 is an integer from 1 to 8. When the said r401 is 2 or more, two or more R401s are the same as or different from each other.

[0292] In one embodiment of the present invention, the said L401 and L402 are the same as or different from each other, and each independently is a direct bond; or a substituted or unsubstituted arylene group.

[0293] In one embodiment of the present invention, the said L401 and L402 are the same as or different from each other, and each independently is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted naphthylene group; or a substituted or unsubstituted anthracene group.

[0294] In one embodiment of the present invention, the chemical formula EH-1 is represented by the following chemical formula EH-2.

Chemical formula

[0295] In the said chemical formula EH-2, L402 to L404 are the same as or different from each other, and each independently is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group. Ar402 and Ar403 are the same as or different from each other, and each independently is hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group. R401 and R402 are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group. l402 to l404 are the same as or different from each other, and are each independently an integer from 1 to 3. When l401 to l404 are each 2 or more, the structures within each pair of parentheses are the same as or different from each other. r401 and r402 are each an integer from 1 to 8. When r401 and r402 are each 2 or more, the structures within each pair of parentheses are the same as or different from each other.

[0296] In one embodiment of the present invention, L402 to L404 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted arylene group.

[0297] In one embodiment of the present invention, L404 is a substituted or unsubstituted arylene group. In one embodiment of the present invention, L404 is a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group. In one embodiment of the present invention, L404 is a phenylene group; a biphenylene group; or a naphthylene group.

[0298] In one embodiment of the present invention, l404 is 3.

[0299] In one embodiment of the present invention, L402 and L403 are each a direct bond.

[0300] In one embodiment of the present invention, Ar401 and Ar402 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group. In one embodiment of the present invention, Ar401 and Ar402 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; or a substituted or unsubstituted naphthyl group. In one embodiment of the present invention, Ar401 and Ar402 are each a substituted or unsubstituted naphthyl group. In one embodiment of the present invention, the Ar401 and Ar402 are each a naphthyl group.

[0301] In one embodiment of the present invention, the Ar403 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, the Ar403 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; or a substituted or unsubstituted naphthyl group. In one embodiment of the present invention, the Ar403 is a substituted or unsubstituted naphthyl group. In one embodiment of the present invention, the Ar403 is a naphthyl group.

[0302] In one embodiment of the present invention, the R401 and R402 are the same as or different from each other, and each independently is hydrogen; or deuterium.

[0303] In one embodiment of the present invention, the chemical formula EH-1 has the following structure. [Chemical formula]

[0304] Examples of the dopant material for the light-emitting layer include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, examples of the aromatic amine derivative include condensed aromatic ring derivatives having a substituted or unsubstituted arylamine group, such as pyrene, anthracene, chrysene, and periflanthene having an arylamine group. The styrylamine compound is a compound in which at least one arylvinyl group is substituted for a substituted or unsubstituted arylamine, and is substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group. Specifically, examples include styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc., but are not limited thereto. Examples of the metal complex include, but are not limited to, iridium complexes and platinum complexes. Specifically, the dopant for the light-emitting layer is a pyrene-based compound having a substituted or unsubstituted arylamine group.

[0305] In one embodiment of the present invention, the dopant of the light-emitting layer includes a compound of the following chemical formula ED-1. [Chemical formula]

[0306] In the chemical formula ED-1, Ar501 to Ar504 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0307] In one embodiment of the present invention, the chemical formula ED-1 is the following chemical formula ED-2. [Chemical formula]

[0308] In the chemical formula ED-2, Ar501 to Ar504 are as defined by the chemical formula ED-1.

[0309] In one embodiment of the present invention, Ar501 to Ar504 are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group. In one embodiment of the present invention, Ar501 to Ar504 are the same as or different from each other, and each independently is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; or a substituted or unsubstituted naphthyl group. In one embodiment of the present invention, Ar501 to Ar504 are the same as or different from each other, and each independently is a phenyl group substituted or unsubstituted with a silyl group; a biphenyl group substituted or unsubstituted with a silyl group; a terphenyl group substituted or unsubstituted with a silyl group; or a naphthyl group substituted or unsubstituted with a silyl group. In one embodiment of the present invention, Ar501 to Ar504 are the same as or different from each other, and each independently is a phenyl group substituted or unsubstituted with a silyl group.

[0310] In the present specification, the silyl group is a group represented by -SiRcRdRe, where Rc, Rd, and Re are the same as or different from each other, and each independently is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group. The number of carbon atoms of the silyl group is not particularly limited, but is preferably 1 to 60.

[0311] In one embodiment of the present invention, the chemical formula ED-1 has the following structure.

Chemical formula

[0312] The hole injection layer is a layer that receives holes. The hole injection material preferably has the ability to transport holes and has an excellent hole receiving effect from the anode and an excellent hole injection effect on the light emitting layer or the light emitting material. Further, a material having an excellent ability to prevent the transfer of excitons generated in the light emitting layer to the electron injection layer or the electron injection material and having an excellent thin film forming ability is preferable. Further, the HOMO of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic substances; hexanitrile hexaazatriphenylene-based organic substances; quinacridone-based organic substances; perylene-based organic substances; polythiophene-based conductive polymers such as anthraquinone and polyaniline, but are not limited thereto. Specifically, the hole injection material is an arylamine-based organic substance.

[0313] In one embodiment of the present invention, the hole injection layer contains a compound of the following chemical formula HI-1.

Chemical formula

[0314] In the chemical formula HI-1, L201 is a substituted or unsubstituted arylene group, R201 to R204 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl; a photocurable group or a thermosetting group.

[0315] In one embodiment of the present invention, the L201 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms. In one embodiment of the present invention, the L201 is an arylene group. In one embodiment of the present invention, the L201 is a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group. In one embodiment of the present invention, the L201 is a phenylene group; a biphenylene group; or a naphthylene group. In one embodiment of the present invention, the L201 is a biphenylene group.

[0316] In one embodiment of the present invention, the R201 to R204 are the same as or different from each other, and each independently is hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms; a photocurable group or a thermosetting group. In one embodiment of the present invention, the R201 to R204 are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a photocurable group or a thermosetting group. In one embodiment of the present invention, the R201 to R204 are the same as or different from each other, and each independently is an aryl group; a photocurable group or a thermosetting group. In one embodiment of the present invention, the R201 to R204 are the same as or different from each other, and each independently is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group; a photocurable group or a thermosetting group. In one embodiment of the present invention, the R201 to R204 are the same as or different from each other, and each independently is a phenyl group; a biphenyl group; a naphthyl group; a photocurable group or a thermosetting group.

[0317] In this specification, the photocurable group or thermosetting group can mean a reactive substituent that crosslinks between compounds or polymers by exposure to light and / or heat. The photocurable group or thermosetting group can be generated by the linking of radicals generated by the decomposition of carbon-carbon multiple bonds or cyclic structures by light irradiation or heat treatment.

[0318] In one embodiment of the present invention, the photocurable group or thermosetting group is any of the following structures.

Chemical formula

[0319] In the above configuration, L50 to L56 are the same as or different from each other and are each independently a direct bond; -O-; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group,

Chemical formula

[0320] In one embodiment of the present invention, the photocurable group or thermosetting group is any of the following structures.

Chemical formula

[0321] In the above structure, L54 is a direct bond; or -O-,

Chemical formula

[0322] In one embodiment of the present invention, the photocurable group or thermosetting group is

Chemical formula

[0323] In one embodiment of the present invention, the photocurable group or thermosetting group is any of the following structures.

Chemical formula

[0324] In one embodiment of the present invention, the chemical formula HI-1 has the following structure.

Chemical formula

[0325] In one embodiment of the present invention, the hole injection layer further contains a p-doping substance.

[0326] In this specification, the p-doping substance means a substance that makes the host substance have p-semiconductor characteristics. The p-semiconductor characteristics mean the characteristics in which holes are injected or transported at the HOMO (highest occupied molecular orbital) energy level, that is, the characteristics of a substance with high hole conductivity.

[0327] In one embodiment of the present invention, the p-doping substance can be represented by any of the following structures, but is not limited thereto.

[0328]

Chemical formula

[0329] In this specification, the p-doping substance may be any substance that has p-semiconductor characteristics, and one or more kinds can be used without limiting the type thereof.

[0330] In one embodiment of the present invention, the content of the p-doping substance is 0 wt% to 500 wt% based on the chemical formula HI-1 compound. Specifically, the content of the p-doping substance is 100 wt% to 400 wt% based on the chemical formula HI-1 compound.

[0331] In one embodiment of the present invention, the p-doping substance is contained in an amount of 0 to 50 wt% based on the solid content of the composition for forming the hole injection layer. In one embodiment of the present invention, the p-doping substance preferably contains 1 to 50 wt% based on the total solid content of the composition, and more preferably contains 10 to 30 wt% based on the total solid content of the composition.

[0332] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and may have a single-layer or multi-layer structure of two or more layers. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer, and a material having a large mobility with respect to holes is preferred.

[0333] In one embodiment of the present invention, the hole transport layer contains a polymer containing a unit of the following chemical formula HT-1.

Chemical formula

[0334] In the chemical formula HT-1, L301 and L302 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group. l302 is an integer of 0 to 3. When l302 is 2 or more, L302 are the same as or different from each other. Ar301 and Ar302 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group. R301 to R307 are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; a hydroxy group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, r304 and r306 are the same as or different from each other, and each independently is an integer from 0 to 3, r305 and r307 are the same as or different from each other, and each independently is an integer from 0 to 4. When each of r304 to r307 is 2 or more, the structures within each pair of parentheses are the same as or different from each other, n is the number of repeating units and is an integer from 2 to 10,000.

[0335] In one embodiment of the present invention, L301 and L302 are the same as or different from each other, and each independently is a direct bond; a substituted or unsubstituted arylene group. In one embodiment of the present invention, L301 and L302 are the same as or different from each other, and each independently is a substituted or unsubstituted arylene group. In one embodiment of the present invention, L301 and L302 are the same as or different from each other, and each independently is a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group. In one embodiment of the present invention, L301 and L302 are the same as or different from each other, and each independently is a phenylene group; a biphenylene group; or a naphthylene group. In one embodiment of the present invention, L301 and L302 are each a phenylene group.

[0336] In one embodiment of the present invention, R301 to R307 are the same as or different from each other, and each independently is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. In one embodiment of the present invention, R301 to R307 are the same as or different from each other, and each independently is hydrogen or deuterium.

[0337] In one embodiment of the present invention, the Ar301 and Ar302 are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group. In one embodiment of the present invention, the Ar301 and Ar302 are the same as or different from each other, and each independently is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted fluorenyl group.

[0338] In one embodiment of the present invention, the chemical formula HT-1 has the following structure.

Chemical formula

[0339] The electron transport layer is a layer that receives electrons and transports them to the light-emitting layer. As the electron transport material, a material that can successfully inject electrons from the cathode and transfer them to the light-emitting layer, and a material with high mobility for electrons is preferred. Specific examples include an Al complex of 8-hydroxyquinoline; a complex containing Alq 3 including complexes; organic radical compounds; hydroxyflavone-metal complexes, etc., but are not limited thereto. The electron transport layer can be used together with any desired cathode material as used in the prior art. In particular, a suitable cathode material has a low work function and is a normal material followed by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium, and samarium, etc., and in each case, an aluminum layer or a silver layer follows. In one embodiment of the present invention, the electron transport material is the compound of Chemical formula 1 described above.

[0340] The electron injection layer is a layer that receives electrons from the electrode. As the electron injection material, those having excellent electron transport ability, excellent electron receiving effect from the cathode, and excellent electron injection effect on the light-emitting layer or light-emitting material are preferable. Further, a material that prevents excitons generated in the light-emitting layer from moving to the hole injection layer and has excellent thin film forming ability is preferable. Specifically, there are fluorenone, anthraquinodimethane, diphenoquinone, thiopyrandioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthrone and their derivatives, metal complex compounds, nitrogen-containing five-membered ring derivatives, etc., but it is not limited thereto. As the metal complex compound, there are lithium 8-hydroxyquinolinate, zinc bis(8-hydroxyquinolinate), copper bis(8-hydroxyquinolinate), manganese bis(8-hydroxyquinolinate), aluminum tris(8-hydroxyquinolinate), aluminum tris(2-methyl-8-hydroxyquinolinate), gallium tris(8-hydroxyquinolinate), beryllium bis(10-hydroxybenzo[h]quinolinate), zinc bis(10-hydroxybenzo[h]quinolinate), gallium bis(2-methyl-8-quinolinato)chloride, gallium bis(2-methyl-8-quinolinato)(o-cresolato), aluminum bis(2-methyl-8-quinolinato)(1-naphtholato), gallium bis(2-methyl-8-quinolinato)(2-naphtholato), etc., but it is not limited thereto. In one embodiment of the present invention, the electron injection material is the compound of Chemical Formula 1 described above.

[0341] In one embodiment of the present invention, at least one of the electron injection layer, electron transport layer, and electron injection and transport layer contains the above-mentioned compound.

[0342] The electron blocking layer is a layer that can prevent electrons injected from the electron injection layer from entering the hole injection layer through the light-emitting layer, and can improve the lifetime or efficiency of the device. As the electron blocking material, known electron blocking materials can be used.

[0343] The hole blocking layer is a layer that prevents holes from reaching the cathode and can generally be formed under the same conditions as the electron injection layer. Specific examples of the hole blocking layer material include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and aluminum complexes.

[0344] The hole injection and transport layer may include the materials of the aforementioned hole injection layer and hole transport layer.

[0345] The electron injection and transport layer may include the materials of the aforementioned electron injection layer and hole transport layer.

[0346] When the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0347] The organic light-emitting device according to the present invention may be a front emission type, a back emission type, or a double-sided emission type depending on the materials used.

[0348] One embodiment of the present invention provides an electronic device including an organic light-emitting device including the compound of Chemical Formula 1 described above, a coating composition containing the same or a cured product thereof, or an organic layer formed using the coating composition.

[0349] The electronic device may include, but is not limited to, an interlayer insulating film of a semiconductor device, a color filter, a black matrix, an overcoat, a column spacer, a passivation film, a buffer coat film, an insulating film for a multilayer printed circuit board, a cover coat of a flexible copper-clad laminate, a buffer coat film, an insulating film for a multilayer printed circuit board, a solder resist film, an insulating film of an OLED, a protective film of a thin film transistor of a liquid crystal display element, an electrode protective film and a semiconductor protective film of an organic EL device, an OLED insulating film, an LCD insulating film, a semiconductor insulating film, a solar module, a touch panel, a display device such as a display panel, etc.

Example

[0350] Hereinafter, examples will be given and described in detail to specifically describe the present invention. However, the examples according to the present invention can be changed into various different forms, and the scope of the present invention should not be construed as being limited to the examples described below. The examples of the present invention are provided to more fully explain the present invention to those with average knowledge in the industry.

[0351] <Synthesis Example> 〔Synthesis Example 1. Synthesis of Compound 1〕

Chemical Formula

[0352] Compound 1a dried by oven drying was dissolved in anhydrous tetrahydrofuran (anhydrous THF) (0.1 M), and then replaced with a nitrogen atmosphere. After lowering the temperature of the solution to -78°C, n-butyllithium (n-BuLi) (3.0 equiv. or more) was added dropwise. After stirring for 30 minutes, compound 1b (2.1 equiv.) was added dropwise. After stirring overnight, the temperature of the solution was lowered to 0°C, and ethanol (EtOH) was added dropwise to terminate the reaction. After separating the aqueous layer, the crude solution was obtained by extraction with ethyl acetate (EtOAc) / H 2 O, and white solid compound 1c was obtained by purification on an EtOAc column. The obtained compound 1c was dissolved in CH 2 Cl 2 After that, the temperature of the solution was lowered to 0°C, and excess H 2 O 2 was slowly added dropwise. Then, after confirming the substitution by thin-layer chromatography (TLC), water was added dropwise to terminate the reaction. Then, the CH 2 Cl 2 layer was separated, and compound 1 was obtained by purification on an EtOAc column. MS: [M + H] + = 736.8

[0353] 〔Synthesis Example 2. Synthesis of Compound 2〕

Chemical Formula

[0354] In Synthesis Example 1, Compound 2 was obtained by the same production method as in Synthesis Example 1, except that Compound 2a was used instead of Compound 1a. MS: [M+H] + =764.9

[0355] [Synthesis Example 3. Synthesis of Compound 3]

Chemical Structure

[0356] In Synthesis Example 1, Compound 3 was obtained by the same production method as in Synthesis Example 1, except that Compound 3a was used instead of Compound 1a. MS: [M+H] + =736.8

[0357] 〔Synthesis Example 4. Synthesis of Compound 4〕

Chemical Structure

[0358] In Synthesis Example 1, Compound 4 was obtained by the same production method as in Synthesis Example 1, except that Compound 4a was used instead of Compound 1a. MS: [M+H] + =786.9

[0359] 〔Synthesis Example 5. Synthesis of Compound 5〕

Chemical Structure

[0360] In Synthesis Example 1, Compound 5 was obtained by a method similar to the production method of Synthesis Example 1, except that Compound 5a was used instead of Compound 1a. MS: [M+H] + =786.9

[0361] 〔Synthesis Example 6. Synthesis of Compound 6〕

Chemical Structure

[0362] In Synthesis Example 1, Compound 6 was obtained in the same manner as the production method of Synthesis Example 1, except that Compound 6a was used instead of Compound 1a and 6b was used instead of Compound 1b. MS: [M+H] + =730.8

[0363] 〔Synthesis Example 7. Synthesis of Compound 7〕

Chemical formula

[0364] In Synthesis Example 6, Compound 7 was obtained in the same manner as the production method of Synthesis Example 6, except that Compound 7a was used instead of Compound 6a. MS: [M+H] + =762.9

[0365] 〔Synthesis Example 8. Synthesis of Compound 8〕

Chemical formula

[0366] In Synthesis Example 6, Compound 8 was obtained in the same manner as the production method of Synthesis Example 6, except that Compound 8a was used instead of Compound 6a. MS: [M+H] + =782.9

[0367] 〔Synthesis Example 9. Synthesis of Compound 9〕

Chemical formula

[0368] Compound 9a, Compound 9b (2.3 equiv.), potassium carbonate (K 2 CO 3 )(3.0 equiv.) and tetrakis(triphenylphosphine)palladium(0) (Tetrakis(triphenylphosphine)palladium(0), Pd(PPh) 3 ) 4)(0.05 equiv.) was dissolved in THF / H 2 O (0.2 M), and then the temperature was raised to 80 °C and stirred for 6 hours. After confirming the completion of the reaction by TLC, the crude solid product was obtained by extraction with EtOAc / H 2 O, and then purified by column chromatography to obtain Compound 9. MS: [M+H] + = 897.1

[0369] [Synthesis Example 10. Synthesis of Compound 10] [Chemical Formula]

[0370] Compound 10 was obtained in the same manner as the production method of Synthesis Example 1, except that Compound 8a was used instead of Compound 1a in Synthesis Example 1. MS: [M+H] + = 803.0

[0371] [Synthesis Example 11. Synthesis of Compound 11] [Chemical Formula]

[0372] Compound 11 was obtained in the same manner as the production method of Synthesis Example 1, except that Compound 6a was used instead of Compound 1a in Synthesis Example 1. MS: [M+H] + = 750.9

[0373] [Device Example] [Example 1] A glass substrate coated with ITO (indium tin oxide) with a thickness of 500 Å was placed in distilled water in which a detergent was dissolved and cleaned with ultrasonic waves. At this time, a product of Fischer Co. was used as the detergent, and distilled water that had been secondarily filtered with a filter of a product of Millipore Co. was used as the distilled water. After cleaning the ITO for 30 minutes, it was repeated twice with distilled water, and ultrasonic cleaning was carried out for 10 minutes. After the distilled water cleaning was completed, ultrasonic cleaning was carried out with solvents of isopropyl and acetone and dried, and then the substrate was cleaned for 5 minutes, and then the substrate was transported to a glove box.

[0374] On the ITO transparent electrode, a coating composition in which the following compound p-dopant and the following compound HIL with a weight ratio of 2:8 were dissolved in cyclohexanone at 5 wt / v% was spin-coated (2500 rpm) and heat-treated (cured) at 230 °C for 30 minutes to form a hole injection layer with a thickness of 1000 Å.

[0375] On the hole injection layer, a coating composition in which the following compound HTL (Mn: 27,900; Mw: 35,600; measured by GPC using a PC standard with an Agilent 1200 series) was dissolved in toluene at 2 wt / v% was spin-coated (2500 rpm) and heat-treated at 230 °C for 20 minutes to form a hole transport layer with a thickness of 1000 Å.

[0376] On the hole transport layer, a coating composition in which the following compound A and the following compound dopant with a weight ratio of 98:2 were dissolved in cyclohexanone at 2 wt / v% was spin-coated (2000 rpm) and heat-treated at 145 °C for 15 minutes to form a light-emitting layer with a thickness of 400 Å.

[0377] On the light-emitting layer, a coating composition prepared by dissolving Compound 1 produced in Synthesis Example 1 and lithium quinolate (Liq) at a weight ratio of 3:7 in a mixed solvent of ethylene glycol and 1-propanol (volume ratio of 8:2) at 2 wt / v% was spin-coated (2000 rpm) and heat-treated at 145 °C for 10 minutes to form an electron injection and transport layer with a thickness of 300 Å.

[0378] Aluminum was deposited on the electron injection and transport layer with a thickness of 1000 Å to form a cathode. In the above process, aluminum maintained a deposition rate of 2 Å / sec, and the vacuum degree during deposition was 5×10 -8 torr ~ 2×10 -7 torr.

[0379]

Chemical formula

[0380] 〔Examples 2 - 11〕 When manufacturing the electron injection and transport layer in Example 1, an organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds described in Table 1 below were used instead of Compound 1.

[0381] 〔Example 12〕 A glass substrate with a 500 Å thin film coating of ITO (indium tin oxide) was placed in distilled water in which a detergent was dissolved and washed with ultrasonic waves. At this time, a product from Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter from Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water, and ultrasonic cleaning was carried out for 10 minutes. After the distilled water washing was completed, ultrasonic cleaning was performed with solvents of isopropyl and acetone and dried, then the substrate was washed for 5 minutes, and then the substrate was transported to a glove box.

[0382] On the ITO transparent electrode, a coating composition in which the compound p-dopant and the compound HIL with a weight ratio of 2:8 were dissolved in cyclohexanone at 5 wt / v% was spin-coated (2500 rpm) and heat-treated (cured) at 230 °C for 30 minutes to form a hole injection layer with a thickness of 1000 Å.

[0383] On the hole injection layer, a coating composition in which the compound HTL was dissolved in toluene at 2 wt / v% was spin-coated (2500 rpm) and heat-treated at 230 °C for 20 minutes to form a hole transport layer with a thickness of 1000 Å.

[0384] On the hole transport layer, a coating composition in which the compound A and the compound dopant with a weight ratio of 98:2 were dissolved in cyclohexanone at 2 wt / v% was spin-coated (2000 rpm) and heat-treated at 145 °C for 15 minutes to form a light-emitting layer with a thickness of 400 Å.

[0385] On the light-emitting layer, the compound 1 produced in Synthesis Example 1 and lithium quinolate (Liq) with a weight ratio of 3:7 were vapor-deposited to a thickness of 200 Å to form an electron injection and transport layer. At this time, the vapor deposition rate was maintained at 1 Å / sec, and the degree of vacuum during vapor deposition was 1×10 -8 torr ~ 5×10 -7 torr was maintained.

[0386] On the electron injection and transport layer, aluminum was vapor-deposited to a thickness of 1000 Å to form a cathode. At this time, the vapor deposition rate was maintained at 2 Å / sec, and the degree of vacuum during vapor deposition was 5×10 -8 torr ~ 2×10 -7 torr was maintained.

[0387] 〔Examples 13 to 15〕 In Example 12, an organic light-emitting device was manufactured in the same manner as in Example 12, except that the compound described in Table 1 below was used instead of the compound 1 when manufacturing the electron injection and transport layer.

[0388] 〔Comparative Examples 1 and 2〕 In Example 1, an organic light-emitting device was fabricated in the same manner as in Example 1, except that the compound described in Table 1 below was used instead of Compound 1 during the production of the electron injection and transport layer.

[0389] [Comparative Examples 3 and 4] In Example 12, an organic light-emitting device was fabricated in the same manner as in Example 12, except that the compound described in Table 1 below was used instead of Compound 1 during the production of the electron injection and transport layer.

[0390] In Table 1 below, the structures of Compounds B to E are as follows. [Chemical formula]

[0391] The driving voltage, current efficiency, power efficiency, luminance, and lifetime (T95) of the organic light-emitting devices fabricated in the above Examples and Comparative Examples were measured at a current density of 10 mA / cm 2 , and the results are shown in Table 1 below. T95 means the time (hr) required for the luminance to decrease from the initial luminance (500 nit) to 95%.

[0392] [Table 1]

[0393] As shown in Table 1 above, it was confirmed that the organic light-emitting devices (Examples 1 to 15) to which the compound of Chemical Formula 1 containing deuterium according to the present invention was applied had a lower driving voltage, improved efficiency, and longer lifetime compared to the organic light-emitting devices (Comparative Examples 1 to 4) to which the compound not containing deuterium was applied. [Explanation of symbols]

[0394] 101 ··· Substrate 201 ··· First electrode 301 ··· Hole injection layer 401 ··· Hole transport layer 501 ··· Light-emitting layer 601 ··· Electron injection and transport layer 701 ··· Second electrode

Claims

1. A compound of the following chemical formula 1: 【Chemical 1】 In the above chemical formula 1, X1 to X4 are the same as or different from each other, and each independently is a group represented by the following chemical formula 2, X11 to X14 are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or combines with an adjacent group to form a substituted or unsubstituted ring, a1 to a4 are each an integer of 0 or 1, and a1 + a2 + a3 + a4 is an integer of 2 to 4, a11 to a14 are each an integer of 0 to 4. When a11 to a14 are each an integer of 2 or more, the substituents in the parentheses are the same as or different from each other, [Chemical 2] In the above chemical formula 2, Y1 is 0, S or Se, L1 is a direct bond; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, R1 and R2 are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, At least one of the above X1 to X4 and X11 to X14 contains deuterium.

2. The compound according to Claim 1, wherein the above chemical formula 1 is the following chemical formula 1-1 or 1-2: 【Chemical Formula 3】 In the above chemical formula 1-1 and 1-2, X1, X3, X4, X11 to X14, a11, a12 and a14 are the same as those defined in the above chemical formula 1, a11’, a13’, and a14’ are each an integer of 1 to 3. When a11’, a13’, and a14’ are each 2 or more, the substituents in the parentheses are the same as or different from each other.

3. The compound according to Claim 1, wherein the above chemical formula 1 is any one of the following chemical formulas 1-4 to 1-6: [Chemical Formula 4] 【Chemical Formula 5】 In the above chemical formulas 1-4 to 1-6, X1 to X4, X11, X13, X14, a1 to a4, a11, a13 and a14 are the same as those defined in chemical formula 1, X15 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group. At least one of X1 to X4, X11, and X13 to X15 contains deuterium, a15 is an integer from 1 to 6, and when a15 is an integer of 2 or more, the structures in parentheses are the same as or different from each other.

4. The compound according to claim 1, wherein R1 and R2 are the same as or different from each other, and each independently is hydrogen; deuterium; or a substituted or unsubstituted aryl group.

5. The compound according to claim 1, wherein X11 to X14 are the same as or different from each other, and each independently is hydrogen; deuterium; or a substituted or unsubstituted alkyl group, or forms a substituted or unsubstituted ring by bonding with an adjacent group.

6. The compound according to claim 1, wherein the compound of Chemical Formula 1 has a deuterium substitution rate of 20% or more.

7. The compound according to claim 1, wherein the compound of Chemical Formula 1 is any of the following structures: 【Chemical Formula 6】 【Chemical Formula 7】 【Chemical Formula 8】 【Chemical Formula 9】 。

8. A coating composition comprising the compound according to any one of claims 1 to 7.

9. A first electrode; A second electrode; and At least one organic layer provided between the first electrode and the second electrode comprising, An organic light-emitting device, wherein at least one layer of the organic layer contains the coating composition according to claim 8 or a cured product thereof.

10. The organic layer includes a light-emitting layer and a first organic layer, The organic light-emitting device according to claim 9, wherein the first organic layer contains the coating composition or a cured product thereof.

11. The second electrode is a cathode, The organic light-emitting device according to claim 10, wherein the first organic layer is provided between the light-emitting layer and the cathode.

12. The organic light-emitting device according to claim 10, wherein the first organic layer is at least one of an electron injection layer; an electron transport layer; and an electron injection and transport layer.

13. Preparing a first electrode; Forming at least one organic layer on the first electrode; and Forming a second electrode on the organic layer comprising, A method for manufacturing an organic light-emitting device, wherein the step of forming the organic layer includes forming at least one organic layer using the coating composition of claim 8.

14. The step of forming at least one organic layer using the coating composition includes Coating the coating composition on the first electrode; and The step of heat-treating or light-treating the coated coating composition The method for manufacturing an organic light-emitting device according to claim 13, comprising the step of

15. The step of preparing a first electrode; The step of forming at least one organic layer on the first electrode; and The step of forming a second electrode on the organic layer comprising The step of forming the organic layer includes the step of depositing the compound according to any one of claims 1 to 7 to form at least one organic layer. The method for manufacturing an organic light-emitting device

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