Novel compounds and organic light-emitting devices utilizing them

Abstract

The present invention provides a novel compound and an organic light-emitting device using the same.

Description

[Technical Field]

[0001] [Cross-reference of related applications] This application claims priority based on Korean Patent Application No. 10-2022-0070957 dated June 10, 2022, and all content disclosed in the said Korean Patent Application is incorporated herein as part of this specification. This invention relates to a novel compound and an organic light-emitting device containing the same. [Background technology]

[0002] Generally, organic luminescence refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting devices that utilize organic luminescence have a wide viewing angle, excellent contrast, and fast response time, and are being extensively researched due to their superior brightness, driving voltage, and response speed characteristics.

[0003] Organic light-emitting devices generally have a structure that includes a positive electrode, a negative electrode, and an organic layer between the positive and negative electrodes. The organic layer is often composed of multiple layers made of different materials to improve the efficiency and safety of the organic light-emitting device, such as a hole injection layer (HIL), a hole transport layer (HTL), an emission layer (EML), an electron transport layer (ETL), and an electron injection layer (HIL). In such an organic light-emitting device structure, when a voltage is applied between the two electrodes, holes are injected into the organic layer at the positive electrode and electrons are injected into the organic layer at the negative electrode. When the injected holes and electrons meet, an exciton is formed, and when this exciton returns to the ground state, it emits light.

[0004] There is a continuing need for the development of new materials for the organic substances used in the aforementioned organic light-emitting devices.

[0005] On the other hand, in recent years, organic light-emitting diodes (OLEDs) have been developed using solution processes, particularly inkjet processes, instead of conventional vapor deposition processes, in order to reduce process costs. Initially, attempts were made to develop OLEDs by coating all OLED layers with solution processes, but current technology has limitations, and hybrid processes are currently being researched in which only the HIL, HTL, and EML layers are carried out with solution processes, and the subsequent processes utilize conventional vapor deposition processes.

[0006] Therefore, the present invention provides a novel organic light-emitting material that can be used in organic light-emitting devices and can also be used in solution processes. [Prior art documents] [Patent Documents]

[0007] [Patent Document 1] Korean Patent Publication No. 10-2000-0051826 [Overview of the project] [Problems that the invention aims to solve]

[0008] This invention relates to a novel compound and an organic light-emitting device containing the same. [Means for solving the problem]

[0009] The present invention provides a compound represented by the following chemical formula 1: [ka]

[0010] In the aforementioned chemical formula 1, D stands for deuterium. R1 and R2 are, independently, hydrogen or deuterium. L1 to L4 are each independently single-bonded, substituted, or unsubstituted arylenes with 6 to 60 carbon atoms. Ar1 and Ar2 are each independently a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a heteroaryl having 2 to 60 carbon atoms containing one or more heteroatoms of N, O, and S, which is substituted or unsubstituted. a and b are each independently an integer from 0 to 8. c and d are each independently an integer from 0 to 5.

[0011] The present invention also provides an organic light-emitting device including a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain a compound represented by Chemical Formula 1.

Effect of the Invention

[0012] The compound represented by Chemical Formula 1 described above can be used as a material for the organic layer of an organic light-emitting device, can also be used in a solution process, and can improve the efficiency and lifetime characteristics in an organic light-emitting device.

Brief Description of the Drawings

[0013] [Figure 1] An example of an organic light-emitting device composed of a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4 is shown. [Figure 2] An example of an organic light-emitting device composed of a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 3, an electron injection and transport layer 7, and a negative electrode 4 is shown.

Embodiments for Carrying Out the Invention

[0014] Hereinafter, a more detailed description will be given for understanding the present invention.

[0015] (Definition of Terms) In this specification, the term “substituted or unsubstituted” means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; halogen groups; cyano groups; nitro groups; hydroxyl groups; carbonyl groups; ester groups; imide groups; amino groups; phosphine oxide groups; alkoxy groups; aryloxy groups; alkylthiooxy groups; arylthiooxy groups; alkylsulfoxy groups; arylsulfoxy groups; silyl groups; boron groups; alkyl groups; cycloalkyl groups; alkenyl groups; aryl groups; aralkyl groups; aralkylkenyl groups; alkylaryl groups; alkylamine groups; aralkylamine groups; heteroarylamine groups; arylamine groups; arylphosphine groups; or heterocyclic groups containing one or more N, O, and S atoms, or substituted or unsubstituted with substituents in which two or more substituents from the above-mentioned substituents are linked. For example, “substituents in which two or more substituents are linked” may be a biphenylyl group. That is, a biphenylyl group may also be an aryl group and can be interpreted as a substituent in which two phenyl groups are linked. For example, the term "substituted or unsubstituted" can be understood as "unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogens, cyano, C1-C10 alkyls, C1-C10 alkoxys, and C6-C20 aryls"; or "unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogens, cyano, methyl, ethyl, phenyl, and naphthyl." Also, in this specification, the term "substituted with one or more substituents" can be understood as "substituted with one to the maximum number of substituted hydrogens." Alternatively, in this specification, the term "substituted with one or more substituents" can be understood as "substituted with one to five substituents," or "substituted with one or two substituents."

[0016] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, the substituent has the following structure, but is not limited thereto. [ka]

[0017] In this specification, the ester group may be substituted with a linear, branched, or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the substituents are, but are not limited to, those shown in the structural formulas below. [ka]

[0018] In this specification, the number of carbon atoms in the imide group is not particularly limited, but it is preferably 1 to 25 carbon atoms. Specifically, the substituent has the following structure, but is not limited thereto. [ka]

[0019] In this specification, a substituted or unsubstituted silyl group means -Si(Z1)(Z2)(Z3), where Z1, Z2, and Z3 can each be independently hydrogen, deuterium, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C1-C60 haloalkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 haloalkenyl group, or a substituted or unsubstituted C6-C60 aryl group. According to one embodiment, Z1, Z2, and Z3 can each be independently hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C1-C10 haloalkyl group, a substituted or unsubstituted C1-C10 haloalkyl group, or a substituted or unsubstituted C6-C20 aryl group. Specific examples of the silyl group include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl groups.

[0020] In this specification, the boron group specifically refers to, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like.

[0021] In this specification, examples of halogen groups include fluoro, chloro, bromo, or iodine.

[0022] In this specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited but is preferably 1 to 40. In one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. In another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. In yet another embodiment, specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethyl-propyl, 1,1-dimethylpropyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2 Examples include, but are not limited to, ethylbutyl, heptyl, n-heptyl, isohexyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2,4,4-trimethyl-1-pentyl, 2,4,4-trimethyl-2-pentyl, 2-propylpentyl, n-nonyl, and 2,2-dimethylheptyl.

[0023] In this specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. In one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. In another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. In yet another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. Specific examples include, but are not limited to, vinyl, 1-profenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, etc.

[0024] In this specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. In one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. In yet another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl.

[0025] In this specification, an aryl group is understood to mean a substituent derived from an aromatic monocyclic or fused polycyclic compound containing only carbon as a ring-forming atom, and the number of carbon atoms is not particularly limited, but is preferably 6 to 60. In one embodiment, the number of carbon atoms of the aryl group is 6 to 30. In another embodiment, the number of carbon atoms of the aryl group is 6 to 20. Examples of monocyclic aryl groups include, but are not limited to, a phenyl group, a biphenylyl group, a terphenylyl group, etc. Examples of polycyclic aryl groups include, but are not limited to, a naphthyl group, anthracenyl group, a phenanthryl group, a pyrenyl group, a perilenyl group, a chrysenyl group, a fluorenyl group, etc.

[0026] In this specification, the fluorenyl group may be substituted, and two substituents may bond to each other to form a spiro structure. When the fluorenyl group is substituted, [ka] These are some examples, but they are not limited to these.

[0027] In this specification, a heteroaryl group means a substituent derived from a monocyclic or fused polycyclic compound that is a ring-forming atom and further contains one or more heteroatoms selected from N, O, and S in addition to carbon, and means an aromatic substituent. In one embodiment, the heteroaryl group has 2 to 60 carbon atoms. In another embodiment, the heteroaryl group has 2 to 30 carbon atoms. In yet another embodiment, the heteroaryl group has 2 to 20 carbon atoms. Examples of the heteroaryl groups mentioned above include, but are not limited to, thiophenyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridinyl, bipyridinyl, pyrimidinyl, triazinyl, acridinyl, pyridadinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyradinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, dibenzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, and phenothiazinyl.

[0028] In this specification, among aralkyl groups, aralkenyl groups, alkylaryl groups, arylamine groups, and arylsilyl groups, the aryl group is the same as the example of aryl group described above. In this specification, among aralkyl groups, alkylaryl groups, and alkylamine groups, the alkyl group is the same as the example of alkyl group described above. In this specification, among heteroarylamines, the heteroaryl can be described using the description of heteroaryl described above. In this specification, among aralkenyl groups, the alkenyl group is the same as the example of alkenyl group described above. In this specification, among arylenes, the description of aryl groups described above can be described using the description of aryl group described above, except that they are divalent groups. In this specification, among heteroarylenes, the description of heteroaryl described above can be described using the description of heteroaryl described above, except that they are divalent groups. In this specification, among hydrocarbon rings, the hydrocarbon ring is not a monovalent group but is formed by the bonding of two substituents. In this specification, among heterocycles, the heterocyclic ring is not a monovalent group but is formed by the bonding of two substituents.

[0029] In this specification, “deuterated or deuterated” means that at least one of the substituted hydrogen atoms in the compound, the divalent linking group, or the monovalent substituent is substituted with deuterium.

[0030] Furthermore, the phrase "unsubstituted or deuterium-substituted" or "deuterium-substituted or unsubstituted" means "unsubstituted or one to the maximum number of replaceable hydrogen atoms are substituted with deuterium." For example, the term "unsubstituted or deuterium-substituted phenanthryl" can be understood as "unsubstituted or phenanthryl with one to nine deuterium atoms," considering that the maximum number of deuterium-substituted hydrogen atoms in a phenanthryl structure is nine.

[0031] Furthermore, the term "deuterated structure" encompasses all compounds, divalent linking groups, or monovalent substituents in which at least one hydrogen atom is substituted with deuterium. For example, the deuterated structure of phenyl can be understood as referring to all monovalent substituents in which at least one substitutable hydrogen atom within the phenyl group is substituted with deuterium, as shown below. [ka]

[0032] Furthermore, the "deuterium substitution rate" or "degree of deuteration" of a compound refers to the ratio, calculated as a percentage, of the number of substituted deuterium atoms to the total number of hydrogen atoms that can exist in the compound (the sum of the number of hydrogen atoms that can be substituted with deuterium and the number of substituted deuterium atoms). Therefore, a "deuterium substitution rate" or "degree of deuteration" of a compound being "K%" means that K% of the hydrogen atoms that can be substituted with deuterium in the compound have been substituted with deuterium.

[0033] At this time, the "deuterium substitution rate" or "degree of deuteration" is determined by MALDI-TOFMS (Matrix-Assisted Laser Desorption / Ionization Time-of-Flight Mass Spectrometer), nuclear magnetic resonance spectroscopy ( 1 The deuterium can be measured using commonly known methods such as 1H NMR, TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or GC / MS (Gas Chromatography / Mass Spectrometry). More specifically, when using MALDI-TOFMS, the "deuterium substitution rate" or "degree of deuteration" can be determined by first finding the number of deuterium atoms substituted in the compound via MALDI-TOFMS analysis, and then calculating the ratio of the number of substituted deuterium atoms to the total number of hydrogen atoms that can exist in the compound, as a percentage.

[0034] (compound) The present invention provides a compound represented by the chemical formula 1.

[0035] Anthracene-based compounds, which have conventionally been used as host materials, are low molecular weight compounds with a molecular weight of 400-600 g / mol. While they have excellent solubility in solvents and can be used to form an emissive layer in a solution process, there is a problem when applying a separate layer, such as an electron transport layer, to the emissive layer in a solution process afterward, due to their poor resistance to the solvent used for electron transport layer formation. This created a need for organic materials that exhibit high solubility in solvents for forming the luminescent layer, while simultaneously showing resistance to solvents for forming hole blocking layers, electron transport layers, or electron injection and transport layers that can be provided on the luminescent layer.

[0036] Therefore, from the viewpoint of molecular orbital activity, the inventors have confirmed that in the case of a compound having a (naphthylene)-(naphthylene) linker and containing two anthracene structures, when the naphthylenes are linked to each other at the 2,2' positions and anthracene is linked to one of the 5,7, and 8 positions and one of the 5',7', and 8' positions, the compound can exhibit high molecular weight sufficient to be resistant to solvents for the formation of separate layers on the luminescent layer, while also exhibiting high solubility in solvents for the formation of the luminescent layer, thus completing the present invention.

[0037] The compound represented by chemical formula 1 is a compound having a structure in which two anthracene rings are linked by a binaphthylene linker, characterized in that the naphthylene groups are linked to each other at the 2,2' positions, and anthracene is linked to one of the 5,7, and8 positions and one of the 5',7', and8' positions.

[0038] The compound represented by chemical formula 1 exhibits superior material stability due to its structural characteristics compared to compounds having a structure in which binaphthylene linkers are bonded to two anthracenes at the 6th and 6' positions, and compounds in which the binaphthylene linkers are not bonded to each other at the 2,2' positions.

[0039] Specifically, compounds with a molecular weight above a certain level face the problem of not dissolving in the solvent used in the solution process due to the increased molecular weight. Therefore, in order to improve solubility in the solvent, an intramolecular twist form should be sufficiently induced. From the perspective of molecular orbital analysis, in the case of a compound that has a (naphthylene)-(naphthylene) linker and contains two anthracene structures, an intramolecular twist form can be effectively induced when the naphthylene groups are linked to each other at the 2,2' positions, and when anthracene is linked to one of the 5,7, and 8 positions and one of the 5',7', and 8' positions.

[0040] As a result, the compound represented by chemical formula 1 has a molecular weight above a certain level and exhibits resistance to solvents for forming a separate layer on the light-emitting layer. At the same time, it has higher solubility to compounds having a different binaphthylene linker than the one represented by chemical formula 1, and the light-emitting layer can be effectively formed in a solution step using the compound. Therefore, the efficiency and lifespan of the final organic light-emitting device containing the compound represented by chemical formula 1 as the light-emitting layer can be improved.

[0041] Specifically, the bonding positions between the binaphthylene linker and L1 and L2 in the compound represented by chemical formula 1 are as follows: [ka]

[0042] In the aforementioned chemical formula 1, L1 is bonded to one of the carbon atoms at position *5, *7, or *8 of the binaphthylene linker. L2 bonds to one of the carbon atoms at the *5', *7', or *8' positions of the binaphthylene linker.

[0043] Specifically, if the bonding positions between the binaphthylene linker and L1 and L2 are denoted as (L1 bonding position, L2 bonding position), then the bonding positions between the binaphthylene linker and L1 and L2 can be (*5, *5'), (*5, *7'), (*5, *8'), (*7, *7'), (*7, *8'), or (*8, *8').

[0044] Of these, it is preferable from the standpoint of ease of synthesis that the bonding positions between the binaphthylene linker and L1 and L2 are (*5, *5'), (*7, *7'), or (*8, *8').

[0045] In the above chemical formula 1, R1 and R2 may all be hydrogen or all be deuterium.

[0046] Furthermore, L1 to L4 can each be independently single-bonded, unsubstituted, or deuterium-substituted arylenes having 6 to 20 carbon atoms.

[0047] Furthermore, L1 to L4 can each independently be a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenyldiyl, or a substituted or unsubstituted naphthylene.

[0048] Furthermore, L1 to L4 can each be independently a single bond; 1,2-phenylene that is unsubstituted or substituted with 1 to 4 deuterium atoms; 1,3-phenylene that is unsubstituted or substituted with 1 to 4 deuterium atoms; or 1,4-phenylene that is unsubstituted or substituted with 1 to 4 deuterium atoms.

[0049] Specifically, are L1 and L2 all single bonds; or One of L1 and L2 is a single bond, and the other can be unsubstituted or a phenylene molecule substituted with 1 to 4 deuterium atoms.

[0050] For example, L1 and L2 are both single bonds; or One of L1 and L2 is a single bond, and the other may be unsubstituted or substituted with 1 to 4 deuterium atoms in 1,2-phenylene; unsubstituted or substituted with 1 to 4 deuterium atoms in 1,3-phenylene; or unsubstituted or substituted with 1 to 4 deuterium atoms in 1,4-phenylene.

[0051] Furthermore, specifically, L3 and L4 are all single bonds; or One of L3 and L4 is a single bond, and the other can be unsubstituted or a phenylene molecule substituted with 1 to 4 deuterium atoms.

[0052] For example, L3 and L4 are both single bonds; or One of L3 and L4 is a single bond, and the other may be unsubstituted or substituted with 1 to 4 deuterium atoms in 1,2-phenylene; unsubstituted or substituted with 1 to 4 deuterium atoms in 1,3-phenylene; or unsubstituted or substituted with 1 to 4 deuterium atoms in 1,4-phenylene.

[0053] Furthermore, L1~L4 are all single bonds; or One of L1 to L4 is either unsubstituted or 1,2-phenylene substituted with 1 to 4 deuterium atoms; 1,3-phenylene substituted with 1 to 4 deuterium atoms; or 1,4-phenylene substituted with 1 to 4 deuterium atoms; and the rest can all be single bonds.

[0054] Furthermore, L1 and L2 may be the same as each other. In different forms, L1 and L2 may be different.

[0055] Furthermore, L3 and L4 may be the same as each other. In different forms, L3 and L4 may be different.

[0056] Furthermore, Ar1 and Ar2 may each independently be substituted or unsubstituted aryl atoms having 6 to 20 carbon atoms; or 2 to 20 carbon atoms having 2 to 20 carbon atoms containing one or two heteroatoms from substituted or unsubstituted N, O, and S.

[0057] Furthermore, Ar1 and Ar2 may each be independently a C6-C20 aryl molecule that is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and phenyl; or a C2-C20 heteroaryl molecule containing one or two heteroatoms from N, O, and S that is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and phenyl.

[0058] Specifically, Ar1 and Ar2 may independently be substituted or unsubstituted phenyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted phenylcarbazolyl.

[0059] More specifically, Ar1 and Ar2 are independently phenyl, biphenylyl, naphthyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, or phenylcarbazolyl. Here, Ar1 and Ar2 can be unsubstituted or substituted with one or more deuterium atoms.

[0060] Furthermore, Ar1 and Ar2 may be the same as each other. In different forms, Ar1 and Ar2 may be different.

[0061] Furthermore, L3-Ar1 and L4-Ar2 may be the same as each other. In different forms, L3-Ar1 and L4-Ar2 may be different.

[0062] Furthermore, a and b, which represent the number of deuterium atoms, are independently 0, 1, 2, 3, 4, 5, 6, 7, or 8, and c and d are independently 0, 1, 2, 3, 4, or 5.

[0063] In one embodiment, a+b+c+d may be 0 or 10 or greater. For example, a+b+c+d is 0, or 10 or greater, 15 or greater, 20 or greater, 25 or greater, 26 or greater, 27 or greater, or 28 or greater, and may be 36 or less.

[0064] Furthermore, the compound can be represented by any of the following chemical formulas 1-1 to 1-3:

[0065] [ka]

[0066] [ka]

[0067] In the above chemical formulas 1-1 to 1-3, R1, R2, L1-L4, Ar1, Ar2, and a-d are as defined in Chemical Formula 1 above.

[0068] Furthermore, the compound may be deuterium-free or may contain one or more deuterium atoms. Specifically, the compound may not contain deuterium, or it may contain 1 or more, 5 or more, 10 or more, 20 or more, 30 or more, 35 or more, or 40 or more, 60 or less, 55 or less, 50 or less, 49 or less, 48 ​​or less, 47 or less, or 46 or less deuterium atoms.

[0069] More specifically, the deuterium substitution rate of the compound may be 0% or 80% or more.

[0070] For example, if the compound contains deuterium, the deuterium substitution rate of the compound may be 1% to 100%. Specifically, the deuterium substitution rate of the compound may be 5% or more, 10% or more, 20% or more, 30% or more, 40% or more, 50% or more, 60% or more, 70% or more, or 80% or more, and may be 100% or less, 95% or less, or 90% or less.

[0071] Furthermore, the compound has a molecular weight of 800 g / mol or more. More specifically, the compound has a molecular weight (g / mol) of 850 or more, 860 or more, 870 or more, 880 or more, 890 or more, 900 or more, 910 or more, 920 or more, or 930 or more, and may be 2,000 or less, 1,500 or less, 1,300 or less, 1,200 or less, 1,100 or less, 1,080 or less, 1,060 or less, 1,040 or less, 1,020 or less, or 1,000 or less.

[0072] In this case, if you wish to indicate the number of deuterium substitutions in the aforementioned compound, you can represent it using the following chemical formula 1D: [ka]

[0073] In the aforementioned chemical formula 1D, Dn means that n hydrogen atoms are replaced by deuterium. Here, n is a non-negative integer, R'1, R'2, L'1-L'4, Ar'1, and Ar'2 refer to the R1, R2, L1-L4, Ar1, and Ar2 substituents, respectively, that are not substituted with deuterium.

[0074] In one embodiment, when the compound has at least one deuterium atom, n in the chemical formula 1D is an integer of 1 or more.

[0075] On the other hand, a typical example of the compound represented by chemical formula 1 is selected from the group of compounds represented by the following chemical formulas and their deuterated structures:

[0076]

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[0077]

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[0078]

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[0079]

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[0080]

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[0081]

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[0082]

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[0083]

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[0084]

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[0085]

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[0086]

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[0087] [ka]

[0088] On the other hand, the compound represented by chemical formula 1 can be produced by a manufacturing method as shown in reaction formula 1 below, for example, when a, b, c, and d are 0. [ka]

[0089] The definitions for each substituent in the above reaction equation 1 are as described above.

[0090] Specifically, the compound represented by chemical formula 1 can be produced through a Suzuki coupling reaction between compound SM1, which has an OTf(-O3SCF3) group introduced as a reactant for the Suzuki coupling reaction, and compound SM2. In this case, the Suzuki coupling reaction is preferably carried out in the presence of a palladium catalyst and a base, respectively. Furthermore, the reactant for the Suzuki coupling reaction may be changed as appropriate.

[0091] Furthermore, compounds represented by chemical formula 1 that contain at least one deuterium (i.e., compounds in chemical formula 1D where n is an integer greater than 0 (an integer n of 1 or more)) can be produced by a manufacturing method as shown in the reaction equation 2 below. [ka]

[0092] The definitions for each substituent in the above reaction equation 2 are as described above.

[0093] Specifically, a compound represented by chemical formula 1 containing at least one deuterium atom can be produced by deuterating a compound represented by chemical formula 1 that is not substituted with deuterium. In this case, the deuterium substitution reaction can be carried out by adding the compound represented by chemical formula 1 that is not substituted with deuterium to a deuterated solvent such as a benzene-D6 (C6D6) solution, and then reacting it with TfOH (trifluoromethane sulfonic acid).

[0094] On the other hand, the compounds represented by chemical formula 1 can be produced by appropriately changing the reactants in reaction formulas 1 and 2, and the methods for producing these compounds will be further elaborated in the production examples described later.

[0095] On the other hand, the compound represented by chemical formula 1 has high solubility in organic solvents used in solution processes, such as cyclohexanone, and is suitable for use in large-area solution processes such as inkjet coating, which use solvents with high boiling points.

[0096] The organic layer containing the compound according to the present invention can be formed using various methods such as vacuum deposition and solution processes, the solution process will be described in detail below.

[0097] (Coating composition) On the other hand, the compound according to the present invention can form an organic layer, particularly a light-emitting layer, of an organic light-emitting device in a solution process. Specifically, the compound can be used as a host material for the light-emitting layer. For this purpose, the present invention provides a coating composition comprising the compound and solvent according to the present invention as described above.

[0098] The solvent is not particularly limited as long as it can dissolve or disperse the compound according to the present invention, and includes, for example, chlorine-based solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, and o-dichlorobenzene; ether-based solvents such as tetrahydrofuran and dioxane; aromatic hydrocarbon-based solvents such as toluene, xylene, trimethylbenzene, mesitylene, 1-methylnaphthalene, and 2-methylnaphthalene; aliphatic hydrocarbon-based solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; ketone-based solvents such as acetone, methyl ethyl ketone, and cyclohexanone; ester-based solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; and ethylene glycol and ethylene glycol mono Examples of solvents include polyhydric alcohols and their derivatives such as butyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, and 1,2-hexanediol; alcoholic solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; and amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; benzoate solvents such as butyl benzoate, methyl-2-methoxybenzoate, and ethyl benzoate; phthalate solvents such as dimethyl phthalate, diethyl phthalate, and diphenyl phthalate; tetralin; and 3-phenoxytoluene. Furthermore, the above solvents can be used individually or in combination of two or more. Preferably, cyclohexanone can be used as the solvent.

[0099] Furthermore, the coating composition may further contain compounds used as dopant materials, and a description of the compounds used as dopant materials will be given later.

[0100] Furthermore, the viscosity of the coating composition is preferably 1 cP or higher. Also, considering the ease of coating, the viscosity of the coating composition is preferably 10 cP or lower. Furthermore, the concentration of the compound according to the present invention in the coating composition is preferably 0.1 wt / v% or higher. Furthermore, in order to ensure that the coating composition is optimally coated, the concentration of the compound according to the present invention in the coating composition is preferably 20 wt / v% or lower.

[0101] Furthermore, the solubility (wt%) of the compound represented by chemical formula 1 at room temperature / atmospheric pressure may be 0.1 wt% or more, more specifically 0.1 wt% to 5 wt%, based on the solvent cyclohexanone. Therefore, the coating composition containing the compound represented by chemical formula 1 and the solvent can be used in solution-based processes.

[0102] Furthermore, the present invention provides a method for forming a light-emitting layer using the above-described coating composition. Specifically, this method includes the steps of: coating the above-described light-emitting layer according to the present invention onto a positive electrode or onto a hole transport layer formed on a positive electrode using a solution process; and heat-treating the coated coating composition.

[0103] The aforementioned solution step is a step using the coating composition according to the present invention described above, and includes, but is not limited to, spin coating, dip coating, doctor bladeding, inkjet printing, screen printing, spray method, and roll coating.

[0104] In the heat treatment step, the heat treatment temperature is preferably 150 to 230°C. The heat treatment time is 1 minute to 3 hours, more preferably 10 minutes to 1 hour. Furthermore, the heat treatment is preferably carried out in an inert gas atmosphere such as argon or nitrogen.

[0105] (Organic light-emitting device) On the other hand, the present invention provides an organic light-emitting device comprising a compound represented by the chemical formula 1. For example, the present invention provides an organic light-emitting device comprising a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprises a compound represented by the chemical formula 1. The organic layer of the organic light-emitting element of the present invention may consist of a single layer, but it can also consist of a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting element of the present invention may have a structure in which the organic layer includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and so on. However, the structure of the organic light-emitting element is not limited thereto and may include fewer organic layers.

[0106] In one embodiment, the organic layer may include a light-emitting layer, in which case the organic layer containing the compound may be the light-emitting layer.

[0107] In other embodiments, the organic layer may include a hole injection layer, a hole transport layer, a light-emitting layer, and an electron injection and transport layer, in which case the organic layer containing the compound may be the light-emitting layer or the electron injection and transport layer.

[0108] In yet another embodiment, the organic layer may include a hole injection layer, a hole transport layer, an electron suppression layer, an emissive layer, and an electron injection and transport layer, in which case the organic layer containing the compound may be an emissive layer or an electron injection and transport layer.

[0109] In yet another embodiment, the organic layer may include a hole injection layer, a hole transport layer, an electron suppression layer, an emitting layer, an electron blocking layer, and an electron injection and transport layer, in which case the organic layer containing the compound may be an emitting layer or an electron injection and transport layer.

[0110] The organic layer of the organic light-emitting element of the present invention may consist of a single layer, but it can also consist of a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting element of the present invention may have a structure in which, in addition to the light-emitting layer, the organic layer further includes a hole injection layer and a hole transport layer between the first electrode and the light-emitting layer, and an electron transport layer and an electron injection layer between the light-emitting layer and the second electrode. However, the structure of the organic light-emitting element is not limited thereto and may include fewer or more organic layers.

[0111] Furthermore, the organic light-emitting element according to the present invention may be an organic light-emitting element with a normal type structure in which the positive electrode, one or more organic layers, and the negative electrode are sequentially stacked on a substrate, with the first electrode being the positive electrode and the second electrode being the negative electrode. Furthermore, the organic light-emitting element according to the present invention may be an organic light-emitting element with an inverted type structure in which the negative electrode, one or more organic layers, and the positive electrode are sequentially stacked on a substrate, with the first electrode being the negative electrode and the second electrode being the positive electrode. For example, the structure of an organic light-emitting element according to one embodiment of the present invention is shown in Figures 1 and 2.

[0112] Figure 1 shows an example of an organic light-emitting device consisting of a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4. In such a structure, the compound represented by chemical formula 1 can be included in the light-emitting layer.

[0113] Figure 2 shows an example of an organic light-emitting element comprising a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 3, an electron injection and transport layer 7, and a negative electrode 4. In such a structure, the compound represented by chemical formula 1 can be included in the light-emitting layer.

[0114] The organic light-emitting element according to the present invention can be manufactured using materials and methods well known in the art, except that the light-emitting layer contains the compound according to the present invention and is manufactured as described above.

[0115] For example, the organic light-emitting element according to the present invention can be manufactured by sequentially stacking a positive electrode, an organic layer, and a negative electrode on a substrate. In this case, a positive electrode can be formed by depositing a metal or a conductive metal oxide, or an alloy thereof, onto a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation. An organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer can then be formed on top of the positive electrode, and finally, a material that can be used as a negative electrode can be deposited on top of that.

[0116] In addition to this method, organic light-emitting diodes can also be manufactured by sequentially depositing a negative electrode material, an organic layer, and a positive electrode material onto a substrate (WO2003 / 012890). However, the manufacturing method is not limited to this.

[0117] For example, the first electrode is a positive electrode and the second electrode is a negative electrode, or the first electrode is a negative electrode and the second electrode is a positive electrode.

[0118] The cathode material is preferably a material with a large work function so that hole implantation is smooth in the organic layer. Specific examples of the cathode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline.

[0119] The anode material is preferably a material with a small work function so as to facilitate electron injection into the organic layer. Specific examples of the anode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer materials such as LiF / Al or LiO2 / Al.

[0120] The hole injection layer is a layer into which holes are injected from the electrode. The hole injection material is preferably a compound that has the ability to transport holes, has a hole injection effect at the positive electrode, has an excellent hole injection effect on the light-emitting layer or light-emitting material, prevents the movement of excitons generated in the light-emitting layer to the electron injection layer or electron injection material, and has excellent thin-film formation ability. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metal porphyrins, oligothiophenes, arylamine-based organic compounds, hexanitrile-hexazatriphenylene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinones, and polyaniline and polythiophene-based conductive polymers.

[0121] The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. The hole transport material is suitable for a material that can receive holes from the positive electrode or hole injection layer and transport them to the light-emitting layer, and has high mobility for holes. The hole transport material can be a compound represented by chemical formula 1, or an arylamine-based organic compound, a conductive polymer, or a block copolymer having both conjugated and non-conjugated parts, but is not limited to these.

[0122] On the other hand, the organic light-emitting element may be provided with an electron suppression layer between the hole transport layer and the light-emitting layer. The electron suppression layer is formed on the hole transport layer and preferably in contact with the light-emitting layer, and plays a role in improving the efficiency of the organic light-emitting element by adjusting the hole mobility, preventing excessive electron movement, and increasing the probability of hole-electron bonding. The electron suppression layer includes an electron-blocking substance, and examples of such an electron-blocking substance include the compound represented by chemical formula 1, or an arylamine-based organic substance, but is not limited to these.

[0123] The light-emitting layer may include a host material and a dopant material. As the host material, the compound represented by chemical formula 1 is used. In addition, as the host material, a condensed aromatic ring derivative or a heterocycle-containing compound may be used together with the compound represented by chemical formula 1. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluorantene compounds, etc., and heterocycle-containing compounds include, but are not limited to, carbazol derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc.

[0124] Furthermore, dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluorantene compounds, and metal complexes. Specifically, aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, such as pyrene, anthracene, chrysene, and perifurantene, which have arylamino groups. Styrylamine compounds include compounds in which at least one arylvinyl group is substituted onto a substituted or unsubstituted arylamine, and which have one or more substituents selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamino groups, which are substituted or unsubstituted. Specifically, these include styrylamine, styryldiamine, styryltriamine, and styryltetraamine, but are not limited to these. Furthermore, metal complexes include iridium complexes and platinum complexes, but are not limited to these.

[0125] On the other hand, the organic light-emitting element may be provided with a hole-blocking layer between the light-emitting layer and the electron transport layer. The hole-blocking layer is formed on the light-emitting layer, preferably in contact with the light-emitting layer, and plays a role in improving the efficiency of the organic light-emitting element by adjusting electron mobility to prevent excessive movement of holes and increasing the probability of hole-electron bonding. The hole-blocking layer contains a hole-blocking substance, and examples of such hole-blocking substances include, but are not limited to, compounds into which electron-withdrawing groups have been introduced, such as triazine-containing azine derivatives; triazole derivatives; oxadiazole derivatives; penanthroline derivatives; and phosphine oxide derivatives.

[0126] The electron injection and transport layer is a layer that simultaneously performs the roles of an electron transport layer and an electron injection layer, injecting electrons from the electrode and transporting the received electrons to the light-emitting layer, and is formed on the light-emitting layer or the hole blocking layer. Suitable electron injection and transport materials are those that can readily receive electron injections from the negative electrode and transport them to the light-emitting layer, and that have high electron mobility. Specific examples of electron injection and transport materials include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; hydroxyflavone-metal complexes; and triazine derivatives. Alternatively, they can be used with, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyrandioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthrone, and their derivatives, metal complex compounds, or nitrogen-containing five-membered ring derivatives.

[0127] The electron injection and transport layers may be formed as separate layers, such as an electron injection layer and an electron transport layer. In such cases, the electron transport layer is formed on the light-emitting layer or the hole-blocking layer, and the electron transport material included in the electron transport layer is one of the electron injection and transport materials described above. The electron injection layer is formed on the electron transport layer, and the electron injection material included in the electron injection layer may be LiF, NaCl, CsF, Li2O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, thiopyrandioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives.

[0128] Examples of the aforementioned metal complex compounds include, but are not limited to, 8-hydroxyquinolina tritium, bis(8-hydroxyquinolina)zinc, bis(8-hydroxyquinolina)copper, bis(8-hydroxyquinolina)manganese, tris(8-hydroxyquinolina)aluminum, tris(2-methyl-8-hydroxyquinolina)aluminum, tris(8-hydroxyquinolina)gallium, bis(10-hydroxybenzo[h]quinolina)beryllium, bis(10-hydroxybenzo[h]quinolina)zinc, bis(2-methyl-8-hydroxyquinolina)chlorogallium, bis(2-methyl-8-hydroxyquinolina)(o-crezolat)gallium, bis(2-methyl-8-hydroxyquinolina)(1-naphthorato)aluminum, and bis(2-methyl-8-hydroxyquinolina)(2-naphthorato)gallium.

[0129] In addition to the materials described above, the light-emitting layer, hole injection layer, hole transport layer, electron transport layer, and electron injection layer may also contain inorganic compounds or polymer compounds such as quantum dots. The quantum dots are, for example, colloidal quantum dots, alloy quantum dots, core-type quantum dots, or core-shell quantum dots. The quantum dots contain elements belonging to groups 2 and 16, groups 13 and 15, groups 13 and 17, groups 11 and 17, or groups 14 and 15, and quantum dots containing elements such as cadmium (Cd), selenium (Se), zinc (Zn), sulfur (S), phosphorus (P), indium (In), tellurium (Te), lead (Pb), gallium (Ga), and arsenic (As) can be used.

[0130] The organic light-emitting element according to the present invention is a back-emitting element, a top-emitting element, or a double-sided light-emitting element, and is particularly a back-emitting element for which relatively high luminous efficiency is required.

[0131] Furthermore, the compounds according to the present invention may be included not only in organic light-emitting devices but also in organic solar cells or organic transistors.

[0132] The manufacture of the compound represented by the above chemical formula 1 and the organic light-emitting element containing it will be specifically described in the following examples. However, the following examples are for illustrative purposes only and do not limit the scope of the present invention. [Examples]

[0133] Manufacturing Example 1: Manufacturing of Compound 1 [ka]

[0134] Compounds 1-a (1.0 eq.) and 1-b (1.1 eq.) were placed in a round-bottom flask and dissolved in THF. Cs2CO3 (5.0 eq.) dissolved in water was added. Pd(PPh3)4 (10 mol%) was added dropwise under a bath temperature of 80°C and the mixture was stirred for 3 days. After the reaction, the reaction mixture was cooled to room temperature, thoroughly diluted with butyl, and then washed with butyl / brine to separate the organic layer. Water was removed with MgSO4 and the mixture was passed through a celite-florisil-silica pad. The resulting solution was concentrated under reduced pressure and then purified by column chromatography to produce compound 1-c (73% yield).

[0135] Compound 1-c (1.0 eq.) was placed in a round-bottom flask and dissolved in anhydrous CH2Cl2. Then, pyridine (2.0 eq.) was added dropwise at room temperature, and the bath temperature was lowered to 0°C and the mixture was stirred for 10 minutes. Subsequently, Tf2O (1.2 eq.) dissolved in anhydrous CH2Cl2 was slowly added dropwise to the mixture using a dropping funnel, and the bath temperature was gradually raised from 0°C to room temperature, after which the mixture was stirred overnight. After the reaction, the reaction product was sufficiently diluted with CH2Cl2, and the organic layer was separated by washing with water using CH2Cl2 / brine. Water was removed with MgSO4 and the mixture was passed through a Celite-Florisil-Silica pad. The resulting solution was concentrated under reduced pressure and purified by column chromatography to produce compound 1-d (99% yield).

[0136] Compounds 1-d (1.0 eq.) and 1-e (1.1 eq.) were placed in a round-bottom flask and dissolved in THF. Na2CO3 (3.0 eq.) dissolved in water was added. Pd(PPh3)4 (10 mol%) was added dropwise under a bath temperature of 80°C and stirred overnight. After the reaction, the reaction mixture was cooled to room temperature, thoroughly diluted with butyl, and then washed with butyl / brine to separate the organic layer. Water was removed with MgSO4 and the mixture was passed through a celite-florisil-silica pad. The resulting solution was concentrated under reduced pressure and purified by column chromatography to produce compound 1-f (71% yield). Compound 1-f (1.0 eq.) was placed in a round-bottom flask and dissolved in anhydrous CH2Cl2. Then, pyridine (2.0 eq.) was added dropwise at room temperature, and the bath temperature was lowered to 0°C and the mixture was stirred for 10 minutes. Subsequently, Tf2O (1.2 eq.) dissolved in anhydrous CH2Cl2 was slowly added dropwise to the mixture using a dropping funnel, and the bath temperature was gradually raised from 0°C to room temperature, after which the mixture was stirred overnight. After the reaction, the reaction product was sufficiently diluted with CH2Cl2, and the organic layer was separated by washing with water using CH2Cl2 / brine. Water was removed with MgSO4 and the solution was passed through a Celite-Florisil-Silica pad. The solution was concentrated under reduced pressure and purified by column chromatography to produce compound 1-g (99% yield).

[0137] Compound 1-g (1.0 eq.) and compound 1-h (1.1 eq.) were placed in a round-bottom flask and dissolved in THF. Na2CO3 (3.0 eq.) dissolved in water was added. Pd(PPh3)4 (10 mol%) was added dropwise under a bath temperature of 80°C and stirred overnight. After the reaction, the reaction mixture was cooled to room temperature, thoroughly diluted with butyl, and then washed with butyl / brine to separate the organic layer. Water was removed with MgSO4 and the mixture was passed through a celite-florisil-silica pad. The resulting solution was concentrated under reduced pressure and purified by column chromatography to produce compound 1 (84% yield). m / z[M+H] + 935.4

[0138] Manufacturing Example 2: Manufacturing of Compound 2 [ka]

[0139] In this synthesis, compound 2 was prepared in the same manner as compound 1, except that compound 2-a was used instead of compound 1-h. m / z[M+H] + 935.4

[0140] Manufacturing Example 3: Manufacturing of Compound 3 [ka]

[0141] In this synthesis, compound 3 was prepared in the same manner as compound 1, except that compound 3-a was used instead of compound 1-h. m / z[M+H] + 935.4

[0142] Manufacturing Example 4: Manufacturing of Compound 4 [ka]

[0143] In this synthesis, compound 4 was prepared in the same manner as compound 1, except that compound 4-a was used instead of compound 1-h. m / z[M+H] + 935.4

[0144] Manufacturing Example 5: Manufacturing of Compound 5 [ka]

[0145] In this synthesis, compound 5 was prepared in the same manner as compound 1, except that compound 5-a was used instead of compound 1-h. m / z[M+H] + 935.4

[0146] Manufacturing Example 6: Manufacturing of Compound 6 [ka]

[0147] In this synthesis, compound 6 was produced in the same manner as compound 1, except that compound 6-a was used instead of compound 1-b, compound 6-b instead of compound 1-c, compound 6-c instead of compound 1-d, compound 6-d instead of compound 1-f, compound 6-e instead of compound 1-g, and compound 6-f instead of compound 1-h. m / z[M+H] + 975.4

[0148] Manufacturing Example 7: Manufacturing of Compound 7 [ka]

[0149] Compound 7 was produced in the same manner as Compound 1, except that Compound 7-a was used instead of Compound 1-b, Compound 7-b was used instead of Compound 1-c, Compound 7-c was used instead of Compound 1-d, Compound 7-d was used instead of Compound 1-f, Compound 7-e was used instead of Compound 1-g, and Compound 7-f was used instead of Compound 1-h. m / z [M+H] + 975.4

[0150] Production Example 8: Production of Compound 8

Chemical Structure

[0151] Compound 8 was produced in the same manner as Compound 7, except that Compound 8-a was used instead of Compound 7-f. m / z [M+H] + 975.4

[0152] Production Example 9: Production of Compound 9

Chemical Structure

[0153] Compound 9 was produced in the same manner as Compound 1, except that Compound 9-a was used instead of Compound 1-a, Compound 7-a was used instead of Compound 1-b, Compound 9-b was used instead of Compound 1-c, Compound 9-c was used instead of Compound 1-d, Compound 9-d was used instead of Compound 1-e, Compound 9-e was used instead of Compound 1-f, Compound 9-f was used instead of Compound 1-g, and Compound 8-a was used instead of Compound 1-h. m / z [M+H] + 975.4

[0154] Production Example 10: Production of Compound 10

Chemical Structure

[0155] In this synthesis, compound 10 was produced in the same manner as compound 1, except that compound 9-a was used instead of compound 1-a, compound 10-a instead of compound 1-c, compound 10-b instead of compound 1-d, compound 9-d instead of compound 1-e, compound 10-c instead of compound 1-f, compound 10-d instead of compound 1-g, and compound 3-a instead of compound 1-h. m / z[M+H] + 935.4

[0156] Manufacturing Example 11: Manufacturing of Compound 11 [ka]

[0157] In this synthesis, compound 11 was produced in the same manner as compound 1, except that compound 11-a was used instead of compound 1-a, compound 11-b instead of compound 1-c, compound 11-c instead of compound 1-d, compound 11-d instead of compound 1-e, compound 11-e instead of compound 1-f, and compound 11-f instead of compound 1-g. m / z[M+H] + 935.4

[0158] Manufacturing Example 12: Manufacturing of Compound 12 [ka]

[0159] In this synthesis, compound 12 was produced in the same manner as compound 1, except that compound 11-a was used instead of compound 1-a, compound 7-a instead of compound 1-b, compound 12-a instead of compound 1-c, compound 12-b instead of compound 1-d, compound 12-c instead of compound 1-e, compound 12-d instead of compound 1-f, compound 12-e instead of compound 1-g, and compound 8-a instead of compound 1-h. m / z[M+H] + 975.4

[0160] Manufacturing Example 13: Manufacturing of Compound 13 [ka]

[0161] Under a nitrogen atmosphere, compound 1 (1.0 eq.) was placed in a round-bottom flask and dissolved in benzene-D6 (150 eq.). Trifluoromethanesulfonic acid (TfOH, 2.0 eq.) was slowly added dropwise to the reaction mixture and stirred at 25°C for 2 hours. D2O was added dropwise to terminate the reaction, and potassium phosphate tribasic (30 wt% in aqueous solution, 2.4 eq.) was added dropwise to adjust the pH of the aqueous layer to 9-10. The organic layer was separated by washing with CH2Cl2 / DI water. Water was removed with MgSO4 and the mixture was passed through a Celite-Florisil-Silica pad. After concentrating the solution under reduced pressure, it was purified by column chromatography to produce compound 13 (a+b+c+d+e+f+g=40-46, 87% yield, deuterium substitution rate 87.0-100%). In this case, the deuterium substitution rate was calculated as the percentage of the number of substituted deuterium atoms relative to the total number of hydrogen atoms that can exist in the chemical formula, after determining the number of substituted deuterium atoms in the compound using MALDI-TOF MS (Matrix-Assisted Laser Desorption / Ionization Time-of-Flight Mass Spectrometer) analysis.

[0162] Manufacturing Example 14: Manufacturing of Compound 14 [ka]

[0163] Under a nitrogen atmosphere, compound 9 (1.0 eq.) was placed in a round-bottom flask and dissolved in benzene-D6 (150 eq.). TfOH (2.0 eq.) was slowly added dropwise to the reaction mixture and stirred at 25°C for 2 hours. D2O was added dropwise to terminate the reaction, and potassium phosphate tribasic (30 wt% in aqueous solution, 2.4 eq.) was added dropwise to adjust the pH of the aqueous layer to 9-10. The organic layer was separated by washing with CH2Cl2 / DI water. Water was removed with MgSO4 and the mixture was passed through a Celite-Florisil-Silica pad. After concentrating the solution under reduced pressure, it was purified by column chromatography to produce compound 14 (a+b+c+d+e+f+g=40-46, 85% yield, deuterium substitution rate 87.0-100%). The deuterium substitution rate was calculated in the same manner as for compound 12.

[0164] Comparative Manufacturing Example 1: Manufacturing of Comparative Compound A [ka]

[0165] In this synthesis, comparative compound A was produced in the same manner as compound 1, except that compound Aa was used instead of compound 1-a, compound Ab instead of compound 1-b, compound Ac instead of compound 1-c, compound Ad instead of compound 1-d, compound Ae instead of compound 1-e, compound Af instead of compound 1-f, compound Ag instead of compound 1-g, and compound Ah instead of compound 1-h. m / z[M+H] + 835.3

[0166] Comparative Manufacturing Example 2: Manufacturing of Comparative Compound B [ka]

[0167] In this synthesis, comparative compound B was prepared in the same manner as compound 1, except that compound Ba was used instead of compound 1-a, compound Bb instead of compound 1-b, compound Bc instead of compound 1-c, compound Bd instead of compound 1-d, compound Be instead of compound 1-e, compound Bf instead of compound 1-f, compound Bg instead of compound 1-g, and compound Bh instead of compound 1-h. m / z[M+H] + 1087.4

[0168] Experimental Example 1: Measurement of Solubility The compounds 1-14, compound A, and compound B produced in the above manufacturing example were each checked to see if they could be dissolved in cyclohexanone at a concentration of 1.3 wt% at 25°C, and the results are shown in Table 1. In this case, "○" indicates that the compound dissolved easily in cyclohexanone, "△" indicates that the compound dissolved in cyclohexanone at 80°C, and "×" indicates that the compound did not dissolve in cyclohexanone.

[0169] [Table 1]

[0170] As can be seen in Table 1 above, all compounds represented by chemical formula 1 were soluble in cyclohexanone at a concentration of 1.3 wt%, but comparative compounds A and B were not soluble at room temperature, indicating that they cannot be used as compounds forming the organic layer when organic light-emitting organic layers are manufactured in a solution process.

[0171] This is because the angle of the (naphthylene)-(naphthylene) linker bond results in a difference in molecular solubility. Comparative compounds A and B, which have a different (naphthylene)-(naphthylene) linker than the compound represented by chemical formula 1, have orbitals of the two sigma bonds of the "naphthylene" linker that do not effectively induce an intramolecular twist form, but only induce a plate-like structure. In contrast, the angle of the (naphthylene)-(naphthylene) linker bond in the compound represented by chemical formula 1 can induce a twist form to a degree sufficient to increase solubility.

[0172] Therefore, the solubility measurement reveals that, for compounds with a molecular weight above a certain level, increasing solubility requires a substructure that can effectively induce a non-plate-like twisted form within the molecule, even if it has the same partial chemical formula.

[0173] Example 1 A glass substrate coated with a 500 Å thick thin film of ITO (indium tin oxide) was ultrasonically cleaned in distilled water containing detergent. Fischer Co. products were used as the detergent, and distilled water that had been secondarily filtered using a Millipore Co. filter was used. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes each time. After the distilled water cleaning, ultrasonic cleaning was performed in isopropyl and acetone solvents, followed by drying. The substrate was then washed for 5 minutes before being transported to a glove box.

[0174] [ka]

[0175] A coating composition prepared by dissolving compound O and compound P (in a weight ratio of 2:8) in cyclohexanone at a ratio of 20 wt / v% was spin-coated (4000 rpm) onto the ITO transparent electrode and then heat-treated (cured) at 200°C for 30 minutes to form a hole-injection layer with a thickness of 400 Å.

[0176] [ka]

[0177] A coating composition prepared by dissolving compound Q (Mn: 27,900; Mw: 35,600; measured by GPC using PC Standard with Agilent 1200 series) at 6 wt / v% in toluene was spin-coated (4000 rpm) onto the hole injection layer and heat-treated at 200°C for 30 minutes to form a hole transport layer with a thickness of 200 Å.

[0178] [ka]

[0179] On the hole transport layer, a coating composition prepared by dissolving compound 1, which was produced in Production Example 1 as a light-emitting layer host, and compound R (in a weight ratio of 98:2) as a light-emitting layer dopant in cyclohexanone at a concentration of 1.3 wt / v% was spin-coated (4000 rpm), and then heat-treated at 180°C for 30 minutes to form a light-emitting layer with a thickness of 400 Å.

[0180] [ka]

[0181] After being transferred to a vacuum deposition apparatus, the compound S was vacuum deposited onto the light-emitting layer to a thickness of 350 Å to form an electron injection and transport layer. LiF was sequentially deposited onto the electron injection and transport layer to a thickness of 10 Å, and then aluminum was deposited to a thickness of 1000 Å to form a cathode.

[0182] In the process described above, the deposition rate of organic materials was maintained at 0.4-0.7 Å / sec, LiF at 0.3 Å / sec, and aluminum at 2 Å / sec, with a vacuum level of 2 × 10⁻¹⁰ during deposition. -7 ~5×10 -8 Torr was maintained.

[0183] Examples 2 to 14 An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds listed in Table 2 below were used as the host for the light-emitting layer instead of compound 1. The compounds used in Examples 1 to 14 are summarized below.

[0184] [ka]

[0185] [ka]

[0186] Comparative Example 1 and Comparative Example 2 An organic light-emitting element was manufactured in the same manner as in Example 1, except that the compounds listed in Table 2 below were used instead of compound 1 as the host for the light-emitting layer.

[0187] Experimental Example 2: Characterization of Organic Light-Emitting Devices When a current is applied to the organic light-emitting element manufactured in the above examples and comparative examples, the current is 10 mA / cm². 2 The results of measuring the drive voltage, external quantum efficiency (EQE), and lifetime at the given current density are shown in Table 3 below. In this case, the external quantum efficiency (EQE) is calculated as "(number of photons emitted) / (number of injected charge carriers) × 100", and T90 represents the time required for the brightness to decrease from the initial brightness (500 nits) to 90%.

[0188] [Table 2]

[0189] As shown in Table 2 above, the organic light-emitting element containing the compound of the present invention as a host in the light-emitting layer was confirmed to exhibit a voltage at a level equivalent to that of the comparative example, as well as improved efficiency and lifespan.

[0190] Specifically, the organic light-emitting device in the example using the compound represented by chemical formula 1 as the host for the light-emitting layer showed significantly improved efficiency and lifetime compared to the organic light-emitting devices of Comparative Examples 1 and 2, which used comparative compounds A and B, respectively, as the host for the light-emitting layer. This is judged to be due to improved material stability resulting from the structural properties of the compound represented by chemical formula 1.

[0191] Therefore, it can be seen that when the compound represented by chemical formula 1 is used as the host material for the organic light-emitting device, the external quantum efficiency and lifetime characteristics of the organic light-emitting device can be improved simultaneously. [Explanation of symbols]

[0192] 1 circuit board 2 Positive electrode 3. Emitting layer 4 Negative electrode 5. Hole injection layer 6. Hole transport layer 7. Electron injection and transport layers

Claims

1. A compound represented by any one of the following chemical formulas 1-1 to 1-3: 【Chemistry 1A】 【Chemistry 1B】 In the aforementioned chemical formulas 1-1 to 1-3, D stands for deuterium. R １ and R ２ These are, independently, hydrogen or deuterium. L1 and L2 are all single bonds; or One of L1 and L2 is a single bond, and the other is unsubstituted or an m- or p-phenylene substituted with 1 to 4 deuterium atoms. L3 and L4 are all single bonds; or One of L3 and L4 is a single bond, and the other is unsubstituted or p-phenylene substituted with 1 to 4 deuterium atoms. Ar1 and Ar2 are independently naphthyl or dibenzofuranyl, Here, Ar1 and Ar2 are either unsubstituted or substituted with one or more deuterium atoms. a and b are each independent integers between 0 and 8. c and d are each independent integers between 0 and 5.

2. R １ and R ２ The compound according to claim 1, wherein all are hydrogen; or all are deuterium.

3. The compound according to claim 1, wherein a + b + c + d is 0 or 10 or more.

4. The compound according to claim 1, wherein the deuterium substitution rate of the compound is 0% or 80% or more.

5. The compound according to claim 1, wherein the compound has a molecular weight of 800 g / mol or more.

6. The compound according to claim 1, wherein the compound is selected from the group consisting of compounds represented by the following chemical formulas and their deuterated structures. 【Chemistry 2A】 【Chemistry 2B】 【Chem.2C】 [Transformation into 2D] 【Transformation 2E】 [Chemical 2F] [Transformation into 2G] [Chemical 2H] 【Chemistry 2I】 【Chemical 2J】 [2K] [2L]

7. An organic light-emitting element comprising a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain a compound according to any one of claims 1 to 6.

8. The organic light-emitting element according to claim 7, wherein the organic layer containing the compound is a light-emitting layer.

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