Heterocyclic compounds, organic light emitting element including the same, and organic layer composition of organic light emitting element

Abstract

The present specification relates to a heterocyclic compound represented by formula 1, an organic light emitting element including the same, and an organic layer composition.

Description

[0001] This application claims priority based on Korean Patent Application No. 10-2020-0153290, filed on November 17, 2020, and the entire contents disclosed in the document of said Korean Patent Application are incorporated into this specification. Technical Field

[0002] The present invention relates to a heterocyclic compound, an organic light-emitting element comprising the heterocyclic compound, and an organic layer composition. Background Technology

[0003] Organic light-emitting elements are a type of self-emitting display element, and they have the advantages of wide viewing angle, excellent contrast and fast response speed.

[0004] An organic light-emitting element (OLED) has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to an OLED with this structure, electrons and holes injected from the two electrodes recombine in the organic thin film to form pairs, and then emit light as they disappear. The organic thin film can be composed of a single layer, or, if necessary, multiple layers.

[0005] If necessary, organic thin film materials can possess light-emitting capabilities. For example, as organic thin film materials, compounds capable of forming a light-emitting layer on their own can be used, or compounds capable of serving as a host or dopant in a host-dopant-based light-emitting layer can be used. Additionally, as organic thin film materials, compounds capable of performing hole injection, hole transport, electron blocking, and similar operations can be used.

[0006] To improve the performance, lifespan, or efficiency of organic light-emitting elements, there is a continuous need to develop organic thin film materials.

[0007] [Previous Technical References]

[0008] [Patent Documents]

[0009] Korean Patent Application Publication No. 10-2011-0013445 Summary of the Invention

[0010] Technical issues

[0011] One object of the present invention is to provide a heterocyclic compound that can impart low driving voltage, excellent luminous efficiency and excellent lifetime properties to organic light-emitting elements.

[0012] Another object of the present invention is to provide an organic light-emitting element comprising the heterocyclic compound.

[0013] Another object of the present invention is to provide an organic layer composition comprising the heterocyclic compound.

[0014] Technical solutions

[0015] This invention provides a heterocyclic compound, which is represented by the following formula 1:

[0016] [Formula 1]

[0017]

[0018] in:

[0019] X and Y are the same or different from each other, and each is independently O or S;

[0020] R1 to R8 may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1 to C60 alkyl, substituted or unsubstituted C2 to C60 alkenyl, substituted or unsubstituted C2 to C60 alkoxy, substituted or unsubstituted C3 to C60 cycloalkyl, substituted or unsubstituted C2 to C60 heterocycloalkyl, substituted or unsubstituted C6 to C60 aryl, substituted or unsubstituted C2 to C60 heteroaryl, The group consisting of -P(=O)R101R102R103 and -NR101R102, wherein R101, R102 and R103 are the same or different from each other, and each is independently a substituted or unsubstituted C1 to C60 alkyl, a substituted or unsubstituted C6 to C60 aryl or a substituted or unsubstituted C2 to C60 heteroaryl; or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic ring or a substituted or unsubstituted C2 to C60 heterocycle;

[0021] R9 and R10 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6 to C60 aryl group, or a substituted or unsubstituted C2 to C60 heteroaryl group;

[0022] L1 and L2 may be the same as or different from each other, and each is independently a direct bond, a substituted or unsubstituted C6 to C60 arylene or a substituted or unsubstituted C2 to C60 heteroarylene;

[0023] m is an integer from 0 to 4, provided that when m is 0, L1 is a direct key, and when m is 2 to 4, each L1 is either the same as or different from the others and is chosen independently.

[0024] n is an integer from 0 to 4, provided that when n is 0, L2 is a direct key, and when n is 2 to 4, each L2 is either the same as or different from the others and is chosen independently.

[0025] o is an integer from 0 to 2, provided that when o is 2, each R2 is either the same as or different from each other and is chosen independently.

[0026] In addition, the present invention provides an organic light-emitting element, the organic light-emitting element comprising:

[0027] First electrode;

[0028] The second electrode is positioned to face the first electrode; and

[0029] One or more organic layers are disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprise the heterocyclic compound represented by Formula 1.

[0030] In addition, the present invention provides an organic layer composition for an organic light-emitting element, the organic layer composition comprising the heterocyclic compound represented by Formula 1.

[0031] Beneficial effects

[0032] The heterocyclic compounds and organic layer compositions comprising the heterocyclic compounds of the present invention can be usefully used as materials for the organic layers of organic light-emitting elements. Specifically, these materials are used as hole transport layer materials, electron blocking layer materials, and light-emitting layer materials, thereby providing significant effects in reducing the driving voltage of organic light-emitting elements, improving luminous efficiency, and improving lifetime properties.

[0033] The organic light-emitting element of the present invention includes the heterocyclic compound or includes the organic layer composition containing the heterocyclic compound, thereby providing excellent driving voltage, luminous efficiency and lifetime properties. Attached Figure Description

[0034] Figures 1 to 3 These are schematic diagrams illustrating the stacked structure of an organic light-emitting element according to an embodiment of the present invention. Detailed Implementation

[0035] The invention will be described in detail below.

[0036] In this invention, the term "substituted" means that a hydrogen atom bonded to a carbon atom in a compound is replaced by another substituent, and the position to be substituted is not limited, as long as it is the position where the hydrogen atom is substituted (i.e., the position where the substituent can be substituted). When two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

[0037] In this invention, the term "substituted or unsubstituted" means that it is not substituted or substituted by one or more substituents selected from the group consisting of C1 to C60 straight-chain or branched alkyl, C2 to C60 straight-chain or branched alkenyl, C2 to C60 straight-chain or branched alkynyl, C3 to C60 monocyclic or polycyclic cycloalkyl, C2 to C60 monocyclic or polycyclic heterocyclic alkyl, C6 to C60 monocyclic or polycyclic aryl, C2 to C60 monocyclic or polycyclic heteroaryl, -SiRR'R", -P(=O)RR', C1 to C20 alkylamine, C6 to C60 monocyclic or polycyclic arylamine and C2 to C60 monocyclic or polycyclic heteroarylamine; or it is not substituted or substituted by substituents to which two or more substituents selected from the substituents exemplified above are attached.

[0038] In this invention, the alkyl group comprises a straight or branched chain having 1 to 60 carbon atoms and may be further substituted by another substituent. The number of carbon atoms in the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tributyl, dibutyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tripentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, trioctyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.

[0039] In this invention, the alkenyl group comprises a straight or branched chain having 2 to 60 carbon atoms and may be further substituted by another substituent. The number of carbon atoms in the alkenyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples include, but are not limited to, vinyl, 1-propenyl, 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, stilbene, styrene, and the like.

[0040] In this invention, the alkynyl group comprises a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The number of carbon atoms in the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0041] In this invention, cycloalkyl groups comprise monocyclic or polycyclic compounds having 3 to 60 carbon atoms and may be further substituted with another substituent. Hereinafter, polycyclic refers to a group in which the cycloalkyl group is directly attached to or condensed with another cyclic group. Hereinafter, the other cyclic group may be a cycloalkyl group, but may be a different type of cyclic group such as heterocycloalkyl, aryl, heteroaryl, and the like. The number of carbon atoms in the cycloalkyl group may be 3 to 60, specifically 3 to 40, more specifically 5 to 20. Specific 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, cyclooctyl, and the like.

[0042] In this invention, the heterocyclic alkyl group includes O, S, Se, N, or Si as heteroatoms, comprising monocyclic or polycyclic groups having 2 to 60 carbon atoms, and may be further substituted by another substituent. Hereinafter, polycyclic refers to a group in which the heterocyclic alkyl group is directly attached to or condensed with another cyclic group. Hereinafter, the other cyclic group may be a heterocyclic alkyl group, but may be a different type of cyclic group such as cycloalkyl, aryl, heteroaryl, and the like. The number of carbon atoms in the heterocyclic alkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0043] In this invention, the aryl group comprises a monocyclic or polycyclic ring having 6 to 60 carbon atoms and may be further substituted with other substituents. Hereinafter, polycyclic refers to a group in which the aryl group is directly attached to or condensed with another cyclic group. Hereinafter, the other cyclic group may be an aryl group, but may be different types of cyclic groups such as cycloalkyl, heterocycloalkyl, heteroaryl, and the like. The aryl group includes spirocyclic groups. The number of carbon atoms in the aryl group may be 6 to 60, specifically 6 to 40, more specifically 6 to 25. Specific examples of aryl groups include, but are not limited to, phenyl, biphenyl, triphenyl, naphthyl, anthracene, etc. Chrysenyl group, phenanthryl group, perylenyl group, fluoranthenyl group, triphenylenyl group, phenalenyl group, pyrenyl group, tetracenyl group, pentaphenylenyl group, fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group, 2,3-dihydro-1H-indenyl group, their condensed cyclic groups and analogues.

[0044] In this invention, the fluorene group can be substituted, and adjacent substituents can bond to each other to form a ring.

[0045] When the fluorene group is substituted, it can be, but is not limited to, the following: and similar substances.

[0046] In this invention, the heteroaryl group includes S, O, Se, N, or Si as heteroatoms, comprising monocyclic or polycyclic groups having 2 to 60 carbon atoms, and may be further substituted with other substituents. Hereinafter, polycyclic refers to a group in which the heteroaryl group is directly attached to or condensed with another cyclic group. Hereinafter, the other cyclic group may be a heteroaryl group, but may be a different type of cyclic group such as cycloalkyl, heterocycloalkyl, aryl, and the like. The number of carbon atoms in the heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples of heteroaryl groups include, but are not limited to, pyridyl, pyrroloyl, pyrimidinyl, pyridazinyl, furanyl, thiophene, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazolyl, oxadiazolyl, thiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiaranyl, diazinyl, oxazinyl, thiazolyl, dioxinyl group, triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, isoquinazolinyl, quinozolylyl (group), naphthidyl, acridineyl, phenanthridineyl, imidazopyridyl, diazanaphthyl, triazaindyl, indoleyl, indoleazinyl, benzothiazolyl, benzoxazolyl, benzoimidazolyl, benzothiopheneyl, benzofuranyl, dibenzothiopheneyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenanthridineyl, indole[2,3-a]carbazolyl, indole[2,3-b]carbazolyl Azolyl, indololinyl, 10,11-dihydro-dibenzo[b,f]azolinyl, 9,10-dihydroacridyl, phenazinyl, phenanthrazinyl, phthalazinyl, naphridinyl, phenolinyl, benzo[c][1,2,5]thiadiazolyl, 5,10-dihydrodibenzo[b,e][1,4]azasilolinyl, pyrazolo[1,5-c]quinazolinyl, pyrido[1,2-b]inzolyl, pyrido[1,2-a]imidazo[1,2-e]indololinyl, 5,11-dihydroindo[1,2-b]carbazoleyl and analogues.

[0047] In this invention, the amino group can be selected from the group consisting of monoalkylamino, monoarylamino, monoheteroarylamino, -NH2, dialkylamino, diarylamino, diheteroarylamino, alkylarylamino, alkylheteroarylamino, and arylheteroarylamino, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amino groups include, but are not limited to, methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, diphenylamino, anthraceneamino, 9-methyl-anthraylamino, diphenylamino, phenylnaphthylamino, xylylamino, phenylxylylamino, triphenylamino, biphenylnaphthylamino, phenylbiphenylamino, biphenylfluorenylamino, phenylbitriphenylamino, biphenylbitriphenylamino, and the like.

[0048] In this invention, arylene refers to a group having two bonding positions on an aryl group, i.e., a divalent group. The description of aryl groups can be applied except that each of these groups is a divalent group. Similarly, heteroarylene refers to a group having two bonding positions on a heteroaryl group, i.e., a divalent group. The description of heteroaryl groups can be applied except that each of these groups is a divalent group.

[0049] In this invention, "adjacent" groups can refer to a substituent that is substituted on an atom directly connected to the atom on which the particular substituent is substituted, a substituent that is spatially closest to the particular substituent, or another substituent that is substituted on the atom on which the particular substituent is substituted. For example, two substituents substituted at an ortho position on a benzene ring and two substituents substituted at the same carbon atom on an aliphatic ring can be interpreted as groups that are "adjacent" to each other.

[0050] In this invention, "where no substituent is indicated in the chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, since deuterium (2H) is an isotope of hydrogen, some hydrogen atoms may be deuterium.

[0051] In one embodiment of the invention, "where no substituent is indicated in the chemical formula or compound structure" may mean that hydrogen or deuterium is present at all positions that can be substituted by substituents. That is, since deuterium is an isotope of hydrogen, some hydrogen atoms may be the isotope deuterium, and the deuterium content may be 0% to 100%.

[0052] In one embodiment of the invention, in the case where "no substituents are indicated in the chemical formula or compound structure", hydrogen and deuterium can be used interchangeably in the compound unless deuterium is explicitly excluded (e.g., "0% deuterium content", "100% hydrogen content", and "all substituents are hydrogen").

[0053] In one embodiment of the present invention, deuterium is an isotope of hydrogen and is an element having a deuterium nucleus consisting of a proton and a neutron, and can be expressed as hydrogen-2, and its element symbol can also be written as D or 2H.

[0054] In one embodiment of the invention, isotopes referring to atoms having the same number of atoms (Z) but different mass numbers (A) can also be interpreted as elements having the same number of protons but different numbers of neutrons.

[0055] In one embodiment of the present invention, the meaning of the T% content of a specific substituent can be defined as follows: T2 / T1×100=T%, where T1 is defined as the total number of substituents that the basic compound may have, and T2 is defined as the number of a specific substituent.

[0056] That is, in one instance, by The indicated 20% deuterium content in a phenyl group may mean that the total number of substituents the phenyl group can have is 5 (T1 in the formula), and the number of deuterium groups is 1 (T2 in the formula). That is, the 20% deuterium content in a phenyl group can be represented by the following structural formula:

[0057]

[0058] Additionally, in one embodiment of the present invention, the case of "phenyl having a deuterium content of 0%" may mean a phenyl that does not contain deuterium atoms (i.e. has 5 hydrogen atoms).

[0059] In this invention, the deuterium content in the heterocyclic compound represented by Formula 1 can be from 0% to 100%, more preferably from 60% to 100%.

[0060] In this invention, C6 to C60 aromatic rings refer to compounds comprising an aromatic ring consisting of C6 to C60 carbons and hydrogens, and include, but are not limited to, for example, benzene, biphenyl, triphenyl, ditriphenylene, naphthalene, anthracene, fenene, fluorene, pyrene, etc. Perylene, azurite, and the like, and including all aromatic cyclic compounds known in this art that satisfy the above number of carbons.

[0061] This invention provides a heterocyclic compound, which is represented by the following formula 1:

[0062] [Formula 1]

[0063]

[0064] in:

[0065] X and Y are the same or different from each other, and each is independently O or S;

[0066] R1 to R8 may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1 to C60 alkyl, substituted or unsubstituted C2 to C60 alkenyl, substituted or unsubstituted C2 to C60 alkoxy, substituted or unsubstituted C3 to C60 cycloalkyl, substituted or unsubstituted C2 to C60 heterocycloalkyl, substituted or unsubstituted C6 to C60 aryl, substituted or unsubstituted C2 to C60 heteroaryl, The group consisting of -P(=O)R101R102R103 and -NR101R102, wherein R101, R102 and R103 are the same or different from each other, and each is independently a substituted or unsubstituted C1 to C60 alkyl, a substituted or unsubstituted C6 to C60 aryl or a substituted or unsubstituted C2 to C60 heteroaryl; or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic ring or a substituted or unsubstituted C2 to C60 heterocycle;

[0067] R9 and R10 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6 to C60 aryl or a substituted or unsubstituted C2 to C60 heteroaryl;

[0068] L1 and L2 may be the same as or different from each other, and each is independently a direct bond, a substituted or unsubstituted C6 to C60 arylene or a substituted or unsubstituted C2 to C60 heteroarylene;

[0069] m is an integer from 0 to 4, provided that when m is 0, L1 is a direct key, and when m is 2 to 4, each L1 is either the same as or different from the others and is chosen independently.

[0070] n is an integer from 0 to 4, provided that when n is 0, L2 is a direct key, and when n is 2 to 4, each L2 is either the same as or different from the others and is chosen independently.

[0071] o is an integer from 0 to 2, provided that when o is 2, each R2 is either the same as or different from each other and is chosen independently.

[0072] In Equation 1 above, X can be O, and X can be S.

[0073] In Equation 1 above, Y can be O, and Y can also be S.

[0074] In one embodiment of the present invention, the heteroatoms in the heteroatom-containing group may be one or more selected from O, S, Se, N or Si.

[0075] In another embodiment of the invention, the heteroatoms in the heteroatom-containing group may be one or more selected from O, S or N.

[0076] In one embodiment of the present invention, R1 may be hydrogen, deuterium, substituted or unsubstituted C1 to C60 alkyl, substituted or unsubstituted C6 to C60 aryl, substituted or unsubstituted C2 to C60 heteroaryl, or -P(=O)R101R102R103, wherein R101, R102, and R103 may be the same as or different from each other, and may each be independently substituted or unsubstituted C6 to C60 aryl or substituted or unsubstituted C2 to C60 heteroaryl.

[0077] In another embodiment of the invention, R1 may be a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, or -P(=O)R101R102R103, wherein R101, R102, and R103 may be the same as or different from each other, and may each be independently a substituted or unsubstituted C6 to C30 aryl or a substituted or unsubstituted C2 to C30 heteroaryl.

[0078] In another embodiment of the present invention, R1 may be phenyl, biphenyl, naphthyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, phenanthrene, ditriphenylene, dibenzothiophene, or dibenzofuranyl, wherein the substituent may be in the form of "substituted or unsubstituted".

[0079] In another embodiment of the invention, R1 may be phenyl, biphenyl, naphthyl, phenanthrene, ditriphenylene, 9,9-dimethylfluorenyl, dibenzothiophene, or dibenzofuranyl, wherein the substituent may be in a "substituted or unsubstituted" form.

[0080] In one embodiment of the invention, R2 to R8 may be the same as or different from each other, and may each be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heteroaryl or -P(=O)R101R102R103, wherein R101, R102 and R103 may be the same as or different from each other, and may each be independently substituted or unsubstituted C6 to C30 aryl or substituted or unsubstituted C2 to C30 heteroaryl.

[0081] In another embodiment of the invention, R2 to R8 may be the same as or different from each other, and may each be independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, substituted or unsubstituted C2 to C20 heteroaryl or -P(=O)R101R102R103, wherein R101, R102 and R103 may be the same as or different from each other, and may each be independently substituted or unsubstituted C6 to C20 aryl or substituted or unsubstituted C2 to C20 heteroaryl.

[0082] In another embodiment of the invention, R2 to R8 may be the same as or different from each other, and may each be independently hydrogen, deuterium, substituted or unsubstituted C1 to C5 alkyl, substituted or unsubstituted C6 to C20 aryl or substituted or unsubstituted C2 to C20 heteroaryl.

[0083] In another embodiment of the invention, R2 to R8 may be the same as or different from each other, and may each be independently hydrogen, deuterium, substituted or unsubstituted C1 to C5 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted ditriphenylene, substituted or unsubstituted dibenzothiophene, or substituted or unsubstituted dibenzofuranyl.

[0084] In another embodiment of the invention, R2 to R8 may be the same as or different from each other, and may be hydrogen or deuterium.

[0085] In one embodiment of the invention, R9 and R10 may be the same as or different from each other, and may each be independently a substituted or unsubstituted C6 to C30 aryl or a substituted or unsubstituted C2 to C30 heteroaryl.

[0086] In one embodiment of the present invention, R9 and R10 may be the same as or different from each other, and may each be independently phenyl, biphenyl, naphthyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, phenanthrene, ditriphenylene, dibenzothiophene, or dibenzofuranyl, wherein the substituent may be in the form of "substituted or unsubstituted".

[0087] In one embodiment of the invention, R9 and R10 may be the same as or different from each other, and may each be independently phenyl, biphenyl, naphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl or spirodifluorenyl, wherein the substituent may be in the form of "substituted or unsubstituted".

[0088] In one embodiment of the invention, L1 to L8 may be the same as or different from each other, and may each be a direct bond, a substituted or unsubstituted C6 to C30 arylene, or a substituted or unsubstituted C2 to C30 heteroarylene.

[0089] In another embodiment of the invention, L1 to L8 may be the same as or different from each other, and may each be a direct bond, a substituted or unsubstituted C6 to C20 arylene, or a substituted or unsubstituted C2 to C20 heteroarylene.

[0090] In another embodiment of the invention, L1 to L8 may be the same as or different from each other, and may each be a direct bond, phenyl, biphenyl, naphthyl, phenanthrene or ditriphenylene, wherein the substituent may be in the form of "substituted or unsubstituted".

[0091] In another embodiment of the invention, L1 to L8 may be the same as or different from each other, and may each be a direct bond, phenyl or biphenyl, wherein the substituent may be in the form of "substituted or unsubstituted".

[0092] In one embodiment of the invention, the substituents substituted on R1 to R10, L1, and L2 may be the same or different from each other, and may each be independently composed of one or more substituents, wherein each of the one or more substituents is independently selected from the group consisting of C1 to C10 straight-chain or branched alkyl, C2 to C10 straight-chain or branched alkenyl, C2 to C10 straight-chain or branched alkynyl, C3 to C15 cycloalkyl, C2 to C20 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, C1 to C10 alkylamine, C6 to C30 arylamine, and C2 to C30 heteroarylamine.

[0093] In another embodiment of the invention, the substituents substituted on R1 to R10, L1 and L2 may be the same or different from each other, and may each be independently composed of one or more substituents, wherein each of the one or more substituents is independently selected from the group consisting of C1 to C10 straight-chain or branched alkyl, C2 to C10 straight-chain or branched alkenyl, C2 to C10 straight-chain or branched alkynyl, C6 to C30 aryl, C2 to C30 heteroaryl, C6 to C30 arylamine and C2 to C30 heteroarylamine.

[0094] In another embodiment of the invention, the substituents substituted on R1 to R10, L1 and L2 may be the same or different from each other, and may each be independently composed of one or more substituents, wherein each of the one or more substituents is independently selected from the group consisting of C1 to C10 straight-chain or branched alkyl, C6 to C30 aryl, C2 to C30 heteroaryl, C6 to C30 arylamine and C2 to C30 heteroarylamine.

[0095] In another embodiment of the invention, the substituents substituted on R1 to R10, L1 and L2 may be the same or different from each other, and may each be independently composed of one or more substituents, wherein each of the one or more substituents is independently selected from the group consisting of C1 to C5 straight-chain or branched alkyl, phenyl, naphthyl, pyridyl, anthracene, carbazole, biphenyl, dibenzothiophene, dibenzofuran and phenanthrene.

[0096] In one embodiment of the present invention, in Formula 1, m is an integer from 0 to 3, wherein when m is 0, L1 is a direct key, and when m is 2 to 3, each L1 is the same or different from each other and is selected independently; and n is an integer from 0 to 3, wherein when n is 0, L2 is a direct key, and when n is 2 to 3, each L2 is the same or different from each other and can be selected independently.

[0097] In another embodiment of the invention, in Equation 1, m is an integer from 0 to 2, provided that when m is 0, L1 is a direct key, and when m is 2, each L1 is either the same as or different from each other and is selected independently; and n is an integer from 0 to 2, provided that when n is 0, L2 is a direct key, and when n is 2, each L2 is either the same as or different from each other and can be selected independently.

[0098] In another embodiment of the invention, in Equation 1, m is an integer that is 0 or 1, provided that when m is 0, L1 is a direct key; and n is an integer that is 0 to 1, provided that when n is 0, L2 can be a direct key.

[0099] In one embodiment of the present invention, o in Formula 1 can be 0, 1 or 2.

[0100] Preferably, a compound of formula 1 can be used, wherein

[0101] X and Y are O or S;

[0102] R1, R9, and R10 may be the same as or different from each other, and may each be independently phenyl, biphenyl, naphthyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, phenanthrene, ditriphenylene, dibenzothiophene, or dibenzofuranyl, wherein the substituent may be in the form of "substituted or unsubstituted";

[0103] In addition, R2 to R8 may be the same or different from each other, and may be hydrogen or deuterium;

[0104] In addition, L1 and L2 are direct bonds or benzene;

[0105] m and n may be the same or different from each other, and each is an independent integer from 0 to 2; and

[0106] o is 1.

[0107] More preferably, a compound of formula 1 can be used, wherein

[0108] X and Y are O or S;

[0109] R1 is a substituted or unsubstituted phenyl, biphenyl, naphthyl, phenanthrene, bitriphenylene, 9,9-dimethylfluorenyl, dibenzothiophene, or dibenzofuranyl;

[0110] R2 to R8 may be the same as or different from each other, and each is independently either hydrogen or deuterium;

[0111] R9 and R10 may be the same as or different from each other, and each may be independently substituted or unsubstituted phenyl, biphenyl, naphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl or spirodifluorenyl;

[0112] L1 and L2 are direct bonds or benzene;

[0113] m and n may be the same or different from each other, and each is an independent integer from 0 to 3; and

[0114] o is 0.

[0115] Even better, where X and Y can be O.

[0116] In one embodiment of the invention, the heterocyclic compound represented by Formula 1 may be a compound represented by any of the following compounds:

[0117] Compounds:

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154] By introducing various substituents into the corresponding structures, compounds of Formula 1 can be synthesized into compounds possessing the inherent properties of the introduced substituents. For example, by introducing substituents primarily used in the manufacture of hole injection layer materials, hole transport layer materials, electron blocking layer materials, light-emitting layer materials, hole blocking layer materials, electron transport layer materials, and electron injection layer materials into the core structure, materials that meet the requirements of each organic layer can be synthesized.

[0155] Furthermore, by introducing various substituents into the structure of the compound of Formula 1, the energy band gap can be precisely controlled, and the applications of the material can be diversified by improving the properties at the interface between organic materials.

[0156] Heterocyclic compounds can be used as one or more of the following materials selected from the organic layers used in organic light-emitting elements: hole injection layer material, hole transport layer material, electron blocking layer material, light-emitting layer material, hole blocking layer material, electron transport layer material, and electron injection layer material, and more particularly, they can be used as hole transport layer material, electron blocking layer material, and light-emitting layer material.

[0157] When heterocyclic compounds are used as luminescent layer materials, they can be used as host materials, and they can be more useful as p-hosts (p-type hosts) with good hole transport capabilities among host materials.

[0158] Furthermore, this invention relates to a light-emitting element, the light-emitting element comprising:

[0159] First electrode;

[0160] The second electrode is positioned to face the first electrode; and

[0161] One or more organic layers are disposed between the first electrode and the second electrode, and

[0162] One or more of the organic layers contain a heterocyclic compound represented by Formula 1.

[0163] In one embodiment of the present invention, the first electrode may be an anode and the second electrode may be a cathode.

[0164] In another embodiment, the first electrode may be a cathode, and the second electrode may be an anode.

[0165] An organic light-emitting element according to an embodiment of the present invention may further include one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, and may have a stacked structure in the order of anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode.

[0166] In one embodiment of the present invention, the organic light-emitting element may be a green organic light-emitting element, and the heterocyclic compound represented by Formula 1 may be used as a material for the green organic light-emitting element.

[0167] In one embodiment of the present invention, the organic light-emitting element may be a blue organic light-emitting element, and the heterocyclic compound represented by Formula 1 may be used as a material for the blue organic light-emitting element.

[0168] In one embodiment of the present invention, the organic light-emitting element may be a red organic light-emitting element, and the heterocyclic compound represented by Formula 1 may be used as a material for the red organic light-emitting element.

[0169] In one embodiment of the present invention,

[0170] In green organic light-emitting elements, blue organic light-emitting elements and red organic light-emitting elements, the heterocyclic compound represented by Formula 1 can be used as a hole injection layer material, a hole transport layer material, an electron blocking layer material, a light-emitting layer material, a hole blocking layer material, an electron transport layer material and an electron injection layer material, and more specifically, it can be preferably used as a hole transport layer material, an electron blocking layer material and a light-emitting layer material.

[0171] When used as a light-emitting layer material, it can be used as a host material, and it can be more useful as a p-host (p-type host) with good hole transport capability among host materials.

[0172] The host material may consist only of heterocyclic compounds represented by Formula 1, or may include a combination of said heterocyclic compounds and other host materials.

[0173] The specific contents of the heterocyclic compounds represented by Formula 1 are the same as those mentioned above.

[0174] In addition to using the aforementioned heterocyclic compounds to form one or more organic layers, the organic light-emitting elements of the present invention can be manufactured using conventional methods and materials for manufacturing organic light-emitting elements.

[0175] When manufacturing organic light-emitting elements, heterocyclic compounds can form organic layers using solution coating and vacuum deposition methods. Solution coating methods refer to, but are not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and similar methods.

[0176] The organic layer of the organic light-emitting element of the present invention may have a single-layer structure, but may also have a multi-layer 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 comprising a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like as organic layers. However, the structure of the organic light-emitting element is not limited to this structure, and may include a smaller or larger number of organic layers.

[0177] In one embodiment of the invention, the light-emitting layer included in the organic layer may further include a phosphorescent dopant.

[0178] As phosphorescent dopant materials, those known in this art can be used. For example, phosphorescent dopant materials represented by LL'MX', LL'L”M, LMX'X”, L2MX', and L3M can be used, but the scope of the invention is not limited to these examples.

[0179] M can be iridium, platinum, osmium, or similar substances.

[0180] Wherein, L is an anionic bidentate ligand coordinated to M via sp2 carbon and heteroatoms, and X can trap electrons or holes. Non-limiting examples of L include 2-(1-naphthyl)benzoxazole, (2-phenylbenzoxazole), (2-phenylbenzothiazole), (7,8-benzoquinoline), (thienopyridine), phenylpyridine, benzothienopyridine, 3-methoxy-2-phenylpyridine, thienopyridine, tolylpyridine, and the like. Non-limiting examples of X' and X” include acetylacetonate (acac), hexafluoroacetylacetonate, salinomycete, picolinate, 8-hydroxyquinoline ester, and the like.

[0181] Specific examples of phosphorescent dopants are shown below, but are not limited to these examples.

[0182]

[0183] In one embodiment of the invention, the light-emitting layer comprises a heterocyclic compound represented by Formula 1 and can be used with an iridium dopant.

[0184] In one embodiment of the present invention, red phosphorescent dopant (piq)2(Ir)(acac), green phosphorescent dopant Ir(ppy)3, and the like can be used as iridium dopants.

[0185] In one embodiment of the invention, the dopant may have a content of 1% to 15%, more preferably 3% to 10%, and even more preferably 5% to 10% over the entire light-emitting layer.

[0186] In an organic light-emitting element according to an embodiment of the present invention, materials other than heterocyclic compounds represented by Formula 1 are listed below, but these are for illustrative purposes only and are not intended to limit the scope of the invention, and can be replaced by materials known in this art.

[0187] Materials with relatively large work functions can be used as anode materials, and transparent conductive oxides, metals, conductive polymers, or the like can be used. Specific examples of anode materials 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; conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; and the like.

[0188] Materials with relatively low work functions can be used as cathode materials, and metals, metal oxides, conductive polymers, or the like can be used. Specific examples of cathode materials include, but are not limited to: metals, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or their alloys; multilayer materials, such as LiF / Al or LiO2 / Al.

[0189] As a hole injection layer material, known hole injection layer materials can be used, such as phthalocyanine compounds, such as copper phthalocyanine and the like disclosed in U.S. Patent No. 4,356,429; or starburst-type amine derivatives disclosed in Advanced Materials, 6, page 677 (1994). aminederivatives, such as tris(4-carbazolyl-9-ylphenyl)amine (TCTA), 4,4',4”-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB); soluble conductive polymers, polyaniline / dodecylbenzenesulfonic acid; or poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), polyaniline / camphorsulfonic acid or polyaniline / poly(4-styrene-sulfonate) and the like.

[0190] As a hole transport layer material, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives and similar materials can be used, and low molecular weight or high molecular weight materials can be used.

[0191] As an electron transport layer material, oxadiazole derivatives, anthraquinone dimethyl ether and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinone dimethyl ether and its derivatives, fluorenone and its derivatives, diphenyl dicyanoethylene and its derivatives, biphenylquinone derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, and similar materials can be used, and both high molecular weight and low molecular weight materials can be used.

[0192] As an electron injection layer material, LiF is commonly used in this technology, for example, but the invention is not limited thereto.

[0193] As the luminescent layer material, red, green, or blue luminescent materials can be used, and if necessary, mixtures of two or more luminescent materials can be used. In this case, two or more luminescent materials can be used as separate sources, or they can be premixed and used as a single source. Additionally, fluorescent or phosphorescent materials can be used as the luminescent layer material. As the luminescent layer material, materials that emit light by combining holes and electrons injected from the anode and cathode respectively can be used, or materials in which the host material and dopant material participate in luminescence together can be used.

[0194] When using a substrate of mixed luminescent layer materials, it can be used by mixing substrates of the same series or by mixing substrates of different series. For example, it can be used by selecting any two or more types of n-type substrate materials and p-type substrate materials as the substrate materials of the luminescent layer.

[0195] Electron blocking layer materials may include, but are not limited to, tri(phenylpyrazole)iridium, 9,9-bis[4-(N,N-bis-biphenyl-4-ylamino)phenyl]-9H-fluorene (BPAPF), bis[4-(p,p-xylamino)phenyl]diphenylsilane, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (BPAPF ... One or more of the following compounds: [yl)-N-phenylamino]biphenyl (NPD), N,N'-dicarbazolyl-3,5-benzene (mCP), and bis[4-(N,N-diethylamino)-2-methylphenyl](4-methylphenyl)methane (MPMP).

[0196] Additionally, the electron blocking layer may contain inorganic compounds. For example, it may contain, but is not limited to, at least one or a combination of the following: halide compounds, such as LiF, NaF, KF, RbF, CsF, FrF, MgF2, CaF2, SrF2, BaF2, LiCl, NaCl, KCl, RbCl, CsCl, FrCl and the like; and oxides, such as Li2O, Li2O2, Na2O, K2O, Rb2O, Rb2O2, Cs2O, Cs2O2, LiAlO2, LiBO2, LiTaO3, LiNbO3, LiWO4, Li2CO, NaWO4, KAlO2, K2SiO3, B2O5, Al2O3, SiO2 and the like.

[0197] Hole-blocking layer materials may include, but are not limited to, dioxazone derivatives, triazole derivatives, phenanthroline derivatives, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), aluminum complexes, and the like.

[0198] In the organic light-emitting element of the present invention, materials known in this art can be used without limitation as materials not described above.

[0199] Depending on the material to be used, the organic light-emitting element according to one embodiment of the present invention may be a top-emitting, bottom-emitting, or dual-emitting type.

[0200] Appendix Figure 1 To be continued Figure 3 The figures illustrate the stacking order of electrodes and organic layers in an organic light-emitting element according to an embodiment of the present invention. However, this is not intended to limit the scope of the invention to these figures, and the structures of organic light-emitting elements known in this art can also be applied to the present invention.

[0201] Reference Figure 1 This illustrates an organic light-emitting element in which an anode 200, an organic layer 300, and a cathode 400 are sequentially stacked on a substrate 100. However, it is not limited to this structure and can be configured as follows: Figure 2 The embodiment shown is an organic light-emitting element in which a cathode, an organic layer, and an anode are sequentially stacked on a substrate.

[0202] Figure 3 This illustrates the case where the organic layers are multilayered. According to... Figure 3The organic light-emitting element includes a hole injection layer 301, a hole transport layer 302, a light-emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306. However, the scope of the present invention is not limited to this stacked structure, and if necessary, the remaining layers other than the light-emitting layer can be omitted, and other necessary functional layers, such as an electron blocking layer, can be further added.

[0203] Furthermore, the present invention relates to an organic layer composition of an organic light-emitting element, the organic layer composition comprising

[0204] Heterocyclic compounds represented by Formula 1.

[0205] The specific contents of the heterocyclic compounds represented by Formula 1 are the same as those mentioned above.

[0206] Organic layer compositions can be used as hole injection layer materials, hole transport layer materials, electron blocking layer materials, light-emitting layer materials, hole blocking layer materials, electron transport layer materials, and electron injection layer materials, and more specifically, they can be preferably used as hole transport layer materials, electron blocking layer materials, and light-emitting layer materials.

[0207] When used as a light-emitting layer material, it can be used as a host material, and it can be more useful as a p-host (p-type host) with good hole transport capability among host materials.

[0208] The host material may consist only of the organic layer composition, or it may include a combination of the organic layer composition and other host materials.

[0209] The organic layer composition may further include materials commonly used in organic layer compositions in this art, as well as heterocyclic compounds represented by Formula 1.

[0210] Furthermore, this invention relates to a method for manufacturing an organic light-emitting element, the method comprising the following steps:

[0211] The process includes: preparing a substrate; forming a first electrode on the substrate; forming one or more organic layers on the first electrode; and forming a second electrode on the organic layers, wherein the step of forming the organic layers includes forming one or more organic layers using a heterocyclic compound represented by Formula 1 of the present invention or the organic layer composition.

[0212] In one embodiment of the invention, the step of forming the organic layer can be performed by a thermal vacuum deposition method using a heterocyclic compound represented by Formula 1 or the organic layer composition to form the organic layer.

[0213] If necessary, the organic layer comprising the organic layer composition may further include other materials commonly used in this technology.

[0214] According to an embodiment of the present invention, the heterocyclic compound represented by Formula 1 can function in organic electronic components, including organic solar cells, organic photoacceptors, organic transistors and the like, in a manner similar to that applied to said organic light-emitting elements.

[0215] In the following sections, preferred examples will be provided to aid in understanding the invention, but these examples are not intended to limit the invention, but rather to promote an understanding of it.

[0216] <Preparation Example>

[0217] [Preparation Example 1] Preparation of Compound 002

[0218]

[0219] 1) Preparation of compound 002-P3

[0220] 1-Bromo-2-chloro-3-fluorobenzene (100 g, 477.46 mmol) and phenylboronic acid (61.13 g, 501.34 mmol) were dissolved in 1000 mL toluene, 200 mL ethanol, and 200 mL distilled water. Pd(PPh3)4 (27.59 g, 23.87 mmol) and K2CO3 (164.98 g, 1193.66 mmol) were then added to the solution and stirred under reflux for 12 hours. After the reaction was complete, ethyl acetate was dissolved in the reaction solution, extracted with distilled water, and the organic layer was dried with anhydrous MgSO4. The solvent was then removed by rotary evaporation, and the solution was purified by column chromatography using dichloromethane and hexane as developing solvents to give compound 002-P3 (88 g, 89%).

[0221] 2) Preparation of compound 002-P2

[0222] Compound 002-P3 (88 g, 425.86 mmol) and 1-iododibenzo[b,d]furan-2-ol (145.26 g, 468.45 mmol) were dissolved in 1000 mL of N,N-dimethylacetamide and heated to 150 °C. Cs₂CO (277.51 g, 851.72 mmol) was then added and the mixture was stirred under reflux for 30 min. After the reaction was complete, the mixture was extracted with dichloromethane and distilled water, and the organic layer was dried with anhydrous MgSO₄. The solvent was then removed by rotary evaporation, and the mixture was purified by column chromatography using dichloromethane and hexane as the developing solvent to give compound 002-P2 (130 g, 61%).

[0223] 3) Preparation of compound 002-P1

[0224] Compound 002-P2 (130 g, 261.72 mmol) was dissolved in 1-methyl-2-pyrrolidone, and then Pd(PPh3)4 (15.12 g, 13.09 mmol), PPh3 (6.86 g, 26.17 mmol), and Na2CO3 (55.48 g, 523.43 mmol) were added and stirred under reflux for 12 hours. After the reaction was complete, the mixture was extracted with dichloromethane and distilled water, and the organic layer was dried with anhydrous MgSO4. The solvent was then removed by rotary evaporator, and the mixture was purified by column chromatography using dichloromethane and hexane as developing solvents to give compound 002-P1 (65 g, 67%).

[0225] 4) Preparation of compound 002

[0226] Compound 002-P1 (10 g, 27.11 mmol) and N-phenyl-[1,1'-biphenyl]-4-amine (6.98 g, 28.47 mmol) were dissolved in 100 mL of xylene. Pd2(dba)3 (1.24 g, 1.36 mmol), P(t-Bu)3 (1.26 mL, 2.71 mmol), and t-BuONa (6.51 g, 67.79 mmol) were then added to the xylene solution and stirred under reflux for 3 hours. After the reaction was complete, MC was dissolved in the reaction solution, extracted with distilled water, and the organic layer was dried with anhydrous MgSO4. The solvent was then removed by rotary evaporation, and the solution was purified by column chromatography using dichloromethane and hexane as developing solvents to give compound 002 (12 g, 77%).

[0227] Table 1 below shows that the target compounds were synthesized in the same manner as in Preparation Example 1, except that compound A was used instead of 1-bromo-2-chloro-3-fluorobenzene in Preparation Example 1, compound B was used instead of phenylboronic acid in Preparation Example 1, and compound C was used instead of N-phenyl-[1,1'-biphenyl]-4-amine in Preparation Example 1.

[0228] [Table 1]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234] [Preparation Example 2] Preparation of Compound 012

[0235]

[0236] 1) Preparation of compound 012

[0237] Compound 002-P1 (10 g, 27.11 mmol) and (4-(diphenylamino)phenyl)boronic acid (8.23 g, 28.47 mmol) were dissolved in 100 mL of 1,4-dioxane and 20 mL of H2O. Pd(dba)2 (0.78 g, 1.36 mmol), xphos (1.29 g, 2.71 mmol), and K2CO3 (9.37 g, 67.79 mmol) were then added to the solution and stirred under reflux for 3 hours. After the reaction was complete, MC was dissolved in the reaction solution, extracted with distilled water, and the organic layer was dried with anhydrous MgSO4. The solvent was then removed by rotary evaporation, and the solution was purified by column chromatography using dichloromethane and hexane as developing solvents to give compound 012 (11 g, 70%).

[0238] Table 2 below shows that the target compound was synthesized in the same manner as in Preparation Example 2, except that compound D was used instead of 002-P1 in Preparation Example 2 and compound E was used instead of (4-(diphenylamino)phenyl)boronic acid in Preparation Example 2.

[0239] [Table 2]

[0240]

[0241] The compound was prepared in the same manner as in the preparation examples above, and the results confirming the synthesis are shown in Tables 3 and 4. Table 3 shows the 1H nuclear magnetic resonance (NMR) measurements (CDCl3, 300 MHz), and Table 4 shows the field desorption mass spectrometry (FD-MS) measurements.

[0242] [Table 3]

[0243]

[0244]

[0245] [Table 4]

[0246] compound FD-MS compound FD-MS 002 m / z=577.67(C42H27NO2=577.20) 005 m / z=693.83(C51H35NO2=693.27) 012 m / z=577.67(C42H27NO2=577.20) 015 m / z=769.93(C57H39NO2=769.30) 019 m / z=693.83(C51H35NO2=693.27) 033 m / z=703.82(C52H33NO2=703.25) 052 m / z=783.95(C58H41NO2=783.31) 080 m / z=844.01(C63H41NO2=843.31) 098 m / z=717.81(C52H31NO3=717.23) 106 m / z=607.62(C42H25NO2S=607.16) 123 m / z=653.77(C48H31NO2=653.24) 125 m / z=693.83(C51H35NO2=693.27) 134 m / z=729.86(C54H35NO2=729.27) 136 m / z=577.67(C42H27NO2=577.20) 160 m / z=791.93(C59H37NO2=791.28) 168 m / z=703.82(C52H33NO2=703.25) 211 m / z=591.65(C42H25NO3=591.18) 229 m / z=723.88(C51H33NO2S=723.22) 243 m / z=653.77(C48H31NO2=653.24) 247 m / z=733.89(C54H39NO2=733.30) 255 m / z=769.93(C57H39NO2=769.30) 257 m / z=653.77(C48H31NO2=653.24) 267 m / z=653.77(C48H31NO2=653.24) 279 m / z=717.85(C53H35NO2=717.27) 292 m / z=783.95(C58H41NO2=783.31) 299 m / z=779.92(C58H37NO2=779.28) 311 m / z=839.97(C63H37NO2=839.28) 334 m / z=707.81(C51H33NO3=707.25) 347 m / z=683.81(C48H29NO2S=683.19) 363 m / z=653.77(C48H31NO2=653.24) 365 m / z=693.83(C51H35NO2=693.27) 371 m / z=739.86(C55H33NO2=739.25) 375 m / z=769.93(C57H39NO2=769.30) 378 m / z=729.86(C54H35NO2=729.27) 395 m / z=743.89(C55H37NO2=743.28) 411 m / z=743.89(C55H37NO2=743.28) 457 m / z=823.97(C60H41NO3=823.31) 603 m / z=769.93(C57H39NO2=769.30) 605 m / z=809.99(C60H43NO2=809.33) 632 m / z=693.83(C51H35NO2=693.27) 651 m / z=809.99(C60H43NO2=809.33) 657 m / z=693.83(C51H35NO2=693.27)

[0247] [Experimental Example]

[0248] <Experimental Example 1>

[0249] (1) Manufacturing of organic light-emitting elements

[0250] A glass substrate coated with a 1500 angstrom ITO film was ultrasonically washed with distilled water. After the distilled water was used up, it was ultrasonically washed with solvents such as acetone, methanol, isopropanol, and the like, and dried. Then, it underwent UV-ozone (UVO) treatment for 5 minutes in an ultraviolet (UV) cleaner. Next, the substrate was transferred to a plasma cleaner (PT) and then subjected to plasma treatment under vacuum to achieve the ITO work function and remove residual film. Finally, it was transferred to a thermal deposition apparatus for organic deposition.

[0251]

[0252] Next, after evacuating the chamber until a vacuum of 10⁻⁶ Torr is achieved, a current is applied to a cell to evaporate 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA), thereby depositing a 600 Å thick hole injection layer on the ITO substrate. N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) is placed in another cell of the vacuum deposition apparatus and evaporated by applying a current to the cell, thereby depositing a 300 Å thick hole transport layer on the hole injection layer.

[0253]

[0254] As described below, a light-emitting layer is thermally vacuum deposited on it. In the light-emitting layer, a 400 Å layer of the compound 9-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-3,3'-bi-9H-carbazole is deposited as the host, and a green phosphorescent dopant is deposited by doping Ir(ppy)3 at 7% concentration. Next, a 60 Å layer of BCP is deposited on it as a hole-blocking layer, and a 200 Å layer of Alq3 is deposited as an electron transport layer. Finally, an electron injection layer is formed by depositing a 10 Å thick layer of lithium fluoride (LiF) on the electron transport layer, and a cathode is then formed by depositing a 1,200 Å thick aluminum (Al) cathode on the electron injection layer, thereby fabricating the light-emitting element.

[0255] On the other hand, before being used in the manufacture of organic light emitting diodes (OLEDs), all organic compounds required for manufacturing OLED devices were vacuum sublimated and purified at 10⁻⁶ Torr to 10⁻⁸ Torr for each material.

[0256] Organic light-emitting elements were prepared in the same manner as in Experimental Example 1, except that the compounds of the present invention described in Table 5 below were used instead of NPB (which is the compound used to form the hole transport layer in Experimental Example 1), and the driving voltage and luminous efficiency of the organic light-emitting elements were measured, and the results are shown in Table 5 below.

[0257] In this case, in addition to NPB, the following compounds were used as comparative examples of hole transport compounds.

[0258]

[0259] (2) Driving voltage and luminous efficiency of organic light-emitting elements

[0260] For the organic light-emitting element manufactured as described above, the electroluminescence (EL) properties were measured using an M7000 from McScience, and based on the measurement results, the T95 was measured using a lifetime measurement element (M6000) manufactured by McScience at a reference luminance of 6,000 candela / m².

[0261] The properties of the organic light-emitting element of the present invention are shown in Table 5 below.

[0262] [Table 5]

[0263]

[0264] As can be seen, compared with the components of Comparative Examples 1 to 6, the components of Examples 1 to 42 according to an embodiment of the present invention have lower drive voltage and excellent efficiency and lifespan.

[0265] <Experimental Example 2>

[0266] (1) Manufacturing of organic light-emitting elements

[0267] The transparent electrode ITO film, obtained from OLED glass (manufactured by Samsung Corning), was ultrasonically washed every 5 minutes using trichloroethylene, acetone, ethanol, and distilled water, and then stored in isopropanol before use. Next, the ITO substrate was mounted in the substrate holder of the vacuum deposition apparatus, and 4,4',4”-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in the cell of the vacuum deposition apparatus.

[0268]

[0269] Next, after evacuating the chamber to a vacuum level of 10⁻⁶ Torr, a current is applied to the cell to evaporate 2-TNATA, thereby depositing a 600 Å thick hole injection layer on the ITO substrate. N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) is placed in another cell of the vacuum deposition apparatus and evaporated by applying a current to the cell, thereby depositing a 300 Å thick hole transport layer on the hole injection layer.

[0270]

[0271] After forming the hole injection layer and hole transport layer in this manner, a blue luminescent material with the following structure is deposited on them as the luminescent layer. Specifically, a blue luminescent host material H1 with a thickness of 200 angstroms is vacuum deposited in a cell of a vacuum deposition apparatus, and a blue luminescent dopant material D1 is vacuum deposited on it at an amount of 5% relative to the host material.

[0272]

[0273] Next, an electron transport layer with a thickness of 300 angstroms is deposited using a compound with the following structural formula E1.

[0274]

[0275] OLED devices were fabricated by depositing an electron injection layer with a thickness of 10 angstroms using lithium fluoride (LiF) and an aluminum cathode with a thickness of 1,000 angstroms. On the other hand, all organic compounds required for the fabrication of OLED devices were vacuum sublimated and purified at 10⁻⁶ Torr to 10⁻⁸ Torr for each material before being used in OLED fabrication.

[0276] Except that the hole transport layer NPB was formed to a thickness of 150 angstroms in Experimental Example 2 above, and an electron blocking layer of 50 angstroms thickness was further formed on the hole transport layer using the compounds of the present invention described in Table 6 below, an organic light-emitting element was fabricated in the same manner as in Experimental Example 2 above. The driving voltage, luminous efficiency, and lifetime of the fabricated blue organic light-emitting element were measured, and the results are shown in Table 6 below.

[0277] In this case, the electron blocking layer compound used as a comparative example is as follows.

[0278]

[0279] [Table 6]

[0280]

[0281] <Experimental Example 3>

[0282] 1) Manufacturing of organic light-emitting elements

[0283] A glass substrate coated with a 1500 angstrom thick indium tin oxide (ITO) film was ultrasonically washed with distilled water. After the distilled water was used up, the substrate was ultrasonically washed with solvents such as acetone, methanol, isopropanol, and the like, dried, and then subjected to UVO treatment in a UV cleaner for 5 minutes. Next, the substrate was transferred to a plasma cleaner (PT) and then subjected to plasma treatment under vacuum to achieve the ITO work function and remove residual film, and then transferred to a thermal deposition apparatus for organic deposition.

[0284] A hole injection layer 2-TNATA (4,4',4”-tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer NPB (N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) are formed on an ITO transparent electrode (anode) as a common layer.

[0285] As described below, a light-emitting layer was thermally vacuum deposited on it. A light-emitting layer with a thickness of 500 Å was deposited using the following method: using the compounds described in Table 7 below as the host, using an n-host (n-type host) with good electron transport capability as a single host or a first host, and using a p-host (p-type host) with good hole transport capability as a second host, two host compounds were deposited from a single source; and (piq)2(Ir)(acac) was used as a red phosphorescent dopant to dope (piq)2(Ir)(acac) in the host at 3% of the host material weight, or Ir(ppy)3 was used as a green phosphorescent dopant to dope Ir(ppy)3 in the host at 7% of the host material weight.

[0286] Next, a 60 angstrom thick BCP is deposited on it as a hole blocking layer, and a 200 angstrom thick Alq3 is deposited as an electron transport layer.

[0287] In this case, when two subjects are used, the compound used as subject n (the first subject) is as follows.

[0288]

[0289] Finally, an electron injection layer is formed by depositing a 10 angstrom thick lithium fluoride (LiF) layer on the electron transport layer, and then a cathode is formed by depositing a 1,200 angstrom thick aluminum (Al) cathode on the electron injection layer, thereby fabricating a light-emitting element.

[0290] Specifically, the compounds used as the main components in Examples 55 to 79 and Comparative Examples 12 to 21 are shown in Table 7 below.

[0291] In this case, the compounds M1 to M5 used as the main components in Comparative Examples 12 to 21 in Table 7 below are as follows.

[0292]

[0293] On the other hand, before being used in the manufacture of organic light-emitting elements, all organic compounds required for the manufacture of organic light-emitting elements were vacuum sublimated and purified at 10⁻⁶ Torr to 10⁻⁸ Torr for each material.

[0294] 2) Driving voltage and luminous efficiency of organic light-emitting elements

[0295] For the organic light-emitting elements manufactured as described above, the electroluminescence (EL) properties were measured using an M7000 from Microscience, and based on the measurement results, the T95 was measured using a lifetime measuring element (M6000) manufactured by Microscience at a reference luminance of 6,000 candela / m². The measurement results for the driving voltage, luminous efficiency, emission color, and lifetime of the organic light-emitting elements manufactured above are shown in Table 7 below.

[0296] [Table 7]

[0297]

[0298] As can be seen from the above experimental example 3, compared with the organic light-emitting elements of Comparative Examples 12, 14, 16, 18 and 20 that do not use the compound according to the present invention as a single host material, the organic light-emitting elements of Examples 55 to 64 that form the light-emitting layer by using the compound according to the present invention as a single host material have excellent luminous efficiency and lifetime.

[0299] As can be seen from the above experimental example 3, compared with the organic light-emitting elements of Comparative Examples 13, 15, 17, 19 and 21 in which the light-emitting layer is formed by using a first host material corresponding to the n host and a compound according to the invention as the second host material corresponding to the p host, the organic light-emitting elements of Examples 65 to 79 in which the light-emitting layer is formed by using a first host material corresponding to the n host and a compound according to the invention as the second host material corresponding to the p host have excellent luminous efficiency and lifetime.

[0300] This result implies that an organic light-emitting element (OLED) using an n-type host with good electron transport capability as the first host and a p-type host with good hole transport capability as the second host is a single host material. Generally, an n-type host with good electron transport capability has superior luminous efficiency and lifetime compared to OLEDs using a single host material. Using the compound according to the present invention as the host material can significantly improve the luminous efficiency and lifetime of the OLED.

[0301] This is attributed to the fact that, when the compound according to the invention is used as the host material, holes and electrons from each charge transport layer can be efficiently injected into the light-emitting layer. Furthermore, this result is attributed to the influence of orientation and space size formed during deposition due to material interactions.

[0302] In summary, since the efficient injection of holes and electrons into the luminescent layer is also affected by the orientation and space size formed by the interaction of materials during deposition, the above results are attributed to the fact that the compounds of the present invention provide better performance than compounds M1 to M5 in terms of orientation properties and space size.

[0303] This invention is not limited to the examples above, but can be manufactured in various different forms, and those skilled in the art will understand that the invention can be implemented in other specific forms without changing the technical spirit or essential characteristics of the invention. Therefore, it should be understood that the above examples are illustrative and not restrictive in any way.

Claims

1. A heterocyclic compound, represented by formula 1: [Formula 1] in: X and Y are O; R1 is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted 9,9-dimethylfluorenyl, a substituted or unsubstituted dibenzothiophene, or a substituted or unsubstituted dibenzofuranyl. R2 to R8 may be the same as or different from each other, and each is independently either hydrogen or deuterium; R9 and R10 may be the same as or different from each other, and each may independently be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted 9,9-dimethylfluorenyl, a substituted or unsubstituted 9,9-diphenylfluorenyl or a substituted or unsubstituted spirodifluorenyl. L1 and L2 may be the same as or different from each other, and each is independently a direct bond or a substituted or unsubstituted phenylene; m is an integer between 0 and 1; n is an integer between 0 and 1; o is an integer between 0 and 1. "Substituted or unsubstituted" means that it is substituted or not substituted by one or more substituents selected from the group consisting of C1 to C10 straight-chain or branched alkyl, C6 to C30 aryl, C2 to C30 heteroaryl, C6 to C30 arylamine and C2 to C30 heteroarylamine.

2. The heterocyclic compound according to claim 1, characterized in that... The heterocyclic compound represented by Formula 1 is a compound represented by any of the following compounds: 。 3. An organic light-emitting element, comprising: First electrode; The second electrode is positioned to face the first electrode; as well as One or more organic layers are disposed between the first electrode and the second electrode, and One or more of the organic layers comprise the heterocyclic compound as described in claim 1 or 2.

4. The organic light-emitting element according to claim 3, characterized in that... The organic layer includes one or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

5. The organic light-emitting element according to claim 3, characterized in that... The organic layer includes a hole transport layer, wherein the hole transport layer contains the heterocyclic compound.

6. The organic light-emitting element according to claim 3, characterized in that... The organic layer includes an electron blocking layer, wherein the electron blocking layer contains the heterocyclic compound.

7. The organic light-emitting element according to claim 3, characterized in that... The organic layer includes a light-emitting layer, wherein the light-emitting layer comprises a host material, wherein the host material comprises only the heterocyclic compound, or comprises a combination of the heterocyclic compound and other host materials.

8. An organic layer composition of an organic light-emitting element, comprising the heterocyclic compound as described in claim 1 or 2.

9. The organic layer composition according to claim 8, characterized in that... The organic layer composition is used for one or more purposes selected from hole injection layer materials, hole transport layer materials, electron blocking layer materials, light-emitting layer materials, hole blocking layer materials, electron transport layer materials, and electron injection layer materials of the organic light-emitting element.

10. The organic layer composition according to claim 9, characterized in that... The organic layer composition is used as the hole transport layer material, the electron blocking layer material, or the light-emitting layer material.

11. The organic layer composition according to claim 10, characterized in that... The light-emitting layer material is the main material.

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