Heterocyclic compounds, organic light emitting elements, and compositions

Abstract

The present application provides a heterocyclic compound represented by formula 1, an organic light emitting element including the same, and a composition for forming an organic layer.

Description

Technical Field

[0001] This application claims priority based on Korean Patent Application No. 10-2020-0153293, filed on November 17, 2020, and the entire contents disclosed in the document of said Korean Patent Application are incorporated herein by reference.

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

[0003] Due to the increasing demand for flat panel display components, organic light-emitting diodes (OLEDs) have recently received much attention. OLEDs are devices that convert electrical energy into light, and their performance is greatly influenced by the organic material positioned between the electrodes.

[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 functionality. For example, as organic thin film materials, compounds capable of forming a light-emitting layer by themselves 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 serving as hole injection layers, hole transport layers, electron blocking layers, electron transport layers, electron injection layers, electron generation layers, and the like 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] Existing technical references

[0008] Patent documents

[0009] Korean Patent No. 10-1838693 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 a composition comprising the said heterocyclic compound for forming an organic layer.

[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] R1 to R4 may be the same as or different from each other, and each is independently 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, or -P(=O)R101R102R103, wherein R101, R102, and R103 may be the same as or different from each other, and each is independently substituted or unsubstituted C6 to C60 aryl or substituted or unsubstituted C2 to C60 heteroaryl;

[0020] R5 and R6 may be the same as or different from each other, and each independently is 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 or substituted or unsubstituted C2 to C60 heteroaryl;

[0021] L1 to L8 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;

[0022] m, n, o, p, q, r, s, and t are either the same or different from each other, and each is an independent integer from 0 to 2, provided that when m, n, o, p, q, r, s, and t are 2, each of L1 to L8 defined by these letters is either the same or different from each other and is independently selected; and

[0023] u is an integer from 0 to 4, provided that when u is from 2 to 4, R6 are either the same as each other or different and are chosen independently.

[0024] In addition, the present invention provides an organic light-emitting element, the organic light-emitting element comprising:

[0025] First electrode;

[0026] The second electrode is positioned to face the first electrode; and

[0027] One or more organic layers are disposed between the first electrode and the second electrode, and

[0028] One or more of the plurality of organic layers contain the heterocyclic compound represented by Formula 1.

[0029] In addition, the present invention provides a composition for forming an organic layer in an organic light-emitting element, the composition comprising the heterocyclic compound represented by Formula 1.

[0030] Beneficial effects

[0031] 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 electron transport layers, charge generation layers, electron injection layers, electron blocking layers, and hole blocking layers, thereby providing significant effects in reducing the driving voltage of organic light-emitting elements, improving luminous efficiency, and improving lifetime properties.

[0032] 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

[0033] Figures 1 to 4 These are schematic diagrams illustrating the stacked structure of an organic light-emitting element according to an embodiment of the present invention.

[0034] [Symbol Explanation]

[0035] 100:Substrate

[0036] 200: Anode

[0037] 300: Organic layer

[0038] 301: Hole Injection Layer

[0039] 302: Hole Transport Layer

[0040] 303: Emissive layer

[0041] 304: Cavity Blocking Layer

[0042] 305: Electron transport layer

[0043] 306: Electron Injection Layer

[0044] 400: Cathode Detailed Implementation

[0045] The invention will be described in detail below.

[0046] 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.

[0047] 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.

[0048] 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.

[0049] 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.

[0050] 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.

[0051] 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.

[0052] 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.

[0053] 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. Benzyl, phenanthrene, perylene, fluoranthracene, dithionyl, fenyl, pyrene, condensed tetraphenyl, condensed pentaphenyl, fluorenyl, indene, acenaphthene, benzofluorenyl, spirodifluorenyl, 2,3-dihydro-1H-indene, their condensed cyclic groups and analogues.

[0054] In this invention, the fluorene group can be substituted, and adjacent substituents can bond to each other to form a ring.

[0055] When the fluorene group is substituted, it can be, but is not limited to, the following: and similar substances.

[0056] 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.

[0057] 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.

[0058] 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.

[0059] 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.

[0060] In this invention, "where no substituents are indicated in the chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, due to deuterium ( 2 H is an isotope of hydrogen, therefore some hydrogen atoms may be deuterium.

[0061] 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%.

[0062] 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").

[0063] In one embodiment of the present invention, deuterium is an isotope of hydrogen, and is an element having a deuterium nucleus consisting of one proton and one neutron, and can be represented as hydrogen-2, and its element symbol can also be written as D or 2 H.

[0064] 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.

[0065] 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.

[0066] 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:

[0067]

[0068] 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).

[0069] In this invention, the deuterium content in the heterocyclic compound represented by Formula 1 can be from 0% to 100%, more preferably from 10% to 50%.

[0070] This invention provides a heterocyclic compound, which is represented by the following formula 1:

[0071] [Formula 1]

[0072]

[0073] in:

[0074] R1 to R4 may be the same as or different from each other, and each is independently 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, or -P(=O)R101R102R103, wherein R101, R102, and R103 may be the same as or different from each other, and each is independently substituted or unsubstituted C6 to C60 aryl or substituted or unsubstituted C2 to C60 heteroaryl;

[0075] R5 and R6 may be the same as or different from each other, and each independently is 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 or substituted or unsubstituted C2 to C60 heteroaryl;

[0076] L1 to L8 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;

[0077] m, n, o, p, q, r, s, and t are either the same or different from each other, and each is an independent integer from 0 to 2, provided that when m, n, o, p, q, r, s, and t are 2, each of L1 to L8 defined by these letters is either the same or different from each other and is independently selected; and

[0078] u is an integer from 0 to 4, provided that when u is from 2 to 4, R6 are either the same or different from each other and can be chosen independently.

[0079] 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.

[0080] In another embodiment of the invention, the heteroatoms in the heteroatom-containing group may be one or more selected from O, S or N.

[0081] In another embodiment of the invention, the heteroatom in the heteroatom-containing group may be N.

[0082] In one embodiment of the invention, R1 to R4 may be the same as or different from each other, and may each be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, 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.

[0083] In another embodiment of the invention, R1 to R4 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 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.

[0084] In another embodiment of the invention, R1 to R4 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.

[0085] In another embodiment of the invention, R1 to R4 may be the same as or different from each other, and may each be independently hydrogen, deuterium, substituted or unsubstituted phenyl, naphthyl, anthracene, or phenanthrene.

[0086] X can be the same or different from each other, and can be a nitrogen atom or a carbon atom, provided that at least one of them can be a nitrogen atom.

[0087] Both of X can be nitrogen atoms.

[0088] The owner of X can be a nitrogen atom.

[0089] In another embodiment of the invention, three or more of R1 to R4 may be the same as or different from each other, and may each be independently a substituted or unsubstituted C6 to C20 aryl, a 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 a substituted or unsubstituted C6 to C20 aryl or a substituted or unsubstituted C2 to C20 heteroaryl, and the other may be hydrogen or deuterium.

[0090] In another embodiment of the invention, R4 may be hydrogen or deuterium.

[0091] In one embodiment of the invention, the substitution of R1 to R4 may each be independently carried out using one or more substituents 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.

[0092] In another embodiment of the invention, the substitution of R1 to R4 may be carried out independently using one or more substituents 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.

[0093] In another embodiment of the invention, the substitution of R1 to R4 can each be carried out independently using one or more substituents selected from the group consisting of 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 substitution of R1 to R4 may be carried out independently using one or more substituents selected from the group consisting of phenyl, naphthyl, pyridyl, anthracene, carbazole, biphenyl, dibenzothiophene, dibenzofuran and phenanthrene.

[0095] In one embodiment of the invention, R5 and R6 may be the same as or different from each other, and may each be independently hydrogen, deuterium, substituted or unsubstituted C6 to C30 aryl or substituted or unsubstituted C2 to C30 heteroaryl.

[0096] In another embodiment of the invention, R5 and R6 may be the same as or different from each other, and may each be independently hydrogen, deuterium, substituted or unsubstituted C6 to C20 aryl or substituted or unsubstituted C2 to C20 heteroaryl.

[0097] In another embodiment of the invention, R5 and R6 may be the same as or different from each other, and may each be independently hydrogen, deuterium, substituted or unsubstituted phenyl, naphthyl, anthraceneyl, phenanthrene, etc.

[0098] X can be the same or different from each other, and can be nitrogen or carbon atoms independently, provided that at least one of them can be a nitrogen atom.

[0099] Both of X can be nitrogen atoms.

[0100] The owner of X can be a nitrogen atom.

[0101] In one embodiment of the invention, the substitution of R5 and R6 may be carried out independently using one or more substituents 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.

[0102] In another embodiment of the invention, the substitution of R5 and R6 may be carried out independently using one or more substituents 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.

[0103] In another embodiment of the invention, the substitution of R5 and R6 may be carried out independently using one or more substituents selected from the group consisting of C6 to C30 aryl, C2 to C30 heteroaryl, C6 to C30 arylamine and C2 to C30 heteroarylamine.

[0104] In another embodiment of the invention, the substitution of R5 and R6 may be carried out independently using one or more substituents selected from the group consisting of phenyl, naphthyl, pyridyl, anthracene, carbazole, biphenyl, dibenzothiophene, dibenzofuran and phenanthrene.

[0105] 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.

[0106] 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.

[0107] In another embodiment of the invention, L1 to L8 may be the same as or different from each other, and may each be independently a direct bond, substituted or unsubstituted benzene, naphthalene, etc. Anthracene, phenanthrene or

[0108] X can be the same or different from each other, and each can be a nitrogen atom or a carbon atom independently, provided that at least one of them is a nitrogen atom; and Y can be the same or different from each other, and each can be a nitrogen atom or a carbon atom independently, provided that at least one of them is a nitrogen atom.

[0109] Both of X can be nitrogen atoms.

[0110] The owner of X can be a nitrogen atom.

[0111] The owner of Y can be a nitrogen atom.

[0112] In another embodiment of the invention, the substitution of L1 to L8 may each be carried out independently using one or more substituents 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.

[0113] In another embodiment of the invention, the substitution of L1 to L8 may be carried out independently using one or more substituents 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.

[0114] In another embodiment of the invention, the substitution of L1 to L8 may be carried out independently using one or more substituents selected from the group consisting of C6 to C30 aryl, C2 to C30 heteroaryl, C6 to C30 arylamine and C2 to C30 heteroarylamine.

[0115] In another embodiment of the invention, the substitution of L1 to L8 may be carried out independently using one or more substituents selected from the group consisting of phenyl, naphthyl, pyridyl, anthracene, carbazole, biphenyl, dibenzothiophene, dibenzofuran and phenanthrene.

[0116] In Formula 1 above, R1 to R3 may be the same as or different from each other, and may each be independently a substituted or unsubstituted C6 to C60 aryl, a 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 a substituted or unsubstituted C6 to C60 aryl or a substituted or unsubstituted C2 to C60 heteroaryl.

[0117] In Equation 1 above, more preferably, any one or more of -(L1)m-(L2)n-R1, -(L3)o-(L4)p-R2, -(L5)q-(L6)r-R3 and -(L7)s-(L8)t-R4 may comprise 2 to 8 aromatic rings with or without heteroatoms, wherein the 2 to 8 aromatic rings may be composed of a monocyclic aromatic ring, an aromatic ring contained in a polycyclic condensed aromatic ring, or an aromatic ring contained in both a monocyclic aromatic ring and a polycyclic condensed aromatic ring.

[0118] Additionally, any one or more of -(L1)m-(L2)n-R1, -(L3)o-(L4)p-R2, -(L5)q-(L6)r-R3 and -(L7)s-(L8)t-R4 may contain 3 to 8 aromatic rings with or without heteroatoms, wherein the 3 to 8 aromatic rings with or without heteroatoms may be composed of a monocyclic aromatic ring, an aromatic ring contained in a polycyclic condensed aromatic ring, or an aromatic ring contained in both a monocyclic aromatic ring and a polycyclic condensed aromatic ring.

[0119] The monocyclic aromatic ring can be phenyl or Furthermore, the polycyclic aromatic ring can be naphthalene, anthracene, phenanthrene, carbazole, dibenzothiophene, dibenzofuran, etc. Or similar substances, wherein X may be the same or different from each other, and may each be a nitrogen atom or a carbon atom independently, provided that at least one of them is a nitrogen atom; and Y may be the same or different from each other, and may each be a nitrogen atom or a carbon atom independently, provided that at least one of them is a nitrogen atom.

[0120] In Formula 1 above, more preferably, R1 to R3 are the same or different from each other, and each is independently a substituted or unsubstituted phenyl, naphthyl, anthracene, phenanthrene,

[0121] R4 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted phenyl, naphthyl, anthracene, phenanthrene,

[0122] R5 and R6 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted C6 to C30 aryl or substituted or unsubstituted C2 to C30 heteroaryl;

[0123] L1 and L8 may be the same as or different from each other, and each is independently a direct bond, substituted or unsubstituted phenylene, naphthalene, Anthracene, phenanthrene or

[0124] Where X are all the same or different, and each is independently a nitrogen atom or a carbon atom, provided that at least one is a nitrogen atom; and Y are all the same or different, and each is independently a nitrogen atom or a carbon atom, provided that at least one is a nitrogen atom; and

[0125] The substitution can be carried out using one or more substituents selected from the group consisting of substituted or unsubstituted phenyl, naphthyl, pyridyl, anthryl, carbazole, biphenyl, dibenzothiophene, dibenzofuran and phenanthrene.

[0126] In Equation 1 above, or even more preferably, the heterocyclic compound represented by Equation 1 can be...

[0127]

[0128] in:

[0129] A may comprise 2 to 8 aromatic rings, with or without heteroatoms, wherein the 2 to 8 aromatic rings may be composed of monocyclic aromatic rings, aromatic rings contained in polycyclic condensed aromatic rings, or aromatic rings contained in both monocyclic aromatic rings and polycyclic condensed aromatic rings; and

[0130] B can be a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0131] The monocyclic aromatic rings and polycyclic aromatic rings are the same as those mentioned above.

[0132] In Equation 1 above, particularly preferably, A can be 5 to 7 aromatic rings with or without heteroatoms.

[0133] In Formula 1 above, particularly preferably, A can be 5 to 7 aromatic rings containing heteroatoms.

[0134] B can be a substituted or unsubstituted phenyl group.

[0135] In one embodiment of the invention, the heterocyclic compound represented by Formula 1 may be a compound represented by any of the following compounds:

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163] 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, electron injection layer materials, and electron generation layer materials, into the core structure, materials that meet the requirements of each organic layer can be synthesized.

[0164] 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.

[0165] 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, electron injection layer material, and electron generation layer material. In essence, they can be used as electron transport layer material, charge generation layer material, electron injection layer material, electron blocking layer material, and hole blocking layer material, and more specifically, they can be used as electron transport layer material and charge generation layer material.

[0166] Furthermore, this invention relates to a light-emitting element, the light-emitting element comprising:

[0167] A first electrode; a second electrode, configured to face the first electrode; and one or more organic layers disposed between the first electrode and the second electrode.

[0168] One or more of the organic layers contain a heterocyclic compound represented by Formula 1.

[0169] In one embodiment of the present invention, the first electrode may be an anode and the second electrode may be a cathode.

[0170] In another embodiment, the first electrode may be a cathode, and the second electrode may be an anode.

[0171] 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.

[0172] 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.

[0173] 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.

[0174] 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.

[0175] In one embodiment of the present invention, the organic light-emitting element may be a white organic light-emitting device (WOLED), and the heterocyclic compound represented by Formula 1 may be used as a material for the white organic light-emitting element.

[0176] The specific contents of the heterocyclic compounds represented by Formula 1 are the same as those mentioned above.

[0177] 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.

[0178] In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 can be used as one or more of the following materials selected from green organic light-emitting elements, blue organic light-emitting elements, red organic light-emitting elements, and white 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, electron injection layer material, and charge generation layer material. In essence, it can be used as an electron transport layer material, charge generation layer material, electron injection layer material, electron blocking layer material, and hole blocking layer material, and more specifically, it can be preferably used as an electron transport layer material and a charge generation layer material.

[0179] Figures 1 to 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.

[0180] 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.

[0181] 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.

[0182] According to one embodiment of the invention, an organic light-emitting element may have a tandem structure in which two or more independent elements are connected in series. In one embodiment, the tandem structure may have the form in which each organic light-emitting element is bonded to a charge-generating layer. Since an element with a tandem structure can be driven with a lower current than a single element for the same brightness, there is an advantage of greatly improving the lifetime properties of the element.

[0183] According to one embodiment of the present invention, the organic layer includes a first stack containing one or more light-emitting layers; a second stack containing one or more light-emitting layers; and one or more charge-generating layers disposed between the first stack and the second stack.

[0184] According to another embodiment of the present invention, the organic layer includes a first stack containing one or more light-emitting layers; a second stack containing one or more light-emitting layers; and a third stack containing one or more light-emitting layers, and includes one or more charge-generating layers between the first stack and the second stack and between the second stack and the third stack, respectively.

[0185] A charge generation layer can refer to a layer in which holes and electrons are generated when a voltage is applied. The charge generation layer can be an N-type charge generation layer or a P-type charge generation layer. In this invention, an N-type charge generation layer refers to a charge generation layer positioned closer to the anode than a P-type charge generation layer, and a P-type charge generation layer refers to a charge generation layer positioned closer to the cathode than an N-type charge generation layer.

[0186] The N-type and P-type charge generation layers can be positioned in contact with each other, forming an NP junction. Through the NP junction, holes readily form in the P-type charge generation layer, and electrons readily form in the N-type charge generation layer. Electrons are transported in the anodic direction via the lowest unoccupied molecular orbital (LUMO) level of the N-type charge generation layer, while holes are transported in the cathode direction via the highest occupied molecular orbital (HOMO) level of the P-type charge generation layer.

[0187] The first stack, the second stack, and the third stack each independently include one or more light-emitting layers, and may further include one or more layers selected from the following: a hole injection layer, a hole transport layer, an electron blocking layer, a layer that simultaneously transports and injects holes (hole injection and transport layer), and a layer that simultaneously transports and injects electrons (electron injection and transport layer).

[0188] Figure 4 The figures illustrate an organic light-emitting diode comprising a first stack and a second stack. However, the scope of the invention is not intended to be limited by these figures, and the structures of organic light-emitting elements known in this art can also be applied to the present invention.

[0189] In some cases, it can be omitted. Figure 4 The first electron blocking layer, the first hole blocking layer, the second hole blocking layer, and the like are described in the text.

[0190] According to one embodiment of the present invention, the charge generation layer comprising the heterocyclic compound of Formula 1 may be an N-type charge generation layer, and the charge generation layer may further comprise dopants known in the art other than the heterocyclic compound of Formula 1.

[0191] 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.

[0192] 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.

[0193] The organic layer of the organic light-emitting element of the present invention may have a single-layer structure, but may also have 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 comprising one or more of 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, an electron injection layer, an electron generating 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.

[0194] 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.

[0195] 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.

[0196] 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.

[0197] 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.

[0198] 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.

[0199] 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.

[0200] As an electron injection layer material, LiF is commonly used in this technology, for example, but the invention is not limited thereto.

[0201] 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.

[0202] 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.

[0203] In the phosphorescent materials described herein, phosphorescent materials known in this art can be used as phosphorescent dopant materials. 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.

[0204] M can be iridium, platinum, osmium, or similar substances.

[0205] Where L is through sp 2An anionic bidentate ligand coordinated to M by carbon and heteroatoms, wherein 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, pyridine carboxylate, 8-hydroxyquinoline ester, and the like.

[0206] Specific examples of phosphorescent dopants are shown below, but are not limited to these examples.

[0207]

[0208] 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.

[0209] 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.

[0210] 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.

[0211] 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).

[0212] In addition, the electron blocking layer material may contain inorganic compounds. For example, it may contain 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.

[0213] 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.

[0214] The N-type charge-generating layer may include, but is not limited to, 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), fluorinated 3,4,9,10-perylenetetracarboxylic dianhydride (PTCDA), cyano-substituted PTCDA, naphthalenetetracarboxylic dianhydride (NTCDA), fluorinated NTCDA, cyano-substituted NTCDA, hexaazatriphenylene derivative, and the like. In one embodiment, the N-type charge-generating layer may simultaneously comprise a benzimidazole-phenanthrene derivative and Li metal.

[0215] P-type charge-generating layers can simultaneously contain aryl amine derivatives and cyano-containing compounds.

[0216] 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.

[0217] 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.

[0218] In addition, the present invention relates to an organic layer composition of an organic light-emitting element, said organic layer composition comprising a heterocyclic compound represented by Formula 1.

[0219] The specific contents of the heterocyclic compounds represented by Formula 1 are the same as those mentioned above.

[0220] The composition used in the organic layer 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, an electron injection layer material, and a charge generation layer material. In essence, it can be used as an electron transport layer material, a charge generation layer material, an electron injection layer material, an electron blocking layer material, and a hole blocking layer material, and more specifically, it can be used as an electron transport layer material and a charge generation layer material.

[0221] If it is used as a charge generation layer material, it can be used as an N-type charge generation layer material.

[0222] 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.

[0223] Furthermore, this invention relates to a method for manufacturing an organic light-emitting element, the method comprising the following steps:

[0224] 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.

[0225] 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 material layer composition to form the organic layer.

[0226] If necessary, the organic layer comprising the organic layer composition may also include other materials commonly used in this art.

[0227] 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.

[0228] Mode of implementing the present invention

[0229] 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.

[0230] <Preparation Example>

[0231] [Preparation Example 1] Preparation of Compound 1

[0232] [Option 1]

[0233]

[0234] 1) Preparation of compound 1-1

[0235] 2-Bromobenzaldehyde (60 g, 324.29 mmol, 1 equivalent), ethynylbenzene (36.4 g, 356.72 mmol, 1.1 equivalent), bis(triphenylphosphine)palladium(II) dichloride (4.56 g, 6.49 mmol, 0.02 equivalent), and copper iodide (0.61 g, 3.24 mmol, 0.01 equivalent) were placed in 600 mL of trimethylamine and stirred at 60 °C for 6 h. The solution was passed through diatomaceous earth and then washed with methylene chloride (MC). The solvent was concentrated and then passed through a silica gel. The solvent was removed to give 58 g of compound 1-1, in 87% yield.

[0236] 2) Preparation of compounds 1-2

[0237] Compound 1-1 (58 g, 281.23 mmol, 1 equivalent) and acetophenone (37.2 g, 309.35 mmol, 1.1 equivalent) were placed in a 10% sodium hydroxide aqueous solution (58 mL) and methanol (580 mL) and stirred at room temperature for 3 hours. After the reaction was complete, the precipitated solid was filtered and washed with water and methanol. 72 g of compound 1-2 was obtained, in 83% yield.

[0238] 3) Preparation of compounds 1-3

[0239] Compounds 1-2 (72 g, 233.48 mmol, 1 equivalent) were added to acetic acid (720 mL), and then (4-bromophenyl)hydrazine (52.4 g, 280.18 mmol, 1.2 equivalent) and iodine (71.1 g, 280.18 mmol, 1.2 equivalent) were added under stirring and refluxed for 8 hours. After the reaction was complete, the reaction solution was cooled to room temperature and diluted with distilled water, and then neutralized with an aqueous sodium bicarbonate solution. Extraction was performed with ethyl acetate and distilled water, followed by separation using a silica gel column (eluent MC:hexane, Hex = 1:5) to give 100 g of compounds 1-3, in 75% yield.

[0240] 4) Preparation of compounds 1-4

[0241] Compounds 1-3 (100 g, 210.35 mmol, 1 equivalent), bis(pinacol)diboron (80.1 g, 315.52 mmol, 1.5 equivalent), PdCl2(dppf) (15.39 g, 21.04 mmol, 0.1 equivalent), and KOAc (41.29 g, 420.70 mmol, 2 equivalent) were placed in 1000 mL of 1,4-dioxane and stirred at 100 °C for 6 h. Extraction was performed with MC and water, and the organic layer was dried with anhydrous Na2SO4 and filtered through a silica gel. After precipitation with MC / MeOH, the precipitate was filtered to give 91 g of compounds 1-4, in 83% yield.

[0242] 5) Preparation of Compound 1

[0243] Compounds 1-4 (11.4 g, 21.86 mmol, 1 equivalent) and 2-bromo-1,10-phenanthroline (5.66 g, 21.86 mmol, 1 equivalent) were dissolved in 110 mL of 1,4-dioxane and 25 mL of distilled water. Pd(PPh3)4 (1.26 g, 1.09 mmol, 0.05 equivalent) and K2CO3 (6.04 g, 43.72 mmol, 2 equivalent) were then added to the solution, and the mixture was stirred under reflux for 15 hours. MC was placed and dissolved in the reaction solution, and then extracted with water. The organic layer was dried with anhydrous Na2SO4. The solution was passed through a silica gel filter and precipitated with MC / MeOH. The precipitated solid was filtered to give 10.8 g of compound 1, in 88% yield.

[0244] The target compound A in Table 1 was synthesized in the same manner as in Preparation Example 1, except that intermediate A in Table 1 was used instead of 2-bromo-1,10-phenobarbital.

[0245] [Table 1]

[0246]

[0247]

[0248]

[0249] [Preparation Example 2] Preparation of Compound 61

[0250] [Option 2]

[0251]

[0252] 1) Preparation of compound 61-1

[0253] Compound 1-1 (58 g, 281.23 mmol, 1 equivalent) and 1-(4-bromophenyl)ethyl-1-one (61.6 g, 309.35 mmol, 1.1 equivalent) were placed in a 10% sodium hydroxide aqueous solution (58 mL) and methanol (580 mL) and stirred at room temperature for 5 hours. After the reaction was complete, the precipitated solid was filtered and washed with water and methanol. 90.4 g of compound 61-1 was obtained, in a yield of 83%.

[0254] 2) Preparation of compound 61-2

[0255] Compound 61-1 (72 g, 233.48 mmol, 1 equivalent) was added to acetic acid (720 mL), followed by the addition of phenylhydrazine (30.3 g, 280.18 mmol, 1.2 equivalent) and iodine (71.1 g, 280.18 mmol, 1.2 equivalent) under stirring, and the mixture was stirred under reflux for 7 hours. After the reaction was complete, the reaction solution was cooled to room temperature and diluted with distilled water, then neutralized with an aqueous sodium bicarbonate solution. Extraction was performed with ethyl acetate and distilled water, followed by separation via a silica gel column (eluent MC:hexane = 1:5) to give 100 g of compound 61-2, in 75% yield.

[0256] 3) Preparation of compound 61-3

[0257] Compound 61-2 (100 g, 210.35 mmol, 1 equivalent), bis(pinacol)diboron (80.1 g, 315.52 mmol, 1.5 equivalent), PdCl2(dppf) (15.39 g, 21.04 mmol, 0.1 equivalent), and KOAc (41.29 g, 420.70 mmol, 2 equivalent) were placed in 1000 mL of 1,4-dioxane and stirred at 100 °C for 9 hours. Extraction was performed with MC and water, and the organic layer was dried with anhydrous Na2SO4 and filtered through a silica gel. After precipitation with MC / MeOH, the precipitate was filtered to give 91 g of compound 61-3, in 83% yield.

[0258] 4) Preparation of compound 61

[0259] Compounds 1-4 (11.4 g, 21.86 mmol, 1 equivalent) and 2-bromo-1,10-phenanthroline (5.66 g, 21.86 mmol, 1 equivalent) were dissolved in 110 mL of 1,4-dioxane and 25 mL of distilled water. Pd(PPh3)4 (1.26 g, 1.09 mmol, 0.05 equivalent) and K2CO3 (6.04 g, 43.72 mmol, 2 equivalent) were then added to the solution, and the mixture was stirred under reflux for 15 hours. MC was placed and dissolved in the reaction solution, and then extracted with water. The organic layer was dried with anhydrous Na2SO4. The solution was passed through a silica gel filter and precipitated with MC / MeOH. The precipitated solid was filtered to give 9.0 g of compound 61, in a yield of 72%.

[0260] The target compound B in Table 2 was synthesized in the same manner as in Preparation Example 2, except that intermediate B in Table 2 was used instead of 2-bromo-1,10-phenobarbital.

[0261] [Table 2]

[0262]

[0263]

[0264]

[0265]

[0266] [Preparation Example 3] Preparation of Compound 121

[0267] [Option 3]

[0268]

[0269] 1) Preparation of compound 121-1

[0270] 2-Bromobenzaldehyde (60 g, 324.29 mmol, 1 equivalent), 1-bromo-4-ethynylbenzene (64.6 g, 356.72 mmol, 1.1 equivalent), bis(triphenylphosphine)palladium(II) dichloride (4.56 g, 6.49 mmol, 0.02 equivalent), and copper iodide (0.61 g, 3.24 mmol, 0.01 equivalent) were placed in 600 mL of trimethylamine and stirred at 60 °C for 5 h. The solution was passed through diatomaceous earth and then washed with MC. The solvent was concentrated and then passed through a silica gel. The solvent was removed to give 80.2 g of compound 121-1, in 87% yield.

[0271] 2) Preparation of compound 121-2

[0272] Compound 121-1 (80.2 g, 281.23 mmol, 1 equivalent) and acetophenone (37.2 g, 309.35 mmol, 1.1 equivalent) were placed in a 10% sodium hydroxide aqueous solution (58 mL) and methanol (580 mL) and stirred at room temperature for 8 hours. After the reaction was complete, the precipitated solid was filtered and washed with water and methanol. 90.4 g of compound 121-2 was obtained, in 83% yield.

[0273] 3) Preparation of compound 121-3

[0274] Compound 121-2 (90.4 g, 233.48 mmol, 1 equivalent) was added to acetic acid (720 mL), followed by the addition of phenylhydrazine (30.3 g, 280.18 mmol, 1.2 equivalent) and iodine (71.1 g, 280.18 mmol, 1.2 equivalent) under stirring, and the mixture was stirred under reflux for 13 hours. After the reaction was complete, the reaction solution was cooled to room temperature and diluted with distilled water, then neutralized with an aqueous sodium bicarbonate solution. Extraction was performed with ethyl acetate and distilled water, followed by separation via a silica gel column (eluent MC:hexane = 1:5) to give 100 g of compound 121-3, in 75% yield.

[0275] 4) Preparation of compound 121-4

[0276] Compound 121-3 (100 g, 210.35 mmol, 1 equivalent), bis(pinacol)diboron (80.1 g, 315.52 mmol, 1.5 equivalent), PdCl2(dppf) (15.39 g, 21.04 mmol, 0.1 equivalent), and KOAc (41.29 g, 420.70 mmol, 2 equivalent) were placed in 1000 mL of 1,4-dioxane and stirred at 100 °C for 12 h. Extraction was performed with MC and water, and the organic layer was dried over anhydrous Na2SO4 and filtered through a silica gel. After precipitation with MC / MeOH, the precipitate was filtered to give 85.7 g of compound 121-4, in a yield of 78%.

[0277] 5) Preparation of compound 121

[0278] Compound 121-4 (11.4 g, 21.86 mmol, 1 equivalent) and 2-bromo-1,10-phenanthroline (5.66 g, 21.86 mmol, 1 equivalent) were dissolved in 110 mL of 1,4-dioxane and 25 mL of distilled water. Pd(PPh3)4 (1.26 g, 1.09 mmol, 0.05 equivalent) and K2CO3 (6.04 g, 43.72 mmol, 2 equivalent) were then added to the solution, and the mixture was stirred under reflux for 15 hours. MC was placed and dissolved in the reaction solution, and then extracted with water. The organic layer was dried with anhydrous Na2SO4. The solution was passed through a silica gel filter and precipitated with MC / MeOH. The precipitated solid was filtered to give 8.8 g of compound 121, in a yield of 70%.

[0279] Except for using intermediate C from Table 3 instead of 2-bromo-1,10-phenobarbital, the target compound C in Table 3 was synthesized in the same manner as in Preparation Example 3.

[0280] [Table 3]

[0281]

[0282]

[0283]

[0284] [Preparation Example 4] Preparation of Compound 321

[0285] [Option 4]

[0286]

[0287] 1) Preparation of compound 321-1

[0288] 2-Bromo-3-chlorobenzaldehyde (71.2 g, 324.29 mmol, 1 equivalent), ethynylbenzene (36.4 g, 356.72 mmol, 1.1 equivalent), bis(triphenylphosphine)palladium(II) dichloride (4.56 g, 6.49 mmol, 0.02 equivalent), and copper iodide (0.61 g, 3.24 mmol, 0.01 equivalent) were placed in 700 mL of trimethylamine and stirred at 60 °C for 8 hours. The solution was passed through diatomaceous earth and then washed with MC. The solvent was concentrated and then passed through a silica gel. The solvent was removed to give 67.7 g of compound 321-1 in 87% yield.

[0289] 2) Preparation of compound 321-2

[0290] Compound 321-1 (67.7 g, 281.23 mmol, 1 equivalent) and acetophenone (37.2 g, 309.35 mmol, 1.1 equivalent) were placed in a 10% sodium hydroxide aqueous solution (67 mL) and methanol (670 mL) and stirred at room temperature for 10 hours. After the reaction was complete, the precipitated solid was filtered and washed with water and methanol. 80 g of compound 321-2 was obtained, in 83% yield.

[0291] 3) Preparation of compound 321-3

[0292] Compound 321-2 (80 g, 233.48 mmol, 1 equivalent) was added to acetic acid (800 mL), followed by the addition of phenylhydrazine (30.3 g, 280.18 mmol, 1.2 equivalent) and iodine (71.1 g, 280.18 mmol, 1.2 equivalent) under stirring, and the mixture was stirred under reflux for 16 hours. After the reaction was complete, the reaction solution was cooled to room temperature and diluted with distilled water, then neutralized with an aqueous sodium bicarbonate solution. Extraction was performed with ethyl acetate and distilled water, followed by separation via a silica gel column (eluent MC:hexane = 1:5) to give 90.6 g of compound 321-3, in 75% yield.

[0293] 4) Preparation of compound 321-4

[0294] Compound 321-3 (90.6 g, 210.35 mmol, 1 equivalent), bis(pinacol)diboron (80.1 g, 315.52 mmol, 1.5 equivalent), PdCl2(dppf) (15.39 g, 21.04 mmol, 0.1 equivalent), and KOAc (41.29 g, 420.70 mmol, 2 equivalent) were placed in 900 mL of 1,4-dioxane and stirred at 100 °C for 18 h. Extraction was performed with MC and water, and the organic layer was dried over anhydrous Na2SO4 and filtered through a silica gel. Precipitation with MC / MeOH was followed by filtration of the precipitate to give 77.6 g of compound 321-4, in 85% yield.

[0295] 5) Preparation of compound 321

[0296] Compound 321-4 (11.4 g, 21.86 mmol, 1 equivalent) and 2-bromo-1,10-phenanthroline (5.66 g, 21.86 mmol, 1 equivalent) were dissolved in 110 mL of 1,4-dioxane and 25 mL of distilled water. Pd(PPh3)4 (1.26 g, 1.09 mmol, 0.05 equivalent) and K2CO3 (6.04 g, 43.72 mmol, 2 equivalent) were then added to the solution, and the mixture was stirred under reflux for 8 hours. MC was added and dissolved in the reaction solution, and then extracted with water. The organic layer was dried with anhydrous Na2SO4. The solution was passed through a silica gel filter and precipitated with MC / MeOH. The precipitated solid was filtered to give 9.7 g of compound 321, in a yield of 77%.

[0297] Except for the use of intermediate D instead of 2-bromo-3-chlorobenzaldehyde and intermediate E instead of 2-bromo-1,10-phenanthroline in Table 4 below, the target compound E in Table 4 below was synthesized in the same manner as in Preparation Example 4.

[0298] [Table 4]

[0299]

[0300]

[0301]

[0302] The compound was prepared in the same manner as in the preparation examples above, and the results of the synthesis confirmation are shown in Tables 5 and 6. Table 5 shows... 1 The measurements were obtained by nuclear magnetic resonance (NMR) (CDCl3, 200 MHz), and Table 6 shows the measurements obtained by field desorption mass spectrometry (FD-MS).

[0303] [Table 5]

[0304]

[0305]

[0306] [Table 6]

[0307]

[0308]

[0309] [Experimental Example]

[0310] <Experimental Example 1>

[0311] 1) Manufacturing of organic light-emitting elements

[0312] A glass substrate coated with a 1500 Å thick 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, dried, and then subjected to 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, and then transferred to a thermal deposition apparatus for organic deposition. An organic layer was formed in a single light-emitting stack structure on the ITO transparent electrode (anode). A hole injection layer was formed by depositing a 50 Å thick HAT-CN, and then a hole transport layer NPD was doped with DNTPD in an amount up to 10% and deposited to a thickness of 1500 Å, and TCTA was continuously deposited to a thickness of 200 Å. Next, a 250 Å thick light-emitting layer containing a third butylperylene dopant was formed on the ADN body. Next, an electron transport layer Alq3 with a thickness of 250 angstroms is formed, an N-type charge generation layer with a thickness of 100 angstroms is formed by doping the compounds described in Table 7 with alkali metal lithium, and a cathode Al with a thickness of about 1,000 angstroms is formed, thereby fabricating an organic light-emitting element.

[0313]

[0314] 2) Driving voltage and luminous efficiency of organic light-emitting elements

[0315] 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 lifetime measurement was performed using a lifetime measurement element (M6000) manufactured by McScience at a reference luminance of 750 candela / m² (cd / m²). 2 T at that time 95 The driving voltage, luminous efficiency, external quantum efficiency, and color coordinates (measured by the International Commission on Illumination, CIE) of the white organic light-emitting element manufactured according to the present invention are shown in Table 7.

[0316] [Table 7]

[0317]

[0318]

[0319] Based on the results in Table 7 above, it is confirmed that, compared to the comparative examples, the blue organic light-emitting elements (single light-emitting stack structure) using the compounds of the present invention as charge-generating layer materials exhibit lower driving voltage and improved luminous efficiency. Specifically, it is confirmed that the examples using compounds 8, 37, 46, 105, 159, 167, and 389 of the present invention provide significantly superior effects in all embodiments regarding driving voltage, efficiency, and lifetime.

[0320] This result is assumed to be due to the fact that the compounds of the present invention are composed of suitable heterocyclic compounds having a framework with suitable length, strength, and flatness, and capable of bonding to metals, thereby forming interstitial states in the N-type charge-generating layer in a doped state of alkali metals or alkaline earth metals. Specifically, since electrons generated from the P-type charge-generating layer are easily injected into the electron transport layer through the interstitial states generated in the N-type charge-generating layer, it is assumed that they exhibit excellent effects.

[0321] That is, assuming that due to the above properties, the P-type charge generation layer can effectively inject and transfer electrons to the N-type charge generation layer, thereby exhibiting a reduced driving voltage and improved luminous efficiency and lifetime properties of the organic light-emitting element.

[0322] Furthermore, it was confirmed that the blue organic light-emitting devices of Comparative Examples 1-3, having an electron-generating layer composed of compounds having the same basic framework as those of the present invention, exhibited poor driving voltage, efficiency, and lifetime properties compared to other comparative examples (1-1 and 1-2). Based on these results, it can be seen that improved electroluminescence and lifetime properties cannot be obtained using only the basic framework of the compounds of the present invention. Additionally, it was confirmed that only when the basic framework is appropriately combined with various substituents, as in the compounds of the present invention, can appropriate physicochemical and thermal properties be provided, and excellent properties and results be exhibited in device evaluation.

[0323] <Experimental Example 2>

[0324] 1) Manufacturing of organic light-emitting elements

[0325] 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 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. Finally, it was transferred to a thermal deposition apparatus for organic deposition.

[0326] An organic layer is formed in a 2-light-emitting stacked WOLED (white organic light-emitting element) structure on an ITO transparent electrode (anode).

[0327] In the case of the first luminescent stack, a hole transport layer is first formed by thermally vacuum depositing a 300 Å thick TAPC. After forming the hole transport layer, a luminescent layer is thermally vacuum deposited thereon as described below. The host TCz1 is doped with the blue phosphorescent dopant FIrpic at an amount of 8% to deposit the 300 Å luminescent layer. After forming a 400 Å electron transport layer using TmPyPB, a 100 Å charge generation layer is formed by doping the compounds described in Table 8 with Cs2CO3 at an amount of 20%.

[0328] In the case of the second light-emitting stack, a hole injection layer is first formed by thermal vacuum deposition of a 50 Å thick MoO3. A hole transport layer as a common layer is formed by doping TAPC with MoO3 at a rate of 20% to form a 100 Å layer, followed by deposition of a 300 Å thick TAPC layer. A 300 Å light-emitting layer is deposited on the host TCz1 by doping it with the green phosphorescent dopant Ir(ppy)3 at a rate of 8%, and then a 600 Å electron transport layer is formed using TmPyPB. Finally, an electron injection layer is formed by depositing a 10 Å thick lithium fluoride (LiF) layer on the electron transport layer, and then a cathode is formed by depositing a 1,200 Å thick aluminum (Al) cathode on the electron injection layer, thereby fabricating the light-emitting element.

[0329] On the other hand, before being used in the manufacture of organic light-emitting diodes (OLEDs), each material is tested at 10... -6 Up to 10 -8 All the organic compounds required for manufacturing OLED components were vacuum sublimated and purified.

[0330]

[0331] 2) Driving voltage and luminous efficiency of organic light-emitting elements

[0332] For the organic light-emitting element manufactured as described above, the electroluminescence (EL) properties were measured using an M7000 from Macquarie, and based on the measurement results, the TL at a reference luminance of 3,500 candela / m² was measured using a lifetime measurement element (M6000) manufactured by Macquarie. 95 The driving voltage, luminous efficiency, external quantum efficiency, and color coordinates (CIE) of the white organic light-emitting element manufactured according to the present invention are shown in Table 8.

[0333] [Table 8]

[0334]

[0335]

[0336] Based on the results in Table 8 above, it is confirmed that, compared to the comparative examples, the white organic light-emitting elements (2-light-emitting stack structure) using the compounds of the present invention as the charge-generating layer material exhibit lower driving voltage and improved luminous efficiency in the examples. Specifically, it is confirmed that the examples using compounds 8, 37, 46, 105, 159, 167, and 389 of the present invention provide significantly superior effects in all embodiments regarding driving voltage, efficiency, and lifetime.

[0337] This result is assumed to be due to the fact that the compounds of the present invention are composed of suitable heterocyclic compounds having a framework with suitable length, strength, and flatness, and capable of bonding to metals, thereby forming interstitial states in the N-type charge-generating layer, which is in a state of being doped with alkali metals or alkaline earth metals. Specifically, since electrons generated from the P-type charge-generating layer can be easily injected into the electron transport layer through the interstitial states generated in the N-type charge-generating layer, it is assumed that they exhibit excellent effects.

[0338] That is, assuming that due to the above properties, the P-type charge generation layer can effectively inject and transfer electrons to the N-type charge generation layer, thereby exhibiting a reduced driving voltage and improved luminous efficiency and lifetime properties of the organic light-emitting element.

[0339] Furthermore, it was confirmed that the white organic light-emitting device of Comparative Example 2-3, having an electron-generating layer composed of a compound having the same basic framework as the compound of the present invention, exhibited poor driving voltage, efficiency, and lifetime properties compared to other comparative examples (2-1 and 2-2). Based on these results, it can be seen that improved electroluminescence and lifetime properties cannot be obtained using only the basic framework of the compound of the present invention. Additionally, it was confirmed that only when the basic framework is appropriately combined with various substituents as in the compound of the present invention can appropriate physicochemical and thermal properties be provided, and excellent properties and results be exhibited in device evaluation.

[0340] <Experimental Example 3>

[0341] 1) Manufacturing of organic light-emitting elements

[0342] The transparent electrode ITO film obtained from the glass used in OLEDs is ultrasonically washed every 5 minutes using trichloroethylene, acetone, ethanol and distilled water, and then stored in isopropanol before use.

[0343] Next, the ITO substrate is mounted in the substrate holder of the vacuum deposition apparatus, and the following 4,4',4”-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) is placed in the cell of the vacuum deposition apparatus.

[0344]

[0345] Next, the chamber is evacuated until the vacuum level reaches 10. -6 After that, an electric current is applied to the cell to evaporate 2-TNATA, thereby depositing a 600 angstrom thick hole injection layer on the ITO substrate.

[0346] The following N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed in another cell of a vacuum deposition apparatus and evaporated by applying an electric current to the cell, thereby depositing a 300 Å thick hole transport layer on the hole injection layer.

[0347]

[0348] 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.

[0349]

[0350] Next, an electron transport layer with a thickness of 300 angstroms was deposited using the compounds in Table 9 below.

[0351]

[0352] OLED devices are fabricated by depositing an electron injection layer with a thickness of 10 angstroms using lithium fluoride (LiF) and an Al cathode with a thickness of 1,000 angstroms.

[0353] On the other hand, before being used in OLED manufacturing, each material is tested at 10... -6 Up to 10 -8 All the organic compounds required for manufacturing OLED components were vacuum sublimated and purified.

[0354] 2) Driving voltage and luminous efficiency of organic light-emitting elements

[0355] For the organic light-emitting element manufactured as described above, the electroluminescence (EL) properties were measured using an M7000 from Macquarie, and based on the measurement results, the TL at a reference luminance of 700 candela / m² was measured using a lifetime measurement element (M6000) manufactured by Macquarie. 95 The driving voltage, luminous efficiency, external quantum efficiency, and color coordinates (CIE) of the blue organic light-emitting element manufactured according to the present invention are shown in Table 9.

[0356] [Table 9]

[0357]

[0358]

[0359]

[0360] Based on the results in Table 9 above, it is confirmed that, compared to the comparative examples, the blue organic light-emitting elements using the compounds of the present invention as electron transport layer materials exhibit lower driving voltages and significantly improved efficiency and lifetime. Specifically, examples using compounds 8, 37, 46, 105, 159, 167, and 389 demonstrate superior results in all embodiments regarding driving voltage, efficiency, and lifetime.

[0361] This result is attributed to the fact that when the compounds of the present invention, possessing suitable length, strength, and flatness, are used as electron transport layer materials, the compounds in the excited state are produced by accepting electrons under certain conditions. Specifically, if an excited state is formed at the heteroskeleton site of the compound, the excited heteroskeleton site returns to a stable state before reacting with other compounds. Therefore, the stabilized compound can react with other compounds to efficiently transfer electrons without decomposition or destruction. For reference, compounds that are stable when excited are aryl, benzobenzene, or polycyclic heterocyclic compounds. Therefore, it is determined that the compounds of the present invention provide excellent effects in all embodiments regarding drive voltage, efficiency, and lifetime due to improved electron transport properties or stability.

[0362] Furthermore, it was confirmed that the blue organic light-emitting element of Comparative Example 3-3, having an electron transport layer composed of a compound having the same basic framework as the compound of the present invention, exhibited poor driving voltage, luminous efficiency, and lifetime properties compared to other comparative examples (3-1 and 3-2). Based on these results, it can be seen that improved electroluminescence and lifetime properties cannot be obtained using only the basic framework of the compound of the present invention. Additionally, it was confirmed that only when the basic framework is appropriately combined with various substituents as in the compound of the present invention can appropriate physicochemical and thermal properties be provided, and excellent properties and results be exhibited in element evaluation.

[0363] This invention is not limited to the examples above, but can be manufactured in various different forms. Those skilled in the art will understand that this invention can be implemented in other specific forms without altering its technical spirit or essential characteristics. 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: R1 to R3 may be the same as or different from each other, and each may be independently substituted or unsubstituted phenyl, naphthyl, anthracene, phenanthrene, , , or ; Where X are the same or different from each other, and each is independently a nitrogen atom or a carbon atom, provided that at least one of them is a nitrogen atom; The substitution can be carried out using one or more substituents selected from the group consisting of phenyl, naphthyl, pyridyl, anthryl, carbazole, biphenyl, dibenzothiophene, dibenzofuran and phenanthrene; R4 is hydrogen, substituted or unsubstituted phenyl, naphthyl, anthracene, phenanthrene, , , or ; Where X are the same or different from each other, and each is independently a nitrogen atom or a carbon atom, provided that at least one of them is a nitrogen atom; The substitution can be carried out using one or more substituents selected from the group consisting of phenyl, naphthyl, pyridyl, anthryl, carbazole, biphenyl, dibenzothiophene, dibenzofuran and phenanthrene; R5 and R6 are hydrogen; L1 to L8 may be the same as or different from each other, and each is independently a direct bond, substituted or unsubstituted phenylene, naphthalene, anthracene, phenanthrene or , Where X are the same or different from each other, and each is independently a nitrogen atom or a carbon atom, provided that at least one of them is a nitrogen atom; and Y are the same or different from each other, and each is independently a nitrogen atom or a carbon atom, provided that at least one of them is a nitrogen atom; The substitution can be carried out using one or more substituents selected from the group consisting of phenyl, naphthyl, pyridyl, anthryl, carbazole, biphenyl, dibenzothiophene, dibenzofuran and phenanthrene; m, n, o, p, q, r, s, and t are either the same or different from each other, and each is an independent integer of 0 or 1, and u is 1; In Formula 1, any one of -(L1)m-(L2)n-R1, -(L3)o-(L4)p-R2, -(L5)q-(L6)r-R3 and -(L7)s-(L8)t-R4 contains 2 to 8 aromatic rings with or without heteroatoms, and the other three are all phenyl, or two of the other two are phenyl and the other is hydrogen.

2. The heterocyclic compound according to claim 1, wherein the 2 to 8 aromatic rings comprise 3 to 8 aromatic rings having or not having heteroatoms.

3. The heterocyclic compound according to claim 1, wherein any one of -(L1)m-(L2)n-R1, -(L3)o-(L4)p-R2, -(L5)q-(L6)r-R3 and -(L7)s-(L8)t-R4 comprises 2 to 8 aromatic rings having heteroatoms.

4. The heterocyclic compound according to claim 1, wherein the heterocyclic compound represented by formula 1 is a compound represented by any of the following compounds: 。 5. 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 plurality of organic layers comprises a heterocyclic compound as described in any one of claims 1 to 4.

6. The organic light-emitting element according to claim 5, wherein the organic layer comprises an electron transport layer, wherein the electron transport layer contains the heterocyclic compound.

7. The organic light-emitting element according to claim 5, wherein the organic layer comprises an electron injection layer or an electron transport layer, wherein the electron injection layer or the electron transport layer comprises the heterocyclic compound.

8. The organic light-emitting element according to claim 5, wherein the organic layer comprises an electron blocking layer or a hole blocking layer, wherein the electron blocking layer or the hole blocking layer contains the heterocyclic compound.

9. The organic light-emitting element of claim 5, wherein the organic layer comprises a first stack containing one or more light-emitting layers; and a second stack containing one or more light-emitting layers, and between the first stack and the second stack comprises one or more charge-generating layers containing the heterocyclic compound.

10. The organic light-emitting element of claim 5, wherein the organic layer comprises a first stack containing one or more light-emitting layers; a second stack containing one or more light-emitting layers; and a third stack containing one or more light-emitting layers, and wherein between the first stack and the second stack and between the second stack and the third stack are one or more charge-generating layers each containing the heterocyclic compound.

11. The organic light-emitting element according to claim 9 or 10, wherein the charge-generating layer is an N-type charge-generating layer.

12. A composition for forming an organic layer of an organic light-emitting element, comprising a heterocyclic compound as described in any one of claims 1 to 4.

13. The composition for forming an organic layer according to claim 12, wherein the organic layer is an electron transport layer, a charge generation layer, an electron injection layer, an electron blocking layer, or a hole blocking layer.

Images