Heterocyclic compound and organic light-emitting element comprising the same

Abstract

The present specification relates to a heterocyclic compound represented by Chemical Formula 1 and an organic light-emitting element including the same. In Chemical Formula 1, the definition of each substituent is the same as that in the embodiment. [Chemical Formula 1]

Description

[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2020-0099811 filed in the Korean Intellectual Property Office on August 10, 2020, the entire contents of which are incorporated herein by reference. Technical Field

[0002] The present invention relates to a heterocyclic compound and an organic light-emitting element comprising the same. Background Art

[0003] An electroluminescent element is a self-luminous display element and has the advantages of a wide viewing angle, a high response speed and an excellent contrast.

[0004] The organic light-emitting element has a structure in which an organic thin film is provided between two electrodes. When a voltage is applied to the organic light-emitting element having such a structure, electrons and holes injected from the two electrodes are combined and paired in the organic thin film, and light is emitted as they are annihilated. The organic thin film can be formed into a single layer or multiple layers as required.

[0005] The material of the organic film may have a light-emitting function as required. For example, as the material of the organic film, a compound that can form a light-emitting layer by itself can be used, or a compound that can play the role of a host or dopant of a light-emitting layer based on a host dopant can also be used. In addition, compounds that can play the role of hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, etc. can also be used as the material of the organic film.

[0006] In order to improve the performance, lifespan or efficiency of organic light emitting devices, there is a constant need to develop organic thin film materials. Summary of the invention

[0007] Technical issues

[0008] The present invention relates to providing a heterocyclic compound and an organic light-emitting element including the same.

[0009] Technical Solutions

[0010] One embodiment of the present specification provides a heterocyclic compound of the following Chemical Formula 1.

[0011] [Chemical formula 1]

[0012]

[0013] In Chemical Formula 1,

[0014] X1 and X2 are each independently N; or CR, and at least one of X1 and X2 is N,

[0015] R, R1 and R2 are each independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted silyl; substituted or unsubstituted phosphine oxide; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, and

[0016] r is an integer of 1 to 4, and when it is 2 or more, R2's are the same as or different from each other.

[0017] In addition, an embodiment of the present application provides an organic light-emitting element, which includes: a first electrode; a second electrode, which is arranged opposite to the first electrode; and an organic material layer, which is arranged between the first electrode and the second electrode, wherein the organic material layer contains one or more heterocyclic compounds of Chemical Formula 1.

[0018] Beneficial effects

[0019] The heterocyclic compound described in this specification can be used as a material for an organic material layer of an organic light-emitting element. The heterocyclic compound can act as a hole injection material, a hole transport material, a light-emitting material, an electron transport material, an electron injection material, a charge generating material, etc. Specifically, the heterocyclic compound can be used as a material for an electron transport layer or a charge generating layer of an organic light-emitting element.

[0020] Chemical formula 1 has a core structure in which a bicyclic heterocycle containing N is fused with phenanthroline, and by enhancing the electron-withdrawing property in the phenanthroline skeleton, anion radicals generated when electrons are injected can be stabilized, and the electron transport capability and charge generation capability can be enhanced by adjusting the band gap and energy level value (T1) in the triplet state.

[0021] Furthermore, when the heterocyclic compound of Chemical Formula 1 is used as a material for an electron transport layer or a charge generation layer of an organic light emitting element, the driving voltage of the element can be reduced, the light efficiency can be improved, and the lifespan property of the element can be improved. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] Figures 1 to 4 are diagrams each showing a stacked structure of an organic light emitting element according to an embodiment of the present specification.

[0023] [Explanation of symbols]

[0024] 100: Substrate

[0025] 200: Anode

[0026] 300: Organic material layer

[0027] 301: Hole injection layer

[0028] 302: Hole transport layer

[0029] 303: Luminous layer

[0030] 304: Electron transport layer

[0031] 305: Electron injection layer

[0032] 400: cathode DETAILED DESCRIPTION

[0033] Hereinafter, the present specification will be described in more detail.

[0034] In the present specification, description that a specific part “includes” specific constituent elements means that other constituent elements can be further included, and other constituent elements are not excluded unless specifically described otherwise.

[0035] In this specification, the T1 value refers to the energy level value in the triplet state.

[0036] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position of substitution is not limited as long as it is a position where the hydrogen atom is substituted (i.e., a position that the substituent can replace), and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

[0037] In the present specification, "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of: deuterium; halogen; cyano; C1 to C60 alkyl; C2 to C60 alkenyl; C2 to C60 alkynyl; C3 to C60 cycloalkyl; C2 to C60 heterocycloalkyl; C6 to C60 aryl; C2 to C60 heteroaryl; silanyl; phosphine oxide; and amine, or is unsubstituted, or is substituted with a substituent connecting two or more substituents selected from the above substituents, or is unsubstituted.

[0038] In this specification, "when no substituent is specified in a chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, due to the deuterium ( 2 H (Deuterium) is an isotope of hydrogen, so some of the hydrogen atoms may be deuterium.

[0039] In one embodiment of the present application, "in the case where no substituent is specified in the chemical formula or compound structure" may mean that all positions that can be substituents may be hydrogen or deuterium. In other words, since deuterium is an isotope of hydrogen, some hydrogen atoms may be deuterium as an isotope, and in this article, the content of deuterium may be 0% to 100%.

[0040] In one embodiment of the present application, in the case where “no substituent is specified in the chemical formula or compound structure”, when deuterium is not explicitly excluded (for example, the deuterium content is 0%, the hydrogen content is 100%, or the substituents are all hydrogen), hydrogen and deuterium may be mixed in the compound.

[0041] In one embodiment of the present application, deuterium is one of the isotopes of hydrogen, is an element having a deuteron formed by one proton and one neutron as a nucleus, and can be represented as hydrogen-2, and the element symbol can also be written as D or 2 H.

[0042] In one embodiment of the present application, isotopes refer to atoms having the same atomic number (atomic number, Z) but different mass numbers (mass number, A), and can also be interpreted as elements having the same proton number but different neutron numbers.

[0043] In one embodiment of the present application, when the total number of substituents that a basic compound may have is defined as T1, and the number of specific substituents therein is defined as T2, the content T% of the specific substituent may be defined as T2 / T1×100=T%.

[0044] In other words, in one example, The phenyl group having a deuterium content of 20% represented by means that the total number of substituents that the phenyl group may have is 5 (T1 in the formula), and the number of deuterium in the substituent is 1 (T2 in the formula). In other words, the phenyl group having a deuterium content of 20% can be represented by the following structural formula.

[0045]

[0046] Furthermore, in one embodiment of the present application, “the deuterium content of the phenyl group is 0%” may refer to a phenyl group that does not include a deuterium atom, that is, a phenyl group that has 5 hydrogen atoms.

[0047] In the present specification, halogen may be fluorine, chlorine, bromine or iodine.

[0048] In the present specification, the alkyl group includes a linear or branched alkyl group, and may be further substituted with other substituents. The number of carbon atoms of the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples thereof may include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, octyl, n-octyl, t-octyl, 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, but are not limited thereto.

[0049] In the present specification, alkenyl includes straight or branched alkenyl, and can be further substituted by other substituents. The carbon number of alkenyl can be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Its specific examples can include 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, distyryl, styryl, etc., but are not limited thereto.

[0050] In the present specification, the alkynyl group includes a straight chain or branched chain alkynyl group, and may be further substituted with other substituents. The number of carbon atoms of the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0051] In this specification, cycloalkyl includes monocyclic or polycyclic cycloalkyl with 3 to 60 carbon atoms, and can be further substituted by other substituents. In this article, polycyclic refers to a group in which the cycloalkyl is directly connected to other cyclic groups or fused with other cyclic groups. In this article, other cyclic groups can be cycloalkyl, but can also be different types of cyclic groups, such as heterocycloalkyl, aryl and heteroaryl. The carbon group number of the cycloalkyl can be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Its specific examples can include 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, etc., but are not limited thereto.

[0052] In this specification, heterocycloalkyl includes O, S, Se, N or Si as heteroatoms, including monocyclic or polycyclic heterocycloalkyl with 2 to 60 carbon atoms, and can be further substituted by other substituents. In this article, polycyclic refers to a group in which heterocycloalkyl is directly connected to other cyclic groups or fused with other cyclic groups. In this article, other cyclic groups can be heterocycloalkyl, but can also be different types of cyclic groups, such as cycloalkyl, aryl and heteroaryl. The number of carbon atoms of heterocycloalkyl can be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0053] In this specification, aryl includes monocyclic or polycyclic aromatic groups having 6 to 60 carbon atoms, and may be further substituted by other substituents. In this article, polycyclic refers to a group in which the aryl is directly connected to other cyclic groups or fused with other cyclic groups. In this article, other cyclic groups may be aryl, but may also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl and heteroaryl. Aryl includes spirocyclic groups. The number of carbon atoms of the aryl may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of aryl may include phenyl, biphenyl, terphenyl (terphenyl), naphthyl, anthracenyl, The invention also includes, but is not limited to, a phenanthrenyl group, a peryl group, a fluoranthenyl group, a triphenylene group, a phenanthrenyl group, a pyrenyl group, a condensed tetraphenyl group, a condensed pentaphenyl group, a fluorenyl group, an indenyl group, an acenaphthenyl group, a benzofluorenyl group, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, and condensed ring groups thereof.

[0054] In the present specification, the terphenyl group may be selected from the following structures.

[0055]

[0056] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0057] When the fluorenyl group is substituted, it may include etc., however, the structure is not limited thereto.

[0058] In this specification, heteroaryl includes O, S, SO 2, Se, N or Si as heteroatoms, including monocyclic or polycyclic heteroaryl groups, and may be further substituted by other substituents. In this article, polycyclic means a group in which a heteroaryl group is directly connected or fused to other cyclic groups. In this article, other cyclic groups may be heteroaryl groups, but may also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl and aryl groups. 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 the heteroaryl group may include pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furanyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazanyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxynyl group, triazinyl, tetrazinyl, quinolyl, isoquinolyl, quinazolinyl, isoquinazolinyl, quinozolinyl, quinolinaz ... group), naphthyridinyl, acridinyl, phenanthridinyl, imidazopyridinyl, naphthyridinyl, triazaindenyl, indolyl, indolizinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenanthrazinyl, dibenzosilyl (dibenzosilole group), spirobis(dibenzosilyl), dihydrophenazinyl, phenoxazinyl, phenanthridinyl, imidazopyridinyl, thienyl, indolo[2,3-a]carbazolyl, indolo[2,3-b]carbazolyl, indolyl, 10,11-dihydro-dibenzo[b,f]azepine, 9,10-dihydroacridinyl, phenazinyl, phenathiazinyl, phthalazinyl, naphthyridinyl, Phanthenyl, benzo[c][1,2,5]thiadiazolyl, 5,10-dihydrobenzo[b,e][1,4]azasilinyl, pyrazolo[1,5-c]quinazolinyl, pyrido[1,2-b]indazolyl, pyrido[1,2-a]imidazo[1,2-e]dihydroindole, benzofurano[2,3-d]pyrimidinyl; benzothieno[2,3-d]pyrimidinyl;benzofurano[2,3-a]carbazolyl, benzothieno[2,3-a]carbazolyl, 1,3-dihydroindole[2,3-a]carbazolyl, benzofurano[3,2-a]carbazolyl, benzothieno[3,2-a]carbazolyl, 1,3-dihydroindole[3,2-a]carbazolyl, benzofurano[2,3-b]carbazolyl, benzothieno[2,3-b]carbazolyl, 1,3-dihydroindole[2,3-b]carbazolyl, benzofurano[3,2-b]carbazolyl, benzothieno[3,2-b]carbazolyl, 1,3-dihydroindole[3,2-b]carbazolyl, benzofurano[2,3-c] Carbazolyl, benzothieno[2,3-c]carbazolyl, 1,3-dihydroindole[2,3-c]carbazolyl, benzofurano[3,2-c]carbazolyl, benzothieno[3,2-c]carbazolyl, 1,3-dihydroindole[3,2-c]carbazolyl, 1,3-dihydroindeno[2,1-b]carbazolyl, 5,11-dihydroindeno[1,2-b]carbazolyl, 5,12-dihydroindeno[1,2-c]carbazolyl, 5,8-dihydroindeno[2,1-c]carbazolyl, 7,12-dihydroindeno[1,2-a]carbazolyl, 11,12-dihydroindeno[2,1-a]carbazolyl, etc., but are not limited thereto. ;

[0059] In this specification, a silyl group is a substituent group containing Si, a Si atom directly attached as a free radical, and is represented by -SiR 101 R 102 R 103 Indicates. 101 To R 103 The same as or different from each other, and each independently may be a substituent formed by at least one of the following: hydrogen; deuterium; halogen; alkyl; alkenyl; alkoxy; cycloalkyl; aryl; and heteroaryl. Specific examples of the silyl group may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but are not limited thereto.

[0060] In this specification, the phosphine oxide group is represented by -P(=O)R 104 R 105 Indicates that, and R 104 With R 105 The phosphine oxide group may be the same as or different from each other, and each may be independently a substituent formed by at least one of the following: hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; aryl group; and heteroaryl group. Specifically, the phosphine oxide group may be substituted by an aryl group, and as the aryl group, the above examples may be applied. Examples of the phosphine oxide group may include a dimethyl phosphine oxide group, a diphenyl phosphine oxide group, a dinaphthyl phosphine oxide group, etc., but are not limited thereto.

[0061] In this specification, the amine group is represented by -NR 106 R 107 Indicates that, and R 106 With R 107 The same as or different from each other, and each independently can be a substituent formed by at least one of the following: hydrogen; deuterium; halogen; alkyl; alkenyl; alkoxy; cycloalkyl; aryl; and heteroaryl. Specifically, the amine group can be selected from -NH 2 The amino group may be selected from the group consisting of: a monoalkylamino group; a monoarylamino group; a monoheteroarylamino group; a dialkylamino group; a diarylamino group; a diheteroarylamino group; an alkylarylamino group; an alkylheteroarylamino group; and an arylheteroarylamino group, and although not particularly limited thereto, the number of carbon atoms is preferably 1 to 30. Specific examples of the amino group may include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, dibiphenylamino, anthracenylamino, 9-methyl-anthrylamino, diphenylamino, phenylnaphthylamino, ditolylamino, phenyltolylamino, triphenylamino, biphenylnaphthylamino, phenylbiphenylamino, biphenylfluorenylamino, phenyltriphenyleneamino, biphenyltriphenyleneamino, etc., but are not limited thereto.

[0062] In the present specification, except that the arylene group is a divalent group, the above-described examples of the arylene group can be applied to the arylene group.

[0063] In the present specification, the above-described examples of the heteroarylene group can be applied to the heteroarylene group except that the heteroarylene group is a divalent group.

[0064] In the present specification, "adjacent groups" may refer to a substituent that replaces an atom directly connected to an atom substituted by a corresponding substituent, a substituent that is spatially located closest to a corresponding substituent, or another substituent that replaces an atom substituted by a corresponding substituent. For example, two substituents that replace ortho positions of a benzene ring, and two substituents that replace the same carbon in an aliphatic ring may be interpreted as "adjacent groups" to each other.

[0065] As the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle or aromatic heterocycle which the adjacent groups may form, the structures shown as the above-mentioned cycloalkyl group, aryl group, heterocycloalkyl group and heteroaryl group can be used respectively except those which are not monovalent groups.

[0066] One embodiment of the present specification provides a heterocyclic compound represented by Chemical Formula 1.

[0067] In one embodiment of the present specification, X1 and X2 are each independently N; or CR, and at least one of X1 and X2 is N.

[0068] In one embodiment of the present specification, X1 is N, and X2 is CR.

[0069] In one embodiment of the present specification, X1 is CR, and X2 is N.

[0070] In one embodiment of the present specification, R and R1 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0071] In one embodiment of the present specification, R and R1 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0072] In one embodiment of the present specification, R and R1 are each independently hydrogen; deuterium; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0073] In one embodiment of the present specification, R and R1 are each independently hydrogen; deuterium; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0074] In one embodiment of the present specification, R is hydrogen; deuterium; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0075] In one embodiment of the present specification, R is hydrogen; deuterium; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0076] In one embodiment of the present specification, R is a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0077] In one embodiment of the present specification, R1 is hydrogen; deuterium; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl.

[0078] In one embodiment of the present specification, R1 is hydrogen; deuterium; substituted or unsubstituted C6 to C30 aryl; or substituted or unsubstituted C2 to C30 heteroaryl.

[0079] In one embodiment of the present specification, R1 is hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted naphthyl; or substituted or unsubstituted phenanthroline.

[0080] In one embodiment of the present specification, R1 is a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0081] In one embodiment of the present specification, R1 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted phenanthroline group.

[0082] In one embodiment of the present specification, R2 is hydrogen; deuterium; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl.

[0083] In one embodiment of the present specification, R2 is hydrogen; deuterium; substituted or unsubstituted C6 to C30 aryl; or substituted or unsubstituted C2 to C30 heteroaryl.

[0084] In one embodiment of the present specification, R2 is hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0085] In one embodiment of the present specification, R2 is hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted pyridyl; substituted or unsubstituted pyrimidinyl; substituted or unsubstituted triazinyl; or substituted or unsubstituted phenanthroline.

[0086] In one embodiment of the present specification, R2 is hydrogen; deuterium; C6 to C20 aryl which is unsubstituted or substituted with a heteroaryl group; or C2 to C20 heteroaryl which is unsubstituted or substituted with an aryl group or a heteroaryl group.

[0087] In one embodiment of the present specification, R1 and R2 are hydrogen; or deuterium.

[0088] In one embodiment of the present specification, R1 is a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group, and R2 is hydrogen; or deuterium.

[0089] In one embodiment of the present specification, R1 is substituted or unsubstituted phenyl; substituted or unsubstituted naphthyl; or substituted or unsubstituted phenanthroline, and R2 is hydrogen; or deuterium.

[0090] In one embodiment of the present specification, R1 is hydrogen, and R2 is a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0091] In one embodiment of the present specification, R1 is hydrogen, and R2 is substituted or unsubstituted phenyl; substituted or unsubstituted naphthyl; or substituted or unsubstituted phenanthroline.

[0092] In one embodiment of the present specification, R1 and R2 are each independently a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0093] In one embodiment of the present specification, Chemical Formula 1 may be represented by the following Chemical Formula 1-1 or Chemical Formula 1-2.

[0094] [Chemical formula 1-1]

[0095]

[0096] [Chemical formula 1-2]

[0097]

[0098] In Chemical Formula 1-1 and Chemical Formula 1-2,

[0099] R1, R2 and r have the same definitions as in Chemical Formula 1,

[0100] L1 and L2 are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0101] Z1 and Z2 are each independently a halogen group; a cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0102] m is an integer of 1 to 5, and when it is 2 or more, L1 are the same as or different from each other,

[0103] n is an integer of 1 to 5, and when n is 2 or more, Z1 are the same as or different from each other,

[0104] p is an integer of 1 to 5, and when p is 2 or more, L2 are the same or different from each other, and

[0105] q is an integer of 1 to 5, and when q is 2 or more, Z2 are the same as or different from each other.

[0106] In one embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 2-1 to 2-4.

[0107] [Chemical formula 2-1]

[0108]

[0109] [Chemical formula 2-2]

[0110]

[0111] [Chemical formula 2-3]

[0112]

[0113] [Chemical formula 2-4]

[0114]

[0115] In Chemical Formula 2-1 to Chemical Formula 2-4,

[0116] R1 and R2 have the same meanings as in Chemical Formula 1,

[0117] L1 and L2 are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0118] Z1 and Z2 are each independently a halogen group; a cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0119] m is an integer of 1 to 5, and when it is 2 or more, L1 are the same as or different from each other,

[0120] n is an integer of 1 to 5, and when n is 2 or more, Z1 are the same as or different from each other,

[0121] p is an integer of 1 to 5, and when p is 2 or more, L2 are the same or different from each other, and

[0122] q is an integer of 1 to 5, and when q is 2 or more, Z2 are the same as or different from each other.

[0123] In one embodiment of the present specification, L1 and L2 are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0124] In one embodiment of the present specification, L1 and L2 are each independently a direct bond; a substituted or unsubstituted C6 to C30 arylene group; or a substituted or unsubstituted C2 to C30 heteroarylene group.

[0125] In one embodiment of the present specification, L1 and L2 are each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted anthracene group; a substituted or unsubstituted divalent pyridyl group; a substituted or unsubstituted divalent pyrimidyl group; a substituted or unsubstituted divalent triazine group; or a substituted or unsubstituted divalent phenanthroline group.

[0126] In one embodiment of the present specification, Z1 and Z2 are each independently a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0127] In one embodiment of the present specification, Z1 and Z2 are each independently a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0128] In one embodiment of the present specification, Z1 and Z2 are each independently a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted phenanthryl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted pyridyl group; a substituted or unsubstituted pyrimidinyl group; a substituted or unsubstituted triazinyl group; or a substituted or unsubstituted phenanthroline group.

[0129] In one embodiment of the present specification, Z1 and Z2 are each independently an unsubstituted or aryl-substituted phosphine oxide group; an unsubstituted or aryl- or heteroaryl-substituted phenyl group; a biphenyl group; a terphenyl group; a naphthyl group; an unsubstituted or aryl-substituted anthracenyl group; a phenanthrenyl group; a substituted or unsubstituted triphenylene group; a 9,9′-spirobi[fluorene] group; an unsubstituted or aryl- or heteroaryl-substituted pyridinyl group; an unsubstituted or aryl-substituted pyrimidinyl group; an unsubstituted or aryl-substituted triazinyl group; or an unsubstituted or aryl-substituted phenanthrinyl group.

[0130] In one embodiment of the present specification, Z1 and Z2 may be each independently represented by any one of the following Chemical Formulae A to C.

[0131] [Chemical formula A]

[0132]

[0133] [Chemical formula B]

[0134]

[0135] [Chemical formula C]

[0136]

[0137] In Chemical Formulae A to C,

[0138] R11 is hydrogen; deuterium; substituted or unsubstituted silyl; substituted or unsubstituted phosphine oxide; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, or adjacent groups may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring,

[0139] r11 is an integer of 1 to 5, and when it is 2 or more, R11 are the same as or different from each other,

[0140] Y1 to Y5 are each independently N or CR12, at least one of which is N, and adjacent groups may be bonded to each other to form a heterocyclic ring, and

[0141] R12 to R14 are each independently hydrogen; deuterium; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl.

[0142] In one embodiment of the present specification, R11 is hydrogen; deuterium; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, or adjacent groups may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

[0143] In one embodiment of the present specification, R11 is hydrogen; deuterium; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group, or adjacent groups may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

[0144] In one embodiment of the present specification, adjacent groups in R11 may be bonded to each other to form a substituted or unsubstituted C6 to C30 hydrocarbon ring.

[0145] In one embodiment of the present specification, adjacent groups in R11 may be bonded to each other to form ring, Ring or A ring, and the ring may be further substituted with an aryl or heteroaryl group.

[0146] In one embodiment of the present specification, Y1 to Y5 are each independently N or CR12, at least one of which is N, and adjacent groups may be bonded to each other to form a heterocyclic ring.

[0147] In one embodiment of the present specification, Y1 to Y5 are each independently N or CR12, and at least two of them may be N.

[0148] In one embodiment of the present specification, Y1 to Y5 are each independently N or CR12, and at least three of them may be N.

[0149] In one embodiment of the present specification, Y1 to Y5 are each independently N or CR12, at least one of which is N, and adjacent groups may be bonded to each other to form a C2 to C30 heterocyclic ring.

[0150] In one embodiment of the present specification, Y1 to Y5 are each independently N or CR12, at least one of which is N, and adjacent groups may be bonded to each other to form A ring, and the ring may be further substituted with an aryl or heteroaryl group.

[0151] In one embodiment of the present specification, R12 to R14 are each independently hydrogen; deuterium; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl.

[0152] In one embodiment of the present specification, R12 to R14 are each independently hydrogen; deuterium; substituted or unsubstituted C6 to C30 aryl; or substituted or unsubstituted C2 to C30 heteroaryl.

[0153] In one embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 3-1 to 3-4.

[0154] [Chemical formula 3-1]

[0155]

[0156] [Chemical formula 3-2]

[0157]

[0158] [Chemical formula 3-3]

[0159]

[0160] [Chemical formula 3-4]

[0161]

[0162] In Chemical Formulae 3-1 to 3-4, each substituent has the same definition as in Chemical Formula 1.

[0163] In one embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 4-1 to 4-4.

[0164] [Chemical formula 4-1]

[0165]

[0166] [Chemical formula 4-2]

[0167]

[0168] [Chemical formula 4-3]

[0169]

[0170] [Chemical formula 4-4]

[0171]

[0172] In Chemical Formula 4-1 to Chemical Formula 4-4,

[0173] Either one of X11 and X12 is N, and the other is CR, and

[0174] R, R1, R2 and r each have the same definition as in Chemical Formula 1.

[0175] In one embodiment of the present specification, X11 is N, and X12 is CR.

[0176] In one embodiment of the present specification, X11 is CR, and X12 is N.

[0177] In one embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following compounds, but is not limited thereto.

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198] In addition, by introducing various substituents into the structure of Chemical Formula 1, a compound having unique properties of the introduced substituents can be synthesized. For example, by introducing substituents commonly used as hole injection layer materials, hole transport layer materials, light emitting layer materials, electron transport layer materials, and charge generation layer materials for manufacturing organic light emitting elements into the core structure, a material that meets the conditions required for each organic material layer can be synthesized.

[0199] Furthermore, by introducing various substituents into the structure of Chemical Formula 1, the energy band gap can be finely controlled, and at the same time, the properties at the interface between organic materials can be enhanced, and material applications can become diversified.

[0200] An embodiment of the present specification provides an organic light-emitting element, which includes: a first electrode; a second electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers contain one or more heterocyclic compounds represented by Chemical Formula 1.

[0201] In one embodiment of the present specification, one or more layers of the organic material layer include a heterocyclic compound represented by Chemical Formula 1.

[0202] In one embodiment of the present specification, the first electrode may be an anode, and the second electrode may be a cathode.

[0203] In another embodiment of the present specification, the first electrode may be a cathode, and the second electrode may be an anode.

[0204] In one embodiment of the present specification, the organic light emitting element may be a blue organic light emitting element, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material of the blue organic light emitting element. For example, the heterocyclic compound represented by Chemical Formula 1 may be included in an electron transport layer or a charge generation layer of the blue organic light emitting element.

[0205] In one embodiment of the present specification, the organic light emitting element may be a green organic light emitting element, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material of the green organic light emitting element. For example, the heterocyclic compound represented by Chemical Formula 1 may be included in an electron transport layer or a charge generation layer of the green organic light emitting element.

[0206] In one embodiment of the present specification, the organic light emitting element may be a red organic light emitting element, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material of the red organic light emitting element. For example, the heterocyclic compound represented by Chemical Formula 1 may be included in an electron transport layer or a charge generation layer of the red organic light emitting element.

[0207] In addition to using the above heterocyclic compounds to form one or more organic material layers, the organic light-emitting element of the present specification can be manufactured using commonly used organic light-emitting element manufacturing methods and materials.

[0208] When manufacturing an organic light emitting element, a compound may be formed into an organic material layer using a solution coating method and a vacuum deposition method. Herein, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray coating, roller coating, etc., but is not limited thereto.

[0209] The organic material layer of the organic light-emitting element of the present specification may be formed as a single-layer structure, but may be formed as a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting element disclosed herein may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as organic material layers. However, the structure of the organic light-emitting element is not limited thereto, and may include a smaller number of organic material layers.

[0210] In the organic light emitting element of the present specification, the organic material layer includes an electron transport layer, and the electron transport layer may include the heterocyclic compound represented by Chemical Formula 1.

[0211] In the organic light emitting element of the present specification, the organic material layer includes a charge generation layer, and the charge generation layer may include the heterocyclic compound represented by Chemical Formula 1.

[0212] The organic light emitting device disclosed herein may further include one, two or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer and a hole blocking layer.

[0213] Figures 1 to 3 The stacking sequence of electrodes and organic material layers of an organic light emitting device according to one embodiment of the present specification is shown. However, the scope of the present application is not limited to these drawings, and the structure of an organic light emitting device known in the art can also be used in the present application.

[0214] Figure 1 1 shows an organic light emitting element in which an anode 200, an organic material layer 300, and a cathode 400 are sequentially stacked on a substrate 100. However, the structure is not limited to this structure, and Figure 2 As shown, an organic light-emitting element can also be obtained in which a cathode, an organic material layer and an anode are successively stacked on a substrate.

[0215] Figure 3 The case where the organic material layer is multi-layered is shown. Figure 3 The organic light-emitting element includes a hole injection layer 301, a hole transport layer 302, a light-emitting layer 303, an electron transport layer 304 and an electron injection layer 305. However, the scope of the present application is not limited to such a stacked structure, and as required, layers other than the light-emitting layer may not be included, and other required functional layers may be further added.

[0216] The organic material layer including the heterocyclic compound represented by Chemical Formula 1 may further include other materials as needed.

[0217] In addition, an embodiment of the present specification provides an organic light-emitting element, which includes a first electrode, a second electrode, and one or more organic material layers arranged between the first electrode and the second electrode, wherein the organic material layers include: a first stack including a first light-emitting layer; a charge generation layer arranged on the first stack; and a second stack arranged on the charge generation layer and including a second light-emitting layer, and the charge generation layer contains a heterocyclic compound represented by Chemical Formula 1.

[0218] In an organic light emitting element according to one embodiment of the present specification, the charge generation layer includes an N-type charge generation layer, and the N-type charge generation layer includes a heterocyclic compound represented by Chemical Formula 1.

[0219] In the organic light emitting element according to one embodiment of the present specification, the charge generation layer may further include a P-type charge generation layer.

[0220] As an organic light emitting element according to one embodiment of the present specification, Figure 4 An organic light emitting element having a 2-stacked tandem structure is shown in FIG.

[0221] In this article, with Figure 4 In the organic light-emitting element of the two-stacked series structure, a first hole injection layer, a first electron blocking layer, a first hole blocking layer, a second electron blocking layer, a second hole blocking layer, a P-type charge generating layer, etc. can be added as needed.

[0222] In an organic light-emitting element according to one embodiment of the present specification, materials other than the heterocyclic compound represented by Chemical Formula 1 are shown below, however, these are only for illustrative purposes and do not limit the scope of the present application, and these materials may be replaced by materials known in the art.

[0223] As the anode material, a material having a relatively large work function can be used, and a transparent conductive oxide, a metal, a conductive polymer, etc. can be used. Specific examples of the anode material include: metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO; 2 :Sb; conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (poly[3,4-(ethylene-1,2-dioxy)thiophene], PEDOT), polypyrrole, and polyaniline, but not limited thereto.

[0224] As the cathode material, a material having a relatively small work function can be used, and metals, metal oxides, conductive polymers, etc. can be used. Specific examples of the cathode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO 2 / Al, etc., but not limited to these.

[0225] As the hole injection material, a known hole injection material can be used, and for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Pat. No. 4,356,429; or a star-shaped sudden-action amine derivative such as tris(4-carbazolyl-9-ylphenyl)amine (TCTA), 4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA) or 1,3,5-tris[4-(3-methylphenylanilino)phenyl]benzene (m-MTDAPB) described in the document [Advanced Material, 6, p. 677 (1994)], polyaniline / dodecylbenzenesulfonic acid (Polyaniline / Dodecylbenzenesulfonic Acid) as a conductive polymer having solubility can be used. acid), Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), Polyaniline / Camphor sulfonic acid or Polyaniline / Poly(4-styrenesulfonate), etc.

[0226] As the hole transport material, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. can be used, and low molecular weight or high molecular weight materials can also be used.

[0227] As electron transport materials, metal complexes of oxadiazole derivatives, anthraquinone dimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinone dimethane and its derivatives, fluorenone derivatives, diphenyl dicyanoethylene and its derivatives, dibenzoquinone derivatives, 8-hydroxyquinoline and its derivatives, etc. can be used, and polymer materials and low molecular weight materials can also be used.

[0228] As an example of the electron injection material, LiF is generally used in the art, however, the present application is not limited thereto.

[0229] As the luminescent material, a red, green or blue luminescent material can be used, and two or more luminescent materials can be mixed and used as needed. In this article, two or more luminescent materials can be used by depositing as individual supply sources or by being premixed and deposited as one supply source. In addition, fluorescent materials can also be used as luminescent materials, however, phosphorescent materials can also be used. As the luminescent material, a material that emits light by combining electrons and holes injected from the anode and cathode, respectively, can be used alone, however, a material having a host material and a dopant material that participate in luminescence together can also be used.

[0230] When mixing the light emitting material host, the same series of hosts may be mixed, or hosts of different series may be mixed. For example, any two or more materials of n-type host materials or p-type host materials may be selected and used as host materials of the light emitting layer.

[0231] The organic light emitting element according to one embodiment of the present specification may be a top emission type, a bottom emission type, or a dual emission type depending on the materials used.

[0232] The compound according to one embodiment of the present specification can also be used in organic electronic devices including organic solar cells, organic photoconductors, organic transistors, etc. under a similar principle used in organic light-emitting devices.

[0233] Hereinafter, the present specification will be described in more detail with reference to examples, however, these are for illustrative purposes only, and the scope of the present application is not limited thereto.

[0234] [Preparation Example] Preparation of Compound 14

[0235]

[0236] 1) Preparation of compound 14-2

[0237] 1,4-Dioxane (400 ml) and H 2 O (100 ml) was introduced into 2-bromo-1,10-phenanthroline (A) (20 g, 0.077 mol, 1 eq.), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (B) (20.3 g, 0.092 mol, 1.2 eq.), K 3 PO 4 (49.1 g, 0.23 mol, 3 eq.) and Pd(PPh 3 ) 4 (tetrakis(triphenylphosphine)palladium(0)) (4.45 g, 0.0038 mol, 0.05 eq.) and stirred at 100°C for 6 hours. After the reaction was terminated by introducing water, the result was extracted with methylene chloride (MC) and water. Then, MgSO 4 Water was removed, and the result was separated using a silica gel column to obtain compound 14-2 (16 g) in a yield of 76%.

[0238] 2) Preparation of compound 14-3

[0239] After dissolving compound 14-2 (16 g, 0.058 mol, 1 eq) and triethylamine (7.1 g, 0.70 mol, 1.2 eq) in MC (160 ml), 4-bromobenzoyl chloride (C) (15.5 g, 0.092 mol, 1.2 eq) was slowly introduced at 0°C, and the result was stirred at room temperature (RT) for 4 hours. After the reaction was terminated by introducing water, the result was extracted with MC and water. Thereafter, MgSO 4 Water was removed, and the result was separated using a silica gel column to obtain compound 14-3 (18 g) in a yield of 67%.

[0240] 3) Preparation of compound 14-4

[0241] Nitrobenzene (180 mL) was introduced into compound 14-3 (18 g, 0.039 mol, 1 eq) and POCl 3 (18.2 g, 0.118 mol, 3 eq.) and stirred at 160°C for 12 hours. After the reaction was terminated by introducing water, the result was extracted with MC and water. Then, MgSO 4 Water was removed, and the result was separated using a silica gel column to obtain compound 14-4 (11 g) in a yield of 64%.

[0242] 4) Preparation of compound 14-5

[0243] 1,4-Dioxane (110 mL) was introduced into compound 14-4 (11 g, 0.025 mol, 1 eq), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (9.6 g, 0.038 mol, 1.5 eq), KOAc (potassium acetate) (7.4 g, 0.075 mol, 3 eq) and Pd(dppf)Cl 2 ([1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II)) (1.8 g, 0.0025 mol, 0.1 equivalent) and stirred at 100°C for 8 hours. After the reaction was terminated by introducing water, the result was extracted with MC and water. Thereafter, MgSO4 Water was removed, and the result was separated using a silica gel column to obtain compound 14-5 (10 g) in a yield of 82%.

[0244] 5) Preparation of compound 14

[0245] 1,4-Dioxane (200 mL) and H 2 O (50 ml) was introduced into compound 14-5 (10 g, 0.02 mol, 1 equivalent), 4-chloro-2,6-diphenylpyrimidine (D) (5.8 g, 0.021 mol, 1.05 equivalent), K 3 PO 4 (13.1 g, 0.062 mol, 3 eq.) and Pd(PPh 3 ) 4 (1.19 g, 0.001 mol, 0.05 eq) and stirred at 100°C for 6 hours. After the reaction was terminated by introducing water, the result was extracted with MC and water. Then, MgSO 4 Water was removed, and the result was separated using a silica gel column to obtain Compound 14 (9 g) in a yield of 74%.

[0246] The compound was synthesized in the same manner as in the Preparation Example, except that the intermediates A, B, C and D in Table 1 below were used instead of 2-bromo-1,10-phenanthroline (A), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (B), 4-bromobenzoyl chloride (C) and 4-chloro-2,6-diphenylpyrimidine (D).

[0247] [Table 1]

[0248]

[0249]

[0250]

[0251] The compounds were prepared in the same manner as in the preparation examples, and the synthesis identification results are shown in Tables 2 and 3. Table 2 shows 1 H NMR (CDCl 3 , 200Mz), and Table 3 shows the measured values ​​of FD-mass spectrometry (FD-MS: Field desorption mass spectrometry).

[0252] [Table 2]

[0253]

[0254] [Table 3]

[0255] Compound FD-MS Compound FD-MS 1 m / z=357.41(C25H15N3=357.13) 3 m / z=433.50(C31H19N3=433.16) 14 m / z=587.67(C41H25N5=587.21) 15 m / z=587.67(C41H25N5=587.21) 24 m / z=611.69(C43H25N5=611.21) 28 m / z=588.66(C40H24N6=588.21) 58 m / z=407.47(C29H17N3=407.14) 63 m / z=507.58(C37H21N3=507.17) 72 m / z=588.66(C40H24N6=588.21) 88 m / z=509.19(C37H23N3=509.60) 98 m / z=587.67(C41H25N5=587.21) 113 m / z=357.41(C25H15N3=357.13) 146 m / z=609.72(C45H27N3=609.22) 186 m / z=587.67(C41H25N5=587.21) 199 m / z=433.50(C31H19N3=533.16) 225 m / z=433.50(C31H19N3=433.16) 226 m / z=664.75(C46H28N6=664.24) 289 m / z=509.60(C37H23N3=509.19) 297 m / z=687.79(C49H29N5=687.24)

[0256] [Experimental example]

[0257] <Experimental Example 1>

[0258] 1) Manufacturing of organic light-emitting elements

[0259] Comparative Example 1-1

[0260] A transparent indium tin oxide (ITO) electrode film obtained from an organic light emitting diode (OLED) glass (manufactured by Samsung-Corning Co., Ltd.) was continuously ultrasonically cleaned for 5 minutes each using trichloroethylene, acetone, ethanol, and distilled water, and the transparent ITO electrode film was stored in isopropanol and used. Next, the ITO substrate was mounted in a substrate folder of a vacuum deposition device, and the following 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine: 2-TNATA) was introduced into a unit in the vacuum deposition device.

[0261]

[0262] Then, the chamber was evacuated until the vacuum level reached 10 -6 The cell was then heated to 400 angstroms and 2-TNATA was evaporated by applying an electric current to the cell to deposit a 600 angstrom thick layer on the ITO substrate. The following N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was introduced into another unit in the vacuum deposition equipment, and evaporated by applying an electric current to the unit to deposit a hole transport layer with a thickness of 300 angstroms on the hole injection layer.

[0263]

[0264] After the hole injection layer and the hole transport layer are formed as above, a blue light-emitting material having the following structure is deposited thereon as a light-emitting layer. Specifically, in a side unit of a vacuum deposition device, a blue light-emitting host material H1 is vacuum deposited to a thickness of 200 angstroms, and a blue light-emitting dopant material D1 is vacuum deposited thereon at 5 wt % relative to the host material.

[0265]

[0266] Subsequently, a compound of the following structural formula E1 was deposited to a thickness of 300 angstroms as an electron transport layer.

[0267]

[0268] As an electron injection layer, lithium fluoride (LiF) was deposited to a thickness of 10 angstroms, and an Al cathode was used to a thickness of 1,000 angstroms, and thus, an OLED was manufactured. -8 Torr to 10 -6 All organic compounds needed to manufacture OLEDs are purified by vacuum sublimation under the support.

[0269] Comparative Examples 1-2 and 1-3 and Examples 1-1 to 1-19

[0270] Organic electroluminescent elements were manufactured in the same manner as in Comparative Example 1-1, except that the compounds shown in Table 4 below were each used instead of E1 used in forming the electron transport layer.

[0271] 2) Measure the driving voltage and luminous efficiency of organic light-emitting elements

[0272] For each of the organic electroluminescent elements manufactured as above, electroluminescent (EL) properties were measured using M7000 manufactured by McScience Inc., and using the measurement results, the lifetime measurement system (M6000) manufactured by McScience Inc. was used to measure the lifetime of the organic electroluminescent elements when the standard brightness was 3,500 cd / m 2 ) 95 The measurement results of the driving voltage, luminous efficiency, color coordinate (CIE) and life of the blue organic light emitting element manufactured according to the present disclosure are shown in Table 4.

[0273] [Table 4]

[0274] Compound Driving voltage(V) Luminous efficiency (cd / A) CIE(x,y) <![CDATA[Life (T 95 )]]> Example 1-1 1 4.90 6.69 (0.134,0.100) 49 Example 1-2 3 4.86 6.80 (0.134,0.101) 47 Example 1-3 14 4.79 6.77 (0.134,0.101) 46 Examples 1-4 15 4.85 6.73 (0.134,0.100) 46 Examples 1-5 24 4.87 6.83 (0.134,0.101) 51 Examples 1-6 28 4.80 6.85 (0.134,0.100) 42 Examples 1-7 58 4.93 6.81 (0.134,0.100) 45 Examples 1-8 63 4.90 6.76 (0.134,0.101) 49 Examples 1-9 72 4.94 6.70 (0.134,0.100) 41 Example 1-10 88 4.78 6.68 (0.134,0.100) 41 Example 1-11 98 4.89 6.80 (0.134,0.100) 46 Example 1-12 113 4.93 6.89 (0.134,0.101) 50 Example 1-13 146 4.83 6.79 (0.134,0.100) 51 Example 1-14 186 4.91 6.63 (0.134,0.101) 47 Example 1-15 199 4.82 6.82 (0.134,0.100) 46 Example 1-16 225 4.97 6.70 (0.134,0.101) 44 Example 1-17 226 4.88 6.88 (0.134,0.100) 47 Example 1-18 289 4.90 6.77 (0.134,0.100) 48 Example 1-19 297 4.81 6.66 (0.134,0.101) 50 Comparative Example 1-1 E1 5.57 6.13 (0.134,0.100) 34 Comparative Example 1-2 E2 5.50 6.20 (0.134,0.101) 35 Comparative Examples 1-3 E3 5.84 5.99 (0.134,0.100) 33

[0275] As can be seen from the results in Table 4, compared with Comparative Examples 1-1 to 1-3, the organic light-emitting device using the electron transport layer material of the blue organic light-emitting device disclosed in the present invention has a lower driving voltage and significantly improved luminous efficiency and lifespan.

[0276] This result is considered to be due to the fact that when a compound having an appropriate length and strength and flatness is used as an electron transport layer, the compound in an excited state is made by receiving electrons under specific conditions, and specifically, when an excited state is formed at a hetero skeleton site of the compound, the excitation energy will move to a stable state before the excited hetero skeleton site undergoes other reactions, and therefore, a relatively stable compound can effectively transport electrons without decomposing or destroying the compound. For reference, a compound that is stable when excited is considered to be an aryl or acene-based compound or a polycyclic hetero compound.

[0277] Therefore, it is believed that the compounds disclosed herein achieve excellent results in all aspects such as driving voltage, luminous efficiency and lifespan, thereby enhancing electron transport properties or improving stability.

[0278] <Experimental Example 2>

[0279] 1) Manufacturing of organic light-emitting elements

[0280] Examples 2-1 to 2-19 and Comparative Examples 2-1 to 2-3

[0281] The glass substrate on which ITO was coated as a thin film to a thickness of 1,500 angstroms was cleaned ultrasonically with distilled water. After cleaning with distilled water, the substrate was ultrasonically cleaned with solvents such as acetone, methanol and isopropanol, then dried and treated with ultraviolet ozone (UVO) for 5 minutes using ultraviolet light in an ultraviolet (UV) cleaner. After that, the substrate was transferred to a plasma cleaner (PT) and after plasma treatment under vacuum to achieve the ITO work function and remove the residual film, the substrate was transferred to a thermal deposition device for organic deposition.

[0282] On the transparent ITO electrode (anode), the organic materials were formed into a 2-stack white organic light emitting device (WOLED) structure. For the first stack, TAPC was first thermally vacuum deposited to a thickness of 300 angstroms to form a hole transport layer. After the hole transport layer was formed, the light emitting layer was thermally vacuum deposited thereon as described below. The light emitting layer was deposited to 300 angstroms by doping the host TCz1 with a blue phosphorescent dopant FIrpic at a rate of 8%. After the electron transport layer was formed to 400 angstroms using TmPyPB, Cs 2 CO 3 The compounds described in the following Table 5 were doped at a ratio of 20% to form a charge generation layer to 100 angstroms.

[0283] For the second stack, MoO 3 Thermal vacuum deposition to a thickness of 50 angstroms was used to form a hole injection layer. TAPC was doped with MoO at a ratio of 20%. 3 Then, TAPC is deposited to 300 angstroms and a hole transport layer as a common layer is formed to 100 angstroms. By using green phosphorescent dopant Ir(ppy) 3 The host TCz1 was doped at a ratio of 8%, a light-emitting layer was deposited thereon to 300 angstroms, and an electron transport layer was formed to 600 angstroms using TmPyPB. Finally, an electron injection layer was formed on the electron transport layer by depositing lithium fluoride (LiF) to a thickness of 10 angstroms, and then a cathode was formed on the electron injection layer by depositing an aluminum (Al) cathode to a thickness of 1,200 angstroms, and thus, an organic electroluminescent element was manufactured.

[0284] At the same time, for each material that will be used in OLED manufacturing, the total number of organic compounds required to make OLEDs is within 10 -8 Support up to 10 -6 Purification was performed by vacuum sublimation under support.

[0285]

[0286] 2) Measure the driving voltage and luminous efficiency of organic light-emitting elements

[0287] For each of the organic electroluminescent elements manufactured as above, electroluminescence (EL) properties were measured using M7000 manufactured by Maxims, and using the measurement results, T when the standard brightness was 3,500 cd / m² was measured by a lifetime measurement system (M6000) manufactured by Maxims. 95The measurement results of the driving voltage, luminous efficiency, external quantum efficiency and color coordinates (CIE) of the white organic electroluminescent element manufactured according to the present disclosure are shown in Table 5.

[0288] [Table 5]

[0289] Compound Driving voltage(V) Luminous efficiency (cd / A) CIE(x,y) <![CDATA[Lifetime (T 95 )]]> Example 2-1 1 7.32 62.78 (0.210,0.414) 83 Example 2-2 3 7.66 63.66 (0.218,0.420) 79 Example 2-3 14 7.39 62.72 (0.217,0.425) 70 Example 2-4 15 7.11 66.29 (0.210,0.427) 88 Example 2-5 24 7.54 63.11 (0.213,0.421) 91 Example 2-6 28 7.07 68.23 (0.206,0.428) 77 Example 2-7 58 7.25 63.88 (0.205,0.433) 83 Example 2-8 63 7.45 60.58 (0.219,0.416) 72 Example 2-9 72 7.56 69.01 (0.209,0.425) 79 Example 2-10 88 7.53 66.74 (0.205,0.427) 70 Example 2-11 98 7.40 61.82 (0.207,0.411) 88 Example 2-12 113 7.24 62.75 (0.221,0.435) 93 Example 2-13 146 7.44 63.45 (0.218,0.429) 95 Example 2-14 186 7.39 64,51 (0.211,0,426) 92 Example 2-15 199 7.37 66.02 (0.216,0.420) 87 Example 2-16 225 7.40 63.52 (0.209,0.425) 89 Example 2-17 226 7.33 66.18 (0.208,0.433) 80 Example 2-18 289 7.17 65.90 (0.211,0.428) 76 Example 2-19 297 7.22 67.63 (0.217,0.430) 84 Comparative Example 2-1 PcqI 8.24 55.65 (0.210,0.432) 57 Comparative Example 2-2 E2 8.02 56.60 (0.212,0,434) 60 Comparative Example 2-3 E3 8.22 55.72 (0.211,0.427) 58

[0290] As can be seen from the results in Table 5, compared to Comparative Examples 2-1 to 2-3, the organic electroluminescent element using the charge generation layer material of the double-stacked white organic electroluminescent element disclosed in the present invention has a lower driving voltage, and improved lifespan and luminous efficiency.

[0291] This result is considered to be due to the fact that the compound of the present disclosure used as the N-type charge generation layer formed of the disclosed skeleton has appropriate length and strength and flatness, and an appropriate hetero compound capable of bonding to a metal forms a gap state in the N-type charge generation layer by doping an alkali metal or an alkaline earth metal into the N-type charge generation layer, and the electrons generated from the P-type charge generation layer are easily injected into the electron transport layer through the gap state generated in the N-type charge generation layer. Therefore, the P-type charge generation layer can advantageously inject and transport electrons to the N-type charge generation layer, and thus, the driving voltage is reduced, and the efficiency and life of the organic light emitting element are improved.

Claims

1. A heterocyclic compound of the following Chemical Formula 1-1 or Chemical Formula 1-2: [Chemical formula 1-1] [Chemical formula 1-2] in, In Chemical Formula 1-1 and Chemical Formula 1-2, R1 and R2 are each independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted silyl; substituted or unsubstituted phosphine oxide; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, r is an integer from 1 to 4, and when it is 2 or more, R2 are the same or different from each other, L1 and L2 are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, Z1 and Z2 are each independently a halogen group; a cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and at least one of Z1 and Z2 is selected from a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, m is an integer of 1 to 5, and when it is 2 or more, L1 are the same as or different from each other, n is an integer of 1 to 5, and when n is 2 or more, Z1 are the same as or different from each other, p is an integer of 1 to 5, and when p is 2 or more, L2 are the same or different from each other, and q is an integer of 1 to 5, and when q is 2 or more, Z2 are the same as or different from each other, Wherein "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of: deuterium; halogen; cyano; C1 to C60 alkyl; C2 to C60 alkenyl; C2 to C60 alkynyl; C3 to C60 cycloalkyl; C2 to C60 heterocycloalkyl; C6 to C60 aryl; C2 to C60 heteroaryl; silanyl; phosphine oxide; and amine, or unsubstituted, and when the number of the substituents selected from the above is two or more, the two or more substituents may be the same as or different from each other.

2. The heterocyclic compound according to claim 1, wherein Z1 and Z2 are each independently a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

3. The heterocyclic compound according to claim 1, wherein R1 is hydrogen; deuterium; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

4. The heterocyclic compound according to claim 1, wherein R2 is hydrogen; deuterium; substituted or unsubstituted C6 to C30 aryl; or substituted or unsubstituted C2 to C30 heteroaryl.

5. The heterocyclic compound according to claim 1, wherein the heterocyclic compound is represented by any one of the following compounds:

6. An organic light emitting element, include: a first electrode; a second electrode; and an organic material layer disposed between the first electrode and the second electrode, The organic material layer comprises one or more heterocyclic compounds as claimed in any one of claims 1 to 5. 7 . The organic light emitting element according to claim 6 , wherein the organic material layer includes an electron transport layer, and the electron transport layer contains the heterocyclic compound. 8 . The organic light emitting element according to claim 6 , further comprising a layer selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer and a hole blocking layer.

9. The organic light emitting element according to claim 6, wherein the organic material layer include: A first stack including a first light emitting layer; a charge generating layer disposed on the first stack; and a second stack disposed on the charge generation layer and comprising a second light emitting layer. 10 . The organic light emitting element according to claim 9 , wherein the charge generating layer comprises the heterocyclic compound. 11 . The organic light emitting element according to claim 9 , wherein the charge generation layer comprises an N-type charge generation layer, and the N-type charge generation layer contains the heterocyclic compound.

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