Heterocyclic Compounds and Organic Light-Emitting Devices Containing the Same

Abstract

This specification relates to a xanthene or thioxanthene compound represented by Chemical Formula 1 and an organic light-emitting device including the same.

Description

Technical Field

[0001] This application claims the priority of Korean Patent Application No. 10-2020-0071737, filed with the Korean Patent Office on June 12, 2020, the entire contents of which are incorporated herein by reference.

[0002] This specification relates to a heterocyclic compound and an organic light-emitting device including the same. Background Art

[0003] An organic light-emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light-emitting device having such a structure, electrons and holes injected from the two electrodes are combined in the organic thin film, and then quenched and emit light. The organic thin film may be composed of a single layer or multiple layers as needed.

[0004] As substances used in organic light-emitting devices, pure organic substances or coordination compounds in which an organic substance and a metal form a complex occupy most of them, and can be classified into a hole injection substance, a hole transport substance, a light-emitting substance, an electron transport substance, an electron injection substance, etc. according to their uses. Here, as a hole injection substance or a hole transport substance, an organic substance having p-type properties, that is, an organic compound that is easily oxidized and has an electrochemically stable state when oxidized, is mainly used. On the other hand, as an electron injection substance or an electron transport substance, an organic substance having n-type properties, that is, an organic compound that is easily reduced and has an electrochemically stable state when reduced, is mainly used. As a light-emitting layer substance, a substance having both p-type properties and n-type properties, that is, a substance having a stable form in both oxidation and reduction states, is preferably used, and a substance having high luminous efficiency that converts excitons formed when holes and electrons recombine in the light-emitting layer into light is preferably used.

[0005] In order to improve the performance, lifespan, or efficiency of organic light-emitting devices, the development of materials for organic thin films has been continuously demanded. Summary of the Invention

[0006] Technical Problem

[0007] This specification provides a heterocyclic compound and an organic light-emitting device including the same.

[0008] Solution to the Problem

[0009] One embodiment of this specification provides a heterocyclic compound represented by the following Chemical Formula 1.

[0010] [Chemical Formula 1]

[0011]

[0012] In Chemical Formula 1 above,

[0013] b is an integer from 1 to 3. When b is 2 or more, the structures within the parentheses are the same as or different from each other. Z is O or S.

[0014] R1 and R2 are the same as or different from each other, and each independently is a substituted or unsubstituted alkyl group, or combine with each other to form an aliphatic ring.

[0015] L is a direct bond, a monocyclic arylene group, or a bicyclic arylene group.

[0016] a is an integer from 1 to 3. When a is 2 or more, two or more Ls are the same as or different from each other.

[0017] X1 to X3 are the same as or different from each other, and each independently is CR3 or N, provided that two or more of X1 to X3 are N.

[0018] R3 is hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0019] G1 and G2 are the same as or different from each other, and each independently is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0020] Another embodiment of the present specification provides an organic light-emitting device, which includes: a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, and one or more of the organic layers contain the heterocyclic compound.

[0021] Advantages of the Invention

[0022] The heterocyclic compound according to an embodiment of the present specification can be used as a material for the organic layer of an organic light-emitting device. By using this compound, an improvement in efficiency, a lower driving voltage, and / or an improvement in lifetime characteristics can be achieved in the organic light-emitting device. Description of the Drawings

[0023] Figures 1 to 4 An organic light-emitting device according to an embodiment of the present specification is illustrated.

[0024] 1: Substrate

[0025] 2: First electrode

[0026] 3: Light-emitting layer

[0027] 4: Second electrode

[0028] 5: Hole injection layer

[0029] 6: Hole transport layer

[0030] 6-1: First hole transport layer

[0031] 6 - 2: The second hole transport layer

[0032] 7: Electron transport layer

[0033] 8: Electron injection layer

[0034] 10: Hole blocking layer. Detailed implementation mode

[0035] Next, this specification will be described in more detail.

[0036] This specification provides a heterocyclic compound represented by the following Chemical Formula 1.

[0037] [Chemical Formula 1]

[0038]

[0039] In the above Chemical Formula 1,

[0040] b is an integer from 1 to 3. When b is 2 or more, the structures in parentheses are the same as or different from each other, Z is O or S,

[0041] R1 and R2 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group, or combine with each other to form an aliphatic ring,

[0042] L is a direct bond, a monocyclic arylene group, or a bicyclic arylene group,

[0043] a is an integer from 1 to 3. When a is 2 or more, two or more Ls are the same as or different from each other,

[0044] X1 to X3 are the same as or different from each other, and are each independently CR3 or N, but two or more of X1 to X3 are N,

[0045] R3 is hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,

[0046] G1 and G2 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0047] In an organic light - emitting device, if the dipole moment of the organic substance increases, an effect that the lifetime of the device is improved is exhibited.

[0048] The compound represented by Chemical Formula 1 of the present invention forms polarization by including substituents only on one side of the xanthene group or thioxanthene group where Z is O or S, thereby showing the effect of an increased dipole moment. In addition, R1 and R2 include an alkyl group to increase the polarization effect between the xanthene group and the substituent (triazine group or pyrimidine group), and include triazine or pyrimidine as a substituent to improve the electron migration characteristics, thereby showing the effect of improved efficiency of the organic light-emitting device.

[0049] In this specification, when it is stated that a certain part "comprises / includes" a certain component, unless there is a particularly contrary record, it means that other components can be further included, rather than excluding other components.

[0050] In this specification, when it is stated that a certain member is "on" another member, it includes not only the case where a certain member is in contact with another member, but also the case where there are other members between the two members.

[0051] In this specification, examples of substituents are described below, but are not limited thereto.

[0052] In this specification, represents a site for binding to other substituents or binding parts.

[0053] The term "substituted" as used above means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent, and the position to be substituted is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can substitute. When two or more are substituted, the two or more substituents may be the same or different from each other.

[0054] In this specification, the term "substituted or unsubstituted" means being substituted by one or two or more substituents selected from deuterium, a halogen group, a cyano group (-CN), an ester group, an imide group, an amino group, an alkoxy group, an alkyl group, a cycloalkyl group, an aryl group, and a heterocyclic group, or being substituted by a substituent formed by linking two or more of the above-exemplified substituents, or having no substituent. For example, the "substituent formed by linking two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent formed by linking two phenyl groups.

[0055] In this specification, the above-mentioned alkyl group may be straight-chain or branched-chain, and there is no particular limitation on the number of carbon atoms, but it is preferably 1 to 30. As specific examples, there are methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 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, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited thereto.

[0056] In this specification, the aryl group is not particularly limited, but an aryl group having 6 to 50 carbon atoms is preferred, for example, an aryl group having 6 to 30 carbon atoms, and the above-mentioned aryl group may be monocyclic or polycyclic.

[0057] When the above-mentioned aryl group is a monocyclic aryl group, there is no particular limitation on the number of carbon atoms, but it is preferably 6 to 30 carbon atoms. Specifically, as the monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, etc., but is not limited thereto.

[0058] When the above-mentioned aryl group is a polycyclic aryl group, there is no particular limitation on the number of carbon atoms, but it is preferably 10 to 30 carbon atoms. Specifically, as the polycyclic aryl group, it may be naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, chrysenyl, perylenyl, fluorenyl, fluoranthenyl, etc., but are not limited thereto.

[0059] In this specification, the above-mentioned fluorenyl group may be substituted, and adjacent groups may be combined with each other to form a ring.

[0060] In the case where the above-mentioned fluorenyl group is substituted, it may become etc., but are not limited thereto.

[0061] In this specification, the above-mentioned arylene group, in addition to being divalent, may refer to the description of the above-mentioned aryl group.

[0062] In this specification, the above-mentioned monocyclic arylene group, in addition to being a divalent group, may refer to the description of the above-mentioned monocyclic aryl group.

[0063] In this specification, the bicyclic arylene group may be naphthylene.

[0064] In this specification, a heterocyclic group contains one or more non-carbon atoms, i.e., heteroatoms. Specifically, the above heteroatoms may include one or more atoms selected from O, N, S, P, etc. The number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 1 to 50, more preferably 2 to 30. The above heterocyclic group may be a monocyclic or polycyclic group. The above heterocyclic group may be an aromatic ring, an aliphatic ring, or a ring formed by their fusion. Examples of the above heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, azolyl, diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuryl, phenanthroline, iso azolyl, thiadiazolyl, phenothiazinyl, and dibenzofuryl, etc., but are not limited thereto.

[0065] In this specification, the above divalent heterocyclic group, in addition to being divalent, may refer to the description of the above heterocyclic group.

[0066] In this specification, the halogen group may be fluorine, chlorine, bromine, or iodine.

[0067] In this specification, the cycloalkyl group is not particularly limited, but preferably a cycloalkyl group having 3 to 30 carbon atoms. Specifically, there are 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.

[0068] In this specification, the aliphatic ring may be selected from the examples of the above cycloalkyl groups.

[0069] In this specification, the above alkoxy group may be straight-chain, branched-chain, or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but preferably the number of carbon atoms is 1 to 30. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc., but are not limited thereto.

[0070] In this specification, the amino group may be selected from -NH2, alkylamino, N-alkylarylamino, arylamino, N-arylheteroarylamino, N-alkylheteroarylamino, and heteroarylamino, and the number of carbon atoms is not particularly limited, but is preferably 0 to 30. Specific examples of the amino group include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, anthrylamino, 9-methyl-anthrylamino, diphenylamino, N-phenylnaphthylamino, xylarylamino, N-phenyltolylamino, triphenylamino, N-phenylbiphenylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthrylamino, N-biphenylphenanthrylamino, N-phenylfluorenylamino, N-phenylterphenylamino, N-phenanthrylfluorenylamino, N-biphenylfluorenylamino, etc., but are not limited thereto.

[0071] In this specification, N-alkylarylamino refers to an amino group in which an alkyl group and an aryl group are substituted on the N of the amino group.

[0072] In this specification, N-arylheteroarylamino refers to an amino group in which an aryl group and a heteroaryl group are substituted on the N of the amino group.

[0073] In this specification, N-alkylheteroarylamino refers to an amino group in which an alkyl group and a heteroaryl group are substituted on the N of the amino group.

[0074] In this specification, the alkyl group in alkylamino, N-arylalkylamino, and N-alkylheteroarylamino is the same as the exemplified alkyl groups above.

[0075] In one embodiment of this specification, the above Z is O or S.

[0076] In one embodiment of this specification, the above Z is O.

[0077] In one embodiment of this specification, the above Z is S.

[0078] In one embodiment of this specification, the above a is 1.

[0079] In one embodiment of this specification, the above a is 2.

[0080] In one embodiment of this specification, the above a is 3.

[0081] In one embodiment of this specification, the above L is a direct bond, a monocyclic arylene group, or a bicyclic arylene group.

[0082] In one embodiment of this specification, the above L is a direct bond, a monocyclic arylene group having 6 to 30 carbon atoms, or a bicyclic arylene group.

[0083] In one embodiment of the present specification, the above-mentioned L is direct bonding, phenylene, biphenylene, terphenyl or naphthylene.

[0084] In one embodiment of the present specification, the above-mentioned X1 to X3 are the same as or different from each other, and are each independently CR3 or N, provided that two or more of X1 to X3 are N.

[0085] In one embodiment of the present specification, each of the above-mentioned X1 to X3 is N.

[0086] In one embodiment of the present specification, the above-mentioned X1 and X2 are N, and X3 is CR3.

[0087] In one embodiment of the present specification, the above-mentioned X1 and X3 are N, and X2 is CR3.

[0088] In one embodiment of the present specification, the above-mentioned X2 and X3 are N, and X1 is CR3.

[0089] In one embodiment of the present specification, the above-mentioned R3 is hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl.

[0090] In one embodiment of the present specification, the above-mentioned R3 is hydrogen, alkyl or aryl.

[0091] In one embodiment of the present specification, the above-mentioned R3 is hydrogen, alkyl having 1 to 30 carbon atoms, or aryl having 6 to 30 carbon atoms.

[0092] In one embodiment of the present specification, the above-mentioned R3 is hydrogen, methyl, ethyl or phenyl.

[0093] In one embodiment of the present specification, the above-mentioned R1 and R2 are the same as or different from each other, and are each independently substituted or unsubstituted alkyl, or are combined with each other to form an aliphatic ring.

[0094] In one embodiment of the present specification, the above-mentioned R1 and R2 are the same as or different from each other, and are each independently substituted or unsubstituted alkyl having 1 to 30 carbon atoms.

[0095] In one embodiment of the present specification, the above-mentioned R1 and R2 are the same as or different from each other, and are each independently substituted or unsubstituted alkyl having 1 to 20 carbon atoms.

[0096] In one embodiment of the present specification, the above-mentioned R1 and R2 are the same as or different from each other, and are each independently substituted or unsubstituted alkyl having 1 to 10 carbon atoms.

[0097] In one embodiment of the present specification, the above-mentioned R1 and R2 are the same as or different from each other, and are each independently alkyl having 1 to 10 carbon atoms.

[0098] In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently is an alkyl group having 1 to 5 carbon atoms.

[0099] In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently is methyl, ethyl, propyl or butyl.

[0100] In one embodiment of the present specification, R1 and R2 are each methyl or ethyl.

[0101] In one embodiment of the present specification, R1 and R2 are combined with each other to form an aliphatic ring.

[0102] In one embodiment of the present specification, R1 and R2 are combined with each other to form an aliphatic ring having 3 to 10 members.

[0103] In one embodiment of the present specification, R1 and R2 are combined with each other to form an aliphatic ring having 3 to 6 members.

[0104] In one embodiment of the present specification, R1 and R2 are combined with each other to form a six-membered ring.

[0105] In one embodiment of the present specification, R1 and R2 are each methyl or ethyl, or are combined with each other to form a six-membered ring.

[0106] In one embodiment of the present specification, G1 and G2 are the same as or different from each other, and each independently is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0107] In one embodiment of the present specification, G1 and G2 are the same as or different from each other, and each independently is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0108] In one embodiment of the present specification, G1 and G2 are the same as or different from each other, and each independently is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms containing one or more of N, O and S.

[0109] In one embodiment of the present specification, G1 and G2 are the same as or different from each other, and each independently is an alkyl group which is substituted or unsubstituted with one or more selected from deuterium, cyano group, alkyl group, aryl group and heterocyclic group; an aryl group which is substituted or unsubstituted with one or more selected from deuterium, cyano group, alkyl group, aryl group and heterocyclic group; or a heterocyclic group which is substituted or unsubstituted with one or more selected from deuterium, cyano group, alkyl group, aryl group and heterocyclic group.

[0110] In one embodiment of the present specification, G1 and G2 are the same as or different from each other, and each independently is an aryl group which is substituted or unsubstituted with one or more selected from deuterium, cyano group, alkyl group, aryl group and heterocyclic group; or a heterocyclic group which is substituted or unsubstituted with one or more selected from deuterium, cyano group, alkyl group, aryl group and heterocyclic group.

[0111] In one embodiment of the present specification, G1 and G2 are the same as or different from each other, and each independently is any one or a group formed by linking two or more selected from phenyl, biphenyl, naphthyl, acenaphthylenyl, phenanthryl, fluoranthenyl, triphenylenyl, terphenylene, pyridyl, pyrimidinyl, triazinyl, quinolinyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzocarbazolyl, phen azinyl, phenothiazinyl and phenoxazinyl, and G1 and G2 are substituted or unsubstituted with one or more substituents selected from deuterium, cyano group, alkyl group and aryl group.

[0112] In one embodiment of the present specification, G1 and G2 are the same as or different from each other, and each independently is any one or a group formed by linking two or more of the following structures.

[0113]

[0114] In the above structure, X10 is NR10, CR10R11, S or O,

[0115] R10 and R11 are the same as or different from each other, and each independently is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group,

[0116] The above structure is substituted or unsubstituted with one or more substituents selected from deuterium, cyano group, alkyl group and aryl group.

[0117] In one embodiment of the present specification, the above structure is substituted or unsubstituted with one or more substituents selected from deuterium, cyano group, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 30 carbon atoms.

[0118] In one embodiment of the present specification, the above structure is substituted or unsubstituted with deuterium, methyl group, phenyl group or cyano group.

[0119] In one embodiment of the present specification, b is an integer from 1 to 3.

[0120] In one embodiment of the present specification, b is 1.

[0121] In one embodiment of the present specification, the above Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-3.

[0122] [Chemical Formula 1-1]

[0123]

[0124] [Chemical Formula 1-2]

[0125]

[0126] [Chemical Formula 1-3]

[0127]

[0128] In the above Chemical Formulas 1-1 to 1-3,

[0129] Z, R1, R2, L, a, X1 to X3, G1 and G2 are the same as defined in Chemical Formula 1.

[0130] In one embodiment of the present specification, the above Chemical Formula 1 is represented by the above Chemical Formula 1-1.

[0131] In one embodiment of the present specification, the above Chemical Formula 1 is represented by the above Chemical Formula 1-2.

[0132] In one embodiment of the present specification, the above Chemical Formula 1 is represented by the above Chemical Formula 1-3.

[0133] In one embodiment of the present specification, the heterocyclic compound of the above Chemical Formula 1 is any one of the following structures.

[0134]

[0135]

[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]

[0164]

[0165] The nuclear structure of Chemical Formula 1 according to an embodiment of the present specification can be manufactured as shown in the following reaction formula, and the substituents can be combined by methods known in the art, and the type, position or number of substituents can be changed according to techniques known in the art.

[0166] <Reaction formula>

[0167]

[0168] In the above reaction formula,

[0169] Z, L, a, R1, R2, G1, G2, and b are the same as defined in Chemical Formula 1,

[0170] A is Cl or Br.

[0171] One embodiment of the present specification provides an organic light-emitting device, which includes: a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, and one or more of the organic layers contain the above-mentioned heterocyclic compound.

[0172] In the organic light-emitting device of the present specification, one or more of the organic layers contain the heterocyclic compound of the present specification, that is, the heterocyclic compound represented by the above Chemical Formula 1. In addition, it can be manufactured using manufacturing methods and materials known in the art.

[0173] For example, the organic light-emitting device of the present specification can be manufactured by sequentially laminating a first electrode, an organic layer, and a second electrode on a substrate. At this time, it can be manufactured as follows: using a physical vapor deposition method (PVD: Physical Vapor Deposition) such as sputtering or electron beam evaporation, depositing a metal or a conductive metal oxide or an alloy thereof on the substrate to form the first electrode, and then forming an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer on the first electrode, and then depositing a material that can be used as the second electrode on the organic layer. In addition to this method, the organic light-emitting device can also be manufactured by sequentially depositing a second electrode material, an organic layer, and a first electrode material on the substrate. In addition, when manufacturing the organic light-emitting device, the heterocyclic compound represented by the above Chemical Formula 1 can be formed into an organic layer not only by vacuum evaporation but also by solution coating. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.

[0174] When the above organic light-emitting device includes a plurality of organic layers, the organic layers can be formed of the same material or different materials.

[0175] The above organic layer may be a multi-layer structure including a hole injection layer, a hole transport layer, a layer that simultaneously performs hole injection and hole transport, an electron blocking layer, a light-emitting layer, and an electron transport layer, an electron injection layer, a layer that simultaneously performs electron injection and electron transport, etc., but is not limited thereto, and may also be a single-layer structure. In addition, various polymer materials may be used for the above organic layer, and it may be manufactured into a smaller number of layers by a solvent process (such as spin coating, dip coating, blade coating, screen printing, inkjet printing, or thermal transfer printing, etc.) other than the evaporation method.

[0176] In one embodiment of the present specification, the above organic layer includes an electron injection layer, an electron transport layer, or a layer that simultaneously performs electron injection and electron transport, and the electron injection layer, the electron transport layer, or the layer that simultaneously performs electron injection and electron transport contains the above heterocyclic compound.

[0177] In one embodiment of the present specification, the above organic layer includes a hole blocking layer, and the hole blocking layer contains the above heterocyclic compound.

[0178] According to one embodiment of the present specification, the above organic layer may further include one or more layers selected from a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.

[0179] In one embodiment of the present specification, the above first electrode is an anode and the second electrode is a cathode.

[0180] According to another embodiment, the above first electrode is a cathode and the second electrode is an anode.

[0181] For example, the structure of the organic light-emitting device of the present specification may have a structure as Figures 1 to 4 shown, but is not limited thereto.

[0182] Figure 1 illustrates the structure of an organic light-emitting device in which a first electrode 2, a light-emitting layer 3, and a second electrode 4 are sequentially stacked on a substrate 1. The above Figure 1 is an exemplary structure of an organic light-emitting device according to one embodiment of the present specification, and may further include other organic layers.

[0183] Figure 2 illustrates the structure of an organic light-emitting device in which a first electrode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 3, an electron transport layer 7, an electron injection layer 8, and a second electrode 4 are sequentially stacked on a substrate 1. The above Figure 2 is an exemplary structure according to the embodiment of the present specification, and may further include other organic layers.

[0184] Figure 3The structure of an organic light-emitting device in which a first electrode 2, a hole injection layer 5, a first hole transport layer 6-1, a second hole transport layer 6-2, a light-emitting layer 3, an electron injection and transport layer 9, and a second electrode 4 are sequentially stacked on a substrate 1 is illustrated. The above Figure 3 is an exemplary structure according to an embodiment of the present specification and may further include other organic layers.

[0185] Figure 4 The structure of an organic light-emitting device in which a first electrode 2, a hole injection layer 5, a first hole transport layer 6-1, a second hole transport layer 6-2, a light-emitting layer 3, a hole blocking layer 10, an electron injection and transport layer 9, and a second electrode 4 are sequentially stacked on a substrate 1 is illustrated. The above Figure 3 is an exemplary structure according to an embodiment of the present specification and may further include other organic layers.

[0186] Specifically, in addition to the structures clearly shown in the above figures, the above organic light-emitting device may have a stacked structure exemplified as follows, but is not limited thereto.

[0187] (1) Anode / Hole transport layer / Light-emitting layer / Cathode

[0188] (2) Anode / Hole injection layer / Hole transport layer / Light-emitting layer / Cathode

[0189] (3) Anode / Hole injection layer / Hole buffer layer / Hole transport layer / Light-emitting layer / Cathode

[0190] (4) Anode / Hole transport layer / Light-emitting layer / Electron transport layer / Cathode

[0191] (5) Anode / Hole transport layer / Light-emitting layer / Electron transport layer / Electron injection layer / Cathode

[0192] (6) Anode / Hole injection layer / Hole transport layer / Light-emitting layer / Electron transport layer / Cathode

[0193] (7) Anode / Hole injection layer / Hole transport layer / Light-emitting layer / Electron transport layer / Electron injection layer / Cathode

[0194] (8) Anode / Hole injection layer / Hole buffer layer / Hole transport layer / Light-emitting layer / Electron transport layer / Cathode

[0195] (9) Anode / Hole injection layer / Hole buffer layer / Hole transport layer / Light-emitting layer / Electron transport layer / Electron injection layer / Cathode

[0196] (10) Anode / Hole transport layer / Electron suppression layer / Light-emitting layer / Electron transport layer / Cathode

[0197] (11) Anode / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0198] (12) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0199] (13) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0200] (14) Anode / Hole Transport Layer / Light Emitting Layer / Hole Blocking Layer / Electron Transport Layer / Cathode

[0201] (15) Anode / Hole Transport Layer / Light Emitting Layer / Hole Blocking Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0202] (16) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Hole Blocking Layer / Electron Transport Layer / Cathode

[0203] (17) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Hole Blocking Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0204] (18) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Hole Blocking Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0205] In one embodiment of the present specification, the above hole transport layer may be composed of a multi-layer structure. For example, it may be composed of a first hole transport layer and a second hole transport layer containing different substances from each other.

[0206] The above anode is an electrode for injecting holes. As the anode material, generally, in order to enable holes to be smoothly injected into the organic layer, a material with a large work function is preferred. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO, Indium Tin Oxide), indium zinc oxide (IZO, Indium Zinc Oxide); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylenedioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but not limited thereto.

[0207] The above-mentioned cathode is an electrode for injecting electrons. As the cathode material, usually in order to facilitate the injection of electrons into the organic layer, a material with a small work function is preferred. 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 their alloys; multilayer structure materials such as LiF / Al or LiO2 / Al, etc., but not limited thereto.

[0208] The above-mentioned hole injection layer is a layer that plays a role in facilitating the injection of holes from the anode to the light-emitting layer. The hole injection material is a material that can well receive holes from the anode at a low voltage. It is preferred that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic compounds, hexanitrile hexaazatriphenylene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, carbazole-based organic compounds, fluorene-based organic compounds, anthraquinone, and conductive polymers such as polyaniline and polythiophene, etc., but not limited thereto. Specifically, as the above-mentioned hole injection material, a compound containing substituted or unsubstituted carbazole and substituted or unsubstituted fluorene can be used, but not limited thereto.

[0209] In one embodiment of the present specification, the thickness of the above-mentioned hole injection layer can be 1 nm to 150 nm. When the thickness of the above-mentioned hole injection layer is 1 nm or more, it has the advantage of preventing the reduction of hole injection characteristics. When it is 150 nm or less, it has the advantage of preventing the driving voltage from rising in order to improve the migration of holes when the thickness of the hole injection layer is too thick.

[0210] The above-mentioned hole transport layer can play a role in facilitating the transport of holes. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer. A material with a large hole mobility is suitable. Examples of the hole transport material include arylamine-based organic compounds, carbazole-based organic compounds, quinoxaline-based organic compounds, fluorene-based organic compounds, conductive polymers, and block copolymers having both a conjugated part and a non-conjugated part, etc., but not limited thereto. Specifically, the above-mentioned hole transport material includes quinoxaline-based compounds and arylamine-based compounds, etc., but not limited thereto.

[0211] A hole buffer layer can be further provided between the hole injection layer and the hole transport layer, which can contain materials known in the art for hole injection or transport.

[0212] An electron blocking layer can be provided between the hole transport layer and the light-emitting layer. The above-mentioned electron blocking layer can use the above-mentioned compounds or materials known in the art.

[0213] The above-mentioned light-emitting layer can emit red, green or blue light and can be composed of phosphorescent materials or fluorescent materials. The above-mentioned light-emitting material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer respectively and combine them to emit light in the visible light region, and is preferably a material with high quantum efficiency for fluorescence or phosphorescence. As a specific example, there are aluminum 8-hydroxyquinoline complex (Alq3), carbazole-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzo azole-based compounds, benzothiazole-based compounds, benzimidazole-based compounds, poly(p-phenylene vinylene) (PPV)-based polymers, spiro compounds, polyfluorene, rubrene, etc., but are not limited thereto.

[0214] In an embodiment of the present specification, the above-mentioned light-emitting layer includes a host and a dopant. The above-mentioned host can include the above-mentioned compounds, aromatic condensed ring derivatives, heterocyclic compounds, etc. Specifically, as aromatic condensed ring derivatives, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and as heterocyclic compounds, there are carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds pyrimidine derivatives, etc., but are not limited thereto.

[0215] As the above dopant, phosphorescent materials such as PIQIr(acac) (bis(1-phenylisoquinoline)acetylacetonate iridium), PQIr(acac) (bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), PtOEP (octaethylporphyrinplatinum), etc., or fluorescent materials such as Alq3 (tris(8-hydroxyquinolino)aluminum) can be used, but not limited thereto. When the light-emitting layer emits green light, as the light-emitting dopant, phosphorescent materials such as Ir(ppy)3 (fac tris(2-phenylpyridine)iridium) or fluorescent materials such as Alq3 (tris(8-hydroxyquinolino)aluminum) can be used, but not limited thereto. When the light-emitting layer emits blue light, as the light-emitting dopant, (4,6-F2ppy)2Irpic, spiro-DPVBi, spiro-6P, divinylbenzene (DSB), divinylarylene (DSA), PFO-based polymers, PPV-based, pyrene-based, arylamine-based compounds, etc. can be used, but not limited thereto.

[0216] In an embodiment of the present specification, a hole-blocking layer may be provided between the above electron transport layer and the light-emitting layer, and materials known in the art can be used for the hole-blocking layer.

[0217] The above electron transport layer can play a role in facilitating the transport of electrons. The electron transport material is a material that can receive electrons well from the cathode and transfer them to the light-emitting layer, and a material with a large electron mobility is suitable. As specific examples, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, anthracene-based compounds, imidazole-based compounds, hydroxyflavone-metal complexes, etc., but not limited thereto. The thickness of the electron transport layer can be 1 nm to 50 nm. When the thickness of the electron transport layer is 1 nm or more, it has the advantage of preventing the reduction of electron transport characteristics. When it is 50 nm or less, it has the advantage of preventing the driving voltage from rising in order to improve the electron migration when the thickness of the electron transport layer is too thick.

[0218] The above-mentioned electron injection layer can play a role in facilitating the injection of electrons. As the electron injection material, the following compounds are preferably used: compounds having the ability to transport electrons, having the effect of injecting electrons from the cathode, having an excellent electron injection effect on the light-emitting layer or light-emitting material, preventing excitons generated in the light-emitting layer from migrating to the hole injection layer, and having excellent thin-film forming ability. Specifically, there are fluorenone, anthraquinodimethane, biphenylquinone, thiopyran dioxide, azole, diazole, triazole, imidazole, perylene tetracarboxylic acid, fluoreneylidene methane, anthrone, anthracene, imidazole, etc. and their derivatives; metal coordination compounds; nitrogen-containing five-membered ring derivatives; and lithium quinolate (LiQ), etc., but not limited thereto.

[0219] In one embodiment of the present specification, the organic layer containing the heterocyclic compound of the above Chemical Formula 1 is an electron injection layer, an electron transport layer, or a layer that simultaneously injects and transports electrons, and the above electron injection layer, electron transport layer, or layer that simultaneously injects and transports electrons further contains a metal complex.

[0220] In one embodiment of the present specification, as examples of the above metal complex, there are Al complex of 8-hydroxyquinoline (Alq3), LiQ, metal coordination compounds, etc., but not limited thereto.

[0221] As the above metal coordination compounds, there are lithium 8-hydroxyquinolate, zinc bis(8-hydroxyquinoline), copper bis(8-hydroxyquinoline), manganese bis(8-hydroxyquinoline), aluminum tris(8-hydroxyquinoline), aluminum tris(2-methyl-8-hydroxyquinoline), gallium tris(8-hydroxyquinoline), beryllium bis(10-hydroxybenzo[h]quinoline), zinc bis(10-hydroxybenzo[h]quinoline), gallium bis(2-methyl-8-quinoline) chloride, gallium bis(2-methyl-8-quinoline)(o-cresol), aluminum bis(2-methyl-8-quinoline)(1-naphthol), and gallium bis(2-methyl-8-quinoline)(2-naphthol), etc., but not limited thereto.

[0222] In one embodiment of the present specification, in the above electron injection layer, electron transport layer, or layer that simultaneously injects and transports electrons, the heterocyclic compound of Chemical Formula 1 and the metal complex can be contained in a mass ratio of 0.5:1.5 to 1.5:0.5.

[0223] The above hole blocking layer is a layer that prevents holes from reaching the cathode, and can usually be formed under the same conditions as the hole injection layer. Specifically, there are diazole derivatives or triazole derivatives, phenanthroline derivatives, BCP, and aluminum complex, etc., but not limited thereto.

[0224] One embodiment of the present specification provides a compound represented by the above Chemical Formula 1 and a composition containing a metal complex.

[0225] The description of the metal complex contained in the above composition is the same as that in the electron injection layer, the electron transport layer, or the layer that simultaneously performs electron injection and electron transport.

[0226] In one embodiment of the present specification, in the above composition, the heterocyclic compound of Chemical Formula 1 and the metal complex may be contained in a mass ratio of 0.5:1.5 to 1.5:0.5.

[0227] Depending on the materials used, the organic light-emitting device according to the present invention may be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0228] Modes for Carrying Out the Invention

[0229] Hereinafter, in order to specifically describe the present specification, examples will be given for detailed description. However, the examples according to the present specification can be deformed into various different forms, and are not construed as limiting the scope of the present specification to the examples detailed below. The examples of the present specification are provided to more completely describe the present specification to those skilled in the art.

[0230] Production Example 1-1: Production of Compound E1

[0231]

[0232] Under a nitrogen atmosphere, E1-A (20 g, 78.7 mmol) and E1-B (27.1 g, 78.7 mmol) were added to 400 ml of tetrahydrofuran, and stirred and refluxed. Then, potassium carbonate (32.6 g, 236.1 mmol) was dissolved in 33 ml of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (2.7 g, 2.4 mmol) was added. After reacting for 1 hour, it was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was put into 20-fold 815 mL of chloroform again and dissolved, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound E1 (24.4 g, 60%, MS: [M+H] + = 518).

[0233] Production Example 1-2: Production of Compound E2

[0234]

[0235] Using each starting material as in the above reaction formula, in addition, the above compound E2 was produced by the same method as in Production Example 1-1 above.

[0236] MS: [M+H] + = 518

[0237] Production Example 1-3: Production of Compound E3

[0238]

[0239] Using each starting material as in the above reaction formula, in addition, the above compound E3 was produced by the same method as in Production Example 1-1 above.

[0240] MS: [M+H] + = 594

[0241] Production Example 1-4: Production of Compound E4

[0242]

[0243] Using each starting material as in the above reaction formula, in addition, the above compound E4 was produced by the same method as in Production Example 1-1 above.

[0244] MS: [M+H] + = 594

[0245] Production Example 1-5: Production of Compound E5

[0246]

[0247] Using each starting material as in the above reaction formula, in addition, the above compound E5 was produced by the same method as in Production Example 1-1 above.

[0248] MS: [M+H] + = 608

[0249] Production Example 1-6: Production of Compound E6

[0250]

[0251] Using each starting material as in the above reaction formula, in addition, the above compound E6 was produced by the same method as in Production Example 1-1 above.

[0252] MS: [M+H] + = 518

[0253] Production Example 1-7: Production of Compound E7

[0254]

[0255] The above compound E7 was prepared by using the respective starting materials as in the above reaction formula, and in addition, by the same method as the production method of the above Production Example 1-1.

[0256] MS: [M+H] + = 568

[0257] Production Example 1-8: Preparation of Compound E8

[0258]

[0259] The above compound E8 was prepared by using the respective starting materials as in the above reaction formula, and in addition, by the same method as the production method of the above Production Example 1-1.

[0260] MS: [M+H] + = 683

[0261] Production Example 1-9: Preparation of Compound E9

[0262]

[0263] The above compound E9 was prepared by using the respective starting materials as in the above reaction formula, and in addition, by the same method as the production method of the above Production Example 1-1.

[0264] MS: [M+H] + = 568

[0265] Production Example 1-10: Preparation of Compound E10

[0266]

[0267] The above compound E10 was prepared by using the respective starting materials as in the above reaction formula, and in addition, by the same method as the production method of the above Production Example 1-1.

[0268] MS: [M+H] + = 619

[0269] Production Example 1-11: Preparation of Compound E11

[0270]

[0271] The above compound E11 was prepared by using the respective starting materials as in the above reaction formula, and in addition, by the same method as the production method of the above Production Example 1-1.

[0272] MS: [M+H] + = 517

[0273] Production Example 1-12: Production of Compound E12

[0274]

[0275] Using each starting material as in the above reaction formula, and in addition, the above Compound E12 was produced by the same method as in Production Example 1-1 above.

[0276] MS: [M+H] + = 556

[0277] Production Example 1-13: Production of Compound E13

[0278]

[0279] Using each starting material as in the above reaction formula, and in addition, the above Compound E13 was produced by the same method as in Production Example 1-1 above.

[0280] MS: [M+H] + = 596

[0281] Production Example 1-14: Production of Compound E14

[0282]

[0283] Using each starting material as in the above reaction formula, and in addition, the above Compound E14 was produced by the same method as in Production Example 1-1 above.

[0284] MS: [M+H] + = 634

[0285] Production Example 1-15: Production of Compound E15

[0286]

[0287] Using each starting material as in the above reaction formula, and in addition, the above Compound E15 was produced by the same method as in Production Example 1-1 above.

[0288] MS: [M+H] + = 608

[0289] Production Example 1-16: Production of Compound E16

[0290]

[0291] Using each starting material as in the above reaction formula, in addition, the above compound E16 was produced by the same method as in Production Example 1-1 above.

[0292] MS: [M+H] + = 535

[0293] Production Example 1-17: Production of Compound E17

[0294]

[0295] Using each starting material as in the above reaction formula, in addition, the above compound E17 was produced by the same method as in Production Example 1-1 above.

[0296] MS: [M+H] + = 640

[0297] Production Example 1-18: Production of Compound E18

[0298]

[0299] Using each starting material as in the above reaction formula, in addition, the above compound E18 was produced by the same method as in Production Example 1-1 above.

[0300] MS: [M+H] + = 609

[0301] Production Example 1-19: Production of Compound E19

[0302]

[0303] Using each starting material as in the above reaction formula, in addition, the above compound E19 was produced by the same method as in Production Example 1-1 above.

[0304] MS: [M+H] + = 659

[0305] Production Example 1-20: Production of Compound E20

[0306]

[0307] Using each starting material as in the above reaction formula, in addition, the above compound E20 was produced by the same method as in Production Example 1-1 above.

[0308] MS: [M+H] + = 684

[0309] Production Example 1-21: Production of Compound E21

[0310]

[0311] Using each starting material as in the above reaction formula, in addition, the above compound E21 was produced by the same method as the production method of the above Production Example 1-1.

[0312] MS: [M+H] + = 660

[0313] Production Example 1-22: Production of Compound E22

[0314]

[0315] Using each starting material as in the above reaction formula, in addition, the above compound E22 was produced by the same method as the production method of the above Production Example 1-1.

[0316] MS: [M+H] + = 526

[0317] Production Example 1-23: Production of Compound E23

[0318]

[0319] Using each starting material as in the above reaction formula, in addition, the above compound E23 was produced by the same method as the production method of the above Production Example 1-1.

[0320] MS: [M+H] + = 660

[0321] [Example 1-1]

[0322] A glass substrate coated with a thin film of ITO (indium tin oxide) with a thickness was placed in distilled water dissolved with a detergent and washed using ultrasonic waves. At this time, a product of Fischer Co. was used as the detergent, and distilled water that had been filtered twice using a filter manufactured by Millipore Co. was used. After washing the ITO for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was performed with solvents of isopropyl alcohol, acetone, and methanol and then dried, and then it was transported to a plasma cleaner. In addition, using oxygen plasma, the above substrate was cleaned for 5 minutes, and then the substrate was transported to a vacuum evaporator.

[0323] On the ITO transparent electrode prepared in this way, the following HI-A compound was used with a The hole injection layer is formed by thermal vacuum evaporation of the thickness. On the above hole injection layer, the following HAT compound is vacuum-evaporated in sequence and the following HT-A compound to form the first hole transport layer and the second hole transport layer.

[0324] Next, on the above second hole transport layer, the following BH compound and BD compound are vacuum-evaporated at a weight ratio of 25:1 with a film thickness of 20 nm to form the light-emitting layer.

[0325] On the above light-emitting layer, the compound E1 manufactured in the above Production Example 1-1 and the following LiQ compound are vacuum-evaporated at a weight ratio of 1:1, so as to form the electron injection and transport layer with a thickness of. On the above electron injection and transport layer, lithium fluoride (LiF) is sequentially formed with a thickness of, and aluminum is formed with a thickness of to form the cathode.

[0326] In the above process, the evaporation rate of the organic matter is maintained / second to / second, the lithium fluoride of the cathode is maintained / second evaporation rate, and aluminum is maintained / second evaporation rate. During evaporation, the vacuum degree is maintained at 1×10 -7 Torr to 5×10 -5 Torr, thereby manufacturing an organic light-emitting device.

[0327]

[0328] Examples 1-2 to 1-23

[0329] The compounds E2 to E23 described in Table 1 below are respectively used to replace the compound E1 in the above Example 1-1. Except for this, an organic light-emitting device is manufactured by the same method as in the above Example 1-1.

[0330] Comparative Examples 1-1 to 1-10

[0331] The compounds ET-A to ET-J in Table 1 below are respectively used to replace the compound E1 in the above Example 1-1. Except for this, an organic light-emitting device is manufactured by the same method as in the above Example 1-1.

[0332]

[0333] For the organic light-emitting devices manufactured in the above Examples 1-1 to 1-23 and Comparative Examples 1-1 to 1-10, at 10 mA / cm 2The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm 2 The time (T90) when the relative initial luminance became 90% was measured at a current density of 2 . The above results are shown in Table 1 below.

[0334] [Table 1]

[0335]

[0336]

[0337]

[0338] As shown in Table 1 above, the compound represented by Chemical Formula 1 according to the present specification can be used in an organic layer of an organic light-emitting device that can simultaneously perform electron injection and electron transport.

[0339] Comparing Examples 1-1 to 1-23 in Table 1 above with Comparative Examples 1-1, 1-2, and 1-5, it can be confirmed that the organic light-emitting device containing the heterocyclic compound of Chemical Formula 1 according to the present specification shows significantly excellent characteristics in terms of lifetime compared to the organic light-emitting device containing a compound substituted with a fluorenyl group.

[0340] Comparing Examples 1-1 to 1-23 in Table 1 above with Comparative Examples 1-3 and 1-4, it can be confirmed that the organic light-emitting device containing the heterocyclic compound of Chemical Formula 1 according to the present specification shows significantly excellent characteristics in terms of lifetime compared to the organic light-emitting device containing a compound in which R1 and R2 are aryl groups or are combined with each other to form an aromatic ring.

[0341] Comparing Examples 1-1 to 1-23 in Table 1 above with Comparative Example 1-6, it can be confirmed that the organic light-emitting device containing the heterocyclic compound of Chemical Formula 1 according to the present specification shows significantly excellent characteristics in terms of efficiency compared to the organic light-emitting device containing a compound in which a heterocyclic group is substituted at the 4-position of xanthene or thioxanthene.

[0342] Comparing Examples 1-1 to 1-23 in Table 1 above with Comparative Examples 1-7 to 1-10, it can be confirmed that the organic light-emitting device containing the heterocyclic compound of Chemical Formula 1 according to the present specification shows significantly excellent characteristics in terms of efficiency compared to the organic light-emitting device containing a compound in which L is an aryl group substituted with a heterocyclic group, an aryl group having three or more rings, or a heterocyclic group.

[0343] [Example 2-1]

[0344] ITO (indium tin oxide) was used at The glass substrate with a thickness coated as a thin film is placed in distilled water dissolved with a detergent and washed using ultrasonic waves. At this time, a product of Fisher Company is used as the detergent, and the distilled water used is the distilled water filtered twice using a filter manufactured by Millipore Corporation. After washing the ITO for 30 minutes, ultrasonic washing is performed twice with distilled water for 10 minutes. After the distilled water washing is completed, ultrasonic washing is performed with a solvent of isopropyl alcohol, acetone, and methanol and then dried, and it is transported to a plasma cleaner. In addition, using oxygen plasma, the above substrate is cleaned for 5 minutes, and then the substrate is transported to a vacuum evaporation machine.

[0345] On the ITO transparent electrode prepared in this way, the following HI-A compound is thermally vacuum-evaporated with a thickness to form a hole injection layer. On the above hole injection layer, the following HAT compound is successively vacuum-evaporated and the following HT-A compound to form a first hole transport layer and a second hole transport layer.

[0346] Next, on the above second hole transport layer, the following BH compound and BD compound are vacuum-evaporated at a weight ratio of 25:1 with a film thickness of 20 nm to form a light-emitting layer.

[0347] On the above light-emitting layer, the compound E1 manufactured in Production Example 1-1 is vacuum-evaporated with a thickness to form a hole blocking layer, and ET-K and the following LiQ compound are vacuum-evaporated at a weight ratio of 1:1, so as to form an electron injection and transport layer with a thickness. On the above electron injection and transport layer, lithium fluoride (LiF) is successively evaporated with a thickness, and aluminum is evaporated with a thickness to form a cathode.

[0348] During the above process, the evaporation rate of the organic matter is maintained at / second to / second, the lithium fluoride of the cathode is maintained at / second evaporation rate, and aluminum is maintained at / second evaporation rate. During evaporation, the vacuum degree is maintained at 1×10 -7 Torr to 5×10 -5 Torr, thereby manufacturing an organic light-emitting device.

[0349]

[0350] Examples 2-2 to 2-23

[0351] The compounds E2 to E23 described in Table 2 below were used to replace compound E1 in Example 2-1 above. Except for this, an organic light-emitting device was fabricated by the same method as in Example 2-1 above.

[0352] Comparative Examples 2-1 to 2-10

[0353] The compounds ET-A to ET-J in Table 2 below were used to replace compound E1 in Example 2-1 above. Except for this, an organic light-emitting device was fabricated by the same method as in Example 2-1 above.

[0354]

[0355] For the organic light-emitting devices fabricated in Examples 2-1 to 2-23 and Comparative Examples 2-1 to 2-10 above, the driving voltage and luminous efficiency were measured at a current density of 10 mA / cm 2 , and the time (T90) to reach 90% of the initial brightness was measured at a current density of 20 mA / cm 2 . The above results are shown in Table 2 below.

[0356] [Table 2]

[0357]

[0358]

[0359]

[0360] As shown in the description of Table 2 above, the compound represented by Chemical Formula 1 in this specification can be used in the organic layer of an organic light-emitting device that can simultaneously perform electron injection and electron transport.

[0361] Comparing Examples 2-1 to 2-23 in Table 2 above with Comparative Examples 2-1, 2-2, and 2-5, it can be confirmed that an organic light-emitting device containing the heterocyclic compound of Chemical Formula 1 in this specification shows significantly superior characteristics in terms of lifetime compared to an organic light-emitting device containing a compound substituted with a fluorenyl group.

[0362] Comparing Examples 2-1 to 2-23 in Table 2 above with Comparative Examples 2-3 and 2-4, it can be confirmed that an organic light-emitting device containing the heterocyclic compound of Chemical Formula 1 in this specification shows significantly superior characteristics in terms of lifetime compared to an organic light-emitting device containing a compound in which R1 and R2 are aryl groups or combine with each other to form an aromatic ring.

[0363] Comparing Example 2-1 to 2-23 of Table 2 above with Comparative Example 2-6, it can be confirmed that the organic light-emitting device containing the heterocyclic compound of Chemical Formula 1 according to this specification shows significantly excellent characteristics in terms of efficiency compared to the organic light-emitting device containing a compound in which a heterocyclic group is substituted at the 4-position of xanthene or thioxanthene.

[0364] Comparing Example 2-1 to 2-23 of Table 2 above with Comparative Examples 2-7 to 2-10, it can be confirmed that the organic light-emitting device containing the heterocyclic compound of Chemical Formula 1 according to this specification shows significantly excellent characteristics in terms of efficiency compared to the organic light-emitting device containing a compound in which L is an aryl group substituted with a heterocyclic group, an aryl group having three or more rings, or a heterocyclic group.

Claims

1. A heterocyclic compound of the following Chemical Formula 1: Chemical Formula 1 In the Chemical Formula 1, b is 1, Z is O or S, R1 and R2 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group, or combine with each other to form a cyclohexyl group, L is a direct bond, a phenylene group, or a naphthylene group, a is an integer from 1 to 3. When a is 2 or more, two or more Ls are the same as or different from each other, X1 to X3 are the same as or different from each other, and are each independently CR3 or N, provided that two or more of X1 to X3 are N, R3 is hydrogen, a methyl group, or a phenyl group, wherein the term "substituted or unsubstituted" means being substituted by one or more substituents selected from deuterium, a halogen group, a cyano group, an ester group, an imide group, an amino group, an alkoxy group, an alkyl group, a cycloalkyl group, an aryl group, and a heterocyclic group, or being substituted by a substituent formed by connecting two or more of the above substituents, or having no substituents, G1 and G2 are the same as or different from each other and each independently is a group selected from the following: phenyl, biphenyl, naphthyl, anthryl, phenanthryl, fluoranthenyl, triphenylenyl, terphenyl, fluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzocarbazolyl, phen azinyl, phenothiazinyl and phenoxazinyl, or a group formed by linking two or more of the above groups, the above G1 and G2 are unsubstituted or substituted by one or more substituents selected from deuterium, a cyano group, an alkyl group, a phenyl group, and a naphthyl group.

2. The heterocyclic compound according to claim 1, wherein, The Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-3: Chemical Formula 1-1 Chemical Formula 1-2 Chemical Formula 1-3 In the Chemical Formulas 1-1 to 1-3, Z, R1, R2, L, a, X1 to X3, G1, and G2 have the same definitions as in Chemical Formula 1.

3. The heterocyclic compound according to claim 1, wherein, The heterocyclic compound of the Chemical Formula 1 is any one of the following structures:

4. An organic light emitting device, wherein, Including: A first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers contain the heterocyclic compound according to any one of claims 1 to 3.

5. The organic light emitting device according to claim 4, wherein, The organic layer includes an electron injection layer, an electron transport layer, or a layer that simultaneously performs electron injection and electron transport, and the electron injection layer, the electron transport layer, or the layer that simultaneously performs electron injection and electron transport contains the heterocyclic compound.

6. The organic light emitting device according to claim 5, wherein, The electron injection layer, the electron transport layer, or the layer that simultaneously performs electron injection and electron transport further contains a metal complex.

7. The organic light emitting device according to claim 4, wherein, The organic layer includes a hole blocking layer, and the hole blocking layer contains the heterocyclic compound.

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