Organic light emitting device

Abstract

The present specification provides an organic light-emitting device including a compound represented by Chemical Formula 3 and a compound represented by Chemical Formula 1.

Description

Technical Field

[0001] This application claims the priority of Korean Patent Application No. 10-2023-0079954 filed with the Korean Patent Office on June 21, 2023 and Korean Patent Application No. 10-2024-0075966 filed with the Korean Patent Office on June 11, 2026, the entire contents of which are incorporated into this specification.

[0002] This specification relates to organic light emitting devices. Background Art

[0003] Generally speaking, the phenomenon of organic light emitting refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic light emitting device using the phenomenon of organic light emitting generally has a structure including an anode and a cathode and an organic layer therebetween. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is mostly formed by a multilayer structure composed of different substances, for example, it can be formed by a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. For such a structure of an organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons re-transition to the ground state, light is emitted.

[0004] There is a continuous demand for the development of new materials for organic light-emitting devices as described above. Summary of the invention

[0005] Technical issues

[0006] This specification provides an organic light-emitting device.

[0007] Solution to the problem

[0008] The present specification provides an organic light-emitting device, comprising: an anode, a cathode, a first light-emitting layer disposed between the anode and the cathode, and a second light-emitting layer disposed between the first light-emitting layer and the cathode and in contact with the first light-emitting layer.

[0009] The first light-emitting layer comprises a compound of the following chemical formula 3:

[0010] The second light emitting layer includes a mixture of a first compound including a compound of the following Chemical Formula 1 and a second compound including a compound of the following Chemical Formula 2.

[0011] [Chemical formula 3]

[0012]

[0013] In the above chemical formula 3,

[0014] L1 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0015] Any one of R1 to R10 is combined with L1, and the others are the same or different and are independently hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group, and one of the others is optionally fused with L1 to form a substituted or unsubstituted hydrocarbon ring, or is optionally fused with adjacent groups to form a substituted or unsubstituted ring,

[0016] Ar1 is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group,

[0017] m is an integer from 0 to 3. When m is 2 or more, the L1 in the brackets are the same or different from each other.

[0018] x is an integer from 1 to 3, and when x is 2 or more, the structures in the brackets are the same or different from each other, y is an integer from 1 to 3, and when y is 2 or more, the Ar1 in the brackets are the same or different from each other,

[0019]

[0020] In the above chemical formula 1,

[0021] At least one of R11 to R20 is bonded to the * site of the above chemical formula 1-1, and the others are the same as or different from each other and are independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted silyl group,

[0022] L2 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0023] Ar2 is a substituted or unsubstituted aryl group,

[0024] p is an integer from 1 to 3,

[0025]

[0026] In the above chemical formula 2,

[0027] At least one of Y1 to Y10 is bonded to the * site of the above chemical formula 2-1, and the others are the same as or different from each other and are independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted silyl group,

[0028] A and B are the same or different from each other, and are each independently a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocycle,

[0029] L3 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0030] q is an integer from 1 to 3.

[0031] Effects of the Invention

[0032] According to the description in the present specification, an organic light emitting device including the compounds represented by the above Chemical Formulae 1 to 3 can reduce driving voltage.

[0033] According to the description in the present specification, an organic light emitting device including the compounds represented by the above Chemical Formulae 1 to 3 can improve light efficiency.

[0034] According to the description in the present specification, an organic light-emitting device including the compounds represented by the above Chemical Formulae 1 to 3 can improve the lifespan characteristics of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0035] Figures 1 to 4 Organic light-emitting devices according to one embodiment of the present specification are respectively illustrated.

[0036] Figure 5 This is a diagram showing the results of HPLC analysis of a film deposited from the mixture of Experimental Example 2.

[0037] Figure 6 This is a diagram showing the results of HPLC analysis of a film deposited from the mixture of Experimental Example 3.

[0038] Explanation of symbols

[0039] 101: Substrate

[0040] 102: Anode

[0041] 103: Hole injection layer

[0042] 104: Hole transport layer

[0043] 105: Hole regulation layer

[0044] 106: Luminous layer

[0045] 106-1: First light-emitting layer

[0046] 106-2: Second light-emitting layer

[0047] 107: Electronic Regulation Layer

[0048] 108: Electron transport layer

[0049] 109: Electron injection layer

[0050] 110: cathode DETAILED DESCRIPTION

[0051] To facilitate understanding, the terms used in this specification are described in more detail below.

[0052] In the present specification, when it is mentioned that a certain component is located “on” another component, it not only includes the case where the certain component is in contact with the other component, but also includes the case where other components exist between the two components.

[0053] In the present specification, when a part is indicated to “include / comprise” a certain component, unless there is a particular description to the contrary, it means that other components may be further included, rather than excluding other components.

[0054] In this specification, the above-mentioned "layer" is interchangeable with the "film" mainly used in this technical field, and refers to a coating covering the target area. The size of the above-mentioned "layer" is not limited, and the sizes of each "layer" can be the same or different. In one embodiment, the size of the "layer" can be equal to the size of the entire device, can be equivalent to the size of a specific functional area, or can be as small as a single sub-pixel.

[0055] In this specification, the meaning of specific substance A contained in layer B includes i) the case where one or more substances A are contained in one layer B, and ii) the case where layer B is composed of one or more layers and substance A is contained in one or more layers of the multiple layers B.

[0056] In this specification, the meaning of a specific substance A being contained in layer C or layer D refers to all of the following situations: i) being contained in one or more layers among one or more layers C, or ii) being contained in one or more layers among one or more layers D, or iii) being contained in one or more layers C and one or more layers D, respectively.

[0057] The organic layer of the organic light-emitting device of the present specification may be formed by a single-layer structure or a multi-layer structure in which two or more organic layers are stacked. For example, it 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, an electron blocking layer, a hole blocking layer, etc. However, the structure of the organic light-emitting device is not limited thereto.

[0058] In the present specification, "deuteration" or "deuterated" means that hydrogen at a substitutable position of a compound is substituted with deuterium.

[0059] In the present specification, "overdeuterated" refers to a compound or group in which all hydrogen in the molecule may be substituted with deuterium, and has the same meaning as "100% deuterated".

[0060] In the present specification, "X% deuterated", "deuteration degree X%", or "deuterium substitution rate X%" means that X% of the hydrogen atoms at the substitutable positions in the structure are substituted with deuterium. For example, when the structure is dibenzofuran, "25% deuterated" dibenzofuran, "deuteration degree 25%" of the dibenzofuran, or "deuterium substitution rate 25%" of the dibenzofuran means that 2 of the 8 hydrogen atoms at the substitutable positions of the dibenzofuran are substituted or not substituted with deuterium.

[0061] In this specification, the "degree of deuteration" or "deuterium substitution rate" can be determined by nuclear magnetic resonance spectroscopy ( 1 The presence of the peptides can be confirmed by known methods such as HNMR (thin-layer chromatography / mass spectrometry), TLC / MS (thin-layer chromatography / mass spectrometry), or GC / MS (gas chromatography / mass spectrometry).

[0062] Specifically, by nuclear magnetic resonance spectroscopy ( 1 When analyzing the "deuteration degree" or "deuterium substitution rate" by H NMR, DMF (dimethylformamide) can be added as an internal standard. 1 The integration ratio on H NMR is used to calculate the degree of deuteration or deuterium substitution rate from the integrated amount of the total peak.

[0063] In addition, when analyzing the "degree of deuteration" or "deuterium substitution rate" by TLC / MS (thin layer chromatography / mass spectrometry), the substitution rate can be calculated based on the maximum value (median value) of the distribution formed by the molecular weight at the end of the reaction. For example, when analyzing the degree of deuteration of the following compound A, the molecular weight of the following starting material is 506, and when the maximum value (median value) of the molecular weight of the following compound A in the MS chart is 527, 21 of the hydrogens (26) at the substitutable positions of the following starting material are substituted with deuterium, and therefore it can be calculated that about 81% of the hydrogens are deuterated.

[0064]

[0065] In this specification, D means deuterium.

[0066] In this manual, *, dotted line or Indicates the connected part.

[0067] In the present specification, Cn means that the number of carbon atoms is n, and Cn-Cm means that the number of carbon atoms is from n to m.

[0068] In this specification, "or / or" means inclusive "or / or" rather than exclusive "or / or". For example, condition A or B satisfies any of the following: A is true (or exists), B is false (or does not exist); A is false (or does not exist), B is true (or exists); A and B are both true (or exist).

[0069] In this specification, "the mixture thereof" or "mixing" refers to a mixture containing two or more substances. The above-mentioned "mixture" or "mixing" may include a uniform and / or non-uniformly mixed state, a dissolved state, a uniform and / or non-uniformly dispersed state, etc., but is not limited thereto.

[0070] In this specification, "energy level" or "energy scale" refers to the energy magnitude. Therefore, the energy level is interpreted as representing the absolute value of the energy value. For example, a low or deep energy level means that the absolute value increases from the vacuum energy level in the negative direction.

[0071] In this specification, "HOMO (highest occupied molecular orbital)" refers to a molecular orbital function (highest occupied molecular orbital) in which electrons are located in the highest energy region among regions that can participate in bonding.

[0072] In addition, "LUMO (lowest unoccupied molecular orbital)" refers to the molecular orbital function (lowest unoccupied molecular orbital) in which the electron is located in the lowest energy region in the antibonding region, and the HOMO energy level refers to the distance from the vacuum energy level to the HOMO. In addition, the LUMO energy level refers to the distance from the vacuum energy level to the LUMO. In order to understand the distribution of electrons in the molecule and to understand the optical properties, a certain structure is required. In addition, the electronic structure has different structures in the neutral, anionic, and cationic states depending on the charge state of the molecule. For the driving of the device, the energy levels of the neutral state; the cationic and anionic states are all important, but the HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) in the neutral state are considered to be representative important properties. In order to determine the molecular structure of the chemical substance, the input structure was optimized using the density functional theory method. The BPW91 algorithm (Becke exchange and Perdew correlation-correlation functional) and DNP (double numerical basis set including polarization functional) basis set can be used for DFT calculations. The BPW91 algorithm is disclosed in the papers "AD Becke, Phys. Rev. A, 38, 3098 (1988)" and "JP Perdew and Y. Wang, Phys. Rev. B, 45, 13244 (1992)", and the DNP basis set is disclosed in the paper "B. Delley, J. Chem. Phys., 92, 508 (1990)".

[0073] In order to perform calculations using the density functional method, the "DMol3" package of Biovia can be used. When the optimal molecular structure is determined using the method given above, energy levels that can be occupied by electrons can be obtained as a result.

[0074] In this specification, "singlet energy" or "singlet energy" is represented by S. It generally refers to an electronic state in which all electrons in a molecule are paired and the spin quantum number is 0.

[0075] In this specification, "triplet energy" is represented by T. It refers to an electronic state in which the spin quantum number is 1 in a molecule. In order to obtain the physical properties of the excited state of the optimal molecular structure determined by the above method, the triplet energy is calculated using the time-dependent density functional theory (TD-DFT) method to calculate the energy levels of the singlet and triplet states. Density functional calculations can be performed using the commercial computing program "Gaussian09" software package developed by Gaussian. In order to calculate the time-dependent density functional, the B3PW91 algorithm (Becke exchange function and Perdew correlation function) and the 6-31G* basis set are used. The 6-31G* basis set is described in the paper "JA Pople et al., J. Chem. Phys. 56, 2257 (1972)". For the optimal molecular structure determined using the density functional method, the energy when the electrons are arranged in singlet and triplet states is calculated using the time-dependent density functional method (TD-DFT).

[0076] In this specification, "stable premixing" means that the composition of a raw material mixed during co-evaporation remains unchanged. Stable premixing enables two main substances (e.g., the compound of the above chemical formula 3, the first compound of the above chemical formula 1, and the second compound of the above chemical formula 2) to evaporate uniformly at the same time, which is an important factor in the sustainability of the performance of the organic light-emitting device.

[0077] In this specification, the "evaporation temperature" of a substance is the temperature at which the substance evaporates at a given distance from the source of evaporation of the substance being evaporated. The evaporation rate (sec) is 1×10 -6 Torr to 1×10 -9 The measurement is performed in a sublimation crucible of a vacuum evaporation tool such as a VTE chamber (vacuum thermal evaporation chamber) at a constant pressure of 1000 torr. As understood by those skilled in the art, various measured values ​​(e.g., temperature, pressure, evaporation rate, etc.) described in this specification are expected to have nominal variations due to expected fair errors in the determination of the calculated quantitative values.

[0078] As long as there is no other definition, all technical terms and scientific terms used in this specification have the same meaning as those generally understood by those skilled in the art. Similar or equivalent methods and materials described in this specification can be used for the implementation or test of embodiments of the present invention, but suitable methods and materials are described later. All publications, patent applications, patents and other references mentioned in this specification are included in this specification as a whole as a reference. When conflicting, if no specific passage is mentioned, the present specification including the definition takes precedence. In addition, materials, methods and embodiments are only illustrative and not intended to be limited.

[0079] The substituents mentioned in the present specification are described below by way of example, but are not limited thereto.

[0080] In this specification, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent. The substituted position 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 be substituted. When there are more than two substitutions, the two or more substituents may be the same or different from each other.

[0081] In the present specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from deuterium, hydroxyl, cyano, halogen group, nitro, alkyl, cycloalkyl, silyl, aryl and heterocyclic groups, or substituted with a substituent formed by connecting two or more substituents among the substituents exemplified above, or having no substituent.

[0082] In this specification, two or more substituents are linked to each other, which means that the hydrogen of any substituent is linked to another substituent. For example, two substituents can be linked to each other to form a phenyl group and a naphthyl group. In addition, the three substituents connected include not only (substituent 1)-(substituent 2)-(substituent 3) connected continuously, but also (substituent 2) and (substituent 3) connected to (substituent 1). For example, phenyl, naphthyl and isopropyl can be connected to form When four or more substituents are linked together, the above definitions also apply.

[0083] In this specification, deuterium can be interchanged with D.

[0084] In the present specification, the hydroxyl group may be -OH or -OD.

[0085] In the present specification, the term cyano group can be used interchangeably with the term nitrile group and is represented by -CN.

[0086] In the present specification, the halogen group is fluorine (—F), chlorine (—Cl), bromine (—Br) or iodine (—I).

[0087] In this specification, a nitro group is represented by -NO2.

[0088] In the present specification, the alkyl group may be a linear or branched group, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 1 to 30, 1 to 20, 1 to 10, or 1 to 5. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, and 5-methylhexyl.

[0089] In the present specification, the cycloalkyl group is not particularly limited, but preferably has a carbon number of 3 to 60, 3 to 30, 3 to 20, or 3 to 6. The cycloalkyl group includes not only a monocyclic group, but also a bicyclic group such as a bridgehead, a fused ring, or a spiro. As a specific example, it can be a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, etc., but is not limited thereto.

[0090] In the present specification, an aryl group refers to a monovalent group (monovalent groups) of a monovalent aromatic hydrocarbon or an aromatic hydrocarbon derivative. An aromatic hydrocarbon refers to a compound containing a planar ring with completely conjugated π electrons. In addition, a group derived from an aromatic hydrocarbon refers to a structure in which an aromatic hydrocarbon or a cyclic aliphatic hydrocarbon is condensed on an aromatic hydrocarbon. In addition, in the present specification, an aryl group includes a monovalent group formed by connecting two or more aromatic hydrocarbons or aromatic hydrocarbon derivatives to each other. The number of carbon atoms of the aryl group is not particularly limited, but preferably the number of carbon atoms is 6 to 50, 6 to 30, 6 to 25, 6 to 20, 6 to 18, or 6 to 13. In addition, the above-mentioned aryl group may be monocyclic or polycyclic. As a specific monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, etc., but it is not limited thereto. As a specific polycyclic aryl group, it may be naphthyl, anthracenyl, phenanthrenyl, triphenyl, pyrenyl, perylenyl, yl, fluorenyl, etc., but are not limited to these.

[0091] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0092] In this specification, when it is indicated that the fluorenyl group may be substituted, the substituted fluorenyl group includes all compounds in which the substituents of the five-membered ring of fluorene are spiro-bonded to each other to form an aromatic hydrocarbon ring. The substituted fluorenyl group may include 9,9'-spirobifluorene, spiro[cyclopentane-1,9'-fluorene], spiro[benzo[c]fluorene-7,9-fluorene], etc., but is not limited thereto.

[0093] In this specification, "adjacent" groups may refer to substituents substituted on atoms directly connected to the atoms substituted by the substituents, substituents closest to the substituents in stereostructure, or other substituents substituted on atoms substituted by the substituents. For example, two substituents substituted in the ortho position in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other. In addition, substituents (a total of 4) connected to two consecutive carbons in an aliphatic ring may also be interpreted as "adjacent" groups.

[0094] In the present specification, the phrase "adjacent groups are bonded to form a ring" in a substituent means that adjacent groups are bonded to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.

[0095] In the present specification, "a five-membered or six-membered ring formed by bonding adjacent groups" means that the ring including the substituents participating in the ring formation is five-membered or six-membered. This may include a case where another ring is fused to the ring including the substituents participating in the ring formation.

[0096] In the present specification, the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a combination thereof.

[0097] In the present specification, a heterocyclic ring is a ring containing a heteroatom, and may be condensed with an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring together with a ring containing a heteroatom. The heterocyclic ring may be an aromatic heterocyclic ring, an aliphatic heterocyclic ring, or a combination thereof.

[0098] In the present specification, an aromatic hydrocarbon ring refers to a planar hydrocarbon ring in which π electrons are completely conjugated, and the above description of the aryl group is applicable except that the aromatic hydrocarbon ring is divalent.

[0099] In this specification, an aliphatic hydrocarbon ring is a structure that is cyclically bonded, and refers to a ring that is not aromatic. Examples of aliphatic hydrocarbon rings include cycloalkane rings, to which the above-mentioned description of the cycloalkyl group can be applied except that the ring is divalent. In addition, substituted aliphatic hydrocarbon rings also include aliphatic hydrocarbon rings fused with aromatic rings.

[0100] In the present specification, the condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring means that the aromatic hydrocarbon ring and the aliphatic hydrocarbon ring form a condensed ring. Examples of the condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring include, but are not limited to, 1,2,3,4-tetrahydronaphthyl and 2,3-dihydro-1H-indenyl.

[0101] In the present specification, when adjacent groups in a substituent are bonded to each other to form a ring, any of the following structures may be formed.

[0102]

[0103] In the above structure,

[0104] A1 to A14 are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0105] a1 to a9 are each an integer from 1 to 4,

[0106] a10 and a14 are each an integer from 1 to 6,

[0107] When a1 to a10 and a14 are each 2 or more, the two or more substituents in the brackets are the same or different from each other.

[0108] * indicates a substituted position.

[0109] According to one embodiment of the present specification, A1 is hydrogen or a substituted or unsubstituted aryl group.

[0110] According to one embodiment of the present specification, A1 is hydrogen or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0111] According to one embodiment of the present specification, the above-mentioned A1 is hydrogen or a substituted or unsubstituted phenyl group.

[0112] According to one embodiment of the present specification, the above-mentioned A1 is hydrogen or phenyl.

[0113] According to one embodiment of the present specification, A2 to A10 and A14 are hydrogen.

[0114] According to one embodiment of the present specification, A11 to A13 are each independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0115] According to one embodiment of the present specification, A11 to A13 are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0116] According to one embodiment of the present specification, A11 and A12 are methyl groups.

[0117] According to one embodiment of the present specification, the above-mentioned A13 is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

[0118] In the present specification, the substituted aryl group may include a form in which an aliphatic ring is condensed to the aryl group.

[0119] In the present specification, a heterocyclic group may refer to a monovalent aromatic heterocyclic ring. Here, an aromatic heterocyclic ring as a monovalent group of an aromatic ring or a derivative of an aromatic ring refers to a group containing one or more of N, O and S as a heteroatom in the ring. The derivatives of the above-mentioned aromatic rings include all structures in which an aromatic ring or an aliphatic ring is condensed in an aromatic ring. In addition, in the present specification, a heterocyclic group includes a monovalent group formed by connecting two or more aromatic rings containing heteroatoms or derivatives of aromatic rings containing heteroatoms to each other. The number of carbon atoms in the above-mentioned heterocyclic group is preferably 2 to 50, 2 to 30, 2 to 20, 2 to 18, or 2 to 13. Examples of heterocyclic groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, pyridinyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, isoquinolyl, indolyl, carbazolyl, benzo Examples of the group include, but are not limited to, oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthrolinyl and dibenzofuranyl.

[0120] In the present specification, the heterocyclic group may be a monocyclic or polycyclic group, and may be an aromatic, aliphatic, or a condensed ring of an aromatic and aliphatic group.

[0121] In the present specification, an arylene group refers to a group having two bonding positions in an aryl group, that is, a divalent group. The above description of the aryl group is applicable to these groups except that they are each a divalent group.

[0122] In the present specification, a heteroarylene group refers to a group having two bonding positions in a heterocyclic group, that is, a divalent group. Except that each of them is a divalent group, the above description of the heterocyclic group is applicable.

[0123] In the present specification, the silyl group may be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, etc. The alkyl group in the alkylsilyl group may be the same as the examples given above for the alkyl group, the aryl group in the arylsilyl group may be the same as the examples given above for the aryl group, and the heteroaryl group in the heteroarylsilyl group may be the same as the examples given above for the heterocyclic group.

[0124] The present inventors have discovered suitable conditions applicable to pyrene-type hosts (hereinafter, compounds represented by Chemical Formula 3) and anthracene-type hosts (hereinafter, compounds represented by Chemical Formulas 1 and 2) that are both useful as blue fluorescent host substances and can provide a stable co-evaporation mixture after premixing.

[0125] The light-emitting layer of an organic light-emitting device showing excellent life and efficiency requires more than 2 components (for example, 3 or 4 components). In this case, a very complicated process and high cost are required compared to a light-emitting layer having only 2 raw materials (i.e., a single host substance and a dopant). Premixing more than 2 materials and evaporating them from one raw material can reduce the complexity of the manufacturing process. The hole transport host(s) used and other types of hosts (such as electron transport hosts) can be mixed and co-evaporated in one crucible, so that stable evaporation can be achieved.

[0126] However, co-evaporation must be stable, which means that the composition of the evaporated film must remain constant during the manufacturing process. Any change in composition may have an adverse effect on device performance. Under vacuum conditions, after a mixture is formed by two or more compounds, a stable co-evaporation mixture is obtained based on the mixture. As a condition for a stable co-evaporation mixture, it is expected that the above compounds should have the same evaporation temperature under the same conditions. However, it is expected that the same evaporation temperature is not the only applicable parameter for obtaining a stable co-evaporation mixture. For example, when mixing two compounds, the two compounds can interact with each other, thereby having different evaporation characteristics from those of a single compound. In addition, even if the two compounds have different evaporation temperatures from each other, a stable co-evaporation mixture can be generated. Therefore, it is difficult to achieve a stable co-evaporation mixture. Although there are various host substances, there are almost no documents that record the exemplary co-evaporation mixtures that can be obtained based on them.

[0127] In this specification, new types of pyrene host materials (represented by chemical formula 3) and anthracene host materials (represented by chemical formula 1) that are useful as blue fluorescent host materials and can be premixed to provide a stable co-evaporation mixture are suggested. Multiple factors other than temperature (e.g., miscibility of different substances, different phase changes) can contribute to evaporation. The inventors have found that when two substances have similar evaporation temperatures, similar mass reduction rates or similar vapor pressures, the two substances can be continuously co-evaporated. The mass reduction rate is defined as the percentage of mass reduction over time (minutes), as measured by thermogravimetric analysis (TGA) under the same constant temperature given to each compound and under the same experimental conditions after the composition reaches a stable evaporation state. It is determined by measuring the time required for the initial 10% mass loss. The given constant temperature is a temperature point selected for the mass reduction rate value to be approximately 0.05 to 0.50% / minute. Those skilled in the art understand that in order to compare two parameters, the experimental conditions must be constant. Methods for measuring mass reduction rate and vapor pressure are known in the art, and can be found, for example, in the document "Bull. et al. Mater. Sci. 2011, 34, 7". In addition, the present inventors have found that in order to achieve a stable co-evaporation mixture, the compounds have similar sublimation temperatures to each other, and when the variation of the composition is within 5%, the compounds can be continuously co-evaporated without deviation in device performance.

[0128] In order to manufacture a blue fluorescent light-emitting layer with such a mixed host material, three evaporation sources (i.e., two host materials and a blue fluorescent dopant) are required. The concentration of the common host and the dopant is crucial to the device performance. Usually, the evaporation rate of each component is measured separately during the evaporation process. However, manufacturing a blue fluorescent light-emitting layer from three evaporation sources requires complex procedures and high costs. Therefore, it is preferred to mix more than two components to reduce the number of evaporation sources.

[0129] In this specification, when two blue fluorescent host materials are premixed and the mixture is manufactured by thermal sublimation, if the difference in composition between the compounds is within a certain range, it is judged that co-evaporation can be performed from one raw material, thereby having stable premixability. The above-mentioned premixability is as described in the above definition. Uniform co-evaporation of the two host materials is crucial to the sustainability of the performance of the device manufactured therefrom.

[0130] The compound of Chemical Formula 3 of the present invention contains pyrene. Compared with a compound having an anthracene structure, it uses an extremely high triplet energy level and can exhibit a further efficiency-increasing effect through electron migration to the triplet energy level of a dopant substance.

[0131] The first compound of Chemical Formula 1 and the second compound of Chemical Formula 2 of the present invention have an anthracene structure. They have the advantages of excellent migration and injection of electrons and holes, but have the disadvantage of low energy efficiency while emitting light through singlet level fluorescence. In the case where the compound of Chemical Formula 3, the first compound of Chemical Formula 1 and the second compound of Chemical Formula 2 are included in the light-emitting layer, the compound of Chemical Formula 3 can be further improved in efficiency while maintaining the appropriate energy levels of the first and second compounds and stable performance through electron / hole balance.

[0132] Next, embodiments of the present specification will be described.

[0133] An organic light-emitting device according to one embodiment of the present specification includes: an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode.

[0134] The light emitting layer includes compounds of the following chemical formulas 1 to 3.

[0135] [Chemical formula 3]

[0136]

[0137] In the above chemical formula 3,

[0138] L1 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0139] Any one of R1 to R10 is combined with L1, and the others are the same or different and are independently hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group, and one of the others is optionally fused with L1 to form a substituted or unsubstituted hydrocarbon ring, or is optionally fused with adjacent groups to form a substituted or unsubstituted ring,

[0140] Ar1 is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group,

[0141] m is an integer from 0 to 3. When m is 2 or more, the L1 in the brackets are the same or different from each other.

[0142] x is an integer from 1 to 3, and when x is 2 or more, the structures in the brackets are the same or different from each other, y is an integer from 1 to 3, and when y is 2 or more, the Ar1 in the brackets are the same or different from each other,

[0143]

[0144] In the above chemical formula 1,

[0145] At least one of R11 to R20 is bonded to the * site of the above chemical formula 1-1, and the others are the same as or different from each other and are independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted silyl group,

[0146] L2 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0147] Ar2 is a substituted or unsubstituted aryl group,

[0148] p is an integer from 1 to 3,

[0149]

[0150] In the above chemical formula 2,

[0151] At least one of Y1 to Y10 is bonded to the * site of the above chemical formula 2-1, and the others are the same as or different from each other and are independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted silyl group,

[0152] A and B are the same or different from each other, and are each independently a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocycle,

[0153] L3 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0154] q is an integer from 1 to 3.

[0155] In one embodiment of the present specification, the light-emitting layer may be composed of a single layer, but may be composed of two or more layers.

[0156] When the light-emitting layer is a single layer, one layer contains the compounds of the above Chemical Formulas 1 to 3. Such a single-layer light-emitting layer can be formed by co-deposition or pre-mixing and then deposition of the compounds of the above Chemical Formulas 1 to 3.

[0157] When the above-mentioned light-emitting layer is two or more plural layers, the compounds represented by the above Chemical Formulas 1 to 3 may be included in one layer, or the compound of the above Chemical Formula 3 and the compounds of the above Chemical Formulas 1 and 2 may be respectively included in different light-emitting layers. For example, the above light-emitting layer may include a first light-emitting layer containing the compound of the above Chemical Formula 3 and a second light-emitting layer containing the compounds of the above Chemical Formulas 1 and 2. At this time, the above second light-emitting layer may be provided between the above first light-emitting layer and the above cathode. The above first light-emitting layer and the above second light-emitting layer may be provided adjacent to each other. When the compounds represented by the above Chemical Formulas 1 to 3 are respectively included as hosts in the above first light-emitting layer and the above second light-emitting layer, the above first light-emitting layer and the above second light-emitting layer further include dopant compounds respectively. At this time, the first light-emitting layer and the above second light-emitting layer may include the same kind of dopant substances as each other, and may include different kinds of dopant substances from each other, but it is preferable to include the same kind of dopant substances.

[0158] In one embodiment of the present specification, the above light-emitting layer of one or more layers includes the compounds represented by the above Chemical Formulas 1 to 3 as hosts.

[0159] The thickness (D1) of the above first light-emitting layer and the thickness (D2) of the above second light-emitting layer satisfy Mathematical Formula 1 (D1 < D2). Specifically, the thickness (D1) of the above first light-emitting layer may be less than the thickness (D2) of the above second light-emitting layer.

[0160] Hereinafter, the compound represented by Chemical Formula 3 will be described in detail.

[0161] In one embodiment of the present specification, L1 may be a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group.

[0162] In one embodiment of the present specification, L1 may be a direct bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C2-C30 divalent heterocyclic group.

[0163] In one embodiment of the present specification, L1 may be a direct bond, a substituted or unsubstituted C6-C20 arylene group, or a substituted or unsubstituted C2-C20 divalent heterocyclic group.

[0164] In one embodiment of the present specification, L1 may be a direct bond, a substituted or unsubstituted C6-C10 arylene group, or a substituted or unsubstituted C2-C10 divalent heterocyclic group.

[0165] In one embodiment of the present specification, L1 is independently a direct bond, phenylene, biphenylene, terphenylene, naphthylene, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, phenanthrenyl, triphenylene, dibenzofuranyl, dibenzothienyl or carbazolyl, wherein L1 may be further substituted or unsubstituted by deuterium, C1-C30 substituted or unsubstituted alkyl, C5-C30 substituted or unsubstituted cycloalkyl, C6-C30 substituted or unsubstituted aryl, C5-C30 substituted or unsubstituted heterocyclic group, or at least one of the substituents of L1 may be combined with an adjacent substituent to form one or more C5-C30 substituted or unsubstituted rings. Here, the "unsubstituted" case means that it is composed entirely of hydrogen.

[0166] In one embodiment of the present specification, L1 is each independently a direct bond, a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a dimethylfluorenyl group, a diphenylfluorenyl group, a spirobifluorenyl group, a phenanthrenyl group, a triphenylene group, a dibenzofuranyl group, a dibenzothiophenyl group or a carbazolyl group, and L1 may be further substituted or unsubstituted by deuterium, a C1-C20 substituted or unsubstituted alkyl group, a C5-C20 substituted or unsubstituted cycloalkyl group, a C6-C20 substituted or unsubstituted aryl group, a C5-C20 substituted or unsubstituted heterocyclic group, or at least one of the substituents of L1 may be combined with an adjacent substituent to form one or more C5-C30 substituted or unsubstituted rings.

[0167] In one embodiment of the present specification, L1 is independently a direct bond, a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a dimethylfluorenyl group, a diphenylfluorenyl group, a spirobifluorenyl group, a phenanthrenyl group, a triphenylene group, a dibenzofuranyl group, a dibenzothiophenyl group or a carbazolyl group, and L1 may be further substituted or unsubstituted by a C1-C10 substituted or unsubstituted alkyl group, a C5-C10 substituted or unsubstituted cycloalkyl group, a C6-C10 substituted or unsubstituted aryl group, or a C5-C10 substituted or unsubstituted heterocyclic group, or at least one of the substituents of L1 may be combined with an adjacent substituent to form one or more C5-C10 substituted or unsubstituted rings.

[0168] In one embodiment of the present specification, L1 is independently a direct bond, a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a dimethylfluorenyl group, a diphenylfluorenyl group, a spirobifluorenyl group, a phenanthrenyl group, a triphenylene group, a dibenzofuranyl group, a dibenzothiophenyl group or a carbazolyl group, and L1 may be further substituted or unsubstituted by one or more substituents selected from deuterium, a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a cyclopentyl group, a cyclohexyl group, a phenyl group, a biphenylene group, a naphthyl group or a carbazolyl group, or at least one of the substituents of L1 may be combined with an adjacent substituent to form one or more C5-C6 substituted or unsubstituted rings.

[0169] In one embodiment of the present specification, L1 may be any one selected from the following structures.

[0170]

[0171]

[0172]

[0173]

[0174]

[0175] In the above structure, the dotted line represents the site connected to any one of R1 to R10 and Ar1, or to another L1 in the above Chemical Formula 3, and the rest except the above dotted line are the same as or different from each other, and each independently can be hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group.

[0176] In one embodiment of the present specification, the dotted line represents a site connected to any one of R1 to R10 of the above Chemical Formula 3, or to another L1, and the rest except the above dotted line are the same as or different from each other, and each independently may be hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C1-C30 alkylsilyl group, a substituted or unsubstituted C6-C90 arylsilyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group.

[0177] In one embodiment of the present specification, the dotted line represents a site connected to any one of R1 to R10 of the above Chemical Formula 3, or to another L1, and the rest except the above dotted line are the same as or different from each other, and each independently may be hydrogen, deuterium, a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C1-C18 alkylsilyl group, a substituted or unsubstituted C6-C40 arylsilyl group, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C20 heterocyclic group.

[0178] In one embodiment of the present specification, the dotted line represents a site connected to any one of R1 to R10 of the above Chemical Formula 3, or to another L1, and the rest except the above dotted line are the same as or different from each other, and each independently may be hydrogen, deuterium, a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted C4-C6 cycloalkyl group, a substituted or unsubstituted C6-C15 aryl group, or a substituted or unsubstituted C4-C15 heterocyclic group.

[0179] In one embodiment of the present specification, the dotted line represents a site connected to any one of R1 to R10 of the above Chemical Formula 3, or to another L1, and the rest except the above dotted line are the same as or different from each other, and each independently may be hydrogen, deuterium, a C3-C6 alkyl group substituted or unsubstituted by deuterium, a C4-C6 cycloalkyl group substituted or unsubstituted by deuterium, a C6-C15 aryl group substituted or unsubstituted by deuterium, or a C4-C15 heterocyclic group substituted or unsubstituted by deuterium.

[0180] In one embodiment of the present specification, in L1, the rest except the above-mentioned dotted line are the same as or different from each other, and each independently can be hydrogen, deuterium, methyl substituted or unsubstituted by deuterium, ethyl substituted or unsubstituted by deuterium, n-propyl substituted or unsubstituted by deuterium, isopropyl substituted or unsubstituted by deuterium, n-butyl substituted or unsubstituted by deuterium, tert-butyl substituted or unsubstituted by deuterium, cyclopentyl substituted or unsubstituted by deuterium, cyclohexyl substituted or unsubstituted by deuterium, phenyl substituted or unsubstituted by deuterium, naphthyl substituted or unsubstituted by deuterium, phenanthrenyl substituted or unsubstituted by deuterium, or carbazolyl substituted or unsubstituted by deuterium.

[0181] In one embodiment of the present specification, in L1, the rest except the above-mentioned dotted line are the same or different from each other, and each independently can be hydrogen, deuterium, unsubstituted tert-butyl, unsubstituted cyclohexyl, deuterium-substituted or unsubstituted phenyl, deuterium-substituted naphthyl, unsubstituted phenanthrenyl, or unsubstituted carbazolyl.

[0182] In one embodiment of the present specification, any one of R1 to R10 is connected to L1, and the groups not connected to L1 are the same as or different from each other, and each independently can be hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group.

[0183] In one embodiment of the present specification, any one of R1 to R10 is connected to L1, and the groups not connected to L1 are the same as or different from each other, and each independently may be hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl.

[0184] In one embodiment of the present specification, any one of R1 to R10 is connected to L1, and the groups not connected to L1 are the same as or different from each other, and each independently may be hydrogen, deuterium, an unsubstituted alkyl group, or an aryl group that may be substituted or unsubstituted with deuterium.

[0185] In one embodiment of the present specification, any one of R1 to R10 is connected to L1, and the groups not connected to L1 are the same as or different from each other, and each independently may be hydrogen, deuterium, isopropyl, or phenyl substituted or unsubstituted with deuterium.

[0186] In this specification, the above Chemical Formula 3 is the following Chemical Formula 3-3.

[0187] [Chemical formula 3-3]

[0188]

[0189] In the above chemical formula 3-3, L1, Ar1, x and y are the same as those in the above chemical formula 3, L2 and L3 are each the same as those in the above L1,

[0190] Any one of R1 to R10 is combined with any one of L1 to L3, and the rest are the same or different and are independently hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic, and are selectively fused with adjacent groups to form a substituted or unsubstituted ring,

[0191] The above Ar1 is combined with any one of L1 to L3, and Ar1 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0192] In this specification, the above Chemical Formula 3 is any one of the following Chemical Formulas 3-3-1 to 3-3-3.

[0193] [Chemical formula 3-3-1]

[0194]

[0195] [Chemical formula 3-3-2]

[0196]

[0197] [Chemical formula 3-3-3]

[0198]

[0199] In the above chemical formulas 3-3-1 to 3-3-3, L1 and Ar1 are the same as those defined in the above chemical formula 3.

[0200] L2 and L3 are each the same as the above definition of L1,

[0201] Any one of R1 to R10 is combined with any one of L1 to L3, and the rest are the same or different and are independently hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic, and are selectively fused with adjacent groups to form a substituted or unsubstituted ring,

[0202] The above Ar1 is combined with any one of L1 to L3, and Ar1 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0203] In one embodiment of the present specification, the above Chemical Formula 3 may be any one of the following Chemical Formulas 3-A to 3-F.

[0204] In one embodiment of the present specification, the above-mentioned chemical formula 3 is the following chemical formula 3-A. In one embodiment of the present specification, the above-mentioned chemical formula 3 is the following chemical formula 3-B. In one embodiment of the present specification, the above-mentioned chemical formula 3 is the following chemical formula 3-C. In one embodiment of the present specification, the above-mentioned chemical formula 3 is the following chemical formula 3-D. In one embodiment of the present specification, the above-mentioned chemical formula 3 is the following chemical formula 3-E. In one embodiment of the present specification, the above-mentioned chemical formula 3 is the following chemical formula 3-F.

[0205] [Chemical Formula 3-A]

[0206]

[0207] [Chemical formula 3-B]

[0208]

[0209] [Chemical formula 3-C]

[0210]

[0211] [Chemical formula 3-D]

[0212]

[0213] [Chemical formula 3-E]

[0214]

[0215] [Chemical formula 3-F]

[0216]

[0217] In the above Chemical Formulae 3-A to 3-F, L1, m, R1 to R10 and Ar1 are the same as defined in the above Chemical Formula 3.

[0218] In one embodiment of the present specification, the above Chemical Formula 3 may be any one of the following Chemical Formulas 3-a to 3-e.

[0219] In one embodiment of the present specification, the above Chemical Formula 3 is the following Chemical Formula 3-a.

[0220] In one embodiment of the present specification, the above Chemical Formula 3 is the following Chemical Formula 3-b.

[0221] In one embodiment of the present specification, the above Chemical Formula 3 is the following Chemical Formula 3-c.

[0222] In one embodiment of the present specification, the above Chemical Formula 3 is the following Chemical Formula 3-d.

[0223] In one embodiment of the present specification, the above Chemical Formula 3 is the following Chemical Formula 3-e.

[0224] [Chemical formula 3-a]

[0225]

[0226] [Chemical formula 3-b]

[0227]

[0228] [Chemical formula 3-c]

[0229]

[0230] [Chemical formula 3-e]

[0231]

[0232] In the above chemical formulae 3-a to 3-e, Ar1 is the same as defined in the above chemical formula 3,

[0233] Any one of R1 to R10 is combined with Ar1, and the rest are the same or different from each other, and are independently hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, and are selectively fused with adjacent groups to form a substituted or unsubstituted ring.

[0234] In one embodiment of the present specification, the above Chemical Formula 3 is represented by any one of the following compounds.

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253] Next, the compound represented by Chemical Formula 1 is described in detail.

[0254] According to one embodiment of the present specification, 1 to 3 of the above R11 to R20 are bonded to the * portion of the above Chemical Formula 1-1, and the rest are hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted silyl group.

[0255] According to another embodiment, 1 to 3 of the above R11 to R20 are bound to the * portion of the above Chemical Formula 1-1, and the rest are hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 2 to 60 carbon atoms, or a substituted or unsubstituted silyl group.

[0256] In another embodiment, the above R19 and R20 are bound to the * portion of the above Chemical Formula 1-1, and the rest are hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted silyl group.

[0257] According to another embodiment, the above R19, R20 and R18 are bound to the * position of the above Chemical Formula 1-1, and the rest are hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted silyl group.

[0258] In another embodiment, the above R19, R20 and R17 are combined with the * position of the above Chemical Formula 1-1, and the rest are hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted silyl group.

[0259] According to one embodiment of the present specification, the substituents not bonded to the above Chemical Formula 1-1 in the above R11 to R20 are the same as or different from each other, and are each independently hydrogen, deuterium or dibenzofuranyl.

[0260] According to one embodiment of the present specification, the above p is an integer of 3, and the three L2s are the same as or different from each other.

[0261] In another embodiment, the above p is an integer of 2, and the two L2 are the same as or different from each other.

[0262] According to one embodiment of the present specification, the above Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-A to 1-C.

[0263] [Chemical Formula 1-A]

[0264]

[0265] [Chemical Formula 1-B]

[0266]

[0267] [Chemical Formula 1-C]

[0268]

[0269] In the above chemical formulas 1-A to 1-C,

[0270] R1' to R8' are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted silyl group,

[0271] L11 to L14 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0272] Ar11 to Ar14 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group.

[0273] According to one embodiment of the present specification, the above-mentioned R1' to R8' are hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or a substituted or unsubstituted silyl group.

[0274] According to one embodiment of the present specification, the above R1′ to R8′ are the same as or different from each other, and are each independently hydrogen, deuterium or dibenzofuranyl.

[0275] According to one embodiment of the present specification, L2 is a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms. L2 may be substituted with deuterium.

[0276] In another embodiment, L2 is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

[0277] According to another embodiment, L2 is a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylene group.

[0278] In another embodiment, L2 is a direct bond, a phenylene group substituted or unsubstituted by deuterium, a biphenylene group substituted or unsubstituted by deuterium, a naphthylene group substituted or unsubstituted by deuterium, a phenanthrenyl group substituted or unsubstituted by deuterium, or a triphenylene group substituted or unsubstituted by deuterium.

[0279] According to one embodiment of the present specification, Ar2 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms. Ar may be substituted with deuterium.

[0280] In another embodiment, Ar2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0281] According to another embodiment, Ar2 is 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 phenanthrenyl group, or a substituted or unsubstituted triphenylene group.

[0282] In another embodiment, Ar2 is phenyl substituted or unsubstituted by deuterium, biphenyl substituted or unsubstituted by deuterium, terphenyl substituted or unsubstituted by deuterium, naphthyl substituted or unsubstituted by deuterium, phenanthryl substituted or unsubstituted by deuterium, or triphenylene substituted or unsubstituted by deuterium.

[0283] According to one embodiment of the present specification, L11 to L14 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms. L11 to L14 may be substituted with deuterium.

[0284] In another embodiment, L11 to L14 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

[0285] According to another embodiment, the above L11 to L14 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted phenanthrenylene, or a substituted or unsubstituted triphenylene.

[0286] In another embodiment, the above L11 to L14 are the same as or different from each other, and are each independently a direct bond, a phenylene group substituted or unsubstituted by deuterium, a biphenylene group substituted or unsubstituted by deuterium, a naphthylene group substituted or unsubstituted by deuterium, a phenanthrenyl group substituted or unsubstituted by deuterium, or a triphenylene group substituted or unsubstituted by deuterium.

[0287] According to one embodiment of the present specification, Ar11 to Ar14 are the same as or different from each other, and are independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms. Ar11 to Ar14 may be substituted with deuterium.

[0288] In another embodiment, the above Ar11 to Ar14 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0289] According to another embodiment, the above Ar11 to Ar14 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylene group.

[0290] In another embodiment, the above Ar11 to Ar14 are the same as or different from each other, and are each independently a deuterium-substituted or unsubstituted phenyl group, a deuterium-substituted or unsubstituted biphenyl group, a deuterium-substituted or unsubstituted naphthyl group, a deuterium-substituted or unsubstituted terphenyl group, a deuterium-substituted or unsubstituted phenanthryl group, or a deuterium-substituted or unsubstituted triphenylene group.

[0291] The second light emitting layer includes a mixture of a first compound of the compound of Chemical Formula 1 and a second compound including a compound of Chemical Formula 2 different from the first compound.

[0292] In one embodiment of the present specification, the chemical formula 1 may be selected from the following structural formulas, but is not limited thereto, and the binding position of deuterium is not limited. In addition, when the chemical formula 1 does not contain deuterium, it may be a structure in which deuterium (-D) is excluded from the following structural formula, but is not limited thereto.

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364]

[0365]

[0366]

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397]

[0398]

[0399]

[0400]

[0401]

[0402]

[0403]

[0404]

[0405]

[0406]

[0407]

[0408]

[0409]

[0410]

[0411]

[0412]

[0413]

[0414]

[0415]

[0416]

[0417]

[0418]

[0419]

[0420]

[0421]

[0422]

[0423]

[0424]

[0425]

[0426]

[0427]

[0428]

[0429]

[0430]

[0431]

[0432]

[0433]

[0434]

[0435]

[0436]

[0437]

[0438]

[0439]

[0440]

[0441]

[0442]

[0443]

[0444]

[0445]

[0446] According to one embodiment of the present specification, the compound of the above Chemical Formula 1 is different from the compound of the above Chemical Formula 2. Specifically, the compound of the above Chemical Formula 1 is a compound that does not include the structure of the above Chemical Formula 2-1. More specifically, the compound of the above Chemical Formula 1 is a compound that does not include a heterocyclic group.

[0447] The compound of the above Chemical Formula 1 is any one of the compounds other than the compounds including the structure of Chemical Formula 2-1 exemplified above, in other words, any one of the compounds not including the structure of Chemical Formula 2-1.

[0448] The compound of the above Chemical Formula 1 is any one of the compounds other than the compounds including a heterocyclic group exemplified above, in other words, any one of the compounds not including a heterocyclic group.

[0449] Next, the compound represented by Chemical Formula 2 is described in detail.

[0450] According to one embodiment of the present specification, at least one of the above Y1 to Y10 is bonded to the * site of the above Chemical Formula 2-1, and the rest are hydrogen, deuterium, or a substituted or unsubstituted aromatic group having 6 to 60 carbon atoms.

[0451] According to one embodiment of the present specification, one to three of the above Y1 to Y10 are bonded to the * portion of the above Chemical Formula 2-1, and the rest are hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted silyl group.

[0452] In one embodiment of the present specification, one to three of the above Y1 to Y10 are bonded to the * portion of the above chemical formula 2-1, and the rest are hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or a substituted or unsubstituted silyl group.

[0453] In another embodiment, the above Y7, Y8 or Y9 is bound to the * portion of the above Chemical Formula 2-1, and the rest is hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted silyl group.

[0454] According to another embodiment, the above Y7 and Y9 are bound to the * portion of the above Chemical Formula 2-1, and the rest are hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted silyl group.

[0455] According to another embodiment, the above Y9 and Y10 are bound to the * portion of the above Chemical Formula 2-1, and the rest are hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted silyl group.

[0456] According to one embodiment of the present specification, the substituents not bound to the above Chemical Formula 2-1 among Y1 to Y10 are the same as or different from each other, and are independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. The substituents not bound to the above Chemical Formula 1-1 among Y1 to Y10 may be substituted with deuterium.

[0457] According to another embodiment, the substituents in the above Y1 to Y10 that are not combined with the above Chemical Formula 2-1 are the same as or different from each other, and are independently hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, or substituted or unsubstituted triphenylene, and the above substituents may be further substituted by deuterium, phenyl substituted or unsubstituted by deuterium, biphenyl substituted or unsubstituted by deuterium, terphenyl substituted or unsubstituted by deuterium, naphthyl substituted or unsubstituted by deuterium, phenanthryl substituted or unsubstituted by deuterium, or triphenylene substituted or unsubstituted by deuterium.

[0458] According to one embodiment of the present specification, the above q is an integer of 1 to 5, and when the above q is 2 or more, two or more L2 are the same as or different from each other.

[0459] In another embodiment, the above q is an integer of 1 to 3. When the above q is 2 or more, two or more L2 are the same as or different from each other.

[0460] According to one embodiment of the present specification, the above Chemical Formula 2 is represented by the following Chemical Formulas 2-A to 2-E.

[0461] [Chemical Formula 2-A]

[0462]

[0463] [Chemical formula 2-B]

[0464]

[0465] [Chemical Formula 2-C]

[0466]

[0467] [Chemical formula 2-D]

[0468]

[0469] [Chemical Formula 2-E]

[0470]

[0471] In the above chemical formulae 2-A to 2-E,

[0472] A1 to A4 and B1 to B4 are the same as or different from each other, and are each independently a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocycle,

[0473] Y1' to Y10' are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted silyl group,

[0474] L21 to L24 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.

[0475] According to one embodiment of the present specification, L3 is a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms. L2 may be substituted with deuterium.

[0476] In another embodiment, L3 is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

[0477] According to another embodiment, L3 is a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylene group.

[0478] In another embodiment, L3 is a direct bond, a phenylene group substituted or unsubstituted by deuterium, a biphenylene group substituted or unsubstituted by deuterium, a naphthylene group substituted or unsubstituted by deuterium, a phenanthrenyl group substituted or unsubstituted by deuterium, or a triphenylene group substituted or unsubstituted by deuterium.

[0479] According to one embodiment of the present specification, A and B are the same or different and are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 60 carbon atoms.

[0480] In one embodiment of the present specification, A and B are the same as or different from each other, and are each independently an aromatic hydrocarbon ring having 6 to 60 carbon atoms, which is substituted or unsubstituted with one or more substituents selected from deuterium and aryl groups substituted or unsubstituted with deuterium, or an aromatic heterocyclic ring having 2 to 60 carbon atoms, which is substituted or unsubstituted with one or more substituents selected from deuterium and aryl groups substituted or unsubstituted with deuterium.

[0481] According to another embodiment, A and B are the same as or different from each other, and are each independently an aromatic hydrocarbon ring having 6 to 60 carbon atoms, which is substituted or unsubstituted with one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted with deuterium, or an aromatic heterocyclic ring having 2 to 60 carbon atoms, which is substituted or unsubstituted with one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted with deuterium.

[0482] In another embodiment, A and B are the same as or different from each other, and are each independently substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, or substituted or unsubstituted dibenzofuran.

[0483] According to another embodiment, A and B are the same as or different from each other, and are each independently benzene substituted or unsubstituted by one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted by deuterium, naphthalene substituted or unsubstituted by one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted by deuterium, phenanthrene substituted or unsubstituted by one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted by deuterium, triphenylene substituted or unsubstituted by one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted by deuterium, or dibenzofuran substituted or unsubstituted by one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted by deuterium.

[0484] According to one embodiment of the present specification, L21 to L24 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms. L21 to L24 may be substituted with deuterium.

[0485] In another embodiment, L21 to L24 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

[0486] According to another embodiment, the above L21 to L24 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted phenanthrenylene, or a substituted or unsubstituted triphenylene.

[0487] In another embodiment, L21 to L24 are the same as or different from each other, and are each independently a direct bond, a phenylene group substituted or unsubstituted by deuterium, a biphenylene group substituted or unsubstituted by deuterium, a naphthyl group substituted or unsubstituted by deuterium, a phenanthrenyl group substituted or unsubstituted by deuterium, or a triphenylene group substituted or unsubstituted by deuterium.

[0488] According to one embodiment of the present specification, A1 to A4 and B1 to B4 are the same as or different from each other, and are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 60 carbon atoms.

[0489] In one embodiment of the present specification, the above-mentioned A1 to A4 and B1 to B4 are the same as or different from each other, and are each independently an aromatic hydrocarbon ring having 6 to 60 carbon atoms, which is substituted or unsubstituted with one or more substituents selected from deuterium and aryl groups substituted or unsubstituted with deuterium, or an aromatic heterocyclic ring having 2 to 60 carbon atoms, which is substituted or unsubstituted with one or more substituents selected from deuterium and aryl groups substituted or unsubstituted with deuterium.

[0490] According to another embodiment, A1 to A4 and B1 to B4 are the same as or different from each other, and are each independently an aromatic hydrocarbon ring having 6 to 60 carbon atoms, which is unsubstituted or substituted by one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted by deuterium, or an aromatic heterocyclic ring having 2 to 60 carbon atoms, which is unsubstituted or substituted by one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted by deuterium.

[0491] In another embodiment, the above A1 to A4 and B1 to B4 are the same as or different from each other, and are each independently substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, or substituted or unsubstituted dibenzofuran.

[0492] According to another embodiment, A1 to A4 and B1 to B4 are the same as or different from each other, and are each independently benzene substituted or unsubstituted by one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted by deuterium, naphthalene substituted or unsubstituted by one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted by deuterium, phenanthrene substituted or unsubstituted by one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted by deuterium, triphenylene substituted or unsubstituted by one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted by deuterium, or dibenzofuran substituted or unsubstituted by one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted by deuterium.

[0493] According to one embodiment of the present specification, Y1' to Y10' are the same as or different from each other, and are independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms. Y1' to Y10' may be substituted with deuterium.

[0494] According to another embodiment, the above-mentioned Y1' to Y10' are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, or substituted or unsubstituted triphenylene, and the above-mentioned substituents may be further substituted by deuterium, phenyl substituted or unsubstituted by deuterium, biphenyl substituted or unsubstituted by deuterium, terphenyl substituted or unsubstituted by deuterium, naphthyl substituted or unsubstituted by deuterium, phenanthryl substituted or unsubstituted by deuterium, or triphenylene substituted or unsubstituted by deuterium.

[0495] In one embodiment of the present specification, the compound of the above chemical formula 2 can be selected from the structural formulas exemplified by the above chemical formula 1. In the structural formula exemplified by the above chemical formula 1, the structural formula selected as the compound of the above chemical formula 2 is different from the compound selected as the compound of the above chemical formula 1. Specifically, the compound of the above chemical formula 2 can be selected from the structural formula exemplified by the above chemical formula 1, which contains one or more structures of the above chemical formula 2-1. At this time, the binding position of deuterium is not limited. When the compound of the above chemical formula 2 does not contain deuterium, it can be a structure in which deuterium (-D) is excluded from the structural formula, but it is not limited thereto.

[0496] According to one embodiment of the present specification, the compound of the above Chemical Formula 1 is a compound not containing a heterocyclic group. In this case, it includes any one of the above-mentioned compounds excluding the compound containing a heterocyclic group.

[0497] According to an organic light-emitting device according to one embodiment of the present specification, the sublimation temperature (T sub1 ) and the sublimation temperature (T sub2 ) satisfies the following formula (1):

[0498] | T sub1 -T sub2 | ≤ 20℃ - Formula (1)

[0499] When the above-mentioned constitution is satisfied, the low voltage and high efficiency provided by the compound represented by the above-mentioned chemical formula 1 are reproduced, and at the same time, the electron injection into the triplet energy level of the dopant provided by the compound represented by the above-mentioned chemical formula 2 becomes easy, thereby improving the formation ratio of excitons, thus having the advantage of improving the luminous efficiency.

[0500] According to an organic light-emitting device according to one embodiment of the present specification, the light-emitting layer includes a first light-emitting layer and a second light-emitting layer.

[0501] The first light-emitting layer includes the compound represented by the above chemical formula 3 as a first host material,

[0502] The second light emitting layer includes, as a second host material, the compounds represented by Chemical Formulae 1 and 2. When such a configuration is satisfied, the efficiency of the organic light emitting device can be further improved.

[0503] According to the organic light-emitting device of one embodiment of the present specification, the second light-emitting layer is provided between the first light-emitting layer and the cathode.

[0504] According to the organic light emitting device of one embodiment of the present specification, the first light emitting layer and the second light emitting layer are provided in a directly contacting manner. When such a structure is satisfied, the efficiency of the organic light emitting device can be further improved.

[0505] According to the organic light-emitting device of one embodiment of the present specification, the first light-emitting layer includes a combination of two or more compounds represented by the chemical formula 3 as the first host material.

[0506] In one embodiment of the present specification, the host of the second light-emitting layer may further include an anthracene compound different from the compounds of Chemical Formulas 1 and 2.

[0507] In one embodiment of the present specification, at least one of the mixed hosts of the second light-emitting layer may contain deuterium. Specifically, each of the mixed hosts of the second light-emitting layer may contain at least one deuterium.

[0508] In one embodiment of the present specification, the difference in dipole moment (|DM|) of the host of the mixed host may be greater than 0.2. In other words, the difference in dipole moment (|DM|) between the compound of the above Chemical Formula 1 and the above anthracene compound may satisfy Mathematical Formula 2 (|DM|>0.2).

[0509] In one embodiment of the present specification, the anthracene compound may be a compound of the following Chemical Formula 4.

[0510] [Chemical formula 4]

[0511]

[0512] In the above chemical formula 4,

[0513] R201 to R208 are the same as or different from each other, and are each independently hydrogen, deuterium, hydroxyl, cyano, halogen, nitro, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic,

[0514] L201 and L202 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0515] Ar201 and Ar202 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0516] In one embodiment of the present specification, the compound of the above Chemical Formula 4 is a compound not selected as any of the compounds of the above Chemical Formulas 1 and 2 among the compounds exemplified by the compound of the above Chemical Formula 1.

[0517] According to the organic light-emitting device of one embodiment of the present specification, the light-emitting layer further includes a dopant substance.

[0518] As described above, the light-emitting layer may include a single layer or two or more light-emitting layers. When the light-emitting layer is a single layer, the compound represented by Chemical Formula 3 and the compound represented by Chemical Formula 1 may further include a single dopant substance or a combination of multiple dopant substances. In addition, when the light-emitting layer is two layers, including a first light-emitting layer including the compound represented by Chemical Formula 3 and a second light-emitting layer including the compound represented by Chemical Formula 1, each light-emitting layer may include the same type of dopant substance, or may include different types of dopant substances. Preferably, the light-emitting layers of more than two layers include the same type of dopant substance.

[0519] According to the organic light-emitting device of one embodiment of the present specification, the dopant substance is a fluorescent dopant.

[0520] According to the organic light-emitting device of one embodiment of the present specification, the fluorescent dopant is a blue fluorescent dopant.

[0521] According to an organic light-emitting device of one embodiment of the present specification, the blue fluorescent dopant is a pyrene based compound or a non-pyrene based compound.

[0522] According to an organic light-emitting device of one embodiment of the present specification, the non-pyrene-based compound is an arylamine-based compound or a boron-based compound.

[0523] Compared with the above-mentioned pyrene compounds, when non-pyrene compounds are used as fluorescent dopants, they can improve efficiency and increase life due to the narrow half-width characteristics.

[0524] The above-mentioned pyrene-based compound can be a pyrene-based compound substituted with a diarylamine, such as BD02 (N1,N1,N6,N6-tetraphenylpyrene-1,6-diamine) having a smaller band gap than the host substance.

[0525] The above-mentioned non-pyrene compounds are compounds that are not pyrene or pyrene derivatives, and can include metal complexes (iridium complexes, platinum complexes, etc.), boron compounds (DABNA-1, etc.), aromatic amine compounds (coumarin 6, etc.), etc., but are not limited to these.

[0526] In one embodiment of the present specification, the pyrene-based compound is represented by the following chemical formula Z1, and the non-pyrene-based compound is represented by the following chemical formulas Z2 (arylamine-based compound) and Z3 (boron-based compound).

[0527] [Chemical formula Z1]

[0528]

[0529] [Chemical formula Z2]

[0530]

[0531] [Chemical formula Z3]

[0532]

[0533] In the above chemical formulae Z1 to Z3,

[0534] X3 and X4 are each hydrogen or deuterium, or are directly bonded to each other to form a ring,

[0535] R41 and R42 are the same or different from each other, and are each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group,

[0536] Ar31 to Ar34, Ar41 to Ar44, Ar51 and Ar52 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0537] Cy1 to Cy3 are the same as or different from each other, and are each independently a monocyclic to polycyclic aromatic hydrocarbon ring, or a monocyclic to polycyclic aromatic heterocyclic ring,

[0538] R31, R32, R43 to R46 and R51 to R53 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are combined with adjacent substituents to form a substituted or unsubstituted ring,

[0539] R41, R42 and R51 to R53 are each an integer of 0 to 4, and when R41, R42 and R51 to R53 are 2 or more, the substituents in the brackets are the same as or different from each other.

[0540] In one embodiment of the present specification, Ar31 to Ar34, Ar41 to Ar44, Ar51 and Ar52 are the same as or different from each other, and are each independently a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group.

[0541] In one embodiment of the present specification, Ar31 to Ar34, Ar41 to Ar44, Ar51 and Ar52 are the same as or different from each other, and are each independently a C6-C20 aryl group substituted or unsubstituted by one or more substituents selected from the group consisting of deuterium, a halogen group and a C1-C6 alkyl group, or a substituent formed by connecting two or more groups selected from the above group; or a C2-C20 heterocyclic group substituted or unsubstituted by one or more substituents selected from the group consisting of deuterium, a halogen group and a C1-C6 alkyl group, or a substituent formed by connecting two or more groups selected from the above group.

[0542] In one embodiment of the present specification, Cy1 to Cy3 are the same as or different from each other, and are each independently a monocyclic to tricyclic aromatic hydrocarbon ring; or a monocyclic to tricyclic aromatic heterocyclic ring containing N, O or S.

[0543] In one embodiment of the present specification, Cy1 to Cy3 are the same as or different from each other, and are each independently a benzene ring, a naphthalene ring, a furan ring, a thiophene ring, a benzofuran ring, a benzothiophene ring, a dibenzofuran ring or a dibenzothiophene ring, and may be further condensed with a C5-C10 aliphatic hydrocarbon ring.

[0544] In one embodiment of the present specification, R31, R32, R43 to R46, and R51 to R53 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C1-C30 alkylsilyl group, a substituted or unsubstituted C6-C90 arylsilyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C1-C30 alkylamino group, a substituted or unsubstituted C6-C60 arylamino group, a substituted or unsubstituted C2-C60 heteroarylamino group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, or are combined with adjacent substituents to form a C3-C30 hydrocarbon ring, or a substituted or unsubstituted C2-C30 heterocyclic ring.

[0545] In one embodiment of the present specification, the chemical formula Z3 as the boron-based compound is any one of the following chemical formulas Z3-1 to Z3-3.

[0546] [Chemical formula Z3-1]

[0547]

[0548] [Chemical formula Z3-2]

[0549]

[0550] [Chemical formula Z3-3]

[0551]

[0552] In the above chemical formulas Z3-1 to Z3-3,

[0553] R51 to R53, r52, Ar51 and Ar52 are the same as defined in the chemical formula Z3,

[0554] X5 is O or S,

[0555] r521 is an integer from 0 to 2. When r521 is 2, R52 are the same as or different from each other.

[0556] In one embodiment of the present specification, Ar51 and Ar52 are the same as or different from each other, and are each independently a C6-C30 aryl group fused with or not fused with an aliphatic hydrocarbon ring, or a C2-C30 heterocyclic group, and the above aryl group or heterocyclic group is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, and a C1-C10 alkyl group, or a substituent formed by connecting two or more groups selected from the above group.

[0557] In one embodiment of the present specification, the aryl group or heterocyclic group of Ar51 includes a substituent other than hydrogen at an ortho-oriented position relative to the nitrogen to which it is connected.

[0558] In one embodiment of the present specification, the aryl group or heterocyclic group of Ar52 includes a substituent other than hydrogen at an ortho-oriented position relative to the nitrogen to which it is connected.

[0559] In one embodiment of the present specification, R51 to R53 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C1-C30 alkylsilyl group, a substituted or unsubstituted C6-C90 arylsilyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C1-C30 alkylamino group, a substituted or unsubstituted C6-C60 arylamino group, a substituted or unsubstituted C2-C60 heteroarylamino group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, or are combined with adjacent substituents to form a C3-C30 aliphatic hydrocarbon ring, or a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring.

[0560] In one embodiment of the present specification, R51 to R53 are the same as or different from each other, and are independently hydrogen, deuterium, methyl, tert-butyl, phenyl, phenyl substituted with tert-butyl, diphenylamino or bis((tert-butyl)phenyl)amino.

[0561] In one embodiment of the present specification, two adjacent R51, two adjacent R52, or two adjacent R53 are combined to form a substituted or unsubstituted ring. In this case, the ring is a C3-C30 aliphatic hydrocarbon ring, or a C6-C30 aromatic hydrocarbon ring, specifically a cyclopentene ring, a cyclohexene ring, a tetralin ring, a benzene ring, or a naphthalene ring.

[0562] In one embodiment of the present specification, the chemical formula Z1 or Z2 may be selected from the following structures, but is not limited thereto.

[0563]

[0564] In one embodiment of the present specification, the chemical formula Z3 is represented by any one of the following compounds.

[0565]

[0566]

[0567]

[0568]

[0569]

[0570]

[0571]

[0572]

[0573]

[0574]

[0575]

[0576]

[0577]

[0578]

[0579]

[0580]

[0581]

[0582]

[0583]

[0584]

[0585]

[0586]

[0587]

[0588]

[0589]

[0590]

[0591]

[0592]

[0593]

[0594]

[0595]

[0596]

[0597]

[0598]

[0599]

[0600]

[0601]

[0602]

[0603]

[0604]

[0605]

[0606]

[0607]

[0608]

[0609]

[0610]

[0611]

[0612]

[0613]

[0614]

[0615]

[0616]

[0617]

[0618]

[0619]

[0620]

[0621] In one embodiment of the present specification, in the light-emitting layer, based on 100 parts by weight of the host material, the dopant material may be contained in an amount of 0.01 to 50 parts by weight, and may be contained in an amount of 0.1 to 30 parts by weight, 1 to 10 parts by weight, or 2 parts by weight. Within the above range, energy transfer from the host to the dopant occurs effectively. At this time, 100 parts by weight of the host material is based on the total weight of the compound of the above Chemical Formula 3 and / or the compound of the Chemical Formula 1.

[0622] According to an organic light-emitting device of one embodiment of the present specification, when one of R1 to R10 is connected to L1, and at least one of the others is a substituted or unsubstituted aromatic group, it is selected from a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a spirobifluorenyl group, a phenanthryl group or a triphenylene group.

[0623] When the above configuration is met, the efficiency of the organic light-emitting device can be further improved.

[0624] According to the organic light-emitting device of one embodiment of the present specification, a deuterium substitution rate of at least one of the compound represented by the above Chemical Formula 3 and the compound represented by the above Chemical Formula 1 is each independently 1% or more and 100% or less.

[0625] In one embodiment of the present specification, the deuterium substitution rate of at least one of the compound represented by the above Chemical Formula 3 and the compound represented by the above Chemical Formula 1 may be independently 1% or more, 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more.

[0626] In one embodiment of the present specification, the deuterium substitution rate of at least one of the compound represented by the above Chemical Formula 3 and the compound represented by the above Chemical Formula 1 may be independently 100% or less, 99% or less, 98% or less, 97% or less, 96% or less, or 95% or less.

[0627] According to the organic light-emitting device of one embodiment of the present specification, a deuterium substitution rate of at least one of the compound represented by the above Chemical Formula 3 and the compound represented by the above Chemical Formula 1 is each independently 40% or more and 99% or less.

[0628] According to one embodiment of the present specification, the deuterium substitution rate of both the compound represented by the above Chemical Formula 3 and the compound represented by the above Chemical Formula 1 is 100%.

[0629] The above-mentioned deuterium substitution rate can be calculated by the above-mentioned method. According to another example, at least one deuterium is directly substituted on the anthracene of the above-mentioned chemical formula 1. The light-emitting layer of the organic light-emitting device is a region of light emission, and is a region where the energy-induced molecular loss is large. The carbon-deuterium bond is stronger than the carbon-hydrogen bond, and deuterium has a higher mass value than hydrogen, which reduces the zero point energy with carbon, so that the bond energy is high. Therefore, the carbon-hydrogen bond contained in the molecule of the compound of the above-mentioned chemical formula 1 is replaced by a carbon-deuterium bond to increase the bond energy of the molecule, so that a device with excellent life can be obtained.

[0630]

[0631] An organic light emitting device including the compound of Chemical Formula 3 and / or Chemical Formula 1 having a deuterium substitution rate according to an embodiment of the present specification has improved heat resistance, having an effect of improving lifespan.

[0632] According to the organic light emitting device of one embodiment of the present specification, the number of nitrogen contained in the compound represented by the above Chemical Formula 3 is 1 at most.

[0633] In the organic light-emitting device according to one embodiment of the present specification, the triplet energy level (T h1 ) is above 2.30 eV.

[0634] In one embodiment of the present specification, the triplet energy level (T h1 ) can be 2.30 eV or more, 2.40 eV or more, or 2.50 eV or more.

[0635] In the organic light-emitting device according to one embodiment of the present specification, the triplet energy level (T h1 ) is greater than the triplet energy level (T h2 ) is high. That is, T h1 >T h2 (Mathematical formula 3).

[0636] In the organic light-emitting device according to one embodiment of the present specification, the triplet energy level (T h1 ) can satisfy 2.30eV≤T h1 ≤2.90eV.

[0637] In one embodiment of the present specification, the triplet energy level (T h1 ) can be greater than 2.30 eV, greater than 2.40 eV, or greater than 2.50 eV.

[0638] In one embodiment of the present specification, the triplet energy level (T h1 ) can be less than 2.90 eV, less than 2.80 eV, or less than 2.70 eV.

[0639] In the organic light-emitting device according to one embodiment of the present specification, the triplet energy level (T h2 ) can satisfy 1.40eV≤T h2 ≤1.80eV.

[0640] In one embodiment of the present specification, the triplet energy level (T h2 ) may be greater than 1.40 eV, greater than 1.45 eV, greater than 1.50 eV, or greater than 1.55 eV.

[0641] In one embodiment of the present specification, the triplet energy level (T h2 ) can be less than 1.80 eV, less than 1.75 eV, less than 1.70 eV, or less than 1.65 eV.

[0642] In the organic light-emitting device according to one embodiment of the present specification, the triplet energy level (T h1 ) and the triplet energy level (T h2 ) can satisfy the following formula (2).

[0643] Δ(T h1 -T h2 )≤ 1.50eV - Formula (2)

[0644] In one embodiment of the present specification, the triplet energy level (T h1 ) and the triplet energy level (T h2 ) difference (Δ(T h1 -T h2 )) can be 1.50 eV or less, 1.45 eV or less, 1.40 eV or less, 1.35 eV or less, or 1.30 eV or less.

[0645] In the organic light-emitting device according to one embodiment of the present specification, the triplet energy level (T h1 ), the triplet energy level (T h2 ) and the triplet energy level (T BD ) can satisfy at least one of the following equations (3) and (4).

[0646] Δ(T BD -T h1 )≤ 0.40eV - Formula (3)

[0647] Δ(T BD -T h2 )≥ 0.40eV - Formula (4)

[0648] In one embodiment of the present specification, the triplet energy level (T h1 ) and the triplet energy level (T BD ) difference (Δ(T BD -T h1 )) can be below 0.40 eV, below 0.35 eV, or below 0.30 eV.

[0649] In one embodiment of the present specification, the triplet energy level (T h2 ) and the triplet energy level (T BD ) difference (Δ(T BD -T h2 )) can be greater than 0.40 eV, greater than 0.45 eV, or greater than 0.50 eV.

[0650] According to the organic light-emitting device of one embodiment of the present specification, the triplet energy level (T L1 ) and the triplet energy level (T h1 ) can satisfy the following formula (5).

[0651] Δ(T L1 -T h1 )≤ 1.50eV - Formula (5)

[0652] In one embodiment of the present specification, the triplet energy level (T L1 ) and the triplet energy level (T h1 ) difference (Δ(T L1 -T h1 )) can be below 1.50 eV, below 1.45 eV, or below 1.40 eV.

[0653] When any one of the above-mentioned structures is satisfied, electron injection into the triplet level of the dopant is facilitated, the formation ratio of excitons is increased, and efficiency is improved.

[0654] In this specification, the triplet energy level (E T1) can be measured using a spectrometer capable of measuring fluorescence and phosphorescence. As for the measurement conditions, a concentration of 10 -6 M solution, irradiating the solution with a light source in the absorption wavelength range of the substance, excluding singlet emission from the emission spectrum, and analyzing and confirming the spectrum of triplet emission. When electrons are excited by the light source, the time they stay in the triplet state is much longer than the time they stay in the singlet state, so the two components can be separated at extremely low temperatures.

[0655] In this specification, triplet energy (E T1 ) can be calculated by the following method. After cooling the sample to 77K, irradiate the sample for phosphorescence measurement with excitation light (360nm), measure the phosphorescence intensity using a streak camera, draw a tangent to the rising point of the phosphorescence spectrum, and find the wavelength value λedge [nm] of the intersection of the tangent and the x-axis. Substitute this wavelength value into the following formula (6), and the energy value E can be calculated. T1 At this time, the emission spectrum was measured using a nitrogen molecule laser (manufactured by Lasertechnik Berlin, MNL200) and a streak camera (manufactured by Hamamatsu Photonics, C4334).

[0656] E T1 [eV] = 1239.85 / λedge – Formula (6)

[0657] In one embodiment of the present specification, the triplet energy level (E T1 ) can be calculated using Gaussian 03, a quantum chemical calculation program manufactured by Gaussian Corporation of the United States. Specifically, for a structure optimized using density functional theory (DFT) using B3LYP (Becke, three-parameter, Lee-Yang-Parr) as a functional and 6-31G* as a basis function, the calculated value of the triplet energy can be obtained by time-dependent density functional theory (TD-DFT).

[0658] According to the organic light-emitting device of one embodiment of the present specification, in the light-emitting layer, the maximum emission wavelengths (λmax) of the compound represented by Chemical Formula 3 and the compound represented by Chemical Formula 1 may each be within a range of 400 nm to 500 nm.

[0659] Preferably, the maximum emission wavelength (λmax) of the compound represented by the above Chemical Formula 3 and the compound represented by the above Chemical Formula 1 may each be within the range of 400 nm to 485 nm, or 400 nm to 470 nm. When such a configuration is satisfied, the light-emitting layer may emit blue light.

[0660] In one embodiment of the present specification, the organic light-emitting device may be a (normal type) organic light-emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

[0661] In one embodiment of the present specification, the organic light emitting device may be an organic light emitting device of a reverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0662] In the organic light-emitting device of the present invention, the organic layer may include an electron blocking layer, and the electron blocking layer may be made of materials known in the technical field.

[0663] For example, the organic light emitting device may have a stacked structure as described below, but is not limited thereto.

[0664] (1) Anode / hole transport layer / light-emitting layer / cathode

[0665] (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode

[0666] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0667] (4) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0668] (5) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0669] (6) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0670] (7) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0671] (8) Anode / hole injection layer / hole transport layer / hole regulation layer / light-emitting layer / electron transport layer / cathode

[0672] (9) Anode / hole injection layer / hole transport layer / hole regulation layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0673] (10) Anode / hole injection layer / hole transport layer / light-emitting layer / electron regulation layer / electron transport layer / electron injection layer / cathode

[0674] (11) Anode / hole injection layer / hole transport layer / hole regulation layer / light-emitting layer / electron regulation layer / electron transport layer / electron injection layer / cathode

[0675] (12) Anode / hole transport layer / first light-emitting layer / second light-emitting layer / cathode

[0676] (13) Anode / hole transport layer / first light-emitting layer / second light-emitting layer / electron transport layer / electron injection layer / cathode

[0677] (14) Anode / hole injection layer / hole transport layer / first light-emitting layer / second light-emitting layer / electron transport layer / cathode

[0678] (15) Anode / hole injection layer / hole transport layer / first light-emitting layer / second light-emitting layer / electron transport layer / electron injection layer / cathode

[0679] (16) Anode / hole injection layer / hole transport layer / hole regulation layer / first light emitting layer / second light emitting layer / electron transport layer / cathode

[0680] (17) Anode / hole injection layer / hole transport layer / hole regulation layer / first light emitting layer / second light emitting layer / electron transport layer / electron injection layer / cathode

[0681] (18) Anode / hole injection layer / hole transport layer / first light-emitting layer / second light-emitting layer / electron regulation layer / electron transport layer / electron injection layer / cathode

[0682] (19) Anode / hole injection layer / hole transport layer / hole regulation layer / first light-emitting layer / second light-emitting layer / electron regulation layer / electron transport layer / electron injection layer / cathode

[0683] The structure of the organic light-emitting device of the present specification may have the following Figures 1 to 4 The structure shown is not limited to this.

[0684] Figure 1 An example of an organic light-emitting device according to an embodiment of the present specification is shown, and a structure of an organic light-emitting device in which a substrate 101, an anode 102, a first light-emitting layer 106-1, a second light-emitting layer 106-2, and a cathode 110 are sequentially stacked is illustrated. In the structure shown above, the compound represented by the above chemical formula 3 may be included in the first light-emitting layer 106-1. Alternatively, the compounds represented by the above chemical formula 1 may each be included in the second light-emitting layer 106-2, or vice versa.

[0685] Figure 2An example of an organic light-emitting device according to an embodiment of the present specification is shown, and a structure of an organic light-emitting device is shown in which a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, a light-emitting layer 106, an electron transport layer 108, an electron injection layer 109, and a cathode 110 are sequentially stacked. In the structure shown above, the compound represented by the above Chemical Formula 3 and the compound represented by Chemical Formula 1 can each be included in a single-layer light-emitting layer 106 or a double-layer light-emitting layer 106.

[0686] Figure 3 An example of an organic light-emitting device according to an embodiment of the present specification is shown, and the structure of the organic light-emitting device is shown, which sequentially stacks a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, a hole regulation layer 105, a light-emitting layer 106, an electron regulation layer 107, an electron transport layer 108, an electron injection layer 109, and a cathode 110. In the structure shown above, the compound represented by the above Chemical Formula 3 and the compound represented by Chemical Formula 1 can each be included in a single-layer light-emitting layer or two or more light-emitting layers.

[0687] Figure 4 An example of an organic light-emitting device according to an embodiment of the present specification is shown, and the structure of the organic light-emitting device is sequentially stacked with a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, a hole adjustment layer 105, a first light-emitting layer 106-1, a second light-emitting layer 106-2, an electron adjustment layer 107, an electron transport layer 108, an electron injection layer 109, and a cathode 110. In the structure shown above, the compound represented by the above chemical formula 3 may be included in the first light-emitting layer 106-1. Alternatively, the compounds represented by the above chemical formula 1 may each be included in the second light-emitting layer 106-2, or vice versa.

[0688] The organic light-emitting device of the present specification can be manufactured using materials and methods known in the technical field, except that the organic layer includes the above-mentioned compound.

[0689] When the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.

[0690] For example, the organic light-emitting device of the present specification can be manufactured by sequentially stacking an anode, an organic layer, and a cathode on a substrate. In this case, the manufacturing method can be as follows: using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation (e-beamevaporation), a metal or a conductive metal oxide or an alloy thereof is evaporated on a substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is evaporated on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially evaporating a cathode substance, an organic layer, and an anode substance on a substrate.

[0691] The organic layer may be a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer, but is not limited thereto and may also be a single layer structure. In addition, the organic layer may be made of various polymer materials and formed into a smaller number of layers by a solvent process other than evaporation, such as spin coating, dip coating, blade coating, screen printing, inkjet printing, or thermal transfer.

[0692] The anode is an electrode for injecting holes. As the anode material, in order to smoothly inject holes into the organic layer, a material with a large work function is preferably used. For example, there are metals such as vanadium, chromium, copper, zinc, gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0693] The cathode is an electrode for injecting electrons. In order to facilitate the injection of electrons into the organic layer, the cathode material is preferably a material with a small work function. For example, there are 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 LiO2 / Al, etc., but are not limited thereto.

[0694] The organic layer includes a light-emitting layer. The light-emitting layer may include a host substance and a dopant substance.

[0695] The host material includes aromatic condensed ring derivatives or heterocyclic compounds, etc. In the present specification, the light emitting layer includes the compound represented by Chemical Formula 3 and the compound represented by Chemical Formula 1 as host materials.

[0696] The above-mentioned dopant substances can be divided into phosphorescent dopants and fluorescent dopants, and the above-mentioned fluorescent dopants can be divided into pyrene compounds or non-pyrene compounds. The above-mentioned pyrene compounds can be pyrene compounds substituted with diarylamines, such as BD02 (N1, N1, N6, N6-tetraphenylpyrene-1, 6-diamine), which have a smaller band gap than the host substance. The above-mentioned non-pyrene compounds, as compounds that are not pyrene or pyrene derivatives, can include metal complexes (iridium complexes, platinum complexes), boron compounds (DABNA-1, etc.), arylamine compounds (coumarin 6, etc.), etc., but are not limited thereto.

[0697] According to one embodiment of the present specification, the non-pyrene compound including the pyrene compound (the above chemical formula Z1), the arylamine compound (the above chemical formula Z2), and the boron compound (the above chemical formula Z3) is the same as described above.

[0698] The above-mentioned organic layer may also include a hole injection layer. The above-mentioned hole injection layer is a layer that receives holes from the electrode. The hole injection material is preferably a material that has the ability to transport holes, has the effect of receiving holes from the anode, and has an excellent hole injection effect for the light-emitting layer or the light-emitting material. In addition, it is preferably a material that has an excellent ability to prevent the excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material. Moreover, it is preferably a material with excellent thin film forming ability. In addition, 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. As specific examples of hole injection materials, there are metal porphyrins, oligothiophenes, and arylamine organics; hexanitrile hexaazatriphenylene organics; quinacridone organics; perylene organics; anthraquinone, polyaniline and polythiophene conductive polymers, etc., but are not limited to this. The thickness of the hole injection layer can be 1 to 150nm. When the thickness of the hole injection layer is 1 nm or more, it has the advantage of preventing the hole injection characteristics from being reduced. When it is 150 nm or less, it has the advantage of preventing the driving voltage from increasing due to the improvement of hole migration when the thickness of the hole injection layer is too thick.

[0699] According to one embodiment of the present specification, the hole injection layer may include a compound represented by the following chemical formula HI-A, but is not limited thereto.

[0700] [Chemical formula HI-A]

[0701]

[0702] In the above chemical formula HI-A,

[0703] At least one of X'1 to X'6 is N, and the others are CH,

[0704] R309 to R314 are the same as or different from each other, and are each independently hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0705] According to one embodiment of the present specification, X'1 to X'6 are N.

[0706] According to one embodiment of the present specification, R309 to R314 are nitrile groups.

[0707] According to one embodiment of the present specification, the chemical formula HI-A can be represented by the following compounds.

[0708]

[0709] According to one embodiment of the present specification, the hole injection layer may include a compound represented by the following chemical formula HI-B, but is not limited thereto.

[0710] [Chemical formula HI-B]

[0711]

[0712] In the above chemical formula HI-B,

[0713] R315 to R317 are the same as or different from each other, and are each independently hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0714] R318 to R332 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and at least three of them are nitrile groups.

[0715] According to one embodiment of the present specification, R315 to R317 are all nitrile groups.

[0716] According to one embodiment of the present specification, one of R318 to R322 is a nitrile group, and the others are fluorine (—F).

[0717] According to one embodiment of the present specification, one of R323 to R327 is a nitrile group, and the others are fluorine (—F).

[0718] According to one embodiment of the present specification, one of R328 to R332 is a nitrile group, and the others are fluorine (—F).

[0719] According to one embodiment of the present specification, the chemical formula HI-B is represented by the following compounds.

[0720]

[0721] The organic layer may further include a hole transport layer. The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. The hole transport layer may be a single layer or a multilayer structure of two or more layers. When the hole transport layer is a multilayer structure of two or more layers, each layer may contain the same or different hole transport substances.

[0722] 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, preferably a material with a large mobility for holes. Specific examples of hole transport materials include arylamine-based organic substances, carbazole-based compounds, conductive polymers, and block copolymers having both conjugated and non-conjugated parts, but are not limited thereto.

[0723] According to one embodiment of the present specification, the hole transport layer may include a compound represented by the following chemical formula HT, but is not limited thereto.

[0724] [Chemical formula HT]

[0725]

[0726] In the above chemical formula HT,

[0727] R333 to R335 are the same as or different from each other, and are each independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic group, and any combination thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0728] r334 is an integer from 1 to 5. When r334 is 2 or more, two or more R334 are the same or different from each other.

[0729] r335 is an integer of 1 to 5. When r335 is 2 or more, two or more R335s may be the same as or different from each other.

[0730] According to one embodiment of the present specification, R333 is any one selected from a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, and a combination thereof.

[0731] According to one embodiment of the present specification, the R333 is any one selected from a dimethylfluorenyl group, a carbazolyl group, a phenyl group, a biphenyl group, and a combination thereof.

[0732] According to one embodiment of the present specification, R334 and R335 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0733] According to one embodiment of the present specification, both R334 and R335 are phenyl.

[0734] According to one embodiment of the present specification, any one of R334 and R335 is a phenyl group, and the other is a carbazolyl group substituted with a phenyl group.

[0735] According to one embodiment of the present specification, the chemical formula HT may be represented by any one of the following compounds.

[0736]

[0737] The organic layer may further include a hole regulating layer. The hole regulating layer is a layer responsible for hole transport and carrier regulation. The hole regulating layer may be a single layer or a multilayer structure of two or more layers. When the hole regulating layer is a multilayer structure of two or more layers, each layer may contain the same or different hole regulating substances.

[0738] The hole regulating substance is preferably a substance that can balance the appropriate influx of holes into the light-emitting layer through efficient migration of holes.

[0739] According to one embodiment of the present specification, the hole regulating layer may include a compound represented by the following chemical formula EB, but is not limited thereto.

[0740] [Chemical formula EB]

[0741]

[0742] In the above chemical formula EB,

[0743] R336 to R338 are the same as or different from each other, and are each independently selected from any one of hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic group, and combinations thereof,

[0744] r336 is an integer from 1 to 5. When the above r336 is 2 or more, the two or more R336 are the same or different from each other.

[0745] r337 is an integer from 1 to 5. When r337 is 2 or more, the two or more R337 are the same or different from each other.

[0746] r338 is an integer of 1 to 5. When r338 is 2 or more, two or more R338s may be the same as or different from each other.

[0747] According to one embodiment of the present specification, R336 is any one selected from a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, and a combination thereof.

[0748] According to one embodiment of the present specification, the above-mentioned R336 is any one selected from a phenyl group, a carbazolyl group, and a combination thereof.

[0749] According to one embodiment of the present specification, R337 and R338 are the same as or different from each other, and are each independently an unsubstituted aryl group.

[0750] According to one embodiment of the present specification, both R337 and R338 are naphthyl or phenanthryl.

[0751] According to one embodiment of the present specification, the chemical formula EB may be any one of the following compounds.

[0752]

[0753] The organic layer may further include an electron regulating layer. The electron regulating layer is a layer that regulates electron migration in order to smoothly inject electrons so as to reduce the potential barrier with the light-emitting layer. The electron regulating layer may be a single layer or a multilayer structure of two or more layers. When the electron regulating layer is a multilayer structure of two or more layers, each layer may contain the same or different electron regulating substances.

[0754] The electron regulating substance is preferably a substance that can balance the appropriate electron inflow into the light-emitting layer by efficient electron transfer.

[0755] According to one embodiment of the present specification, the electron adjustment layer may include a compound represented by the following chemical formula HB, but is not limited thereto.

[0756] [Chemical formula HB]

[0757]

[0758] In the above chemical formula HB,

[0759] At least one of X'7 to X'9 is N, and the others are CH,

[0760] R339 to R341 are the same as or different from each other, and are each independently any one selected from hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and combinations thereof.

[0761] According to one embodiment of the present specification, X'7 to X'9 are N.

[0762] According to one embodiment of the present specification, R339 and R340 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0763] According to one embodiment of the present specification, both R339 and R340 are phenyl.

[0764] According to one embodiment of the present specification, R341 is any one selected from a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, and a combination thereof.

[0765] According to one embodiment of the present specification, the chemical formula HB may be any one of the following compounds.

[0766]

[0767] The organic layer may further include an electron transport layer. The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer. The electron transport layer may be a single layer or a multilayer structure of two or more layers. When the electron transport layer is a multilayer structure of two or more layers, each layer may contain the same or different electron transport substances.

[0768] The electron transport material is a material that can well receive electrons from the cathode and transfer them to the light-emitting layer, preferably a material with a large mobility for electrons. Specific examples of the electron transport material include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited thereto.

[0769] The electron transport layer can be used together with any desired cathode material as used in the prior art. 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 electron transport characteristics from being reduced. When it is less than 50 nm, it has the advantage of preventing the driving voltage from increasing in order to improve the migration of electrons when the thickness of the electron transport layer is too thick.

[0770] According to one embodiment of the present specification, the electron transport layer may include a compound represented by the following chemical formula ET, but is not limited thereto.

[0771] [Chemical formula ET]

[0772]

[0773] In the above chemical formula ET,

[0774] At least one of X'10 to X'12 is N, and the rest are CH,

[0775] R342 to R344 are the same as or different from each other, and are each independently any one selected from hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and combinations thereof.

[0776] According to one embodiment of the present specification, X'10 to X'12 are N.

[0777] According to one embodiment of the present specification, R342 and R344 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0778] According to one embodiment of the present specification, R342 and R343 are the same as or different from each other, and are each independently a phenyl group, or a phenyl group substituted with a nitrile group.

[0779] According to one embodiment of the present specification, R344 is any one selected from a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, and a combination thereof.

[0780] According to one embodiment of the present specification, the chemical formula ET may be the following compound.

[0781]

[0782] According to one embodiment of the present specification, the electron transport layer includes the compound of the chemical formula ET and a metal complex.

[0783] According to one embodiment of the present specification, the electron transport layer includes the compound of the chemical formula ET and lithium quinolate (Liq).

[0784] According to one embodiment of the present specification, the electron transport layer may include the compound of the chemical formula ET and the metal complex in a weight ratio of 1:10 to 10:1.

[0785] According to one embodiment of the present specification, the electron transport layer may include the compound of the chemical formula ET1 or ET2 and lithium quinoline at a weight ratio of 5:5 to 7:3. Specifically, the compound of the chemical formula ET1 or ET2 and lithium quinoline are included at a weight ratio of 7:3.

[0786] The organic layer may further include an electron injection layer. The electron injection layer is a layer that receives electrons from an electrode.

[0787] The electron injection material preferably has excellent electron transport capability, has the effect of receiving electrons from the second electrode, and has excellent electron injection effect on the light-emitting layer or the light-emitting material. In addition, it is preferably a material that prevents the excitons generated in the light-emitting layer from migrating to the hole injection layer and has excellent thin film forming ability. Specific examples of the electron injection material include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.

[0788] Examples of the metal coordination compounds include, but are not limited to, 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo[h]quinoline) beryllium, bis(10-hydroxybenzo[h]quinoline) zinc, bis(2-methyl-8-quinoline) gallium chloride, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, and bis(2-methyl-8-quinoline)(2-naphthol) gallium.

[0789] The above-mentioned covering layer is formed to prevent a large amount of light from being lost through total reflection of light in the organic light-emitting device. The covering layer has the property of fully protecting the lower cathode and the light-emitting layer from external moisture penetration or contamination. It has a high refractive index and can prevent light loss due to total reflection, and existing materials can be used without restrictions.

[0790] According to one embodiment of the present specification, the cover layer includes a compound of the following chemical formula CP-1, but is not limited thereto.

[0791] [Chemical formula CP-1]

[0792]

[0793] In the above chemical formula CP-1,

[0794] L501 and L502 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0795] R501 and Ar501 to Ar504 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group, or adjacent groups are combined to form a substituted or unsubstituted ring.

[0796] According to one embodiment of the present specification, L501 and L502 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0797] According to one embodiment of the present specification, L501 and L502 are phenylene groups.

[0798] According to one embodiment of the present specification, the above R501 and Ar501 to Ar504 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, or are combined with adjacent groups to form a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0799] According to one embodiment of the present specification, R501 and Ar501 to Ar504 are phenyl groups, or are combined with adjacent groups to form carbazole substituted or unsubstituted with a phenyl group.

[0800] According to one embodiment of the present specification, Ar501 and L501 are bonded to form a carbazole substituted with a phenyl group.

[0801] According to one embodiment of the present specification, Ar503 and L503 are bonded to form a carbazole substituted with a phenyl group.

[0802] According to one embodiment of the present specification, the chemical formula CP-1 is the following compound.

[0803]

[0804] The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a bi-directional emission type according to the materials used.

[0805] The organic light-emitting device according to the present specification can be included in various electronic devices for use. For example, the electronic device can be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.

[0806] Below, in order to specifically describe the application, embodiments will be cited and described in detail. However, various forms can be deformed according to the embodiments of the application, and it is not interpreted that the scope of the application is limited to the embodiments described in detail below. The embodiments of the application are provided to more completely describe the application to those skilled in the art.

[0807] [Production Example 1] Synthesis of Chemical Formula 1

[0808]

[0809] Here, Ra has the same definition as R11 to R20, L4 has the same definition as L2, Ar3 has the same definition as Ar2, u is an integer greater than 1, r is 10-u, l4 has the same definition as p, Dz refers to the number of deuterium substitutions, and z is greater than 1 and less than the maximum number of hydrogen atoms that can be substituted with deuterium.

[0810] The reactant (1 equivalent) and trifluoromethanesulfonic acid (catalyst (cat.)) are added to C6D6 (10 to 50 times the mass ratio relative to the reactant), and stirred at 70°C for 10 to 100 minutes. After the reaction is completed, D2O (excess) is added, and after stirring for 30 minutes, trimethylamine (excess) is added dropwise. The reaction solution is transferred to a separatory funnel and extracted with water and chloroform. After the extract is dried with MgSO4, it is heated with toluene for recrystallization to obtain the product shown in Table 1 below.

[0811] [Table 1]

[0812]

[0813]

[0814]

[0815]

[0816] The degree of deuterium substitution of each product varies depending on the reaction time. + ) value determines the substitution rate.

[0817] Compounds A to W as the above-mentioned reactants were synthesized with reference to existing documents such as JP4070676B2, KR1477844B1, US6465115B2, JP3148176B2, JP4025136B2, JP4188082B2, JP5015459B2, KR1979037B1, KR1550351B1, KR1503766B1, KR0826364B1, KR0749631B1 and KR1115255B1. In addition, compounds 1-A to 1-W as deuterium-substituted products were synthesized with reference to the existing document KR1538534B1.

[0818] [Production Example 2] Synthesis of Chemical Formula 2

[0819]

[0820] Here, Ra has the same definition as Y1 to Y10, L4 has the same definition as L3 in Chemical Formula 2-1, A and B have the same definition as in Chemical Formula 2-1, u is an integer greater than 1, r is 10-u, l4 has the same definition as q, Dz refers to the number of deuterium substitutions, and z is greater than 1 and less than the maximum number of hydrogen atoms that can be substituted with deuterium.

[0821] The reactant (1 equivalent) and trifluoromethanesulfonic acid (catalyst) are added to C6D6 (10 to 50 times the mass ratio relative to the reactant) and stirred at 70°C for 10 to 100 minutes. After the reaction is completed, D2O (excess) is added, stirred for 30 minutes, and trimethylamine (excess) is added dropwise. The reaction solution is transferred to a separatory funnel and extracted with water and chloroform. After the extract is dried with MgSO4, it is heated with toluene for recrystallization to obtain the products shown in [Table 2] and [Table 3] below.

[0822] [Table 2]

[0823]

[0824]

[0825]

[0826]

[0827]

[0828] The degree of deuterium substitution of each product differed depending on the reaction time, and the substitution rate was determined from the maximum m / z (M+) value.

[0829] Compounds 1 to 27 as the above-mentioned reactants were synthesized with reference to the company's existing documents such as KR1964435B1, KR1899728B1, KR1975945B1, KR2018-0098122A, KR2018-0102937A and KR2018-0103352A. In addition, compounds 2-1 to 2-27 as deuterium-substituted products were synthesized with reference to the existing document KR1538534B1.

[0830] [Table 3]

[0831]

[0832]

[0833]

[0834]

[0835] The degree of deuterium substitution of each product differed depending on the reaction time, and the substitution rate was determined from the maximum m / z (M+) value.

[0836] Compounds 28 to 47 as the above-mentioned reactants were synthesized with reference to the existing documents of our company such as KR1994238B1, KR1670193B1, KR1754445B1 and KR1368164B1. In addition, compounds 2-28 to 2-47 as deuterium-substituted products were synthesized with reference to the existing document KR1538534B1.

[0837] [Experimental Example 1] Dipole moment (DM) and sublimation temperature of manufacturing examples 1 to 2

[0838] [Table 4]

[0839]

[0840]

[0841] At this time, the unit of dipole moment (DM) is debye, and the unit of sublimation temperature is °C.

[0842] The physical properties of the compounds synthesized in the above-mentioned preparation examples are shown in the above-mentioned [Table 4]. Regarding the physical properties of compounds A to W, although compounds 1-A to 1-W have chemical structural differences in carbon-hydrogen skeletons and carbon-deuterium skeletons, the basic chemical skeletons are the same, and the differences in dipole moments are almost the same, so the relevant numerical values ​​are replaced by compounds A to W. In addition, the relevant numerical values ​​of compounds 1 to 47 are also replaced by compounds 1 to 47 for the same reason.

[0843] Among the compounds synthesized in the above-mentioned manufacturing examples 1 and 2, the compounds equivalent to chemical formula 1 and the compounds equivalent to chemical formula 2 have a difference in dipole moment in the chemical structure. Compounds A to W equivalent to chemical formula 1 have a skeleton based only on carbon and hydrogen by having an aryl-based substituent, and form limited electron-rich and less partitions within the chemical structure, thereby showing a dipole moment (DM) of no more than 0.3 Debye. On the contrary, it can be confirmed that compounds 1 to 47 equivalent to chemical formula 2 have a potential that can deepen the electronic partition in the chemical structure having a carbon-hydrogen skeleton by replacing furan containing an aryl or heteroaryl group with relatively abundant electrons on the anthracene skeleton, and have a high dipole moment (DM) compared to compounds A to W equivalent to chemical formula 1. Therefore, the combination of the two structures suggested in this document has a range in which the difference in DM of the two main bodies is at least greater than 0.2.

[0844] |DMhost1 –DM host2 |>0.2

[0845] Furthermore, it was confirmed that the sublimation temperature of the compound synthesized in the above production example was lower than 400° C. If the sublimation temperature was higher than 400° C., there would be many limitations in the use as a material for an organic electroluminescent device.

[0846] Furthermore, in order to pre-sublimate a mixture of one of the compounds corresponding to Chemical Formula 1 and one of the hosts corresponding to Chemical Formula 2, it is preferable that the following formula is satisfied.

[0847] |T sub1 –T sub2 |<20℃

[0848] [Experimental Example 2] Preparation Example of Mixture

[0849]

[0850] The premixability of the film formed by evaporating two compounds (one compound each of Chemical Formula 1 and Chemical Formula 2) corresponding to the two main bodies to be mixed was tested by high pressure liquid chromatography (HPLC) analysis. In this Experimental Example 2, the above-mentioned compound J (Chemical Formula 1) and the above-mentioned compound 6 (Chemical Formula 2) were used.

[0851] For this purpose, 0.15 g of compound J (or compound 1-J) and 0.15 g of compound 6 (or compound 2-6) were mixed at a 1:1 (mass ratio) and pulverized. 0.3 g of the mixture was placed in the evaporation source of the VTE vacuum chamber. The chamber was evacuated to reduce the pressure to 10 -7 torr. In order to avoid cooling of the raw materials and keep them at an appropriate temperature, the evaporation process is not interrupted. After the film was formed, the substrate was replaced twice in succession. The evaporated film was analyzed by HPLC and the results are shown in Figure 5 Take 3 such substrate samples and Figure 5 In the figure, the composition of the component compound J (chemical formula 1) and the compound 6 (chemical formula 2) does not change significantly from film 1 to film 3. The concentration change before and after evaporation within 10%, preferably within 5%, throughout the entire process is considered to be excellent and useful for commercial OLED applications, showing that the difference in sublimation temperature of the two mixed compounds can maintain the above concentration change at a temperature difference of 20°C or less. The difference in sublimation temperature between the above compound J and compound 6 is 10°C.

[0852] like Figure 5The slight change in concentration does not show any trend on the device. Sample collection and HPLC analysis can be explained by the following formula (7). More specifically, the first compound (Compound J) or the second compound (Compound 6) has a concentration C1 in the above mixture. -4 Torr to 1×10 -9 In high vacuum evaporation equipment with a chamber base pressure of to The film formed by evaporating at a rate of evaporation onto a surface located at a predetermined distance from where the mixture is evaporated has a concentration C2, satisfying the following formula (7). Here, |(C1-C2) / C1| can be less than 10%, less than 9%, less than 8%, less than 7%, less than 6%, less than 5%, or less than 4%.

[0853] |(C1-C2) / C1 | < 10% - Formula (7)

[0854] When the concentration C1 of the compound represented by compound 6 in the above composition is 48.85%, the concentration of membrane 1 is 47.69%, so the concentration change is 2.3%, the concentration of membrane 2 is 46.94%, so the concentration change is 3.9%, and the concentration of membrane 3 is 47.71%, so the concentration change is 2.3%.

[0855] In the films 1 to 3 produced, the concentration change did not vary significantly, and it was observed that the variation between the films was small. Therefore, the condition of the above formula (7) was satisfied.

[0856] [Experimental Example 3] Comparative Preparation Example of Mixture

[0857] The following are exemplary results of mixture examples that deviate from the conditions suggested in this document. In the comparative preparation example of the following mixture, compound B (Chemical Formula 1) and compound 26 (Chemical Formula 2) were used.

[0858] For mixing, 0.21 g of compound B (or compound 1-B) and 0.09 g of compound 26 (or compound 2-26) were mixed at a mass ratio of 7:3 and crushed. The preparation conditions were the same as those of the above-mentioned Experimental Example 2, and the results are shown in Figure 6 .

[0859] According to the above formula (7), when the concentration C1 of the compound represented by compound B in the above composition is 69.30%, the concentration of membrane 1 is 65.42%, so the concentration change is 5.5%, the concentration of membrane 2 is 61.22%, so the concentration change is 11.6%, and the concentration of membrane 3 is 62.82%, so the concentration change is 9.3%.

[0860] In the films 1 to 3 produced, the concentration changes significantly varied, and in particular, a change of 10% or more was observed, and large variations were observed between the films. Therefore, the condition of the above formula (7) was not satisfied.

[0861] [Production Example 3] Synthesis of Chemical Formula 3

[0862]

[0863] Here, L1, m, R1 to R10, x, and y are defined the same as in the above Chemical Formula 3, Dz refers to the number of deuterium substitutions, and z is greater than or equal to 1 and less than or equal to the maximum number of hydrogen atoms that can be substituted with deuterium.

[0864] The reactant (1 equivalent) and trifluoromethanesulfonic acid (catalyst) were added to C6D6 (10 to 50 times the mass ratio relative to the reactant) and stirred at 70°C for 10 to 100 minutes. After the reaction was completed, D2O (excessive) was added, stirred for 30 minutes, and trimethylamine (excessive) was added dropwise. The reaction solution was transferred to a separatory funnel and extracted with water and chloroform. After the extract was dried with MgSO4, it was heated with toluene and recrystallized to obtain the product shown in [Table 5] below.

[0865] [Table 5]

[0866]

[0867]

[0868]

[0869] The degree of deuterium substitution of each product varies depending on the reaction time. + ) value, determines the substitution rate.

[0870] Compounds 3A to 3M as the above-mentioned reactants were synthesized with reference to the prior art documents of our company such as KR1790854B1. In addition, compounds 3-1 to 3-13 as deuterium-substituted products were synthesized with reference to the prior art document KR1538534B1.

[0871] [Experimental Example 4] Fabrication of OLED

[0872] <Example 1>

[0873] The ITO / Ag / ITO as anode is The substrate to be deposited was cut into a size of 50 mm × 50 mm × 0.5 mm, placed in distilled water dissolved with a dispersant, and washed with ultrasound. The detergent used was a product of Fischer Co., and the distilled water used was distilled water filtered twice using a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was performed in sequence with solvents of isopropanol, acetone, and methanol, and then dried.

[0874] On the anode prepared in this way, HI-1 was placed A hole injection layer is formed by thermal vacuum deposition with a thickness of 1000 mm / s. On the hole injection layer, HT1 as a hole transporting material is deposited with a thickness of 1000 mm / s. Vacuum evaporation was performed to form a hole transport layer. Then, EB1 Then, the host compound 3-2 synthesized in Preparation Example 3 and the dopant BD1 (2 wt%) were mixed with A first light-emitting layer was formed by vacuum deposition with a thickness of 1000 nm, and then a mixture prepared by using the host compound A synthesized in Preparation Example 1 and the compound 2-1 synthesized in Preparation Example 2 and a dopant BD1 (2 wt %) were added to form a first light-emitting layer. Vacuum evaporation was performed to form a second light-emitting layer. Then, HB1 was evaporated To form an electron regulating layer, the compound ET1 and Liq were mixed at a mass ratio of 5:5 to form a layer having a thickness of The electron transport layer of After forming a 1000-mm thick magnesium and lithium fluoride (LiF) film as an electron injection layer, a cathode is formed using magnesium and silver (1:4). After that, CP1 The thickness of the organic matter is evaporated to form a covering layer, thereby completing the device. In the above process, the evaporation rate of the organic matter is maintained at

[0875] The comparison of physical properties of Examples 1 to 43 and Comparative Examples 1 to 6 and the device results of Examples 1 to 43, Comparative Examples 1 to 6 and Comparative Examples 13 to 16 are shown in [Table 6] and [Table 7].

[0876] [Table 6]

[0877]

[0878]

[0879]

[0880]

[0881] [Table 7]

[0882]

[0883]

[0884]

[0885]

[0886]

[0887]

[0888] It can be confirmed in the existing document KR2021-0148951A that the above-mentioned embodiment using a mixture containing a deuterium-substituted host as a blue fluorescent host can be observed to be excellent in life, especially in comparison with a host not substituted with deuterium. In this document, by applying two light-emitting layers, using a deuterium-containing pyrene host as the host of the first light-emitting layer, and setting the host of the second light-emitting layer to a device composed of a host containing two anthracenes, it can be confirmed that the blue organic light-emitting device having two light-emitting layers of the above structure has an effect of improving voltage, efficiency, and life compared with Comparative Examples 1 to 6 used as blue fluorescent hosts.

[0889] By mixing and using different series of anthracene hosts (chemical formula 1 and chemical formula 2), the possibility of achieving low voltage and high efficiency is increased. Here, by introducing deuterium, a blue light-emitting device with significantly excellent life span can be achieved, and two light-emitting layers are applicable and a pyrene derivative is introduced in the first light-emitting layer. By injecting holes in the hole transport region and controlling the flow of holes, it can be observed that the overall voltage and efficiency can be further improved. In addition, by introducing deuterium into the host of the first light-emitting layer, i.e., the pyrene derivative, the part of the interface with the hole transport region that greatly affects the life span is improved, and the low voltage and high efficiency of the device can be maintained, while achieving further improvement in life span.

[0890] In addition, it can be confirmed that compared with Examples 3 and 4 in which two main bodies are co-evaporated to form a mixture layer, Examples 1 and 2 in which two different main bodies are premixed more finely and uniformly to form a layer improve the stability, voltage, efficiency, and life of the device.

[0891] <Example 44> Production of OLED

[0892] The ITO / Ag / ITO as anode is The substrate to be deposited was cut into a size of 50 mm × 50 mm × 0.5 mm, placed in distilled water dissolved with a dispersant, and washed with ultrasound. The detergent used was a product of Fischer Co., and the distilled water used was distilled water filtered twice using a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was performed in sequence with solvents of isopropanol, acetone, and methanol, and then dried.

[0893] On the anode prepared in this way, HI-1 was placed A hole injection layer is formed by thermal vacuum deposition with a thickness of 1000 mm / s. On the hole injection layer, HT1 as a hole transporting material is deposited with a thickness of 1000 mm / s. Vacuum evaporation was performed to form a hole transport layer. Then, EB1 Then, the host compound 3-2 synthesized in Preparation Example 3 and the dopant BD1 (2 wt%) were mixed with Then, a mixture prepared by using the host compound B synthesized in Preparation Example 1 and the compound 2-3 synthesized in Preparation Example 2 and a dopant BD2 (2 wt %) were added to form a first light-emitting layer with a thickness of 1000 nm. Then, HB1 was vacuum-deposited with a thickness of The electron adjustment layer is formed by vapor deposition with a thickness of , and the compound ET1 and Liq are mixed at a ratio of 5:5 (mass ratio) to form a layer with a thickness of The electron transport layer of After forming a 1000-mm thick magnesium and lithium fluoride (LiF) film as an electron injection layer, a cathode is formed using magnesium and silver (1:4). After that, CP1 The thickness of the organic matter is evaporated to complete the device. In the above process, the evaporation rate of the organic matter is maintained at

[0894] The physical property comparison of Examples 44 to 84 and Comparative Examples 7 to 12 and the device results of Examples 44 to 84, Comparative Examples 7 to 12 and Comparative Examples 17 to 20 are shown in [Table 8] and [Table 9].

[0895] [Table 8]

[0896]

[0897]

[0898]

[0899]

[0900] [Table 9]

[0901]

[0902]

[0903]

[0904]

[0905]

[0906] It can be confirmed that the above-mentioned Examples 44 to 84 show the same tendency as the results of Examples 1 to 43 of [Table 7], but in addition to the blue fluorescent dopant based on pyrene, even if a blue fluorescent dopant based on boron is used, the performance advantages and characteristics of the dopant can be maintained, and it is also effective on a device that uses two light-emitting layers and uses pyrene as the first light-emitting layer.

Claims

1. An organic light-emitting device, wherein: include: an anode, a cathode, a first light-emitting layer disposed between the anode and the cathode, and a second light-emitting layer disposed between the first light-emitting layer and the cathode and in contact with the first light-emitting layer, The first light-emitting layer comprises a compound of the following chemical formula 3, The second light emitting layer includes a mixture of a first compound including a compound of the following Chemical Formula 1 and a second compound including a compound of the following Chemical Formula 2: [Chemical formula 3] In the chemical formula 3, L1 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, Any one of R1 to R10 is combined with L1, and the others are the same or different and are independently hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic, and one of the others is selectively fused with L1 to form a substituted or unsubstituted hydrocarbon ring, or selectively fused with adjacent groups to form a substituted or unsubstituted ring, Ar1 is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group, m is an integer from 0 to 3. When m is 2 or more, the L1 in the brackets are the same or different from each other. x is an integer from 1 to 3. When x is 2 or more, the structures in the brackets are the same or different from each other. y is an integer from 1 to 3. When y is 2 or more, the Ar1 in the brackets are the same or different from each other. In the chemical formula 1, At least one of R11 to R20 is bonded to the * site of the chemical formula 1-1, and the others are the same as or different from each other and are independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted silyl group, L2 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, Ar2 is a substituted or unsubstituted aryl group, p is an integer from 1 to 3, In the chemical formula 2, At least one of Y1 to Y10 is bound to the * site of the chemical formula 2-1, and the others are the same or different from each other and are independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted silyl group, A and B are the same or different from each other, and are each independently a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocycle, L3 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, q is an integer from 1 to 3.

2. The organic light emitting device according to claim 1, wherein: The chemical formula 3 is any one of the following chemical formulas 3-A to 3-F: [Chemical Formula 3-A] [Chemical formula 3-B] [Chemical formula 3-C] [Chemical formula 3-D] [Chemical formula 3-E] [Chemical formula 3-F] In the Chemical Formulae 3-A to 3-F, L1, m, R1 to R10 and Ar1 are the same as defined in the Chemical Formula 3.

3. The organic light emitting device according to claim 1, wherein: The chemical formula 3 is any one of the following chemical formulas 3-a to 3-e: [Chemical formula 3-a] [Chemical formula 3-b] [Chemical formula 3-c] [Chemical formula 3-d] [Chemical formula 3-e] In the chemical formulae 3-a to 3-e, Ar1 is the same as defined in the chemical formula 3, Any one of R1 to R10 is combined with Ar1, and the rest are the same or different from each other, and are independently hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group, and are selectively fused with adjacent groups to form a substituted or unsubstituted ring.

4. The organic light emitting device according to claim 1, wherein: At least one of R12, R13, and R19 to R20 is bonded to the * site of the chemical formula 1-1.

5. The organic light emitting device according to claim 1, wherein: The thickness (D1) of the first light-emitting layer is smaller than the thickness (D2) of the second light-emitting layer.

6. The organic light emitting device according to claim 1, wherein: A deuterium substitution rate of at least one of the compound of Chemical Formula 3, the first compound, and the second compound is 1% to 100%.

7. The organic light emitting device according to claim 1, wherein: A deuterium substitution rate of at least one of the compound of Chemical Formula 3, the first compound, and the second compound is 40% to 99%.

8. The organic light emitting device according to claim 1, wherein: The sublimation temperature (T sub1 ) and the sublimation temperature (T sub2 ) satisfies the following formula (1): |T sub1 –T sub2 |≤15℃-Formula (1).

9. The organic light emitting device according to claim 1, wherein: The evaporation temperatures of the first compound and the second compound are each less than 400°C.

10. The organic light emitting device according to claim 1, wherein: The first compound or the second compound has a concentration C1 in the mixture, and the mixture is prepared by mixing the mixture at a concentration of 1×10 -4 Up to 1x10 -9 In high vacuum evaporation equipment with a chamber base pressure of to The film formed by evaporating at a rate of 10000 rpm onto a surface located at a predetermined distance from where the mixture is evaporated has a concentration C2 that satisfies the following formula 2: |(C1-C2) / C1|<10%-Formula (2).

11. The organic light emitting device according to claim 10, wherein: The value of |(C1-C2) / C1| in Formula 2 is less than 3%.

12. The organic light emitting device according to claim 1, wherein: The triplet energy level (T h1 ), the triplet energy level of the first compound (T h2 ) and the triplet energy level of the second compound (T h3 ) satisfies the following equations 3 and 4: T h1 > T h2 - Formula (3) T h1 >T h3 -Formula (4).

13. The organic light emitting device according to claim 1, wherein: A deuterium substitution rate of at least one of the first compound and the second compound is 10% to 100%.

14. The organic light emitting device according to claim 1, wherein: The deuterium substitution rates of the first compound and the second compound are each 10% to 100%.

15. The organic light emitting device according to claim 1, wherein: The mass ratio of the first compound to the second compound is 1:9 to 9:

1.

16. The organic light emitting device according to claim 1, wherein: The mixture is evaporated from a source to form the second light-emitting layer.

17. The organic light emitting device according to claim 1, wherein: The light-emitting layer of the organic light-emitting device is suitable for use in one or more layers of a stacked device.

18. The organic light emitting device according to claim 1, wherein: The maximum emission spectrum (λmax) is in the range of 400nm to 470nm.

19. The organic light emitting device according to claim 1, wherein: The first light-emitting layer and the second light-emitting layer each include a dopant.

20. The organic light emitting device according to claim 19, wherein: The dopant is a fluorescent dopant.

21. The organic light emitting device according to claim 19, wherein: The dopant includes a pyrene-based compound.

22. The organic light emitting device according to claim 19, wherein: The dopant includes a non-pyrene compound.

23. The organic light emitting device according to claim 22, wherein: The non-pyrene-based compound includes a boron-based compound.

24. The organic light emitting device according to claim 22, wherein: The non-pyrene-based compound includes a condensed carbazole-based compound.

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