Composition, deposition source, organic electroluminescent device comprising the composition and method for manufacturing the same

By using deuterium-substituted anthracene derivatives as mixed host materials, the contradiction between high efficiency and life of organic electroluminescent devices is solved, and the stability and life of the devices, especially the performance of blue devices, are improved.

CN114287069BActive Publication Date: 2025-09-16LG CHEM LTD
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Patent Information

Application Number
CN202180005059.8
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Priority Date
2020-06-01
Filing Date
2021-06-01
Publication Date
2025-09-16
Estimated Expiration
2041-06-01

AI Technical Summary

Technical Problem

It is difficult to improve the device life of existing organic electroluminescent devices while maintaining high efficiency, especially the performance of blue devices.

Method used

Anthracene derivatives containing deuterium substitution are used as mixed host materials, and carbon-deuterium bonds are used to replace carbon-hydrogen bonds to increase the bond energy of the molecule to prepare the light-emitting layer material.

Benefits of technology

The lifetime of organic electroluminescent devices is significantly improved while maintaining high efficiency, especially the performance of blue devices.

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Abstract

The present disclosure relates to a composition, a deposition source, an organic electroluminescent device comprising the composition, and a method for manufacturing the organic electroluminescent device.
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Description

Technical Field

[0001] This specification claims priority to and the benefit of Korean Patent Application No. 10-2020-0065928, filed in the Korean Intellectual Property Office on June 1, 2020, the entire contents of which are incorporated herein by reference.

[0002] The present disclosure relates to compositions, deposition sources, organic electroluminescent devices comprising the compositions, and methods for making organic electroluminescent devices. Background Art

[0003] An organic electroluminescent device (OLED) has an organic thin film interposed between two electrodes. When voltage is applied to an OLED with this structure, electrons and holes injected from the two electrodes combine and form pairs in the organic thin film, annihilating each other and generating light. Depending on the needs, the organic thin film can be formed as a single layer or multiple layers.

[0004] Most of the materials used in organic electroluminescent devices are pure organic materials or complex compounds in which organic materials and metals form complexes, and can be divided into hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, etc. according to the application. In this article, as hole injection materials or hole transport materials, organic materials with p-type characteristics are generally used, that is, organic materials that are easily oxidized and have an electrochemically stable state when oxidized. At the same time, as electron injection materials or electron transport materials, organic materials with n-type characteristics are generally used, that is, organic materials that are easily reduced and have an electrochemically stable state when reduced. As light-emitting layer materials, preferably materials with both p-type characteristics and n-type characteristics, that is, materials with stable forms in both oxidized and reduced states, and preferably materials with high luminous efficiency of converting excitons into light when excitons generated by recombination of holes and electrons in the light-emitting layer are formed.

[0005] There is a continuing need to develop organic thin film materials for improving the performance, lifetime or efficiency of organic electroluminescent devices. Summary of the Invention

[0006] Technical issues

[0007] The present specification aims to provide a material for an organic electroluminescent device that has high stability and exhibits excellent characteristics when used in the device.

[0008] Technical Solution

[0009] One embodiment of the present specification provides a composition including a compound of the following Chemical Formula 1 and a compound of the following Chemical Formula 2, wherein at least one type of the compound of the following Chemical Formula 1 and the compound of the following Chemical Formula 2 includes at least one deuterium.

[0010]

[0011] In chemical formula 1,

[0012] At least one of R1 to R10 is bonded to the * site of Chemical Formula 1-1, and the rest 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 heteroaryl group, or a substituted or unsubstituted silyl group,

[0013] L1 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0014] Ar is a substituted or unsubstituted aryl group, and

[0015] p is an integer from 1 to 5,

[0016]

[0017] In Chemical Formula 2,

[0018] At least one of Y1 to Y10 is bonded to the * position of Chemical Formula 2-1, and the rest 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 heteroaryl group, or a substituted or unsubstituted silyl group,

[0019] A and B 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,

[0020] L2 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, and

[0021] q is an integer from 1 to 5.

[0022] One embodiment of the present specification provides a deposition source prepared using the composition.

[0023] Furthermore, one embodiment of the present specification provides an organic electroluminescent device including a cathode; an anode; and a light-emitting layer disposed between the cathode and the anode, wherein the light-emitting layer includes the composition.

[0024] Finally, one embodiment of the present specification provides a method for manufacturing an organic electroluminescent device, the method comprising: preparing the composition; preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layer, wherein the formation of the one or more organic material layers comprises forming the one or more organic material layers using the composition.

[0025] Beneficial effects

[0026] The composition according to the embodiment described in this specification has very excellent stability, and when used in an organic electroluminescent device, excellent efficiency characteristics, driving voltage characteristics, and lifespan characteristics are obtained in the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0027] Figure 1 and Figure 3 Each shows an organic electroluminescent device according to one embodiment of the present specification.

[0028] Figure 2 This is a TLC-MS chart used to calculate the deuterium substitution rate.

[0029] <Reference Signs>

[0030] 10: Organic electroluminescent devices

[0031] 20: Base

[0032] 30: Anode

[0033] 40: Luminous layer

[0034] 50: cathode

[0035] 60: Hole injection layer

[0036] 70: Hole transport layer

[0037] 80: Hole control layer

[0038] 90: Electronic control layer

[0039] 100: Electron transport layer

[0040] 110: Electron injection layer

[0041] 120: Covering DETAILED DESCRIPTION

[0042] Hereinafter, this specification will be described in detail.

[0043] The composition according to one embodiment of the present invention includes a compound of Chemical Formula 1 and a compound of Chemical Formula 2, wherein at least one type of compound of Chemical Formula 1 and the compound of Chemical Formula 2 includes at least one deuterium. When an organic electroluminescent device including the composition is manufactured, a device having significantly improved lifespan while maintaining excellent efficiency can be obtained.

[0044] Anthracene derivatives such as those in Chemical Formulas 1 and 2 exhibit stable performance when used as hosts in organic electroluminescent devices and have been commercialized to date. However, a single host has opposing effects on lifetime and efficiency, and achieving both is difficult. Mixed hosts have been used as an alternative, but these have failed to achieve performance beyond the fundamentals of organic compounds and have been difficult to improve the performance of the resulting blue devices.

[0045] Therefore, deuteration of anthracene-based hosts has been sought as a way to maximize the efficiency of the light-emitting layer while maintaining the lifetime, and the present description significantly improves the lifetime problem while maintaining the efficiency of organic electroluminescent devices by introducing deuterium-substituted anthracene derivatives as hybrid hosts.

[0046] The light-emitting layer of an organic electroluminescent device is the region that directly affects luminescence and is the portion where energy-induced molecular losses are greatest. Carbon-deuterium bonds are stronger than carbon-hydrogen bonds, and deuterium has a high bond energy due to its high mass, which reduces its zero-point energy with carbon. Therefore, by replacing the carbon-hydrogen bonds contained in the molecules of the compound of Chemical Formula 1 and / or the compound of Chemical Formula 2 with carbon-deuterium bonds, the molecular bond energy is increased. Therefore, when manufacturing devices containing the deuterium-containing compound of Chemical Formula 1 and / or the deuterium-containing compound of Chemical Formula 2, the device lifetime is improved.

[0047]

[0048] In the present specification, unless specifically stated otherwise, a description that a part “includes” certain constituent elements means that the part can further include the additional constituent elements, and does not exclude the additional constituent elements.

[0049] In the present specification, “deuterated” or “deuterated” means that hydrogen at a substitutable position of a compound is substituted with deuterium.

[0050] In this specification, "X% deuterated," "a degree of deuteration of X%," or "a deuterium substitution rate of X%" means that X% of hydrogen atoms at substitutable positions in the corresponding structure are substituted with deuterium. For example, when the corresponding structure is dibenzofuran, "dibenzofuran is 25% deuterated," "a degree of deuteration of dibenzofuran of 25%," or "a deuterium substitution rate of dibenzofuran of 25%" means that two of the eight hydrogen atoms at substitutable positions in dibenzofuran are substituted with deuterium.

[0051] In the present specification, the "degree of deuteration" or "deuterium substitution rate" can be determined using a known method such as nuclear magnetic resonance (1HNMR), TLC / MS (thin layer chromatography / mass spectrometry) or GC / MS (gas chromatography / mass spectrometry).

[0052] Specifically, when the "deuteration degree" or "deuterium substitution rate" is analyzed using nuclear magnetic resonance (1H NMR), the deuteration degree or deuterium substitution rate can be calculated from the integrated amount of the total peak by integrating the ratio in 1H NMR after adding DMF (dimethylformamide) as an internal standard.

[0053] In addition, when the "deuteration degree" or "deuterium substitution rate" is analyzed by TLC / MS (thin layer chromatography / mass spectrometry), the deuteration 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, in the analysis of the deuteration degree of the following compound A, when the molecular weight of the following starting material is 506 and Figure 2 When the maximum molecular weight (median value) of the following compound A in the MS graph is 527, 21 of the 26 hydrogen atoms at the substitutable positions of the following starting material are substituted by deuterium, and thus it can be calculated that approximately 81% of the hydrogen atoms are deuterated.

[0054]

[0055] In this specification, D means deuterium.

[0056] Examples of the substituent in the present specification are described below, however, the substituent is not limited thereto.

[0057] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position of substitution is not limited as long as it is a position where a hydrogen atom is substituted (i.e., a position where a substituent can be substituted), and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

[0058] In the present specification, the term "substituted or unsubstituted" means substituted with one, two or more substituents selected from the following: deuterium; a halogen group; a nitrile group; a nitro group; an imide group; an amide group; a carbonyl group; an ester group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; a substituted or unsubstituted alkylsulfonyl; substituted or unsubstituted arylsulfonyl; substituted or unsubstituted alkenyl; substituted or unsubstituted silyl; substituted or unsubstituted boronyl; substituted or unsubstituted amine; substituted or unsubstituted arylphosphino; substituted or unsubstituted phosphine oxide; substituted or unsubstituted aryl; and substituted or unsubstituted heterocyclic group, or substituted with two or more of the above-exemplified substituents linked together, or without substituents. For example, "a substituent in which two or more substituents are linked together" may be a heteroaryl substituted with an aryl group; or an aryl substituted with a heteroaryl group. Furthermore, a biphenyl group may be an aryl group, or may be interpreted as a substituent in which two phenyl groups are linked together.

[0059] In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.

[0060] In the present specification, the alkyl group may be linear or branched, and although not particularly limited thereto, the number of carbon atoms is preferably 1 to 30. Specific examples thereof may include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

[0061] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms. Specific examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0062] In this specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 30. Specific examples thereof may include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc., but are not limited thereto.

[0063] In the present specification, the amine group can be selected from: -NH2; alkylamine group; N-alkylarylamine group; arylamine group; N-arylheteroarylamine group; N-alkylheteroarylamine group and heteroarylamine group, and although not particularly limited thereto, the number of carbon atoms is preferably 0 to 30. Specific examples of amino groups may include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, anthrylamino, 9-methyl-anthrylamino, diphenylamino, N-phenylnaphthylamino, ditolylamino, N-phenyltolylamino, triphenylamino, N-phenylbiphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthrenylamino, N-biphenylphenanthrenylamino, N-phenylfluorenylamino, N-phenylterphenylamino, N-phenanthrenylfluorenylamino, N-biphenylfluorenylamino, etc., but are not limited thereto.

[0064] In the present specification, the N-alkylarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and an aryl group.

[0065] In the present specification, the N-arylheteroarylamine group means an amine group in which N of the amine group is substituted with an aryl group and a heteroaryl group.

[0066] In the present specification, the N-alkylheteroarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and a heteroaryl group.

[0067] In the present specification, the alkyl group in the alkylamino group, N-arylalkylamino group, alkylthio group, alkylsulfonyl group and N-alkylheteroarylamino group is the same as the above-mentioned examples of the alkyl group.

[0068] The number of carbon atoms of the alkylthio group is not particularly limited, but is preferably 1 to 30. Specific examples thereof may include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group, an octylthio group, and the like, and examples of the alkylsulfonyl group may include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, and the like, but are not limited thereto.

[0069] In the present specification, the alkenyl group may be linear or branched, and although not particularly limited thereto, the number of carbon atoms is preferably 2 to 30. Specific examples thereof may include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylethen-1-yl, 2-phenylethen-1-yl, 2,2-diphenylethen-1-yl, 2-phenyl-2-(naphthyl-1-yl)ethen-1-yl, 2,2-bis(diphenyl-1-yl)ethen-1-yl and the like, but are not limited thereto.

[0070] In the present specification, the alkynyl group may be linear or branched, and although not particularly limited thereto, the number of carbon atoms is preferably 2 to 20. Specific examples thereof may include ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl and the like, but are not limited thereto.

[0071] In the present specification, the silyl group may be an alkylsilyl group or an arylsilyl group, and further, may be a trialkylsilyl group or a triarylsilyl group. The number of carbon atoms of the silyl group is not particularly limited, but is preferably 1 to 30, and the number of carbon atoms of the alkylsilyl group may be 1 to 30, and the number of carbon atoms of the arylsilyl group may be 5 to 30. Specific examples thereof may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but are not limited thereto.

[0072] In this specification, the boron group can be -BR 100 R 101 . R 100 and R 101 are the same as or different from each other and may each be independently selected from hydrogen; deuterium; halogen; nitrile; substituted or unsubstituted monocyclic or polycyclic cycloalkyl having 3 to 30 carbon atoms; substituted or unsubstituted linear or branched alkyl having 1 to 30 carbon atoms; substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 30 carbon atoms; and substituted or unsubstituted monocyclic or polycyclic heteroaryl having 2 to 30 carbon atoms.

[0073] In the present specification, specific examples of the phosphine oxide group may include a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, and the like, but are not limited thereto.

[0074] In the present specification, the aryl group is not particularly limited but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

[0075] When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Specific examples of the monocyclic aryl group may include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.

[0076] When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 30. Specific examples of the polycyclic aryl group may include naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, phenanthrenyl, perylene, 1-Hydroxy, ...

[0077] In this specification, the fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.

[0078] When the fluorenyl group is substituted, it may include etc., however, the structure is not limited thereto.

[0079] In the present specification, the aryl group in the aryloxy group, arylthio group, arylsulfonyl group, N-arylalkylamino group, N-arylheteroarylamino group and arylphosphino group is the same as the above-mentioned examples of the aryl group.

[0080] The number of carbon atoms of the aryloxy group is not particularly limited, but is preferably 6 to 30. Specific examples thereof may include phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenyloxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthryloxy, 2-anthryloxy, 9-anthryloxy, 1-phenanthryloxy, 3-phenanthryloxy, 9-phenanthryloxy and the like.

[0081] The number of carbon atoms in the arylthio group is not particularly limited, but is preferably 5 to 30, and further preferably 6 to 30. Specific examples of the arylthio group may include a phenylthio group, a 2-methylphenylthio group, a 4-tert-butylphenylthio group, and the like, and specific examples of the arylsulfonyl group may include a benzenesulfonyl group, a p-toluenesulfonyl group, and the like, however, the arylthio group and the arylsulfonyl group are not limited thereto.

[0082] In this specification, examples of arylamine groups include substituted or unsubstituted monoarylamine groups, or substituted or unsubstituted diarylamine groups. The aryl group in the arylamine group can be a monocyclic aryl group or a polycyclic aryl group. The arylamine group containing two or more aryl groups can contain a monocyclic aryl group, a polycyclic aryl group, or both a monocyclic aryl group and a polycyclic aryl group. For example, the aryl group in the arylamine group can be selected from the examples of the above-mentioned aryl groups.

[0083] In this specification, a heterocyclic group is a group containing one or more non-carbon atoms (i.e., heteroatoms), and specifically, the heteroatoms may include one or more atoms selected from O, N, S, P, etc. Although not particularly limited thereto, the number of carbon atoms is preferably 2 to 50, and more preferably 2 to 30, and the heterocyclic group may be monocyclic or polycyclic. The heterocyclic group may be an aromatic ring, an aliphatic ring, and a fused ring thereof. Examples of heterocyclic groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazole, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo[omicron] oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthroline, isothiophene oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, etc., but are not limited thereto.

[0084] Heteroaryl means a monovalent aromatic heterocyclic group, and heteroarylene means a divalent aromatic heterocyclic group. The description of heterocyclic groups provided above can be applied to heteroaryl and heteroarylene, except that these are aromatic heterocyclic groups.

[0085] In this specification, examples of heteroarylamine groups include substituted or unsubstituted monoheteroarylamine groups, or substituted or unsubstituted diheteroarylamine groups. Heteroarylamine groups containing two or more heteroaryl groups may include monocyclic heteroaryl groups, polycyclic heteroaryl groups, or both monocyclic heteroaryl groups and polycyclic heteroaryl groups. For example, the heteroaryl groups in the heteroarylamine group may be selected from the examples of heteroaryl groups described above.

[0086] In the present specification, examples of the heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as the examples of the heteroaryl group described above.

[0087] Hereinafter, Chemical Formula 1 will be described.

[0088] According to one embodiment of the present specification, one to three of R1 to R10 are bonded to the * position of 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 heteroaryl group, or a substituted or unsubstituted silyl group.

[0089] According to another embodiment, one to three of R1 to R10 are bonded to the * position of 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 heteroaryl group having 2 to 60 carbon atoms, or a substituted or unsubstituted silyl group.

[0090] In another embodiment, R9 and R10 are bonded to the * position of Chemical Formula 1-1, and the remainder 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 heteroaryl group, or a substituted or unsubstituted silyl group.

[0091] According to another embodiment, R9, R10 and R8 are bonded to the * position of 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 heteroaryl group, or a substituted or unsubstituted silyl group.

[0092] In another embodiment, R9, R10, and R7 are bonded to the * position of Chemical Formula 1-1, and the remainder 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 heteroaryl group, or a substituted or unsubstituted silyl group.

[0093] According to one embodiment of the present specification, substituents not bonded to Chemical Formula 1-1 in R1 to R10 are the same as or different from each other, and are each independently hydrogen, deuterium, or a dibenzofuranyl group.

[0094] According to one embodiment of the present specification, p is an integer of 1 to 5, and when p is 2 or greater, two or more L1s are the same as or different from each other.

[0095] In another embodiment, p is an integer from 1 to 3, and when p is 2 or greater, two or more L1 are the same as or different from each other.

[0096] According to one embodiment of the present specification, Chemical Formula 1 is any one of the following Chemical Formulas 1-A to 1-C.

[0097] [Chemical Formula 1-A]

[0098]

[0099] [Chemical Formula 1-B]

[0100]

[0101] [Chemical Formula 1-C]

[0102]

[0103] In Chemical Formulas 1-A to 1-C,

[0104] 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 heteroaryl group, or a substituted or unsubstituted silyl group,

[0105] 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, and

[0106] Ar11 to Ar14 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group.

[0107] According to one embodiment of the present specification, 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 heteroaryl group having 2 to 60 carbon atoms, or a substituted or unsubstituted silyl group.

[0108] According to one embodiment of the present specification, R1' to R8' are the same as or different from each other, and are each independently hydrogen, deuterium or dibenzofuranyl.

[0109] According to one embodiment of the present specification, L1 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. L1 may be substituted with deuterium.

[0110] In another embodiment, L1 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.

[0111] According to another embodiment, L1 is a direct bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthrenylene, or substituted or unsubstituted trimphenylene.

[0112] In another embodiment, L 1 is a direct bond, unsubstituted or deuterium-substituted phenylene, unsubstituted or deuterium-substituted biphenylene, unsubstituted or deuterium-substituted naphthylene, unsubstituted or deuterium-substituted phenanthrenylene, or unsubstituted or deuterium-substituted triphenylene.

[0113] According to one embodiment of the present specification, Ar is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms. Ar may be substituted with deuterium.

[0114] In another embodiment, Ar is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0115] According to another embodiment, Ar is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, or substituted or unsubstituted triphenylene.

[0116] In another embodiment, Ar is unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted biphenyl, unsubstituted or deuterium-substituted terphenyl, unsubstituted or deuterium-substituted naphthyl, unsubstituted or deuterium-substituted phenanthrenyl, or unsubstituted or deuterium-substituted triphenylene.

[0117] According to one embodiment of the present specification, L11 to L14 are the same 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.

[0118] 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.

[0119] 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 phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrenylene group, or a substituted or unsubstituted triphenylene group.

[0120] In another embodiment, L11 to L14 are the same as or different from each other, and are each independently a direct bond, unsubstituted or deuterium-substituted phenylene, unsubstituted or deuterium-substituted biphenylene, unsubstituted or deuterium-substituted naphthylene, unsubstituted or deuterium-substituted phenanthrenylene, or unsubstituted or deuterium-substituted triphenylene.

[0121] According to one embodiment of the present specification, 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 60 carbon atoms. Ar11 to Ar14 may be substituted with deuterium.

[0122] In another embodiment, 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.

[0123] According to another embodiment, 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.

[0124] In another embodiment, Ar11 to Ar14 are the same as or different from each other and are each independently unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted biphenyl, unsubstituted or deuterium-substituted naphthyl, unsubstituted or deuterium-substituted terphenyl, unsubstituted or deuterium-substituted phenanthrenyl, or unsubstituted or deuterium-substituted triphenylene.

[0125] In one embodiment of the present specification, Chemical Formula 1 may be selected from the following structural formulas, but is not limited thereto, and the bonding position of deuterium is not limited. In addition, when Chemical Formula 1 does not contain deuterium, it may be a structure that does not contain deuterium (-D) in the following structural formulas, however, the structure is not limited thereto.

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134] Hereinafter, Chemical Formula 2 will be described.

[0135] According to one embodiment of the present specification, at least one of Y1 to Y10 is bonded to the * site of Chemical Formula 2-1, and the rest are hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0136] According to one embodiment of the present specification, one to three of Y1 to Y10 are bonded to the * position of 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 heteroaryl group, or a substituted or unsubstituted silyl group.

[0137] In one embodiment of the present specification, one to three of Y1 to Y10 are bonded to the * position of Chemical Formula 2-1, and the remainder 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 heteroaryl group having 2 to 60 carbon atoms, or a substituted or unsubstituted silyl group.

[0138] In another embodiment, Y7, Y8 or Y9 is bonded to the * position of 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 heteroaryl group, or a substituted or unsubstituted silyl group.

[0139] According to another embodiment, Y7 and Y9 are bonded to the * position of Chemical Formula 2-1, and the remainder 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 heteroaryl group, or a substituted or unsubstituted silyl group.

[0140] According to another embodiment, Y9 and Y10 are bonded to the * position of Chemical Formula 2-1, and the remainder 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 heteroaryl group, or a substituted or unsubstituted silyl group.

[0141] According to one embodiment of the present specification, the substituents not bonded to Chemical Formula 2-1 among Y1 to Y10 are the same as or different from each other and are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. The substituents not bonded to Chemical Formula 2-1 among Y1 to Y10 may be substituted with deuterium.

[0142] According to another embodiment, the substituents not bonded to Chemical Formula 2-1 in 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 phenanthrenyl, or substituted or unsubstituted triphenylene, and the substituents may be further substituted with deuterium, unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted biphenyl, unsubstituted or deuterium-substituted terphenyl, unsubstituted or deuterium-substituted naphthyl, unsubstituted or deuterium-substituted phenanthrenyl, or unsubstituted or deuterium-substituted triphenylene.

[0143] According to one embodiment of the present specification, q is an integer of 1 to 5, and when q is 2 or greater, two or more L2 are the same as or different from each other.

[0144] In another embodiment, q is an integer from 1 to 3, and when q is 2 or greater, two or more L2 are the same as or different from each other.

[0145] According to one embodiment of the present specification, Chemical Formula 2 is the following Chemical Formulas 2-A to 2-E.

[0146] [Chemical Formula 2-A]

[0147]

[0148] [Chemical Formula 2-B]

[0149]

[0150] [Chemical Formula 2-C]

[0151]

[0152] [Chemical Formula 2-D]

[0153]

[0154] [Chemical Formula 2-E]

[0155]

[0156] In Chemical Formulas 2-A to 2-E,

[0157] 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,

[0158] 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 heteroaryl group, or a substituted or unsubstituted silyl group, and

[0159] 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.

[0160] 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.

[0161] 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.

[0162] According to another embodiment, L2 is a direct bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthrenylene, or substituted or unsubstituted trimphenylene.

[0163] In another embodiment, L2 is a direct bond, unsubstituted or deuterium-substituted phenylene, unsubstituted or deuterium-substituted biphenylene, unsubstituted or deuterium-substituted naphthylene, unsubstituted or deuterium-substituted phenanthrenylene, or unsubstituted or deuterium-substituted triphenylene.

[0164] According to one embodiment of the present specification, A and B 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 heterocycle having 2 to 60 carbon atoms.

[0165] 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 unsubstituted or substituted with one or more substituents selected from deuterium and unsubstituted or deuterium-substituted aryl groups; or an aromatic heterocycle having 2 to 60 carbon atoms which is unsubstituted or substituted with one or more substituents selected from deuterium and unsubstituted or deuterium-substituted aryl groups.

[0166] 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 unsubstituted or substituted with one or more substituents selected from deuterium and an unsubstituted or deuterium-substituted aryl group having 6 to 30 carbon atoms; or an aromatic heterocycle having 2 to 60 carbon atoms which is unsubstituted or substituted with one or more substituents selected from deuterium and an unsubstituted or deuterium-substituted aryl group having 6 to 30 carbon atoms.

[0167] 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.

[0168] According to another embodiment, A and B are the same as or different from each other and are each independently benzene which is unsubstituted or substituted with one or more substituents selected from deuterium and an unsubstituted or deuterium-substituted aryl group having 6 to 30 carbon atoms; naphthalene which is unsubstituted or substituted with one or more substituents selected from deuterium and an unsubstituted or deuterium-substituted aryl group having 6 to 30 carbon atoms; phenanthrene which is unsubstituted or substituted with one or more substituents selected from deuterium and an unsubstituted or deuterium-substituted aryl group having 6 to 30 carbon atoms; triphenylene which is unsubstituted or substituted with one or more substituents selected from deuterium and an unsubstituted or deuterium-substituted aryl group having 6 to 30 carbon atoms; or dibenzofuran which is unsubstituted or substituted with one or more substituents selected from deuterium and an unsubstituted or deuterium-substituted aryl group having 6 to 30 carbon atoms.

[0169] According to one embodiment of the present specification, L21 to L24 are the same 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.

[0170] 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.

[0171] According to another embodiment, L21 and L24 are the same as or different from each other, and are each independently 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 phenanthrenylene group, or a substituted or unsubstituted triphenylene group.

[0172] In another embodiment, L21 to L24 are the same as or different from each other, and are each independently a direct bond, unsubstituted or deuterium-substituted phenylene, unsubstituted or deuterium-substituted biphenylene, unsubstituted or deuterium-substituted naphthylene, unsubstituted or deuterium-substituted phenanthrenylene, or unsubstituted or deuterium-substituted triphenylene.

[0173] 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 heterocycle having 2 to 60 carbon atoms.

[0174] In 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 an aromatic hydrocarbon ring having 6 to 60 carbon atoms which is unsubstituted or substituted with one or more substituents selected from deuterium and unsubstituted or deuterium-substituted aryl groups; or an aromatic heterocycle having 2 to 60 carbon atoms which is unsubstituted or substituted with one or more substituents selected from deuterium and unsubstituted or deuterium-substituted aryl groups.

[0175] 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 with one or more substituents selected from deuterium and an unsubstituted or deuterium-substituted aryl group having 6 to 30 carbon atoms; or an aromatic heterocycle having 2 to 60 carbon atoms which is unsubstituted or substituted with one or more substituents selected from deuterium and an unsubstituted or deuterium-substituted aryl group having 6 to 30 carbon atoms.

[0176] In another embodiment, A1-A4 and B1-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.

[0177] 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 which is unsubstituted or substituted with one or more substituents selected from deuterium and an unsubstituted or deuterium-substituted aryl group having 6 to 30 carbon atoms; naphthalene which is unsubstituted or substituted with one or more substituents selected from deuterium and an unsubstituted or deuterium-substituted aryl group having 6 to 30 carbon atoms; phenanthrene which is unsubstituted or substituted with one or more substituents selected from deuterium and an unsubstituted or deuterium-substituted aryl group having 6 to 30 carbon atoms; triphenylene which is unsubstituted or substituted with one or more substituents selected from deuterium and an unsubstituted or deuterium-substituted aryl group having 6 to 30 carbon atoms; or dibenzofuran which is unsubstituted or substituted with one or more substituents selected from deuterium and an unsubstituted or deuterium-substituted aryl group having 6 to 30 carbon atoms.

[0178] According to one embodiment of the present specification, Y1' to Y10' are the same as or different from each other and are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms. Y1' to Y10' may be substituted with deuterium.

[0179] According to another embodiment, 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 phenanthrenyl, or substituted or unsubstituted triphenylene, and the substituents may be further substituted with deuterium, unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted biphenyl, unsubstituted or deuterium-substituted terphenyl, unsubstituted or deuterium-substituted naphthyl, unsubstituted or deuterium-substituted phenanthrenyl, or unsubstituted or deuterium-substituted triphenylene.

[0180] In one embodiment of the present specification, Chemical Formula 2 may be selected from the following structural formulas, but is not limited thereto, and the bonding position of deuterium is not limited. In addition, when Chemical Formula 2 does not contain deuterium, it may be a structure that does not contain deuterium (-D) in the following structural formulas, however, the structure is not limited thereto.

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210] According to one embodiment of the present specification, the deuterium substitution rate of one type of the compound of Chemical Formula 1 and the compound of Chemical Formula 2 is 10% to 100%, and when the deuterium substitution rate is less than 10%, synthesis is difficult and the effect of improving lifespan when used in a device is not significant.

[0211] In one embodiment of the present invention, the deuterium substitution rate of one of the compounds of Chemical Formula 1 and Chemical Formula 2 is 40% to 100%. When a compound having a deuterium substitution rate of 40% to 100% is used, the effect of improving lifespan when used in a device is very excellent.

[0212] According to one embodiment of the present specification, the deuterium substitution rate of both types of compounds of Chemical Formula 1 and Chemical Formula 2 is 10% to 100%. When the deuterium substitution rate of both types of hosts is 10% to 100%, excellent efficiency and lifespan are obtained in the device.

[0213] According to one embodiment of the present specification, the mass ratio of the compound of Chemical Formula 1 to the compound of Chemical Formula 2 (mass of Chemical Formula 1:mass of Chemical Formula 2) is 1:9 to 9:1.

[0214] In one embodiment of the present specification, the compound of Chemical Formula 1 and the compound of Chemical Formula 2 satisfy the following Formula 1. When the following Formula 1 is satisfied, the two types of compounds have very different dipole moment values, and when the two types of compounds are used in a light-emitting layer in a device, one type of compound effectively improves hole injection, and the other type of compound controls the exciton generation region by controlling the entry of electrons into the light-emitting layer, and thus, device performance can be improved.

[0215] [Formula 1]

[0216] │DM 主体1 -DM 主体2 │>0.2

[0217] DM 主体1 is the dipole moment value of the compound of Chemical Formula 1, and

[0218] DM 主体2 is the dipole moment value of the compound of Chemical Formula 2.

[0219] According to one embodiment of the present specification, the dipole moment value of the compound of Chemical Formula 1 is greater than or equal to 0 and less than 1D, or greater than or equal to 0 and less than 0.5D.

[0220] According to one embodiment of the present specification, the dipole moment value of the compound of Chemical Formula 2 is 0.5D to 2D, or greater than or equal to 0.7D and less than 2D.

[0221] In this specification, the dipole moment is a physical quantity indicating the degree of polarity and can be calculated by the following mathematical equation 1, with the unit being Debye (D).

[0222] [Mathematical equation 1]

[0223]

[0224] *ρ(r0): molecular density

[0225] *V; volume

[0226] *r; observation point

[0227] *d 3 r0: volume element

[0228] The value of the dipole moment can be obtained by calculating the molecular density in Mathematical Equation 1. For example, the molecular density can be obtained by obtaining the charge and dipole of each atom using a method called Hirshfeld charge analysis, and then calculating according to the following equation. The dipole moment can be obtained by substituting the calculated result into Mathematical Equation 1.

[0229] Weight function

[0230]

[0231] *ρ α (rR α ) : spherical average ground state atomic density

[0232] * :promolecule density

[0233] Deformation density

[0234]

[0235] *ρ(t): molecular density

[0236] *ρ α (rR α ): Located at coordinate R α The density of free atoms α at

[0237] Atomic charge

[0238] q(α)=-∫ρ A (r)W α (r)d 3 r

[0239] *W α (r): weight function

[0240] According to one embodiment of the present specification, the compound of Chemical Formula 1 and the compound of Chemical Formula 2 satisfy the following Formula 2. When the organic material layer is formed through one deposition source by premixing the compound of Chemical Formula 1 and the compound of Chemical Formula 2, a mixture having excellent uniformity can be obtained by satisfying the following Formula 2, and a uniform film can also be obtained in the step of manufacturing a device.

[0241] [Formula 2]

[0242] |T sub1 -T sub2 |≤20℃

[0243] T sub1 is the evaporation temperature of the compound of Chemical Formula 1, and

[0244] T sub2 is the evaporation temperature of the compound of Chemical Formula 2.

[0245] According to one embodiment of the present specification, “|T sub1 -T sub2 |" value can be 15℃ or lower.

[0246] In the present specification, the composition includes the compound of Chemical Formula 1 and the compound of Chemical Formula 2 in a mixed form, and the mixing ratio of the compound of Chemical Formula 1 to the compound of Chemical Formula 2 and the like are not limited.

[0247] In one embodiment of the present specification, the composition may mean a composition in which the compound of Chemical Formula 1 and the compound of Chemical Formula 2 are physically mixed, or may mean a sublimation mixture composition in which physically mixed materials are placed in a boat of a sublimator and sublimated at high temperature and high pressure.

[0248] One embodiment of the present specification provides a deposition source prepared using the composition. The deposition source comprises a composition in which the compound of Chemical Formula 1 and the compound of Chemical Formula 2 are physically mixed, or comprises a sublimation mixture composition in which the physically mixed materials are placed in a boat of a sublimator and sublimed at high temperature and high pressure. In the sublimation mixture composition prepared by the sublimator as above, the compounds are uniformly mixed, so that when used in a device, the device life or efficiency is improved.

[0249] One embodiment of the present specification provides an organic electroluminescent device including a cathode; an anode; and a light-emitting layer disposed between the cathode and the anode, wherein the light-emitting layer includes the composition.

[0250] To form a light emitting layer including the composition, co-deposition of the compound of Chemical Formula 1 and the compound of Chemical Formula 2 may be used, respectively, by different deposition sources, or a method of pre-mixing the compound of Chemical Formula 1 and the compound of Chemical Formula 2 and depositing them by one deposition source may be used.

[0251] According to one embodiment of the present specification, the material of the light-emitting layer may include the compound of Chemical Formula 1 and the compound of Chemical Formula 2 as a blue fluorescent host, and may include an additional dopant material. When using co-deposition to prepare a blue fluorescent light-emitting layer having such a mixed host material, three deposition sources are generally required, making the process very complex and expensive. Therefore, by pre-mixing two or more types of materials from three or more types of compounds and evaporating them from a single deposition source to form an organic material layer, the complexity of the manufacturing process can be reduced, and stable deposition can be achieved by simultaneous evaporation.

[0252] The two types of hosts (compounds of Chemical Formula 1 and Chemical Formula 2) exhibit stable miscibility and can be deposited simultaneously from a single deposition source because the composition variation after mixing is within a certain range. Uniform simultaneous evaporation of the two types of hosts is important for the performance consistency of the fabricated organic electroluminescent devices.

[0253] According to one embodiment of the present specification, the light-emitting layer includes the compound of Chemical Formula 1 and the compound of Chemical Formula 2 as a host, and further includes a dopant material. Here, the dopant material may be included in an amount of approximately 0.01% to 20% by mass, or 0.01% to 10% by mass, relative to the total mass of the compound of Chemical Formula 1 and the compound of Chemical Formula 2 in the light-emitting layer.

[0254] According to one embodiment of the present specification, the organic electroluminescent device is a multi-stack type, and one or two stacks thereof include the composition.

[0255] According to one embodiment of the present specification, the λmax of the emission spectrum of the light-emitting layer including the composition is within a range of 400 nm to 470 nm.

[0256] According to one embodiment of the present specification, the light-emitting layer further includes a fluorescent dopant.

[0257] According to one embodiment of the present specification, the light-emitting layer further includes a pyrene-based compound as a dopant.

[0258] According to another embodiment, the light-emitting layer further comprises an unsubstituted or deuterium-substituted pyrene-based compound as a dopant.

[0259] According to one embodiment, the light-emitting layer further comprises a non-pyrene-based compound as a dopant.

[0260] According to another embodiment, the light-emitting layer further comprises an unsubstituted or deuterium-substituted non-pyrene-based compound as a dopant.

[0261] According to one embodiment of the present specification, the non-pyrene-based compound includes a boron-based compound.

[0262] According to another embodiment, the non-pyrene-based compounds include unsubstituted or deuterium-substituted boron-based compounds.

[0263] In another embodiment, the compound of Chemical Formula 1 and the compound of Chemical Formula 2 each have an evaporation temperature below 400°C.

[0264] In another embodiment, the evaporation temperature of the compound of Chemical Formula 1 is higher than or equal to 200°C and lower than 400°C, or higher than or equal to 230°C and lower than or equal to 370°C.

[0265] According to another embodiment, the evaporation temperature of the compound of Chemical Formula 2 is higher than or equal to 200°C and lower than 400°C, or higher than or equal to 230°C and lower than or equal to 370°C.

[0266] When the compound of Chemical Formula 1 and the compound of Chemical Formula 2 are pre-mixed before deposition according to one embodiment of the present disclosure, they are evaporated simultaneously by one deposition source and need to be stable during the evaporation process. In other words, the film composition needs to remain constant during the manufacturing process, and for this reason, the composition variation of the mixed material needs to be within a certain range. Large variations in composition may adversely affect the performance of the manufactured device. Therefore, the materials to be mixed need to have small differences in evaporation temperature values. At a chamber base pressure of 1×10 -4 Up to 1×10 -9 In a high vacuum deposition apparatus of a VTE device, at a location where an evaporation source of the material is evaporated, for example, on a surface located at a determined distance from an evaporation crucible in the VTE device, As will be appreciated by those skilled in the art, due to expected errors in making various measurements, such as temperature, pressure, and deposition rate, such quantitative values ​​disclosed in this specification are expected to have nominal variations.

[0267] The “determined distance” means the distance between the evaporation source and the deposition surface in the deposition apparatus and is determined according to the chamber size.

[0268] According to one embodiment of the present specification, the compound of Chemical Formula 1 or the compound of Chemical Formula 2 has a concentration C1 in the composition, and the chamber base pressure is 1×10 -4 Up to 1×10 -9 In the high vacuum deposition device of the Seconds to / second, has a concentration C2 in a film formed by evaporating the composition on a surface located at a certain distance from a position where the composition is evaporated, and satisfies the following Formula 3.

[0269] [Formula 3]

[0270] │(C1-C2) / C1│<10%

[0271] According to one embodiment of the present specification, both the compound of Chemical Formula 1 and the compound of Chemical Formula 2 satisfy Formula 3.

[0272] In one embodiment of the present specification, concentrations C1 and C2 are the relative concentrations of the compound of Chemical Formula 1 or the compound of Chemical Formula 2. Therefore, the conventional requirements for the two compounds forming the above-mentioned composition mean that the relative concentration (C2) of the compound of Chemical Formula 1 in the deposited film needs to be as close as possible to the original relative concentration (C1) of the compound of Chemical Formula 1 in the evaporation source composition. It will be understood by those skilled in the art that the concentrations of each component are expressed as relative percentages. The concentrations of each component in the composition can be measured using appropriate analytical methods such as high pressure liquid chromatography (HPLC) and nuclear magnetic resonance (NMR) spectroscopy. The inventors of the present disclosure use HPLC and calculate the percentage by dividing the integral area under the HPLC scan line of each component by the total integral area. HPLC can use different detectors, such as UV-vis, photodiode array detectors, refractive index detectors, fluorescence detectors, and light scattering detectors. Due to different material properties, the components in the composition may react differently. Thus, the measured concentration may differ from the actual concentration in the composition. However, the relative ratio of (C1-C2) / C1 is independent of the above variables, as long as the experimental conditions are calculated to be constant, for example, assuming that all concentrations need to be maintained under exactly the same HPLC parameters for each component. Sometimes it is preferred to select measurement conditions so that the calculated concentration is close to the actual concentration. However, this is not required. It is important to select detection conditions that accurately detect each component. For example, when one of the components is not fluorescent, a fluorescence detector is not used.

[0273] In one embodiment of the present specification, the organic material layer obtained by depositing the composition through one deposition source may be a light emitting layer.

[0274] One embodiment of the present specification provides a method for manufacturing an organic electroluminescent device, the method comprising: preparing a composition; preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layer, wherein the forming of the one or more organic material layers comprises forming the one or more organic material layers using the composition.

[0275] The organic material layer of the organic electroluminescent device of the present specification may be formed in a single-layer structure, but may also be formed in a multilayer structure in which two or more organic material layers are laminated. For example, as a representative example of the organic electroluminescent device of the present specification, the organic electroluminescent device may include only one light-emitting layer as the organic material layer, but may have a structure that includes the following in addition to the light-emitting layer: a hole injection layer, a hole transport layer, a layer that simultaneously performs hole injection and hole transport, an electron control layer, a hole control layer, another light-emitting layer, an electron transport layer, an electron injection layer, a layer that simultaneously performs electron injection and electron transport, and the like.

[0276] In one embodiment of the present specification, the organic electroluminescent device may be an organic electroluminescent device (normal type) having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

[0277] In one embodiment of the present specification, the organic electroluminescent device may be an organic electroluminescent device having an inverted structure (inverted type) in which a cathode, one or more organic material layers, and an anode are sequentially laminated on a substrate.

[0278] In this specification, description that a certain member is placed “on” another member includes not only a case where one member is in contact with another member but also a case where another member exists between the two members.

[0279] In this specification, "layer" has a meaning compatible with the "film" mainly used in the field, and refers to a coating covering a target area. The size of the "layer" is not limited, and each "layer" can have the same or different sizes. According to one embodiment, the size of the "layer" can be the same as the entire device, can correspond to the size of a specific functional area, or can be as small as a single sub-pixel.

[0280] In this specification, the meaning that a specific A material is contained in the B layer includes both the following: i) one or more types of A materials are contained in one B layer, and ii) the B layer is formed into one or more layers, and the A material is contained in one or more of the B layers.

[0281] In this specification, the meaning that a specific A material is contained in the C layer or the D layer includes both of the following: i) contained in one or more layers among the one or more C layers, ii) contained in one or more layers among the one or more D layers, or iii) contained in each of the one or more C layers and the one or more D layers.

[0282] For example, the structure of an organic electroluminescent device according to one embodiment of the present specification is shown in Figure 1 and Figure 3 middle. Figure 1 and Figure 3 Only the organic electroluminescent device is shown, and the organic electroluminescent device is not limited thereto.

[0283] Figure 1 The structure of the organic electroluminescent device 10 is shown in which a substrate 20, an anode 30, a light-emitting layer 40, and a cathode 50 are sequentially laminated.

[0284] Figure 3 The structure of an organic electroluminescent device is shown in which a substrate 20, an anode 30, a hole injection layer 60, a hole transport layer 70, a hole control layer 80, a light-emitting layer 40, an electron control layer 90, an electron transport layer 100, an electron injection layer 110, a cathode 50 and a covering layer 120 are sequentially stacked.

[0285] The organic electroluminescent device of the present specification can be manufactured using materials and methods known in the art, except that one or more of the light-emitting layers comprises the above composition.

[0286] When the organic electroluminescent device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

[0287] For example, the organic electroluminescent device according to the present specification can be manufactured as follows: an anode is formed on a substrate by depositing a metal, a conductive metal oxide, or an alloy thereof using a physical vapor deposition (PVD) method (such as sputtering or electron beam evaporation), and an organic material layer including one or more of the following is formed on the anode: a hole injection layer, a hole transport layer, a layer that simultaneously performs hole injection and hole transport, an electron control layer, a hole control layer, a light-emitting layer, an electron transport layer, an electron injection layer, a layer that simultaneously performs electron injection and electron transport, and then a material that can be used as a cathode is deposited on the organic material layer. In addition to such a method, the organic electroluminescent device can also be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0288] One or more organic material layers can be formed using methods known in the art, such as deposition methods and solvent methods. When the organic material layer comprises two or more materials in the deposition method, co-deposition can be used in which the two or more materials are deposited using different deposition sources, or a method in which the two or more materials are pre-mixed and then deposited using a single deposition source can be used. Examples of solvent methods include spin coating, dip coating, doctor blade coating, screen printing, inkjet printing, thermal transfer methods, and the like.

[0289] The anode is an electrode that injects holes, and as an anode material, a material with a large work function is generally preferred so that the hole injection into the organic material layer is smooth. Specific examples of anode materials that can be used in the present disclosure include: metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or 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.

[0290] The cathode is an electrode that injects electrons. Cathode materials are generally preferably materials with a low work function to facilitate electron injection into the organic material layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO2 / Al.

[0291] The hole injection layer is a layer that smoothly injects holes from the anode into the light-emitting layer, and the hole injection material is a material that can advantageously receive holes from the anode at low voltage. The highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. The specific example of the hole injection material includes metal porphyrins, oligothiophenes, organic materials based on arylamines, organic materials based on hexanitrile hexaazatriphenylene, organic materials based on quinacridone, organic materials based on perylene, anthraquinone, and conductive polymers based on polyaniline and polythiophene, but is not limited thereto.

[0292] According to one embodiment of the present specification, the hole injection layer includes a compound of the following Chemical Formula HI-1, but is not limited thereto.

[0293] [Chemical formula HI-1]

[0294]

[0295] In the chemical formula HI-1,

[0296] At least one of X'1 to X'6 is N, and the rest are CH, and

[0297] R309 to R314 are the same as or different from each other and are each independently hydrogen; deuterium; cyano; substituted or unsubstituted alkyl; substituted or unsubstituted amino; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, or bond with an adjacent group to form a substituted or unsubstituted ring.

[0298] According to one embodiment of the present specification, X'1 to X'6 are N.

[0299] According to one embodiment of the present specification, R309 to R314 are cyano groups.

[0300] According to one embodiment of the present specification, the chemical formula HI-1 is the following compound.

[0301]

[0302] The hole transport layer can smoothly transport holes. Suitable hole transport materials include those that can receive holes from the anode or hole injection layer, transfer the holes to the light-emitting layer, and have high hole mobility. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0303] In one embodiment of the present specification, the hole transport layer includes a compound of the following Chemical Formula HT-1.

[0304] [Chemical formula HT-1]

[0305]

[0306] In the chemical formula HT-1,

[0307] L101 is a direct bond; or a substituted or unsubstituted arylene group, and

[0308] R101 and R102 are the same as or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amino group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0309] In one embodiment of the present specification, L101 is a substituted or unsubstituted phenylene group; or a substituted or unsubstituted naphthylene group.

[0310] In one embodiment of the present specification, L101 is a substituted or unsubstituted phenylene group.

[0311] In one embodiment of the present specification, L101 is a phenylene group.

[0312] In one embodiment of the present specification, R101 and R102 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group.

[0313] In one embodiment of the present specification, R101 and R102 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic aryl group.

[0314] In one embodiment of the present specification, R101 and R102 are the same as or different from each other, and are each independently substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted anthracenyl; substituted or unsubstituted phenanthrenyl; substituted or unsubstituted triphenylene; substituted or unsubstituted pyrenyl; or substituted or unsubstituted fluorenyl.

[0315] In one embodiment of the present specification, R101 and R102 are the same as or different from each other, and are each independently a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted fluorenyl group.

[0316] In one embodiment of the present specification, R101 and R102 are the same as or different from each other, and are each independently a biphenyl group; or a fluorenyl group substituted with an alkyl group.

[0317] In one embodiment of the present specification, the chemical formula HT-1 is the following compound.

[0318]

[0319] A hole control layer may be provided between the hole transport layer and the light emitting layer, and materials known in the art may be used as the hole control layer.

[0320] According to one embodiment of the present specification, the hole control layer includes a compound of the following Chemical Formula EB-1, but is not limited thereto.

[0321] [Chemical formula EB-1]

[0322]

[0323] In chemical formula EB-1,

[0324] R315 to R317 are the same as or different from each other and are each independently any one selected from the following: hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl; and combinations thereof, or bonded to an adjacent group to form a substituted or unsubstituted ring,

[0325] r315 is an integer of 1 to 5, and when r315 is 2 or greater, two or more R315 are the same as or different from each other, and

[0326] r316 is an integer of 1 to 5, and when r316 is 2 or greater, two or more R316 are the same as or different from each other.

[0327] According to one embodiment of the present specification, R317 is any one selected from substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl; and combinations thereof.

[0328] According to one embodiment of the present specification, R317 is any one selected from phenyl; biphenyl; and combinations thereof.

[0329] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group.

[0330] According to one embodiment of the present specification, R315 and R316 are each independently a substituted or unsubstituted polycyclic aromatic group.

[0331] According to one embodiment of the present specification, R315 and R316 are each independently a substituted or unsubstituted phenanthrenyl group.

[0332] According to one embodiment of the present specification, R315 and R316 are phenanthrenyl.

[0333] According to one embodiment of the present specification, Chemical Formula EB-1 is the following compound.

[0334]

[0335] An electron control layer may be provided between the electron transport layer and the light emitting layer. The electron control layer is a layer that blocks holes from reaching the cathode and can generally be formed under the same conditions as the hole injection layer. For example, materials for the electron control layer may include Oxadiazole derivatives, triazole derivatives, triazine derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., but not limited thereto. Specifically, triazine derivatives can be used, however, the electron control layer is not limited thereto.

[0336] In one embodiment of the present specification, the electron control layer includes a compound of the following Chemical Formula HB-1.

[0337] [Chemical formula HB-1]

[0338]

[0339] In the chemical formula HB-1,

[0340] L501 to L503 are the same as or different from each other and are each independently a direct bond; or a substituted or unsubstituted arylene group,

[0341] R501 and R502 are the same as or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amino group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclyl group.

[0342] In one embodiment of the present specification, L501 to L503 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted naphthylene group.

[0343] In one embodiment of the present specification, L501 to L503 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted phenylene group.

[0344] In one embodiment of the present specification, L501 to L503 are the same as or different from each other, and are each independently a direct bond; or a phenylene group.

[0345] In one embodiment of the present specification, R501 and R502 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group.

[0346] In one embodiment of the present specification, R501 and R502 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic aryl group.

[0347] In one embodiment of the present specification, R501 and R502 are the same as or different from each other, and are each independently substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted anthracenyl; substituted or unsubstituted phenanthrenyl; substituted or unsubstituted triphenylene; substituted or unsubstituted pyrenyl; or substituted or unsubstituted fluorenyl.

[0348] In one embodiment of the present specification, R501 and R502 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; or a substituted or unsubstituted naphthyl group.

[0349] In one embodiment of the present specification, R501 and R502 are the same as or different from each other, and are each independently a phenyl group; or a naphthyl group.

[0350] In one embodiment of the present specification, the chemical formula HB-1 is the following compound.

[0351]

[0352] The light-emitting layer can emit red, green, or blue light and can be formed of a phosphorescent material or a fluorescent material. The light-emitting material is a material that can emit light in the visible region by receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining the holes and electrons, and is preferably a material with favorable quantum efficiency for fluorescence or phosphorescence.

[0353] In addition to the two types of hosts in the above-mentioned composition, the host material of the light-emitting layer also includes fused aromatic ring derivatives, heterocyclic compounds, etc. Specifically, the fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and the heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc. However, the host material is not limited thereto.

[0354] When the light-emitting layer emits red light, a phosphorescent material such as bis(1-phenylisoquinoline)iridium acetylacetonate (PIQIr(acac)), bis(1-phenylquinoline)iridium acetylacetonate (PQIr(acac)), tris(1-phenylquinoline)iridium (PQIr) or platinum octaethylporphyrin (PtOEP), or a fluorescent material such as tris(8-hydroxyquinoline)aluminum (Alq3) can be used as a light-emitting dopant, however, the light-emitting dopant is not limited thereto. When the light-emitting layer emits green light, a phosphorescent material such as face tris(2-phenylpyridine)iridium (Ir(ppy)3), or a fluorescent material such as tris(8-hydroxyquinoline)aluminum (Alq3), anthracene-based compound, pyrene-based compound or boron-based compound can be used as a light-emitting dopant, however, the light-emitting dopant is not limited thereto. When the light-emitting layer emits blue light, a phosphorescent material such as (4,6-F2ppy)2Irpic, or a fluorescent material such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), PFO-based polymers, PPV-based polymers, anthracene-based compounds, pyrene-based compounds or boron-based compounds can be used as a light-emitting dopant, however, the light-emitting dopant is not limited thereto.

[0355] According to one embodiment of the present specification, the dopant includes a compound of the following Chemical Formula D-1, but is not limited thereto.

[0356] [Chemical Formula D-1]

[0357]

[0358] In Chemical Formula D-1,

[0359] T1 to T5 are the same as or different from each other and are each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amino group; or a substituted or unsubstituted aryl group.

[0360] t3 and t4 are each an integer from 1 to 4,

[0361] t5 is an integer from 1 to 3,

[0362] When t3 is 2 or more, two or more T3 are the same as or different from each other,

[0363] When t4 is 2 or greater, two or more T4 are the same as or different from each other, and

[0364] When t5 is 2 or greater, two or more T5s are the same as or different from each other.

[0365] According to one embodiment of the present specification, T1 to T5 are the same as or different from each other and are each independently hydrogen; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0366] According to one embodiment of the present specification, T1 to T5 are the same as or different from each other and are each independently hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms.

[0367] According to one embodiment of the present specification, T1 to T5 are the same as or different from each other, and are each independently hydrogen; a methyl group; a tert-butyl group; or a phenyl group which is unsubstituted or substituted with a tert-butyl group.

[0368] According to one embodiment of the present specification, Chemical Formula D-1 is the following compound.

[0369]

[0370] In one embodiment of the present specification, the dopant includes a compound of the following Chemical Formula D-2.

[0371] [Chemical Formula D-2]

[0372]

[0373] In chemical formula D-2,

[0374] L401 and L402 are the same as or different from each other and are each independently a direct bond; or a substituted or unsubstituted arylene group, and

[0375] R401 to R404 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amino group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0376] In one embodiment of the present specification, L401 and L402 are each a direct bond.

[0377] In one embodiment of the present specification, R401 to R404 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.

[0378] In one embodiment of the present specification, R401 to R404 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic aryl group; or a substituted or unsubstituted heterocyclic group.

[0379] In one embodiment of the present specification, R401 to R404 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 terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted pyrenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothienyl group.

[0380] In one embodiment of the present specification, R401 to R404 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; or a substituted or unsubstituted dibenzofuranyl group.

[0381] In one embodiment of the present specification, R401 to R404 are the same as or different from each other, and are each independently an unsubstituted or alkyl-substituted phenyl group; or an unsubstituted or alkyl-substituted dibenzofuranyl group.

[0382] In one embodiment of the present specification, Chemical Formula D-2 is the following compound.

[0383]

[0384] The electron transport layer facilitates electron transport. Suitable electron transport materials include those that can efficiently receive electrons from the cathode, transfer them to the light-emitting layer, and exhibit high electron mobility. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic free radical compounds; and hydroxyflavone-metal complexes.

[0385] The electron injection layer can play a role in smoothly injecting electrons. As the electron injection material, a compound that has electron transport ability, has an effect of injecting electrons from the cathode, has an excellent electron injection effect on the light-emitting layer or the light-emitting material, prevents the excitons generated in the light-emitting layer from migrating to the hole injection layer, and also has excellent thin film forming ability. Specific examples thereof may include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylmethane, anthrone, etc., and derivatives thereof; metal complex compounds; nitrogen-containing 5-membered ring derivatives; etc., but not limited thereto.

[0386] Metal complex compounds include 8-hydroxyquinolinate lithium, bis(8-hydroxyquinolinate) zinc, bis(8-hydroxyquinolinate) copper, bis(8-hydroxyquinolinate) manganese, tris(8-hydroxyquinolinate) aluminum, tris(2-methyl-8-hydroxyquinolinate) aluminum, tris(8-hydroxyquinolinate) gallium, bis(10-hydroxybenzo[h]quinolinate) beryllium, bis(10-hydroxybenzo[h]quinolinate) zinc, bis(2-methyl-8-quinolinate) chlorogallium, bis(2-methyl-8-quinolinate)(o-cresol) gallium, bis(2-methyl-8-quinolinate)(1-naphthol) aluminum, bis(2-methyl-8-quinolinate)(2-naphthol) gallium, and the like, but are not limited thereto.

[0387] The organic electroluminescent device according to the present disclosure may be a top emission type, a bottom emission type, or a dual emission type depending on the materials used.

[0388] Embodiments of the invention

[0389] Hereinafter, the present invention will be described in more detail by way of examples. However, the following examples are for illustrative purposes only and are not intended to limit the present invention.

[0390] [Preparation Example]

[0391] Preparation Example 1. Synthesis of Chemical Formula 1

[0392] Reaction material (1 equivalent) and trifluoromethanesulfonic acid (catalyst, cat.) are introduced into C6D6 (mass ratio relative to reaction material is 10 times to 50 times), and mixture is stirred at 70 ℃ for 10 minutes to 100 minutes.After reaction is completed, D2O (excessive) is introduced thereto, gained is stirred 30 minutes, and trimethylamine (excessive) is added dropwise thereto. Reaction solution is transferred to separating funnel, and is extracted with water and chloroform. By extract MgSO4 drying, heat with toluene, and recrystallize to obtain the product of following table 1.

[0393] [Table 1]

[0394]

[0395]

[0396]

[0397]

[0398] [Each product has a different degree of deuterium substitution depending on the reaction time, and the substitution rate is determined by the maximum m / z (M+) value] Compounds A to W as reaction materials were synthesized with reference to existing literature such as JP 4070676B2, KR 10-1477844B1, US6465115B2, JP 3148176B2, JP4025136B2, JP 4188082 B2, JP 5015459 B2, KR 10-1979037B1, KR10-1550351B1, KR 10-1503766B1, KR 10-0826364B1, KR 10-0749631B1 and KR10-1115255B1. Furthermore, compounds 1-A to 1-W, which are deuterium-substituted products, were synthesized with reference to the existing document KR 10-1538534B1.

[0399] In Table 1, deuterium (—D) bonded to the synthesized product means that it is capable of bonding to a designated position, and does not necessarily mean that deuterium is bound to the designated position.

[0400] Preparation Example 2. Synthesis of Chemical Formula 2

[0401] Reaction material (1 equivalent) and trifluoromethanesulfonic acid (catalyst) are introduced into C6D6 (mass ratio relative to reaction material is 10 times to 50 times), and mixture is stirred at 70 ℃ for 10 minutes to 100 minutes.After the reaction is completed, D2O (excessive) is introduced therein, gained is stirred 30 minutes, and trimethylamine (excessive) is added dropwise thereto. Reaction solution is transferred to separating funnel, and is extracted with water and chloroform. By extract MgSO4 drying, heat with toluene, and recrystallize to obtain the product of following table 2 and table 3.

[0402] [Table 2]

[0403]

[0404]

[0405]

[0406]

[0407]

[0408] [Each product has a different degree of deuterium substitution depending on the reaction time, and the substitution rate is determined by the maximum m / z (M+) value]

[0409] Compounds 1 to 27 as reaction materials were synthesized with reference to the applicant's prior art documents such as KR10-1964435B1, KR 10-1899728B1, KR 10-1975945B1, KR10-2018-0098122A, KR 10-2018-0102937A, and KR 10-2018-0103352A. In addition, compounds 2-1 to 2-27 as deuterium-substituted products were synthesized with reference to the prior art document KR10-1538534B1.

[0410] In Table 2, deuterium (—D) bonded to the synthesized product means capable of bonding to a designated position, and does not necessarily mean that deuterium is bound to the designated position.

[0411] [Table 3]

[0412]

[0413]

[0414]

[0415]

[0416] [Each product has a different degree of deuterium substitution depending on the reaction time, and the substitution rate is determined by the maximum m / z (M+) value]

[0417] Compounds 28 to 47 as reaction materials were synthesized with reference to the applicant's prior literature such as KR 10-1994238 B1, KR 10-1670193 B1, KR 10-1754445 B1, and KR 10-1368164 B1. In addition, compounds 2-28 to 2-47 as deuterium-substituted products were synthesized with reference to the prior literature KR 10-1538534 B1.

[0418] In Table 3, deuterium (—D) bonded to the synthesized product means that it is capable of bonding to a designated position, and does not necessarily mean that deuterium is bound to the designated position.

[0419] The dipole moment (DM) and evaporation temperature of each reaction material described in the preparation examples are shown in the following [Table 4].

[0420] [Table 4]

[0421]

[0422]

[0423] The chemical structures of the carbon-hydrogen skeleton and the carbon-deuterium skeleton of compounds A to W and compounds 1-A to 1-W are different, but have the same basic chemical skeleton and have almost the same dipole moment value, therefore, it can be considered that the dipole moment value and evaporation temperature value of compounds A to W are the same as those of compounds 1-A to 1-W. In addition, it can be considered that compounds 1 to 47 have the same dipole moment value and evaporation temperature value as compounds 2-1 to 2-47. The compound corresponding to the compound of Chemical Formula 1 and the compound corresponding to the compound of Chemical Formula 2 in the compound synthesized in the preparation example have a difference in dipole moment chemically and structurally. Compounds A to W corresponding to Chemical Formula 1 have a skeleton based only on carbon and hydrogen by having an aryl-based substituent, and the sectionalization of a few and many electrons is limited in the chemical structure, resulting in a result where the maximum value of the dipole moment (DM) value is not greater than 0.3 Debye. On the other hand, compared to compounds A to W according to Chemical Formula 1, compounds 1 to 47 according to Chemical Formula 2 have an anthracene skeleton substituted with a furan containing an aromatic or heteroaryl group with relatively electron-sufficient oxygen, and have been shown to have a relatively higher dipole moment (DM) due to the potential for deepening electron partitioning in chemical structures having a carbon-hydrogen skeleton. Therefore, the combination of the two structures proposed in this document has a range in which the DM difference between the two materials is greater than a minimum of 0.2.

[0424] [Experimental example]

[0425] [Experimental Example 1]

[0426] <Preparation of mixture>

[0427] It was determined that the evaporation temperature of the compound synthesized in the preparation example was lower than 400°C, and having a higher evaporation temperature revealed many limitations of materials used as organic electroluminescent devices. In addition, in order to pre-mix a mixture of one type of compound corresponding to Chemical Formula 1 and one type of compound corresponding to Chemical Formula 2 before evaporation by one evaporation source, it is necessary to preferably satisfy the following formula 2. When the following formula 2 is satisfied, a mixture with excellent uniformity can be obtained, and a uniform film can also be obtained in the step of manufacturing the device. In order to show such an effect, the following experiments (1) and (2) were performed.

[0428] [Formula 2]

[0429] │T sub1 -T sub2 │≤20℃

[0430] (T sub1 is the evaporation temperature of the compound of Chemical Formula 1, T sub2 is the evaporation temperature of the compound of Chemical Formula 2. (1)

[0432] To determine the miscibility of the compound of Chemical Formula 1 and the compound of Chemical Formula 2, a film formed by premixing the materials and then evaporating the mixture was tested using high pressure liquid chromatography (HPLC) analysis. Compound J prepared in Preparation Example was used as the compound of Chemical Formula 1, and Compound 6 prepared in Preparation Example was used as the compound of Chemical Formula 2.

[0433] Specifically, 0.15 g of compound J (or compound 1-J) and 0.15 g of compound 6 (or compound 2-6) were mixed (mass ratio 1:1) and crushed to obtain a composition, and the obtained composition was prepared into a sublimation mixture composition using a sublimator. Thereafter, the prepared sublimation mixture composition was loaded onto a crucible in a VTE vacuum chamber. The chamber was evacuated to 10 -7 The pressure of the support. The premixed components are deposited onto the glass substrate at a rate of 1000 ppm / s. Deposition is performed without interrupting the deposition process. The film is made of a film to avoid cooling of the raw materials and to keep the raw materials at a suitable temperature, and the process is repeated twice to replace the substrate. Three such substrate samples are taken to analyze the deposited films by HPLC, and the results are shown as Film 1 to Film 3 in Figure [1] below. From the experimental results of Figure [1] below, it is determined that the composition of Compound J and Compound 6 does not change significantly. Throughout the process, the concentration change before and after deposition (Formula 3 below) is 10% or less and preferably 5% or less, which is considered to be excellent and used for commercial OLED applications. The above concentration change is considered to be maintained when the evaporation temperature difference between the two mixed compounds is 20°C or less. (Evaporation temperature difference between Compound J and Compound 6: 10°C)

[0434] Slight changes in the concentration range of Formula 3 below did not reveal any device-wise trends, and sample collection and HPLC analysis can be explained by Formula 3 below.

[0435] [Formula 3]

[0436] │(C1-C2) / C1│<10%

[0437] Based on formula 3,

[0438] When the concentration C1 of compound 6 in the composition is 48.85%,

[0439] 1) The concentration of film 1 (C2) is 47.69%, so the concentration change is 2.3%,

[0440] 2) The concentration of film 2 (C2) is 46.94%, so the concentration change is 3.9%,

[0441] 3) The concentration (C2) of film 3 is 47.71%, so the concentration change is 2.3%.

[0442] [Figure[1]]

[0443]

[0444] - Reference: Composition of mixture before sublimation

[0445] - R1: mixture composition after sublimation (sublimation mixture composition)

[0446] -Boat: The composition remaining after preparing the sublimation mixture composition

[0447] - Films 1 to 3: Films prepared using sublimation mixture compositions

[0448] - Crucible: The composition remaining after preparing a film by loading the sublimation mixture composition on a deposition source

[0449] It was observed that the concentration variation was not significant in the above-prepared membranes 1 to 3, and the deviation between the membranes was small. Therefore, it was determined that the above conditions and Formula 2 were preferable. (2)

[0451] Results are shown for examples of mixtures that do not satisfy Formula 2. Here, Compound B and Compound 24 were used.

[0452] For mixing, 0.21 g of compound B (or compound 1-B) and 0.09 g of compound 24 (or compound 2-24) were mixed (mass ratio 7:3) and pulverized. The preparation conditions were the same as in (1), and the results are shown in Figure [2] below.

[0453] Based on formula 3,

[0454] When the concentration C1 of compound 24 in the composition is 69.30%,

[0455] 1) The concentration of film 1 (C2) is 65.42%, so the concentration change is 5.5%,

[0456] 2) The concentration of film 2 (C2) is 61.22%, so the concentration change is 11.6%,

[0457] 3) The concentration (C2) of film 3 is 62.82%, so the concentration change is 9.3%.

[0458] [Figure[2]]

[0459]

[0460] The concentration variation was significant in the films 1 to 3 prepared above, and in particular, a large deviation was observed between the films within a variation of 10% or more. Therefore, when a combination of a compound of Chemical Formula 1 that does not satisfy Formula 2 and a compound of Chemical Formula 2 was premixed and formed into a film using one evaporation source, a uniform film could not be obtained.

[0461] [Experimental Example 2] OLED Manufacturing

[0462] <Example 1>

[0463] As the anode, it will have a The ITO / Ag / ITO substrate was cut into a size of 50 mm × 50 mm × 0.5 mm, placed in distilled water dissolved with a dispersant, and ultrasonically cleaned. A product of Fischer Co. was used as a dispersant, and distilled water filtered twice using a filter manufactured by Millipore Co. was used as distilled water. After cleaning the ITO for 30 minutes, ultrasonic cleaning was repeated twice using distilled water for 10 minutes. After cleaning with distilled water, the substrate was ultrasonically cleaned with isopropyl alcohol, acetone, and methanol solvents in this order and then dried.

[0464] On the anode prepared as above, HI-1 was thermally vacuum deposited onto The hole injection layer is formed by vacuum depositing HT1 (a material for transporting holes) onto the hole injection layer. The hole transport layer is formed using EB1. A hole control layer was formed, and then a mixture prepared by using Compound A synthesized in Preparation Example 1 and Compound 2-1 synthesized in Preparation Example 2 and a dopant BD1 (2% by mass) was vacuum-deposited onto the Then, HB1 is deposited to form a light-emitting layer. The electron control layer is formed by mixing the compound ET1 and Liq in a ratio of 5:5 (mass ratio) to form a layer with a thickness of The electron transport layer is made of The magnesium and lithium fluoride (LiF) are continuously formed into a film as an electron injection layer, and then magnesium and silver (1:4) are formed into a film. as cathode, and then deposit CP1 onto To complete the device. In this process, the deposition rate of the organic material is kept at / Second.

[0465]

[0466] <Examples 2 to 43, Example 1-1, and Comparative Examples 1 to 6>

[0467] The devices of Examples 2 to 43, Example 1-1, and Comparative Examples 1 to 6 were manufactured in the same manner as in Example 1, except that the materials described in Table 6 below were used as the light-emitting layer materials and different light-emitting layer formation methods were used. In Example 1, the light-emitting layer was formed by pre-mixing Compound A and Compound 2-1 before forming the layer as in Experimental Example 1 and using one deposition source, and in the Comparative Examples and Examples having a deposition method as co-deposition in Table 6 below, the light-emitting layer was formed by depositing the first host, the second host, and the dopant each via a different deposition source.

[0468] The differences in dipole moment values ​​and evaporation temperatures between two types of host materials used as light-emitting layer materials in Comparative Examples 1 to 6 and Examples 1 to 43 are shown in Table 5 below.

[0469] [Table 5]

[0470]

[0471]

[0472]

[0473]

[0474] For the devices manufactured in Comparative Examples 1 to 6 and Examples 1 to 43, the 2 The driving voltage, luminous efficiency, color coordinates, and the time taken for the luminance to become 95% relative to the initial luminance (T95) were measured at a current density of 1.5 Å. The results are shown in Table 6 below.

[0475] [Table 6]

[0476]

[0477]

[0478]

[0479]

[0480]

[0481] The results in Table 6 indicate that, compared to Comparative Examples 1 to 6, which used mixtures of at least one type of deuterium-substituted compound (one type: Examples 1 to 13, two types: Examples 14 to 43) as blue fluorescent hosts, devices 1 to 43, which used mixtures of at least one type of deuterium-substituted compound (one type: Examples 1 to 13, two types: Examples 14 to 43), exhibited superior device characteristics, particularly lifetime, compared to Comparative Examples 1 to 6, which used mixtures of non-deuterium-substituted compounds as blue fluorescent hosts. This, like existing conventional methods, increases the potential for achieving low voltage and high efficiency by using a mixture of different series of anthracene hosts (aryl-based anthracene compounds and heteroaryl-based anthracene compounds). The introduction of deuterium enables the production of blue light-emitting devices with significantly superior lifetimes, suggesting improvements in existing blue devices. Furthermore, Comparative Examples 1 and 4, as well as Examples 1, 2, and 16, which formed the light-emitting layer from a single deposition source after premixing the two types of host materials prior to forming the light-emitting layer, exhibited superior device characteristics (voltage, efficiency, lifetime) compared to Comparative Examples 5 and 6, and Examples 3, 4, and 14, which formed the light-emitting layer from a single deposition source after co-depositing the same materials.

[0482] <Example 44> Production of OLED

[0483] As the anode, it will have a The ITO / Ag / ITO substrate was cut into a size of 50 mm × 50 mm × 0.5 mm, placed in distilled water dissolved with a dispersant, and ultrasonically cleaned. A product of Fischer Co. was used as a dispersant, and distilled water filtered twice using a filter manufactured by Millipore Co. was used as distilled water. After cleaning the ITO for 30 minutes, ultrasonic cleaning was repeated twice using distilled water for 10 minutes. After cleaning with distilled water, the substrate was ultrasonically cleaned with isopropyl alcohol, acetone, and methanol solvents in this order and then dried.

[0484] On the anode prepared as above, HI-1 was thermally vacuum deposited onto The hole injection layer is formed by vacuum depositing HT1 (a material for transporting holes) onto the hole injection layer. The hole transport layer is formed using EB1. A hole control layer was formed by vacuum depositing a mixture prepared using the compound B synthesized in Preparation Example 1 and the compound 2-3 synthesized in Preparation Example 2 and a dopant BD2 (2% by mass) onto the Then, HB1 is deposited to form a light-emitting layer. The electron control layer is formed by mixing compound ET1 and Liq at a ratio of 5:5 (mass ratio) to form a layer with a thickness of The electron transport layer is made of Mg and lithium fluoride (LiF) are continuously formed into a film as an electron injection layer (EIL), and then Mg and Ag (1:4) are formed into a film. as cathode, and then deposit CP1 onto To complete the device. In this process, the deposition rate of the organic material is kept at / Second.

[0485]

[0486] <Examples 45 to 84 and Comparative Examples 7 to 12>

[0487] The devices of Examples 45 to 84 and Comparative Examples 7 to 12 were manufactured in the same manner as in Example 44, except that the materials described in Table 8 below were used as the light-emitting layer materials and different light-emitting layer formation methods were used. In Example 44, the light-emitting layer was formed by pre-mixing Compound B and Compound 2-3 before forming the layer as in Experimental Example 1 and using one deposition source, and in the comparative examples and examples having a deposition method as co-deposition in Table 8 below, the light-emitting layer was formed by depositing the first host, the second host, and the dopant each via a different deposition source.

[0488] The differences in dipole moment values ​​and evaporation temperatures between two types of host materials used as light-emitting layer materials in Comparative Examples 7 to 12 and Examples 44 to 84 are shown in Table 7 below.

[0489] [Table 7]

[0490]

[0491]

[0492]

[0493]

[0494] For the devices manufactured in Comparative Examples 7 to 12 and Examples 44 to 84, the 2 The driving voltage, luminous efficiency, color coordinates, and the time taken for the luminance to become 95% relative to the initial luminance (T95) were measured at a current density of 1.5 Å. The results are shown in Table 8 below.

[0495] [Table 8]

[0496]

[0497]

[0498]

[0499]

[0500]

[0501] Examples 44 to 84 showed the same trend as Examples 1 to 43 of Table 6, and it was confirmed that the advantages and characteristics of dopant performance can be maintained when a boron-based blue fluorescent dopant is used in addition to a pyrene-based blue fluorescent dopant. Examples 44 to 84 were confirmed to have superior device characteristics compared to Comparative Examples 7 to 12, which contained mixtures of compounds not substituted with deuterium.

[0502] In addition, it was determined that Comparative Examples 7 and 9 and Examples 44 and 45, in which the light-emitting layer was formed by one deposition source after pre-mixing two types of host materials before forming the light-emitting layer, had excellent device characteristics (voltage, efficiency, and life) compared with Comparative Examples 11 and 12 and Examples 46 and 47, in which the light-emitting layer was formed by co-depositing the same material.

Claims

1. A deposition source, prepared using a composition comprising: The compound of the following Chemical Formula 1; and The compound of the following chemical formula 2, wherein the deposition source comprises pre-mixed compounds of Chemical Formula 1 and Chemical Formula 2, and the mixture is deposited by one deposition source: In Chemical Formula 1, One to three of R1 to R10 are bonded to the * site of Chemical Formula 1-1, and the rest are the same as or different from each other and are each independently hydrogen or deuterium; L1 is a direct bond, unsubstituted or deuterium-substituted phenylene, or unsubstituted or deuterium-substituted biphenylene; Ar is unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted biphenyl, unsubstituted or deuterium-substituted terphenyl, unsubstituted or deuterium-substituted naphthyl, unsubstituted or deuterium-substituted phenanthrenyl, or unsubstituted or deuterium-substituted triphenylene; and p is an integer from 1 to 5, In Chemical Formula 2, One to three of Y1 to Y10 are bonded to the * position of Chemical Formula 2-1, and the rest 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 phenanthrenyl, or substituted or unsubstituted triphenylene, and the "substituted" refers to substitution with deuterium, unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted biphenyl, unsubstituted or deuterium-substituted terphenyl, unsubstituted or deuterium-substituted naphthyl, unsubstituted or deuterium-substituted phenanthrenyl, or unsubstituted or deuterium-substituted triphenylene; A and B are the same as or different from each other and are each independently benzene which is unsubstituted or substituted with one or more substituents selected from deuterium and an unsubstituted or deuterium-substituted aryl group having 6 to 30 carbon atoms; unsubstituted or deuterium-substituted naphthalene; unsubstituted or deuterium-substituted phenanthrene; unsubstituted or deuterium-substituted triphenylene; or unsubstituted or deuterium-substituted dibenzofuran; L2 is a direct bond, unsubstituted or deuterium-substituted phenylene, unsubstituted or deuterium-substituted biphenylene, or unsubstituted or deuterium-substituted naphthylene; q is an integer from 1 to 5, The deuterium substitution rate of one or both of the compound of Chemical Formula 1 and the compound of Chemical Formula 2 is 50% to 100%.

2. The deposition source according to claim 1, wherein Chemical Formula 1 is any one of the following Chemical Formulas 1-A to 1-C: [Chemical Formula 1-A] [Chemical Formula 1-B] [Chemical Formula 1-C] In Chemical Formulas 1-A to 1-C, R1' to R8' are the same as or different from each other, and are each independently hydrogen or deuterium; L11 to L14 are the same as or different from each other, and are each independently a direct bond, an unsubstituted or deuterium-substituted phenylene group, or an unsubstituted or deuterium-substituted biphenylene group; and Ar11 to Ar14 are the same as or different from each other, and are each independently an unsubstituted or deuterium-substituted phenyl group, an unsubstituted or deuterium-substituted biphenyl group, an unsubstituted or deuterium-substituted terphenyl group, an unsubstituted or deuterium-substituted naphthyl group, an unsubstituted or deuterium-substituted phenanthrenyl group, or an unsubstituted or deuterium-substituted triphenyl group.

3. The deposition source according to claim 1, wherein the compound of Chemical Formula 1 and the compound of Chemical Formula 2 satisfy the following Formula 1: [Formula 1] │DM 主体1 -DM 主体2 │>0.2 DM 主体1 is the dipole moment value of the compound of Chemical Formula 1; and DM 主体2 is the dipole moment value of the compound of Chemical Formula 2. 4 . The deposition source according to claim 1 , wherein a mass ratio of the compound of Chemical Formula 1 to the compound of Chemical Formula 2 is 1:9 to 9:

1.

5. The deposition source according to claim 1, wherein the compound of Chemical Formula 1 and the compound of Chemical Formula 2 satisfy the following Formula 2: [Formula 2] │T sub1 -T sub2 │≤20℃ T sub1 is the evaporation temperature of the compound of Chemical Formula 1; and T sub2 is the evaporation temperature of the compound of Chemical Formula 2. 6 . The deposition source of claim 1 , wherein the compound of Chemical Formula 1 and the compound of Chemical Formula 2 have an evaporation temperature lower than 400° C.

7. The deposition source according to claim 1, wherein the compound of Chemical Formula 1 or the compound of Chemical Formula 2 has a concentration C1 in the composition, and the chamber base pressure is 1×10 -4 Up to 1×10 -9 In the high vacuum deposition device of the / second to / second, has a concentration C2 in a film formed by evaporating the composition on a surface located at a determined distance from a position where the composition is evaporated, and satisfies the following formula 3: [Formula 3] │(C1-C2) / C1│<10%.

8. An organic electroluminescent device comprising: cathode; anode; and A light-emitting layer is provided between the cathode and the anode, wherein the light-emitting layer comprises a composition comprising: The compound of the following chemical formula 1; and The compound of the following chemical formula 2, The light-emitting layer is deposited using a pre-mixed compound of Chemical Formula 1 and a pre-mixed compound of Chemical Formula 2, and the light-emitting layer is deposited by a deposition source: In Chemical Formula 1, One to three of R1 to R10 are bonded to the * site of Chemical Formula 1-1, and the rest are the same as or different from each other and are each independently hydrogen or deuterium; L1 is a direct bond, unsubstituted or deuterium-substituted phenylene, or unsubstituted or deuterium-substituted biphenylene; Ar is unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted biphenyl, unsubstituted or deuterium-substituted terphenyl, unsubstituted or deuterium-substituted naphthyl, unsubstituted or deuterium-substituted phenanthrenyl, or unsubstituted or deuterium-substituted triphenylene; and p is an integer from 1 to 5, In Chemical Formula 2, One to three of Y1 to Y10 are bonded to the * position of Chemical Formula 2-1, and the rest 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 phenanthrenyl, or substituted or unsubstituted triphenylene, and the "substituted" refers to substitution with deuterium, unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted biphenyl, unsubstituted or deuterium-substituted terphenyl, unsubstituted or deuterium-substituted naphthyl, unsubstituted or deuterium-substituted phenanthrenyl, or unsubstituted or deuterium-substituted triphenylene; A and B are the same as or different from each other and are each independently benzene which is unsubstituted or substituted with one or more substituents selected from deuterium and an unsubstituted or deuterium-substituted aryl group having 6 to 30 carbon atoms; unsubstituted or deuterium-substituted naphthalene; unsubstituted or deuterium-substituted phenanthrene; unsubstituted or deuterium-substituted triphenylene; or unsubstituted or deuterium-substituted dibenzofuran; L2 is a direct bond, unsubstituted or deuterium-substituted phenylene, unsubstituted or deuterium-substituted biphenylene, or unsubstituted or deuterium-substituted naphthylene; q is an integer from 1 to 5, The deuterium substitution rate of one or both of the compound of Chemical Formula 1 and the compound of Chemical Formula 2 is 50% to 100%. 9 . The organic electroluminescent device according to claim 8 , which is a multi-stack type, and one or two stacks thereof contain the composition. 10 . The organic electroluminescent device according to claim 8 , wherein the λmax of the emission spectrum of the light-emitting layer comprising the composition is within a range of 400 nm to 470 nm. The organic electroluminescent device according to claim 8 , wherein the light-emitting layer further comprises a fluorescent dopant. 12 . The organic electroluminescent device according to claim 8 , wherein the light-emitting layer further comprises a pyrene-based compound as a dopant. 13 . The organic electroluminescent device according to claim 8 , wherein the light-emitting layer further comprises a non-pyrene-based compound as a dopant. The organic electroluminescent device according to claim 13 , wherein the non-pyrene-based compound comprises a boron-based compound.

15. A method for manufacturing an organic electroluminescent device, the method comprising: preparing the deposition source according to claim 1; Prepare the substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; as well as forming a second electrode on the organic material layer, The forming of the one or more organic material layers includes forming the one or more organic material layers using the deposition source.

Citation Information

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