Organic electroluminescent device

Abstract

An organic electroluminescent device includes: a first electrode; a second electrode; and an organic layer formed between the first electrode and the second electrode. The organic layer comprises a light-emitting layer formed using a solution containing an organic electroluminescent material and a solvent. The organic electroluminescent material comprises a first substrate as shown in [Chemical Formula 1], a second substrate as shown in [Chemical Formula 2], and a dopant. [Chemical Formula 1] [Chemical Formula 2]

Description

Technical Field

[0001] This invention relates to an organic electroluminescent device, and more specifically, to an organic electroluminescent device in which the operating characteristics of the device, such as luminous efficiency, driving voltage, and lifetime, are improved by including an organic electroluminescent material with high solubility in a solvent.

[0002] For reference, this invention is part of a research project of the Korea Institute for Industrial Technology Evaluation and Management under the Ministry of Trade, Industry and Energy of Korea. The project aims to establish a display innovation process platform as a future growth driver for the materials and components industry. It is the result of a research project conducted by SFC Co., Ltd. under the project title "Development of High-Performance, Long-Life Emitting Layer Ink Materials and Device Technology for Printing Processes" (Project No.: 20011059), with a research period from April 1, 2020 to December 31, 2024. Background Technology

[0003] Organic light-emitting devices (OLEDs) are display devices that utilize the phenomenon of self-emission. They have a wide viewing angle, can be thinner and smaller than liquid crystal displays (LCDs), and have a fast response speed, so they are used as full-color displays or lighting.

[0004] Generally, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic electroluminescent devices (OLEDs) utilizing organic light emission typically have a structure including an anode, a cathode, and an organic layer between them. To improve the luminous efficiency and stability of OLEDs, the organic layer is usually composed of a multilayer structure of different materials; for example, it can consist of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In this structure, when a voltage is applied between the two electrodes, holes are injected from the anode, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed. When these excitons return to their ground state, they emit light. These OLEDs are known to possess characteristics such as self-emission, high brightness, high luminous efficiency, low driving voltage, wide viewing angle, high contrast, and high-speed response.

[0005] Currently, displays are becoming increasingly larger. When using deposition processes to manufacture large displays, there are drawbacks such as reduced yield and increased investment costs as the substrate size increases. Furthermore, because deposition processes involve evaporating single-molecule materials under vacuum conditions and depositing them onto the substrate, materials with high glass transition temperatures are required to prevent decomposition at the high evaporation temperatures, thus presenting limitations.

[0006] On the other hand, when large displays are manufactured by preparing a solution by dissolving organic electroluminescent materials in a solvent and then coating the solution onto a substrate, the process cost is lower than that of deposition processes and the process steps are relatively simple. However, organic electroluminescent materials typically have low solubility in solvents, making it difficult to guarantee the luminous efficiency, brightness, power efficiency, lifetime, and thermal stability of the device.

[0007] Therefore, there is an ongoing need to develop organic electroluminescent materials that have high solubility in solvents and can improve the luminous efficiency, brightness, power efficiency, lifetime, and thermal stability of devices. Summary of the Invention

[0008] In order to solve the problems mentioned above, the present invention aims to provide an organic electroluminescent device that uses an organic electroluminescent material with high solubility in a solvent, thereby having a lower driving voltage and improving luminous efficiency and lifetime characteristics.

[0009] The problems to be solved by this invention are not limited to those described above, and those skilled in the art will clearly understand from the following description other problems not mentioned.

[0010] <1> The organic electroluminescent device of the present invention includes a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode. The organic layer includes a light-emitting layer formed using a solution containing an organic electroluminescent material and a solvent. The organic electroluminescent material may include a first host as shown in [Chemical Formula 1], a second host as shown in [Chemical Formula 2], and a dopant.

[0011] [Chemical Formula 1]

[0012]

[0013] In the [Chemical Formula 1], each L1 is independently selected from the group consisting of substituted or unsubstituted C1-C20 alkylene, substituted or unsubstituted C6-C30 arylene, and substituted or unsubstituted C2-C30 heteroarylene.

[0014] The R and R1 to R 12They may be identical or different from each other, and each independently is selected from hydrogen atom, deuterium atom, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C5-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C30 alkylthiooxy, substituted or unsubstituted C6-C30 arylthiooxy, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C6-C30 The R1 to R1 groups comprise any one of the following groups: arylamine, substituted or unsubstituted C2-C30 heteroarylamine, substituted or unsubstituted C12-C24 diarylamine, substituted or unsubstituted C2-C24 diheteroarylamine, substituted or unsubstituted C7-C24 aryl (heteroaryl)amine, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C3-C50 heteroaryl, substituted or unsubstituted C8-C50 mixed cyclic group, substituted or unsubstituted C1-C30 alkylsilyl, and substituted or unsubstituted C6-C30 arylsilyl. 12 One of them is a single bond connected to the linking group L1.

[0015] Ar1 is selected from the group consisting of substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C50 heteroaryl groups, and substituted or unsubstituted C8-C50 mixed cyclic groups.

[0016] n is an integer from 1 to 5. When n is 2 or more, each L1 is either the same as or different from the others.

[0017] m1 is an integer from 0 to 8. When m1 is 2 or greater, each R is either the same as or different from the others.

[0018] [Chemical Formula 2]

[0019]

[0020] In the [Chemical Formula 2], the R 13 To R 20Each may be the same or different, and independently selected from hydrogen atom, deuterium atom, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C5-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C30 alkylsulfoxy The following are included: alkyl, substituted or unsubstituted C6-C30 arylsulfoxy, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C2-C50 heteroaryl with heteroatoms O, N or S, cyano, nitro, halogen atom, substituted or unsubstituted C1-C30 alkylsilyl, and substituted or unsubstituted C6-C30 arylsilyl.

[0021] The L 11 and L 12 They may be identical or different from each other, and each is independently selected from the group consisting of single bonds, substituted or unsubstituted C1-C20 alkylene groups, substituted or unsubstituted C6-C30 arylene groups, and substituted or unsubstituted C2-C30 heteroarylene groups.

[0022] The Ar 11 and Ar 12 Each group, whether identical or different, and independently selected from the group consisting of substituted or unsubstituted C6-C50 aryl groups, substituted or unsubstituted C2-C50 heteroaryl groups, and substituted or unsubstituted C8-C50 mixed cyclic groups, may be the same or different.

[0023] The condition is that Ar 11 and Ar 12 At least one of them is a group represented by the following [structural formula Ar-11] or [structural formula Ar-12]:

[0024]

[0025] In the aforementioned [structural formula Ar-11] and [structural formula Ar-12],

[0026] The "*" indicates that it is related to L. 11 or L 12 The bonding position of L 11 or L 12 When it is a single bond, it indicates the bonding position with anthracene.

[0027] X is selected from the group consisting of O, S, C(R')2, NR', and Si(R')2.

[0028] The R 21 R22 R and R' are either the same as or different from each other, and are each independently selected from the group consisting of hydrogen atom, deuterium atom, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C5-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C30 alkylthiooxy, substituted or unsubstituted C6-C30 arylthiooxy, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C3-C50 heteroaryl, substituted or unsubstituted C1-C30 alkylsilyl, and substituted or unsubstituted C6-C30 arylsilyl, and two or more adjacent R's. 21 Or R 22 They can combine with each other to form alicyclic or aromatic monocyclic or polycyclic compounds.

[0029] Where n1 is an integer from 1 to 7, and n2 is an integer from 1 to 5, when n1 and n2 are 2 or more, each R 21 and R 22 They are the same or different from each other.

[0030] <2> In the <1> middle,

[0031] The compound shown in [Chemical Formula 1] can be substituted with at least one deuterium atom.

[0032] <3> In the <2> middle,

[0033] The degree of deuteration of the compound shown in [Chemical Formula 1] can be 30% or more.

[0034] <4> In the <1> to <3> middle,

[0035] The compound shown in [Chemical Formula 1] may contain at least one substituted or unsubstituted C3-C30 heteroaryl group.

[0036] <5> In the <1> to <4> middle,

[0037] The molecular weight of the compound shown in [Chemical Formula 1] can be 650 or higher.

[0038] <6> In the <1> to <5> middle,

[0039] In the aforementioned [Chemical Formula 1],

[0040] The L1 can be a substituted or unsubstituted C6-C20 arylene.

[0041] <7> In the <1> to <6> middle,

[0042] In the aforementioned [Chemical Formula 1],

[0043] The number n can be an integer from 2 to 5.

[0044] <8> In the <1> to <6> middle,

[0045] The first subject may be as shown in any of [1-1] to [1-65] below.

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053] <9> In the <1> to <8> middle,

[0054] The second entity shown in [Chemical Formula 2] can be any one of the compounds shown in [Chemical Formula 2-1] to [Chemical Formula 2-4] below.

[0055]

[0056] The R 13 To R 22 L 11 L 12 Ar 11 n1 and n2 are as follows <1> Defined in [Chemical Formula 2].

[0057] <10> In the <9> middle,

[0058] In the aforementioned [Chemical Formula 2-1] and [Chemical Formula 2-2],

[0059] The R 21 At least one of them can be a substituted or unsubstituted C6-C30 aryl group, in [Chemical Formula 2-3] and [Chemical Formula 2-4], the R 22 At least one of them can be a substituted or unsubstituted C6-C30 aryl group.

[0060] <11> In the <1> to <10> middle,

[0061] The second body may be as shown in any of [2-1] to [2-159] below.

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079] <12> In the <1> to <11> middle,

[0080] The solvent may include at least one of chlorinated solvents, ether solvents, aromatic solvents, aliphatic solvents, ketone solvents, ester solvents, alcohol solvents, amide solvents, and benzoic acid ester solvents.

[0081] <13> In the <1> to <12> middle,

[0082] The solubility of both the first and second components in the solvent can be greater than 1% by weight.

[0083] <14> In the <1> to <13> middle,

[0084] The dopant can be a compound shown in [Chemical Formula 3-1] or [Chemical Formula 3-2] below.

[0085]

[0086] In the aforementioned [Chemical Formula 3-1] and [Chemical Formula 3-2],

[0087] T1 to T3 may be the same as or different from each other, and are independently C6-C50 aromatic hydrocarbon rings or C2-C40 aromatic heterocycles.

[0088] T1 to T3 can each be independently controlled by at least one R T Replacement, when replaced by two or more R T When replaced, these R T Whether they are the same or different,

[0089] The R T The atom is selected from any one of the following groups: hydrogen atom, deuterium atom, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C24 alkynyl, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C5-C30 cycloalkenyl, substituted or unsubstituted C2-C50 heteroaryl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C30 alkylthiooxy, substituted or unsubstituted C5-C30 arylthiooxy, -N(R”)2, substituted or unsubstituted C1-C30 alkylsilyl, substituted or unsubstituted C5-C30 arylsilyl, cyano, and halogen atom.

[0090] The R's may be the same as or different from each other, and each is independently selected from the group consisting of hydrogen atoms, deuterium atoms, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C2-C30 alkenyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C5-C30 cycloalkenyl groups, substituted or unsubstituted C6-C50 aryl groups, and substituted or unsubstituted C3-C50 heteroaryl groups. The R's can combine with each other to form alicyclic or aromatic monocyclic or polycyclic rings.

[0091] Y1 is selected from NR 31 CR 32 R 33 O, S, Se and SiR 34 R 35 any of them,

[0092] Y2 is selected from NR 36 CR 37 R 38 O, S and SiR 39 R 40 any of them,

[0093] Y3 is selected from NR 41 CR 42 R 43 O, S and SiR 44 R 45 any of them,

[0094] The R 31 To R 45 Each may be the same as or different from the others, and independently selected from hydrogen atom, deuterium atom, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C5-C30 cycloalkenyl, substituted or unsubstituted C2-C50 heteroaryl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C30 alkylsulfoxy The R group comprises any one of the following: substituted or unsubstituted C5-C30 arylsulfooxy group, substituted or unsubstituted C1-C30 alkylamino group, substituted or unsubstituted C6-C30 arylamino group, substituted or unsubstituted C2-C30 heteroarylamino group, substituted or unsubstituted C12-C24 diarylamino group, substituted or unsubstituted C2-C24 diheteroarylamino group, substituted or unsubstituted C7-C24 aryl (heteroaryl)amino group, substituted or unsubstituted C1-C30 alkylsilyl group, substituted or unsubstituted C5-C30 arylsilyl group, cyano group, and halogen atom. 31 To R 45 Each can combine with one or more rings selected from T1 to T3 to further form alicyclic or aromatic monocyclic or polycyclic rings.

[0095] <15> In the <14> middle,

[0096] The compounds shown in [Chemical Formula 3-1] and [Chemical Formula 3-2] may contain at least one -N(R”)2.

[0097] <16> In the <1> to <15> middle,

[0098] In addition to the light-emitting layer, the organic layer may also include at least one of the following: a hole injection layer, a hole transport layer, a functional layer that has both hole injection and hole transport functions, an electron transport layer, and an electron injection layer.

[0099] <17> In the <1> to <16> middle,

[0100] The organic layer can be formed by any of the following methods: spin coating, dip coating, doctor blade coating, spray coating, roller coating, inkjet printing, and screen printing.

[0101] The organic electroluminescent device of the present invention can be prepared using organic electroluminescent materials with high solubility in solvents, and has excellent device operating characteristics and lifetime characteristics, such as luminous efficiency and driving voltage. Attached Figure Description

[0102] Figure 1 This is a simplified cross-sectional view of an organic electroluminescent device according to an example of the present invention.

[0103] Explanation of reference numerals in the attached figures

[0104] 10: Substrate

[0105] 20: First electrode

[0106] 30: Hole injection layer

[0107] 40: Hole transport layer

[0108] 50: Emissive layer

[0109] 60: Electron transport layer

[0110] 70: Electron Injection Layer

[0111] 80: Second electrode Detailed Implementation

[0112] In this specification, "substituted or unsubstituted" can mean substituted by one or more substituents selected from the group consisting of deuterium, cyano, halogen group, hydroxyl, nitro, C1-C30 alkyl, C2-C30 alkenyl, C2-C24 alkynyl, C3-C30 cycloalkyl, C5-C30 cycloalkenyl, C1-C24 heteroalkyl, C6-C50 aryl, C7-C24 arylalkyl, C7-C24 alkylaryl, C2-C50 heteroaryl, C2-C24 heteroarylalkyl, C1-C30 alkoxy, C1-C30 alkylsulfoxy, C6-C30 arylsulfoxy, -N(R")2, C1-C30 alkylsilyl, C6-C30 arylsilyl, C6-C30 aryloxy, and C6-C24 arylthionyl.

[0113] Furthermore, considering the range of alkyl or aryl groups in "substituted or unsubstituted C1-C30 alkyl", "substituted or unsubstituted C6-C50 aryl", etc., the range of carbon atoms in C1-C30 alkyl and C6-C50 aryl, etc., respectively refers to the total number of carbon atoms constituting the alkyl or aryl moiety when the substituent is considered unsubstituted and the substituted portion is disregarded. For example, a phenyl group substituted at the para-butyl position should be considered as corresponding to an aryl group with 6 carbon atoms substituted by a butyl group having 4 carbon atoms.

[0114] In this specification, aryl refers to an aromatic system composed of hydrocarbons containing one or more rings. When the aryl group has substituents, it can be further fused with adjacent substituents to form a (mixed) ring.

[0115] Specific examples of the aryl group include phenyl, o-phenyl, meta-phenyl, para-phenyl, o-terphenyl, meta-terphenyl, para-terphenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, indene, fluorenyl, perylene, etc. Aromatic groups such as benzo[a], tetraphenyl, fluoranyl, and benzo[a]phenanthryl.

[0116] In this specification, a heteroaryl group refers to a cyclic aromatic system containing 2 to 24 carbon atoms, comprising 1, 2, or 3 heteroatoms selected from N, O, P, Si, S, Ge, Se, or Te, with the remaining ring atoms being carbon. These rings can be fused to form (mixed) rings. Furthermore, one or more hydrogen atoms in the heteroaryl group can be substituted with substituents in the same manner as those in the aryl group.

[0117] Specific examples of the aforementioned heteroaryl groups include furanyl, benzofuranyl, dibenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, pyrroleyl, indolyl, carbazoyl, pyridyl, quinolinyl, imidazoyl, benzimidazolyl, oxazolyl, benzoxazolyl, triazinyl, triazolyl, piperidinyl, acridineyl, phenoxazinyl, thiazoyl, benzothiazoyl, pyrimidinyl, pyrazinyl, etc.

[0118] In this specification, arylene and heteroarylene refer to divalent groups from which one hydrogen atom is further removed, respectively, from the aryl and heteroaryl groups.

[0119] In this specification, the mixed ring (group) is an aliphatic-aromatic mixed ring (group), which can refer to a ring formed by the connection and fusion of two or more rings, that is, a ring formed by the fusion of (hetero)aliphatic rings and (hetero)aromatic rings, and can be formed by the interconnection of adjacent substituents of the aryl or heteroaryl groups. More specifically, it can be an aromatic hydrocarbon ring (group) fused with an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring (group) fused with a heteroaliphatic hydrocarbon ring, a heteroaliphatic hydrocarbon ring (group) fused with an aliphatic hydrocarbon ring, a heteroaliphatic hydrocarbon ring (group) fused with a heteroaliphatic hydrocarbon ring, an aliphatic hydrocarbon ring (group) fused with an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring (group) fused with a heteroaliphatic hydrocarbon ring, a heteroaliphatic hydrocarbon ring (group) fused with an aromatic hydrocarbon ring, a heteroaliphatic hydrocarbon ring (group) fused with a heteroaliphatic hydrocarbon ring, etc. The mixed ring group can be a C8-C50 mixed ring group. Specific examples include tetrahydronaphthyl, tetrahydrobenzocycloheptenyl, tetrahydrophenanthryl, tetrahydroanthryl, octahydrobenzophenanthryl, tetrahydrobenzothiopheneyl, tetrahydrobenzofuranyl, tetrahydrocarbazoleyl, tetrahydroquinolinyl, etc. Furthermore, in rings (groups) formed by the fusion of aliphatic and aromatic rings, carbon can be replaced by heteroatoms such as N, O, S, Si, Ge, or P.

[0120] In this specification, alkyl groups are either straight-chain or branched. Specific examples include methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, etc., and one or more hydrogen atoms of the alkyl group can be substituted by substituents in the same way as those of the aryl group.

[0121] In this specification, heteroalkyl refers to one or more carbon atoms in the main chain of the alkyl group, preferably 1 to 5 carbon atoms are replaced by heteroatoms such as oxygen, sulfur, nitrogen, and phosphorus. Furthermore, one or more hydrogen atoms in the heteroalkyl group may be replaced by substituents in the same manner as in the case of the alkyl group.

[0122] In this specification, "cycloalkyl" refers to a substituent having a structure that can form a monocyclic or polycyclic ring of a saturated hydrocarbon in an alkyl group. Specific examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, methylcyclohexyl, ethylcyclopentyl, ethylcyclohexyl, adamantyl, dicyclobenzeneyl, decahydronaphthyl, norbornyl, bornyl, isobornyl, etc., and one or more hydrogen atoms in the cycloalkyl group can be substituted by substituents in the same way as those in the case of aryl groups.

[0123] In this specification, alkoxy is a substituent with an oxygen atom attached to the end of an alkyl or cycloalkyl group. Specific examples include methoxy, ethoxy, propoxy, isobutoxy, sec-butoxy, pentoxy, isopentoxy, and hexoxy, etc., and one or more hydrogen atoms of the alkoxy group can be substituted by substituents in the same way as those of the aryl group.

[0124] In this specification, specific examples of aryl alkyl groups include benzyl (benzyl), phenethyl, phenylpropyl, naphthylmethyl, naphthylethyl, etc., and one or more hydrogen atoms of the aryl alkyl group may be substituted with substituents in the same manner as those of the aryl group.

[0125] In this specification, specific examples of alkylsilanes include trimethylsilane, triethylsilane, and methylcyclobutylsilane, etc., and one or more hydrogen atoms in the alkylsilane can be substituted with substituents in the same way as in the case of the aryl group.

[0126] In this specification, specific examples of arylsilanes include triphenylsilane, diphenylmethylsilane, and diphenylvinylsilane, etc., and one or more hydrogen atoms of the arylsilane may be substituted with substituents in the same manner as the aryl group.

[0127] In this specification, alkenyl refers to an alkyl substituent comprising a carbon-carbon double bond formed by two carbon atoms, and ynyl refers to an alkyl substituent comprising a carbon-carbon triple bond formed by two carbon atoms.

[0128] In this specification, a diarylamine group refers to an amino group consisting of two identical or different aryl groups bonded to a nitrogen atom as described above. Furthermore, a diheteroarylamine group in the compounds of the present invention refers to an amino group consisting of two identical or different heteroaryl groups bonded to a nitrogen atom. Additionally, an aryl (heteroaryl)amine group refers to an amino group consisting of the aryl and heteroaryl groups bonded to a nitrogen atom, respectively.

[0129] Reference Figure 1 An example of the organic electroluminescent device of the present invention may include a first electrode 20, a second electrode 80 opposite to the first electrode 20, and an organic layer formed between the first electrode 20 and the second electrode 80.

[0130] For example, the first electrode 20 can be an anode, and the second electrode 80 can be a cathode. The organic layer may include a light-emitting layer 50 formed using a solution containing an organic electroluminescent material and a solvent. Depending on the need, in addition to the light-emitting layer, the organic layer may also include at least one of a hole injection layer 30, a hole transport layer 40, a functional layer that has both hole injection and hole transport functions, an electron transport layer 60, and an electron injection layer 70. Furthermore, it may include one or more intermediate layers.

[0131] The organic layer can be formed by deposition or solution processing.

[0132] The organic layer can be formed by any of the following methods: spin coating, dip coating, doctor blade coating, spray coating, roller coating, inkjet printing, and screen printing.

[0133] For example, the deposition process can refer to a method of forming a thin film by evaporating a material substance through methods such as heating under vacuum or low pressure. For example, the solution process can refer to a method of forming a thin film by mixing a material substance with a solvent to form a solution and then using the solution to form a thin film through methods such as spin coating, dip coating, doctor blade coating, spray coating, roll coating, inkjet printing, and screen printing.

[0134] Hole injection layer (HIL) 30 can be provided between first electrode 20 and hole transport layer 40. For example, hole injection layer 30 may contain poly(3,4-ethylenedioxythiophene):poly(styrenesulfonic acid) (AI4083), [4,4',4”-tris[2-naphthyl(phenyl)amino]-triphenylamine] (2-TNATA), [N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine] (NPD), [N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine] (TPD), [N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine] (DNTPD), copper phthalocyanine (Copper The substance may contain, but is not limited to, phthalocyanine or starburst-type amines such as [4,4',4”-tris(N-carbazolyl)triphenylamine] (TCTA), [4,4',4”-tris-(3-methylphenylphenylamino)triphenylamine] (m-MTDATA), and may contain substances commonly used in the art as hole injection layers.

[0135] A hole transport layer (HTL) 40 may be provided between the hole injection layer 30 and the light-emitting layer 50. The hole transport layer 40 may contain an electron-supplying material with a small ionization potential. More specifically, the hole transport layer 40 may primarily contain diamine, triamine, or tetraamine derivatives with triphenylamine as the basic backbone, such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), N,N'-di(naphthyl-1-yl)-N,N'-diphenylbenzidine (a-NPD), poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine)] (TFB), etc.

[0136] An electron transport layer (ETL) 60 may be provided between the second electrode 80 and the light-emitting layer 50. For example, the electron transport layer 60 may contain oxadiazole derivatives, triazine derivatives, Liq, Alq3, etc.

[0137] An electron injection layer (EIL) 70 may be provided between the second electrode 80 and the electron transport layer 60. For example, the electron injection layer 70 may contain Liq, LiF, NaCl, CsF, Li2O, BaO, etc., but is not limited to these, and may contain substances commonly used in the art as electron injection layers.

[0138] The light-emitting layer 50 can be provided between the hole transport layer 40 and the electron transport layer 60. The light-emitting layer 50 can be formed using a solution containing an organic electroluminescent material and a solvent.

[0139] The organic electroluminescent material may comprise a host and a dopant. The host may include a first host and a second host.

[0140] The first entity may contain the compound shown in [Chemical Formula 1].

[0141] [Chemical Formula 1]

[0142]

[0143] In the above [Chemical Formula 1], each symbol and index is as defined above.

[0144] In one embodiment of the present invention, preferably, each L1 is independently selected from the group consisting of substituted or unsubstituted C1-C10 alkylene, substituted or unsubstituted C6-C20 arylene, and substituted or unsubstituted C3-C30 heteroarylene; more preferably, it is selected from the group consisting of substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, and substituted or unsubstituted phenanthrene; and particularly preferably, it can be substituted or unsubstituted phenylene or naphthylene, or a combination of two or more thereof.

[0145] In one embodiment of the present invention, preferably, R and R1 to R 12 They may be identical or different from each other, and each independently is selected from any one of the group consisting of hydrogen atoms, deuterium atoms, substituted or unsubstituted C1-C10 alkyl groups, substituted or unsubstituted C3-C10 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, and substituted or unsubstituted C8-C50 mixed cyclic groups. More preferably, they may be selected from hydrogen atoms, deuterium atoms, substituted or unsubstituted phenyl groups, o-biphenyl, meta-biphenyl, para-biphenyl, o-terphenyl, meta-terphenyl, para-terphenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, indene, fluorenyl, perylene, etc. The group may be selected from the following: benzo[a], tetraphenyl, fluoranthyl, benzo[a]phenanthryl, furanyl, benzo[a]furanyl, dibenzo[a]furanyl, thienyl, benzo[a]thienyl, dibenzo[a]thienyl, pyrroleyl, indolyl, carbazolyl, pyridyl, tetrahydronaphthyl, tetrahydrobenzocycloheptenyl, tetrahydrophenanthryl, tetrahydroanthryl, octahydrobenzo[a]phenanthryl, particularly preferably, selected from hydrogen atoms, deuterium atoms, and substituted or unsubstituted dibenzo[a]furanyl groups.

[0146] In one embodiment of the present invention, Ar1 is selected from the group consisting of substituted or unsubstituted C1-C10 alkyl groups, substituted or unsubstituted C3-C10 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C50 heteroaryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, and substituted or unsubstituted C8-C50 mixed cyclic groups. More preferably, it is selected from substituted or unsubstituted phenyl groups, o-biphenyl, meta-biphenyl, para-biphenyl, o-terphenyl, meta-terphenyl, para-terphenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, indene, fluorenyl, perylene, etc. The phenyl group may be selected from substituted or unsubstituted phenyl or dibenzofuranyl groups, particularly preferably from tetraphenyl, fluoranthracene, benzophenanthryl, furanyl, benzofuranyl, dibenzofuranyl, tetrahydronaphthyl, tetrahydrobenzocycloheptenyl, tetrahydrophenanthryl, and octahydrobenzophenanthryl.

[0147] In one embodiment of the present invention, n is an integer from 1 to 5, preferably an integer from 2 to 5, more preferably an integer of 2 or 3. When n is 2 or more, each L1 can be the same or different from each other. m1 is an integer from 0 to 8, preferably an integer from 1 to 8. When m1 is 2 or more, each R can be the same or different from each other.

[0148] In one embodiment of the present invention, the compound represented by [Chemical Formula 1] may contain at least one substituted or unsubstituted C3-C30 heteroaryl group.

[0149] The second body may contain the compound shown in [Chemical Formula 2].

[0150] [Chemical Formula 2]

[0151]

[0152] In the above [Chemical Formula 2], each symbol is as defined above.

[0153] In one embodiment of the present invention, preferably, the R 13 To R 20Each may be the same or different, and independently selected from hydrogen atom, deuterium atom, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl having heteroatoms O, N or S, cyano, nitro, and halogen atom; more preferably, it may be selected from hydrogen atom, deuterium atom, substituted or unsubstituted phenyl, o-biphenyl, meta-biphenyl, para-biphenyl, o-terphenyl, meta-terphenyl, para-terphenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, indene, fluorenyl, tetrahydronaphthyl, perylene, Among the following: alkyl, tetraphenyl, fluoranthyl, benzophenanthryl, furanyl, benzofuranyl, dibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, pyrroleyl, indolyl, carbazoleyl, and pyridyl.

[0154] In one embodiment of the present invention, preferably, the L 11 and L 12 The components may be identical or different from each other, and each is independently selected from the group consisting of single bonds, substituted or unsubstituted C1-C10 alkylene groups, substituted or unsubstituted C6-C20 arylene groups, and substituted or unsubstituted C5-C20 heteroarylene groups. More preferably, they are selected from the group consisting of substituted or unsubstituted phenylene groups, substituted or unsubstituted naphthylene groups, and substituted or unsubstituted phenanthrene groups. Particularly preferred, they may be substituted or unsubstituted phenylene or naphthylene groups, or combinations of two or more of them.

[0155] In one embodiment of the present invention, preferably, the Ar 11 and Ar 12 The groups, whether identical or different and independently selected, are chosen from the group consisting of substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, and substituted or unsubstituted C8-C50 mixed cyclic groups. More preferably, they may be selected from substituted or unsubstituted phenyl, o-biphenyl, meta-biphenyl, para-biphenyl, o-terphenyl, meta-terphenyl, para-terphenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, indene, fluorenyl, perylene, etc. Among the following: alkyl, tetraphenyl, fluoranthryl, benzo[a]phenanthryl, furanyl, benzo[a]furanyl, dibenzo[a]furanyl, thiophene, benzo[a]thiophene, dibenzo[a]thiophene, pyrrole, indolyl, carbazolyl, pyridyl, tetrahydronaphthyl, tetrahydrobenzocycloheptenyl, tetrahydrophenanthryl, tetrahydroanthryl, and octahydrobenzo[a]phenanthryl.

[0156] The condition is that Ar 11 and Ar 12 At least one of them can be a group shown below as [Structural Formula Ar-11] or [Structural Formula Ar-12].

[0157]

[0158] In the aforementioned [structural formula Ar-11] and [structural formula Ar-12],

[0159] The asterisk (*) indicates a resemblance to L in [Chemical Formula 2]. 11 or L 12 The bonding position of L 11 or L 12 When it is a single bond, it indicates the bonding position with anthracene, and each symbol and index are defined as above.

[0160] In one embodiment of the present invention, X is preferably O or S, more preferably O.

[0161] In one embodiment of the present invention, preferably, the R 21 R 22 R and R' may be the same as or different from each other, and each is independently selected from the group consisting of hydrogen atom, deuterium atom, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl, more preferably selected from substituted or unsubstituted phenyl, o-phenyl, meta-phenyl, para-phenyl, o-terphenyl, meta-terphenyl, para-terphenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, indene, fluorenyl, tetrahydronaphthyl, perylene, Among the following: alkyl, tetraphenyl, fluoranthyl, benzophenanthryl, furanyl, benzofuranyl, dibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, pyrroleyl, indolyl, carbazoleyl, and pyridyl.

[0162] Two or more adjacent R 21 Or R 22 They can combine with each other to form alicyclic or aromatic monocyclic or polycyclic compounds.

[0163] In one embodiment of the present invention, n1 is an integer from 0 to 7, preferably an integer from 1 to 7, and n2 is an integer from 0 to 5, preferably an integer from 1 to 5. When n1 and n2 are 2 or more, each R 21 and R 22 They can be the same as or different from each other.

[0164] In one embodiment of the present invention, the second entity shown in [Chemical Formula 2] can be any one of the compounds shown in [Chemical Formula 2-1] to [Chemical Formula 2-4] below.

[0165]

[0166]

[0167] In the [Chemical Formulas 2-1] to [Chemical Formulas 2-4], each symbol and index is as defined above.

[0168] In one embodiment of the present invention, preferably, in [Chemical Formula 2-1] and [Chemical Formula 2-2], the R 21 At least one of them can be a substituted or unsubstituted C6-C30 aryl group, preferably, in [Chemical Formula 2-3] and [Chemical Formula 2-4], the R 22 At least one of them can be a substituted or unsubstituted C6-C30 aryl group, more preferably, it can be a substituted or unsubstituted phenyl, o-biphenyl, meta-biphenyl, para-biphenyl, o-terphenyl, meta-terphenyl, para-terphenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, indene, fluorenyl, tetrahydronaphthyl, perylene, The substituent is alkyl, tetraphenyl, fluoranyl, benzo[a]phenanthryl, or a combination of two or more thereof, and when substituted, the substituent is preferably a deuterium atom, a halogen atom, a C1-C6 alkyl group, or a C1-C6 alkylsilyl group.

[0169] In one embodiment of the present invention, the compound represented by [Chemical Formula 1] or [Chemical Formula 2] may be substituted with at least one deuterium atom. When the compound represented by [Chemical Formula 1] or [Chemical Formula 2] is substituted with at least one deuterium atom, the solubility of the compound represented by [Chemical Formula 1] or [Chemical Formula 2] in the solvent may increase. Preferably, the degree of deuteration of the compound represented by [Chemical Formula 1] or [Chemical Formula 2] may be 15% or more, more preferably 30% or more, 40% or more, or 50% or more.

[0170] When the compounds shown in [Chemical Formula 1] or [Chemical Formula 2] are replaced with deuterium atoms, the ground state energy is lower than that of the CH bond, and the heat resistance is further improved and the lifetime can be increased as the bonding force increases.

[0171] In one embodiment of the present invention, the molecular weight of the compound represented by [Chemical Formula 1] can be 650 or more, preferably 700 or more, more preferably 750 or more, and even more preferably 800 or more.

[0172] In one embodiment of the present invention, the molecular weight of the compound represented by [Chemical Formula 2] can be 400 or more, preferably 450 or more, and more preferably 500 or more.

[0173] The lower the molecular weight of the compound represented by [Chemical Formula 1] or [Chemical Formula 2], the easier it is to cause contamination of adjacent pixels in inkjet printing, i.e., interference effect. The higher the molecular weight of the compound represented by [Chemical Formula 1] or [Chemical Formula 2], the higher its solubility in solvent.

[0174] According to an embodiment of the present invention, the preferred compound of the first subject may be any one of the compounds shown in the chemical formulas [1-1] to [1-65], and preferably, may be any one of the compounds shown in the chemical formulas [1-7], [1-19], [1-40] and [1-61].

[0175] As the first subject, one compound may be used, or two or more compounds may be used simultaneously.

[0176] According to one embodiment of the present invention, the preferred compound of the second subject may be any one of the compounds shown in the chemical formulas [2-1] to [2-159].

[0177] As the second subject, one compound may be used, or two or more compounds may be used simultaneously.

[0178] The solubility of the main component in the solvent can be 0.1% by weight or more and 50% by weight or less, 0.5% by weight or more and 20% by weight or less, preferably 1% by weight or more, and more preferably 2% by weight or more. The solubility of both the first and second main components in the solvent can be 1% by weight or more.

[0179] The solvent may include at least one of chlorinated solvents, ether solvents, aromatic solvents, aliphatic solvents, ketone solvents, ester solvents, alcohol solvents, amide solvents, and benzoate solvents. The solvent may be a single pure substance or a mixture, and preferably, it may be a benzoate solvent.

[0180] For example, the chlorine solvents may include chloroform, dichloromethane, or chlorobenzene; the ether solvents may include tetrahydrofuran or dioxane; the aromatic solvents may include toluene, xylene, or trimethylbenzene; the aliphatic solvents may include cyclohexane, n-pentane, or n-hexane; the ketone solvents may include acetone, methyl ethyl ketone, or cyclohexanone; the ester solvents may include ethyl acetate or butyl acetate; the alcohol solvents may include methanol, ethanol, propanol, or cyclohexanol; the amide solvents may include N,N-dimethylformamide; and the benzoate solvents may include methyl benzoate, ethyl benzoate, or butyl benzoate.

[0181] The solvent can be used alone, or it can be used in combination with two or more solvents.

[0182] The boiling point of the solvent can be from 60°C to 300°C, preferably from 130°C to 300°C, but is not limited thereto.

[0183] The viscosity of the solvent can be from 1 cP to 10 cP, preferably from 2 cP to 8 cP, but is not limited thereto.

[0184] Solutions containing the compound shown in [Chemical Formula 1], the compound shown in [Chemical Formula 2], and a solvent are suitable for manufacturing organic electroluminescent devices using solution processes.

[0185] The solution may also contain fluorescent or phosphorescent dopants.

[0186] For example, the fluorescent dopant may include pyrene compounds, deuterated pyrene compounds, aromatic amines, deuterated aromatic amines, perylene compounds, deuterated perylene compounds, pyrrole compounds, deuterated pyrrole compounds, boron compounds, fluorene compounds, deuterated fluorene compounds, hydrazone compounds, deuterated hydrazone compounds, carbazole compounds, deuterated carbazole compounds, stilbene compounds, deuterated stilbene compounds, starburst compounds, deuterated starburst compounds, oxadiazole compounds, deuterated oxadiazole compounds, coumarine, deuterated coumarine, but is not limited thereto.

[0187] Examples of phosphorescent dopants include, but are not limited to, organometallic compounds comprising iridium, platinum, osmium, titanium, zirconium, hafnium, europium, terbium, thulium, iron, cobalt, nickel, ruthenium, rhodium, palladium, or combinations thereof.

[0188] The dopant can be a boron-based compound.

[0189] The dopant may contain compounds shown in [Chemical Formula 3-1] or [Chemical Formula 3-2] below.

[0190]

[0191] In [Chemical Formula 3-1] and [Chemical Formula 3-2], each symbol and index is as defined above.

[0192] In one embodiment of the present invention, the compounds shown in [Chemical Formula 3-1] and [Chemical Formula 3-2] may contain at least one -N(R”)2.

[0193] The compound represented by either [Chemical Formula 3-1] or [Chemical Formula 3-2] can be selected from any of the following chemical formulas [D 201] to [D350].

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203] The amount of fluorescent or phosphorescent dopant may be from 0.01 parts by weight to 20 parts by weight, based on the total weight of 100 parts by weight of the main body.

[0204] The content of the organic electroluminescent material in the solution can be 0.5% by weight or more, preferably 1.0% by weight or more, more preferably 2.0% by weight or more, but is not limited thereto.

[0205] Below, we will refer to Figure 1 A method for manufacturing an organic electroluminescent device according to an embodiment of the present invention is described.

[0206] A substrate 10 can be prepared. The substrate 10 can be an organic substrate or a transparent plastic substrate with excellent transparency, smooth surface, easy handling and water resistance, but is not limited to these, and may include substrates commonly used in organic electroluminescent devices.

[0207] The first electrode 20 can be formed by coating the upper surface of the substrate 10 with an anode electrode material. The anode electrode material may include a transparent material with excellent conductivity, such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), and / or zinc oxide (ZnO).

[0208] A hole injection layer 30 can be formed by vacuum thermal deposition or spin-coating of a hole injection layer material on the upper surface of the first electrode 20. A hole transport layer 40 can be formed by vacuum thermal deposition or spin-coating of a hole transport layer material on the upper surface of the hole injection layer 30.

[0209] An electron blocking layer (not shown) can be formed by selectively vacuum thermally depositing or spin-coating an electron blocking layer material on the upper surface of the hole transport layer 40. The electron blocking layer prevents electrons injected from the electron injection layer 70 from passing through the light-emitting layer 50 and entering the hole transport layer 40, thereby improving device lifetime and efficiency. The electron blocking layer can be formed in a suitable portion between the light-emitting layer 50 and the hole injection layer 30, preferably between the light-emitting layer 50 and the hole transport layer 40.

[0210] The light-emitting layer 50 can be formed on the upper surface of the hole transport layer 40 or the electron blocking layer. The light-emitting layer 50 can be formed using a solution containing the organic electroluminescent material and the solvent. More specifically, the light-emitting layer 50 can be formed by coating the solution onto the upper surface of the hole transport layer 40 using any one of spin coating, dip coating, doctor blade coating, spray coating, roller coating, inkjet printing, and screen printing.

[0211] According to an embodiment of the present invention, the thickness of the light-emitting layer 50 can be [missing information]. to

[0212] A hole-blocking layer (not shown) can be selectively formed on the upper surface of the light-emitting layer 50 using vacuum deposition or spin coating. Since the lifetime and efficiency of organic electroluminescent devices decrease when holes pass through the light-emitting layer 50 and flow into the second electrode 80, the hole-blocking layer, containing a hole-blocking material with a very low highest occupied molecular orbital (HOMO) energy level, can prevent holes from passing through the light-emitting layer 50 and flowing into the second electrode 80. The hole-blocking material is not particularly limited, but it can have electron transport capabilities and a higher ionization potential than organic electroluminescent materials. The hole-blocking material can include, for example, Balq, BCP, TPBI, etc.

[0213] An electron injection layer 70 can be formed by depositing an electron transport layer 60 on the upper surface of the light-emitting layer 50 or the hole-blocking layer using vacuum deposition or spin coating. A second electrode 80 is then formed by vacuum thermal deposition of a cathode electrode metal on the upper surface of the electron injection layer 70. The cathode electrode metal may include, for example, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. When manufacturing a top-emitting organic light-emitting device, the cathode electrode metal may include indium tin oxide (ITO) or indium zinc oxide (IZO).

[0214] An organic electroluminescent device according to an example of the present invention can be manufactured by the manufacturing method described above.

[0215] The organic electroluminescent device of the present invention will now be described with reference to preferred embodiments. However, these embodiments are provided to illustrate the invention in more detail, and it will be apparent to those skilled in the art that the scope of the invention is not limited thereto.

[0216] Synthesis Example 1: Synthesis of [1-7]

[0217] Synthesis Example 1-(1): Synthesis of <1-a>

[0218]

[0219] 6-Bromobenzo[c]phenanthrene (15.3 g, 0.05 mol) and tetrahydrofuran (145.2 mL) were added to a 1 L flask. The reactor was cooled to -78 °C under a nitrogen atmosphere and stirred. Butyllithium (1.6 M) (32 mL) was added dropwise, and the mixture was stirred at the same temperature for 1 hour. Trimethyl borate (8 mL) was added dropwise, and the reaction mixture was stirred at room temperature for 2 hours. After the reaction was complete, 100 mL of 2 M hydrochloric acid solution was added and stirred. The mixture was extracted with ethyl acetate (50 mL), concentrated under reduced pressure, and filtered through excess heptane to obtain 10.6 g of <1-a>. (Yield: 78%)

[0220] Synthesis Example 1-(2): Synthesis of <1-b>

[0221]

[0222] In a 500 mL flask, <1-a> (16.6 g, 0.061 mol), 1-bromo-5-iodonaphthalene (21.0 g, 0.063 mol), tetrakis(triphenylphosphine)palladium (1.68 g, 0.001 mol), potassium carbonate (20.08 g, 0.145 mol), toluene (125 mL), ethanol (125 mL), and water (50 mL) were added. The reactor was refluxed under a nitrogen atmosphere. After the reaction was complete, excess methanol was added to filter the resulting solid. The filtered solid was then filtered to obtain 17.4 g of <1-b>. (Yield: 66%)

[0223] Synthesis Example 1-(3): Synthesis of <1-c>

[0224]

[0225] Except for replacing <1-a> in synthetic example 1-(2) above with β-[10-(phenyl-2,3,4,5,6-D5)-9-anthrayl-1,2,3,4,5,6,7,8-D8]-boronic acid, and replacing 1-bromo-5-iodonaphthalene with 6-bromo-1-iodonaphthalene, <1-c> was synthesized by the same method. (Yield: 70%)

[0226] Synthesis Example 1-(4): Synthesis of <1-d>

[0227]

[0228] Except that <1-c> was used instead of 6-bromobenzo[c]phenanthrene in the above synthetic example 1-(1), <1-d> was synthesized by the same method. (Yield: 75%)

[0229] Synthesis Example 1-(5): Synthesis of [1-7]

[0230]

[0231] [1-7] were synthesized by the same method except that <1-d> was used instead of <1-a> in synthetic example 1-(2) above, and <1-b> was used instead of 1-bromo-5-iodonaphthalene. (Yield: 81%)

[0232] MS (MALDI-TOF): m / z 745.36 [M + ]

[0233] Synthesis Example 2: Synthesis of [1-19]

[0234] Synthesis Example 2-(1): Synthesis of <2-a>

[0235]

[0236] Except that β-1-dibenzofuranylboronic acid was used instead of <1-a> in the above synthetic example 1-(2), and 9-bromo-10-iodoanthracene was used instead of 1-bromo-5-iodonaphthalene, <2-a> was synthesized by the same method to obtain <2-a>. (Yield: 63%)

[0237] Synthesis Example 2-(2): Synthesis of <2-b>

[0238]

[0239] Except that β-(3-bromo-1-naphthyl)boronic acid was used instead of <1-a> in the above synthetic example 1-(2), and <2-a> was used instead of 1-bromo-5-iodonaphthalene, <2-b> was synthesized by the same method. (Yield: 52%)

[0240] Synthesis Example 2-(3): Synthesis of <2-c>

[0241]

[0242] Except that 1,3-phenylenediboric acid was used instead of <1-a> in Synthetic Example 1-(2) above, and 6-bromobenzo[c]phenanthrene was used instead of 1-bromo-5-iodonaphthalene, <2-c> was synthesized by the same method to obtain <2-c>. (Yield: 68%)

[0243] Synthesis Example 2-(4): Synthesis of [1-19]

[0244]

[0245] Except that <2-c> was used instead of <1-a> in the above synthetic example 1-(2), and <2-b> was used instead of 1-bromo-5-iodonaphthalene, [1-19] was synthesized by the same method. (Yield: 78%)

[0246] MS (MALDI-TOF): m / z 772.28 [M] + ]

[0247] Synthesis Example 3: Synthesis of [1-40]

[0248] Synthesis Example 3-(1): Synthesis of <3-a>

[0249]

[0250] Except that β-(1-dibenzofuranyl-2,3,4,6,7,8,9-D7)boronic acid was used instead of β-1-dibenzofuranylboronic acid in the above synthetic example 2-(1), the same method was used to synthesize <3-a>. (Yield: 72%)

[0251] Synthesis Example 3-(2): Synthesis of <3-b>

[0252]

[0253] In a 1000 mL four-necked round-bottom flask, <3-a> (35.3 g, 0.082 mol), Pd(PPh3)4 (1.5 g, 0.001 mol), potassium carbonate (18.1 g, 0.13 mol), and phenyl-1,3-diboronic acid (11.6 g, 0.07 mol) were added. Then, 250 mL of toluene, 125 mL of ethanol, and 125 mL of water were added. The reactor was refluxed under a nitrogen atmosphere. After the reaction was complete, excess methanol was poured in to filter the resulting solid. The filtered solid was then filtered to obtain 22.1 g of <3-b>. (Yield: 67%)

[0254] Synthesis Example 3-(3): Synthesis of <3-c>

[0255]

[0256] Except that <3-b> was used instead of <1-a> in the above synthetic example 1-(2), and 2-bromo-1-iodonaphthalene was used instead of 1-bromo-5-iodonaphthalene, <3-c> was synthesized by the same method. (Yield: 72%)

[0257] Synthesis Example 3-(4): Synthesis of <3-d>

[0258]

[0259] Under a nitrogen atmosphere, 13.5 g (0.035 mol) of 5,8-dibromobenzo[c]phenanthrene, 7.9 g (0.036 mol) of β-(1-dibenzofuranyl-2,3,4,6,7,8,9-D7)boric acid, 0.8 g (0.00065 mol) of Pd(PPh3)4, 9 g (0.065 mol) of potassium carbonate, 100 mL of toluene, and 30 mL of water were added to a round-bottom flask, and the mixture was refluxed for 12 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the layers were separated, the organic layer was concentrated, separated by column chromatography, and recrystallized to obtain 10.1 g of <3-d>. (Yield: 60%)

[0260] Synthesis Example 3-(5): Synthesis of <3-e>

[0261]

[0262] Except that <3-d> was used instead of <3-a> in the above synthetic example 3-(2), <3-e> was synthesized in the same manner to obtain <3-e>. (Yield: 66%)

[0263] Synthesis Example 3-(6): Synthesis of [1-40]

[0264]

[0265] Except for replacing <1-d> in synthetic example 1-(5) above with <3-e> and <1-b> with <3-c>, [1-40] was synthesized in the same manner to obtain [1-40]. (Yield: 82%)

[0266] MS (MALDI-TOF): m / z 1028.44 [M + ]

[0267] Synthesis Example 4: Synthesis of [1-61]

[0268] Synthesis Example 4-(1): Synthesis of <4-a>

[0269]

[0270] Except that 1-bromo-5-iodonaphthalene was used instead of 6-bromo-1-iodonaphthalene in Synthetic Example 1-(3) above, <4-a> was synthesized by the same method to obtain <4-a>. (Yield: 65%)

[0271] Synthetic Example 4-(2): Synthesis of Intermediate 4-b

[0272]

[0273] Except that <4-a> was used instead of <1-c> in the above synthetic example 1-(4), <4-b> was synthesized in the same manner. (Yield: 74%)

[0274] Synthesis Example 4-(3): Synthesis of [1-61]

[0275]

[0276] Except for using <4-b> instead of <1-d> in the above synthetic examples 1-(5), [1-61] were synthesized in the same manner to obtain [1-61]. (Yield: 81%)

[0277] MS (MALDI-TOF): m / z 745.36 [M + ]

[0278] Synthesis Example 5: Synthesis of [2-89]

[0279] Synthesis Example 5-(1): Synthesis of <5-a>

[0280]

[0281] 7-Bromodibenzofuran-1-ol (20.8 g), phenyl-D5-boronic acid (12.0 g), tetrakis(triphenylphosphine)palladium (2.74 g), and potassium carbonate (32.8 g) were added to a 500 mL reactor, followed by 200 mL of toluene, 60 mL of ethanol, and 60 mL of water. The reactor temperature was raised to 80 °C, and the mixture was stirred for 12 hours. After the reaction was completed, the mixture was extracted, and the organic layer was separated by column chromatography to obtain 18.5 g of <5-a>.

[0282] (Yield: 88%)

[0283] Synthesis Example 5-(2): Synthesis of <5-b>

[0284]

[0285] Under a nitrogen atmosphere, 10.6 g of <5-a> was added to a 500 mL reactor, followed by dissolution with 136 mL of dichloromethane. The reaction solution was cooled to 0 °C, and 10 mL of pyridine was added, followed by dropwise addition of trifluoromethanesulfonic anhydride (12.7 g) while maintaining the same temperature. The mixture was stirred at room temperature for 12 hours, then 20 mL of water was added to the reaction solution and stirred. The organic layer was extracted with water and dichloromethane, and then recrystallized from heptane to give 7.5 g of <5-b>. (Yield: 47%)

[0286] Synthesis Example 5-(3): Synthesis of [2-89]

[0287]

[0288] Except that <5-b> was used instead of 7-bromodibenzofuran-1-ol in the above synthetic example 5-(1), and <5-c> was used instead of phenyl-D5-boronic acid, 6.2 g of [2-89] was obtained by the same method. (Yield: 65%)

[0289] MS (MALDI-TOF): m / z 506.25 [M + ]

[0290] Synthesis Example 6: Synthesis of [2-101]

[0291] Synthesis Example 6-(1): Synthesis of <6-b>

[0292]

[0293] Except that <6-a> was used instead of 7-bromodibenzofuran-1-ol in the above synthetic example 5-(1), <6-b> was obtained by the same method.

[0294] (Yield: 70%)

[0295] Synthesis Example 6-(2): Synthesis of <6-c>

[0296]

[0297] <6-b> (21.4 g, 0.106 mol) and dichloromethane were added to a 500 mL reactor and cooled to -10 °C. Bromine was then added and the mixture was stirred for 1 hour. An aqueous solution of sodium thiosulfate was added to the reaction mixture and stirred, allowing the layers to separate. The organic layer was concentrated under reduced pressure. Ethanol was added, and the mixture was cooled to -10 °C. Potassium hydroxide dissolved in ethanol was then added, and the mixture was heated and refluxed for 4 hours. After the reaction was complete, the reactants were separated into layers. The organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain 21.2 g of <6-c>. (Yield: 71%)

[0298] Synthesis Example 6-(3): Synthesis of [2-101]

[0299]

[0300] [2-101] was obtained by the same method except that <6-c> was used instead of 7-bromodibenzofuran-1-ol in the above synthetic example 5-(1) and <6-d> was used instead of phenyl-d5-boronic acid. (Yield: 68%)

[0301] MS (MALDI-TOF): m / z 468.31 [M + ]

[0302] Synthesis Example 7: Synthesis of [D-265]

[0303] The following compound [D-265] was prepared by referring to the method for synthesizing the dopant compound described in Patent Publication No. 10-2148296.

[0304]

[0305] Examples 1 to 8

[0306] Poly(3,4-ethylenedioxythiophene):poly(styrenesulfonic acid) (AI4083), widely used as a hole injection layer, was spin-coated onto an ITO transparent electrode to form a 60 nm thick film, and then baked at 200 °C for 30 minutes to form a hole injection layer. TFB was spin-coated onto the hole injection layer to form a 20 nm thick film, and then baked at 130 °C for 10 minutes to form a hole transport layer. A methyl benzoate solution containing a 2% by weight concentration of the host material (a mixture of the first host material shown in [Chemical Formula 1] and the second host material shown in [Chemical Formula 2] of the present invention, as shown in Table 1 below, in a 5:5 weight ratio (weight percentage)) and dopant [D 265] (the weight ratio of the first host material and the second host material to the dopant is 97:3) was spin-coated onto the hole transport layer to form a 30 nm thick film, and then baked at 180 °C for 30 minutes to form a light-emitting layer. The material was baked at 130°C for 10 minutes under a nitrogen atmosphere, and then [E-1] and [E-2] were deposited in a 1:1 ratio as electron transport layers to form a 25 nm thick film. [E-2] was then deposited on top of the electron transport layers as an electron injection layer to form a 1 nm thick film. Finally, aluminum was deposited as a cathode on the electron injection layers to fabricate an organic electroluminescent device. (The last sentence appears to be incomplete and possibly refers to a different process.) 2 The luminescence characteristics of the above-mentioned organic electroluminescent devices were measured.

[0307] Comparative Examples 1 to 4

[0308] Poly(3,4-ethylenedioxythiophene):poly(styrenesulfonic acid) (AI4083), widely used as a hole injection layer, was spin-coated onto an ITO transparent electrode to form a 60 nm thick film, and then baked at 200 °C for 30 minutes to form a hole injection layer. TFB was spin-coated onto the hole injection layer to form a 20 nm thick film, and then baked at 130 °C for 10 minutes to form a hole transport layer. A methyl benzoate solution containing a 2 wt% concentration of the host compound and dopant [D 265] (host:dopant weight ratio = 97:3) was spin-coated onto the hole transport layer to form a 30 nm thick film, and then baked at 180 °C for 30 minutes to form a light-emitting layer. This was then baked at 130 °C for 10 minutes under a nitrogen atmosphere, and then [E-1] and [E-2] were deposited in a 1:1 ratio as electron transport layers to form a 25 nm thick film. [E-2] was deposited as an electron injection layer on the electron transport layer to form a film with a thickness of 1 nm. Finally, aluminum was deposited as a cathode on the electron injection layer with a thickness of 100 nm to fabricate an organic electroluminescent device. At 10 mA / cm² 2 The luminescence characteristics of the above-mentioned organic electroluminescent devices were measured.

[0309]

[0310]

[0311] Table 1. Example Data

[0312]

[0313] Table 2. Comparative Data

[0314] main body Drive voltage (V) Efficiency (cd / A) T95 (hr) Comparative Example 1 [1-7] 4.0 5.1 52 Comparative Example 2 [1-19] 4.2 5.0 55 Comparative Example 3 [1-40] 4.2 4.7 54 Comparative Example 4 [1-61] 4.3 4.9 59

[0315] The driving voltage, efficiency, and lifetime of the organic electroluminescent devices manufactured according to Examples 1 to 8 and Comparative Examples 1 to 4 were measured, and the results are shown in Tables 1 and 2. T95 refers to the time required for the brightness to decrease to 95% of the initial brightness.

[0316] It has been confirmed that, compared with the organic electroluminescent devices of Comparative Examples 1 to 4 that use only the first body as the main material, the organic electroluminescent devices of Examples 1 to 8 of the present invention, which contain a second body shown in [Chemical Formula 2] in addition to the same first body, have good driving voltage and efficiency, and have improved lifetime characteristics.

Claims

1. An organic electroluminescent device, comprising: First electrode; Second electrode; An organic layer is formed between the first electrode and the second electrode, and the organic electroluminescent device is characterized in that... The organic layer includes a light-emitting layer formed using a solution containing organic electroluminescent materials and a solvent. The organic electroluminescent material comprises a first host as shown in [Chemical Formula 1], a second host as shown in [Chemical Formula 2], and a dopant: [Chemical Formula 1] In the [Chemical Formula 1], each L1 is independently selected from the group consisting of substituted or unsubstituted C1-C20 alkylene, substituted or unsubstituted C6-C30 arylene, and substituted or unsubstituted C2-C30 heteroarylene. The R and R1 to R 12 They may be identical or different from each other, and each independently is selected from hydrogen atom, deuterium atom, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C5-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C30 alkylthiooxy, substituted or unsubstituted C6-C30 arylthiooxy, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C6-C30 The R1 to R1 groups comprise any one of the following groups: arylamine, substituted or unsubstituted C2-C30 heteroarylamine, substituted or unsubstituted C12-C24 diarylamine, substituted or unsubstituted C2-C24 diheteroarylamine, substituted or unsubstituted C7-C24 aryl (heteroaryl)amine, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C3-C50 heteroaryl, substituted or unsubstituted C8-C50 mixed cyclic group, substituted or unsubstituted C1-C30 alkylsilyl, and substituted or unsubstituted C6-C30 arylsilyl. 12 One of them is a single bond connected to the linking group L1. Ar1 is selected from the group consisting of substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C50 heteroaryl groups, and substituted or unsubstituted C8-C50 mixed cyclic groups. n is an integer from 1 to 5. When n is 2 or more, each L1 is either the same as or different from the others. m1 is an integer from 0 to 8. When m1 is 2 or greater, each R is either the same as or different from the others. [Chemical Formula 2] In the [Chemical Formula 2], the R 13 To R 20 Each may be the same or different, and independently selected from hydrogen atom, deuterium atom, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C5-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C30 alkylsulfoxy The following are included: alkyl, substituted or unsubstituted C6-C30 arylsulfoxy, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C2-C50 heteroaryl with heteroatoms O, N or S, cyano, nitro, halogen atom, substituted or unsubstituted C1-C30 alkylsilyl, and substituted or unsubstituted C6-C30 arylsilyl. The L 11 and L 12 They may be identical or different from each other, and each is independently selected from the group consisting of single bonds, substituted or unsubstituted C1-C20 alkylene groups, substituted or unsubstituted C6-C30 arylene groups, and substituted or unsubstituted C2-C30 heteroarylene groups. The Ar 11 and Ar 12 Each group, whether identical or different, and independently selected from the group consisting of substituted or unsubstituted C6-C50 aryl groups, substituted or unsubstituted C2-C50 heteroaryl groups, and substituted or unsubstituted C8-C50 mixed cyclic groups, may be the same or different. The condition is that Ar 11 and Ar 12 At least one of them is a group represented by the following [structural formula Ar-11] or [structural formula Ar-12]: In the aforementioned [structural formula Ar-11] and [structural formula Ar-12], The "*" indicates that it is related to L. 11 or L 12 The bonding position of L 11 or L 12 When it is a single bond, it indicates the bonding position with anthracene. X is selected from the group consisting of O, S, C(R')2, NR', and Si(R')2. The R 21 R 22 R and R' are either the same as or different from each other, and are each independently selected from the group consisting of hydrogen atom, deuterium atom, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C5-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C30 alkylthiooxy, substituted or unsubstituted C6-C30 arylthiooxy, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C3-C50 heteroaryl, substituted or unsubstituted C1-C30 alkylsilyl, and substituted or unsubstituted C6-C30 arylsilyl, and two or more adjacent R's. 21 Or R 22 They can combine with each other to form alicyclic or aromatic monocyclic or polycyclic compounds. Where n1 is an integer from 1 to 7, and n2 is an integer from 1 to 5, when n1 and n2 are 2 or more, each R 21 and R 22 They are the same or different from each other.

2. The organic electroluminescent device according to claim 1, characterized in that, The compound shown in [Chemical Formula 1] is substituted with at least one deuterium atom.

3. The organic electroluminescent device according to claim 2, characterized in that, The compound shown in [Chemical Formula 1] has a deuteration degree of 30% or more.

4. The organic electroluminescent device according to claim 1, characterized in that, The compound shown in [Chemical Formula 1] contains at least one substituted or unsubstituted C3-C30 heteroaryl group.

5. The organic electroluminescent device according to claim 1, characterized in that, The compound shown in [Chemical Formula 1] has a molecular weight of 650 or more.

6. The organic electroluminescent device according to claim 1, characterized in that, In the [Chemical Formula 1], L1 is a substituted or unsubstituted C6-C20 arylene.

7. The organic electroluminescent device according to claim 1, characterized in that, In the [Chemical Formula 1], n is an integer from 2 to 5.

8. The organic electroluminescent device according to claim 1, characterized in that, The first body is shown in any one of [1-1] to [1-65] below:

9. The organic electroluminescent device according to claim 1, characterized in that, The second entity shown in [Chemical Formula 2] is any one of the compounds shown in [Chemical Formula 2-1] to [Chemical Formula 2-4] below: The R 13 To R 22 L 11 L 12 Ar 11 n1 and n2 are as defined in [Chemical Formula 2] as in claim 1.

10. The organic electroluminescent device according to claim 9, characterized in that, In [Chemical Formula 2-1] and [Chemical Formula 2-2], the R 21 At least one of them is a substituted or unsubstituted C6-C30 aryl group. In [Chemical Formula 2-3] and [Chemical Formula 2-4], the R 22 At least one of them is a substituted or unsubstituted C6-C30 aryl group.

11. The organic electroluminescent device according to claim 1, characterized in that, The second body is shown in any one of [2-1] to [2-159] below:

12. The organic electroluminescent device according to claim 1, characterized in that, The solvent includes at least one of chlorinated solvents, ether solvents, aromatic solvents, aliphatic solvents, ketone solvents, ester solvents, alcohol solvents, amide solvents, and benzoic acid ester solvents.

13. The organic electroluminescent device according to claim 1, characterized in that, The solubility of both the first and second components in the solvent is greater than 1% by weight.

14. The organic electroluminescent device according to claim 1, characterized in that, The dopant is a compound shown in [Chemical Formula 3-1] or [Chemical Formula 3-2] below: In the aforementioned [Chemical Formula 3-1] and [Chemical Formula 3-2], T1 to T3 may be the same as or different from each other, and are independently C6-C50 aromatic hydrocarbon rings or C2-C40 aromatic heterocycles. T1 to T3 can each be independently controlled by at least one R T Replacement, when replaced by two or more R T When replaced, these R T Whether they are the same or different, The R T The atom is selected from any one of the following groups: hydrogen atom, deuterium atom, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C24 alkynyl, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C5-C30 cycloalkenyl, substituted or unsubstituted C2-C50 heteroaryl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C30 alkylthiooxy, substituted or unsubstituted C5-C30 arylthiooxy, -N(R”)2, substituted or unsubstituted C1-C30 alkylsilyl, substituted or unsubstituted C5-C30 arylsilyl, cyano, and halogen atom. The R's may be the same as or different from each other, and each is independently selected from the group consisting of hydrogen atoms, deuterium atoms, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C2-C30 alkenyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C5-C30 cycloalkenyl groups, substituted or unsubstituted C6-C50 aryl groups, and substituted or unsubstituted C3-C50 heteroaryl groups. The R's can combine with each other to form alicyclic or aromatic monocyclic or polycyclic rings. Y1 is selected from NR 31 CR 32 R 33 O, S, Se and SiR 34 R 35 any of them, Y2 is selected from NR 36 CR 37 R 38 O, S and SiR 39 R 40 any of them, Y3 is selected from NR 41 CR 42 R 43 O, S and SiR 44 R 45 any of them, The R 31 To R 45 Each may be the same as or different from the others, and independently selected from hydrogen atom, deuterium atom, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C5-C30 cycloalkenyl, substituted or unsubstituted C2-C50 heteroaryl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C30 alkylsulfoxy The R group comprises any one of the following: substituted or unsubstituted C5-C30 arylsulfooxy group, substituted or unsubstituted C1-C30 alkylamino group, substituted or unsubstituted C6-C30 arylamino group, substituted or unsubstituted C2-C30 heteroarylamino group, substituted or unsubstituted C12-C24 diarylamino group, substituted or unsubstituted C2-C24 diheteroarylamino group, substituted or unsubstituted C7-C24 aryl (heteroaryl)amino group, substituted or unsubstituted C1-C30 alkylsilyl group, substituted or unsubstituted C5-C30 arylsilyl group, cyano group, and halogen atom. 31 To R 45 Each can combine with one or more rings selected from T1 to T3 to further form alicyclic or aromatic monocyclic or polycyclic rings.

15. The organic electroluminescent device according to claim 14, characterized in that, The compounds shown in [Chemical Formula 3-1] and [Chemical Formula 3-2] contain at least one -N(R”)2.

16. The organic electroluminescent device according to claim 1, characterized in that, In addition to the light-emitting layer, the organic layer also includes at least one of the following: a hole injection layer, a hole transport layer, a functional layer that has both hole injection and hole transport functions, an electron transport layer, and an electron injection layer.

17. The organic electroluminescent device according to claim 1, characterized in that, The organic layer is formed by any one of spin coating, dip coating, doctor blade coating, spray coating, roller coating, inkjet printing, and screen printing.

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