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 including a light-emitting layer formed using a solution containing an organic electroluminescent material and a solvent, the organic electroluminescent material containing a host and a dopant, the host being one or more compounds represented by the following [Chemical Formula A]. [Chemical Formula A] # imgabs0 #

Description

Technical Field

[0001] The present invention relates to an organic electroluminescent device, and more particularly, to an organic electroluminescent device in which the operating characteristics of the device, such as luminous efficiency, driving voltage, and lifespan, are improved by including an organic electroluminescent material having high solubility in a solvent.

[0002] For reference, the present invention is part of a research project of the Korea Institute of Industrial Technology Evaluation and Management under the Ministry of Industry, Trade and Energy of Korea, aiming to establish future growth drivers for the materials and components industry - display innovation process platform. It is the research result of SFC Co., Ltd. under the project name of "Development of High-performance, Long-life Luminescent Layer Ink Materials and Device Technology for Printing Process" (Project No.: 20011059), and the research period is from April 1, 2020 to December 31, 2024. Background Art

[0003] An organic electroluminescent device is a display device that utilizes the self-luminescence phenomenon. It has a large viewing angle, can be thinner, lighter, shorter, and smaller than a liquid crystal display, and has advantages such as a fast response speed. Therefore, it is used as a full-color display or lighting.

[0004] Generally, the organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using an organic substance. An organic electroluminescent device utilizing the organic light-emitting phenomenon typically has a structure including an anode, a cathode, and an organic layer therebetween. Among them, in order to improve the luminous efficiency and stability of the organic electroluminescent device, the organic layer is usually composed of a multi-layer structure of different substances. For example, it can be composed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In this structure of the organic electroluminescent device, 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 the excitons fall back to the ground state, light is emitted. Such an organic light-emitting device is known to have characteristics such as self-luminescence, high brightness, high luminous efficiency, low driving voltage, wide viewing angle, high contrast, and high-speed response.

[0005] Currently, displays are becoming larger and larger. When manufacturing large displays using a deposition process, there are disadvantages such as a decrease in production yield and an increase in investment costs as the substrate becomes larger. In addition, since the deposition process evaporates single-molecule substances under vacuum conditions and deposits them on the substrate, in order to prevent decomposition at the high evaporation temperature, substances with a high glass transition temperature need to be used, so there are limitations.

[0006] On the other hand, when manufacturing a large display by preparing a solution by dissolving an organic electroluminescent material in a solvent and then coating the solution on a substrate, it has advantages such as lower process cost than the deposition process and relatively simple process steps. However, organic electroluminescent materials generally have low solubility in solvents, so it is difficult to ensure the luminous efficiency, brightness, power efficiency, lifespan, and thermal stability of the device.

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

[0008] Technical Problem

[0009] In order to solve the problems described above, an object of the present invention is to provide an organic electroluminescent device that has a lower driving voltage, improved luminous efficiency, and improved lifespan characteristics by using an organic electroluminescent material having high solubility in a solvent.

[0010] The problems to be solved by the present invention are not limited to the problems described above, and those skilled in the art can clearly understand other problems not mentioned from the following description.

[0011] Technical Solution

[0012] <1> The organic electroluminescent device of the present invention is an organic electroluminescent device including a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode. The organic layer may include a light-emitting layer formed using a solution containing an organic electroluminescent material and a solvent. The organic electroluminescent material may include a host and a dopant, and the host may be one or more compounds represented by the following [Chemical Formula A].

[0013] [Chemical Formula A]

[0014]

[0015] In the [Chemical Formula A], the L1s are the same or different from each other and are each independently selected from the group consisting of a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms.

[0016] The R and R1 to R 12The same as or different from each other, and each independently is selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 2 to 30 carbon atoms, a substituted or unsubstituted diarylamino group having 12 to 24 carbon atoms, a substituted or unsubstituted diheteroarylamino group having 2 to 24 carbon atoms, a substituted or unsubstituted aryl(heteroaryl)amino group having 7 to 24 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and one of the R1 to R 12 in 12 is a single bond connected to the linking group L1,

[0017] Ar1 is selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms,

[0018] n1 is an integer from 1 to 5. When n1 is 2 or more, each L1 is the same as or different from each other,

[0019] m1 is an integer from 0 to 8. When m1 is 2 or more, each R is the same as or different from each other.

[0020] <2> In <1>,

[0021] the compound represented by [Chemical Formula A] can be substituted by at least one deuterium atom.

[0022] <3> In <1> and <2>,

[0023] the degree of deuteration of the compound represented by [Chemical Formula A] can be 30% or more.

[0024] <4> In <1> to <3>,

[0025] The compound represented by [Chemical formula A] may contain at least one substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0026] <5>In the <4>,

[0027] The compound represented by [Chemical formula A] may contain at least one group represented by the following [Chemical formula A-1] or [Chemical formula A-2]:

[0028]

[0029] In the [Chemical formula A-1] and [Chemical formula A-2],

[0030] The X is selected from the group consisting of O, S, NR', and Si(R')2.

[0031] The Z and R' are the same as or different from each other, and each independently is selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 2 to 30 carbon atoms, a substituted or unsubstituted diarylamino group having 12 to 24 carbon atoms, a substituted or unsubstituted diheteroarylamino group having 2 to 24 carbon atoms, a substituted or unsubstituted aryl(heteroaryl)amino group having 7 to 24 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms.

[0032] The n2 is an integer from 0 to 7, the n3 is an integer from 0 to 5, and when n2 and n3 are 2 or more, each Z is the same as or different from each other.

[0033] <6>In the <5>,

[0034] The X may be O.

[0035] <7>In the <1> to <6>,

[0036] The molecular weight of the compound represented by [Chemical formula A] may be 650 or more.

[0037] <8> Among <1> to <7> above,

[0038] L1 may be a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

[0039] <9> Among <1> to <8> above,

[0040] n1 may be 2 to 5.

[0041] <10> Among <1> to <9> above,

[0042] The solvent may include at least one of a chlorine-based solvent, an ether-based solvent, an aromatic solvent, an aliphatic solvent, a ketone-based solvent, an ester-based solvent, an alcohol-based solvent, an amide-based solvent, and a benzoate-based solvent.

[0043] <11> Among <1> to <10> above,

[0044] The host may be dissolved in the solvent in an amount of 1 wt% or more.

[0045] <12> Among <1> to <11> above,

[0046] The host may be represented by any one of the following [1] to

[63] :

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054] <13> Among <1> to <12> above,

[0055] The dopant may be a compound represented by the following [Chemical formula B-1] or [Chemical formula B-2]:

[0056]

[0057] In the [Chemical formula B-1] and [Chemical formula B-2],

[0058] Each of T1 to T3 is the same as or different from one another, and independently of one another is an aromatic hydrocarbon ring having 6 to 50 carbon atoms or an aromatic heterocyclic ring having 2 to 40 carbon atoms,

[0059] Each of T1 to T3 can be independently substituted by at least one R T When substituted by two or more Rs, T these Rs T are the same as or different from one another,

[0060] The R T is any one selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, -N(R”)2, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a cyano group, and a halogen,

[0061] The R”s are the same as or different from one another, and are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms. The R”s can combine with each other to form an alicyclic or aromatic monocyclic or polycyclic ring,

[0062] The Y1 is any one selected from the group consisting of N-R 13 , CR 14 R 15 , O, S, and SiR 16 R 17 ;

[0063] The Y2 is any one selected from the group consisting of N-R 18 , CR 19 R 20 , O, S, and SiR 21 R 22Any one of the groups formed

[0064] Said Y3 is selected from the group consisting of N-R 23 , CR 24 R 25 , O, S, and SiR 26 R 27 Any one of the groups formed

[0065] Said R 13 to R 27 are each the same as or different from one another and are each independently selected from the group consisting of hydrogen, deuterium atom, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 24 carbon atoms, substituted or unsubstituted aryl having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl having 5 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 50 carbon atoms, substituted or unsubstituted alkoxy having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkylthioxy having 1 to 30 carbon atoms, substituted or unsubstituted arylthioxy having 5 to 30 carbon atoms, substituted or unsubstituted alkylamino having 1 to 30 carbon atoms, substituted or unsubstituted arylamino having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylamino having 2 to 30 carbon atoms, substituted or unsubstituted diarylamino having 12 to 24 carbon atoms, substituted or unsubstituted diheteroarylamino having 2 to 24 carbon atoms, substituted or unsubstituted aryl(heteroaryl)amino having 7 to 24 carbon atoms, substituted or unsubstituted alkylsilyl having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl having 5 to 30 carbon atoms, cyano, and halogen. Said R 13 to R 27 can each bind to one or more rings selected from the group consisting of said T1 to T3 to further form an alicyclic or aromatic monocyclic or polycyclic ring.

[0066] <14>In the <13>,

[0067] The compound represented by [Chemical Formula B-1] and [Chemical Formula B-2] may contain at least one -N(R”)2.

[0068] <15>In the <1> to <14>,

[0069] In addition to the light-emitting layer, the organic layer may further include at least one of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, an electron transport layer, and an electron injection layer.

[0070] <16>In <1> to <15> above,

[0071] The organic layer can be formed by any one of spin coating, dip coating, blade coating, spray coating, roll coating, inkjet printing, and screen printing.

[0072] Effects of the Invention

[0073] The organic electroluminescent device of the present invention can be prepared using an organic electroluminescent material having high solubility in a solvent, and has excellent device operating characteristics and lifetime characteristics, such as luminous efficiency and driving voltage. Description of the Drawings

[0074] Figure 1 It is a schematic cross-sectional view of an organic electroluminescent device according to an example of the present invention.

[0075] Description of Reference Numerals

[0076] 10: Substrate

[0077] 20: First electrode

[0078] 30: Hole injection layer

[0079] 40: Hole transport layer

[0080] 50: Light-emitting layer

[0081] 60: Electron transport layer

[0082] 70: Electron injection layer

[0083] 80: Second electrode Detailed Description of the Invention

[0084] Referring to Figure 1 , an organic electroluminescent device according to an example 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.

[0085] For example, the first electrode 20 may be an anode, and the second electrode 80 may 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. Optionally, in addition to the light-emitting layer, the organic layer may further include at least one of a hole injection layer 30, a hole transport layer 40, a functional layer having both a hole injection function and a hole transport function, an electron transport layer 60, and an electron injection layer 70. Additionally, it may further include a single or multiple intermediate layers.

[0086] The organic layer can be formed by a deposition process or a solution process.

[0087] For example, the deposition process may refer to a method of forming a thin film by evaporating a material substance through a method such as heating in a vacuum or low-pressure state. For example, the solution process may refer to a method of forming a solution by mixing a material substance with a solvent and then using the solution to form a thin film by methods such as spin coating, dip coating, blade coating, spray coating, roll coating, inkjet printing, and screen printing.

[0088] A hole injection layer (HIL, Hole Injecting Layer) 30 may be provided between the first electrode 20 and the hole transport layer 40. For example, the hole injection layer 30 may include poly(3,4-ethylenedioxythiophene): poly(styrenesulfonic acid) (AI4083), [4,4',4”-tris[2-naphthyl(phenyl)amino]-triphenylamine] (2-TNATA), [N,N'-bis(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, or [4,4',4”-tris(N-carbazolyl)triphenylamine] (TCTA), [4,4',4”-tris-(3-methylphenylphenylamino)triphenylamine] (m-MTDATA), etc. belonging to starburst amines, but is not limited thereto, and may include substances commonly used as hole injection layers in the art.

[0089] A hole transport layer (HTL, Hole Transport Layer) 40 may be provided between the hole injection layer 30 and the light-emitting layer 50. The hole transport layer 40 may include an electron-donating substance having a small ionization potential. More specifically, the hole transport layer 40 may mainly include diamine, triamine, or tetraamine derivatives having a triphenylamine as a basic skeleton. For example, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), N,N'-bis(naphthalen-1-yl)-N,N'-diphenylbenzidine (a-NPD), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine)] (TFB), etc.

[0090] An electron transport layer (ETL, Electron Transport Layer) 60 may be provided between the second electrode 80 and the light-emitting layer 50. For example, the electron transport layer 60 may include oxadiazole derivatives, triazine derivatives, Liq, Alq3, etc.

[0091] The electron injection layer (EIL, Electron Injecting Layer) 70 can be provided between the second electrode 80 and the electron transport layer 60. For example, the electron injection layer 70 can include, but is not limited to, Liq, LiF, NaCl, CsF, Li2O, BaO, etc., and can include substances commonly used as electron injection layers in the art.

[0092] 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.

[0093] The organic electroluminescent material can include a host and a dopant, and the host can be one or more compounds represented by the following [Chemical Formula A]:

[0094] [Chemical Formula A]

[0095]

[0096] In the [Chemical Formula A], the L1s are the same or different from each other, and each independently is selected from the group consisting of a substituted or unsubstituted alkylene having 1 to 20 carbon atoms, a substituted or unsubstituted arylene having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms.

[0097] The R and R1 to R 12identical to or different from each other, and each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 2 to 30 carbon atoms, a substituted or unsubstituted diarylamino group having 12 to 24 carbon atoms, a substituted or unsubstituted diheteroarylamino group having 2 to 24 carbon atoms, a substituted or unsubstituted aryl(heteroaryl)amino group having 7 to 24 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and one of the R1 to R 12 is a single bond connected to the linking group L1,

[0098] Ar1 is selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms,

[0099] n1 is an integer from 1 to 5, and when n1 is 2 or more, each L1 is identical to or different from each other,

[0100] m1 is an integer from 0 to 8, and when m1 is 2 or more, each R is identical to or different from each other.

[0101] In one example of the present invention, the compound represented by [Chemical Formula A] can be substituted with at least one deuterium atom. When the compound represented by [Chemical Formula A] is substituted with at least one deuterium, the solubility of the compound represented by [Chemical Formula A] in a solvent can be increased. Preferably, the degree of deuteration of the compound represented by [Chemical Formula A] can be 15% or more, more preferably 30% or more, 40% or more, or 50% or more.

[0102] When the compound represented by [Chemical Formula A] is deuterium-substituted, compared with the C-H bond, the ground state energy is reduced, and as the bond force increases, the heat resistance is further improved and the lifespan can be increased.

[0103] In one embodiment of the present invention, the compound represented by [Chemical Formula A] may include at least one substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms.

[0104] In one embodiment of the present invention, the compound represented by [Chemical Formula A] may include at least one group represented by the following [Chemical Formula A-1] or [Chemical Formula A-2]:

[0105]

[0106] In the [Chemical Formula A-1] and [Chemical Formula A-2],

[0107] X is selected from the group consisting of O, S, NR', and Si(R')2.

[0108] Z and R' are the same as or different from each other, and are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy having 6 to 30 carbon atoms, a substituted or unsubstituted alkylamino having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino having 2 to 30 carbon atoms, a substituted or unsubstituted diarylamino having 12 to 24 carbon atoms, a substituted or unsubstituted diheteroarylamino having 2 to 24 carbon atoms, a substituted or unsubstituted aryl(heteroaryl)amino having 7 to 24 carbon atoms, a substituted or unsubstituted aryl having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl having 1 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl having 6 to 30 carbon atoms.

[0109] n2 is an integer from 0 to 7, n3 is an integer from 0 to 5, and when n2 and n3 are 2 or more, each Z is the same as or different from each other.

[0110] In one embodiment of the present invention, X of [Chemical Formula A] may be O.

[0111] In one embodiment of the present invention, the molecular weight of the compound represented by [Chemical Formula A] may be 650 or more, preferably 700 or more, more preferably 750 or more, and still more preferably 800 or more.

[0112] The lower the molecular weight of the compound represented by [Chemical Formula A], the more likely it is to cause contamination of adjacent pixels, i.e., the interference effect, in the inkjet process. The higher the molecular weight of the compound represented by [Chemical Formula A], the higher its solubility in the solvent.

[0113] In one embodiment of the present invention, L1 of [Chemical Formula A] may be a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, preferably a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted phenanthrylene group.

[0114] In one embodiment of the present invention, n1 of [Chemical Formula A] may be 2 to 5, preferably 2 or 3.

[0115] The "substitution" in the "substituted or unsubstituted" means being substituted by one or more substituents selected from the group consisting of a deuterium atom, a cyano group, a halogen, a hydroxyl group, a nitro group, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a cycloalkenyl group having 5 to 30 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 50 carbon atoms, an arylalkyl group having 7 to 24 carbon atoms, an alkylaryl group having 7 to 24 carbon atoms, a heteroaryl group having 2 to 50 carbon atoms, a heteroarylalkyl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an alkylthioxy group having 1 to 30 carbon atoms, an arylthioxy group having 6 to 30 carbon atoms, -N(R")2, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, and an arylsulfinyl group having 6 to 24 carbon atoms.

[0116] Moreover, considering the ranges of the alkyl or aryl groups in the "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms", "substituted or unsubstituted aryl group having 6 to 50 carbon atoms", etc., the ranges of the number of carbon atoms in the alkyl group having 1 to 30 carbon atoms and the aryl group having 6 to 50 carbon atoms, etc., respectively refer to the total number of carbon atoms constituting the alkyl part or the aryl part when considering the unsubstituted case without taking into account the substituted part. For example, a phenyl group substituted with a para-butyl group should be regarded as corresponding to an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

[0117] In this specification, an aryl group refers to an aromatic system composed of a hydrocarbon containing more than one ring. When the aryl group has substituents, it can further fuse with adjacent substituents to form a ring.

[0118] Specific examples of the aryl group include phenyl, o - biphenylyl, m - biphenylyl, p - biphenylyl, o - terphenyl, m - terphenyl, p - terphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, indenyl, fluorenyl, tetrahydronaphthyl, perylenyl, -yl, tetracenyl, fluoranthenyl, benzophenanthryl and other aromatic groups.

[0119] In this specification, a heteroaryl group refers to a cyclic aromatic system having 2 - 24 carbon atoms containing 1, 2 or 3 heteroatoms selected from N, O, P, Si, S, Ge, Se or Te and the remaining ring atoms being carbon, and these rings can fuse to form a ring. One or more hydrogen atoms in the heteroaryl group can be substituted by the same substituents as in the case of the aryl group.

[0120] Specific examples of the heteroaryl group include furyl, benzofuryl, dibenzofuryl, thienyl, benzothienyl, dibenzothienyl, pyrrolyl, indolyl, carbazolyl, pyridyl, quinolinyl, imidazolyl, benzimidazolyl, oxazolyl, benzoxazolyl, triazinyl, triazolyl, piperidinyl, acridinyl, phenoxazinyl, thiazolyl, benzothiazolyl, pyrimidinyl, pyrazinyl and the like.

[0121] In this specification, an alkyl group is linear or branched. Specific examples thereof include methyl, ethyl, propyl, isopropyl, isobutyl, sec - butyl, tert - butyl, pentyl, isopentyl, hexyl and the like. One or more hydrogen atoms in the alkyl group can be substituted by the same substituents as in the case of the aryl group.

[0122] In this specification, a heteroalkyl group means that one or more carbon atoms, preferably 1 - 5 carbon atoms, in the main chain of the alkyl group are substituted by heteroatoms such as oxygen atoms, sulfur atoms, nitrogen atoms, phosphorus atoms and the like. One or more hydrogen atoms in the heteroalkyl group can be substituted by the same substituents as in the case of the alkyl group.

[0123] In this specification, the "ring" in a cycloalkyl group refers to a substituent having a structure capable of forming a saturated hydrocarbon monocyclic or polycyclic ring in an alkyl group. Specific examples of the cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, methylcyclohexyl, ethylcyclopentyl, ethylcyclohexyl, adamantyl, bicyclobenzodienyl, decahydronaphthyl, norbornyl, borneol, isoborneol and the like. One or more hydrogen atoms in the cycloalkyl group can be substituted by the same substituents as in the case of the aryl group.

[0124] In the present specification, an alkoxy group is a substituent in which an oxygen atom is bonded to the end of an alkyl group or a cycloalkyl group. Specific examples thereof include a methoxy group, an ethoxy group, a propoxy group, an isobutoxy group, a sec-butoxy group, a pentyloxy group, an isopentyloxy group, and a hexyloxy group, etc. One or more hydrogen atoms in the alkoxy group may be substituted with the same substituents as those in the case of the aryl group.

[0125] In the present specification, specific examples of an arylalkyl group include a benzyl group, a phenethyl group, a phenylpropyl group, a naphthylmethyl group, a naphthylethyl group, etc. One or more hydrogen atoms in the arylalkyl group may be substituted with the same substituents as those in the case of the aryl group.

[0126] In the present specification, specific examples of an alkylsilyl group include a trimethylsilyl group, a triethylsilyl group, and a methylcyclobutylsilyl group, etc. One or more hydrogen atoms in the alkylsilyl group may be substituted with the same substituents as those in the case of the aryl group.

[0127] In the present specification, specific examples of an arylsilyl group include a triphenylsilyl group, a diphenylmethylsilyl group, and a diphenylvinylsilyl group, etc. One or more hydrogen atoms in the arylsilyl group may be substituted with the same substituents as those in the case of the aryl group.

[0128] In the present specification, an alkenyl group means an alkyl substituent containing a carbon-carbon double bond formed by two carbon atoms, and an alkynyl group means an alkyl substituent containing a carbon-carbon triple bond formed by two carbon atoms.

[0129] In the present specification, a diarylamino group means an amino group in which two identical or different aryl groups as described above are bonded to a nitrogen atom, and a diheteroarylamino group of the compound of the present invention means an amino group in which two identical or different heteroaryl groups are bonded to a nitrogen atom. In addition, the aryl(heteroaryl)amino group means an amino group in which the aryl group and the heteroaryl group are respectively bonded to a nitrogen atom.

[0130] According to an example of the present invention, a preferred compound of the host may be any one selected from the compounds represented by [Chemical Formulas [1] to

[63] ].

[0131] As the host, one compound may be used, or two or more compounds may be used together.

[0132] The solubility of the host in the solvent may be 0.1 wt% or more and 50 wt% or less, 0.5 wt% or more and 20 wt% or less, preferably 1 wt% or more, and more preferably 2 wt% or more.

[0133] The solvent may include at least one of a chlorine-based solvent, an ether-based solvent, an aromatic solvent, an aliphatic solvent, a ketone-based solvent, an ester-based solvent, an alcohol-based solvent, an amide-based solvent, and a benzoate-based solvent. The solvent may be a single pure substance or a mixture, and preferably, it may be a benzoate-based solvent.

[0134] For example, the chlorine-based solvent may include chloroform, dichloromethane, or chlorobenzene, the ether-based solvent may include tetrahydrofuran or dioxane, the aromatic solvent may include toluene, xylene, or trimethylbenzene, the aliphatic solvent may include cyclohexane, n-pentane, or n-hexane, the ketone-based solvent may include acetone, methyl ethyl ketone, or cyclohexanone, the ester-based solvent may include ethyl acetate or butyl acetate, the alcohol-based solvent may include methanol, ethanol, propanol, or cyclohexanol, the amide-based solvent may include N,N-dimethylformamide, and the benzoate-based solvent may include methyl benzoate, ethyl benzoate, or butyl benzoate.

[0135] The solvent may be used alone or two or more solvents may be mixed and used.

[0136] The boiling point of the solvent may be 60°C to 300°C, and preferably, it may be 130°C to 300°C, but is not limited thereto.

[0137] The viscosity of the solvent may be 1 cP to 10 cP, and preferably, it may be 2 cP to 8 cP, but is not limited thereto.

[0138] The solution containing the compound represented by [Chemical Formula A] and the solvent may be suitable for manufacturing an organic electroluminescent device using a solution process.

[0139] The solution may further contain a fluorescent dopant or a phosphorescent dopant.

[0140] For example, the fluorescent dopant may include a pyrene compound, a deuterium-substituted pyrene compound, an arylamine, a deuterium-substituted arylamine, a perylene compound, a deuterium-substituted perylene compound, a pyrrole compound, a deuterium-substituted pyrrole compound, a boron compound, a fluorene compound, a deuterium-substituted fluorene compound, a hydrazone compound, a deuterium-substituted hydrazone compound, a carbazole compound, a deuterium-substituted carbazole compound, a stilbene compound, a deuterium-substituted stilbene compound, a starburst compound, a deuterium-substituted starburst compound, an oxadiazole compound, a deuterium-substituted oxadiazole compound, coumarine, a deuterium-substituted coumarine, but is not limited thereto.

[0141] As the phosphorescent dopant, an organometallic compound containing iridium, platinum, osmium, titanium, zirconium, hafnium, europium, terbium, thulium, iron, cobalt, nickel, ruthenium, rhodium, palladium, or a combination thereof may be mentioned, but is not limited thereto.

[0142] The dopant may be a compound represented by the following [Chemical Formula B-1] or [Chemical Formula B-2]:

[0143]

[0144] In the [Chemical Formula B-1] and [Chemical Formula B-2],

[0145] each of T1 to T3 is the same as or different from each other and is independently an aromatic hydrocarbon ring having 6 to 50 carbon atoms or an aromatic heterocyclic ring having 2 to 40 carbon atoms,

[0146] each of T1 to T3 can be independently substituted by at least one R T When substituted by two or more Rs, T these Rs T are the same as or different from each other,

[0147] the R T is selected from the group consisting of hydrogen, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, -N(R”)2, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a cyano group, and a halogen,

[0148] the R”s are the same as or different from each other and are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and the R”s can combine with each other to form an alicyclic or aromatic monocyclic or polycyclic ring,

[0149] the Y1 is selected from the group consisting of N-R 13 、CR 14 R 15 、O、S and SiR 16 R17 any one of the group consisting of

[0150] said Y2 is selected from the group consisting of N-R 18 , CR 19 R 20 , O, S and SiR 21 R 22 any one of the group consisting of

[0151] said Y3 is selected from the group consisting of N-R 23 , CR 24 R 25 , O, S and SiR 26 R 27 any one of the group consisting of

[0152] said R 13 to R 27 are each the same as or different from one another, and are each independently selected from the group consisting of hydrogen, deuterium atom, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 24 carbon atoms, substituted or unsubstituted aryl having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl having 5 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 50 carbon atoms, substituted or unsubstituted alkoxy having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkylthioxy having 1 to 30 carbon atoms, substituted or unsubstituted arylthioxy having 5 to 30 carbon atoms, substituted or unsubstituted alkylamino having 1 to 30 carbon atoms, substituted or unsubstituted arylamino having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylamino having 2 to 30 carbon atoms, substituted or unsubstituted diarylamino having 12 to 24 carbon atoms, substituted or unsubstituted diheteroarylamino having 2 to 24 carbon atoms, substituted or unsubstituted aryl(heteroaryl)amino having 7 to 24 carbon atoms, substituted or unsubstituted alkylsilyl having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl having 5 to 30 carbon atoms, cyano and halogen, and said R 13 to R 27 each can be combined with one or more rings selected from the group consisting of said T1 to T3 to further form an alicyclic or aromatic monocyclic or polycyclic ring.

[0153] In the compound represented by any one of [Chemical Formula B-1] and [Chemical Formula B-2], details of the substituents are as described in the compound represented by [Chemical Formula A].

[0154] In one example of the present invention, the compounds represented by [Chemical Formula B-1] and [Chemical Formula B-2] may contain at least one -N(R”)2.

[0155] The compound represented by any one of [Chemical Formula B-1] and [Chemical Formula B-2] may be any one selected from the group consisting of the following chemical formulas [D 201] to [D 350]:

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165] Based on 100 parts by weight of the host, the amount of the fluorescent dopant or phosphorescent dopant may be from 0.01 part by weight to 20 parts by weight.

[0166] The content of the organic electroluminescent material containing the compound represented by [Chemical Formula A] in the solution may be 0.5 wt% or more, preferably 1.0 wt% or more, more preferably 2.0 wt% or more, but not limited thereto.

[0167] Next, with reference to Figure 1 A method for manufacturing an organic electroluminescent device according to an embodiment of the present invention will be described.

[0168] A substrate 10 may be prepared. The substrate 10 may be an organic substrate or a transparent plastic substrate having excellent transparency, surface smoothness, handleability, and waterproofness, but is not limited thereto, and may include substrates commonly used for organic electroluminescent devices.

[0169] A first electrode 20 may be formed by coating a material for an anode electrode on the upper surface of the substrate 10. The material for the anode electrode may include a material that is transparent and has excellent conductivity, such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), and / or zinc oxide (ZnO).

[0170] The 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. The 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.

[0171] An electron blocking layer (not shown) can be formed by selectively vacuum thermal 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 the lifetime and efficiency of the device. The electron blocking layer can be formed at an appropriate portion between the light emitting layer 50 and the hole injection layer 30, and preferably, can be formed between the light emitting layer 50 and the hole transport layer 40.

[0172] 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 on the upper surface of the hole transport layer 40 by any one of spin coating, dip coating, blade coating, spraying, roll coating, inkjet printing, and screen printing.

[0173] According to an example of the present invention, the thickness of the light emitting layer 50 can be to

[0174] A hole blocking layer (not shown) can be selectively formed on the upper surface of the light emitting layer 50 by vacuum deposition or spin coating. Since the lifetime and efficiency of the organic electroluminescent device will decrease when holes pass through the light emitting layer 50 and flow into the second electrode 80, if the hole blocking layer contains a hole blocking material having a very low highest occupied molecular orbital (HOMO) energy level, holes can be prevented from passing through the light emitting layer 50 and flowing into the second electrode 80. The hole blocking material is not particularly limited, but can have electron transport ability and a higher ionization potential than the organic electroluminescent material. The hole blocking material can include, for example, Balq, BCP, TPBI, etc.

[0175] The 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 by vacuum deposition or spin coating, and the second electrode 80 can be formed by vacuum thermally depositing a metal for the cathode electrode on the upper surface of the electron injection layer 70. The metal for the cathode electrode can 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 electroluminescent device, the metal for the cathode electrode can include indium tin oxide (ITO) or indium zinc oxide (IZO).

[0176] An organic electroluminescent device according to an example of the present invention can be manufactured by the manufacturing method described above.

[0177] Hereinafter, the organic electroluminescent device of the present invention will be described with reference to preferred embodiments. However, these embodiments are for more specifically illustrating the present invention, and it is obvious to those skilled in the art that the scope of the present invention is not limited thereto.

[0178] Synthesis Example 1: Synthesis of [7]

[0179] Synthesis Example 1-(1): Synthesis of Intermediate 1-a

[0180]

[0181] 6-Bromobenzo[c]phenanthrene (15.3 g, 0.05 mol) and tetrahydrofuran (145.2 mL) were added to a 1 L flask, and the inside of 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 solution was stirred at room temperature for 2 hours. After the reaction was completed, it was poured into a 2 M hydrochloric acid aqueous solution (100 mL) and stirred, extracted with ethyl acetate (50 mL), concentrated under reduced pressure, and then poured into an excess of heptane to filter the resulting solid, obtaining <Intermediate 1-a> (10.6 g, 78%).

[0182] Synthesis Example 1-(2): Synthesis of Intermediate 1-b

[0183]

[0184] In a 500 mL flask, <Intermediate 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, and the inside of the reactor was refluxed under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was poured into an excess of methanol, and the resulting solid was filtered. The filtered solid was further filtered to obtain <Intermediate 1-b> (17.4 g, 66%).

[0185] Synthesis Example 1-(3): Synthesis of Intermediate 1-c

[0186]

[0187]

[0188] Except for using B-[10-(phenyl-2,3,4,5,6-d5)-9-anthryl-1,2,3,4,5,6,7,8-d8]-boronic acid instead of <Intermediate 1-a> used in Synthesis Example 1-(2) and using 6-bromo-1-iodonaphthalene instead of 1-bromo-5-iodonaphthalene, the synthesis was carried out in the same manner to obtain <Intermediate 1-c>. (Yield: 70%)

[0189] Synthesis Example 1-(4): Synthesis of Intermediate 1-d

[0190]

[0191] Except for using <Intermediate 1-c> instead of 6-bromobenzo[c]phenanthrene used in Synthesis Example 1-(1), the synthesis was carried out in the same manner to obtain <Intermediate 1-d>. (Yield: 75%)

[0192] Synthesis Example 1-(5): Synthesis of [7]

[0193]

[0194] Except for using <Intermediate 1-d> instead of <Intermediate 1-a> used in Synthesis Example 1-(2) and using <Intermediate 1-b> instead of 1-bromo-5-iodonaphthalene, the synthesis was carried out in the same manner to obtain [7]. (Yield: 81%)

[0195] MS (MALDI-TOF): m / z 745.36 [M+]

[0196] Synthesis Example 2: Synthesis of

[19]

[0197] Synthesis Example 2-(1): Synthesis of Intermediate 2-a

[0198]

[0199] Except for using B-1-dibenzofuranylboronic acid instead of <Intermediate 1-a> used in Synthesis Example 1-(2), and using 9-bromo-10-iodoanthracene instead of 1-bromo-5-iodonaphthalene, it was synthesized in the same manner to obtain <Intermediate 2-a>. (Yield: 63%)

[0200] Synthesis Example 2-(2): Synthesis of Intermediate 2-b

[0201]

[0202] Except for using B-(3-bromo-1-naphthyl)boronic acid instead of <Intermediate 1-a> used in Synthesis Example 1-(2), and using <Intermediate 2-a> instead of 1-bromo-5-iodonaphthalene, it was synthesized in the same manner to obtain <Intermediate 2-b>. (Yield: 52%)

[0203] Synthesis Example 2-(3): Synthesis of Intermediate 2-c

[0204]

[0205] Except for using 1,3-phenylenediboronic acid instead of <Intermediate 1-a> used in Synthesis Example 1-(2), and using 6-bromobenzo[c]phenanthrene instead of 1-bromo-5-iodonaphthalene, it was synthesized in the same manner to obtain <Intermediate 2-c>. (Yield: 68%)

[0206] Synthesis Example 2-(4): Synthesis of

[19]

[0207]

[0208] Except for using <Intermediate 2-c> instead of <Intermediate 1-a> used in Synthesis Example 1-(2), and using <Intermediate 2-b> instead of 1-bromo-5-iodonaphthalene, it was synthesized in the same manner to obtain

[19] . (Yield: 78%)

[0209] MS(MALDI-TOF): m / z 772.28 [M +

[0210] Synthesis Example 3: Synthesis of

[40]

[0211] Synthesis Example 3-(1): Synthesis of Intermediate 3-a

[0212]

[0213] ​Except for using B-(1-dibenzofuranyl-2,3,4,6,7,8,9-d7)boronic acid instead of B-1-dibenzofuranylboronic acid used in Synthesis Example 2-(1), it was synthesized in the same method to obtain <Intermediate 3-a>. (Yield: 72%)

[0214] Synthesis Example 3-(2): Synthesis of Intermediate 3-b

[0215]

[0216] Add <Intermediate 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), 1,3-benzenediboronic acid (11.6 g, 0.07 mol) into a 1000 mL four-necked round-bottom flask, then add 250 mL of toluene, 125 mL of ethanol, and 125 mL of water, and reflux the inside of the reactor under a nitrogen atmosphere. After the reaction is completed, pour it into an excess of methanol and filter the generated solid. Filter the filtered solid to obtain <Intermediate 3-b> (22.1 g, 67%).

[0217] Synthesis Example 3-(3): Synthesis of Intermediate 3-c

[0218]

[0219] Except for using <Intermediate 3-b> instead of <Intermediate 1-a> used in Synthesis Example 1-(2) and using 2-bromo-1-iodonaphthalene instead of 1-bromo-5-iodonaphthalene, it was synthesized in the same method to obtain <Intermediate 3-c>. (Yield: 72%)

[0220] Synthesis Example 3-(4): Synthesis of Intermediate 3-d

[0221]

[0222] Under a nitrogen atmosphere, add 5,8-dibromobenzo[c]phenanthrene (13.5 g, 0.035 mol), B-(1-dibenzofuranyl-2,3,4,6,7,8,9-d7)boronic acid (7.9 g, 0.036 mol), Pd(PPh3)4 (0.8 g, 0.00065 mol), potassium carbonate (9 g, 0.065 mol), 100 ml of toluene and 30 ml of water into a round-bottom flask, and reflux for 12 hours. After the reaction is completed, cool the reaction solution to room temperature, separate the layers, concentrate the organic layer, separate by column chromatography, and then recrystallize to obtain <Intermediate 3-d> (10.1 g, 60%).

[0223] Synthesis Example 3-(5): Synthesis of Intermediate 3-e

[0224]

[0225] Except for using <Intermediate 3-d> instead of <Intermediate 3-a> used in Synthesis Example 3-(2), it was synthesized in the same manner to obtain <Intermediate 3-e>. (Yield: 66%)

[0226] Synthesis Example 3-(6): Synthesis of

[40]

[0227]

[0228] Except for using <Intermediate 3-e> instead of <Intermediate 1-d> used in Synthesis Example 1-(5) and using <Intermediate 3-c> instead of <Intermediate 1-b>, it was synthesized in the same manner to obtain

[40] . (Yield: 82%)

[0229] MS (MALDI-TOF): m / z 1028.44 [M +

[0230] Synthesis Example 4: Synthesis of

[61]

[0231] Synthesis Example 4-(1): Synthesis of Intermediate 4-a

[0232]

[0233] Except for using 1-bromo-5-iodonaphthalene instead of 6-bromo-1-iodonaphthalene used in Synthesis Example 1-(3), it was synthesized in the same manner to obtain <Intermediate 4-a>. (Yield: 65%)

[0234] Synthesis Example 4-(2): Synthesis of Intermediate 4-b

[0235]

[0236] Except for using <Intermediate 4-a> instead of <Intermediate 1-c> used in Synthesis Example 1-(4), it was synthesized in the same manner to obtain <Intermediate 4-b>. (Yield: 74%)

[0237] Synthesis Example 4-(3): Synthesis of

[61]

[0238]

[0239]

[0240] Except for using <Intermediate 4-b> instead of <Intermediate 1-d> used in Synthesis Example 1-(5), it was synthesized in the same manner to obtain

[61] . (Yield: 81%)

[0241] ​MS (MALDI-TOF): m / z 745.36 [M +

[0242] Examples 1 to 4

[0243] Poly(3,4-ethylenedioxythiophene):poly(styrenesulfonic acid) (AI4083), which is widely used as a hole injection layer, was spin-coated on the ITO transparent electrode to form a film with a thickness of 60 nm, and then baked at 200 °C for 30 minutes to form a hole injection layer. TFB was spin-coated on the hole injection layer to form a film with a thickness of 20 nm, and then baked at 130 °C for 10 minutes to form a hole transport layer. A 2 wt% solution of methyl benzoate containing the host compound and dopant [D 265] (weight ratio of host:dopant: 97:3) of the present invention as shown in Table 1 below was spin-coated on the hole transport layer to form a film with a thickness of 30 nm, and then baked at 180 °C for 30 minutes to form a light-emitting layer. It was baked at 130 °C for 10 minutes in a nitrogen atmosphere, and then [E-1] and [E-2] were deposited in a ratio of 1:1 as an electron transport layer to form a film with a thickness of 25 nm. [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 light-emitting device. The luminescence characteristics of the organic light-emitting device were measured at 10 mA / cm 2 2.

[0244] Comparative Examples 1 to 2

[0245] Except for using [BH1] and [BH2] instead of the compound of the present invention in the device structure of the above embodiments, an organic light-emitting device of a comparative example was fabricated in the same manner, and the luminescence characteristics of the organic light-emitting device were measured at 10 mA / cm 2 2.

[0246]

[0247]

[0248] Table 1

[0249] Main body Driving voltage (V) Efficiency (cd / A) T95 (hr) Example 1 [7] 4.0 5.1 52 Example 2

[19] 4.2 5.0 55 Example 3

[40] 4.2 4.7 54 Example 4

[61] 4.3 4.9 59 Comparative Example 1 [BH1] 4.6 4.5 45 Comparative Example 2 [BH2] 4.7 4.4 45

[0250] The voltage, efficiency, and lifetime of the organic electroluminescent devices fabricated in Examples 1 to 4 and Comparative Examples 1 to 2 were measured, and the results are shown in Table 1. Among them, T95 refers to the time required for the luminance to decrease to 95% of the initial luminance.

[0251] ​It has been confirmed that the devices of the examples using the compounds of the present invention exhibit good driving voltage and efficiency, and the lifetime characteristics are improved compared to the devices of the comparative examples.

Claims

1. An organic electroluminescent device, comprising: a first electrode; a second electrode; and an organic layer formed between the first electrode and the second electrode, wherein the organic electroluminescent device is characterized in that: The organic layer includes a light-emitting layer formed using a solution containing an organic electroluminescent material and a solvent, The organic electroluminescent material comprises a host and a dopant, The host is one or more compounds represented by the following [Chemical Formula A]: [Chemical formula A] In the [Chemical Formula A], the L1 are the same as or different from each other, and are each independently selected from the group consisting of a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms. R and R1 to R 12 The same as or different from each other and are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthiooxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthiooxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or any one of the group consisting of an unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamine group having 2 to 30 carbon atoms, a substituted or unsubstituted diarylamine group having 12 to 24 carbon atoms, a substituted or unsubstituted diheteroarylamine group having 2 to 24 carbon atoms, a substituted or unsubstituted aryl (heteroaryl)amine group having 7 to 24 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, wherein R1 to R 12 One of them is a single bond connected to the linking group L1, Ar1 is selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, The n1 is an integer from 1 to 5. When n1 is 2 or more, each L1 is the same as or different from each other. The m1 is an integer of 0 to 8. When m1 is 2 or more, each R is the same as or different from each other.

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

3. The organic electroluminescent device according to claim 2, characterized in that: The degree of deuteration of the compound represented by [Chemical Formula A] is 30% or more.

4. The organic electroluminescent device according to claim 1, characterized in that: The compound represented by [Chemical Formula A] includes at least one substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

5. The organic electroluminescent device according to claim 4, characterized in that: The compound represented by [Chemical Formula A] contains at least one group represented by the following [Chemical Formula A-1] or [Chemical Formula A-2]: In the above [Chemical Formula A-1] and [Chemical Formula A-2], The X is selected from the group consisting of O, S, NR', Si(R')2, The Z and R' are the same as or different from each other and are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthiooxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthiooxy group having 6 to 30 carbon atoms, a substituted or unsubstituted The group consisting of alkylamino groups, substituted or unsubstituted arylamino groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylamino groups having 2 to 30 carbon atoms, substituted or unsubstituted diarylamino groups having 12 to 24 carbon atoms, substituted or unsubstituted diheteroarylamino groups having 2 to 24 carbon atoms, substituted or unsubstituted aryl (heteroaryl)amine groups having 7 to 24 carbon atoms, substituted or unsubstituted aryl groups having 6 to 50 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 50 carbon atoms, substituted or unsubstituted alkylsilyl groups having 1 to 30 carbon atoms, and substituted or unsubstituted arylsilyl groups having 6 to 30 carbon atoms, The n2 is an integer of 0 to 7, and the n3 is an integer of 0 to 5. When n2 and n3 are 2 or more, each Z is the same as or different from each other.

6. The organic electroluminescent device according to claim 5, characterized in that: The X is O.

7. The organic electroluminescent device according to claim 1, characterized in that: The molecular weight of the compound represented by [Chemical Formula A] is 650 or more.

8. The organic electroluminescent device according to claim 1, characterized in that: The L1 is a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

9. The organic electroluminescent device according to claim 1, characterized in that: The n1 is 2 to 5.

10. The organic electroluminescent device according to claim 1, characterized in that: The solvent includes at least one of chlorine solvents, ether solvents, aromatic solvents, aliphatic solvents, ketone solvents, ester solvents, alcohol solvents, amide solvents and benzoate solvents.

11. The organic electroluminescent device according to claim 1, characterized in that: The main body is dissolved in the solvent in an amount of 1 weight percent or more.

12. The organic electroluminescent device according to claim 1, characterized in that: The subject is represented by any one of the following [1] to [63]:

13. The organic electroluminescent device according to claim 1, characterized in that: The dopant is a compound represented by the following [Chemical Formula B-1] or [Chemical Formula B-2]: In the above [Chemical Formula B-1] and [Chemical Formula B-2], The T1 to T3 are the same as or different from each other, and are independently an aromatic hydrocarbon ring having 6 to 50 carbon atoms, or an aromatic heterocyclic ring having 2 to 40 carbon atoms, The T1 to T3 can each be independently represented by at least one R T Replaced by two or more R T When replaced, these R T Same or different from each other, The R T The alkyl radical is selected from hydrogen, a deuterium atom, a substituted or unsubstituted alkyl radical having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl radical having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl radical having 2 to 24 carbon atoms, a substituted or unsubstituted aryl radical having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl radical having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl radical having 5 to 30 carbon atoms, a substituted or unsubstituted heteroaryl radical having 2 to 50 carbon atoms, a substituted or any one of the group consisting of an unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthiooxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthiooxy group having 5 to 30 carbon atoms, -N(R")2, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a cyano group and a halogen group, The R" are the same as or different from each other, and are independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and the R" can be combined with each other to form an alicyclic or aromatic monocyclic or polycyclic ring, The Y1 is selected from NR 13 , CR 14 R 15 , O, S and SiR 16 R 17 Any of the groups consisting of The Y2 is selected from NR 18 , CR 19 R 20 , O, S and SiR 21 R 22 Any of the groups consisting of The Y3 is selected from NR 23 , CR 24 R 25 , O, S and SiR 26 R 27 Any of the groups consisting of The R 13 To R 27 each being the same as or different from each other and independently selected from hydrogen, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsulfonyl group having 1 to 30 carbon atoms any one of the group consisting of an oxy group, a substituted or unsubstituted arylthiooxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 2 to 30 carbon atoms, a substituted or unsubstituted diarylamino group having 12 to 24 carbon atoms, a substituted or unsubstituted diheteroarylamino group having 2 to 24 carbon atoms, a substituted or unsubstituted aryl (heteroaryl)amino group having 7 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a cyano group and a halogen group, wherein R 13 To R 27 Each of them can be combined with one or more rings selected from the group consisting of T1 to T3 to further form an alicyclic or aromatic monocyclic or polycyclic ring.

14. The organic electroluminescent device according to claim 13, characterized in that: The compounds represented by [Chemical Formula B-1] and [Chemical Formula B-2] contain at least one -N(R")2.

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

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

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