Organic electroluminescent compounds, host materials, and organic electroluminescent devices containing the same
The combination of compounds in OLEDs as host materials addresses the limitations of existing OLEDs by enhancing stability and efficiency, leading to longer-lasting and more efficient devices.
Patent Information
- Application Number
- JP2020201742
- Authority / Receiving Office
- JP · JP
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2019-12-24
- Filing Date
- 2020-12-04
- Publication Date
- 2025-09-04
- Estimated Expiration
- 2040-12-04
AI Technical Summary
Existing organic electroluminescent devices (OLEDs) face challenges with insufficient lifetime and efficiency, particularly in medium- and large-sized panels, necessitating the development of materials with high thermal stability, electrochemical stability, and uniform emissive layers for improved performance.
The use of a specific compound represented by Formula 1 in combination with another compound (Formula 2) as host materials in OLEDs, which are designed to enhance the stability and efficiency of the emissive layer, thereby extending the device's lifespan.
The proposed host materials result in OLEDs with extended lifetimes and improved efficiency, suitable for display and lighting systems.
Smart Images

Figure 0007733979000001 
Figure 0007733979000002 
Figure 0007733979000003
Abstract
Description
[Technical Field]
[0001] The present disclosure relates to organic electroluminescent compounds, host materials comprising specific combinations of compounds, and organic electroluminescent devices comprising the same. [Background technology]
[0002] Electroluminescent (EL) devices are self-emitting display devices that have the advantages of providing a wider viewing angle, a larger contrast ratio, and a faster response time. In 1987, Eastman Kodak developed the first organic EL device by using small aromatic diamine molecules and aluminum complexes as materials for forming the light-emitting layer (see Non-Patent Document 1).
[0003] Organic electroluminescent devices (OLEDs) convert electrical energy into light by applying electricity to organic electroluminescent materials and typically include an anode, a cathode, and organic layers formed between the two electrodes. The organic layers of an OLED can include a hole injection layer, a hole transport layer, a hole auxiliary layer, an emissive auxiliary layer, an electron blocking layer, an emissive layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. Materials used in the organic layers can be classified according to their functions as hole injection materials, hole transport materials, hole auxiliary materials, emissive auxiliary materials, electron blocking materials, emissive materials (including host materials and dopant materials), electron buffer materials, hole blocking materials, electron transport materials, and electron injection materials. In OLEDs, application of a voltage causes holes from the anode and electrons from the cathode to be injected into the emissive layer, and recombination of the holes and electrons generates high-energy excitons. The organic emissive compound transitions to an excited state by the energy, and when the organic emissive compound returns to its ground state, it emits light from the energy.
[0004] The most important factor determining the luminous efficiency of OLEDs is the emissive material. The emissive material must have high quantum efficiency and high electron and hole mobility, and the formed emissive layer must be uniform and stable. Emitting materials can be classified into blue, green, and red emissive materials based on the emitted color, and can also include yellow or orange emissive materials. Additionally, emissive materials can be classified into host materials and dopant materials based on their function. In recent years, there has been an urgent need to develop OLEDs with high efficiency and long lifetimes. In particular, given the EL performance requirements for medium- and large-sized OLED panels, there is an urgent need to develop materials that exhibit superior properties to conventional materials. Therefore, as a solid-state solvent and energy transfer material, the host material should preferably have high purity and molecular weight suitable for vacuum deposition. Furthermore, the material must have a high glass transition temperature and high thermal decomposition temperature to achieve thermal stability, high electrochemical stability to achieve a long lifetime, easy formation of amorphous thin films, good adhesion to adjacent layer materials, and non-migration to other layers.
[0005] Currently, OLEDs primarily use phosphorescent materials, which have excellent luminous efficiency in panel implementations. However, for many applications, such as televisions and lighting, the lifetime of OLEDs is insufficient, and high OLED efficiency is still required. Typically, the higher the brightness of an OLED, the shorter its lifetime. Therefore, new luminescent materials with long lifetime characteristics are required for long-term use and high resolution displays. [Prior art documents] [Non-patent literature]
[0006] [Non-Patent Document 1] Appl.Phys.Lett.51,913,1987 Summary of the Invention [Problem to be solved by the invention]
[0007] The object of the present disclosure is to provide an organic electroluminescent compound having a new structure suitable for application in an organic electroluminescent device. Another object of the present disclosure is to provide an improved host material that can provide an organic electroluminescent device with long-life characteristics. [Means for solving the problem]
[0008] The present inventors have found that the above object can be achieved by a compound represented by the following formula 1. The compound represented by the following formula 1 can be applied to an organic electroluminescent device as a plurality of host materials in combination with a compound represented by the following formula 2: [ka] (In the formula, W represents a single bond, O, S, CR6R7, or NL-R8; Y represents O, S, CR6R7, or NL-R8; L's each independently represent a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30-membered) heteroarylene; R1 to R8 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3 to 30 membered) heteroaryl, substituted or unsubstituted tri(C1 to C30) alkylsilyl, substituted or unsubstituted di(C1 to C30) alkyl(C6 to C30) arylsilyl, substituted or unsubstituted (C1 to C30) alkyldi(C6 to C30) arylsilyl, substituted or unsubstituted tri(C6 to C30) arylsilyl, substituted or unsubstituted mono- or di-(C1 to C30) alkylamino, substituted or unsubstituted (C1 to C30) alkyl(C6 to C30) arylamino, or substituted or unsubstituted mono- or di-(C6 to C30) arylamino, or adjacent pairs of R1 to R8 can be bonded to form a ring; a to d each independently represent an integer of 1 to 4, e represents an integer of 1 or 2, each of a to e is an integer of 2 or greater, and each of R1, R2, R3, R4, and R5 may be the same or different; [ka] (In the formula, L1 represents a single bond or a substituted or unsubstituted (C6 to C30) arylene; Ar1 represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted nitrogen-containing (13-30 membered) heteroaryl; R9 and R 10 each independently represent deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-50 membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, or substituted or unsubstituted mono- or di-(C6-C30) arylamino; or R9 and R 10 can be joined to form a substituted or unsubstituted ring, provided that R or R 10 represents a substituted (C6-C30) aryl, the substituent of the substituted (C6-C30) aryl is not carbazolyl or dibenzofuranyl, but is R or R 10 forms a substituted ring, provided that the substituents on the substituted ring do not include triazinyl; f and g each independently represent an integer of 0 to 4, provided that f and g are not simultaneously zero, and when f and g each represent an integer of 2 or more, each of R9 and R 10 (Provided that each of the can be the same or different).
[0009] Advantageous Effects of the Invention The organic electroluminescent compounds according to the present disclosure exhibit suitable performance for use in organic electroluminescent devices. In addition, by including a specific combination of compounds according to the present disclosure as a host material, an organic electroluminescent device having a longer life span than conventional organic electroluminescent devices can be provided, which can be used to manufacture a display system or a lighting system. DETAILED DESCRIPTION OF THE INVENTION
[0010] The present disclosure will be described in detail hereinafter. However, the following description is intended to illustrate the present disclosure and is not intended to limit the scope of the present disclosure in any way.
[0011] The term "organic electroluminescent material" in the present disclosure refers to a material that can contain at least one compound and can be used in an organic electroluminescent device. The organic electroluminescent material can be included in any layer that constitutes an organic electroluminescent device, as needed. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, an emitting auxiliary material, an electron blocking material, an emitting material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material.
[0012] The term "multiple organic electroluminescent materials" in the present disclosure refers to an organic electroluminescent material that includes a combination of at least two compounds and can be included in any layer constituting an organic electroluminescent device. It can refer to both the material before being included in the organic electroluminescent device (e.g., before deposition) and the material after being included in the organic electroluminescent device (e.g., after deposition). For example, the multiple organic electroluminescent materials can be a combination of at least two compounds that can be included in at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. Depending on the method used in the art, the at least two compounds can be included in the same layer or different layers, and can be mixedly evaporated or co-evaporated, or evaporated separately.
[0013] The term "multiple host materials" in the present disclosure refers to a host material that includes a combination of at least two compounds and can be included in any light-emitting layer constituting an organic electroluminescent device. It can refer to both a material before being included in an organic electroluminescent device (for example, before vapor deposition) and a material after being included in an organic electroluminescent device (for example, after vapor deposition). For example, the multiple host materials of the present disclosure can be a combination of at least two host materials, and can optionally further include a conventional material included in an organic electroluminescent material. The at least two compounds included in the multiple host materials can be included together in one light-emitting layer, or can be included in different light-emitting layers. For example, the at least two host materials can be mixed and evaporated or co-evaporated, or can be evaporated separately.
[0014] As used herein, the term "(C1-C30) alkyl" refers to a straight-chain or branched alkyl having 1 to 30 carbon atoms constituting the chain, preferably 1 to 10, and more preferably 1 to 6. Alkyl may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and the like. The term "(C3-C30) cycloalkyl" refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 skeletal carbon atoms, preferably 3 to 20, and more preferably 3 to 7 carbon atoms. Cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like. The term "(3- to 7-membered) heterocycloalkyl" refers to a cycloalkyl having 3 to 7 skeletal atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably O, S, and N. Heterocycloalkyl may include tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, and the like. The term "(C6-C30)aryl(ene)" refers to a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 skeletal carbon atoms. Aryl may be partially saturated and may contain a spiro structure. Aryl may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, spiro[fluorene-benzofluorene]yl, and the like. Specifically, aryl includes phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 4-chrysenyl, 5-chrysenyl,6-chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo[a]fluorenyl, benzo[b]fluorenyl, benzo[c]fluorenyl, dibenzofluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2- p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenylyl, 4''-tert-butyl-p-terf phenyl-4-yl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 11,11-dimethyl-1-benzo[a]fluorenyl, 11,11-dimethyl-2-benzo[a]fluorenyl, 11,11-dimethyl-3-benzo[a]fluorenyl, 11,11-dimethyl-4- Benzo[a]fluorenyl, 11,11-dimethyl-5-benzo[a]fluorenyl, 11,11-dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 11,11-dimethyl-10-benzo[a]fluorenyl, 11,11-dimethyl-1-benzo[b]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl, 11,11-dimethyl-3-benzo[b]fluorenyl,11,11-dimethyl-4-benzo[b]fluorenyl, 11,11-dimethyl-5-benzo[b]fluorenyl, 11,11-dimethyl-6-benzo[b]fluorenyl, 11,11-dimethyl-7-benzo[b]fluorenyl, 11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[b]fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl-2-benzo[c]fluorenyl, 11,11-dimethyl- 3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c]fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]fluorenyl, 11,11-dimethyl-9-benzo[c]fluorenyl, 11,11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl, 11,11-diphenyl-2-benzo[a]fluorenyl fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl, 11,11-diphenyl-4-benzo[a]fluorenyl, 11,11-diphenyl-5-benzo[a]fluorenyl, 11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl, 11,11-diphenyl-8-benzo[a]fluorenyl, 11,11-diphenyl-9-benzo[a]fluorenyl, 11,11-diphenyl-10-benzo[a]fluorenyl, 11,11-diphenyl-1-benzo[b]fluorenyl nyl, 11,11-diphenyl-2-benzo[b]fluorenyl, 11,11-diphenyl-3-benzo[b]fluorenyl, 11,11-diphenyl-4-benzo[b]fluorenyl, 11,11-diphenyl-5-benzo[b]fluorenyl, 11,11-diphenyl-6-benzo[b]fluorenyl, 11,11-diphenyl-7-benzo[b]fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl, 11,11-diphenyl-10-benzo[b]fluorenyl,11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2-benzo[c]fluorenyl, 11,11-diphenyl-3-benzo[c]fluorenyl, 11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c]fluorenyl, 11,11-diphenyl-6-benzo[c]fluorenyl, 11,11-diphenyl-7-benzo[c]fluorenyl, 11,11-diphenyl-8-benzo[c]fluorenyl, 11,11-diphenyl-9-benzo[c]fluorenyl, 11,11-diphenyl-10-benzo[c]fluorenyl, and the like may be included.
[0015] The term "(3- to 50-membered)heteroaryl(ene)" refers to an aryl or arylene having 3 to 50 skeletal ring atoms, preferably 3 to 30 skeletal ring atoms, and containing at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, and P. The heteroaryl(ene) may be a monocyclic ring or a fused ring fused with at least one benzene ring, may be partially saturated, may be formed by attaching at least one heteroaryl or aryl group to a heteroaryl group via a single bond, and may include a spiro structure. Heteroaryl includes monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl, as well as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, naphthophenyl, and the like. and fused-ring heteroaryls such as benzofuranyl, naphthobenzothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, and the like. More specifically, heteroaryl includes 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizinyl, 2-indolizinyl, 3-indolizinyl, 5-indolizinyl, 6-indolizinyl, 7-indolizinyl, 8-indolizinyl, 2-imidazopyridyl, 3-imidazopyridyl, 5-imidazopyridyl, 6-imidazopyridyl, 7-imidazopyridyl, 8-imidazopyridyl, 3-pyridyl, 4-pyridyl, 1-indolyl,2-Indolyl, 3-Indolyl, 4-Indolyl, 5-Indolyl, 6-Indolyl, 7-Indolyl, 1-Isoindolyl, 2-Isoindolyl, 3-Isoindolyl, 4-Isoindolyl, 5-Isoindolyl, 6-Isoindolyl, 7-Isoindolyl, 2-Furyl, 3-Furyl, 2-Benzofuranyl, 3-Benzofuranyl, 4-Benzofuranyl, 5-Benzofuranyl, 6-Benzofuranyl, 7-Benzofuranyl, 1-Isobenzofuranyl, 3-Isobenzofuranyl, 4-Isobenzofuranyl, 5-Isobenzofuranyl, 6-Isobenzofuranyl yl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazolyl-1-yl, azacarbazolyl-2-yl, azacarbazolyl-3-yl, azacarbazolyl Azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarbazolyl-6-yl, azacarbazolyl-7-yl, azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl allyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-tert-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl,2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho-[1,2-b]-benzofuranyl, 3 -naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho-[1,2-b]-benzofuranyl, 6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl, 8-naphtho-[1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl, 1-naphtho-[2,3-b]-benzofuranyl, 2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl 1-naphtho-[2,3-b]-benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b]-benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl, 10-naphtho-[2,3-b]-benzofuranyl, 1-naphtho-[2,1-b]-benzofuranyl, 2-naphtho-[2,1-b]-benzofuranyl, 3-naphtho-[2,1-b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[ 2,1-b]-benzofuranyl, 6-naphtho-[2,1-b]-benzofuranyl, 7-naphtho-[2,1-b]-benzofuranyl, 8-naphtho-[2,1-b]-benzofuranyl, 9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-benzothiophenyl, 2-naphtho-[1,2-b]-benzothiophenyl, 3-naphtho-[1,2-b]-benzothiophenyl, 4-naphtho-[1,2-b]-benzothiophenyl, 5-naphtho-[1,2-b]-benzothiophenyl,6-naphtho-[1,2-b]-benzothiophenyl, 7-naphtho-[1,2-b]-benzothiophenyl, 8-naphtho-[1,2-b]-benzothiophenyl, 9-naphtho-[1,2-b]-benzothiophenyl, 10-naphtho-[1,2-b]-benzothiophenyl, 1-naphtho-[2,3-b]-benzothiophenyl, 2-naphtho-[2,3-b]-benzothiophenyl, 3-naphtho-[2,3-b]-benzothiophenyl, 4-naphtho-[2,3-b]-benzothiophenyl, 5-naphtho-[2,3-b]-benzothiophenyl, 1-naphtho-[2,1-b]-benzothiophenyl, 2-naphtho-[2,1-b]-benzothiophenyl, 3 Examples of "halogen" include 1-naphtho-[2,1-b]-benzothiophenyl, 4-naphtho-[2,1-b]-benzothiophenyl, 5-naphtho-[2,1-b]-benzothiophenyl, 6-naphtho-[2,1-b]-benzothiophenyl, 7-naphtho-[2,1-b]-benzothiophenyl, 8-naphtho-[2,1-b]-benzothiophenyl, 9-naphtho-[2,1-b]-benzothiophenyl, 10-naphtho-[2,1-b]-benzothiophenyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl, and the like. "Halogen" includes F, Cl, Br, and I.
[0016] Additionally, the term "substituted" in the phrase "substituted or unsubstituted" means that a hydrogen atom in a particular functional group is replaced with another atom or another functional group, i.e., a substituent. In the present disclosure, the substituents of substituted alkyl, substituted aryl(ene), substituted heteroaryl(ene), substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted mono- or di-alkylamino, substituted alkylarylamino, substituted mono- or di-arylamino, and substituted rings are each independently selected from deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C30) alkyl, halo(C1-C30) alkyl, (C2-C30) Alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C3-C30)cycloalkyl, (C3-C30)cycloalkenyl, (3-7 membered)heterocycloalkyl, (C6-C30)aryloxy, (C6-C30)arylthio, (3-30 membered)heteroaryl unsubstituted or substituted with (C6-C30)aryl, (C6-C30)aryl unsubstituted or substituted with (3-30 membered)heteroaryl, tri(C1-C30)alkylsilyl, tri(C6- (C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C30)arylsilyl, amino, mono- or di-(C1-C30)alkylamino, mono- or di-(C2-C30)alkenylamino, unsubstituted or (C1-C30)alkyl-substituted mono- or di-(C6-C30)arylamino, mono- or di-(3-30 membered)heteroarylamino, (C1-C30)alkyl(C2-C30)alkenylamino, (C1-C30)a alkyl(C6-C30)arylamino, (C1-C30)alkyl(3-30 membered)heteroarylamino, (C2-C30)alkenyl(C6-C30)arylamino, (C2-C30)alkenyl(3-30 membered)heteroarylamino, (C6-C30)aryl(3-30 membered)heteroarylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl,and at least one selected from the group consisting of (C1-C30) alkyl(C6-C30) arylboronyl, (C6-C30) aryl(C1-C30) alkyl, and (C1-C30) alkyl(C6-C30) aryl. According to one embodiment of the present disclosure, the substituents are each independently at least one selected from the group consisting of deuterium, cyano, (C1-C20) alkyl, (5-25 membered) heteroaryl unsubstituted or substituted with (C6-C25) aryl, unsubstituted (C6-C25) aryl, and tri(C6-C25) arylsilyl. According to another embodiment of the present disclosure, the substituents are each independently at least one selected from the group consisting of cyano, (C1-C10) alkyl, (5-20 membered) heteroaryl unsubstituted or substituted with (C6-C18) aryl, unsubstituted (C6-C18) aryl, and tri(C6-C18) arylsilyl. For example, the substituents may each independently be at least one selected from the group consisting of cyano, methyl, phenyl, naphthalene, biphenyl, naphthylphenyl, terphenyl, triphenylenyl, triazinyl substituted with at least one of phenyl, naphthyl, and biphenyl, pyridyl substituted with phenyl, pyrimidinyl substituted with phenyl, dibenzofuranyl, carbazolyl substituted with phenyl, and triphenylsilyl.
[0017] As used herein, the term "ring formed by the bonding of adjacent substituents" refers to at least two adjacent substituents bonded or fused to each other to form a substituted or unsubstituted monocyclic or polycyclic (3-30 membered) alicyclic or aromatic ring, or a combination thereof, preferably a substituted or unsubstituted monocyclic or polycyclic (3-26 membered) alicyclic or aromatic ring, or a combination thereof, more preferably a monocyclic or polycyclic (5-25 membered) aromatic ring unsubstituted or substituted with at least one of a (C6-C18) aryl and a (3-20 membered) heteroaryl. In addition, the formed ring may contain at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S. For example, the ring can be a benzene ring, an indole ring substituted with at least one of phenyl, biphenyl, naphthyl, naphthylphenyl, phenylnaphthyl, terphenyl, triphenylenyl, phenylpyridyl, and phenylpyrimidinyl, an unsubstituted or phenylcarbazolyl-substituted spiro[indene-xanthene] ring, an unsubstituted or phenylcarbazolyl-substituted xanthene ring, and the like.
[0018] In the present disclosure, heteroaryl, heteroarylene, and heterocycloalkyl can each independently contain at least one heteroatom selected from B, N, O, S, Si, and P. In addition, the heteroatom may be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C2-C30) alkenyl and substituted or unsubstituted (C1-C30) alkyl(C2-C30) arylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, substituted or unsubstituted mono- or di-(3-30 membered) heteroarylamino, substituted or unsubstituted (C1-C30) alkyl(C2-C30) alkenylamino, substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, substituted or unsubstituted (C1-C30) alkyl(3-30 membered) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl(C6-C30) arylamino, substituted or unsubstituted (C2-C30) alkenyl(3-30 membered) heteroarylamino, and substituted or unsubstituted (C6-C30) aryl(3-30 membered) heteroarylamino.
[0019] The multiple host materials of the present disclosure include a first host material and a second host material, where the first host material includes a compound represented by Formula 1 and the second host material includes a compound represented by Formula 2. According to one embodiment of the present disclosure, the compound represented by Formula 1 and the compound represented by Formula 2 are different from each other.
[0020] In Formula 1, W represents a single bond, O, S, CR6R7, or NL-R8. According to one embodiment of the present disclosure, W represents a single bond, O, or S.
[0021] In Formula 1, Y represents O, S, CR6R7, or NL-R8. According to one embodiment of the present disclosure, Y represents O, S, or NL-R8.
[0022] In Formula 1, each L independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene. According to one embodiment of the present disclosure, each L independently represents a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (5-25 membered) heteroarylene. According to another embodiment of the present disclosure, each L independently represents a single bond, an unsubstituted (C6-C18) arylene, or a (5-20 membered) heteroarylene unsubstituted or substituted with a (C6-C18) aryl. For example, each L independently may be a single bond, phenylene, or naphthylene.
[0023] In Formula 1, R1 to R8 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, or substituted or unsubstituted mono- or di-(C6-C30) arylamino, or adjacent groups of R1 to R8 can be bonded to each other to form a ring. According to one embodiment of the present disclosure, at least one of R1 to R8 includes a substituted or unsubstituted (3 to 30-membered) heteroaryl containing at least one nitrogen. For example, at least one of R1 to R8 includes a substituted triazinyl, a substituted quinazolinyl, a substituted quinoxalinyl, a substituted quinolyl, a substituted carbazolyl, etc. According to another embodiment of the present disclosure, at least one of R1 to R5 includes a substituted or unsubstituted (3 to 30-membered) heteroaryl containing at least one nitrogen. According to one embodiment of the present disclosure, R1 to R8 each independently represent hydrogen, a substituted or unsubstituted (C6 to C25) aryl, or a substituted or unsubstituted (5 to 25-membered) heteroaryl, or adjacent R1 to R8 can be bonded to each other to form a ring. According to another embodiment of the present disclosure, R1 to R8 each independently represent hydrogen, (C6-C18)aryl unsubstituted or substituted with (3-30 membered)heteroaryl, or (5-20 membered)heteroaryl unsubstituted or substituted with at least one of (C6-C18)aryl and (5-20 membered)heteroaryl, or adjacent ones of R1 to R8 can be bonded to each other to form a ring.For example, R1, R2, and R5 can each independently be hydrogen, phenyl, or triazinyl substituted with phenyl; R3 can be hydrogen, phenyl, carbazolyl substituted with phenyl, or triazinyl substituted with at least one of phenyl, biphenyl, and dibenzofuranyl; or two adjacent R3's can be bonded to each other to form a benzene ring; R4 can be hydrogen, substituted or unsubstituted phenyl, substituted naphthyl, substituted pyridyl, substituted triazinyl, quinolyl substituted with phenyl, quinazolyl substituted with phenyl, quinoxalinyl substituted with phenyl, or carbazolyl substituted with phenyl; or two adjacent R4's can be bonded to each other to form a benzene ring, in which case substituted The substituents of the phenyl, substituted naphthyl, and substituted pyridyl can each independently be diphenyltriazinyl, phenylbiphenyltriazinyl, or phenylnaphthyltriazinyl, and the substituents of the substituted triazinyl can be at least one of phenyl, naphthyl, biphenyl, terphenyl, naphthylphenyl, phenylnaphthyl, and dibenzofuranyl, and R8 can be unsubstituted phenyl, unsubstituted naphthyl, unsubstituted biphenyl, substituted triazinyl, substituted quinazolinyl, substituted quinoxalinyl, or unsubstituted dibenzofuranyl, in which case the substituents of the substituted triazinyl, substituted quinazolinyl, and substituted quinoxalinyl can each independently be at least one of phenyl, naphthyl, biphenyl, and dibenzofuranyl.
[0024] In Formula 1, a to d each independently represent an integer of 1 to 4, e represents an integer of 1 or 2, and each of a to e is an integer of 2 or greater, and each of R1, R2, R3, R4, and R5 can be the same or different. According to one embodiment of the present disclosure, a, b, and e can be an integer of 1, and c and d can be integers of 1 or 2.
[0025] According to one embodiment of the present disclosure, Formula 1 can be represented by at least one of the following Formulas 1-1 to 1-4. [ka]
[0026] In formulas 1-1 to 1-4, W, Y, R1 to R5, and a to e are as defined in formula 1.
[0027] In Formula 2, L1 represents a single bond or a substituted or unsubstituted (C6-C30) arylene. According to one embodiment of the present disclosure, L1 represents a single bond or a substituted or unsubstituted (C6-C25) arylene. According to another embodiment of the present disclosure, L1 represents a single bond or an unsubstituted (C6-C18) arylene. For example, L1 can be a single bond, phenylene, naphthylene, or biphenylene.
[0028] In Formula 2, Ar1 represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 membered) heteroaryl containing at least one nitrogen (N). According to one embodiment of the present disclosure, Ar1 represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (13-30 membered) heteroaryl (N) containing at least one nitrogen (N). According to another embodiment of the present disclosure, Ar1 represents an unsubstituted (C6-C25) aryl or a (13-25 membered) heteroaryl substituted with an unsubstituted or (C6-C18) aryl containing at least one nitrogen (N). For example, Ar1 can be a substituted or unsubstituted phenyl, naphthyl, biphenyl, terphenyl, triphenylenyl, dimethylfluorenyl, diphenylfluorenyl, or unsubstituted or phenyl-substituted carbazolyl, where the substituted phenyl can be at least one of cyano, methyl, and triphenylsilyl.
[0029] In Formula 2, R9 and R 10each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-50 membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, or substituted or unsubstituted mono- or di-(C6-C30) arylamino; or R9 and R 10 Adjacent groups of can be bonded to each other to form a ring, in which case R 10 represents a substituted or unsubstituted (3 to 50 membered) heteroaryl, or R 10 Two or more adjacent R or R groups can be bonded to each other to form a ring. 10 When R or R represents a substituted (C6-C30)aryl, the substituent of the substituted aryl may not be a (3-30 membered)heteroaryl, for example, carbazolyl or dibenzofuranyl. 10 represents a substituted or unsubstituted carbazolyl, R or R 10 can be attached to the backbone at the 9-position of the carbazolyl. According to one embodiment of the present disclosure, R or R 10 When R and R form a substituted ring, the substituents of the substituted ring do not include triazinyl. For example, the substituents of the substituted ring may not be diphenyltriazinyl or phenyl substituted with diphenyltriazinyl. According to one embodiment of the present disclosure, R and R 10 each independently represents hydrogen, a substituted or unsubstituted (C6-C25) aryl, or a substituted or unsubstituted (5-40 membered) heteroaryl, or R and R 10 According to another embodiment of the present disclosure, adjacent ones of R and R can be bonded to each other to form a ring. 10represents hydrogen, unsubstituted (C6-C18) aryl, or unsubstituted or (C6-C18) aryl-substituted (5-20 membered) heteroaryl; R9 and R 10 The other represents a (5-35-membered) heteroaryl or a (5-20-membered) heteroaryl unsubstituted or substituted with a (C6-C18) aryl, or adjacent ones can be bonded to each other to form a ring. For example, R9 can be hydrogen, phenyl, or carbazolyl substituted with phenyl, and R 10 can be a substituted or unsubstituted carbazolyl or a 33-membered heteroaryl containing nitrogen and oxygen and substituted with phenyl, or R 10 two or more adjacent ones of the above may be bonded to each other to form a substituted indole ring or a substituted or unsubstituted spiro[indene-xanthene] ring, in which case the substituent of the substituted carbazolyl may be at least one of phenyl, naphthyl, biphenyl, terphenyl, triphenylenyl, and phenyl-substituted pyridyl, the substituent of the substituted indole ring may be at least one of phenyl, biphenyl, naphthyl, naphthylphenyl, phenylnaphthyl, terphenyl, triphenylenyl, phenyl-substituted pyridyl, and phenyl-substituted pyrimidinyl, and the substituent of the substituted spiro[indene-xanthene] ring may be phenyl-substituted carbazolyl.
[0030] In Formula 2, f and g each independently represent an integer of 0 to 4. When f and g each represent an integer of 2 or more, each of R9 and R 10 can be the same or different. According to one embodiment of the present disclosure, f and g are not simultaneously zero (0). According to another embodiment of the present disclosure, f can be an integer of 1, and g can be an integer of 1 or 2.
[0031] According to one embodiment of the present disclosure, Formula 2 can be represented by at least one of the following Formulas 2-1 to 2-3. [ka]
[0032] In formulas 2-1 and 2-3, X and Y are each independently N-L2-Ar2, O, S, or CR. 14 CR 15 According to one embodiment of the present disclosure, X represents O, S, or CR. 14 CR 15 and Y is N-L2-Ar2, O, S, or CR. 14 CR 15 According to another embodiment of the present disclosure, X and Y each independently represent N-L2-Ar2 or CR 14 CR 15 For example, Y can be N-L2-Ar2.
[0033] L2 represents a single bond or a substituted or unsubstituted (C6-C30) arylene. According to one embodiment of the present disclosure, L2 represents a single bond or an unsubstituted (C6-C25) arylene. For example, L2 can be a single bond, phenylene, naphthylene, or biphenylene.
[0034] Ar2 represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 membered) heteroaryl containing at least one nitrogen (N). According to one embodiment of the present disclosure, Ar2 represents a substituted or unsubstituted (C6-C30) aryl. According to another embodiment of the present disclosure, Ar2 represents a substituted or unsubstituted (C6-C25) aryl. According to a further embodiment of the present disclosure, Ar2 represents a (C6-C18) aryl that is unsubstituted or substituted with at least one of cyano, (C1-C6) alkyl, and tri(C6-C18) arylsilyl. For example, Ar2 can be a substituted phenyl, naphthyl, biphenyl, terphenyl, triphenylenyl, dimethylfluorenyl, or diphenylfluorenyl, where the substituent of the substituted phenyl can be at least one of cyano, methyl, and triphenylsilyl.
[0035] In Equations 2-1 to 2-3, R 11 ~R 15each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, or substituted or unsubstituted mono- or di-(C6-C30) arylamino, or two or more adjacent R 11 The 's can be bonded to each other to form a ring, and two or more adjacent R 12 The 's can be bonded to each other to form a ring, and two or more adjacent R 13 The 's can be bonded to each other to form a ring, and R 14 and R 15 can be bonded to each other to form a ring. According to one embodiment of the present disclosure, in formula 2-3, R 12 is not triazinyl. According to one embodiment of the present disclosure, R 11 ~R 15 each independently represents hydrogen, a substituted or unsubstituted (C1-C20) alkyl, a substituted or unsubstituted (C6-C25) aryl, or a substituted or unsubstituted (5-20 membered) heteroaryl, or two or more adjacent R 12 The 's can be bonded to each other to form a ring, and R 14 and R 15 can be bonded to each other to form a ring. According to another embodiment of the present disclosure, R 11 ~R 15 each independently represents hydrogen, unsubstituted (C1-C10) alkyl, unsubstituted (C6-C18) aryl, or (5-18 membered) heteroaryl unsubstituted or substituted with (C6-C18) aryl, or two or more adjacent R 12 The 's can be bonded to each other to form a ring, and R 14 and R 15can be bonded to each other to form a ring. For example, R 11 and R 13 can be hydrogen, and R 12 can be hydrogen, phenyl, or unsubstituted or phenyl-substituted carbazolyl, or two or more adjacent R 12 's can be joined together to form a spiro[indene-xanthene] ring or a phenyl-substituted indole ring; R 14 and R 15 can be linked together to form an unsubstituted or phenylcarbazolyl-substituted xanthene ring.
[0036] In formulas 2-1 to 2-3, i and l each independently represent an integer of 1 to 4, h and j each independently represent an integer of 1 to 3, and k represents an integer of 1 or 2, in which case h to j each independently represent an integer of 2 or more, and R 11 Each of R 12 and R 13 can be the same or different. According to one embodiment of the present disclosure, h, j, and k can be integers of 1, and i can be an integer of 1 or 2.
[0037] In formulas 2-1 to 2-3, L1, Ar1, R9, and f are as defined in formula 2.
[0038] In one embodiment of the present disclosure, Equation 2 can be expressed as Equation 3 below: [ka]
[0039] In Formula 3, L1 and L2 each independently represent a single bond or a substituted or unsubstituted (C6-C30) arylene. According to one embodiment of the present disclosure, L1 and L2 each independently represent a single bond or a substituted or unsubstituted (C6-C25) arylene. According to another embodiment of the present disclosure, L1 and L2 each independently represent a single bond or an unsubstituted (C6-C18) arylene. For example, L1 and L2 each independently may be a single bond, phenylene, naphthylene, or biphenylene.
[0040] In Formula 3, Ar1 and Ar2 each independently represent a substituted or unsubstituted (C6-C30) aryl. According to one embodiment of the present disclosure, Ar1 and Ar2 each independently represent a substituted or unsubstituted (C6-C25) aryl. According to another embodiment of the present disclosure, Ar1 and Ar2 each independently represent a (C6-C25) aryl that is unsubstituted or substituted with at least one of cyano, (C1-C6) alkyl, and tri(C6-C18) arylsilyl. For example, Ar1 and Ar2 each independently can be substituted or unsubstituted phenyl, naphthyl, biphenyl, terphenyl, triphenylenyl, dimethylfluorenyl, or diphenylfluorenyl, where the substituent on the substituted phenyl can be at least one of cyano, methyl, and triphenylsilyl.
[0041] In Formula 3, R9 and R 11 ~R 13each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted (-C1-C30) alkyl(C6-C30) arylamino, or substituted or unsubstituted mono- or di-(C6-C30) arylamino, or two or more adjacent R's can be bonded to each other to form a ring, and two or more adjacent R's 11 The 's can be bonded to each other to form a ring, and two or more adjacent R 12 The 's can be bonded to each other to form a ring, and two or more adjacent R 13 According to one embodiment of the present disclosure, R and R 11 ~R 13 each independently represents hydrogen, a substituted or unsubstituted (C1-C20) alkyl, a substituted or unsubstituted (C6-C25) aryl, or a substituted or unsubstituted (5-25 membered) heteroaryl. According to another embodiment of the present disclosure, R9 and R 11 ~R 13 are each independently hydrogen, unsubstituted (C1-C10) alkyl, unsubstituted (C6-C18) aryl, or (5-20 membered) heteroaryl unsubstituted or substituted with (C6-C18) aryl. For example, R9 and R 12 may each independently be hydrogen, methyl, phenyl, or carbazolyl substituted with phenyl; R 11 and R 13 can be hydrogen.
[0042] In Formula 3, f and i each independently represent an integer of 1 to 4, and h and j each independently represent an integer of 1 to 3, where f, h, i, and j are integers of 2 or greater, and each of R9, R11 Each of R 12 and R 13 can be the same or different.
[0043] Specifically, the compound represented by formula 1 can be exemplified by, but not limited to, the following compounds: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0044] Specifically, the compound represented by formula 2 can be exemplified by, but not limited to, the following compounds: [ka] [ka] [ka] [ka]
[0045] A combination of at least one of compounds C-1 to C-148 and at least one of compounds H-1 to H-50 and H2-1 to H2-40 can be used in an organic electroluminescent device. According to one embodiment of the present disclosure, a combination of at least one of compounds C-1 to C-148 and at least one of compounds H-1 to H-50 can be used in an organic electroluminescent device. According to another embodiment of the present disclosure, a combination of at least one of compounds C-11 to C-23, C-41 to C-43, C-45 to C-49, C-54, C-55, C61 to C-63, C-66, C-67, C-71, C-72, C-75 to C-131, C-133 to C-148, and compounds H2-1 to H2-40 can be used in an organic electroluminescent device.
[0046] The present disclosure provides an organic electroluminescent compound represented by Formula 1, wherein at least one of R1 to R5 comprises a substituted or unsubstituted (3-30 membered) heteroaryl containing at least one nitrogen. According to one embodiment of the present disclosure, when Y represents NL-R8, at least one of R3 to R5 comprises a substituted or unsubstituted (3-30 membered) heteroaryl containing at least one nitrogen. According to one embodiment of the present disclosure, when Y represents NL-R8, R4 is not 9-phenylcarbazolyl or (9-carbazolyl)phenyl. According to one embodiment of the present disclosure, in the organic electroluminescent compound, at least one of R1 to R5 may comprise a (5-25 membered) heteroaryl containing at least one nitrogen and substituted with at least one of a (C6-C18) aryl and a (3-30 membered) heteroaryl. According to another embodiment of the present disclosure, in the organic electroluminescent compound, at least one of R1 to R5 may include a substituted or unsubstituted (6- to 10-membered) heteroaryl containing at least one nitrogen atom. Specifically, in the organic electroluminescent compound, at least one of R1 to R5 may include a substituted or unsubstituted triazinyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, or a substituted or unsubstituted carbazolyl. More specifically, in the organic electroluminescent compound, at least one of R1 to R5 may include a substituted triazinyl, a phenyl-substituted quinolyl, a phenyl-substituted quinazolinyl, a phenyl-substituted quinoxalinyl, or a phenyl-substituted carbazolyl, in which case the substituent of the substituted triazinyl may be at least one, preferably two, selected from the group consisting of phenyl, naphthyl, biphenyl, terphenyl, naphthylphenyl, phenylnaphthyl, and dibenzofuranyl.For example, in the organic electroluminescent compound, at least one of R1 to R5 may comprise a substituted triazinyl, a phenyl substituted with a substituted triazinyl, a naphthyl substituted with a substituted triazinyl, a pyridyl substituted with a substituted triazinyl, a quinolyl substituted with a phenyl, a quinazolinyl substituted with a phenyl, a quinoxalinyl substituted with a phenyl, or a carbazolyl substituted with a phenyl, wherein the substituents of the substituted triazinyl may be two selected from the group consisting of phenyl, naphthyl, biphenyl, terphenyl, naphthylphenyl, phenylnaphthyl, and dibenzofuranyl, and the two substituents may be the same or different.
[0047] According to one embodiment of the present disclosure, in the organic electroluminescent compound, R8 can be an unsubstituted (C6-C18)aryl, such as phenyl, naphthyl, biphenyl, and the like.
[0048] Specifically, the organic electroluminescent compounds can be exemplified as, but not limited to, compounds C-11 to C-23, C-41 to C-43, C-45 to C-49, C-54, C-55, C-61 to C-63, C-66, C-67, C-71, C-72, C-75 to C-131, and C-133 to C-148.
[0049] The present disclosure can provide an organic electroluminescent device comprising an organic electroluminescent compound, and in this case, the organic electroluminescent compound can be comprised in an emitting layer.In addition, the present disclosure can provide a plurality of host materials, including an organic electroluminescent compound and a compound represented by formula 2 as a first host material, for example, a compound represented by formula 3 as a second host material, and an organic electroluminescent device comprising the same.
[0050] The compounds represented by Formulas 1 to 3 and 2-1 to 2-3 according to the present disclosure can be prepared by synthetic methods known to those skilled in the art. For example, the compound represented by Formula 1 can be prepared as shown in the following Reaction Schemes 1 and 2, and the compound represented by Formula 2 can be prepared as shown in the following Reaction Schemes 3 to 5, but is not limited thereto. [Reaction Scheme 1] [ka] [Reaction Scheme 2] [ka] [Reaction Scheme 3] [ka] [Reaction Scheme 4] [ka] [Reaction Scheme 5] [ka]
[0051] In Reaction Schemes 1 to 5, W, Y, X, R1 to R5, L1, Ar1, R9, and R 11 ~R 13 , a to f, and h to l are as defined in formulas 1, 2, and 2-1 to 2-3, and Hal represents I, Br, Cl, ONf (nonafluorobutanesulfonyl), or OTf (triflate).
[0052] While exemplary synthetic examples of compounds represented by Formulas 1 and 2 of the present disclosure are described above, one skilled in the art will readily appreciate that all of these are based on Buchwald-Hartwig cross-coupling reactions, N-arylation reactions, Miyaura borylation reactions, Suzuki cross-coupling reactions, Pd(II)-catalyzed oxidative cyclization reactions, Heck reactions, cyclodehydration reactions, SN1 substitution reactions, SN2 substitution reactions, phosphine-mediated reductive cyclization reactions, Ullmann reactions, Wittig reactions, and the like, and that the above reactions will proceed even when substituents defined in Formulas 1 and 2 above but not specified in the particular synthetic examples are attached.
[0053] An organic electroluminescent device according to the present disclosure may include an anode, a cathode, and at least one organic layer between the anode and the cathode, where the organic layer may include a plurality of organic electroluminescent materials including a compound represented by Formula 1 as a first organic electroluminescent material and a compound represented by Formula 2 as a second organic electroluminescent material. According to one embodiment of the present disclosure, an organic electroluminescent device according to the present disclosure may include an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, where the light-emitting layer may include a plurality of host materials including a compound represented by Formula 1 as a first host material and a compound represented by Formula 2 as a second host material.
[0054] The light-emitting layer includes a host and a dopant. In this case, the host includes multiple host materials, and the multiple host materials include a first host material and a second host material. The first host material may consist solely of the compound represented by Formula 1, or may consist of at least one compound represented by Formula 1 and may further include conventional materials included in organic electroluminescent devices. The second host material may consist solely of the compound represented by Formula 2, or may consist of at least one compound represented by Formula 2 and may further include conventional materials included in organic electroluminescent devices. The weight ratio of the first host compound to the second host compound is about 1:99 to about 99:1, preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30, even more preferably about 40:60 to about 60:40, and even more preferably about 50:50.
[0055] In this specification, the light-emitting layer is a layer that emits light, and can be a single layer or a multi-layer structure in which two or more layers are stacked. The first host material and the second host material can all be included in one layer, or the first host material and the second host material can be included in different light-emitting layers. According to one embodiment of the present disclosure, the doping concentration of the dopant compound relative to the host compound included in the light-emitting layer can be less than 20% by weight.
[0056] The organic electroluminescent device of the present disclosure may further include at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, an emission auxiliary layer, an electron transport layer, an electron injection layer, an intermediate layer, an electron buffer layer, a hole blocking layer, and an electron blocking layer. According to one embodiment of the present disclosure, the organic electroluminescent device of the present disclosure may further include an amine-based compound as at least one of the hole injection material, the hole transport material, the hole auxiliary material, the emission material, the emission auxiliary material, and the electron blocking material, in addition to the plurality of host materials of the present disclosure. Furthermore, according to one embodiment of the present disclosure, the organic electroluminescent device of the present disclosure may further include an azine-based compound as at least one of the electron transport material, the electron injection material, the electron buffer material, and the hole blocking material, in addition to the plurality of host materials of the present disclosure.
[0057] In the organic electroluminescent device of the present disclosure, a hole injection layer, a hole transport layer, or an electron blocking layer, or a combination thereof, can be used between the anode and the light-emitting layer. The hole injection layer can be a multilayer structure to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, and each of the multilayer structures can simultaneously use two compounds. The hole transport layer or the electron blocking layer can also be a multilayer structure.
[0058] In addition, an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be used between the light-emitting layer and the cathode. The electron buffer layer may be a multilayer structure to control electron injection and improve the interfacial properties between the light-emitting layer and the electron injection layer. In this case, each of the multiple layers may simultaneously use two compounds. Also, the hole blocking layer or the electron transport layer may be a multilayer structure, and each of the multiple layers may use multiple compounds.
[0059] The dopant that is included in the organic electroluminescent device of the present disclosure can be at least one phosphorescent or fluorescent dopant, and preferably at least one phosphorescent dopant.The phosphorescent dopant material that is used in the organic electroluminescent device of the present disclosure is not particularly limited, but can preferably be selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt) metallized complex compound, more preferably be selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt) ortho-metallized complex compound, and even more preferably be ortho-metallized iridium complex compound.
[0060] Dopants included in the organic electroluminescent devices of the present disclosure can include, but are not limited to, compounds represented by Formula 101 below: [ka]
[0061] In Formula 101, L is selected from the following structures 1 and 2: [ka] Selected from R 100 ~R 103 each independently represent hydrogen, deuterium, halogen, unsubstituted or deuterium- or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3-30 membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy, or can be bonded to adjacent substituents to form a ring together with the pyridine, for example, a substituted or unsubstituted quinoline, benzofuropyridine, benzothienopyridine, indenopyridine, benzofuroquinoline, benzothienoquinoline, or indenoquinoline ring; R 104 ~R 107 each independently represent hydrogen, deuterium, halogen, unsubstituted or deuterium- or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy, or may be bonded to adjacent substituents to form a ring together with benzene, such as a substituted or unsubstituted naphthyl, fluorene, dibenzothiophene, dibenzofuran, indenopyridine, benzofuropyridine, or benzothienopyridine ring; R 201 ~R 211 each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium- or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl, or may be bonded to adjacent substituents to form a ring; s represents an integer of 1 to 3.
[0062] Specific examples of the dopant compound are as follows, but are not limited to these. [ka] [ka] [ka] [ka]
[0063] To form each layer of the organic electroluminescent device of the present disclosure, dry film-forming methods such as vacuum deposition, sputtering, plasma, ion plating methods, etc., or wet film-forming methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating methods, etc. can be used.
[0064] When using a wet film-forming method, a thin film can be formed by dissolving or diffusing the material for forming each layer in any appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent as long as it can dissolve or diffuse the material for forming each layer and does not cause any problems in film-forming ability.
[0065] The compounds represented by Formulas 1 and 2 of the present disclosure can be formed into films by the above-mentioned methods, generally by a co-evaporation process or a mixed evaporation process. Co-evaporation is a mixed evaporation method in which two or more materials are placed in separate crucible sources and current is applied to both cells simultaneously to evaporate the materials. Mixed evaporation is a mixed evaporation method in which two or more materials are mixed in a single crucible source before evaporating them and current is applied to the cell to evaporate the materials. Furthermore, when the first and second host compounds are present in the same layer or different layers of an organic electroluminescent device, the two host compounds can form films separately. For example, the first host compound can be evaporated followed by the second host compound.
[0066] The present disclosure can provide a display device by using an organic electroluminescent compound represented by Formula 1 or a plurality of host materials including a compound represented by Formula 1 and a compound represented by Formula 2. That is, a display system or a lighting system can be manufactured by using the organic electroluminescent compound of the present disclosure or a plurality of host materials of the present disclosure. Specifically, the organic electroluminescent compound of the present disclosure or a plurality of host materials of the present disclosure can be used to manufacture a display system such as a display system for a smartphone, tablet, notebook, PC, television, or automobile, or a lighting system such as an outdoor or indoor lighting system.
[0067] Hereinafter, the preparation methods of the compounds according to the present disclosure and their properties will be described in detail with reference to representative compounds of the present disclosure. However, the present disclosure is not limited by the following examples. [Example]
[0068] Example 1: Preparation of Compound C-11 [ka] Synthesis of Compound A-1 9-Phenyl-9H-carbazol-3-ylboronic acid (51 g, 178 mmol), 1-bromo-3-chloro-2-iodobenzene (60 g, 189 mmol), Pd(PPh3)4 (2.1 g, 1.82 mmol), and potassium carbonate (65 g, 473 mmol) were dissolved in 170 mL of distilled water, 400 mL of toluene, and 400 mL of THF in a flask, and the mixture was reacted at 70 °C for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate and the remaining water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound A-1 (46 g, yield: 57%).
[0069] Synthesis of Compound A-2 Compound A-1 (39 g, 90 mmol) and 350 mL of THF were added to a flask under a nitrogen atmosphere, and the mixture was cooled to -78 °C. Next, n-butyllithium (40 mL, 99 mmol) was slowly added dropwise to the mixture. Next, xanthone (16 g, 81 mmol) was added dropwise, and the mixture was allowed to react for 2 hours. After the reaction was completed, water was added to the mixture to quench the reaction, and the organic layer was extracted with ethyl acetate. The remaining water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound A-2 (40 g, yield: 80%).
[0070] Synthesis of Compound A-3 Compound A-2 (46 g, 83 mmol), sulfuric acid (24 g, 250 mmol), and 850 mL of toluene were added to a flask under a nitrogen atmosphere, and the mixture was stirred for 2 hours at 80°C. o C. After the reaction was completed, the mixture was neutralized, the organic layer was extracted with ethyl acetate, and residual water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound A-3 (19 g, yield: 50%).
[0071] Synthesis of compound A-4 Compound A-3 (21 g, 40 mmol), bis(pinacolato)diboron (12 g, 50 mmol), Pd2(dba)3 (0.45 g, 0.5 mmol), potassium acetate (7.8 g, 80 mmol), tricyclohexylphosphine (0.43 g, 1.5 mmol), and 400 mL of toluene were added to a flask, and the mixture was refluxed for 6 hours. After completion of the reaction, distilled water was added to the mixture to quench the reaction. The organic layer was extracted with ethyl acetate, and residual water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound A-4 (15 g, yield: 61%).
[0072] Synthesis of compound C-11 In a flask, compound A-4 (5 g, 8 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (3 g, 10 mmol), Pd(PPh3)4 (0.46 g, 0.4 mmol), and potassium carbonate (2.7 g, 20 mmol) were dissolved in 32 mL of toluene, 8 mL of distilled water, and 8 mL of ethanol, and the mixture was refluxed for 5 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate and the remaining water was removed using magnesium sulfate. The residue was separated by column chromatography to obtain compound C-11 (2.1 g, yield: 36%).
[0073] [Table 1]
[0074] Example 2: Preparation of Compound C-12 [ka] In a flask, compound A-4 (5 g, 8 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.4 g, 10 mmol), Pd(PPh3)4 (0.46 g, 0.4 mmol), and potassium carbonate (2.7 g, 20 mmol) were dissolved in 32 mL of toluene, 8 mL of distilled water, and 8 mL of ethanol, and the mixture was refluxed for 5 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate and the remaining water was removed using magnesium sulfate. The residue was separated by column chromatography to obtain compound C-12 (2.9 g, yield: 45%).
[0075] [Table 2]
[0076] Example 3: Preparation of Compound C-131 [ka] Synthesis of Compound B-1 9,9'-Spirobi[9H-fluoren]-4-ol (114 g, 343 mmol), 2-bromo-1-chloro-3-fluorobenzene (144 g, 686 mmol), potassium carbonate (224 g, 686 mmol), and 1 L of N-methyl-2-pyrrolidone (NMP) were added to a flask, and the mixture was reacted at 150 °C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate and the remaining water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound B-1 (155 g, yield: 86%).
[0077] Synthesis of Compound B-2 Compound B-1 (155 g, 300 mmol), Pd(OAc) (3.3 g, 15 mmol), tricyclohexylphosphine (8.4 g, 30 mmol), potassium carbonate (124 g, 900 mmol), and 1.5 L of dimethylacetamide (DMAc) were added to a flask, and the mixture was reacted at 150 °C for 10 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and residual water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound B-2 (95 g, yield: 72%).
[0078] Synthesis of Compound B-3 Compound B-2 (35 g, 79 mmol), potassium acetate (15 g, 158 mmol), bis(pinacolato)diboron (30 g, 119 mmol), Pd(dba)2 (0.9 g, 2%), tricyclohexylphosphine (0.9 g, 4 mol%), 18-crown-6 (0.3 g, 1 mol%), and 600 mL of toluene were added to a flask, and the mixture was reacted at 110 °C for 8 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and residual water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound B-3 (12 g, yield: 30%).
[0079] Synthesis of compound C-131 Compound B-3 (5 g, 9.4 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (3.5 g, 13 mmol), Pd(PPh3)4 (0.5 g, 0.47 mmol), potassium carbonate (3 g, 23 mmol), 50 mL of toluene, 12 mL of ethanol, and 12 mL of distilled water were added to a flask, and the mixture was refluxed for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate and the remaining water was removed using magnesium sulfate. The residue was separated by column chromatography to obtain compound C-131 (5.2 g, 87% yield).
[0080] [Table 3]
[0081] Example 4: Preparation of Compound C-76 [ka]
[0082] Synthesis of compound E-1 Spiro[fluoren-9,9'-xanthene]-2-ol (90 g, 258 mmol), 2-bromo-1-chloro-3-fluorobenzene (54 g, 258 mmol), potassium carbonate (53 mg, 387 mmol), and 900 mL of NMP were added to a flask, and the mixture was refluxed at 160 °C for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and residual water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound E-1 (97 g, yield: 70%).
[0083] Synthesis of compound E-2 Compound E-1 (100 g, 186 mmol), Pd(OAc) (2 g, 9.3 mmol), tricyclohexylphosphine (5.2 g, 18 mmol), potassium carbonate (77 g, 558 mmol), and 1.5 L of DMAc were added to a flask, and the mixture was reacted at 150 °C for 10 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and residual water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound E-2 (43 g, yield: 50%).
[0084] Synthesis of compound E-3 Compound E-2 (43 g, 94 mmol), potassium acetate (27 g, 282 mmol), bis(pinacolato)diboron (31 g, 122 mmol), Pd(dba)2 (1 g, 0.2 mol%), tricyclohexylphosphine (1 g, 0.4 mol%), 18-crown-6 (0.5 g, 0.2 mol%), and 1.2 L of toluene were added to a flask, and the mixture was reacted at 110 °C for 8 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate and the remaining water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound E-3 (39 g, yield: 75%).
[0085] Synthesis of compound C-76 Compound E-3 (10 g, 18 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (4.9 g, 18 mmol), Pd(PPh3)4 (0.4 g, 4 mol%), potassium carbonate (9.8 g, 45 mmol), toluene (100 mL), ethanol (25 mL), and distilled water (25 mL) were added to a flask, and the mixture was refluxed for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate and the remaining water was removed using magnesium sulfate. The residue was separated by column chromatography to obtain compound C-76 (5.1 g, yield: 43%).
[0086] [Table 4]
[0087] Hereinafter, the characteristics of an organic electroluminescent device (OLED) according to one embodiment of the present disclosure will be described. However, the following examples only serve to explain the characteristics of the OLED according to the present disclosure in detail, and the present disclosure is not limited to the following examples.
[0088] Device Examples 1-1 to 1-5: Fabrication of OLEDs Comprising a First Host Compound and a Second Host Compound According to the Present Disclosure An OLED according to the present disclosure was fabricated. A transparent indium tin oxide (ITO) thin film (10 Ω / sq) electrode on an OLED glass substrate (Geomatec Co., Ltd., Japan) was ultrasonically cleaned in acetone and isopropyl alcohol, and then stored in isopropanol. The ITO substrate was then attached to a substrate holder in a vacuum evaporation system. Compound HI-1, shown in Table 4 below, was introduced into one cell of the vacuum evaporation system, and compound HT-1, shown in Table 4 below, was introduced into another cell of the vacuum evaporation system. The two materials were evaporated at different ratios, and compound HI-1 was deposited at a doping amount of 3 wt % based on the total amount of compound HI-1 and compound HT-1 to form a 10 nm-thick first hole injection layer on the ITO substrate. Compound HT-1 was then deposited on the first hole injection layer to form an 80 nm-thick first hole transport layer. Next, compound HT-2 was introduced into another cell of the vacuum evaporation system, and a current was passed through the cell to evaporate it, thereby forming a 30-nm-thick second hole-transporting layer on the first hole-transporting layer. After forming the hole-injection layer and hole-transporting layer, an emitting layer was formed thereon as follows. The first and second host compounds shown in Table 1 below were introduced into two cells of the vacuum evaporation system as hosts, and compound D-50 was introduced into another cell as a dopant. The two host materials were evaporated in different ratios of 2:1, and the dopant materials were simultaneously evaporated in different ratios. The dopant was deposited at a doping amount of 10 wt % based on the total amount of host and dopant, forming a 40-nm-thick emitting layer on the second hole-transporting layer. Compounds ETL-1 and EIL-1 were evaporated in a weight ratio of 40:60 to form a 35-nm-thick electron-transporting layer on the emitting layer. After depositing the compound EIL-1 as an electron injection layer to a thickness of 2 nm on the electron transport layer, an 80 nm thick Al cathode was deposited on the electron injection layer using another vacuum deposition device. In this way, an OLED was fabricated. All materials used to fabricate the OLED were used in 10 -6 It was purified by vacuum sublimation at torr.
[0089] The emission colors and the time it takes for the brightness to decrease from 100% to 50% (lifetime, T50) at a brightness of 20,000 nits for the OLEDs fabricated in Device Examples 1-1 to 1-5 are shown in Table 1 below.
[0090] [Table 5]
[0091] Device Example 2-1: Fabrication of an OLED containing a compound according to the present disclosure An OLED was fabricated in the same manner as in Device Example 1-1, except that the light-emitting layer was formed as follows: Compound C-131 was introduced as a host into one cell of a vacuum deposition apparatus, and Compound D-50 was introduced as a dopant into the other cell. The two materials were evaporated at different rates to deposit the dopant at a doping amount of 10 wt % based on the total amount of the host and dopant, thereby forming a light-emitting layer with a thickness of 40 nm on the second hole-transporting layer.
[0092] Comparative Example 2-1: Preparation of an OLED containing a comparative compound as a host An OLED was fabricated in the same manner as in Device Example 2-1, except that the compound shown in Table 2 below was used instead of Compound C-131 as the host in the emissive layer.
[0093] The emission color and the time it takes for the brightness to decrease from 100% to 50% (lifetime, T50) at a brightness of 20,000 nits of the OLEDs prepared in Device Example 2-1 and Comparative Example 2-1 are shown in Table 2 below.
[0094] [Table 6]
[0095] Device Examples 3-1 to 3-4: Fabrication of OLEDs Comprising a First Host Material and a Second Host Material According to the Present Disclosure The OLED was fabricated in the same manner as in Device Example 1-1, except that the first host compound and the second host compound shown in Table 3 below were used.
[0096] Comparative Example 3-1: Preparation of an OLED containing a comparative compound as a host The OLED was fabricated in the same manner as Device Example 3-1, except that the compound shown in Table 3 below was used as the first host in the emissive layer.
[0097] The emission color and the time it takes for the brightness to decrease from 100% to 50% (lifetime, T50) at a brightness of 20,000 nits for the OLEDs fabricated in Device Examples 3-1 to 3-4 and Comparative Example 3-1 are shown in Table 3 below.
[0098] [Table 7]
[0099] From Table 2 above, it can be seen that OLEDs containing the compounds according to the present disclosure as host materials exhibited longer lifetime characteristics compared to conventional organic electroluminescent devices. That is, it can be seen that the organic electroluminescent compounds according to the present disclosure have better light-emitting properties than conventional materials. In addition, from Tables 1 and 3 above, it can be seen that devices using specific combinations of the compounds according to the present disclosure as multiple host materials exhibited improved lifetime characteristics.
[0100] The compounds used in the device examples and comparative examples are shown in Table 4 below.
[0101] [Table 8]
Claims
1. A plurality of host materials including a first host material containing a compound represented by the following formula 1 and a second host material containing a compound represented by any one of the following formulas 2-2 and 2-3, wherein the compound represented by the following formula 1 and the compound represented by any one of the following formulas 2-2 and 2-3 are different from each other: 【Chemical 1】 (In the formula, W is a single bond, O, S, or CR 6 R 7 , or N-L-R 8 represents Y is O, S, CR 6 R 7 , or N-L-R 8 represents Each L independently represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; R 1 ~R 8 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, or substituted or unsubstituted mono- or di-(C6-C30) arylamino; or R 1 ~R 8 adjacent ones of can be linked to each other to form a ring, a to d each independently represent an integer of 1 to 4, e represents an integer of 1 or 2, and each of a to e represents an integer of 2 or more; R 1 Each of R 2 Each of R 3 Each of R 4 and R 5 each of which can be the same or different), 【Chemistry 2】 (In the formula, L 1 represents a single bond or a deuterated or unsubstituted (C6-C30) arylene; Ar 1 represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted nitrogen-containing (13-30 membered) heteroaryl; Y represents N-L 2 -Ar 2 , O, S, or CR 14 CR 15 ; L 2 represents a single bond or a substituted or unsubstituted (C6-C30) arylene; Ar 2 represents a substituted or unsubstituted (C6-C30) aryl; R 9 represents deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-50 membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, or substituted or unsubstituted mono- or di-(C6-C30) arylamino, or adjacent R 9 may be bonded to each other to form a substituted or unsubstituted ring, with the proviso that R provided that when R 9 represents a substituted (C6-C30) aryl, a substituent of the substituted (C6-C30) aryl is not carbazolyl or dibenzofuranyl, when R 9 forms a substituted ring, a substituent of the substituted ring does not include triazinyl, and when R 9 represents a substituted or unsubstituted carbazolyl, R 9 is bonded to the skeleton at the 9-position of the carbazolyl; R 11 to R 15 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, or substituted or unsubstituted mono- or di-(C6-C30) arylamino; or two or more adjacent R 11 s can be bonded to each other to form a ring, and two or more adjacent R 12 can be bonded to each other to form a ring, two or more adjacent R 13 can be bonded to each other to form a ring, R 14 and R 15 can be bonded to each other to form a ring; However, in formula 2-3, R 12 does not contain triazinyl; f represents an integer of 0 to 4, and when f is an integer of 2 or more, each R 9 may be the same or different; i represents an integer of 1 to 4, j represents an integer of 1 to 3, k represents an integer of 1 or 2, and when each of i to k is an integer of 2 or greater, each of R 11 , each of R 12 , and each of R 13 can be the same or different).
2. The formula 1 is represented by the following formulas 1-1 to 1-4: 【Chemistry 3】 (Wherein W, Y, R 1 ~R 5 , and a to e are as defined in claim 1) 2. The host material of claim 1, wherein the host material is one of:
3. The substituted alkyl, substituted aryl(ene), substituted heteroaryl(ene), substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted mono- or di-alkylamino, substituted alkylarylamino, substituted mono- or di-arylamino, and substituents of the substituted ring are each independently deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C30) alkyl, halo(C1-C30) alkyl, (C2-C30) alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C3-C30)cycloalkyl, (C3-C30)cycloalkenyl, (3- to 7-membered)heterocycloalkyl, (C6-C30)aryloxy, (C6-C30)arylthio, (3- to 30-membered)heteroaryl unsubstituted or substituted with (C6-C30)aryl, (C6-C30)aryl unsubstituted or substituted with (3- to 30-membered)heteroaryl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, di(C1-C30)aryl alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C30)arylsilyl, amino, mono- or di-(C1-C30)alkylamino, mono- or di-(C2-C30)alkenylamino, unsubstituted or (C1-C30)alkyl-substituted mono- or di-(C6-C30)arylamino, mono- or di-(3- to 30-membered)heteroarylamino, (C1-C30)alkyl(C2-C30)alkenylamino, (C1-C30)alkyl(C6-C30)arylamino, (C1-C30)alkyl(3- to 30-membered) heteroarylamino, (C2-C30)alkenyl(C6-C30)arylamino, (C2-C30)alkenyl(3-30 membered)heteroarylamino, (C6-C30)aryl(3-30 membered)heteroarylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl, (C6-C30)aryl(C1-C30)alkyl,10. The plurality of host materials of claim 1, wherein the at least one is selected from the group consisting of (C1-C30) alkyl(C6-C30) aryl.
4. The compound represented by formula 1 is the following compound: 【Chemistry 4】 【Chemistry 5】 【Chemistry 6】 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 10. The plurality of host materials of claim 1, wherein the host material is at least one selected from:
5. The compound represented by formula 2 is the following compound: 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 10. The plurality of host materials of claim 1, wherein the host material is at least one selected from:
6. 10. An organic electroluminescent device comprising: an anode; a cathode; and at least one light-emitting layer between the anode and the cathode, wherein at least one of the light-emitting layers comprises a plurality of host materials according to claim 1.
7. Formula 1 below: 【Chemistry 15】 (In the formula, W is O, S, or NLR 8 represents Y is O, S, CR 6 R 7 , or N-L-R 8 represents Each L independently represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; R 1 ~R 8 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, or substituted or unsubstituted mono- or di-(C6-C30) arylamino; or R 1 ~R 8 adjacent ones of can be linked to each other to form a ring, R 1 ~R 5 at least one of comprises a substituted or unsubstituted nitrogen-containing (3- to 30-membered) heteroaryl; However, Y is N-L-R 8 When R represents 3 ~R 5 at least one of which comprises a substituted or unsubstituted nitrogen-containing (3-30 membered) heteroaryl, and Y is N-L-R 8 When R represents 4 is not 9-phenylcarbazolyl or (9-carbazolyl)phenyl, a to d each independently represent an integer of 1 to 4, e represents an integer of 1 or 2, and each of a to e represents an integer of 2 or more; R 1 Each of R 2 Each of R 3 Each of R 4 and R 5 can be the same or different) An organic electroluminescent compound represented by the formula:
8. A first host material comprising the compound represented by formula 1 according to claim 7 and a compound represented by formula 3: 【Chemistry 16】 (In the formula, L 1 and L 2 each independently represents a single bond or a substituted or unsubstituted (C6 to C30) arylene; Ar 1 and Ar 2 each independently represents a substituted or unsubstituted (C6-C30) aryl; R 9 and R 11 ~R 13 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or represents di-(C1-C30)alkylamino, substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, or substituted or unsubstituted mono- or di-(C6-C30)arylamino; or two or more adjacent R9 can be bonded to each other to form a ring; two or more adjacent R11 can be bonded to each other to form a ring; two or more adjacent R12 can be bonded to each other to form a ring; or two or more adjacent R13 can be bonded to each other to form a ring; f and i each independently represent an integer of 1 to 4, and h and j each independently represent an integer of 1 to 3, in which case f, h, i, and j are integers of 2 or more, and R 9 Each of R 11 Each of R 12 and R 13 can be the same or different) and a second host material comprising a compound represented by the formula:
9. The compound represented by formula 1 is the following compound: 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 【Chemical 21】 【Chemical 22】 8. The organic electroluminescent compound according to claim 7, selected from:
10. The compound represented by formula 3 is the following compound: 【Chemical 23】 【Chemistry 24】 9. The plurality of host materials of claim 8 selected from:
11. An organic electroluminescent device comprising the organic electroluminescent compound of claim 7.
12. 10. An organic electroluminescent device comprising an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein at least one of the light-emitting layers comprises a plurality of host materials according to claim 8.
Citation Information
Patent Citations
Heterocyclic compound and organic light-emitting device containing the same
JP2018535185A
Compounds for electronic devices
US20140225040A1
Compound for organic optoelectronic device, organic light emitting diode comprising same, and display device comprising organic light emitting diode
US20150144937A1
Condensed-cyclic compound and organic light emitting device including the same
US20160293848A1
Materials for organic electroluminescent devices
US20170141327A1