Compound and organic electroluminescent device

Abstract

Disclosed are a compound and an organic electroluminescent device. The compound has a nitrogen-containing fused ring structure represented by formula (1), wherein formula (1) is the same as described in the detailed description. The organic electroluminescent device has an emission layer including a compound having a nitrogen-containing condensed ring structure. The emission layer of the organic electroluminescent device may further include a phosphorescent complex. # imgabs0 #

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the priority of Korean Patent Application No. 10-2024-0010785 filed on January 24, 2024 in the Korean Intellectual Property Office and Japanese Patent Application No. 2023-180968 filed on October 20, 2023 in the Japan Patent Office, and all rights and interests arising therefrom, the contents of which are incorporated herein in their entirety by reference. Technical Field

[0003] The present disclosure relates to compounds and organic electroluminescent devices including the compounds. Background Art

[0004] Recently, organic electroluminescent devices (hereinafter, also referred to as "organic EL devices") have been used as various light-emitting devices, including smart phones or televisions. Luminescent materials have been used in the emission layer of organic EL devices, and fluorescent materials, phosphorescent materials, and thermally activated (activated) delayed fluorescent materials have been reported as luminescent materials (for example, as disclosed in: "Device Properties of Organic Semiconductors", compiled by Chihaya Adachi, Kodansha, March 22, 2012). Among organic EL devices, organic EL devices using fluorescent materials that utilize only fluorescence emission from a singlet state have been put into practical use due to their light-emitting principles, and in typical organic EL devices, the luminous efficiency may be 5% or less. For organic EL devices using phosphorescent materials, the luminous efficiency of the device may exceed 20%, and these organic EL devices have been typically put into practical use for green and red light emission. However, for blue light, fluorescent emission is generally used to provide satisfactory device life, and improvement in performance is desirable.

[0005] Recently, BT.2100, which is a new international standard for television broadcasting, has been announced, and in order to comply with the standard, there is a demand for further improving the color purity of the emission wavelength of the light-emitting device. By introducing a microcavity structure into an organic EL device using a conventional light-emitting material, the color purity can be improved and the half width (FWHM) of the emission wavelength can be narrowed. However, in the case of a light-emitting device with a wide emission spectrum FWHM, the luminous efficiency of the light-emitting device may be reduced because light deviating from the target wavelength is not used. Therefore, there is still a demand for a light-emitting material having a small emission spectrum FWHM and improved luminous efficiency. Summary of the invention

[0006] Disclosed is a compound having a peak wavelength in an emission spectrum in a blue wavelength region and capable of providing luminescence with high color purity and high efficiency. In addition, an organic electroluminescent device having an emission layer including such a compound is provided. In addition, the organic electroluminescent device has a peak wavelength in an emission spectrum in a blue wavelength region and can provide luminescence with high color purity and high efficiency.

[0007] Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.

[0008] The inventors have found that by using a compound having a specific nitrogen-containing fused polycyclic structure, including such a compound in the emission layer of an organic electroluminescent device, and in particular by using a combination of such a compound and a phosphorescent material in the emission layer, the desired luminescent properties can be provided. Although the uses of such compounds are not limited to those described herein, such compounds can be included in the emission layer, in particular by being included in the emission layer in combination with a phosphorescent material, so that a significant improvement in luminous efficiency can be achieved.

[0009] A compound represented by formula (1) is provided.

[0010]

[0011] In formula (1),

[0012] R 1 To R 16 At least one of the substituents is a substituent W represented by formula (2) (* represents a bonding site to the benzene ring),

[0013] as well as

[0014] R other than the substituent W 1 To R 16 Each is independently any one atom or group of (a1) to (a10):

[0015] (a1) Hydrogen or deuterium atoms;

[0016] (a2) halogen atoms;

[0017] (a3) cyano;

[0018] (a4) a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms;

[0019] (a5) a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms;

[0020] (a6) a substituted or unsubstituted arylamino group having 6 to 20 carbon atoms;

[0021] (a7) a substituted or unsubstituted triarylsilyl group, an alkyldiarylsilyl group, a dialkylarylsilyl group, or a trialkylsilyl group (wherein the aryl group is an aryl group having 6 to 20 carbon atoms, and the alkyl group is an alkyl group having 1 to 20 carbon atoms);

[0022] (a8) a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms;

[0023] (a9) a substituted or unsubstituted heterocyclic group having 3 to 30 ring atoms; and

[0024] (a10) a substituted or unsubstituted saturated hydrocarbon group or a saturated heterocyclic group, each of which is bonded to R 1 To R 16 The ring is formed by two adjacent groups in the ring and has 5 to 9 ring atoms.

[0025] Provided is a compound represented by formula (1), wherein R 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 , and R 15 At least two of may each be a substituent W.

[0026] Provided is an organic electroluminescent device including an emission layer containing a compound represented by formula (1).

[0027] An organic electroluminescent device including an emission layer is provided. The emission layer may include a phosphorescent complex and a compound represented by formula (1). BRIEF DESCRIPTION OF THE DRAWINGS

[0028] The above and other aspects, features, and advantages of some embodiments of the present disclosure will become more apparent from the following description considered in conjunction with the accompanying drawings, in which:

[0029] Figure 1 is a schematic cross-sectional view of an embodiment of an organic electroluminescent device;

[0030] Figure 2 is a schematic cross-sectional view of an embodiment of an organic electroluminescent device;

[0031] Figure 3 is a schematic cross-sectional view of an embodiment of an organic electroluminescent device according to another embodiment;

[0032] Figure 4is a graph showing the photoluminescence intensity (arbitrary unit, au) versus wavelength (nanometers, nm) of the emission spectra of Compound 1 and Comparative Compound C1 in toluene solution; and

[0033] Figure 5 Graphs showing photoluminescence intensity (au) versus wavelength (nm) of emission spectra of thin films formed by co-depositing Compound 1 or Comparative Compound C1 with a host compound. DETAILED DESCRIPTION

[0034] Embodiments will now be described in detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout the specification. In this regard, the present embodiment may have different forms and should not be construed as being limited to the description set forth herein. Therefore, embodiments are described below with reference to the accompanying drawings to illustrate aspects. As used herein, the term "and / or" includes any and all combinations of one or more of the related enumerated items. When before or after a list of elements, a statement such as "at least one (kind) of" modifies the entire list of elements and does not modify the individual elements of the list.

[0035] Hereinafter, embodiments of the present disclosure are described. In addition, the present disclosure is not limited to the following embodiments, and various modifications may be made without departing from the scope as defined by the claims. In addition, the embodiments described herein may be arbitrarily combined to form other embodiments.

[0036] It will be understood that when an element is referred to as being “on” another element, it can be directly on the other element or intervening elements may be present. In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements present.

[0037] It will be understood that although the terms "first", "second", "third", etc. may be used in this article to describe various elements, components, regions, layers, and / or parts, these elements, components, regions, layers, and / or parts should not be limited by these terms. These terms are only used to distinguish an element, component, region, layer, or part from another element, component, region, layer, or part. Therefore, without departing from the teachings herein, the "first element", "component", "region", "layer", or "part" discussed below may be referred to as a second element, component, region, layer, or part.

[0038] The terms used herein are only used to describe the purpose of specific embodiments and are not intended to be restrictive. As used herein, "one (kind) (indefinite article) (a, an)", "said (the)" and "at least one (kind)" do not represent the limitation of quantity, and are intended to include both the singular and the plural, unless the context clearly indicates otherwise. For example, "element" has the same meaning as "at least one element", unless the context clearly indicates otherwise. "At least one (kind)" will not be interpreted as being limited to "one (kind)". "Or" means "and / or". As used herein, the term "and / or" includes any and all combinations of one or more of the related enumerated items. It will be further understood that the term "comprising" or "including" when used in this specification, indicates that there are stated features, regions, wholes, steps, operations, elements, and / or components, but does not exclude the presence or addition of one or more other features, regions, wholes, steps, operations, elements, components, and / or their sets.

[0039] In addition, relative terms, such as "lower" or "bottom" and "upper" or "top", may be used herein to describe the relationship of one element to another element as shown in the figure. It will be understood that in addition to the directions depicted in the figures, relative terms are also intended to cover different directions of the device. For example, if the device in one of the figures is turned over, the element described as being on the "lower" side of the other element will be oriented on the "upper" side of the other element. Therefore, depending on the specific direction of the figure, the term "lower" can cover both "lower" and "upper" directions. Similarly, if the device in one of the figures is turned over, the element described as "below" or "below" the other element will be oriented as "above" the other element. Therefore, the term "below..." or "below..." can cover both "above..." and "below..." directions.

[0040] As used herein, "about" or "approximately" is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art taking into account the measurement in question and the errors associated with the measurement of the particular quantity (i.e., the limitations of the measurement system). For example, "about" can mean within one or more standard deviations, or within ±10% or 5% relative to the stated value.

[0041] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which the present disclosure belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning consistent with their meaning in the context of the present disclosure and the relevant art, and will not be interpreted in an idealized or overly formal sense unless clearly so defined herein.

[0042] Embodiments are described herein with reference to cross-sectional views as schematic diagrams of idealized embodiments. Thus, deviations from the shapes of the figures as a result of, for example, manufacturing techniques and / or tolerances are to be expected. Therefore, the embodiments described herein should not be construed as being limited to the specific shapes of the regions as illustrated herein, but rather include deviations in shape, for example, caused by manufacturing. For example, a region illustrated or described as flat may typically have rough and / or nonlinear features. In addition, the illustrated sharp corners may be rounded. Therefore, the regions shown in the figures are schematic in nature, and their shapes are not intended to illustrate the precise shapes of the regions and are not intended to limit the scope of the claims.

[0043] As used herein, the expression "XY" is used to indicate a range that includes the values ​​X and Y as lower and upper boundaries, respectively, and refers to "at least X and not more than Y". As used herein, the expression "P and Q are each independently" refers to P and Q being the same as or different from each other. In addition, as used herein, the expression "A and / or B" refers to including A and B individually and a combination of A and B. In addition, unless otherwise specifically mentioned, the expressions "concentration" and "%" refer to "mass concentration" or "weight %", respectively, and unless otherwise specifically mentioned, the expression "ratio" refers to a weight ratio. In addition, unless otherwise specifically mentioned, measurements such as operations and properties are performed under the conditions of room temperature (20-25°C) / relative humidity RH of 40-50%.

[0044] As used herein, the term "ring-derived group" refers to a group having free valences by removing hydrogen atoms directly bonded to the ring-forming atoms in the ring structure as many as the valence number. In this regard, the ring-forming atoms represent atoms that directly form the ring structure. For example, in the case of a benzene ring, the ring-forming atoms are carbon atoms, and hydrogen atoms are not included in the ring-forming atoms.

[0045] Recently, as a method of increasing the life of organic EL devices and improving the luminous efficiency, it has been proposed to use an organic EL device in which a phosphor (phosphor) sensitizer and a luminescent material are combined for emission (see Nature Communications, 2018, 9, 4990. DOI: 10.1038 / s41467-018-07432-2). In conventional organic EL devices, a host material and a luminescent material are used in an emission layer, and excitons generated in the molecules of the host material in the emission layer transfer energy to the luminescent material, resulting in luminescence. Typically, when a fluorescent material is used as a luminescent material, the luminous efficiency reaches a maximum value of 5%. However, since when a phosphor sensitizer is added to the emission layer, the triplet energy that is conventionally unavailable can become available for luminescence, the luminous efficiency of the organic EL device can be improved by up to 10% or more. In addition, it has been reported that the device lifetime is longer than in the case of using a phosphor sensitizer as a light-emitting material, and therefore, an organic EL device using a phosphor sensitizer in addition to a light-emitting material is attracting attention as a candidate for the next-generation organic EL device.

[0046] In order to reduce the FWHM of the emission spectrum of the luminescent material, it is usually necessary to suppress the vibration excitation within the molecule and ensure a small change in the conformation or bond length of the molecule between the ground state and the excited state. In order to suppress the conformational change of the molecule, a fused compound in which the bond distance between atoms is suppressed can be used. The synthesis and basic properties of nitrogen-containing fused polycyclic compounds (S1) exhibiting a blue emission wavelength have been reported in Tetrahedron.2013,69,3302-3307 and New J.Chem.2010,34,1243-1246. These reports show that nitrogen-containing fused polycyclic compounds (S1) are promising luminescent materials due to their emission spectra with small Stokes shift and small FWHM in the solution state.

[0047]

[0048] As disclosed in WO2013 / 084805, when a derivative of a nitrogen-containing fused polycyclic compound (S1) is used as an active (active) layer of an organic transistor, the active layer exhibits p-type channel characteristics and high hole mobility. In addition, in JP2020-107742, a derivative of a nitrogen-containing fused polycyclic compound (S1) introducing an aromatic group as a substituent acts as a light-emitting material for an organic EL device, and the organic EL device provides a high luminous efficiency. In this way, it can be seen that the nitrogen-containing fused polycyclic compound (S1) is excellent as a basic skeleton for an organic semiconductor material. In JP 2020-107742, the manufactured organic EL device also emits blue light with a FWHM of 20nm or less and has a narrow FWHM, and the organic EL device uses a derivative of a nitrogen-containing fused polycyclic compound (S1) as a light-emitting material in combination with a phosphorescent complex to provide a luminous efficiency of 5% or more.

[0049] However, in order to put the derivative using the nitrogen-containing condensed polycyclic compound (S1) as a basic skeleton into practical use as an organic EL device, further improvement in light emission efficiency is required.

[0050] According to the present disclosure, a compound capable of providing high efficiency without damaging optical properties to an organic electroluminescent (EL) device is provided. A method for promoting an organic EL device having high efficiency without damaging optical properties of a luminescent material (considering the prior art) is also disclosed. The following compound is provided: a 2,4,6-tri-tert-butylphenyl group ("substituent W", represented by formula (2)) which is a substituent that can be expected to have high aggregation inhibition and is bulky is introduced into a nitrogen-containing fused polycyclic compound (S1). The compound is represented by formula (1). The compound represented by formula (1) enables the provision of: a blue luminescent material having a peak emission wavelength of about 440nm to about 480nm and realizing luminescence with a narrow spectrum having an emission spectrum width (half width (FWHM)) of 20nm or less; a composition utilizing the blue luminescent material; an organic EL device; and an organic EL display including the organic EL device. Additionally, in the present disclosure, hereinafter, the substituent represented by formula (2) may also be interchangeably referred to as "substituent W" or "2,4,6-tri-tert-butylphenyl group".

[0051] The compound represented by formula (1)

[0052] The present disclosure relates to compounds represented by formula (1):

[0053]

[0054] Among them, in formula (1),

[0055] R 1To R 16 At least one of may be a substituent W represented by formula (2) (* represents a bonding site to the benzene ring),

[0056] as well as

[0057] R other than the substituent W 1 To R 16 can be independently any one of the atoms or groups from (a1) to (a10):

[0058] (a1) Hydrogen or deuterium atoms;

[0059] (a2) halogen atoms;

[0060] (a3) cyano;

[0061] (a4) a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms;

[0062] (a5) a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms;

[0063] (a6) a substituted or unsubstituted arylamino group having 6 to 20 carbon atoms;

[0064] (a7) a substituted or unsubstituted triarylsilyl group, an alkyldiarylsilyl group, a dialkylarylsilyl group, or a trialkylsilyl group (wherein the aryl group is an aryl group having 6 to 20 carbon atoms, and the alkyl group is an alkyl group having 1 to 20 carbon atoms);

[0065] (a8) a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms;

[0066] (a9) a substituted or unsubstituted heterocyclic group having 3 to 30 ring atoms; and

[0067] (a10) a substituted or unsubstituted saturated hydrocarbon group or a saturated heterocyclic group, each of which is bonded to R 1 To R 16 The ring is formed by two adjacent groups in the ring and has 5 to 9 ring atoms.

[0068] Hereinafter, the compound represented by formula (1) according to the present disclosure is also referred to by the term "compound of formula (1)". "R other than the substituent W 1 To R 16 The group that can be independently (a10) means R 1 To R 16Two adjacent groups in the formula (1) are bonded to each other and fused with the benzene ring to form a substituted or unsubstituted saturated hydrocarbon group or saturated heterocyclic group having 5 to 9 ring atoms, two of which are from the benzene ring of the formula (1).

[0069] Without wishing to be bound by theory, it is believed that the emission wavelength of the luminescent material depends not only on the skeleton structure, but also on the type of the substituent. Due to the introduction of a specific substituent (substituent W), the compound of formula (1) undergoes a long-wave shift to have a peak wavelength in the emission spectrum within the blue wavelength region. As a result, the compound of formula (1) provides satisfactory characteristics as a luminescent material for an organic EL device, particularly as a blue luminescent material for an organic EL device. In particular, the introduction of the substituent suppresses intermolecular aggregation and improves the solubility (degree) of the molecule itself, resulting in improved purification accuracy. Therefore, the color purity of the luminescence is also improved.

[0070] When a nitrogen-containing condensed polycyclic compound (S1) having a high flatness is used as a light-emitting material for an organic EL device, the distance between the nitrogen-containing condensed polycyclic compound (S1) and the adjacent host molecule in the emission layer is reduced, thereby promoting Dexter-type energy transfer. In addition, because the nitrogen-containing condensed polycyclic compound (S1) is a planar molecule, aggregation between the light-emitting materials can easily occur, and it is believed that the aggregation leads to a degradation of the color purity of the emission spectrum. Therefore, as a means to solve these problems, a method for introducing a spatially bulky substituent into the nitrogen-containing condensed polycyclic compound (S1) has been obtained.

[0071] Mesitylene, p-tert-butylphenyl, and 3,5-di-tert-butylphenyl are known as bulky substituents, and compounds having these substituents introduced into their molecular skeletons or the aryl group of a diarylamino group are reported as light-emitting materials (e.g., JP 2012-176928, WO 2017 / 188111, etc.).

[0072] These bulky substituents are usually introduced by Suzuki-Miyaura coupling reaction or Buchwald-Hartwig reaction to form carbon-carbon bonds or carbon-nitrogen bonds. When these substituents are introduced into a compound, the substituents at the ortho position (o position) of the aryl group, for example, the substituents at the ortho position of the phenyl group in the case of mesitylene, are typically not bulky and therefore do not hinder the reaction to facilitate the ease of introduction of the o-position substituent.

[0073] It is considered that in order to form a compound with a larger volume of substituents, 2,4,6-tri-tert-butylphenyl is introduced into a nitrogen-containing condensed polycyclic compound (S1). However, the attempt to synthesize such a compound by introducing 2,4,6-tri-tert-butylphenyl (substituent W) into a nitrogen-containing condensed polycyclic compound (S1) via a Suzuki-Miyaura coupling reaction is unsuccessful, and the desired compound cannot be obtained. It is believed that due to the bulky tert-butyl group present at the ortho position of the phenyl in 2,4,6-tri-tert-butylphenyl, the Suzuki-Miyaura coupling reaction is not carried out.

[0074] The present inventors have found that by using the Negishi coupling reaction, 2,4,6-tri-tert-butylphenyl (substituent W) can be introduced into the nitrogen-containing fused polycyclic compound (S1) and the compound of formula (1) can be prepared. In addition, the present inventors have demonstrated that the compound of formula (1) exhibits excellent luminescent properties.

[0075] For example, in each benzene ring located in the outer part of the compound of formula (1) (four benzene rings other than the central benzene ring), there are four sites (for example, R 1 To R 16 The substitution positions of these benzene rings are numbered sequentially from positions 1 to 4 starting from the side closest to the fused carbon atom closest to the nitrogen atom (e.g., in the case of a phenyl ring having R 1 To R 4 In the benzene ring, R 1 is 1, R 2 is 2, R 3 is 3 bits, and R 4 is 4 bits; in the case of R 5 To R 8 In the benzene ring, R 8 is 1, R 7 is 2, R 6 is 3 bits, and R 5 In the present disclosure, even when a substituent W is introduced at any position of the benzene ring, the compound of formula (1) can exhibit excellent optical properties. The substituent W may be at the 3-position or the 4-position, and for example, the substituent W may be at the 2-position or the 3-position in each of the two benzene rings facing each other.

[0076] As described above, according to the compound of formula (1), it is assumed (thought) that Dexter type energy transfer is suppressed because the substituent W is bulky, making it difficult for the molecules of the compound of formula (1) to approach each other. Therefore, the aggregation between the molecules of the compound of formula (1) is suppressed. In general luminescent materials, intermolecular aggregation can lead to luminescence from an aggregated state, thereby leading to a trend of broadening of the emission spectrum and degradation of color purity. However, since intermolecular aggregation is unlikely to occur in the compound of formula (1), degradation of color purity is also unlikely to occur, and luminescence with high color purity can be achieved. In addition, as a result, luminous efficiency can be improved. When the concentration of the compound of formula (1) increases, aggregation can become more likely to occur. However, even when the concentration of the compound of formula (1) increases, aggregation can still be suppressed, so that luminescence with high color purity and high efficiency can be achieved. In addition, when both the compound of formula (1) and the phosphorescent complex are used, a significant increase in the efficiency of the organic EL device can be achieved. As described above, the use of the light-emitting material of the compound of formula (1) in an organic EL device can provide excellent optical characteristics and high light-emitting efficiency.

[0077] The mechanism presented above is based on assumptions, and whether the assumed mechanism is right or wrong does not affect the technical scope of the present disclosure. In addition, regarding other assumptions made herein, whether such assumptions are right or wrong does not affect the technical scope of the present disclosure.

[0078] Thus, one aspect of the present disclosure relates to a compound represented by formula (1). In addition, another aspect of the present disclosure relates to an organic EL device having an emission layer including a compound represented by formula (1). In addition, another aspect of the present disclosure relates to an organic EL device having an emission layer including a compound represented by formula (1) and a phosphorescent complex.

[0079] Hereinafter, a compound represented by formula (1) according to an embodiment and a compound represented by formula (1) included in an emission layer of an organic EL device according to an embodiment are described.

[0080] In formula (1), R 1 To R 16 At least one of them is a substituent W (2,4,6-tri-tert-butylphenyl) represented by formula (2):

[0081]

[0082] In formula (2), * represents the bonding site with the benzene ring of formula (1). 1 To R 16 The two R may each be a substituent W (2,4,6-tri-tert-butylphenyl). 1 To R16 Any one of may be a substituent W, for example, R in formula (1) 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 , and R 15 At least two of may each be a substituent W. In addition, when R 1 To R 16 When the two of are each a substituent W, the substituted group may be the following combination: For example, R 2 and R 10 ; R 3 and R 11 ; R 6 and R 14 ; R 7 and R 15 ; or a combination thereof.

[0083] In formula (1), R other than the substituent W 1 To R 16 can be independently any one of the atoms or groups from (a1) to (a10):

[0084] (a1) Hydrogen or deuterium atoms;

[0085] (a2) halogen atoms;

[0086] (a3) cyano;

[0087] (a4) a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms;

[0088] (a5) a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms;

[0089] (a6) a substituted or unsubstituted arylamino group having 6 to 20 carbon atoms;

[0090] (a7) a substituted or unsubstituted triarylsilyl group, an alkyldiarylsilyl group, a dialkylarylsilyl group, or a trialkylsilyl group (wherein the aryl group is an aryl group having 6 to 20 carbon atoms, and the alkyl group is an alkyl group having 1 to 20 carbon atoms);

[0091] (a8) a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms;

[0092] (a9) a substituted or unsubstituted heterocyclic group having 3 to 30 ring atoms; and

[0093] (a10) a substituted or unsubstituted saturated hydrocarbon group or a saturated heterocyclic group, each of which is bonded to R1 To R 16 The ring is formed by two adjacent groups in the ring and has 5 to 9 ring atoms.

[0094] In formula (1), among the atoms or groups (a1) to (a9), preferably, the atoms or groups (a1), (a4), (a7), (a8), and (a10) can be selected, and more preferably, the atoms or groups (a1), (a4), and (a10) can be selected.

[0095] In formula (1), when the groups (a3) ​​to (a10) are substituted groups, the substituents substituted into such groups are not particularly limited. However, in formula (1), the substituents substituted into the groups (a3) ​​to (a10) may each independently be at least one substituent selected from the following: a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, and a substituted or unsubstituted heterocyclic group having 3 to 30 ring atoms.

[0096] In the case of the hydrogen atom of (a1), the benzene ring is in an unsubstituted state. In addition, among the stable isotopes of hydrogen, (a) may include a deuterium atom containing one proton and one neutron in its nucleus. The deuterium atom is written as 2 H or D (the first letter of deuterium).

[0097] The halogen atom of (a2) is not particularly limited, and examples thereof include a fluorine atom (F), a chlorine atom (Cl), a bromine atom (Br), or an iodine atom (I). In particular, the halogen group may be a fluorine atom in view of light emission efficiency.

[0098] The cyano group in (a3) ​​is written as CN.

[0099] The alkyl group having 1 to 20 carbon atoms of (a4) is not particularly limited, and may be linear, branched or cyclic. In particular, the alkyl group may be branched in view of luminescent color purity. In view of solubility and luminescent color purity, the number of carbon atoms in the alkyl group may be 2 or more, such as 3 or more, or, for example, 4 or more. In addition, in view of luminous efficiency, the number of carbon atoms in the alkyl group may be 10 or less, such as 8 or less, or, for example, 6 or less. From the above viewpoint, the number of carbon atoms in the alkyl group may be 4. Examples of the alkyl group may include, but are not particularly limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl (s-butyl), tert-butyl (t-butyl), isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethyl Heptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, etc. In particular, the alkyl group may be a branched alkyl group such as isopropyl, or a tert-butyl group, such as a tert-butyl group.

[0100] In addition, the term "substituted alkyl group having 1 to 20 carbon atoms" refers to a group formed by substituting an unsubstituted alkyl group having 1 to 20 carbon atoms with a substituent. Therefore, the number of carbon atoms in the substituted alkyl group may be greater than 20.

[0101] The alkoxy group with 1 to 20 carbon atoms of (a5) is not particularly limited, and the alkoxy group may be linear, branched or cyclic. In particular, in view of luminous efficiency, the alkoxy group may be linear. In view of luminous efficiency, the number of carbon atoms in the alkoxy group may be 1 to 10. From the same point of view, the number of carbon atoms in the alkoxy group may be 1 to 8, such as 1 to 6, or such as 1. Examples of the alkyl group constituting the alkoxy group may include, but are not particularly limited to, those mentioned in the above description of the alkyl group. Examples of the alkoxy group may include, but are not particularly limited to, methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, etc. In particular, the alkoxy group may be a methoxy group.

[0102] In addition, the term "substituted alkoxy group having 1 to 20 carbon atoms" refers to a group formed by substituting an unsubstituted alkoxy group having 1 to 20 carbon atoms with a substituent. Therefore, the number of carbon atoms in the substituted alkoxy group may be greater than 20.

[0103] The nitrogen atom of the arylamino group with 6 to 20 carbon atoms of (a6) can be bonded to the ring-forming carbon atom of the benzene ring (in the four benzene rings other than the central benzene ring) on ​​the outside of the compound of formula (1) via a single bond. In addition, in this article, even in the case where the group includes a nitrogen atom, when the nitrogen atom is a ring-forming atom of a heterocycle, the group is treated as a heterocyclic group to be described below, rather than an arylamino group. Examples of the aryl group constituting the arylamino group may include, but are not particularly limited to, for example, a group with 6 to 20 carbon atoms in the aromatic hydrocarbon group of (a8). The arylamino group may be, but is not particularly limited to, a monoarylamino group or a diarylamino group. Examples of the arylamino group may include, but are not particularly limited to, N-phenylamino, N-biphenylamino, N-terphenylamino, N,N-diphenylamino, N-biphenyl-N-phenylamino, etc.

[0104] In addition, the term "substituted arylamino group having 6 to 20 carbon atoms" refers to a group formed by substituting an unsubstituted arylamino group having 6 to 20 carbon atoms with a substituent. Therefore, the number of carbon atoms in the substituted arylamino group may be greater than 20.

[0105] The silicon (Si) group of the triarylsilyl group, alkyldiarylsilyl group, dialkylarylsilyl group, or trialkylsilyl group of (a7) may be bonded to a ring-forming carbon atom of a benzene ring (in four benzene rings other than the central benzene ring) located on the outside of the compound of formula (1) via a single bond. The aryl group constituting the triarylsilyl group, the alkyldiarylsilyl group, and the dialkylarylsilyl group may be an aryl group having 6 to 20 carbon atoms, and examples thereof may include groups having 6 to 20 carbon atoms in the aromatic hydrocarbon group to be described below. The alkyl group constituting the alkyldiarylsilyl group, the dialkylarylsilyl group, and the trialkylsilyl group may be an alkyl group having 1 to 20 carbon atoms, and examples thereof may be the same as the examples of the alkyl group having 1 to 20 carbon atoms of (a4). Examples of the triarylsilyl group may include, but are not particularly limited to, triphenylsilyl, tri(tert-butylphenyl)silyl, di-tert-butylphenyl(phenyl)silyl, and the like. Examples of the alkyldiarylsilyl group may include, but are not particularly limited to, diphenylmethylsilyl, diphenyl(tert-butyl)silyl, di-tert-butylphenyl(methyl)silyl, di-tert-butylphenyl(tert-butyl)silyl, and the like. Examples of the dialkylarylsilyl group may include, but are not particularly limited to, dimethylphenylsilyl, and the like. Examples of the trialkylsilyl group may include, but are not particularly limited to, trimethylsilyl, tri-tert-butylsilyl, di-tert-butyl(methyl)silyl, and the like.

[0106] In addition, the term "each substituted triarylsilyl, alkyldiarylsilyl, dialkylarylsilyl, or trialkylsilyl" refers to a group formed by substituting an unsubstituted aryl group having 6 to 20 carbon atoms and / or an unsubstituted alkyl group having 1 to 20 carbon atoms with a substituent. Therefore, the number of carbon atoms of the aryl group of the substituted triarylsilyl, alkyldiarylsilyl, and dialkylarylsilyl groups may be greater than 20, and the number of carbon atoms of the alkyl group of the substituted alkyldiarylsilyl, dialkylarylsilyl, and trialkylsilyl groups may be greater than 20.

[0107] The aromatic hydrocarbon group having 6 to 30 carbon atoms of (a8) refers to a group derived from at least one aromatic hydrocarbon ring. The term "aromatic hydrocarbon ring" as used herein refers to a hydrocarbon ring which is partially or completely aromatic.

[0108] When the aromatic hydrocarbon group includes at least two aromatic hydrocarbon rings, these rings may be fused to each other or bonded to each other via a single bond. In addition, when the aromatic hydrocarbon group includes at least two aromatic hydrocarbon rings, one atom may serve as a ring-forming atom of any of these rings.

[0109] The number of carbon atoms in the aromatic hydrocarbon group may be 6 to 20, for example, 6 to 12, or for example, 6, in view of luminescent color purity.

[0110] Examples of the aromatic hydrocarbon group may include, but are not particularly limited to, phenyl, mesityl, tert-butylphenyl, bis(tert-butyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, anthracenyl, quaterphenyl, pentaphenyl, hexaphenyl, benzo[9,10]phenanthryl, pyrenyl, benzofluorenyl, base, or a combination thereof.

[0111] In addition, the term "substituted aromatic hydrocarbon group" refers to a group formed by substituting an unsubstituted aromatic hydrocarbon group with a substituent. Therefore, when the number of carbon atoms in the aromatic hydrocarbon group is equal to or less than a certain upper limit of the number of carbon atoms, such as 30 or less, the number of carbon atoms in the substituted aromatic hydrocarbon group may be greater than the upper limit.

[0112] The heterocyclic group having 3 to 30 ring atoms of (a9) refers to a group derived from at least one heteroatom-containing ring. The heterocyclic group may be, but is not particularly limited to, an aromatic heterocyclic group or a non-aromatic heterocyclic group. In particular, in view of the purity of the luminescent color, the heterocyclic group may be an aromatic heterocyclic group.

[0113] The term "aromatic heterocyclic group" refers to a group derived from at least one aromatic heteroatom-containing ring. As used herein, the term "aromatic heterocycle" refers to a heterocycle that is partially or completely aromatic. When the aromatic heterocycle is partially aromatic, the aromaticity may be derived from the heterocyclic portion of the ring or from the hydrocarbon ring portion of the ring. The aromatic heterocycle is not particularly limited, and may be, for example, a ring having at least one heteroatom (e.g., nitrogen atom (N), oxygen atom (O), phosphorus atom (P), sulfur atom (S), or silicon atom (Si)) as a ring-forming atom, wherein the remaining ring-forming atoms are carbon atoms (C). The atoms constituting the ring structure may be bonded to atoms outside the ring via double bonds. For example, the carbon atoms constituting the ring structure may constitute a ketone group (C=O group), a thiol group (C=S group), or a C=NH group, or the sulfur atom constituting the ring structure may constitute a sulfinyl group (S=O group) or a sulfonyl group (S(=O)=O group). In this case, as used herein, the exocyclic atom forming a double bond with the atom constituting the ring structure may be a part of an aromatic heterocycle. In addition, when the exocyclic atom forming a double bond is bonded to a hydrogen atom via a single bond, the hydrogen atom may also be a part of the aromatic heterocycle. Examples of the aromatic heterocycle may include, but are not particularly limited to, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, a quinazoline ring, a naphthyridine ring, an acridine ring, a phenazine ring, a benzoquinoline ring, a benzoisoquinoline ring, a phenanthridine ring, a phenanthroline ring, a benzoquinone ring, a coumarin ring, an anthraquinone ring, a fluorenone ring, a furan ring, a thiophene ring, a benzofuran ring, a benzothiophene ring, a dibenzofuran ring, a dibenzothiophene ring, a pyrrole ring, an indole ring, a carbazole ring, an indole and carbazole ring, an imidazole ring, a pyrrole ring, a thiophene ring, a benzofuran ring, a benzothiophene ring, a dibenzofuran ring, a dibenzothiophene ring, a pyrrole ring, a indole ring, a carbazole ring, a indole and carbazole ring, an imidazole ring, a pyrrol ring, a pyrrolidine ... ring, benzimidazole ring, pyrazole ring, indazole ring, oxazole ring, isoxazole ring, benzoxazole ring, benzisoxazole ring, thiazole ring, isothiazole ring, benzothiazole ring, benzisothiazole ring, imidazolidinone ring, benzimidazolinone ring, imidazopyridine ring, imidazopyrimidine ring, imidazophenanthridine ring, benzimidazolophenanthridine ring, azadibenzofuran ring, azacarbazole ring, azadibenzothiophene ring, diazadibenzofuran ring, diazacarbazole ring, diazadibenzothiophene ring, xanthene ring, thioxanthone ring and the like.

[0114] When the aromatic heterocyclic group includes at least two aromatic heterocyclic rings, these rings may be fused to each other or bonded to each other via a single bond. In addition, when the aromatic heterocyclic group includes at least two aromatic heterocyclic rings, one atom may serve as a ring-forming atom of any of these rings.

[0115] In view of the peak wavelength in the emission spectrum and the purity of the emission color, the number of ring-forming atoms in the aromatic heterocyclic group (the sum of the number of ring-forming carbon atoms and the number of ring-forming heteroatoms) may be 3 to 30, and may be 5 to 20, for example, 6 to 14. In view of the peak wavelength in the emission spectrum and the purity of the emission color, the number of ring-forming heteroatoms in the aromatic heterocyclic group may be, but is not particularly limited to, 1 to 10. In addition, the number of ring-forming heteroatoms in the aromatic heterocyclic group may be 1 to 5, for example, 1 to 3. In addition, as described above, the term "ring-forming atom" refers to an atom that directly forms a ring structure.

[0116] Examples of the aromatic heterocyclic group may include, but are not particularly limited to, thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothiphenyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoxazolyl, thiadiazolyl, phenothiazinyl, dibenzosilyl, dibenzofuranyl, xanthonyl and the like. Specifically, the aromatic heterocyclic group may be a triazine group, a carbazolyl group, a benzoxazolyl group, or a xanthone group.

[0117] In addition, the term "non-aromatic heterocyclic group" refers to a group derived from at least one non-aromatic heterocycle. As used herein, the term "non-aromatic heterocycle" refers to a completely non-aromatic heterocycle. The non-aromatic heterocycle is not particularly limited, and may be, for example, a ring having at least one heteroatom (e.g., nitrogen atom (N), oxygen atom (O), phosphorus atom (P), sulfur atom (S), or silicon atom (Si)) as a ring-forming atom, wherein the remaining ring-forming atoms are carbon atoms (C). In view of the peak wavelength and luminescent color purity in the emission spectrum, the heteroatom may be a nitrogen atom (N) or an oxygen atom (O). The atoms constituting the ring structure may be bonded to the exocyclic atom via a double bond. For example, the carbon atoms constituting the ring structure may constitute a ketone group (C=O group), a thione group (C=S group), or an imine group (C=NH group), or the sulfur atom constituting the ring structure may constitute a sulfinyl group (S=O group) or a sulfonyl group (S(=O)=O group). In this case, as used herein, the exocyclic atom forming a double bond with the atom constituting the ring structure may be part of the non-aromatic heterocycle. In addition, when the exocyclic atom forming a double bond is bonded to a hydrogen atom via a single bond, the hydrogen atom may also be part of the non-aromatic heterocycle. Examples of the non-aromatic heterocycle may include, but are not particularly limited to, a pyrrolidine ring, a tetrahydrofuran ring, a tetrahydrothiophene ring, a piperidine ring, a tetrahydropyran ring, a tetrahydrothiopyran ring, a dioxane ring, a morpholine ring, a dioxolane ring, etc.

[0118] When the non-aromatic heterocyclic group includes at least two non-aromatic heterocyclic rings, these rings may be fused to each other or bonded to each other via a single bond. In addition, when the non-aromatic heterocyclic group includes at least two non-aromatic heterocyclic rings, one atom may serve as a ring-forming atom in any of these rings.

[0119] In view of the peak wavelength in the emission spectrum and the luminescent color purity, the number of ring-forming atoms in the non-aromatic heterocyclic group (the sum of the number of ring-forming carbon atoms and the number of ring-forming heteroatoms) may be 3 to 30, and may be 5 to 20, for example, 6 to 14. In view of the peak wavelength in the emission spectrum and the luminescent color purity, the number of ring-forming heteroatoms in the non-aromatic heterocyclic group may be, but is not particularly limited to, 1 to 10. From the same point of view, the number of ring-forming heteroatoms in the non-aromatic heterocyclic group may be 1 to 5, for example, 1 to 3. In addition, as described above, the term "ring-forming atoms" refers to atoms that directly form a ring structure. Therefore, when there are exocyclic atoms that form double bonds with atoms constituting the ring structure, the exocyclic atoms may not be included in the ring-forming atoms.

[0120] Examples of the non-aromatic heterocyclic group may include, but are not particularly limited to, pyrrolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, piperidinyl, tetrahydropyranyl, tetrahydrothiopyranyl, dioxanyl, morpholinyl, dioxolanyl, and the like.

[0121] In addition, the term "substituted heterocyclic group" refers to a group formed by substituting an unsubstituted heterocyclic group with a substituent. Therefore, when the number of ring-forming atoms in the heterocyclic group is equal to or less than a certain upper limit of the number of ring-forming atoms, for example, 30 or less, and the substituent forms a ring structure, the number of ring-forming atoms in the substituted heterocyclic group may be greater than the upper limit.

[0122] In (a10), the "substituted or unsubstituted saturated hydrocarbon group or saturated heterocyclic group" each of which is bonded to R 1 To R 16 In the case of "formed by two adjacent groups in the formula (1) and having 5 to 9 ring-forming atoms", R each bonded to a ring-forming carbon atom of a benzene ring (in four benzene rings other than the central benzene ring) located on the outside of the compound of formula (1) is 1 To R 16 Two adjacent groups (e.g., R 1 and R 2 ; R 2 and R 3 ; or R 3 and R 4 ) are each bonded to a ring-forming carbon atom of the benzene ring via a single bond or are bonded to each other via a single bond. In other words, in the case of the group (a10), R 1 To R16 Two adjacent groups in are bonded to each other to form a saturated hydrocarbon group or a saturated heterocyclic group each fused with a benzene ring and having 5 to 9 ring atoms. 1 To R 16 The position of the fused ring formed by the two adjacent groups in (the position of fusion in the benzene ring) can be at the 2-position and 3-position of the benzene ring, and therefore, R 2 and R 3 ; R 6 and R 7 ; R 10 and R 11 ; or R 14 and R 15 may be bonded to each other to form a saturated hydrocarbon group or a saturated heterocyclic group each having 5 to 9 ring atoms. 2 and R 3 ; and R 10 and R 11 may be bonded to each other to form a saturated hydrocarbon group or a saturated heterocyclic group each having 5 to 9 ring atoms, or R 6 and R 7 ; and R 14 and R 15 may be bonded to each other to form a saturated hydrocarbon group or a saturated heterocyclic group each having 5 to 9 ring atoms. 1 To R 16 When a ring condensed with a benzene ring (condensed ring) is formed, the number of the condensed rings (condensed rings) may be two.

[0123] The condensed ring (saturated hydrocarbon ring) formed by the saturated hydrocarbon group having 5 to 9 ring atoms may include, for example, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, a cyclooctane ring, a cyclononane ring, etc. The condensed ring (saturated heterocycle) formed by the saturated heterocyclic group having 5 to 9 ring atoms may include a group having 5 to 9 ring atoms in a non-aromatic heterocyclic group. Examples of the condensed ring (saturated heterocycle) formed by the saturated heterocyclic group having 5 to 9 ring atoms may include a pyrrolidine ring, a tetrahydrofuran ring, a tetrahydrothiophene ring, a piperidine ring, a tetrahydropyran ring, a tetrahydrothiopyran ring, a dioxane ring, a morpholine ring, a dioxolane ring, etc.

[0124] In addition, the term "substituted saturated hydrocarbon group or saturated heterocyclic group having 5 to 9 ring-forming atoms" refers to a group formed by substituting an unsubstituted saturated hydrocarbon group or saturated heterocyclic group with a substituent. Therefore, when the number of ring-forming atoms in the saturated hydrocarbon group or saturated heterocyclic group is equal to or less than a certain upper limit of the number of ring-forming atoms, for example, 9 or less, and the substituent forms a ring structure, the number of ring-forming atoms in the substituted saturated hydrocarbon group or saturated heterocyclic group may be greater than the upper limit.

[0125] The halogen atoms, cyano groups, unsubstituted alkyl groups having 1 to 20 carbon atoms, unsubstituted alkoxy groups having 1 to 20 carbon atoms, unsubstituted arylamino groups having 6 to 20 carbon atoms, unsubstituted aromatic hydrocarbon groups having 6 to 30 carbon atoms, and unsubstituted heterocyclic groups having 3 to 30 ring-forming atoms as substituents substituted into the groups (a4) to (a10) may each be the same as the unsubstituted groups in the descriptions of (a2) to (a10).

[0126] Examples of unsubstituted haloalkyl groups having 1 to 20 carbon atoms as substituents substituted into groups (a4) to (a10) may include groups in which at least one hydrogen atom in the alkyl group described in (a4) is replaced by a halogen atom described in (a2). In view of luminous efficiency, the halogen atom may be a fluorine atom. Examples of haloalkyl groups may include trifluoromethyl, trichloromethyl, tribromomethyl, triiodomethyl, etc. In particular, haloalkyl groups may be fluoroalkyl groups, or, for example, trifluoromethyl groups.

[0127] In the unsubstituted alkylamino group having 1 to 20 carbon atoms as a substituent for the group substituted with (a4) to (a10), the nitrogen atom of the unsubstituted alkylamino group is bonded to any atom constituting the unsubstituted group of (a4) to (a10) in formula (1) via a single bond. The alkyl group substituted with the alkylamino group is not particularly limited, but may be the same as described with respect to (a4). The alkylamino group may be, but is not particularly limited to, a monoalkylamino group or a dialkylamino group. Examples of the alkylamino group may include, but are not particularly limited to, N-methylamino, N-ethylamino, N-n-propylamino, N-isopropylamino, N-butylamino, N-isobutylamino, N-sec-butylamino, N-tert-butylamino, N-pentylamino, N-hexylamino, N,N-dimethylamino, N-methyl-N-ethylamino, N,N-diethylamino, N,N-dipropylamino, N,N-diisopropylamino, N,N-dibutylamino, N,N-diisobutylamino, N,N-dipentylamino, and N,N-dihexylamino.

[0128] In this regard, the substituents substituted into the groups (a4) to (a10) may be, for example, halogen atoms, cyano groups, unsubstituted alkyl groups having 1 to 20 carbon atoms, unsubstituted alkoxy groups having 1 to 20 carbon atoms, or unsubstituted arylamino groups having 6 to 20 carbon atoms. In addition, in particular, the substituents may be, for example, halogen atoms, unsubstituted alkyl groups having 1 to 20 carbon atoms, or, for example, fluorine atoms or unsubstituted linear or branched alkyl groups having 1 to 20 carbon atoms. For example, the substituents may be fluorine atoms, methyl groups, ethyl groups, isopropyl groups, or tert-butyl groups.

[0129] In an embodiment, the substituent substituted into the groups of (a4) to (a10) may be an unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms. Specifically, the substituent may be a group derived from a benzene ring (phenyl).

[0130] In an embodiment, the substituent of the group substituted with (a4) to (a10) may be an unsubstituted heterocyclic group having 3 to 30 ring atoms. In particular, the heterocyclic group may be a heterocyclic group including oxygen or nitrogen atoms, such as a dibenzofuranyl group, a carbazolyl group, or a benzoxazolyl group. In addition, the heterocyclic group may be a dibenzofuranyl group or a carbazolyl group.

[0131] The substituents substituted into the group of (a4) may be halogen atoms or unsubstituted alkyl groups having 1 to 20 carbon atoms. Therefore, the substituents of the "substituted alkyl groups having 1 to 20 carbon atoms" may be halogen atoms or unsubstituted alkyl groups having 1 to 20 carbon atoms. In particular, the substituents may be unsubstituted linear or branched alkyl groups having 1 to 20 carbon atoms. In addition, the substituents may be methyl, ethyl, isopropyl, or tert-butyl.

[0132] The substituents substituted into the group of (a7) may be halogen atoms or unsubstituted alkyl groups having 1 to 20 carbon atoms. Therefore, the substituents of the "substituted triarylsilyl, alkyldiarylsilyl, dialkylarylsilyl, or trialkylsilyl" may be halogen atoms or unsubstituted alkyl groups having 1 to 20 carbon atoms. In particular, the substituents may be unsubstituted linear or branched alkyl groups having 1 to 20 carbon atoms. For example, the substituents may be methyl, ethyl, isopropyl, or tert-butyl.

[0133] The substituent to be substituted into the group of (a10) may be a halogen atom or an unsubstituted alkyl group having 1 to 20 carbon atoms. 1 To R 16 The substituent "formed by two adjacent groups in and having 5 to 9 ring-forming atoms" may be a halogen atom or an unsubstituted alkyl group having 1 to 20 carbon atoms. In particular, the substituent may be an unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms. For example, the substituent may be a methyl group, an ethyl group, an isopropyl group, or a tert-butyl group.

[0134] When the groups (a4) to (a10) are substituted groups, the substituents substituted into the groups (a4) to (a10) may be further substituted by another substituent. The other substituent is not particularly limited, but may be, for example, a substituent in the case where the groups (a4) to (a10) are substituted groups, or one of these groups substituted by these groups.

[0135] In an embodiment, R other than the substituent W in the compound of formula (1) 1 To R 16 At least one selected from the following group X may be included. In other words, in the embodiment, R in the compound of formula (1) 1 To R 16 At least one (eg, at least two) (eg, R 2 and R 10 ; and / or R 3 and R 11 ) may be a substituent W, and R 1 To R 16 At least one (eg, at least two) (eg, R 6 and R 14 ; R 7 and R 15 ; R 6 and R 7 ; and / or R 14 and R 15 ) may be a group selected from the following group X. In addition, in the compound of formula (1), R 1 To R 4 At least one and R 9 To R 12 At least one of each may be a substituent W, and R 5 To R 8 At least one and R 13 To R 16 At least one of each may be a group selected from the following Group X.

[0136] Group X

[0137]

[0138] Among the above substituents, a substituent having two bonding sites (*) to a benzene ring is bonded to R 1 To R 16 The following groups (a-1) and (b-1) are fused to the benzene ring to form a fused ring. For example, the following group (a-1) is fused to the benzene ring to form a 5-membered ring (a-2), and the following group (b-1) is fused to the benzene ring to form a 6-membered ring (b-2).

[0139]

[0140] In addition, in an embodiment, R other than the substituent W in the compound of formula (1) 1 To R 16 At least one selected from the following group Y may be included. In other words, in the embodiment, R in the compound of formula (1) 1 To R 16At least one (eg, at least two) (eg, R 2 and R 10 ; and / or R 3 and R 11 ) may be a substituent W, and R 1 To R 16 At least one (eg, at least two) (eg, R 6 and R 14 ; R 7 and R 15 ; R 6 and R 7 ; and / or R 14 and R 15 ) may be a group selected from the following group Y. In addition, in the compound of formula (1), R 1 To R 4 At least one and R 9 To R 12 At least one of each may be a substituent W, and R 5 To R 8 At least one and R 13 To R 16 At least one of each may be a group selected from the following Group Y.

[0141] Group Y

[0142]

[0143] Hereinafter, the compound of formula (1) according to the embodiment is described in detail. However, the present disclosure is not limited to such examples. For example, an example of the compound of formula (1) according to the embodiment can be represented by one of compounds (100) to (117).

[0144]

[0145]

[0146] For example, examples of the compound of formula (1) may include compounds (101), (102), (105), (108), (110), (111), (113), and the like.

[0147] The compound of formula (1) according to the present disclosure may have a peak wavelength in the emission spectrum in the blue wavelength region, and may provide luminescence with high color purity. In addition, the blue wavelength region as used herein refers to a wavelength region of at least about 380 nanometers (nm) and not more than about 500 nm. The peak wavelength of the emission of the photoluminescence (PL) of the compound of formula (1) according to the present disclosure is not particularly limited, but may be about 440 nm to about 480 nm. In addition, the peak wavelength may be in a wavelength region of about 445 nm to about 470 nm, for example, about 450 nm to about 470 nm, for example, about 450 nm to about 465 nm. When the peak wavelength is within the above range, excellent luminescence, particularly blue luminescence, may be obtained. The FWHM of the peak of the emission spectrum of the PL may be 30 nm or less, for example, 20 nm or less, for example, 15 nm or less (the lower limit is greater than 0 nm). In addition, the peak wavelength of PL emission and the FWHM of the peak of the PL emission spectrum can be measured by using a fluorescence spectrophotometer F7000 manufactured by Hitachi High-Tech Co., Ltd. More specifically, such a fluorescence spectrophotometer can be used to evaluate 1×10 -7 M (mol / L), mole / cubic decimeter (mol / dm 3 )) of a toluene solution of a compound of formula (1) according to the present disclosure, or a thin film formed by depositing a compound of formula (1) according to the present disclosure and a host molecule by using the method described in the following examples.

[0148] Quantum chemical calculations can be used to predict the narrow FWHM and quarter width (quarter full width maximum) (FWQM), thermally activated delayed fluorescence (TADF) properties and emission wavelength required for molecules used as dopants.

[0149] The method for synthesizing a compound of formula (1) according to the present disclosure includes introducing 2,4,6-tri-tert-butylphenyl (substituent W) into a nitrogen-containing fused polycyclic compound (S1) by using a Negishi coupling reaction, and other aspects of the synthesis method can refer to known synthesis methods. More particularly, the synthesis can be carried out according to or in view of the method described in the embodiments. For example, the synthesis can be carried out by changing the raw materials or reaction conditions in the method described in the embodiments, adding or deleting some processes, or appropriately combining known synthesis methods.

[0150] The method for determining the structure of the compound of formula (1) according to the present disclosure is not particularly limited. The structure of the compound of formula (1) according to the present disclosure can be confirmed by, for example, known methods (e.g., nuclear magnetic resonance spectroscopy (NMR), liquid chromatography-mass spectrometry (LC-MS), etc.).

[0151] Materials for organic EL devices

[0152] Another aspect of the present disclosure relates to a material for an organic electroluminescent device, the material comprising a compound of formula (1). The material may be a material for an emission layer.

[0153] The material for an organic electroluminescent device according to an embodiment may include a compound of formula (1) and other materials used in an organic electroluminescent device. The other materials used in an organic electroluminescent device are not particularly limited, but may be a phosphorescent compound or a host material. In addition, the other materials may be a phosphorescent complex and a host material. In this regard, the compound of formula (1) may be used as a dopant material, and the phosphorescent complex may be used as an auxiliary dopant material. By using both the compound of formula (1) and the phosphorescent complex or the host material (e.g., the phosphorescent complex and the host material), the luminous efficiency may be significantly improved. Without wishing to be bound by theory, it is believed that when the material for an organic electroluminescent device contains the host material, the phosphorescent complex receives energy from the host material. In addition, it is envisioned that the phosphorescent complex transfers energy to the compound of formula (1) by a fluorescence resonance energy transfer (FRET) mechanism. As a result, efficient energy transfer from the phosphorescent complex to the compound of formula (1) may occur. In addition, other materials used in an organic electroluminescent device may include other materials known in the art.

[0154] The amount of the compound of formula (1) relative to the total weight of the material (particularly, the material for the emission layer) used for the organic electroluminescent device is not particularly limited, but may be 0.05 weight percent (wt%) or greater. In addition, the amount of the compound of formula (1) may be 0.1 wt% or greater, such as 0.2 wt% or greater. Within this range, an organic electroluminescent device having excellent luminescent color purity and high luminescent efficiency can be obtained. The amount of the compound of formula (1) relative to the total weight of the material used for the organic electroluminescent device may be 50 wt% or less. In addition, the amount of the compound of formula (1) may be 30 wt% or less, such as 25 wt% or less, 10 wt% or less, 5 wt% or less, or 2 wt% or less. Within this range, an organic electroluminescent device having excellent luminescent color purity and high luminescent efficiency can be obtained. In addition, in the emission layer of the organic electroluminescent device described later, the amount of the compound of formula (1) relative to the total weight of the emission layer may be the same as described above.

[0155] Phosphorescent complex

[0156] In addition to the compound of formula (1), the material for an organic electroluminescent device according to an embodiment may further include a phosphorescent complex. By including the phosphorescent complex, the luminous efficiency can be significantly improved. By using both the compound of formula (1) and the phosphorescent complex, the luminous efficiency can be significantly improved. It is envisioned that the reason for the improved performance is that the phosphorescent complex transfers energy to the compound of formula (1) via the FRET mechanism. As a result, efficient energy transfer from the phosphorescent complex to the compound of formula (1) can occur. It is envisioned that, because efficient energy transfer from the phosphorescent complex to the compound of formula (1) is possible, the above technical effects are achieved.

[0157] In view of luminous efficiency, the phosphorescent complex is not particularly limited, but may be a metal complex. From the same point of view, the phosphorescent complex may be a platinum complex or a palladium complex, such as a platinum complex. Therefore, in the material for an organic electroluminescent device according to an embodiment, for example, the phosphorescent complex may be a platinum complex.

[0158] The phosphorescent complex is not particularly limited in view of luminescent color purity and luminescent efficiency, but may be, for example, a compound having a structure of formula (4).

[0159]

[0160] M in formula (4) may be a metal ion having a coordination number of 4,

[0161] R 41 , R 42 , R 43 , and R 44 may each independently be a substituted or unsubstituted (e.g., C3 to C30, such as C5 to C20, or C6 to C10) hydrocarbon cyclic group, or a substituted or unsubstituted (e.g., C1 to C30, such as C3 to C20, or C5 to C10) heterocyclic group,

[0162] L 41 Can be connected to R 41 and R 42 The connecting group

[0163] L 42 Can be connected to R 42 and R 43 A linking group, and

[0164] L 43 Can be connected to R 43 and R 44 of the connecting group.

[0165] The hydrocarbon ring group in formula (4) refers to a group derived from at least one hydrocarbon ring. When the hydrocarbon ring group includes at least two hydrocarbon rings, some or all of these rings may be bonded to each other or fused to each other via a single bond. In addition, when the hydrocarbon ring group includes at least two hydrocarbon rings, one atom may be used as a ring-forming atom of any of these rings.

[0166] The hydrocarbon cyclic group in formula (4) may be as described for the aromatic hydrocarbon group of (a8) in formula (1) or the saturated hydrocarbon group in the group of (a10), except that the valence thereof may be different. The heterocyclic group in formula (4) may be as described for the monovalent heterocyclic group of the group of (a9) in formula (1), except that the valence thereof may be different.

[0167] The substituent substituted into the hydrocarbon ring group or heterocyclic group in formula (4) is not particularly limited, but may be a substituent substituted into the groups (a4) to (a10) in formula (1).

[0168] M in formula (4) may be, for example, a platinum (Pt) ion or a palladium (Pd) ion, for example, a platinum (Pt) ion.

[0169] Known compounds can be used as the phosphorescent complex. For example, the platinum complex described in Tyler Fleetham et al., "Efficient "Pure" Blue OLEDs Employing Tetradentate Pt Complexes with a Narrow Spectral Bandwidth", Advanced Materials, 2014, 26, 7116-7121; the platinum complex described in European Patent Publication No. EP 3670520; the platinum complex and palladium complex described in Japanese Patent Publication No. JP 2019-029500; or the platinum complex described in U.S. Patent Publication No. US2015 / 0162552 can be used.

[0170] Hereinafter, the phosphorescent complex according to the embodiment is described in detail. However, the present disclosure is not limited to such examples. Examples of the phosphorescent complex may include compounds P1 to P120, or a combination thereof.

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181] The amount of the phosphorescent complex relative to the total weight of the material used for the organic electroluminescent device (particularly, the material used for the emission layer) is not particularly limited, but may be 0.1 wt % or more, for example, 0.2 wt % or more. In addition, the amount of the phosphorescent complex may be 0.5 wt % or more, for example, 1 wt % or more. In addition, the amount of the phosphorescent complex may be 3 wt % or more, for example, 5 wt % or more. Within this range, an organic electroluminescent device having excellent luminescent color purity and high luminescent efficiency can be obtained. In addition, the amount of the phosphorescent complex relative to the total weight of the material used for the organic electroluminescent device may be 50 wt % or less. In addition, the amount of the phosphorescent complex may be 40 wt % or less, for example, 30 wt % or less, 20 wt % or less, or 15 wt % or less. Within this range, an organic electroluminescent device having excellent luminescent color purity and high luminescent efficiency can be obtained. In addition, in an emission layer of an organic electroluminescent device described later, the amount of the phosphorescent complex relative to the total weight of the emission layer may be the same as described above.

[0182] When the material for an organic electroluminescent device (particularly, the material for the emission layer) includes the phosphorescent complex, the amount of the phosphorescent complex may be 100% by weight or more, based on 100% by weight of the compound of formula (1). In addition, the amount of the phosphorescent complex may be 150% by weight or more, such as 200% by weight or more, based on 100% by weight of the compound of formula (1). Within this range, an organic electroluminescent device having excellent luminescent color purity and high luminescent efficiency can be obtained. In addition, the amount of the phosphorescent complex is not particularly limited, but may be 10,000% by weight or less, based on 100% by weight of the compound of formula (1). In addition, the amount of the phosphorescent complex may be 7,500% by weight or less, such as 5,000% by weight or less, based on 100% by weight of the compound of formula (1). Within this range, an organic electroluminescent device having excellent luminescent color purity and high luminescent efficiency can be obtained. In addition, in the emission layer of the organic electroluminescent device described later, the amount (parts by weight) of the phosphorescent complex relative to 100% by weight of the compound of formula (1) may be the same as described above.

[0183] Main material

[0184] The material for an organic electroluminescent device according to an embodiment may further include a host material in addition to the compound of formula (1). By using both the compound of formula (1) as a dopant material and the host material, excellent luminous efficiency can be achieved in an organic electroluminescent device.

[0185] The host material is not particularly limited, and a known host material can be used as the host material. For example, the known host material can be an anthracene derivative, a pyrene derivative, a fluoranthene derivative, Derivatives, dihydrobenzanthracene derivatives, or benzo[9,10]phenanthrene derivatives. 9-(1-naphthyl)-10-(2-naphthyl)anthracene (Compound HT4) can be used as an anthracene derivative.

[0186]

[0187] Examples of the host material may include a compound having a carbazole ring structure (however, excluding compounds represented by formula (1)), a compound having a ring structure in which at least one ring-forming carbon atom of the carbazole ring is replaced by a nitrogen atom (however, excluding compounds represented by formula (1) and the compounds having a carbazole ring structure), or a compound having a triazine ring structure (however, excluding compounds represented by formula (1), the compounds having a carbazole ring structure, and the compounds having a ring structure in which at least one ring-forming carbon atom of the carbazole ring is replaced by a nitrogen atom). In particular, the host material may be a compound having a carbazole ring structure. By using such a compound as a host material, efficient energy transfer in the emission layer can be promoted. In addition, the balance of carrier mobility between electrons and holes can be improved. In addition, the hydrogen atoms bonded to the ring-forming atoms of the ring in the carbazole ring structure, the ring structure in which at least one ring-forming carbon atom of the carbazole ring is replaced by a nitrogen atom, and the triazine ring structure of the above compounds may be replaced by other atoms or substituents. In addition, two or more of such substituents may constitute a ring structure.

[0188] The compound having a carbazole ring structure, or the compound having a ring structure in which at least one ring-forming carbon atom of the carbazole ring is replaced by a nitrogen atom is not particularly limited, but may be a compound having a structure represented by formula (5).

[0189]

[0190] In formula (5),

[0191] Z 51 Can be CH, CR 51 , or N,

[0192] Z 52 Can be CH, CR 52 , or N,

[0193] Z 53 Can be CH, CR 53 , or N,

[0194] Z 54 Can be CH, CR 54 , or N,

[0195] Z 55 Can be CH, CR 55 , or N,

[0196] Z 56 Can be CH, CR 56 , or N,

[0197] Z 57 Can be CH, CR 57 , or N,

[0198] Z 58 Can be CH, CR 58 , or N,

[0199] R 51 To R 58 The groups may each independently be any one of (5a) to (5h):

[0200] (5a) cyano;

[0201] (5b) a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms;

[0202] (5c) a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms;

[0203] (5d) a substituted or unsubstituted arylamino group having 6 to 20 carbon atoms;

[0204] (5e) substituted or unsubstituted phosphoryl (-POH 2 Group);

[0205] (5f) substituted or unsubstituted silyl (-SiH 3 Group);

[0206] (5g) a substituted or unsubstituted monovalent aromatic hydrocarbon group; and

[0207] (5h) a substituted or unsubstituted monovalent heterocyclic group,

[0208] Ar 51 is a group including at least one of an aromatic hydrocarbon group and a heterocyclic group, and

[0209] m can be 1, 2, 3, 4, 5, or 6,

[0210] Where R 51 and R 52 , R 52 and R 53 , R 53 and R 54 , R 55 and R 56 , R 56 and R 57 , or R 57 and R 58 They may be optionally bonded to each other to form an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, or a heterocyclic ring each including the bonded carbon atoms.

[0211] The descriptions of the groups (5b) to (5d), (5g), and (5h) in formula (5) are the same as the descriptions of the groups (a4) to (a6), (a8), and (a9) in formula (1), respectively.

[0212] In addition, Ar 51 The aromatic hydrocarbon group in may be the same as the monovalent aromatic hydrocarbon group provided in the description of the group of (a8) in formula (1), except that the valence thereof may be different.

[0213] In addition, Ar 51 The heterocyclic group in may be the same as the monovalent heterocyclic group provided in the description of the group of (a9) in formula (1), except that the valence thereof may be different.

[0214] In formula (5), Z 51 To Z 58 All of may not be N, or one of them may be N. In an embodiment, Z 51 To Z 58 All of may not be N.

[0215] When the groups (5b) to (5h) in formula (5) are substituted groups, the substituents substituted into the groups (5b) to (5h) are not particularly limited. For example, the substituents may be groups (5a) to (5h). Examples of substituents substituted into the groups (5b) to (5h) are not particularly limited, but may include a cyano group; an unsubstituted alkyl group having 1 to 20 carbon atoms; an alkoxy group having 1 to 20 carbon atoms substituted by a monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, the monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms being further substituted by an unsubstituted alkenyl group having 2 to 30 carbon atoms; a substituted or unsubstituted arylamino group having 6 to 20 carbon atoms; an unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms; group; a monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms substituted by a cyano group; a monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms substituted by an unsubstituted alkenyl group having 2 to 30 carbon atoms; a monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms substituted by an unsubstituted arylamino group having 6 to 20 carbon atoms; an unsubstituted monovalent heterocyclic group having 3 to 30 ring-forming atoms; and a monovalent heterocyclic group having 3 to 30 ring-forming atoms substituted by an unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms.

[0216] In formula (5), Ar 51 There is no special restriction, as long as Ar 51 is a group including at least one of an aromatic hydrocarbon group and a heterocyclic group. 51 Examples may include a substituted or unsubstituted aromatic hydrocarbon group; a substituted or unsubstituted heterocyclic group; a group in which at least one substituted or unsubstituted aromatic hydrocarbon group is bonded to at least one substituted or unsubstituted heterocyclic group via a single bond; or a group in which at least two substituted or unsubstituted aromatic hydrocarbon groups or substituted or unsubstituted heterocyclic groups are bonded to each other via a connecting group other than the at least two groups.

[0217] In this regard, in the group in which at least two substituted or unsubstituted aromatic hydrocarbon groups or substituted or unsubstituted heterocyclic groups are bonded to each other via a connecting group other than the at least two groups, the connecting group is not particularly limited. Examples of the connecting group may include Si groups, N groups, P=O groups, S(=O)=O groups, C=O groups, etc.

[0218] When Ar in formula (5) 51When the group is a substituted group, the substituents substituted into such a group are not particularly limited. For example, the substituents may be groups of (5a) to (5h). Examples of substituents substituted into such a group are not particularly limited, but may include a cyano group, an unsubstituted alkyl group having 1 to 20 carbon atoms, a monovalent heterocyclic group having 3 to 30 ring atoms substituted by an unsubstituted alkyl group having 1 to 20 carbon atoms, and the like.

[0219] In this regard, the substituents of the groups (5b) to (5h), or the substituents constituting Ar 51 Among the substituents of the group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, and a monovalent heterocyclic group having 3 to 30 ring-forming atoms are respectively the same as described for the groups (a4) to (a10) in formula (1).

[0220] In addition, the substituents of the groups (5c) to (5h) or the substituents constituting Ar 51 The alkenyl group with 2 to 30 carbon atoms in the substituent of the group is not particularly limited, and can be straight-chain, branched or cyclic. The example of the alkenyl group is not particularly limited, but can include, for example, vinyl, 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, etc.

[0221] In formula (5), m may be 1, 2, 3, or 4, for example, 2.

[0222] Hereinafter, as a host material according to an embodiment, a compound having a carbazole ring structure and a compound having a ring structure in which at least one ring-forming carbon atom of the carbazole ring is replaced by a nitrogen atom are described in detail. However, the present disclosure is not limited to such examples.

[0223] The host material may include one of compounds H1 to H88, HT1 to HT2, or a combination thereof.

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232] Therefore, the material for an organic EL device according to an embodiment and the organic electroluminescent device according to an embodiment described later may include a compound of formula (1) and a host material, wherein the host material may include at least one (for example, two) compounds having a structure represented by formula (5). In addition, the material for an organic EL device according to an embodiment and the organic electroluminescent device according to an embodiment described later may include a compound of formula (1), a phosphorescent complex and a host material, wherein the host material may include a compound having a structure represented by formula (5). In addition, the material for an organic EL device according to an embodiment and the organic electroluminescent device according to an embodiment described later may include a compound of formula (1), a phosphorescent complex and a host material, wherein the host material may include at least two compounds having a structure represented by formula (5). For example, the compound having a structure represented by formula (5) may include HT1 and HT2.

[0233] The compound having a triazine ring structure is not particularly limited, but may be a compound having a structure represented by formula (6).

[0234]

[0235] In formula (6),

[0236] Ar 61 To Ar 63 They may each independently be a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent heterocyclic group.

[0237] In formula (6), the substituted or unsubstituted monovalent aromatic hydrocarbon group is as described in the description of the group (a8) in formula (1). In addition, the substituted or unsubstituted monovalent heterocyclic group is as described in the description of the group (a9) in formula (1).

[0238] The substituents substituted into the monovalent aromatic hydrocarbon group or the monovalent heterocyclic group in formula (6) are not particularly limited, but may be substituents substituted into the groups (a4) to (a10) in formula (1). In addition, the substituents may be silyl groups substituted with unsubstituted monovalent aromatic hydrocarbon groups. In addition, the unsubstituted monovalent aromatic hydrocarbon groups are as described in the description of the unsubstituted groups in (a8).

[0239] As the compound having a triazine ring structure, a compound including a silyl group (a compound having a triazine ring structure possessing a silyl group) may be preferred.

[0240] In addition, the compound having a triazine ring structure may be used in combination with the compound having a carbazole ring structure or the compound having a ring structure in which at least one ring-forming carbon atom of the carbazole ring is replaced by a nitrogen atom.

[0241] Hereinafter, the compound having a triazine structure as a host material according to an embodiment is described in detail. However, the present disclosure is not limited to such examples. Examples of the compound having a triazine structure include H86, H87, H88, HT2, and the like.

[0242]

[0243] Therefore, the material for an organic electroluminescent device according to the embodiment and the organic electroluminescent device according to the embodiment described later may include a compound of formula (1) and a host material, wherein the host material may include a compound having a structure represented by formula (6). In addition, the material for an organic electroluminescent device according to the embodiment and the organic electroluminescent device according to the embodiment described later may include a compound of formula (1), a phosphorescent complex and a host material, wherein the host material may include a compound having a structure represented by formula (6). In addition, the material for an organic electroluminescent device according to the embodiment may include a compound of formula (1), a phosphorescent complex and a host material, wherein the host material may include a compound having a structure represented by formula (5) and a compound having a structure represented by formula (6). In addition, the organic electroluminescent device according to the embodiment may include a compound of formula (1) and a host material, wherein the host material may include a compound having a structure represented by formula (5) and a compound having a structure represented by formula (6).

[0244] The amount of the main material relative to the total weight of the material for the organic electroluminescent device (especially the material for the emission layer) is not particularly limited, but may be 5 weight % or more. In addition, the amount of the main material may be 10 weight % or more, for example, 20 weight % or more. Within this range, an organic electroluminescent device with excellent luminescent color purity and high luminescent efficiency can be obtained. In addition, the amount of the main material relative to the total weight of the material for the organic electroluminescent device (especially the material for the emission layer) is not particularly limited, but may be 99 weight % or less. In addition, the amount of the main material may be 98 weight % or less, for example, 95 weight % or less. Within this range, an organic electroluminescent device with excellent luminescent color purity and high luminescent efficiency can be obtained. In addition, in the emission layer of the organic electroluminescent device described later, the amount of the main material relative to the total weight of the emission layer may be the same as described above.

[0245] When the material used for the organic electroluminescent device (particularly, the material for the emission layer) includes a host material, the amount of the host material may be 1,000 wt % or more, based on 100 wt % of the compound of formula (1). In addition, the amount of the host material may be 2,000 wt % or more, for example 3,000 wt % or more, based on 100 wt % of the compound of formula (1). Within this range, an organic electroluminescent device with excellent luminescent color purity and high luminescent efficiency can be obtained. In addition, the amount of the host material is not particularly limited, but may be 200,000 wt % or less, based on 100 wt % of the compound of formula (1). In addition, the amount of the host material may be 150,000 wt % or less, for example 100,000 wt % or less, based on 100 wt % of the compound of formula (1). Within this range, an organic electroluminescent device with excellent luminescent color purity and high luminescent efficiency can be obtained. In addition, in the emission layer of the organic electroluminescent device described later, the amount (parts by weight) of the host material relative to 100 wt % of the compound of formula (1) may be the same as described above.

[0246] Liquid composition

[0247] Another aspect of the present disclosure relates to a liquid composition comprising the material for an organic electroluminescent device, and a solvent, wherein the material for an organic electroluminescent device comprises the compound of formula (1).

[0248] The solvent is not particularly limited, and may be a solvent having a boiling point of at least about 100°C and not more than about 350°C at atmospheric pressure (101.3 kilopascals (kPa), 1 atmosphere (atm)). The boiling point of the solvent at atmospheric pressure may be about 150°C to about 320°C, for example, about 180°C to about 300°C. When the boiling point of the solvent at atmospheric pressure is within the above range, the processability or film forming ability of the wet film forming method, especially the inkjet method, may be improved. The solvent having a boiling point of about 100°C to about 350°C at atmospheric pressure is not particularly limited, and known solvents may be suitably used. Hereinafter, a solvent having a boiling point of about 100°C to about 350°C at atmospheric pressure is described in detail, but the present disclosure is not limited thereto. Examples of hydrocarbon-based solvents may include octane, nonane, decane, undecane, dodecane, and the like. Examples of aromatic hydrocarbon-based solvents may include toluene, xylene, ethylbenzene, n-propylbenzene, isopropylbenzene, mesitylene, n-butylbenzene, sec-butylbenzene, 1-phenylpentane, 2-phenylpentane, 3-phenylpentane, phenylcyclopentane, phenylcyclohexane, 2-ethylbiphenyl, 3-ethylbiphenyl, etc. Examples of ether-based solvents may include 1,4-dioxane, 1,2-diethoxyethane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, anisole, ethoxybenzene, 3-methylanisole, m-dimethoxybenzene, etc. Examples of ketone-based solvents may include 2-hexanone, 3-hexanone, cyclohexanone, 2-heptanone, 3-heptanone, 4-heptanone, cycloheptanone, etc. Examples of ester-based solvents may include butyl acetate, butyl propionate, butyl butyrate, propylene carbonate, methyl benzoate, ethyl benzoate, 1-propyl benzoate, 1-butyl benzoate, etc. Examples of nitrile-based solvents may include benzonitrile, 3-methylbenzonitrile, etc. Examples of amide-based solvents may include dimethylformamide, dimethylacetamide, N-methylpyrrolidone, etc. Such solvents may be used alone or in combination of two or more.

[0249] In an embodiment, the amounts of the compound of formula (1) and the material for an organic electroluminescent device in the liquid composition are not particularly limited.

[0250] In an embodiment, the liquid composition may be used as a coating liquid for forming an organic layer of an organic electroluminescent device. In addition, the liquid composition may be used as a coating liquid for forming an emission layer among coating liquids for forming an organic layer.

[0251] Organic electroluminescent devices

[0252] Another aspect of the present disclosure relates to an organic electroluminescent device having an emission layer comprising a compound of formula (1). In addition, the emission layer in the organic electroluminescent device may include a compound of formula (1) and a phosphorescent complex, wherein in addition to the compound of formula (1) and the phosphorescent complex, the emission layer may further include a host material. In this case, the phosphorescent complex may be a platinum complex.

[0253] In addition, another aspect of the present disclosure relates to an organic electroluminescent device including the material for an organic electroluminescent device. In addition, the material for an organic electroluminescent device in the organic electroluminescent device may further include a host material. In addition, the phosphorescent complex included in the organic electroluminescent device may be a platinum complex.

[0254] The host material included in the organic electroluminescent device may be the compound having a carbazole ring structure, the compound having a ring structure in which at least one ring-forming carbon atom of the carbazole ring is replaced by a nitrogen atom, or the compound having a triazine ring structure. In addition, the host material included in the organic electroluminescent device may include a compound having a structure represented by formula (5). In addition, the host material included in the organic electroluminescent device may include a compound having a structure represented by formula (6). In addition, the host material included in the organic electroluminescent device may include a compound having a structure represented by formula (5) and a compound having a structure represented by formula (6).

[0255] In addition, the phosphorescent complex included in the organic electroluminescent device may be a compound having a structure represented by formula (4).

[0256] The organic electroluminescent device according to the embodiment is not particularly limited, and may include, for example, a first electrode, a second electrode, and a single organic layer or a plurality of organic layers. The second electrode may be disposed on the first electrode.

[0257] Herein, when a portion of a layer, film, region, plate, etc. is said to be "on" or "over" another portion, this includes not only the case where the portion is "directly on" the other portion but also the case where an intermediate layer exists therebetween. In addition, when a portion of a layer, film, region, plate, etc. is said to be "under" or "beneath" another portion, this includes not only the case where the portion is "directly under" the other portion but also the case where an intermediate layer exists therebetween. Herein, being disposed "on" includes not only being disposed on the top surface but also being disposed on the lower or bottom surface.

[0258] The organic electroluminescent device according to the embodiment may include a first electrode, a second electrode, and a single layer or multiple layers between the first electrode and the second electrode. In this regard, the single layer or multiple layers may include at least one organic layer, and at least one of the organic layers may include a compound of formula (1) or the material for an organic electroluminescent device. The organic layer including the compound of formula (1) or the material for an organic electroluminescent device may include an emission layer. Light emission with high color purity can be achieved by these organic electroluminescent devices.

[0259] Thus, the emissive layer may include at least one compound of formula (1).

[0260] The emission layer may be a single layer composed of a single material or a single layer composed of a plurality of different materials. In addition, the emission layer may have a multi-layer structure having a plurality of layers composed of a plurality of different materials.

[0261] The emission layer is not particularly limited, and may include, for example, a host material and a dopant material. The compound of formula (1) may be used as the dopant material.

[0262] In an embodiment, the organic electroluminescent device may include an emission layer, wherein the emission layer may include a compound of formula (1) or the material for an organic electroluminescent device. In addition, the emission layer may include the material for an organic electroluminescent device. In view of the peak wavelength in the emission spectrum, the purity of the luminescent color and the luminous efficiency, in addition to the compound of formula (1), the material for an organic electroluminescent device may also include a host material. In an embodiment, in addition to the compound of formula (1), the material for an organic electroluminescent device may also include a phosphorescent complex and a host material. In addition, the amount or ratio of the compound of formula (1), the phosphorescent complex and the host material in the emission layer may be the same as the amount or ratio in the material for an organic electroluminescent device.

[0263] The thickness of the emission layer is not particularly limited, but may be at least about 1 nm and not more than about 100 nm, for example, at least about 10 nm and not more than about 50 nm.

[0264] Examples of the film forming method of the emission layer are not particularly limited, but may include known film forming methods such as vacuum deposition, spin coating, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, or laser induced thermal imaging (LITI).

[0265] The emission wavelength of the organic electroluminescent device is not particularly limited. The emission wavelength of the organic electroluminescent device may be the same as the peak wavelength of the emission of the PL of the compound of formula (1) according to the present disclosure, for example. In particular, in the specification of currently commercialized products, in the case of blue light emission, the organic electroluminescent device may emit light having a peak in a wavelength region of about 445nm to about 470nm, for example, about 450nm to about 470nm, for example, about 450nm to about 465nm.

[0266] In addition, the FWHM of the peak of the emission spectrum of the organic electroluminescent device can be reduced. The FWHM of the peak of the emission spectrum can be 30nm or less, for example, 25nm or less. The FWHM of the peak of the emission spectrum can be 20nm or less (the lower limit is greater than 0nm).

[0267] Hereinafter, the following case is described in detail with reference to the accompanying drawings: in which, in addition to the emission layer, the organic electroluminescent device according to the embodiment further includes an organic layer. In the description of the accompanying drawings, the same components will be represented by the same reference numerals, and their redundant description will be omitted. In addition, for the convenience of description, the dimensional ratios in the accompanying drawings may be exaggerated and therefore may be different from the actual ratios.

[0268] Figures 1 to 3 Each is a schematic cross-sectional view showing an embodiment of an organic electroluminescent device. However, the structure of the organic electroluminescent device according to the present disclosure is not limited to Figures 1 to 3 Those shown in .

[0269] Figure 1 Schematic cross-sectional view of an embodiment of an organic electroluminescent device. An organic electroluminescent device 10 according to an embodiment includes a substrate 1, a first electrode 2, a hole transport region 3, an emission layer 4, an electron transport region 5, and a second electrode 6, which are sequentially stacked in the stated order.

[0270] Figure 2 Schematic cross-sectional view of an embodiment of an organic electroluminescent device. The organic electroluminescent device 10 according to the embodiment includes a substrate 1, a first electrode 2, a hole transport region 3, an emission layer 4, an electron transport region 5, and a second electrode 6, which are sequentially stacked in the order of the statements. Figure 2 In the embodiment, the hole transport region 3 includes a hole injection layer 31 and a hole transport layer 32, which are sequentially stacked in the order of this statement. Figure 2 , the electron transport region 5 includes an electron transport layer 52 and an electron injection layer 51, which are sequentially stacked in the order stated.

[0271] Figure 3Schematic cross-sectional view of an embodiment of an organic electroluminescent device. The organic electroluminescent device 10 according to the embodiment includes a substrate 1, a first electrode 2, a hole transport region 3, an emission layer 4, an electron transport region 5, and a second electrode 6, which are sequentially stacked in the order of the statements. Figure 3 In the embodiment, the hole transport region 3 includes a hole injection layer 31, a hole transport layer 32, and an electron blocking layer 33, which are sequentially stacked in the order of this statement. Figure 3 In FIG. 5 , the electron transport region 5 includes a hole blocking layer 53 , an electron transport layer 52 , and an electron injection layer 51 , which are sequentially stacked in the order stated.

[0272] Hereinafter, the substrate, each region, and each layer are described in detail.

[0273] Substrate 1

[0274] The organic electroluminescent device 10 may have a substrate 1. As the substrate 1, any substrate used in a general organic electroluminescent device may be used. For example, the substrate 1 may be a glass substrate, a semiconductor substrate such as a silicon substrate, or a transparent plastic substrate.

[0275] First electrode 2

[0276] The first electrode 2 may be conductive. In the organic electroluminescent device 10 according to the embodiment, the first electrode 2 may be an anode. In addition, the first electrode 2 may be a pixel electrode. In addition, the first electrode 2 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

[0277] The material used to form the first electrode 2 is not particularly limited, and may be, for example, a metal, a metal alloy, or a conductive compound. When the first electrode 2 is a transmissive electrode, the first electrode 2 may include a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc. In addition, when the first electrode 2 is a semi-transmissive electrode or a reflective electrode, the first electrode 2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or a compound (compound) or a mixture thereof (e.g., a mixture of Ag and Mg).

[0278] The first electrode 2 may be a single layer composed of a single material or a single layer composed of a plurality of different materials. In addition, the first electrode 2 may have a multilayer structure having a plurality of layers composed of a plurality of different materials.

[0279] The thickness of the first electrode 2 is not particularly limited, but may be at least about 10 nm and not more than about 1,000 nm, for example, at least about 50 nm and not more than about 300 nm.

[0280] Hole transport region 3

[0281] The hole transport region 3 is provided on the first electrode 2. The hole transport region 3 may include at least one of a hole injection layer 31, a hole transport layer 32, a hole buffer layer (not shown), and an electron blocking layer 33.

[0282] The hole transport region 3 may be a single layer composed of a single material or a single layer composed of a plurality of different materials. In addition, the hole transport region 3 may have a multilayer structure having a plurality of layers composed of a plurality of different materials.

[0283] For example, the hole transport region 3 may have a single-layer structure including a hole injection layer 31 or a hole transport layer 32. In addition, for example, the hole transport region 3 may have a single-layer structure including a hole injection material and a hole transport material. In addition, for example, the hole transport region 3 may have a structure of hole injection layer 31 / hole transport layer 32, wherein the constituent layers are sequentially stacked from the first electrode 2. In addition, for example, the hole transport region 3 may have a structure of hole injection layer 31 / hole transport layer 32 / hole buffer layer (not shown). In addition, for example, the hole transport region 3 may have a structure of hole injection layer 31 / hole buffer layer (not shown), wherein the constituent layers are sequentially stacked from the first electrode 2. In addition, for example, the hole transport region 3 may have a structure of hole transport layer 32 / hole buffer layer (not shown), wherein the constituent layers are sequentially stacked from the first electrode 2. In addition, for example, the hole transport region 3 may have a structure of hole injection layer 31 / hole transport layer 32 / electron blocking layer 33 in which constituent layers are sequentially stacked from the first electrode 2. However, the structure of the hole transport region is not limited to the above example.

[0284] The hole injection layer 31 constituting the hole transport region 3 is not particularly limited, but may include, for example, a known hole injection material. Examples of the hole injection material may include phthalocyanine compounds such as copper phthalocyanine, N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine (DNTPD), 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tris{N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4-styrene sulfonate) (PEDOT / PSS), polyphenylene oxide ... Amine / dodecylbenzenesulfonic acid (PANI / DBSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), N,N'-di(naphthalene-1-yl)-N,N'-diphenylbenzidine (NPB), polyetherketone including triphenylamine (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate, dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexanitrile (HAT-CN), 1,3,4,5,7,8-hexafluorotetracyano-2,6-naphthoquinone dimethane (F6-TCNNQ), etc.

[0285] In addition, the hole transport layer 32 constituting the hole transport region 3 is not particularly limited, and may include, for example, a known hole transport material. Examples of the hole transport material may include carbazole-based derivatives such as N-phenylcarbazole, polyvinylcarbazole, etc., fluorene-based derivatives, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'diamine (TPD), triphenylamine-based derivatives such as 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPB), 4,4'-cyclohexylidenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), 1,3-bis(N-carbazolyl)benzene (mCP), compound HTM1, compound HTM2, compound HT3, etc.

[0286]

[0287] In addition to the hole injection material or the hole transport material, the hole transport region 3 may further include a charge generating material to improve conductivity. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region 3 or its layers. The charge generating material is not particularly limited, but examples thereof may include known charge generating materials. The charge generating material may be, for example, a p-dopant. Examples of the p-dopant may include quinone derivatives such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyanoquinodimethane (F4-TCNQ), etc., metal oxides such as tungsten oxide, molybdenum oxide, etc., cyano-containing compounds, etc.

[0288] The hole buffer layer (not shown) may compensate for the optical resonance distance according to the wavelength of light emitted from the emission layer 4 to improve the photoluminescence emission efficiency. The material included in the hole buffer layer (not shown) is not particularly limited, and materials used in known hole buffer layers may be used. For example, a compound that may be included in the hole transport region 3 may be used.

[0289] The electron blocking layer 33 can prevent electrons from being injected from the electron transport region 5 to the hole transport region 3. The material included in the electron blocking layer 33 is not particularly limited, and materials used in known electron blocking layers can be used. For example, host materials such as compounds H55, H86, and H87 included in the emission layer (the material for an organic electroluminescent device) can be used.

[0290] The thickness of the hole transport region 3 is not particularly limited, but may be from about 1 nm to about 1,000 nm, for example, from about 10 nm to about 500 nm. In addition, with respect to the layers constituting the hole transport region 3, the thickness of the hole injection layer 31 may be, but is not particularly limited to, from about 3 nm to about 200 nm. The thickness of the hole transport layer 32 may be, but is not particularly limited to, from about 3 nm to about 200 nm. The thickness of the electron blocking layer 33 may be, but is not particularly limited to, from about 1 nm to about 100 nm. In addition, the thickness of the hole buffer layer (not shown) is not particularly limited, as long as the hole buffer layer acts as a hole buffer layer and does not interfere with the function of the organic electroluminescent device. When the thickness of the hole transport region 3, the hole injection layer 31, the hole transport layer 32, or the electron blocking layer 33 is within the above range, excellent hole transport characteristics can be obtained while suppressing a significant increase in the driving voltage.

[0291] Examples of the film-forming method of the hole transport region 3 or each layer thereof are not particularly limited, but may include known film-forming methods such as vacuum deposition, spin coating, LB deposition, inkjet printing, laser printing, or LITI.

[0292] Emission layer 4

[0293] The emission layer 4 is provided on the hole transport region 3. The details of the emission layer 4 are as described above.

[0294] Electron transport region 5

[0295] The electron transport region 5 is disposed on the emission layer 4. The electron transport region 5 includes at least one of an electron injection layer 51, an electron transport layer 52, and a hole blocking layer 53, but the embodiment is not limited thereto.

[0296] The electron transport region 5 may be a single layer composed of a single material or a single layer composed of a plurality of different materials. In addition, the electron transport region 5 may have a multilayer structure having a plurality of layers composed of a plurality of different materials. For example, the electron transport region 5 may have a single-layer structure including an electron injection layer 51 or an electron transport layer 52. In addition, for example, the electron transport region 5 may have a single-layer structure composed of an electron injection material and an electron transport material. In addition, for example, the electron transport region 5 may have a structure of an electron transport layer 52 / electron injection layer 51, wherein the constituent layers are stacked sequentially from the emission layer 4. In addition, for example, the electron transport region 5 may have a structure of a hole blocking layer 53 / electron transport layer 52 / electron injection layer 51, wherein the constituent layers are stacked sequentially from the emission layer 4. However, the structure of the electron transport region 5 is not limited to the above examples.

[0297] The electron injection layer 51 constituting the electron transport region 5 is not particularly limited, but may include, for example, a known electron injection material. Examples of the electron injection material may include lanthanide metals such as Yb, LiF, 8-hydroxyquinoline lithium (LiQ), Li 2 O, BaO, or metal halides such as NaCl, CsF, or RbCl. The electron injection layer 51 is not particularly limited, and may include, for example, an electron injection material and an insulating organic metal salt. The organic metal salt is not particularly limited, and may be, for example, a material having an energy band gap of 4 electron volts (eV) or greater. The organic metal salt may be, for example, an acetate metal salt, a benzoate metal salt, an acetoacetate metal salt, an acetylacetone metal salt, or a stearate metal salt.

[0298] The electron transport layer 52 constituting the electron transport region 5 is not particularly limited and may include, for example, a known electron transport material. Examples of the electron transport material may include an anthracene-based compound, tris(8-hydroxyquinoline)aluminum (Alq 3), 1,3,5-tris[(3-pyridyl)-phenyl-3-yl]benzene, 2,4,6-tris(3'-pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazol-1-ylphenyl)-9,10-dinaphthylanthracene, 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bph en), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD), bis(2-methyl-8-hydroxyquinolinolato-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), bis(benzoquinolinolato-10-hydroxy)beryllium (Bebq 2 ), 9,10-di(naphthalene-2-yl)anthracene (ADN), 8-hydroxyquinoline lithium (LiQ), compound ET1, H91, etc. In addition, TRE314 (product of Toray Co., Ltd., electron transport material) and the like can be used.

[0299]

[0300] The hole blocking layer 53 can prevent holes from being injected from the hole transport region 3 to the electron transport region 5. The material included in the hole blocking layer 53 is not particularly limited, and the material used in the known hole blocking layer can be used. The hole blocking layer 53 may include, for example, a known hole blocking material. Examples of the hole blocking material may include 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (BPhen), etc. In addition, for example, a host material included in the emission layer (the material for the organic electroluminescent device) such as compounds H77 and H87 can be used.

[0301] The thickness of the electron transport region 5 is not particularly limited, but may be from about 0.1 nm to about 200 nm, for example, from about 30 nm to about 150 nm. In addition, with respect to each layer constituting the electron transport region 5, the thickness of the electron transport layer 52 may be, but is not particularly limited to, from about 10 nm to about 100 nm, for example, from about 15 nm to about 500 nm. The thickness of the hole blocking layer 53 is not particularly limited, but may be from about 1 nm to about 100 nm, for example, from about 5 nm to about 30 nm. The thickness of the electron injection layer 51 is not particularly limited, but may be from about 0.1 nm to about 10 nm, for example, from about 0.3 nm to about 9 nm. When the thickness of the electron injection layer 51 is within the above range, excellent electron injection characteristics can be obtained while suppressing a significant increase in the driving voltage. In addition, when the thickness of the electron transport region 5, the electron injection layer 51, the electron transport layer 52, or the hole blocking layer 53 is within the above range, excellent electron transport characteristics can be obtained while suppressing a significant increase in the driving voltage.

[0302] Examples of the film-forming method of the electron transport region 5 or each layer thereof are not particularly limited, but may include known film-forming methods such as vacuum deposition, spin coating, LB deposition, inkjet printing, laser printing, or LITI.

[0303] Second electrode 6

[0304] The second electrode 6 is disposed on the electron transport region 5. The second electrode 6 is conductive. The second electrode 6 in the organic electroluminescent device according to the embodiment may be a common electrode or a cathode. In addition, the second electrode 6 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

[0305] The material used to form the second electrode 6 is not particularly limited, but may be, for example, a metal, a metal alloy, or a conductive compound. When the second electrode 6 is a transmissive electrode, the second electrode 6 may include a transparent metal oxide, such as ITO, IZO, ZnO, ITZO, etc. When the second electrode 6 is a semi-transmissive electrode or a reflective electrode, the second electrode 6 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or a compound (compound) or a mixture thereof (e.g., a mixture of Ag and Mg).

[0306] The second electrode 6 may be a single layer composed of a single material or a single layer composed of a plurality of different materials. In addition, the second electrode 6 may have a multilayer structure having a plurality of layers composed of a plurality of different materials.

[0307] The thickness of the second electrode 6 may be, but is not particularly limited to, about 10 nm to about 1,000 nm.

[0308] The second electrode 6 may be connected to an auxiliary electrode (not shown). Since the second electrode 6 is connected to the auxiliary electrode, the resistance of the second electrode 6 may be further reduced.

[0309] In addition, a capping layer (not shown) may be further provided on the second electrode 6. The capping layer (not shown) is not particularly limited, but may be, for example, a material including α-NPD, NPB, TPD, m-MTDATA, Alq 3 , CuPc, N4,N4,N4',N4'-tetrakis(biphenyl-4-yl)biphenyl-4,4'diamine (TPD15), 4,4',4"-tri-9-carbazolyltriphenylamine (TCTA), N,N'-bis(naphthalene-1-yl)-N,N'-bis(phenyl)benzidine (NPB), etc.

[0310] In addition, materials constituting each layer and each electrode may be used alone or in combination of two or more.

[0311] exist Figures 1 to 3 In the organic electroluminescent device 10, the compound of formula (1) or the material for an organic electroluminescent device may be included in the emission layer 4, but may also be included in an organic layer other than the emission layer 4. In addition, the compound of formula (1) or the material for an organic electroluminescent device may be included in the emission layer 4 and the organic layer other than the emission layer 4.

[0312] exist Figures 1 to 3 In the organic electroluminescent device 10, since a voltage is applied to each of the first electrode 2 and the second electrode 6, holes provided from the first electrode 2 may move toward the emission layer 4 through the hole transport region 3, and electrons provided from the second electrode 6 may move toward the emission layer 4 through the electron transport region 5. The holes and the electrons may be recombined in the emission layer 4 to generate excitons, and these excitons may transition from an excited state to a ground state to thereby generate light.

[0313] While embodiments of the present disclosure have been described in detail, it will be understood that these embodiments are illustrative and not intended to be limiting, and that the scope of the present disclosure should be interpreted in accordance with the appended claims.

[0314] The present disclosure includes the following aspects and embodiments.

[0315] Aspect 1. A compound represented by formula (1):

[0316]

[0317] Among them, in formula (1),

[0318] R 1 To R 16 At least one of

[0319] The substituent W represented by formula (2) (* represents the bonding site to the benzene ring),

[0320] as well as

[0321] R other than the substituent W 1 To R 16 can be independently any one of the atoms or groups from (a1) to (a10):

[0322] (a1) Hydrogen or deuterium atoms;

[0323] (a2) halogen atoms;

[0324] (a3) cyano;

[0325] (a4) a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms;

[0326] (a5) a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms;

[0327] (a6) a substituted or unsubstituted arylamino group having 6 to 20 carbon atoms;

[0328] (a7) a substituted or unsubstituted triarylsilyl group, an alkyldiarylsilyl group, a dialkylarylsilyl group, or a trialkylsilyl group (wherein the aryl group is an aryl group having 6 to 20 carbon atoms, and the alkyl group is an alkyl group having 1 to 20 carbon atoms);

[0329] (a8) a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms;

[0330] (a9) a substituted or unsubstituted heterocyclic group having 3 to 30 ring atoms; and

[0331] (a10) a substituted or unsubstituted saturated hydrocarbon group or a saturated heterocyclic group, each of which is bonded to R 1 To R 16 The ring is formed by two adjacent groups in the ring and has 5 to 9 ring atoms.

[0332] Aspect 2. The compound according to aspect 1, wherein R 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 , and R 15 At least two of may each be a substituent W.

[0333] Aspect 3. An organic electroluminescent device having an emission layer comprising the compound according to aspect 1 or 2.

[0334] Aspect 4. The organic electroluminescent device according to aspect 3, wherein the emission layer further comprises a phosphorescent complex.

[0335] Example

[0336] Hereinafter, the present disclosure will be described in more detail with reference to the following Examples and Comparative Examples, but the technical scope of the present disclosure is not limited thereto.

[0337] Synthesis of compounds

[0338] Compounds 1 to 4 were synthesized according to the following synthesis examples for use in the manufacture of organic electroluminescent devices. In addition, comparative compounds C1 to C4 were prepared for use in the manufacture of comparative organic electroluminescent devices. Compounds 1 to 4 correspond to the above-mentioned compounds (110), (111), (113) and (105), respectively.

[0339]

[0340]

[0341] Synthesis Example 1

[0342] Compound 1 was synthesized according to the following scheme.

[0343]

[0344] Synthesis of intermediate 1

[0345] Under a nitrogen atmosphere, 6-bromoindole (15 grams (g), 76.5 millimoles (mmol)) and N,N-dimethylformamide (DMF) (600 milliliters (mL)) were combined in a 1L three-necked flask and then cooled to 0°C. Sodium hydride (3.7 g, 91.8 mmol) (60% by weight of sodium hydride dispersed in liquid paraffin) was added in three portions, and the obtained reaction solution was stirred at 0°C for 1 hour. After that, the reaction solution was heated to room temperature, stirred for 1 hour, and then cooled to 0°C. After cooling, 2-(chloromethoxy)ethyltrimethylsilane ("SEM-Cl" in the above scheme) (15.3 g, 91.8 mmol) was slowly added dropwise to the reaction solution and stirred at room temperature for 12 hours. Next, the aqueous suspension obtained by injecting the reaction solution into ice was extracted with hexane (200 mL×3). The extracted organic layer was washed with a saturated saline solution (200 mL) and then dried with anhydrous sodium sulfate (desiccant). After filtration, the solvent in the organic layer was removed by distillation under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: hexane) to provide Intermediate 1 (25.5 g, 85% yield) as a colorless liquid. In addition, in the above scheme, "SEM" refers to "(CH 3 ) 3 SiC 2 CH 2 OCH 2 ”.

[0346] Synthesis of intermediate 2

[0347] Under a nitrogen atmosphere, magnesium (3.74 g, 153 mmol) and anhydrous tetrahydrofuran (THF) (150 mL) were combined in a 1L three-necked flask, and a small amount of 1,2-dibromoethane was added thereto, followed by stirring at room temperature for 30 minutes. A solution of 2,4,6-tri-tert-butylbromobenzene (25 g, 76.9 mmol) in anhydrous tetrahydrofuran (150 mL) was slowly added dropwise to the reaction solution, followed by stirring at 60°C for 2 hours to prepare a Grignard reagent solution. Intermediate 1 (12.5 g, 38.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (“Pd 2 (dba) 3”) (1.76 g, 1.92 mmol), 2-dicyclohexylphosphino-2'-6'-dimethoxybiphenyl ("SPhos") (1.58 g, 3.84 mmol), and toluene (100 mL) were added to another 1L 3-necked flask, and then stirred. The Grignard reagent solution prepared above was added dropwise to the solution at room temperature, and the resulting reaction solution was stirred at 70°C for 10 hours. Thereafter, the reaction solution was cooled to room temperature, and insoluble components in the reaction solution were removed by filtration using diatomaceous earth. The organic layer of the reaction solution was washed with a saturated saline solution (200 mL×2), and then dried over anhydrous sodium sulfate (desiccant). After filtration, the solvent in the organic layer was removed by distillation under reduced pressure. The obtained residue was dissolved in DMF (100 mL), and to the solution were added tetrabutylammonium fluoride hydrate (30.1 g, 115 mmol) and Ethylenediamine (6.92g, 115mmol), and stirred for 6 hours at 100 ℃. The obtained reaction solution is cooled to room temperature, the reaction solution is added to 200mL of water, and the solution is extracted with ethyl acetate (200mLx3). The extracted organic layer is washed with saturated saline solution (300mL), then dried with anhydrous sodium sulfate (desiccant). After filtration, the solvent in the organic layer is removed by distillation under reduced pressure. The residue obtained is purified by silica gel column chromatography (eluent: hexane: ethyl acetate (volume ratio=95:5)) to provide intermediate 2 (7.0g, 50% yield) as a white solid.

[0348] Synthesis of intermediate 3

[0349] Under nitrogen atmosphere, 5-tert-butyl-2-chlorobenzaldehyde (2.2g, 11.1mmol), intermediate 2 (4.0g, 11.1mmol) and 110.6mL of acetonitrile are combined in a 100mL three-necked flask. The resulting reaction solution is heated to 80°C, and 57% by weight of hydroiodic acid (0.3mL, 2.2mmol) is added thereto and stirred for 2 hours. After the reaction solution is cooled to room temperature, the precipitated solid is filtered off, and the solid obtained is washed with cooling acetonitrile to provide intermediate 3 (4.3g, 73% yield) as a white powder.

[0350] Synthesis of compound 1

[0351] Under nitrogen atmosphere, intermediate 3 (4.3g, 4.1mmol), tetrabutylammonium hydroxide (37 wt% methanol solution) (17.2mL, 20.3mmol), cuprous iodide (I) (3.9g, 20.3mmol) and 41mL of dimethylformamide are combined in a 100mL three-necked flask, and the resulting reaction solution is heated and stirred at 140°C. Tetrabutylammonium hydroxide (37 wt% methanol solution) (17.2mL, 20.3mmol) and cuprous iodide (I) (3.9g, 20.3mmol) are added to the reaction solution every 8 hours, and the reaction is allowed to proceed for 24 hours. Afterwards, the reaction solution is cooled to room temperature, and the precipitated solid is filtered out. The filtered solid, 200ml of methanol and 50mL of ethylenediamine are combined and stirred in a 500mL conical flask, and the solid is filtered out and extracted. The solid thus obtained was dispersed and washed with THF-acetone to provide Compound 1 (1.5 g, 35% yield) as a yellow solid. LC-MS: 1005 ([M+H] + ).

[0352] Compound data of compound 1 (confirmation data)

[0353] The structure of the obtained compound 1 was confirmed by nuclear magnetic resonance spectroscopy:

[0354] 1 H NMR data (400 MHz, CD 2 Cl 2 )(parts per million, ppm) 1.24 (36H, s), 1.47 (18H, s), 1.85 (18H, s), 7.61 (2H, dd, J=7.8, 1.2 Hz), 7.69 (4H, s), 7.76 (2H, dd, J=8.7, 1.8 Hz), 8.03 (2H, d, J=8.7 Hz), 8.14 (2H, d, J=1.2 Hz), 8.55 (2H, d, J=7.8 Hz), 8.69 (2H, d, J=1.8 Hz).

[0355] Synthesis Example 2

[0356] Compound 2 was synthesized according to the following scheme.

[0357]

[0358] Synthesis of intermediate 4

[0359] Intermediate 4 was synthesized in the same manner as Intermediate 3. Intermediate 4 (4.64 g, 63% yield) was obtained using Intermediate 2 (3.96 g, 10.95 mmol) and 3',5'-di-(tert-butyl)-3-chloro-4-formyl-[1,1'-biphenyl] (3.6 g, 10.95 mmol).

[0360] Synthesis of compound 2

[0361] Compound 2 was synthesized in the same manner as Compound 1. Intermediate 4 (2.32 g, 1.73 mmol) was used for synthesis to obtain Compound 2 (1.75 g, 80% yield) as a yellow solid. LC-MS: 1269 ([M] + ).

[0362] Synthesis Example 3

[0363] Compound 3 was synthesized according to the following scheme.

[0364]

[0365] Synthesis of intermediate 5

[0366] Intermediate 5 was synthesized in the same manner as Intermediate 1. Intermediate 5 (27.5 g, 85% yield) was obtained as a colorless liquid using 5-bromoindole (15 g, 76.5 mmol).

[0367] Synthesis of intermediate 6

[0368] Intermediate 6 was synthesized in the same manner as Intermediate 2. Intermediate 6 (7.0 g, 30% yield) was obtained as a white solid using Intermediate 5 (25 g, 127 mmol).

[0369] Synthesis of intermediate 7

[0370] Intermediate 7 was synthesized in the same manner as Intermediate 3. Intermediate 7 (3.1 g, 43% yield) was obtained using Intermediate 6 (3.96 g, 10.95 mmol) and 3',5'-di-(tert-butyl)-3-chloro-4-formyl-[1,1'-biphenyl] (3.6 g, 10.95 mmol).

[0371] Synthesis of compound 3

[0372] Compound 3 was synthesized in the same manner as Compound 1. Intermediate 7 (2.12 g, 1.58 mmol) was used for synthesis to obtain Compound 3 (1.2 g, 60% yield) as a yellow solid. LC-MS: 1269 ([M] + ).

[0373] Synthesis Example 4

[0374] Compound 4 was synthesized according to the following scheme.

[0375]

[0376] Synthesis of intermediate 8

[0377] Intermediate 8 was synthesized in the same manner as Intermediate 3. Intermediate 8 (3.6 g, 40% yield) was obtained using Intermediate 6 (2.7 g, 7.6 mmol) and 3-chloro-5,5,8,8-tetramethyl-2-formyl-5,6,7,8-tetrahydronaphthalene (1.9 g, 7.6 mmol).

[0378] Synthesis of compound 4

[0379] Compound 4 was synthesized in the same manner as Compound 1. Intermediate 8 (3.0 g, 2.5 mmol) was used to carry out the reaction to obtain Compound 4 (1.9 g, 68% yield) as a yellow solid. LC-MS: 1114 ([M+H] + ).

[0380] Emission spectrum of solution

[0381] Measurement method

[0382] The fluorescence spectrophotometer F-7000 manufactured by Hitachi High-Tech Co., Ltd. was used at room temperature with an excitation wavelength of 320 nm and a 1×10 -7 The fluorescence spectrum of photoluminescence (PL) was obtained from a toluene solution with a concentration of 1:1 M. The peak wavelength and the emission spectrum width were determined from the measured emission spectrum. The wavelength at which the emission intensity in the emission spectrum is the maximum value is defined as the "peak emission wavelength", the wavelength width corresponding to half of the maximum value of the emission intensity is defined as the "half width (FWHM)", and the wavelength width corresponding to one quarter of the maximum value of the emission intensity is defined as the "quarter width (FWQM)".

[0383] In addition, in this evaluation, the peak emission wavelength may be in a blue emission region, and may be about 454 nm to about 475 nm.

[0384] In this evaluation, it is considered that the smaller the emission spectrum width (FWHM and FWQM), the better the color purity.

[0385] Table 1 provides the peak emission wavelength (nm) and emission spectrum width (FWHM and FWQM) of the emission spectrum of each of Compounds 1 to 4 and Comparative Compound C1 in a toluene solution used for the above-mentioned measurement method.

[0386] In addition, the emission spectra of compound 1 and comparative compound C1 used in the above measurement method in toluene solution are shown in Figure 4 middle.

[0387] Table 1. Emission spectra in toluene solution

[0388]

[0389]

[0390] As shown in Table 1, the peak emission wavelengths of compounds 1 to 4 of the present disclosure are 454 nm to 460 nm, indicating blue emission. In addition, the FWQM of compounds 1 to 4 is 17 nm to 22 nm, which is 13 nm to 18 nm smaller than the FWQM of comparative compound C1. These results are considered to be due to the fact that the intensity of the second emission peak is suppressed by the effect of the substituent W (tri-tert-butylphenyl) introduced into compounds 1 to 4. Figure 4 As shown in the emission spectrum of , the peak of the emission spectrum of Compound 1 of the present disclosure has a longer wavelength than that of Comparative Compound C1, making it suitable for blue emission.

[0391] Film properties

[0392] Method for manufacturing thin film

[0393] The compounds shown in Tables 2 and 3 were -5 A thin film having a thickness of 50 nm (hereinafter referred to as a "host dispersion film") was co-deposited with the host compound at a weight ratio of 1 wt % relative to the host compound on a quartz substrate under a vacuum pressure of 100 Pascals (Pa). Compound HT1 and compound HT2 were used as host compounds, and the weight ratio was set to compound HT1:compound HT2=60:40. In addition, the structures of HT1 and HT2 are as follows.

[0394]

[0395] Photoluminescence (PL) measurements

[0396] The film (main dispersion film) produced using the compound in Table 2 was cut into a strip shape having a width of 6 millimeters (mm) and subjected to PL measurement at room temperature using a fluorescence spectrophotometer F-7000 manufactured by Hitachi High-Tech Co., Ltd. From the obtained emission spectrum, the peak wavelength (maximum emission wavelength) and the wavelength width (FWHM) at which the emission intensity is halved were calculated. These evaluation results are shown in Table 2.

[0397] In addition, the emission spectra of the thin films (host dispersion films) prepared using Compound 1 and Comparative Compound C1 are shown in Figure 5 middle.

[0398] Table 2. Emission spectra in bulk dispersed films

[0399]

[0400] The peak emission wavelengths of compounds 1 and 2 of the film are 459nm and 466nm, respectively, indicating blue emission as for the emission spectrum of toluene solution. In addition, the FWHM of the film emission spectrum of compounds 1 and 2 of the present disclosure is 17nm and 19nm, respectively, and the difference between it and the FWHM of the emission spectrum in toluene solution is less than the difference of the FWHM of the emission spectrum in toluene solution of the comparison compound C1 in the film relative to the comparison compound C1. These results are considered to be due to the newly introduced spatially bulky substituent W effectively suppressing the intermolecular aggregation in the main dispersion state, and the compounds 1 and 2 of the present disclosure can reduce the increase of FWHM. At the same time, the comparison compound C1 has a peak emission wavelength of 457nm (indicating blue emission), a large FWHM of 24nm, and an emission spectrum shape for the film different from the emission spectrum in toluene solution. The observed effect is assumed to be because the comparison compound C1 is a planar molecule, resulting in aggregation between the molecules of the comparison compound C1, resulting in an increase in FWHM.

[0401] Measurement of Photoluminescence Quantum Yield (PLQY)

[0402] For the thin films (mass dispersion films) produced using the compounds in Table 3, PLQY was measured using Quantaurus-QY absolute PLQY measurement equipment C11347-01 manufactured by Hamamatsu Photonics Co., Ltd. The excitation wavelength was measured by scanning at intervals of 10 nm from 280 nm to 350 nm, and the following excitation wavelength region was adopted: where the compound absorption value provided an excitation light intensity ratio of 20% or more. The value of PLQY was taken as the highest value in the adopted excitation wavelength region. These evaluation results are shown in Table 3.

[0403] Table 3. Quantum yields in bulk dispersed films

[0404]

[0405] As shown in Table 3, Compound 1 of the present disclosure has a PLQY that is 13% greater than that of Comparative Compound C1. In addition, it can be confirmed that Compound 1 has a significantly greater PLQY than that of Comparative Compound C4, which has a di-tert-butylphenyl group as a bulky substituent instead of the substituent W (tri-tert-butylphenyl group). Therefore, it is believed that the aggregation inhibition effect due to the substituent W (tri-tert-butylphenyl group) provides improved PLQY, and Compound 1 can be used as a superior light-emitting dopant.

[0406] Evaluation of OLED devices

[0407] Fabrication of organic EL devices

[0408] Preparation of materials for forming each layer

[0409] As materials for forming each layer of the organic EL device, the following materials were prepared in addition to the obtained Compound 1, Compound 2, and Comparative Compound C1.

[0410]

[0411] Fabrication of organic EL devices1

[0412] Example 1

[0413] The glass substrate of ITO electrode patterning is cut into the size of 50mm×50mm×0.7mm, with acetone, isopropanol, and pure water in the order of this statement ultrasonic treatment, each 15 minutes, then by being exposed to UV ozone and cleaning 30 minutes.By using vacuum deposition equipment, the following layers are deposited on the ITO electrode (anode) of described glass substrate.

[0414] First, HAT-CN was deposited on the ITO electrode to form a hole injection layer with a thickness of 10 nm. Next, compound HT3 was deposited on the hole injection layer to form a hole transport layer with a thickness of 140 nm. Then, compound HT1 was deposited on the hole transport layer to form an electron blocking layer with a thickness of 5 nm. As a result, a hole transport region was formed.

[0415] The compound HT1, compound HT2, and compound 1 obtained above are co-deposited on the hole transport region obtained above to form an emission layer having a thickness of 40 nm. At this point, the formation of the emission layer is performed so that the weight ratio of compound HT1 and compound HT2 in the emission layer is set to compound HT1: compound HT2 = 60: 40. In addition, the formation of the emission layer is performed so that the concentration of compound 1 is set to 1.5 wt % based on the total weight of compound HT1, compound HT2, and compound 1 (i.e., the total weight of the emission layer). In addition, compound HT1 and compound HT2 are main materials.

[0416] Compound HT2 was vacuum deposited on the emission layer obtained above to form a hole blocking layer with a thickness of 5 nm. Next, compound H91 and LiQ were co-deposited on the hole blocking layer at a weight ratio of compound H91:LiQ=5:5 (unit: weight parts) to form an electron transport layer with a thickness of 30 nm. Then, LiQ was deposited on the electron transport layer to form an electron injection layer with a thickness of 1 nm. As a result, an electron transport region was formed.

[0417] Aluminum (cathode) having a thickness of 100 nm was deposited on the electron injection layer obtained above to thereby manufacture an organic EL device.

[0418] Then, in a glove box under a nitrogen atmosphere with a moisture concentration of 1 ppm or less and an oxygen concentration of 1 ppm or less, the organic EL device manufactured in the above process is sealed with a glass sealing tube having a desiccant and an ultraviolet curing resin (manufactured by MORESCO, product name WB90US). As a result, the manufacture of the organic EL device is completed.

[0419] Example 2

[0420] An organic EL device was fabricated and sealed in the same manner as in Example 1 to prepare an organic EL device, except that Compound 2 was used instead of Compound 1 in the emission layer during the formation of the emission layer in Example 1.

[0421] Comparative Example 1

[0422] An organic EL device was fabricated and sealed in the same manner as in Example 1 to prepare a completed organic EL device, except that during the formation of the emission layer of Example 1, Comparative Compound C1 was used instead of Compound 1 in the emission layer.

[0423] Manufacturing of organic EL devices2

[0424] Example 3

[0425] The glass substrate of ITO electrode patterning is cut into the size of 50mm×50mm×0.7mm, with acetone, isopropanol, and pure water in the order of this statement ultrasonic treatment, each 15 minutes, then by being exposed to UV ozone and cleaning 30 minutes.By using vacuum deposition equipment, the following layers are deposited on the ITO electrode (anode) of described glass substrate.

[0426] First, HAT-CN was deposited on the ITO electrode to form a hole injection layer with a thickness of 10 nm. Next, compound HT3 was deposited on the hole injection layer to form a hole transport layer with a thickness of 140 nm. Then, compound HT1 was deposited on the hole transport layer to form an electron blocking layer with a thickness of 5 nm. As a result, a hole transport region was formed.

[0427] The compound HT1, compound HT2, phosphorescent complex P1, and compound 1 obtained above are co-deposited on the hole transport region obtained above to form an emission layer having a thickness of 40 nm. At this point, the formation of the emission layer is performed so that the weight ratio of the compound HT1, compound HT2, and phosphorescent complex P1 in the emission layer is set to compound HT1: compound HT2: phosphorescent complex P1 = 60: 40: 13. In addition, the formation of the emission layer is performed so that the concentration of compound 1 is set to 0.4 wt % based on the total weight of compound HT1, compound HT2, phosphorescent complex P1, and compound 1 (i.e., the total weight of the emission layer). In addition, compound HT1 and compound HT2 are host materials.

[0428] Compound HT2 was vacuum deposited on the emission layer obtained above to form a hole blocking layer with a thickness of 5 nm. Next, compound H91 and LiQ were co-deposited on the hole blocking layer at a weight ratio of compound H91:LiQ=5:5 (unit: weight parts) to form an electron transport layer with a thickness of 30 nm. Then, LiQ was deposited on the electron transport layer to form an electron injection layer with a thickness of 1 nm. As a result, an electron transport region was formed.

[0429] Aluminum (cathode) having a thickness of 100 nm was deposited on the electron injection layer obtained above to thereby manufacture an organic EL device.

[0430] Then, in a glove box under a nitrogen atmosphere with a moisture concentration of 1 ppm or less and an oxygen concentration of 1 ppm or less, the organic EL device manufactured in the above process is sealed with a glass sealing tube having a desiccant and an ultraviolet curing resin (manufactured by MORESCO, product name WB90US). As a result, the manufacture of the organic EL device is completed.

[0431] Example 4

[0432] An organic EL device was manufactured and sealed in the same manner as in Example 3, except that Compound 2 was used instead of Compound 1 in the emission layer during the formation of the emission layer in Example 3 to complete the organic EL device.

[0433] Comparative Example 2

[0434] An organic EL device was manufactured and sealed in the same manner as in Example 3 to complete an organic EL device, except that during the formation of the emission layer of Example 3, Comparative Compound C1 was used instead of Compound 1 in the emission layer.

[0435] Evaluation of organic EL devices

[0436] For each of the organic EL devices of Examples 1 to 4 and Comparative Examples 1 and 2, the peak emission wavelength, the emission spectrum width (FWHM), and the emission intensity at 1,000 candela / m2 (cd / m 2 ) at a brightness of .

[0437] External quantum efficiency

[0438] A DC constant voltage power supply (Light Source Meter 2400 manufactured by KEITHLEY) was used to allow each organic EL device to emit light while changing the voltage applied to it, and a brightness measuring device (Multi-channel spectrometer PMA12 manufactured by Hamamatsu Photonics Co., Ltd.) was used to measure the brightness, emission spectrum, and luminous intensity at this time.

[0439] At this point, the external quantum efficiency was calculated from the emission spectrum, luminance, and current value at the time of measurement. 2 The external quantum efficiency at a brightness of is defined as EQE [%].

[0440] Peak emission wavelength and emission spectrum width (FWHM)

[0441] The peak emission wavelength and the emission spectrum width are determined from the measured emission spectrum.

[0442] In addition, in this evaluation, the peak emission wavelength may be in a blue emission region, and may be about 454 nm to about 475 nm.

[0443] In this evaluation, it is considered that the smaller the emission spectrum width (FWHM), the better the color purity.

[0444] The results of evaluating the organic EL devices of Examples 1 to 4 and Comparative Examples 1 and 2 are shown in Tables 4 and 5.

[0445] Table 4. Evaluation of organic EL device (Manufacture 1)

[0446]

[0447] ※External quantum efficiency (EQE) is a relative value when the value of Comparative Example 1 is set to 1.

[0448] Table 5. Evaluation of organic EL device (Manufacture 2)

[0449]

[0450] ※External quantum efficiency (EQE) is a relative value when the value of Comparative Example 2 is set to 1.

[0451] The organic EL devices manufactured using compounds 1 and 2 of the present disclosure as light-emitting materials each have an external quantum efficiency greater than that of the organic EL devices manufactured using comparative compound C1 as light-emitting materials. It is believed that the sterically bulky substituents in the compounds of the present disclosure contribute to the efficiency improvement by suppressing aggregation. In addition, the FWHM of each of Examples 1 to 4 is less than that of the corresponding Comparative Example 1 or 2, and thus the compounds of the present disclosure can be used as excellent light-emitting dopants.

[0452] As described above, it is observed that in the organic EL devices of Examples 1 to 4 including the compounds according to the present disclosure, the FWHM of the emission spectrum is narrow, luminescence with high color purity is achieved, and the external quantum efficiency is also excellent. In other words, compared with devices using conventional luminescent materials, the use of the compounds of the present disclosure as luminescent materials can manufacture blue electroluminescent devices with narrower spectral width, higher performance, higher efficiency, and higher color purity.

[0453] In this way, the compound according to the present disclosure presents an accurately adjusted blue emission color, excellent color purity, and high luminous efficiency in an organic EL device. In addition, in particular, when the compound according to the present disclosure is used in combination with a phosphorescent material, a significant improvement in luminous efficiency is shown. It is believed that these results fully meet the specifications required for future wide color gamut devices such as BT2100, making it possible to achieve high-precision next-generation displays.

[0454] According to one aspect of the present disclosure, a compound having a peak wavelength in an emission spectrum in a blue wavelength region and capable of providing luminescence with high color purity and high efficiency can be prepared. In addition, according to another aspect of the present disclosure, an organic electroluminescent device including the compound can be provided. In addition, according to another aspect of the present disclosure, a means for obtaining a peak wavelength in an emission spectrum in a blue wavelength region and high color purity and high efficiency luminescence in an organic electroluminescent device can be provided.

[0455] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for limiting purposes. The description of features or aspects in each embodiment should typically be considered to be applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those of ordinary skill in the art that various changes in form and detail may be made therein without departing from the spirit and scope as defined by the appended claims.

Claims

1. A compound represented by formula (1): in, In formula (1), R 1 To R 16 At least one of them is a substituent W represented by formula (2), wherein * represents a bonding site with the benzene ring in formula (1): as well as R other than the substituent W 1 To R 16 Each is independently any one atom or group of (a1) to (a10): (a1) hydrogen or deuterium atoms; (a2) halogen atoms; (a3) cyano; (a4) a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; (a5) a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; (a6) a substituted or unsubstituted arylamino group having 6 to 20 carbon atoms; (a7) a substituted or unsubstituted triarylsilyl group, an alkyldiarylsilyl group, a dialkylarylsilyl group, or a trialkylsilyl group, wherein the aryl group is an aryl group having 6 to 20 carbon atoms, and the alkyl group is an alkyl group having 1 to 20 carbon atoms; (a8) a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms; (a9) a substituted or unsubstituted heterocyclic group having 3 to 30 ring atoms; and (a10) a substituted or unsubstituted saturated hydrocarbon group or a saturated heterocyclic group, each of which is bonded to R 1 To R 16 The ring is formed by two adjacent groups in the ring and has 5 to 9 ring atoms.

2. The compound according to claim 1, wherein R 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 , and R 15 At least two of them are each a substituent W.

3. The compound according to claim 1, wherein R 2 and R 10 ; R 3 and R 11 ; R 6 and R 14 ; or R 7 and R 15 The combination of each is a substituent W.

4. The compound according to claim 1, wherein R other than the substituent W 1 To R 16 Each is independently an atom or group of (a1), (a4), (a7), (a8) or (a10).

5. The compound according to claim 1, wherein R other than the substituent W 1 To R 16 comprising at least one group selected from Group X: Group X in, In the at least one group selected from Group X, * represents the binding site to the benzene ring of formula (1), and The group with two * is bonded to R 1 To R 16 Two adjacent positions in the ring and are fused with the benzene ring to form a fused ring.

6. The compound according to claim 5, wherein R 1 To R 4 At least one of R 9 To R 12 at least one of each is a substituent W, and R 5 To R 8 At least one of R 13 To R 16 At least one of each is a group selected from Group X.

7. The compound according to claim 1, wherein R other than the substituent W 1 To R 16 comprising at least one group selected from Group Y: Group 2 in, In the at least one group selected from Group Y, * represents the binding site to the benzene ring of formula (1), and The group with two * is bonded to R 1 To R 16 Two adjacent positions in the ring and are fused with the benzene ring to form a fused ring.

8. The compound according to claim 7, wherein R 1 To R 4 At least one of R 9 To R 12 At least one of each is a substituent W, and R 5 To R 8 At least one of R 13 To R 16 At least one of each is a group selected from Group Y.

9. The compound according to claim 1, wherein the compound represented by formula (1) is represented by any one of compounds (100) to (117):

10. An organic electroluminescent device comprising an emission layer comprising a compound according to any one of claims 1 to 9. The organic electroluminescent device according to claim 10 , wherein the emission layer further comprises a phosphorescent complex. 12 . The organic electroluminescent device according to claim 11 , wherein the phosphorescent complex is a platinum complex.

13. The organic electroluminescent device according to claim 11, wherein the phosphorescent complex is a compound having a structure represented by formula (4): Wherein M in formula (4) is a metal ion having a coordination number of 4, R 41 , R 42 , R 43 , and R 44 are each independently a substituted or unsubstituted hydrocarbon cyclic group, or a substituted or unsubstituted heterocyclic group, L 41 To connect R 41 and R 42 The connecting group L 42 To connect R 42 and R 43 A linking group, and L 43 To connect R 43 and R 44 of the connecting group. The organic electroluminescent device according to claim 10 , wherein the emission layer further comprises a host material. 15 . The organic electroluminescent device according to claim 14 , wherein the host material comprises a compound having a carbazole ring structure, or a compound having a ring structure in which at least one ring-forming carbon atom of the carbazole ring is replaced by a nitrogen atom.

16. The organic electroluminescent device according to claim 15, wherein the host material comprises a compound having a structure represented by formula (5): in, In formula (5), Z 51 CH, CR 51 , or N, Z 52 CH, CR 52 , or N, Z 53 CH, CR 53 , or N, Z 54 CH, CR 54 , or N, Z 55 CH, CR 55 , or N, Z 56 CH, CR 56 , or N, Z 57 CH, CR 57 , or N, Z 58 CH, CR 58 , or N, R 51 To R 58 Each group is independently any one of (5a) to (5h): (5a) cyano; (5b) a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; (5c) a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; (5d) a substituted or unsubstituted arylamino group having 6 to 20 carbon atoms; (5e) substituted or unsubstituted phosphoryl; (5f) a substituted or unsubstituted silyl group; (5g) a substituted or unsubstituted monovalent aromatic hydrocarbon group; and (5h) a substituted or unsubstituted monovalent heterocyclic group, Ar 51 is a group including at least one of an aromatic hydrocarbon group and a heterocyclic group, and m is 1, 2, 3, 4, 5, or 6, Where R 51 and R 52 , R 52 and R 53 , R 53 and R 54 , R 55 and R 56 , R 56 and R 57 , R 57 and R 58 , or a combination thereof are optionally bonded to each other to form an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, or a heterocyclic ring each including the bonded carbon atoms. 17 . The organic electroluminescent device according to claim 14 , wherein the host material comprises a compound having a triazine ring structure.

18. The organic electroluminescent device according to claim 17, wherein the host material comprises a compound having a structure represented by formula (6): in, In formula (6), Ar 61 To Ar 63 Each is independently a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent heterocyclic group.

19. The organic electroluminescent device according to claim 14, wherein the compound is the dopant material.

20. A method for synthesizing a compound according to any one of claims 1 to 9, The method comprises introducing a substituent W represented by formula (2) into R in formula (1) by using a Negishi coupling reaction. 1 To R 16 at least one of .

Images