KR20210006283A - A plurality of host materials and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to multiple host materials and an organic electroluminescence element including the same. According to the present invention, by comprising the host materials, the organic electroluminescence element having high power efficiency and/or long lifespan characteristics can be manufactured.

Description

A plurality of host materials and an organic electroluminescent device including the same TECHNICAL FIELD {A PLURALITY OF HOST MATERIALS AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME}

The present application relates to a plurality of host materials and an organic electroluminescent device comprising the same.

An electroluminescent device (EL device) is a self-luminous display device and has an advantage in that it has a wide viewing angle, excellent contrast, and fast response speed. In 1987, Eastman Kodak Co., Ltd. first developed an organic EL device using a low-molecular aromatic diamine and aluminum complex as a material for forming a light emitting layer [see Appl. Phys. Lett. 51, 913, 1987].

The light-emitting material of the organic electroluminescent device is the most important factor in determining the luminous efficiency of the device. The light-emitting material must have high quantum efficiency and high mobility of electrons and holes, and the formed light-emitting material layer must be uniform and stable. The light emitting material may be classified into a host material and a dopant material in terms of functionality, and a host and a dopant may be mixed and used to improve color purity, luminous efficiency, and stability. Desirable properties of the host material serving as a solid solvent and an energy carrier must be of high purity and have an appropriate molecular weight to enable vacuum deposition. In addition, thermal stability must be secured due to high glass transition temperature and thermal decomposition temperature, high electrochemical stability is required for long life, easy to form amorphous thin film, and good adhesion to materials of other adjacent layers, while interlayer It is desirable not to move. When using such a dopant/host material system, the host material has a great influence on the efficiency and lifespan of the light emitting device, so the selection is important.

Until now, various compounds have been known as such host materials, but in the case of an organic electroluminescent device using a conventionally known material, there has been a demand for a new material due to high driving voltage, low efficiency, and short lifespan. Accordingly, there is a need to develop a host material that enables the implementation of an organic electroluminescent device having excellent lifetime characteristics even at low voltage driving and high luminance.

Korean Patent Application Publication No. 2019-0013353 discloses an organic optoelectronic device in which a compound having a benzonaphtho-based heteroaryl moiety as a basic skeleton as a host of a light emitting layer is used with a compound having a carbazole-carbazole moiety. As described above, a plurality of host materials used together with a compound having a phenanthro-based heteroaryl moiety as a basic skeleton is not disclosed.

Korean Patent Application Publication No. 2019-0013353 (published on February 11, 2019)

An object of the present invention is to firstly provide a plurality of host materials capable of manufacturing an organic electroluminescent device having high power efficiency and/or long life characteristics, and secondly, an organic electroluminescent device comprising the host material Is to provide.

As a result of intensive research to solve the above technical problem, the present inventors have found a plurality of species including a first host material including a compound represented by the following formula (1) and a second host material including a compound represented by the following formula (2). The present invention was completed by finding that the host material of achieves the above object.

[Formula 1]

In Formula 1,

Y ₁ is O, S, CR ₁₁ R ₁₂ , or NR ₁₃ ;

R ₁₁ to R ₁₃ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted ( C3-C30)cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl, or ; R ₁₁ and R ₁₂ may be linked to each other to form a ring;

R ₁ to R ₃ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3 -30 membered) Heteroaryl, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30) ) Alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted (C1 -C30) alkyl (C6-C30) arylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, substituted or unsubstituted mono- or di- (3-30 membered) heteroarylamino, Or a substituted or unsubstituted (C6-C30) aryl (3-30 membered) heteroarylamino; Adjacent substituents may be linked to each other to form a ring;

Provided that at least one of R ₁₃ , R ₂ , and R ₃ is -L ₁ -(Ar ₁ ) _d ;

L ₁ is a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene;

Each Ar ₁ is independently a substituted or unsubstituted (3-30 membered) heteroaryl containing at least one nitrogen (N);

a and c are each independently an integer of 1 to 4, b and d are an integer of 1 or 2;

When a to d are integers of 2 or more, each R ₁ , each R ₂ , each R ₃ , and each Ar ₁ may be the same as or different from each other;

[Formula 2]

In Chemical Formula 2,

X ₂₁ and Y ₂₁ are each independently -N=, -NR ₂₄ -, -O-, or -S-, provided that any one of X ₂₁ and Y ₂₁ is -N=, and X ₂₁ and Y ₂₁ The other is -NR ₂₄ -, -O-, or -S-;

R ₂₁ is substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered) heteroaryl;

R ₂₂ to R ₂₄ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3 -30 membered) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted Substituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, A substituted or unsubstituted (C3-C30) aliphatic ring and a fused ring group of (C6-C30) aromatic ring, substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted Mono- or di- (C6-C30) arylamino, substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino, substituted or unsubstituted mono- or di- (3-30 membered) heteroaryl Amino, or a substituted or unsubstituted (C6-C30)aryl (3-30 membered) heteroarylamino; May be linked with adjacent substituents to form a ring;

Provided that at least one of R ₂₂ and R ₂₃ is -L ₂₁ -Ar ₂₁ ;

L ₂₁ is a single bond or a substituted or unsubstituted (C6-C30)arylene;

Ar ₂₁ is substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic Fused ring group of the ring, substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, substituted or unsubstituted (C1- C30) alkyl (C6-C30) arylamino, substituted or unsubstituted mono- or di- (3-30 membered) heteroarylamino, or substituted or unsubstituted (C6-C30) aryl (3-30 membered) hetero Arylamino;

f is an integer of 1 or 2, g is an integer of 1 to 4;

When f and g are integers of 2 or more, each R ₂₂ and each R ₂₃ may be the same or different from each other.

By using a plurality of host materials according to the present invention, it is possible to manufacture an organic electroluminescent device having high power efficiency and/or long life characteristics.

Hereinafter, the present application will be described in more detail, but this is for the purpose of explanation and should not be construed as a way to limit the scope of the present application.

The present application provides a plurality of host materials and the host material including at least one first host material including the compound represented by Formula 1 and at least one second host material including the compound represented by Formula 2 It relates to an organic electroluminescent device comprising.

As used herein, "organic electroluminescent material" refers to a material that can be used for an organic electroluminescent device, may include one or more compounds, and may be included in any layer constituting the organic electroluminescent device, if necessary. For example, the organic electroluminescent material is a hole injection material, a hole transport material, a hole auxiliary material, a light emission auxiliary material, an electron blocking material, a light emitting material (including a host material and a dopant material), an electron buffer material, a hole blocking material, It may be an electron transport material, an electron injection material, or the like.

As used herein, "plural kinds of host material" means a host material including a combination of two or more compounds that can be included in any light emitting layer constituting the organic electroluminescent device, and before being included in the organic electroluminescent device (for example, For example, it may mean both materials before deposition) and after being included (eg, after deposition). For example, the plurality of host materials of the present application is a combination of two or more host materials, and optionally, may further include a conventional material included in the organic electroluminescent material. Two or more types of compounds included in the plurality of host materials of the present application may be included together in one emission layer or may be included in different emission layers through a method used in the art. For example, the two or more compounds may be deposited together or co-deposited, or separately deposited.

As used herein, the "hole transport zone" refers to a region in which holes move between the first electrode and the light emitting layer, for example, at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, and an electron blocking layer. Can include. Each of the hole injection layer, the hole transport layer, the hole auxiliary layer, the light emission auxiliary layer, and the electron blocking layer may be a single layer or a plurality of layers in which two or more layers are stacked. According to an example of the present application, the hole transport zone may include a first hole transport layer and a second hole transport layer. The second hole transport layer may be at least one of a plurality of hole transport layers, and may include at least one of a hole auxiliary layer, a light emission auxiliary layer, and an electron blocking layer. In addition, according to another example of the present application, the hole transport zone includes a first hole transport layer and a second hole transport layer, the first hole transport layer may be located between the first electrode and the light emitting layer, the The second hole transport layer may be located between the first hole transport layer and the emission layer, and the second hole transport layer may be a layer serving as a hole transport layer, a light emission auxiliary layer, a hole auxiliary layer, and/or an electron blocking layer. .

As used herein, "(C1-C30)alkyl" refers to a straight or branched chain alkyl having 1 to 30 carbon atoms constituting a chain, wherein the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. . Specific examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert -butyl. As used herein, "(C3-C30)cycloalkyl" refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, and preferably 3 to 20 carbon atoms, and more preferably 3 to 7 carbon atoms. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. As used herein, "(C3-C30)cycloalkenyl" is a monocyclic or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, which means containing a double bond in the ring skeleton, and preferably 3 to 20 carbon atoms And 3 to 7 are more preferable. Examples of the cycloalkenyl include cyclopropenyl, cyclobutenyl, and cyclopentenyl. As used herein, "(3-7 membered) heterocycloalkyl" has 3 to 7, preferably 5 to 7 ring skeleton atoms, and the group consisting of B, N, O, S, Si and P, preferably O , S and N means a cycloalkyl containing one or more heteroatoms selected from the group consisting of, for example, tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, and the like. As used herein, "(C6-C30)aryl (ene)" refers to a monocyclic or fused cyclic radical derived from an aromatic hydrocarbon having 6 to 30 ring skeleton carbon atoms, and may be partially saturated, and includes a spiro structure. The number of ring skeleton carbon atoms is preferably 6 to 20, more preferably 6 to 15. As an example of the aryl, specifically, phenyl, biphenyl, terphenyl, quarterphenyl, naphthyl, binapthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, di Phenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthrenyl, benzophenanthrenyl, phenylphenanthrenyl, anthracenyl, benzanthracenyl, indenyl, triphenylenyl , Pyrenyl, tetracenyl, perylenyl, chrysenyl, benzochrycenyl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, cumenyl ( cumenyl) spiro[fluorene-fluoren]yl (spirobifluorenyl), spiro[fluorene-benzofluoren]yl, azulenyl, and the like. More specifically, the aryl is o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-kumenyl Menyl, p-cumenyl, pt-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-t-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl , p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluore Nyl, 4-fluorenyl, 9-fluorenyl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl , 9,9-diphenyl-4-fluorenyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9 -Phenanthryl, 1-Chrysenyl, 2-Chrycenyl, 3-Chrycenyl, 4-Chrysenyl, 5-Chrycenyl, 6-Chrycenyl, benzo[c]phenanthryl, benzo[g]Chrycenyl, 1- Triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl In the present application, "(3-30 membered) heteroaryl (ene)" has 3 to 30 ring skeleton atoms, and one selected from the group consisting of B, N, O, S, Si, P, and Ge It means an aryl group containing more than one heteroatom, wherein the number of ring skeleton atoms is preferably 5 to 25. The number of heteroatoms is preferably 1 to 4, and is a monocyclic system or a fused ring system condensed with one or more benzene rings. In addition, the heteroaryl herein also includes a form in which one or more heteroaryl groups or aryl groups are linked to a heteroaryl group by a single bond, as an example of the heteroaryl, specifically, furyl. , Thiophenyl, Pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, Monocyclic heteroaryl such as pyrazinyl, pyrimidinyl, and pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl , Benzoisothiazolyl, benzoisoxazolyl, benzooxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, Quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazyl, phenanthridinyl, benzodioxolyl, indolizidine, acridinyl, silafluorenyl, ger Fused ring heteroaryl such as marflowenyl and the like. More specifically, the heteroaryl is 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazine-4-yl, 1,2,4-triazine-3-yl, 1,3,5-triazine-2-yl , 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizydinyl, 2-indorizidinyl, 3-indolizedinyl, 5-indolizedinyl, 6-indolizedinyl, 7- Indolizinyl, 8-indolizinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2 -Isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3 -Benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl , 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2- Quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazolyl-1-yl, aza Carbazolyl-2-yl, azacarbazolyl-3-yl, azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarbazolyl-6-yl, azacarbazolyl-7-yl, azacarbazolyl -8-yl, azacarbazolyl-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8 -Phenantridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxa Zolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrole-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrole- 5-yl, 2-t-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl -3-Indolyl, 4-methyl-3-indolyl, 2-t-butyl-1-indolyl, 4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl, 4- t-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl , 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl , 2-germafluorenyl, 3-germafluorenyl, and 4-germafluorenyl. In the present application, "the fused ring group of the aliphatic ring of (C3-C30) and the aromatic ring of (C6-C30)" refers to 3 to 30, preferably 3 to 25, more preferably 3 to 18 ring skeleton carbon atoms. It refers to a functional group of a ring in which at least one individual aliphatic ring and at least one aromatic ring having 6 to 30, preferably 6 to 25, more preferably 6 to 18 carbon atoms in the ring skeleton are fused. For example, a fused ring group of one or more benzene and one or more cyclohexane, or a fused ring group of one or more naphthalene and one or more cyclopentane, and the like may be mentioned. Herein, the carbon atom of the fused ring group of the aliphatic ring of (C3-C30) and the aromatic ring of (C6-C30) is at least one heteroatom selected from B, N, O, S, Si and P, preferably N, It may be replaced by one or more heteroatoms selected from O and S. “Halogen” herein includes F, Cl, Br and I atoms.

In addition, "ortho; o-)", "meta; m-)" and "para; p-)" mean the position of substitution of all substituents, and the ortho position means the position of the substituent. Represents a neighboring compound, for example, in the case of benzene, it means 1st and 2nd digits, and the meta position represents the next substitutional position of the immediate neighboring substitutional position, for example, in the case of benzene, it means 1st and 3rd digits, and para ( The para) position is the next substitution position of the meta position, for example, in the case of benzene, it means 1 or 4 digits.

As used herein, "a ring formed by linking with adjacent substituents" refers to a substituted or unsubstituted (3-30 membered) monocyclic or polycyclic alicyclic, aromatic or combination thereof formed by linking or fusion of two or more adjacent substituents. Means, and preferably, a substituted or unsubstituted (3-26 membered) monocyclic or polycyclic alicyclic, aromatic, or a combination thereof may be used. In addition, the formed ring may contain one or more heteroatoms selected from B, N, O, S, Si and P, preferably one or more heteroatoms selected from N, O and S. According to an example of the present application, the number of ring skeleton atoms is (5-20 members), and according to another example of the present application, the number of ring skeleton atoms is (5-15 members).

In addition, in the description of "substituted or unsubstituted" herein, "substituted" means that a hydrogen atom is replaced with another atom or another functional group (ie, a substituent) in a certain functional group. In the present application R ₁ to R ₄ , R ₁₁ to R ₁₃ , R ₂₁ to R ₂₆ , L ₁ , Ar ₁ , L ₂₁ , and Ar ₂₁ substituted (C1-C30)alkyl, substituted (C3-C30)cyclo Alkyl, substituted (C3-C30) cycloalkenyl, substituted (3-7 membered) heterocycloalkyl substituted (C6-C30) aryl (ene), substituted (3-30 membered) heteroaryl (ene), Substituted tri(C1-C30)alkylsilyl, substituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted tri(C6) -C30) arylsilyl, a fused ring group of a substituted (C3-C30) aliphatic ring and an aromatic ring of (C6-C30), a substituted mono- or di- (C1-C30) alkylamino, substituted (C1- C30) alkyl (C6-C30) arylamino, substituted mono- or di- (C6-C30) arylamino, substituted mono- or di- (3-30 membered) heteroarylamino, substituted (C6-C30) Aryl (3-30 membered) heteroarylamino, and the substituents of the substituted ring are each independently deuterium, halogen, cyano, carboxyl, nitro, hydroxy, (C1-C30)alkyl, halo (C1-C30) Alkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C3-C30)cycloalkyl, (C3-C30)cycloalkenyl, (3-7 member) heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, (5-30 member) heteroaryl unsubstituted or substituted with (C6-C30) aryl, (5- 30 membered) Heteroaryl substituted or unsubstituted (C6-C30)aryl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl , (C1-C30)alkyldi(C6-C30)arylsilyl, amino, mono- or di- (C1-C30)alkylamino, mono- or di-(C6) unsubstituted or substituted with (C1-C30)alkyl -C30) arylamino, (C1-C30) alkyl (C6-C30) arylamino, (C1-C30) alkylcarbonyl, (C1-C30) alkoxycarbonyl, (C6-C30) arylcarbonyl, Di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl, (C6-C30)ar(C1-C30)alkyl , And (C1-C30) alkyl (C6-C30) is preferably at least one selected from the group consisting of aryl, for example, the substituent is substituted or unsubstituted methyl, substituted or unsubstituted phenyl, substituted or unsubstituted Substituted naphthyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted benzofluorenyl , Substituted or unsubstituted triphenylenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted spiro[benzofluorene-fluoren]yl, substituted or unsubstituted Substituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted Substituted phenylbiphenylamino, substituted or unsubstituted phenylterphenylamino, substituted or unsubstituted naphthylphenylamino, substituted or unsubstituted naphthylbiphenylamino, substituted or unsubstituted naphthylterphenylamino, substituted or unsubstituted Substituted naphthylphenanthrenylamino, substituted or unsubstituted dibiphenylamino, substituted or unsubstituted difluorenylamino, substituted or unsubstituted biphenylfluorenylamino, or substituted or unsubstituted biphenyldi Benzofuranylamino and the like.

Hereinafter, a host material according to an embodiment will be described.

The plurality of host materials according to an embodiment includes a first host material including a compound represented by Formula 1 and a second host material including a compound represented by Formula 2, and the organic It may be included in the emission layer of the electroluminescent device.

The first host material, which is a host material according to an embodiment, may include a compound represented by Formula 1 below.

[Formula 1]

In Formula 1,

Y ₁ is O, S, CR ₁₁ R ₁₂ , or NR ₁₃ ;

R ₁₁ to R ₁₃ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted ( C3-C30)cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl, or ; R ₁₁ and R ₁₂ may be linked to each other to form a ring;

R ₁ to R ₃ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3 -30 membered) Heteroaryl, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30) ) Alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted (C1 -C30) alkyl (C6-C30) arylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, substituted or unsubstituted mono- or di- (3-30 membered) heteroarylamino, Or a substituted or unsubstituted (C6-C30) aryl (3-30 membered) heteroarylamino; Adjacent substituents may be linked to each other to form a ring;

Provided that at least one of R ₁₃ , R ₂ , and R ₃ is -L ₁ -(Ar ₁ ) _d ;

L ₁ is a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene;

Each Ar ₁ is independently a substituted or unsubstituted (3-30 membered) heteroaryl containing at least one nitrogen (N);

a and c are each independently an integer of 1 to 4, b and d are an integer of 1 or 2;

When a to d is an integer of 2 or more, each R ₁ , each R ₂ , each R ₃ , and each Ar ₁ may be the same or different from each other.

For example, Y ₁ is O, S, CR ₁₁ R ₁₂ , or NR ₁₃ , and R ₁₁ and R ₁₂ are each independently a substituted or unsubstituted (C1-C30)alkyl or a substituted or unsubstituted (C6- C30) aryl; Can be connected to each other to form a substituted or unsubstituted (3-30 membered) monocyclic or polycyclic alicyclic, aromatic ring, and R ₁₃ is substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted May be (3-30 membered) heteroaryl, and preferably, R ₁₁ and R ₁₂ are each independently a substituted or unsubstituted (C1-C10)alkyl or a substituted or unsubstituted (C6-C18)aryl Or; May be connected to each other to form a substituted or unsubstituted (5-30 membered) polycyclic aromatic ring, and R ₁₃ is a substituted or unsubstituted (C6-C25)aryl or a substituted or unsubstituted (5-30 membered) ) It may be heteroaryl. More preferably, R ₁₁ and R ₁₂ are each independently a substituted or unsubstituted (C1-C4)alkyl or a substituted or unsubstituted (C6-C12)aryl; May be connected to each other to form a substituted or unsubstituted (5-25 membered) polycyclic aromatic ring, and R ₁₃ is a substituted or unsubstituted (C6-C18)aryl or a substituted or unsubstituted (5-25 membered) ) It may be heteroaryl. For example, R ₁₁ and R ₁₂ are each independently substituted or unsubstituted methyl, substituted or unsubstituted phenyl; May be linked to each other to form a fluorene ring, R ₁₃ is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted p-biphenyl, It may be a substituted or unsubstituted fluorenyl, a substituted or unsubstituted phenanthrenyl, or a substituted or unsubstituted dibenzothiophenyl.

For example, R ₁ and R ₂ may each independently be hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl, preferably , Hydrogen, (C6-C25) aryl, or a substituted or unsubstituted (5-25 member) heteroaryl, more preferably, hydrogen, (C6-C18) aryl, or a substituted or unsubstituted (5 -18 won) It may be heteroaryl. For example, R ₁ and R ₂ are each independently substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted m-biphenyl, substituted Or unsubstituted p-biphenyl, substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted phenanthrenyl.

For example, R ₃ may each independently be hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl, preferably hydrogen, It may be a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5-25 membered) heteroaryl containing at least one nitrogen (N), and more preferably, hydrogen, substituted or unsubstituted It may be a substituted (C6-C18)aryl, or a substituted or unsubstituted (5-18 membered) heteroaryl containing at least two nitrogens (N). For example, R ₃ is each independently hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted triazinyl, substituted or unsubstituted Quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted quinazolinyl, or substituted or unsubstituted benzoquinazolinyl.

However, in Formula 1, at least one of R ₁₃ , R ₂ , and R ₃ is -L ₁ -(Ar ₁ ) _d ; L ₁ is a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene; Ar ₁ may each independently be a substituted or unsubstituted nitrogen-containing (3-30 membered) heteroaryl containing at least one nitrogen (N).

For example, at least one of R ₁₃ and R ₃ may be -L ₁ -(Ar ₁ ) _d , and preferably, R ₃ may be -L ₁ -(Ar ₁ ) _d .

For example, L ₁ may be a single bond or a substituted or unsubstituted (C6-C30) arylene, preferably, a single bond or a substituted or unsubstituted (C6-C25) arylene, and more preferably , It may be a single bond or a substituted or unsubstituted (C6-C18)arylene. For example, L ₁ is a single bond, or substituted or unsubstituted phenylene, substituted or unsubstituted o-biphenylene, substituted or unsubstituted m-biphenylene, substituted or unsubstituted naphthylene, substituted Or it may be unsubstituted phenylnaphthylene, or substituted or unsubstituted phenanthrenylene.

For example, Ar ₁ may each independently be a substituted or unsubstituted nitrogen-containing (5-25 membered) heteroaryl containing at least one nitrogen (N), and preferably, at least two nitrogens (N) It may be a substituted or unsubstituted nitrogen-containing (5-18 membered) heteroaryl including.

Ar ₁ according to an example is each independently substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyri Dazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted quinolyl, substituted Or unsubstituted benzoquinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted benzoisoquinolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted naphthyridi Nyl, or a substituted or unsubstituted benzothienopyrimidine, preferably, substituted or unsubstituted triazinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or It may be unsubstituted quinazolinyl, or substituted or unsubstituted benzoquinazolinyl. For example, substituted or unsubstituted (C6-C30) aryl and substituted or unsubstituted (5-30 membered) heteroaryl substituted or unsubstituted with at least one of, triazinyl, quinazolinyl, quinoxalinyl, benzo It may be quinazolinyl, or benzoquinoxalinyl.

The compound represented by Formula 1 may be represented by any one of Formulas 1-1 to 1-9 below.

[Formula 1-1] [Formula 1-2]

[Formula 1-3] [Formula 1-4]

[Formula 1-5] [Formula 1-6]

[Formula 1-7] [Formula 1-8]

[Formula 1-9]

In Formulas 1-1 to 1-9,

Y ₁ , L ₁ , Ar ₁ , R ₁ to R ₃ , and a to d are the same as defined in Formula 1;

Each R ₄ is independently the same as the definition of R ₃ ;

e is an integer of 1 to 3, and when e is an integer of 2 or more, each R ₄ may be the same or different.

For example, in Formula 1-1, Y ₁ is O, S, CR ₁₁ R ₁₂ , or NR ₁₃ ; R ₁ and R ₂ are each independently hydrogen, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl; L ₁ is a single bond or a substituted or unsubstituted (C6-C30)arylene; Ar ₁ is a substituted or unsubstituted (3-30 membered) heteroaryl containing at least 2 nitrogens; d may be 1.

For example, in Formulas 1-2 and 1-3, Y ₁ is O, S, CR ₁₁ R ₁₂ , or NR ₁₃ ; Both R ₁ and R ₂ are hydrogen; L ₁ is a single bond or a substituted or unsubstituted (C6-C30)arylene; Ar ₁ is a substituted or unsubstituted (3-30 membered) heteroaryl containing at least 2 nitrogens; d may be 1.

According to an example, the first host material may be exemplified as the following compound, but is not limited thereto.

The compound represented by Formula 1 according to the present application may be prepared as shown in Schemes 1 to 4 below, but is not limited thereto, and may be prepared by a synthetic method known to those skilled in the art.

[Scheme 1]

[Scheme 2]

[Scheme 3]

[Scheme 4]

The definition of each substituent in Reaction Schemes 1 to 4 is as defined in Chemical Formulas 1-1 to 1-9, and Hal means a halogen atom.

Exemplary synthesis examples for the compounds represented by Formula 1, specifically the compounds of Formulas 1-1 to 1-9, have been described above, but these are all Suzuki cross-coupling reaction, Wittig reaction, Miyaura borylation reaction, Ullmann reaction. , Buchwald-Hartwig cross coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, Intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, Cyclic Dehydration reaction, SN ₁ It is based on a substitution reaction, SN ₂ substitution reaction, and a phosphine-mediated reductive cyclization reaction, and those skilled in the art know that the reaction proceeds even if other substituents defined in Formulas 1-1 to 1-9 are bonded in addition to the substituents specified in the specific synthesis examples. It will be easy to understand.

Another host material according to an embodiment, the second host material may include a compound represented by Formula 2 below.

[Formula 2]

In Chemical Formula 2,

X ₂₁ and Y ₂₁ are each independently -N=, -NR ₂₄ -, -O-, or -S-, provided that any one of X ₂₁ and Y ₂₁ is -N=, and X ₂₁ and Y ₂₁ The other is -NR ₂₄ -, -O-, or -S-;

R ₂₁ is substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered) heteroaryl;

R ₂₂ to R ₂₄ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3 -30 membered) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted Substituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, A substituted or unsubstituted (C3-C30) aliphatic ring and a fused ring group of (C6-C30) aromatic ring, substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted Mono- or di- (C6-C30) arylamino, substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino, substituted or unsubstituted mono- or di- (3-30 membered) heteroaryl Amino, or a substituted or unsubstituted (C6-C30)aryl (3-30 membered) heteroarylamino; May be linked with adjacent substituents to form a ring;

Provided that at least one of R ₂₂ and R ₂₃ is -L ₂₁ -Ar ₂₁ ;

L ₂₁ is a single bond or a substituted or unsubstituted (C6-C30)arylene;

Ar ₂₁ is substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic Fused ring group of the ring, substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, substituted or unsubstituted (C1- C30) alkyl (C6-C30) arylamino, substituted or unsubstituted mono- or di- (3-30 membered) heteroarylamino, or substituted or unsubstituted (C6-C30) aryl (3-30 membered) hetero Arylamino;

f is an integer of 1 or 2, g is an integer of 1 to 4;

When f and g are integers of 2 or more, each R ₂₂ and each R ₂₃ may be the same or different from each other.

For example, when X ₂₁ is -N=, Y ₂₁ may be -O- or -S-, and when Y ₂₁ is -N=, X ₂₁ may be -O- or -S-.

For example, L ₂₁ may be a single bond or a substituted or unsubstituted (C6-C25) arylene, and preferably, a single bond or a substituted or unsubstituted (C6-C18) arylene. For example, L ₂₁ may be a single bond, substituted or unsubstituted phenylene, or substituted or unsubstituted naphthylene.

For example, Ar ₂₁ is a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 membered) heteroaryl, a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) ) Of an aromatic ring fused ring group, substituted or unsubstituted mono- or di- (C6-C30) arylamino, substituted or unsubstituted mono- or di- (3-30 membered) heteroarylamino, or substituted or It may be unsubstituted (C6-C30)aryl (3-30 membered) heteroarylamino, and preferably, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C5-C25) aliphatic A fused ring group of a ring and an aromatic ring of (C6-C25), a substituted or unsubstituted mono- or di- (C6-C25) arylamino, or a substituted or unsubstituted (C6-C25) aryl (5-25 membered ) Heteroarylamino may be, more preferably, a substituted or unsubstituted (C6-C30)aryl, a fused ring of a substituted or unsubstituted (C5-C18) aliphatic ring and an (C6-C18) aromatic ring A group, a substituted or unsubstituted di(C6-C18)arylamino, or a substituted or unsubstituted (C6-C18)aryl (5-18 member) heteroarylamino, wherein the di(C6-C30) At least one carbon of the arylamino may include one or more hetero atoms selected from the group consisting of N, O, and S. For example, Ar ₂₁ is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted p-ratio Phenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted phenanthrenyl, Substituted or unsubstituted chrysenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted Substituted spiro[cyclopentane-fluoren]yl, substituted or unsubstituted spiro[dihydroinden-fluoren]yl, substituted or unsubstituted spiro[benzofluorene-fluoren]yl, substituted or unsubstituted Substituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted dibenzocarbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzonaphtho Thiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, or substituted or unsubstituted benzonaphthofuranyl, or phenyl, naphthyl, naphthylphenyl, phenylnaphthyl, o -Biphenyl, m-biphenyl p-biphenyl, o-terphenyl, m-terphenyl, p-terphenyl, fluorenyl, benzofluorenyl, phenanthrenyl, benzonaphthofuranyl, dibenzothio It may be amino substituted with at least one of phenyl, and dibenzofuranyl, preferably, Ar ₂₁ is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted o-biphenyl, substituted Or unsubstituted m-biphenyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted p-terphenyl, substituted Or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted spiro[cyclopentane-fluoren]yl, substituted or unsubstituted Spiro[dihydroinden-fluoren]yl, substituted or unsubstituted spiro[benzofluorene- Fluoren]yl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted chrycenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted diphenylamino, substituted Or unsubstituted phenylbiphenylamino, substituted or unsubstituted phenylterphenylamino, substituted or unsubstituted naphthylphenylamino, substituted or unsubstituted naphthylbiphenylamino, substituted or unsubstituted naphthylterphenylamino, substituted Or unsubstituted naphthylphenanthrenylamino, substituted or unsubstituted dibiphenylamino, substituted or unsubstituted difluorenylamino, substituted or unsubstituted biphenylfluorenylamino, substituted or unsubstituted biphenyl Benzofluorenylamino, or substituted or unsubstituted biphenylbenzofluorenylamino; Naphthyl, p-biphenyl, m-biphenyl, o-biphenyl, terphenyl, phenanthrenyl, phenylnaphthyl, dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, and benzonaphthofuranyl It may be amino substituted with two substituents selected from, in this case, at least one of the substituents of the amino group may be dibenzofuranyl or dibenzothiophenyl.

For example, R ₂₁ may be a substituted or unsubstituted (C6-C30)aryl, preferably, a substituted or unsubstituted (C6-C25)aryl, and more preferably a substituted or unsubstituted ( It may be C6-C18)aryl. For example, R ₂₁ may be substituted or unsubstituted phenyl or substituted or unsubstituted p-biphenyl.

For example, R ₂₂ to R ₂₄ may each independently be hydrogen, deuterium, halogen, or cyano, and preferably hydrogen or deuterium. For example, all of R ₂₂ to R ₂₄ may be hydrogen.

The compound represented by Formula 2 may be represented by any one of Formulas 2-1 to 2-5 below.

[Formula 2-1] [Formula 2-2]

[Formula 2-3] [Formula 2-4]

[Formula 2-5]

In Formulas 2-1 to 2-5,

X ₂₁ , Y ₂₁ , L ₂₁ , Ar ₂₁ , R ₂₁ to R ₂₃ , f, and g are the same as defined in Formula 2;

R ₂₅ and R ₂₆ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3 -30 membered) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted Substituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, Substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono-or di-(C6-C30)arylamino, substituted or unsubstituted (C1-C30)alkyl(C6- C30) arylamino, substituted or unsubstituted mono- or di- (3-30 membered) heteroarylamino, or substituted or unsubstituted (C6-C30) aryl (3-30 membered) heteroarylamino; May be linked with adjacent substituents to form a ring;

g'is an integer of 1 or 2, h and i are each independently an integer of 1 to 3, and i'is an integer of 1 to 4;

When g', h, and i are integers of 2 or more, each R ₂₃ , each R ₂₅ , and each R ₂₆ may be the same or different from each other.

For example, in Formulas 2-1 to 2-5, any one of X ₂₁ and Y ₂₁ is -N=, and the other of X ₂₁ and Y ₂₁ is -O- or -S-; L ₂₁ is a single bond or a substituted or unsubstituted (C6-C30)arylene; Ar ₂₁ is substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted di(C6-C30)arylamino; R ₂₁ is substituted or unsubstituted (C6-C30)aryl; All of R ₂₂ to R ₂₄ may be hydrogen.

According to an example, the second host material may be exemplified as the following compound, but is not limited thereto.

The compound of Formula 2 according to the present application may be prepared by a synthesis method known to those skilled in the art, and in particular, a synthesis method disclosed in a number of patent documents may be used. For example, it may be synthesized with reference to the method disclosed in Korean Patent Publication No. 2017-0022865 (published on March 2, 2017), but is not limited thereto.

According to another embodiment, the present application provides an organic electroluminescent compound represented by the following formula 3-1.

[Formula 3-1]

In Formula 3-1,

X ₂₁ , Y ₂₁ , R ₂₁ to R ₂₃ , R ₂₆ , f, g', and i'are the same as defined in Formulas 2-1 to 2-5;

L ₂₁ is a single bond or a substituted or unsubstituted (C6-C30)arylene;

R ₃₁ and R ₃₂ are each independently, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted Or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl; However, at least one of R ₃₁ and R ₃₂ is a substituted or unsubstituted (3-30 membered) heteroaryl.

For example, in Formula 3-1, when X ₂₁ is -N=, Y ₂₁ may be -O- or -S-, preferably, X ₂₁ is -N= and Y ₂₁ is -O-yl I can.

For example, L ₂₁ may be a single bond or a substituted or unsubstituted (C6-C25) arylene, and preferably, a single bond or a substituted or unsubstituted (C6-C18) arylene. For example, L ₂₁ may be a single bond, substituted or unsubstituted phenylene, or substituted or unsubstituted naphthylene.

For example, R ₃₁ and R ₃₂ may each independently be a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5-30 membered) heteroaryl, preferably, a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5-25 member) heteroaryl, more preferably, a substituted or unsubstituted (C6-C18) aryl or a substituted or unsubstituted (5- 18 won) It may be a heteroaryl. However, at least one of R ₃₁ and R ₃₂ is a substituted or unsubstituted (3-30 membered) heteroaryl, for example, both of R ₃₁ and R ₃₂ are substituted or unsubstituted (3-30 membered) heteroarylyl I can. For example, R ₃₁ and R ₃₂ are each independently substituted or unsubstituted p-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted Phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted Or it may be unsubstituted benzonaphthofuranyl.

According to an example, the organic electroluminescent compound of Formula 3-1 may be more specifically exemplified as the following compounds, but is not limited thereto.

Hereinafter, an organic electroluminescent device to which a plurality of types of host materials and organic electroluminescent compounds are applied will be described.

An organic electroluminescent device according to an embodiment includes a first electrode; A second electrode; And at least one organic layer interposed between the first electrode and the second electrode, and according to an example, a first host material including a compound represented by Formula 1 and a compound represented by Formula 2 The second host material may be included in the same organic layer or may be included in different organic layers.

The organic layer includes at least one emission layer, and the emission layer includes at least one first host material including a compound represented by Formula 1 and at least one second host material including a compound represented by Formula 2 A host material including a plurality of types may be included, or an organic electroluminescent compound represented by Formula 3-1 may be included alone. According to an example, the emission layer includes at least one of compounds C-1 to C-597 as first host materials represented by Formula 1 and H-1 to H-215 as second host materials represented by Formula 2 It may contain at least one compound of. According to another embodiment, the organic layer may include an organic electroluminescent compound represented by Formula 3-1. For example, the compound of Formula 3-1 may be included as a material for a hole transport layer in an emission layer or a hole transport band of an organic electroluminescent device.

One of the first electrode and the second electrode may be an anode (anode) and the other may be a cathode (cathode). In this case, the first electrode and the second electrode may each be formed of a transparent conductive material, or may be formed of a transflective or reflective conductive material. In addition to the emission layer, the organic layer is 1 selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, an electron blocking layer, and an electron buffer layer. It may further include more than one layer.

The organic layer may further include an amine compound and/or an azine compound in addition to the light emitting material of the present application. Specifically, the hole injection layer, the hole transport layer, the hole auxiliary layer, the light emitting layer, the light emitting auxiliary layer, or the electron blocking layer is an amine compound, for example, an arylamine compound, a styrylarylamine compound, etc. It can be included as an injection material, a hole transport material, a hole auxiliary material, a light emitting material, a light emission auxiliary material, and an electron blocking material. In addition, the electron transport layer, electron injection layer, electron buffer layer, and hole blocking layer may include an azine compound as an electron transport material, an electron injection material, an electron buffer material, and a hole blocking material. In addition, the organic layer is one or more metals selected from the group consisting of group 1, group 2, period 4 transition metal, period 5 transition metal, lanthanum metal, and organometals of d-transition elements, or at least one It may further contain a complex compound.

A plurality of host materials according to an example may be used as a light emitting material for a white organic light emitting device. The white organic electroluminescent device is a side-by-side method or a stacking method according to the arrangement of R (red), G (green) or YG (yellow green), B (blue) light emitting units. , Or a color conversion material (CCM) method, and various structures have been proposed. In addition, a plurality of host materials according to an example may be used for an organic electroluminescent device including a quantum dot (QD).

A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be used between the anode and the light emitting layer. For the hole injection layer, a plurality of layers may be used for the purpose of lowering a hole injection barrier (or a hole injection voltage) from an anode to a hole transport layer or an electron blocking layer, and two compounds may be used simultaneously for each layer. Also, the hole injection layer may be doped with p-dopant. The electron blocking layer is located between the hole transport layer (or the hole injection layer) and the emission layer, and blocks overflow of electrons from the emission layer to confine excitons in the emission layer to prevent leakage of light. A plurality of layers may be used for the hole transport layer or the electron blocking layer, and a plurality of compounds may be used for each layer.

An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be used between the light emitting layer and the cathode. In the electron buffer layer, a plurality of layers may be used for the purpose of controlling electron injection and improving interfacial properties between the light emitting layer and the electron injection layer, and two compounds may be used simultaneously for each layer. A plurality of layers may be used for the hole blocking layer or the electron transport layer, and a plurality of compounds may be used for each layer. In addition, the electron injection layer may be doped with n-dopant.

The light emitting auxiliary layer is a layer positioned between the anode and the light emitting layer, or between the cathode and the light emitting layer, and when the light emitting auxiliary layer is positioned between the anode and the light emitting layer, it facilitates injection and/or transfer of holes or It can be used for blocking overflow, and when the light emitting auxiliary layer is located between the cathode and the light emitting layer, it can be used to facilitate injection and/or transmission of electrons or block overflow of holes. In addition, the hole auxiliary layer is located between the hole transport layer (or the hole injection layer) and the light emitting layer, and may exhibit an effect of smoothing or blocking a hole transfer rate (or injection rate), and accordingly, a charge balance ) Can be adjusted. When the organic electroluminescent device includes two or more hole transport layers, the additionally included hole transport layer may be used as a hole auxiliary layer or an electron blocking layer. The light emission auxiliary layer, the hole auxiliary layer, or the electron blocking layer may have an effect of improving the efficiency and/or lifespan of the organic electroluminescent device.

In the organic electroluminescent device of the present application, on the inner surface of at least one of the pair of electrodes, at least one layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as "surface layer" It is desirable to place ). Specifically, it is preferable to provide a silicon and aluminum chalcogenide (including oxide) layer on the surface of the anode on the side of the light-emitting medium layer, and a metal halide layer or a metal oxide layer on the surface of the cathode on the side of the light-emitting medium layer. Drive stabilization of the organic electroluminescent device can be obtained by the surface layer. Preferred examples of the chalcogenide include SiO _X (1≤X≤2), AlO _X (1≤X≤1.5), SiON, SiAlON, etc., and preferred examples of the metal halide are LiF, MgF ₂ , CaF ₂ , fluoride Rare earth metals and the like, and preferred examples of metal oxides include Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO, and the like.

Further, in the organic electroluminescent device of the present application, it is also preferable to arrange a mixed region of an electron transport compound and a reducing dopant or a mixed region of a hole transport compound and an oxidizing dopant on at least one surface of the pair of electrodes. In this way, since the electron transfer compound is reduced to an anion, it becomes easy to inject and transfer electrons from the mixed region to the light emitting medium. In addition, since the hole transport compound is oxidized to become a cation, it becomes easy to inject and transfer holes from the mixed region to the light emitting medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds, and preferable reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, it is possible to manufacture an organic electroluminescent device emitting white light having two or more light emitting layers by using the reducing dopant layer as a charge generating layer.

According to an example, the emission layer of the organic electroluminescent device may be a single layer as a layer that emits light, and may be a plurality of layers in which two or more layers are stacked. One or more dopants may be further included in the emission layer, and a doping concentration of the dopant compound to the host compound of the emission layer may be less than 20% by weight, preferably less than 10% by weight.

As the dopant included in the organic electroluminescent device of the present application, one or more phosphorescent or fluorescent dopants may be used, and a phosphorescent dopant is preferable. The phosphorescent dopant material applied to the organic electroluminescent device of the present application is not particularly limited, but may be a complex compound of metal atoms selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt). , In some cases, preferably, it may be an ortho-metallization complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and in some cases, more preferably, It may be an ortho metallized iridium complex compound.

The formation of each layer of the organic electroluminescent device of the present application is a dry film deposition method such as vacuum deposition, sputtering, plasma, ion plating, etc., ink jet printing, nozzle printing, slot coating, Any one of wet film forming methods such as spin coating, dip coating, and flow coating can be applied. In the case of wet film formation, a thin film is formed by dissolving or dispersing the material forming each layer in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc., and the solvent is dissolved or dispersed in the material forming each layer. It can be made, and any one may be used as long as there is no problem with the film forming property.

When depositing the first host material and the second host material according to an example, the film may be formed by the above-described method, and preferably, the film may be formed by a co-deposition or a mixed deposition process. The co-deposition refers to a method in which two or more isomeric materials are placed in each individual crucible source, and current is applied to two cells at the same time to evaporate the material, and the mixed deposition is a method of depositing two or more isomeric materials into one After mixing in a crucible source, an electric current is applied to one cell to evaporate the material, followed by mixed deposition.

According to an example, when the first host material and the second host material are present in the same layer or different layers in the organic electroluminescent device, the two host materials may be separately formed. For example, after depositing the first host material, a second host material may be deposited.

According to one embodiment, the present invention uses a plurality of host materials including the compound represented by Formula 1 and the compound represented by Formula 2, and includes a display device, for example, a smartphone, a tablet, a laptop computer, A display device for a PC, a TV or a vehicle, or a lighting device, for example, an outdoor or indoor lighting device can be provided.

Hereinafter, for a detailed understanding of the present application, a method for preparing a compound according to the present application and its physical properties will be described by taking the synthesis method of the representative compound or intermediate compound of the present application as an example.

[Example 1] Synthesis of Compound H-216

1) Synthesis of compound 1

Dibenzofuran-2-amine (20 g, 144.7 mmol), 2-bromo dibenzofuran (23.8 g, 96.47 mmol), Pd(OAc)2 (1.1 g, 4.82 mmol), S-Phos (3.9 g, 9.65 mmol), NaOt-Bu (13.9 g, 144.7 mmol), and 485 mL of o-xylene were added and stirred at 160°C for 3 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound 1 (4.9 g, yield: 10%).

2) Synthesis of Compound H-216

In a flask, compound 1 (4.9 g, 12.76 mmol), compound 2 (4.2 g, 14.0 mmol), Pd(dba ₃ ) ₂ (0.584 g, 0.638 mmol), S-Phos (0.523 g, 1.276 mmol), NaOt-Bu (1.8 g, 19.14 mmol), and 65 mL of o-xylene were added and stirred at 160 degrees for 2 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound H-216 (5.6 g, yield: 68.3%).

[Example 2] Synthesis of Compound H-183

In a flask, compound 3 (25 g, 74.48 mmol), compound 2 (42.58 g, 81.93 mmol), Pd(OAc) ₂ (0.16 g, 7.5 mmol), P(t-Bu) ₃ (0.28 g, 7.5 mmol), NaOt-Bu (14.31 g, 150 mmol), and 284.09 mL of o-xylene were added, followed by stirring at 160°C for 2 hours. After the reaction was completed, the reaction was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound H-183 (23.4 g, yield: 50%).

[Example 3] Synthesis of Compound H-231

In a flask, compound 4 (20 g, 56.96 mmol), compound 2 (18.8 g, 57.13 mmol), Pd(OAc)2 (0.13 g, 5.7 mmol), P(t-Bu) ₃ (0.22 g, 5.7 mmol), NaOt-Bu (11 g, 113.92 mmol), and 227.27 mL of o-xylene were added, followed by stirring at 160 degrees for 2 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound H-231 (12.5 g, yield: 34%).

[Example 4] Synthesis of Compound C-5

In a flask, compound 4-1 (4.0 g, 11.1 mmol), compound 4-2 (4.6 g, 13.3 mmol), Pd(PPh ₃ ) ₄ (0.6 g, 0.56 mmol), K ₂ CO ₃ (3.1 g, 22.2 mmol) ), 5.0 mL of EtOH, 40 mL of toluene, and 11 mL of distilled water were added, and the mixture was stirred under reflux for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, stirred, and methanol (MeOH) was added thereto, and the resulting solid was filtered under reduced pressure and separated by column chromatography with MC/Hex to give compound C-5 (4.9 g, yield: 81%). .

[Example 5] Synthesis of Compound C-146

In a flask, compound 5-1 (4.0 g, 14.9 mmol), compound 5-2 (7.1 g, 16.4 mmol), Pd ₂ (dba) ₃ (0.7 g, 0.8 mmol), s-phos (0.6 g, 1.5 mmol) , NaOt-Bu (3.5 g, 37.3 mmol) and 80 mL of o-xylene were added and stirred under reflux for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, stirred, and MeOH was added thereto, and the resulting solid was filtered under reduced pressure and separated by column chromatography using MC/Hex to obtain compound C-146 (3.6 g, yield: 45%).

[Example 6] Synthesis of Compound C-160

In a flask, compound 4-1 (4.5 g, 12.49 mmol), compound 6-2 (6.6 g, 14.20 mmol), tetrakis (triphenylphosphine) palladium (0) (Pd (PPh ₃ ) ₄ ) (0.4 g, 0.34 mmol), sodium carbonate (3.0 g, 28.38 mmol), 55 mL of toluene, 14 mL of ethanol, and 14 mL of distilled water were added and stirred at 130°C for 4 hours. After the reaction was completed, the precipitated solid was washed with distilled water and methanol. After that, it was purified by column chromatography to obtain compound C-160 (3.9 g, yield: 51%).

[Example 7] Synthesis of Compound C-230

In a flask, compound 7-1 (4.5 g, 13.07 mmol), compound 7-2 (5 g, 13.07 mmol), Pd(PPh ₃ ) ₄ (0.75 g, 0.653 mmol), potassium carbonate (5.4 g, 39.22 mol), 80 mL of toluene, 20 mL of ethanol, and 20 mL of water were added, followed by reflux stirring for 2 hours. After the reaction was completed, the mixture was cooled to room temperature, methanol was added dropwise, and the resulting solid was filtered under reduced pressure, dissolved in dimethyl chloride, and separated by column chromatography to obtain compound C-230 (3.7 g, yield: 53%).

[Example 8] Synthesis of Compound C-167

In a flask, compound 8-1 (5 g, 19.03 mmol), compound 8-2 (9.1 g, 20.94 mmol), Pd ₂ (dba) ₃ (0.88 g, 0.97 mmol), s-phos (0.79 g, 1.93 mmol) , NaOt-Bu (4.63 g, 48.3 mmol), and 100 mL of o-xylene were added and dissolved, followed by reflux stirring for 4 hours. After the reaction was completed, the mixture was extracted with ethyl acetate and separated by column chromatography to obtain compound C-167 (5 g, yield: 50%).

[Example 9] Synthesis of Compound C-489

In a flask, compound 4-1 (5.0 g, 13.9 mmol), compound 9-1 (6.1 g, 13.9 mmol), Pd(PPh ₃ ) ₄ (0.8 g, 0.7 mmol), potassium carbonate (3.9 g, 27.8 mmol), 30 mL of toluene, 10 mL of ethanol, and 14 mL of distilled water were added and stirred at 130°C for 5 hours. After the reaction was completed, the precipitated solid was washed with distilled water and methanol. After that, it was purified by column chromatography to obtain compound C-489 (3.6 g, yield: 44%).

[Example 10] Synthesis of Compound C-249

In a flask, compound 10-1 (4.0 g, 14.9 mmol), compound 8-2 (7.1 g, 16.4 mmol), Pd ₂ (dba) ₃ (0.7 g, 0.74 mmol), s-phos (0.6 g, 1.49 mmol) , NaOt-Bu (3.5 g, 37.3 mmol), and 80 mL of o-xylene were added and stirred at 165° C. for 5 hours. After the reaction was completed, the mixture was cooled to room temperature and the organic layer was extracted with ethyl acetate. After removing residual moisture from the organic layer extracted using magnesium sulfate, it was dried, and the solvent was removed with a rotary evaporator. After that, the resultant was separated by column chromatography to obtain compound C-249 (4.2 g, yield: 81%).

[Example 11] Synthesis of Compound C-174

In a flask, compound 11-1 (6.0 g, 23.7 mmol), compound 8-2 (11.4 g, 26.1 mmol), Pd ₂ (dba) ₃ (1.1 g, 1.2 mmol), s-phos (0.98 g, 2.4 mmol) , Potassium phosphate (12.6 g, 59.3 mmol), and 120 mL of o-xylene were added, followed by stirring at 165° C. for 5 hours. After the reaction was completed, the mixture was cooled to room temperature and the organic layer was extracted with ethyl acetate. After removing residual moisture in the organic layer extracted with magnesium sulfate, it was dried, and the solvent was removed with a rotary evaporator. After that, it was purified by column chromatography to obtain compound C-174 (4.0 g, yield: 32%).

[Example 12] Synthesis of Compound C-582

In a flask, compound 12-1 (4.23 g, 11.4 mmol), compound 12-2 (5.04 g, 13.7 mmol), Pd(PPh ₃ ) ₄ (0.66 g, 0.57 mmol), potassium carbonate (3.15 g, 22.8 mmol), and 35 mL of toluene, 7 mL of ethanol, and 11 mL of distilled water were added and stirred at 130°C for 15 hours. Upon completion of the reaction, the precipitated solid was washed with distilled water and methanol. Thereafter, purification was performed by column chromatography to obtain compound C-582 (4.5 g, yield: 69%).

[Example 13] Synthesis of Compound H-239

1) Synthesis of compound 13-1

In a flask, 3-aminobiphenyl (54 g, 319 mmol), 3-bromobiphenyl (70 g, 301 mmol), Pd(OAc) ₂ (0.33 g, 1.47 mmol), tricyclohexylphosphine (0.84 g, 2.8 mmol), NaOt-Bu (57 g, 593 mmol), and 280 mL of toluene were added and stirred at 95°C for 8 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound 13-1 (60.23 g, yield: 85%).

2) Synthesis of Compound H-239

In a flask, compound 13-1 (60.23 g, 187.5 mmol), compound 2 (60 g, 182.33 mmol), Pd(OAc) ₂ (0.41 g, 1.83 mmol), S-phos (1.74 g, 4.23 mmol), NaOt- Bu (26.23 g, 272 mmol), and 300 mL of xylene were added and stirred at 110°C for 10 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound H-239 (36.9 g, yield: 33%).

[Example 14] Synthesis of Compound H-240

1) Synthesis of compound 14-1

Dibenzofuran-2-amine (29.24 g, 159.7 mmol), 2-bromodibenzothiophene (40 g, 152.7 mmol), Pd(OAc) ₂ (0.17 g, 0.75 mmol), tricyclohexylphosphine in a flask (0.43 g, 1.45 mmol), NaOt-Bu (29.22 g, 304 mmol), and 250 mL of toluene were added and stirred at 95°C for 8 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound 14-1 (17.12 g, yield: 86%).

2) Synthesis of Compound H-240

In a flask, compound 14-1 (17.12 g, 46.89 mmol), compound 2 (15 g, 45.58 mmol), Pd(OAc) ₂ (0.05 g, 0.22 mmol), S-phos (0.22 g, 0.535 mmol), NaOt- Bu (6.56 g, 68.2 mmol), and 75 mL of xylene were added and stirred at 110°C for 10 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound H-240 (10.2 g, yield: 34%).

[Example 15] Synthesis of Compound H-189

In a flask, compound 2 (5.0 g, 15.2 mmol), di([1,1′-biphenyl]-4-yl)amine (4.9 g, 15.2 mmol), Pd(OAc) ₂ (0.2 g, 0.8 mmol), P(t-Bu) ₃ (0.8 mL, 1.5 mmol), NaOt-Bu (2.9 g, 30.4 mmol), and 76 mL of xylene were added, followed by stirring at 160° C. for 5 hours. After the reaction was completed, it was cooled to room temperature, and the precipitated solid was washed with distilled water and methanol. After separation by column chromatography, compound H-189 (5.5 g, yield: 59%) was obtained.

[Example 16] Synthesis of Compound H-146

In a flask, compound 2 (4 g, 12 mmol), bis(biphenyl-4-yl)[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane- 2-yl)phenyl]amine (6.8 g, 13 mmol), Pd(OAc) ₂ (0.3 g, 1 mmol), s-Phos (0.9 g, 2 mmol), Cs ₂ CO ₃ (11.5 g, 35 mmol) , o-xylene 60 mL, EtOH 15 mL, and distilled water 15 mL were added, followed by reflux stirring at 150° C. for 3 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, washed with distilled water, and the organic layer was extracted with ethyl acetate, the residual moisture was removed with magnesium sulfate, dried, and separated by column chromatography, compound H-146 (2.2 g, yield: 27% ).

[Example 17] Synthesis of Compound H-175

In a flask, compound 17 (4.8 g, 11.34 mmol), N-(4-bromophenyl)-N-phenyl-[1,1'-biphenyl]-4-amine (5 g, 12.47 mmol), Pd(PPh ₃ ) ₄ (0.4 g, 0.34 mmol), Na ₂ CO ₃ (3.0 g, 28.35 mmol), 57 mL of toluene, 14 mL of ethanol, and 14 mL of distilled water were added, followed by stirring at 120°C for 4 hours. After the reaction was completed, the mixture was added dropwise to methanol, and the resulting solid was filtered. The resulting solid was purified by column chromatography to obtain compound H-175 (1.4 g, yield: 20.0%).

[Example 18] Synthesis of Compound H-212

1) Synthesis of compound 18-1

In a flask, compound 2 (10.0 g, 30.3 mmol), [1,1'-biphenyl]-3-amine (6.7 g, 39.4 mmol), Pd(OAc) ₂ (0.34 g, 1.5 mmol), P(t- Bu) ₃ (1.5 mL, 3.03 mmol), NaOt-Bu (5.8 g, 60.6 mmol), and 150 mL of xylene were added, followed by stirring at 160° C. for 6 hours. After the reaction was completed, the reaction was washed with distilled water, the organic layer was extracted with ethyl acetate, dried over magnesium sulfate, and the solvent was removed by a rotary evaporator and then separated by column chromatography to give compound 18-1 (10.8 g, yield: 36%). .

2) Synthesis of Compound H-212

In a flask, compound 18-1 (5.0 g, 10.8 mmol), 3-bromo dibenzofuran (3.2 g, 12.9 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.54 mmol), S-Phos (0.45 g, 1.08 mmol), NaOt-Bu (2.0 g, 21.6 mmol), and o-xylene 60 mL were added, followed by stirring at 160° C. for 6 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound H-212 (1.45 g, yield: 21%).

Hereinafter, for a detailed understanding of the present application, a method of manufacturing an organic electroluminescent device including a plurality of host materials according to the present application and characteristics thereof will be described.

[Device Examples 1 and 2] OLED manufacturing by depositing a plurality of host materials according to the present application as a host

An OLED comprising the compound according to the present application was prepared. First, the transparent electrode ITO thin film (10Ω/□) obtained from OLED glass (manufactured by Geomatec) was subjected to ultrasonic cleaning by sequentially using acetone, trichloroethylene, acetone, ethanol, and distilled water, and then stored in isopropanol. Used. Next, after mounting the ITO substrate on the substrate holder of the vacuum evaporation equipment, insert the compound HI-1 into the cell in the vacuum evaporation equipment, evacuate until the vacuum level in the chamber reaches 10 ^-6 torr, and then apply a current to the cell. Then, evaporation was performed to deposit a first hole injection layer having a thickness of 80 nm on the ITO substrate. Subsequently, compound HI-2 was put into another cell in a vacuum deposition equipment, and a second hole injection layer having a thickness of 5 nm was deposited on the first hole injection layer by evaporation by applying a current to the cell. Subsequently, compound HT-1 was put into a cell in a vacuum deposition equipment, and a current was applied to the cell to evaporate to deposit a first hole transport layer having a thickness of 10 nm on the second hole injection layer. Compound HT-2 was added to another cell in the vacuum deposition equipment, and a second hole transport layer having a thickness of 60 nm was deposited on the first hole transport layer by evaporation by applying a current to the cell. After forming the hole injection layer and the hole transport layer, a light emitting layer was deposited thereon as follows: The first host material and the second host material described in Table 1 below were put as hosts in a cell in a vacuum deposition equipment, and another cell Compound D-39 was added as a dopant, and then the two host materials were evaporated at a rate of 1:1, and the dopant material was evaporated at a different rate. By doping with, a light emitting layer having a thickness of 40 nm was deposited on the hole transport layer. Subsequently, compound ET-1 and compound EI-1 were evaporated at a rate of 1:1 in two other cells to deposit an electron transport layer having a thickness of 35 nm on the emission layer. Subsequently, compound EI-1 as an electron injection layer was deposited on the electron transport layer to a thickness of 2 nm, and then an Al cathode was deposited on the electron injection layer to a thickness of 80 nm using other vacuum deposition equipment to prepare an OLED. .

[Device Example 3] Fabrication of OLED by depositing multiple types of host materials according to the present application as a host

The same as in Device Example 1, except that a second hole transport layer having a thickness of 45 nm was deposited using compound HT-3 , and an electron blocking layer having a thickness of 15 nm was deposited using compound EB-1 thereon. OLED was manufactured by the method.

[Comparative Device Examples 1 to 4] Manufacture of OLED containing a comparative compound as a host

An OLED was manufactured in the same manner as in Device Example 1, except that the compound of Table 1 was used as the host of the light emitting layer.

The power efficiency of the organic electroluminescent devices of Device Examples 1 to 3 and Device Comparative Examples 1 to 4 manufactured as described above, power efficiency based on 1,000 nits luminance and intensity of light at 5,000 nits fell from 100% to 95%. The time taken (life; T95) was measured and the results are shown in Table 1 below.

From Table 1 above, the organic electroluminescent device comprising a compound of a specific combination according to the present application as a host material uses a single host material (Comparative Devices Examples 1 and 2), or is used as a host material in combination with a conventional host compound. (Comparative device examples 3 and 4) It can be seen that compared to the organic electroluminescent device, while exhibiting an efficiency equal to or higher than that of the organic electroluminescent device, in particular, the lifetime is significantly improved.

The compounds used in the device examples and device comparative examples are shown in Table 2 below.

[Device Examples 4 to 10] OLED fabrication by depositing a plurality of host materials according to the present application

An OLED according to the present application was prepared. First, a transparent electrode ITO thin film (10Ω/□) on a glass for OLED (manufactured by Geomatech) substrate was subjected to ultrasonic cleaning by sequentially using acetone and isopropyl alcohol, and then stored in isopropyl alcohol and used. Next, after mounting the ITO substrate on the substrate holder of the vacuum evaporation equipment, compound HI-3 is put in a cell in the vacuum evaporation equipment, and compound HT-1 is put in another cell, and the two substances are evaporated at different rates to form a compound. With respect to the total amount of HI-3 and compound HT-1 , compound HI-3 was doped in an amount of 3% by weight to deposit a hole injection layer having a thickness of 10 nm. Subsequently, compound HT-1 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 80 nm. Subsequently, compound HT-2 was put into another cell in a vacuum deposition equipment, and a second hole transport layer having a thickness of 60 nm was deposited on the first hole transport layer by evaporation by applying a current to the cell. After forming the hole injection layer and the hole transport layer, a light emitting layer was deposited thereon as follows: Each of the first host material and the second host material described in Table 3 below were put as hosts in two cells in the vacuum deposition equipment. , After putting compound D-39 as a dopant in another cell, the two host materials were evaporated at a rate of 1:1, and the dopant material was evaporated at different rates at the same time, so that the dopant was 3 for the total amount of the host and the dopant. By doping in an amount of weight %, a light emitting layer having a thickness of 40 nm was deposited on the second hole transport layer. Subsequently, compound ET-1 and compound EI-1 as electron transport materials were deposited on the light emitting layer in a weight ratio of 50:50 to deposit an electron transport layer having a thickness of 35 nm. Subsequently, compound EI-1 was deposited as an electron injection layer to a thickness of 2 nm on the electron transport layer, and then an Al cathode was deposited on the electron injection layer to a thickness of 80 nm using other vacuum deposition equipment to prepare an OLED. . Each compound was used by vacuum sublimation purification under 10 ^-6 torr for each material.

[Comparative Device Example 5] Manufacture of OLED containing a comparative compound as a host

An OLED was manufactured in the same manner as in Device Example 4, except that the compound of Table 3 was used as the host of the light emitting layer.

The driving voltage, luminous efficiency, luminescence color, and light intensity based on the luminance of 5,000 nits of the organic electroluminescent devices of Device Examples 4 to 10 and Device Comparative Example 5 prepared as described above were from 100% to 95%. The time taken to fall (life: T95) was measured and shown in Table 3 below.

From Table 3 above, it can be seen that the driving voltage, luminous efficiency, and/or lifetime characteristics of the organic electroluminescent device including the host material of the compound of the specific combination according to the present disclosure are improved.

The compounds used in the device examples are shown in Table 4 below.

[Device Example 11] Fabrication of an OLED containing the organic electroluminescent compound according to the present application

An OLED according to the present application was prepared. First, a transparent electrode ITO thin film (10Ω/□) on a glass for OLED (manufactured by Geomatech) substrate was subjected to ultrasonic cleaning by sequentially using acetone and isopropyl alcohol, and then stored in isopropyl alcohol and used. Next, after mounting the ITO substrate on the substrate holder of the vacuum evaporation equipment, compound HI-3 is put in a cell in the vacuum evaporation equipment, and compound HT-1 is put in another cell, and the two substances are evaporated at different rates to form a compound. With respect to the total amount of HI-3 and compound HT-1 , compound HI-3 was doped in an amount of 3% by weight to deposit a hole injection layer having a thickness of 10 nm. Subsequently, compound HT-1 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 80 nm. Subsequently, compound H-221 was put into another cell in the vacuum deposition equipment, and a second hole transport layer having a thickness of 60 nm was deposited on the first hole transport layer by evaporation by applying a current to the cell. After forming the hole injection layer and the hole transport layer, a light emitting layer was deposited thereon as follows: RH was put as a host in a vacuum evaporation equipment, compound D-39 as a dopant was put in another cell, and then the two materials were mixed. By evaporating at a different rate and doping in an amount of 3% by weight, respectively, a light emitting layer having a thickness of 40 nm was deposited on the second hole transport layer. Subsequently, compound ET-1 and compound EI-1 as electron transport materials were deposited on the light emitting layer in a weight ratio of 50:50 to deposit an electron transport layer having a thickness of 35 nm. Subsequently, compound EI-1 was deposited as an electron injection layer to a thickness of 2 nm on the electron transport layer, and then an Al cathode was deposited on the electron injection layer to a thickness of 80 nm using other vacuum deposition equipment to prepare an OLED. . Each compound was used by vacuum sublimation purification under 10 ^-6 torr for each material.

[Comparative Device Example 6] Manufacture of OLED containing a comparative compound as a second hole transport layer material

An OLED was manufactured in the same manner as in Device Example 11, except that the compound H-179 was used as the material for the second hole transport layer.

From 100% to 95% of light intensity based on 1,000 nits luminance, driving voltage, luminous efficiency, luminescence color, and 5,000 nits luminance of the organic electroluminescent devices of Device Example 11 and Device Comparative Example 6 manufactured as described above. The time taken (life: T95) was measured and shown in Table 5 below.

From Table 5, it can be seen that the driving voltage, luminous efficiency, and/or lifetime characteristics of the organic electroluminescent device including the organic electroluminescent compound according to the present disclosure as a material for the hole transport layer are improved.

The compounds used in the device examples and device comparative examples are shown in Table 6 below.

Claims (12)

A plurality of host materials including a first host material comprising a compound represented by the following formula (1) and a second host material comprising a compound represented by the following formula (2):
[Formula 1]

In Formula 1,
Y ₁ is O, S, CR ₁₁ R ₁₂ , or NR ₁₃ ;
R ₁₁ to R ₁₃ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted ( C3-C30)cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl, or ; R ₁₁ and R ₁₂ may be linked to each other to form a ring;
R ₁ to R ₃ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3 -30 membered) Heteroaryl, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30) ) Alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted (C1 -C30) alkyl (C6-C30) arylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, substituted or unsubstituted mono- or di- (3-30 membered) heteroarylamino, Or a substituted or unsubstituted (C6-C30) aryl (3-30 membered) heteroarylamino; Adjacent substituents may be linked to each other to form a ring;
Provided that at least one of R ₁₃ , R ₂ , and R ₃ is -L ₁ -(Ar ₁ ) _d ;
L ₁ is a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene;
Each Ar ₁ is independently a substituted or unsubstituted (3-30 membered) heteroaryl containing at least one nitrogen (N);
a and c are each independently an integer of 1 to 4, b and d are an integer of 1 or 2;
When a to d are integers of 2 or more, each R ₁ , each R ₂ , each R ₃ , and each Ar ₁ may be the same as or different from each other;
[Formula 2]

In Formula 2,
X ₂₁ and Y ₂₁ are each independently -N=, -NR ₂₄ -, -O-, or -S-, provided that any one of X ₂₁ and Y ₂₁ is -N=, and X ₂₁ and Y ₂₁ The other is -NR ₂₄ -, -O-, or -S-;
R ₂₁ is substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered) heteroaryl;
R ₂₂ to R ₂₄ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3 -30 membered) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted Substituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, A substituted or unsubstituted (C3-C30) aliphatic ring and a fused ring group of (C6-C30) aromatic ring, substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted Mono- or di- (C6-C30) arylamino, substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino, substituted or unsubstituted mono- or di- (3-30 membered) heteroaryl Amino, or a substituted or unsubstituted (C6-C30)aryl (3-30 membered) heteroarylamino; May be linked with adjacent substituents to form a ring;
Provided that at least one of R ₂₂ and R ₂₃ is -L ₂₁ -Ar ₂₁ ;
L ₂₁ is a single bond or a substituted or unsubstituted (C6-C30)arylene;
Ar ₂₁ is substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic Fused ring group of the ring, substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, substituted or unsubstituted (C1- C30) alkyl (C6-C30) arylamino, substituted or unsubstituted mono- or di- (3-30 membered) heteroarylamino, or substituted or unsubstituted (C6-C30) aryl (3-30 membered) hetero Arylamino;
f is an integer of 1 or 2, g is an integer of 1 to 4;
When f and g are integers of 2 or more, each R ₂₂ and each R ₂₃ may be the same or different from each other. The host material of claim 1, wherein Formula 1 is represented by any one of the following Formulas 1-1 to 1-9:
[Formula 1-1] [Formula 1-2]

[Formula 1-3] [Formula 1-4]

[Formula 1-5] [Formula 1-6]

[Formula 1-7] [Formula 1-8]

[Formula 1-9]

In Formulas 1-1 to 1-9,
Y ₁ , L ₁ , Ar ₁ , R ₁ to R ₃ , and a to d are the same as defined in claim 1;
Each R ₄ is independently the same as the definition of R ₃ ;
e is an integer of 1 to 3, and when e is an integer of 2 or more, each R ₄ may be the same or different. The host material of claim 1, wherein Formula 2 is represented by any one of the following Formulas 2-1 to 2-5:
[Formula 2-1] [Formula 2-2]

[Formula 2-3] [Formula 2-4]

[Formula 2-5]

In Formulas 2-1 to 2-5,
X ₂₁ , Y ₂₁ , L ₂₁ , Ar ₂₁ , R ₂₁ to R ₂₃ , f, and g are the same as defined in claim 1;
R ₂₅ and R ₂₆ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3 -30 membered) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted Substituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, Substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono-or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6 -C30) arylamino, substituted or unsubstituted mono- or di- (3-30 membered) heteroarylamino, or substituted or unsubstituted (C6-C30) aryl (3-30 membered) heteroarylamino; May be linked with adjacent substituents to form a ring;
g'is an integer of 1 or 2, h and i are each independently an integer of 1 to 3, and i'is an integer of 1 to 4;
When g', h, i, and i'are integers of 2 or more, each R ₂₃ , each R ₂₅ , and each R ₂₆ may be the same or different from each other. The method of claim 1, wherein Ar ₁ is each independently substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted Substituted pyridazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted quinolyl , Substituted or unsubstituted benzoquinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted benzoisoquinolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted Naphthyridinyl, or a substituted or unsubstituted benzothienopyrimidinyl, the host material. The method of claim 1, wherein Ar ₂₁ is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted p -Biphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted phenanthre Nyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirobifluorenyl, substituted Or unsubstituted spiro[cyclopentane-fluoren]yl, substituted or unsubstituted spiro[dihydroinden-fluoren]yl, substituted or unsubstituted spiro[benzofluorene-fluoren]yl, substituted or Unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted dibenzocarbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzo Naphthothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzonaphthofuranyl, or phenyl, naphthyl, naphthylphenyl, phenylnaphthyl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl, p-terphenyl, fluorenyl, benzofluorenyl, phenanthrenyl, benzonaphthofuranyl, di The host material, which is amino substituted with at least one of benzothiophenyl, and dibenzofuranyl. The host material of claim 1, wherein the compound represented by Formula 1 is at least one selected from the following compounds.

The host material of claim 1, wherein the compound represented by Formula 2 is at least one selected from the following compounds.

anode; cathode; And at least one light emitting layer between the anode and the cathode, wherein the light emitting layer of the at least one layer comprises a plurality of types of host materials according to claim 1. Organic electroluminescent compound represented by the following formula 3-1:
[Formula 3-1]

In Formula 3-1,
X ₂₁ , Y ₂₁ , R ₂₁ to R ₂₃ , R ₂₆ , f, g', and i'are the same as defined in claim 3;
L ₂₁ is a single bond or a substituted or unsubstituted (C6-C30)arylene;
R ₃₁ and R ₃₂ are each independently, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted Or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl; However, at least one of R ₃₁ and R ₃₂ is a substituted or unsubstituted (3-30 membered) heteroaryl. The organic electroluminescent compound of claim 9, wherein the compound represented by Formula 3-1 is selected from the following compounds.

An organic electroluminescent device comprising the organic electroluminescent compound according to claim 10. The organic electroluminescent device according to claim 11, wherein the organic electroluminescent compound is included in the hole transport band and/or the emission layer.