KR102640739B1 - Silole compound and organic light emitting device including the same - Google Patents

Abstract

The present invention relates to sirole compounds and organic electroluminescent devices containing them. A sirole compound according to an embodiment of the present invention is represented by the following formula (1).
[Formula 1]

Description

SILOLE COMPOUND AND ORGANIC LIGHT EMITTING DEVICE INCLUDING THE SAME}

The present invention relates to sirole compounds and organic electroluminescent devices containing them.

Recently, as an image display device, organic light emitting displays have been actively developed. An organic electroluminescent display device is different from a liquid crystal display device, and is a so-called self-luminous type device that realizes display by recombining holes and electrons injected from the anode and cathode in the light emitting layer to emit light from a light emitting material containing an organic compound in the light emitting layer. It is a display device of

As an organic electroluminescent device, for example, an organic electroluminescent device composed of an anode, a hole transport region disposed on the anode, a light emitting layer disposed on the hole transport region, an electron transport region disposed on the light emitting layer, and a cathode disposed on the electron transport region. The element is known. Holes are injected from the anode, and the injected holes move and are injected into the light emitting layer. Meanwhile, electrons are injected from the cathode, and the injected electrons move and are injected into the light-emitting layer. When holes and electrons injected into the light-emitting layer recombine, excitons are generated within the light-emitting layer. An organic electroluminescent element emits light using light generated by the radiative inactivity of its excitons. Additionally, the organic electroluminescent element is not limited to the structure described above, and various modifications are possible.

When applying organic electroluminescent devices to display devices, lower driving voltage, higher luminous efficiency, and longer lifespan of organic electroluminescent devices are required. In order to realize lower driving voltage, higher luminous efficiency, and longer lifespan of organic electroluminescent devices, normalization and stabilization of the hole transport region are being studied. Carbazole-based compounds are known as hole transport materials used in the hole transport region. However, organic electroluminescent devices using carbazole-based compounds are difficult to have a sufficient luminescence lifespan and have high luminous efficiency when driven at low voltage. A carbazole-based compound may include carbazole in the structure of the compound.

The purpose of the present invention is to provide a sirole compound that can be used in an organic electroluminescent device with high luminous efficiency.

Another object of the present invention is to provide an organic electroluminescent device with high luminous efficiency.

A sirole compound according to an embodiment of the present invention is represented by the following formula (1).

[Formula 1]

In Formula 1, R ₁ is a substituted or unsubstituted ring-forming aryl group with 6 to 10 carbon atoms, or an alkyl group with 1 to 20 carbon atoms, and Ar ₁ to Ar ₅ are each independently a hydrogen atom, a deuterium atom, or a halogen. Atom, substituted or unsubstituted ring-forming aryl group with 6 to 30 carbon atoms, substituted or unsubstituted ring-forming heteroaryl group with 5 to 30 carbon atoms, substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, or unsubstituted is a substituted or unsubstituted silyl group having 3 to 60 carbon atoms, L ₁ to L ₃ are each independently a single bond or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and a, b and c are Each is independently an integer between 0 and 4.

Formula 1 may be represented by Formula 2 below.

[Formula 2]

The L ₁ may be a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group.

At least one of Ar ₄ and Ar ₅ may be a substituted or unsubstituted naphthyl group.

Ar ₄ and Ar ₅ are each independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted dibenzo. It may be a furan group or a substituted or unsubstituted phenanthrene group.

The R1 may be a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group.

Ar ₁ and Ar ₂ may each independently form a ring with an adjacent group.

Ar ₁ and Ar ₂ may each independently be a hydrogen atom or a substituted or unsubstituted phenyl group.

Formula 1 may be selected from compounds represented in compound group 1 below.

[Compound Group 1]

The organic electroluminescent device according to an embodiment of the present invention includes an anode, a hole transport region, a light emitting layer, an electron transport region, and a cathode. The hole transport region is provided on the anode. The light-emitting layer is provided on the hole transport region. The electron transport region is provided on the light emitting layer. The cathode is provided on the electron transport region. The hole transport region includes a sirole compound represented by the following formula (1).

[Formula 1]

In Formula 1, R ₁ is a substituted or unsubstituted ring-forming aryl group with 6 to 10 carbon atoms, or an alkyl group with 1 to 20 carbon atoms, and Ar ₁ to Ar ₅ are each independently a hydrogen atom, a deuterium atom, or a halogen. Atom, substituted or unsubstituted ring-forming aryl group with 6 to 30 carbon atoms, substituted or unsubstituted ring-forming heteroaryl group with 5 to 30 carbon atoms, substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, or unsubstituted is a substituted or unsubstituted silyl group having 3 to 60 carbon atoms, L ₁ to L ₃ are each independently a single bond or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and a, b and c are Each is independently an integer between 0 and 4.

The hole transport region includes a hole injection layer and a hole transport layer provided on the hole injection layer. At least one of the hole injection layer and the hole transport layer may include a sirole compound represented by Formula 1.

Formula 1 may be represented by Formula 2 below.

[Formula 2]

The L ₁ may be a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group.

At least one of Ar ₄ and Ar ₅ may be a substituted or unsubstituted naphthyl group.

Ar ₄ and Ar ₅ are each independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted dibenzo. It may be a furan group or a substituted or unsubstituted phenanthrene group.

The R1 may be a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group.

Ar ₁ and Ar ₂ may each independently form a ring with an adjacent group.

Ar ₁ and Ar ₂ may each independently be a hydrogen atom or a substituted or unsubstituted phenyl group.

Formula 1 may be selected from compounds represented in compound group 1 below.

[Compound Group 1]

An organic electroluminescent device containing a sirole compound according to an embodiment of the present invention can achieve high luminous efficiency.

1 is a cross-sectional view schematically showing an organic electroluminescent device according to an embodiment of the present invention.
Figure 2 is a cross-sectional view schematically showing an organic electroluminescent device according to an embodiment of the present invention.

The above objects, other objects, features and advantages of the present invention will be easily understood through the following preferred embodiments related to the attached drawings. However, the present invention is not limited to the embodiments described herein and may be embodied in other forms. Rather, the embodiments introduced herein are provided so that the disclosed content will be thorough and complete and so that the spirit of the present invention can be sufficiently conveyed to those skilled in the art.

While describing each drawing, similar reference numerals are used for similar components. In the attached drawings, the dimensions of the structures are enlarged from the actual size for clarity of the present invention. Terms such as first, second, etc. may be used to describe various components, but the components should not be limited by the terms. The above terms are used only for the purpose of distinguishing one component from another. For example, a first component may be named a second component, and similarly, the second component may also be named a first component without departing from the scope of the present invention. Singular expressions include plural expressions unless the context clearly dictates otherwise.

In this application, terms such as “comprise” are intended to designate the presence of features, numbers, steps, operations, components, parts, or combinations thereof described in the specification, but are not intended to include one or more other features, numbers, or steps. , it should be understood that it does not exclude in advance the possibility of the existence or addition of operations, components, parts, or combinations thereof. Additionally, when a part of a layer, membrane, region, plate, etc. is said to be “on” another part, this includes not only being “directly above” the other part, but also cases where there is another part in between. Conversely, when a part of a layer, membrane, region, plate, etc. is said to be "underneath" another part, this includes not only being "immediately below" the other part, but also cases where there is another part in between.

In this specification, “substituted or unsubstituted” refers to deuterium, halogen group, nitrile group, nitro group, amino group, silyl group, boron group, phosphine oxide group, alkyl group, alkoxy group, alkenyl group, fluorenyl group, and aryl group. and may mean substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups. Additionally, each of the above-exemplified substituents may be substituted or unsubstituted. For example, a biphenyl group may be interpreted as an aryl group, or as a phenyl group substituted or unsubstituted with a phenyl group.

In the present specification, "forming a ring by combining with adjacent groups" may mean combining with adjacent groups to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted hetero ring. Hydrocarbon rings include aliphatic hydrocarbon rings and aromatic hydrocarbon rings. Heterocycles include aliphatic heterocycles and aromatic heterocycles. Hydrocarbon rings and heterocycles may be monocyclic or polycyclic. Additionally, a ring formed by combining adjacent groups may be connected to another ring to form a spiro structure.

As used herein, “adjacent group” may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, another substituent substituted on the atom on which the substituent is substituted, or a substituent that is sterically closest to the substituent. there is. For example, in 1,2-dimethylbenzene, two methyl groups can be interpreted as “adjacent groups,” and in 1,1-diethylcyclopentene, two methyl groups can be interpreted as “adjacent groups.” The ethyl groups can be interpreted as “adjacent groups”.

In this specification, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

As used herein, alkyl groups may be straight chain, branched chain, or cyclic. The carbon number of the alkyl group is 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of alkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, t-butyl group, i-butyl group, 2-ethylbutyl group, and 3, 3-dimethylbutyl group. , n-pentyl group, i-pentyl group, neopentyl group, t-pentyl group, cyclopentyl group, 1-methylpentyl group, 3-methylpentyl group, 2-ethylpentyl group, 4-methyl-2-pentyl group. , n-hexyl group, 1-methylhexyl group, 2-ethylhexyl group, 2-butylhexyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-t-butylcyclohexyl group, n-heptyl group, 1 -Methylheptyl group, 2, 2-dimethylheptyl group, 2-ethylheptyl group, 2-butylheptyl group, n-octyl group, t-octyl group, 2-ethyloctyl group, 2-butyloctyl group, 2-hexyl group Siloctyl group, 3, 7-dimethyloctyl group, cyclooctyl group, n-nonyl group, n-decyl group, adamantyl group, 2-ethyldecyl group, 2-butyldecyl group, 2-hexyldecyl group, 2-octyl group Tyldecyl group, n-undecyl group, n-dodecyl group, 2-ethyldodecyl group, 2-butyldodecyl group, 2-hexyldodecyl group, 2-octyldodecyl group, n-tridecyl group, n-tetradecyl group, n -Pentadecyl group, n-hexadecyl group, 2-ethylhexadecyl group, 2-butylhexadecyl group, 2-hexylhexadecyl group, 2-octylhexadecyl group, n-heptadecyl group, n-octadecyl group , n-nonadecyl group, n-icosyl group, 2-ethyl icosyl group, 2-butyl icosyl group, 2-hexyl icosyl group, 2-octyl icosyl group, n-henicosyl group, n-docosyl group, n-tricosyl group Examples include syl group, n-tetracosyl group, n-pentacosyl group, n-hexacosyl group, n-heptacosyl group, n-octacosyl group, n-nonacosyl group, and n-triacontyl group. It is not limited to

As used herein, an aryl group refers to any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. The ring-forming carbon number of the aryl group may be 6 to 30 or 6 to 20. Examples of aryl groups include phenyl group, naphthyl group, fluorenyl group, anthracenyl group, phenanthryl group, biphenyl group, terphenyl group, quaternophenyl group, quincphenyl group, sexiphenyl group, triphenylene group, pyrenyl group, benzofluoranthenyl group, Examples include chrysenyl group, but it is not limited to these.

In the present specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure.

In the present specification, the heteroaryl group may be a heteroaryl group containing one or more of O, N, and S as heterogeneous elements. The number of ring carbon atoms in the heteroaryl group is 2 to 30 or 2 to 20. Examples of heteroaryl groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phenoxazyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , isoquinoline group, indole group, carbazole group, N-arylcarbazole group, N-heteroarylcarbazole group, N-alkylcarbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, thienothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothia Zinyl group and dibenzofuranyl group, etc., but are not limited to these.

In this specification, the description regarding the aryl group described above can be applied, except that the arylene group is a divalent group.

In this specification, silyl groups include alkyl silyl groups and aryl silyl groups. Examples of silyl groups include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. It is not limited.

As used herein, boron groups include alkyl boron groups and aryl boron groups. Examples of boron groups include, but are not limited to, trimethyl boron group, triethyl boron group, t-butyldimethyl boron group, triphenyl boron group, diphenyl boron group, and phenyl boron group.

Hereinafter, a sirole compound according to an embodiment of the present invention will be described.

A sirole compound according to an embodiment of the present invention is represented by the following formula (1).

[Formula 1]

In Formula 1, R ₁ is a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, or an alkyl group having 1 to 20 carbon atoms.

R ₁ may be, for example, a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group.

Ar ₁ to Ar ₅ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted aryl group with 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group with 5 to 30 ring carbon atoms, A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or an unsubstituted or unsubstituted silyl group having 3 to 60 carbon atoms, and L ₁ to L ₃ each independently form a single bond or a substituted or unsubstituted ring. It is an aryl group having 6 to 12 carbon atoms, and a, b and c are each independently an integer of 0 to 4.

Ar ₁ and Ar ₂ may each independently form a ring with an adjacent group.

Ar ₁ and Ar ₂ may each independently be, for example, a hydrogen atom or a substituted or unsubstituted phenyl group.

At least one of Ar ₄ and Ar ₅ may be, for example, a substituted or unsubstituted naphthyl group.

Ar ₄ and Ar ₅ are each independently, for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted group, It may be a dibenzofuran group or a substituted or unsubstituted phenanthrene group.

Formula 1 may be represented by Formula 2 below.

[Formula 2]

Formula 1 may be selected from compounds represented in compound group 1 below.

[Compound Group 1]

The sirole compound according to an embodiment of the present invention contains an amine group and may have strong electron resistance. In addition, in the sirole compound according to an embodiment of the present invention, L ₁ of the amine group and Si of the sirole compound are bonded to each other at the meta position, thereby controlling diffusion of the HOMO (highest occupied molecular orbital) orbital of the amine group, and the molecular Amorphous properties can be improved by breaking symmetry. Accordingly, an organic electroluminescent device containing a sirole compound according to an embodiment of the present invention can achieve long lifespan and high luminous efficiency.

Hereinafter, an organic electroluminescent device according to an embodiment of the present invention will be described. Hereinafter, the differences from the sirole compound according to an embodiment of the present invention described above will be described in detail, and parts not described will be in accordance with the sirole compound according to an embodiment of the present invention described above.

1 is a cross-sectional view schematically showing an organic electroluminescent device according to an embodiment of the present invention. Figure 2 is a cross-sectional view schematically showing an organic electroluminescent device according to an embodiment of the present invention.

1 and 2, the organic electroluminescent device 10 according to an embodiment of the present invention includes an anode (AN), a hole transport region (HTR), an emission layer (EML), an electron transport region (ETR), and a cathode. Includes (CAT).

The anode (AN) is conductive. The anode (AN) may be a pixel electrode or an anode. The anode (AN) may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the anode (AN) is a transparent electrode, the anode (AN) is a transparent metal oxide, for example, indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO). It can be done as follows. When the anode (AN) is a transflective electrode or a reflective electrode, the anode (AN) is Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, It may include LiF/Al, Mo, Ti, or a compound or mixture thereof (for example, a mixture of Ag and Mg). Or a plurality of layer structure including a reflective film or semi-transmissive film formed of the above materials and a transparent conductive film formed of ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc. It can be.

A hole transport region (HTR) is provided on the anode (AN). The hole transport region (HTR) may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), a hole buffer layer, and an electron blocking layer. The thickness of the hole transport region (HTR) may be, for example, about 1000 Å to about 1500 Å.

The hole transport region (HTR) may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.

For example, the hole transport region (HTR) may have a single-layer structure of a hole injection layer (HIL) or a hole transport layer (HTL), or may have a single-layer structure composed of a hole injection material and a hole transport material. In addition, the hole transport region (HTR) has a single-layer structure made of a plurality of different materials, or has a hole injection layer (HIL)/hole transport layer (HTL), a hole injection layer ( The structure of HIL)/hole transport layer (HTL)/hole buffer layer, hole injection layer (HIL)/hole buffer layer, hole transport layer (HTL)/hole buffer layer or hole injection layer (HIL)/hole transport layer (HTL)/electron blocking layer. You can have it, but it is not limited to this.

The hole transport region (HTR) is created using various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB), inkjet printing, laser printing, and laser induced thermal imaging (LITI). It can be formed using

At least one of the hole injection layer (HIL) and the hole transport layer (HTL) may include a sirole compound represented by Formula 1 below.

[Formula 1]

In Formula 1, R ₁ is a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, or an alkyl group having 1 to 20 carbon atoms.

R ₁ may be, for example, a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group.

Ar ₁ to Ar ₅ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted aryl group with 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group with 5 to 30 ring carbon atoms, A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or an unsubstituted or unsubstituted silyl group having 3 to 60 carbon atoms, and L ₁ to L ₃ each independently form a single bond or a substituted or unsubstituted ring. It is an aryl group having 6 to 12 carbon atoms, and a, b and c are each independently an integer of 0 to 4.

Ar ₁ and Ar ₂ may each independently form a ring with an adjacent group.

Ar ₁ and Ar ₂ may each independently be, for example, a hydrogen atom or a substituted or unsubstituted phenyl group.

At least one of Ar ₄ and Ar ₅ may be, for example, a substituted or unsubstituted naphthyl group.

Ar ₄ and Ar ₅ are each independently, for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted group, It may be a dibenzofuran group or a substituted or unsubstituted phenanthrene group.

Formula 1 may be represented by Formula 2 below.

[Formula 2]

The hole transport region (HTR) may include at least one of the compounds shown in compound group 1 below.

[Compound Group 1]

The hole injection layer (HIL) includes, for example, phthalocyanine compounds such as copper phthalocyanine; DNTPD(N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine), m-MTDATA(4,4' ,4"-tris(3-methylphenylphenylamino)triphenylamine), TDATA(4,4'4"-Tris(N,N-diphenylamino)triphenylamine), 2-TNATA(4,4',4"-tris{N,- (2-naphthyl)-N-phenylamino}-triphenylamine), PEDOT/PSS(Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate)), PANI/DBSA(Polyaniline/Dodecylbenzenesulfonic acid), PANI/CSA(Polyaniline) /Camphor sulfonicacid), PANI/PSS((Polyaniline)/Poly(4-styrenesulfonate)), NPB(N,N'-di(naphthalene-l-yl)-N,N'-diplienyl-benzidine), triphenylamine It may also include polyether ketone (TPAPEK), 4-Isopropyl-4'-methyldiphenyliodonium Tetrakis(pentafluorophenyl)borate], etc.

The hole transport layer (HTL) is, for example, carbazole-based derivatives such as N-phenylcarbazole and polyvinylcarbazole, fluorine-based derivatives, TPD (N,N'-bis(3-methylphenyl)-N, Triphenylamine derivatives such as N'-diphenyl-[1,1-biphenyl]-4,4'-diamine), TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine), NPB(N ,N'-di(1-naphthyl)-N,N'-diphenylbenzidine), TAPC(4,4'-Cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine]), HMTPD(4,4'- It may also include Bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl).

The thickness of the hole transport region (HTR) may be about 100 Å to about 10000 Å, for example, about 100 Å to about 1000 Å. When the hole transport region (HTR) includes both a hole injection layer (HIL) and a hole transport layer (HTL), the thickness of the hole injection layer (HIL) is about 100 Å to about 10000 Å, for example, about 100 Å to about 1000 Å, The thickness of the hole transport layer (HTL) may be about 30Å to about 1000Å. When the thickness of the hole transport region (HTR), hole injection layer (HIL), and hole transport layer (HTL) satisfies the above-described range, satisfactory hole transport characteristics can be obtained without a substantial increase in driving voltage.

In addition to the previously mentioned materials, the hole transport region (HTR) may further include a charge generating material to improve conductivity. The charge generating material may be uniformly or non-uniformly dispersed within the hole transport region (HTR). The charge generating material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, non-limiting examples of p-dopants include quinone derivatives such as TCNQ (Tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-tetrafluoro-tetracyanoquinodimethane), metal oxides such as tungsten oxide and molybdenum oxide, etc. Examples include, but are not limited to.

As mentioned above, the hole transport region (HTR) may further include at least one of a hole buffer layer and an electron blocking layer in addition to the hole injection layer (HIL) and the hole transport layer (HTL). The hole buffer layer can increase light emission efficiency by compensating for the resonance distance according to the wavelength of light emitted from the light emitting layer (EML). The material included in the hole buffer layer may be a material that can be included in the hole transport region (HTR). The electron blocking layer is a layer that serves to prevent electron injection from the electron transport region (ETR) to the hole transport region (HTR).

The light emitting layer (EML) is provided on the hole transport region (HTR). The thickness of the light emitting layer (EML) may be, for example, about 100 Å to about 300 Å. The light emitting layer (EML) may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multi-layer structure having a plurality of layers made of a plurality of different materials.

The light emitting layer (EML) may emit one of red light, green light, blue light, white light, yellow light, and cyan light. The light emitting layer (EML) may include a fluorescent material or a phosphorescent material. Additionally, the light emitting layer (EML) may include a host and a dopant.

The host is not particularly limited as long as it is a commonly used material, for example, Alq3 (tris(8-hydroxyquinolino)aluminum), CBP (4,4'-bis(N-carbazolyl)-1,1'-biphenyl), PVK(poly(n-vinylcabazole), ADN(9,10-di(naphthalene-2-yl)anthracene), TCTA(4,4',4''-Tris(carbazol-9-yl)-triphenylamine), TPBi (1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene), TBADN(3-tert-butyl-9,10-di(naphth-2-yl)anthracene), DSA(distyrylarylene), CDBP( 4,4'-bis(9-carbazolyl)-2,2''-dimethyl-biphenyl), MADN (2-Methyl-9,10-bis(naphthalen-2-yl)anthracene), etc. can be used.

Dopants include, for example, styryl derivatives (e.g., 1, 4-bis[2-(3-N-ethylcarbazoryl)vinyl]benzene(BCzVB), 4-(di-p-tolylamino)-4'-[ (di-p-tolylamino)styryl]stilbene(DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl )-N-phenylbenzenamine (N-BDAVBi), perylene and its derivatives (e.g., 2, 5, 8, 11-Tetra-t-butylperylene (TBP)), pyrene and its derivatives (e.g., 1, It may contain dopants such as 1-dipyrene, 1, 4-dipyrenylbenzene, 1, 4-Bis(N, N-Diphenylamino)pyrene).

When the light-emitting layer (EML) emits red light, the light-emitting layer (EML) is a fluorescent material containing, for example, PBD:Eu(DBM) ₃ (Phen)(tris(dibenzoylmethanato)phenanthoroline europium) or perylene. may include. When the emitting layer (EML) emits red color, the dopant included in the emitting layer (EML) is, for example, PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonate iridium), PQIr(acac)(bis(1-phenylquinoline) Metal complexes or organometallic complexes such as acetylacetonate iridium, PQIr (tris(1-phenylquinoline)iridium), and PtOEP (octaethylporphyrin platinum), rubrene and its derivatives, and 4-dicyano It can be selected from methylene-2-(p-dimethylaminostyryl)-6-methyl-4H-pyran (DCM) and its derivatives.

When the light emitting layer (EML) emits green light, the light emitting layer (EML) may include a fluorescent material including, for example, tris(8-hydroxyquinolino)aluminum (Alq3). When the emitting layer (EML) emits green color, the dopant included in the emitting layer (EML) is, for example, a metal complex such as Ir(ppy) ₃ (fac-tris(2-phenylpyridine)iridium) or an organic dopant. It can be selected from metal complexes (organometallic complexes) and coumarin and its derivatives.

When the light emitting layer (EML) emits blue light, the light emitting layer (EML) is, for example, spiro-DPVBi (spiro-DPVBi), spiro-6P (spiro-6P), distyryl-benzene (DSB), distyryl-benzene (DSB), distyryl-benzene (DSB), and distyryl-benzene (DSB). arylene), PFO (polyfluorene)-based polymer, and PPV (poly(p-phenylene vinylene))-based polymer. It may contain a fluorescent material containing any one selected from the group consisting of. When the light-emitting layer (EML) emits blue light, The dopant included in the emitting layer (EML) can be selected from, for example, a metal complex such as (4,6-F2ppy) ₂ Irpic, an organometallic complex, perlene, and its derivatives. there is.

An electron transport region (ETR) is provided on the light emitting layer (EML). The electron transport region (ETR) may include at least one of an electron blocking layer, an electron transport layer (ETL), and an electron injection layer (EIL), but is not limited thereto.

The electron transport region (ETR) may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.

For example, the electron transport region (ETR) may have a single-layer structure of an electron injection layer (EIL) or an electron transport layer (ETL), or may have a single-layer structure composed of an electron injection material and an electron transport material. In addition, the electron transport region (ETR) has a single-layer structure made of a plurality of different materials, or an electron transport layer (ETL)/electron injection layer (EIL), a hole blocking layer/layer sequentially stacked from the anode (AN). It may have an electron transport layer (ETL)/electron injection layer (EIL) structure, but is not limited thereto. The thickness of the electron transport region (ETR) may be, for example, about 1000Å to about 1500Å.

The electron transport region (ETR) is created using various methods such as vacuum deposition, spin coating, cast, LB (Langmuir-Blodgett), inkjet printing, laser printing, and laser induced thermal imaging (LITI). It can be formed using

When the electron transport region (ETR) includes an electron transport layer (ETL), the electron transport region (ETR) is Alq3 (Tris(8-hydroxyquinolinato)aluminum), , 1,3,5-tri[(3-pyridyl)- phen-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzoimidazolyl -1-ylphenyl)-9,10-dinaphthylanthracene, TPBi(1,3,5-Tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl), BCP(2,9-Dimethyl-4 ,7-diphenyl-1,10-phenanthroline), Bphen(4,7-Diphenyl-1,10-phenanthroline), TAZ(3-(4-Biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2 ,4-triazole), NTAZ(4-(Naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), tBu-PBD(2-(4-Biphenylyl)-5-( 4-tert-butylphenyl)-1,3,4-oxadiazole), BAlq(Bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-Biphenyl-4-olato)aluminum), Bebq2( It may include, but is not limited to, berylliumbis (benzoquinolin-10-olate), ADN (9,10-di(naphthalene-2-yl)anthracene), and mixtures thereof. The thickness of the electron transport layers (ETL) is approximately It may be 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layers (ETL) satisfies the range described above, satisfactory electron transport characteristics can be obtained without a substantial increase in driving voltage. .

When the electron transport region (ETR) includes an electron injection layer (EIL), the electron transport region (ETR) is a lanthanide metal such as LiF, LiQ (Lithium quinolate), Li ₂ O, BaO, NaCl, CsF, Yb, Alternatively, halogenated metals such as RbCl and RbI may be used, but are not limited thereto. The electron injection layer (EIL) may also be made of a mixture of an electron transport material and an insulating organo metal salt. Organic metal salts can be materials with an energy band gap of approximately 4 eV or more. Specifically, for example, the organometallic salt may include metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate, or metal stearate. You can. The thickness of the electron injection layers (EIL) may be about 1Å to about 100Å, or about 3Å to about 90Å. When the thickness of the electron injection layers (EIL) satisfies the range described above, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.

The electron transport region (ETR) may include a hole blocking layer, as previously mentioned. The hole blocking layer may include, for example, at least one of BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline) and Bphen (4,7-diphenyl-1,10-phenanthroline). However, it is not limited to this.

A cathode (CAT) is provided on the electron transport region (ETR). The cathode (CAT) may be a common electrode or a cathode. The cathode (CAT) may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the cathode (CAT) is a transparent electrode, the cathode (CAT) is a transparent metal oxide, for example, indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO). It can be done as follows.

When the cathode (CAT) is a transflective electrode or a reflective electrode, the cathode (CAT) is Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, It may include LiF/Al, Mo, Ti, or a compound or mixture thereof (for example, a mixture of Ag and Mg). Or a plurality of layer structure including a reflective film or semi-transmissive film formed of the above materials and a transparent conductive film formed of ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc. It can be.

Although not shown, the cathode (CAT) may be connected to an auxiliary electrode. When the cathode (CAT) is connected to the auxiliary electrode, the resistance of the cathode (CAT) can be reduced.

In the organic electroluminescent device 10, as voltage is applied to the anode (AN) and the cathode (CAT), holes injected from the anode (AN) pass through the hole transport region (HTR) to the light emitting layer (EML). The electrons injected from the cathode (CAT) move to the light emitting layer (EML) through the electron transport region (ETR). Electrons and holes recombine in the light emitting layer (EML) to generate excitons, and the excitons emit light as they fall from the excited state to the ground state.

When the organic electroluminescent device 10 is a top-emission type, the anode (AN) may be a reflective electrode, and the cathode (CAT) may be a transmissive electrode or a semi-transmissive electrode. When the organic electroluminescent device 10 is a bottom-emitting type, the anode (AN) may be a transmissive electrode or a semi-transmissive electrode, and the cathode (CAT) may be a reflective electrode.

In the organic electroluminescent device 10 according to an embodiment of the present invention, it has been described as an example that the sirole compound represented by Chemical Formula 1 is included in the hole transport region (HTR), but it is not limited thereto, and the light emitting layer (EML) ) or may also be included in the electron transport region (ETR).

The sirole compound included in the organic electroluminescent device according to an embodiment of the present invention includes an amine group and may have strong electron resistance. In addition, in the sirole compound included in the organic electroluminescent device according to an embodiment of the present invention, L ₁ of the amine group and Si of the sirole compound are bonded to each other at the meta position, thereby controlling diffusion of the HOMO orbital of the amine group, Amorphous properties can be improved by breaking molecular symmetry. Accordingly, the organic electroluminescent device according to an embodiment of the present invention can achieve long lifespan and high luminous efficiency.

Hereinafter, the present invention will be described in more detail through specific examples. The following examples are merely examples to aid understanding of the present invention, and the scope of the present invention is not limited thereto.

Example

[Synthesis example]

[Synthesis of Compound 1]

(Synthesis of Compound A)

Add 2,2'-dibromobiphenyl (25.00 g, 80.13 mmol) and dehydrated THF (Tetrahydrofuran) (240 mL) to an argon-substituted reaction vessel, cool to -78°C, and add n-butyllithium and hexane solution (1.6 M). , 106.50mL, 168.27mmoL) was added dropwise.

Stirring was continued for 1 hour after dropwise addition, and trichlorophenylsilane (12.84mL, 80.13mmol) was added dropwise. After dropwise addition, the solution temperature was gradually returned to room temperature and stirring was continued for 2 hours to obtain solution a.

Add 1,3-dibromobenzene (20.79g, 88.14mmol) and dehydrated THF (240mL) to another reaction vessel, cool to -78°C, and add n-butyllithium hexane solution (1.6M, 55.78mL, 88.14mmoL). Dropped. Stirring was continued for 1 hour after the dropwise addition was completed. Solution a was dropped here and stirred for 2 hours while lowering the solution temperature to room temperature. It was quenched by adding water and extracted with ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate, filtered, and the filtrate was concentrated using a vacuum rotary concentrator. The obtained crude product was purified by silica gel column chromatography (developing solvent: toluene and hexane), and the obtained solid was recrystallized with ethanol to obtain 14.90 g, yield 56%, of a white powder-like solid represented as Compound A (FAB-MS: C ₂₄ H ₁₇ BrSi, measured 412.03). FAB-MS was measured using JMS-700 manufactured by JEOL.

(Synthesis of Compound 1)

Add compound A (5.00 g, 12.10 mmol), compound B (7.63 g, 13.30 mmol), toluene (48 mL), ethanol (24 mL), and 2M potassium phosphate (K ₃ PO ₄ ) aqueous solution (12 mL) to the reaction vessel. The inside of the container was replaced with argon. Next, Pd(PPh ₃ ) ₄ (0.84g, 24.19mmol) was added. Afterwards, it was stirred under reflux for 2 hours. After cooling, the organic layer was extracted, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated using a vacuum rotary concentrator. The obtained crude product was purified by silica gel column chromatography (developing solvent: toluene and hexane), and the obtained solid was recrystallized with toluene and ethanol to obtain 8.5 g of a white powder-like solid, represented by Compound 1, with a yield of 90% (FAB-MS: C ₅₈ H ₄₁ NSi, measured 779.30). FAB-MS was measured using JMS-700 manufactured by JEOL.

[Synthesis of Compound 3]

(Synthesis of Compound D)

1-Bromonaphthalene (4.12g, 19.91mmol) and THF (100mL) were added to an argon-substituted reaction vessel, cooled to -78°C, and n-butyllithium and 1.6M hexane solution (12.44mL) were added dropwise. . After dropping, it was stirred for 1 hour. A mixed solution of compound C (5.00 g, 19.91 mmol) and THF (100 mL) was added dropwise thereto, and then stirred for 30 minutes. Then, it was slowly returned to room temperature and continued to be stirred for 2 hours. After completion of the reaction, THF and unreacted 1-bromonaphthalene were distilled. No further production was carried out and it was used in the following reaction. FAB-MS was measured using JMS-700 manufactured by JEOL.

(Synthesis of Compound E)

Add 1,3-dibromonaphthalene (4.70g, 19.91mmol) and THF (100mL) to an argon-substituted reaction vessel, cool to -78°C, and add n-butyllithium and 1.6M hexane solution (12.44mL). was added dropwise. After dropwise addition, it was stirred for 1 hour. The mixed solution of compound D (6.83 g, 19.91 mmol) synthesized above and THF (100 mL) was added dropwise here, and stirred for 30 minutes. Then, it was slowly returned to room temperature, and stirring was continued for 2 hours. After completion of the reaction, water and ethyl acetate were added to the reaction solution to extract the organic layer. The obtained organic layer was dried with anhydrous magnesium sulfate, filtered, and the filtrate was concentrated using a vacuum rotary concentrator. The obtained crude product was purified by silica gel column chromatography (developing solvent: toluene and hexane) to obtain 6.2 g of colorless transparent oil represented by the target compound E, yield 67% (FAB-MS: C ₂₈ H ₁₉ BrSi measured value) 462.04). FAB-MS was measured using JMS-700 manufactured by JEOL.

(Synthesis of Compound 3)

Compound E (3.00 g, 6.47 mmol), compound B (4.08 g, 7.12 mmol), toluene (26 mL), ethanol (13 mL), and 2M potassium phosphate aqueous solution (6.5 mL) were added to the reaction vessel, and the inside of the vessel was replaced with argon. . Next, Pd(PPh ₃ ) ₄ (0.84g, 24.19mmol) was added. Afterwards, it was stirred under reflux dropwise for 2 hours. After cooling, the organic layer was extracted, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated using a vacuum rotary concentrator. The obtained crude product was purified by silica gel column chromatography (developing solvent: toluene and hexane), and the obtained solid was recrystallized with toluene and ethanol. As a result, 5.0 g of a light yellow powder solid represented by Compound 3, the target product, was obtained in a yield of 78%. (FAB-MS: C ₆₂ H ₄₃ NSi measured 829.32). FAB-MS was measured using JMS-700 manufactured by JEOL.

[Synthesis of Compound 5]

Add compound A (4.00g, 9.68mmol), compound C (3.95g, 10.64mmol), Pd(dba)2 (0.28g, 0.48mmol), and sodium t-butoxide (0.93g, 9.68mmol) to the reaction vessel. and argon was substituted. Next, dehydrated toluene (97 mL) and tri(t-butyl)phosphine toluene solution (1.5 M, 1.29 mL, 1.94 mmol) were added, followed by heating and stirring at 80°C for 1 hour. After standing to cool, water was added to the reaction solution to extract the organic layer. The obtained organic layer was dried with anhydrous magnesium sulfate, filtered, and the filtrate was concentrated using a vacuum rotary concentrator. The obtained crude product was purified by silica gel column chromatography (developing solvents: toluene and hexane), and the obtained solid was recrystallized with toluene and ethanol. As a result, 6.47 g of a white powder solid represented by the target compound 5 was obtained in a yield of 95% ( FAB-MS: C ₅₂ H ₃₇ NSi measured 703.27). FAB-MS was measured using JMS-700 manufactured by JEOL.

[Synthesis of Compound 14]

(Synthesis of Compound F)

Compound A (5.00 g, 12.10 mmol) and THF (60 mL) were added to an argon-substituted reaction vessel, cooled to -78°C, and n-butyllithium and 1.6M hexane solution (9.1 mL) were added dropwise. After dropwise addition, it was stirred for 1 hour. Subsequently, trimethoxyborane (2.7 mL, 18.1 mmol) was added dropwise. After stirring for 2 hours, the temperature was slowly raised to room temperature, 2M hydrochloric acid (60 mL) was added, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, extraction was performed with ethyl acetate. The obtained organic layer was dried with anhydrous magnesium sulfate, filtered, and the filtrate was concentrated using a vacuum rotary concentrator. The obtained product was washed with hexane, and 4.5 g of a white powder solid represented as the target Compound F was obtained in a yield of 98% (FAB-MS: C ₂₄ H ₁₉ BO ₂ Si measured value 378.12). FAB-MS was measured using JMS-700 manufactured by JEOL.

(Synthesis of Compound G)

Add compound F (2.50 g, 9.34 mmol), 3-bromo-4-chlorobiphenyl (3.88 g, 10.30 mmol), toluene (40 mL), ethanol (20 mL), and 2M potassium phosphate aqueous solution (10 mL) to the reaction vessel. , the inside of the container was replaced with argon. Next, Pd(PPh ₃ ) ₄ (0.65g, 18.69mmol) was added. Afterwards, it was stirred under reflux for 2 hours. After cooling, the organic layer was extracted, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated using a vacuum rotary concentrator. The obtained crude product was purified by silica gel column chromatography (developing solvent: toluene and hexane), and the obtained solid was recrystallized with toluene and ethanol. As a result, 3.70 g of a white powder solid represented by the target compound 3 was obtained in a yield of 76%. (FAB-MS: C ₃₆ H ₂₅ ClSi measured 520.14). FAB-MS was measured using JMS-700 manufactured by JEOL.

(Synthesis of Compound 14)

Compound G (3.5 g, 6.72 mmol), N-phenyl-1-naphthyl amine (1.62 g, 7.39 mmol), Pd(dba) ₂ (0.19 g, 0.34 mmol), and sodium t-butoxide (1.29 mmol) were added to the reaction vessel. g, 13.43 mmol) was added and replaced with argon. Next, dehydrated toluene (67 mL) and tri(t-butyl)phosphine toluene solution (1.5 M, 0.90 mL, 1.34 mmol) were added, followed by heating and stirring at 80°C for 1 hour. After standing to cool, water was added to the reaction solution to extract the organic layer. The obtained organic layer was dried with anhydrous magnesium sulfate, filtered, and the filtrate was concentrated using a vacuum rotary concentrator. The obtained crude product was purified by silica gel column chromatography (developing solvents: toluene and hexane), and the obtained solid was recrystallized with toluene and ethanol. As a result, 4.5 g of a white powder solid represented as the target compound 5 was obtained in a yield of 95% ( FAB-MS: C ₅₂ H ₃₇ NSi measured 703.27). FAB-MS was measured using JMS-700 manufactured by JEOL.

[Fabrication of organic electroluminescent devices]

An anode was formed with 150 nm thick ITO, a hole injection layer was formed with 60 nm thick 2-TNATA, a 30 nm thick hole transport layer was formed, and a 25 nm thick light emitting layer was formed by doping ADN with 3% TBP. A 25 nm thick electron transport layer was formed with Alq3, a 1 nm thick electron injection layer was formed with LiF, and a 100 nm thick cathode was formed with Al.

The compounds used to form the hole transport layer in Examples 1 to 4 and Comparative Examples 1 to 5 are shown in Table 2.

The C9920-11 luminance orientation characteristic measuring device manufactured by Hamamatsu Photonics was used to evaluate the device characteristics.

Device creation example hole transport layer Current density (mA/cm ² ) Voltage
(V) Luminous efficiency (cd/A) Example 1 Example Compound 1 10 5.8 6.7 Example 2 Example Compound 3 10 5.6 6.7 Example 3 Example Compound 5 10 5.5 7.0 Example 4 Example Compound 14 10 5.9 7.0 Comparative Example 1 Comparative Example Compound A-1 10 6.5 5.2 Comparative Example 2 Comparative Example Compound A-2 10 6.5 5.0 Comparative Example 3 Comparative Example Compound A-3 10 7.0 5.5 Comparative Example 4 Comparative Example Compound A-4 10 6.9 5.6 Comparative Example 5 Comparative Example Compound A-5 10 7.2 5.3

Example Compound 1 Example Compound 3 Example Compound 5 Example Compound 14 Comparative Example Compound A-1 Comparative Example Compound A-2 Comparative Example Compound A-3 Comparative Example Compound A-4 Comparative Example Compound A-5

Referring to Table 1, it can be seen that the organic electroluminescent devices of Examples 1 to 4 have a longer lifespan than the organic electroluminescent devices of Comparative Examples 1 to 5. Examples 1 to 4 use a sirole compound in which a sirole group and an amine group are linked. The sirol compounds of Examples 1 to 4 contain a sirol group and an amine group and have strong electron resistance. The sirol group and the amine group are connected to each other at the meta position, which can limit the diffusion of the HOMO orbital of the amine group. In addition, the sirole compounds of Examples 1 to 4 can improve hole transport properties while suppressing deterioration of the device that may occur due to electrons infiltrating the hole transport layer, thereby improving the luminous efficiency of the organic electroluminescent device. I was able to.

However, in the compounds of Comparative Examples 1, 2, 3, and 5, the amine group and sirole group are connected to each other at the para position, so the HOMO orbital is diffused, resulting in low efficiency compared to Examples 1 to 4. In addition, the compounds of Comparative Examples 3 and 4 have a spiro structure and have LUMO (lowest unoccupied molecular orbital) decreases, resulting in low efficiency.

Above, embodiments of the present invention have been described with reference to the attached drawings, but those skilled in the art will understand that the present invention can be implemented in other specific forms without changing its technical idea or essential features. You will understand that it exists. Therefore, the embodiments described above should be understood in all respects as illustrative and not restrictive.

10: Organic electroluminescent device AN: Anode
HTR: hole transport region EML: emitting layer
ETR: electron transport region CAT: cathode

Claims (19)

Sirole compounds represented by the following formula (1):
[Formula 1]

In Formula 1,
R ₁ is an unsubstituted methyl group, an unsubstituted phenyl group, or an unsubstituted naphthyl group,
Ar ₁ and Ar ₂ are each independently a hydrogen atom or an unsubstituted phenyl group, or combine with an adjacent group to form a ring,
a and b are each independently 0 or 1,
is represented by any one of the following formulas L-1 to formula L-6,
[Formula L-1] [Formula L-2]

[Formula L-3] [Formula L-4]

[Formula L-5] [Formula L-6]

In Formula L-1 to Formula L-6 is the position bonded to N, is the position bonded to Si,
and is each independently an unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted naphthyl group, an unsubstituted dibenzofuran group, or an unsubstituted phenanthryl group, or one of the formulas A-1 to A-8 below: displayed as one,
[Formula A-1] [Formula A-2] [Formula A-3]

[Formula A-4]

[Formula A-5]

[Formula A-6]

[Formula A-7] [Formula A-8]

In Formula A-1 to Formula A-8 is the position bonded to N,
The sirole compound contains only one amine group. According to paragraph 1,
The formula 1 is a sirole compound represented by the following formula 2:
[Formula 2]

In Formula 2,
Ar ₁ to Ar ₅ , a to c, and L ₁ to L ₃ are the same as defined in Formula 1 above. delete delete delete delete According to paragraph 1,
Ar ₁ and Ar ₂ are each independently,
A sirole compound that forms a ring with adjacent groups. According to paragraph 1,
Ar ₁ and Ar ₂ are each independently,
A sirole compound that is a hydrogen atom or an unsubstituted phenyl group. According to paragraph 1,
The formula 1 is a sirole compound selected from compounds represented in compound group 1 below:
[Compound Group 1]


. anode;
a hole transport region provided on the anode;
a light-emitting layer provided on the hole transport region;
an electron transport region provided on the light emitting layer; and
Comprising a cathode provided on the electron transport region,
The hole transport region is
An organic electroluminescent device comprising a sirole compound represented by the following formula (1):
[Formula 1]

In Formula 1,
R ₁ is an unsubstituted methyl group, an unsubstituted phenyl group, or an unsubstituted naphthyl group,
Ar ₁ and Ar ₂ are each independently a hydrogen atom or an unsubstituted phenyl group, or combine with an adjacent group to form a ring,
a and b are each independently 0 or 1,
is represented by any one of the following formulas L-1 to formula L-6,
[Formula L-1] [Formula L-2]

[Formula L-3] [Formula L-4]

[Formula L-5] [Formula L-6]

In Formula L-1 to Formula L-6 is the position bonded to N, is the position bonded to Si,
and is each independently an unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted naphthyl group, an unsubstituted dibenzofuran group, or an unsubstituted phenanthryl group, or one of the formulas A-1 to A-8 below: displayed as one,
[Formula A-1] [Formula A-2] [Formula A-3]

[Formula A-4]

[Formula A-5]

[Formula A-6]

[Formula A-7] [Formula A-8]

In Formula A-1 to Formula A-8 is the position bonded to N,
The sirole compound contains only one amine group. According to clause 10,
The hole transport region is
hole injection layer; and
It includes a hole transport layer provided on the hole injection layer,
At least one of the hole injection layer and the hole transport layer
An organic electroluminescent device comprising a sirole compound represented by Formula 1. According to clause 10,
An organic electroluminescent device wherein Formula 1 is represented by Formula 2:
[Formula 2]

In Formula 2,
Ar ₁ to Ar ₅ , a to c, and L ₁ to L ₃ are the same as defined in Formula 1 above. delete delete delete delete According to clause 10,
Ar ₁ and Ar ₂ are each independently,
An organic electroluminescent device that forms a ring with adjacent groups. According to clause 10,
Ar ₁ and Ar ₂ are each independently,
An organic electroluminescent device comprising a hydrogen atom or an unsubstituted phenyl group. According to clause 10,
The formula 1 is an organic electroluminescent device selected from compounds represented by the following compound group 1:
[Compound Group 1]


.

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