WO2024117762A1 - Organic light emitting device - Google Patents

Abstract

The present invention provides an organic light emitting device having improved driving voltage, efficiency, and lifespan.

Description

organic light emitting device

Cross-Citation with Related Application(s)

This application claims the benefit of priority based on Korean Patent Application No. 10-2022-0165647 dated December 1, 2022 and Korean Patent Application No. 10-2023-0168055 dated November 28, 2023, and the relevant Korean patent applications All content disclosed in the literature is incorporated as part of this specification.

The present invention relates to an organic light emitting device with improved driving voltage, efficiency, and lifespan.

In general, organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic light-emitting devices using the organic light-emitting phenomenon have a wide viewing angle, excellent contrast, fast response time, and excellent luminance, driving voltage, and response speed characteristics, so much research is being conducted.

Organic light emitting devices generally have a structure including an anode, a cathode, and an organic layer between the anode and the cathode. The organic material layer is often composed of a multi-layer structure made of different materials to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of this organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton When it falls back to the ground state, it glows.

In organic light-emitting devices as described above, there is a continuous need for the development of organic light-emitting devices with improved driving voltage, efficiency, and lifespan.

Prior art literature

patent literature

(Patent Document 0001) Korean Patent Publication No. 10-2000-0051826

The present invention relates to an organic light emitting device with improved driving voltage, efficiency, and lifespan.

The present invention provides the following organic light emitting device:

anode;

cathode;

a light-emitting layer between the anode and the cathode;

A hole blocking layer between the cathode and the light emitting layer; and

It includes an electron transport layer, an electron injection layer, or an electron transport and injection layer between the hole blocking layer and the cathode,

The hole blocking layer includes a first compound represented by the following formula (1),

The electron transport layer, electron injection layer, or electron transport and injection layer includes a second compound represented by the following formula (2),

The values of the dipole moment of the first compound represented by Formula 1 and the dipole moment of the second compound represented by Formula 2 satisfy the following equation 1:

[Formula 1]

In Formula 1,

X is O or S,

At least one of R ₁ is represented by the following formula A, and the others are each independently hydrogen, deuterium, substituted or unsubstituted C _1-60 alkyl, substituted or unsubstituted C _6-60 aryl, and substituted or unsubstituted It is C _2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of N, O, S and Si, or two adjacent R ₁ are bonded to each other to form a substituted or unsubstituted aromatic ring, ,

[Formula A]

In Formula A,

X ₁ is each independently N or CR ₂ , but at least one of X ₁ is N,

R ₂ is hydrogen, deuterium, or combined with an adjacent substituent -(L _2-- ) _l2 -Ar ₂ or -(L ₃ ) _l3 -Ar ₃ to form a substituted or unsubstituted aromatic ring;

L ₁ to L ₃ are each independently a single bond, a substituted or unsubstituted C _6-60 arylene, or one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, S and Si. It is C _2-60 heteroarylene containing,

Ar ₂ and Ar ₃ are each independently, substituted or unsubstituted C _1-60 alkyl, substituted or unsubstituted C _1-60 alkoxy, substituted or unsubstituted C _6-60 aryl, substituted or unsubstituted N, C _2-60 heteroaryl containing at least one heteroatom selected from the group consisting of O, S and Si, or -Si(Z ₁ )(Z ₂ )(Z ₃ ),

Here, Z ₁ to Z ₃ are each independently substituted or unsubstituted C _1-60 alkyl, or substituted or unsubstituted C _6-60 aryl,

l ₁ to l ₃ are each independently an integer of 1 to 3,

When l ₁ is 2 or more, two or more L ₁ are the same or different from each other,

When l ₂ is 2 or more, two or more L ₂ are the same or different from each other,

When l ₃ is 2 or more, two or more L ₃ are the same or different from each other,

[Formula 2]

In Formula 2,

X ₂ is each independently N or CR ₃ , but at least two of X ₂ are N,

X ₃ is each independently N or CR ₄ , but at least two of X ₃ are N,

R ₃ and R ₄ are each independently hydrogen, deuterium, substituted or unsubstituted C _1-60 alkyl, or substituted or unsubstituted C _6-60 aryl, or two adjacent R ₃ or R ₄ are bonded to each other Forming a substituted or unsubstituted aromatic ring,

L ₄ and L ₅ are each independently a single bond or substituted or unsubstituted C _6-60 arylene,

Ar ₄ is phenylene or biphenyldiyl,

Ar ₄ is unsubstituted or substituted with one or more deuterium,

At least one of R ₃ , R ₄ and Ar ₄ is substituted with cyano,

However, when L ₄ and L ₅ are a single bond, Ar ₄ is unsubstituted or deuterium-substituted phenylene or biphenyldiyl,

[Equation 1]

P _EI > P _EB + 2

In equation 1 above,

P _EI means the dipole moment value of the compound represented by Formula 2,

P _EB refers to the dipole moment value of the compound represented by Formula 1.

The organic light emitting device described above is excellent in driving voltage, efficiency, and lifespan.

Figure 1 shows an example of an organic light emitting device consisting of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.

2 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (3), a hole blocking layer (7), an electron transport and injection layer (8), and a cathode (4). ) shows an example of an organic light-emitting device made of.

Hereinafter, the present invention will be described in more detail to aid understanding.

In this specification,

or

means a bond connected to another substituent.

As used herein, the term “substituted or unsubstituted” refers to deuterium; halogen group; Nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkylthioxy group; Arylthioxy group; Alkyl sulphoxy group; Aryl sulfoxy group; silyl group; boron group; Alkyl group; Cycloalkyl group; alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkylamine group; heteroarylamine group; Arylamine group; Arylphosphine group; or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups containing one or more of N, O and S atoms, or substituted or unsubstituted with two or more of the above-exemplified substituents linked. do. For example, “a substituent group in which two or more substituents are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.

In this specification, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, the substituent may have the following structure, but is not limited thereto.

In the present specification, the oxygen of the ester group may be substituted with a straight-chain, branched-chain, or ring-chain alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a substituent of the following structural formula, but is not limited thereto.

In this specification, the carbon number of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, the substituent may have the following structure, but is not limited thereto.

In the present specification, the silyl group specifically includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited to this.

In this specification, the boron group specifically includes trimethyl boron group, triethyl boron group, t-butyldimethyl boron group, triphenyl boron group, and phenyl boron group, but is not limited thereto.

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

In the present specification, the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10. According to another embodiment, the carbon number of the alkyl group is 1 to 6. Specific examples of alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n. -pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, etc., but is not limited to these.

In the present specification, the alkenyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group, etc., but are not limited to these.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, Examples include, but are not limited to, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as a phenyl group, biphenyl group, or terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.

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

It can be etc. However, it is not limited to this.

In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si, and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of heterocyclic 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, and acridyl group. , pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , carbazole group, benzooxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, isoxazolyl group, thiadia These include, but are not limited to, a zolyl group, a phenothiazinyl group, and a dibenzofuranyl group.

In the present specification, an aromatic ring refers to a condensed monocyclic or condensed polycyclic ring that contains only carbon as a ring-forming atom and has aromaticity throughout the molecule. The carbon number of the aromatic ring is 6 to 60, or 6 to 30, or 6 to 20, but is not limited thereto. Additionally, the aromatic ring may be a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyrene ring, etc., but is not limited thereto.

In this specification, the aryl group among the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above. In this specification, the aralkyl group, alkylaryl group, and alkylamine group are the same as the examples of the alkyl group described above. In the present specification, the description regarding the heterocyclic group described above may be applied to heteroaryl among heteroarylamines. In this specification, the alkenyl group among the aralkenyl groups is the same as the example of the alkenyl group described above. In the present specification, the description of the aryl group described above can be applied, except that arylene is a divalent group. In the present specification, the description of the heterocyclic group described above can be applied, except that heteroarylene is a divalent group. In the present specification, the description of the aryl group or cycloalkyl group described above can be applied, except that the hydrocarbon ring is not monovalent and is formed by combining two substituents. In the present specification, the description of the heterocyclic group described above can be applied, except that the heterocycle is not a monovalent group and is formed by combining two substituents.

Meanwhile, in order to improve the efficiency of organic light-emitting devices, compounds with a high dipole moment, that is, high intramolecular polarity, are used as electron transport layer materials located in the electron transport region between the cathode and the light-emitting layer. However, when the electron transport layer containing a compound with a high dipole moment is in contact with the light-emitting layer, excitons generated at the interface are lost, which may cause a problem in which the efficiency of the organic light-emitting device is reduced.

Accordingly, the organic light emitting device according to the present invention further includes a hole blocking layer between the light emitting layer and the electron transport layer including a compound having a dipole moment value smaller than the compound included in the electron transport layer, so that the interface between the light emitting layer and the electron transport layer Prevents excitons from being lost.

Specifically, the dipole moment values of the first compound included in the hole blocking layer and the second compound included in the electron transport layer satisfy the following [Equation 1].

[Equation 1]

P _EI > P _EB + 2

In equation 1 above,

P _EI means the dipole moment value of the compound represented by Formula 2,

P _EB refers to the dipole moment value of the compound represented by Formula 1.

As in Equation 1 above, when the difference between the dipole moment value of the second compound included in the electron transport layer and the dipole moment value of the first compound included in the hole blocking layer is greater than 2, the loss of excitons at the interface with the light-emitting layer This can prevent and increase the lifespan of the organic light emitting device.

For example, the dipole moment value of the first compound may be greater than +2, greater than +2.1, greater than +2.2, greater than +2.3, greater than +2.4, or greater than +2.5 than the dipole moment value of the second compound. .

In addition, the more similar moieties the first compound included in the hole blocking layer and the second compound included in the electron transport layer have, the more smoothly the movement of electrons from the cathode-electron transport layer-hole blocking layer-light emitting layer can be achieved. . Therefore, it is necessary that the materials included in the hole blocking layer and the electron transport layer have similar moieties and a dipole moment in the above-mentioned range, and to realize this, the organic light-emitting device of the present invention has a hole blocking layer, as described later. It includes a first compound represented by the following formula (1) that does not contain a cyano group, and at the same time, the electron transport layer includes a second compound represented by the following formula (2) that necessarily includes a cyano group.

As a result, the organic light-emitting device does not have a cyano group, preventing loss of excitons in the light-emitting layer due to the hole blocking layer exhibiting a low dipole moment value, and at the same time, the density of the electron transport layer according to the compound substituted with the cyano group is increased, thereby increasing the cyano group Compared to an organic light emitting device having a hole blocking layer containing a compound substituted with a and an electron transport layer not containing a compound substituted with a cyano group, it exhibits high efficiency and increased lifespan.

Meanwhile, the dipole moment in the present invention is a physical quantity indicating the degree of polarity, and can be calculated using Equation 1 below, and “Debye (D)” is used as the unit.

[Equation 1]

By calculating the molecular density in Equation 1 above, the value of the dipole moment can be obtained. For example, molecular density can be obtained by calculating the charge and dipole of each atom using a method called Hirshfeld Charge Analysis and calculating it according to the equation below, and putting the calculation result into Equation 1 above to obtain the dipole moment. (Dipole Moment) can be obtained.

In addition, in order to obtain a high-efficiency organic light-emitting device that can be driven at a low voltage, the holes and electrons injected into the organic light-emitting device must be smoothly transferred to the light-emitting layer, while preventing the injected holes and electrons from escaping out of the light-emitting layer. To achieve this, a material having an appropriate HOMO (Highest occupied molecular orbital) energy level, LUMO (Lowest Unoccupied Molecular Orbital) energy level, and bandgap must be used. In particular, the LUMO energy levels of the host material used in the light-emitting layer and the material used in the electron transport layer are important in terms of controlling the charge balance of the entire device.

At this time, the term 'LUMO energy level' used in this specification refers to the distance from the vacuum level to the lowest unoccupied molecular orbital, and the 'HOMO energy level' refers to the distance from the vacuum level to the highest occupied molecular orbital, Even when the energy level is displayed in the minus (-) direction from the vacuum level, the energy level is interpreted to mean the absolute value of the corresponding energy value.

This LUMO energy level can be obtained after measuring the HOMO energy level, which is obtained through UV photoelectron spectroscopy, which measures the ionization potential (IP) of a material by detecting electrons that protrude when UV is irradiated to the thin film surface. It can be obtained experimentally through (ultraviolet photoemission spectroscopy, UPS). At this time, the HOMO energy level and LUMO energy level can each be calculated as shown in Equation 1 below.

[Equation 1]

HOMO (eV) = IP

LUMO (eV) = HOMO - Optical energy gap (Optical gap)

Alternatively, the HOMO energy level and LUMO energy level can be measured using the oxidation potential and reduction potential obtained through voltage sweep after dissolving the measurement target material in a solvent together with an electrolyte, respectively. there is.

Specifically, the HOMO energy level measures the onset potential (E _onset ) at which oxidation of the material to be measured begins, measures the potential of ferrocene (E _1/2(Fc) ) under the same conditions, and then converts the potential of ferrocene into the vacuum energy level. By setting the contrast to 4.8 eV, it can be calculated using Equation 2 below.

[Equation 2]

HOMO (eV) = 4.8 + (E _onset - E _1/2(Fc) )

In addition, the LUMO energy level can be calculated using the absorption spectrum, using the absorption edge wavelength (λ _edge ) of the measurement target material as the band gap, and converting it into energy units, using Equation 3 below. At this time, the band gap means the difference between the LUMO energy level and the HOMO energy level.

[Equation 3]

Bandgap (eV) = 1240 / λ _edge

LUMO (eV) = HOMO (eV) - Bandgap (eV)

Meanwhile, the organic light emitting device according to the present invention includes a material having a specific LUMO energy level in each of the hole blocking layer, electron transport layer, electron injection layer, or electron transport and injection layer, so that electrons injected from the cathode are smoothly transferred to the light emitting layer. And the transferred electrons are efficiently recombined with holes, resulting in low driving voltage and high efficiency.

Specifically, the LUMO energy level of the first compound of the organic light-emitting device is 2.6 eV to 2.85 eV, and the LUMO energy level of the second compound is 2.85 eV to 3.2 eV. The hole blocking material is a xanthe-based compound and has a structure represented by Chemical Formula 1, described later, and the electron transport and/or injection material is an azine-based compound and has a structure represented by Chemical Formula 2, described later, containing at least one cyano group. . If the LUMO energy level of the hole blocking material is outside the above-described range, it may cause holes to leak from the light-emitting layer to the adjacent layer, and if the LUMO energy level of the electron transport and/or injection material is outside the above-mentioned range. , electron transfer from the electron transport layer, etc. to the light emitting layer may be inhibited. Therefore, the hole blocking layer and the electron transport layer according to the present invention can improve the characteristics of the organic light-emitting device by appropriately aligning the LUMO levels of molecules through which electrons can move.

Hereinafter, the present invention will be described in detail for each configuration.

anode and cathode

The anode and cathode used in the present invention refer to electrodes used in organic light-emitting devices.

The anode material is generally preferably a material with a large work function to facilitate hole injection into the organic layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline are included, but are not limited to these.

The cathode material is generally preferably a material with a small work function to facilitate electron injection into the organic layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layer structure materials such as LiF/Al or LiO ₂ /Al, but they are not limited to these.

luminescent layer

The light-emitting material included in the light-emitting layer is a material that can emit light in the visible range by transporting holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining them, and a material with good quantum efficiency for fluorescence or phosphorescence is preferable.

Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV) series polymer; Spiro compounds; Polyfluorene, rubrene, etc., but are not limited to these.

The light emitting layer may include a host material and a dopant material. Host materials include condensed aromatic ring derivatives or heterocyclic ring-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds. These include, but are not limited to, furan compounds and pyrimidine derivatives.

Meanwhile, the dopant material is not particularly limited as long as it is a material used in organic light-emitting devices. Examples include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, and periplanthene, and styrylamine compounds include substituted or unsubstituted arylamino groups. It is a compound in which at least one arylvinyl group is substituted on the arylamine, and is substituted or unsubstituted with one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group, and arylamino group. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc. are included, but are not limited thereto. Additionally, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

hole transport layer

The organic light emitting device according to the present invention may include a hole transport layer between the light emitting layer and the anode.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light-emitting layer. It is a hole transport material that can receive holes from the anode or hole injection layer and transfer them to the light-emitting layer, and is a material with high mobility for holes. This is suitable.

Specific examples of the hole transport material include arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions, but are not limited to these.

Hole injection layer

The organic light emitting device according to the present invention may further include a hole injection layer between the anode and the hole transport layer, if necessary.

The hole injection layer is a layer that injects holes from an electrode. The hole injection material has the ability to transport holes, has an excellent hole injection effect at the anode, a light-emitting layer or a light-emitting material, and has an excellent hole injection effect on the light-emitting layer or light-emitting material. A compound that prevents movement of excitons to the electron injection layer or electron injection material and has excellent thin film forming ability is preferred. Additionally, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer.

Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrilehexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. organic substances, anthraquinone, polyaniline, and polythiophene series conductive polymers, etc., but are not limited to these.

hole blocking layer

The hole blocking layer is formed on the light emitting layer. Specifically, the hole blocking layer is provided in contact with the light emitting layer, and serves to improve the efficiency of the organic light emitting device by preventing excessive movement of holes and increasing the probability of hole-electron coupling. This means the layer that In particular, in the present invention, the first compound represented by Formula 1 may be used as a material for the hole blocking layer.

Preferably, at least one of R ₁ is represented by the formula A, and the others are each independently hydrogen, deuterium, methyl, n-propyl, n-butyl, tert-butyl, phenyl, biphenylyl, terphenylyl , naphthyl, dimethylfluorenyl, or triphenylenyl, or two adjacent R ₁ are combined with each other to form an unsubstituted or deuterium-substituted benzene ring; Here, the phenyl is unsubstituted or substituted with one or more deuterium, methyl, or tert-butyl.

Preferably, one or both of R ₁ are represented by formula A above.

Preferably, at least two of X ₁ are N.

Preferably, R- ₂ is hydrogen, deuterium, or unsubstituted in combination with an adjacent substituent -(L _2-- ) _l2 -Ar ₂ or -(L ₃ ) _l3 -Ar ₃ , or substituted with deuterium. Forms a benzene ring.

Preferably, l ₁ is 1 or 2,

L ₁ is each independently a single bond, phenylene, biphenyldiyl, naphthyldiyl, dibenzothiophenylene, dibenzofuranylene, dimethylfluorenylene, furanylene, thiophenylene, carbazol-9-ylene , pyridinylene, indolodimethylfluorenylene, 9-phenylcarbazolylene, dimethylsilylfluorenylene, phenoxathiinilene, phenoxazinylene, 9-phenylbenzocarbazolylene, or benzocarbazole-9- It's Ilen; Here, L ₁ is unsubstituted or substituted with one or more deuterium, methyl, phenyl, or dimethylphenyl.

More preferably, the phenylene is unsubstituted or substituted with one or more deuterium or methyl, and the 9-phenylcarbazolylene and 9-phenylbenzocarbazolylene are unsubstituted or substituted with one or more deuterium or methyl. , phenyl, or dimethylphenyl.

Preferably, l ₂ and l ₃ are each independently 1 or 2; L ₂ and L ₃ are each independently a single bond, phenylene, biphenyldiyl, dibenzothiophenylene, dibenzofuranilene, carbazol-9-ylene, or 9-phenylcarbazolylene; Here, when L ₂ and L ₃ are phenylene, biphenyldiyl, dibenzothiophenylene, dibenzofuranylene, carbazol-9-ylene and 9-phenylcarbazolylene, L ₂ and L ₃ are unsubstituted or , or one or more substituents selected from the group consisting of deuterium, methyl, phenyl, and tolyl.

Preferably, Ar ₂ and Ar ₃ are each independently selected from phenyl, biphenylyl, naphthyl, terphenylyl, triphenylenyl, phenalenyl, dimethylfluorenyl, phenanthrenyl, fluoranthenyl, carbazole- 9-yl, 9-phenylcarbazolyl, dibenzothiophenyl, phenoxazinyl, phenoxathiinyl, phenothiazinyl, benzocarbazolyl, dibenzofuranyl, pyridinyl, indolodimethylfluorenyl, phenylindolo dimethylfluorenyl, dimethylsilafluorenyl, triphenylsilyl, dimethylacridinyl, or quinolinyl; Here, Ar ₂ and Ar ₃ are unsubstituted or phenyl substituted with deuterium, cyano, methyl, trifluoromethyl, trifluoromethoxy, cyano, trimethylsilyl, triphenylsilyl, carbazol-9-yl, It is substituted with one or more substituents selected from the group consisting of dibenzothiophenyl, and dibenzofuranyl.

Representative examples of the first compound represented by Formula 1 are as follows:

.

On the other hand, if any one of R ₁ among the first compounds represented by Formula 1 is represented by Formula A and the remainder is hydrogen, it can be prepared, for example, by a production method as shown in Scheme 1 below, and the remaining compounds can also be manufactured similarly.

[Scheme 1]

In Scheme 1, all elements except Z are as previously defined, and Z is halogen, preferably bromo or chloro.

The reaction is preferably performed in the presence of a palladium catalyst and a base, and the reactor for the reaction can be changed according to what is known in the art. The manufacturing method may be further detailed in the manufacturing examples described later.

Electron transport layer, electron injection layer or electron transport and injection layer

The organic light emitting device according to the present invention may include an electron transport layer, an electron injection layer, or an electron transport and injection layer between the light emitting layer and the cathode.

The electron transport layer is a layer that receives electrons from the cathode or the electron injection layer formed on the cathode and transports electrons to the light-emitting layer, and also suppresses the transfer of holes from the light-emitting layer. The electron transport material is used to effectively inject electrons from the cathode. As a material that can receive and transfer to the light-emitting layer, a material with high mobility for electrons is suitable, and in the present invention, it may include a compound represented by Formula 2 above.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an excellent electron injection effect from the cathode, a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer. It is preferable to use a compound that prevents movement to the layer and has excellent thin film forming ability, and in the present invention, it may include the compound represented by Formula 2 above.

The electron transport and injection layer is a layer that simultaneously transports and injects electrons, and may include a second compound represented by Formula 2.

Preferably, R ₃ and R ₄ are each independently hydrogen, deuterium, methyl, iso-propyl, phenyl, biphenylyl, terphenylyl, naphthyl, phenyl naphthyl, naphthyl phenyl, phenyl naphthyl phenyl, or pyridinyl, or combined with each other to form an unsubstituted or deuterium-substituted benzene ring; Here, R ₃ and R ₄ are unsubstituted or substituted with one or more substituents selected from the group consisting of methyl, tert-butyl, cyclohexyl, and cyano.

Preferably, L ₄ and L ₅ are each independently phenylene, biphenyldiyl, or naphthylene.

The substituent -L ₄ -Ar ₄ -L ₅ - may be, for example, any one selected from the group consisting of the following substituents:

In the above group,

a is an integer from 0 to 4,

b is an integer from 0 to 3,

c is an integer from 0 to 6.

Representative examples of the second compound represented by Formula 2 are as follows:

.

Meanwhile, the second compound represented by Chemical Formula 2 can be prepared, for example, by the preparation method shown in Scheme 2 below, and the remaining compounds can be prepared similarly.

[Scheme 2]

In Scheme 2, all elements except Z are as defined above, and Z is halogen, preferably bromo or chloro.

The reaction is preferably performed in the presence of a palladium catalyst and a base, and the reactor for the reaction can be changed according to what is known in the art. The manufacturing method may be further detailed in the manufacturing examples described later.

The electron transport layer may further include a metal complex compound. Specific examples of the metal complex compound include Al complex of 8-hydroxyquinoline; Complex containing Alq ₃ ; organic radical compounds; Hydroxyflavone-metal complexes, etc., but are not limited to these. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials with a low work function followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

Specific examples of materials that can be used as the electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, and preore. Examples include, but are not limited to, nylidene methane, anthrone, etc. and their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives.

Examples of the metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, Tris(2-methyl-8-hydroxyquinolinato)aluminum, Tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-hydroxyquinolinato)chlorogallium, bis(2-methyl-8-hydroxyquinolinato) Nolinato) (o-cresolato) gallium, bis (2-methyl-8-hydroxyquinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-hydroxyquinolinato) (2- Naphtolato) gallium, etc., but is not limited thereto.

organic light emitting device

The structure of an organic light-emitting device according to the present invention is illustrated in Figure 1. Figure 1 shows an example of an organic light emitting device consisting of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. 2 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (3), a hole blocking layer (7), an electron transport and injection layer (8), and a cathode (4). ) shows an example of an organic light-emitting device made of.

The organic light emitting device according to the present invention can be manufactured by sequentially stacking the above-described structures. At this time, a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation is used to deposit a metal or a conductive metal oxide or an alloy thereof on the substrate to form an anode. It can be manufactured by forming each of the above-described layers thereon and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device can be made by sequentially depositing a cathode material on a substrate and then an anode material in the reverse order of the above-described configuration (WO 2003/012890). Additionally, the light-emitting layer can be formed by using a solution coating method as well as a vacuum deposition method for the host and dopant. Here, the solution application method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

In addition to this method, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited to this.

Meanwhile, the organic light-emitting device according to the present invention may be a bottom-emitting device, a top-emitting device, or a double-sided light-emitting device. In particular, it may be a bottom-emitting device that requires relatively high luminous efficiency.

Below, preferred embodiments are presented to aid understanding of the present invention. However, the following examples are provided only to make the present invention easier to understand, and the content of the present invention is not limited thereto.

[Manufacturing example]

Preparation Example 1: Preparation of Compound H1

In a nitrogen atmosphere, H1-A (20 g, 43.6 mmol) and H1-B (16.9 g, 43.6 mmol) were added to 400 ml of tetrahydrofuran, stirred, and refluxed. Afterwards, potassium carbonate (18.1 g, 130.9 mmol) was dissolved in 18 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in 557 mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to prepare white solid compound H1 (16.4 g, 59%).

MS: [M+H] ⁺ = 639

Preparation Example 2: Preparation of Compound H2

Compound H2 was prepared in the same manner as in Synthesis Example 1, except that each starting material was prepared according to the above reaction formula.

MS: [M+H] ⁺ = 537

Preparation Example 3: Preparation of Compound H3

Compound H3 was prepared in the same manner as in Synthesis Example 1, except that each starting material was used according to the above reaction scheme.

MS: [M+H] ⁺ = 728

Preparation Example 4: Preparation of Compound H4

In a nitrogen atmosphere, H4-A (20 g, 34.2 mmol) and H4-B (9.2 g, 34.2 mmol) were added to 400 ml of tetrahydrofuran, stirred, and refluxed. Afterwards, potassium carbonate (14.2 g, 102.7 mmol) was dissolved in 14 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (1.2 g, 1 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in 544 mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to prepare white solid compound H4 (19 g, 70%).

MS: [M+H] ⁺ = 795

Preparation Example 5: Preparation of Compound H5

Compound H5 was prepared in the same manner as in Synthesis Example 1, except that each starting material was used according to the above reaction formula.

MS: [M+H] ⁺ = 762

Preparation Example 6: Preparation of Compound H6

Compound H6 was prepared in the same manner as in Synthesis Example 1, except that each starting material was used according to the above reaction scheme.

MS: [M+H] ⁺ = 640

Preparation Example 7: Preparation of compound H7

Compound H7 was prepared in the same manner as in Synthesis Example 1, except that each starting material was used according to the above reaction scheme.

MS: [M+H] ⁺ = 640

Preparation Example 8: Preparation of Compound H8

Compound H8 was prepared in the same manner as in Synthesis Example 1, except that each starting material was used according to the above reaction formula.

MS: [M+H] ⁺ = 690

Preparation Example 9: Preparation of Compound H9

Compound H9 was prepared in the same manner as in Synthesis Example 1, except that each starting material was prepared according to the above reaction scheme.

MS: [M+H] ⁺ = 746

Preparation Example 10: Preparation of Compound H10

Compound H10 was prepared in the same manner as in Synthesis Example 1, except that each starting material was used according to the above reaction formula.

MS: [M+H] ⁺ = 792

Preparation Example 11: Preparation of Compound E1

In a nitrogen atmosphere, E1-A (20 g, 76.7 mmol) and E1-B (66.8 g, 153.4 mmol) were added to 400 ml of tetrahydrofuran, stirred, and refluxed. Afterwards, potassium carbonate (31.8 g, 230 mmol) was dissolved in 32 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (2.7 g, 2.3 mmol) was added. After reacting for 1 hour, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in 1100 mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to prepare white solid compound E1 (27.5 g, 50%).

MS: [M+H] ⁺ = 718

Preparation Example 12: Preparation of Compound E2

Compound E2 was prepared in the same manner as in Synthesis Example 1, except that each starting material was prepared according to the above reaction scheme.

MS: [M+H] ⁺ = 718

Preparation Example 13: Preparation of Compound E3

Compound E3 was prepared in the same manner as in Synthesis Example 11, except that each starting material was used according to the above reaction scheme.

MS: [M+H] ⁺ = 744

Preparation Example 14: Preparation of Compound E4

Compound E4 was prepared in the same manner as in Synthesis Example 1, except that each starting material was used according to the above reaction formula.

MS: [M+H] ⁺ = 594

Preparation Example 15: Preparation of Compound E5

Compound E5 was prepared in the same manner as in Synthesis Example 11, except that each starting material was used according to the above reaction scheme.

MS: [M+H] ⁺ = 794

Preparation Example 16: Preparation of Compound E6

Compound E6 was prepared in the same manner as in Synthesis Example 1, except that each starting material was prepared according to the above reaction scheme.

MS: [M+H] ⁺ = 794

Preparation Example 17: Preparation of Compound E7

Compound E7 was prepared in the same manner as in Synthesis Example 1, except that each starting material was used according to the above reaction scheme.

MS: [M+H] ⁺ = 718

Preparation Example 18: Preparation of Compound E8

Compound E8 was prepared in the same manner as in Synthesis Example 1, except that each starting material was used according to the above reaction scheme.

MS: [M+H] ⁺ = 794

Preparation Example 19: Preparation of Compound E9

Compound E9 was prepared in the same manner as in Synthesis Example 1, except that each starting material was prepared according to the above reaction scheme.

MS: [M+H] ⁺ = 799

Preparation Example 20: Preparation of Compound E10

Compound E10 was prepared in the same manner as in Synthesis Example 1, except that each starting material was used according to the above reaction scheme.

MS: [M+H] ⁺ = 691

[Example]

Example 1: Device example

A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1000 Å was placed in distilled water with a detergent dissolved in it and washed with ultrasonic waves. At this time, a detergent from Fischer Co. was used, and distilled water filtered secondarily using a filter from Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, it was ultrasonic washed with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned for 5 minutes using oxygen plasma and then transported to a vacuum evaporator.

On the ITO transparent electrode prepared in this way, the following HI-A compound was thermally vacuum deposited to a thickness of 600 Å to form a hole injection layer. On the hole injection layer, 50 Å of the HAT compound below and 60 Å of the HT-A compound below were sequentially vacuum deposited to form a first hole transport layer and a second hole transport layer. Subsequently, the following BH compound and compound BD were vacuum deposited on the second hole transport layer to a film thickness of 200 Å at a weight ratio of 50:1 to form a light emitting layer. Compound H1 prepared in Preparation Example 1 was vacuum deposited on the light emitting layer to a thickness of 50 Å to form a hole blocking layer, and Compound E1 prepared in Preparation Example 11 and the following LiQ compound were vacuum deposited at a weight ratio of 1:1. Thus, an electron transport and injection layer was formed with a thickness of 300Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 10 Å and aluminum to a thickness of 1000 Å on the electron transport and injection layer.

In the above process, the deposition rate of organic materials was maintained at 0.4 Å/sec to 0.9 Å/sec, the deposition rate of lithium fluoride of the cathode was maintained at 0.3 Å/sec, and aluminum was maintained at 2 Å/sec, and the vacuum level during deposition was An organic light emitting device was manufactured by maintaining 1 * 10 ^-7 torr to 5 * 10 ^-5 torr.

Examples 2 to 100

An organic light emitting device was manufactured in the same manner as in Example 1-1, except that the compounds listed in Table 1 below were used instead of compounds H1 and E1 in Example 1-1.

Comparative Examples 1 to 100

An organic light-emitting device was manufactured in the same manner as Example 1, except that the compounds listed in Table 1 below were used instead of compounds H1 and E1 of Example 1.

Experimental Example 1: Evaluation of device characteristics

For the organic light-emitting devices manufactured in Examples 1 to 100 and Comparative Examples 1 to 100, the driving voltage and luminous efficiency were measured at a current density of 10 mA/cm ² , and the luminance was 90% of the initial luminance at a current density of 20 mA/cm ^2. The time (T90) was measured, and the results are shown in Table 1 below. Additionally, the LUMO energy level values of each compound are listed in Table 1 below.

Meanwhile, the calculation of the LUMO energy level (eV) was performed using the quantum chemical calculation program DMol3 manufactured by Biovia, using density functional theory (DFT), Bpw91 as the functional function, and dnd as the basis function. For the optimized structure, the dipole moment was calculated using time-dependent density functional theory (TD-DFT).

division	hole blocking layer		Electron transport and injection layer		OLED characteristics
	compound	LUMO (eV)	compound	LUMO (eV)	Voltage (V) (@10mA/cm 2 )	Efficiency (cd/A) (@10mA/cm 2 )	Color coordinates (x, y)	T90(hr) (@20mA/cm 2 )
Example 1	H1	2.96	E1	2.85	3.40	4.51	(0.135, 0.088)	302
Example 2	H1	2.96	E2	2.95	3.33	4.69	(0.135, 0.089)	332
Example 3	H1	2.96	E3	2.85	3.47	4.28	(0.135, 0.087)	272
Example 4	H1	2.96	E4	2.97	3.50	4.37	(0.135, 0.088)	278
Example 5	H1	2.96	E5	2.95	3.57	4.06	(0.135, 0.089)	326
Example 6	H1	2.96	E6	2.88	3.30	4.74	(0.135, 0.087)	314
Example 7	H1	2.96	E7	2.86	3.32	4.74	(0.135, 0.088)	293
Example 8	H1	2.96	E8	2.97	3.37	4.64	(0.135, 0.088)	287
Example 9	H1	2.96	E9	2.88	3.30	4.74	(0.135, 0.089)	320
Example 10	H1	2.96	E10	2.98	3.47	4.58	(0.135, 0.087)	269
Example 11	H2	2.71	E1	2.85	3.50	4.28	(0.135, 0.088)	269
Example 12	H2	2.71	E2	2.95	3.43	4.46	(0.135, 0.089)	296
Example 13	H2	2.71	E3	2.85	3.57	4.07	(0.135, 0.087)	242
Example 14	H2	2.71	E4	2.97	3.61	4.16	(0.135, 0.088)	247
Example 15	H2	2.71	E5	2.95	3.68	3.86	(0.135, 0.088)	290
Example 16	H2	2.71	E6	2.88	3.40	4.50	(0.135, 0.089)	280
Example 17	H2	2.71	E7	2.86	3.41	4.51	(0.135, 0.087)	261
Example 18	H2	2.71	E8	2.97	3.47	4.40	(0.135, 0.088)	255
Example 19	H2	2.71	E9	2.88	3.40	4.50	(0.135, 0.089)	285
Example 20	H2	2.71	E10	2.98	3.57	4.35	(0.135, 0.087)	239
Example 21	H3	2.79	E1	2.85	3.33	4.60	(0.135, 0.088)	293
Example 22	H3	2.79	E2	2.95	3.27	4.78	(0.135, 0.088)	322
Example 23	H3	2.79	E3	2.85	3.40	4.37	(0.135, 0.089)	264
Example 24	H3	2.79	E4	2.97	3.43	4.46	(0.135, 0.087)	270
Example 25	H3	2.79	E5	2.95	3.50	4.14	(0.135, 0.088)	316
Example 26	H3	2.79	E6	2.88	3.23	4.83	(0.135, 0.089)	305
Example 27	H3	2.79	E7	2.86	3.25	4.84	(0.135, 0.087)	284
Example 28	H3	2.79	E8	2.97	3.30	4.73	(0.135, 0.088)	278
Example 29	H3	2.79	E9	2.88	3.23	4.83	(0.135, 0.088)	311
Example 30	H3	2.79	E10	2.98	3.40	4.67	(0.135, 0.089)	261
Example 31	H4	2.85	E1	2.85	3.47	4.33	(0.135, 0.087)	347
Example 32	H4	2.85	E2	2.95	3.40	4.50	(0.135, 0.088)	382
Example 33	H4	2.85	E3	2.85	3.54	4.11	(0.135, 0.089)	313
Example 34	H4	2.85	E4	2.97	3.57	4.20	(0.135, 0.087)	320
Example 35	H4	2.85	E5	2.95	3.64	3.90	(0.135, 0.088)	375
Example 36	H4	2.85	E6	2.88	3.36	4.55	(0.135, 0.088)	361
Example 37	H4	2.85	E7	2.86	3.38	4.55	(0.135, 0.089)	337
Example 38	H4	2.85	E8	2.97	3.43	4.45	(0.135, 0.087)	330
Example 39	H4	2.85	E9	2.88	3.36	4.55	(0.135, 0.088)	368
Example 40	H4	2.85	E10	2.98	3.54	4.39	(0.135, 0.089)	309
Example 41	H5	2.85	E1	2.85	3.47	4.37	(0.135, 0.087)	326
Example 42	H5	2.85	E2	2.95	3.40	4.55	(0.135, 0.088)	359
Example 43	H5	2.85	E3	2.85	3.54	4.16	(0.135, 0.088)	294
Example 44	H5	2.85	E4	2.97	3.57	4.24	(0.135, 0.089)	300
Example 45	H5	2.85	E5	2.95	3.64	3.94	(0.135, 0.087)	352
Example 46	H5	2.85	E6	2.88	3.36	4.59	(0.135, 0.088)	339
Example 47	H5	2.85	E7	2.86	3.38	4.60	(0.135, 0.089)	316
Example 48	H5	2.85	E8	2.97	3.43	4.50	(0.135, 0.087)	310
Example 49	H5	2.85	E9	2.88	3.36	4.59	(0.135, 0.088)	346
Example 50	H5	2.85	E10	2.98	3.54	4.44	(0.135, 0.088)	290
Example 51	H6	2.72	E1	2.85	3.30	4.65	(0.135, 0.089)	272
Example 52	H6	2.72	E2	2.95	3.23	4.83	(0.135, 0.087)	299
Example 53	H6	2.72	E3	2.85	3.36	4.41	(0.135, 0.088)	245
Example 54	H6	2.72	E4	2.97	3.40	4.51	(0.135, 0.089)	250
Example 55	H6	2.72	E5	2.95	3.46	4.18	(0.135, 0.087)	294
Example 56	H6	2.72	E6	2.88	3.20	4.88	(0.135, 0.088)	283
Example 57	H6	2.72	E7	2.86	3.22	4.89	(0.135, 0.088)	264
Example 58	H6	2.72	E8	2.97	3.27	4.78	(0.135, 0.089)	258
Example 59	H6	2.72	E9	2.88	3.20	4.88	(0.135, 0.087)	288
Example 60	H6	2.72	E10	2.98	3.36	4.71	(0.135, 0.088)	242
Example 61	H7	2.71	E1	2.85	3.33	4.60	(0.135, 0.089)	299
Example 62	H7	2.71	E2	2.95	3.27	4.78	(0.135, 0.087)	329
Example 63	H7	2.71	E3	2.85	3.40	4.37	(0.135, 0.088)	269
Example 64	H7	2.71	E4	2.97	3.43	4.46	(0.135, 0.088)	275
Example 65	H7	2.71	E5	2.95	3.50	4.14	(0.135, 0.089)	323
Example 66	H7	2.71	E6	2.88	3.23	4.83	(0.135, 0.087)	311
Example 67	H7	2.71	E7	2.86	3.25	4.84	(0.135, 0.088)	290
Example 68	H7	2.71	E8	2.97	3.30	4.73	(0.135, 0.089)	284
Example 69	H7	2.71	E9	2.88	3.23	4.83	(0.135, 0.087)	317
Example 70	H7	2.71	E10	2.98	3.40	4.67	(0.135, 0.088)	266
Example 71	H8	2.77	E1	2.85	3.37	4.56	(0.135, 0.088)	284
Example 72	H8	2.77	E2	2.95	3.30	4.74	(0.135, 0.089)	312
Example 73	H8	2.77	E3	2.85	3.43	4.33	(0.135, 0.087)	255
Example 74	H8	2.77	E4	2.97	3.47	4.42	(0.135, 0.088)	261
Example 75	H8	2.77	E5	2.95	3.53	4.10	(0.135, 0.089)	307
Example 76	H8	2.77	E6	2.88	3.27	4.78	(0.135, 0.087)	295
Example 77	H8	2.77	E7	2.86	3.28	4.79	(0.135, 0.088)	275
Example 78	H8	2.77	E8	2.97	3.33	4.68	(0.135, 0.088)	270
Example 79	H8	2.77	E9	2.88	3.27	4.78	(0.135, 0.089)	301
Example 80	H8	2.77	E10	2.98	3.43	4.62	(0.135, 0.087)	253
Example 81	H9	2.80	E1	2.85	3.43	4.33	(0.135, 0.088)	275
Example 82	H9	2.80	E2	2.95	3.37	4.50	(0.135, 0.089)	302
Example 83	H9	2.80	E3	2.85	3.50	4.11	(0.135, 0.087)	247
Example 84	H9	2.80	E4	2.97	3.54	4.20	(0.135, 0.088)	253
Example 85	H9	2.80	E5	2.95	3.61	3.90	(0.135, 0.088)	297
Example 86	H9	2.80	E6	2.88	3.33	4.55	(0.135, 0.089)	286
Example 87	H9	2.80	E7	2.86	3.35	4.55	(0.135, 0.087)	267
Example 88	H9	2.80	E8	2.97	3.40	4.45	(0.135, 0.088)	261
Example 89	H9	2.80	E9	2.88	3.33	4.55	(0.135, 0.089)	291
Example 90	H9	2.80	E10	2.98	3.50	4.39	(0.135, 0.087)	245
Example 91	H10	2.74	E1	2.85	3.37	4.65	(0.135, 0.088)	276
Example 92	H10	2.74	E2	2.95	3.30	4.83	(0.135, 0.088)	304
Example 93	H10	2.74	E3	2.85	3.43	4.41	(0.135, 0.089)	249
Example 94	H10	2.74	E4	2.97	3.47	4.51	(0.135, 0.087)	254
Example 95	H10	2.74	E5	2.95	3.53	4.18	(0.135, 0.088)	298
Example 96	H10	2.74	E6	2.88	3.27	4.88	(0.135, 0.089)	287
Example 97	H10	2.74	E7	2.86	3.28	4.89	(0.135, 0.087)	268
Example 98	H10	2.74	E8	2.97	3.33	4.78	(0.135, 0.088)	263
Example 99	H10	2.74	E9	2.88	3.27	4.88	(0.135, 0.088)	293
Example 100	H10	2.74	E10	2.98	3.43	4.71	(0.135, 0.089)	246
Comparative Example 1	H1	2.96	-		4.76	1.80	(0.135, 0.089)	36
Comparative Example 2	H2	2.71	-		4.90	1.71	(0.135, 0.087)	32
Comparative Example 3	H3	2.79	-		4.66	1.84	(0.135, 0.088)	35
Comparative Example 4	H4	2.85	-		4.86	1.73	(0.135, 0.089)	42
Comparative Example 5	H5	2.85	-		4.86	1.75	(0.135, 0.087)	39
Comparative Example 6	H6	2.72	-		4.62	1.86	(0.135, 0.088)	33
Comparative Example 7	H7	2.71	-		4.66	1.84	(0.135, 0.088)	36
Comparative Example 8	H8	2.77	-		4.71	1.82	(0.135, 0.089)	34
Comparative Example 9	H9	2.80	-		4.81	1.73	(0.135, 0.087)	33
Comparative Example 10	H10	2.74	-		4.71	1.86	(0.135, 0.088)	33
Comparative Example 11	-		E1	2.85	3.91	3.25	(0.135, 0.089)	211
Comparative Example 12	-		E2	2.95	3.83	3.38	(0.135, 0.087)	233
Comparative Example 13	-		E3	2.85	3.99	3.08	(0.135, 0.088)	190
Comparative Example 14	-		E4	2.97	4.03	3.15	(0.135, 0.088)	194
Comparative Example 15	-		E5	2.95	4.11	2.92	(0.135, 0.089)	228
Comparative Example 16	-		E6	2.88	3.79	3.41	(0.135, 0.087)	220
Comparative Example 17	-		E7	2.86	3.81	3.42	(0.135, 0.088)	205
Comparative Example 18	-		E8	2.97	3.87	3.34	(0.135, 0.089)	201
Comparative Example 19	-		E9	2.88	3.79	3.41	(0.135, 0.087)	224
Comparative Example 20	-		E10	2.98	3.99	3.30	(0.135, 0.088)	188
Comparative Example 21	HB-1	2.96	E1	2.85	4.11	2.75	(0.135, 0.088)	91
Comparative Example 22	HB-1	2.96	E2	2.95	4.03	2.86	(0.135, 0.089)	100
Comparative Example 23	HB-1	2.96	E3	2.85	4.20	2.61	(0.135, 0.087)	82
Comparative Example 24	HB-1	2.96	E4	2.97	4.24	2.67	(0.135, 0.088)	83
Comparative Example 25	HB-1	2.96	E5	2.95	4.32	2.48	(0.135, 0.089)	98
Comparative Example 26	HB-1	2.96	E6	2.88	3.99	2.89	(0.135, 0.087)	94
Comparative Example 27	HB-1	2.96	E7	2.86	4.01	2.89	(0.135, 0.088)	88
Comparative Example 28	HB-1	2.96	E8	2.97	4.07	2.83	(0.135, 0.088)	86
Comparative Example 29	HB-1	2.96	E9	2.88	3.99	2.89	(0.135, 0.089)	96
Comparative Example 30	HB-1	2.96	E10	2.98	4.20	2.79	(0.135, 0.087)	81
Comparative Example 31	HB-2	2.88	E1	2.85	4.42	2.84	(0.135, 0.088)	106
Comparative Example 32	HB-2	2.88	E2	2.95	4.33	2.95	(0.135, 0.089)	116
Comparative Example 33	HB-2	2.88	E3	2.85	4.51	2.70	(0.135, 0.087)	95
Comparative Example 34	HB-2	2.88	E4	2.97	4.55	2.76	(0.135, 0.088)	97
Comparative Example 35	HB-2	2.88	E5	2.95	4.64	2.56	(0.135, 0.088)	114
Comparative Example 36	HB-2	2.88	E6	2.88	4.29	2.98	(0.135, 0.089)	110
Comparative Example 37	HB-2	2.88	E7	2.86	4.31	2.99	(0.135, 0.087)	103
Comparative Example 38	HB-2	2.88	E8	2.97	4.38	2.92	(0.135, 0.088)	100
Comparative Example 39	HB-2	2.88	E9	2.88	4.29	2.98	(0.135, 0.088)	112
Comparative Example 40	HB-2	2.88	E10	2.98	4.51	2.88	(0.135, 0.089)	94
Comparative Example 41	H1	2.96	ET-1	3.14	3.74	3.16	(0.135, 0.087)	187
Comparative Example 42	H1	2.96	ET-2	3.00	3.71	3.25	(0.135, 0.088)	193
Comparative Example 43	H1	2.96	ET-3	3.08	3.91	3.29	(0.135, 0.089)	196
Comparative Example 44	H1	2.96	ET-4	2.88	3.81	3.23	(0.135, 0.087)	181
Comparative Example 45	H1	2.96	ET-5	2.69	3.30	3.61	(0.135, 0.088)	85
Comparative Example 46	H1	2.96	ET-6	2.70	3.30	3.70	(0.135, 0.088)	97
Comparative Example 47	H2	2.71	ET-1	3.14	3.85	3.00	(0.135, 0.089)	167
Comparative Example 48	H2	2.71	ET-2	3.00	3.82	3.08	(0.135, 0.087)	172
Comparative Example 49	H2	2.71	ET-3	3.08	4.03	3.13	(0.135, 0.088)	175
Comparative Example 50	H2	2.71	ET-4	2.88	3.92	3.07	(0.135, 0.088)	161
Comparative Example 51	H2	2.71	ET-5	2.69	3.40	3.43	(0.135, 0.089)	75
Comparative Example 52	H2	2.71	ET-6	2.70	3.40	3.51	(0.135, 0.087)	86
Comparative Example 53	H3	2.79	ET-1	3.14	3.67	3.22	(0.135, 0.088)	182
Comparative Example 54	H3	2.79	ET-2	3.00	3.63	3.31	(0.135, 0.089)	187
Comparative Example 55	H3	2.79	ET-3	3.08	3.83	3.36	(0.135, 0.087)	190
Comparative Example 56	H3	2.79	ET-4	2.88	3.73	3.29	(0.135, 0.088)	176
Comparative Example 57	H3	2.79	ET-5	2.69	3.23	3.68	(0.135, 0.088)	82
Comparative Example 58	H3	2.79	ET-6	2.70	3.24	3.77	(0.135, 0.089)	94
Comparative Example 59	H4	2.85	ET-1	3.14	3.81	3.03	(0.135, 0.087)	215
Comparative Example 60	H4	2.85	ET-2	3.00	3.78	3.12	(0.135, 0.088)	222
Comparative Example 61	H4	2.85	ET-3	3.08	3.99	3.16	(0.135, 0.088)	226
Comparative Example 62	H4	2.85	ET-4	2.88	3.88	3.10	(0.135, 0.089)	208
Comparative Example 63	H4	2.85	ET-5	2.69	3.36	3.46	(0.135, 0.087)	97
Comparative Example 64	H4	2.85	ET-6	2.70	3.37	3.55	(0.135, 0.088)	111
Comparative Example 65	H5	2.85	ET-1	3.14	3.81	3.06	(0.135, 0.089)	202
Comparative Example 66	H5	2.85	ET-2	3.00	3.78	3.15	(0.135, 0.087)	209
Comparative Example 67	H5	2.85	ET-3	3.08	3.99	3.19	(0.135, 0.088)	212
Comparative Example 68	H5	2.85	ET-4	2.88	3.88	3.13	(0.135, 0.088)	196
Comparative Example 69	H5	2.85	ET-5	2.69	3.36	3.50	(0.135, 0.089)	91
Comparative Example 70	H5	2.85	ET-6	2.70	3.37	3.59	(0.135, 0.087)	104
Comparative Example 71	H6	2.72	ET-1	3.14	3.63	3.25	(0.135, 0.088)	169
Comparative Example 72	H6	2.72	ET-2	3.00	3.59	3.34	(0.135, 0.088)	174
Comparative Example 73	H6	2.72	ET-3	3.08	3.79	3.39	(0.135, 0.089)	177
Comparative Example 74	H6	2.72	ET-4	2.88	3.69	3.33	(0.135, 0.087)	163
Comparative Example 75	H6	2.72	ET-5	2.69	3.20	3.72	(0.135, 0.088)	76
Comparative Example 76	H6	2.72	ET-6	2.70	3.21	3.81	(0.135, 0.089)	87
Comparative Example 77	H7	2.71	ET-1	3.14	3.67	3.22	(0.135, 0.087)	185
Comparative Example 78	H7	2.71	ET-2	3.00	3.63	3.31	(0.135, 0.088)	191
Comparative Example 79	H7	2.71	ET-3	3.08	3.83	3.36	(0.135, 0.088)	194
Comparative Example 80	H7	2.71	ET-4	2.88	3.73	3.29	(0.135, 0.089)	179
Comparative Example 81	H7	2.71	ET-5	2.69	3.23	3.68	(0.135, 0.087)	84
Comparative Example 82	H7	2.71	ET-6	2.70	3.24	3.77	(0.135, 0.088)	96
Comparative Example 83	H8	2.77	ET-1	3.14	3.70	3.19	(0.135, 0.088)	176
Comparative Example 84	H8	2.77	ET-2	3.00	3.67	3.28	(0.135, 0.089)	182
Comparative Example 85	H8	2.77	ET-3	3.08	3.87	3.33	(0.135, 0.087)	185
Comparative Example 86	H8	2.77	ET-4	2.88	3.77	3.26	(0.135, 0.088)	170
Comparative Example 87	H8	2.77	ET-5	2.69	3.27	3.64	(0.135, 0.089)	79
Comparative Example 88	H8	2.77	ET-6	2.70	3.27	3.74	(0.135, 0.087)	91
Comparative Example 89	H9	2.80	ET-1	3.14	3.78	3.03	(0.135, 0.088)	170
Comparative Example 90	H9	2.80	ET-2	3.00	3.74	3.12	(0.135, 0.088)	176
Comparative Example 91	H9	2.80	ET-3	3.08	3.95	3.16	(0.135, 0.089)	179
Comparative Example 92	H9	2.80	ET-4	2.88	3.85	3.10	(0.135, 0.087)	165
Comparative Example 93	H9	2.80	ET-5	2.69	3.33	3.46	(0.135, 0.088)	77
Comparative Example 94	H9	2.80	ET-6	2.70	3.34	3.55	(0.135, 0.088)	88
Comparative Example 95	H10	2.74	ET-1	3.14	3.70	3.25	(0.135, 0.089)	171
Comparative Example 96	H10	2.74	ET-2	3.00	3.67	3.34	(0.135, 0.087)	177
Comparative Example 97	H10	2.74	ET-3	3.08	3.87	3.39	(0.135, 0.088)	180
Comparative Example 98	H10	2.74	ET-4	2.88	3.77	3.33	(0.135, 0.089)	166
Comparative Example 99	H10	2.74	ET-5	2.69	3.27	3.72	(0.135, 0.087)	77
Comparative Example 100	H10	2.74	ET-6	2.70	3.27	3.81	(0.135, 0.088)	88
Comparative Example 101	ET-7	2.76	ET-7	2.76	3.65	2.67	(0.135, 0.088)	235

As shown in Table 1, the organic light-emitting device in which the compound represented by Formula 1 of the present invention is used as a hole blocking layer and the compound represented by Formula 2 is used in the electron transport region has the following characteristics in terms of driving voltage, efficiency, and lifespan. It was confirmed to have a significant effect.

Examples 1 to 100 and Comparative Examples 21 to 40 of Table 1 and a device in which the compound represented by Formula 1 was used as a hole blocking layer and ET-5 or ET-6 was used as an electron transport layer (Comparative Examples 45, 46, 51, 52, 57, 58, 63, 64, 69, 70, 75, 76, 81, 82, 87, 88, 93, 94, 99 and 100), the organic light emitting device according to the present invention has a lifespan of It can be confirmed that it shows significantly excellent characteristics.

Experimental Example 2

Comparison of dipole moment (Debye) values of formulas H1 to H10, E1 to E10, HB-1 to HB-2, and ET-1 to ET-6 according to an exemplary embodiment of the present specification with Examples 1 to 100 In the organic light emitting devices of Examples 1 to 101, whether Equation 1 is satisfied is shown in Table 2 below.

division	hole blocking layer	P Eb (debye)	electron transport layer	P EI (debye)	P EI -P EB	Is Equation 1 satisfied?
Example 1	H1	1.65	E1	4.88	3.23	O
Example 2	H1	1.65	E2	5.33	3.68	O
Example 3	H1	1.65	E3	7.01	5.36	O
Example 4	H1	1.65	E4	4.66	3.01	O
Example 5	H1	1.65	E5	7.69	6.04	O
Example 6	H1	1.65	E6	5.02	3.37	O
Example 7	H1	1.65	E7	4.81	3.16	O
Example 8	H1	1.65	E8	5.60	3.95	O
Example 9	H1	1.65	E9	4.99	3.34	O
Example 10	H1	1.65	E10	5.69	4.04	O
Example 11	H2	2.25	E1	4.88	2.63	O
Example 12	H2	2.25	E2	5.33	3.08	O
Example 13	H2	2.25	E3	7.01	4.76	O
Example 14	H2	2.25	E4	4.66	2.41	O
Example 15	H2	2.25	E5	7.69	5.44	O
Example 16	H2	2.25	E6	5.02	2.77	O
Example 17	H2	2.25	E7	4.81	2.56	O
Example 18	H2	2.25	E8	5.60	3.35	O
Example 19	H2	2.25	E9	4.99	2.74	O
Example 20	H2	2.25	E10	5.69	3.44	O
Example 21	H3	1.51	E1	4.88	3.37	O
Example 22	H3	1.51	E2	5.33	3.82	O
Example 23	H3	1.51	E3	7.01	5.5	O
Example 24	H3	1.51	E4	4.66	3.15	O
Example 25	H3	1.51	E5	7.69	6.18	O
Example 26	H3	1.51	E6	5.02	3.51	O
Example 27	H3	1.51	E7	4.81	3.3	O
Example 28	H3	1.51	E8	5.60	4.09	O
Example 29	H3	1.51	E9	4.99	3.48	O
Example 30	H3	1.51	E10	5.69	4.18	O
Example 31	H4	1.27	E1	4.88	3.61	O
Example 32	H4	1.27	E2	5.33	4.06	O
Example 33	H4	1.27	E3	7.01	5.74	O
Example 34	H4	1.27	E4	4.66	3.39	O
Example 35	H4	1.27	E5	7.69	6.42	O
Example 36	H4	1.27	E6	5.02	3.75	O
Example 37	H4	1.27	E7	4.81	3.54	O
Example 38	H4	1.27	E8	5.60	4.33	O
Example 39	H4	1.27	E9	4.99	3.72	O
Example 40	H4	1.27	E10	5.69	4.42	O
Example 41	H5	1.77	E1	4.88	3.11	O
Example 42	H5	1.77	E2	5.33	3.56	O
Example 43	H5	1.77	E3	7.01	5.24	O
Example 44	H5	1.77	E4	4.66	2.89	O
Example 45	H5	1.77	E5	7.69	5.92	O
Example 46	H5	1.77	E6	5.02	3.25	O
Example 47	H5	1.77	E7	4.81	3.04	O
Example 48	H5	1.77	E8	5.60	3.83	O
Example 49	H5	1.77	E9	4.99	3.22	O
Example 50	H5	1.77	E10	5.69	3.92	O
Example 51	H6	0.97	E1	4.88	3.91	O
Example 52	H6	0.97	E2	5.33	4.36	O
Example 53	H6	0.97	E3	7.01	6.04	O
Example 54	H6	0.97	E4	4.66	3.69	O
Example 55	H6	0.97	E5	7.69	6.72	O
Example 56	H6	0.97	E6	5.02	4.05	O
Example 57	H6	0.97	E7	4.81	3.84	O
Example 58	H6	0.97	E8	5.60	4.63	O
Example 59	H6	0.97	E9	4.99	4.02	O
Example 60	H6	0.97	E10	5.69	4.72	O
Example 61	H7	1.27	E1	4.88	3.61	O
Example 62	H7	1.27	E2	5.33	4.06	O
Example 63	H7	1.27	E3	7.01	5.74	O
Example 64	H7	1.27	E4	4.66	3.39	O
Example 65	H7	1.27	E5	7.69	6.42	O
Example 66	H7	1.27	E6	5.02	3.75	O
Example 67	H7	1.27	E7	4.81	3.54	O
Example 68	H7	1.27	E8	5.60	4.33	O
Example 69	H7	1.27	E9	4.99	3.72	O
Example 70	H7	1.27	E10	5.69	4.42	O
Example 71	H8	1.47	E1	4.88	3.41	O
Example 72	H8	1.47	E2	5.33	3.86	O
Example 73	H8	1.47	E3	7.01	5.54	O
Example 74	H8	1.47	E4	4.66	3.19	O
Example 75	H8	1.47	E5	7.69	6.22	O
Example 76	H8	1.47	E6	5.02	3.55	O
Example 77	H8	1.47	E7	4.81	3.34	O
Example 78	H8	1.47	E8	5.60	4.13	O
Example 79	H8	1.47	E9	4.99	3.52	O
Example 80	H8	1.47	E10	5.69	4.22	O
Example 81	H9	1.36	E1	4.88	3.52	O
Example 82	H9	1.36	E2	5.33	3.97	O
Example 83	H9	1.36	E3	7.01	5.65	O
Example 84	H9	1.36	E4	4.66	3.3	O
Example 85	H9	1.36	E5	7.69	6.33	O
Example 86	H9	1.36	E6	5.02	3.66	O
Example 87	H9	1.36	E7	4.81	3.45	O
Example 88	H9	1.36	E8	5.60	4.24	O
Example 89	H9	1.36	E9	4.99	3.63	O
Example 90	H9	1.36	E10	5.69	4.33	O
Example 91	H10	1.17	E1	4.88	3.71	O
Example 92	H10	1.17	E2	5.33	4.16	O
Example 93	H10	1.17	E3	7.01	5.84	O
Example 94	H10	1.17	E4	4.66	3.49	O
Example 95	H10	1.17	E5	7.69	6.52	O
Example 96	H10	1.17	E6	5.02	3.85	O
Example 97	H10	1.17	E7	4.81	3.64	O
Example 98	H10	1.17	E8	5.60	4.43	O
Example 99	H10	1.17	E9	4.99	3.82	O
Example 100	H10	1.17	E10	5.69	4.52	O
Comparative Example 1	H1	1.65	-	-	-	-
Comparative Example 2	H2	2.25	-	-	-	-
Comparative Example 3	H3	1.51	-	-	-	-
Comparative Example 4	H4	1.27	-	-		-
Comparative Example 5	H5	1.77	-	-	-	-
Comparative Example 6	H6	0.97	-	-	-	-
Comparative Example 7	H7	1.27	-	-	-	-
Comparative Example 8	H8	1.47	-	-	-	-
Comparative Example 9	H9	1.36	-	-	-	-
Comparative Example 10	H10	1.17	-	-	-	-
Comparative Example 11	-	-	E1	4.88	-	-
Comparative Example 12	-	-	E2	5.33	-	-
Comparative Example 13	-	-	E3	7.01	-	-
Comparative Example 14	-	-	E4	4.66	-	-
Comparative Example 15	-	-	E5	7.69	-	-
Comparative Example 16	-	-	E6	5.02	-	-
Comparative Example 17	-	-	E7	4.81	-	-
Comparative Example 18	-	-	E8	5.60	-	-
Comparative Example 19	-	--	E9	4.99	-	-
Comparative Example 20	-	-	E10	5.69	-	-
Comparative Example 21	HB-1	5.37	E1	4.88	-0.49	X
Comparative Example 22	HB-1	5.37	E2	5.33	-0.04	X
Comparative Example 23	HB-1	5.37	E3	7.01	1.64	X
Comparative Example 24	HB-1	5.37	E4	4.66	-0.71	X
Comparative Example 25	HB-1	5.37	E5	7.69	2.32	O
Comparative Example 26	HB-1	5.37	E6	5.02	-0.35	X
Comparative Example 27	HB-1	5.37	E7	4.81	-0.56	X
Comparative Example 28	HB-1	5.37	E8	5.60	0.23	X
Comparative Example 29	HB-1	5.37	E9	4.99	-0.38	X
Comparative Example 30	HB-1	5.37	E10	5.69	0.32	X
Comparative Example 31	HB-2	5.80	E1	4.88	-0.92	X
Comparative Example 32	HB-2	5.80	E2	5.33	-0.47	X
Comparative Example 33	HB-2	5.80	E3	7.01	1.21	X
Comparative Example 34	HB-2	5.80	E4	4.66	-1.14	X
Comparative Example 35	HB-2	5.80	E5	7.69	1.89	X
Comparative Example 36	HB-2	5.80	E6	5.02	-0.78	X
Comparative Example 37	HB-2	5.80	E7	4.81	-0.99	X
Comparative Example 38	HB-2	5.80	E8	5.60	-0.2	X
Comparative Example 39	HB-2	5.80	E9	4.99	-0.81	X
Comparative Example 40	HB-2	5.80	E10	5.69	-0.11	X
Comparative Example 41	H1	1.65	ET-1	5.78	4.13	O
Comparative Example 42	H1	1.65	ET-2	5.44	3.79	O
Comparative Example 43	H1	1.65	ET-3	5.18	3.53	O
Comparative Example 44	H1	1.65	ET-4	8.83	7.18	O
Comparative Example 45	H1	1.65	ET-5	0.08	-1.57	X
Comparative Example 46	H1	1.65	ET-6	0.64	-1.01	X
Comparative Example 47	H2	2.25	ET-1	5.78	3.53	O
Comparative Example 48	H2	2.25	ET-2	5.44	3.19	O
Comparative Example 49	H2	2.25	ET-3	5.18	2.93	O
Comparative Example 50	H2	2.25	ET-4	8.83	6.58	O
Comparative Example 51	H2	2.25	ET-5	0.08	-2.17	X
Comparative Example 52	H2	2.25	ET-6	0.64	-1.61	X
Comparative Example 53	H3	1.51	ET-1	5.78	4.27	O
Comparative Example 54	H3	1.51	ET-2	5.44	3.93	O
Comparative Example 55	H3	1.51	ET-3	5.18	3.67	O
Comparative Example 56	H3	1.51	ET-4	8.83	7.32	O
Comparative Example 57	H3	1.51	ET-5	0.08	-1.43	X
Comparative Example 58	H3	1.51	ET-6	0.64	-0.87	X
Comparative Example 59	H4	1.27	ET-1	5.78	4.51	O
Comparative Example 60	H4	1.27	ET-2	5.44	4.17	O
Comparative Example 61	H4	1.27	ET-3	5.18	3.91	O
Comparative Example 62	H4	1.27	ET-4	8.83	7.56	O
Comparative Example 63	H4	1.27	ET-5	0.08	-1.19	X
Comparative Example 64	H4	1.27	ET-6	0.64	-0.63	X
Comparative Example 65	H5	1.77	ET-1	5.78	4.01	O
Comparative Example 66	H5	1.77	ET-2	5.44	3.67	O
Comparative Example 67	H5	1.77	ET-3	5.18	3.41	O
Comparative Example 68	H5	1.77	ET-4	8.83	7.06	O
Comparative Example 69	H5	1.77	ET-5	0.08	-1.69	X
Comparative Example 70	H5	1.77	ET-6	0.64	-1.13	X
Comparative Example 71	H6	0.97	ET-1	5.78	4.81	O
Comparative Example 72	H6	0.97	ET-2	5.44	4.47	O
Comparative Example 73	H6	0.97	ET-3	5.18	4.21	O
Comparative Example 74	H6	0.97	ET-4	8.83	7.86	O
Comparative Example 75	H6	0.97	ET-5	0.08	-0.89	X
Comparative Example 76	H6	0.97	ET-6	0.64	-0.33	X
Comparative Example 77	H7	1.27	ET-1	5.78	4.51	O
Comparative Example 78	H7	1.27	ET-2	5.44	4.17	O
Comparative Example 79	H7	1.27	ET-3	5.18	3.91	O
Comparative Example 80	H7	1.27	ET-4	8.83	7.56	O
Comparative Example 81	H7	1.27	ET-5	0.08	-1.19	X
Comparative Example 82	H7	1.27	ET-6	0.64	-0.63	X
Comparative Example 83	H8	1.47	ET-1	5.78	4.31	O
Comparative Example 84	H8	1.47	ET-2	5.44	3.97	O
Comparative Example 85	H8	1.47	ET-3	5.18	3.71	O
Comparative Example 86	H8	1.47	ET-4	8.83	7.36	O
Comparative Example 87	H8	1.47	ET-5	0.08	-1.39	X
Comparative Example 88	H8	1.47	ET-6	0.64	-0.83	X
Comparative Example 89	H9	1.36	ET-1	5.78	4.42	O
Comparative Example 90	H9	1.36	ET-2	5.44	4.08	O
Comparative Example 91	H9	1.36	ET-3	5.18	3.82	O
Comparative Example 92	H9	1.36	ET-4	8.83	7.47	O
Comparative Example 93	H9	1.36	ET-5	0.08	-1.28	X
Comparative Example 94	H9	1.36	ET-6	0.64	-0.72	X
Comparative Example 95	H10	1.17	ET-1	5.78	4.61	O
Comparative Example 96	H10	1.17	ET-2	5.44	4.27	O
Comparative Example 97	H10	1.17	ET-3	5.18	4.01	O
Comparative Example 98	H10	1.17	ET-4	8.83	7.66	O
Comparative Example 99	H10	1.17	ET-5	0.08	-1.09	X
Comparative Example 100	H10	1.17	ET-6	0.64	-0.53	X
Comparative Example 101	ET-7	2.98	ET-7	2.98	0	X

The calculation of the Dipole Moment (Debye) was performed using the quantum chemical calculation program Gaussian 03 manufactured by Gaussian, USA, and using density functional theory (DFT), B3LYP as the functional and 6- as the basis function. For the structure optimized using 31G*, the dipole moment was calculated using time-dependent density functional theory (TD-DFT).

[Explanation of symbols]

1: Substrate 2: Anode

3: light emitting layer 4: cathode

5: hole injection layer 6: hole transport layer

7: Hole blocking layer 8: Electron transport and injection layer

Claims (13)

1. anode;

   cathode;

   a light-emitting layer between the anode and the cathode;

   A hole blocking layer between the cathode and the light emitting layer; and

   It includes an electron transport layer, an electron injection layer, or an electron transport and injection layer between the hole blocking layer and the cathode,

   The hole blocking layer includes a first compound represented by the following formula (1),

   The electron transport layer, electron injection layer, or electron transport and injection layer includes a second compound represented by the following formula (2),

   The values of the dipole moment of the first compound represented by Formula 1 and the dipole moment of the second compound represented by Formula 2 satisfy the following formula 1,

   Organic light emitting device:

   [Formula 1]

   

   In Formula 1,

   X is O or S,

   At least one of R ₁ is represented by the following formula A, and the others are each independently hydrogen, deuterium, substituted or unsubstituted C _1-60 alkyl, substituted or unsubstituted C _6-60 aryl, and substituted or unsubstituted It is C _2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of N, O, S and Si, or two adjacent R ₁ are bonded to each other to form a substituted or unsubstituted aromatic ring, ,

   [Formula A]

   

   In Formula A,

   X ₁ is each independently N or CR ₂ , but at least one of X ₁ is N,

   R ₂ is hydrogen, deuterium, or combined with an adjacent substituent -(L _2-- ) _l2 -Ar ₂ or -(L ₃ ) _l3 -Ar ₃ to form a substituted or unsubstituted aromatic ring;

   L ₁ to L ₃ are each independently a single bond, a substituted or unsubstituted C _6-60 arylene, or one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, S and Si. It is C _2-60 heteroarylene containing,

   Ar ₂ and Ar ₃ are each independently, substituted or unsubstituted C _1-60 alkyl, substituted or unsubstituted C _1-60 alkoxy, substituted or unsubstituted C _6-60 aryl, substituted or unsubstituted N, C _2-60 heteroaryl containing at least one heteroatom selected from the group consisting of O, S and Si, or -Si(Z ₁ )(Z ₂ )(Z ₃ ),

   Here, Z ₁ to Z ₃ are each independently substituted or unsubstituted C _1-60 alkyl, or substituted or unsubstituted C _6-60 aryl,

   l ₁ to l ₃ are each independently an integer of 1 to 3,

   When l ₁ is 2 or more, two or more L ₁ are the same or different from each other,

   When l ₂ is 2 or more, two or more L ₂ are the same or different from each other,

   When l ₃ is 2 or more, two or more L ₃ are the same or different from each other,

   [Formula 2]

   

   In Formula 2,

   X ₂ is each independently N or CR ₃ , but at least two of X ₂ are N,

   X ₃ is each independently N or CR ₄ , but at least two of X ₃ are N,

   R ₃ and R ₄ are each independently hydrogen, deuterium, substituted or unsubstituted C _1-60 alkyl, or substituted or unsubstituted C _6-60 aryl, or two adjacent R ₃ or R ₄ are bonded to each other Forming a substituted or unsubstituted aromatic ring,

   L ₄ and L ₅ are each independently a single bond or substituted or unsubstituted C _6-60 arylene,

   Ar ₄ is phenylene or biphenyldiyl,

   Ar ₄ is unsubstituted or substituted with one or more deuterium,

   At least one of R ₃ , R ₄ and Ar ₄ is substituted with cyano,

   However, when L ₄ and L ₅ are a single bond, Ar ₄ is unsubstituted or deuterium-substituted phenylene or biphenyldiyl,

   [Equation 1]

   P _EI > P _EB + 2

   In equation 1 above,

   P _EI means the dipole moment value of the compound represented by Formula 2,

   P _EB means the dipole moment value of the compound represented by Formula 1.
2. According to paragraph 1,

   The LUMO energy level of the first compound is 2.6 eV to 2.85 eV,

   The LUMO energy level of the second compound is 2.85 eV to 3.2 eV,

   Organic light emitting device.
3. According to paragraph 1,

   At least one of R ₁ is represented by the formula A, and the others are each independently hydrogen, deuterium, methyl, n-propyl, n-butyl, tert-butyl, phenyl, biphenylyl, terphenylyl, naphthyl, Dimethylfluorenyl, triphenylenyl, or two adjacent R ₁ are combined with each other to form an unsubstituted or deuterium-substituted benzene ring,

   wherein the phenyl is unsubstituted or substituted with one or more deuterium, methyl, or tert-butyl,

   Organic light emitting device.
4. According to paragraph 1,

   One or two of R ₁ are represented by the formula A,

   Organic light emitting device.
5. According to paragraph 1,

   At least two of X ₁ are N,

   Organic light emitting device.
6. According to paragraph 1,

   R- ₂ is hydrogen, deuterium, or combined with an adjacent substituent -(L _2-- ) _l2 -Ar ₂ or -(L ₃ ) _l3 -Ar ₃ to form an unsubstituted or deuterium-substituted benzene ring. ,

   Organic light emitting device.
7. According to paragraph 1,

   l ₁ is 1 or 2,

   L ₁ is each independently a single bond, phenylene, biphenyldiyl, naphthyldiyl, dibenzothiophenylene, dibenzofuranylene, dimethylfluorenylene, furanylene, thiophenylene, carbazol-9-ylene , pyridinylene, indolodimethylfluorenylene, 9-phenylcarbazolylene, dimethylsilylfluorenylene, phenoxathiinilene, phenoxazinylene, 9-phenylbenzocarbazolylene, or benzocarbazole-9- It's Illen,

   where L ₁ is unsubstituted or substituted with one or more deuterium, methyl, phenyl, or dimethylphenyl,

   Organic light emitting device.
8. According to paragraph 1,

   l ₂ and l ₃ are each independently 1 or 2,

   L ₂ and L ₃ are each independently a single bond, phenylene, biphenyldiyl, dibenzothiophenylene, dibenzofuranylene, carbazol-9-ylene, or 9-phenylcarbazolylene,

   Here, when L ₂ and L ₃ are phenylene, biphenyldiyl, dibenzothiophenylene, dibenzofuranylene, carbazol-9-ylene and 9-phenylcarbazolylene, L ₂ and L ₃ are unsubstituted or , or one or more substituents selected from the group consisting of deuterium, methyl, phenyl, and tolyl,

   Organic light emitting device.
9. According to paragraph 1,

   Ar ₂ and Ar ₃ are each independently selected from phenyl, biphenylyl, naphthyl, terphenylyl, triphenylenyl, phenalenyl, dimethylfluorenyl, phenanthrenyl, fluoranthenyl, carbazol-9-yl, 9-phenylcarbazolyl, dibenzothiophenyl, phenoxazinyl, phenoxathiinyl, phenothiazinyl, benzocarbazolyl, dibenzofuranyl, pyridinyl, indolodimethylfluorenyl, phenylindolodimethylfluorenyl , dimethylsilafluorenyl, triphenylsilyl, dimethylacridinyl, or quinolinyl,

   Here, Ar ₂ and Ar ₃ are unsubstituted or phenyl substituted with deuterium, cyano, methyl, trifluoromethyl, trifluoromethoxy, cyano, trimethylsilyl, triphenylsilyl, carbazol-9-yl, Substituted with one or more substituents selected from the group consisting of dibenzothiophenyl, and dibenzofuranyl,

   Organic light emitting device.
10. According to paragraph 1,

    The first compound represented by Formula 1 is any one selected from the group consisting of:

    Organic light emitting device:

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

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11. According to paragraph 1,

    R ₃ and R ₄ are each independently hydrogen, deuterium, methyl, iso-propyl, phenyl, biphenylyl, terphenylyl, naphthyl, phenyl naphthyl, naphthyl phenyl, phenyl naphthyl phenyl, or pyridinyl. , or combined with each other to form an unsubstituted or deuterium-substituted benzene ring,

    where R ₃ and R ₄ are unsubstituted or substituted with one or more substituents selected from the group consisting of methyl, tert-butyl, cyclohexyl, and cyano,

    Organic light emitting device.
12. According to paragraph 1,

    L ₄ and L ₅ are each independently phenylene, biphenyldiyl, or naphthylene,

    Organic light emitting device.
13. According to paragraph 1,

    The second compound represented by Formula 2 is any one selected from the group consisting of:

    Organic light emitting device:

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

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