WO2022191569A1 - Novel compound and organic light emitting device comprising same - Google Patents

Abstract

The present invention provides a novel compound and an organic light emitting device comprising same.

Description

Novel compound and organic light emitting device using same

Cross-Citation with Related Application(s)

This application claims the benefit of priority based on Korean Patent Application No. 10-2021-0030416 dated March 8, 2021 and Korean Patent Application No. 10-2022-0029047 dated March 8, 2022, All content disclosed in the literature is incorporated as a part of this specification.

The present invention relates to a novel compound and an organic light emitting device comprising the same.

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.

An organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode. The organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, it may be made of an electron injection layer, etc. When a voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons It lights up when it falls back to the ground state.

The development of new materials for organic materials used in organic light emitting devices as described above is continuously required.

Meanwhile, in order to reduce process costs, an organic light emitting device using a solution process, particularly an inkjet process, is being developed instead of a conventional deposition process. In the early days, all organic light emitting device layers were coated with a solution process to develop an organic light emitting device, but the current technology has limitations. Therefore, only HIL, HTL, and EML are processed in a solution process in a regular structure, and subsequent processes are performed using the conventional deposition process. A hybrid process using

Accordingly, the present invention provides a material for a novel organic light emitting device that can be used in an organic light emitting device and can be used in a solution process at the same time.

[Prior art literature]

[Patent Literature]

(Patent Document 1) Korean Patent Publication No. 10-2000-0051826

The present invention relates to a novel compound and an organic light emitting device comprising the same.

The present invention provides a compound represented by Formula 1 or 2:

[Formula 1]

[Formula 2]

In Formulas 1 and 2,

X ₁ to X ₃ are each independently CH or N, wherein at least one of X ₁ to X ₃ is N,

Y is O or S;

Ar is substituted or unsubstituted C _1-30 alkyl, substituted or unsubstituted C _3-30 cycloalkyl, substituted or unsubstituted C _6-60 aryl, or substituted or unsubstituted N, O and S C _2-60 heteroaryl including any one or more heteroatoms selected from the group,

L ₁ and L ₂ are each independently a single bond, phenylene, biphenylene, or terphenylene,

R ₁ and R ₂ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C _1-60 alkyl, substituted or unsubstituted C _6-60 aryl, or substituted or unsubstituted N, O and C _2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of S,

m is an integer from 1 to 7, n is an integer from 1 to 8,

wherein Ar is substituted with one or more deuterium, or at least one of R ₁ and R ₂ is deuterium,

The compound represented by Formula 1 or 2 includes 4 or more deuterium in the compound.

In addition, the present invention is a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Formula 1 or 2, organic light emitting diode provide the element.

The compound represented by Chemical Formula 1 or 2 described above can be used as a material for an organic material layer of an organic light emitting device, and can also be used in a solution process, and improve efficiency, low driving voltage and/or lifespan characteristics in an organic light emitting device can do it

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

2 is a substrate (1), anode (2), hole injection layer (5), hole transport layer (6), electron blocking layer (7), light emitting layer (8), hole blocking layer (9), electron transport layer (10) , an example of an organic light emitting device including an electron injection layer 11 and a cathode 4 is shown.

Hereinafter, it will be described in more detail to help the understanding of the present invention.

(Definition of Terms)

In this specification,

or

means a bond connected to another substituent.

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; cyano group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkyl thiooxy group; arylthioxy group; an alkyl sulfoxy group; arylsulfoxy group; silyl group; boron group; an alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; heteroarylamine group; arylamine group; an aryl phosphine group; or N, O, and S atoms, which is substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl containing one or more . For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but it is preferably from 1 to 40 carbon atoms. Specifically, the carbonyl group may have a structure as follows, but is not limited thereto.

In the present specification, in the ester group, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group may have a structure as follows, but is not limited thereto.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but it is preferably from 1 to 25 carbon atoms. Specifically, the imide group may have a structure as follows, but is not limited thereto.

In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. However, the present invention is not limited thereto.

In the present specification, the boron group specifically includes, but is not limited to, a dimethyl boron group, a diethyl boron group, a t-butylmethyl boron group, a diphenyl boron group, a phenyl boron group, and the like.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group 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, 2-methylhexyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the carbon number of the alkenyl group is 2 to 10. According to another exemplary 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, and the like, but are not limited thereto.

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

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 an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, or a fluorenyl group, but is not limited thereto.

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

etc. can be However, the present invention is not limited thereto.

In the present specification, heteroaryl is a heteroaryl containing at least one of O, N, Si and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but is preferably from 2 to 60 carbon atoms. Examples of heteroaryl include xanthene, thioxanthen, thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridyl, bipyridyl, Pyrimidyl group, triazine group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyridopyrazinyl group, pyrazino Pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group ( phenanthroline), an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.

In the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, the arylamine group, and the arylsilyl group is the same as the examples of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the above-described alkyl group. In the present specification, as for heteroaryl among the heteroarylamine groups, the description of the above-described heteroaryl may be applied. In the present specification, the alkenyl group among the aralkenyl groups is the same as the examples of the above-described alkenyl groups. In the present specification, the description of the above-described aryl group may be applied except that arylene is a divalent group. In the present specification, the description of the aforementioned heteroaryl may be applied, except that heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the above-described aryl group or cycloalkyl group may be applied, except that it is formed by combining two substituents. In the present specification, the heterocycle is not a monovalent group, and the description of the above-described heteroaryl may be applied, except that it is formed by combining two substituents.

(compound)

The present invention provides a compound represented by Formula 1 or 2.

The compound represented by Formula 1 or 2 contains 4 or more deuterium in the compound, preferably 4 to 30 deuterium, more preferably 4 to 20, and still more preferably 4 Dogs to 15.

Further, in Formulas 1 and 2, preferably, X ₁ to X ₃ are each N.

In addition, in Formulas 1 and 2, preferably, Ar is C _6-20 aryl, wherein Ar is unsubstituted or substituted with 5 to 15 deuterium.

More preferably, Ar is phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, phenanthrenyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylflu orenyl or triphenylenyl, wherein Ar is unsubstituted or substituted with 5 to 13 deuterium. Even more preferably, Ar is unsubstituted or substituted with 5, 9, 11 or 13 deuterium.

In addition, in Formulas 1 and 2, preferably, L ₁ is a single bond, phenylene, biphenylene, or terphenylene, and L ₂ is a single bond; or L ₁ is a single bond, and L ₂ is phenylene or biphenylene.

In addition, in Formulas 1 and 2, preferably, R ₁ and R ₂ are each independently hydrogen or deuterium.

more preferably R ₁ and R ₂ are each hydrogen; R ₁ is deuterium, R ₂ is hydrogen, m is an integer of 4, 6, or 7, and n is an integer of 8; R ₁ is hydrogen, R ₂ is deuterium, m is an integer of 7, and n is an integer of 4, 6, or 8; or R ₁ and R ₂ are each deuterium, m is an integer of 4, 6, or 7, and n is an integer of 4, 6, or 8.

More preferably, in Formulas 1 and 2, Ar is phenyl, biphenyl, terphenyl, or triphenylenyl, wherein Ar is substituted with 5 to 13 deuterium, and R ₁ and R ₂ are each is hydrogen. Even more preferably in this case, Ar is phenyl substituted with 5 deuterium, biphenyl substituted with 5 or 9 deuterium, terphenyl substituted with 5 or 13 deuterium, or substituted with 11 deuterium triphenylenyl, and R ₁ and R ₂ are each hydrogen.

Also, more preferably, in Formulas 1 and 2, Ar is phenyl, biphenyl, terphenyl, or triphenylenyl, wherein Ar is unsubstituted, and at least one of R ₁ and R ₂ is deuterium; The rest is hydrogen. In this case, m is an integer of 1 to 7, n is an integer of 1 to 8, and the compound represented by Formula 1 or 2 includes 4 to 15 deuterium in the compound. Even more preferably in this case, Ar is phenyl, biphenyl, terphenyl, or triphenylenyl, wherein Ar is unsubstituted, R ₁ is deuterium, R ₂ is hydrogen, and m is 4, 6, or 7 is an integer of, n is an integer of 8; R ₁ is hydrogen, R ₂ is deuterium, m is an integer of 7, and n is an integer of 4, 6, or 8; or R ₁ and R ₂ are each deuterium, m is an integer of 4, 6, or 7, and n is an integer of 4, 6, or 8.

More preferably, in Formulas 1 and 2, Ar is substituted with one or more deuterium, and at least one of R ₁ and R ₂ is deuterium, specifically, Ar is phenyl, biphenyl, terphenyl, or triphenylenyl, wherein Ar is substituted with 5 to 13 deuterium, at least one of R ₁ and R ₂ is deuterium, and the remainder is hydrogen, wherein m is an integer from 1 to 7, n is an integer from 1 to 8; Even more preferably in this case, Ar is phenyl substituted with 5 deuterium, biphenyl substituted with 5 or 9 deuterium, terphenyl substituted with 5 or 13 deuterium, or substituted with 11 deuterium triphenylenyl, R ₁ is deuterium, R ₂ is hydrogen, m is an integer of 4, 6, or 7, and n is an integer of 8; R ₁ is hydrogen, R ₂ is deuterium, m is an integer of 7, and n is an integer of 4, 6, or 8; or R ₁ and R ₂ are each deuterium, m is an integer of 4, 6, or 7, and n is an integer of 4, 6, or 8.

Representative examples of the compound represented by Formula 1 or 2 are as follows:

.

Meanwhile, the present invention provides a method for preparing a compound represented by Formula 1 as shown in Scheme 1 below, and a compound represented by Formula 2 may also be prepared by applying the following Reaction Scheme.

[Scheme 1]

In Scheme 1, definitions other than X and Z are the same as defined above, and X and Z are each independently halogen, preferably bromo or chloro.

The steps S11 and S12 are amine substitution reactions, preferably performed in the presence of a palladium catalyst and a base, and the reactor for the amine substitution reaction can be changed as known in the art.

In another embodiment, the present invention provides a method for preparing a compound represented by Formula 1 as shown in Scheme 2 below, and the compound represented by Formula 2 may also be prepared by applying the following Reaction Scheme.

[Scheme 2]

In Scheme 2, definitions other than Z are the same as defined above, and Z is halogen, preferably bromo or chloro.

The reaction of compound (iii) and compound (iv) in step S21 is an amine substitution reaction, preferably performed in the presence of a palladium catalyst and a base, and the reactor for the amine substitution reaction can be changed as known in the art. do.

As another example, a method for preparing a compound represented by Formula 1 as shown in Scheme 3 is provided, and a compound represented by Formula 2 may also be prepared by applying the following Reaction Scheme.

[Scheme 3]

In Scheme 3, definitions other than W ₁ , W ₂ and V are the same as defined above. W ₁ and W ₂ are each independently halogen, preferably bromo or chloro. V is a boron-containing organic group such as a boronic acid group, a boronic acid ester group, or a boronic acid pinacol ester group.

The reaction of compound (iv) and compound (v) in step S31 in Scheme 3 is an amine substitution reaction, and is preferably performed in the presence of a palladium catalyst and a base, and the reactor for the amine substitution reaction is as known in the art. change is possible

In addition, the reaction of compound (vi) and compound (vii) in step S32 is a Suzuki-coupling reaction, preferably performed under a palladium catalyst and a base, and the reactor for the Suzuki-coupling reaction is subject to change as known in the art. It is possible.

The above-described manufacturing methods may be more specific in Synthesis Examples to be described later.

(organic light emitting element)

In addition, the present invention provides an organic light emitting device including the compound represented by the formula (1) or (2). In one example, the present invention provides a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a compound represented by Formula 1 or 2 above. provides

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or an electron injection and transport layer that simultaneously injects and transports electrons as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

In addition, the organic layer may include an emission layer, and the emission layer includes a compound represented by Chemical Formula 1 or 2. In particular, the compound according to the present invention can be used as a host for the light emitting layer.

Also, the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. Also, the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of the organic light emitting diode according to an embodiment of the present invention is illustrated in FIGS. 1 and 2 .

1 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , an organic material layer 3 , and a cathode 4 . In such a structure, the compound represented by Formula 1 or 2 may be included in the emission layer.

2 is a substrate (1), anode (2), hole injection layer (5), hole transport layer (6), electron blocking layer (7), light emitting layer (8), hole blocking layer (9), electron transport layer (10) , an example of an organic light emitting device comprising an electron injection layer 11 and a cathode 4 is shown. In such a structure, the compound represented by Formula 1 or 2 may be included in the emission layer.

The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1 or 2. Also, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode. and, after forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, it can be prepared by depositing a material that can be used as a cathode thereon.

In addition, the compound represented by Formula 1 or 2 may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.

In one example, the first electrode is an anode, the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

As the anode material, a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, 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 compounds such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multi-layered material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode, and as a hole injection material, it has the ability to transport holes, so it has a hole injection effect at the anode, an excellent hole injection effect on the light emitting layer or the light emitting material, and is produced in the light emitting layer A compound that prevents the exciton from moving to the electron injection layer or the electron injection material and is excellent in the ability to form a thin film is preferable. In particular, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, and conductive compounds of polyaniline and polythiophene series, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light emitting layer. The hole transport material is a material that can transport holes from the anode or the hole injection layer to the light emitting layer and transfer them to the light emitting layer. material is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive compound, and a block copolymer having a conjugated portion and a non-conjugated portion together.

The electron suppression layer is formed on the hole transport layer, and is preferably provided in contact with the light emitting layer to control hole mobility and prevent excessive movement of electrons to increase the hole-electron coupling probability, thereby increasing the efficiency of the organic light emitting device. plays a role in improving The electron blocking layer includes an electron blocking material, and an arylamine-based organic material may be used as an example of the electron blocking material, but is not limited thereto.

The light emitting layer is positioned between the anode and the cathode, and includes the compound of Formula 1 or 2 as a host material. Accordingly, excitons can emit light evenly throughout the light emitting layer, thereby exhibiting low voltage driving and high luminous efficiency of the organic light emitting diode, while exhibiting significantly improved lifespan characteristics.

In addition, the light emitting layer may further include a commonly used host material (hereinafter referred to as a second host) together with the compound of Formula 1 or 2 above. Specifically, as the second host, there is a condensed aromatic ring derivative or a heterocyclic compound containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Meanwhile, the emission layer may further include a dopant material in addition to the host material. Examples of the dopant material include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group. As the styrylamine compound, a substituted or unsubstituted It is a compound in which at least one arylvinyl group is substituted in the arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but is not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.

The hole blocking layer is formed on the light emitting layer, preferably provided in contact with the light emitting layer, to improve the efficiency of the organic light emitting device by controlling electron mobility and preventing excessive movement of holes to increase the hole-electron coupling probability layer that plays a role. The hole blocking layer includes a hole blocking material, and examples of the hole blocking material include azine derivatives including triazine; triazole derivatives; oxadiazole derivatives; phenanthroline derivatives; A compound into which an electron withdrawing group is introduced, such as a phosphine oxide derivative, may be used, but the present invention is not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer, and is formed on the emission layer or the hole blocking layer. As the electron transport material included in the electron transport layer, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high electron mobility is suitable. Specific examples include Al complex of 8-hydroxyquinoline; complexes comprising Alq3; organic radical compounds; hydroxyflavone-metal complexes; and triazine derivatives, but is not limited thereto. or fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and derivatives thereof, metal complex compounds , or may be used together with a nitrogen-containing 5-membered ring derivative, and the like, but is not limited thereto.

In addition, the electron injection layer is formed on the electron transport layer, and the electron injection material included in the electron injection layer is LiF, NaCl, CsF, Li ₂ O, BaO, fluorenone, anthraquinodimethane, diphenoquinone. , thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, etc. can be used.

Examples of the metal complex compound 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-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. Accordingly, the present invention is not limited thereto.

On the other hand, the organic light emitting device instead of the electron transport layer and the electron injection layer, injecting electrons from the electrode, and simultaneously performing the roles of the electron transport layer and the electron injection layer for transporting the received electrons to the light emitting layer, electron injection and transport layer may include As the electron injection and transport material, the above-described electron injection material or electron transport material may be used.

The organic light emitting device according to the present invention may be a top emission type, a back emission type, or a double side emission type depending on the material used.

In addition, the compound according to the present invention may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

Hereinafter, preferred embodiments are presented to help the understanding of the present invention. However, the following examples are only for illustrating the present invention, and the content of the present invention is not limited by the following examples.

Synthesis Example 1: Synthesis of Compound 1

1) Synthesis of compound A-1

2,4-dichloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine (20 g, 63.3 mmol) and (phenyl-d5)boronic acid (8 g , 63.3 mmol) was added to 400 ml of toluene, stirred and refluxed. Thereafter, potassium carbonate (26.2 g, 189.8 mmol) was dissolved in 79 ml of water, and after sufficient stirring, bis (tri-tert-butylphosphine) palladium (1 g, 1.9 mmol) was added. After the reaction for 6 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and then the organic layer was distilled. The resulting product was dissolved in 1148 mL of tetrahydrofuran (an amount corresponding to 50 times the total volume of the obtained product), washed twice with water, and then the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using tetrahydrofuran and ethyl acetate to obtain a white solid compound A-1 (13.1 g, 57%, MS: [M+H] ⁺ = 363.8).

2) Synthesis of compound B-1

Compound A-1 (10 g, 27.6 mmol) and 2-bromo-9H-carbazole (6.8 g, 27.6 mmol) were placed in 100 ml of dimethylacetamide in a nitrogen atmosphere, and stirred and refluxed. Thereafter, potassium triphosphate (17.6 g, 82.7 mmol) was added, followed by heating and stirring. After the reaction for 2 hours, it was cooled to room temperature, and the resulting solid was obtained by filtration. The resulting solid was dissolved in 473 mL of chloroform (an amount corresponding to 30 times the total volume of the solid), washed twice with water, and then the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to obtain a white solid compound B-1 (11.8 g, 75%, MS: [M+H] ⁺ = 573.5).

3) Synthesis of compound 1

Compound B-1 (20 g, 34.9 mmol) and 9H-carbazole (5.8 g, 34.9 mmol) were added to 400 ml of xylene in a nitrogen atmosphere, stirred and refluxed. Thereafter, potassium triphosphate (10.1 g, 104.8 mmol) was added, and after sufficient stirring, bis (tri-tert-butylphosphine) palladium (0.5 g, 1 mmol) was added. After the reaction for 2 hours, the mixture was cooled to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. The resulting product was dissolved in 230 mL of chloroform (an amount corresponding to 10 times the total volume of the obtained product), washed twice with water, and then the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to obtain a white solid compound 1 (12.9 g, 56%, MS: [M+H] ⁺ = 659.8).

Synthesis Example 2: Synthesis of compound 2

1) Synthesis of compound A-2

In a nitrogen atmosphere, 2-bromo-9H-carbazole-1,3,4,5,6,7,8-d7 (20 g, 79 mmol) and 9H-carbazole (13.2 g, 79 mmol) were added to 400 ml of xylene and stirred. and reflux. Thereafter, potassium triphosphate (22.8 g, 237 mmol) was added, and after sufficient stirring, bis (tri-tert-butylphosphine) palladium (1.2 g, 2.4 mmol) was added. After the reaction for 3 hours, the mixture was cooled to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. The resulting product was again dissolved in 268 mL of chloroform (an amount corresponding to 10 times the total volume of the obtained product), washed twice with water, and then the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to obtain a white solid compound A-2 (19 g, 71%, MS: [M+H] ⁺ = 340.5).

2) Synthesis of compound 2

Compound A-2 (20 g, 58.9 mmol) and 2-(4-chlorophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine in nitrogen atmosphere (25.6 g, 58.9 mmol) was added to 400 ml of xylene, stirred and refluxed. Thereafter, potassium triphosphate (17 g, 176.8 mmol) was added, and after sufficient stirring, bis (tri-tert-butylphosphine) palladium (0.9 g, 1.8 mmol) was added. After the reaction for 4 hours, it was cooled to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. The resulting product was again dissolved in 434 mL of chloroform (an amount corresponding to 10 times the total volume of the obtained product), washed twice with water, and then the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound 2 (23.9 g, 55%, MS: [M+H] ⁺ = 737.9).

Synthesis Example 3: Synthesis of compound 3

1) Synthesis of compound A-3

4,4,5,5-tetramethyl-2-(triphenylen-2-yl-d11)-1,3,2-dioxaborolane (20 g, 54.7 mmol) and 2,4-dichloro-6-(dibenzo [b,d]thiophen-3-yl)-1,3,5-triazine (18.2 g, 54.7 mmol) was added to 400 ml of toluene, and the mixture was stirred and refluxed. Thereafter, potassium carbonate (22.7 g, 164.2 mmol) was dissolved in 68 ml of water, and after sufficient stirring, bis (tri-tert-butylphosphine) palladium (0.8 g, 1.6 mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and then the organic layer was distilled. The resulting product was dissolved in 1465 mL of tetrahydrofuran (an amount corresponding to 50 times the total volume of the obtained product), washed twice with water, and then the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from tetrahydrofuran and ethyl acetate to obtain a white solid compound A-3 (21.1 g, 72%, MS: [M+H] ⁺ = 536.1).

2) Synthesis of compound 3

Compound A-3 (20 g, 37.4 mmol) and 9H-2,9'-bicarbazole (12.4 g, 37.4 mmol) were added to 400 ml of xylene in a nitrogen atmosphere, stirred and refluxed. Thereafter, potassium triphosphate (10.8 g, 112.1 mmol) was added, and after sufficient stirring, bis (tri-tert-butylphosphine) palladium (0.6 g, 1.1 mmol) was added. After the reaction for 5 hours, it was cooled to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. The resulting product was dissolved in 311 mL of chloroform (an amount corresponding to 10 times the total volume of the obtained product), washed twice with water, and then the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to obtain a white solid compound 3 (21.4 g, 69%, MS: [M+H] ⁺ = 832.1).

Synthesis Example 4: Synthesis of compound 4

1) Synthesis of compound A-4

2-chloro-4-(5'-chloro-[1,1':3',1''-terphenyl]-4-yl)-6-(dibenzo[b,d]furan-3-yl under nitrogen atmosphere )-1,3,5-triazine (20 g, 36.7 mmol) and (phenyl-d5)boronic acid (4.7 g, 36.7 mmol) were added to 400 ml of toluene, stirred and refluxed. Thereafter, potassium carbonate (15.2 g, 110.2 mmol) was dissolved in 46 ml of water, and after sufficient stirring, bis (tri-tert-butylphosphine) palladium (0.6 g, 1.1 mmol) was added. After the reaction for 7 hours, it was cooled to room temperature, and the resulting solid was filtered. The resulting solid was dissolved in 1086 mL of tetrahydrofuran (an amount corresponding to 50 times the total volume of the solid), washed twice with water, and then the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from tetrahydrofuran and ethyl acetate to obtain a white solid compound A-4 (11.1 g, 51%, MS: [M+H] ⁺ = 592.1).

2) Synthesis of compound 4

In a nitrogen atmosphere, compound A-4 (20 g, 33.8 mmol) and 9H-2,9'-bicarbazole (11.2 g, 33.8 mmol) were added to 400 ml of xylene, stirred and refluxed. Thereafter, potassium triphosphate (9.8 g, 101.5 mmol) was added, and after sufficient stirring, bis (tri-tert-butylphosphine) palladium (0.5 g, 1 mmol) was added. After the reaction for 5 hours, it was cooled to room temperature, and the resulting solid was filtered. The resulting solid was dissolved in 900 mL of chloroform (an amount corresponding to 30 times the total volume of the solid), washed twice with water, and then the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to obtain a white solid compound 4 (18.3 g, 61%, MS: [M+H] ⁺ = 888.1).

Synthesis Example 5: Synthesis of compound 5

1) Synthesis of compound A-5

400 ml of xylene with 2-bromo-9H-carbazole (20 g, 81.3 mmol) and 9H-carbazole-1,2,3,4,5,6,7,8-d8 (14.2 g, 81.3 mmol) in nitrogen atmosphere was added, stirred and refluxed. Thereafter, potassium triphosphate (23.4 g, 243.8 mmol) was added, and after sufficient stirring, bis (tri-tert-butylphosphine) palladium (1.2 g, 2.4 mmol) was added. After the reaction for 6 hours, it was cooled to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. The resulting product was dissolved in 830 mL of toluene (an amount corresponding to 30 times the total volume of the obtained product), washed twice with water, and then the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to obtain a white solid compound A-5 (15.5 g, 56%, MS: [M+H] ⁺ = 341.5).

2) Synthesis of compound 5

Compound A-5 (15 g, 44.1 mmol) and 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-(dibenzo[b,d]furan-3-yl under nitrogen atmosphere )-1,3,5-triazine (19.1 g, 44.1 mmol) was placed in 150 ml of dimethylacetamide, stirred and refluxed. Thereafter, potassium triphosphate (28.1 g, 132.2 mmol) was added, followed by heating and stirring. After the reaction for 1 hour, it was cooled to room temperature, and the resulting solid was filtered. The resulting solid was dissolved in 975 mL of chloroform (an amount corresponding to 30 times the total volume of the solid), washed twice with water, and then the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound 5 (24.4 g, 75%, MS: [M+H] ⁺ = 738.9).

Synthesis Example 6: Synthesis of compound 6

1) Synthesis of compound A-6

400 ml of xylene with 4-bromo-9H-carbazole (20 g, 81.3 mmol) and 9H-carbazole-1,2,3,4,5,6,7,8-d8 (14.2 g, 81.3 mmol) in a nitrogen atmosphere was added, stirred and refluxed. Thereafter, potassium triphosphate (23.4 g, 243.8 mmol) was added, and after sufficient stirring, bis (tri-tert-butylphosphine) palladium (1.2 g, 2.4 mmol) was added. After the reaction for 2 hours, it was cooled to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. The resulting product was dissolved in 830 mL of toluene (an amount corresponding to 30 times the total volume of the obtained product), washed twice with water, and then the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to obtain a white solid compound A-6 (16.3 g, 59%, MS: [M+H] ⁺ = 341.5).

2) Synthesis of compound 6

Compound A-6 (15 g, 44.1 mmol) and 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (15.8 g, 44.1 mmol) was added to 150 ml of dimethylacetamide, stirred and refluxed. Thereafter, potassium triphosphate (28.1 g, 132.2 mmol) was added, followed by heating and stirring. After the reaction for 3 hours, it was cooled to room temperature, and the resulting solid was filtered. The resulting solid was dissolved in 875 mL of chloroform (an amount corresponding to 30 times the total volume of the solid), washed twice with water, and then the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to obtain a white solid compound 6 (19 g, 65%, MS: [M+H] ⁺ = 662.8).

Synthesis Example 7: Synthesis of compound 7

1) Synthesis of compound A-7

In a nitrogen atmosphere, 4-bromo-9H-carbazole (20 g, 81.3 mmol) and 9H-carbazole (13.6 g, 81.3 mmol) were added to 400 ml of xylene, stirred and refluxed. Thereafter, potassium triphosphate (23.4 g, 243.8 mmol) was added, and after sufficient stirring, bis (tri-tert-butylphosphine) palladium (1.2 g, 2.4 mmol) was added. After the reaction for 3 hours, it was cooled to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. The resulting product was dissolved in 810 mL of toluene (an amount corresponding to 30 times the total volume of the obtained product), washed twice with water, and then the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to obtain a white solid compound A-7 (15.9 g, 59%, MS: [M+H] ⁺ = 333.4).

2) Synthesis of compound B-2

Compound A-7 (15 g, 45.1 mmol) and 2-chloro-4-(3-chlorophenyl)-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine in nitrogen atmosphere (17.7 g, 45.1 mmol) was added to 150 ml of dimethylacetamide, stirred and refluxed. Thereafter, potassium triphosphate (28.7 g, 135.4 mmol) was added, followed by heating and stirring. After reaction for 1 hour, the mixture was cooled to room temperature and the resulting solid was filtered. The obtained solid was dissolved in 932 mL of chloroform (an amount corresponding to 30 times the total volume of the solid), washed twice with water, and then the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to obtain a white solid compound B-2 (21.7 g, 70%, MS: [M+H] ⁺ = 689.2).

3) Synthesis of compound 7

Compound B-2 (15 g, 21.8 mmol) and (phenyl-d5)boronic acid (2.8 g, 21.8 mmol) were added to 300 ml of Diox in a nitrogen atmosphere, and stirred and refluxed. Thereafter, potassium triphosphate (13.9 g, 65.4 mmol) was dissolved in 14 ml of water and thoroughly stirred, followed by dibenzylideneacetone palladium (0.4 g, 0.7 mmol) and tricyclohexylphosphine (0.4 g, 1.3 mmol). was put in. After the reaction for 6 hours, the resulting solid was filtered after cooling to room temperature. The resulting solid was dissolved in 481 mL of dichlorobenzene (DCB) (an amount corresponding to 30 times the total volume of the solid), washed twice with water, and then the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. As a result, the concentrated compound was recrystallized from DCB and ethyl acetate to obtain a yellow solid compound 7 (9.8 g, 61%, MS: [M+H] ⁺ = 735.9).

Synthesis Example 8: Synthesis of compound 8

1) Synthesis of compound A-8

2,4-dichloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine (20 g, 63.3 mmol) and 2-([1,1'-biphenyl) in nitrogen atmosphere ]-3-yl-2',3',4',5',6'-d5)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (18 g, 63.3 mmol) to toluene It was added to 400ml, stirred and refluxed. Thereafter, potassium carbonate (26.2 g, 189.8 mmol) was dissolved in 79 ml of water, and after sufficient stirring, bis (tri-tert-butylphosphine) palladium (1 g, 1.9 mmol) was added. After the reaction for 3 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. The resulting product was dissolved in 1388 mL of tetrahydrofuran (an amount corresponding to 50 times the total volume of the obtained product), washed twice with water, and then the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using tetrahydrofuran and ethyl acetate, and as a result, a white solid compound A-8 (21.4 g, 77%, MS: [M+H] ⁺ = 439.9) was obtained. .

2) Synthesis of compound 8

In a nitrogen atmosphere, compound A-8 (10 g, 22.8 mmol) and compound A-9 (7.7 g, 22.8 mmol) were added to 100 ml of dimethylacetamide, and stirred and refluxed. Thereafter, potassium triphosphate (14.5 g, 68.3 mmol) was added, followed by heating and stirring. After the reaction for 3 hours, it was cooled to room temperature, and the resulting solid was filtered. The obtained solid was dissolved in 506 mL of chloroform (an amount corresponding to 30 times the total volume of the solid), and the organic layer was separated after washing twice with water. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. As a result, the concentrated compound was recrystallized from chloroform and ethyl acetate to obtain a white solid compound 8 (13.2 g, 78%, MS: [M+H] ⁺ = 741.9).

Example 1

A glass substrate coated with ITO (Indium Tin Oxide) to a thickness of 1,400 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. In this case, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

A hole injection layer was formed by thermal vacuum deposition of the following HT-A compound and 5% by weight of PD on the prepared ITO transparent electrode to a thickness of 100 Å, and only the HT-A compound was deposited thereon to a thickness of 1150 Å to form a hole transport layer did. On the hole transport layer, the following HT-B compound was thermally vacuum deposited to a thickness of 450 Å to form an electron blocking layer. Then, as a first host, compound 1 prepared in Synthesis Example 1 and a GH-A compound as a second host were mixed in a weight ratio of 40:60 to constitute a host, and 15% by weight of GD based on the total weight of the host Using the compound as a dopant, it was vacuum-deposited to a thickness of 400 Å on the electron suppression layer to form a light emitting layer. Then, the following ET-A compound was vacuum-deposited to a thickness of 50 Å on the light emitting layer to form a hole blocking layer. Then, the following ET-B compound and Liq compound were thermally vacuum deposited on the hole blocking layer in a weight ratio of 2:1 to form an electron transport layer to a thickness of 250 Å. On the electron transport layer, LiF and magnesium were vacuum-deposited to a thickness of 30 Å in a weight ratio of 1:1 to form an electron injection layer. Magnesium and silver were deposited on the electron injection layer in a weight ratio of 1:4 to form a cathode to a thickness of 160 Å, thereby manufacturing an organic light emitting diode.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7 Å/sec, the deposition rate of magnesium and silver was maintained at 2 Å/sec, and the vacuum degree during deposition was 1 x 10 ^-7 ~ 5 x 10 ^-8 torr. kept.

Examples 2 to 8, and Comparative Examples 1 to 5

The organic light emitting devices of Examples 2 to 8 and Comparative Examples 1 to 5 were manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used as the first host when the light emitting layer was formed. did. In this case, when a mixture of two types of compounds is used as the host, the weight ratio between the host compounds is indicated in parentheses.

The structures of the compounds used in Comparative Examples 1 to 5 are as follows.

<Test Example: Evaluation of Device Characteristics>

The organic light-emitting devices prepared in Examples 1 to 8 and Comparative Examples 1 to 5 were heat-treated in an oven at 100° C. for 30 minutes, then taken out, and voltage, efficiency, and lifespan (T95) were measured while applying a current, and the results were obtained. It is shown in Table 1 below. At this time, the voltage and efficiency were measured by applying a current density of 10 mA/cm ² , and the lifetime (T95) was measured for the time (hr) required for the luminance to decrease from the initial luminance to 95% at a current density of 20 mA/cm ² .

	1st host	@ 10mA/cm 2		@ 20mA/cm 2
		Voltage (V)	efficiency (cd/A)	life span (T95, hr)
Example 1	compound 1	4.1	67.2	88
Example 2	compound 2	4.3	66.5	91
Example 3	compound 3	3.9	64.3	84
Example 4	compound 4	4.4	65.4	84
Example 5	compound 5	4.1	64.9	98
Example 6	compound 6	4.3	69.2	96
Example 7	compound 7	4.2	69.5	81
Example 8	compound 8	4.1	68.2	95
Comparative Example 1	CE 1	4.1	63.2	66
Comparative Example 2	CE 2	4.3	55.3	35
Comparative Example 3	CE 3	4.4	66.5	63
Comparative Example 4	CE 4	4.1	67.0	74
Comparative Example 5	CE 5	4.5	60.1	52

As a result of the experiment, the organic light emitting devices of Examples 1 to 8 including the deuterium substituted compound exhibited a significantly improved effect in terms of lifespan characteristics while exhibiting the same level of low voltage and high efficiency as compared to Comparative Examples 1 to 5. It was. In particular, when Example 1 and Comparative Examples 1, 3, and 4 are compared, the effect of improving lifespan characteristics according to deuterium substitution in the first host compound included in the emission layer is more clear.

From the above results, it can be seen that when the compound of Formula 1 is used in the light emitting layer of the organic electroluminescent device, it is possible to realize a more improved effect in terms of lifespan characteristics while exhibiting a low driving voltage and excellent efficiency.

[Explanation of code]

1: Substrate 2: Anode

3: organic layer 4: cathode

5: hole injection layer 6: hole transport layer

7: electron suppression layer 8: light emitting layer

9: hole blocking layer 10: electron transport layer

11: electron injection layer

Claims (13)

1. A compound represented by Formula 1 or 2:

   [Formula 1]

   

   [Formula 2]

   

   In Formulas 1 and 2,

   X ₁ To X ₃ are each independently CH, or N, wherein at least one of X ₁ To X ₃ is N,

   Y is O, or S;

   Ar is substituted or unsubstituted C _1-30 alkyl, substituted or unsubstituted C _3-30 cycloalkyl, substituted or unsubstituted C _6-60 aryl, or substituted or unsubstituted N, O and S C _2-60 heteroaryl including any one or more heteroatoms selected from the group,

   L ₁ and L ₂ are each independently a single bond, phenylene, biphenylene, or terphenylene,

   R ₁ and R ₂ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C _1-60 alkyl, substituted or unsubstituted C _6-60 aryl, or substituted or unsubstituted N, O and C _2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of S,

   m is an integer from 1 to 7,

   n is an integer from 1 to 8,

   wherein Ar is substituted with one or more deuterium, or at least one of R ₁ and R ₂ is deuterium,

   The compound represented by Formula 1 or 2 includes 4 or more deuterium in the compound.
2. According to claim 1,

   The compound represented by Formula 1 or 2 contains 4 to 20 deuterium in the compound,

   compound.
3. According to claim 1,

   X ₁ to X ₃ are each N,

   compound.
4. According to claim 1,

   Ar is C _6-20 aryl,

   Ar is unsubstituted or substituted with 5 to 15 deuterium,

   compound.
5. According to claim 1,

   Ar is phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, phenanthrenyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, or tri phenylenyl,

   Ar is unsubstituted or substituted with 5 to 13 deuterium,

   compound.
6. According to claim 1,

   L ₁ is a single bond, phenylene, biphenylene, or terphenylene, and L ₂ is a single bond; or

   L ₁ is a single bond and L ₂ is phenylene or biphenylene,

   compound.
7. According to claim 1,

   R ₁ and R ₂ are each independently hydrogen or deuterium;

   compound.
8. According to claim 1,

   Ar is phenyl, biphenyl, terphenyl, or triphenylenyl;

   Wherein Ar is substituted with 5 to 13 deuterium,

   R ₁ and R ₂ are each hydrogen;

   compound.
9. According to claim 1,

   Ar is phenyl, biphenyl, terphenyl, or triphenylenyl;

   Ar is unsubstituted,

   At least one of R ₁ and R ₂ is deuterium, the other is hydrogen,

   m is an integer from 1 to 7, n is an integer from 1 to 8,

   The compound represented by Formula 1 or 2 contains 4 to 15 deuterium in the compound,

   compound.
10. According to claim 1,

    Ar is phenyl, biphenyl, terphenyl, or triphenylenyl;

    Wherein Ar is substituted with 5 to 13 deuterium,

    At least one of R ₁ and R ₂ is deuterium, the other is hydrogen,

    m is an integer from 1 to 7, n is an integer from 1 to 8,

    compound.
11. According to claim 1,

    The compound represented by Formula 1 or 2 is any one selected from the group consisting of

    compound:

    

    

    

    

    

    

    

    

    .
12. a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound according to claim 1 .
13. 13. The method of claim 12,

    The organic material layer containing the compound is a light emitting layer,

    organic light emitting device.

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