KR20220120495A - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a novel compound and an organic light emitting device using the same. The present invention provides a compound represented by chemical formula 1. The compound represented by chemical formula 1 can be used as a material for an organic layer of the organic light emitting device, and thus can improve efficiency, lower driving voltage, and/or improve lifespan characteristics of the organic light emitting device.

Description

Novel compound and organic light emitting device comprising the same

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.

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 the following formula (1):

[Formula 1]

In Formula 1,

Y is O or S;

D means deuterium,

L is a single bond; substituted or unsubstituted C _6-60 arylene; or C _2-60 heteroarylene containing one or more heteroatoms among substituted or unsubstituted N, O and S;

L ₁ and L ₂ are each independently a single bond; Or a substituted or unsubstituted C _6-60 arylene,

Ar ₁ and Ar ₂ are each independently substituted or unsubstituted C _6-60 aryl; C _4-60 heteroaryl containing O atom; C _4-60 heteroaryl containing an S atom; C _2-60 heteroaryl containing a substituted or unsubstituted N atom; or C _2-60 heteroaryl containing two or more heteroatoms among substituted or unsubstituted N, O and S;

R is hydrogen; or C _6-60 aryl unsubstituted or substituted with deuterium.

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 above. .

The compound represented by Chemical Formula 1 described above may be used as a material for the organic material layer of the organic light emitting device, and may improve efficiency, low driving voltage and/or lifespan characteristics in the organic light emitting device.

FIG. 1 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , a light emitting 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 (3), electron transport layer (8), electron injection layer (9) and an example of an organic light emitting device including a cathode 4 .

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

(Definition of Terms)

및

는 다른 치환기에 연결되는 결합을 의미한다.In this specification,

and

means a bond connected to another substituent.

As used herein, the term "substituted or unsubstituted" refers to deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkyl group Thioxy group, arylthioxy group, alkylsulfoxy group, arylsulfoxy group, silyl group, boron group, alkyl group, cycloalkyl group, alkenyl group, aryl group, aralkyl group, aralkenyl group, alkylaryl group, alkylamine group, aralkylamine substituted or unsubstituted with one or more substituents selected from the group consisting of a group, a heteroarylamine group, an arylamine group, an arylphosphine group, or a heteroaryl group containing at least one of N, O and S atoms; It means a substituted or unsubstituted one in which two or more substituents among the above-exemplified substituents are connected. 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. For example, the term "substituted or unsubstituted" means "unsubstituted or at least one selected from the group consisting of deuterium, halogen, C _1-10 alkyl, C _1-10 alkoxy and C _6-20 aryl. , for example, substituted with 1 to 5 substituents. Also, as used herein, the term "substituted with one or more substituents" shall be understood to mean, for example, "substituted with 1 to 5 substituents", or "substituted with 1 or 2 substituents". can

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, it may be a substituent having the following structure, 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, it may be a substituent of the following structural formula, 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, it may be a substituent having the following structure, 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 a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like, but is not limited thereto.

In the present specification, examples of the halogen group include fluoro, chloro, bromo, or iodo.

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, 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-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethyl-propyl, 1,1-dimethylpropyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, isohexyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5 -Methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2,4,4-trimethyl-1-pentyl, 2,4,4- trimethyl-2-pentyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 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 is 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 having aromaticity. 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 triphenylenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, and the like, but 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 a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an acridyl group, Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinoline group, indole group, Carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, isoxazolyl group, thiadiazolyl group group, phenothiazinyl group, dibenzofuranyl group, and the like, but is 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 heteroarylamines, the description regarding heteroaryl described above 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)

On the other hand, the present invention provides a compound represented by the above formula (1).

Specifically, the compound represented by Formula 1 has a dibenzofuran/dibenzothiophene core, and a phenyl group (phenyl-D5) substituted with 5 deuteriums at position 6 of the core is substituted, and at position 1 It has a structure in which a triazinyl group is further substituted. In addition, the compound may have a structure in which carbon at position 8 of the dibenzofuran/dibenzothiophene is unsubstituted or substituted with aryl substituted with deuterium.

In particular, the compound having a structure in which a triazinyl group is substituted at the 1st position and a phenyl group substituted with 5 deuterium at the 6th position of the dibenzofuran/dibenzothiophene core is a C-D bond bond energy (bond energy) ) is greater than the binding energy of the C-H bond, so it has a stronger binding energy in the molecule compared to the compound without a phenyl group substituted with deuterium, and thus improved material stability may be exhibited. In addition, since deuterium is not directly substituted in the dibenzofuran/dibenzothiophene core, the compound may exhibit higher electronic stability than a compound in which deuterium is directly substituted in the core.

Accordingly, the lifespan characteristics of the organic light emitting device employing the compound may be remarkably improved.

Meanwhile, in the compound, Ar ₁ and Ar ₂ which are substituents of the triazinyl group are any one substituent selected from the group consisting of:

i) substituted or unsubstituted C _6-60 aryl;

ii) C _4-60 heteroaryl comprising an unsubstituted O atom;

iii) C _4-60 heteroaryl comprising an unsubstituted S atom;

iv) C _2-60 heteroaryl comprising a substituted or unsubstituted N atom; and

v) C _2-60 heteroaryl containing at least two heteroatoms among substituted or unsubstituted N, O and S

Here, "C _4-60 heteroaryl containing an O atom" refers to a monovalent heterocyclic group having 4 to 60 carbon atoms while including at least one O atom which is a hetero atom, and including the O atom Examples of C _4-60 heteroaryl include thiofuranyl, dibenzofuranyl, benzonaphthofuranyl and dinaphthofuranyl.

In addition, "C _4-60 heteroaryl containing an S atom" refers to a monovalent heterocyclic group having 4 to 60 carbon atoms while including at least one S atom, which is a hetero atom, and including the S atom. Examples of C _4-60 heteroaryl include thiophenyl, benzothiophenyl, dibenzothiophenyl, benzonaphthothiophenyl and dinaphthothiophenyl.

In addition, "C _2-60 heteroaryl containing an N atom" means a monovalent heterocyclic group having 2 to 60 carbon atoms while including at least one N atom, which is a hetero atom, and including the N atom Examples of C _2-60 heteroaryl include imidazolyl, pyrrolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, indolyl, carbazolyl and benzocarba sleepiness, etc. are mentioned.

In addition, "C _2-60 heteroaryl containing two or more heteroatoms from N, O and S" means having 2 to 60 carbon atoms while including two or more types of heteroatoms N, O and S atoms. Means a heterocyclic group, and examples of C _2-60 heteroaryl containing two or more heteroatoms among N, O and S include thiazolyl, oxazolyl, benzoxazolyl, isoxazolyl, phenothiazinyl and thiadia sleepiness, etc. are mentioned.

In other words, in Formula 1, Ar ₁ and Ar ₂ do not include C _4-60 heteroaryl including an O atom substituted with a substituent and C _4-60 heteroaryl including an S atom substituted with a substituent. This is because the compound may exhibit high electronic stability when used as a host material of the light emitting layer compared to the compound in which Ar ₁ and/or Ar ₂ is an O or S-containing heteroaryl group substituted with a substituent such as a phenyl group.

Specifically, Ar ₁ and Ar ₂ are each independently C _6-20 aryl unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, methyl and phenyl; unsubstituted dibenzofuranyl; unsubstituted dibenzothiophenyl; or C _2-20 heteroaryl comprising N atoms unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, methyl and phenyl.

More specifically, Ar ₁ and Ar ₂ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl;

Here, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl and carbazolyl are each independently unsubstituted or at least one selected from the group consisting of deuterium, methyl and phenyl, preferably It may be substituted with 1 to 5 substituents.

For example, Ar ₁ and Ar ₂ may each independently be any one selected from the group consisting of, but are not limited thereto:

.

.

In this case, Ar ₁ and Ar ₂ may be the same as each other. Alternatively, Ar ₁ and Ar ₂ may be different.

Also, in one embodiment, at least one of Ar ₁ and Ar ₂ may be unsubstituted or substituted C _6-12 aryl with deuterium.

,

,

, 또는

일 수 있다. For example, at least one of Ar ₁ and Ar ₂ is

,

,

, or

can be

Also, in one embodiment, L, L ₁ and L ₂ may be a single bond, or C _6-20 arylene unsubstituted or substituted with deuterium.

Specifically, L may be a single bond.

In addition, L ₁ and L ₂ may each independently be a single bond or phenylene. In other words, L ₁ and L ₂ may each independently be a single bond, 1,2-phenylene, 1,3-phenylene, or 1,4-phenylene.

For example, L ₁ and L ₂ are both single bonds; or

One of L ₁ and L ₂ may be a single bond, and the other may be 1,2-phenylene, 1,3-phenylene, or 1,4-phenylene.

In this case, L ₁ and L ₂ may be the same as each other. or L ₁ and L ₂ may be different.

Also, in one embodiment, R is hydrogen; or unsubstituted or substituted C _6-20 aryl with deuterium.

More specifically, R is hydrogen; phenyl unsubstituted or substituted with deuterium; biphenylyl unsubstituted or substituted with deuterium; or unsubstituted or naphthyl substituted with deuterium.

,

,

, 또는

일 수 있다.For example, R is hydrogen,

,

,

, or

can be

Further, in one embodiment, when R is not hydrogen, that is, when R is C _6-60 aryl unsubstituted or substituted with deuterium, R may be the same as Ar ₁ or Ar ₂ .

Also, in one embodiment, the compound may be represented by any one of the following 1-1 to 1-5:

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

In Formulas 1-1 to 1-5,

Y, L ₁ , L ₂ , Ar ₁ and Ar ₂ are as defined in Formula 1 above.

On the other hand, representative examples of the compound represented by Formula 1 are as follows:

.

On the other hand, the compound represented by the formula (1) can be prepared by a preparation method as shown in Scheme 1 below, for example:

[Scheme 1]

In Scheme 1, X is halogen, preferably bromo, or chloro, and the description of the remaining substituents is as defined above.

Specifically, the compound represented by Formula 1 may be prepared by Suzuki-coupling reaction of reactants A1 and A2. At this time, the Suzuki-coupling reaction is preferably performed under a palladium catalyst and a base, and the reactor for the reaction may be changed to a reactor known in the art. Such a manufacturing method may be more specific in Preparation Examples to be described later.

(organic light emitting element)

On the other hand, the present invention provides an organic light emitting device including the compound represented by the formula (1). 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 the compound represented by Formula 1 above. .

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, etc. 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 one embodiment, the organic material layer may include a light emitting layer, wherein the organic material layer including the compound may be a light emitting layer.

In another embodiment, the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein the organic material layer including the compound may be a light emitting layer or an electron transport layer.

In another embodiment, the organic material layer may include a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein the organic material layer containing the compound may be a light emitting layer or an electron transport layer.

In another embodiment, the organic material layer may include a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer, wherein the organic material layer comprising the compound is a light emitting layer or an electron transport layer can be

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 further comprises a hole injection layer and a hole transport layer between the first electrode and the light emitting layer, and an electron transport layer and an electron injection layer between the light emitting layer and the second electrode in addition to the light emitting layer as an organic layer can have a structure that However, the structure of the organic light emitting device is not limited thereto and may include a smaller number or a larger number of organic layers.

In addition, in the organic light emitting device according to the present invention, an anode, one or more organic material layers and a cathode are sequentially stacked on a substrate, wherein the first electrode is an anode and the second electrode is a cathode. may be small. In addition, in the organic light emitting device according to the present invention, the first electrode is a cathode and the second electrode is an anode, and a cathode, one or more organic material layers and an anode are sequentially stacked on a substrate of an inverted type organic structure. It may be a light emitting device. 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 .

FIG. 1 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , a light emitting layer 3 , and a cathode 4 . In such a structure, the compound represented by Formula 1 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 (3), electron transport layer (8), electron injection layer (9) and an example of an organic light emitting device including a cathode 4 . In such a structure, the compound represented by Formula 1 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 Formula 1 above. 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 a first electrode, an organic material layer, and a second electrode 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 forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, the compound represented by Formula 1 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 polymers 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.

In addition, 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 in the light emitting layer A compound that prevents the generated 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 preferred. 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, polyaniline and polythiophene-based conductive polymers, and the like, but are not limited thereto.

In addition, the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer, and as a hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and transferring them to the light emitting layer Mobility with respect to holes This large material is suitable. An arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion may be used as the hole transport material, but the present invention is not limited thereto.

In addition, the electron blocking layer is formed on the hole transport layer, preferably provided in contact with the light emitting layer, to adjust the hole mobility and prevent excessive movement of electrons by increasing the hole-electron coupling probability by increasing the organic light emitting device It means a layer that plays a role in improving the efficiency of The electron blocking layer includes an electron blocking material, and an example of such an electron blocking material may be an arylamine-based organic material, but is not limited thereto.

In addition, the emission layer may include a host material and a dopant material. As such a host material, the compound represented by Formula 1 may be used. In addition, the host material may further include a condensed aromatic ring derivative or a hetero ring-containing compound in addition to the compound represented by Formula 1 above. 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.

In one embodiment, the light emitting layer may further include a compound represented by the following formula (2) in addition to the compound represented by the formula (1):

[Formula 2]

In Formula 2,

Ar' ₁ and Ar' ₂ are each independently, substituted or unsubstituted C _6-60 aryl; or C _2-60 heteroaryl containing one or more heteroatoms among substituted or unsubstituted N, O and S;

R′ ₁ and R′ ₂ are each independently hydrogen; heavy hydrogen; C _1-60 alkyl; C _6-60 aryl; or C _2-60 heteroaryl containing one or more heteroatoms among N, O and S;

r and s are each independently an integer of 0 to 7.

When the organic light emitting device further includes a compound represented by Formula 2 capable of efficiently transferring holes to a dopant material as a host material of the emission layer, together with the compound represented by Formula 1 having excellent electron transport ability in the emission layer The probability of recombination of holes and electrons of the organic light emitting diode increases, and thus the efficiency and lifespan of the organic light emitting diode may be improved.

According to one embodiment, the compound represented by Formula 2 may be represented by Formula 2':

[Formula 2']

In Formula 2',

Ar′ ₁ , Ar′ ₂ , R′ ₁ , R′ ₂ , r and s are as defined in Formula 2 above.

In addition, in Formula 2, Ar' ₁ and Ar' ₂ are each independently C _6-20 aryl, or C _2-20 heteroaryl including one heteroatom among N, O and S;

Here, Ar′ ₁ may be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and C _6-20 aryl.

For example, Ar' ₁ and Ar' ₂ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, dibenzofuranyl, or dibenzothiophenyl;

Here, Ar′ ₁ may be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and C _6-20 aryl.

In this case, at least one of Ar' ₁ and Ar' ₂ may be phenyl or biphenylyl.

In addition, in Formula 2, R' ₁ and R' ₂ may each independently be hydrogen, deuterium, or C _6-20 aryl.

For example, R′ ₁ and R′ ₂ may each independently be hydrogen, deuterium, or phenyl, but is not limited thereto.

In addition, r and s, each representing the number of R′ ₁ and R′ ₂ , may each independently be 0, 1, 2, 3, 4, 5, 6, or 7.

More specifically, r and s may each independently be 0, 1, or 7.

For example, r+s may be 0 or 1.

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

.

.

The two host materials, the compound represented by Formula 1 and the compound represented by Formula 2, may be included in the light emitting layer in a weight ratio of 10:90 to 90:10, for example, 50:50.

Further, 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.

In addition, the hole blocking layer is formed on the light emitting layer, preferably provided in contact with the light emitting layer, to control electron mobility and prevent excessive movement of holes to increase the hole-electron coupling probability, thereby increasing the efficiency of the organic light emitting device. It means the layer that plays a role in improving. 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.

In addition, the electron transport layer serves to transport the electrons received from the electron injection layer to the emission layer, and is formed on the emission layer or the hole blocking layer. The electron transport layer includes an electron transport material, and as the electron transport material, a material having high electron mobility is suitable. Specific examples of the electron transport material include an Al complex of 8-hydroxyquinoline; complexes containing Alq ₃ ; 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, metals A complex compound or a nitrogen-containing 5-membered ring derivative may be used together as an electron transport material.

In addition, the electron injection layer serves to inject electrons from the electrode, and is formed on the electron transport layer. Examples of the electron injection material included in the electron injection layer include LiF, NaCl, CsF, Li ₂ O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, Imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, etc. derivatives thereof, metal complex compounds and nitrogen-containing 5-membered ring derivatives may be used, but the present invention is not limited thereto.

Here, as the metal complex compound, 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-hydroxy Roxyquinolinato)(o-crezolato)gallium, bis(2-methyl-8-hydroxyquinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-hydroxyquinolinato)( 2-naphtolato) gallium, and the like, but are not limited thereto.

The organic light emitting device according to the present invention may be a bottom emission device, a top emission device, or a double-sided light emitting device, and in particular, may be a bottom emission device requiring relatively high luminous efficiency.

In addition, the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

The compound represented by Formula 1 and the preparation of an organic light emitting device including the same will be described in detail in Examples below. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

Preparation Example 1: Preparation of compound A-4

1) Preparation of compound A-1

In a nitrogen atmosphere, 2-bromo-6-iodophenol (100 g, 336.1 mmol) and (2-chloro-6-fluorophenyl)boronic acid (58.5 g, 336.1 mmol) were added to 2000 mL of tetrahydrofuran, stirred and refluxed. Thereafter, potassium carbonate (139.4 g, 1008.4 mmol) was dissolved in 139 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (11.6 g, 10.1 mmol) was added. After 2 hours of reaction, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 5041 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 from chloroform and ethyl acetate to prepare a white solid compound A-1 (59.5 g, 59%, MS: [M+H] ⁺ = 300.9).

2) Preparation of compound A-2

In a nitrogen atmosphere, A-1 (50 g, 166.7 mmol) was put into 250 mL of dimethylformamide, potassium carbonate was added, and stirred and heated to 140°C. After 3 hours of reaction, the mixture was cooled to room temperature, and then water was added. After this, the formed solid was filtered. This was again added to 497 mL of chloroform to dissolve, 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 purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound A-2 (29.3 g, 59%, MS: [M+H] ⁺ = 298.9).

3) Preparation of compound A-3

In a nitrogen atmosphere, A-2 (50 g, 178.6 mmol) and phenylboronic acid-D5 (22.7 g, 178.6 mmol) were added to 1000 mL of tetrahydrofuran, stirred and refluxed. Thereafter, potassium carbonate (74.1 g, 535.8 mmol) was dissolved in 74 mL of water, and the mixture was sufficiently stirred, and then tetrakistriphenyl-phosphinopalladium (6.2 g, 5.4 mmol) was added. After the reaction for 3 hours, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again put into 1011 mL of chloroform to dissolve, 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 from chloroform and ethyl acetate to prepare a yellow solid compound A-3 (26.3 g, 52%, MS: [M+H] ⁺ = 284.1).

4) Preparation of compound A-4

In a nitrogen atmosphere, A-3 (50 g, 139.2 mmol) and bis (pinacolato) diboron (38.9 g, 153.2 mmol) were added to 1000 mL of 1,4-dioxane, stirred and refluxed. After that, potassium acetate (40.1 g, 417.7 mmol) was added, and after sufficient stirring, palladium dibenzylideneacetone palladium (2.4 g, 4.2 mmol) and tricyclohexylphosphine (2.3 g, 8.4 mmol) were added. After the reaction for 3 hours, after cooling to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. This was again added to 628 mL of chloroform to dissolve, 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 from chloroform and ethanol to prepare a gray solid compound A-4 (52.8 g, 84%, MS: [M+H] ⁺ = 452.2).

Preparation Example 2: Preparation of compound B-4

1) Preparation of compound B-2

In a nitrogen atmosphere, A-1 (50 g, 166.7 mmol) and phenylboronic acid-D5 (21.2 g, 166.7 mmol) were placed in 1000 mL of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (69.1 g, 500.1 mmol) was dissolved in 69 mL of water, and the mixture was sufficiently stirred, and then tetrakistriphenyl-phosphinopalladium (5.8 g, 5 mmol) was added. After the reaction for 3 hours, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again put into 1011 mL of chloroform to dissolve, 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 from chloroform and ethyl acetate to prepare a yellow solid compound B-2 (26.8 g, 53%, MS: [M+H] ⁺ = 304.1).

2) Preparation of compound B-3

B-2 (50 g, 165 mmol) and N-Bromosuccinimide (32.3 g, 181.5 mmol) were added to 250 mL of dimethylformamide in a nitrogen atmosphere, and after reaction for 3 hours, cooled in an ice bath and water was added. After this, the formed solid was filtered. This was added to 596 mL of chloroform to dissolve, 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 purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound B-3 (37.5 g, 63%, MS: [M+H] ⁺ = 362).

2) Preparation of compound B-4

In a nitrogen atmosphere, B-3 (50 g, 131.2 mmol) was put into 250 mL of dimethylformamide, potassium carbonate was added, and stirred and heated to 140°C. After the reaction for 4 hours, it was cooled to room temperature, and then water was added. After this, the formed solid was filtered. This was added to 474 mL of chloroform to dissolve, 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 purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound B-4 (33.2 g, 70%, MS: [M+H] ⁺ = 362).

Preparation Example 3: Preparation of compound C-1

1) Preparation of compound C-1

In a nitrogen atmosphere, B-4 (50 g, 138.5 mmol) and phenylboronic acid (16.9 g, 138.5 mmol) were placed in 1000 mL of tetrahydrofuran, stirred and refluxed. Thereafter, potassium carbonate (57.4 g, 415.5 mmol) was dissolved in 57 mL of water, and the mixture was sufficiently stirred, and then tetrakistriphenyl-phosphinopalladium (4.8 g, 4.2 mmol) was added. After reaction for 1 hour, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again added to 995 mL of chloroform to dissolve, 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 from chloroform and ethyl acetate to prepare a white solid compound C-1 (30.8 g, 62%, MS: [M+H] ⁺ = 360.1).

2) Preparation of compound C-2

In a nitrogen atmosphere, C-1 (50 g, 139.2 mmol) and bis (pinacolato) diboron (38.9 g, 153.2 mmol) were added to 1000 mL of 1,4-dioxane, and stirred and refluxed. After that, potassium acetate (40.1 g, 417.7 mmol) was added, and after sufficient stirring, palladium dibenzylideneacetone palladium (2.4 g, 4.2 mmol) and tricyclohexylphosphine (2.3 g, 8.4 mmol) were added. After reaction for 7 hours, after cooling to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. This was again added to 628 mL of chloroform to dissolve, 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 from chloroform and ethanol to prepare a gray solid compound C-2 (50.9 g, 81%, MS: [M+H] ⁺ = 452.2).

Preparation Example 4: Preparation of compound D-1

1) Preparation of compound D-1

In a nitrogen atmosphere, B-4 (50 g, 138.5 mmol) and phenylboronic acid-D5 (17.6 g, 138.5 mmol) were added to 1000 mL of tetrahydrofuran, and the mixture was stirred and refluxed. Thereafter, potassium carbonate (57.4 g, 415.5 mmol) was dissolved in 57 mL of water, and the mixture was sufficiently stirred, and then tetrakistriphenyl-phosphinopalladium (4.8 g, 4.2 mmol) was added. After reaction for 1 hour, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again added to 1009 mL of chloroform to dissolve, 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 from chloroform and ethyl acetate to prepare a yellow solid compound D-1 (29.3 g, 58%, MS: [M+H] ⁺ = 365.1).

2) Preparation of compound D-2

In a nitrogen atmosphere, D-1 (50 g, 139.2 mmol) and bis(pinacolato)diboron (38.9 g, 153.2 mmol) were added to 1000 mL of 1,4-dioxane, and the mixture was stirred and refluxed. After that, potassium acetate (40.1 g, 417.7 mmol) was added, and after sufficient stirring, palladium dibenzylideneacetone palladium (2.4 g, 4.2 mmol) and tricyclohexylphosphine (2.3 g, 8.4 mmol) were added. After reaction for 7 hours, after cooling to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. This was again added to 635 mL of chloroform to dissolve, 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 from chloroform and ethanol to prepare a gray solid compound D-2 (50.8 g, 80%, MS: [M+H] ⁺ = 457.2).

Preparation Example 5: Preparation of compound E-1

1) Preparation of compound E-1

In a nitrogen atmosphere, B-4 (50 g, 114.9 mmol) and bis(pinacolato)diboron (32.1 g, 126.4 mmol) were added to 1000 mL of 1,4-dioxane, and the mixture was stirred and refluxed. After that, potassium acetate (33.1 g, 344.7 mmol) was added, and after sufficient stirring, palladium dibenzylideneacetone palladium (2 g, 3.4 mmol) and tricyclohexylphosphine (1.9 g, 6.9 mmol) were added. After the reaction for 4 hours, after cooling to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. This was added to 500 mL of chloroform to dissolve, 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 from chloroform and ethanol to prepare a gray solid compound E-1 (25.5 g, 51%, MS: [M+H] ⁺ = 436.1).

2) Preparation of compound E-2

In a nitrogen atmosphere, E-1 (50 g, 114.9 mmol) and bis(pinacolato)diboron (32.1 g, 126.4 mmol) were added to 1000 mL of 1,4-dioxane, and the mixture was stirred and refluxed. After that, potassium acetate (33.1 g, 344.7 mmol) was added, and after sufficient stirring, palladium dibenzylideneacetone palladium (2 g, 3.4 mmol) and tricyclohexylphosphine (1.9 g, 6.9 mmol) were added. After the reaction for 3 hours, after cooling to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. This was again added to 606 mL of chloroform to dissolve, 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 from chloroform and ethanol to prepare a gray solid compound E-2 (41.8 g, 69%, MS: [M+H] ⁺ = 528.3).

Preparation Example 6: Preparation of compound F-1

1) Preparation of compound F-1

In a nitrogen atmosphere, B-4 (50 g, 138.5 mmol) and naphthalen-2-ylboronic acid (23.8 g, 138.5 mmol) were added to 1000 mL of tetrahydrofuran, and the mixture was stirred and refluxed. Thereafter, potassium carbonate (57.4 g, 415.5 mmol) was dissolved in 57 mL of water, and the mixture was sufficiently stirred, and then tetrakistriphenyl-phosphinopalladium (4.8 g, 4.2 mmol) was added. After the reaction for 2 hours, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in 1133 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 from chloroform and ethyl acetate to prepare a white solid compound F-1 (40.2 g, 71%, MS: [M+H] ⁺ = 410.1).

2) Preparation of compound F-2

In a nitrogen atmosphere, F-1 (50 g, 122.2 mmol) and bis(pinacolato)diboron (34.2 g, 134.4 mmol) were added to 1000 mL of 1,4-dioxane, and the mixture was stirred and refluxed. After that, potassium acetate (35.2 g, 366.6 mmol) was added, and after sufficient stirring, palladium dibenzylideneacetone palladium (2.1 g, 3.7 mmol) and tricyclohexylphosphine (2.1 g, 7.3 mmol) were added. After the reaction for 5 hours, after cooling to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. This was added to 613 mL of chloroform to dissolve, 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 from chloroform and ethanol to prepare a gray solid compound F-2 (47.2 g, 77%, MS: [M+H] ⁺ = 502.3).

Preparation Example 7: Preparation of compound G-2

1) Preparation of compound G-1

In a nitrogen atmosphere, 1-chloro-6-iododibenzo[b,d]thiophene (50 g, 145.4 mmol) and phenylboronic acid-D5 (18.5 g, 145.4 mmol) were added to 1000 mL of tetrahydrofuran, stirred and refluxed. Thereafter, potassium carbonate (60.3 g, 436.2 mmol) was dissolved in 60 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (5 g, 4.4 mmol) was added. After the reaction for 2 hours, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again added to 861 mL of chloroform to dissolve, 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 from chloroform and ethyl acetate to prepare a white solid compound G-1 (31 g, 72%, MS: [M+H] ⁺ = 297.1).

2) Preparation of compound G-2

In a nitrogen atmosphere, G-1 (50 g, 168.9 mmol) and bis (pinacolato) diboron (47.2 g, 185.8 mmol) were added to 1000 mL of 1,4-dioxane, stirred and refluxed. After that, potassium acetate (48.7 g, 506.7 mmol) was added, and after sufficient stirring, palladium dibenzylideneacetone palladium (2.9 g, 5.1 mmol) and tricyclohexylphosphine (2.8 g, 10.1 mmol) were added. After the reaction for 6 hours, after cooling to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. This was again added to 661 mL of chloroform to dissolve, 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 from chloroform and ethanol to prepare a gray solid compound G-2 (34.4 g, 52%, MS: [M+H] ⁺ = 392.2).

Synthesis Example 1: Preparation of compound 1

In a nitrogen atmosphere, A-4 (20 g, 53.3 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (14.2 g, 53.3 mmol) were placed in 400 mL of tetrahydrofuran, stirred and refluxed. . After that, potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.8 g, 1.6 mmol) was added. After the reaction for 2 hours, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 1280 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 from chloroform and ethyl acetate to prepare a white solid compound Compound 1 (16.4 g, 64%, MS: [M+H] ⁺ = 481.2).

Synthesis Example 2: Preparation of compound 2

A-4 (20 g, 53.3 mmol) and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (18.3 g, 53.3 mmol) was added to 400 mL of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.8 g, 1.6 mmol) was added. After the reaction for 3 hours, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 1482 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 from chloroform and ethyl acetate to prepare a white solid compound Compound 2 (17.5 g, 59%, MS: [M+H] ⁺ = 557.2).

Synthesis Example 3: Preparation of compound 3

A-4 (20 g, 53.3 mmol) and 2-([1,1'-biphenyl]-4-yl)-3-chloro-6-phenyl-1,3,5-triazine (18.3 g, 53.3 mmol) was added to 400 mL of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.8 g, 1.6 mmol) was added. After the reaction for 3 hours, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 1482 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 from chloroform and ethyl acetate to prepare a white solid compound Compound 3 (21.1 g, 71%, MS: [M+H] ⁺ = 557.2).

Synthesis Example 4: Preparation of compound 4

A-4 (20 g, 53.3 mmol) and 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (19 g, 53.3 mmol) was added to 400 mL of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.8 g, 1.6 mmol) was added. After the reaction for 1 hour, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 1520 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 from chloroform and ethyl acetate to prepare a white solid compound Compound 4 (17.3 g, 57%, MS: [M+H] ⁺ = 571.2).

Synthesis Example 5: Preparation of compound 5

A-4 (20 g, 53.3 mmol) and 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine (19.9 g, 53.3 mmol) was added to 400 mL of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.8 g, 1.6 mmol) was added. After 2 hours of reaction, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 1562 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 from chloroform and ethyl acetate to prepare a white solid compound Compound 5 (22.8 g, 73%, MS: [M+H] ⁺ = 587.2).

Synthesis Example 6: Preparation of compound 6

A-4 (20 g, 53.3 mmol) and 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (16.9 g, 53.3 mmol) were mixed with tetrahydrofuran in a nitrogen atmosphere. It was added to 400 mL, stirred and refluxed. After that, potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.8 g, 1.6 mmol) was added. After the reaction for 1 hour, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 1413 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 from chloroform and ethyl acetate to prepare a white solid compound Compound 6 (18.1 g, 64%, MS: [M+H] ⁺ = 531.2).

Synthesis Example 7: Preparation of compound 7

A-4 (20 g, 53.3 mmol) and 2-chloro-4-(4-(naphthalen-1-yl)phenyl)-6-phenyl-1,3,5-triazine (21 g, 53.3 mmol) in nitrogen atmosphere ) was added to 400 mL of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.8 g, 1.6 mmol) was added. After the reaction for 1 hour, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 1616 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 from chloroform and ethyl acetate to prepare a white solid compound Compound 7 (24.6 g, 76%, MS: [M+H] ⁺ = 607.3).

Synthesis Example 8: Preparation of compound 8

A-4 (20 g, 53.3 mmol) and 2-chloro-3-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (19 g, 53.3 mmol) was added to 400 mL of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.8 g, 1.6 mmol) was added. After 2 hours of reaction, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 1520 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 from chloroform and ethyl acetate to prepare a white solid compound Compound 8 (21.6 g, 71%, MS: [M+H] ⁺ = 571.2).

Synthesis Example 9: Preparation of compound 9

C-2 (20 g, 44.3 mmol) and 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (15.2 g, 44.3 mmol) was added to 400 mL of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (18.4 g, 133 mmol) was dissolved in 18 mL of water and thoroughly stirred, and then tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After 2 hours of reaction, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 1401 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 from chloroform and ethyl acetate to prepare a white solid compound Compound 9 (21 g, 75%, MS: [M+H] ⁺ = 633.3).

Synthesis Example 10: Preparation of compound 10

In a nitrogen atmosphere, D-2 (20 g, 43.8 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (17.2 g, 43.8 mmol) were added to 400 mL of tetrahydrofuran, stirred and refluxed. . After that, potassium carbonate (18.2 g, 131.5 mmol) was dissolved in 18 mL of water, and the mixture was sufficiently stirred, and then tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After 2 hours of reaction, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 1329 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 from chloroform and ethyl acetate to prepare a white solid compound Compound 10 (15.9 g, 60%, MS: [M+H] ⁺ = 607.3).

Synthesis Example 11: Preparation of compound 11

A-4 (20 g, 53.3 mmol) and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (18.3 g, 53.3 mmol) was added to 400 mL of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.8 g, 1.6 mmol) was added. After the reaction for 3 hours, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 1698 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 from chloroform and ethyl acetate to prepare a white solid compound Compound 11 (26.8 g, 79%, MS: [M+H] ⁺ = 638.3).

Synthesis Example 12: Preparation of compound 12

A-4 (20 g, 53.3 mmol) and 2-([1,1'-biphenyl]-4-yl)-3-chloro-6-phenyl-1,3,5-triazine (18.3 g, 53.3 mmol) was added to 400 mL of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.8 g, 1.6 mmol) was added. After the reaction for 1 hour, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 1698 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 from chloroform and ethyl acetate to prepare a white solid compound Compound 12 (21.7g, 64%, MS: [M+H] ⁺ = 638.3).

Synthesis Example 13: Preparation of compound 13

A-4 (20 g, 53.3 mmol) and 2-([1,1'-biphenyl]-4-yl)-3-chloro-6-phenyl-1,3,5-triazine (18.3 g, 53.3 mmol) was added to 400 mL of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.8 g, 1.6 mmol) was added. After the reaction for 3 hours, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 1736 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 from chloroform and ethyl acetate to prepare a white solid compound Compound 12 (20.8 g, 60%, MS: [M+H] ⁺ = 652.3).

Synthesis Example 14: Preparation of compound 14

A-4 (20 g, 53.3 mmol) and 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (19 g, 53.3 mmol) was added to 400 mL of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.8 g, 1.6 mmol) was added. After 2 hours of reaction, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 1778 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 from chloroform and ethyl acetate to prepare a white solid compound Compound 13 (24.9 g, 70%, MS: [M+H] ⁺ = 668.3).

Synthesis Example 15: Preparation of compound 15

D-2 (20 g, 43.8 mmol) and 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (13.9 g, 43.8 mmol) were mixed with tetrahydrofuran in a nitrogen atmosphere. It was added to 400 mL, stirred and refluxed. After that, potassium carbonate (18.2 g, 131.5 mmol) was dissolved in 18 mL of water, and the mixture was sufficiently stirred, and then tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After the reaction for 1 hour, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 1340 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 from chloroform and ethyl acetate to prepare a white solid compound Compound 15 (19.6 g, 73%, MS: [M+H] ⁺ = 612.3).

Synthesis Example 16: Preparation of compound 16

D-2 (20 g, 43.8 mmol) and 2-chloro-4-(4-(naphthalen-1-yl)phenyl)-6-phenyl-1,3,5-triazine (17.2 g, 43.8 mmol) in nitrogen atmosphere ) was added to 400 mL of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (18.2 g, 131.5 mmol) was dissolved in 18 mL of water, and the mixture was sufficiently stirred, and then tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After the reaction for 3 hours, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 1507 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 from chloroform and ethyl acetate to prepare a white solid compound Compound 16 (20.5 g, 68%, MS: [M+H] ⁺ = 688.7).

Synthesis Example 17: Preparation of compound 17

D-2 (20 g, 43.8 mmol) and 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (15.7 g, 43.8 mmol) was added to 400 mL of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (18.2 g, 131.5 mmol) was dissolved in 18 mL of water, and the mixture was sufficiently stirred, and then tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After 2 hours of reaction, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 1427 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 from chloroform and ethyl acetate to prepare a white solid compound Compound 17 (20g, 70%, MS: [M+H] ⁺ = 652.3).

Synthesis Example 18: Preparation of compound 18

In a nitrogen atmosphere, E-2 (20 g, 37.9 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (10.1 g, 37.9 mmol) were placed in 400 mL of tetrahydrofuran, stirred and refluxed. . Thereafter, potassium carbonate (15.7 g, 113.8 mmol) was dissolved in 16 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.3 g, 1.1 mmol) was added. After the reaction for 1 hour, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 1199 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 from chloroform and ethyl acetate to prepare a white solid compound Compound 18 (15.8 g, 66%, MS: [M+H] ⁺ = 633.3).

Synthesis Example 19: Preparation of compound 19

In a nitrogen atmosphere, F-2 (20 g, 39.9 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (10.7 g, 39.9 mmol) were placed in 400 mL of tetrahydrofuran, stirred and refluxed. . Thereafter, potassium carbonate (16.5 g, 119.7 mmol) was dissolved in 17 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.4 g, 1.2 mmol) was added. After the reaction for 3 hours, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 1209 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 from chloroform and ethyl acetate to prepare a white solid compound Compound 19 (18.6 g, 77%, MS: [M+H] ⁺ = 607.3).

Synthesis Example 20: Preparation of compound 20

G-2 (20 g, 51.1 mmol) and 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine (19.1 g, 51.1 mmol) was added to 400 mL of tetrahydrofuran, stirred and refluxed. Thereafter, potassium carbonate (21.2 g, 153.4 mmol) was dissolved in 21 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.8 g, 1.5 mmol) was added. After 2 hours of reaction, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 1539 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 from chloroform and ethyl acetate to prepare a white solid compound Compound 20 (23.7 g, 77%, MS: [M+H] ⁺ = 603.2).

Example 1: Manufacture of organic light emitting device

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,300 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, 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 ITO for 30 minutes, ultrasonic cleaning 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 HI-1 compound to a thickness of 50 Å on the ITO transparent electrode prepared as described above. The following HT-1 compound was thermally vacuum-deposited to a thickness of 250 Å on the hole injection layer to form a hole transport layer, and the following HT-2 compound was vacuum-deposited to a thickness of 50 Å on the HT-1 deposition film to form an electron blocking layer.

Compound 1 prepared in Synthesis Example 1 above, the following YGH-1 compound, and phosphorescent dopant YGD-1 as a light emitting layer on the HT-2 deposited film were co-deposited in a weight ratio of 44:44:12 to form a light emitting layer having a thickness of 400 Å.

The following ET-1 compound was vacuum deposited to a thickness of 250 Å on the light emitting layer to form an electron transport layer, and the following ET-2 compound and LiF were vacuum deposited at a weight ratio of 98:2 on the electron transport layer to form an electron injection layer with a thickness of 100 Å formed. A cathode was formed by depositing aluminum to a thickness of 1000 Å on the electron injection layer.

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

Examples 2 to 20

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of Compound 1 of Synthesis Example 1 as one of the host materials of the light emitting layer in Example 1.

At this time, the structures of the compounds used in Examples 1 to 20 are summarized as follows.

Comparative Examples 1 to 5

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of Compound 1 of Synthesis Example 1 as one of the host materials of the light emitting layer in Example 1. At this time, the compounds of CE1 to CE5 of Table 1 are as follows.

Experimental Example 1: Evaluation of device characteristics

For each of the organic light emitting devices prepared in Examples and Comparative Examples, voltage and efficiency were measured at a current density of 10 mA/cm ² , and lifetimes were measured at a current density of 50 mA/cm ² The results are shown in Table 1 below. shown in At this time, LT95 means the time at which the initial luminance becomes 95%.

compound Voltage (V)
(@ 10mA/cm ² ) Efficiency (Cd/A)
(@ 10mA/cm ² ) color coordinates
(x,y) Life (h)
(LT ₉₅ at 50mA/cm ² ) Example 1 compound 1 4.1 75 0.45, 0.53 200 Example 2 compound 2 4.2 76 0.44, 0.54 210 Example 3 compound 3 4.3 74 0.45, 0.54 250 Example 4 compound 4 4.2 77 0.44, 0.53 220 Example 5 compound 5 4.1 78 0.45, 0.53 230 Example 6 compound 6 4.3 77 0.44, 0.54 240 Example 7 compound 7 4.2 75 0.45, 0.53 250 Example 8 compound 8 4.2 77 0.44, 0.54 250 Example 9 compound 9 4.2 80 0.45, 0.54 190 Example 10 compound 10 4.1 81 0.44, 0.53 200 Example 11 compound 11 4.2 82 0.45, 0.54 230 Example 12 compound 12 4.3 81 0.44, 0.53 240 Example 13 compound 13 4.2 82 0.45, 0.53 230 Example 14 compound 14 4.1 81 0.44, 0.54 270 Example 15 compound 15 4.4 80 0.45, 0.53 220 Example 16 compound 16 4.3 79 0.44, 0.54 230 Example 17 compound 17 4.2 81 0.45, 0.54 290 Example 18 compound 18 4.2 82 0.44, 0.53 260 Example 19 compound 19 4.3 80 0.44, 0.54 240 Example 20 compound 20 4.2 80 0.45, 0.54 270 Comparative Example 1 CE1 4.1 75 0.45, 0.53 100 Comparative Example 2 CE2 4.2 82 0.44, 0.53 130 Comparative Example 3 CE3 4.6 64 0.45, 0.54 25 Comparative Example 4 CE4 4.6 75 0.44, 0.53 150 Comparative Example 5 CE5 4.9 72 0.44, 0.53 140

As shown in Table 1, the organic light emitting device of the example using the compound represented by Formula 1 as the host material of the light emitting layer is significantly improved without a decrease in efficiency compared to the organic light emitting device of the comparative example using a compound having a different structure. It can be seen that the lifetime characteristics are shown. Therefore, it is confirmed that the compound of the present invention can improve the characteristics of the organic light emitting device compared to the comparative compound, considering that the luminous efficiency and lifespan characteristics of the organic light emitting device have a trade-off relationship with each other in general. It is possible.

1: Substrate 2: Anode
3: light emitting layer 4: cathode
5: hole injection layer 6: hole transport layer
7: electron blocking layer 8: electron transport layer
9: electron injection layer

Claims (14)

A compound represented by the following formula (1):
[Formula 1]

In Formula 1,
Y is O or S;
D means deuterium,
L is a single bond; substituted or unsubstituted C _6-60 arylene; or C _2-60 heteroarylene containing one or more heteroatoms among substituted or unsubstituted N, O and S;
L ₁ and L ₂ are each independently a single bond; Or a substituted or unsubstituted C _6-60 arylene,
Ar ₁ and Ar ₂ are each independently substituted or unsubstituted C _6-60 aryl; C _4-60 heteroaryl containing O atom; C _4-60 heteroaryl containing an S atom; C _2-60 heteroaryl containing a substituted or unsubstituted N atom; or C _2-60 heteroaryl containing two or more heteroatoms among substituted or unsubstituted N, O and S;
R is hydrogen; or C _6-60 aryl unsubstituted or substituted with deuterium.
According to claim 1,
L is a single bond,
compound.
According to claim 1,
L ₁ and L ₂ are each independently a single bond, or phenylene,
compound.
According to claim 1,
Ar ₁ and Ar ₂ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl;
Herein, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl and carbazolyl are each independently unsubstituted or with one or more substituents selected from the group consisting of deuterium, methyl and phenyl substituted,
compound.
5. The method of claim 4,
Ar ₁ and Ar ₂ are each independently any one selected from the group consisting of
compound:

.
According to claim 1,
At least one of Ar ₁ and Ar ₂ is unsubstituted or substituted C _6-12 aryl with deuterium;
compound.
According to claim 1,
R is hydrogen; phenyl unsubstituted or substituted with deuterium; biphenylyl unsubstituted or substituted with deuterium; or naphthyl unsubstituted or substituted with deuterium;
compound.
8. The method of claim 7,
R is hydrogen,

,

,

, or

sign,
compound.
According to claim 1,
The compound is represented by any one of the following formulas 1-1 to 1-5,
compound:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

In Formulas 1-1 to 1-5,
Y, L ₁ , L ₂ , Ar ₁ and Ar ₂ are as defined in claim 1.
According to claim 1,
The compound is any one selected from the group consisting of the following compounds,
compound:

.
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 contains the compound according to any one of claims 1 to 10 which is an organic light emitting device.
12. The method of claim 11,
The organic layer containing the compound is a light emitting layer,
organic light emitting device.
13. The method of claim 12,
The light emitting layer further comprises a compound represented by the following formula (2),
Organic light emitting device:
[Formula 2]

In Formula 2,
Ar' ₁ and Ar' ₂ are each independently, substituted or unsubstituted C _6-60 aryl; or C _2-60 heteroaryl containing one or more heteroatoms among substituted or unsubstituted N, O and S;
R′ ₁ and R′ ₂ are each independently hydrogen; heavy hydrogen; C _1-60 alkyl; C _6-60 aryl; or C _2-60 heteroaryl containing one or more heteroatoms among N, O and S;
r and s are each independently an integer of 0 to 7.
14. The method of claim 13,
The compound represented by Formula 2 is any one selected from the group consisting of the following compounds,
Organic light emitting device:

.

Images