KR20210089524A - 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 comprising the same. The present invention provides a compound represented by chemical formula 1. The compound represented by the chemical formula 1 described above can be used as a material for an organic material layer of the organic light emitting device, and also can improve efficiency, lower driving voltage, and/or improve lifespan characteristics in 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 layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light-emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of the organic light emitting device, when a voltage is applied between the two electrodes, 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 When it falls back to the ground state, it lights up.

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 organic light emitting material 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,

A is a benzene ring, a naphthalene ring, or a phenanthrene ring fused with an adjacent pentacyclic ring,

B is a naphthalene ring or a phenanthrene ring fused with an adjacent pentagonal ring,

Ra and Rb are each independently hydrogen; heavy hydrogen; substituted or unsubstituted C _1-60 alkyl; substituted or unsubstituted C _3-60 cycloalkyl; substituted or unsubstituted C _2-60 alkenyl; substituted or unsubstituted C _6-60 aryl; _{Or substituted or unsubstituted C 2-60} heteroaryl comprising any one or more selected from the group consisting of N, O and S,

Y ₁ to Y ₃ are each independently CH or N, provided that at least one of _{Y 1} to Y _{3 is N,}

Ar ₁ is adamantyl; substituted or unsubstituted C _6-60 aryl; _{Or substituted or unsubstituted C 2-60} heteroaryl comprising any one or more selected from the group consisting of N, O and S,

L ₁ to L ₃ are each independently a single bond, or a substituted or unsubstituted C _6-60 arylene;

R ₁ is each independently hydrogen; heavy hydrogen; substituted or unsubstituted C _1-60 alkyl; substituted or unsubstituted C _3-60 cycloalkyl; substituted or unsubstituted C _2-60 alkenyl; substituted or unsubstituted C _6-60 aryl; _{Or substituted or unsubstituted C 2-60} heteroaryl comprising any one or more selected from the group consisting of N, O and S,

a is an integer from 0 to 7.

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 Formula 1 described above may be used as a material for an organic material layer of an organic light emitting device, and may improve efficiency, low driving voltage, and/or lifespan characteristics in an organic light emitting device. In particular, the compound represented by the above formula (1) may be used as a hole injection, hole transport, hole control, light emission, electron control, electron transport, or electron injection material.

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), hole control layer (7), light emitting layer (3), electron control layer (8), electron transport layer (9) , an example of an organic light emitting device including an electron injection layer 10 and a cathode 4 is shown.

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

The present invention provides a compound represented by the above formula (1).

, 또는

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

, or

means a bond connected to another substituent.

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; 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 arylphosphine group; or N, O, and S atom means that it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group containing one or more atoms, or substituted or unsubstituted with two or more substituents connected among the above-exemplified substituents . 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, and may be interpreted as a substituent in which two phenyl groups are connected.

In the present specification, the number of carbon atoms in the carbonyl group is not particularly limited, but preferably 1 to 40 carbon atoms. Specifically, it may be a compound 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 compound 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 compound 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, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron 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-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are 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 phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.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, the heterocyclic group is a heterocyclic group including at least one of O, N, P, Si and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but it is preferably from 2 to 60 carbon atoms. Examples of the heterocyclic group 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, pyrido pyrimidinyl group, pyrido pyrazinyl 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, isoxazolyl group, thiadia and a jolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but is not limited thereto.

In the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group is the same as the above-described aryl group. 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 of the above-described heterocyclic group may be applied. In the present specification, the alkenyl group among the aralkenyl groups is the same as the above-described examples of the alkenyl group. 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 above-described heterocyclic group 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 heterocyclic group is not a monovalent group, and the description of the above-described heterocyclic group may be applied, except that it is formed by combining two substituents.

Preferably, A may be a benzene ring fused with an adjacent pentacyclic ring, and B may be a naphthalene ring fused with an adjacent pentacyclic ring, or a phenanthrene ring.

Preferably, Chemical Formula 1 may be represented by the following Chemical Formulas 1-1 to 1-4:

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4,

Y ₁ to Y ₃ , Ar ₁ , L ₁ to L ₃ , Ra, Rb, R ₁ and a are the same as defined in Formula 1 above.

Preferably, Ra and Rb are each independently hydrogen; heavy hydrogen; substituted or unsubstituted C _1-10 alkyl; substituted or unsubstituted C _6-20 aryl; Or it may be _{a C 2-20} heteroaryl comprising at least one selected from the group consisting of substituted or unsubstituted N, O and S,

More preferably, Ra and Rb may each be methyl.

Preferably, Ar ₁ is adamantyl; substituted or unsubstituted C _6-20 aryl; Or it may be _{a C 2-20} heteroaryl comprising at least one selected from the group consisting of substituted or unsubstituted N, O and S,

More preferably, Ar ₁ may be adamantyl, phenyl, biphenylyl, naphthyl, phenanthrenyl, phenanthrenyl phenyl, phenyl naphthyl, naphthyl phenyl, or dibenzofuranyl,

Most preferably, Ar ₁ may be adamantyl, phenyl, or any one selected from the group consisting of:

Preferably, L ₁ to L ₃ may each independently be a single bond, or a substituted or unsubstituted C _6-20 arylene,

More preferably, L ₁ to L ₃ may each independently be any one selected from the group consisting of a single bond or the following;

In the group,

R ₂ are each independently hydrogen; heavy hydrogen; halogen; cyano; nitro; amino; substituted or unsubstituted C _1-60 alkyl; substituted or unsubstituted C _3-60 cycloalkyl; substituted or unsubstituted C _2-60 alkenyl; substituted or unsubstituted C _6-60 aryl; _{Or substituted or unsubstituted C 2-60} heteroaryl comprising any one or more selected from the group consisting of N, O and S.

More preferably, L ₁ to L ₃ may each independently be a single bond, phenylene, biphenylylene, or naphthylene,

Most preferably, L ₁ to L ₃ may each independently be any one selected from the group consisting of a single bond or the following:

.

.

Preferably, _{each R 1} is independently hydrogen; heavy hydrogen; substituted or unsubstituted C _1-10 alkyl; substituted or unsubstituted C _3-10 cycloalkyl; substituted or unsubstituted C _2-10 alkenyl; substituted or unsubstituted C _6-20 aryl; Or it may be _{a C 2-20} heteroaryl comprising at least one selected from the group consisting of substituted or unsubstituted N, O and S,

More preferably, _{each R 1} may be hydrogen or deuterium,

Most preferably, _{each R 1} may be hydrogen.

Preferably, a may be zero.

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

.

.

The compound represented by Chemical Formula 1 may be prepared by, for example, a preparation method as in Scheme 1 below, and other compounds may be prepared similarly.

[Scheme 1]

In Scheme 1, Y ₁ to Y ₃ , Ar ₁ , L ₁ to L ₃ , Ra, Rb, R ₁ and a are as defined in Formula 1, X is halogen, preferably X is chloro or it's bromo

The Suzuki coupling reaction in Scheme 1 is preferably performed in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be changed as known in the art. The manufacturing method may be more specific in Preparation Examples to be described later.

In addition, 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. do.

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 hole control layer, a light emitting layer, an electron control layer, an electron transport layer, an electron injection layer 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 a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, the hole transport layer, or a layer that simultaneously injects and transports holes is represented by Formula 1 It may include the indicated compound.

In addition, the organic layer may include an emission layer, and the emission layer may include a compound represented by Formula 1 above.

In addition, the organic layer may include an electron control layer, an electron transport layer, an electron injection layer, or a layer that simultaneously transports and injects electrons, and the electron control layer, the electron transport layer, the electron injection layer, or the electron transport and electron injection layer. The layer for simultaneous injection may include the compound represented by Formula 1 above.

In addition, the organic layer may include a light emitting layer and an electron injection and transport layer, and the electron injection and transport layer may include the compound represented by Formula 1 above.

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 device 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 . 2 is a substrate (1), anode (2), hole injection layer (5), hole transport layer (6), hole control layer (7), light emitting layer (3), electron control layer (8), electron transport layer (9) , an example of an organic light emitting device including an electron injection layer 10 and a cathode 4 is shown. In such a structure, the compound represented by Formula 1 may be included in at least one of the light emitting layer and the electron transport 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 application method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

In addition to this 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 multilayer structure 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 with respect to the light emitting layer or the light emitting material, and is produced in the light emitting layer A compound which prevents the movement of excitons to the electron injection layer or the electron injection material and is excellent in the ability to form a thin film is preferable. Preferably, 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.

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

The hole control layer refers to a layer that controls the mobility of holes according to the energy level of the light emitting layer in the organic light emitting device.

The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

The emission layer may include a host material and a dopant material. The host material includes a condensed aromatic ring derivative or a compound containing a hetero ring. 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. Preferably, the compound represented by Formula 1 may be included as a 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, and the styrylamine compound is a substituted or unsubstituted derivative. 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 electron control layer refers to a layer that controls the mobility of electrons according to the energy level of the light emitting layer in the organic light emitting device.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light emitting layer. As an electron transport material, it is a material that can receive electrons from the cathode and transfer them to the light emitting layer, and a material with high electron mobility is suitable. Do. Specific examples include Al complex of 8-hydroxyquinoline; complexes containing Alq _{3 ;} organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function and followed by a layer of aluminum or silver. Specifically cesium, barium, calcium, ytterbium and samarium, followed in each case by an aluminum layer or a silver layer. Preferably, the compound represented by Formula 1 may be included as a material of the electron transport layer. Preferably, the compound represented by Formula 1 may be included as a material of the electron transport layer.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer. A compound which prevents movement to a layer and is excellent in the ability to form a thin film is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto. Preferably, the compound represented by Formula 1 may be included as a material of the electron injection layer.

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. However, the present invention is not limited thereto.

On the other hand, in the present invention, the "electron injection and transport layer" is a layer that performs both the role of the electron injection layer and the electron transport layer, and the materials serving the respective layers may be used alone or in combination, but limited thereto. doesn't happen Preferably, the compound represented by Formula 1 may be included as a material for the electron injection and transport layer.

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 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 for illustrating the present invention, and the scope of the present invention is not limited thereto.

Preparation Example 1: Preparation of Compound 1

Compound 2-(11,11-dimethyl-11H-benzo[b]fluoren-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ( 8.16 g, 22.06 mmol) and compound a-1 (8.67 g, 19.18 mmol) were completely dissolved in 180 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (90 ml) was added, and tetrakis-(triphenylphosphine)palladium (0.46 g, 0.40 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 210 ml of tetrahydrofuran to prepare compound 1 (7.78 g, yield: 61%).

MS[M+H] ⁺ = 660

Preparation Example 2: Preparation of compound 2

Compound 2-(11,11-dimethyl-11H-benzo[a]fluoren-8-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ( 5.64 g, 15.25 mmol) and compound a-2 (7.11 g, 13.26 mmol) were completely dissolved in 180 ml of tetrahydrofuran, and 2M aqueous potassium carbonate solution (90 ml) was added thereto, followed by tetrakis-(triphenylphosphine)palladium. (0.46 g, 0.40 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 210 ml of tetrahydrofuran to prepare compound 2 (6.44 g, yield: 65%).

MS[M+H] ⁺ = 745

Preparation Example 3: Preparation of compound 3

Compound 2-(7,7-dimethyl-7H-benzo[c]fluoren-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ( 9.83 g, 26.56 mmol) and compound a-3 (9.26 g, 23.09 mmol) were completely dissolved in 180 ml of tetrahydrofuran, and 2M aqueous potassium carbonate solution (90 ml) was added thereto, followed by tetrakis-(triphenylphosphine)palladium. (0.80 g, 0.69 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 210 ml of tetrahydrofuran to prepare compound 3 (6.44 g, yield: 65%).

MS[M+H] ⁺ = 610

Preparation Example 4: Preparation of compound 4

Compound compound 2-(9,9-dimethyl-9H-indeno[2,1-l]phenanthren-10-yl)-4,4,5,5-tetramethyl-1,3 in a 500 ml round bottom flask under nitrogen atmosphere ,2-dioxaborolane (8.30 g, 22.44 mmol) and compound a-4 (8.82 g, 19.51 mmol) were completely dissolved in 180 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (90 ml) was added, and tetrakis-(tri Phenylphosphine) palladium (0.68 g, 0.59 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 230 ml of tetrahydrofuran to prepare compound 4 (8.11 g, yield: 59%).

MS[M+H] ⁺ = 710

Preparation Example 5: Preparation of compound 5

Compound compound 2-(11,11-dimethyl-11H-benzo[b]fluoren-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in a 500 ml round bottom flask under nitrogen atmosphere (6.08 g, 16.43 mmol) and compound a-5 (7.66 g, 14.29 mmol) were completely dissolved in 180 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (90 ml) was added, and tetrakis-(triphenylphosphine) After adding palladium (0.50 g, 0.43 mmol), the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 230 ml of tetrahydrofuran to prepare compound 5 (7.24 g, yield: 61%).

MS[M+H] ⁺ = 834

Preparation Example 6: Preparation of compound 6

Compound compound 2-(11,11-dimethyl-11H-benzo[a]fluoren-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in a 500 ml round bottom flask under nitrogen atmosphere (9.89 g, 26.72 mmol) and compound a-6 (9.34 g, 23.23 mmol) were completely dissolved in 180 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (90 ml) was added, and tetrakis-(triphenylphosphine) After adding palladium (0.81 g, 0.70 mmol), the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250 ml of tetrahydrofuran to prepare compound 6 (8.37 g, yield: 59%).

MS[M+H] ⁺ = 610

Preparation Example 7: Preparation of compound 7

Compound compound 2-(7,7-dimethyl-7H-benzo[c]fluoren-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in a 500 ml round bottom flask under nitrogen atmosphere (6.87 g, 18.58 mmol) and compound a-7 (8.11 g, 16.16 mmol) were completely dissolved in 180 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (90 ml) was added, and tetrakis-(triphenylphosphine) After adding palladium (0.56 g, 0.48 mmol), the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250 ml of tetrahydrofuran to prepare compound 7 (6.89 g, yield: 60%).

MS[M+H] ⁺ = 710

Preparation 8: Preparation of compound 8

Compound compound 2-(9,9-dimethyl-9H-indeno[2,1-l]phenanthren-6-yl)-4,4,5,5-tetramethyl-1,3 in a 500 ml round bottom flask under nitrogen atmosphere ,2-dioxaborolane (7.26 g, 19.61 mmol) and compound a-8 (8.56 g, 17.05 mmol) were completely dissolved in 180 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (90 ml) was added, and tetrakis-(tri Phenylphosphine) palladium (0.59 g, 0.51 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250 ml of tetrahydrofuran to prepare compound 8 (7.25 g, yield: 60%).

MS[M+H] ⁺ = 710

Preparation Example 9: Preparation of compound 9

Compound compound 2-(11,11-dimethyl-11H-benzo[b]fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in a 500 ml round bottom flask under nitrogen atmosphere (8.23 g, 22.25 mmol) and compound a-9 (9.25 g, 19.35 mmol) were completely dissolved in 180 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (90 ml) was added, and tetrakis-(triphenylphosphine) After adding palladium (0.67 g, 0.58 mmol), the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250 ml of tetrahydrofuran to prepare compound 9 (6.88 g, yield: 52%).

MS[M+H] ⁺ = 686

Preparation 10: Preparation of compound 10

Compound compound 2-(11,11-dimethyl-11H-benzo[a]fluoren-7-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in a 500 ml round bottom flask under nitrogen atmosphere (7.74 g, 20.91 mmol) and compound a-10 (8.22 g, 18.19 mmol) were completely dissolved in 180 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (90 ml) was added, and tetrakis-(triphenylphosphine) After adding palladium (0.63 g, 0.55 mmol), the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250 ml of tetrahydrofuran to prepare compound 10 (5.99 g, yield: 50%).

MS[M+H] ⁺ = 660

Preparation Example 11: Preparation of compound 11

Compound 2-(7,7-dimethyl-7H-benzo[c]fluoren-10-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ( 5.29 g, 14.30 mmol) and compound a-11 (6.89 g, 12.44 mmol) were completely dissolved in 180 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (90 ml) was added, and tetrakis-(triphenylphosphine)palladium (0.43 g, 0.37 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 230 ml of tetrahydrofuran to prepare compound 11 (5.78 g, yield: 61%).

MS[M+H] ⁺ = 763

Preparation 12: Preparation of compound 12

Compound 2-(9,9-dimethyl-9H-indeno[2,1-l]phenanthren-10-yl)-4,4,5,5-tetramethyl-1,3, in a 500 ml round bottom flask under nitrogen atmosphere 2-dioxaborolane (5.69 g, 15.38 mmol) and compound a-12 (7.25 g, 13.38 mmol) were completely dissolved in 180 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (90 ml) was added, and tetrakis-(triphenyl) Phosphine) palladium (0.46 g, 0.40 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 230 ml of tetrahydrofuran to prepare compound 12 (6.24 g, yield: 58%).

MS[M+H] ⁺ = 801

Example 1-1

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1000 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 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, dried, and then 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.

The following compound HI-1 was formed to a thickness of 1150 Å as a hole injection layer on the thus prepared ITO transparent electrode, and the following compound A-1 was p-doped with 1.5 wt% of compound HI-1. The following compound HT-1 was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 800 Å. Then, the following compound EB-1 was vacuum-deposited to a film thickness of 150 Å on the hole transport layer to form a hole control layer. Then, on the hole control layer, the compound 1 prepared above and the compound Dp-7 below were vacuum-deposited in a weight ratio of 98:2 to form a light emitting layer having a thickness of 400 Å . The following compound HB-1 was vacuum-deposited to a thickness of 30 Å on the light emitting layer to form an electron control layer. Then, on the electron control layer, the following compound ET-1 and the following compound LiQ were vacuum-deposited at a weight ratio of 2:1 to form an electron injection and transport layer to a thickness of 300 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1000 Å on the electron injection and transport layer.

In the above process, the deposition rate of the organic material was maintained at 0.4 Å/sec to 0.7 Å/sec, the deposition rate of lithium fluoride of the negative electrode was 0.3 Å/sec, and the deposition rate of aluminum was 2 Å/sec, and the vacuum degree during deposition was 2×10 ^-7 to 5×10 ^-6 torr was maintained.

Examples 1-2 to Examples 1-12

An organic light emitting diode was manufactured in the same manner as in Example 1-1, except that the compound of Table 1 was used instead of Compound 1.

Comparative Examples 1 to 3

An organic light emitting diode was manufactured in the same manner as in Example 1-1, except that the compound of Table 1 was used instead of Compound 1. Compounds RH-2, RH-3 and RH-4 used in Table 1 below are as follows.

Experimental example

Examples and Comparative Examples at a current density of 10 mA / cm ² for each of the organic light emitting device were measured drive voltage and luminous efficiency, the luminance at a current density of 10 mA / cm ² initial brightness (5000nit) compared to that of 98% Time (T ₉₈ ) was measured. In addition, the emission color was observed with the naked eye. The results are shown in Table 1 below.

light emitting layer drive voltage
(V) efficiency
(cd/A) T ₉₈
(hr) luminous color Comparative Example 1 RH-2 4.4 32.7 135 Red Comparative Example 2 RH-3 4.7 31.9 126 Red Comparative Example 3 RH-4 4.8 32.8 114 Red Example 1-1 compound 1 3.8 34.4 171 Red Example 1-2 compound 2 3.8 34.6 175 Red Examples 1-3 compound 3 3.7 35.3 188 Red Examples 1-4 compound 4 3.9 37.5 175 Red Examples 1-5 compound 5 3.6 36.1 169 Red Examples 1-6 compound 6 3.7 36.2 176 Red Examples 1-7 compound 7 3.7 35.6 178 Red Examples 1-8 compound 8 3.8 36.4 188 Red Examples 1-9 compound 9 4.2 34.5 173 Red Examples 1-10 compound 10 4.1 36.7 162 Red Examples 1-11 compound 11 4.0 34.9 181 Red Examples 1-12 compound 12 3.8 35.1 187 Red

As shown in Table 1, in the organic light emitting device using the compound of the present invention as the light emitting layer, it was confirmed that the efficiency, driving voltage, and lifespan characteristics of the organic light emitting device were improved.

In Examples 1-1 to 1-12, the organic light emitting device using the compound of the present invention was prepared using the compounds RH-2, RH-3, and RH-4 to which the triazine substituent not containing adamantene was connected Compared to the organic light emitting diodes of Comparative Examples 1, 2, and 3, low voltage, high efficiency, and long life were exhibited.

1: Substrate 2: Anode
3: light emitting layer 4: cathode
5: hole injection layer 6: hole transport layer
7: hole control layer 8: electron control layer
9: electron transport layer 10: electron injection layer

Claims (10)

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

In Formula 1,
A is a benzene ring, a naphthalene ring, or a phenanthrene ring fused with an adjacent pentacyclic ring,
B is a naphthalene ring or a phenanthrene ring fused with an adjacent pentagonal ring,
Ra and Rb are each independently hydrogen; heavy hydrogen; substituted or unsubstituted C _1-60 alkyl; substituted or unsubstituted C _3-60 cycloalkyl; substituted or unsubstituted C _2-60 alkenyl; substituted or unsubstituted C _6-60 aryl; _{Or substituted or unsubstituted C 2-60} heteroaryl comprising any one or more selected from the group consisting of N, O and S,
Y ₁ to Y ₃ are each independently CH or N, provided that at least one of _{Y 1} to Y _{3 is N,}
Ar ₁ is adamantyl; substituted or unsubstituted C _6-60 aryl; _{Or substituted or unsubstituted C 2-60} heteroaryl comprising any one or more selected from the group consisting of N, O and S,
L ₁ to L ₃ are each independently a single bond, or a substituted or unsubstituted C _6-60 arylene;
R ₁ is each independently hydrogen; heavy hydrogen; substituted or unsubstituted C _1-60 alkyl; substituted or unsubstituted C _3-60 cycloalkyl; substituted or unsubstituted C _2-60 alkenyl; substituted or unsubstituted C _6-60 aryl; _{Or substituted or unsubstituted C 2-60} heteroaryl comprising any one or more selected from the group consisting of N, O and S,
a is an integer from 0 to 7.
According to claim 1,
A is a benzene ring fused with an adjacent pentacyclic ring,
B is a naphthalene ring or a phenanthrene ring fused with an adjacent pentagonal ring,
compound.
According to claim 1,
Formula 1 is represented by the following Formulas 1-1 to 1-4,
compound:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4,
Y ₁ to Y ₃ , Ar ₁ , L ₁ to L ₃ , Ra, Rb, R ₁ and a are the same as defined in claim 1 .
According to claim 1,
Ra and Rb are each methyl;
compound.
According to claim 1,
Ar ₁ is adamantyl, phenyl, biphenylyl, naphthyl, phenanthrenyl, phenanthrenyl phenyl, phenyl naphthyl, naphthyl phenyl, or dibenzofuranyl;
compound.
According to claim 1,
L _{1 To} L _{3 Are} each independently any one selected from the group consisting of a single bond or the following,
compound:

In the group,
R ₂ are each independently hydrogen; heavy hydrogen; halogen; cyano; nitro; amino; substituted or unsubstituted C _1-60 alkyl; substituted or unsubstituted C _3-60 cycloalkyl; substituted or unsubstituted C _2-60 alkenyl; substituted or unsubstituted C _6-60 aryl; _{Or substituted or unsubstituted C 2-60} heteroaryl comprising any one or more selected from the group consisting of N, O and S.
According to claim 1,
L ₁ to L ₃ are each independently a single bond, phenylene, biphenylrylene, or naphthylene,
compound.
According to claim 1,
R ₁ is each independently hydrogen or deuterium,
compound.
According to claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of
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 9 doing,
organic light emitting device.

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