KR20230108911A - Indenophenanthrene compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention relates to an indenophenanthrene compound and an organic light emitting device including the same. It is a polycyclic heterocyclic structure having a fused multi-ring backbone as a mother nucleus and having one nitrogen atom in the mother nucleus, and can be used as a material for an organic material layer of an organic light emitting device.

Description

Indenophenanthrene compound and an organic light emitting device containing the same

The present invention relates to an indenopenanthrene compound having a novel structure and an organic light emitting device including the same.

In general, the organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic electronic device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer between the anode. Here, the organic material layer is often composed of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electric device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

Materials used as organic layers in organic electronic devices may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, according to their functions. In addition, the light emitting material can be classified into a high molecular weight type and a low molecular weight type according to molecular weight, and can be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. can In addition, light emitting materials may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural colors according to the light emitting color.

In particular, several studies are being conducted on organic materials inserted into a hole transport layer or a buffer layer for excellent lifespan characteristics of organic electronic devices. A hole injection layer material having high uniformity and low crystallinity upon formation is required.

It delays penetration and diffusion of metal oxide from the anode electrode (ITO) into the organic layer, which is one of the causes of shortening the lifespan of organic electronic devices, and has stable characteristics against Joule heating generated during device operation, that is, high glass transition temperature. It is necessary to develop a hole injection layer material having In addition, it has been reported that the low glass transition temperature of the material for the hole transport layer greatly affects the lifetime of the device according to the property that the uniformity of the surface of the thin film collapses during device operation. In addition, since the deposition method is the mainstream in the formation of OLED devices, there is a need for a material with strong heat resistance that can withstand such a deposition method for a long time.

On the other hand, when only one material is used as a light emitting material, the maximum emission wavelength moves to a longer wavelength due to intermolecular interactions, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect. Therefore, color purity increases and energy transfer A host/dopant system may be used as a light emitting material in order to increase luminous efficiency. The principle is that when a small amount of a dopant having a smaller energy band gap than the host forming the light emitting layer is mixed into the light emitting layer, excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength range of the dopant, light of a desired wavelength can be obtained according to the type of dopant used.

In order to fully exhibit the excellent characteristics of the above-mentioned organic electronic device, materials constituting the organic layer in the device, such as hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials, etc. are supported by stable and efficient materials. Although this should be preceded, stable and efficient organic material layer materials for organic electric devices have not yet been sufficiently developed, and therefore, development of new materials is continuously required.

KR 10-2015-0000398 A US 2015-0255727 A1

An object of the present invention is to provide an indenopenanthrene compound having a novel structure that can be used as a material for an organic layer of an organic light emitting device.

In addition, an object of the present invention is to provide an organic light emitting device including the indenophenanthrene compound as an organic material layer material.

The present invention relates to an indenophenanthrene compound having a novel structure and an organic light emitting device including the same. It is a polycyclic heterocyclic structure having a multi-ring skeleton in which multiple fused rings are fused as a mother nucleus and having one nitrogen atom in the mother nucleus, and can be used as an organic material layer material of an organic light emitting device.

The present invention provides an indenophenantrene compound represented by Formula 1 below.

[Formula 1]

In Formula 1,

A ₁ and A ₂ are each independently CH or N;

R ₁ is deuterium, C1-C60 alkyl, cyano, C2-C60 alkenyl, C2-C60 alkynyl, C3-C60 cycloalkyl, C2-C60 heterocycloalkyl, hydroxy, C1-C60 alkoxy, C6-C60 aryl oxy, C6-C60 aryl, C2-C60 heteroaryl or -NR _1a R _1b ;

R ₂ is hydrogen or -NR _2a R _2b ;

R ₃ and R ₄ are each independently hydrogen, deuterium, cyano, C1-C60 alkyl, C2-C60 alkenyl, C2-C60 alkynyl, C3-C60 cycloalkyl, C2-C60 heterocycloalkyl, C6-C60 aryl , C2-C60 heteroaryl or -NR _3a R _3b ;

R _1a , R _1b , R _2a , R _2b , R _3a and R _3b are each independently hydrogen, deuterium, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C2-C60 heteroaryl or amino;

Alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, alkoxy, aryloxy, aryl and heteroaryl of R ₁ , Alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl of R ₃ and R ₄ , Aryl and heteroaryl, alkyl, cycloalkyl, aryl and heteroaryl of R _1a , R _1b , R _2a , R _2b , R _3a and R _3b are deuterium, C1-C60 alkyl, haloC1-C60 alkyl, halogen, cyano , C3-C60 Cycloalkyl, C2-C60 Heterocycloalkyl, C1-C60 Alkoxy, C6-C60 Aryl, C6-C60 Aryloxy, C6-C60 ArylC1-C60 Alkyl, C1-C60 AlkylC6-C60 Aryl, C2- may be further substituted with one or more selected from the group consisting of C60 heteroaryl, -NR'R'', nitro and hydroxy;

R' and R'' are each independently hydrogen, C1-C60 alkyl, C6-C60 aryl, C2-C60 heteroaryl or amino;

a is an integer from 0 to 4;

The heterocycloalkyl and heteroaryl include one or more heteroatoms selected from N, O, S and Se.

In addition, the present invention is an organic light-emitting device including an anode, a cathode, and one or more organic material layers provided between the anode and the cathode, wherein at least one layer of the organic material layer includes the indenophenanthrene compound of Formula 1. provide a small

The indenophenanthrene compound according to the present invention has a multi-ring skeleton in which multiple fused rings are fused around dihydrophenanthrene or dihydrophenanthridine as a mother nucleus, and has one nitrogen atom in the mother nucleus. It has a polycyclic heterocyclic structure, and can be used as an organic material layer material of an organic light emitting device. The indenophenanthrene compound may serve as a light emitting material, a hole injection material, a hole transport material, a light emitting material, an electron transport material, or an electron injection material in an organic light emitting device.

The indenophenanthrene compound according to the present invention can be employed as an organic layer material such as a light emitting material, a hole injection material, a hole transport material, a light emitting material, an electron transport material, and an electron injection material due to its structural specificity, and an organic light emitting device employing the same has a high hole mobility, thereby having a high efficiency and a low driving voltage at the same time, and life characteristics can also be surprisingly improved.

That is, the indenophenanthrene compound according to the present invention has excellent electron mobility due to its structural specificity, thereby improving the current characteristics of the device and intensifying the driving voltage, thereby inducing an increase in power efficiency to produce an organic light emitting device with improved power consumption. can be produced

The present invention is detailed below, but unless there is another definition in the technical and scientific terms used at this time, it has the meaning commonly understood by those of ordinary skill in the art to which this invention belongs, and in the following description Descriptions of well-known functions and configurations that may unnecessarily obscure the subject matter of the invention will be omitted.

Throughout this specification, unless the context requires otherwise, the terms "comprise" and "comprising" include a given step or component, or group of steps or components, but any other step or component, or It is to be understood that steps or groups of components are not excluded.

In this specification, “substituent”, “radical”, “group”, “moiety”, and “fragment” may be used interchangeably.

In the present specification, “C _A -C _B ” means “a number of carbon atoms greater than or equal to A and less than or equal to B”.

In the present specification, "alkyl", "alkoxy" and other substituents including "alkyl" moieties include both straight-chain and branched forms.

In the present specification, "alkyl" includes a straight chain or branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents. The number of carbon atoms of the alkyl may be 1 to 60, specifically 1 to 30, more specifically, 1 to 20, preferably 1 to 10.

In the present specification, "alkenyl" is a monovalent radical of a straight-chain or branched unsaturated hydrocarbon containing at least one double bond between two or more carbon atoms, including a straight-chain or branched chain of 2 to 60 carbon atoms, and other It may be further substituted by substituents. The number of carbon atoms of alkenyl may be 2 to 60, specifically 2 to 30, more specifically, 2 to 20, preferably 2 to 10. Specifically, vinyl, allyl, prop-1-en-2yl, 1-butenyl, 2-butenyl, isobutylenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 2 -Methyl-2-butenyl, 2,3-dimethyl-2-butenyl and the like, but are not limited thereto.

In the present specification, "alkynyl" includes straight or branched chains having 2 to 60 carbon atoms, and may be further substituted by other substituents. The number of carbon atoms of alkynyl may be 2 to 60, specifically 2 to 30, more specifically, 2 to 20, preferably 2 to 10.

As used herein, "cycloalkyl" is a monovalent saturated or unsaturated carbocyclic radical composed of one or more rings and is not aromatic. The cycloalkyl includes a monocyclic or polycyclic ring having 3 to 60 carbon atoms, and may be further substituted with other substituents. Here, the polycyclic means a group directly connected or condensed with another cyclic group, or a spiro-type ring system. Here, the other ring group may be cycloalkyl, but other types of ring groups such as heterocycloalkyl, aryl, heterocyclic, etc. may also be used. Cycloalkyl may have 3 to 60 carbon atoms, specifically 3 to 30, and more specifically 5 to 20 carbon atoms. Specific examples of cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like.

As used herein, "heterocycloalkyl" is a monovalent radical of a non-aromatic heterocycle containing at least one selected from N, O, S, and Se as a heteroatom, and the non-aromatic heterocycle is a saturated or unsaturated monovalent radical. All in cyclic, polycyclic or spirocyclic form, which may be bonded through a heteroatom or carbon atom, and the nitrogen, carbon, oxygen or sulfur atoms in non-aromatic heterocyclic radicals may optionally be oxidized to various oxidation states. . In addition, nitrogen atoms in non-aromatic heterocyclic radicals may optionally be quaternized. The heterocycloalkyl includes at least one heteroatom selected from N, O, S, and Se, and includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic means a group in which heterocycloalkyl is directly connected or condensed with another ring group. Here, the other ring group may be heterocycloalkyl, but may also be other types of ring groups, such as cycloalkyl, aryl, and heterocyclic. Heterocycloalkyl may have 2 to 60, specifically 2 to 30, and more specifically 3 to 20 carbon atoms. Examples of heterocycloalkyl radicals include aziridine, pyrrolidine, pyrrolidinone, azetidine, piperidine, tetrahydropyridine, piperazine, morpholine, thiomorpholine, 4,5,6,7-tetrahydrobenzo [b] thiophene, 2,3-dihydrobenzofuran, benzo [d] [1,3] dioxole, 3,4-dihydro-2H-chromene, naphthalen-2 (1H) -one, 2H- chromen-2-one, 2,3-dihydrobenzo[b][1,4]dioxin, benzo[d]oxazol-2(3H)-one, pyrimidin-2,4(1H,3H)- Dione, quinazoline-2,4(1H,3H)-dione, benzo[cd]indol-2(1H)-one, 3-azabicyclo[3.1.0]hexane, octahydropyrrolo[3,4- c] pyrrole, 2,7-diazaspiro[4.4]nonane, 2-azaspiro[4.4]nonane, and the like, may include a monovalent radical of a non-aromatic heterocyclic ring.

In the present specification, "aryl" is an organic radical derived from an aromatic hydrocarbon by removing one hydrogen, and includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted with other substituents. Here, the polycyclic means a group in which aryl is directly connected or condensed with another ring group, or a spiro ring. Here, the other ring group may be aryl, but may also be other types of ring groups, such as cycloalkyl, heterocycloalkyl, heterocyclic, and the like. The number of carbon atoms of aryl may be 6 to 60, specifically 6 to 30. Specific examples of aryl include phenyl, biphenyl, triphenyl, naphthyl, anthryl, chrysenyl, phenanthrenyl, perylenyl, fluoranthenyl, triphenylenyl, phenalenyl, pyrenyl, tetracenyl, pentacenyl, fluorenyl, indenyl, acenaphthylenyl, fluorenyl, spirofluorenyl, etc., but are not limited thereto.

In the present specification, "heterocyclic group" includes at least one selected from N, O, S, and Se as a hetero atom, and includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted by another substituent. can Heteroaryl is included in the scope of a heterocyclic group and is a heteroaromatic ring group. Here, the polycyclic means a group in which a heterocyclic group is directly connected or condensed with another cyclic group. Here, the other ring group may be a heterocyclic group, but may also be another type of ring group, such as cycloalkyl, heterocycloalkyl, aryl, and the like. The number of carbon atoms in the heterocyclic group may be 2 to 60, specifically 2 to 30, and more specifically 3 to 20. Specific examples of the heterocyclic group include pyridyl, pyrrolyl, pyrimidyl, pyridazinyl, furanyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, Furazanil, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranil, thiopyranil, diazinyl, oxazinyl, thiazinyl, dioxynyl, triazinyl, tetrazinyl, quinolyl, iso Quinolyl, quinazolinyl, isoquinazolinyl, naphthyridyl, acridinyl, phenanthridinyl, imidazopyridinyl, diazanaphthalenyl, triazinden, indolyl, indolizinyl, benzothiazolyl, Benzoxazolyl, benzoimidazolyl, benzothiophene group, benzofuran group, dibenzothiophene group, dibenzofuran group, carbazolyl, benzocarbazolyl, phenazinyl, etc., or condensed rings thereof, but limited thereto it is not going to be

As used herein, "heteroaryl" refers to an aryl group including at least one heteroatom selected from N, O, S, and Se as an aromatic ring skeletal atom, and the remaining aromatic ring skeletal atoms being carbon. 6-membered monocyclic heteroaryl, and polycyclic heteroaryl condensed with one or more benzene rings, which may be partially saturated. In addition, the heteroaryl in the present invention includes a form in which one or more heteroaryls are connected by a single bond. Specific examples include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, isoxazolyl, oxazolyl, triazinyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc. Monocyclic heteroaryl of; Benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, quinolyl, iso polycyclic heteroaryls such as quinolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, and benzocarbazolyl; and the like, but are not limited thereto.

As used herein, "alkylaryl" means an aryl radical substituted with at least one alkyl, where alkyl and aryl are as defined above. Examples of such alkylaryl radicals include, but are not limited to, tolyl and the like.

As used herein, "alkoxy" is an -O-alkyl radical, wherein alkyl is as defined above. Specific examples include, but are not limited to, methoxy, ethoxy, isopropoxy, butoxy, isobutoxy, t-butoxy, and the like.

In this specification, "aryloxy" means -O-aryl radical, where aryl is as defined above. Examples of such aryloxy radicals include, but are not limited to, phenoxy, naphthoxy, and the like.

In this specification, "halo" or "halogen" represents a halogen group element, and includes, for example, fluoro, chloro, bromo, and iodo.

In the present specification, "amino" means -NH ₂ , "hydroxy" means -OH, and "cyano" means -CN.

As used herein, "haloalkyl" refers to an alkyl group wherein each of one or more hydrogen atoms is replaced with a halogen atom, wherein alkyl and halogen are as defined above. For example, haloalkyl includes fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, perfluoroethyl and the like.

As used herein, "arylalkyl" refers to an alkyl radical substituted with at least one aryl, where aryl and alkyl are as defined above. For example, arylalkyl can include benzyl, naphthylmethyl, and the like.

The present invention relates to an indenopenanthrene compound and an organic light emitting device including the same, and more particularly, the indenopenanthrene compound according to the present invention may be represented by the following formula (1):

[Formula 1]

In Formula 1,

A ₁ and A ₂ are each independently CH or N;

R ₁ is deuterium, C1-C60 alkyl, cyano, C2-C60 alkenyl, C2-C60 alkynyl, C3-C60 cycloalkyl, C2-C60 heterocycloalkyl, hydroxy, C1-C60 alkoxy, C6-C60 aryl oxy, C6-C60 aryl, C2-C60 heteroaryl or -NR _1a R _1b ;

R ₂ is hydrogen or -NR _2a R _2b ;

R ₃ and R ₄ are each independently hydrogen, deuterium, cyano, C1-C60 alkyl, C2-C60 alkenyl, C2-C60 alkynyl, C3-C60 cycloalkyl, C2-C60 heterocycloalkyl, C6-C60 aryl , C2-C60 heteroaryl or -NR _3a R _3b ;

R _1a , R _1b , R _2a , R _2b , R _3a and R _3b are each independently hydrogen, deuterium, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C2-C60 heteroaryl or amino;

Alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, alkoxy, aryloxy, aryl and heteroaryl of R ₁ , Alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl of R ₃ and R ₄ , Aryl and heteroaryl, alkyl, cycloalkyl, aryl and heteroaryl of R _1a , R _1b , R _2a , R _2b , R _3a and R _3b are deuterium, C1-C60 alkyl, haloC1-C60 alkyl, halogen, cyano , C3-C60 Cycloalkyl, C2-C60 Heterocycloalkyl, C1-C60 Alkoxy, C6-C60 Aryl, C6-C60 Aryloxy, C6-C60 ArylC1-C60 Alkyl, C1-C60 AlkylC6-C60 Aryl, C2- may be further substituted with one or more selected from the group consisting of C60 heteroaryl, -NR'R'', nitro and hydroxy;

R' and R'' are each independently hydrogen, C1-C60 alkyl, C6-C60 aryl, C2-C60 heteroaryl or amino;

a is an integer from 0 to 4;

The heterocycloalkyl and heteroaryl include one or more heteroatoms selected from N, O, S and Se.

Specifically, the indenophenanthrene compound of Formula 1 has a multi-ring skeleton in which multiple fused rings are fused around dihydrophenanthrene or dihydrophenanthridine as a mother nucleus, and one in the mother nucleus It has a polycyclic heterocyclic structure having a nitrogen atom of, is thermally stable, and can exhibit maximized electron mobility, so it can be used as an organic material layer material of an organic light emitting device. The indenophenanthrene compound of Chemical Formula 1 lowers the driving voltage, improves luminous efficiency and color purity, and has surprisingly improved lifespan characteristics when employed as an organic layer of an organic light emitting device, particularly as a hole transport material of an organic light emitting device, due to the above structural characteristics can represent

In one embodiment, one of A ₁ and A ₂ may be CH, and the other may be N.

In one embodiment, the indenopenanthrene compound may be represented by Formula 2 below.

[Formula 2]

In Formula 2, R ₁ , R ₂ and a are the same as defined in Formula 1;

One of A ₁ and A ₂ is CH, and the other is N.

In one embodiment, A ₁ is CH, A ₂ is N; R ₁ is deuterium, C1-C30 alkyl, cyano, C2-C30 alkenyl, hydroxy, C1-C30 alkoxy, C6-C30 aryloxy, C6-C30 aryl, C2-C30 heteroaryl or -NR _1a R _1b ; ; R ₂ is hydrogen or -NR _2a R _2b ; R _1a , R _1b , R _2a and R _2b are each independently hydrogen, deuterium, C1-C30 alkyl, C6-C30 aryl, C2-C30 heteroaryl or amino; The alkyl, alkenyl, alkoxy, aryloxy, aryl and heteroaryl of R ₁ , the alkyl, aryl and heteroaryl of R _1a , R _1b , R _2a and R _2b are deuterium, C1-C30 alkyl, haloC1-C30 alkyl , halogen, cyano, C1-C30 alkoxy, C6-C30 aryl, C6-C30 aryloxy, C6-C30 arylC1-C30 alkyl, C1-C30 alkylC6-C30 aryl, C2-C30 heteroaryl and -NR'R may be further substituted with one or more selected from the group consisting of '';R' and R'' are each independently hydrogen, C1-C30 alkyl, C6-C30 aryl, C2-C30 heteroaryl or amino; a may be an integer from 0 to 4.

In one embodiment, A ₁ is N, A ₂ is CH; R ₁ is deuterium, C1-C30 alkyl, cyano, C2-C30 alkenyl, hydroxy, C1-C30 alkoxy, C6-C30 aryloxy, C6-C30 aryl, C2-C30 heteroaryl or -NR _1a R _1b ; ; R ₂ is hydrogen or -NR _2a R _2b ; R _1a , R _1b , R _2a and R _2b are each independently hydrogen, deuterium, C1-C30 alkyl, C6-C30 aryl, C2-C30 heteroaryl or amino; The alkyl, alkenyl, alkoxy, aryloxy, aryl and heteroaryl of R ₁ , the alkyl, aryl and heteroaryl of R _1a , R _1b , R _2a and R _2b are deuterium, C1-C30 alkyl, haloC1-C30 alkyl , halogen, cyano, C1-C30 alkoxy, C6-C30 aryl, C6-C30 aryloxy, C6-C30 arylC1-C30 alkyl, C1-C30 alkylC6-C30 aryl, C2-C30 heteroaryl and -NR'R may be further substituted with one or more selected from the group consisting of '';R' and R'' are each independently hydrogen, C1-C30 alkyl, C6-C30 aryl, C2-C30 heteroaryl or amino; a may be an integer from 0 to 4.

In one embodiment, R ₁ is deuterium, C1-C20 alkyl, cyano, vinyl, allyl, hydroxy, C1-C20 alkoxy, C6-C30 arylC1-C20 alkoxy, C6-C30 aryloxy, C1-C20 alkylC6-C30 aryloxy, C6-C30 aryl, C2-C20 heteroaryl or amino; R ₂ is hydrogen or -NR _2a R _2b ; R _2a and R _2b are each independently hydrogen, deuterium, C1-C20 alkyl, C6-C30 aryl or C2-C20 heteroaryl; The alkyl, aryl and heteroaryl of R ₁ , the alkyl, aryl and heteroaryl of R _2a and R _2b are deuterium, C1-C20 alkyl, cyano, C1-C20 alkoxy, C6-C30 aryl, C6-C30 aryloxy, may be further substituted with one or more selected from the group consisting of C6-C30 arylC1-C20 alkyl, C1-C20 alkylC6-C30 aryl, C2-C20 heteroaryl and -NR'R'';R' and R'' are each independently hydrogen, C1-C20 alkyl, C6-C30 aryl or C2-C20 heteroaryl; a may be an integer from 0 to 4.

In one embodiment, R ₁ is deuterium, C1-C10 alkyl, cyano, vinyl, allyl, hydroxy, C1-C10 alkoxy, C6-C20 arylC1-C10 alkoxy, C6-C20 aryloxy, C1-C10 AlkylC6-C20 aryloxy or amino, or may be selected from, but not limited to, the following structures:

In the above structure,

X ₁ is NR _X1 , O or S;

Y ₁ is CR _Y1 R _Y2 , O or S;

R _X1 is hydrogen, deuterium, C1-C10 alkyl, C6-C12 aryl or C3-C12 heteroaryl;

R _Y1 and R _Y2 are each independently hydrogen, deuterium, C1-C10 alkyl, C6-C12 aryl or C3-C12 heteroaryl;

R ₄₁ , R ₄₂ and R ₄₃ are independently of each other hydrogen, deuterium, C1-C10 alkyl, cyano, C1-C10 alkoxy, C6-C12 aryl, C3-C12 heteroaryl or -NR'R'';

R' and R'' are each independently C1-C10 alkyl, C6-C12 aryl or C3-C12 heteroaryl;

R ₄₄ and R ₄₅ are each independently hydrogen, deuterium, C1-C10 alkyl or C6-C12 aryl.

In one embodiment, the indenopenanthrene compound may be represented by Formula 3 or Formula 4 below.

[Formula 3]

[Formula 4]

In Formulas 3 and 4,

R _A , R _B , R _C and R _D are each independently hydrogen, deuterium, C1-C30 alkyl, cyano, C2-C30 alkenyl, hydroxy, C1-C30 alkoxy, C6-C30 aryloxy, C6-C30 aryl, C2-C30 heteroaryl or -NR _1a R _1b ;

R ₂ is hydrogen or -NR _2a R _2b ;

R _1a , R _1b , R _2a and R _2b are each independently hydrogen, deuterium, C1-C30 alkyl, C6-C30 aryl, C2-C30 heteroaryl or amino;

Alkyl, alkenyl, alkoxy, aryloxy, aryl and heteroaryl of R _A , R _B , R _C and R _D , alkyl, aryl and heteroaryl of R _1a , R _1b , R _2a and R _2b are deuterium, C1 -C30 Alkyl, HaloC1-C30 Alkyl, Halogen, Cyano, C1-C30 Alkoxy, C6-C30 Aryl, C6-C30 Aryloxy, C6-C30 ArylC1-C30 Alkyl, C1-C30 AlkylC6-C30 Aryl, C2 may be further substituted with one or more selected from the group consisting of -C30 heteroaryl and -NR'R'';

R' and R'' are each independently hydrogen, C1-C30 alkyl, C6-C30 aryl, C2-C30 heteroaryl or amino.

In one embodiment, R _A , R _B , R _C and R _D are each independently hydrogen, deuterium, C1-C20 alkyl, cyano, vinyl, allyl, hydroxy, C1-C20 alkoxy, C6-C30 aryl C1-C20 alkoxy, C6-C30 aryloxy, C1-C20 alkylC6-C30 aryloxy, C6-C30 aryl, C2-C20 heteroaryl or amino; R ₂ is hydrogen or -NR _2a R _2b ; R _2a and R _2b are each independently hydrogen, deuterium, C1-C20 alkyl, C6-C30 aryl or C2-C20 heteroaryl; Alkyl, aryl and heteroaryl of R _A , R _B , R _C and R _D , alkyl, aryl and heteroaryl of R _2a and R _2b are deuterium, C1-C20 alkyl, cyano, C1-C20 alkoxy, C6- Further substituted with one or more selected from the group consisting of C30 aryl, C6-C30 aryloxy, C6-C30 arylC1-C20 alkyl, C1-C20 alkylC6-C30 aryl, C2-C20 heteroaryl and -NR'R'' can be; R' and R'' may each independently be hydrogen, C1-C20 alkyl, C6-C30 aryl or C2-C20 heteroaryl.

In one embodiment, the R _A , R _B , R _C and R _D are each independently hydrogen, deuterium, C1-C10 alkyl, cyano, vinyl, allyl, hydroxy, C1-C10 alkoxy, C6-C20 aryl C1-C10 alkoxy, C6-C20 aryloxy, C1-C10 alkylC6-C20 aryloxy, or amino, or may be selected from, but not limited to:

In the above structure,

X ₁ is NR _X1 , O or S;

Y ₁ is CR _Y1 R _Y2 , O or S;

R _X1 is hydrogen, deuterium, C1-C10 alkyl, C6-C12 aryl or C3-C12 heteroaryl;

R _Y1 and R _Y2 are each independently hydrogen, deuterium, C1-C10 alkyl, C6-C12 aryl or C3-C12 heteroaryl;

R ₄₁ , R ₄₂ and R ₄₃ are independently of each other hydrogen, deuterium, C1-C10 alkyl, cyano, C1-C10 alkoxy, C6-C12 aryl, C3-C12 heteroaryl or -NR'R'';

R' and R'' are each independently C1-C10 alkyl, C6-C12 aryl or C3-C12 heteroaryl;

R ₄₄ and R ₄₅ are each independently hydrogen, deuterium, C1-C10 alkyl or C6-C12 aryl.

In one embodiment, the R _A , R _B , R _C and R _D are each independently hydrogen, deuterium, C1-C7 alkyl, cyano, vinyl, allyl, hydroxy, C1-C7 alkoxy or amino, or structure can be selected.

In the above structure,

X ₁ is NR _X1 , O or S;

R _X1 is hydrogen, deuterium, C1-C10 alkyl or C6-C12 aryl;

R ₄₁ , R ₄₂ and R ₄₃ are independently of each other hydrogen, deuterium, C1-C10 alkyl, cyano, C1-C10 alkoxy, C6-C12 aryl, C3-C12 heteroaryl or -NR'R'';

R' and R'' are each independently C1-C10 alkyl or C6-C12 aryl;

R ₄₄ and R ₄₅ are each independently hydrogen, deuterium, C1-C10 alkyl or C6-C12 aryl.

In one embodiment, R ₂ is hydrogen or -NR _2a R _2b , and R _2a and R _2b are each independently hydrogen, deuterium, C1-C10 alkyl or C6-C20 arylC1-C10 alkyl, or in the following structure Can be selected, but is not limited to:

In the above structure,

X ₂ is NR _X2 , O or S;

Y ₂ is CR _Y3 R _Y4 , O or S;

R _X2 is hydrogen, deuterium, C1-C10 alkyl, C6-C12 aryl or C3-C12 heteroaryl;

R _Y3 and R _Y4 are each independently hydrogen, deuterium, C1-C10 alkyl, C6-C12 aryl or C3-C12 heteroaryl;

R ₅₁ , R ₅₂ and R ₅₃ independently of each other are hydrogen, deuterium, C1-C10 alkyl, cyano, C1-C10 alkoxy, C6-C12 aryl, C3-C12 heteroaryl or -NR'R'';

R' and R'' are each independently C1-C10 alkyl, C6-C12 aryl or C3-C12 heteroaryl;

R ₅₄ and R ₅₅ are each independently hydrogen, deuterium, C1-C10 alkyl or C6-C12 aryl.

In one embodiment, the R _A , R _B , R _C and R _D are each independently hydrogen, deuterium, C1-C7 alkyl, cyano, vinyl, allyl, hydroxy, C1-C7 alkoxy or amino, or structure can be selected.

In one embodiment, the R ₂ may be hydrogen.

In one embodiment, R ₂ is -NR _2a R _2b , and R _2a and R _2b are each independently hydrogen, deuterium, C1-C7alkyl or C6-C12arylC1-C7alkyl, or selected from the following structures: can:

In the above structure,

X ₂ is NR _X2 , O or S;

R _X2 is hydrogen, deuterium, C1-C7 alkyl or C6-C12 aryl;

R ₅₁ , R ₅₂ and R ₅₃ are independently of each other hydrogen, deuterium, C1-C7 alkyl, cyano, C1-C7 alkoxy, C6-C12 aryl, C3-C12 heteroaryl or -NR'R'';

R' and R'' are each independently C1-C7 alkyl or C6-C12 aryl;

R ₅₄ and R ₅₅ are each independently hydrogen, deuterium, C1-C7 alkyl or C6-C12 aryl.

In one embodiment, the indenophenantrene compound may be selected from the following, but is not limited thereto.

The indenophenanthrene compound according to an embodiment of the present invention can be used in an organic layer of an organic light emitting device due to its structural specificity, and specifically, an electron transport material, an electron injection material, a light emitting material, a hole injection material, a hole transport material, etc. can play the role of

In addition, the aforementioned compounds can be prepared based on Preparation Examples/Examples described below. In Preparation Examples/Examples to be described later, representative examples are described, but, if necessary, substituents may be added or excluded, and the position of the substituent may be changed. In addition, based on techniques known in the art, starting materials, reactants, reaction conditions, and the like can be changed. Changing the type or position of the substituents at the remaining positions, if necessary, can be performed by those skilled in the art using techniques known in the art.

In addition, the present invention provides an organic light emitting device including the indenophenantrene compound of Formula 1 above.

Specifically, the organic light emitting device according to the present invention includes an anode, a cathode, and at least one organic material layer provided between the anode and the cathode, and at least one layer of the organic material layer includes the indenophenantrene compound represented by Chemical Formula 1.

However, structures of organic light emitting devices known in the art may also be applied to the present invention. The scope of the present invention is not limited by such a laminated structure.

The organic light emitting device according to the present invention may be manufactured with materials and methods known in the art, except for including the indenophenanthrene compound of Chemical Formula 1 in at least one of the organic material layers.

The indenopenanthrene compound of Chemical Formula 1 alone may constitute one or more layers of the organic material layer of the organic light emitting device. However, if necessary, the organic material layer may be formed by mixing with other materials.

The indenophenanthrene compound of Chemical Formula 1 may be used as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, and the like in an organic light emitting device. The indenophenanthrene compound may be used as a material for one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. As an example, the indenophenanthrene compound may be used as a material for a hole injection and transport layer of an organic light emitting device. As an example, the indenopenanthrene compound may be used as a material for an electron injection and transport layer of an organic light emitting device. As another example, the indenophenanthrene compound may be used as a material for a light emitting layer of an organic light emitting device. As another example, the indenopenanthrene compound may be used as a host material for a phosphorescent light emitting layer of an organic light emitting device. Preferably, the indenophenanthrene compound may be used as a hole transport layer material of an organic light emitting device.

In the organic light emitting device according to the present invention, materials other than the indenophenanthrene compound are exemplified below, but these are for illustration only and are not intended to limit the scope of the present invention, and materials known in the art can be replaced with

As the anode material, materials having a relatively large work function may be used. Specific examples include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc. Metal oxides such as oxide (IZO), combinations of metals and oxides such as ZnO:Al or SnO2:Sb, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiol Ofene] (PEDT), conductive polymers such as polypyrrole and polyaniline may be used, but are not limited thereto. In addition, the anode layer may be formed of only one type of the above materials or may be formed of a mixture of a plurality of materials, and a multilayer structure composed of a plurality of layers of the same composition or different compositions may be formed.

Materials with a relatively low work function may be used as the anode material, and specific examples include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof , a multi-layer structure material such as LiF/Al or LiO/Al may be used.

As the hole injection material, a known hole injection material may be used. For example, a phthalocyanine compound such as CuPc (copper phthalocyanine) disclosed in U.S. Patent No. 4,356,429 or a document [Advanced Material, 6, p.677 (1994)] , such as TCTA (tris(4-carbazoyl-9-ylphenyl)amine), m-MTDATA (4,4',4"-tris(3-Methylphenylphenylamino)triphenylamine), m- MTDAPB (1,3,5-tris[4-(3-metylphenylphenylamino)phenyl]benzene), soluble conductive polymer Pani/DBSA (Polyaniline/Dodecylbenzenesulfonic acid) or PEDOT:PSS (poly(3,4-ethylenedioxythiophene) -poly(styrnesulfonate)), Pani/CSA (Polyaniline/Camphor sulfonic acid), or PANI/PSS (Polyaniline/Poly(4-styrene-sulfonate)) may be used.

As the hole transport material, the indenophenanthrene compound according to an embodiment of the present invention may be used alone or in combination with known hole transport materials.

Specifically, the hole transport material includes an indenopenanthrene compound according to an embodiment of the present invention, but may be used together with pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc., and low molecular or high molecular materials may be used together. As a specific example, NPB (N, N'-bis (naphthalen-1-yl) -N, N'-bis (phenyl) -benzidine), NPD (N, N'-bis (naphthalen-1-yl) -N, N'-bis(phenyl)-2,2'-dimethylbenzidine), mCP (1,3-Bis(N-carbazolyl)benzene), TPD (N,N'-Bis(3-methylphenyl)-N,N'- diphenylbenzidine), TTB (N,N,N',N'-tetrakis(4-methylphenyl)-(1,1'-biphenyl)-4,4-diamine), TTP (N1,N4-diphenyl-N1,N4- dim-tolylbenzene-1,4-diamine), ETPD (N,N'-bis(4-methylphenyl)-N,N'-bis(4-ethylphenyl)-[1,1'-(3,3'-dimethyl )biphenyl]-4,4'-diamine), VNPB (N4,N4'-di(naphthalen-1-yl)-N4,N4'-bis(4-vinylphenyl)biphenyl-4,4'-diamine), ONPB (N4,N4'-bis(4-(6-((3-ethyloxetan-3-yl)methoxy)hexyl)phenyl)-N4,N4'-diphenylbiphenyl-4,4'-diamine), OTPD (N4,N4 small molecule hole transporters such as '-bis(4-(6-((3-ethyloxetan-3-yl)methoxy)hexyl)phenyl)-N4,N4'-diphenylbiphenyl-4,4'-diamine); There are polymer hole transport materials such as PVK (poly-N-vinylcarbazole), polyaniline, and (phenylmenyl) polysilane.

Examples of the electron transport material include oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinodimethane and derivatives thereof, and fluorenone. Metal complexes of derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, 8-hydroxyquinoline and its derivatives, etc. may be used, and high molecular materials as well as low molecular materials may be used. As specific examples, TSPO1 (diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide), TPBI (1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene); Alq ₃ (tris(8-hydroxyquinolinato)aluminum); BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline); PBD (2-(4-biphenyl)-5-(4-tert-butyl-phenyl)-1,3,4-oxadizole), TAZ (3-(4-biphenyl)-4-phenyl-5-(4- tert-butyl-phenyl)-1,2,4-triazole), OXD-7 (1,3-bis[2-(4-tert-butylphenyl)-1,3,4-oxadiazo-5-yl]benzene) azole compounds such as; tris(phenylquinoxaline) (TPQ); TmPyPB (3,3'-[5'-[3-(3-Pyridinyl)phenyl][1,1':3',1''-terphenyl]-3,3''-diyl]bispyridine) etc. may, but is not limited thereto.

As an electron injection material, for example, LIF or Liq (lithium quinolate) is typically used in the art, but is not limited thereto.

A red, green or blue light emitting material may be used as the light emitting material, and if necessary, two or more light emitting materials may be mixed and used. In addition, a fluorescent material can be used as a light emitting material, but it can also be used as a phosphorescent material. As the light emitting material, a material that emits light by combining holes and electrons respectively injected from the anode and the cathode may be used, but materials in which a host material and a dopant material are involved in light emission may also be used.

The light emitting layer may be formed by a method such as a vacuum deposition method, a spin coating method, a cast method, an LB method, etc. of a light emitting material. In general, it can be selected from almost the same range of conditions as the formation of the hole injection layer. In addition, a known compound can be used as a host or dopant for the light emitting layer material.

Also, for example, as a material for the light emitting layer, as a fluorescent dopant, IDE102 or IDE105 from Idemitsu, BD-331 or BD-142 (N ⁶ ,N ¹² -bis(3,4-dimethylphenyl)-N ⁶ ,N ¹² -Dimesityl trisene-6,12-diamine) can be used, and as the phosphorescent dopant, green phosphorescent dopant Ir(ppy) ₃ (tris(2-phenylpyridine)iridium), blue dopant F2Irpic (iridium(III) bis[ 4,6-difluorophenyl)-pyridinato-N,C2']picolinate), UDC's red phosphorescent dopant RD61, etc. may be co-evaporated (doped).

The phosphorescent dopant is a compound capable of emitting light from triplet excitons, and is not particularly limited as long as it emits light from triplet excitons. A specific example may be a metal complex including one or more metals selected from the group consisting of Ir, Ru, Pd, Pt, Os, and Re, and may be a porphyrin metal complex or an ortho metallized metal complex.

The porphyrin metal complex may be specifically a porphyrin platinum complex.

The ortho metallized metal complex is a 2-phenylpyridine (ppy) derivative, a 7,8-benzoquinoline derivative, a 2-(2-thienyl)pyridine (2-(2-thienyl)pyridine, tp) derivative , 2-(1-naphthyl)pyridine (2-(1-naphthyl)pyridine, npy) derivatives, 2-phenylquinoline (2-phenylquinoline, pq) derivatives, etc. may be included as a ligand. At this time, these derivatives may have a substituent as needed. As an auxiliary ligand, it may further have ligands other than the above ligands, such as acetylacetonato (acac) and picric acid. Specific examples include bisthienylpyridine acetylacetonate iridium, bis(2-benzo[b]thiophen-2-yl-pyridine)(acetylacetonato)iridium(III) (bis(2- benzo[b]thiophen-2-yl-pyridine)(acetylacetonato)iridium(III), Ir(btp) ₂ (acac)), bis(2-phenylbenzothiazole)(acetylacetonato)iridium(III) ( bis(2-phenylbenzothiazole)(acetylacetonato)iridium(III), Ir(bt) ₂ (acac)), bis(1-phenylisoquinoline)(acetylacetonato)iridium(III) (bis(1-phenylisoquinoline)( acetylacetonato)Iridium(III), Ir(piq) ₂ (acac)), tris(1-phenylisoquinoline)iridium(III) (tris(1-phenylisoquinoline)iridium(III), Ir(piq) ₃ ), tris( 2-phenylpyridine) iridium (III) (tris (2-phenylpyridine) iridium (III), Ir (ppy) ₃ ), tris (2-biphenylpyridine) iridium (tris (2-biphenylpyridine) iridium), tris (3 - Biphenylpyridine) iridium (tris (3-biphenylpyridine) iridium), tris (4-biphenylpyridine) iridium (tris (4-biphenylpyridine) iridium), and the like, but are not limited thereto.

In addition, when used with a phosphorescent dopant in the light emitting layer, a hole blocking material (HBL) may be additionally laminated by vacuum deposition or spin coating to prevent diffusion of triplet excitons or holes into the electron transport layer. The hole blocking material that can be used at this time is not particularly limited, but can be selected and used arbitrarily from known ones used as hole blocking materials. For example, it may be an oxadiazole derivative or a triazole derivative or a phenanthroline derivative, specifically Balq (bis(8-hydroxy-2-methylquinolinato)-aluminum biphenoxide), phenanthrolines type compounds (: BCP (vasocuproin) from UDC), etc. can be used.

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

The indenopenanthrene compound according to an embodiment of the present invention may act in organic electronic devices including organic solar cells, organic photoreceptors, and organic transistors on a principle similar to that applied to organic light emitting devices.

Hereinafter, the present invention will be described in more detail through examples, but these are only for exemplifying the present invention and are not intended to limit the scope of the present invention.

Example I: Preparation of Compound P1

Preparation of compound a-2

Compound a-1 13.32g (60mmol), Pd (PPh _{3 ) 4} 2.9g (2.5mmol), K ₂ CO ₃ 16.6g ( 120 mmol) and 3-iodopyridine-2-amine (3-iodopyridine-2-amine) 11 g (50 mmol) were added thereto, followed by stirring at 80 ° C. for 12 hours under a nitrogen atmosphere. After the reaction was completed, extraction was performed using water and EA, sodium sulfate was added to the EA layer to retain moisture, and the mixture was filtered. After removing the solvent, column was performed to obtain 11 g (81%) of compound a-2.

Preparation of compound a-3

8g (29.6mmol) of compound a-2 and 81.38ml (325.5mmol) of 4M HCl were added to 80ml of CH ₃ CN, followed by stirring at 0°C. After dissolving 2.5 g (35.5 mmol) of NaNO ₂ in water, it was slowly added for 15 minutes and stirred at 0 °C for 30 minutes. After dissolving 11.8g (71mmol) of KI in water, it was slowly added for 10 minutes and stirred for 18 hours while slowly raising the temperature from 0°C to room temperature. After extraction using water and EA, sodium sulfate was added to the EA layer to retain moisture, and then filtered. After removing the solvent, column was performed to obtain 7 g (62%) of compound a-3.

Preparation of compound P1

In 224ml of toluene, compound a-3 (67.3mmol), 1,2-diphenylethane compound b (26.9mmol), bis(allyl)dichloropalladium (1.1mmol), sodium tert-butoxide After adding (Sodium tert-butoxide) (4.5mmol), the mixture was stirred at 80℃ for 12 hours under a nitrogen atmosphere. After cooling to room temperature, DCM was added thereto, celite was filtered, the solvent was removed, and then the target compound P1 was obtained by column.

Example II: Preparation of Compound P2

Preparation of compound a-4

Compound a-4 was obtained by reacting in the same manner as in the synthesis method of compound P1 in Example I, except that 1,2-bis(4-halophenyl)ethane was used instead of 1,2-diphenylethane compound b. .

Preparation of compound P2

Compound a-4 (17mmol), substituted boronic acid or boronic ester compound (20.4mmol), K ₂ CO ₃ (34mmol) and tetrakis (triphenyl) in Toluene/Ethanol water (volume ratio 4:1:1, 56mL) After adding phosphine)palladium (Pd(PPh ₃ ) ₄ ) (0.9 mmol), the mixture was refluxed and stirred at 120° C. under a nitrogen atmosphere. When the reaction was completed, the mixture was filtered using celite and florisil, and then washed with MC. The target compound P2 was obtained by recrystallization and purification using EA and Hex.

Example III: Preparation of Compound P3

Preparation of compound c-1

Compound a-2 of Example I except for using 3-iodopyridine-2,5-diamine instead of 3-iodopyridine-2-amine. 10.8 g (81%) of compound c-1 was obtained by reacting in the same manner as in the synthesis method.

Preparation of compound c-2

Except for using compound c-1 instead of compound a-2, 5.1 g (62%) of compound c-2 was obtained in the same manner as in the synthesis method of compound a-3 in Example I.

Preparation of compound P3

Compound P3 was obtained by reacting in the same manner as in the synthesis method of Compound P1 in Example I, except that Compound c-2 was used instead of Compound a-3.

Example IV: Preparation of Compound P4

Compound P3 (17.9mmol), bromobenzene (37.6mmol), palladium acetate (1.43mmol), tri-tert-butyl phosphine (5.37mmol), Sodium-tert-butoxide (50.2 mmol) was added and stirred at 110° C. for 1 hour. After cooling to room temperature, the catalyst was removed by filtering. After extraction using water and EA, sodium sulfate was added to the EA layer to retain moisture, and then filtered. After removing the solvent, the column was performed to obtain the target compound P4.

Example V: Preparation of Compound P5

Preparation of compound d-2

10g (38.7mmol) of compound d-1 was added to 129ml of THF, and 19.4ml (48.4mmol) of n-BuLi was slowly added under a -78°C nitrogen atmosphere, followed by stirring at the same temperature for 1 hour. When stirring was completed, 10 g of trimethyl borate was slowly added at the same temperature, stirred for 2 hours, and then the temperature was slowly raised to room temperature. After the reaction was completed, a 4M HCl solution was added, extracted with DCM, the solvent was removed, and recrystallized with EA to obtain 6.9 g (80%) of compound d-2.

Preparation of compound d-3

Compound d- ₂ 8.9g (40mmol), Pd (PPh ₃ ) ₄ 1.9g (1.7mmol), K ₂ CO ₃ 11g (80mmol) in 1,4-Dioxane/H 2 O 84ml (v/v=10/2) ) and 1,2-diiodobenzene (1,2-diiodobenzene) 11g (33.3mmol) was added, and then the mixture was stirred for 12 hours at 80° C. under a nitrogen atmosphere. After the reaction was completed, extraction was performed using water and EA, sodium sulfate was added to the EA layer to retain moisture, and then the mixture was filtered. After removing the solvent, column was performed to obtain 10.8 g (85%) of compound d-3.

Preparation of compound P5

Compound P5 was obtained by reacting in the same manner as in the synthesis method of compound P1 in Example I, except that compound d-3 was used instead of compound a-3.

Example VI: Preparation of Compound P6

Preparation of compound d-4

Compound d-4 was obtained by reacting in the same manner as in the synthesis method of Compound P1 in Example I, except that 1,2-bis(4-halophenyl)ethane was used instead of 1,2-diphenylethane compound b. .

Preparation of compound P6

Except for using compound d-4 instead of compound a-4, the reaction was performed in the same manner as in Example II for synthesizing compound P2 to obtain target compound P6.

[Example 1] Preparation of compound 1-1

10.3g (67.3mmol) of compound a-3 in 224ml of toluene, 4g (26.9mmol) of 1,2-diphenylethyne (compound b-1), bis(allyl)dichloropalladium (Bis(allyl) After adding 0.41 g (1.1 mmol) of dichloropalladium and 0.43 g (4.5 mmol) of sodium tert-butoxide, the mixture was stirred at 80° C. for 12 hours under a nitrogen atmosphere. After cooling to room temperature, DCM was added thereto, celite was filtered, the solvent was removed, and 7.55 g (78%) of target compound 1-1 was obtained by column.

[Example 2] Preparation of compound 1-24

Preparation of compound a-4-1

Compound a-4- was reacted in the same manner as in the synthesis method of Compound 1-1 in Example 1, except that 1,2-bis(4-bromophenyl)ethane was used instead of 1,2-diphenylethane. 1 9.4 g (45%) was obtained.

Preparation of compounds 1-24

Compound a-4-1 10g (17mmol) and phenylboronic acid 2.5g (20.4mmol), K ₂ CO ₃ 4.7g (34mmol) in Toluene/Ethanol water (volume ratio 4:1:1, 56mL) ) and Pd(PPh ₃ ) ₄ 1 g (0.9 mmol) was added thereto, and the mixture was refluxed and stirred at 120° C. under a nitrogen atmosphere. When the reaction was completed, the mixture was filtered using celite and florisil, and then washed with MC. Recrystallization and purification using EA and Hex yielded 8.7 g (88%) of the target compound 1-24.

[Example 3] Preparation of compound 2-1

7.62 g (76%) of the target compound 2-1 was obtained by reacting in the same manner as in Example 1 for synthesizing compound 1-1, except that compound c-2 was used instead of compound a-3.

[Example 4] Preparation of compound 2-3

Toluene 60ml compound 2-1 8g (17.9mmol), bromobenzene (Bromobenzene) 3.8ml (37.6mmol), palladium acetate (palladium acetate) 0.3g (1.43mmol), tri-tert-butylphosphine (tri tert-butyl phosphine) 1.1g (5.37mmol) and sodium tert-butoxide (sodium-tert-butoxide) 4.8g (50.2mmol) were added and stirred at 110 ° C. for 1 hour. After cooling to room temperature, the catalyst was removed by filtering. After extraction using water and EA, sodium sulfate was added to the EA layer to retain moisture, and then filtered. After removing the solvent, column was performed to obtain 9.22 g (86%) of target compound 2-3.

[Example 5] Preparation of compound 3-1

7.7 g (79%) of the target compound 3-1 was obtained by reacting in the same manner as in the synthesis method of compound 1-1 in Example 1, except that compound d-3 was used instead of compound a-3.

[Example 6] Preparation of compound 3-24

Preparation of compound d-4-1

9.8 g (47%) of compound a-4-1 was obtained by reacting in the same manner as in the synthesis method of compound 1-24 of Example 2, except that compound d-3 was used instead of compound a-3.

Preparation of compounds 3-24

Except for using compound a-4-1 instead of compound a-4-1, the reaction was performed in the same manner as in Example 2 for synthesizing compound 1-24 to obtain 8.3 g (84%) of target compound 3-24. .

Compounds 1-1 to 1-39, 2-1 to 2-36, and 3-1 to 3-39 of Table 1 were prepared using the methods of the above examples.

[Table 1]

¹ H NMR and MS values of the prepared compounds 1-1 to 1-39, 2-1 to 2-36, and 3-1 to 3-39 are shown in Table 2 below.

[Table 2]

Example VII: Preparation and Evaluation of Organic Light-Emitting Devices

An organic light emitting device was manufactured according to a conventional method using the compounds obtained in Examples as hole transport layers, respectively.

First, an ITO substrate is installed in the substrate folder of the vacuum deposition equipment, and 2-TNATA (4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine) is applied on the ITO layer (anode) formed on the glass substrate. was vacuum-deposited to form a hole injection layer having a thickness of 10 nm, and then the indenophenanthrene compound prepared in Example of the present invention was vacuum-deposited to form a hole transport layer having a thickness of 20 nm.

Subsequently, BD-331 (Idemitsu Co.) was used as a light emitting dopant, AND (9,10-Bis(2-naphthyl)anthracene) was used as a host material, and the doping concentration was fixed at 4% to form a layer on the hole transport layer. A light emitting layer was deposited with a thickness of 30 nm.

Subsequently, Alq3 (tris-(8-hydroxyquinoline)aluminum) was vacuum deposited to a thickness of 40 nm as an electron transport layer on the light emitting layer. Thereafter, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm, followed by Al to a thickness of 150 nm, and Al/LiF was used as a cathode to fabricate an organic light emitting device.

[Comparative Examples 1 to 3]

An organic light emitting diode was manufactured in the same manner as in Example VII, except that Comparative Compound A, Comparative Compound B, or Comparative Compound C was used instead of the indenopenanthrene compound of the present invention as a hole transport material.

A forward bias DC voltage was applied to each of the organic light emitting devices manufactured by Example VII and Comparative Examples 1 to 3 of the present invention, and electroluminescence (EL) characteristics were measured with PR-650 of Photoresearch, 300 cd / m ² At the standard luminance, T95 life was measured through life measurement equipment manufactured by McScience. T95 means the time taken for the luminance of the light emitting device to reach 95% of the initial luminance.

It can be seen that the indenophenanthrene compounds developed in the present invention, as hole transport materials, can improve power consumption by inducing an increase in power efficiency by lowering the driving voltage along with better light emission characteristics than conventional hole transport materials, In addition, it can be seen that a significant increase is also observed in life characteristics.

Therefore, the indenophenanthrene compound of the present invention can be used as a material for forming an organic layer such as a hole transport material to manufacture an organic light emitting device exhibiting low driving voltage, excellent color purity, high luminous efficiency, and long lifespan. In addition, it is obvious that the same effect can be obtained even if the indenophenanthrene compounds of the present invention are used in other organic material layers of the organic light emitting device, for example, a light emitting layer, a hole injection layer, an electron injection layer, and an electron transport layer.

That is, the indenophenanthrene compound according to the present invention has excellent electron mobility due to its structural specificity, thereby improving the current characteristics of the device and intensifying the driving voltage, thereby inducing an increase in power efficiency to produce an organic light emitting device with improved power consumption. can be produced

Claims (10)

An indenopenanthrene compound represented by Formula 1 below:
[Formula 1]

In Formula 1,
A ₁ and A ₂ are each independently CH or N;
R ₁ is deuterium, C1-C60 alkyl, cyano, C2-C60 alkenyl, C2-C60 alkynyl, C3-C60 cycloalkyl, C2-C60 heterocycloalkyl, hydroxy, C1-C60 alkoxy, C6-C60 aryl oxy, C6-C60 aryl, C2-C60 heteroaryl or -NR _1a R _1b ;
R ₂ is hydrogen or -NR _2a R _2b ;
R ₃ and R ₄ are each independently hydrogen, deuterium, cyano, C1-C60 alkyl, C2-C60 alkenyl, C2-C60 alkynyl, C3-C60 cycloalkyl, C2-C60 heterocycloalkyl, C6-C60 aryl , C2-C60 heteroaryl or -NR _3a R _3b ;
R _1a , R _1b , R _2a , R _2b , R _3a and R _3b are each independently hydrogen, deuterium, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C2-C60 heteroaryl or amino;
Alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, alkoxy, aryloxy, aryl and heteroaryl of R ₁ , alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl of R ₃ and R ₄ , Aryl and heteroaryl, alkyl, cycloalkyl, aryl and heteroaryl of R _1a , R _1b , R _2a , R _2b , R _3a and R _3b are deuterium, C1-C60 alkyl, haloC1-C60 alkyl, halogen, cyano , C3-C60 Cycloalkyl, C2-C60 Heterocycloalkyl, C1-C60 Alkoxy, C6-C60 Aryl, C6-C60 Aryloxy, C6-C60 ArylC1-C60 Alkyl, C1-C60 AlkylC6-C60 Aryl, C2- may be further substituted with one or more selected from the group consisting of C60 heteroaryl, -NR'R'', nitro and hydroxy;
R' and R'' are each independently hydrogen, C1-C60 alkyl, C6-C60 aryl, C2-C60 heteroaryl or amino;
a is an integer from 0 to 4;
The heterocycloalkyl and heteroaryl include one or more heteroatoms selected from N, O, S and Se. According to claim 1,
One of A ₁ and A ₂ is CH, and the other is N, an indenopenanthrene compound. According to claim 1,
The indenophenanthrene compound is an indenophenanthrene compound represented by Formula 2 below:
[Formula 2]

In Formula 2, R ₁ , R ₂ and a are the same as defined in Formula 1 of claim 1;
One of A ₁ and A ₂ is CH, and the other is N. According to claim 1,
The indenophenanthrene compound is represented by the following formula (3) or formula (4), an indenopenanthrene compound:
[Formula 3]

[Formula 4]

In Formulas 3 and 4,
R _A , R _B , R _C and R _D are each independently hydrogen, deuterium, C1-C30 alkyl, cyano, C2-C30 alkenyl, hydroxy, C1-C30 alkoxy, C6-C30 aryloxy, C6-C30 aryl, C2-C30 heteroaryl or -NR _1a R _1b ;
R ₂ is hydrogen or -NR _2a R _2b ;
R _1a , R _1b , R _2a and R _2b are each independently hydrogen, deuterium, C1-C30 alkyl, C6-C30 aryl, C2-C30 heteroaryl or amino;
Alkyl, alkenyl, alkoxy, aryloxy, aryl and heteroaryl of R _A , R _B , R _C and R _D , alkyl, aryl and heteroaryl of R _1a , R _1b , R _2a and R _2b are deuterium, C1 -C30 Alkyl, HaloC1-C30 Alkyl, Halogen, Cyano, C1-C30 Alkoxy, C6-C30 Aryl, C6-C30 Aryloxy, C6-C30 ArylC1-C30 Alkyl, C1-C30 AlkylC6-C30 Aryl, C2 may be further substituted with one or more selected from the group consisting of -C30 heteroaryl and -NR'R'';
R' and R'' are each independently hydrogen, C1-C30 alkyl, C6-C30 aryl, C2-C30 heteroaryl or amino. According to claim 4,
Wherein R _A , R _B , R _C and R _D are each independently hydrogen, deuterium, C1-C20 alkyl, cyano, vinyl, allyl, hydroxy, C1-C20 alkoxy, C6-C30 arylC1-C20 alkoxy, C6 -C30 aryloxy, C1-C20 alkylC6-C30 aryloxy, C6-C30 aryl, C2-C20 heteroaryl or amino;
R ₂ is hydrogen or -NR _2a R _2b ;
R _2a and R _2b are each independently hydrogen, deuterium, C1-C20 alkyl, C6-C30 aryl or C2-C20 heteroaryl;
Alkyl, aryl and heteroaryl of R _A , R _B , R _C and R _D , alkyl, aryl and heteroaryl of R _2a and R _2b are deuterium, C1-C20 alkyl, cyano, C1-C20 alkoxy, C6- Further substituted with one or more selected from the group consisting of C30 aryl, C6-C30 aryloxy, C6-C30 arylC1-C20 alkyl, C1-C20 alkylC6-C30 aryl, C2-C20 heteroaryl and -NR'R'' can be;
wherein R' and R'' are each independently hydrogen, C1-C20 alkyl, C6-C30 aryl or C2-C20 heteroaryl. According to claim 3,
R ₁ is deuterium, C1-C10 alkyl, cyano, vinyl, allyl, hydroxy, C1-C10 alkoxy, C6-C20 arylC1-C10 alkoxy, C6-C20 aryloxy, C1-C10 alkylC6-C20 aryloxy Or an amino, or an indenopenanthrene compound selected from the following structures.

In the above structure,
X ₁ is NR _X1 , O or S;
Y ₁ is CR _Y1 R _Y2 , O or S;
R _X1 is hydrogen, deuterium, C1-C10 alkyl, C6-C12 aryl or C3-C12 heteroaryl;
R _Y1 and R _Y2 are each independently hydrogen, deuterium, C1-C10 alkyl, C6-C12 aryl or C3-C12 heteroaryl;
R ₄₁ , R ₄₂ and R ₄₃ are independently of each other hydrogen, deuterium, C1-C10 alkyl, cyano, C1-C10 alkoxy, C6-C12 aryl, C3-C12 heteroaryl or -NR'R'';
R' and R'' are each independently C1-C10 alkyl, C6-C12 aryl or C3-C12 heteroaryl;
R ₄₄ and R ₄₅ are each independently hydrogen, deuterium, C1-C10 alkyl or C6-C12 aryl. According to claim 3,
Wherein R ₂ is hydrogen or -NR _2a R _2b , and R _2a and R _2b are each independently hydrogen, deuterium, C1-C10 alkyl or C6-C20 arylC1-C10 alkyl, or selected from the following structures, Nophenanthrene compounds.

In the above structure,
X ₂ is NR _X2 , O or S;
Y ₂ is CR _Y3 R _Y4 , O or S;
R _X2 is hydrogen, deuterium, C1-C10 alkyl, C6-C12 aryl or C3-C12 heteroaryl;
R _Y3 and R _Y4 are each independently hydrogen, deuterium, C1-C10 alkyl, C6-C12 aryl or C3-C12 heteroaryl;
R ₅₁ , R ₅₂ and R ₅₃ independently of each other are hydrogen, deuterium, C1-C10 alkyl, cyano, C1-C10 alkoxy, C6-C12 aryl, C3-C12 heteroaryl or -NR'R'';
R' and R'' are each independently C1-C10 alkyl, C6-C12 aryl or C3-C12 heteroaryl;
R ₅₄ and R ₅₅ are each independently hydrogen, deuterium, C1-C10 alkyl or C6-C12 aryl. According to claim 1,
The indenophenanthrene compound is selected from the following, an indenopenanthrene compound:

An anode, a cathode, and at least one organic material layer provided between the anode and the cathode, wherein at least one layer of the organic material layer contains the indenophenanthrene compound according to any one of claims 1 to 8 organic light emitting device. According to claim 9,
The organic material layer is at least one layer selected from a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, an organic light emitting device.