KR20210139190A - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a novel compound and an organic light emitting device using the same. The present invention provides a compound represented by chemical formula 1. The compound represented by chemical formula 1 above can be used as a material for an organic layer of the organic light emitting device, and 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 using same {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, for example, a hole injection layer, a hole transport layer, an electron suppression layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron. It may be formed of an injection layer or 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 compound and an organic light emitting device comprising the same.

The present invention provides a compound represented by the following formula (1):

[Formula 1]

In Formula 1,

Y is O or S;

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

n1 is an integer from 0 to 6,

n2 is an integer from 0 to 3,

One of R ₂ is of Formula 2, and the rest is hydrogen or deuterium;

[Formula 2]

In Formula 2,

L is a single bond; Or a substituted or unsubstituted C _6-60 arylene,

X is N, or CH, provided that at least two or more of X are N;

Ar ₁ and Ar ₂ are each independently substituted or unsubstituted C _6-60 aryl; _{or a substituted or unsubstituted C 2-60} heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S.

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 layer of the organic material layer comprises a compound represented by the formula (1). to provide.

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

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), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (6), a light emitting layer (3), a hole blocking layer (8), an electron injection and transport layer ( 9) and an example of an organic light emitting device including a cathode 4 are shown.

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

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, 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 example of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the above-described alkyl group. In the present specification, as for heteroaryl among heteroarylamines, the description 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.

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

The compound represented by Formula 1 is a fluoranthene ring and a heterocyclic ring containing two or more N is bonded to a specific position of the parent nucleus structure in which a bicyclic heterocyclic ring containing O or S is condensed. It is possible to improve the characteristics of the organic light emitting device. In particular, the compound represented by Formula 1 uses a polycyclic aromatic core that connects a plurality of aromatic rings, thereby increasing molecular rigidity, increasing stability with respect to electrons and holes, and can exhibit better light emitting properties, thereby Due to this, quantum efficiency and lifetime can be improved.

In Formula 1, the compound represented by Formula 1 may be represented by Formula 1-1 or 1-2, depending on a specific position at which a heterocyclic ring containing two or more N is bonded:

[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,

Y, R ₁ , n1, n2, L, X, Ar ₁ and Ar ₂ are as defined in Formula 1 above.

Specifically, in Formula 1, Formula 1-1, and Formula 1-2, Y is O or S.

Specifically, in Formula 1, Formula 1-1, and Formula 1-2, R ₁ is each hydrogen, deuterium, halogen, or cyano, or substituted or unsubstituted C _1-20 alkyl, or C _1-12 alkyl, or C _1-6 alkyl, or substituted or unsubstituted C _1-20 alkoxy, or C _1-12 alkoxy, or C _1-6 alkoxy, or substituted or unsubstituted C _2-20 alkenyl, or C _2-12 alkenyl, or C _2-6 alkenyl, or substituted or unsubstituted C _2-20 alkynyl, or C _2-12 alkynyl, or C _2-6 alkynyl, or substituted or unsubstituted C _3-30 cycloalkyl, or C _3-25 cycloalkyl, or C _3-20 cycloalkyl, or substituted or unsubstituted C _6-30 aryl, or C _6-28 aryl, or C _{6- 25} aryl, or C _{6-20 aryl, or substituted or unsubstituted C 3-30} heteroaryl comprising at least one heteroatom selected from the group consisting of N, O and S, or C _5-28 heteroaryl , or C _5-25 heteroaryl, or C _6-20 heteroaryl, or C _12-18 heteroaryl.

For example, _{each of R 1} may be hydrogen or deuterium. Also, _{all of R 1} may be hydrogen.

Specifically, in Formula 1, Formula 1-1, and Formula 1-2, n1 and n2 may each be an integer of 0 to 2, or 0 or 1.

Specifically, in Formula 1, Formula 1-1, and Formula 1-2, L is a single bond; or substituted or unsubstituted C _6-30 arylene, or C _6-28 arylene, or C _6-25 arylene, or C _6-20 arylene. Preferably, L is a single bond; or phenylene, biphenylrylene, terphenylrylene, quaterphenylrylene, or naphthylene.

For example, L is a single bond; Or it may be one represented by any one selected from the group consisting of:

.

.

Specifically, in Chemical Formulas 1, 1-1, and 1-2, two of X may be N, the rest may be CH, or all of X may be N.

Specifically, in Formulas 1 and 1-1, and Formula 1-2, Ar ₁ and Ar ₂ are each substituted or unsubstituted C _6-30 aryl, or C _6-28 aryl, or C _6-25 aryl; or C _6-20 aryl; _{or substituted or unsubstituted C 3-30} heteroaryl, or C _5-28 heteroaryl, or C _5-25 heteroaryl, containing any one or more heteroatoms selected from the group consisting of N, O and S; or C _6-20 heteroaryl, or C _12-18 heteroaryl.

More specifically, Ar ₁ and Ar ₂ are each phenyl, naphthyl substituted phenyl, dibenzofuranyl substituted phenyl, dibenzothiophenyl substituted phenyl, carbazolyl substituted phenyl, biphenyl, terphenyl, naphthyl, phenyl substituted naphthyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, or phenyl substituted carbazolyl.

In particular, _{at least one of Ar 1} and Ar ₂ may be phenyl, naphthyl substituted phenyl, biphenyl, naphthyl, or phenyl substituted naphthyl.

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

.

Meanwhile, the compound represented by Chemical Formula 1 may be prepared by a preparation method such as Scheme 1 or Scheme 2 below. The manufacturing method may be more specific in the Synthesis Examples to be described later.

[Scheme 1]

In Scheme 1, Y, R ₁ , R ₂ , n1, and n2 are as defined in Formula 1 above, and one of _{Q 1 is BO 2} C ₂ (CH ₃ ) ₄ , or B(OH) ₂ , the remainder is hydrogen or deuterium, Q ₂ is a halogen group, preferably Cl, Br, or I, more preferably Cl;

[Scheme 2]

In Scheme 2, Y, R ₁ , R ₂ , n1, and n2 are as defined in Formula 1 above, and _{one of Q 3} is a halogen group, preferably Cl, Br, or I, and more preferably is Cl, the _{remainder of Q 3} is hydrogen or deuterium, and Q ₄ is BO ₂ C ₂ (CH ₃ ) ₄ , or B(OH) ₂ .

Specifically, Scheme 1 and Scheme 2 introduce a heteroaryl substituent containing at least two or more N at a specific position in the parent nucleus structure in which a fluoranthene ring and a bicyclic heterocyclic ring containing O or S are condensed. is the reaction In this reaction, when _{a leaving group such as BO 2} C ₂ (CH ₃ ) ₄ , or B(OH) ₂ is bonded to an intermediate compound including a fluoranthene ring, the compound of Formula 1 can be prepared according to Scheme 1. And, when the BO ₂ C ₂ (CH ₃ ) ₄ , or a leaving group such as B(OH) ₂ is bonded to an intermediate compound including a heteroaryl substituent containing at least two or more N, according to Scheme 2, Formula 1 compounds can be prepared.

For example, in Scheme 1, one of Q ₁ is a pinacolborane group, BO ₂ C ₂ (CH ₃ ) ₄ , or a boronic acid group, B(OH) ₂ , and a fluoranthene ring. A polycyclic compound in which a bicyclic heterocyclic ring containing O or S is condensed, and a heterocyclic compound _{containing Q 2} as a halogen group and at least two or more N are prepared by a palladium catalyst (Pd) in the presence of a base. reaction with a catalyst). _{Through this reaction, a pinacolborone group BO 2} C ₂ (CH ₃ ) ₄ , or B(OH) in a polycyclic compound in which a fluoranthene ring and a bicyclic heterocycle including O or S are condensed ) ₂ is to introduce a heteroaryl group containing at least two or more N at the position of Q _{1 .} Preferably, in Scheme 1, Q ₁ is BO ₂ C ₂ (CH ₃ ) ₄ , and Q ₂ may be chlorine. Specific reaction conditions of Scheme 1 may be performed with reference to known reactions known in the art. The manufacturing method may be more specific in the Synthesis Examples to be described later.

In another example, in Scheme 2 _{, one of Q 3} is a halogen group, and a polycyclic compound in which a fluoranthene ring and a bicyclic heterocyclic ring including O or S are condensed, and BO ₂ C ₂ (CH _{3 )} ) ₄ , or a boronic acid group, B(OH) ₂ , which is Q ₄ , and a heterocyclic compound containing at least two or more N is reacted with a palladium catalyst (Pd catalyst) in the presence of a base It is done by doing Through this reaction, a heteroaryl group containing at least two or more N is introduced at the _{Q 3} position, which is a halogen group, of a polycyclic compound in which a fluoranthene ring and a bicyclic hetero ring containing O or S are condensed will be. Preferably, in Scheme 2, Q ₃ may be chlorine, and Q ₄ may be BO ₂ C ₂ (CH ₃ ) ₄ . Specific reaction conditions of Scheme 2 may be performed with reference to known reactions known in the art. The manufacturing method may be more specific in the Synthesis Examples to be described later.

In addition, in Schemes 1 and 2, the base component is potassium carbonate (K ₂ CO ₃ ), sodium bicarbonate (NaHCO ₃ ), cesium carbonate (Cesium carbonate, Cs ₂ CO ₃ ), sodium acetate (sodium acetate, NaOAc), potassium acetate (KOAc), sodium tert-butoxide (NaOtBu), sodium ethoxide (NaOEt), or triethylamine (Et ₃₎ N), N,N-diisopropylethylamine (N,N-diisopropylethylamine, EtN(iPr) ₂ ) and the like may be used. Preferably, the base component is potassium carbonate (K ₂ CO ₃ ), cesium carbonate (Cs ₂ CO ₃ ), potassium acetate (KOAc), sodium tert-butoxide (sodium tert- butoxide, NaOtBu), or N,N-diisopropylethylamine (N,N-diisopropylethylamine, EtN(iPr) ₂ ).

In addition, in Schemes 1 and 2, the palladium catalyst is tetrakis (triphenylphosphine) palladium (0) (tetrakis (triphenylphosphine) palladium (0), tris (dibenzylideneacetone) dipalladium (0) ( tris(dibenzylideneacetone)-dipalladium (0), Pd ₂ (dba) ₃ ), bis(tri-(tert-butyl)phosphine)palladium (0) (bis(tri-(tert-butyl)phosphine)palladium(0) , Pd(P-tBu ₃ ) ₂ ), bis(dibenzylideneacetone)palladium (0) (bis(dibenzylideneacetone)palladium (0), Pd(dba) ₂ ), Pd(PPh ₃ ) ₄ ) or palladium (II) ) acetate (palladium(II) acetate, Pd(OAc) ₂ ) may be used. Preferably, the palladium catalyst is tetrakis(triphenylphosphine)palladium (0) (tetrakis(triphenylphosphine)palladium (0), Pd(PPh ₃ ) ₄ ), bis(tri-(tert-butyl)phosphine) palladium (0) (bis(tri-(tert-butyl)phosphine)palladium(0), Pd(P-tBu ₃ ) ₂ ), or bis(dibenzylideneacetone)palladium (0) (bis(dibenzylideneacetone)palladium ( 0), Pd(dba) ₂ ). In particular, in Scheme 1, tetrakis(triphenylphosphine)palladium (0) (tetrakis(triphenylphosphine)palladium (0), Pd(PPh ₃ ) ₄ ) may be used as a catalyst, and in Scheme 2, bis(tri- (tert-butyl)phosphine)palladium (0) (bis(tri-(tert-butyl)phosphine)palladium(0), Pd(P-tBu ₃ ) ₂ ), may be used as a catalyst.

As used herein, equivalent (eq.) means molar equivalent.

Meanwhile, the present invention provides an organic light emitting device including the compound represented by Formula 1 above. 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, an electron suppression layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

In addition, the organic layer may include a hole injection layer, a hole transport layer, or a layer that injects and transports holes at the same time, and the hole injection layer, the hole transport layer, or a layer that simultaneously injects and transports holes is represented by Formula 1 The compounds shown are included.

Also, the organic layer may include an electron blocking layer, and the electron blocking layer includes the compound represented by Formula 1 above.

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

In addition, the light emitting layer further includes a dopant compound.

In addition, the light emitting layer includes the compound of Formula 1 and a dopant.

For example, the light emitting layer includes the compound of Formula 1 and a dopant, and includes the compound of Formula 1 and the dopant in a content ratio of 100:1 to 1:1.

In addition, the light emitting layer includes the compound of Formula 1 and the dopant, and the compound of Formula 1 and the dopant in a content ratio of 100:1 to 2:1.

In addition, the emission layer includes the compound of Formula 1 and the dopant, and the compound of Formula 1 and the dopant in a content ratio of 100:1 to 5:1.

For example, the dopant is a metal complex.

Specifically, the dopant is an iridium-based metal complex.

In addition, the organic material layer includes an emission layer, the emission layer includes a dopant, and the dopant material is selected from the following structural formulas.

.

.

The structures specified above are not limited to dopant compounds.

In addition, the organic layer may include a hole blocking layer, the hole blocking layer includes the compound represented by the formula (1).

In addition, the organic layer may include an electron transport layer, an electron injection layer, or a layer that simultaneously injects and transports electrons, and the electron transport layer, the electron injection layer, or a layer that simultaneously injects and transports electrons is represented by Formula 1 The compounds shown are included.

In addition, the organic layer may include a light emitting layer and a hole transport layer, and the light emitting layer or the hole transport layer may include a 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 .

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

2 is a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (6), a light emitting layer (3), a hole blocking layer (8), an electron injection and transport layer ( 9) and an example of an organic light emitting device including a cathode 4 are shown. In such a structure, the compound represented by Formula 1 may be included in at least one of the hole injection layer, the hole transport layer, the electron suppression layer, the light emitting layer, the hole blocking layer, and the electron injection and transport layer. Specifically, the compound represented by Formula 1 may be included in the light emitting layer or the hole transport layer, for example, may be included as a host material of the light emitting 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. After forming an organic material layer including a hole injection layer, a hole transport layer, an electron suppression layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer thereon, a material that can be used as a cathode is deposited thereon. can do. 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. In particular, the compound represented by Formula 1 has excellent solubility in a solvent used for the solution coating method, and thus it is easy to apply the solution coating method. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

Accordingly, the present invention provides a coating composition comprising the compound represented by Formula 1 and a solvent.

The solvent is not particularly limited as long as it is a solvent capable of dissolving or dispersing the compound according to the present invention, and for example, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o - Chlorine solvents, such as dichlorobenzene; ether solvents such as tetrahydrofuran and dioxane; aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; ketone solvents such as acetone, methyl ethyl ketone, and cyclohexanone; ester solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; Polyvalents such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, and 1,2-hexanediol alcohols and derivatives thereof; alcohol solvents such as methanol, ethanol, propanol, isopropanol and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; and amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; benzoate solvents such as butylbenzoate and methyl-2-methoxybenzoate; tetralin; and solvents such as 3-phenoxy-toluene. In addition, the above-mentioned solvent may be used alone or in combination of two or more solvents.

In addition, the viscosity of the coating composition is preferably 1 cP to 10 cP, and coating is easy in the above range. In addition, the concentration of the compound according to the present invention in the coating composition is preferably 0.1 wt/v% to 20 wt/v%.

In addition, the present invention provides a method of forming a functional layer using the above-described coating composition. Specifically, coating the coating composition according to the present invention as described above in a solution process; and heat-treating the coated coating composition.

The heat treatment temperature in the heat treatment step is preferably 150 ℃ to 230 ℃. In addition, the heat treatment time is 1 minute to 3 hours, more preferably 10 minutes to 1 hour. In addition, the heat treatment is preferably performed in an inert gas atmosphere such as argon or nitrogen.

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, and conductive polymers of polyaniline and polythiophene series, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light emitting layer. A material capable of transporting holes from the anode or hole injection layer to the light emitting layer as a hole transport material. 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 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, and the like, 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 according to the present invention is used as the host material.

Examples of the dopant material include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group, 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, but is not limited to, an iridium complex, a platinum complex, and the like. Preferably, an iridium-based metal complex is used as the dopant material.

The light emitting layer may be a red light emitting layer, and when the compound according to the present invention is used as a host material, stability for electrons and holes is increased, and energy transfer from the host to the red dopant is well achieved, the driving voltage of the organic light emitting device, It is possible to improve luminous efficiency and lifespan characteristics.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light emitting layer. 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.

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.

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.

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

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

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.

Synthesis Example A. Synthesis of intermediate compound a

1) Preparation of compound a-3

2-bromo-1-chlorodibenzo[b,d]furan 300 g (1.0 eq), bis(pinacolato)diboron 297.7 g (1.1 eq) in [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), [ Pd(dppf)Cl ₂ ] 15.6 g (0.02 eq) and 313.7 g (3.00 eq) of potassium acetate (KOAc) were added to 1,4-dioxnae 6000 mL, refluxed and stirred. When the reaction was completed after 3 hours, the solvent was removed under reduced pressure. The filtered solid _{was completely dissolved in CHCl 3} , washed with water, and the solution in which the product was dissolved was concentrated under reduced pressure to remove about 90% of the solvent. After adding ethanol under reflux, crystals were dropped, cooled, and filtered to obtain 273.1 g of compound a-3 (yield 78%). [M+H] ⁺ =330.

2) Preparation of compound a-2

Compound a-3 273.1 g (1.0 eq.) and 1,8-diiodonaphthalene 347.4 g (1.1 eq.) were added to 5462 mL of tetrahydrofuran (THF), followed by stirring and reflux. After that, 344.6 g (3.0 eq.) of potassium carbonate (K ₂ CO ₃ ) was dissolved in 1034 mL of water and thoroughly stirred, and then tetrakis(triphenylphosphine)palladium(0) [Pd(PPh ₃ ) ₄ ] 19.2 g (0.02 eq.) .) was added. After 5 hours, the reaction was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. After that, it was completely dissolved in ethyl acetate, washed with water, and again under reduced pressure to remove about 80% of the solvent. At reflux, hexane was added, crystals were dropped, cooled, and filtered. This was purified by silica gel column chromatography to obtain 238.1 g of compound a-2 (yield 63%). [M+H] ⁺ =456.

3) Preparation of compound a-1

Compound a-2 238.1 g (1.0 eq) bis(tri-tert-butylphosphine)palladium(0) [Pd(P-tBu ₃ ) ₂ ] 2.7 g (0.01 eq), potassium carbonate (K ₂ CO ₃ ) 144.7 g (2.00 eq) was added to 2.5 L of N,N-Dimethylacetamide (DMAC), refluxed and stirred. After 3 hours, the reaction product was poured into water to drop crystals and filtered. The filtered solid was completely dissolved in 1,2-dichlorobenzene, washed with water, and the solution in which the product was dissolved was concentrated under reduced pressure to drop crystals, cooled, and filtered. This was purified by silica gel column chromatography to obtain 78.7 g of compound a-1 (yield 46%). [M+H] ⁺ =328.

4) Preparation of compound a

Compound a-1 78.7 g (1.0 eq.) and bis(pinacolato)diboron 67.3 g (1.1 eq.) were refluxed in 1574 mL of 1,4-dioxane and stirred. After that, 70.9 g (3.0 eq.) of potassium acetate (KOAc) was added and sufficiently stirred, bis(dibenzylideneacetone)palladium (0) [Pd(dba) ₂ ] 4.2 g (0.03 eq.) and tricyclohexylphosphine ( PCy ₃ ) 4.1 g (0.06 eq.) was added. After reacting for 3 hours, the mixture was distilled under reduced pressure, dissolved again in chloroform, and washed twice with water. Thereafter, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 80.6 g of compound a (yield 80%). [M+H] ⁺ = 419.

Synthesis Example B. Synthesis of intermediate compound b

1) Preparation of compound b-5

Add 400.0 g (1.0 eq.) of 4-bromo-1-fluoro-2-iodobenzene, 229.1 g (1.0 eq.) of (2-chloro-6-hydroxyphenyl)boronic acid to 8000 mL of tetrahydrofuran (THF), stir and refluxed. After that, 551.2 g (3.0 eq.) of potassium carbonate (K ₂ CO ₃ ) was dissolved in 1654 mL of water and thoroughly stirred, and then tetrakis(triphenylphosphine)palladium(0) [Pd(PPh ₃ ) ₄ ] 30.7 g (0.02 eq.) .) was added. After 5 hours, the reaction was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. After that, it was completely dissolved in ethyl acetate, washed with water, and again under reduced pressure to remove about 80% of the solvent. At reflux, hexane was added, crystals were dropped, cooled, and filtered. This was purified by silica gel column chromatography to obtain 240.5 g of compound b-5 (yield: 60%). [M+H] ⁺ =303.

2) Preparation of compound b-4

Compound b-5 240.5 g (1.0 eq.) and potassium carbonate (K ₂ CO ₃ ) 330.7 g (3.0 eq.) were placed in 2405 mL of N,N-Dimethylacetamide (DMAC) and stirred under reflux. After 4 hours, the reaction product was poured into water to drop crystals and filtered. The filtered solid was completely dissolved in chloroform, washed with water, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 206.6 g of compound b-4 (yield 92%). [M+H] ⁺ = 283.

3) Preparation of compound b-3

Compound b-3 was synthesized in the same manner as in the preparation method of compound a-3, except that compound b-4 was used instead of 2-bromo-1-chlorodibenzo[b,d]furan.

4) Preparation of compound b-2

Compound b-2 was synthesized in the same manner as in the preparation method of compound a-2, except that compound b-3 was used instead of compound a-3.

5) Preparation of compound b-1

Except for using compound b-2 instead of compound a-2, compound b-1 was synthesized in the same manner as in the preparation method of compound a-1 described above.

6) Preparation of compound b

Compound b was synthesized in the same manner as in the above-described method for preparing compound a, except that compound b-1 was used instead of compound a-1.

Synthesis Example C. Synthesis of intermediate compound c

1) Preparation of compound c-1

Except for using 2-bromo-1-chlorodibenzo[b,d]thiophene instead of 2-bromo-1-chlorodibenzo[b,d]furan, the following compound c-1 was synthesized.

2) Preparation of compound c

Except for using the compound c-1 instead of the compound a-1, the following formula c was synthesized in the same manner as in the preparation method of the compound a described above.

Synthesis Example D. Synthesis of intermediate compound d

1) Preparation of compound d-6

(4-bromo-2-iodophenyl)(methyl)sulfane 300.0 g (1.0 eq.), (2-chlorophenyl)boronic acid 142.6 g (1.0 eq.) was added to 6000 mL of tetrahydrofuran (THF), stirred and refluxed. . After that, 378.1 g (3.0 eq.) of potassium carbonate (K ₂ CO ₃ ) was dissolved in 1134 mL of water and thoroughly stirred. Then, tetrakis(triphenylphosphine)palladium(0) [Pd(PPh ₃ ) ₄ ] 21.1 g (0.02 eq.) .) was added. After 2 hours, the reaction was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. After that, it was completely dissolved in ethyl acetate, washed with water, and again under reduced pressure to remove about 80% of the solvent. At reflux, hexane was added, crystals were dropped, cooled, and filtered. This was purified by silica gel column chromatography to obtain 214.5 g of compound d-6 (yield 75%). [M+H] ⁺ =315.

2) Preparation of compound d-5

Compound d-6 214.5 g (1.0 eq) of H ₂ O ₂ 46.5 g (2.00 eq) was added to 1 L of acetic acid (AcOH), and the mixture was refluxed and stirred. After 1 hour, the reaction product was poured into water to drop crystals and filtered. The filtered solid was completely dissolved in ethyl acetate, washed with water, and again under reduced pressure to remove about 80% of the solvent. At reflux, hexane was added, crystals were dropped, cooled, and filtered. This was purified by silica gel column chromatography to obtain 81.2 g of compound d-5 (yield 36%). [M+H] ⁺ =331.

3) Preparation of compound d-4

Compound d-5 81.2 g (1.0 eq), H ₂ SO ₄ 450 mL was put, and the mixture was refluxed and stirred while dissolving. When the reaction was completed after 2 hours, the reaction product was poured into water to drop crystals and filtered. The filtered solid _{was completely dissolved in CHCl 3} , washed with water, and the solution in which the product was dissolved was concentrated under reduced pressure to remove about 80% of the solvent. After adding hexane under reflux, the crystals were dropped, cooled, and filtered to obtain 27.9 g of compound d-4 (yield 38%). [M+H] ⁺ =299.

4) Preparation of compound d-3

Compound d-3 was synthesized in the same manner as in the preparation method of compound a-3, except that compound d-4 was used instead of 2-bromo-1-chlorodibenzo[b,d]furan.

5) Preparation of compound d-2

Except for using compound d-3 instead of compound a-3, compound d-2 was synthesized in the same manner as in the preparation method of compound a-2 described above.

6) Preparation of compound d-1

Except for using compound d-2 instead of compound a-2, compound d-1 was synthesized in the same manner as in the preparation method of compound a-1 described above.

7) Preparation of compound d

Except for using compound d-1 instead of compound a-1, compound d was synthesized in the same manner as in the preparation method of formula (a) described above.

Synthesis Example 1. Synthesis of compound 1

Compound sub 1 (15 g, 38.1 mmol) and compound a (17.5 g, 41.9 mmol) were added to 300 mL of THF, stirred and refluxed. After that, potassium carbonate (15.8 g, 114.3 mmol) was dissolved in 47 mL of water and stirred sufficiently, and then tetrakis(triphenylphosphine)palladium(0) (0.9 g, 0.8 mmol) was added. After the reaction for 11 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.3 g of Compound 1. (Yield 70%, MS: [M+H] ⁺ = 651).

Synthesis Example 2. Synthesis of compound 2

Compound sub 2 (15 g, 40.1 mmol) and compound a (18.5 g, 44.1 mmol) were added to 300 mL of THF, stirred and refluxed. After that, potassium carbonate (16.6 g, 120.4 mmol) was dissolved in 50 mL of water and stirred sufficiently, and then tetrakis(triphenylphosphine)palladium(0) (0.9 g, 0.8 mmol) was added. After the reaction for 12 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.2 g of Compound 2. (Yield 60%, MS: [M+H] ⁺ = 631).

Synthesis Example 3. Synthesis of compound 3

Compound sub 3 (15 g, 42 mmol) and compound a (19.3 g, 46.2 mmol) were added to 300 mL of THF, stirred and refluxed. After that, potassium carbonate (17.4 g, 126.1 mmol) was dissolved in 52 mL of water and stirred sufficiently, and then tetrakis(triphenylphosphine)palladium(0) (1 g, 0.8 mmol) was added. After the reaction for 11 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 20.6 g of compound 3. (yield 80%, MS: [M+H] ⁺ = 614).

Synthesis Example 4. Synthesis of compound 4

Compound sub 4 (15 g, 38.1 mmol) and compound a (17.5 g, 41.9 mmol) were added to 300 mL of THF, stirred and refluxed. After that, potassium carbonate (15.8 g, 114.3 mmol) was dissolved in 47 mL of water and stirred sufficiently, and then tetrakis(triphenylphosphine)palladium(0) (0.9 g, 0.8 mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.1 g of compound 4. (yield 69%, MS: [M+H] ⁺ = 651)

Synthesis Example 5. Synthesis of compound 5

Compound sub 5 (15 g, 40.8 mmol) and compound a (18.8 g, 44.9 mmol) were added to 300 mL of THF, stirred and refluxed. After that, potassium carbonate (16.9 g, 122.3 mmol) was dissolved in 51 mL of water, and after stirring sufficiently, tetrakis(triphenylphosphine)palladium(0) (0.9 g, 0.8 mmol) was added. After the reaction for 11 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 20.3 g of compound 5. (yield 80%, MS: [M+H] ⁺ = 625)

Synthesis Example 6. Synthesis of compound 6

Compound sub 6 (15 g, 30.9 mmol) and compound a-1 (10.1 g, 30.9 mmol) were added to 300 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (12.8 g, 92.7 mmol) was dissolved in 38 mL of water, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.9 g of compound 6. (yield 69%, MS: [M+H] ⁺ = 651).

Synthesis Example 7. Synthesis of compound 7

Compound sub 7 (15 g, 47.2 mmol) and compound b (21.7 g, 51.9 mmol) were added to 300 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (19.6 g, 141.6 mmol) was dissolved in 59 mL of water, and after sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (1.1 g, 0.9 mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 21.7 g of compound 7. (Yield 80%, MS: [M+H] ⁺ = 575).

Synthesis Example 8. Synthesis of compound 8

Compound sub 8 (15 g, 41.9 mmol) and compound b (19.3 g, 46.1 mmol) were added to 300 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (17.4 g, 125.8 mmol) was dissolved in 52 mL of water, and after sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (1 g, 0.8 mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.5 g of compound 8. (Yield 72%, MS: [M+H] ⁺ = 615).

Synthesis Example 9. Synthesis of compound 9

Compound sub 9 (15 g, 38.1 mmol) and compound b (17.5 g, 41.9 mmol) were added to 300 mL of THF, stirred and refluxed. After that, potassium carbonate (15.8 g, 114.3 mmol) was dissolved in 47 mL of water and stirred sufficiently, and then tetrakis(triphenylphosphine)palladium(0) (0.9 g, 0.8 mmol) was added. After the reaction for 12 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16.6 g of compound 9. (Yield 67%, MS: [M+H] ⁺ = 651).

Synthesis Example 10. Synthesis of compound 10

Compound sub 10 (15 g, 34.6 mmol) and compound b (15.9 g, 38.1 mmol) were added to 300 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (14.4 g, 103.9 mmol) was dissolved in 43 mL of water, and after stirring sufficiently, tetrakis(triphenylphosphine)palladium(0) (0.8 g, 0.7 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16 g of compound 10. (Yield 67%, MS: [M+H] ⁺ = 690).

Synthesis Example 11. Synthesis of compound 11

Compounds sub 11 (15 g, 26.1 mmol) and b-1 (8.5 g, 26.1 mmol) were added to 300 mL of THF, stirred and refluxed. After that, potassium carbonate (10.8 g, 78.2 mmol) was dissolved in 32 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.1 g of compound 11. (Yield 73%, MS: [M+H] ⁺ = 741).

Synthesis Example 12. Synthesis of compound 12

Compound sub 12 (15 g, 34.5 mmol) and compound b-1 (11.3 g, 34.5 mmol) were added to 300 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (14.3 g, 103.4 mmol) was dissolved in 43 mL of water, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After the reaction for 11 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.8 g of compound 12. (Yield 62%, MS: [M+H] ⁺ = 601).

Synthesis Example 13. Synthesis of compound 13

Compound sub 13 (15 g, 56 mmol) and compound c (26.8 g, 61.6 mmol) were added to 300 mL of THF, stirred and refluxed. After that, potassium carbonate (23.2 g, 168.1 mmol) was dissolved in 70 mL of water, and after sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.1 mmol) was added. After the reaction for 12 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 23 g of compound 13. (Yield 76%, MS: [M+H] ⁺ = 541).

Synthesis Example 14. Synthesis of compound 14

Compound sub 14 (15 g, 35.9 mmol) and compound c (17.1 g, 39.5 mmol) were added to 300 mL of THF, stirred and refluxed. After that, potassium carbonate (14.9 g, 107.7 mmol) was dissolved in 45 mL of water, and after sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.8 g, 0.7 mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.3 g of compound 14. (Yield 74%, MS: [M+H] ⁺ = 691).

Synthesis Example 15. Synthesis of compound 15

Compound sub 15 (15 g, 35.7 mmol) and compound c (17.1 g, 39.3 mmol) were added to 300 mL of THF, stirred and refluxed. After that, potassium carbonate (14.8 g, 107.2 mmol) was dissolved in 44 mL of water, and after stirring sufficiently, tetrakis(triphenylphosphine)palladium(0) (0.8 g, 0.7 mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.8 g of compound 15. (yield 76%, MS: [M+H] ⁺ = 693).

Synthesis Example 16. Synthesis of compound 16

Compound sub 16 (15 g, 40.1 mmol) and compound c (19.2 g, 44.1 mmol) were added to 300 mL of THF, stirred and refluxed. After that, potassium carbonate (16.6 g, 120.4 mmol) was dissolved in 50 mL of water and stirred sufficiently, and then tetrakis(triphenylphosphine)palladium(0) (0.9 g, 0.8 mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16.3 g of compound 16. (Yield 63%, MS: [M+H] ⁺ = 647).

Synthesis Example 17. Synthesis of compound 17

Compound sub 17 (15 g, 30.9 mmol) and compound c-1 (10.6 g, 30.9 mmol) were added to 300 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (12.8 g, 92.7 mmol) was dissolved in 38 mL of water, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After the reaction for 12 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.3 g of compound 17. (Yield 60%, MS: [M+H] ⁺ = 667).

Synthesis Example 18. Synthesis of compound 18

Compound sub 18 (15 g, 43.6 mmol) and compound d (20.8 g, 48 mmol) were added to 300 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (18.1 g, 130.9 mmol) was dissolved in 54 mL of water, and after sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (1 g, 0.9 mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.3 g of compound 18. (Yield 68%, MS: [M+H] ⁺ = 617).

Synthesis Example 19. Synthesis of compound 19

Compound sub 19 (15 g, 41.9 mmol) and compound d (20 g, 46.1 mmol) were added to 300 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (17.4 g, 125.8 mmol) was dissolved in 52 mL of water, and after sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (1 g, 0.8 mmol) was added. After the reaction for 11 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16.9 g of compound 19. (Yield 64%, MS: [M+H] ⁺ = 631).

Synthesis Example 20. Synthesis of compound 20

Compound sub 20 (15 g, 35.7 mmol) and compound d (17.1 g, 39.3 mmol) were added to 300 mL of THF, stirred and refluxed. After that, potassium carbonate (14.8 g, 107.2 mmol) was dissolved in 44 mL of water, and after stirring sufficiently, tetrakis(triphenylphosphine)palladium(0) (0.8 g, 0.7 mmol) was added. After the reaction for 11 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.8 g of compound 20. (yield 76%, MS: [M+H] ⁺ = 693).

Synthesis Example 21. Synthesis of compound 21

Compound sub 21 (15 g, 28 mmol) and compound d-1 (9.6 g, 28 mmol) were added to 300 mL of THF, stirred and refluxed. After that, potassium carbonate (11.6 g, 84 mmol) was dissolved in 35 mL of water, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After the reaction for 11 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.6 g of compound 21. (Yield 78%, MS: [M+H] ⁺ = 717).

Synthesis Example 22. Synthesis of compound 22

Compound sub 22 (15 g, 34.6 mmol) and compound d (16.6 g, 38.1 mmol) were added to 300 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (14.4 g, 103.9 mmol) was dissolved in 43 mL of water, and after stirring sufficiently, tetrakis(triphenylphosphine)palladium(0) (0.8 g, 0.7 mmol) was added. After the reaction for 11 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.9 g of compound 22. (Yield 61%, MS: [M+H] ⁺ = 706).

Example 1

A glass substrate coated with a thin film of indium tin oxide (ITO) to a thickness of 1,000 angstrom (Å, angstrom) 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 transferred to a vacuum evaporator.

As a hole injection layer on the prepared ITO transparent electrode, the following compound HI-1 was thermally vacuum deposited to a thickness of 1150 Å to form a hole injection layer, but the following compound A-1 was p-doped at a concentration of 1.5%. 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 an electron blocking layer. Then, the following compound 1 and the following compound Dp-7 were vacuum-deposited in a weight ratio of 98:2 on the EB-1 deposited layer to form a red light emitting layer having a thickness of 400 Å. A hole blocking layer was formed by vacuum-depositing the following compound HB-1 to a thickness of 30 Å on the light emitting layer. Then, on the hole blocking 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 1,000 Å on the electron injection and transport layer.

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.

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 By maintaining 2x10 ^-7 to 5x10 ^-6 torr, an organic light emitting diode was manufactured.

Examples 2 to 22

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compounds 2 to 22 described in Table 1 were used instead of Compound 1 in the organic light emitting device of Example 1, respectively.

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.

Comparative Examples 1 to 8

An organic light emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of Compound 1 in the organic light emitting device of Example 1. The compounds of C-1, C-2, C-3, C-4, C-5, C-6, C-7, and C-8 used in Table 1 are as follows.

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.

When a current was applied to the organic light emitting diodes prepared in Examples and Comparative Examples, voltage and efficiency were measured (15 mA/cm ² ), and the results are shown in Table 1 below. The lifetime T95 means the time it takes for the luminance to decrease from the initial luminance (6000 nit) to 95%.

division matter Driving voltage (V) Efficiency (cd/A) Life T95 (hr) luminous color Example 1 compound 1 3.71 18.8 135 Red Example 2 compound 2 3.79 17.3 107 Red Example 3 compound 3 3.78 17.0 114 Red Example 4 compound 4 3.73 18.2 122 Red Example 5 compound 5 3.68 18.7 105 Red Example 6 compound 6 3.74 18.3 121 Red Example 7 compound 7 3.68 19.0 134 Red Example 8 compound 8 3.63 19.6 156 Red Example 9 compound 9 3.65 19.3 123 Red Example 10 compound 10 3.72 18.5 118 Red Example 11 compound 11 3.70 18.2 106 Red Example 12 compound 12 3.61 19.9 142 Red Example 13 compound 13 3.82 17.3 125 Red Example 14 compound 14 3.78 17.8 131 Red Example 15 compound 15 3.76 18.0 117 Red Example 16 compound 16 3.85 17.3 105 Red Example 17 compound 17 3.89 17.0 103 Red Example 18 compound 18 3.72 18.7 126 Red Example 19 compound 19 3.80 17.8 101 Red Example 20 compound 20 3.68 18.5 109 Red Example 21 compound 21 4.76 17.7 106 Red Example 22 compound 22 3.71 18.3 122 Red Comparative Example 1 C-1 4.20 14.9 84 Red Comparative Example 2 C-2 4.25 13.6 72 Red Comparative Example 3 C-3 4.01 15.3 79 Red Comparative Example 4 C-4 4.51 8.9 13 Red Comparative Example 5 C-5 4.59 7.8 10 Red Comparative Example 6 C-6 4.06 15.1 62 Red Comparative Example 7 C-7 3.97 16.4 93 Red Comparative Example 8 C-8 4.05 15.3 81 Red

When a current was applied to the organic light emitting devices manufactured in Examples 1 to 22 and Comparative Examples 1 to 8, the results shown in Table 1 were obtained. As described above, the red organic light emitting device of Example 1 used a conventionally widely used material, and had a structure using Compound EB-1 as an electron suppression layer and Compound 1 and Compound Dp-7 as a red light emitting layer. In Comparative Examples 1 to 8, organic light emitting devices were prepared by using Compounds C-1 to C-8 instead of Compound 1.

As shown in Table 1 above, according to the present invention, the compound represented by Formula 1, that is, N at a specific position in the parent nucleus structure in which a fluoranthene ring and a bicyclic heterocyclic ring containing O or S are condensed is 2 The organic light emitting devices of Examples 1 to 22 in which a compound having a specific polycyclic structure including at least two heteroaryl substituents is used in the light emitting layer is C-1, C-2, C-3, C-4, C-5 , C-6, C-7, and C-8, compared to the organic light emitting devices of Comparative Examples 1 to 8 prepared using the compound, the driving voltage was significantly lowered, and it was found that the red plate in the host was significantly increased in terms of efficiency. It could be seen that the energy transfer to Tro was well done. In addition, it was found that the organic light emitting devices of Examples 1 to 22 can significantly improve lifespan characteristics while maintaining high efficiency. It can be determined that this is because the compound of the example according to the present invention has higher stability to electrons and holes than the compound of the comparative example. In conclusion, it can be confirmed that when the compound of the present invention is used as a host for the red light emitting layer, the driving voltage, luminous efficiency and lifespan characteristics of the organic light emitting device can be improved.

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

Claims (11)

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

In Formula 1,
Y is O or S;
R ₁ is each independently hydrogen; heavy hydrogen; halogen; cyano; substituted or unsubstituted C _1-60 alkyl; substituted or unsubstituted C _1-60 alkoxy; substituted or unsubstituted C _2-60 alkenyl; substituted or unsubstituted C _2-60 alkynyl; substituted or unsubstituted C _3-60 cycloalkyl; substituted or unsubstituted C _6-60 aryl; _{Or a substituted or unsubstituted C 2-60} heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S;
n1 is an integer from 0 to 6,
n2 is an integer from 0 to 3,
One of R ₂ is represented by the following formula (2), the rest is hydrogen or deuterium,
[Formula 2]

In Formula 2,
L is a single bond; Or a substituted or unsubstituted C _6-60 arylene,
X is N, or CH, provided that at least two or more of X are N;
Ar ₁ and Ar ₂ are each independently substituted or unsubstituted C _6-60 aryl; _{or a substituted or unsubstituted C 2-60} heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S.
According to claim 1,
The compound represented by Formula 1 is that represented by the following Formula 1-1 or 1-2,
[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,
Y, R ₁ , n1, n2, L, X, Ar ₁ and Ar ₂ are as defined in claim 1.
According to claim 1,
R ₁ is each hydrogen or deuterium;
compound.
According to claim 1,
L is a single bond; or phenylene, biphenylrylene, terphenylrylene, quaterphenyllylene, or naphthylene;
compound.
According to claim 1,
L is a single bond; Or which is represented by any one selected from the group consisting of:
compound:

.
According to claim 1,
X is all N,
compound.
According to claim 1,
Ar ₁ and Ar ₂ are each substituted or unsubstituted C _6-30 aryl; _{Or a substituted or unsubstituted C 5-30} heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S;
compound.
According to claim 1,
Ar ₁ and Ar ₂ are each phenyl, naphthyl substituted phenyl, dibenzofuranyl substituted phenyl, dibenzothiophenyl substituted phenyl, carbazolyl substituted phenyl, biphenyl, terphenyl, naphthyl, phenyl substituted naph which is tyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, or phenyl substituted carbazolyl;
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 which is an organic light emitting device.
11. The method of claim 10,
The organic material layer containing the compound is a light emitting layer,
organic light emitting device.

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