KR20210006867A - 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 compound is represented by chemical formula 1 and can improve the efficiency of the organic light emitting device.

Description

Novel compound and organic light emitting device comprising the same

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

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

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

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,

Ar ₁ and Ar ₂ are each independently substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S,

R ₁ to R ₆ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl including any one or more selected from the group consisting of N, O and S, or two adjacent to each other among R ₁ to R ₄ are substituted or unsubstituted A C _6-60 aromatic ring or a substituted or unsubstituted C _2-60 heteroaromatic ring including any one or more heteroatoms selected from the group consisting of N, O and S,

a is an integer from 0 to 3,

b is an integer from 0 to 6,

A is a substituent represented by the following formula (2),

[Formula 2]

In Chemical Formula 2,

X is O or S,

R ₇ and R ₈ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl including any one or more selected from the group consisting of N, O and S, or substituted or unsubstituted C _6-60 aromatic by bonding with adjacent substituents A ring or a substituted or unsubstituted C _2-60 heteroaromatic ring including any one or more heteroatoms selected from the group consisting of N, O and S,

c is an integer from 0 to 3,

d is an integer from 0 to 4,

When a, b, c and d are each 2 or more, the substituents in parentheses are the same or different from each other.

In addition, the present invention is a first electrode; A second electrode provided to face the first electrode; And an emission layer provided between the first electrode and the second electrode, wherein the emission layer includes a compound represented by Formula 1 above.

The compound represented by Formula 1 described above is used as a material of the organic material layer of the organic light emitting device, thereby improving the efficiency, low driving voltage, and/or lifetime characteristics of the organic light emitting device.

1 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
2 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron suppressing layer 7, a hole blocking layer 8, an electron injection and transport layer ( 8) and the cathode 4 shows an example of an organic light emitting device.

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

(Definition of Terms)

및

는 다른 치환기에 연결되는 결합을 의미한다.In this specification,

And

Means a bond connected to another substituent.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Cyano group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Arylsulfoxy group; Silyl group; Boron group; Alkyl group; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or it means substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl containing one or more of N, O and S atoms, or substituted or unsubstituted with two or more substituents connected among the above-exemplified substituents. . For example, "a substituent to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent to which two phenyl groups are connected.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the ester group may be substituted with an oxygen of the ester group with a straight chain, 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 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 is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.

In the present specification, the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, and the like, but is not limited thereto.

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

In the present specification, the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. 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 a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. 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 is preferably 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 cycloalkyl group has 3 to 20 carbon atoms. 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 are not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, 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. However, it is not limited thereto.

In the present specification, heteroaryl is a heteroaryl containing at least one of O, N, Si, and S as a heterogeneous element, and the number of carbons is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of heteroaryl include xanthene, thioxanthen, thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, Pyrimidyl group, triazine group, 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 ( phenanthroline), isoxazolyl group, thiadiazolyl group, phenothiazinyl group, and dibenzofuranyl group, but are not limited thereto.

The term "aromatic ring" as used herein refers to condensation having a plurality of aromatics such as a fluorene ring as well as a condensed monocyclic or condensed polycyclic ring having only carbon as a ring-forming atom and having aromaticity in the entire molecule. It is understood that the monocyclic ring also includes a condensed polycyclic ring formed by linking adjacent substituents. At this time, the number of carbon atoms of the aromatic ring is 6 to 60, or 6 to 30, or 6 to 20, but is not limited thereto. Further, the aromatic ring may be a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyrene ring, a fluorene ring, and the like, but is not limited thereto.

The term "heterocyclic ring" as used herein refers to a hetero-condensed monocyclic or hetero-condensed ring containing at least one heteroatom among O, N, and S other than carbon as a ring-forming atom and having aromaticity in the entire molecule. It means a polycyclic ring. The number of carbon atoms of the hetero ring is 2 to 60, or 2 to 30, or 2 to 20, but is not limited thereto. In addition, the hetero ring may be a benzofuran ring, a benzothiophene ring, a dibenzofuran ring, a dibenzothiophene ring, and the like, but is not limited thereto.

In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, arylamine group, and arylsilyl 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 aforementioned alkyl group. In the present specification, for heteroaryl among heteroarylamines, the above-described description of heteroaryl may be applied. In the present specification, the alkenyl group of the aralkenyl group is the same as the example of the alkenyl group described above. In the present specification, the description of the aryl group described above may be applied except that the arylene is a divalent group. In the present specification, the description of the above-described heteroaryl may be applied except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the aryl group or the cycloalkyl group described above may be applied except that the hydrocarbon ring is formed by bonding of two substituents. In the present specification, the heteroaryl is not a monovalent group, and the description of the above-described heteroaryl may be applied except that two substituents are bonded to each other.

(compound)

The present invention provides a compound represented by Chemical Formula 1.

The compound represented by Formula 1 has a structure in which a triazinyl substituent and a benzocarbazolyl-based substituent are connected by dibenzofuranylphenylene or dibenzothiophenylphenylene. In particular, the compound is characterized in that the benzocarbazolyl-based substituent and the dibenzofuranyl/dibenzothiophenyl substituent are bonded to the ortho position in the benzene ring. When such a compound is used as a host material of the light emitting layer, energy transfer to the dopant is compared to the compound in which the benzocarbazolyl substituent and the dibenzofuranyl/dibenzothiophenyl substituent are bonded to the meta or para position. This is done well, while lowering the driving voltage of the organic light-emitting device, it is possible to significantly improve the efficiency and life characteristics.

Preferably, R ₁ to R ₆ are each independently hydrogen, deuterium, or C _6-20 aryl; or

R ₅ and R ₆ are each independently hydrogen, deuterium, or C _6-20 aryl, and two adjacent ones of R ₁ to R ₄ are bonded to each other and unsubstituted, or benzene substituted with deuterium or C _6-20 aryl To form a ring, and the remainder may each independently be hydrogen, deuterium, or C _6-20 aryl.

In this case, a and b mean the number of R ₅ and R ₆ , respectively, a is 0, 1, 2, or 3, and b is 0, 1, 2, 3, or 4.

Specifically, when two adjacent ones of R ₁ to R ₄ are bonded to each other to form a benzene ring, the compound may be represented by the following Formula 1A:

[Formula 1A]

In Formula 1A,

R ₁ to R ₆ are each independently hydrogen, deuterium, or C _6-20 aryl,

Ar ₁ , Ar ₂ , R ₅ , R ₆ , a, b and A are as defined in Chemical Formula 1.

Alternatively, when two adjacent ones of R ₁ to R ₄ are bonded to each other to form a benzene ring, the compound may be represented by the following Formula 1B:

[Formula 1B]

In Formula 1B,

R, R ₅ , R ₆ and R ₁₁ to R ₁₄ are each independently hydrogen, deuterium, or C _6-20 aryl,

Ar ₁ , Ar ₂ , a, b and A are as defined in Chemical Formula 1.

Preferably, the compound is represented by any one of the following formulas 1-1 to 1-4:

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4,

R ₁ to R ₆ and R ₁₁ to R ₁₄ are each independently hydrogen, deuterium, or C _6-20 aryl,

Ar ₁ , Ar ₂ , a, b and A are as defined in Chemical Formula 1.

In Formulas 1-1 to 1-4,

R ₅ and R ₆ are each independently hydrogen or deuterium,

R ₁ to R ₄ and R ₁₁ to R ₁₄ may each independently be hydrogen, deuterium, or phenyl.

In addition, in Formula 1-1,

R ₁ to R ₄ are each independently hydrogen or deuterium; or

One of R ₁ to R ₄ may be phenyl, and the others may each independently be hydrogen or deuterium.

More specifically, in Chemical Formula 1-1,

All of R ₁ to R ₄ are hydrogen; Or R ₄ may be phenyl, and R ₁ to R ₃ may be hydrogen.

In addition, in Formula 1-2,

R _1, R ₂ and R ₁₁ to R ₁₄ are each independently hydrogen or deuterium; or

One of R _1, R ₂ and R ₁₁ to R ₁₄ may be phenyl, and the others may each independently be hydrogen or deuterium.

In addition, in Chemical Formula 1-3,

R _1, R ₄ and R ₁₁ to R ₁₄ are each independently hydrogen or deuterium; or

One of R _1, R ₄ and R ₁₁ to R ₁₄ may be phenyl, and the others may each independently be hydrogen or deuterium.

In addition, in Formula 1-4,

R _3, R ₄ and R ₁₁ to R ₁₄ are each independently hydrogen or deuterium; or

One of R _3, R ₄ and R ₁₁ to R ₁₄ may be phenyl, and the others may each independently be hydrogen or deuterium.

Preferably, Ar ₁ and Ar ₂ are each independently C _6-20 aryl unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and phenyl; Or it may be a C _2-20 heteroaryl containing one heteroatom from the group consisting of N, O and S unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and phenyl.

More preferably, Ar ₁ and Ar ₂ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, anthryl, phenanthryl, triphenylenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl ego,

The Ar ₁ and Ar ₂ may be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and phenyl.

For example, Ar ₁ and Ar ₂ may each independently be any one selected from the group consisting of:

.

.

In addition, one of Ar ₁ and Ar ₂ is phenyl, and the rest are biphenylyl, terphenylyl, naphthyl, anthryl, phenanthryl, triphenylenyl, dibenzofuranyl, dibenzothiophenyl, or 9-phenyl Is carbazolyl;

Ar ₁ and Ar ₂ are both phenyl;

Ar ₁ and Ar ₂ are both biphenylyl;

Ar ₁ and Ar ₂ are both terphenylyl;

Ar ₁ and Ar ₂ are both naphthyl;

Ar ₁ and Ar ₂ are both anthryl;

Ar ₁ and Ar ₂ are both phenanthryl;

Ar ₁ and Ar ₂ are both triphenylenyl;

Ar ₁ and Ar ₂ are both dibenzofuranyl;

Ar ₁ and Ar ₂ are both dibenzothiophenyl; or

Both Ar ₁ and Ar ₂ may be 9-phenylcarbazole.

At this time, Ar ₁ and Ar ₂ may be the same as or different from each other.

Further, R ₇ and R ₈ are each independently hydrogen or deuterium;

R ₇ and R ₈ are each independently hydrogen or deuterium;

Two adjacent two of R ₇ are bonded to each other to form a benzene ring, and the remaining R ₇ and R ₈ are each independently hydrogen or deuterium;

Two adjacent two of R ₈ are bonded to each other to form a benzene ring, and the remaining R ₈ and R ₇ are each independently hydrogen or deuterium; or

Two adjacent two out of R ₇ and two adjacent two out of R ₈ are each bonded to each other to form a benzene ring, and the remaining R ₇ and R ₈ may each independently be hydrogen or deuterium.

At this time, c and d mean the number of R ₇ and R ₈ , respectively, c is 0, 1, 2, or 3, and d is 0, 1, 2, 3, or 4.

More preferably, A is dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, or benzonaphthothiophenyl, wherein A may be unsubstituted or substituted with one or more deuterium.

Most preferably, A is any one selected from the group consisting of:

.

.

In addition, the compound may be represented by any one of the following Formulas 1-1-1, 1-1-2, 1-2-1, 1-3-1, and 1-4-1:

In Formulas 1-1-1, 1-1-2, 1-2-1, 1-3-1, and 1-4-1,

Ar ₁ , Ar ₂ and A are as defined in Chemical Formula 1.

For example, the compound is any one selected from the group consisting of the following compounds:

.

On the other hand, the compound represented by Formula 1 may be prepared by a manufacturing method such as the following Scheme 1 as an example.

[Scheme 1]

In Reaction Scheme 1, each of X is independently halogen, preferably bromo or chloro, and definitions for other substituents are as described above.

Specifically, the compound represented by Formula 1 is prepared by combining starting materials SM1 and SM2 through an amine substitution reaction. This amine substitution reaction is preferably carried out in the presence of a palladium catalyst and a base. In addition, the reactor for the amine substitution reaction may be appropriately changed, and the method for preparing the compound represented by Formula 1 may be more specific in Preparation Examples to be described later.

(Organic light emitting device)

In addition, the present invention provides an organic light-emitting device including the compound represented by Chemical Formula 1. For example, the present invention provides a first electrode; A second electrode provided to face the first electrode; And an emission layer provided between the first electrode and the second electrode, wherein the emission layer includes the compound represented by Formula 1 above.

In addition, the organic light-emitting device according to the present invention is 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 in which a first electrode is an anode and a second electrode is a cathode. Can be In addition, the organic light-emitting device according to the present invention has 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 in which the first electrode is the cathode and the second electrode is the anode. Can be For example, the structure of an 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 comprising a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. In such a structure, the compound represented by Formula 1 may be included in the emission layer.

2 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron suppressing layer 7, a hole blocking layer 8, an electron injection and transport layer ( 8) and the cathode 4 shows an example of an organic light emitting device. In such a structure, the compound represented by Formula 1 may be included in the emission layer.

The organic light-emitting device according to the present invention can be manufactured by materials and methods known in the art, except that the emission layer includes the compound according to the present invention and is manufactured as described above.

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

In addition to such a method, an organic light-emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.

For 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 preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the cathode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; Conductive compounds such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.

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

The hole injection layer is a layer that injects holes from an electrode, and has the ability to transport holes as a hole injection material, so that it has a hole injection effect at the anode, an excellent hole injection effect for a light emitting layer or a light emitting material. A compound that prevents the movement of excitons to the electron injection layer or the electron injection material and has excellent ability to form a thin film is preferable. It is preferable that the HOMO (highest occupied molecular orbital) 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 hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive compounds, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer, and the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the emission layer, and has high mobility for holes. The material is suitable. Specific examples include an arylamine-based organic material, a conductive compound, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The organic light-emitting device according to an embodiment may further include an electron suppression layer on the hole transport layer. The electron suppression layer is formed on the hole transport layer and is preferably provided in contact with the light emitting layer to control hole mobility and prevent excessive movement of electrons, thereby increasing the probability of hole-electron coupling, thereby increasing the efficiency of the organic light-emitting device. It refers to the layer that plays a role in improving the value. The electron-suppressing layer includes an electron-blocking material, and examples of such an electron-blocking material include a compound represented by Formula 1 or an arylamine-based organic material, but are not limited thereto.

The emission layer may include a host material and a dopant material. As the host material, the compound represented by Formula 1 may be used. In addition, as the host material, a condensed aromatic ring derivative or a heterocyclic-containing compound may be additionally used in addition to the compound represented by Formula 1 above. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Further, the dopant material includes 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 substituted or unsubstituted As a compound in which at least one arylvinyl group is substituted on the arylamine, one or two or more substituents selected from the group consisting of an aryl group, silyl group, alkyl group, cycloalkyl group, and arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.

More specifically, the following compound may be used as the dopant material, but is not limited thereto:

.

.

In addition, the organic light-emitting device according to an embodiment may further include a hole blocking layer on the emission layer. The hole blocking layer is formed on the light emitting layer, preferably provided in contact with the light emitting layer, to improve the efficiency of the organic light emitting device by increasing the probability of hole-electron coupling by controlling electron mobility and preventing excessive movement of holes. It means the layer that plays a role. The hole-blocking layer includes a hole-blocking material, and examples of the hole-blocking material include azine derivatives including triazine; Triazole derivatives; Oxadiazole derivatives; Phenanthroline derivatives; A compound into which an electron withdrawing group such as a phosphine oxide derivative has been introduced may be used, but is not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer. As an electron transport material, a material capable of receiving electrons from the cathode and transferring them to the emission layer is a material having high mobility for electrons. Suitable. 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 can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium and samarium, and in each case an aluminum layer or a silver layer follows.

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 that prevents migration to the layer and has excellent thin film formation ability is preferable. Specifically, LiF, NaF, NaCl, CsF, Li ₂ O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid , Fluorenylidene methane, anthrone, and the like, derivatives thereof, metal complex compounds, and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include lithium 8-hydroxyquinolinato, 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-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited thereto.

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

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

Preparation of the compound represented by Formula 1 and an organic light emitting device including the same will be described in detail in the following examples. However, the following examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

Synthesis Example A: Preparation of Compound a

1) Preparation of compound a-1

Naphthalen-2-amine 300.0 g (1.0 eq), 1-bromo-2-iodobenzene 592.7 g (1.0 eq), NaOtBu 302.0 g (1.5 eq), Pd(OAc) ₂ 4.70 g (0.01 eq), Xantphos It dissolved in 12.12 g (0.01 eq) and 5 L of 1,4-dioxane, and the mixture was refluxed and stirred. When the reaction was completed after 3 hours, the pressure was reduced to remove the solvent. After that, it was completely dissolved in ethyl acetate, washed with water, and reduced pressure to remove about 70% of the solvent. Hexane was added under reflux again, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain 443.5 g (yield 71%) of compound a-1. [M+H]=299

2) Preparation of compound a(5H-benzo[b]carbazole)

To 443.5 g (1.0 eq) of compound a-1, Pd(t-Bu ₃ P) ₂ 8.56 g (0.01 eq) and 463.2 g (2.00 eq) of K ₂ CO ₃ were added to 4 L of dimethylacetamide and refluxed. And stirred. After 3 hours, the reaction 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 containing the product was concentrated under reduced pressure to drop crystals, cool, and then filtered. This was purified by column chromatography to obtain 174.8 g (yield 48%) of a compound a(5H-benzo[b]carbazole).

[M+H] ⁺ =218

Synthesis Example B: Preparation of Compound b

Compound b(7H-dibenzo[b,g]carbazol using the same method as in Synthesis Example a above, except that 1-bromo-2-iodonaphthalene was used instead of 1-bromo-2-iodobenzene. ).

[M+H] ⁺ =268

Synthesis Example C: Preparation of Compound c

Compound c(6H-dibenzo[b,h]carbazole) was prepared in the same manner as in Synthesis Example a, except that 2,3-dibromonaphthalene was used instead of 1-bromo-2-iodobenzene. Got it.

[M+H] ⁺ =268

Synthesis Example D: Preparation of Compound d

Compound d(13H-dibenzo[a,h]carbazole) using the same method as in Synthesis Example a, except that 2-bromo-1-iodonaphthalene was used instead of 1-bromo-2-iodobenzene. ).

[M+H] ⁺ =268

Synthesis Example 1: Preparation of Compound 1

In a nitrogen atmosphere, compound 1-1 (20 g, 35.7 mmol), compound a (7.8 g, 35.7 mmol), and sodium tert-butoxide (6.9 g, 71.4 mmol) were added to 400 ml of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.7 mmol) was added. When the reaction was terminated after 3 hours, it was cooled to room temperature and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated 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 16.1 g of compound 1.

(Yield 61%, MS: [M+H]+= 742)

Synthesis Example 2: Preparation of Compound 2

In a nitrogen atmosphere, compound 2-1 (20 g, 33.3 mmol), compound a (7.2 g, 33.3 mmol), and sodium tert-butoxide (6.4 g, 66.7 mmol) were added to 400 ml of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.7 mmol) was added. When the reaction was terminated after 3 hours, it was cooled to room temperature and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated 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 14.1 g of compound 2.

(Yield 54%, MS: [M+H]+= 782).

Synthesis Example 3: Preparation of Compound 3

In a nitrogen atmosphere, compound 3-1 (20 g, 28.9 mmol), compound a (6.3 g, 28.9 mmol), and sodium tert-butoxide (5.6 g, 57.9 mmol) were added to 400 ml of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. When the reaction was terminated after 3 hours, it was cooled to room temperature and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated 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 16.4 g of compound 3.

(Yield 65%, MS: [M+H]+= 873)

Synthesis Example 4: Preparation of Compound 4

In a nitrogen atmosphere, compound 4-1 (20 g, 30.8 mmol), compound a (6.7 g, 30.8 mmol), and sodium tert-butoxide (5.9 g, 61.5 mmol) were added to 400 ml of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. When the reaction was terminated after 3 hours, it was cooled to room temperature and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated 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 15.1 g of compound 4.

(Yield 59%, MS: [M+H]+= 832)

Synthesis Example 5: Preparation of compound 5

In a nitrogen atmosphere, compound 5-1 (20 g, 27.5 mmol), compound a (6 g, 27.5 mmol), and sodium tert-butoxide (5.3 g, 54.9 mmol) were added to 400 ml of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. When the reaction was terminated after 3 hours, it was cooled to room temperature and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated 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 16.2 g of compound 5.

(Yield 65%, MS: [M+H]+= 910)

Synthesis example 6: Preparation of compound 6

In a nitrogen atmosphere, compound 6-1 (20 g, 30 mmol), compound a (6.5 g, 30 mmol), and sodium tert-butoxide (5.8 g, 60 mmol) were added to 400 ml of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. When the reaction was terminated after 3 hours, it was cooled to room temperature and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated 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 17.3 g of compound 6.

(Yield 68%, MS: [M+H]+= 848)

Synthesis Example 7: Preparation of compound 7

In a nitrogen atmosphere, compound 7-1 (20 g, 30.7 mmol), compound a (6.7 g, 30.7 mmol), and sodium tert-butoxide (5.9 g, 61.3 mmol) were added to 400 ml of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. When the reaction was terminated after 3 hours, it was cooled to room temperature and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated 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 12.3 g of compound 7.

(Yield 48%, MS: [M+H]+= 834)

Synthesis Example 8: Preparation of compound 8

In a nitrogen atmosphere, compound 8-1 (20 g, 30.8 mmol), compound a (6.7 g, 30.8 mmol), and sodium tert-butoxide (5.9 g, 61.5 mmol) were added to 400 ml of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. When the reaction was terminated after 3 hours, it was cooled to room temperature and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated 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 12.3 g of compound 8.

(Yield 48%, MS: [M+H]+= 832)

Synthesis example 9: Preparation of compound 9

In a nitrogen atmosphere, compound 9-1 (20 g, 32.8 mmol), compound a (7.1 g, 32.8 mmol), and sodium tert-butoxide (6.3 g, 65.6 mmol) were added to 400 ml of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.7 mmol) was added. When the reaction was terminated after 3 hours, it was cooled to room temperature and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated 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 15.6 g of compound 9.

(Yield 60%, MS: [M+H]+= 792)

Synthesis Example 10: Preparation of Compound 10

In a nitrogen atmosphere, compound 10-1 (20 g, 29.3 mmol), compound a (6.4 g, 29.3 mmol), and sodium tert-butoxide (5.6 g, 58.6 mmol) were added to 400 ml of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. When the reaction was terminated after 3 hours, it was cooled to room temperature and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated 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 16.2 g of compound 10.

(Yield 64%, MS: [M+H]+= 864)

Synthesis Example 11: Preparation of compound 11

In a nitrogen atmosphere, compound 11-1 (20 g, 27.1 mmol), compound a (5.9 g, 27.1 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 400 ml of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. When the reaction was terminated after 3 hours, it was cooled to room temperature and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated 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 10 g of compound 11.

(Yield 40%, MS: [M+H]+= 920)

Synthesis Example 12: Preparation of Compound 12

In a nitrogen atmosphere, compound 12-1 (20 g, 27.5 mmol), compound a (6 g, 27.5 mmol), and sodium tert-butoxide (5.3 g, 55.1 mmol) were added to 400 ml of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. When the reaction was terminated after 3 hours, it was cooled to room temperature and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated 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 17.5 g of compound 12.

(Yield 70%, MS: [M+H]+= 908)

Synthesis example 13: Preparation of compound 13

In a nitrogen atmosphere, compound 13-1 (20 g, 29 mmol), compound a (6.3 g, 29 mmol), and sodium tert-butoxide (5.6 g, 58 mmol) were added to 400 ml of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. When the reaction was terminated after 3 hours, it was cooled to room temperature and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated 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 15.4 g of compound 13.

(Yield 61%, MS: [M+H]+= 872)

Synthesis example 14: Preparation of compound 14

In a nitrogen atmosphere, compound 14-1 (20 g, 28.3 mmol), compound c (7.6 g, 28.3 mmol), and sodium tert-butoxide (5.4 g, 56.6 mmol) were added to 400 ml of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. When the reaction was terminated after 3 hours, it was cooled to room temperature and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated 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 11.7 g of compound 14.

(Yield 44%, MS: [M+H]+= 938)

Synthesis Example 15: Preparation of compound 15

In a nitrogen atmosphere, compound 15-1 (20 g, 38 mmol), compound c (10.2 g, 38 mmol), and sodium tert-butoxide (7.3 g, 76 mmol) were added to 400 ml of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. When the reaction was terminated after 3 hours, it was cooled to room temperature and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated 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 15 g of compound 15.

(Yield 52%, MS: [M+H]+= 758)

Synthesis Example 16: Preparation of Compound 16

Compound 16-1 (20 g, 29 mmol), 1-phenyl-5H-benzo[b]carbazole (8.5 g, 29 mmol), sodium tert-butoxide (5.6 g, 58 mmol) was added to xylene 400 in a nitrogen atmosphere. ml and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. When the reaction was terminated after 3 hours, it was cooled to room temperature and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated 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 14.5 g of compound 16.

(Yield 53%, MS: [M+H]+= 948)

Synthesis Example 17: Preparation of compound 17

Compound 17-1 (20 g, 31.9 mmol), 1-phenyl-5H-benzo[b]carbazole (9.4 g, 31.9 mmol), sodium tert-butoxide (6.1 g, 63.9 mmol) was added to xylene 400 in a nitrogen atmosphere. ml and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. When the reaction was terminated after 3 hours, it was cooled to room temperature and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated 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 17.5 g of compound 17.

(Yield 62%, MS: [M+H]+= 884)

Synthesis Example 18: Preparation of Compound 18

In a nitrogen atmosphere, compound 18-1 (20 g, 30.2 mmol), compound d (8.1 g, 30.2 mmol), and sodium tert-butoxide (5.8 g, 60.4 mmol) were added to 400 ml of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. When the reaction was terminated after 3 hours, it was cooled to room temperature and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated 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 15.6 g of compound 18.

(Yield 58%, MS: [M+H]+= 894)

Synthesis example 19: Preparation of compound 19

In a nitrogen atmosphere, compound 19-1 (20 g, 31.9 mmol), compound d (8.5 g, 31.9 mmol), and sodium tert-butoxide (6.1 g, 63.9 mmol) were added to 400 ml of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. When the reaction was terminated after 3 hours, it was cooled to room temperature and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated 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 18.1 g of compound 19.

(Yield 66%, MS: [M+H]+= 858)

Synthesis Example 20: Preparation of Compound 20

In a nitrogen atmosphere, compound 20-1 (20 g, 38 mmol), compound b (10.2 g, 38 mmol), and sodium tert-butoxide (7.3 g, 76 mmol) were added to 400 ml of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. When the reaction was terminated after 3 hours, it was cooled to room temperature and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated 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 17.6 g of compound 20.

(Yield 61%, MS: [M+H]+= 758)

Synthesis Example 21: Preparation of Compound 21

In a nitrogen atmosphere, compound 21-1 (20 g, 32.8 mmol), compound b (8.8 g, 32.8 mmol), and sodium tert-butoxide (6.3 g, 65.6 mmol) were added to 400 ml of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.7 mmol) was added. When the reaction was terminated after 3 hours, it was cooled to room temperature and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated 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 13.2 g of compound 21.

(Yield 48%, MS: [M+H]+= 842)

Synthesis example 22: Preparation of compound 22

In a nitrogen atmosphere, compound 22-1 (20 g, 29.6 mmol), compound a (6.4 g, 29.6 mmol), sodium tert-butoxide (5.7 g, 59.2 mmol) was added to 400 ml of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. When the reaction was terminated after 3 hours, it was cooled to room temperature and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated 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 15.7 g of compound 22.

(Yield 62%, MS: [M+H]+= 857)

Synthesis example 23: Preparation of compound 23

In a nitrogen atmosphere, compound 23-1 (20 g, 29.6 mmol), compound a (6.4 g, 29.6 mmol), and sodium tert-butoxide (5.7 g, 59.2 mmol) were added to 400 ml of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. When the reaction was terminated after 3 hours, it was cooled to room temperature and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated 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 11.4 g of compound 23.

(Yield 45%, MS: [M+H]+= 858)

Synthesis Example 24: Preparation of Compound 24

In a nitrogen atmosphere, compound 24-1 (20 g, 28.9 mmol), compound a (6.3 g, 28.9 mmol), and sodium tert-butoxide (5.6 g, 57.9 mmol) were added to 400 ml of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. When the reaction was terminated after 3 hours, it was cooled to room temperature and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated 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 11.4 g of compound 24.

(Yield 45%, MS: [M+H]+= 873)

Synthesis example 25: Preparation of compound 25

In a nitrogen atmosphere, compound 25-1 (20 g, 32.8 mmol), compound a (7.1 g, 32.8 mmol), and sodium tert-butoxide (6.3 g, 65.6 mmol) were added to 400 ml of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.7 mmol) was added. When the reaction was terminated after 3 hours, it was cooled to room temperature and reduced pressure to remove the solvent. After that, the compound was completely dissolved again in chloroform, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.9 g of compound 25.

(Yield 42%, MS: [M+H]+= 792)

Comparative example One

A glass substrate coated with a thin film of ITO (indium tin oxide) having a thickness of 1,000Å was placed in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a product made by Fischer Co. was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

The following HI-1 compound was formed as a hole injection layer on the prepared ITO transparent electrode to a thickness of 1150Å, but the following compound A-1 was p-doping at a concentration of 1.5%. The following HT-1 compound was vacuum deposited on the hole injection layer to form a hole transport layer having a thickness of 800 Å. Subsequently, an electron suppressing layer was formed by vacuum depositing the following EB-1 compound with a film thickness of 150 Å on the hole transport layer.

Subsequently, the following RH-1 compound as a host material and the following Dp-7 compound as a dopant material were vacuum-deposited on the electron-suppression layer at a weight ratio of 98:2 to form a 400 Å-thick red light emitting layer.

A hole blocking layer was formed by vacuum depositing the following HB-1 compound with a thickness of 30 Å on the emission layer. Subsequently, the following ET-1 compound and the following LiQ compound were vacuum-deposited at a weight ratio of 2:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300Å.

Lithium fluoride (LiF) in a thickness of 12 Å and aluminum in a thickness of 1,000 Å were sequentially deposited on the electron injection and transport layer to form a negative electrode.

Was maintained at the deposition rate was 0.4 ~ 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, the deposition rate of aluminum was maintained 2Å / sec, the degree of vacuum upon deposition 2ⅹ10 ^-7 ~ An organic light-emitting device was fabricated by maintaining 5x10 ^-6 torr.

Examples 1 to 25

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the compound shown in Table 1 below was used instead of the host material RH-1 in the organic light-emitting device of Comparative Example 1. At this time, the specific structures of the compounds used in the examples are as follows.

Comparative Examples 2 to 13

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the compound shown in Table 1 below was used instead of the host material RH-1 in the organic light-emitting device of Comparative Example 1. At this time, the specific structures of the compounds used in the comparative example are as follows.

Experimental Example 1: Evaluation of device characteristics

When a current was applied to the organic light emitting devices prepared in Examples 1 to 25 and Comparative Examples 1 to 13, voltage, efficiency, and lifetime were measured (10 mA/cm ² ), and the results are shown in Table 1 below. Shown in. Life T95 refers to the time it takes for the luminance to decrease from the initial luminance (6000 nit) to 95%.

division Emitting layer
Host Driving voltage
(V) efficiency
(cd/A) Life T95
(hr) Luminous color Comparative Example 1 RH-1 4.12 21.1 133 Red Example 1 Compound 1 3.60 25.5 181 Red Example 2 Compound 2 3.61 24.7 170 Red Example 3 Compound 3 3.64 25.8 167 Red Example 4 Compound 4 3.62 26.1 168 Red Example 5 Compound 5 3.73 26.5 176 Red Example 6 Compound 6 3.70 25.3 161 Red Example 7 Compound 7 3.71 24.9 188 Red Example 8 Compound 8 3.61 25.5 177 Red Example 9 Compound 9 3.60 26.3 163 Red Example 10 Compound 10 3.65 25.1 162 Red Example 11 Compound 11 3.63 25.8 177 Red Example 12 Compound 12 3.68 24.3 189 Red Example 13 Compound 13 3.64 26.9 175 Red Example 14 Compound 14 3.51 28.1 227 Red Example 15 Compound 15 3.50 29.0 234 Red Example 16 Compound 16 3.49 28.2 217 Red Example 17 Compound 17 3.52 29.6 210 Red Example 18 Compound 18 3.47 27.9 223 Red Example 19 Compound 19 3.50 28.1 230 Red Example 20 Compound 20 3.48 28.5 214 Red Example 21 Compound 21 3.53 29.6 208 Red Example 22 Compound 22 3.71 26.3 175 Red Example 23 Compound 23 3.67 25.7 151 Red Example 24 Compound 24 3.69 26.5 187 Red Example 25 Compound 25 3.65 25.3 174 Red Comparative Example 2 C-1 3.85 20.1 105 Red Comparative Example 3 C-2 3.80 20.9 118 Red Comparative Example 4 C-3 4.01 20.1 109 Red Comparative Example 5 C-4 3.95 19.3 84 Red Comparative Example 6 C-5 4.51 15.2 15 Red Comparative Example 7 C-6 4.57 15.8 24 Red Comparative Example 8 C-7 4.69 14.2 18 Red Comparative Example 9 C-8 4.39 13.4 57 Red Comparative Example 10 C-9 4.11 21.6 84 Red Comparative Example 11 C-10 4.15 22.5 79 Red Comparative Example 12 C-11 4.39 15.7 21 Red Comparative Example 13 C-12 4.31 18.6 46 Red

As shown in the table above, the organic light-emitting device of the Example using the compound represented by Formula 1 as the host material of the red light-emitting layer, compared to the organic light-emitting device of Comparative Example, has a low driving voltage, high efficiency, and a long lifespan. Done. This is considered to be due to the fact that the compound represented by Chemical Formula 1 has better energy transfer to the red dopant than the compound having a structure different from that of the present application used in the comparative example. Accordingly, when the compound represented by Formula 1 is used as the host material of the organic light-emitting device, it can be seen that the driving voltage, luminous efficiency, and/or lifetime characteristics of the organic light-emitting device are improved.

1: substrate 2: anode
3: light emitting layer 4: cathode
5: hole injection layer 6: hole transport layer
7: electron suppression layer 8: hole blocking layer
9: electron injection and transport layer

Claims (9)

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

In Formula 1,
Ar ₁ and Ar ₂ are each independently substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S,
R ₁ to R ₆ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl including any one or more selected from the group consisting of N, O and S, or two adjacent to each other among R ₁ to R ₄ are substituted or unsubstituted A C _6-60 aromatic ring or a substituted or unsubstituted C _2-60 heteroaromatic ring including any one or more heteroatoms selected from the group consisting of N, O and S,
a is an integer from 0 to 3,
b is an integer from 0 to 6,
A is a substituent represented by the following formula (2),
[Formula 2]

In Formula 2,
X is O or S,
R ₇ and R ₈ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl including any one or more selected from the group consisting of N, O and S, or substituted or unsubstituted C _6-60 aromatic by bonding with adjacent substituents A ring or a substituted or unsubstituted C _2-60 heteroaromatic ring including any one or more heteroatoms selected from the group consisting of N, O and S,
c is an integer from 0 to 3,
d is an integer from 0 to 4.
The method of claim 1,
The compound is represented by any one of the following formulas 1-1 to 1-4,
compound:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4,
R ₁ to R ₆ and R ₁₁ to R ₁₄ are each independently hydrogen, deuterium, or C _6-20 aryl,
Ar ₁ , Ar ₂ , a, b and A are as defined in claim 1.
The method of claim 1,
Ar ₁ and Ar ₂ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, anthryl, phenanthryl, triphenylenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl,
The Ar ₁ and Ar ₂ are unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and phenyl,
compound.
The method of claim 1,
Ar ₁ and Ar ₂ are each independently any one selected from the group consisting of,
compound.

.
The method of claim 1,
R ₇ and R ₈ are each independently hydrogen or deuterium;
Two adjacent two of R ₇ are bonded to each other to form a benzene ring, and the remaining R ₇ and R ₈ are each independently hydrogen or deuterium;
Two adjacent two of R ₈ are bonded to each other to form a benzene ring, and the remaining R ₈ and R ₇ are each independently hydrogen or deuterium; or
Two adjacent two of R ₇ and two adjacent two of R ₈ are each bonded to each other to form a benzene ring, and the remaining R ₇ and R ₈ are each independently hydrogen or deuterium,
compound.
The method of claim 1,
A is any one selected from the group consisting of,
compound:

.
The method of claim 1,
The compound is represented by any one of the following formulas 1-1-1, 1-1-2, 1-2-1, 1-3-1, and 1-4-1,
compound:

In Formulas 1-1-1, 1-1-2, 1-2-1, 1-3-1, and 1-4-1,
Ar ₁ , Ar ₂ and A are as defined in claim 1.
The method of claim 1,
The compound is any one selected from the group consisting of the following compounds,
compound:

.
A first electrode; A second electrode provided to face the first electrode; And an emission layer provided between the first electrode and the second electrode, wherein the emission layer comprises a compound according to any one of claims 1 to 8, .

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