NOVEL HETEROCYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME

Abstract

Provided is a heterocyclic compound of Chemical Formula 1:

Description

TECHNICAL FIELD

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

BACKGROUND

In general, an organic light emitting phenomenon refers to a phenomenon where electric energy is converted into light energy by using an organic material. The organic light emitting device using the organic light emitting phenomenon has characteristics such as a wide viewing angle, an excellent contrast, a fast response time, excellent luminance, driving voltage and response speed, and thus many studies have proceeded.

The organic light emitting device generally has a structure which comprises an anode, a cathode, and an organic material layer interposed between the anode and the cathode. The organic material layer frequently have a multilayered structure that comprises different materials in order to enhance efficiency and stability of the organic light emitting device, and for example, the organic material layer 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 the organic light emitting device, if a voltage is applied between two electrodes, the holes are injected from an anode into the organic material layer and the electrons are injected from the cathode to the organic material layer, and when the injected holes and the electrons meet each other, an exciton is formed, and light is emitted when the exciton falls to a ground state again.

There is a continuing demand for developing a new material for organic materials used in such organic light emitting devices.

PRIOR ART LITERATURE

Patent Literature

(Patent Literature 1) Korean Patent Laid-open Publication No. 10-2000-0051826

BRIEF DESCRIPTION

Technical Problem

It is one object of the present invention to provide a novel heterocyclic compound and an organic light emitting device comprising the same.

Technical Solution

The present invention provides a compound represented by the following Chemical Formula 1:

In Chemical Formula 1,

X₁ is O or S,

L₁ and L₂ are each independently a single bond; a substituted or unsubstituted C_6-60 arylene; or a substituted or unsubstituted C_1-60 heteroarylene containing one or more heteroatoms selected from the group consisting of O, N, Si and S,

Y₁ to Y₃ are each independently N or CR₃, provided that at least one of Y₁ to Y₃ is N,

Ar_1a and Ar_1b are each independently a substituted or unsubstituted C_6-60 aryl; or a substituted or unsubstituted C_1-60 heteroaryl containing 1 to 3 heteroatoms selected from the group consisting of N, O and S,

Ar₂ is a substituted or unsubstituted C_6-60 aryl,

R₁ to R₃ are each independently hydrogen; deuterium; halogen; cyano; nitro; amino; a substituted or unsubstituted C_1-60 alkyl; a substituted or unsubstituted C_1-60 haloalkyl; a substituted or unsubstituted C_1-60 alkoxy; a substituted or unsubstituted C_1-60 haloalkoxy; a substituted or unsubstituted C_3-60 cycloalkyl; a substituted or unsubstituted C_2-60 alkenyl; a substituted or unsubstituted C_6-60 aryl; a substituted or unsubstituted CF-so aryloxy; or a substituted or unsubstituted C_1-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S, and

n₁ and n₂ are each independently an integer of 0 to 3.

In addition, the present invention provides an organic light emitting device comprising a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprises a compound represented by Chemical Formula 1.

Advantageous Effects

The compound represented by Chemical Formula 1 can be used as a material of an organic material layer of an organic light emitting device and can exhibit improved efficiency, a low driving voltage and/or improved lifetime characteristics of the organic light emitting device. In particular, the compound represented by Chemical Formula 1 can be used as a host material of the light emitting layer.

BRIEF DESCRIPTION OF DRAWINGS

FIG. 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.

FIG. 2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4.

DETAILED DESCRIPTION

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

In the present specification,

means a bond connected to another substituent group, and a single bond means when a separate atom does not exist in a portion denoted by L₁ and L₂.

As used herein, the term “substituted or unsubstituted” means that substitution is performed by one or more substituent groups selected from the group consisting of deuterium; a halogen group; a cyano group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthioxy group; an arylthioxy group; an alkylsulfoxy group; an arylsulfoxy group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; an aralkyl groups; an aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; a heteroarylamine group; an arylamine group; an arylphosphine group; or heteroaryl containing at least one of N, O, and S atoms, or there is no substituent group, or substitution is performed by a substituent group where two or more substituent groups of the exemplified substituent groups are connected or there is no substituent group. For example, the term “substituent group where two or more substituent groups are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent group where two phenyl groups are connected.

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

In the present specification, oxygen of an ester group may be substituted by a straight-chain, branched-chain, or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group may be compounds having the following structures, but is not limited thereto:

In the present specification, the number of carbon atoms in an imide group is not particularly limited but is preferably 1 to 25. Specifically, the imide group may be compounds having the following structures, 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, but is not limited thereto.

In the present specification, the boron group specifically includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like, but is not limited thereto.

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

In the present specification, an alkyl group may be a straight chain or a branched chain, and the number of carbon atoms thereof is not particularly limited but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to still another 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 straight chain or a branched chain, and the number of carbon atoms thereof is not particularly limited but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to still another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples thereof 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, a stilbenyl group, a styrenyl group, and the like, but are not limited thereto.

In the present specification, a cycloalkyl group is not particularly limited, but the number of carbon atoms thereof is preferably 3 to 60. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples thereof include 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 preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. Examples of the polycyclic aryl group include a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group or the like, but is not limited thereto.

In the present specification, a fluorenyl group may be substituted, and two substituent groups may be bonded to each other to form a spiro structure. In the case where the fluorenyl group is substituted,

and the like can be formed. However, the structure is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as a heteroatom, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a triazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, a triazole group, an acridyl group, a pyridazine group, a pyrazinyl group, a quinolinyl group, a quinazoline group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, an indole group, a carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline group, a thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, a dibenzofuranyl group, and the like, but are 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 aforementioned examples of the aryl group. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group and the alkylamine group is the same as the aforementioned examples of the alkyl group. In the present specification, the heteroaryl in the heteroarylamines can be applied to the aforementioned description of the heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the aforementioned examples of the alkenyl group. In the present specification, the aforementioned description of the aryl group may be applied except that the arylene is a divalent group. In the present specification, the aforementioned description of the heterocyclic group can be applied except that the heteroarylene is a divalent group. In the present specification, the aforementioned description of the aryl group or cycloalkyl group can be applied except that the hydrocarbon ring is not a monovalent group but formed by combining two substituent groups. In the present specification, the aforementioned description of the heterocyclic group can be applied, except that the heterocycle is not a monovalent group but formed by combining two substituent groups.

Meanwhile, the present invention also provides a compound represented by Chemical Formula 1.

Specifically, the compound represented by Chemical Formula 1 can be represented by the following Chemical Formulas 1-1 to 1-4:

In the above chemical formulas 1-1 to 1-4, L₁, L₂, Y₁ to Y₃, Ar_1a, Ar_1b, Ar₂, R₁, R₂, n1 and n2 are as defined in Chemical Formula 1.

Preferably, in Chemical Formula 1, L₁ and L₂ are each independently a single bond; or a substituted or unsubstituted C_6-20 arylenyl.

For example, L₁ and L₂ are each independently a single bond; a substituted or unsubstituted phenylene; a substituted or unsubstituted naphthylene; or a substituted or unsubstituted biphenylenyl.

Specifically, for example, L₁ and L₂ may each independently be a single bond, or any one selected from the group consisting of:

Preferably, in Chemical Formula 1,

Y₁ is N, Y₂ is N, and Y₃ is N; or

Y₁ is N, Y₂ is N, and Y₃ is CR₃; or

Y₁ is N, Y₂ is CR₃, and Y₃ is N; or

Y₁ is N, Y₂ is CR₃, and Y₃ or CR₃; or

Y₁ is CR₃, Y₂ is CR₃, and Y₃ is N.

Preferably, in Chemical Formula 1,

Y₁ is N, Y₂ is N, and Y₃ is N; or

Y₁ is N, Y₂ is N, and Y₃ is CH; or

Y₁ is N, Y₂ is CH, and Y₃ is N; or

Y₁ is N, Y₂ is CH, and Y₃ is CH; or

Y₁ is CH, Y₂ is CH, and Y₃ is N.

Preferably, in Chemical Formula 1, Ar_1a and Ar_1b are each independently a substituted or unsubstituted C_6-20 aryl; or a substituted or unsubstituted C_1-20 heteroaryl containing one heteroatom selected from the group consisting of N, O, and S.

For example, Ar₁₁ and Ar_1b may be each independently any one selected from the group consisting of:

wherein,

X₂ is O, S, NZ₄, or CZ₅Z₆,

Z₁ to Z₆ are each independently hydrogen; deuterium; halogen; cyano; nitro; amino; a substituted or unsubstituted C_1-20 alkyl, a substituted or unsubstituted C_1-20 haloalkyl, a substituted or unsubstituted C_1-20 aryl, or a substituted or unsubstituted C_1-20 heteroaryl containing one or more heteroatoms selected from the group consisting of N, O and S,

c1 is an integer of 0 to 5,

c2 is an integer of 0 to 4, and

c3 is an integer of 0 to 3.

In this case, c1 represents the number of Z₁, and when c1 is 2 or more, two or more Z₁ may be the same as or different from each other. The description of c2 and c3 can be understood with reference to the description of c1 and the structure of the above chemical formula.

Specifically, for example, Ar_1a and Ar_1b may be each independently any one selected from the group consisting of:

Further, in Chemical Formula 1, Ar₂ is substituted or unsubstituted C_6-60 aryl. Here, aryl does not include non-aromatic condensed rings. Specifically, a substituted or unsubstituted fluorenyl group is excluded from Ar₂ of the present invention.

Preferably, Ar₂ is a C_6-60 aryl which unsubstituted or substituted by a substituent independently selected from the group consisting of: deuterium; halogen; cyano; nitro; amino; a substituted or unsubstituted C_1-60 alkyl; a substituted or unsubstituted C_1-60 haloalkyl; Si(Q₁)(Q₂)(Q₃); C(Q₄)(Q₅)(Q₆) and C_6-60 aryl, wherein Q₁ to Q₆ are each independently hydrogen; deuterium; halogen;

cyano; nitro; amino; a substituted or unsubstituted C_1-20 alkyl; or a substituted or unsubstituted C_6-20 aryl.

For example, Ar₂ may be any one selected from the group consisting of:

wherein

Z₁₁ to Z₁₄ are each independently hydrogen; deuterium; halogen; cyano; nitro; amino; a substituted or unsubstituted C_1-60 alkyl; a substituted or unsubstituted C_1-60 haloalkyl; Si(Q₁)(Q₂)(Q₃); C(Q₄)(Q)(Q₆) and C_6-60 aryl,

• • wherein Q₁ to Q₆ are each independently hydrogen: deuterium; halogen; cyano: nitro; amino; a substituted or unsubstituted C_1-20 alkyl; or a substituted or unsubstituted C_6-20 aryl,

c11 is an integer of 0 to 5,

c12 is an integer of 0 to 7,

c13 is an integer of 0 to 9,

c14 is an integer of 0 to 4,

c15 is an integer of 0 to 3,

c16 is an integer of 0 to 11,

c17 is an integer of 0 to 9,

c18 is an integer of 0 to 6, and

c19 is an integer of 0 to 12.

Here, c11 represents the number of Z₁₁, and when c11 is 2 or more, two or more Z₁₁ may be the same as or different from each other. The description of c12 to c19 can be understood with reference to the description of c11 and the structure of the above chemical formula.

Preferably, Q₁ to Q₆ are hydrogen; deuterium; halogen; cyano; nitro; amino; methyl; or phenyl.

Specifically, for example, Ar₂ may be any one selected from the group consisting of:

Further, in Chemical Formula 1, R₁ to R₃ are each independently hydrogen; deuterium; cyano; or a substituted or unsubstituted C_1-10 alkyl.

For example, R₁ and R₂ may be each independently hydrogen, deuterium, cyano, methyl, or deuterium-substituted methyl, and R₃ may be hydrogen.

In Chemical Formula 1, n1 represents the number of R₁, and when n1 is 2 or more, two or more R₁ may be the same as or different from each other. The description of n2 can be understood with reference to the description of n1 and the structure of Chemical Formula 1.

For example, the compound may be selected from the group consisting of the following compounds:

The compound represented by Chemical Formula 1 has a structure in which an N-atom-containing heteroaryl substituent group such as a pyridinyl group, a pyrimidinyl group, or a triazinyl group is connected to a specific position of dibenzofuran or dibenzothiophene core, and an aryl substituent group which is an aromatic group is connected to a specific position of the dibenzofuran or dibenzothiophene core, and thereby an organic light emitting device using the same has a higher efficiency, a lower driving voltage and a longer life time than an organic light emitting device using a compound in which a non-aromatic condensed ring group such as a fluorenyl group is connected.

Meanwhile, the compound represented by Chemical Formula 1 can be prepared in the same manner as shown in the following Reaction Scheme 1:

In Reaction Scheme 1, L₁, L₂, Y₁ to Y₃, Ar_1a, Ar_1b and Ar₂ are as defined in Chemical Formula 1.

The compound represented by Chemical Formula 1 can be prepared by appropriately substituting the starting material in accordance with the structure of the compound to be prepared with reference to Reaction Scheme 1.

In addition, the present invention provides an organic light emitting device comprising the compound represented by Chemical Formula 1. In one example, the present invention provides an organic light emitting device comprising: a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers comprise the compound of Chemical Formula 1.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, or a multilayered structure in which two or more organic material layers are laminated. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as the organic material layer. However, the structure of the organic light emitting device is not limited thereto, but may include a smaller number of organic layers.

Specifically, the organic material layer may include a light emitting layer, and the light emitting layer includes the compound represented by Chemical Formula 1.

In this case, the compound represented by Chemical Formula 1 can be used as a host material in the light emitting layer.

Further, the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) where an anode, one or more organic material layers, and a cathode are sequentially laminated on a substrate. Further, the organic light emitting device according to the present invention may be an organic light emitting device having an inverted direction structure (inverted type) where the cathode, one or more organic material layers, and the anode are sequentially laminated on the substrate. For example, the structure of the organic light emitting device according to one embodiment of the present invention is illustrated in FIGS. 1 and 2.

FIG. 1 illustrates 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 Chemical Formula 1 may be included in the light emitting layer.

FIG. 2 illustrates an example of an organic light emitting device including a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4. In such a structure, the compound represented by Chemical Formula 1 may be included in one or more layers of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.

The organic light emitting device according to the present invention may be manufactured by using materials and methods known in the art, except that one or more of organic material layers include the compound represented by Chemical Formula 1. Further, in the case where the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same materials or different materials.

For example, the organic light emitting device according to the present invention may be manufactured by sequentially laminating the first electrode, the organic material layer, and the second electrode on the substrate. In this case, the organic light emitting device may be manufactured by depositing a metal, metal oxides having conductivity, or an alloy thereof on the substrate by using a PVD (physical vapor deposition) method such as a sputtering method or an e-beam evaporation method to form the anode, forming the organic material layer including the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer thereon, and then depositing a material that can be used as the cathode thereon. In addition to such a method, the organic light emitting device may be manufactured by sequentially depositing a cathode material, the organic material layer, and an anode material on the substrate.

Further, the compound represented by Chemical Formula 1 may be formed as the organic material layer by a vacuum deposition method as well as a solution coating method during the production of the organic light emitting device. Herein, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, a spray method, roll coating, or the like, but is not limited thereto.

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

In one example, the first electrode is the anode, and the second electrode is the cathode, and alternatively, the first electrode is the cathode, and the second electrode is the anode.

As the anode material, generally, a material having a large work function is preferably used so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material include metals such as vanadium, chrome, copper, zinc, and gold, or an alloy thereof; metal oxides such as zinc oxides, indium oxides, indium tin oxides (ITO), and indium zinc oxides (IZO); a combination of metals and oxides, such as ZnO:Al or SNO₂:Sb; conductive polymers 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.

As the cathode material, generally, a material having a small work function is preferably used so that electrons can be easily injected into the organic material layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or an alloy thereof; a multilayered structure material such as LiF/Al or LiO₂/Al, and the like, but are not limited thereto.

The hole injection material layer is a layer injecting the holes from the electrode, and the hole injection material is preferably a compound which has an ability of transporting the holes, a hole injection effect in the anode and an excellent hole injection effect to the light emitting layer or the light emitting material, prevents movement of an exciton generated in the light emitting layer to the electron injection layer or the electron injection material, and has an excellent thin film forming ability. It is preferable that a HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and a HOMO of a peripheral organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, an arylamine-based organic material, a hexanitrilehexaazatriphenylene-based organic material, a quinacridone-based organic material, a perylene-based organic material, anthraquinone, polyaniline and polythiophene-based conductive polymer, and the like, but are not limited thereto.

The hole transport layer is a layer receiving the holes from the hole injection layer and transporting the holes to the light emitting layer, and the hole transport material is a material that can receive the holes from the anode or the hole injection layer and transport the holes to the light emitting layer, and a material having large mobility to the holes is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, a block copolymer in which a conjugate portion and a non-conjugate portion are present together, and the like, but are not limited thereto.

The light emitting material layer is a material that can receive the holes and the electrons from the hole transport layer and the electron transport layer, respectively, and bond the holes and the electrons to emit light in a visible ray region, and is preferably a material having good quantum efficiency to fluorescence or phosphorescence. Specific examples thereof include a 8-hydroxy-quinoline aluminum complex (Alq₃); a carbazole-based compound; a dimerized styryl compound; BAlq; a 10-hydroxybenzoquinoline-metal compound; benzoxazole, benzothiazole, and benzimidazole-based compounds; a poly(p-phenylenevinylene) (PPV)-based polymer; a spiro compound; polyfluorene, rubrene, and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. Examples of the host material include a condensation aromatic cycle derivative, a heterocycle-containing compound, or the like. Specific examples of the condensation aromatic cycle derivative include an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the like, and specific examples of the heterocycle-containing compound include a carbazole derivative, a dibenzofuran derivative, a ladder-type furan compound, a pyrimidine derivative, and the like, but are not limited thereto.

Examples of the dopant material include an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. Specifically, the aromatic amine derivative is a condensation aromatic cycle derivative having a substituted or unsubstituted arylamino group, examples thereof include pyrene, anthracene, chrysene, and periflanthene having the arylamino group, and the like, the styrylamine compound is a compound where at least one arylvinyl group is substituted in substituted or unsubstituted arylamine, in which one or two or more substituent groups 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. Specific examples thereof include styrylamine, styryldiamine, styryltriamine, styryltetramine, and the like, but are not limited thereto. Further, examples of the metal complex include an iridium complex, a platinum complex, and the like, but are not limited thereto.

The electron transport material is a layer receiving the electrons from the electron injection layer and transporting the electrons to the light emitting layer, the electron transport material is a material that can receive the electrons well from the cathode and transport the electrons to the light emitting layer, and a material having large mobility to the electrons is suitable. Specific examples thereof include an 8-hydroxyquinoline Al complex; a complex including Alq₃; an organic radical compound; a hydroxyflavone-metal complex, and the like, but are not limited thereto. Particularly, it is preferable to use the compound represented by the above-mentioned chemical formula 1 as an electron transport material. The electron transport layer may be used together with a predetermined desired cathode material as used according to the prior art. Particularly, an example of an appropriate cathode material is a general material having the low work function and followed by an aluminum layer or a silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium, and samarium, and each case is followed by the aluminum layer or the silver layer.

The electron injection layer is a layer injecting the electrons from the electrode, and a compound which has an ability of transporting the electrons, an electron injection effect from the cathode, and an excellent electron injection effect to the light emitting layer or the light emitting material, prevents movement of an exciton generated in the light emitting layer to the hole injection layer, and has an excellent thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, a metal complex compound, a nitrogen-containing 5-membered cycle derivative, and the like, 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-cresolato)-gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, and the like, but are not limited thereto.

The organic light emitting device according to the present invention may be a front side emission type, a back side emission type, or a double side emission type according to the used material.

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

The preparation of the compound represented by Chemical Formula 1 and the organic light emitting device including the same will be described in detail in the following examples. However, these examples are presented for illustrative purposes only, and the scope of the present invention is not limited thereto.

Synthesis Example 1: Preparation of Intermediate Compound P-6

1-Bromo-3-fluoro-2-iodobenzene (100 g, 333.5 mmol) and (5-chloro-2-methoxyphenyl)boronic acid (62.2 g, 333.5 mmol) were dissolved in 800 ml of tetrahydrofuran (THF). Then, 2M sodium carbonate (Na₂CO₃) solution (500 mL) and tetrakis(triphenylphosphine)palladium(0) [Pd(PPh₃)₄] (7.7 g, 6.7 mmol) were added thereto, and the mixture was refluxed for 12 hours. After completion of the reaction, the mixture was cooled to room temperature, and then was extracted three times with water and toluene. The toluene layer was separated and dried with magnesium sulfate, and the filtrate was distilled under reduced pressure. The resulting mixture was recrystallized three times using chloroform and ethanol to obtain Compound P-1 (53.7 g, yield 51%; MS: [M+H]⁺=314),

Compound P-1 (50.0 g, 158.5 mmol) was dissolved in dichloromethane (600 ml) and then cooled to 0° C. Boron tribromide (15.8 ml, 166.4 mmol) was slowly added dropwise thereto and then stirred for 12 hours. After completion of the reaction, the mixture was washed three times with water, dried with magnesium sulfate, and filtered. The filtrate was distilled under reduced pressure and purified by column chromatography to obtain Compound P-2 (47.4 g, yield 99%; MS:[M+H]⁺=300).

Compound P-2 (40.0 g, 132.7 mmol) was dissolved in distilled dimethylformamide (DMF) (400 ml). This solution was cooled to 0° C. and sodium hydride (3.5 g, 145.9 mmol) was slowly added dropwise thereto. After stirring for 20 minutes, the mixture was stirred at 100° C. for 1 hour. After completion of the reaction, the reaction mixture was cooled to room temperature and 100 ml of ethanol was slowly added. The mixture was distilled under reduced pressure, and the resulting mixture was recrystallized from chloroform and ethyl acetate to obtain Compound P-3 (30.3 g, yield 81%: MS: [M+H]⁺=280).

After Compound P-3 (30.0 g, 106.6 mmol) was dissolved in tetrahydrofuran (300 ml), the temperature was lowered to −78° C. and 1.7M tert-butyllithium (t-BuLi) (62.7 ml, 106.6 mmol) was slowly added. After stirring at the same temperature for one hour, triisopropyl borate (B(OiPr)₃) (28.3 ml, 213.1 mmol) was added and stirred for 3 hours while gradually increasing the temperature to room temperature. To the reaction mixture was added 2N aqueous hydrochloric acid solution (200 mil) and then stirred at room temperature for 1.5 hours. The resulting precipitate was filtered, washed sequentially with water and ethyl ether, and dried under vacuum. After drying, the mixture was dispersed in ethyl ether, stirred for 2 hours, filtered and dried to obtain Compound P-4 (24.4 g, yield 93%; MS: [M+H]⁺=247).

After Compound P-4 (20.0 g, 81.2 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (21.8 g, 81.2 mmol) were dispersed in tetrahydrofuran (250 ml), 2M aqueous potassium carbonate solution (aq. K₂CO₃) (33.6 ml, 243.5 mmol) was added, tetrakis(triphenylphosphine)palladium [Pd(PPh₃)₄] (1.9 g, 2 mol %) was added, and then the mixture was stirred and refluxed for 4 hours. The temperature was lowered to room temperature and the resulting solid was filtered. The filtrated solid was recrystallized from tetrahydrofuran and ethyl acetate, filtered and then dried to obtain Compound P-5 (32.4 g, yield 92%; MS:[M+H]⁺=434).

Compound P-5 (30 g, 69.2 mmol), bis(pinacolato)diboron (19.3 g, 76.1 mmol), potassium acetate (20.4 g, 207.5 mmol), and tetrakis (triphenylphosphine)palladium(0) [Pd(PPh₃)₄] (1.6 g, 2 mol %) was added to tetrahydrofuran (300 ml) and refluxed for 12 hours. After completion of the reaction, the mixture was cooled to room temperature and distilled under reduced pressure to remove the solvent. This was dissolved in chloroform, washed three times with water, and then the organic layer was separated, dried with magnesium sulfate and then distilled under reduced pressure to obtain Compound P-6 (34.5 g, yield 95%; MS: [M+H]⁺=526).

Synthesis Example 1-1: Preparation of Compound 1

After Compound P-6 (20.0 g, 38.1 mmol) and 2-bromophenanthrene (9.8 g, 38.1 mmol) were dispersed in tetrahydrofuran (250 ml), 2M aqueous potassium carbonate solution (aq. K₂CO₃) (57.2 ml, 114.3 mmol) was added and tetrakis(triphenylphosphine)palladium [Pd(PPh₃)₄] (1.4 g, 2 mol %) was added, and then the mixture was stirred and refluxed for 5 hours. The temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethyl acetate, filtered and then dried to obtain Compound 1 (17.8 g, yield 81%; MS: [M+H]⁺=576).

Synthesis Example 1-2: Preparation of Compound 2

Compound 2 (18.4 g, yield 84%; MS:[M+H]⁺=576) was prepared in the same manner as in Synthesis Example 1-1, except that 9-bromophenanthrene (9.8 g, 38.1 mmol) was used instead of 2-bromophenanthrene.

Synthesis Example 1-3: Preparation of Compound 3

Compound 3 (18.8 g, yield 82%; MS:[M+H]⁺=602) was prepared in the same manner as in Synthesis Example 1-1, except that 1-bromo-4-phenylnaphthalene (10.8 g, 38.1 mmol) was used instead of 2-bromophenanithrene.

Synthesis Example 1-4: Preparation of Compound 4

Compound 4 (21.0 g, yield 88%; MS:[M+H]⁺=626) was prepared in the same manner as in Synthesis Example 1-1, except that 2-bromotriphenylene (11.7 g, 38.1 mmol) was used instead of 2-bromophenanthrene.

Synthesis Example 1-5: Preparation of Compound 11

Compound 11 (19.9 g, yield 80%; MS:[M+H]⁺=652) was prepared in the same manner as in Synthesis Example 1-1, except that 9-(4-bromophenyl)phenanthrene (12.7 g, 38.1 mmol) was used instead of 2-bromophenanthrene.

Synthesis Example 1-6: Preparation of Compound 12

Compound 12 (22.5 g, yield 81%; MS:[M+H]⁺=728) was prepared in the same manner as in Synthesis Example 1-1, except that 9-(2′-bromo-[1,1′-biphenyl]-2-yl)phenanthrene (15.6 g, 38.1 mmol) was used instead of 2-bromophenanthrene.

Synthesis Example 1-7: Preparation of Compound 13

Compound 13 (21.8 g, yield 76%; MS:[M+H]⁺=752) was prepared in the same manner as in Synthesis Example 1-1, except that 7-(4-bromophenyl)-10-phenylfluoranthene (16.5 g, 38.1 mmol) was used instead of 2-bromophenanthrene.

Synthesis Example 1-8: Preparation of Compound 25

Compound 25 (24.3 g, yield 89%; MS:[M+H]⁺=718) was prepared in the same manner as in Synthesis Example 1-1, except that ((4-bromophenyl)methanetriyl)tribenzene (15.2 g, 38.1 mmol) was used instead of 2-bromophenanthrene.

Synthesis Example 1-9: Preparation of Compound 26

Compound 26 (19.9 g, yield 83%; MS:[M+H]⁺=628) was prepared in the same manner as in Synthesis Example 1-1, except that 4-bromo-1,1′:3′,1″-terphenyl (11.8 g, 38.1 mmol) was used instead of 2-bromophenanthrene.

Synthesis Example 1-10: Preparation of Compound 28

Compound 28 (21.7 g, yield 81%; MS:[M+H]⁺=704) was prepared in the same manner as in Synthesis Example 1-1, except that 4-bromo-5′-phenyl-1,1′:3′,1″-terphenyl (14.7 g, 38.1 mmol) was used instead of 2-bromophenanthrene.

Synthesis Example 1-11: Preparation of Compound 46

Compound 46 (22.3 g, yield 83%; MS:[M+H]⁺=704) was prepared in the same manner as in Synthesis Example 1-1, except that 4′″-bromo-1, 1:3′,1:4,1′″-quaterphenyl (14.7 g, 38.1 mmol) was used instead of 2-bromophenanthrene.

Synthesis Example 1-12: Preparation of Compound 55

Compound 55 (20.6 g, yield 86%; MS:[M+H]⁺=628) was prepared in the same manner as in Synthesis Example 1-1, except that 3-bromo-1,1′:4′,1″-terphenyl (11.8 g, 38.1 mmol) was used instead of 2-bromophenanthrene.

Synthesis Example 1-13: Preparation of Compound 57

Compound 57 (20.4 g, yield 82%; MS:[M+H]⁺=652) was prepared in the same manner as in Synthesis Example 1-1, except that 9-(3-bromophenyl)phenanthrene (12.7 g, 38.1 mmol) was used instead of 2-bromophenanthrene.

Synthesis Example 1-14: Preparation of Compound 62

Compound 62 (22.3 g, yield 83%; MS:[M+H]⁺=704) was prepared in the same manner as in Synthesis Example 1-1, except that 3-bromo-5′-phenyl-1,1:3′,1″-terphenyl (14.7 g, 38.1 mmol) was used instead of 2-bromophenanthrene.

Synthesis Example 1-15: Preparation of Compound 65

Compound 65 (21.7 g, yield 81%; MS:[M+H]⁺=704) was prepared in the same manner as in Synthesis Example 1-1, except that 5′-bromo-1,1:3,1″:3″,1″-quaterphenyl (14.7 g, 38.1 mmol) was used instead of 2-bromophenanthrene.

Synthesis Example 1-16: Preparation of Compound 66

Compound 66 (20.6 g, yield 77%; MS:[M+H]⁺=704) was prepared in the same manner as in Synthesis Example 1-1, except that 2-bromo-1,1′:3′,1 “:3”,1′″quaterphenyl (14.7 g, 38.1 mmol) was used instead of 2-bromophenanthrene.

Synthesis Example 1-17: Preparation of Compound 68

Compound 68 (22.9 g, yield 79%; MS:[M+H]⁺=760) was prepared in the same manner as in Synthesis Example 1-1, except that 4,4′,4″-((4-bromophenyl)methanetriyl)tris(methylbenzene) (16.9 g, 38.1 mmol) was used instead of 2-bromophenanthrene.

Synthesis Example 1-18: Preparation of Compound 72

Compound 72 (20.7 g, yield 76%; MS:[M+H]⁺=714) was prepared in the same manner as in Synthesis Example 1-1, except that 5′-(4-bromophenyl)-1,1′:3′,1″-terphenyl-2,2″,3,3″,4,4″,5,5″,6,6″-d10 (15.1 g, 38.1 mmol) was used instead of 2-bromophenanthrene.

Synthesis Example 1-19: Preparation of Compound 81

Compound 81 (18.9 g, yield 76%; MS:[M+H]⁺=652) was prepared in the same manner as in Synthesis Example 1-1, except that 3-(3-bromophenyl)phenanthrene (12.7 g, 38.1 mmol) was used instead of 2-bromophenanthrene.

Synthesis Example 1-20: Preparation of Compound 59

Compound 59 (19.5 g, yield 73%; MS:[M+H]⁺=702) was prepared in the same manner as in Synthesis Example 1-1, except that 2-(3-bromophenyl)triphenylene (14.6 g, 38.1 mmol) was used instead of 2-bromophenanthrene.

Synthesis Example 1-21: Preparation of Compound 45

Compound 45 (19.4 g, yield 81%; MS:[M+H]⁺=628) was prepared in the same manner as in Synthesis Example 1-1, except that 5′-bromo-1,1′:3′,1″-terphenyl (11.8 g, 38.1 mmol) was used instead of 2-bromophenanthrene.

Synthesis Example 1-22: Preparation of Compound 54

Compound 54 (21.2 g, yield 79%; MS:[M+H]⁺=704) was prepared in the same manner as in Synthesis Example 1-1, except that 5′-bromo-1,1:3,1″:4″,1″-quaterphenyl (14.7 g, 38.1 mmol) was used instead of 2-bromophenanthrene.

Synthesis Example 1-23: Preparation of Compound 29

Compound 29 (15.6 g, yield 74%; MS:[M+H]⁺=552) was prepared in the same manner as in Synthesis Example 1-1, except that 2-bromo-1,1′-biphenyl (8.9 g, 38.1 mmol) Was used instead of 2-bromophenanthrene.

Synthesis Example 2: Preparation of Intermediate Compound P-8

After Compound P-4 (40.0 g, 162.3 mmol) and 2-([1,1′-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (55.8 g, 162.3 mmol) were dispersed in tetrahydrofuran (500 ml), 2M potassium carbonate aqueous solution (aq. K₂CO₃) (67.2 ml, 486.9 mmol) was added and then tetrakis(triphenylphosphine) palladium [Pd(PPh₃)₄] (3.8 g, 2 mol %) was added, and the mixture was stirred and refluxed for 4 hours. The temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was recrystallized from tetrahydrofuran and ethyl acetate, filtered and then dried to obtain Compound P-7 (73.7 g, yield 89%; MS: [M+H]⁺=510).

Compound P-7 (70.5 g, 138.3 mmol), bis(pinacolato)diboron (38.6 g, 152.13 mmol), potassium acetate (40.7 g, 414.9 mmol), and tetrakis(triphenylphosphine)palladium(0) [Pd(PPha)₄] (3.2 g, 2 mol %) were added to tetrahydrofuran (600 ml) and refluxed for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and distilled under reduced pressure to remove the solvent. This was dissolved in chloroform and washed three times with water. The organic layer was separated, dried with magnesium sulfate, and then distilled under reduced pressure to obtain Compound P-8 (75.7 g, yield 91%; MS: [M+H]⁺=602).

Synthesis Example 2-1: Preparation of Compound 9

Compound 9 (19.9 g, yield 77%; MS:[M+H]⁺=678) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound P-8 (22.9 g, 38.1 mmol) instead of Compound P-6, and 2-(3-bromophenyl)naphthalene (10.8 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 2-2: Preparation of Compound 27

Compound 27 (21.2 g, yield 79%; MS:[M+H]⁺=704) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound P-8 (22.9 g, 38.1 mmol) instead of Compound P-6, and 4-bromo-1,1′:4′,1″-terphenyl (11.8 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 3: Preparation of Intermediate Compound P-10

After Compound P-4 (40.0 g, 162.3 mmol) and 2-([1,1′-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (55.8 g, 162.3 mmol) were dispersed in tetrahydrofuran (500 ml), 2M potassium carbonate aqueous solution (aq. K₂CO₃) (67.2 ml, 486.9 mmol) was added and tetrakis(triphenylphosphine)palladium [Pd(PPh₃)₄](3.8 g, 2 mol %) was added, and then the mixture was stirred and refluxed for 4 hours. The temperature was lowered to room temperature and the resulting solid was filtered. The filtrated solid was recrystallized from tetrahydrofuran and ethyl acetate, filtered and then dried to obtain Compound P-9 (69.5 g, yield 84%; MS: [M+H]⁺=510).

Compound P-9 (70.5 g, 138.3 mmol) bis(pinacolato)diboron (38.6 g, 152.13 mmol), potassium acetate (40.7 g, 414.9 mmol) and tetrakis (triphenylphosphine)palladium(0) [Pd(PPh₃)₄](3.2 g, 2 mol %) were added to tetrahydrofuran (600 ml) and refluxed for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and distilled under reduced pressure to remove the solvent. This was dissolved in chloroform and washed three times with water. The organic layer was separated, dried with magnesium sulfate, and distilled under reduced pressure to obtain Compound P-10 (73.5 g, yield 88%/o; MS: [M+H]⁺=602).

Synthesis Example 3-1: Preparation of Compound 6

Compound 6 (20.3 g, yield 76%; MS:[M+H]⁺=702) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound P-10 (22.9 g, 38.1 mmol) instead of Compound P-6, and 2-bromotriphenylene (11.7 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 3-2: Preparation of Compound 36

Compound 36 (21.1 g, yield 78%; MS:[M+H]⁺=709) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound P-10 (22.9 g, 38.1 mmol) instead of Compound P-6, and 4-bromo-1,1′:4′,1″-terphenyl-2″,3″,4″,5″,6″-d5 (12.0 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 3-3: Preparation of Compound 49

Compound 49 (20.4 g, yield 71%; MS:[M+H]⁺=754) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound P-10 (22.9 g, 38.1 mmol) instead of Compound P-6, and 1-([1,1′-biphenyl]-2-yl)-4-bromonaphthalene (13.7 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 3-4: Preparation of Compound 61

Compound 61 (19.8 g, yield 74%; MS:[M+H]⁺=704) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound P-10 (22.9 g, 38.1 mmol) instead of Compound P-6, and 4-bromo-1,1′:4′,1″-terphenyl (11.8 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 3-5: Preparation of Compound 70

Compound 70 (20.2 g, yield 68%; MS:[M+H]⁺=780) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound P-10 (22.9 g, 38.1 mmol) instead of Compound P-6, and 6′-bromo-1,1′:3′,1″:4″,1′″-quaterphenyl (14.7 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 4: Preparation of Intermediate Compound Q-4

Compound Q-1 (81.6 g, yield 87%; MS:[M+H]⁺=280) was prepared in the same manner as in Synthesis Example 1-1, except that (2-methoxyphenyl)boronic acid (50.7 g, 333.5 mmol) was used instead of (5-chloro-2-methoxyphenyl)boronic acid (62.2 g, 333.5 mmol).

Compound Q-2 (71.2 g, yield 99%; MS:[M+H]⁺=266) was prepared in the same manner as in Synthesis Example 1-1, except that Compound Q-1 (75.7 g, 269.4 mmol) was used instead of Compound P-1 (85.0 g, 269.4 mmol).

Compound Q-3 (62.3 g, yield 95%; MS:[M+H]⁺=246) was prepared in the same manner as in Synthesis Example 1-1, except that Compound Q-2 (70.9 g, 265.3 mmol) was used instead of Compound P-2 (80.0 g, 265.3 mmol).

Compound Q-3 (40 g, 161.9 mmol) was dissolved in 200 ml of acetic acid, to which iodine (4.16 g, 81.0 mmol), iodic acid (6.3 g, 36.0 mmol) and sulfuric acid (10 mi) were added and stirred at 65° C. for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and water was added. The resulting solid was filtered, washed with water and then recrystallized from toluene and ethyl acetate to obtain Compound Q-4 (50.1 g, yield 83%; MS: [M+H]⁺=372).

Synthesis Example 4-1: Preparation of Intermediate Compound Q-5

Compound Q-4 (30 g, 80.4 mmol) and 4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g, 80.4 mmol) were dissolved in 300 ml of tetrahydrofuran (THF), to which 2M sodium carbonate (Na₂CO₃) solution (120 mL) and tetrakis (triphenylphosphine)palladium(0) [Pd(PPh₃)₄](1.9 g, 2 mol %) and refluxed for 6 hours. After completion of the reaction, the mixture was cooled to room temperature, and the resulting mixture was extracted three times with water and toluene. The toluene layer was separated and dried over magnesium sulfate.

The filtrate was distilled under reduced pressure, and the obtained mixture was recrystallized from chloroform and ethyl acetate to obtain Compound Q-5 (28.9 g, yield 76%; MS: [M+H]⁺=473).

Synthesis Example 4-2: Preparation of Intermediate Compound Q-6

Compound Q-5 (25 g, 52.8 mmol), bis(pinacolato)diboron (14.9 g, 58.1 mmol), potassium acetate (15.5 g, 158.4 mmol) and tetrakis(triphenylphosphine) palladium(0) [Pd(PPh₃)₄] (1.2 g, 2 mol %) was added to tetrahydrofuran (300 ml) and refluxed for 12 hours. After completion of the reaction, the mixture was cooled to room temperature and distilled under reduced pressure to remove the solvent. This was dissolved in chloroform and washed three times with water. The organic layer was separated, dried with magnesium sulfate, and then distilled under reduced pressure to obtain Compound Q-6 (25.0 g, yield 91%; MS: [M+H]⁺=521).

Synthesis Example 4-3: Preparation of Compound 7

Compound 7 (19.0 g, yield 71%; MS:[M+H]⁺=702) was prepared in the same manner as in Synthesis Example 1-1, except for using 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (16.6 g, 38.1 mmol) instead of Compound P-6, and Compound Q-5 (18.0 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 4-4: Preparation of Compound 8

Compound 8 (19.9 g, yield 73%; MS:[M+H]⁺=716) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound Q-6 (19.8 g, 38.1 mmol) instead of Compound P-6, and 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (13.6 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 4-5: Preparation of Compound 19

Compound 19 (19.5 g, yield 70%; MS:[M+H]⁺=732) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound Q-6 (19.8 g, 38.1 mmol) instead of Compound P-6, and 2-chloro-4-(dibenzo[b,d]thiophen-3-yl)-6-phenyl-1,3,5-triazine (14.2 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 4-6: Preparation of Compound 48

Compound 48 (22.3 g, yield 74%; MS:[M+H]⁺=791) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound Q-6 (19.8 g, 38.1 mmol) instead of Compound P-6, and 4-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-9-phenyl-9H-carbazole (16.5 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 4-7: Preparation of Compound 58

Compound 58 (18.7 g, yield 62%; MS:[M+H]⁺=792) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound Q-6 (19.8 g, 38.1 mmol) instead of Compound P-6, and 2-(2-bromophenyl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (18.2 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 5-1: Preparation of Intermediate Compound Q-7

Compound Q-7 (20.0 g, yield 59%; MS:[M+H]⁺=423) was prepared in the same manner as in Synthesis Example 4-1, except that 4,4,5,5-tetramethyl-2-(phenanthren-2-yl)-1,3,2-dioxaborolane (24.5 g, 80.4 mmol) was used instead of 4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g, 80.4 mmol).

Synthesis Example 5-2: Preparation of Intermediate Compound Q-8

Compound Q-8 (21.6 g, yield 87%; MS:[M+H]⁺=471) was prepared in the same manner as in Synthesis Example 4-2, except that Compound Q-7 (22.4 g, 52.8 mmol) was used instead of Compound Q-5 (25 g, 52.8 mmol).

Synthesis Example 5-3: Preparation of Compound 10

Compound 10 (18.4 g, yield 65%; MS:[M+H]⁺=742) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound Q-8 (17.9 g, 38.1 mmol) instead of Compound P-6, and 2-(4-chlorophenyl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (16.5 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 5-4: Preparation of Compound 15

Compound 15 (15.8 g, yield 54%; MS:[M+H]⁺=768) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound Q-8 (17.9 g, 38.1 mmol) instead of Compound P-6, and 2-chloro-4-(4-(9,9-dimethyl-9H-fluoren-1-yl)phenyl)-6-phenyl-1,3,5-triazine (17.5 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 6-1: Preparation of Intermediate Compound Q-9

Compound Q-9 (20.8 g, yield 61%; MS:[M+H]⁺=423) was prepared in the same manner as in Synthesis Example 4-1, except that 4,4,5,5-tetramethyl-2-(phenanthren-9-yl)-1,3,2-dioxaborolane (24.5 g, 80.4 mmol) was used instead of 4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g, 80.4 mmol).

Synthesis Example 6-2: Preparation of Intermediate Compound Q-10

Compound Q-10 (21.1 g, yield 85%; MS:[M+H]⁺=471) was prepared in the same manner as in Synthesis Example 4-2, except that Compound Q-7 (22.4 g, 52.8 mmol) was used instead of Compound Q-5 (25 g, 52.8 mmol)

Synthesis Example 6-3: Preparation of Compound 50

Compound 50 (14.4 g, yield 51%; MS:[M+H]⁺=742) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound Q-8 (17.9 g, 38.1 mmol) instead of Compound P-6, and 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (16.6 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 7-1: Preparation of Intermediate Compound Q-11

Compound Q-11 (23.6 g, yield 62%; MS:[M+H]⁺=473) was prepared in the same manner as in Synthesis Example 4-1, except that 2-(chrysen-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (28.4 g, 80.4 mmol) was used instead of 4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g, 80.4 mmol).

Synthesis Example 7-2: Preparation of Intermediate Compound Q-12

Compound Q-12 (22.5 g, yield 82%; MS:[M+H]⁺=521) was prepared in the same manner as in Synthesis Example 4-2, except that Compound Q-11 (25.0 g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 7-3: Preparation of Compound 14

Compound 14 (14.5 g, yield 48%; MS:[M+H]⁺=792) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound Q-12 (17.9 g, 38.1 mmol) instead of Compound P-6, and 2-(2-chlorophenyl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (16.5 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 8-1: Preparation of Intermediate Compound Q-13

Compound Q-13 (29.3 g, yield 73%; MS:[M+H]⁺=499) was prepared in the same manner as in Synthesis Example 4-1, except that 4,4,5,5-tetramethyl-2-(4-(phenanthren-9-yl)phenyl)-1,3,2-dioxaborolane (30.6 g, 80.4 mmol) was used instead of 4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g, 80.4 mmol).

Synthesis Example 8-2: Preparation of Intermediate Compound Q-14

Compound Q-14 (24.5 g, yield 85%; MS:[M+H]⁺=547) was prepared in the same manner as in Synthesis Example 4-2, except that Compound Q-13 (26.4 g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 8-3: Preparation of Compound 17

Compound 17 (18.9 g, yield 68%; MS:[M+H]⁺=728) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound Q-14 (20.8 g, 38.1 mmol) instead of Compound P-6, and 2-([1,1′-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (13.1 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 9-1: Preparation of Intermediate Compound Q-15

Compound Q-15 (25.7 g, yield 80%; MS:[M+H]⁺=399) was prepared in the same manner as in Synthesis Example 4-1, except that 2-([1,1′-biphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (22.5 g, 80.4 mmol) was used instead of 4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g, 80.4 mmol).

Synthesis Example 9-2: Preparation of Intermediate Compound Q-16

Compound Q-16 (20.3 g, yield 86%; MS:[M+H]⁺=447) was prepared in the same manner as in Synthesis Example 4-2, except that Compound Q-13 (21.1 g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 9-3: Preparation of Compound 30

Compound 30 (18.9 g, yield 69%; MS:[M+H]⁺=718) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound Q-16 (17.0 g, 38.1 mmol) instead of Compound P-6, and 2-chloro-4-(3-(dibenzo[b,d]furan-1-yl)phenyl)-6-phenyl-1,3,5-triazine (16.5 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 9-4: Preparation of Compound 39

Compound 39 (17.4 g, yield 65%; MS:[M+H]⁺=704) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound Q-16 (17.0 g, 38.1 mmol) instead of Compound P-6, and 2-([1,1′:3′,1″-terphenyl]-5′-yl)-4-chloro-6-phenyl-1,3,5-triazine (16.0 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 9-5: Preparation of Compound 44

Compound 44 (19.4 g, yield 62%; MS:[M+H]⁺=820) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound Q-16 (17.0 g, 38.1 mmol) instead of Compound P-6, and 2-(3-chlorophenyl)-4-(4-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-6-phenyl-1,3,5-triazine (20.4 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 9-6: Preparation of Compound 63

Compound 63 (17.4 g, yield 65%; MS:[M+H]⁺=704) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound Q-16 (17.0 g, 38.1 mmol) instead of Compound P-6, and 2-([1,1′:3′,1″-terphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (16.0 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 9-7: Preparation of Compound 64

Compound 64 (17.5 g, yield 64%; MS:[M+H]⁺=718) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound Q-16 (17.0 g, 38.1 mmol) instead of Compound P-6, and 2-chloro-4-(3-(dibenzo[b,d]furan-4-yl)phenyl)-6-phenyl-1,3,5-triazine (16.5 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 9-8: Preparation of Compound 74

Compound 74 (17.3 g, yield 62%; MS:[M+H]⁺=734) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound Q-16 (17.0 g, 38.1 mmol) instead of Compound P-6, and 2-(4-chlorophenyl)-4-(dibenzo[b,d]thiophen-2-yl)-6-phenyl-1,3,5-triazine (17.1 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 10-1: Preparation of Intermediate Compound Q-17

Compound Q-17 (28.0 g, yield 63%; MS:[M+H]⁺=551) was prepared in the same manner as in Synthesis Example 4-1, except that 6′-chloro-1,1′:3′,1 “:4”,1′″-quaterphenyl (27.4 g, 80.4 mmol) was used instead of 4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g, 80.4 mmol).

Synthesis Example 10-2: Preparation of Intermediate Compound Q-18

Compound Q-18 (25.9 g, yield 82%; MS:[M+H]⁺=599) was prepared in the same manner as in Synthesis Example 4-2, except that Compound Q-17 (29.1 g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 10-3: Preparation of Compound 31

Compound 31 (18.2 g, yield 68%; MS:[M+H]⁺=703) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound Q-18 (22.8 g, 38.1 mmol) instead of Compound P-6, and 4-chloro-2,6-diphenylpyrimidine (10.2 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 11-1: Preparation of Intermediate Compound Q-19

Compound Q-19 (25.2 g, yield 66%; MS:[M+H]⁺=475) was prepared in the same manner as in Synthesis Example 4-1, except that 2-([1,1′:2′,1″-terphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (28.6 g, 80.4 mmol) was used instead of 4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g, 80.4 mmol).

Synthesis Example 11-2: Preparation of Intermediate Compound Q-20

Compound Q-20 (22.1 g, yield 80%; MS:[M+H]⁺=523) was prepared in the same manner as in Synthesis Example 4-2, except that Compound Q-19 (25.1 g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 11-3: Preparation of Compound 32

Compound 32 (15.8 g, yield 61%; MS:[M+H]⁺=678) was prepared in the same manner as in Synthesis Example 1-1, except for using Q-20 (19.9 g, 38.1 mmol) instead of Compound P-6, and 2-chloro-4-(naphthalen-1-yl)-6-phenyl-1,3,5-triazine (12.1 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 12-1: Preparation of Compound Q-21

Compound Q-21 (27.1 g, yield 71%; MS:[M+H]⁺=475) was prepared in the same manner as in Synthesis Example 4-1, except that [1,1′:4′,1″-terphenyl]-3-ylboronic acid (22.0 g, 80.4 mmol) was used instead of 4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g, 80.4 mmol).

Synthesis Example 12-2: Preparation of Compound Q-22

Compound Q-22 (21.5 g, yield 78%; MS:[M+H]⁺=523) was prepared in the same manner as in Synthesis Example 4-2, except that Compound Q-21 (25.1 g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 12-3: Preparation of Compound 33

Compound 33 (18.8 g, yield 69%; MS:[M+H]⁺=718) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound Q-22 (19.9 g, 38.1 mmol) instead of Compound P-6, and 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (13.6 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 12-4: Preparation of Compound 67

Compound 67 (17.2 g, yield 63%; MS:[M+H]⁺=718) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound Q-22 (19.9 g, 38.1 mmol) instead of Compound P-6, and 2-chloro-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (13.6 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 13-1: Preparation of Intermediate Compound Q-23

Compound Q-23 (24.5 g, yield 64%; MS:[M+H]⁺=475) was prepared in the same manner as in Synthesis Example 4-1, except that [1,1′:3′,1″-terphenyl]-3-ylboronic acid (22.0 g, 80.4 mmol) was used instead of 4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g, 80.4 mmol).

Synthesis Example 13-2: Preparation of Intermediate Compound Q-24

Compound Q-24 (20.7 g, yield 75%; MS:[M+H]⁺=523) was prepared in the same manner as in Synthesis Example 4-2, except that Compound Q-23 (25.1 g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 13-3: Preparation of Compound 34

Compound 34 (19.6 g, yield 73%; MS:[M+H]⁺=704) was prepared in the same manner as in Synthesis Example 4-1, except for using Q-24 (19.9 g, 38.1 mmol) instead of Compound P-6, and 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (13.1 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 13-4: Preparation of Compound 69

Compound 69 (18.8 g, yield 70%; MS:[M+H]⁺=704) was prepared in the same manner as in Synthesis Example 1-1, except for using Q-24 (19.9 g, 38.1 mmol) instead of Compound P-6, and 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (13.1 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 14-1: Preparation of Intermediate Compound Q-25

Compound Q-25 (21.8 g, yield 68%; MS:[M+H]⁺=399) was prepared in the same manner as in Synthesis Example 4-1, except that [1,1′-biphenyl]-3-ylboronic acid (15.9 g, 80.4 mmol) was used instead of 4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g, 80.4 mmol).

Synthesis Example 14-2: Preparation of Intermediate Compound Q-26

Compound Q-26 (16.5 g, yield 70%; MS:[M+H]⁺=447) was prepared in the same manner as in Synthesis Example 4-2, except that Compound Q-25 (21.1 g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 14-3: Preparation of Compound 35

Compound 35 (17.4 g, yield 65%; MS:[M+H]⁺=704) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound Q-26 (19.9 g, 38.1 mmol) instead of Compound P-6, and 2-([1,1′:2′,1″-terphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (16.0 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 14-4: Preparation of Compound 71

Compound 71 (15.8 g, yield 59%; MS-[M+H]⁺=704) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound Q-26 (19.9 g, 38.1 mmol) instead of Compound P-6, and 2-([1,1′-3′,1″-terphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (16.0 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 15-1: Preparation of Intermediate Compound Q-27

Compound Q-27 (27.4 g, yield 62%; MS:[M+H]⁺=549) was prepared in the same manner as in Synthesis Example 4-1, except that (4-(triphenylen-2-yl)phenyl)boronic acid (28.0 g, 80.4 mmol) was used instead of 4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g, 80.4 mmol).

Synthesis Example 15-2: Preparation of Intermediate Compound Q-28

Compound Q-28 (26.1 g, yield 83%; MS:[M+H]⁺=597) was prepared in the same manner as in Synthesis Example 4-2, except that Compound Q-27 (29.0 g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 15-3: Preparation of Compound 47

Compound 47 (20.2 g, yield 68%; MS:[M+H]⁺=778) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound Q-28 (19.9 g, 38.1 mmol) instead of Compound P-6, and 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (13.1 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 16-1: Preparation of Intermediate Compound Q-29

Compound 29 (22.5 g, yield 59%; MS:[M+H]⁺=473) was prepared in the same manner as in Synthesis Example 4-1, except that chrysen-2-ylboronic acid (21.9 g, 80.4 mmol) was used instead of 4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g, 80.4 mmol).

Synthesis Example 16-2: Preparation of Intermediate Compound Q-30

Compound Q-30 (23.9 g, yield 87%; MS:[M+H]⁺=521) was prepared in the same manner as in Synthesis Example 4-2, except that Compound Q-29 (25.0 g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 16-3: Preparation of Compound 51

Compound 51 (17.0 g, yield 61%; MS:[M+H]⁺=732) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound Q-30 (19.8 g, 38.1 mmol) instead of Compound P-6, and 2-chloro-4-(dibenzo[b,d]thiophen-2-yl)-6-phenyl-1,3,5-triazine (14.2 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 17-1: Preparation of Intermediate Compound Q-31

Compound Q-31 (22.8 g, yield 63%; MS:[M+H]⁺=449) was prepared in the same manner as in Synthesis Example 4-1, except that (3a1,5a1-dihydropyren-1-yl)boronic acid (19.9 g, 80.4 mmol) was used instead of 4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g, 80.4 mmol).

Synthesis Example 17-2: Preparation of Intermediate Compound Q-32

Compound Q-32 (22.3 g, yield 85%; MS:[M+H]⁺=497) was prepared in the same manner as in Synthesis Example 4-2, except that Compound Q-31 (23.7 g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 17-3: Preparation of Compound 52

Compound 52 (17.0 g, yield 62%; MS:[M+H]⁺=718) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound Q-32 (18.9 g, 38.1 mmol) instead of Compound P-6, and 2-chloro-4-(9,9-dimethyl-9H-fluoren-1-yl)-6-phenyl-1,3,5-triazine (14.6 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 18-1: Preparation of Intermediate Compound Q-33

Compound Q-33 (27.3 g, yield 60%; MS:[M+H]⁺=565) was prepared in the same manner as in Synthesis Example 4-1, except that (3-tritylphenyl)boronic acid (29.3 g, 80.4 mmol) was used instead of 4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g, 80.4 mmol).

Synthesis Example 18-2: Preparation of Intermediate Compound Q-34

Compound Q-34 (28.1 g, yield 87%; MS:[M+H]⁺=613) was prepared in the same manner as in Synthesis Example 4-2, except that Compound Q-33 (13.4 g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 18-3: Preparation of Compound 56

Compound 56 (20.3 g, yield 64%; MS:[M+H]⁺=834) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound Q-34 (23.3 g, 38.1 mmol) instead of Compound P-6, and 2-chloro-4-(9,9-dimethyl-9H-fluoren-4-yl)-6-phenyl-1,3,5-triazine (14.6 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 19-1: Preparation of Intermediate Compound Q-35

Compound Q-35 (21.0 g, yield 55%; MS:[M+H]⁺=475) was prepared in the same manner as in Synthesis Example 4-1, except that [1,1′:4′,1″-terphenyl]-4-ylboronic acid (22.0 g, 80.4 mmol) was used instead of 4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g, 80.4 mmol).

Synthesis Example 19-2: Preparation of Intermediate Compound Q-36

Compound Q-36 (24.6 g, yield 89%; MS:[M+H]⁺=523) was prepared in the same manner as in Synthesis Example 4-2, except that Compound Q-35 (25.1 g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 19-3: Preparation of Compound 75

Compound 75 (16.0 g, yield 67%; MS:[M+H]⁺=627) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound Q-36 (19.9 g, 38.1 mmol) instead of Compound P-6, and 4-chloro-2,6-diphenylpyrimidine (10.2 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 20: Preparation of Intermediate Compound R-6

1-Bromo-3-iodobenzene (50 g, 176.7 mmol) and 2-bromothiophenol (40.1 g, 212.0 mmol) were dispersed in ethanol (EtOH, 500 ml) to which NaOH (9.2 g, 229.7 mmol) was added and then refluxed for 6 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and water was added thereto. The obtained organic layer was distilled under reduced pressure. The mixture was filtered through silica gel to obtain Compound R-1 (48.6 g, yield 80%; MS: [M+H]⁺=342).

After Compound R-1 (40.0 g, 116.3 mmol) was dissolved in 500 ml of dichloromethane (DCM), 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (31.6 g, 140.0 mmol) was added thereto and stirred at room temperature for 24 hours. After completion of the reaction, the mixture was extracted three times with an excess amount of water. The organic layer was dried over magnesium sulfate and then distilled under reduced pressure to obtain Compound R-2 (21.7 g, yield 71%; MS: [M+H]⁺=262).

After Compound R-2 (20 g, 76.0 mmol) was dissolved in tetrahydrofuran (250 ml), the temperature was lowered to −78° C. and 1.7M tert-butyllithium (t-BuLi) (44.7 ml, 76.0 mmol) was slowly added. After stirring at the same temperature for one hour, triisopropylborate (B(OiPr)₃) (20.1 ml, 152.0 mmol) was added and stirred for 3 hours while gradually raising the temperature to room temperature. To the reaction mixture was added 2N aqueous hydrochloric acid solution (100 ml) and the mixture was stirred at room temperature for 1.5 hours. The resulting precipitate was filtered, washed sequentially with water and ethyl ether, and dried under vacuum. After drying, the reaction mixture was dispersed in ethyl ether, stirred for two hours, filtered and dried to obtain Compound R-3 (151 g, yield 87%; MS: [M+H]⁺=229).

After Compound R-3 (15.0 g, 65.8 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (17.6 g, 162.3 mmol) were dispersed in tetrahydrofuran (200 ml), 2M potassium aqueous solution (aq.K₂CO₃) (98.7 ml, 197.4 mmol) was added and tetrakis(triphenylphosphine)palladium [Pd(PPh₃)₄] (1.5 g, 2 mol %) was added. The mixture was stirred and refluxed for 5 hours. The temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was recrystallized from tetrahydrofuran and ethyl acetate, filtered and then dried to obtain compound R-4 (24.1 g, yield 88%; MS: [M+H]⁺=416).

Compound R-4 (40 g, 96.3 mmol) was dissolved in chloroform (350 mL) to which acetic acid (350 mL) was added and Br₂ (5.2 mL, 101.1 mmol) was added dropwise at 0° C. The obtained mixture was warmed to room temperature and stirred for 5 hours. After completion of the reaction, the reaction solution was concentrated and recrystallized from ethanol to obtain Compound R-5 (34.3 g, yield 72%; MS: [M+H]⁺=494).

Compound R-5 (40 g, 80.9 mmol), bis(pinacolato)diboron (24.7 g, 97.1 mmol), potassium acetate (33.5 g, 242.7 mmol) and tetrakis(triphenylphosphine)palladium(0) [Pd(PPh₃)₄] (1.9 g, 2 mol %) were added to tetrahydrofuran (500 ml) and refluxed for 12 hours. After completion of the reaction, the mixture was cooled to room temperature, and distilled under reduced pressure to remove the solvent. This was dissolved in chloroform and washed three times with water. The organic layer was separated, dried with magnesium sulfate and distilled under reduced pressure to obtain Compound R-6 (39.9 g, yield 91%; MS: [M+H]⁺=542).

Synthesis Example 20-1: Preparation of Compound 5

Compound 5 (17.9 g, yield 76%; MS:[M+H]⁺=616) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound R-6 (20.6 g, 38.1 mmol) instead of Compound P-6, and 3-bromofluoranthene (10.7 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 20-2: Preparation of Compound 53

Compound 53 (18.9 g, yield 69%; MS:[M+H]⁺=718) was prepared in the same manner as in Synthesis Example 1-1, except for using Compound R-6 (20.6 g, 38.1 mmol) instead of Compound P-6, and 3-(6-bromonaphthalen-2-yl)phenanthrene (14.6 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 21: Preparation of Intermediate Compound S-2

Compound S-1 (68.6 g, yield 86%; MS:[M+H]⁺=492) was prepared in the same manner as manner as in the preparation method of Compound R-4 of Synthesis Example 20, except that 2-([1,1′-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (55.8 g, 162.3 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (17.6 g, 162.3 mmol).

Compound S-2 (50.5 g, yield 92%; MS:[M+H]⁺=492) was prepared in the same manner as manner as in the preparation method of Compound R-5 of Synthesis Example 20, except that Compound S-1 (47.3 g, 96.3 mmol) was used instead of Compound R-4 (40 g, 96.3 mmol).

Synthesis Example 21-1: Preparation of Compound 78

Compound 78 (14.8 g, yield 54%; MS:[M+H]⁺=720) was prepared in the same manner as manner as in Synthesis Example 1-1, except for using Compound S-2 (20.6 g, 38.1 mmol) instead of Compound P-6, and [1,1′:4′,1″-terphenyl]-2′-ylboronic acid (10.4 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 22: Preparation of Intermediate Compound S-3

Compound S-3 (71.0 g, yield 89%; MS:[M+H]⁺=492) was prepared in the same manner as manner as in the preparation method of Compound R-4 of Synthesis Example 20, except that 2-([1,1′-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (55.8 g, 162.3 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (17.6 g, 162.3 mmol).

Compound S-4 (49.4 g, yield 90%; MS:[M+H]⁺=570) was prepared in the same manner as manner as in the preparation method of Compound R-5 of Synthesis Example 20, except that Compound S-3 (47.3 g, 96.3 mmol) was used instead of Compound R-4 (40 g, 96.3 mmol).

Synthesis Example 22-1: Preparation of Compound 79

Compound 79 (20.6 g, yield 68%; MS:[M+H]⁺=796) was prepared in the same manner as manner as in Synthesis Example 1-1, except for using S-4 (21.7 g, 38.1 mmol) instead of Compound P-6, and (4′-phenyl-[1,1′:3′,1″-terphenyl]-4-yl)boronic acid (13.3 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 23: Preparation of Intermediate Compound S-6

Compound S-5 (57.9 g, yield 86%; MS:[M+H]⁺=415) was prepared in the same manner as manner as in the preparation method of Compound R-4 of Synthesis Example 20, except that 2-chloro-4,6-diphenylpyrimidine (43.3 g, 162.3 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (17.6 g, 162.3 mmol).

Compound S-6 (41.3 g, yield 87%; MS:[M+H]⁺=493) was prepared in the same manner as manner as in the preparation method of Compound R-5 of Synthesis Example 20, except that Compound S-3 (39.9 g, 96.3 mmol) was used instead of Compound R-4 (40 g, 96.3 mmol).

Synthesis Example 23-1: Preparation of Compound 43

Compound 43 (18.4 g, yield 67%; MS:[M+H]⁺=719) was prepared in the same manner as manner as in Synthesis Example 1-1, except for using S-6 (18.8 g, 38.1 mmol) instead of Compound P-6, and [1,1′:3′,1″:3″,1′″-quaterphenyl]-4-ylboronic acid (13.3 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 23-2: Preparation of Compound 80

Compound 80 (17.8 g, yield 65%; MS:[M+H]⁺=719) was prepared in the same manner as manner as in Synthesis Example 1-1, except for using S-6 (18.8 g, 38.1 mmol) instead of Compound P-6, and [1,1′:2′,1″:4″,1′″-quaterphenyl]-4′″-ylboronic acid (13.3 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 24: Preparation of Intermediate Compound S-8

Compound S-7 (80.5 g, yield 83%; MS:[M+H]⁺=598) was prepared in the same manner as manner as in the preparation method of Compound R-4 of Synthesis Example 20, except that 2-(4-chlorophenyl)-4-(dibenzo[b,d]thiophen-2-yl)-6-phenyl-1,3,5-triazine (73.0 g, 162.3 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (17.6 g, 162.3 mmol).

Compound S-8 (52.8 g, yield 81%; MS:[M+H]⁺=676) was prepared in the same manner as manner as in the preparation method of Compound R-5 of Synthesis Example 20, except that Compound S-7 (57.6 g, 96.3 mmol) was used instead of Compound R-4 (40 g, 96.3 mmol).

Synthesis Example 24-1: Preparation of Compound 18

Compound 18 (17.5 g, yield 54%; MS:[M+H]⁺=850) was prepared in the same manner as manner as in Synthesis Example 1-1, except for using Compound S-8 (18.8 g, 38.1 mmol) instead of Compound P-6, and 4,4,5,5-tetramethyl-2-(10-phenylphenanthren-9-yl)-1,3,2-dioxaborolane (14.5 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 25: Preparation of Intermediate Compound S-10

Compound S-9 (71.4 g, yield 87%; MS:[M+H]⁺=506) was prepared in the same manner as manner as in the preparation method of Compound R-4 of Synthesis Example 20, except that 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (58.1 g, 162.3 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (17.6 g, 162.3 mmol).

Compound S-10 (46.2 g, yield 82%; MS:[M+H]⁺=584) was prepared in the same manner as manner as in the preparation method of Compound R-5 of Synthesis Example 20, except that Compound S-9 (48.7 g, 96.3 mmol) was used instead of Compound R-4 (40 g, 96.3 mmol).

Synthesis Example 25-1: Preparation of Compound 20

Compound 20 (18.7 g, yield 67%; MS:[M+H]⁺=732) was prepared in the same manner as manner as in Synthesis Example 1-1, except for using Compound S-10 (34.5 g, 38.1 mmol) instead of Compound P-6, and triphenylen-2-ylboronic acid (10.4 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 26: Preparation of Intermediate Compound S-12

Compound S-11 (71.6 g, yield 89%; MS:[M+H]⁺=496) was prepared in the same manner as manner as in the preparation method of Compound R-4 of Synthesis Example 20, except that 2-([1,1′-biphenyl]-4-yl-2′,3′,4′,5′,6′-d5)-4-chloro-6-phenylpyrimidine (56.5 g, 162.3 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (17.6 g, 162.3 mmol).

Compound S-12 (47.0 g, yield 85%; MS:[M+H]⁺=574) was prepared in the same manner as manner as in the preparation method of Compound R-5 of Synthesis Example 20, except that Compound S-11 (47.7 g, 96.3 mmol) was used instead of Compound R-4 (40 g, 96.3 mmol).

Synthesis Example 26-1: Preparation of Compound 24

Compound 24 (19.5 g, yield 71%; MS:[M+H]⁺=722) was prepared in the same manner as manner as in Synthesis Example 1-1, except for using Compound S-12 (21.9 g, 38.1 mmol) instead of Compound P-6, and triphenylen-2-ylboronic acid (10.4 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 27-1: Preparation of Intermediate Compound Q-37

Compound Q-37 (30.6 g, yield 60%; MS:[M+H]⁺=581) was prepared in the same manner as manner as in Synthesis Example 4-1, except that (3-(triphenylsilyl)phenyl)boronic acid (30.6 g, 80.4 mmol) was used instead of 4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g, 80.4 mmol).

Synthesis Example 27-2: Preparation of Intermediate Compound Q-38

Compound Q-38 (28.5 g, yield 86%; MS:[M+H]⁺=629) was prepared in the same manner as in Synthesis Example 4-2, except that Compound Q-37 (30.7 g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 27-3: Preparation of Compound 38

Compound 38 (19.2 g, yield 60%; MS:[M+H]⁺=840) was prepared in the same manner as manner as in Synthesis Example 1-1, except for using Q-38 (24.0 g, 38.1 mmol) instead of Compound P-6, and 2-chloro-4-(dibenzo[b,d]thiophen-2-yl)-6-phenyl-1,3,5-triazine (14.2 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 28: Preparation of Intermediate Compound S-14

Compound S-13 (71.4 g, yield 87%; MS:[M+H]⁺=506) was prepared in the same manner as manner as in the preparation method of Compound R-4 of Synthesis Example 20, except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (58.1 g, 162.3 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (17.6 g, 162.3 mmol).

Compound S-14 (50.1 g, yield 89%; MS:[M+H]⁺=584) was prepared in the same manner as manner as in the preparation method of Compound R-5 of Synthesis Example 20, except that Compound S-13 (48.7 g, 96.3 mmol) was used instead of Compound R-4 (40 g, 96.3 mmol).

Synthesis Example 28-1: Preparation of Compound 41

Compound 41 (19.3 g, yield 69%; MS:[M+H]⁺=734) was prepared in the same manner as manner as in Synthesis Example 1-1, except for using Compound S-14 (21.9 g, 38.1 mmol) instead of Compound P-6, and [1,1′:2′,1″-terphenyl]-3-ylboronic acid (10.4 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 29: Preparation of Intermediate Compound S-16

Compound S-15 (78.7 g, yield 93%; MS:[M+H]⁺=522) was prepared in the same manner as manner as in the preparation method of Compound R-4 of Synthesis Example 20, except that 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine (60.7 g, 162.3 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (17.6 g, 162.3 mmol).

Compound S-16 (50.3 g, yield 87%; MS:[M+H]⁺=600) was prepared in the same manner as manner as in the preparation method of Compound R-5 of Synthesis Example 20, except that Compound S-15 (50.2 g, 96.3 mmol) was used instead of Compound R-4 (40 g, 96.3 mmol).

Synthesis Example 29-1: Preparation of Compound 42

Compound 42 (20.6 g, yield 72%; MS:[M+H]⁺=750) was prepared in the same manner as manner as in Synthesis Example 1-1, except for using Compound S-16 (22.9 g, 38.1 mmol) instead of Compound P-6, and [1,1′:3′,1″-terphenyl]-3-ylboronic acid (10.4 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 30: Preparation of Compound 23

After Compound 6 (20 g, 28.5 mmol) was dissolved in tetrahydrofuran (500 ml), the temperature was lowered to −78° C. and 1.7 M tert-butyllithium (t-BuLi) (16.8 ml, 28.5 mmol) was slowly added thereto. After stirring at the same temperature for one hour, excess D₂O was added dropwise to terminate the reaction. The temperature is gradually increased to room temperature, the organic layer was separated, dried with magnesium sulfate and distilled under reduced pressure. The obtained mixture was purified by column chromatography with hexane/ethyl acetate (10:1) to obtain Compound 23 (9.6 g, yield 48%; MS: [M+H]⁺=703)

Synthesis Example 31: Preparation of Compound 60

Compound 60 (8.6 g, yield 42%; MS:[M+H]⁺=718) was prepared in the same manner as manner as in Synthesis Example 30, except that Compound 8 (20.4 g, 28.5 mmol) and 1.7M tert-butyllithium (t-BuLi) (33.5 ml, 57.0 mmol) were used instead of Compound P-6.

Synthesis Example 32-1: Preparation of Intermediate Compound Q-39

Compound Q-39 (22.0 g, yield 82%; MS:[M+H]⁺=704) was prepared in the same manner as manner as in Synthesis Example 1-1, except for using Compound Q-36 (19.9 g, 38.1 mmol) instead of Compound P-6, and 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (13.1 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 32-2: Preparation of Compound 73

Compound 73 (9.9 g yield 49%; MS:[M+H]⁺=705) was prepared in the same manner as manner as in Synthesis Example 30, except that Compound Q-39 (20.1 g, 28.5 mmol) was used instead of Compound 6.

Synthesis Example 33: Preparation of Intermediate Compound T-7

Compound T-1 (65.3 g, yield 62%; MS:[M+H]⁺=314) was prepared in the same manner as manner as in the preparation method of Compound P-1 of Synthesis Example 1, except that (4-chloro-2-methoxyphenyl)boronic acid)(62.2 g, 333.5 mmol) was used instead of (5-chloro-2-methoxyphenyl)boronic acid) (62.2 g, 333.5 mmol).

Compound T-2 (43.0 g, yield 90%; MS:[M+H]⁺=300) was prepared in the same manner as manner as in the preparation method of Compound P-2 of Synthesis Example 1, except that Compound T-1 (50.0 g, 158.5 mmol) was used instead of Compound P-1 (50.0 g, 158.5 mmol).

Compound T-3 (30.6 g, yield 82%; MS:[M+H]⁺=280) was prepared in the same manner as manner as in the preparation method of Compound P-3 of Synthesis Example 1, except that Compound T-2 (40.0 g, 132.7 mmol) was used instead of Compound P-2 (40.0 g, 132.7 mmol).

Compound T-4 (25.0 g, yield 95%; MS:[M+H]⁺=247) was prepared in the same manner as manner as in the preparation method of Compound P-4 of Synthesis Example 1, except that Compound T-3 (30.0 g, 106.6 mmol) was used instead of Compound P-3 (30.0 g, 106.6 mmol).

Compound T-5 (31.7 g, yield 90%; MS:[M+H]⁺=434) was prepared in the same manner as manner as in the preparation method of Compound P-5 of Synthesis Example 1, except that Compound T-4 (20.0 g, 81.2 mmol) was used instead of Compound P-4 (20.0 g, 81.2 mmol).

Compound T-6 (37.1 g, yield 83%; MS:[M+H]⁺=550) was prepared in the same manner as manner as in the preparation method of Compound P-5 of Synthesis Example 1, except for using Compound T-4 (20.0 g, 81.2 mmol) instead of Compound P-4 (20.0 g, 81.2 mmol), and 2-chloro-4-(9,9-dimethyl-9H-fluoren-2-yl)-6-phenyl-1,3,5-triazine (31.1 g, 81.2 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

Compound T-7 (29.4 g, yield 71%; MS:[M+H]⁺=510) was prepared in the same manner as manner as in the preparation method of Compound P-5 of Synthesis Example 1, except for using Compound T-4 (20.0 g, 81.2 mmol) instead of Compound P-4 (20.0 g, 81.2 mmol), and 2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (27.9 g, 81.2 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

Synthesis Example 33-1: Preparation of Compound 76

Compound 76 (23.9 g, yield 89%; MS:[M+H]⁺=704) was prepared in the same manner as manner as in Synthesis Example 1-1, except for using Compound T-5 (16.5 g, 38.1 mmol) instead of Compound P-6, and [1,1′:3′,1″:4″,1′″-quaterphenyl]-4-ylboronic acid (13.3 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 33-2: Preparation of Compound 40

Compound 40 (26.6 g, yield 82%; MS:[M+H]⁺=850) was prepared in the same manner as manner as in Synthesis Example 1-1, except for using Compound T-6 (21.0 g, 38.1 mmol) instead of Compound P-6, and 4-(triphenylsilyl)phenyl)boronic acid (14.5 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 33-3: Preparation of Compound 21

Compound 21 (22.1 g, yield 86%; MS:[M+H]⁺=676) was prepared in the same manner as manner as in Synthesis Example 1-1, except for using Compound T-7 (19.4 g, 38.1 mmol) instead of Compound P-6, and fluoranthen-3-ylboronic acid (9.4 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 34: Preparation of Intermediate Compound U-8

After 1,3-dibromo-2-methoxybenzene (113.2 g, 426.4 mmol) was dissolved in tetrahydrofuran (1000 ml), the temperature was lowered to −78° C. and 17M tert-butyl lithium (t-BuLi) (251.7 ml, 426.4 mmol) was slowly added. After stirring at the same temperature for one hour, triisopropyl borate (B(OiPr)₃) (113.2 ml, 852.4 mmol) was added and stirred for 3 hours while gradually raising the temperature to room temperature. To the reaction mixture was added 2N aqueous hydrochloric acid solution (800 ml) and the mixture was stirred at room temperature for 1.5 hours. The resulting precipitate was filtered, washed sequentially with water and ethyl ether, and dried under vacuum. After drying, the residue was recrystallized from chloroform and ethyl acetate and dried to obtain (3-bromo-2-methoxyphenyl)boronic acid (89.6 g, yield 91%; MS: [M+H]=230).

Compound U-1 (55.8 g, yield 53%; MS:[M+H]⁺=314) was prepared in the same manner as manner as in the preparation method of Compound P-1 of Synthesis Example 1, except for using 1-chloro-3-fluoro-2-iodobenzene (85.5 g, 333.5 mmol) instead of 1-bromo-3-fluoro-2-iodobenzene, and (3-bromo-2-methoxyphenyl)boronic acid (77.0 g, 333.5 mmol) instead of (5-chloro-2-methoxyphenyl)boronic acid.

Compound U-2 (39.7 g, yield 83%; MS:[M+H]⁺=300) was prepared in the same manner as manner as in the preparation method of Compound P-2 of Synthesis Example 1, except that Compound U-1 (50.0 g, 158.5 mmol) was used instead of Compound P-1 (50.0 g, 158.5 mmol).

Compound U-3 (31.4 g, yield 84%; MS:[M+H]⁺=280) was prepared in the same manner as manner as in the preparation method of Compound P-3 of Synthesis Example 1, except that Compound U-2 (40.0 g, 132.7 mmol) was used instead of Compound P-2 (40.0 g, 132.7 mmol).

Compound U-4 (25.5 g, yield 97%; MS:[M+H]⁺=247) was prepared in the same manner as manner as in the preparation method of Compound P-4 of Synthesis Example 1, except that Compound U-3 (30.0 g, 106.6 mmol) was used instead of Compound P-3 (30.0 g, 106.6 mmol).

Compound U-5 (31.1 g, yield 86%; MS:[M+H]⁺=445) was prepared in the same manner as manner as in the preparation method of Compound P-5 of Synthesis Example 1, except for using Compound U-4 (20.0 g, 81.2 mmol) instead of Compound P-4 (20.0 g, 81.2 mmol), and triphenylen-2-ylboronic acid (22.1 g, 81.2 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

Compound U-6 (24.7 g, yield 90%; MS:[M+H]⁺=521) was prepared in the same manner as in Synthesis Example 4-2, except that Compound U-5 (22.6 g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Compound U-7 (30.8 g, yield 88%; MS:[M+H]⁺=431) was prepared in the same manner as manner as in the preparation method of Compound P-5 of Synthesis Example 1, except for using Compound U-4 (20.0 g, 81.2 mmol) instead of Compound P-4, and [1,1′:4′,1″-terphenyl]-4-ylboronic acid (22.3 g, 81.2 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

Compound U-8 (24.3 g, yield 88%; MS:[M+H]⁺=523) was prepared in the same manner as in Synthesis Example 4-2, except that Compound U-7 (22.8 g, 52.8 mmol) was used instead of Compound Q-5.

Synthesis Example 34-1: Preparation of Compound 22

Compound 22 Compound 22 (35.4 g, yield 93%; MS:[M+H]⁺=702) was prepared in the same manner as manner as in Synthesis Example 1-1, except for using Compound U-6 (19.8 g, 38.1 mmol) instead of Compound P-6, and 2-([1,1′-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (13.1 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 34-2: Preparation of Compound 77

Compound 77 (24.9 g, yield 91%; MS:[M+H]⁺=718) was prepared in Synthesis Example 1-1, except for using Compound U-8 (19.9 g, 38.1 mmol) instead of Compound P-6, and 2-chloro-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (13.6 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 35: Preparation of Intermediate Compound W-8

After 2-bromo-1,3-dimethoxybenzene (92.6 g, 426.4 mmol) was dissolved in tetrahydrofuran (1000 ml), the temperature was lowered to −78° C. and 1.7M tert-butyl lithium (t-BuLi) (251.7 ml, 426.4 mmol) was slowly added. After stirring at the same temperature for 1 hour, triisopropylborate (B(OiPr)₃) (113.2 ml, 852.4 mmol) was added and the mixture was stirred for 3 hours while gradually raising the temperature to room temperature. To the reaction mixture was added 2N aqueous hydrochloric acid solution (800 ml) and the mixture was stirred at room temperature for 1.5 hours. The resulting precipitate was filtered, washed sequentially with water and ethyl ether, and dried under vacuum. After drying, the reaction product was recrystallized from chloroform and ethyl acetate and dried to obtain (2,6-dimethoxyphenyl)boronic acid (63.6 g, yield 82%; MS: [M+H]⁺=183).

Compound W-1 (35.6 g, yield 40%; MS:[M+H]⁺=267) was prepared in the same manner as manner as in the preparation method of Compound P-1 of Synthesis Example 1, except for using 1-chloro-3-fluoro-2-iodobenzene (85.5 g, 333.5 mmol) instead of 1-bromo-3-fluoro-2-iodobenzene, and (2,6-dimethoxyphenyl)boronic acid (60.7 g, 333.5 mmol) instead of (5-chloro-2-methoxyphenyl)boronic acid.

Compound W-2 (33.3 g, yield 88%; MS:[M+H]⁺=239) was prepared in the same manner as manner as in the preparation method of Compound P-2 of Synthesis Example 1, except that Compound W-1 (42.3 g, 158.5 mmol) was used instead of Compound P-1 (50.0 g, 158.5 mmol), and boron tribromide (31.6 ml, 332.9 mmol) was used.

Compound W-3 (23.5 g, yield 81%; MS:[M+H]⁺=219) was prepared in the same manner as manner as in the preparation method of Compound P-3 of Synthesis Example 1, except that Compound W-2 (31.7 g, 132.7 mmol) was used instead of Compound P-2 (40.0 g, 132.7 mmol).

After Compound W-3 (20.0 g, 91.5 mmol) was dispersed in acetonitrile (250 ml), calcium carbonate (51.2 g, 109.8 mmol) and nonafluorobutanesulfonyl fluoride (41.6 g, 137.3 mmol) were added thereto. The mixture was stirred at 80° C. for 1 hour. The reaction mixture was cooled to room temperature, filtered, washed with ethanol and water, and then dried to obtain Compound W-4 (38.9 g, yield 85%; MS: [M+H]⁺=500).

Compound W-5 (21.6 g, yield 62%; MS:[M+H]⁺=429) was prepared in the same manner as manner as in the preparation method of Compound P-5 of Synthesis Example 1, except for using Compound W-4 (40.7 g, 81.2 mmol) instead of Compound P-4, and triphenylen-2-ylboronic acid (22.1 g, 81.2 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

Compound W-6 (23.4 g, yield 85%; MS:[M+H]⁺=521) was prepared in the same manner as in Synthesis Example 4-2, except that Compound W-5 (22.6 g, 52.8 mmol) was used instead of Compound Q-5.

Compound W-7 (22.0 g, yield 63%; MS:[M+H]⁺=431) was prepared in the same manner as manner as in the preparation method of Compound P-5 of Synthesis Example 1, except for using Compound W-4 (40.7 g, 81.2 mmol) instead of Compound P-4, and [1,1′:4′,1″-terphenyl]-3-ylboronic acid (22.3 g, 81.2 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

Compound W-8 (22.1 g, yield 80%; MS:[M+H]⁺=523) was prepared in the same manner as in Synthesis Example 4-2, except that Compound W-7 (22.8 g, 52.8 mmol) was used instead of Compound Q-5.

Synthesis Example 35-1: Preparation of Compound 16

Compound 16 (19.5 g, yield 73%; MS:[M+H]⁺=702) was prepared in the same manner as manner as in Synthesis Example 1-1, except for using Compound W-6 (19.8 g, 38.1 mmol) instead of Compound P-6, and 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (13.1 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 35-2: Preparation of Compound 37

Compound 37 (15.5 g, yield 65%; MS:[M+H]⁺=628) was prepared in the same manner as manner as in Synthesis Example 1-1, except for using Compound W-8 (19.9 g, 38.1 mmol) instead of Compound P-6, and 2-chloro-4,6-diphenyl-1,3,5-triazine (10.2 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 36: Preparation of Compound A

After 50 g (23.0 mmol) of 2-chlorodibenzothiophene was diluted with 300 mL of chloroform, 18 mL (0.34 mol) of bromine was slowly added and stirred at room temperature for 12 hours. After completion of the reaction, the precipitated solid was filtered, dissolved again in excess chloroform by heating, and then washed with 20% sodium thiosulfate aqueous solution, and the organic layer was separated. This was washed again with a saturated aqueous sodium hydrogen carbonate solution, the organic layer was separated, water was dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. To the concentrated compound was added 300 mL of ethyl acetate, and the mixture was stirred under reflux. The resulting slurry was cooled at room temperature, filtered, and then dried under nitrogen to obtain a light brown compound X-1 (32 g, yield 47%; MS: [M+H]⁺=296).

After 48 g (0.16 mol) of Compound X-1 was dissolved in 500 mL of 1,4-dioxane, 49 g (0.19 mol) of bis(pinacolato)diboron was added thereto. 31.4 g (0.32 mol) of potassium acetate was then added with stirring, and the mixture was heated to reflux. Under stirring and reflux, 2.7 g (0.005 mol) of dibenzylidene acetone palladium and 2.7 g (0.01 mol) of tricyclohexylphosphine were added, and the mixture was stirred under reflux for 12 hours. After completion of the reaction, the reactant was cooled to room temperature, washed with water, and extracted twice with chloroform. The collected organic layer was washed once with water, and water was removed with anhydrous magnesium sulfate, followed by filtration and concentration. The concentrate was heated under stirring with a small amount of ethyl acetate and an excess of hexane mixed solution and filtered to obtain a white compound X-2 (43 g, yield 78%; MS [M+H]⁺=345).

10 g (0.03 mol) of Compound X-2 and 8.4 g (0.03 mol) of 2-chloro-4,6-diphenyl-1,3,5-triazine were dissolved in 100 mL of 1,4-dioxane to which K₃PO₄ 19 g (0.09 mol) was added and the mixture was stirred under reflux. To this mixture were added 570 mg (0.001 mol) of dibenzylideneacetone palladium and 560 mg (0.002 mol) of tricyclohexylphosphine, and the mixture was stirred under reflux for 12 hours. After completion of the reaction, the reactant was cooled to room temperature, washed with water, extracted twice with ethyl acetate, water was removed with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure so that a small amount of ethyl acetate remained. An excess amount of acetone was added to the concentrated compound, slurried and then filtered to obtain a white compound X-3 (11 g, yield 83%; MS: [M+H]⁺=150).

10 g (0.022 mol) of Compound 1-3 and 6.0 g (0.022 mol) of triphenylen-2-ylboronic acid were diluted in 80 mL of 1,4-dioxane, and 13.9 g (0.066 mol) of K₃PO₄ was added to the mixed solution, followed by heating, and the mixture was stirred under reflux. To this mixture was added 380 mg (0.66 mmol) of dibenzylideneacetone palladium and 370 mg (1.3 mmol) of tricyclohexylphosphine and stirred under reflux for 12 hours. After completion of the reaction, the reactant was cooled to room temperature, and the precipitated solid was filtered, dissolved in chloroform, and washed twice with water. The collected organic layer was dried over anhydrous magnesium sulfate, filtered and purified by recrystallization using chloroform and ethyl acetate as a mixed solution to obtain a white Compound A (9.6 g, yield 68%; MS: [M+H]⁺=642).

Synthesis Example 37: Preparation of Compound B

Compound B (35.5 g, yield 92%; MS:[M+H]⁺=476) was prepared in the same manner as manner as in the preparation method of Compound P-5 of Synthesis Example 1, except for using Compound Q-3 (20.1 g, 81.2 mmol) instead of Compound P-4, and (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid (28.7 g, 81.2 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

Synthesis Example 38: Preparation of Compound C

After 4,6-dibromodibenzofuran (20 g, 61.4 mmol), and [1,1′:4′,1″-terphenyl]-3-ylboronic acid (17.6 g, 61.4 mmol) were dispersed in tetrahydrofuran (400 ml), 2M potassium carbonate aqueous solution (aq. K₂CO₃) (92.1 ml, 184.2 mmol) was added and tetrakis(triphenylphosphine)palladium [Pd(PPh₃)₄] (1.4 g, 2 mol %) was added, and the mixture was stirred under reflux. After lowering the temperature to room temperature, the mixture was extracted with water and toluene, and the organic layer was dried with magnesium sulfate (MgSO₄) and then distilled under reduced pressure. The resulting mixture was purified by column chromatography on silica gel with hexane: ethyl acetate (15:1) to obtain Compound X-4 (54.3 g, yield 62%; MS: [M+H]⁺=475).

Compound X-5 (25.4 g, yield 92%; MS:[M+H]⁺=523) was prepared in the same manner as in Synthesis Example 4-2, except that Compound X-4 (25.1 g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Compound C (19.9 g, yield 83%; MS:[M+H]⁺=628) was prepared in the same manner as manner as in Synthesis Example 1-1, except for using Compound X-5 (19.9 g, 38.1 mmol) instead of Compound P-6, and 2-chloro-4,6-diphenyl-1,3,5-triazine (10.2 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 39: Preparation of Compound D

Dibenzo[b,d]furan-4-ylboronic acid (21.2 g, yield 94%; MS:[M+H]⁺=213) was prepared in the same manner as manner as in the preparation method of Compound P-4 of Synthesis Example 1, except that 4-bromodibenzo[b,d]furan (26.3 g, 106.6 mmol) was used instead of Compound P-3.

Compound X-6 (25.3 g, yield 89%; MS:[M+H]⁺=351) was prepared in the same manner as manner as in the preparation method of Compound P-5 of Synthesis Example 1, except for using 4-bromodibenzo[b,d]thiophene (21.4 g, 81.2 mmol) instead of Compound P-4, and dibenzo[b,d]furan-4-ylboronic acid (17.2 g, 81.2 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

A mixture was prepared in the same manner as manner as in the preparation method of Compound P-5 of Synthesis Example 20, except for using Compound X-6 (25.0 g, 71.3 mmol), chloroform (200 ml), acetic acid (200 ml) and Br₂ (3.8 mL, 74.9 mmol) instead of Compound R-4, and then purified by column chromatography on silica gel with hexane: ethyl acetate (10:1) to obtain Compound X-7 (14.4 g, yield 47%; MS: [M+H]⁺=428).

Compound X-8 (23.9 g, yield 95%; MS:[M+H]⁺=477) was prepared in the same manner as in Synthesis Example 4-2, except that Compound X-7 (22.7 g, 52.8 mmol) was used instead of Compound Q-5.

Compound D (19.7 g, yield 89%; MS:[M+H]⁺=582) was prepared in the same manner as manner as in Synthesis Example 1-1, except for using Compound X-8 (18.2 g, 38.1 mmol) instead of Compound Q-5, and 2-chloro-4,6-diphenyl-1,3,5-triazine (10.2 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 40: Preparation of Compound E

Compound X-9 (56.3 g, yield 87%; MS:[M+H]⁺=280) was prepared in the same manner as manner as in the preparation method of Compound X-1 of Synthesis Example 36, except that 2-chlorodibenzofuran (46.6 g, 230.0 mmol) was used instead of 2-chlorodibenzothiophene.

Compound X-10 (21.7 g, yield 96%; MS:[M+H]⁺=279) was prepared in the same manner as manner as in the preparation method of Compound P-5 of Synthesis Example 1, except for using Compound X-9 (22.9 g, 81.2 mmol) instead of Compound P-4, and phenylboronic acid (17.3 g, 81.2 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

Compound E (15.6 g, yield 87%; MS:[M+H]⁺=471) was prepared in the same manner as manner as in Synthesis Example 1-1, except for using Compound X-10 (10.6 g, 38.1 mmol) instead of Compound P-6, and triphenylen-2-ylboronic acid (10.4 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 41: Preparation of Compound F

Compound X-11 (29.0 g, yield 89%; MS:[M+H]⁺=400) was prepared in the same manner as manner as in the preparation method of Compound P-5 of Synthesis Example 1, except for using dibenzo[b,d]furan-4-ylboronic acid (17.2 g, 81.2 mmol) instead of Compound P-4, and 2-chloro-4,6-diphenyl-1,3,5-triazine (21.7 g, 81.2 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

A mixture was obtained in the same manner as manner as in the preparation method of Compound R-5 of Synthesis Example 20, except for using Compound X-12 (28.5 g, 71.3 mmol), chloroform (200 ml), acetic acid (200 ml) and Br₂ (3.8 mL, 74.9 mmol) instead of Compound R-4, and then purified by column chromatography on silica gel with hexane: ethyl acetate (10:1) to obtain Compound X-12 (23.5 g, yield 69%; MS: [M+H]⁺=478).

Compound F (21.7 g, yield 91%; MS:[M+H]⁺=626) was prepared in the same manner as manner as in Synthesis Example 1-1, except for using Compound X-12 (18.2 g, 38.1 mmol) instead of Compound P-6, and triphenylen-2-ylboronic acid (10.4 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 42: Preparation of Compound G

Compound G (19.8 g, yield 94%; MS:[M+H]⁺=552) was prepared in the same manner as manner as in Synthesis Example 1-1, except for using Compound X-12 (18.2 g, 38.1 mmol) instead of Compound P-6, and [1,1′-biphenyl]-4-ylboronic acid (7.5 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 43: Preparation of Compound H

Compound H (16.2 g, yield 72%; MS:[M+H]⁺=560) was prepared in the same manner as manner as in Synthesis Example 1-1, except that 2-bromo-9,9-dimethyl-9H-fluorene (10.4 g, 38.1 mmol) was used instead of 2-bromophenanthrene.

Example 1

A glass substrate on which a thin film of ITO (indium tin oxide) was coated in a thickness of 1,300 Å was put into distilled water containing the detergent dissolved therein and washed by the ultrasonic wave. The used detergent was a product commercially available from Fisher Co. and the distilled water was one which had been twice filtered by using a filter commercially available from Millipore Co. The ITO was washed for 30 minutes, and washing with ultrasonic waves was then repeated twice for 10 minutes by using distilled water. After the washing with distilled water was completed, the substrate was ultrasonically washed with isopropyl alcohol, acetone, and methanol solvent, and dried, after which it was transported to a plasma cleaner. Then, the substrate was cleaned with oxygen plasma for 5 minutes, and then transferred to a vacuum evaporator.

On the ITO transparent electrode thus prepared, a compound of HI-1 as described below was thermally deposited under vacuum to a thicknesses of 50 Å to form the hole injection layer.

On the hole injection layer, the compound of HT-1 was thermally deposited under vacuum to a thicknesses of 250 Å to form a hole transport layer, and a compound of HT-2 was deposited under vacuum to a thickness of 50 Å on the HT-1 deposition layer to form an electron blocking layer.

Next, on the HT-2 vapor deposition layer, the compound 1 prepared in Synthesis Example 1-1 was co-deposited with 12% by weight of a phosphorescent dopant YGD-1 to form a light emitting layer having a thickness of 400 Å.

On the light emitting layer, a material of ET-1 was deposited under vacuum to a thickness of 250 Å, and additionally a material of ET-2 was co-deposited with 2% by weight of L₁ to a thickness of 100 Å to form an electron transport layer and an electron injection layer. Aluminum was deposited on the electron injection layer to a thickness of 1000 Å to form a cathode.

In the above process, the vapor deposition rate of the organic material was maintained at 0.4 to 0.7 Å/sec, the deposition rate of aluminum was maintained at 2 Å/sec, and the degree of vacuum during vapor deposition was maintained at 2×10⁻⁷˜5×10⁻⁶ torr.

Examples 2 to 49

The organic light emitting devices of Examples 2 to 49 were each fabricated in the same manner as in Example 1, except that the phosphorescent host material and the dopant content at the time of forming the light emitting layer were changed as shown in Tables 1 to 3 below.

Comparative Examples 1 to 10

The organic light emitting devices of Comparative Examples 1 to 10 were each fabricated in the same manner as in Example 1, except that the phosphorescent host material and the dopant content at the time of forming the light emitting layer were changed as shown in Table 3 below. Here, the host materials represented by compound A to compound I used in Comparative Examples are as follows.

Experimental Example 1

After an electric current was applied to each of the organic light emitting devices fabricated in Examples 1 to 49 and Comparative Examples 1 to 10, the voltage, efficiency, luminance, color coordinate and life time were measured, and the results are shown in Tables 1 to 3 below. In this case, T95 means the time required for the luminance to be reduced to 95% when the initial luminance at a light density of 50 mA/cm² was taken as 100%.

TABLE 1
	Host: dopant	Voltage(V)	Efficiency	Color	Life time
	(thickness, Å)	(@ 10 mA/	(Cd/A)	coordinate	(T95, h)
No.	dopant content	cm2)	(@10 mA/cm2)	(x, y)	(@50 mA/cm2)
Example	compound 1:	2.99	62.8	(0.46, 0.54)	47.5
1	YGD-1 (400)12%
Example	compound 2:	2.99	64.1	(0.46, 0.53)	50.5
2	YGD-1(400)12%
Example	compound 3:	2.97	65.0	(0.46, 0.52)	47.0
3	YGD-1(400)16%
Example	compound 4:	3.15	62.8	(0.46, 0.53)	78.6
4	YGD-1 (400)12%
Example	compound 5:	3.11	53.8	(0.47, 0.52)	46.4
5	YGD-1(400)14%
Example	compound 6:	3.23	62.7	(0.47, 0.53)	49.9
6	YGD-1(400)12%
Example	compound 7:	3.20	63.1	(0.46, 0.53)	50.3
7	YGD-1(400)12%
Example	compound 8:	3.30	55.7	(0.47, 0.52)	87.9
8	YGD-1(400)16%
Example	compound 9:	2.97	64.2	(0.46, 0.54)	70.5
9	YGD-1(400)16%
Example	compound 10:	3.12	60.3	(0.47, 0.53)	47.7
10	YGD-1(400)16%
Example	compound 11:	2.89	63.0	(0.46, 0.53)	69.8
11	YGD-1(400)16%
Example	compound 14:	3.08	56.1	(0.45, 0.54)	47.6
12	YGD-1(400)16%
Example	compound 15:	3.00	63.0	(0.46, 0.53)	47.1
13	YGD-1(400)12%
Example	compound 16:	3.28	63.2	(0.46, 0.53)	41.8
14	YGD-1(400)12%
Example	compound 12:	3.55	65.9	(0.46, 0.52)	126.2
15	YGD-1(200:200)16%
Example	compound 13:	3.51	67.2	(0.46, 0.53)	116.0
16	PH-1:YGD-1(160:240)16%
Example	compound 4: PH-	3.57	67.7	(0.46, 0.53)	191.9
17	2:YGD-1(160:240)12%
Example	compound 17:	3.53	67.8	(0.47, 0.53)	125.1
18	PH-2:YGD-1(200:200)16%
Example	compound 18:	3.56	70.2	(0.45, 0.53)	132.8
19	PH-2:YGD-1(160:240)12%
Example	compound 19:	3.50	68.9	(0.46, 0.53)	352.0
20	PH-2:YGD-1(200:200)15%

TABLE 2
	Host: dopant	Voltage(V)	Efficiency	Color	Life time
	(thickness, Å)	(@ 10 mA/	(Cd/A)	coordinate	(T95, h)
No.	dopant content	cm2)	(@ 10 mA/cm2)	(x, y)	(@50 mA/cm2)
Example	compound 20:	3.64	65.4	(0.45, 0.54)	155.7
21	PH-3:YGD-1(160:240)12%
Example	compound 21:	3.58	64.1	(0.46, 0.54)	100.3
22	PH-2:YGD-1(200:200)14%
Example	compound 22:	3.60	66.5	(0.46, 0.54)	115.6
23	PH-3:YGD-1(200:200)16%
Example	compound 23:	3.71	66.8	(0.46, 0.53)	180.3
24	PH-2:YGD-1(160:240)12%
Example	compound 24:	3.48	67.1	(0.46, 0.53)	230.7
25	PH-2:YGD-1(160:240)12%
Example	compound 25:	3.12	60.3	(0.46, 0.52)	48.3
26	YGD-1 (400)16%
Example	compound 26:	3.01	61.7	(0.48, 0.51)	84.9
27	YGD-1 (400)12%
Example	compound 27:	2.98	58.5	(0.48, 0.51)	76.1
28	YGD-1 (400)16%
Example	compound 28:	3.00	67.1	(0.47, 0.52)	87.2
29	YGD-1 (400)16%
Example	compound 29:	3.04	65.4	(0.46, 0.53)	68.1
30	YGD-1(400)16%
Example	compound 30:	3.01	66.1	(0.46, 0.52)	73.6
31	YGD-1(400)16%
Example	compound 31:	3.12	60.2	(0.46, 0.53)	77.2
32	YGD-1(400)12%
Example	compound 32:	3.08	64.2	(0.45, 0.53)	76.8
33	YGD-1(400)12%
Example	compound 33:	3.11	52.6	(0.45, 0.53)	46.2
34	YGD-1(400)16%
Example	compound 34:	2.97	59.9	(0.46, 0.54)	74.3
35	YGD-1(400)16%
Example	compound 35:	3.04	62.4	(0.45, 0.53)	79.8
36	YGD-1(400)12%
Example	compound 36:	3.10	59.15	(0.45, 0.55)	48.4
37	YGD-1(400)16%
Example	compound 37:	3.01	59.2	(0.45, 0.53)	44.1
38	YGD-1(400)14%
Example	compound 38:	3.52	67.2	(0.46, 0.53)	160.3
39	PH-1:YGD-1(200:200)12%
Example	compound 39:	3.49	72.4	(0.45, 0.54)	265.8
40	PH-2:YGD-1(160:240)16%

TABLE 3
	Host: dopant	Voltage(V)	Efficiency	Color	Life time
	(thickness, Å)	(@ 10 mA/	(Cd/A)	coordinate	(T95, h)
No.	dopant content	cm2)	(@ 10 mA/cm2)	(x, y)	(@50 mA/cm2)
Example	compound 40:	3.61	62.6	(0.44, 0.54)	102.8
41	PH-3:YGD-1 (200:200)16%
Example	compound 41:	3.48	65.1	(0.47, 0.53)	272.1
42	PH-2:YGD-1(160:240)16%
Example	compound 42:	3.52	67.7	(0.45, 0.54)	326.1
43	PH-2:YGD-1(160:240)12%
Example	compound 43:	3.55	62.4	(0.45, 0.53)	239.8
44	PH-3:YGD-1(160:240)12%
Example	compound 44:	3.60	60.0	(0.46, 0.52)	154.2
45	PH-3:YGD-1(200:200)16%
Example	compound 46:	3.62	64.68	(0.45, 0.53)	175.3
46	PH-1:YGD-1(160:240)16%
Example	compound 28:	3.51	67.9	(0.45, 0.54)	330.2
47	PH-2:YGD-1(160:240)16%
Example	compound 81:	3.53	65.3	(0.47, 0.54)	289.6
48	PH-2:YGD-1(160:240)12%
Example	compound 45:	3.50	68.1	(0.45, 0.52)	349.8
49	PH-2:YGD-1(160:240)12%
Comparative	compound A:	3.21	61.9	(0.46, 0.53)	25.9
Example 1	YGD-1(400)12%
Comparative	compound B:	3.17	56.2	(0.47, 0.52)	27.3
Example 2	YGD-1(400)12%
Comparative	compound C:	2.92	62.2	(0.48, 0.50)	20.3
Example 3	YGD-1(400)12%
Comparative	compound D:	3.11	67.3	(0.48, 0.53)	26.2
Example 4	YGD-1(400)12%
Comparative	compound E:	4.73	28.11	(0.47, 0.51)	22.2
Example 5	YGD-1(400)12%
Comparative	compound F:	3.15	53.2	(0.48, 0.50)	27.5
Example 6	YGD-1(400)12%
Comparative	compound G:	3.14	52.7	(0.49, 0.50)	26.9
Example 7	YGD-1(400)12%
Comparative	compound H:	3.14	56.8	(0.49, 0.50)	28.9
Example 8	YGD-1(400)12%
Comparative	compound I:	3.0	60	(0.46, 0.53)	31.5
Example 9	YGD-1(400)12%
Comparative	compound A:	3.63	64.3	(0.47, 0.53)	63.2
Example10	PH-1:YGD-1(160:240)16%

Example 50

A compound of HI-1 described below was thermally deposited under vacuum to a thicknesses of 150 Å on the ITO transparent electrode prepared as in Example 1 to form the hole injection layer.

On the hole injection layer, the compound of HT-1 was thermally deposited under vacuum to a thicknesses of 1150 Å, and then a compound of HT-3 was deposited under vacuum to a thickness of 500 Å to form a hole transport layer.

Next, on the hole transport layer, the compound 47 prepared in Synthesis Example 15-3 was co-deposited with 5% by weight of a phosphorescent dopant GD-1 to form a light emitting layer having a thickness of 400 Å.

On the light emitting layer, a material of ET-3 was deposited under vacuum to a thickness of 50 Å to form a hole blocking layer, and a material of ET-4 and LIQ were deposited under vacuum at a weight ratio of 1:1 to form an electron transport layer. Lithium fluoride (LiF) was sequentially deposited on the electron transport layer in a thickness of 10 Å, and Mg was deposited with Ag of 10% by weight on the electron transport layer to form an electron injection layer having a thickness of 200 Å. Aluminum was deposited thereon in a thickness of 1000 Å to form a cathode.

In the above process, the vapor deposition rate of the organic material was maintained at 0.4 to 0.7 Å/sec, the lithium fluoride of the cathode was maintained at a deposition rate of 0.3 Å/sec, and the deposition rate of aluminum was maintained at 2 Å/sec. The degree of vacuum during vapor deposition was maintained at 1×10⁻⁷˜5×10⁻⁸ torr.

Examples 51 to 90

The organic light emitting devices of Examples 51 to 90 were each fabricated in the same manner as in Example 50, except that the phosphorescent host material and the dopant content at the time of forming the light emitting layer were changed as shown in Tables 4 and 5 below.

Comparative Examples 11 to 19

The organic light emitting devices of Comparative Examples 11 to 19 were each fabricated in the same manner as in Example 50, except that the phosphorescent host material and the dopant content at the time of forming the light emitting layer were changed as shown in Table 6 below. In this case, the host materials represented by compound A to compound I used in Comparative Examples are as described above.

Experimental Example 2

After an electric current was applied to each of the organic light emitting devices fabricated in Examples 50 to 90 and Comparative Examples 11 to 19, the voltage, efficiency, luminance, color coordinate and life time were measured, and the results are shown in Tables 4 to 6 below. In this case, T95 means the time required for the luminance to be reduced to 95% when the initial luminance at a light density of 20 mA/cm² was taken as 100%.

TABLE 4
	Host: dopant	Voltage(V)	Efficiency	Color	Life time
	(thickness, Å)	(@ 10 mA/	(Cd/A)	coordinate	(T95, h)
No.	dopant content	cm2)	(@ 10 mA/cm2)	(x, y)	(@50 mA/cm2)
Example	compound 47:	4	50.8	(0.349, 0.612)	52.9
50	GD-1(400)5%
Example	compound 48:	4.01	51.1	(0.350, 0.610)	66.4
51	GD-1(400)5%
Example	compound 49:	3.98	51.2	(0.350, 0.611)	59.65
52	GD-1(400)7%
Example	compound 50:	4.11	51.8	(0.348, 0.612)	51.8
53	GD-1(400)5%
Example	compound 51:	4.09	50.2	(0.345, 0.612)	51.4
54	GD-1(400)5%
Example	compound 52:	4.1	50.8	(0.348. 0.610)	51.5
55	GD-1(400)7%
Example	compound 16:	4.08	49.1	(0.349, 0.610)	46.7
56	GD-1(400)5%
Example	compound 53:	4.02	51.8	(0.348, 0.612)	55.5
57	GD-1(400)7%
Example	compound 20:	3.97	52.8	(0.349, 0.611)	67.7
58	GD-1(400)5%
Example	compound 54:	4.01	52.4	(0.350, 0.613)	66.2
59	GD-1(400)5%
Example	compound 46:	4.0	52.9	(0.349, 0.612)	65.6
60	GD-1(400)5%
Example	compound 55:	3.99	52.7	(0.350, 0.611)	65.8
61	GD-1(400)5%
Example	compound 56:	3.99	52.4	(0.347, 0.612)	51.3
62	GD-1(400)10%
Example	compound 4:	3.71	55.1	(0.351, 0.609)	110.2
63	PH-2:GD-1(200:200)5%
Example	compound 57:	4.07	52.9	(0.348, 0.612)	79.9
64	PH-3:GD-1(200:200)5%
Example	compound 58:	4.2	51.7	(0.347, 0.610)	88.7
65	PH-1:GD-1(200:200)5%
Example	compound 6:	4.21	53.4	(0.347, 0.613)	100.1
66	PH-2:GD-1(200:200)5%
Example	compound 50:	4.17	58.1	(0.348, 0.612)	78.9
67	PH-2:GD-1(160:240)7%
Example	compound 60:	4.23	51.7	(0.347, 0.611)	89.2
68	PH-2:GD-1(160:240)5%
Example	compound 61:	4.11	54.2	(0.351, 0.613)	106.2
69	PH-3:GD-1(200:200)5%
Example	compound 62:	4.22	51.9	(0.351, 0.613)	170.7
70	PH-2:GD-1(160:240)5%

TABLE 5
	Host: dopant	Voltage(V)	Efficiency	Color	Life time
	(thickness, Å)	(@ 10 mA/	(Cd/A)	coordinate	(T95, h)
No.	dopant content	cm2)	(@ 10 mA/cm2)	(x, y)	(@50 mA/cm2)
Example	compound 63:	4.31	54.2	(0.349, 0.613)	134.9
71	PH-3:GD-1(200:200)5%
Example	compound 64:	4.30	54.3	(0.347, 0.612)	135.4
72	PH-1:GD-1(160:240)7%
Example	compound 65:	4.19	52.9	(0.351, 0.613)	170.9
73	PH-2:GD-1(200:200)5%
Example	compound 66:	3.92	52.3	(0.351, 0.613)	171.4
74	PH-1:GD-1(160:240)10%
Example	compound 67:	4.12	54.9	(0.350, 0.611)	128.2
75	PH-2:GD-1(200:200)5%
Example	compound 68:	3.76	56.8	(0.352, 0.609)	104
76	PH-1:GD-1(160:240)5%
Example	compound 69:	4.10	55.1	(0.351, 0.613)	103.2
77	PH-2:GD-1(160:240)7%
Example	compound 70:	4.17	56.53	(0.351, 0.613)	104.5
78	PH-1:GD-1(160:240)5%
Example	compound 71:	4.24	54.6	(0.346, 0.612)	137.9
79	PH-3:GD-1(200:200)7%
Example	compound 72:	4.32	56.1	(0.350, 0.612)	158.8
80	PH-2:GD-1(200:200)5%
Example	compound 73:	4.42	51.24	(0.346, 0.611)	102.5
81	PH-2:GD-1(160:240)5%
Example	compound 74:	4.13	54.7	(0.350, 0.611)	119.9
82	PH-2:GD-1(160:240)10%
Example	compound 75:	4.43	50.35	(0.346, 0.613)	95.2
83	PH-3:GD-1(200:200)7%
Example	compound 76:	4.14	52.8	(0.346, 0.612)	105.7
84	PH-3:GD-1(160:240)10%
Example	compound 77:	4.35	56.4	(0.347, 0.611)	62.9
85	PH-1:GD-1(200:200)5%
Example	compound 78:	3.92	54	(0.352, 0.609)	81.2
86	PH-1:GD-1(200:200)5%
Example	compound 79:	4.16	56.13	(0.351, 0.613)	104.3
87	PH-3:GD-1(160:240)5%
Example	compound 80:	4.32	50.89	(0.346, 0.611)	100.4
88	PH-1:GD-1(160:240)5%
Example	compound 59:	4.29	53.7	(0.347, 0.614)	92.6
89	PH-1:GD-1(160:240)6%
Example	compound 45:	4.31	57.3	(0.350, 0.611)	168.1
90	PH-1:GD-1(160:240)7%

TABLE 6
	Host: dopant	Voltage(V)	Efficiency	Color	Life time
	(thickness, Å)	(@ 10 mA/	(Cd/A)	coordinate	(T95, h)
No.	dopant content	cm2)	(@ 10 mA/cm2)	(x, y)	(@50 mA/cm2)
Comparative	compound A:	4.18	51.2	(0.351, 0.609)	18.3
Example 11	GD-1(400)5%
Comparative	compound B:	4.16	46.1	(0.352, 0.611)	23.1
Example 12	GD-1(400)5%
Comparative	compound C:	4.10	61.8	(0.351, 0.610)	16.3
Example 13	GD-1(400)5%
Comparative	compound D:	4.21	62.4	(0.351, 0.609)	19.8
Example 14	GD-1(400)5%
Comparative	compound E:	5.80	37.1	(0.350, 0.611)	14.7
Example 15	GD-1(400)5%
Comparative	compound F:	4.08	44.0	(0.352, 0.609)	22.8
Example16	GD-1(400)5%
Comparative	compound G:	4.09	43.2	(0.352, 0.609)	22.0
Example 17	GD-1(400)5%
Comparative	compound H:	4.19	51.0	(0.352, 0.610)	27.1
Example 18	GD-1(400)5%
Comparative	compound I:	4.1	47	(0.349, 0.611)	32.2
Example 19	GD-1(400)5%

As shown in Tables 1 to 6 above, the organic light emitting devices fabricated using the compound according to the present invention as a phosphorescent host material exhibited excellent performance in terms of driving voltage, current efficiency, and lifetime as compared with the organic light emitting devices of Comparative Examples.

Particularly, the organic light emitting devices according to Examples showed an increase in lifetime of at least 150% as compared with the organic light emitting devices according to Comparative Examples 9 and 19 using Compound I, which is a phosphorescent host material commonly used in the art. Further, the organic light emitting devices according to Examples 4, 8 and 50 showed an increase in lifetime of about 250% as compared with the organic light emitting devices according to Comparative Examples 1, 6, 11 and 16 using Compounds A and F in which the substitution position of triazinyl group is different from that of the compound according to the present invention. Further, the organic light emitting device according to Example 28 also showed an increase in lifetime of about 370% or more as compared with the organic light emitting device according to Comparative Example 3 using Compound C, and the organic light emitting device according to Examples 30 and 31 also showed an increase in lifetime of about 250% or more as compared with the organic light emitting device according to Comparative Example 7 using Compound G.

In addition, it could be seen that the driving voltage, current efficiency and lifetime of the organic light emitting device according to Comparative Example 5 using the compound E containing no triazinyl group were significantly lower than those of the organic light emitting device according to Examples. Further, the organic light emitting device according to Comparative Examples 8 and 18 using the compound H substituted with a dimethylfluorenyl group showed a remarkably low life time as compared with the organic light emitting device according to Examples, which is believed to be due to the generation of impurities resulting from the formation of radicals by dimethylfluorenyl in the polymer.

Explanation of Signs
1: substrate            2:anode
3: light emitting layer 4: cathode
5: hole injection layer 6: hole transport layer
7: light emitting layer 8: electron transport layer

Claims

1. A compound of Chemical Formula 1:

2. The compound of claim 1, wherein L2 is a single bond, or any one selected from the group consisting of:

3. The compound of claim 1, wherein Y1 is N, Y2 is N, and Y3 is N; orY1 is N, Y2 is N, and Y3 is CH; orY1 is N, Y2 is CH, and Y3 is N; orY1 is N, Y2 is CH, and Y3 is CH; orY1 is CH, Y2 is CH, and Y3 is N.

4. The compound of claim 1, wherein Ar1a and Ar1b are each independently any one selected from the group consisting of:

5. The compound of claim 4, wherein Ar1a and Ar1b are each independently any one selected from the group consisting of:

6. The compound of claim 1, wherein the compound is any one compound selected from the group consisting of:

7. An organic light emitting device comprising: a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers include the compound of claim 1.

8. The organic light emitting device of claim 7, wherein the organic material layer containing the compound is a light emitting layer.

9. The organic light emitting device of claim 8, wherein the compound is used as a host material.