KR102692902B1 - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent device comprising the same. The compound according to the present invention can improve the luminous efficiency, driving voltage, lifespan, etc. of the organic electroluminescent device by being used in an organic layer of the organic electroluminescent device, preferably a light-emitting layer, an electron transport layer, or an electron transport auxiliary layer.

Description

Organic compounds and organic electroluminescent devices comprising the same {ORGANIC COMPOUNDS AND ORGANIC ELECTRO LUMINESCENCE DEVICE COMPRISING THE SAME}

The present invention relates to a novel organic compound that can be used as a material for an organic electroluminescent device and an organic electroluminescent device comprising the same.

Starting with Bernanose's observation of organic thin film luminescence in the 1950s, research on organic electroluminescent (EL) devices continued, leading to blue electroluminescence using anthracene single crystals in 1965, and in 1987, Tang proposed an organic EL device with a laminated structure divided into functional layers, a hole layer and an emission layer. Since then, in order to create high-efficiency, long-life organic EL devices, development has been made by introducing characteristic organic layers in the device, which has led to the development of specialized materials used for this.

In an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic layer from the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted. At this time, the material used as the organic layer can be classified into light-emitting materials, hole injection materials, hole transport materials, electron transport materials, and electron injection materials according to their functions.

Luminescent materials can be classified into blue, green, and red luminescent materials according to their luminescent colors, and yellow and orange luminescent materials for better natural color realization. In addition, a host/dopant system can be used as the luminescent material to increase color purity and luminescent efficiency through energy transfer.

Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. At this time, since the development of phosphorescent materials can theoretically improve luminescence efficiency by up to four times compared to fluorescence, research is being conducted not only on phosphorescent dopants but also on phosphorescent host materials.

Up to now, NPB, BCP, Alq ₃ , etc. have been widely known as materials for hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, and anthracene derivatives have been reported as materials for emitting layers. In particular, metal complex compounds containing Ir, such as Firpic, Ir(ppy) ₃ , and (acac)Ir(btp) ₂ , which have advantages in terms of improving efficiency among emitting layer materials, are being used as blue, green, and red phosphorescent dopant materials, and 4,4-dicarbazolybiphenyl (CBP) is being used as a phosphorescent host material.

However, although conventional organic layer materials have advantages in terms of luminescence characteristics, their glass transition temperature is low and their thermal stability is very poor, so they are not satisfactory in terms of the lifespan of organic electroluminescent devices. Therefore, the development of organic layer materials with excellent performance is required.

The present invention aims to solve the above-mentioned problems by providing a novel compound capable of improving the efficiency, lifespan, stability, etc. of an organic electroluminescent device and an organic electroluminescent device using the compound.

To achieve the above purpose, the present invention provides a compound represented by the following chemical formula 1:

[Chemical Formula 1]

In the above chemical formula 1,

L ₁ is selected from the group consisting of a single bond, an arylene group having C ₆ to C ₁₈ , and a heteroarylene group having 5 to 18 nuclear atoms;

Ar ₁ and Ar ₂ are each independently hydrogen, deuterium, halogen, cyano group, C ₁ to C ₃₀ alkyl group, C ₂ to C ₃₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 5 to 7 nuclear atoms, C ₆ to C ₃₀ aryl group, heteroaryl group having 5 to 30 nuclear atoms, C ₁ to C ₃₀ alkyloxy group, C ₆ to C ₃₀ aryloxy group, C ₁ to C ₃₀ alkylsilyl group, C ₅ to C ₃₀ arylsilyl group, C ₁ to C ₃₀ alkylboron group, C ₆ to C ₃₀ arylborone group, C ₆ to C ₃₀ Selected from the group consisting of an arylphosphanyl group, a C ₆ to C ₃₀ mono- or diarylphosphinyl group, and a C ₆ to C ₃₀ arylamine group;

The _arylene group and _{heteroarylene} group of the above L ₁ , and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group of the above Ar 1 and Ar 2 are each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ One or more substituents selected from the group consisting of an alkyloxy group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphanyl group, a C ₆ to C ₆₀ mono- or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group are unsubstituted or substituted, and when substituted with multiple substituents, they may be the same as or different from each other.

The present invention provides an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises a compound of the chemical formula 1.

“Alkyl” in the present invention is a monovalent substituent derived from a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms, examples of which include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, etc.

“Alkenyl” in the present invention is a monovalent substituent derived from an unsaturated hydrocarbon having 2 to 40 carbon atoms and a straight or branched chain having at least one carbon-carbon double bond, and examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, etc.

“Alkynyl” in the present invention is a monovalent substituent derived from an unsaturated hydrocarbon having 2 to 40 carbon atoms and a straight or branched chain having at least one carbon-carbon triple bond, examples of which include, but are not limited to, ethynyl and 2-propynyl.

The term “aryl” in the present invention refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, which is a single ring or a combination of two or more rings. In addition, a monovalent substituent in which two or more rings are condensed with each other, contains only carbon as a ring-forming atom (for example, the number of carbon atoms may be 8 to 60), and the entire molecule has non-aromaticity may be included. Examples of such aryls include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and fluorenyl.

The term “heteroaryl” in the present invention refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom selected from N, O, P, S, and Se. In addition, it is interpreted to include a monovalent group in which two or more rings are simply attached to or condensed with each other, and includes a heteroatom selected from N, O, P, S, and Se in addition to carbon as a ring-forming atom, and the entire molecule has non-aromacity. Examples of such heteroaryl include a 6-membered monocyclic ring such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl; but are not limited to, 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, etc.

“Aryloxy” in the present invention is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.

“Alkyloxy” in the present invention refers to a monovalent substituent represented by R’O-, wherein R’ means 1 to 40 alkyl, and is interpreted as including a linear, branched, or cyclic structure. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.

“Arylamine” in the present invention means an amine substituted with an aryl having 6 to 60 carbon atoms.

“Cycloalkyl” in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.

“Heterocycloalkyl” in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.

In the present invention, “alkylsilyl” means silyl substituted with alkyl having 1 to 40 carbon atoms, and “arylsilyl” means silyl substituted with aryl having 5 to 60 carbon atoms.

The term “fused ring” in the present invention means a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring, or a combination thereof.

Since the compound of the present invention has excellent thermal stability, carrier transport ability, luminescence ability, etc., it can be usefully applied as an organic layer material of an organic electroluminescent device.

In addition, an organic electroluminescent device including the compound of the present invention in an organic layer has greatly improved aspects such as luminescence performance, driving voltage, lifespan, and efficiency, and can be effectively applied to full-color display panels, etc.

FIG. 1 is a cross-sectional view of an organic electroluminescent device according to one embodiment of the present invention.
FIG. 2 is a cross-sectional view of an organic electroluminescent device according to one embodiment of the present invention.

Hereinafter, the present invention will be described in detail.

1. New organic compounds

The novel compound of the present invention can be represented by the following chemical formula 1:

[Chemical Formula 1]

In the above chemical formula 1,

L ₁ is selected from the group consisting of a single bond, an arylene group having C ₆ to C ₁₈ , and a heteroarylene group having 5 to 18 nuclear atoms;

Ar ₁ and Ar ₂ are each independently hydrogen, deuterium, halogen, cyano group, C ₁ to C ₃₀ alkyl group, C ₂ to C ₃₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 5 to 7 nuclear atoms, C ₆ to C ₃₀ aryl group, heteroaryl group having 5 to 30 nuclear atoms, C ₁ to C ₃₀ alkyloxy group, C ₆ to C ₃₀ aryloxy group, C ₁ to C ₃₀ alkylsilyl group, C ₅ to C ₃₀ arylsilyl group, C ₁ to C ₃₀ alkylboron group, C ₆ to C ₃₀ arylborone group, C ₆ to C ₃₀ Selected from the group consisting of an arylphosphanyl group, a C ₆ to C ₃₀ mono- or diarylphosphinyl group, and a C ₆ to C ₃₀ arylamine group;

The _arylene group and _{heteroarylene} group of the above L ₁ , and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group of the above Ar 1 and Ar 2 are each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ One or more substituents selected from the group consisting of an alkyloxy group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphanyl group, a C ₆ to C ₆₀ mono- or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group are unsubstituted or substituted, and when substituted with multiple substituents, they may be the same as or different from each other.

The compound represented by the chemical formula 1 of the present invention substitutes a phenyl group and benzo[d]oxazole on a fluorene structure having excellent thermal stability and carrier transport ability, and combines an EWG structure having high electron mobility, thereby facilitating energy transfer through interaction with an iridium dopant, and improved current efficiency can be expected. Accordingly, when the compound of the present invention is used as a material for an electron transport layer, the performance thereof can be improved to increase the efficiency of an organic electroluminescent device, and the light emission efficiency of the device can be improved by contributing to an increase in the number of excitons in the light emitting layer, and the durability and stability of the device can be improved, so that the lifespan of the device can be efficiently increased.

According to a preferred embodiment of the present invention, the compound may be a compound represented by the following chemical formula 2 or 3:

[Chemical formula 2]

[Chemical Formula 3]

In the above chemical formulas 2 and 3,

Each of L ₁ , Ar ₁ and Ar ₂ is as defined in the chemical formula 1.

According to a preferred embodiment of the present invention, Ar ₁ may be selected from the group consisting of a C ₁ to C ₃₀ alkyl group, a C ₆ to C ₃₀ aryl group, and a heteroaryl group having 5 to 30 nuclear atoms.

According to a preferred embodiment of the present invention, Ar ₁ may be selected from the group consisting of a phenyl group, a biphenyl group, and a naphthalenyl group.

According to a preferred embodiment of the present invention, L ₁ may be a single bond or a linker represented by any one of the following chemical formulae A-1 to A-3:

In the above chemical formulas A-1 to A-3,

* indicates the part where the combination takes place.

According to a preferred embodiment of the present invention, L ₁ may be a single bond or a linker represented by the chemical formula A-1.

According to a preferred embodiment of the present invention, Ar ₂ may be a substituent represented by any one of the following chemical formulas 4 to 8:

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical formula 6]

[Chemical formula 7]

[Chemical formula 8]

In the above chemical formulas 4 to 8,

* indicates the part where the combination takes place;

m and n are each independently an integer from 0 to 4;

Z ₁ to Z ₅ are each independently N or C(R ₃ );

T ₁ is C(R ₄ )(R ₅ ) or N(R ₆ );

R ₁ and R ₂ are each independently deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₃ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to C ₆₀ arylborone group, C ₆ to C ₆₀ An arylphosphanyl group, a C ₆ to C ₆₀ mono- or diarylphosphinyl group, and a C ₆ to C ₆₀ arylamine group are selected from the group consisting of, or are combined with an adjacent group to form a condensed ring, and when there are plural of each of R ₁ and R ₂ , they are the same as or different from each other;

R ₃ to R ₆ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₃ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to C ₆₀ arylborone group, C ₆ to C ₆₀ is selected from the group consisting of an arylphosphanyl group, a C ₆ to C ₆₀ mono- or diarylphosphinyl group, and a C ₆ to C ₆₀ arylamine group, or forms a condensed ring by combining with an adjacent group, and when there are multiple R ₃ , they are the same or different from each other;

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl _{group ,} arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group of the above R 1 to R 6 are each independently deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ arylamine group, One or more substituents selected from the group consisting of a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylborone group, a C ₆ to C ₆₀ arylphosphanyl group, a C ₆ to C ₆₀ mono- or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group are unsubstituted or substituted, and when substituted with multiple substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, R ₁ to R ₆ may each independently be selected from the group consisting of a C ₁ to C ₃₀ alkyl group, a C ₆ to C ₃₀ aryl group, and a heteroaryl group having 5 to 30 nuclear atoms.

According to a preferred embodiment of the present invention, R ₁ to R ₆ may each independently be selected from the group consisting of a phenyl group, a biphenyl group, and a naphthalenyl group.

According to a preferred embodiment of the present invention, the substituent represented by the chemical formula 4 may be a substituent represented by the following chemical formula 9:

[Chemical formula 9]

In the above chemical formula 9,

* indicates the part where the combination takes place;

R ₇ and R ₈ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₃ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to C ₆₀ arylborone group, C ₆ to C ₆₀ is selected from the group consisting of an arylphosphanyl group, a C ₆ to C ₆₀ mono- or diarylphosphinyl group, and a C ₆ to C ₆₀ arylamine group, or forms a condensed ring by combining with an adjacent group;

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl _{group ,} arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group of the above R 7 and R 8 are each independently deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ arylamine group, is unsubstituted or substituted with one or more substituents selected from the group consisting of a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylborone group, a C ₆ to C ₆₀ arylphosphanyl group, a C ₆ to C ₆₀ mono- or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group, and when substituted with multiple substituents, they are the same as or different from each other;

Each of Z ₁ , Z ₃ and Z ₅ is as defined in the chemical formula 4.

According to a preferred embodiment of the present invention, Ar ₂ may be a substituent represented by any one of the following chemical formulas B-1 to B-7:

In the above chemical formulas B-1 to B-7,

* indicates the part where the combination takes place;

m and n are each independently an integer from 0 to 4;

R ₁ and R ₂ are each independently deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₃ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to C ₆₀ arylborone group, C ₆ to C ₆₀ An arylphosphanyl group, a C ₆ to C ₆₀ mono- or diarylphosphinyl group, and a C ₆ to C ₆₀ arylamine group are selected from the group consisting of, or are combined with an adjacent group to form a condensed ring, and when there are plural of each of R ₁ and R ₂ , they are the same as or different from each other;

R ₇ and R ₈ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₃ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to C ₆₀ arylborone group, C ₆ to C ₆₀ is selected from the group consisting of an arylphosphanyl group, a C ₆ to C ₆₀ mono- or diarylphosphinyl group, and a C ₆ to C ₆₀ arylamine group, or forms a condensed ring by combining with an adjacent group;

The _alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, _arylamine group, _alkylsilyl group, _alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group of the above R 1 , R 2 , R 7 and R 8 are each independently deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C A compound of claim _{1, wherein the compound is unsubstituted or substituted with one or more substituents selected from the group consisting of an arylamine group having 60} carbon atoms, a cycloalkyl group having ₃ to ₄₀ carbon atoms, a heterocycloalkyl group having 3 to ₄₀ carbon atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphanyl group, a C ₆ to C 60 mono- or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group, and when substituted with multiple substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, R ₁ , R ₂ , R ₇ and R ₈ may each independently be selected from the group consisting of a C ₁ to C ₃₀ alkyl group, a C ₆ to C ₃₀ aryl group and a heteroaryl group having 5 to 30 nuclear atoms.

According to a preferred embodiment of the present invention, R ₁ , R ₂ , R ₇ and R ₈ may each be independently selected from the group consisting of a phenyl group, a biphenyl group and a naphthalenyl group.

According to a preferred embodiment of the present invention, Ar ₂ may be a substituent represented by the following chemical formula 10:

[Chemical Formula 10]

In the above chemical formula 10,

* indicates the part where the combination takes place;

R ₉ and R ₁₀ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₃ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to C ₆₀ arylborone group, C ₆ to C ₆₀ is selected from the group consisting of an arylphosphanyl group, a C ₆ to C ₆₀ mono- or diarylphosphinyl group, and a C ₆ to C ₆₀ arylamine group, or forms a condensed ring by combining with an adjacent group;

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl _{group ,} arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group of the above R 9 and R 10 are each independently deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphanyl group, a C ₆ to C ₆₀ mono- or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group are unsubstituted or substituted with one or more substituents selected from the group consisting of, and when substituted with multiple substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, R ₉ and R ₁₀ may each independently be selected from the group consisting of a C ₁ to C ₃₀ alkyl group, a C ₆ to C ₃₀ aryl group, and a heteroaryl group having 5 to 30 nuclear atoms.

According to a preferred embodiment of the present invention, R ₉ and R ₁₀ may each independently be selected from the group consisting of a phenyl group, a biphenyl group, a naphthalenyl group, and a fluorenyl group.

The compound represented by chemical formula 1 of the present invention can be represented by the following compounds, but is not limited thereto:

The compound of chemical formula 1 of the present invention can be synthesized according to a general synthetic method ( see Chem. Rev. , 60 :313 (1960); J. Chem . SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995) etc.). The detailed synthetic process for the compound of the present invention will be specifically described in the synthetic examples described below.

2. Organic Electric field Light-emitting element

Meanwhile, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising a compound represented by chemical formula 1 according to the present invention.

Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises a compound represented by the chemical formula 1. At this time, the compounds may be used alone or in a mixture of two or more.

The organic layer above one or more layers may be at least one of a hole injection layer, a hole transport layer, a light-emitting layer, a light-emitting auxiliary layer, a life-span improvement layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one of the organic layers among these may include a compound represented by the chemical formula 1.

The structure of the organic electroluminescent device according to the present invention described above is not particularly limited, but as an example, referring to FIG. 1, for example, it includes an anode (10) and a cathode (20) facing each other, and an organic layer (30) positioned between the anode (10) and the cathode (20). Here, the organic layer (30) may include a hole transport layer (31), a light-emitting layer (32), and an electron transport layer (34). In addition, a hole transport auxiliary layer (33) may be included between the hole transport layer (31) and the light-emitting layer (32), and an electron transport auxiliary layer (35) may be included between the electron transport layer (34) and the light-emitting layer (32).

As another example of the present invention, referring to FIG. 2, the organic layer (30) may further include a hole injection layer (37) between the hole transport layer (31) and the anode (10), and may further include an electron injection layer (36) between the electron transport layer (34) and the cathode (20).

In the present invention, the hole injection layer (37) laminated between the hole transport layer (31) and the anode (10) not only improves the interface characteristics between the ITO used as the anode and the organic material used as the hole transport layer (31), but also has the function of smoothing the surface of the ITO by being applied on top of the ITO whose surface is not flat. Any material commonly used in the relevant technical field may be used without special limitation, and for example, an amine compound may be used, but is not limited thereto.

In addition, the electron injection layer (36) is a layer laminated on top of the electron transport layer to facilitate electron injection from the cathode, ultimately performing the function of improving power efficiency. Any material commonly used in the relevant technical field can be used without special restrictions, and for example, materials such as LiF, Liq, NaCl, CsF, Li ₂ O, and BaO can be used.

In addition, although not shown in the drawing, the present invention may further include a light-emitting auxiliary layer between the hole transport auxiliary layer (33) and the light-emitting layer (32). The light-emitting auxiliary layer may serve to transport holes to the light-emitting layer (32) and adjust the thickness of the organic layer (30). The light-emitting auxiliary layer may include a hole transport material and may be made of the same material as the hole transport layer (31).

In addition, although not shown in the drawing, the present invention may further include a life improvement layer between the electron transport auxiliary layer (35) and the light-emitting layer (32). The light-emitting layer (32) prevents holes, which move along the ionization potential level within the organic light-emitting device, from diffusing or moving to the electron transport layer due to the high energy barrier of the life improvement layer, thereby limiting the holes to the light-emitting layer. This function of limiting the holes to the light-emitting layer can contribute to improving the life of the organic light-emitting device by preventing the holes from diffusing to the electron transport layer that moves electrons by reduction, thereby suppressing the phenomenon of life reduction through irreversible decomposition reaction by oxidation.

The compound represented by the chemical formula 1 of the present invention substitutes a phenyl group and benzo[d]oxazole on a fluorene structure having excellent thermal stability and carrier transport ability, and combines an EWG structure having high electron mobility, so that energy transfer through interaction with an iridium dopant becomes easy, and improved current efficiency can be expected. Therefore, when the compound of the present invention is used as a material for an electron transport layer, the performance thereof can be improved to increase the efficiency of an organic electroluminescent device, and the light emitting layer can contribute to an increase in the number of excitons, so that the light emitting efficiency of the device can be improved, and the durability and stability of the device can be improved, so that the lifespan of the device can be efficiently increased. Therefore, the organic layer including the compound represented by the chemical formula 1 is preferably a light emitting layer, an electron transport layer, or an electron transport auxiliary layer, and more preferably, it can be an electron transport layer or an electron transport auxiliary layer.

In addition, the compound according to the present invention can also be used as a light-emitting layer material, and specifically, the compound represented by the chemical formula 1 can be used as a phosphorescent host, fluorescent host or dopant material of the light-emitting layer, and preferably can be used as a phosphorescent host (blue, green and/or red phosphorescent host material).

In addition, in the organic electroluminescent device of the present invention, in addition to the above-described sequentially stacking of an anode, one or more organic layers, and a cathode, it may additionally include an insulating layer or an adhesive layer at the interface between the electrode and the organic layer.

The organic electroluminescent device of the present invention can be manufactured by forming other organic layers and electrodes using materials and methods known in the art, except that at least one of the organic layers (e.g., an electron transport auxiliary layer) is formed to include a compound represented by the chemical formula 1.

The above organic layer can be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

The substrate usable in the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films and sheets, etc. can be used.

In addition, the anode material can be made of a conductor with a high work function to facilitate hole injection, for example, and includes, but is not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black.

In addition, the cathode material may be made of a conductor with a low work function to facilitate electron injection, for example, and may include, but is not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and multilayered materials such as LiF/Al or LiO ₂ /Al.

Hereinafter, the present invention will be described in detail through examples. However, the following examples are only intended to illustrate the present invention, and the present invention is not limited to the following examples.

[ Preparation 1] Synthesis of 2-phenyl-5-(9-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole

<Step 1> N-(2,5- Dibromophenyl ) Benzamide's Synthesis

2,5-Dibromoaniline (250.9 g, 1.0 mol) was charged into the reactor, methylene chloride (1,000 ml) was added, and the mixture was stirred. Benzoyl chloride (116 mL, 1.0 mol) and pyridine (161.8 mL, 2.0 mol) were added dropwise to the reactor, mixed, and stirred at room temperature for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, column chromatography was used to obtain the target compound, N-(2,5-dibromophenyl)benzamide (252.1 g, yield 71%).

¹ H-NMR: δ 7.52 (d 1H), 7.59 (d, 1H), 7.63 (dd, 2H), 7.70 (t, 1H), 7.98 (s, 1H), 8.03 (d, 2H), 9.15 (b , 1H)

[LCMS] : 355

<Step 2> 5- Bromo -2- Phenylbenzo[d]oxazole Synthesis

In Preparation Example 1 <Step 1>, N-(2,5-dibromophenyl)benzamide (251.1 g, 710 mmol) synthesized in was mixed with K ₂ CO ₃ (196.3 g, 1420 mmol) and DMSO (7100 ml), and stirred at 140 ℃ for 1.5 h. After completion of the reaction, the mixture was extracted with ethyl acetate, followed by adding MgSO ₄ and filtering. After removing the solvent in the filtered organic layer, column chromatography was used to obtain the target compound, 5-bromo-2-phenylbenzo[d]oxazole (147.9 g, yield 76%).

¹ H-NMR: δ 7.41 (t, 1H) 7.43 (s, 1H), 7.51 (m, 3H), 7.60 (d, 1H), 8.05 (d, 2H)

[LCMS] : 274.1

<Step 3> Phenyl(2-phenylbenzo[d]oxazol-5-yl)methanone Synthesis

In the reactor, 5-bromo-2-phenylbenzo[d]oxazole (147.9 g, 539.5 mmol) synthesized in <Step 2> is added, THF 1000 ml is injected, stirred, placed in a dry ice bath, and the internal temperature is set to -78 ℃. n-BuLi (356.1 ml, 593.5 mmol) is slowly injected using a syringe, and stirred for 30 minutes. Benzaldehyde (47.7 g, 449.5 mmol) is dissolved in THF 100 ml, and then slowly added dropwise. Slowly warm to room temperature. After concentrating the reactant, I ₂ (241.0 g, 949.6 mmol), K ₂ CO ₃ (246.1 g, 1780.5 mmol), add 1000 ml of t-BuOH and heat under reflux for 7 hours. After completion of the reaction, extract with ethyl acetate, add MgSO ₄ and filter.

After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, column chromatography was used to obtain the target compound, phenyl(2-phenylbenzo[d]oxazol-5-yl)methanone (94.2 g, yield 70%).

¹ H-NMR: δ 7.41 (t, 1H) 7.51-7.52 (m, 2H), 7.55-7.61 (m, 3H), 7.78-7.79 (m, 3H), 8.05-8.06 (m, 3H), 8.59 ( s, 1H)

[LCMS] : 299.3

<Step 4> (2'- Chloro -[1,1'-biphenyl]-2-yl)(phenyl)(2- Phenylbenzo[d]oxazole -5-day) Synthesis of methanol

2-Bromo-2'-chloro-1,1'-biphenyl (101.0 g, 377.6 mmol) is placed in a reactor, 500 ml of THF is injected, stirred, placed in a dry ice bath, and the internal temperature is set to -78 ℃. n-BuLi (250 ml, 415.4 mmol) is slowly injected using a syringe, stirred for 30 minutes. Phenyl(2-phenylbenzo[d]oxazol-5-yl)methanone (94.2 g, 314.7 mmol) synthesized in <Step 3> of Preparation Example 1 is dissolved in 500 ml of THF, and then slowly added dropwise. Slowly increase the temperature to room temperature to terminate the reaction. After termination of the reaction, extraction was performed with ethyl acetate, MgSO ₄ was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain the target compound, (2'-chloro-[1,1'-biphenyl]-2-yl)(phenyl)(2-phenylbenzo[d]oxazol-5-yl)methanol (98.3 g, yield 64%).

¹ H-NMR: δ 3.65 (s, 1H), 7.34-7.36 (m, 5H), 7.38-7.39 (m, 4H), 7.41-7.44 (m, 3H) 7.51-7.52 (m, 2H), 7.55 ( d, 1H), 7.69 (s, 1H), 7.72-7.73 (m, 3H), 8.05 (d, 2H)

[LCMS] : 487.9

<Step 5> 5-(4- Chloro -9-Phenyl-9H- Fluorene -9-day)-2- Phenylbenzo[d]oxazole Synthesis

In the reactor, (2'-chloro-[1,1'-biphenyl]-2-yl)(phenyl)(2-phenylbenzo[d]oxazol-5-yl)methanol (98.3 g, 201.4 mmol) synthesized in <Step 4> was dissolved in 1000 ml of toluene, and 20 ml of sulfuric acid was added while stirring vigorously. The temperature was raised to 100 ℃, stirred for 8 hours, and then cooled to room temperature. Set. After completion of the reaction, the mixture was extracted with methylene chloride, followed by adding MgSO ₄ and filtering. After removing the solvent in the filtered organic layer, column chromatography was used to obtain the target compound, 5-(4-chloro-9-phenyl-9H-fluoren-9-yl)-2-phenylbenzo[d]oxazole (68.1 g, yield 72%).

¹ H-NMR: δ 7.11 (d, 2H), 7.22-7.23 (m, 2H), 7.26-7.28 (m, 2H), 7.33(t, 2H), 7.38-7.39 (m, 2H), 7.41-7.43 (m, 2H), 7.51(t, 2H), 7.55-7.56 (m,2H), 7.67 (d, 1H), 7.87 (d, 1H), 8.05 (d, 2H)

[LCMS] : 469.9

<Step 6> Synthesis of 2-phenyl-5-(9-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole

In Preparation Example 1 <Step 5>, 5-(4-chloro-9-phenyl-9H-fluoren-9-yl)-2-phenylbenzo[d]oxazole (68.1 g, 145.1 mmol) synthesized and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (44.2 g, 174.2 mmol) and Pd(dppf)Cl ₂ (3.56 g, 4.4 mmol), KOAc (28.5 g, 290.3 mmol), Xphos (6.9 g, 14.5 mmol) were added to 1000 ml of 1,4-dioxane and heated under reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain the target compound, 2-phenyl-5-(9-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (46.3 g, yield 69%).

¹ H-NMR: δ 1.24 (s, 12H), 7.07-7.11 (m, 4H), 7.14-7.17 (m, 3H), 7.23-7.26 (m, 2H), 7.33-7.34 (m, 4H), 7.41 -7.42 (m, 1H), 7.44(s, 1H), 7.51 (t, 2H), 7.87 (d, 1H), 8.05 (d, 2H)

[LCMS] : 561.4

[ Preparation 2] Synthesis of 2-phenyl-5-(9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole

The same process as in [Preparation Example 1] was followed except that 2-bromo-3'-chloro-1,1'-biphenyl was used as the reactant in Step 4, thereby obtaining 67.1 g (yield 12%) of the target compound.

¹ H-NMR: δ 1.24 (s, 12H), 7.07-7.11 (m, 4H), 7.17 (t, 1H), 7.23 (d, 1H), 7.26-7.33 (m, 3H), 7.34-7.41 (m , 2H), 7.51 (t, 2H), 7.56 (s, 1H), 7.63 (s, 1H), 7.67 (d, 1H), 7.87 (d, 2H), 8.05 (d, 2H)

[LCMS] : 561.4

[ Preparation 3] Synthesis of 2-phenyl-5-(9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole

The same process as in [Preparation Example 1] was followed except that 2-bromo-4'-chloro-1,1'-biphenyl was used as the reactant in Step 4, thereby obtaining 72.7 g (yield 13%) of the target compound.

¹ H-NMR: δ 1.24 (s, 12H), 7.05-7.11 (m, 3H), 7.15-7.17 (m, 2H), 7.23 (d, 1H), 7.26-7.33 (m, 3H), 7.34(s , 1H), 7.35-7.40 (m, 2H), 7.51 (t, 2H), 7.56 (s, 1H), 7.67 (d, 1H), 7.87 (d, 2H), 8.05 (d, 2H)

[LCMS] : 561.4

[ Preparation 4] Synthesis of 2-phenyl-6-(9-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole

The same process as in [Preparation Example 1] was followed except that 2,4-dibromoaniline was used as the reactant in Step 1, thereby obtaining 67.1 g (yield 12%) of the target compound.

¹ H-NMR: δ 1.24 (s, 12H), 7.07-7.11 (m, 4H), 7.14-7.17 (m, 3H), 7.23-7.26 (m, 2H), 7.33-7.34 (m, 4H), 7.41 -7.42 (m, 1H), 7.44(s, 1H), 7.51 (t, 2H), 7.87 (d, 1H), 8.05 (d, 2H)

[LCMS] : 561.4

[ Preparation 5] Synthesis of 2-phenyl-6-(9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole

The same process as in [Preparation Example 4] was followed except that 2-bromo-3'-chloro-1,1'-biphenyl was used as the reactant in Step 4, thereby obtaining 67.0 g (yield 12%) of the target compound.

¹ H-NMR: δ 1.24 (s, 12H), 7.07-7.15 (m, 6H), 7.23-7.26 (m, 2H), 7.33-7.34 (m, 4H), 7.41-7.42 (m, 1H), 7.44 (s, 1H), 7.51 (t, 2H), 7.63 (s, 1H), 7.87 (d, 1H), 8.05 (d, 2H)

[LCMS] : 561.4

[ Preparation 6] Synthesis of 2-phenyl-6-(9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole

The same process as in [Preparation Example 4] was followed except that 2-bromo-4'-chloro-1,1'-biphenyl was used as the reactant in Step 4, thereby obtaining 78.3 g (yield 14%) of the target compound.

¹ H-NMR: δ 1.24 (s, 12H), 7.07-7.17 (m, 6H), 7.23-7.26 (m, 2H), 7.33-7.34 (m, 4H), 7.41-7.44 (m, 2H), 7.51 (t, 2H), 7.87 (d, 2H), 8.05 (d, 2H)

[LCMS] : 561.4

[ Synthetic example 1] Synthesis of compound A-3

2-Phenyl-5-(9-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol) of Preparation Example 1, 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (3.1 g, 8.9 mmol), and Pd(OAc) ₂ (0.1 g, 0.4 mmol), Cs ₂ CO ₃ (5.8 g, 17.8 mmol), and Xphos (0.4 g, 0.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and heated under reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent from the filtered organic layer, the target compound A-3 (6.6 g, yield 82%) was obtained using column chromatography.

[LCMS] : 742.8

[ Synthetic example 2] Synthesis of compound A-5

2-Phenyl-5-(9-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol) of Preparation Example 1, 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.1 g, 8.9 mmol), and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol) and K ₂ CO ₃ (3.7 g, 26.7 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and heated under reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent from the filtered organic layer, the target compound A-5 (4.7 g, yield 72%) was obtained using column chromatography.

[LCMS] : 742.8

[ Synthetic example 3] Synthesis of compound A-14

In Preparation Example 1, 2-phenyl-5-(9-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 4-([1,1'-biphenyl]-4-yl)-2-(4-chlorophenyl)-6-phenylpyrimidine (3.7 g, 8.9 mmol), and Pd(OAc) ₂ (0.1 g, 0.4 mmol), Cs ₂ CO ₃ (5.8 g, 17.8 mmol), and Xphos (0.4 g, 0.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and the mixture was heated under reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain the target compound A-14 (5.1 g, yield 70%).

[LCMS] : 817.9

[ Synthetic example 4] Synthesis of compound A-26

In Preparation Example 1, 2-phenyl-5-(9-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 2-(4-chlorophenyl)-6-phenyl-[1,2,4]triazolo[1,5-a]pyridine (2.7 g, 8.9 mmol), and Pd(OAc) ₂ (0.1 g, 0.4 mmol), Cs ₂ CO ₃ (5.8 g, 17.8 mmol), and Xphos (0.4 g, 0.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and the mixture was heated under reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain the target compound A-26 (4.6 g, yield 74%).

[LCMS] : 704.8

[ Synthetic example 5] Synthesis of compound A-36

In Preparation Example 1, 2-phenyl-5-(9-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 9-([1,1'-biphenyl]-4-yl)-3-chloro-9H-carbazole (3.2 g, 8.9 mmol), and Pd(OAc) ₂ (0.1 g, 0.4 mmol), Cs ₂ CO ₃ (5.8 g, 17.8 mmol), and Xphos (0.4 g, 0.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and heated under reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent from the filtered organic layer, the target compound A-36 (4.5 g, yield 67%) was obtained using column chromatography.

[LCMS] : 752.9

[ Synthetic example 6] Synthesis of compound B-2

In Preparation Example 2, 2-phenyl-5-(9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (3.1 g, 8.9 mmol), and Pd(OAc) ₂ (0.1 g, 0.4 mmol), Cs ₂ CO ₃ (5.8 g, 17.8 mmol), and Xphos (0.4 g, 0.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and heated under reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent from the filtered organic layer, the target compound B-2 (4.7 g, yield 71%) was obtained using column chromatography.

[LCMS] : 742.8

[ Synthetic example 7] Synthesis of compound B-6

In Preparation Example 2, 2-phenyl-5-(9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 2-([1,1'-biphenyl]-4-yl)-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine (3.7 g, 8.9 mmol), and Pd(OAc) ₂ (0.1 g, 0.4 mmol), Cs ₂ CO ₃ (5.8 g, 17.8 mmol), and Xphos (0.4 g, 0.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and the mixture was heated under reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, column chromatography was used to obtain the target compound B-6 (5.2 g, yield 72%).

[LCMS] : 818.9

[ Synthetic example 8] Synthesis of compound B-13

In Preparation Example 2, 2-phenyl-5-(9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine (3.1 g, f8.9 mmol), and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), K ₂ CO ₃ (3.7 g, 26.7 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and heated under reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent from the filtered organic layer, the target compound B-13 (4.7 g, yield 72%) was obtained using column chromatography.

[LCMS] : 741.8

[ Synthetic example 9] Synthesis of compound B-27

In Preparation Example 2, 2-phenyl-5-(9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 2-(4-chlorophenyl)-6-phenyl-[1,2,4]triazolo[1,5-a]pyridine (2.7 g, 8.9 mmol), and Pd(OAc) ₂ (0.1 g, 0.4 mmol), Cs ₂ CO ₃ (5.8 g, 17.8 mmol), and Xphos (0.4 g, 0.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and the mixture was heated under reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, column chromatography was used to obtain the target compound B-27 (4.1 g, yield 65%).

[LCMS] : 704.8

[ Synthetic example 10] Synthesis of compound B-35

In Preparation Example 2, 2-phenyl-5-(9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 9-([1,1'-yl)-9H-fluoren-9-yl)benzobiphenyl]-3-yl)-3-chloro-9H-carbazole (3.2 g, 8.9 mmol), and Pd(OAc) ₂ (0.1 g, 0.4 mmol), Cs ₂ CO ₃ (5.8 g, 17.8 mmol), and Xphos (0.4 g, 0.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and the mixture was heated under reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain the target compound B-35 (4.5 g, yield 67%).

[LCMS] : 752.9

[ Synthetic example 11] Synthesis of compound C-4

In Preparation Example 3, 2-phenyl-5-(9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (3.7 g, 8.9 mmol), and Pd(OAc) ₂ (0.1 g, 0.4 mmol), Cs ₂ CO ₃ (5.8 g, 17.8 mmol), and Xphos (0.4 g, 0.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and the mixture was heated under reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, column chromatography was used to obtain the target compound C-4 (5.2 g, yield 72%).

[LCMS] : 818.9

[ Synthetic example 12] Synthesis of compound C-7

In Preparation Example 3, 2-phenyl-5-(9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (3.7 g, 8.9 mmol), and Pd(OAc) ₂ (0.1 g, 0.4 mmol), Cs ₂ CO ₃ (5.8 g, 17.8 mmol), and Xphos (0.4 g, 0.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and the mixture was heated under reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, column chromatography was used to obtain the target compound C-7 (4.7 g, yield 65%).

[LCMS] : 818.9

[ Synthetic example 13] Synthesis of compound C-12

In Preparation Example 3, 2-phenyl-5-(9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenylpyrimidine (3.7 g, 8.9 mmol), and Pd(OAc) ₂ (0.1 g, 0.4 mmol), Cs ₂ CO ₃ (5.8 g, 17.8 mmol), and Xphos (0.4 g, 0.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and heated under reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent from the filtered organic layer, the target compound C-12 (4.9 g, yield 68%) was obtained using column chromatography.

[LCMS] : 817.9

[ Synthetic example 14] Synthesis of compound C-22

In Preparation Example 3, 2-phenyl-5-(9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 4-([1,1'-biphenyl]-4-yl)-6-(4-chlorophenyl)-2-phenylpyrimidine (3.7 g, 8.9 mmol), and Pd(OAc) ₂ (0.1 g, 0.4 mmol), Cs ₂ CO ₃ (5.8 g, 17.8 mmol), and Xphos (0.4 g, 0.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and the mixture was heated under reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, column chromatography was used to obtain the target compound C-22 (5.2 g, yield 71%).

[LCMS] : 817.9

[ Synthetic example 15] Synthesis of compound C-28

In Preparation Example 3, 2-phenyl-5-(9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 2-(4-chlorophenyl)-[1,2,4]triazolo[1,5-a]pyridine (2.1 g, 8.9 mmol), and Pd(OAc) ₂ (0.1 g, 0.4 mmol), Cs ₂ CO ₃ (5.8 g, 17.8 mmol), and Xphos (0.4 g, 0.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and heated under reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent from the filtered organic layer, the target compound C-28 (3.9 g, yield 71%) was obtained using column chromatography.

[LCMS] : 628.7

[ Synthetic example 16] Synthesis of compound D-3

In Preparation Example 4, 2-phenyl-6-(9-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (3.1 g, 8.9 mmol), and Pd(OAc) ₂ (0.1 g, 0.4 mmol), Cs ₂ CO ₃ (5.8 g, 17.8 mmol), and Xphos (0.4 g, 0.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and heated under reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent from the filtered organic layer, the target compound D-3 (6.6 g, yield 82%) was obtained using column chromatography.

[LCMS] : 742.8

[ Synthetic example 17] Synthesis of compound D-5

In Preparation Example 4, 2-phenyl-6-(9-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.1 g, 8.9 mmol), and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol) and K ₂ CO ₃ (3.7 g, 26.7 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and heated under reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent from the filtered organic layer, the target compound D-5 (4.7 g, yield 72%) was obtained using column chromatography.

[LCMS] : 742.8

[ Synthetic example 18] Synthesis of compound D-14

In Preparation Example 4, 2-phenyl-6-(9-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 4-([1,1'-biphenyl]-4-yl)-2-(4-chlorophenyl)-6-phenylpyrimidine (3.7 g, 8.9 mmol), and Pd(OAc) ₂ (0.1 g, 0.4 mmol), Cs ₂ CO ₃ (5.8 g, 17.8 mmol), and Xphos (0.4 g, 0.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and the mixture was heated under reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain the target compound D-14 (5.1 g, yield 70%).

[LCMS] : 817.9

[ Synthetic example 19] Synthesis of compound D-26

In Preparation Example 1, 2-phenyl-5-(9-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 2-(4-chlorophenyl)-6-phenyl-[1,2,4]triazolo[1,5-a]pyridine (2.7 g, 8.9 mmol), and Pd(OAc) ₂ (0.1 g, 0.4 mmol), Cs ₂ CO ₃ (5.8 g, 17.8 mmol), and Xphos (0.4 g, 0.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and the mixture was heated under reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain the target compound D-26 (4.6 g, yield 74%).

[LCMS] : 704.8

[ Synthetic example 20] Synthesis of compound D-36

In Preparation Example 4, 2-phenyl-6-(9-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 9-([1,1'-biphenyl]-4-yl)-3-chloro-9H-carbazole (3.2 g, 8.9 mmol), and Pd(OAc) ₂ (0.1 g, 0.4 mmol), Cs ₂ CO ₃ (5.8 g, 17.8 mmol), and Xphos (0.4 g, 0.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and heated under reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent from the filtered organic layer, the target compound D-36 (4.5 g, yield 67%) was obtained using column chromatography.

[LCMS] : 752.9

[ Synthetic example 21] Synthesis of compound E-2

In Preparation Example 5, 2-phenyl-6-(9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (3.1 g, 8.9 mmol), and Pd(OAc) ₂ (0.1 g, 0.4 mmol), Cs ₂ CO ₃ (5.8 g, 17.8 mmol), and Xphos (0.4 g, 0.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and heated under reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent from the filtered organic layer, the target compound B-2 (4.7 g, yield 71%) was obtained using column chromatography.

[LCMS] : 742.8

[ Synthetic example 22] Synthesis of compound E-6

In Preparation Example 5, 2-phenyl-6-(9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 2-([1,1'-biphenyl]-4-yl)-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine (3.7 g, 8.9 mmol), and Pd(OAc) ₂ (0.1 g, 0.4 mmol), Cs ₂ CO ₃ (5.8 g, 17.8 mmol), and Xphos (0.4 g, 0.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and the mixture was heated under reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, column chromatography was used to obtain the target compound E-6 (5.2 g, yield 72%).

[LCMS] : 818.9

[ Synthetic example 23] Synthesis of compound E-13

In Preparation Example 5, 2-phenyl-6-(9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine (3.1 g, 8.9 mmol), and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol) and K ₂ CO ₃ (3.7 g, 26.7 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and heated under reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent from the filtered organic layer, the target compound E-13 (4.7 g, yield 72%) was obtained using column chromatography.

[LCMS] : 741.8

[ Synthetic example 24] Synthesis of compound E-27

In Preparation Example 5, 2-phenyl-6-(9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 2-(4-chlorophenyl)-6-phenyl-[1,2,4]triazolo[1,5-a]pyridine (2.7 g, 8.9 mmol), and Pd(OAc) ₂ (0.1 g, 0.4 mmol), Cs ₂ CO ₃ (5.8 g, 17.8 mmol), and Xphos (0.4 g, 0.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and the mixture was heated under reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, column chromatography was used to obtain the target compound E-27 (4.1 g, yield 65%).

[LCMS] : 704.8

[ Synthetic example 25] Synthesis of compound E-35

In Preparation Example 5, 2-phenyl-6-(9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 9-([1,1'-biphenyl]-3-yl)-3-chloro-9H-carbazole (3.2 g, 8.9 mmol), and Pd(OAc) ₂ (0.1 g, 0.4 mmol), Cs ₂ CO ₃ (5.8 g, 17.8 mmol), and Xphos (0.4 g, 0.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and heated under reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent from the filtered organic layer, the target compound E-35 (4.5 g, yield 67%) was obtained using column chromatography.

[LCMS] : 752.9

[ Synthetic example 26] Synthesis of compound F-4

In Preparation Example 6, 2-phenyl-6-(9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (3.7 g, 8.9 mmol), and Pd(OAc) ₂ (0.1 g, 0.4 mmol), Cs ₂ CO ₃ (5.8 g, 17.8 mmol), and Xphos (0.4 g, 0.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and the mixture was heated under reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, column chromatography was used to obtain the target compound F-4 (5.2 g, yield 72%).

[LCMS] : 818.9

[ Synthetic example 27] Synthesis of compound F-7

In Preparation Example 6, 2-phenyl-6-(9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (3.7 g, 8.9 mmol), and Pd(OAc) ₂ (0.1 g, 0.4 mmol), Cs ₂ CO ₃ (5.8 g, 17.8 mmol), and Xphos (0.4 g, 0.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and the mixture was heated under reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, column chromatography was used to obtain the target compound C-7 (4.7 g, yield 65%).

[LCMS] : 818.9

[ Synthetic example 28] Synthesis of compound F-12

In Preparation Example 6, 2-phenyl-6-(9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenylpyrimidine (3.7 g, 8.9 mmol), and Pd(OAc) ₂ (0.1 g, 0.4 mmol), Cs ₂ CO ₃ (5.8 g, 17.8 mmol), and Xphos (0.4 g, 0.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and heated under reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent from the filtered organic layer, the target compound F-12 (4.9 g, yield 68%) was obtained using column chromatography.

[LCMS] : 817.9

[ Synthetic example 29] Synthesis of compound F-22

In Preparation Example 6, 2-phenyl-6-(9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 4-([1,1'-biphenyl]-4-yl)-6-(4-chlorophenyl)-2-phenylpyrimidine (3.7 g, 8.9 mmol), and Pd(OAc) ₂ (0.1 g, 0.4 mmol), Cs ₂ CO ₃ (5.8 g, 17.8 mmol), and Xphos (0.4 g, 0.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and the mixture was heated under reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, column chromatography was used to obtain compound F-22 (5.2 g, yield 71%).

[LCMS] : 817.9

[ Synthetic example 30] Synthesis of compound F-28

In Preparation Example 6, 2-phenyl-6-(9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)benzo[d]oxazole (5 g, 8.9 mmol), 2-(4-chlorophenyl)-[1,2,4]triazolo[1,5-a]pyridine (2.1 g, 8.9 mmol), and Pd(OAc) ₂ (0.1 g, 0.4 mmol), Cs ₂ CO ₃ (5.8 g, 17.8 mmol), and Xphos (0.4 g, 0.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H ₂ O, and heated under reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent from the filtered organic layer, the target compound F-28 (3.9 g, yield 71%) was obtained using column chromatography.

[LCMS] : 628.7

[ Example 1 ~ 30] Blue organic Electric field Fabrication of light-emitting elements

In the synthetic examples, the synthesized compounds A-3, A-5, A-14, A-26, A-36, B-2, B-6, B-13, B-27, B-35, C-4, C-7, C-12, C-22, C-28, D-3, D-5, D-14, D-26, D-36, E-2, E-6, E-13, E-27, E-35, F-4, F-7, F-12, F-22, F-28 were purified by high purity sublimation using a commonly known method, and a blue organic electroluminescent device was manufactured as follows.

First, a glass substrate coated with a 1500 Å thick ITO (Indium tin oxide) film was ultrasonically washed in distilled water. After the distilled water washing was completed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was then cleaned for 5 minutes using UV and transferred to a vacuum deposition machine.

On the ITO transparent electrode prepared as described above, DS-205 (Doosan Electronics Co., Ltd., 80 nm)/NPB (15 nm)/ADN + 5% DS-405 (Doosan Electronics Co., Ltd., 30 nm)/compounds A-3, A-5, A-14, A-26, A-36, B-2, B-6, B-13, B-27, B-35, C-4, C-7, C-12, C-22, C-28, D-3, D-5, D-14, D-26, D-36, E-2, E-6, E-13, E-27, E-35, F-4, F-7, F-12, F-22, F-28 were sequentially laminated to fabricate an organic electroluminescent device.

[ Comparative example 1] Blue organic Electric field Fabrication of light-emitting elements

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Alq3 was used instead of compound A-3 as the electron transport layer material.

[ Comparative example 2] Blue organic Electric field Fabrication of light-emitting elements

Except that compound A-3 was not used as an electron transport layer material, the above

A blue organic electroluminescent device was manufactured in the same manner as in Example 1.

However, the structures of NPB, AND and Alq3 used in Examples 1 to 20 and Comparative Examples 1 and 2 are as follows.

[ Evaluation example 1]

For each of the blue organic electroluminescent devices manufactured in Examples 1 to 30 and Comparative Examples 1 to 2, the driving voltage, current efficiency, and luminescence peak at a current density of (10) mA/cm2 were measured, and the results are shown in Table 1 below.

Sample ingredient Driving voltage
(V) EL peak
(nm) Current efficiency
(cd/A) Example 1 A-3 3.4 458 7.0 Example 2 A-5 4.6 459 7.1 Example 3 A-14 4.1 458 6.8 Example 4 A-26 4.0 455 6.9 Example 5 A-36 4.6 456 6.7 Example 6 B-2 3.2 457 6.7 Example 7 B-6 3.9 456 6.9 Example 8 B-13 3.8 452 7.1 Example 9 B-27 3.6 448 6.9 Example 10 B-35 3.7 460 7.1 Example 11 C-4 3.2 455 6.8 Example 12 C-7 3.6 456 6.8 Example 13 C-12 3.9 457 6.9 Example 14 C-22 3.9 452 6.8 Example 15 C-28 3.3 448 6.7 Example 16 D-3 3.6 460 6.8 Example 17 D-5 3.5 465 6.9 Example 18 D-14 3.9 457 6.8 Example 19 D-26 3.8 456 6.4 Example 20 D-36 4.1 465 6.8 Example 21 E-2 3.6 457 6.9 Example 22 E-6 3.6 456 6.9 Example 23 E-13 3.2 457 7.1 Example 24 E-27 3.2 456 6.8 Example 25 E-35 4.1 455 6.5 Example 26 F-4 3.6 459 6.5 Example 27 F-7 3.7 461 6.9 Example 28 F-12 3.9 464 7.1 Example 29 F-22 3.6 467 7.1 Example 30 F-28 3.8 467 6.7 Comparative Example 1 Alq ₃ 4.7 458 5.6 Comparative Example 2 - 4.8 460 6.2

As shown in Table 1 above, the compound of the present invention was used in the electron transport layer.

It was found that the blue organic electroluminescent devices (Examples 1 to 30) exhibited superior performance in terms of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent device using conventional Alq3 in the electron transport layer (Comparative Example 1) and the blue organic electroluminescent device without an electron transport layer (Comparative Example 2).

10: Anode 20: Cathode
30: Organic layer 31: Hole transport layer
32: Emitting layer 33: Hole transporting auxiliary layer
34: Electron transport layer 35: Electron transport auxiliary layer
36: Electron injection layer 37: Hole injection layer

Claims (14)

A compound represented by the following chemical formula 2 or 3:
[Chemical formula 2]

[Chemical Formula 3]

In the above chemical formulas 2 and 3
L ₁ is a single bond or an arylene group having C6 to C18;
Ar ₁ is an aryl group having C ₆ to C ₃₀ ;

Ar ₂ is a substituent represented by any one of the following chemical formulas B-1 to B-3, B-5 to B-7;

* indicates the part where the combination takes place;
m, n are integers from 0 to 1;
R ₁ and R ₂ are each independently selected from the group consisting of hydrogen or an aryl group having C ₆ to C ₆₀ ;
R ₇ and R ₈ are each independently selected from the group consisting of hydrogen or an aryl group having C ₆ to C ₆₀ .
delete delete delete delete delete delete delete delete delete delete In the first paragraph,
The compound is characterized in that the compound is selected from the group consisting of the following compounds:











An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode,
An organic electroluminescent device characterized in that at least one of the organic layers of one or more layers comprises a compound represented by chemical formula 2 or 3 of claim 1. In Article 13,
An organic electroluminescent device, wherein the organic layer includes at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and a light-emitting layer.