KR102389616B1 - 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 including the same, wherein the compound according to the present invention is used in an organic material layer, preferably a light emitting layer, an electron transporting layer or an electron transporting auxiliary layer of an organic electroluminescent device. of luminous efficiency, driving voltage, lifespan, etc. can be improved.

Description

Organic compound and organic electroluminescent 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 including the same.

Taking the observation of organic thin film emission by Bernanose in the 1950s as a starting point, research on organic electroluminescent (EL) devices that led to blue electroluminescence using anthracene single crystals in 1965 continued. ) presented an organic electroluminescent device with a stacked structure divided into a functional layer of a hole layer and a light emitting layer. Since then, in order to make a high-efficiency, long-life organic electroluminescent device, it has been developed in the form of introducing each characteristic organic material layer in the device, leading to the development of a specialized material used for this.

In an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, an exciton is formed, and when the exciton falls to the ground state, light is emitted. In this case, the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc. according to their function.

The light emitting material may be divided into blue, green, and red light emitting materials and yellow and orange light emitting materials for realizing better natural colors according to the emission color. In addition, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system may be used as a light emitting material.

The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times compared to the fluorescence, studies on phosphorescent host materials as well as the phosphorescent dopant are in progress.

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

However, conventional organic material layer materials are advantageous in terms of light emitting properties, but have not reached a satisfactory level in terms of the lifespan of the organic electroluminescent device because the glass transition temperature is low and thermal stability is not very good. Accordingly, there is a demand for the development of an organic layer material having excellent performance.

An object of the present invention is to provide a novel compound capable of improving the efficiency, lifespan, stability, etc. of an organic electroluminescent device and an organic electroluminescent device using the compound in order to solve the above problems.

In order to achieve the above object, the present invention provides a compound represented by the following formula (1):

[Formula 1]

In Formula 1,

X is O or N(R ₅ );

Rings Q ₁ to Q ₃ are each independently selected from the group consisting of C ₆ -C ₃₀ arene and heteroarene having 5 to 30 nuclear atoms;

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

p and q are each independently an integer from 0 to 3;

R ₁ To R ₄ are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ of a cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ of Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ of an arylphosphanyl group, a C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and a C ₆ ~ C ₆₀ arylamine group selected from the group consisting of, or combined with an adjacent group to form a condensed ring, wherein the R ₁ to When each of R ₄ is a plurality, they are the same as or different from each other;

R ₅ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha a nyl group, a C ₆ ~ C ₆₀ mono or diarylphosphinyl group and a C ₆ ~ C ₆₀ arylamine group selected from the group consisting of, or combined with an adjacent group to form a condensed ring;

The R ₁ To R ₅ Alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, aryl Boron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ One or more substituents selected from the group consisting of arylsilyl group When substituted with or unsubstituted and substituted with a plurality of substituents, they are the same or different from each other;

Ar ₁ is a substituent represented by any one of Formulas 2 to 4;

[Formula 2]

[Formula 3]

[Formula 4]

In Formulas 2 to 4,

* means the part where the bond is formed;

Z ₁ to Z ₅ are each independently N or C(R ₆ );

R ₆ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha Nyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylamine group is selected from the group, or combined with an adjacent group to form a condensed ring, and when R ₆ is a plurality of these are the same or different from each other;

An _alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkylboron group, an arylboron group, The arylphosphanyl group, the mono or diarylphosphinyl group and the arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ of arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ of an aryl boron group, a C ₆ ~ C ₆₀ aryl phosphanyl group, a C ₆ ~ C ₆₀ mono or diaryl phosphinyl group, and a C ₆ ~ C ₆₀ arylsilyl group substituted with one or more substituents selected from the group, or When unsubstituted and substituted with a plurality of substituents, they are the same as or different from each other.

The present invention provides an organic electroluminescent device comprising an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer includes the compound of Formula 1 .

"Alkyl" in the present invention is a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, and hexyl. and the like, but is not limited thereto.

"Alkenyl" in the present invention is a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds, and examples thereof include vinyl, Allyl (allyl), isopropenyl (isopropenyl), there are 2-butenyl (2-butenyl) and the like, but is not limited thereto.

"Alkynyl" in the present invention is a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds, an example of which is ethynyl) , 2-propynyl, and the like, but is not limited thereto.

“Aryl” in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, in which a single ring or two or more rings are combined. In addition, two or more rings are condensed with each other, contain only carbon as a ring-forming atom (eg, the number of carbon atoms may be 8 to 60), and the whole molecule is monovalent having non-aromaticity Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, and the like.

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. In this case, at least one carbon, preferably 1 to 3 carbons in the ring are substituted with a heteroatom selected from N, O, P, S and Se. In addition, two or more rings are simply attached to or condensed with each other, and contain a hetero atom selected from N, O, P, S and Se in addition to carbon as a ring forming atom, and the entire molecule is non-aromatic (non-aromatic). It is interpreted to include a monovalent group having aromacity). Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycylates such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl click ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but is not limited thereto.

"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, diphenyloxy, and the like.

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

"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, adamantine, and the like.

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

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

"Condensed ring" in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

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

In addition, the organic electroluminescent device comprising the compound of the present invention in an organic material layer has greatly improved aspects such as light emitting performance, driving voltage, lifespan, and efficiency, and thus can be effectively applied to a full color display panel.

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

Hereinafter, the present invention will be described in detail.

1. Novel Organic Compounds

The novel compound of the present invention may be represented by the following formula (1):

[Formula 1]

In Formula 1,

X is O or N(R ₅ );

Rings Q ₁ to Q ₃ are each independently selected from the group consisting of C ₆ -C ₃₀ arene and heteroarene having 5 to 30 nuclear atoms;

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

p and q are each independently an integer from 0 to 3;

R ₁ To R ₄ are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ of a cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ of Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ of an arylphosphanyl group, a C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and a C ₆ ~ C ₆₀ arylamine group selected from the group consisting of, or combined with an adjacent group to form a condensed ring, wherein the R ₁ to When each of R ₄ is a plurality, they are the same as or different from each other;

R ₅ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha a nyl group, a C ₆ ~ C ₆₀ mono or diarylphosphinyl group and a C ₆ ~ C ₆₀ arylamine group selected from the group consisting of, or combined with an adjacent group to form a condensed ring;

The R ₁ To R ₅ Alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, aryl Boron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ One or more substituents selected from the group consisting of arylsilyl group When substituted with or unsubstituted and substituted with a plurality of substituents, they are the same or different from each other;

Ar ₁ is a substituent represented by any one of Formulas 2 to 4;

[Formula 2]

[Formula 3]

[Formula 4]

In Formulas 2 to 4,

* means the part where the bond is formed;

Z ₁ to Z ₅ are each independently N or C(R ₆ );

R ₆ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha Nyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylamine group is selected from the group, or combined with an adjacent group to form a condensed ring, and when R ₆ is a plurality of these are the same or different from each other;

An _alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkylboron group, an arylboron group, The arylphosphanyl group, the mono or diarylphosphinyl group and the arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ of arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ of an aryl boron group, a C ₆ ~ C ₆₀ aryl phosphanyl group, a C ₆ ~ C ₆₀ mono or diaryl phosphinyl group, and a C ₆ ~ C ₆₀ arylsilyl group substituted with one or more substituents selected from the group, or When unsubstituted and substituted with a plurality of substituents, they are the same as or different from each other.

The novel organic compound represented by Formula 1 of the present invention is an electron withdrawing agent with high electron absorption, such as a nitrogen-containing heterocyclic ring (eg, pyrimidine, triazine, quinazoline, quinoline, triazolopyridinyl, etc.) in the spiro moiety. Groups (EWG) form a basic backbone connected by various linkers (phenyl, biphenyl, naphthalene, fluorene, carbazolyl, phenanthrene, etc.).

In the compound represented by Formula 1 of the present invention, the spiro moiety has very good electrochemical stability, high glass transition temperature and excellent carrier transport ability, and in particular electron mobility is very good, so that it can be used as an electron transport layer or an electron transport auxiliary layer. When used as a material of , blue light emitting efficiency is increased. In addition, the structure in which the benzene ring is condensed on the spiro moiety is expected as a long-life material by enhancing the thermal stability of the device because it increases the conjugation length while maintaining the properties of the material.

According to a preferred embodiment of the present invention, in Formula 2, at least two of Z ₁ to Z ₅ are N, and in Formulas 3 and 4, at least two of Z ₁ to Z ₃ are N, which is organic electroluminescence. When applied to a device, a low driving voltage and high luminous efficiency can be secured.

According to a preferred embodiment of the present invention, each of the rings Q ₁ to Q ₃ may be independently represented by any one of the following Chemical Formulas 5 to 8:

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

In Formulas 5 to 8,

The dotted line indicates the portion where the condensation takes place;

r is an integer from 0 to 4;

R ₇ is each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group , A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ Arylox Period, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Arylphos A panyl group, a C ₆ ~ C ₆₀ mono or diarylphosphinyl group and a C ₆ ~ C ₆₀ arylamine group are selected from the group consisting of, or combine with an adjacent group to form a condensed ring, wherein R ₇ is a plurality They are the same or different from each other;

An _alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkylboron group, an arylboron group, The arylphosphanyl group, the mono or diarylphosphinyl group and the arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ of arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ of an aryl boron group, a C ₆ ~ C ₆₀ aryl phosphanyl group, a C ₆ ~ C ₆₀ mono or diaryl phosphinyl group, and a C ₆ ~ C ₆₀ arylsilyl group substituted with one or more substituents selected from the group, or When unsubstituted and substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, the compound may be a compound represented by any one of the following formulas 9 to 14:

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

In Formulas 9 to 14,

X, R ₁ to R ₄ , l, m, n, p, q, and Ar ₁ are each as defined in Formula 1 above.

According to a preferred embodiment of the present invention, the compound may be a compound represented by Formula 13.

According to a preferred embodiment of the present invention, the substituent represented by the formula (2) may be a substituent represented by the following formula (15):

[Formula 15]

In the formula (15),

* means the part where the bond is formed;

Z ₁ , Z ₃ and Z ₅ are each independently N or C(R ₆ );

R ₆ , R ₈ and R ₉ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ It is selected from the group consisting of an arylamine group, or combines with an adjacent group to form a condensed ring, , When R ₆ is a plurality, they are the same as or different from each other;

R ₆ , R ₈ and R ₉ Alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron Group, aryl boron group, aryl phosphanyl group, mono or diaryl phosphinyl group and aryl silyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alke nyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group , C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group , C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ Arylsilyl group 1 selected from the group consisting of When substituted or unsubstituted with more than one kind of substituent, and substituted with a plurality of substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, Ar ₁ may be a substituent represented by any one of the following formulas A-1 to A-5:

In Formulas A-1 to A-5,

* means the part where the bond is formed;

R ₈ and R ₉ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ 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 ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Arylphosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ Arylamine group is selected from the group consisting of, or combined with an adjacent group to form a condensed ring;

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, aryl of R ₈ and R ₉ Boron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ One or more substituents selected from the group consisting of arylsilyl group When substituted with or unsubstituted, and substituted with a plurality of substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, R ₈ and R ₉ are each independently hydrogen, a C ₁ to C ₄₀ alkyl group, C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. may be selected from the group.

According to a preferred embodiment of the present invention, R ₈ and R ₉ may be each independently selected from the group consisting of hydrogen, a phenyl group, a biphenyl group and a naphthalenyl group.

The compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:

The compound of Formula 1 of the present invention can be synthesized according to general synthetic methods ( Chem. Rev. , 60 :313 (1960); J. Chem . SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995). ), etc.). The detailed synthesis process for the compound of the present invention will be described in detail in the following Synthesis Examples.

2. Organic electric field light emitting element

On the other hand, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by 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 material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is and a compound represented by Formula 1 above. In this case, the compounds may be used alone or in mixture of two or more.

The at least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a light emitting auxiliary layer, a life improvement layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, of which at least one organic material layer is the above formula It may include a compound represented by 1.

The structure of the organic electroluminescent device according to the present invention is not particularly limited, but referring to FIG. 1 as an example, for example, the anode 10 and the cathode 20 facing each other, and the anode 10 and the cathode ( 20) and an organic layer 30 positioned between them. 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 emission layer 32 , and an electron transport auxiliary layer 35 is included between the electron transport layer 34 and the emission layer 32 . can do.

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

In the present invention, the hole injection layer 37 laminated between the hole transport layer 31 and the anode 10 improves the interfacial properties between ITO used as the anode and the organic material used as the hole transport layer 31 as well. Rather, it is a layer that is applied on top of ITO whose surface is not flat and has a function of making the surface of ITO soft, and it can be used without particular limitation as long as it is commonly used in the art, for example, an amine compound can be used. However, the present invention is not limited thereto.

In addition, the electron injection layer 36 is laminated on the electron transport layer 34 to facilitate the injection of electrons from the cathode to ultimately improve power efficiency, and is commonly used in the art. As long as it can be used without any particular limitation, for example, a material such as LiF, Liq, NaCl, CsF, Li ₂ O, BaO may be used.

In addition, although not shown in the drawings in the present invention, a light emitting auxiliary layer may be further included 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 to 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 drawings in the present invention, a lifespan improving layer may be further included between the electron transport auxiliary layer 35 and the light emitting layer 32 . Holes moving at the ionization potential level in the organic light emitting layer to the light emitting layer 32 are blocked by the high energy barrier of the life improvement layer and cannot diffuse or move to the electron transport layer, and consequently, the holes are restricted to the light emitting layer. . This function of limiting holes to the light emitting layer prevents the diffusion of holes into the electron transport layer, which moves electrons by reduction, and suppresses the decrease in lifespan through an irreversible decomposition reaction due to oxidation, thereby contributing to the improvement of the lifespan of the organic light emitting device. can

In the compound represented by Formula 1 of the present invention, the spiro moiety has very excellent electrochemical stability, high glass transition temperature and excellent carrier transport ability, and in particular, excellent electron mobility, resulting in increased blue light emitting efficiency. indicates. In addition, since the benzene ring is condensed on the spiro moiety to increase the conjugation length while maintaining the properties of the material, it is expected as a long-life material by enhancing the thermal stability of the device. In addition, a nitrogen-containing heterocycle with high electron absorption (eg, pyrimidine, triazine, quinazoline, quinoline, triazolopyridinyl, etc.) is linked to the above moiety to provide particularly excellent electron mobility and high glass transition temperature and excellent thermal stability. Accordingly, the organic material layer including the compound represented by Formula 1 is preferably a light emitting layer, an electron transport layer, or an electron transport auxiliary layer, and more preferably an electron transport layer or an electron transport auxiliary layer.

In addition, in the present invention, the organic electroluminescent device may further include an insulating layer or an adhesive layer at the interface between the electrode and the organic material layer, as well as sequentially stacking an anode, one or more organic material layers, and a cathode as described above.

The organic electroluminescent device of the present invention uses materials and methods known in the art, except that at least one of the organic material layers (eg, an electron transport auxiliary layer) is formed to include the compound represented by Formula 1 above. It can be manufactured by forming another organic material layer and an electrode using it.

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

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

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

In addition, the anode material may be made of, for example, a conductor having a low work function to facilitate electron injection, and may be formed of magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead. the same metal or alloys thereof; and a multi-layered material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

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

[ preparation example One] Core 1 synthesis

<Step 1> 9- Bromo -7-(2-( diphenylamino )phenyl)-7H- benzo[c]fluorene Synthesis of -7-ol

To 50 g (0.15 mol) of 2-bromo-N,N-diphenylaniline, 500 mL of THF was added. Next, the temperature of the reaction solution was lowered to -78 ° C., 47.7 g (0.15 mol) of 9-bromo-7H-benzo [c] fluoren-7-one was dissolved in 500 mL of THF and slowly added to the reaction solution. The mixture was stirred at room temperature for 1 hour, and further stirred at room temperature for 24 hours. Then, 500 mL of purified water was added to the reaction solution to terminate the reaction, followed by extraction with 1.5 L of EA, and washing with distilled water. Then, the obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 55.6 g (yield 65%) of the target compound.

¹ H-NMR: δ 6.68 (s, 1H), 7.05 (m, 8H), 7.26 (m, 8H), 7.45 (t, 1H), 7.76 (d, 1H), 7.90 (s, 1H), 7.96 ( d, 1H), 8.11 (d, 2H), 8.94 (d, 1H)

<Step 2> Core 1 synthesis

To 50 g (0.09 mol) of 9-bromo-7-(2-(diphenylamino)phenyl)-7H-benzo[c]fluoren-7-ol, 250 mL (0.36 mol) of methanesulfonic acid was added. The mixture was heated and refluxed at 120°C for 12 hours. The temperature was cooled to room temperature, and the reaction was terminated with 300 mL of purified water in the reaction solution. After extracting the mixture with 1.0 L of CH ₂ Cl ₂ , the separated organic layer was neutralized with 500 mL of saturated calcium carbonate and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 60.3 g of the target compound (yield 73%).

¹ H-NMR: δ 7.24 (m, 15H), 7.42 (t, 1H), 7.73 (d, 1H), 7.90 (m, 2H), 8.12 (d, 2H), 8.88 (d, 1H)

<Step 3> 10-phenyl-9'-(4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2-yl)-10H- of spiro [acridine-9,7'-benzo [c] fluorene] synthesis

Core 1 50 g (0.09 mol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) ) was added 500 mL of dioxane to 27.5 g (0.11 mol). Next, 3.3 g (0.005 mol) of Pd(dppf)Cl ₂ and 26.5 g (0.27 mol) of KOAc were added, followed by heating and refluxing at 130° C. for 4 hours. Then, the temperature was cooled to room temperature, and 500 mL of an aqueous ammonium chloride solution was added to the reaction solution to terminate the reaction, extracted with 1.0 L of EA, and washed with distilled water. Then, the obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 41 g of the target compound (yield 78%).

¹ H-NMR: δ 1.18 (s, 12H), 7.22 (m, 16H), 7.41 (t, 1H), 7.49 (s, 1H), 7.87 (d, 1H), 8.06 (d, 1H), 8.23 ( d, 1H), 8.92 (d, 1H)

[ preparation example 2] Core 2 synthesis

<Step 1> 2- Bromo -11-(2-( diphenylamino )phenyl)-11H- Benzo[b]fluorene Synthesis of -11-ol

Reaction of step 1 of Preparation Example 1 except for using 2-bromo-11H-benzo [b] fluoren-11-one instead of 9-bromo-7H-benzo [c] fluoren-7-one 62.4 g (yield 73%) of the target compound was obtained by performing the same procedure as above.

¹ H-NMR: δ 6.72 (s, 1H), 7.04 (m, 7H), 7.19 (m, 7H), 7.54 (t, 2H), 7.72 (d, 1H), 8.03 (m, 4H), 8.11 ( d, 1H), 8.25 (s, 1H)

<Step 2> Core 2 synthesis

2-bromo-11-(2-(diphenylamino)phenyl)-11H-benzo[b]fluoren-11-ol was prepared in the same manner as in Step 2 of Preparation Example 1 to prepare 31.4 g of the target compound (yield 65 %) was obtained.

¹ H-NMR: δ 7.14 (m, 13H), 7.55 (t, 2H), 7.72 (d, 1H), 7.84 (s, 1H), 7.89 (s, 1H), 8.01 (d, 2H), 8.13 ( d, 2H)

<Step 3> 10-phenyl-2'-(4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2-yl)-10H- of spiro[acridine-9,11'-benzo[b]fluorene] synthesis

Except for using Core 2 instead of Core 1, the same procedure as in Step 3 of Preparation Example 1 was performed to obtain 41.0 g of the target compound (yield 78%).

¹ H-NMR: δ 1.18 (s, 12H), 6.98 (m, 3H), 7.17 (m, 11H), 7.33 (t, 1H), 7.54 (m, 3H), 7.82 (s, 1H), 8.01 ( d, 2H), 8.15 (s, 1H), 8.23 (d, 1H)

[ preparation example 3] Core 3 synthesis

<Step 1> 3- Bromo -11-(2-( diphenylamino )phenyl)-11H- Benzo[b]fluorene Synthesis of -11-ol

Reaction of step 1 of Preparation Example 1 except for using 3-bromo-11H-benzo [b] fluoren-11-one instead of 9-bromo-7H-benzo [c] fluoren-7-one 58.2 g (yield 68%) of the target compound was obtained by performing the same procedure as above.

¹ H-NMR: δ 6.69 (s, 1H), 7.04 (m, 7H), 7.25 (m, 7H), 7.57 (m, 4H), 8.01 (m, 3H), 8.25 (s, 1H), 8.37 ( s, 1H)

<Step 2> Core 3 synthesis

3-bromo-11-(2-(diphenylamino)phenyl)-11H-benzo[b]fluoren-11-ol was prepared in the same manner as in Step 2 of Preparation Example 1 to 38.2 g of the target compound (yield 79) %) was obtained.

¹ H-NMR: δ 7.15 (m, 13H), 7.56 (m, 3H), 7.82 (s, 1H), 8.01 (d, 2H), 8.13 (s, 1H), 8.31 (s, 1H)

<Step 3> 10-phenyl-3'-(4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2- yl )-10H- of spiro[acridine-9,11'-benzo[b]fluorene] synthesis

Except for using Core 3 instead of Core 1, the same procedure as in Step 3 of Preparation Example 1 was performed to obtain 43.1 g of the target compound (yield 82%).

¹ H-NMR: δ 1.18 (s, 12H), 6.98 (t, 3H), 7.21 (m, 12H), 7.55 (m, 3H), 7.82 (s, 1H), 8.01 (m, 3H), 8.12 ( s, 1H)

[ preparation example 4] Core 4 synthesis

<Step 1> 4- Bromo -11-(2-( diphenylamino )phenyl)-11H- Benzo[b]fluorene Synthesis of -11-ol

Reaction of step 1 of Preparation Example 1 except for using 4-bromo-11H-benzo [b] fluoren-11-one instead of 9-bromo-7H-benzo [c] fluoren-7-one 53.0 g (yield 62%) of the target compound was obtained by performing the same procedure as above.

¹ H-NMR: δ 6.72 (s, 1H), 7.07 (m, 7H), 7.26 (m, 8H), 7.57 (t, 2H), 7.79 (d, 2H), 8.02 (d, 3H), 8.23 ( s, 1H)

<Step 2> Core of 4

4-Bromo-11-(2-(diphenylamino)phenyl)-11H-benzo[b]fluoren-11-ol was prepared in the same manner as in Step 2 of Preparation Example 1 to prepare 35.3 g of the target compound (yield 73) %) was obtained.

¹ H-NMR: δ 7.25 (m, 14H), 7.54 (t, 2H), 7.79 (d, 2H), 7.86 (s, 1H), 7.99 (d, 2H), 8.12 (s, 1H)

<Step 3> 10-phenyl-4'-(4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2-yl)-10H- of spiro[acridine-9,11'-benzo[b]fluorene] synthesis

Except for using Core 4 instead of Core 1, the same procedure as in Step 3 of Preparation Example 1 was performed to obtain 41.6 g (yield 79%) of the target compound.

¹ H-NMR: δ 1.18 (s, 12H), 7.02 (t, 3H), 7.21 (m, 12H), 7.33 (d, 1H), 7.56 (m, 3H), 7.83 (s, 1H), 7.99 ( d, 2H), 8.12 (s, 1H)

[ preparation example 5] Core 5 synthesis

<Step 1> 9- Bromo -11-(2-( diphenylamino )phenyl)-11H- Benzo[a]fluorene Synthesis of -11-ol

Reaction of step 1 of Preparation Example 1 except for using 9-bromo-11H-benzo [a] fluoren-11-one instead of 9-bromo-7H-benzo [c] fluoren-7-one 64.1 g (yield 75%) of the target compound was obtained by performing the same procedure as described above.

¹ H-NMR: δ 6.72 (s, 1H), 7.01 (m, 7H), 7.23 (m, 8H), 7.64 (m, 2H), 7.72 (d, 1H), 7.92 (s, 1H), 8.11 ( d, 3H), 8.28 (d, 1H)

<Step 2> Core 5 of synthesis

9-bromo-11-(2-(diphenylamino)phenyl)-11H-benzo[a]fluoren-11-ol was prepared in the same manner as in Step 2 of Preparation Example 1 to 33.4 g of the target compound (yield 69) %) was obtained.

¹ H-NMR: δ 7.19 (m, 14H), 7.61 (m, 2H), 7.72 (d, 1H), 7.94 (m, 2H), 8.09 (d, 3H)

<Step 3> 10-phenyl-9'-(4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2-yl)-10H- of spiro [acridine-9,11'-benzo [a] fluorene] synthesis

Except for using Core 5 instead of Core 1, the same procedure as in Step 3 of Preparation Example 1 was performed to obtain 43.1 g of the target compound (yield 82%).

¹ H-NMR: δ 1.18 (s, 12H), 6.98 (t, 3H), 7.18 (m, 11H), 7.33 (m, 2H), 7.53 (s, 1H), 7.61 (m, 2H), 7.96 ( d, 1H), 8.05 (d, 1H), 8.23 (d, 2H)

[ preparation example 6] Core 6 synthesis

<Step 1> 11- Bromo -13-(2-( diphenylamino )phenyl)-13H- Indeno[1,2-l]phenanthrene Synthesis of -13-ol

Preparation Example 1 except that 11-bromo-13H-indeno [1,2-l] phenanthren-13-one was used instead of 9-bromo-7H-benzo [c] fluoren-7-one 66.2 g (yield 71%) of the target compound was obtained by performing the same procedure as in the reaction of step 1.

¹ H-NMR: δ 6.72 (s, 1H), 7.01 (m, 7H), 7.25 (m, 7H), 7.72 (m, 5H), 7.92 (s, 1H), 8.15 (d, 3H), 8.98 ( d, 1H), 9.05 (d, 1H)

<Step 2> Core 6 synthesis

11-Bromo-13-(2-(diphenylamino)phenyl)-13H-indeno[1,2-l]phenanthren-13-ol was prepared in the same manner as in Step 2 of Preparation Example 1 to prepare the target compound 34.9 g (yield 66%) was obtained.

¹ H-NMR: δ 7.18 (m, 13H), 7.71 (m, 5H), 7.90 (s, 1H), 8.15 (d, 3H), 8.97 (d, 1H), 9.10 (d, 1H)

<Step 3> 10-phenyl-11'-(4,4,5,5- tetramethyl -1,3,2- dioxaborolan Synthesis of -2-yl)-10H-spiro[acridine-9,13'-indeno[1,2-l]phenanthrene]

Except for using Core 6 instead of Core 1, the same procedure as in Step 3 of Preparation Example 1 was performed to obtain 47.9 g (yield 84%) of the target compound.

¹ H-NMR: δ 1.18 (s, 12H), 7.20 (m, 13H), 7.34 (d, 1H), 7.53 (s, 1H), 7.65 (t, 4H), 8.16 (d, 2H), 8.21 ( d, 1H), 8.99 (d, 1H), 9.10 (d, 1H)

[ preparation example 7] Core 7 synthesis

<Step 1> Core 7 synthesis

To 50 g (0.19 mol) of 9-bromo-7H-benzo [c] fluoren-7-one and 152.2 g (1.62 mol) of phenol were added 63 g (0.65 mol) of methanesulfonic acid. The mixture was heated and refluxed at 120°C for 12 hours. The temperature was cooled to room temperature, and the reaction was terminated with 300 mL of purified water in the reaction solution. After the mixture was extracted with CH ₂ Cl ₂ 1.0 L, the separated organic layer was neutralized with 500 mL of saturated calcium carbonate, and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 58.2 g of the target compound (yield 78%).

¹ H-NMR: δ 7.13 (m, 7H), 7.35 (t, 4H), 7.72 (d, 1H), 7.89 (m, 2H), 8.08 (d, 2H), 8.88 (d, 1H)

<Step 2> 4,4,5,5- tetramethyl -2-( spiro [ benzo[c]fluorene Synthesis of -7,9'-xanthene]-9-yl)-1,3,2-dioxaborolane

Except for using Core 7 instead of Core 1, the same procedure as in Step 3 of Preparation Example 1 was performed to obtain 45.2 g (yield 82%) of the target compound.

¹ H-NMR: δ 1.18 (s, 12H), 7.13 (m, 7H), 7.37 (t, 5H), 7.54 (s, 1H), 7.86 (d, 1H), 8.11 (d, 1H), 8.21 ( d, 1H), 8.89 (d, 1H)

[ preparation example 8] Core Synthesis of 8

<Step 1> Core Synthesis of 8

Same as step 1 of Preparation Example 7, except that 2-bromo-11H-benzo [b] fluoren-11-one was used instead of 9-bromo-7H-benzo [c] fluoren-7-one The process was carried out to obtain 58.9 g of the target compound (yield 79%).

¹ H-NMR: δ 6.98 (t, 2H), 7.15 (d, 4H), 7.29 (t, 2H), 7.56 (t, 2H), 7.73 (d, 1H), 7.99 (m, 4H), 8.15 ( d, 2H)

<Step 2> 4,4,5,5- tetramethyl -2-( spiro [ benzo[b]fluorene Synthesis of -11,9'-xanthene]-2-yl)-1,3,2-dioxaborolane

Except for using Core 8 instead of Core 1, the same procedure as in Step 3 of Preparation Example 1 was performed to obtain 46.8 g (yield 85%) of the target compound.

¹ H-NMR: δ 1.18 (s, 12H), 7.09 (d, 2H), 7.16 (d, 4H), 7.33 (m, 3H), 7.56 (m, 3H), 7.16 (s, 1H), 8.01 ( d, 2H), 8.16 (s, 1H), 8.22 (d, 1H)

[ preparation example 9] Core 9 synthesis

<Step 1> Core 9 synthesis

Same as Step 1 of Preparation Example 7, except that 3-bromo-11H-benzo [b] fluoren-11-one was used instead of 9-bromo-7H-benzo [c] fluoren-7-one The process was carried out to obtain 59.7 g (yield 80%) of the target compound.

¹ H-NMR: δ 7.08 (t, 2H), 7.15 (d, 4H), 7.32 (t, 2H), 7.58 (m, 4H), 7.87 (s, 1H), 8.01 (d, 2H), 8.15 ( s, 1H), 8.33 (s, 1H)

<Step 2> 4,4,5,5- tetramethyl -2-( spiro [ benzo[b]fluorene Synthesis of -11,9'-xanthene]-3-yl)-1,3,2-dioxaborolane

Except for using Core 9 instead of Core 1, the same procedure as in Step 3 of Preparation Example 1 was performed to obtain 48.5 g (yield 88%) of the target compound.

¹ H-NMR: δ 1.18 (s, 12H), 7.02 (t, 3H), 7.17 (d, 5H), 7.32 (t, 2H), 7.56 (m, 3H), 7.86 (s, 1H), 7.99 ( m, 3H), 8.13 (s, 1H)

[ preparation example 10] Core 10 Composite

<Step 1> Core 10 Composite

Same as step 1 of Preparation Example 7, except that 4-bromo-11H-benzo [b] fluoren-11-one was used instead of 9-bromo-7H-benzo [c] fluoren-7-one The process was carried out to obtain 55.2 g (yield 74%) of the target compound.

¹ H-NMR: δ 7.02 (t, 2H), 7.16 (d, 4H), 7.28 (t, 3H), 7.56 (t, 2H), 7.72 (d, 2H), 7.85 (s, 1H), 8.02 ( d, 2H), 8.13 (s, 1H)

<Step 2> 4,4,5,5- tetramethyl -2-( spiro [ benzo[b]fluorene Synthesis of -11,9'-xanthene]-4-yl)-1,3,2-dioxaborolane

Except for using Core 10 instead of Core 1, the same procedure as in Step 3 of Preparation Example 1 was performed to obtain 44.6 g (yield 81%) of the target compound.

¹ H-NMR: δ 1.18 (s, 12H), 7.09 (t, 2H), 7.17 (m, 5H), 7.33 (m, 3H), 7.56 (m, 3H), 7.83 (s, 1H), 8.02 ( d, 2H), 8.15 (s, 1H)

[ preparation example 11] Core 11 synthesis

<Step 1> Core 11 synthesis

Same as step 1 of Preparation Example 7, except that 9-bromo-11H-benzo [a] fluoren-11-one was used instead of 9-bromo-7H-benzo [c] fluoren-7-one The process was carried out to obtain 58.9 g of the target compound (yield 79%).

¹ H-NMR: δ 7.06 (t, 2H), 7.16 (d, 4H), 7.30 (t, 3H), 7.58 (m, 2H), 7.72 (d, 1H), 7.95 (m, 2H), 8.15 ( d, 3H)

<Step 2> 4,4,5,5- tetramethyl -2-( spiro [ Benzo[a]fluorene Synthesis of -11,9'-xanthene]-9-yl)-1,3,2-dioxaborolane

Except for using Core 11 instead of Core 1, the same procedure as in Step 3 of Preparation Example 1 was performed to obtain 43.5 g of the target compound (yield 79%).

¹ H-NMR: δ 6.98 (t, 2H), 7.19 (d, 4H), 7.35 (m, 4H), 7.54 (s, 1H), 7.61 (m, 2H), 7.98 (d, 1H), 8.09 ( d, 1H), 8.22 (d, 2H)

[ preparation example 12] Core 12 Synthesis

<Step 1> Core 12 Synthesis

Preparation Example 7 except for using 11-bromo-13H-indeno [1,2-l] phenanthren-13-one instead of 9-bromo-7H-benzo [c] fluoren-7-one 49.8 g (yield 70%) of the target compound was obtained by performing the same process as in step 1.

¹ H-NMR: δ 7.08 (t, 2H), 7.16 (d, 4H), 7.32 (t, 2H), 7.68 (m, 5H), 7.67 (s, 1H), 8.19 (d, 3H), 8.97 ( d, 1H), 9.07 (d, 1H)

<Step 2> 4,4,5,5- tetramethyl -2-( spiro [ indeno[1,2-l]phenanthrene Synthesis of -13,9'-xanthene]-11-yl)-1,3,2-dioxaborolane

Except for using Core 12 instead of Core 1, the same procedure as in Step 3 of Preparation Example 1 was performed to obtain 43.1 g of the target compound (yield 79%).

¹ H-NMR: δ 1.18 (s, 12H), 7.00 (t, 2H), 7.18 (d, 4H), 7.33 (m, 3H), 7.51 (s, 1H), 7.68 (t, 4H), 8.11 ( d, 2H), 8.25 (d, 1H), 8.94 (d, 1H), 9.09 (d, 1H)

[ preparation example 13] Core 13 synthesis

<Step 1> N-( methoxymethyl )-N-(naphthalen-1-yl)naphthalene-1- amine synthesis

To 54 g (0.2 mol) of di(naphthalen-1-yl)amine and 30 g (0.24 mol) of bromo(methoxy)methane was added 400 ml of THF. After addition of 30.4 g (0.3 mol) of triethylamine, the mixture was heated and refluxed at 120° C. for 3 hours. The temperature was cooled to room temperature, and the reaction was terminated with 500 mL of purified water in the reaction solution. The mixture was extracted with 1.0 L of EA and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 45.1 g of the target compound (yield 72%).

¹ H-NMR: δ 3.28 (s, 3H), 5.13 (s, 2H), 7.54 (m, 8H), 7.79 (d, 2H), 8.17 (d, 4H)

<Step 2> 4,4,5,5- tetramethyl -2-( spiro [ indeno[1,2-l]phenanthrene Synthesis of -13,9'-xanthene]-11-yl)-1,3,2-dioxaborolane

To 40 g (0.13 mol) of N-(methoxymethyl)-N-(naphthalen-1-yl)naphthalen-1-amine, 500 mL of THF was added. Next, the temperature of the reaction solution was lowered to -78°C, and 33.5 g (0.15 mol) of 2-chloro-9H-fluoren-9-one was dissolved in 500 mL of THF, slowly added to the reaction solution, and then at the same temperature for 1 hour. After stirring, the mixture was further stirred at room temperature for 24 hours. Then, 500 mL of purified water was added to the reaction solution to terminate the reaction, followed by extraction with 1.5 L of EA, and washing with distilled water. Then, the obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography.

60 mL of HCl was added to the purified solid. The reaction solution was heated to reflux at 100° C. for 2 hours. After cooling the temperature to room temperature, and adding 500 mL of purified water to the reaction solution to terminate the reaction, the resulting solid was filtered under reduced pressure and dried with hot air to obtain 33.9 g (yield 56%) of the target compound.

¹ H-NMR: δ 7.11 (m, 2H), 7.25 (m, 2H), 7.40 (m, 6H), 7.59 (m, 4H), 7.87 (d, 2H), 8.06 (m, 2H), 8.19 ( d, 2H)

<Step 3> Core 13 synthesis

2'-chloro-14H-spiro[dibenzo[c,h]acridine-7,9'-fluorene] 23.3 g, (50 mmol) with iodinebenzene 10.2 g (50 mmol) and Pd ₂ (dba) ₃ 2.3 g (2.5 mmol), P(t-Bu) ₃ 2.0 g, (10 mmol), and sodium tert-butoxide 9.6 g (100 mmol) were put in 100 ml toluene and stirred at 110° C. for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, 17.1 g of the target compound (yield 63%) was obtained by column chromatography.

¹ H-NMR: δ 7.05 (m, 5H), 7.26 (t, 3H), 7.40 (m, 6H), 7.63 (m, 4H), 7.87 (d, 2H), 8.05 (d, 2H), 7.09 ( d, 2H)

<Step 4> 14-phenyl-2'-(4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2-yl)-14H- spiro[dibenzo[c,h] Synthesis of acridine-7,9'-fluorene]

13.5 g (yield 77%) of the target compound was obtained in the same manner as in Step 3 of Preparation Example 1 except for using Core 13 instead of Core 1.

¹ H-NMR: δ 1.18 (s, 12H), 7.18 (m, 10H), 7.32 (m, 2H), 7.42 (t, 4H), 7.58 (d, 2H), 7.88 (d, 2H), 8.02 ( d, 2H), 8.15 (d, 2H)

[ preparation example 14] Core Synthesis of 14

<Step 1> N-( methoxymethyl )-N-(naphthalen-1-yl)naphthalene-1- amine synthesis

43.8 g (yield 70%) of the target compound was obtained in the same manner as in Step 1 of Preparation Example 13, except that di(naphthalen-2-yl)amine was used instead of di(naphthalen-1-yl)amine.

¹ H-NMR: δ 3.28 (s, 3H), 5.12 (s, 2H), 7.10 (s, 2H), 7.42 (m, 8H), 7.75 (d, 4H)

<Step 2> 4,4,5,5- tetramethyl -2-( spiro [ Indeno[1,2-l]phenanthrene Synthesis of -13,9'-xanthene]-11-yl)-1,3,2-dioxaborolane

Except for using N-(methoxymethyl)-N-(naphthalen-2-yl)naphthalen-2-amine instead of N-(methoxymethyl)-N-(naphthalen-1-yl)naphthalen-1-amine was performed the same procedure as in Step 2 of Preparation Example 13 to obtain 21.2 g (yield 35%) of the target compound.

¹ H-NMR: δ 6.98 (s, 4H), 7.35 (m, 8H), 7.58 (m, 4H), 7.73 (d, 2H), 7.88 (d, 2H)

< Step 3 > Core Synthesis of 14

2'-Chloro-14H-spiro[dibenzo[c,h]acridine-7,9'-fluorene] In the same manner as in step 3 of Preparation Example 13, except for using iodinebenzene instead of 19.5 g of the target compound (yield 72%) was obtained.

¹ H-NMR: δ 6.98 (m, 7H), 7.33 (m, 9H), 7.64 (m, 4H), 7.75 (d, 2H), 7.86 (d, 2H)

<Step 4> 14-phenyl-2'-(4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2-yl)-14H- spiro[dibenzo[c,h] Synthesis of acridine-7,9'-fluorene]

10.7 g (yield 68%) of the target compound was obtained in the same manner as in Step 3 of Preparation Example 1 except for using Core 14 instead of Core 1.

¹ H-NMR: δ 1.18 (s, 12H), 7.02 (m, 8H), 7.35 (m, 10H), 7.62 (d, 2H), 7.75 (d, 2H), 7.88 (d, 2H)

[ preparation example 15] Core 15 Synthesis

<Step 1> 3'- Chloro -14H- spiro[dibenzo[c,h] acridine-7,9'- fluorene Synthesis of ]

Using 3-chloro-9H-fluoren-9-one as the compound of Step 1 of Preparation Example 13, the same procedure as in Step 2 of Preparation 13 was performed to obtain 37.6 g (yield 62%) of the target compound.

¹ H-NMR: δ 7.08 (m, 2H), 7.37 (m, 12H), 7.88 (m, 2H), 8.03 (d, 2H), 8.16 (d, 2H)

<Step 2> Core 15 Synthesis

3'-chloro-14H-spiro[dibenzo[c,h]acridine-7 instead of 2'-chloro-14H-spiro[dibenzo[c,h]acridine-7,9'-fluorene] ,9'-fluorene] was carried out in the same manner as in Step 3 of Preparation Example 13, except that 19.8 g (yield 73%) of the target compound was obtained.

¹ H-NMR: δ 7.08 (m, 5H), 7.32 (m, 13H), 7.88 (m, 2H), 8.03 (d, 2H), 8.15 (d, 2H)

<Step 3> 14-phenyl-3'-(4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2-yl)-14H- spiro Synthesis of [dibenzo[c,h]acridine-7,9'-fluorene]

12.6 g (yield 72%) of the target compound was obtained in the same manner as in Step 3 of Preparation Example 1 except for using Core 15 instead of Core 1.

¹ H-NMR: δ 1.18 (s, 12H), 7.18 (m, 10H), 7.28 (d, 2H), 7.42 (t, 4H), 7.61 (m, 3H), 7.88 (d, 1H), 8.01 ( d, 2H), 8.15 (d, 2H)

[ preparation example 16] Core 16 synthesis

<Step 1> 2'- Chloro -6H- spiro[dibenzo[b,i] acridine-13,9'- fluorene Synthesis of ]

Using 3-chloro-9H-fluoren-9-one as the compound of Step 1 of Preparation Example 14, the same procedure as in Step 2 of Preparation Example 13 was performed to obtain 19.4 g (yield 32%) of the target compound.

¹ H-NMR: δ 6.98 (m, 4H), 7.35 (m, 8H), 7.62 (m, 4H), 7.73 (d, 2H), 7.88 (m, 2H)

<Step 2> Core 16 synthesis

3'-chloro-6H-spiro[dibenzo[b,i]acridine-13 instead of 2'-chloro-14H-spiro[dibenzo[c,h]acridine-7,9'-fluorene] ,9'-fluorene] was performed in the same manner as in Step 3 of Preparation Example 13, except that 18.4 g (yield 68%) of the target compound was obtained.

¹ H-NMR: δ 7.17 (m, 7H), 7.32 (m, 9H), 7.58 (m, 4H), 7.73 (d, 2H), 7.85 (m, 2H)

<Step 3> 6-phenyl-3'-(4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2-yl)-6H- spiro[dibenzo[b,i] Synthesis of acridine-13,9'-fluorene]

13.2 g (yield 75%) of the target compound was obtained in the same manner as in Step 3 of Preparation Example 1 except for using Core 16 instead of Core 1.

¹ H-NMR: δ 1.18 (s, 12H), 7.05 (m, 9H), 7.32 (m, 9H), 7.59 (m, 3H), 7.71 (d, 2H), 7.89 (d, 1H)

[ Synthesis example 1] Synthesis of compound 2

10-phenyl-9'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,7'-benzo To 20 g (0.03 mol) of [c]fluorene] and 9.2 g (0.03 mol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 400 mL of dioxane and 100 mL of H ₂ O added. After the addition of Pd(PPh ₃ ) ₄ 2 g (0.002 mol), K ₂ CO ₃ 9.5 g (0.07 mol), the mixture was heated and refluxed at 120° C. for 3 hours. The temperature was cooled to room temperature, and the reaction was terminated with 500 mL of purified water in the reaction solution. The mixture was extracted with 1.0 L of EA and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 18.4 g (yield 78%) of the target compound.

[LCMS]: 688

[ Synthesis example 2] Synthesis of compound 7

4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine was performed in the same manner as in Synthesis Example 1, except that 20.1 g of the target compound (yield 77%) ) was obtained.

[LCMS] : 763

[ Synthesis example 3] Synthesis of compound 15

Core 1 and 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxa) The same procedure as in Synthesis Example 1 was performed except that borolan-2-yl)phenyl)-1,3,5-triazine was used to obtain 23.5 g (yield 75%) of the target compound.

[LCMS]: 841

[ Synthesis example 4] Synthesis of compound 24

Except for using Core 1 and 4-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)quinazoline In the same manner as in Synthesis Example 1, 21.7 g of the target compound (yield 79%) was obtained.

[LCMS]: 737

[ Synthesis example 5] Synthesis of compound 26

Core 1 and 2,4-diphenyl-6-(3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1' -Biphenyl]-3-yl)-1,3,5-triazine was performed in the same manner as in Synthesis Example 1, except that 25.1 g of the target compound (yield 80%) was obtained.

[LCMS]: 841

[ Synthesis example 6] Synthesis of compound 38

10-phenyl-2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,11'-benzo [b] Fluorene] and 2-chloro-4,6-diphenylpyrimidine was performed in the same manner as in Synthesis Example 1, except that 16.9 g (yield 72%) of the target compound was obtained.

[LCMS]: 687

[ Synthesis example 7] Synthesis of compound 47

Core 2 and 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3, 21.1 g (yield 74%) of the target compound was obtained in the same manner as in Synthesis Example 1 except that 5-triazine was used.

[LCMS]: 764

[ Synthesis example 8] Synthesis of compound 51

Core 2 and 4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxa) The same procedure as in Synthesis Example 1 was performed except that borolan-2-yl)phenyl)pyrimidine was used to obtain 24.1 g of the target compound (yield 77%).

[LCMS]: 840

[ Synthesis example 9] Synthesis of compound 53

Core 2 and 6,8-diphenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,2 ,4]triazolo[1,5-a]pyridine was used, and the same procedure as in Synthesis Example 1 was followed to obtain 22.1 g of the target compound (yield 74%).

[LCMS]: 802

[ Synthesis example 10] Synthesis of compound 57

Core 2 and 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxa) The same procedure as in Synthesis Example 1 was performed except that borolan-2-yl)phenyl)-1,3,5-triazine was used to obtain 22.6 g (yield 72%) of the target compound.

[LCMS]: 841

[ Synthesis example 11] Synthesis of compound 72

10-phenyl-3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,11'-benzo [b] 19.4 g (yield 82%) of the target compound was obtained in the same manner as in Synthesis Example 1 except that [b] fluorene] was used.

[LCMS]: 688

[ Synthesis example 12] Synthesis of compound 78

10-phenyl-3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,11'-benzo [b] Fluorene] and 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine The same procedure as in Synthesis Example 1 was performed except that Compound 21.2 g (yield 81%) was obtained.

[LCMS] : 763

[ Synthesis example 13] Synthesis of compound 87

Except using Core 3 and 4-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)quinazoline was performed the same procedure as in Synthesis Example 1 to obtain 22 g of the target compound (yield 80%).

[LCMS]: 737

[ Synthesis example 14] Synthesis of compound 96

Core 3 and 2,4-diphenyl-6-(3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1' -Biphenyl]-3-yl)-1,3,5-triazine was performed in the same manner as in Synthesis Example 1, except that 24.5 g of the target compound (yield 78%) was obtained.

[LCMS]: 841

[ Synthesis example 15] Synthesis of compound 108

10-phenyl-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,11'-benzo [b] Fluorene] and 2-chloro-4,6-diphenylpyrimidine was performed in the same manner as in Synthesis Example 1, except that 18.6 g (yield 79%) of the target compound was obtained.

[LCMS]: 687

[ Synthesis example 16] Synthesis of compound 117

Core 4 and 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3, 21.9 g (yield 77%) of the target compound was obtained in the same manner as in Synthesis Example 1 except that 5-triazine was used.

[LCMS]: 764

[ Synthesis example 17] Synthesis of compound 123

Core 4 and 6,8-diphenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,2 22.5 g (yield 75%) of the target compound was obtained in the same manner as in Synthesis Example 1 except that ,4]triazolo[1,5-a]pyridine was used.

[LCMS]: 802

[ Synthesis example 18] Synthesis of compound 140

Core 4 and 2,4-diphenyl-6-(3''-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1 ':3',1''-terphenyl]-3-yl)-1,3,5-triazine was performed in the same manner as in Synthesis Example 1, except that 25.9 g of the target compound (yield 76%) got

[LCMS]: 917

[ Synthesis example 19] Synthesis of compound 142

10-phenyl-9'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,11'-benzo [a] Fluorene] was carried out in the same manner as in Synthesis Example 1 except that 17 g (yield 72%) of the target compound was obtained.

[LCMS]: 688

[ Synthesis example 20] Synthesis of compound 156

Core 5 and 4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxa) 22.8 g (yield 73%) of the target compound was obtained in the same manner as in Synthesis Example 1 except that borolan-2-yl)phenyl)pyrimidine was used.

[LCMS]: 840

[ Synthesis example 21] Synthesis of compound 164

Except for using Core 5 and 4-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)quinazoline The same procedure as in Synthesis Example 1 was performed to obtain 18.9 g of the target compound (yield 69%).

[LCMS]: 737

[ Synthesis example 22] Synthesis of compound 166

Core 5 and 2,4-diphenyl-6-(3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1' -Biphenyl]-3-yl)-1,3,5-triazine was carried out in the same manner as in Synthesis Example 1, except that 22.6 g (yield 72%) of the target compound was obtained.

[LCMS]: 841

[ Synthesis example 23] Synthesis of compound 179

10-phenyl-11'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,13'-indo 17 g (yield 73%) of the target compound was obtained in the same manner as in Synthesis Example 1 except that no [1,2-l] phenanthrene] and 4-chloro-2,6-diphenylpyrimidine were used. .

[LCMS]: 737

[ Synthesis example 24] Synthesis of compound 187

Core 6 and 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3, 20.3 g (yield 73%) of the target compound was obtained in the same manner as in Synthesis Example 1 except that 5-triazine was used.

[LCMS]: 814

[ Synthesis example 25] Synthesis of compound 193

Core 6 and 6,8-diphenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,2 21.5 g (yield 74%) of the target compound was obtained in the same manner as in Synthesis Example 1 except that ,4]triazolo[1,5-a]pyridine was used.

[LCMS]: 853

[ Synthesis example 26] Synthesis of compound 208

Core 6 and 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(3'-(4,4,5,5-tetramethyl-1,3,2-di Oxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)-1,3,5-triazine was performed in the same manner as in Synthesis Example 1, except that the target compound 23.1 g (yield 70%) was obtained.

[LCMS] : 967

[ Synthesis example 27] Synthesis of compound 216

4,4,5,5-tetramethyl-2-(spiro[benzo[c]fluorene-7,9'-xanthene]-9-yl)-1,3,2-dioxaborolane and 2 -([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine The same procedure as in Synthesis Example 1 was followed except that the target compound was used. 16.8 g (yield 62%) was obtained.

[LCMS]: 689

[ Synthesis example 28] Synthesis of compound 223

Core 7 and 4,6-diphenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine Except for the same procedure as in Synthesis Example 1, 18.8 g of the target compound (yield 63%) was obtained.

[LCMS]: 688

[ Synthesis example 29] Synthesis of compound 227

Except for using Core 7 and 4-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)quinazoline In the same manner as in Synthesis Example 1, 18.4 g (yield 64%) of the target compound was obtained.

[LCMS]: 662

[ Synthesis example 30] Synthesis of compound 249

4,4,5,5-tetramethyl-2-(spiro[benzo[b]fluorene-11,9'-xanthene]-2-yl)-1,3,2-dioxaborolane and 4 -Chloro-2,6-diphenylpyrimidine was performed in the same manner as in Synthesis Example 1, except that 15.9 g (yield 66%) of the target compound was obtained.

[LCMS]: 612

[ Synthesis example 31] Synthesis of compound 257

Core 8 and 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3, 19.1 g (yield 64%) of the target compound was obtained in the same manner as in Synthesis Example 1 except that 5-triazine was used.

[LCMS]: 689

[ Synthesis example 32] Synthesis of compound 270

Core 8 and 6,8-diphenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,2 21.1 g (yield 67%) of the target compound was obtained in the same manner as in Synthesis Example 1 except that ,4]triazolo[1,5-a]pyridine was used.

[LCMS] : 727

[ Synthesis example 33] Synthesis of compound 286

4,4,5,5-tetramethyl-2-(spiro[benzo[b]fluorene-11,9'-xanthene]-3-yl)-1,3,2-dioxaborolane and 2 -([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine was performed in the same manner as in Synthesis Example 1, except that the target compound 18.4 g (yield 68%) was obtained.

[LCMS]: 689

[ Synthesis example 34] Synthesis of compound 296

Core 9 and 4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxa) 22.8 g (yield 69%) of the target compound was obtained in the same manner as in Synthesis Example 1 except that borolan-2-yl)phenyl)pyrimidine was used.

[LCMS]: 764

[ Synthesis example 35] Synthesis of compound 297

Except for using Core 9 and 4-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)quinazoline In the same manner as in Synthesis Example 1, 18.4 g (yield 64%) of the target compound was obtained.

[LCMS]: 662

[ Synthesis example 36] Synthesis of compound 306

Core 9 and 2,4-diphenyl-6-(3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1' -Biphenyl]-3-yl)-1,3,5-triazine was carried out in the same manner as in Synthesis Example 1, except that 21.9 g (yield 66%) of the target compound was obtained.

[LCMS]: 765

[ Synthesis example 37] Synthesis of compound 318

4,4,5,5-tetramethyl-2-(spiro[benzo[b]fluorene-11,9'-xanthene]-4-yl)-1,3,2-dioxaborolane and 2 -Chloro-4,6-diphenylpyrimidine was carried out in the same manner as in Synthesis Example 1 except that 16.6 g (yield 69%) of the target compound was obtained.

[LCMS]: 612

[ Synthesis example 38] Synthesis of compound 327

Core 10 and 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3, 18.5 g (yield 62%) of the target compound was obtained in the same manner as in Synthesis Example 1 except that 5-triazine was used.

[LCMS]: 689

[ Synthesis example 39] Synthesis of compound 333

Core 10 and 6,8-diphenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,2 20.8 g (yield 66%) of the target compound was obtained in the same manner as in Synthesis Example 1 except that ,4]triazolo[1,5-a]pyridine was used.

[LCMS] : 727

[ Synthesis example 40] Synthesis of compound 352

Using 4,4,5,5-tetramethyl-2-(spiro[benzo[a]fluorene-11,9'-xanthene]-9-yl)-1,3,2-dioxaborolane 15.2 g (yield 63%) of the target compound was obtained in the same manner as in Synthesis Example 1 except that.

[LCMS]: 613

[ Synthesis example 41] Synthesis of compound 366

Core 11 and 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3, 20.5 g (yield 62%) of the target compound was obtained in the same manner as in Synthesis Example 1 except that 5-triazine was used.

[LCMS]: 764

[ Synthesis example 42] Synthesis of compound 374

Except for using Core 11 and 4-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)quinazoline In the same manner as in Synthesis Example 1, 18.4 g (yield 64%) of the target compound was obtained.

[LCMS]: 662

[ Synthesis example 43] Synthesis of compound 392

4,4,5,5-tetramethyl-2-(spiro[indeno[1,2-l]phenanthrene-13,9'-xanthene]-11-yl)-1,3,2-dioxa 16.7 g of the target compound by the same procedure as in Synthesis Example 1 except that borolane and 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine were used (Yield 63%) was obtained.

[LCMS] : 738

[ Synthesis example 44] Synthesis of compound 404

Core 12 and 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3, 19.4 g (yield 67%) of the target compound was obtained in the same manner as in Synthesis Example 1 except that 5-triazine was used.

[LCMS] : 739

[ Synthesis example 45] Synthesis of compound 403

Core 12 and 6,8-diphenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,2 21.9 g (yield 65%) of the target compound was obtained in the same manner as in Synthesis Example 1 except that ,4]triazolo[1,5-a]pyridine was used.

[LCMS]: 777

[ Synthesis example 46] Synthesis of compound 420

Core 12 and 2,4-diphenyl-6-(3''-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1 ':3',1''-terphenyl]-3-yl)-1,3,5-triazine was performed in the same manner as in Synthesis Example 1, except that 25.5 g of the target compound (yield 66%) got

[LCMS]: 892

[ Synthesis example 47] Synthesis of compound 422

14-phenyl-2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-14H-spiro[dibenzo[c,h]acridine -7,9'-fluorene] and 2-chloro-4,6-diphenyl-1,3,5-triazine were performed in the same manner as in Synthesis Example 1, except that 16.8 g of the target compound (yield 72%) was obtained.

[LCMS] : 738

[ Synthesis example 48] Synthesis of compound 436

Core 13 and 4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxa) 24.3 g (yield 74%) of the target compound was obtained in the same manner as in Synthesis Example 1 except that borolan-2-yl)phenyl)pyrimidine was used.

[LCMS]: 890

[ Synthesis example 49] Synthesis of compound 448

Core 13 and 4-phenyl-2-(3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl ]-3-yl) The same procedure as in Synthesis Example 1 was performed except that quinazoline was used to obtain 23.3 g (yield 73%) of the target compound.

[LCMS]: 864

[ Synthesis example 50] Synthesis of compound 462

6-phenyl-2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6H-spiro[dibenzo[b,i]acridine The same procedure as in Synthesis Example 1 was followed except that -13,9'-fluorene] and 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine were used. 19.8 g (yield 77%) of the target compound was obtained.

[LCMS]: 814

[ Synthesis example 51] Synthesis of compound 467

Core 14 and 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3, 23.4 g (yield 78%) of the target compound was obtained in the same manner as in Synthesis Example 1 except that 5-triazine was used.

[LCMS]: 814

[ Synthesis example 52] Synthesis of compound 473

Core 14 and 6,8-diphenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,2 23.6 g (yield 75%) of the target compound was obtained in the same manner as in Synthesis Example 1 except that ,4]triazolo[1,5-a]pyridine was used.

[LCMS]: 853

[ Synthesis example 53] Synthesis of compound 494

14-phenyl-3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-14H-spiro[dibenzo[c,h]acridine -7,9'-fluorene] and 4-chloro-2,6-diphenylpyrimidine were used in the same manner as in Synthesis Example 1 to obtain 16.1 g (yield 69%) of the target compound.

[LCMS]: 737

[ Synthesis example 54] Synthesis of compound 505

Core 15 and 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxa) Borolan-2-yl)phenyl)-1,3,5-triazine was performed in the same manner as in Synthesis Example 1, except that 22.4 g (yield 68%) of the target compound was obtained.

[LCMS]: 891

[ Synthesis example 55] Synthesis of compound 514

Except for using Core 15 and 4-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)quinazoline The same procedure as in Synthesis Example 1 was performed to obtain 19.5 g of the target compound (yield 67%).

[LCMS]: 787

[ Synthesis example 56] Synthesis of compound 513

6-phenyl-3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6H-spiro[dibenzo[b,i]acridine Except for using -13,9'-fluorene] and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine The same procedure as in Synthesis Example 1 was performed to obtain 16.9 g (yield 66%) of the target compound.

[LCMS]: 814

[ Synthesis example 57] Synthesis of compound 537

Core 16 and 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3, 19.2 g (yield 64%) of the target compound was obtained in the same manner as in Synthesis Example 1 except that 5-triazine was used.

[LCMS]: 814

[ Synthesis example 58] Synthesis of compound 543

Core 16 and 6,8-diphenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,2 20.5 g (yield 65%) of the target compound was obtained in the same manner as in Synthesis Example 1, except that ,4]triazolo[1,5-a]pyridine was used.

[LCMS]: 853

[ Example 1 to 58] blue organic electric field Fabrication of light emitting devices

After high-purity sublimation purification of the compounds 2 to 543 synthesized in Synthesis Example by a commonly known method, a blue organic electroluminescent device was manufactured according to the following procedure.

First, a glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 Å was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. and transferred the substrate to a vacuum evaporator.

On the ITO transparent electrode prepared as above, DS-205 (Doosan Electronics Co., Ltd. 80 nm)/NPB (15 nm)/ADN + 5 % DS-405 (Doosan Electronics Co., Ltd., 30 nm)/ Compound 5- Compound 330 (5 nm) /Alq ₃ (25 nm)/LiF (1 nm)/Al (200 nm) were stacked in the order to prepare an organic electroluminescent device.

[ comparative example 1] blue organic electric field Manufacturing of light emitting devices

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 2 was not used as the electron transport auxiliary layer material, and Alq ₃ , an electron transport layer material, was deposited at 30 nm instead of 25 nm. .

The structures of NPB, AND, and Alq ₃ used in Examples 1 to 58 and Comparative Example 1 are as follows.

[ evaluation example One]

For the organic electroluminescent devices prepared in Examples 1 to 58 and Comparative Example 1, respectively, the driving voltage, emission wavelength, and current efficiency at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 1 below.

Sample electron transport auxiliary layer drive voltage
(V) luminescence peak
(nm) current efficiency
(cd/A) Example 1 compound 2 4.0 456 7.8 Example 2 compound 7 3.9 452 7.9 Example 3 compound 15 4.1 450 7.8 Example 4 compound 24 4.1 452 7.8 Example 5 compound 26 4.2 455 7.8 Example 6 compound 38 3.9 452 7.7 Example 7 compound 47 3.8 455 7.7 Example 8 compound 51 3.7 455 8.2 Example 9 compound 53 3.7 452 8.3 Example 10 compound 57 4.0 455 8.1 Example 11 compound 72 4.0 455 8.1 Example 12 compound 78 4.2 458 7.8 Example 13 compound 87 4.2 455 7.8 Example 14 compound 96 3.9 456 7.7 Example 15 compound 108 4.1 455 7.6 Example 16 compound 117 4.1 458 8.2 Example 17 compound 123 3.7 455 8.2 Example 18 compound 140 4.0 456 8.0 Example 19 compound 142 4.0 455 8.0 Example 20 compound 156 3.9 458 7.6 Example 21 compound 164 3.9 458 7.6 Example 22 compound 166 3.8 456 7.5 Example 23 compound 179 3.8 458 7.9 Example 24 compound 187 3.7 458 8.0 Example 25 compound 193 4.0 456 8.1 Example 26 compound 208 3.9 457 8.2 Example 27 compound 216 3.7 457 7.7 Example 28 compound 223 4.0 458 7.9 Example 29 compound 227 4.1 458 7.9 Example 30 compound 249 4.1 459 7.8 Example 31 compound 257 3.8 457 7.8 Example 32 compound 270 3.7 456 7.7 Example 33 compound 286 3.7 457 8.0 Example 34 compound 296 3.7 458 8.2 Example 35 compound 297 3.9 456 8.2 Example 36 compound 306 4.0 458 8.2 Example 37 compound 318 4.2 458 8.3 Example 38 compound 327 4.0 457 7.9 Example 39 compound 333 4.0 457 7.9 Example 40 compound 352 4.1 456 7.6 Example 41 compound 366 4.1 456 8.0 Example 42 compound 374 3.8 455 7.7 Example 43 compound 392 4.0 456 8.0 Example 44 compound 404 3.8 457 8.1 Example 45 compound 403 4.0 457 8.1 Example 46 compound 420 3.9 456 8.2 Example 47 compound 422 4.0 457 7.9 Example 48 compound 436 4.1 456 7.9 Example 49 compound 448 4.1 456 7.8 Example 50 compound 462 4.1 455 7.8 Example 51 compound 467 3.9 456 8.0 Example 52 compound 473 3.9 456 8.1 Example 53 compound 494 3.7 457 7.9 Example 54 compound 505 4.0 457 7.9 Example 55 compound 514 4.0 457 8.1 Example 56 compound 513 4.0 456 7.9 Example 57 compound 537 4.1 456 8.0 Example 58 compound 543 4.1 457 8.2 Comparative Example 1 Alq ₃ 4.8 458 6.2

As shown in Table 1, the blue organic electroluminescent device (Examples 1 to 58) using the compound of the present invention for the electron transport auxiliary layer compared to the blue organic electroluminescent device without the electron transport auxiliary layer (Comparative Example 1) It was found that excellent performance was exhibited in terms of current efficiency, emission peak and driving voltage.

[ Example 59 to 76] blue organic electric field Fabrication of light emitting devices

After high-purity sublimation purification of the compounds 2 to 531 synthesized in Synthesis Example by a commonly known method, a blue organic electroluminescent device was manufactured as follows.

first. A glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. The substrate was transferred to a vacuum evaporator.

On the ITO transparent electrode prepared as above, DS-205 (Doosan Electronics, 80 nm)/NPB (15 nm)/ADN + 5 % DS-405 (Doosan Electronics, 30 nm)/Compound 2 to Compound 531 Each compound (30 nm)/LiF (1 nm)/Al (200 nm) were stacked in the order to fabricate an organic electroluminescent device.

[ comparative example 2] blue organic electric field Fabrication of light emitting devices

A blue organic electroluminescent device was manufactured in the same manner as in Example 59, except that Alq ₃ was used instead of Compound 2 as the electron transport layer material.

[ comparative example 3] blue organic electric field Fabrication of light emitting devices

A blue organic electroluminescent device was manufactured in the same manner as in Example 59, except that Compound 2 was not used as the electron transport layer material.

[ evaluation example 2]

For the blue organic electroluminescent devices manufactured in Examples 59 to 76 and Comparative Examples 2 and 3, respectively, the driving voltage, current efficiency, and emission wavelength at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 2 below. indicated.

Sample electron transport layer drive voltage
(V) luminescence peak
(nm) current efficiency
(cd/A) Example 59 compound 2 4.1 456 7.7 Example 60 compound 26 4.1 452 7.8 Example 61 compound 47 3.9 450 8.1 Example 62 compound 57 3.8 452 7.9 Example 63 compound 96 3.8 455 8.0 Example 64 compound 123 4.0 452 7.8 Example 65 compound 142 4.0 455 8.2 Example 66 compound 187 3.7 455 8.0 Example 67 compound 223 4.0 452 8.0 Example 68 compound 249 4.1 455 7.9 Example 69 compound 296 3.9 455 7.8 Example 70 compound 327 4.0 458 7.9 Example 71 compound 352 4.2 455 8.1 Example 72 compound 403 3.9 456 8.0 Example 73 compound 422 3.8 455 8.0 Example 74 compound 467 4.0 458 7.8 Example 75 compound 505 4.0 455 7.8 Example 76 compound 531 3.7 456 7.9 Comparative Example 1 Alq ₃ 4.7 458 5.6 Comparative Example 2 - 4.8 460 6.2

As shown in Table 2, the blue organic electroluminescent device (Examples 59 to 76) using the compound of the present invention for the electron transport layer is a blue organic electroluminescent device using the conventional Alq ₃ for the electron transport layer (Comparative Example 2) and It was found that the blue organic EL device without an electron transport layer (Comparative Example 3) exhibited superior performance in terms of driving voltage, emission peak and current efficiency.

10: positive electrode 20: negative electrode
30: organic layer 31: hole transport layer
32: light emitting layer 33: hole transport auxiliary layer
34: electron transport layer 35: electron transport auxiliary layer
36: electron injection layer 37: hole injection layer

Claims (11)

A compound represented by any one of the following formulas 9 to 12:
[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

In Formulas 9 to 12,
X is O;
q is an integer from 0 to 3;
Ar ₁ is a substituent represented by any one of Formulas A-1 to A-5;

In Formulas A-1 to A-5,
* means the part where the bond is formed;
R ₈ and R ₉ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ 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 ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Arylphosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ Arylamine group is selected from the group consisting of, or combined with an adjacent group to form a condensed ring;
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, aryl of R ₈ and R ₉ Boron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ One or more substituents selected from the group consisting of arylsilyl group When substituted with or unsubstituted, and substituted with a plurality of substituents, they are the same or different from each other. delete delete delete delete delete delete According to claim 1,
The R ₈ and R ₉ are each independently selected from the group consisting of hydrogen, a C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. A compound characterized in that it is selected from the group consisting of the following compounds:

An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic material layers interposed between the anode and the cathode,
At least one of the one or more organic material layers is an organic electroluminescent device comprising a compound represented by any one of Chemical Formulas 9 to 12 of claim 1. 11. The method of claim 10,
The organic material layer is an organic electroluminescent device comprising one or more layers 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.

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