KR102617611B1 - 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 containing the same. The compound according to the present invention is used in an organic material layer, preferably a light-emitting layer, an electron transport layer, or a hole transport layer, to emit light in the organic electroluminescent device. Efficiency, driving voltage, lifespan, etc. can be improved.

Description

Organic compounds and organic electroluminescent devices containing 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 containing the same.

Beginning with the observation of organic thin film luminescence by Bernanose in the 1950s, research on organic electroluminescent (EL) devices continued, leading to blue electroluminescence using anthracene single crystals in 1965, and Tang in 1987. ) presented an organic electroluminescent device with a layered structure divided into a hole layer and a functional layer of the light-emitting layer. Since then, in order to create high-efficiency, long-life organic electroluminescent devices, there has been development in the form of introducing each characteristic organic material layer within the device, leading 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 material layer from the anode, and electrons are injected into the organic material layer from the cathode. When the injected hole and electron meet, an exciton is formed, and when this exciton falls to the ground state, light is emitted. At this time, the material used as the organic material layer can be classified into light-emitting material, hole injection material, hole transport material, electron transport material, electron injection material, etc., depending on its function.

Light-emitting materials can be divided into blue, green, and red light-emitting materials according to their emission color, and yellow and orange light-emitting materials to achieve better natural colors. Additionally, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system can be used as a luminescent material.

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, because the development of phosphorescent materials can theoretically improve luminous efficiency by up to 4 times compared to fluorescence, much research is being conducted on phosphorescent host materials as well as phosphorescent dopants.

So far, hole injection layer and hole transport layer. NPB, BCP, Alq ₃ , etc. are widely known as hole blocking layer and electron transport layer materials, and anthracene derivatives are reported as light emitting layer materials. In particular, metal complex compounds containing Ir, such as Firpic, Ir(ppy) ₃ , and (acac)Ir(btp) ₂ , which have advantages in terms of efficiency improvement among light emitting layer materials, produce blue, green, and red colors. (red) is used as a phosphorescent dopant material, and 4,4-dicarbazolybiphenyl (CBP) is 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 at a satisfactory level in terms of the lifespan of organic electroluminescent devices. Therefore, the development of organic layer materials with excellent performance is required.

In order to solve the above problems, the present invention aims to provide a new compound that can improve the efficiency, lifespan, and stability of an organic electroluminescent device and an organic electroluminescent device using the compound.

In order to achieve the above object, the present invention provides a compound represented by the following formula (2):

[Formula 2]

In Formula 2,

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

Ar ₁ and Ar ₂ 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 with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 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 ~ It may be selected from the group consisting of a C ₆₀ arylphosphine group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylamine group, or may be combined with an adjacent group to form a condensed ring;

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

R ₁ to R ₃ 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 with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 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 A condensed ring may be formed by combining with an arylphosphine group, a C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and a C ₆ ~ C ₆₀ arylamine group or by combining with an adjacent group, and the R ₁ to When each of R ₃ is plural, they are the same or different from each other;

The arylene group and heteroarylene group of L ₁ to L ₅ , the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group of Ar ₁ , Ar ₂ and R ₁ to R ₃ , Cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine group, mono or diarylphosphinyl group, and arylsilyl group are each independently a deuterium, halogen, cyano, or 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 with 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 with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group and arylsilyl groups of C ₆ to C ₆₀ .

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

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

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

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

In the present invention, “aryl” refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, either a single ring or a combination of two or more rings. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.

In the present invention, “heteroaryl” 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, preferably 1 to 3 carbons, of the ring is replaced with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply pendant or condensed may be included, and it is further interpreted to include a condensed form with an aryl group. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl. polycyclic ring; Examples include 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, etc., but are not limited thereto.

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

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

In the present invention, “arylamine” refers to an amine substituted with aryl having 6 to 60 carbon atoms.

“Cycloalkyl” in the present invention refers to 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.

In the present invention, “heterocycloalkyl” refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon, preferably 1 to 3 carbons in the ring, 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 and piperazine.

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 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, the organic electroluminescent device containing the compound of the present invention in the organic material layer has greatly improved aspects such as luminous performance, driving voltage, lifespan, and efficiency, and can be effectively applied to full color display panels.

Hereinafter, the present invention will be described in detail.

1. Novel organic compounds

The new compound of the present invention can be represented by the following formula (1):

[Formula 1]

In Formula 1,

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

Ar ₁ and Ar ₂ 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 with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 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 ~ A group selected from or adjacent to the group consisting of a C ₆₀ arylphosphine group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylamine group (e.g., any one of L ₂ to L ₅ , or Ar ₁ or Ar ₂ , etc.) to form a condensed ring;

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

R ₁ to R ₃ 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 with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 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 A condensed ring may be formed by combining with an arylphosphine group, a C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and a C ₆ ~ C ₆₀ arylamine group or by combining with an adjacent group, and the R ₁ to When each of R ₃ is plural, they are the same or different from each other;

The arylene group and heteroarylene group of L ₁ to L ₅ , the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group of Ar ₁ , Ar ₂ and R ₁ to R ₃ , Cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine group, mono or diarylphosphinyl group, and arylsilyl group are each independently a deuterium, halogen, cyano, or 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 with 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 with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group and arylsilyl groups of C ₆ to C ₆₀ .

According to a preferred embodiment of the present invention, the new compound of the present invention is a heterocyclic compound bonded to the phenyl of 9-phenyl-9H-carbazole, more preferably to the ortho-position of the phenyl. is used as the basic framework. Because an electron withdrawing group (EWG) with high electron absorption, such as a nitrogen-containing heteroaromatic ring (e.g., pyridine group, pyrimidine group, triazine group, etc.) is bonded to the basic skeleton, the entire molecule has bipolar characteristics. , the binding force between holes and electrons can be increased.

The compounds of the present invention have steric hindrance due to their ortho-substituted structure. As a result, it has high triplet energy and can prevent excitons generated in the light-emitting layer from diffusing into the electron transport layer or hole transport layer adjacent to the light-emitting layer. By increasing the number of excitons contributing to light emission within the light-emitting layer, the light-emitting efficiency of the device can be improved, and the durability and stability of the device can be improved, effectively increasing the lifespan of the device. Specifically, the new compound of the present invention is preferably a compound represented by the following formula (2):

[Formula 2]

In Formula 2,

Each of L ₁ to L ₅ , Ar ₁ , Ar ₂ , l, m, n, and R ₁ to R ₃ is as defined in Formula 1 above.

According to a preferred embodiment of the present invention, at least one of R ₁ to R ₃ , Ar ₁ and Ar ₂ is a substituent represented by any one of the following formulas 3 to 10, so that the luminous efficiency is improved, and the durability and stability of the device are improved. This improvement is desirable because the lifespan of the device is also increased, but is not limited to this:

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

In Formulas 3 to 10,

* refers to the part where the combination takes place:

Z ₁ to Z ₁₂ are each independently N or C(R ₆ );

In Formulas 4, 8 and 9, any one of Z ₁ to Z ₄ bonded to Formula 1 is C(R ₆ ), and in Formula 10, any one of Z ₉ and Z ₁₀ bonded to Formula 1 is C(R ₆ ), wherein R ₆ is absent;

X ₁ is O, S, N(R ₇ ) or C(R ₈ )(R ₉ );

p and q are each independently integers from 0 to 4,

R ₄ and R ₅ 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 with 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₃ to C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms Heterocycloalkyl group, C ₆ ~ C ₆₀ arylamine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ is selected from the group consisting of an arylphosphine group, a C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and a C ₆ ~ C ₆₀ arylsilyl group, or an adjacent group (for example, any one of L ₁ to L ₅ , or may form a condensed ring by combining with any one of adjacent R ₇ to R ₉ or another R ₄ or R ₅ , etc.), and when each of R ₄ and R ₅ is plural, they are the same or different from each other;

R ₆ to R ₉ 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 ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₃ to C ₄₀ cycloalkyl group, 3 nuclear atoms to 40 heterocycloalkyl groups, C ₆ to C ₆₀ arylamine group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₆₀ aryl boron group, C ₆ to selected from the group consisting of a C ₆₀ arylphosphine group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group, or an adjacent group (e.g., any one of L ₁ to L ₅ , or other adjacent R ₄ , R _{6 ,} etc.) may be combined to form a condensed ring, and when there are a plurality of R ₆ , 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, aryl group of R ₄ to R ₉ Boron group, arylphosphine 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 with 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 with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ Substituted with one or more substituents selected from the group consisting of C ₆₀ arylboron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and C ₆ ~ C ₆₀ arylsilyl group. When substituted or unsubstituted and substituted with a plurality of substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, it is preferable in terms of luminous efficiency that at least one of R ₁ , Ar ₁ and Ar ₂ is a substituent represented by any one of Formulas 3 to 10 above.

According to a preferred embodiment of the present invention, it is most preferable in terms of luminous efficiency that at least one of Ar ₁ and Ar ₂ is a substituent represented by Formula 3 or 4.

According to a preferred embodiment of the present invention, the substituent represented by the formulas 3 to 10 may be a compound selected from the group consisting of the following formulas F-1 to F-24:

In the above formulas F-1 to F-24,

* refers to the part where the combination takes place;

t is an integer from 0 to 5;

u is an integer from 0 to 4;

v is an integer from 0 to 3;

w is an integer from 0 to 2;

R ₁₀ is 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, nuclear atom Heteroaryl group with 5 to 60 atoms, aryloxy group with C ₆ to C ₆₀ , alkyloxy group with C ₁ to C ₄₀ , cycloalkyl group with C ₃ to C ₄₀ , heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ arylamine group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₆₀ aryl boron group, C ₆ to C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ It is selected from the group consisting of mono or diarylphosphinyl group and C ₆ ~ C ₆₀ arylsilyl group, or an adjacent group (for example, any one of L ₁ to L ₅ , or adjacent R ₆ or other R _{10 ,} etc.) may be combined to form a condensed ring, and when R ₁₀ is plural, they may be 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, alkyl boron group, aryl boron group, Arylphosphine 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 to C ₆₀ aryl group, heteroaryl group with 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, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ Unsubstituted or substituted with one or more substituents selected from the group consisting of arylboron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and C ₆ ~ C ₆₀ arylsilyl group. When substituted with a plurality of substituents, they may be the same or different from each other;

p, q and R ₄ to R ₉ are as defined in Formulas 3 to 10 above.

According to a preferred embodiment of the present invention, at least one of Ar ₁ and Ar ₂ is a substituent selected from the group consisting of Formulas F-2 to F-6 and F-8 to F-13, in terms of luminous efficiency. Preferred, and more preferably, may be the formula F-6 or F-8.

According to a preferred embodiment of the present invention, it is preferable in terms of luminous efficiency that at least one of R ₁ to R ₃ , Ar ₁ and Ar ₂ is a substituent represented by any one of the following formulas 11 to 13, but is limited thereto. no:

[Formula 11]

[Formula 12]

[Formula 13]

In Formulas 11 to 13,

* refers to the part where the combination takes place;

R ₁₁ to R ₁₃ 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 ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₃ to C ₄₀ cycloalkyl group, 3 nuclear atoms to 40 heterocycloalkyl groups, C ₆ to C ₆₀ arylamine group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₆₀ aryl boron group, C ₆ to selected from the group consisting of a C ₆₀ arylphosphine group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group, or an adjacent group (e.g., any one of L ₁ to L ₅ , or other R ₁₁ , R ₁₂ or R ₁₃ , etc.) may be combined 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 group of R ₁₁ to R ₁₃ Boron group, arylphosphine 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 with 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 with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ Substituted with one or more substituents selected from the group consisting of C ₆₀ arylboron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and C ₆ ~ C ₆₀ arylsilyl group. When substituted or unsubstituted and substituted with a plurality of substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, it is preferable in terms of luminous efficiency that at least one of Ar ₁ and Ar ₂ is a substituent represented by any one of Formulas 11 to 13 above.

According to a preferred embodiment of the present invention, R ₁₁ to R ₁₃ may each independently be selected from the group consisting of hydrogen, an aryl group of C ₆ to C ₆₀ , and a heteroaryl group of 5 to 60 nuclear atoms.

According to a preferred embodiment of the present invention, R ₁₁ to R ₁₃ may each be independently selected from the group consisting of hydrogen, phenyl group, biphenyl group, naphthalenyl group, fluorenyl group, spirobifluorenyl group, and carbazolyl group. there is.

According to a preferred embodiment of the present invention, L ₁ to L ₅ are each independently a single bond, a phenylene group, a biphenylene group, a naphthalenyl group, a fluorenyl group, a carbazolyl group, a quinazolinyl group, and a quinolinyl group. It can be selected from a group consisting of:

In addition, according to a preferred embodiment of the present invention, L ₁ to L ₅ may each independently be a single bond or a linker represented by any of the following formulas 14 to 16, but are not limited thereto:

[Formula 14]

[Formula 15]

[Formula 16]

In Formulas 14 to 16,

* refers to the part where the combination takes place;

Y ₁ to Y ₈ are each independently N or C(R ₁₄ );

In Formula 14, at least two of Y ₁ to Y ₆ are C(R ₁₄ ), and in Formula 15, at least one of Y ₁ to Y ₄ is C(R ₁₄ ), and at least one of Y ₅ to Y ₈ is C(R ₁₄ ), and at least two of Y ₁ to Y ₄ in Formula 16 are C(R ₁₄ );

R ₁₄ is absent or represents 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 with 3 to 40 nuclear atoms, aryl group with C ₆ to C ₆₀ , heteroaryl group with 5 to 60 nuclear atoms, alkyloxy group with C ₁ to C ₄₀ , 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 selected from the group consisting of an arylphosphine group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylamine group, and when R ₁₄ is plural, 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, alkyl boron group, aryl boron group, Arylphosphine 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 to C ₆₀ aryl group, heteroaryl group with 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, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ Unsubstituted or substituted with one or more substituents selected from the group consisting of arylboron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and C ₆ ~ C ₆₀ arylsilyl group. And when substituted with a plurality of substituents, these may be the same or different from each other.

According to a preferred embodiment of the present invention, m is an integer of 2 to 4, and adjacent substituted R ₁ may be combined with each other to form a condensed ring. Specifically, the present invention may be a compound represented by the following formula (17), but is not limited thereto:

[Formula 17]

In Formula 17 above,

Each of L ₁ to L ₅ , Ar ₁ , Ar ₂ , l, n, R ₂ and R ₃ is as defined in Formula 1 above.

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

In the present invention, the compound represented by Formula 1 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 synthesis examples described later.

2. Organic electric field light emitting element

Meanwhile, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) containing the compound represented by Formula 1 according to the above-described 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 It includes a compound represented by Formula 1 above. At this time, the above compounds may be used alone or in combination of two or more.

The one or more organic material layers 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 lifespan improvement layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one of these organic materials layers has the formula above. It may include a compound represented by 1.

In the present invention, the compound represented by Formula 1 has a basic skeleton in which a hetero ring is bonded to the phenyl of 9-phenyl-9H-carbazole, more preferably to the ortho-position of the phenyl. , an electron withdrawing group (EWG) with high electron absorption, such as a nitrogen-containing heteroaromatic ring (e.g., pyridine group, pyrimidine group, triazine group, etc.) is bonded to the basic skeleton, making the entire molecule bipolar. Because it has a , the binding force between holes and electrons can be increased. Therefore, in the present invention, the organic material layer containing the compound represented by Formula 1 is preferably an electron transport layer, a hole transport layer, or a light-emitting layer depending on the substituent to which it is bonded.

According to one example of the present invention, the light emitting layer of the organic electroluminescent device may include a host material, and in this case, the host material may include the compound represented by Formula 1 above. In this way, when the compound represented by Formula 1 is included as a light-emitting layer material of an organic electroluminescent device, preferably a green phosphorescent host, the binding force between holes and electrons in the light-emitting layer increases, thereby increasing the efficiency (light emission) of the organic electroluminescent device. efficiency and power efficiency), lifespan, brightness, and driving voltage can be improved.

The structure of the organic electroluminescent device according to the present invention described above is not particularly limited, and may be, for example, a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode are sequentially stacked. At this time, an electron transport auxiliary layer may be additionally laminated between the light emitting layer and the electron transport layer, and an electron injection layer may be additionally laminated on the electron transport layer. In the present invention, one or more of the hole injection layer, hole transport layer, light emitting layer, electron transport layer, electron transport auxiliary layer, and electron injection layer may include the compound represented by Formula 1, and preferably the light emitting layer, electron transport layer, or hole The transport layer may include the compound represented by Formula 1 above.

In addition, the structure of the organic electroluminescent device of the present invention may be one in which an anode, one or more organic material layers, and a cathode are sequentially stacked, and an insulating layer or adhesive layer is inserted at the interface between the electrode and the organic material layer.

The organic electroluminescent device of the present invention uses materials known in the art, except that at least one of the organic layers (e.g., a light-emitting layer, an electron transport layer, or a hole transport layer) includes the compound represented by Formula 1 above. and can be manufactured by forming other organic layers and electrodes using methods.

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

There is no particular limitation on the substrate that can be used in the present invention, and silicon wafers, quartz, glass plates, metal plates, plastic films and sheets, etc. can be used.

In addition, the anode material includes 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, but are not limited thereto.

Additionally, the cathode material includes metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and multilayer structure materials such as LiF/Al or LiO ₂ /Al, etc., but are not limited thereto.

Hereinafter, the present invention will be described in detail through examples. However, the following examples are merely illustrative of the present invention, and the present invention is not limited by the following examples.

[ Preparation example One] Synthesis of Intermediate-1

Carbazole (10.0 g, 59.81 mmol), 2-bromoaniline (10.29 g, 59.81 mmol) Pd ₂ (dba) ₃ (1.64 g, 1.79 mmol), P(t-bu) ₃ (2.42 g, 11.96 mmol), NaO(t-bu) (11.50 g, 119.61 mmol) and 100 ml of toluene were mixed and stirred at 110°C for 4 hours. After completion of the reaction, it was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, 11.59 g (yield: 75%) of the target compound was obtained using column chromatography.

GC-Mass (theoretical value: 258.32 g/mol, measured value: 258 g/mol)

¹ H-NMR: δ 5.32 (s, 2H), 6.94 (d, 1H), 7.20 (m, 4H), 7.35 (t, 1H), 7.50 (m, 3H), 7.95 (m, 3H)

[ Preparation example 2] intermediate -composition of 2

Intermediate-1 (10.0 g, 38.71 mmol), iodobenzene (7.90 g, 38.71 mmol) Pd ₂ (dba) ₃ (1.06 g, 1.16 mmol), P(t-bu) ₃ (1.57 g, 7.74 mmol) under nitrogen stream. ), NaO(t-bu) (7.44 g, 77.42 mmol), and 100 ml of toluene were mixed and stirred at 110°C for 4 hours. After completion of the reaction, it was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, 10.36 g (yield: 80%) of the target compound was obtained using column chromatography.

GC-Mass (theoretical value: 334.42 g/mol, measured value: 334 g/mol)

¹ H-NMR: δ 7.02 (t, 1H), 7.40 (m, 12H), 7.75 (d, 1H), 7.94 (d, 1H), 8.20 (d, 1H), 8.55 (d, 1H), 10.48 ( s, 1H)

[ Preparation example 3] intermediate -composition of 3

The same process as Preparation Example 2 was performed except that 2-bromonaphthalene (8.02 g, 38.71 mmol) was used instead of iodobenzene, and 10.72 g (yield: 72%) of the target compound was obtained.

GC-Mass (theoretical value: 384.48 g/mol, measured value: 384 g/mol)

¹ H-NMR: δ 7.30 (m, 16H), 7.95 (d, 1H), 8.20 (d, 1H), 8.55 (d, 1H), 10.48 (s, 1H)

[ Preparation example 4] intermediate -composition of 4

The same process as Preparation Example 2 was performed except that 2-bromo-9,9-dimethyl-9H-fluorene (10.57 g, 38.71 mmol) was used instead of iodobenzene, and 13.08 g of the target compound (yield: 75%) was obtained. ) was obtained.

GC-Mass (theoretical value: 450.59 g/mol, measured value: 450 g/mol)

¹ H-NMR: δ 1.70 (s, 6H), 7.40 (m, 10H), 7.65 (m, 3H), 7.70 (d, 1H), 7.90 (m, 3H), 8.19 (d, 1H), 8.55 ( d, 1H), 10.50 (s, 1H)

[ Preparation example 5] intermediate Composition of -5

The same procedure as in Preparation Example 2 was performed except that 3-bromo-9-phenyl-9H-carbazole (12.47 g, 38.71 mmol) was used instead of iodobenzene, and 15.47 g (yield: 80%) of the target compound was obtained. Acquired.

GC-Mass (theoretical value: 499.62 g/mol, measured value: 499 g/mol)

¹ H-NMR: δ 7.40 (m, 10H), 7.50 (m, 9H), 7.94 (m, 2H), 8.20 (d, 1H), 8.55 (d, 2H), 10.50 (s, 1H)

[ Preparation example 6] intermediate -6 synthesis

The same procedure as Preparation Example 2 was performed except that 10-bromo-7-phenyl-7H-benzo[c]carbazole (14.41 g, 38.71 mmol) was used instead of iodobenzene, and 15.75 g of the target compound (yield: 74%) was obtained.

GC-Mass (theoretical value: 549.68 g/mol, measured value: 549 g/mol)

¹ H-NMR: δ 6.50 (d, 1H), 7.40 (m, 6H), 7.65 (m, 12H), 8.01 (m, 4H), 8.20 (d, 1H), 8.55 (d, 2H), 10.50 ( s, 1H)

[ Preparation example 7] intermediate Composition of -7

11.94 g (yield: 70%) of the target compound was obtained by performing the same process as Preparation Example 2, except that 2-bromodibenzo[b,d]thiophene (10.19 g, 38.71 mmol) was used instead of iodobenzene. did.

GC-Mass (theoretical value: 440.56 g/mol, measured value: 440 g/mol)

¹ H-NMR: δ 7.50 (m, 12H), 7.80 (m, 4H), 8.20 (d, 1H), 8.55 (m, 2H), 10.50 (s, 1H)

[ Preparation example 8] intermediate Composition of -8

The same process as Preparation Example 2 was performed except that 2-bromodibenzo[b,d]furan (9.57 g, 38.71 mmol) was used instead of iodobenzene, and 11.94 g (yield: 72%) of the target compound was obtained. .

GC-Mass (theoretical value: 424.50 g/mol, measured value: 424 g/mol)

¹ H-NMR: δ 7.50 (m, 12H), 7.80 (m, 4H), 8.20 (d, 1H), 8.55 (m, 2H), 10.50 (s, 1H)

[ Preparation example 9] intermediate -composition of 9

The same process as Preparation Example 1 was performed except that 9-phenyl-9H,9'H-3,3'-bicarbazole (10.00 g, 24.48 mmol) was used instead of carbazole, and 7.95 g (yield) of the target compound was obtained. : 65%) was obtained.

GC-Mass (theoretical value: 499.62 g/mol, measured value: 499 g/mol)

¹ H-NMR: δ 5.30 (s, 2H), 6.94 (d, 1H), 7.65 (m, 12H), 7.77 (d, 2H), 7.99 (m, 6H), 8.55 (d, 2H)

[ Preparation example 10] intermediate -10 composite

The same process as Preparation Example 2 was performed except that Intermediate-9 (10.00 g, 20.02 mmol) was used instead of Intermediate-2, and 7.72 g (yield: 67%) of the target compound was obtained.

GC-Mass (theoretical value: 575.72 g/mol, measured value: 575 g/mol)

¹ H-NMR: δ 7.50 (m, 19H), 7.99 (m, 6H), 8.55 (d, 1H), 10.50 (s, 1H)

[ Preparation example 11] intermediate Composition of -11

The same process as Preparation Example 1 was performed except that 10-(9H-carbazol-3-yl)-7-phenyl-7H-benzo[c]carbazole (10.00 g, 21.81 mmol) was used instead of carbazole. 8.39 g (yield: 70%) of the target compound was obtained.

GC-Mass (theoretical value: 549.68 g/mol, measured value: 549 g/mol)

¹ H-NMR: δ 5.32 (s, 2H), 6.94 (s, 1H), 7.16 (m, 3H), 7.35 (t, 1H), 7.62 (m, 10H), 7.77 (d, 1H), 7.99 ( m, 5H), 8.13 (d, 1H), 8.30 (d, 1H), 8.54 (m, 2H)

[ Preparation example 12] intermediate Composition of -12

The same process as Preparation Example 2 was performed except that Intermediate-11 (10.00 g, 18.19 mmol) was used instead of Intermediate-2, and 8.54 g (yield: 75%) of the target compound was obtained.

GC-Mass (theoretical value: 625.78 g/mol, measured value: 625 g/mol)

¹ H-NMR: δ 7.02 (t, 1H), 7.65 (m, 20H), 7.80 (m, 5H), 8.13 (d, 1H), 8.30 (d, 1H), 8.55 (m, 2H), 10.50 ( s, 1H)

[ Synthesis example One] A5's synthesis

Intermediate-2 (10.0 g, 29.90 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (8.01 g, 29.90 mmol), Pd ₂ (dba) ₃ (0.82 g) under nitrogen stream. , 0.90 mmol), P(t-bu) ₃ (1.21 g, 5.98 mmol), NaO(t-bu) (5.75 g, 59.81 mmol) and 100 ml of toluene were mixed and stirred at 110°C for 4 hours. After completion of the reaction, it was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, 12.69 g (yield: 75%) of the target compound was obtained using column chromatography.

GC-Mass (theoretical value: 565.68 g/mol, measured value: 565 g/mol)

[ Synthesis example 2] A10's synthesis

2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (11.61 g, 29.90 13.43 g (yield: 70%) of the target compound was obtained by performing the same process as Synthesis Example 1 except for using mmol).

GC-Mass (theoretical value: 641.78 g/mol, measured value: 641 g/mol)

[ Synthesis example 3] A20's synthesis

2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl instead of 2-chloro-4,6-diphenyl-1,3,5-triazine The same procedure as in Synthesis Example 1 was performed except for using -1,3,5-triazine (13.89 g, 29.90 mmol) to obtain 15.46 g (yield: 72%) of the target compound.

GC-Mass (theoretical value: 717.88 g/mol, measured value: 717 g/mol)

[ Synthesis example 4] A112 synthesis

3-bromo-9-(3-(4,6-diphenylpyrimidin-2-yl)phenyl)-9H-carba instead of 2-chloro-4,6-diphenyl-1,3,5-triazine The same process as Synthesis Example 1 was performed except for using sol (16.52 g, 29.90 mmol) to obtain 18.08 g (yield: 75%) of the target compound.

GC-Mass (theoretical value: 805.99 g/mol, measured value: 805 g/mol)

[ Synthesis example 5] A114 synthesis

3-bromo-9-(3-(4,6-diphenyl-1,3,5-triazine-2-yl instead of 2-chloro-4,6-diphenyl-1,3,5-triazine ) The same process as Synthesis Example 1 was performed except for using phenyl)-9H-carbazole (16.55 g, 29.90 mmol) to obtain 18.10 g (yield: 75%) of the target compound.

GC-Mass (theoretical value: 806.97 g/mol, measured value: 806 g/mol)

[ Synthesis example 6] A125's synthesis

Same procedure as Synthesis Example 1 except that (3-bromophenyl)triphenylsilane (12.42 g, 29.90 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. was performed to obtain 14.20 g (yield: 71%) of the target compound.

GC-Mass (theoretical value: 668.92 g/mol, measured value: 668 g/mol)

[ Synthesis example 7] A135's synthesis

Synthesis Example 1 except that (3-bromophenyl)diphenylphosphine oxide (10.68 g, 29.90 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. The same process was performed to obtain 13.70 g (yield: 75%) of the target compound.

GC-Mass (theoretical value: 610.70 g/mol, measured value: 610 g/mol)

[ Synthesis example 8] B21's synthesis

The same process as Synthesis Example 1 was performed except that 2-chloro-4-phenylquinazoline (7.20 g, 29.90 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. 12.89 g (yield: 80%) of the target compound was obtained.

GC-Mass (theoretical value: 538.65 g/mol, measured value: 538 g/mol)

[ Synthesis example 9] A34's synthesis

Intermediate-4 (10.0 g, 22.19 mmol), 4-(3-bromophenyl)-2,6-diphenylpyrimidine (8.59 g, 22.19 mmol), Pd ₂ (dba) ₃ (0.61 g, 0.67 mmol), P(t-bu) ₃ (0.90 g, 4.44 mmol), NaO(t-bu) (4.27 g, 44.39 mmol) and 100 ml of toluene were mixed and stirred at 110°C for 4 hours. After completion of the reaction, it was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, 13.44 g (yield: 80%) of the target compound was obtained using column chromatography.

GC-Mass (theoretical value: 756.95 g/mol, measured value: 756 g/mol)

[ Synthesis example 10] B21's synthesis

2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine instead of 4-(3-bromophenyl)-2,6-diphenylpyrimidine (8.62 g, 22.19 mmol ) was performed in the same manner as in Synthesis Example 9, except that 13.12 g (yield: 78%) of the target compound was obtained.

GC-Mass (theoretical value: 757.94 g/mol, measured value: 757 g/mol)

[ Synthesis example 11] A40's synthesis

Instead of 4-(3-bromophenyl)-2,6-diphenylpyrimidine, 2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl- The same process as Synthesis Example 9 was performed except for using 1,3,5-triazine (10.31 g, 22.19 mmol) to obtain 14.81 g (yield: 80%) of the target compound.

GC-Mass (theoretical value: 834.04 g/mol, measured value: 834 g/mol)

[ Synthesis example 12] A42's synthesis

Intermediate-5 (10.0 g, 20.02 mmol), 4-(3-bromophenyl)-2,6-diphenylpyrimidine (7.75 g, 20.02 mmol), Pd ₂ (dba) ₃ (0.55 g, 0.60 mmol), P(t-bu) ₃ (0.81 g, 4.00 mmol), NaO(t-bu) (3.85 g, 40.03 mmol) and 100 ml of toluene were mixed and stirred at 110°C for 4 hours. After completion of the reaction, it was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, 12.10 g (yield: 75%) of the target compound was obtained using column chromatography.

GC-Mass (theoretical value: 805.99 g/mol, measured value: 805 g/mol)

[ Synthesis example 13] A46's synthesis

2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine instead of 4-(3-bromophenyl)-2,6-diphenylpyrimidine (7.77 g, 20.02 mmol ) was performed in the same manner as in Synthesis Example 12, except that 12.28 g (yield: 76%) of the target compound was obtained.

GC-Mass (theoretical value: 806.97 g/mol, measured value: 806 g/mol)

[ Synthesis example 14] A48's synthesis

Instead of 4-(3-bromophenyl)-2,6-diphenylpyrimidine, 2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl- The same process as Synthesis Example 12 was performed except for using 1,3,5-triazine (9.29 g, 20.02 mmol) to obtain 14.14 g (yield: 80%) of the target compound.

GC-Mass (theoretical value: 883.07 g/mol, measured value: 883 g/mol)

[ Synthesis example 15] B63's synthesis

The same process as Synthesis Example 12 was performed except that 2-chloro-4-phenylquinazoline (4.82 g, 20.02 mmol) was used instead of 4-(3-bromophenyl)-2,6-diphenylpyrimidine. 10.71 g (yield: 76%) of the target compound was obtained.

GC-Mass (theoretical value: 703.85 g/mol, measured value: 703 g/mol)

[ Synthesis example 16] A50's synthesis

Intermediate-7 (10.0 g, 22.70 mmol), 4-(3-bromophenyl)-2,6-diphenylpyrimidine (8.79 g, 22.70 mmol), Pd ₂ (dba) ₃ (0.62 g, 0.68 mmol), P(t-bu) ₃ (0.92 g, 4.54 mmol), NaO(t-bu) (4.36 g, 45.40 mmol) and 100 ml of toluene were mixed and stirred at 110°C for 4 hours. After completion of the reaction, it was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, 13.56 g (yield: 80%) of the target compound was obtained using column chromatography.

GC-Mass (theoretical value: 746.93 g/mol, measured value: 746 g/mol)

[ Synthesis example 17] A54's synthesis

2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine instead of 4-(3-bromophenyl)-2,6-diphenylpyrimidine (8.81 g, 22.70 mmol ), the same process as Synthesis Example 16 was performed except that 12.22 g (yield: 72%) of the target compound was obtained.

GC-Mass (theoretical value: 747.92 g/mol, measured value: 747 g/mol)

[ Synthesis example 18] A56's synthesis

Instead of 4-(3-bromophenyl)-2,6-diphenylpyrimidine, 2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl- The same process as Synthesis Example 16 was performed except for using 1,3,5-triazine (10.54 g, 20.02 mmol) to obtain 14.03 g (yield: 75%) of the target compound.

GC-Mass (theoretical value: 824.02 g/mol, measured value: 824 g/mol)

[ Synthesis example 19] A58's synthesis

Intermediate-8 (10.0 g, 23.56 mmol), 4-(3-bromophenyl)-2,6-diphenylpyrimidine (9.12 g, 23.56 mmol), Pd ₂ (dba) ₃ (0.65 g, 0.71 mmol), P(t-bu) ₃ (0.95 g, 4.71 mmol), NaO(t-bu) (4.53 g, 47.11 mmol) and 100 ml of toluene were mixed and stirred at 110°C for 4 hours. After completion of the reaction, extraction was performed with dichloromethane, MgSO ₄ was added, and the mixture was filtered. After removing the solvent in the filtered organic layer, 12.40 g (yield: 72%) of the target compound was obtained using column chromatography.

GC-Mass (theoretical value: 730.97 g/mol, measured value: 730 g/mol)

[ Synthesis example 20] A62's synthesis

2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine instead of 4-(3-bromophenyl)-2,6-diphenylpyrimidine (9.15 g, 23.56 mmol ) was performed in the same manner as in Synthesis Example 19, except that 12.93 g (yield: 75%) of the target compound was obtained.

GC-Mass (theoretical value: 731.86 g/mol, measured value: 731 g/mol)

[ Synthesis example 21] A64's synthesis

Instead of 4-(3-bromophenyl)-2,6-diphenylpyrimidine, 2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl- The same process as Synthesis Example 19 was performed except for using 1,3,5-triazine (10.94 g, 23.56 mmol) to obtain 13.51 g (yield: 71%) of the target compound.

GC-Mass (theoretical value: 807.96 g/mol, measured value: 807 g/mol)

[ Synthesis example 22] A66's synthesis

Intermediate-3 (10.0 g, 26.01 mmol), 4-(3-bromophenyl)-2,6-diphenylpyrimidine (10.07 g, 26.01 mmol), Pd ₂ (dba) ₃ (0.71 g, 0.78 mmol), P(t-bu) ₃ (1.05 g, 5.20 mmol), NaO(t-bu) (5.00 g, 52.02 mmol) and 100 ml of toluene were mixed and stirred at 110°C for 4 hours. After completion of the reaction, extraction was performed with dichloromethane, MgSO ₄ was added, and the mixture was filtered. After removing the solvent in the filtered organic layer, 13.48 g (yield: 13%) of the target compound was obtained using column chromatography.

GC-Mass (theoretical value: 690.85 g/mol, measured value: 690 g/mol)

[ Synthesis example 23] A70's synthesis

2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine instead of 4-(3-bromophenyl)-2,6-diphenylpyrimidine (10.10 g, 26.01 mmol) ), the same process as Synthesis Example 22 was performed except that 14.40 g (yield: 80%) of the target compound was obtained.

GC-Mass (theoretical value: 691.84 g/mol, measured value: 691 g/mol)

[ Synthesis example 24] A72's synthesis

Instead of 4-(3-bromophenyl)-2,6-diphenylpyrimidine, 2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl- The same process as Synthesis Example 22 was performed except for using 1,3,5-triazine (12.08 g, 26.01 mmol) to obtain 15.18 g (yield: 76%) of the target compound.

GC-Mass (theoretical value: 767.94 g/mol, measured value: 767 g/mol)

[ Synthesis example 25] B23's synthesis

The same process as Synthesis Example 22 was performed except that 2-chloro-4-phenylquinazoline (6.26 g, 26.01 mmol) was used instead of 4-(3-bromophenyl)-2,6-diphenylpyrimidine. 11.48 g (yield: 75%) of the target compound was obtained.

GC-Mass (theoretical value: 588.71 g/mol, measured value: 588 g/mol)

[ Synthesis example 26] A97's synthesis

Intermediate-1 (10.0 g, 38.71 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (20.73 g, 77.42 mmol), Pd ₂ (dba) ₃ (1.06 g) under nitrogen stream. , 1.16 mmol), P(t-bu) ₃ (1.57 g, 7.74 mmol), NaO(t-bu) (7.44 g, 77.42 mmol) and 100 ml of toluene were mixed and stirred at 110°C for 4 hours. After completion of the reaction, extraction was performed with dichloromethane, MgSO ₄ was added, and the mixture was filtered. After removing the solvent in the filtered organic layer, 20.93 g (yield: 75%) of the target compound was obtained using column chromatography.

GC-Mass (theoretical value: 720.84 g/mol, measured value: 720 g/mol)

[ Synthesis example 27] A119's synthesis

Intermediate-10 (10.0 g, 17.37 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (9.30 g, 34.74 mmol), Pd ₂ (dba) ₃ (0.48 g) under nitrogen stream. , 0.52 mmol), P(t-bu) ₃ (0.70 g, 3.47 mmol), NaO(t-bu) (3.34 g, 34.74 mmol) and 100 ml of toluene were mixed and stirred at 110°C for 4 hours. After completion of the reaction, extraction was performed with dichloromethane, MgSO ₄ was added, and the mixture was filtered. After removing the solvent in the filtered organic layer, 9.81 g (yield: 70%) of the target compound was obtained using column chromatography.

GC-Mass (theoretical value: 806.97 g/mol, measured value: 806 g/mol)

[ Synthesis example 28] A122's synthesis

Except for using 4-(3-bromophenyl)-2,6-diphenylpyrimidine (13.45 g, 17.37 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. Then, the same process as Synthesis Example 27 was performed to obtain 11.03 g (yield: 72%) of the target compound.

GC-Mass (theoretical value: 882.08 g/mol, measured value: 882 g/mol)

[ Synthesis example 29] A124 synthesis

2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (6.74 g, 17.37 11.50 g (yield: 75%) of the target compound was obtained by performing the same process as Synthesis Example 27 except for using mmol).

GC-Mass (theoretical value: 883.07 g/mol, measured value: 883 g/mol)

[ Synthesis example 30] B5's synthesis

Intermediate-11 (10.0 g, 15.98 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (4.28 g, 15.98 mmol), Pd ₂ (dba) ₃ (0.44 g) under nitrogen stream. , 0.48 mmol), P(t-bu) ₃ (0.65 g, 3.20 mmol), NaO(t-bu) (3.07 g, 31.96 mmol) and 100 ml of toluene were mixed and stirred at 110°C for 4 hours. After completion of the reaction, it was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, 9.59 g (yield: 70%) of the target compound was obtained using column chromatography.

GC-Mass (theoretical value: 857.03 g/mol, measured value: 857 g/mol)

[ Synthesis example 31] B10's synthesis

2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (6.20 g, 15.98 The same process as Synthesis Example 30 was performed except for using mmol) to obtain 11.18 g (yield: 75%) of the target compound.

GC-Mass (theoretical value: 933.13 g/mol, measured value: 933 g/mol)

[ Synthesis example 32] B65's synthesis

Intermediate-6 (10.0 g, 18.19 mmol), 2-chloro-4-phenylquinazoline (4.38 g, 18.19 mmol), Pd ₂ (dba) ₃ (0.50 g, 0.55 mmol), P(t-bu) under nitrogen stream. ) ₃ (0.74 g, 3.64 mmol), NaO(t-bu) (3.50 g, 36.38 mmol) and 100 ml of toluene were mixed and stirred at 110°C for 4 hours. After completion of the reaction, it was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, 9.60 g (yield: 70%) of the target compound was obtained using column chromatography.

GC-Mass (theoretical value: 753.91 g/mol, measured value: 753 g/mol)

[ Example 1] Organic electric field Fabrication of light emitting devices

A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1500 Å was washed with distilled water ultrasonic waves. After cleaning with distilled water, ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, and methanol, drying, transferring to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then cleaning the substrate for 5 minutes using UV. Afterwards, the substrate was transferred to a vacuum laminate.

DS-205 (80 nm) / NPB (15 nm) / ADN + 5% DS-405 (30 nm) / each compound specified in Table 1 (80 nm) / LiF (1 nm) / Al ( 200nm), an organic electroluminescent device was manufactured in this order.

[ Example 2 ~ 30] Organic electric field Fabrication of light emitting devices

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compounds listed in Table 1 below were used instead of Compound A-3, which was used as the electron transport layer material when forming the electron transport layer in Example 1.

[ Comparative example One] abandonment electric field Fabrication of light emitting devices

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Alq ₃ was used as the electron transport layer material instead of Compound A-3 when forming the electron transport layer in Example 1.

DS-205 and DS-405 used in device manufacturing are products of Doosan Electronics BG, and the structures of NPB, AND, and Alq ₃ are as follows.

[ Evaluation example One]

The driving voltage and current efficiency were measured at a current density of 10 mA/cm2 for the organic electroluminescent devices manufactured in Examples 1 to 30 and Comparative Example 1, and the results are shown in Table 1 below.

Sample electron transport layer driving voltage
(V) Current efficiency
(cd/A) Example 1 Compound A-3 4.2 8.2 Example 2 Compound A-4 3.7 8.5 Example 3 Compound A-5 3.5 7.2 Example 4 Compound A-6 3.5 8.8 Example 5 Compound A-7 3.7 9.1 Example 6 Compound A-19 3.8 8.5 Example 7 Compound A-20 4.5 8.5 Example 8 Compound A-21 4.5 7.8 Example 9 Compound A-22 3.9 7.9 Example 10 Compound A-23 3.6 8.2 Example 11 Compound A-24 3.3 8.1 Example 12 Compound A-25 3.4 8.5 Example 13 Compound A-26 3.7 8.6 Example 14 Compound A-27 4.2 8 Example 15 Compound A-28 4.1 8.9 Example 16 Compound A-29 4.2 8.2 Example 17 Compound A-30 3.7 8.5 Example 18 Compound A-31 3.5 7.2 Example 19 Compound A-32 3.5 8.8 Example 20 Compound A-33 3.7 9.1 Example 21 Compound A-34 3.8 8.5 Example 22 Compound A-35 4.5 8.5 Example 23 Compound A-36 4.5 7.8 Example 24 Compound A-37 3.9 7.9 Example 25 Compound A-38 3.6 8.2 Example 26 Compound A-39 3.3 8.1 Example 27 Compound A-40 3.4 8.5 Example 28 Compound A-41 3.7 8.6 Example 29 Compound A-42 4.2 8 Example 30 Compound A-43 4.1 8.9 Comparative Example 1 Alq ₃ 4.7 5.6

As shown in Table 1, the organic electroluminescent device using the compound according to the present invention as an electron transport layer (organic electroluminescent device prepared in Examples A-1 to A-33, respectively) is a conventional organic electroluminescent device using Alq ₃ . It can be seen that it exhibits better performance in terms of current efficiency and driving voltage compared to the light emitting device (organic electroluminescent device of Comparative Example 1).

[ Example 31] Green Organic electric field Fabrication of light emitting devices

After purifying the synthesized compound to high purity by sublimation using a commonly known method, a green organic electroluminescent device was manufactured as follows.

A glass substrate coated with a 1500 Å thin film of ITO (indium tin oxide) was washed with distilled water ultrasonic waves. After cleaning with distilled water, ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, and methanol, drying, transferring to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then washing the substrate for 5 minutes using UV. After cleaning, the substrate was transferred to a vacuum evaporator.

On the ITO transparent electrode prepared as above, m-MTDATA (60 nm)/TCTA (80 nm)/each compound specified in Table 2 (40 nm)/CBP + 10% Ir(ppy)3 (300 nm)/BCP (10 An organic electroluminescent device was manufactured by stacking in the following order: nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm).

The structures of m-MTDATA, TCTA, Ir(ppy)3, CBP and BCP used are as follows.

[ Example 32 ~ 58] Green Organic electric field Fabrication of light emitting devices

An organic electroluminescent device was manufactured in the same manner as Example 31, except that the compounds listed in Table 2 below were used instead of Compound A-15, which was used as the green light-emitting layer material in Example 31 when forming the green light-emitting layer.

[ Comparative example 2] Green Organic electric field Fabrication of light emitting devices

A green organic electroluminescent device was manufactured in the same manner as Example 31, except that Compound A-15 was not used in Example 31.

[ Evaluation example 2]

For the organic electroluminescent devices prepared in Examples 31 to 58 and Comparative Example 2, the driving voltage, current efficiency, and luminescence peak were measured at a current density of 10 mA/cm2, and the results are shown in Table 2 below. .

Sample luminescent layer Driving voltage (V) Current efficiency (cd/A) Example 31 Compound A-15 6.7 41.9 Example 32 Compound A-16 6.85 42.1 Example 33 Compound A-17 6.8 44.8 Example 34 Compound A-18 6.8 47.5 Example 35 Compound A-19 6.85 41.5 Example 36 Compound A-20 6.9 41.9 Example 37 Compound A-21 6.95 42.4 Example 38 Compound A-22 6.8 42.3 Example 39 Compound A-27 6.9 45.2 Example 40 Compound A-28 6.8 44.6 Example 41 Compound A-29 6.7 44.1 Example 42 Compound A-30 6.65 43.6 Example 43 Compound A-31 6.7 42.6 Example 44 Compound A-61 6.9 44.1 Example 45 Compound A-62 6.8 42.8 Example 46 Compound A-63 6.7 41.4 Example 47 Compound A-64 6.7 41.8 Example 48 Compound A-65 6.65 45.3 Example 49 Compound A-66 6.7 45.1 Example 50 Compound A-67 6.65 42.6 Example 51 Compound A-68 6.6 41.3 Example 52 Compound A-69 6.6 42.1 Example 53 Compound A-70 6.7 41.9 Example 54 Compound A-71 6.9 42.1 Example 55 Compound A-72 6.8 44.8 Example 56 Compound A-73 6.8 47.5 Example 57 Compound A-74 6.85 41.5 Example 58 Compound A-75 6.85 41.9 Comparative Example 2 - 6.93 38.2

As shown in Table 2, the green organic electroluminescent device using the compound according to the present invention as a light-emitting material (green organic electroluminescent device prepared in Examples 31 to 58, respectively) is a green organic electroluminescent device using only conventional CBP as a material for the light-emitting layer. It can be seen that it exhibits better performance in terms of current efficiency and driving voltage compared to the organic electroluminescent device (the organic electroluminescent device of Comparative Example 2).

[ Example 59] Red Organic electric field Fabrication of light emitting devices

The synthesized compound was purified to high purity by sublimation using a commonly known method, and then a red organic electroluminescent device was manufactured according to the process below.

First, a glass substrate coated with a 1500Å thin film of ITO (indium tin oxide) was washed with distilled water ultrasonic waves. After washing with distilled water, the substrate is ultrasonic cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech). Then, the substrate is cleaned using UV for 5 minutes and then vacuum evaporated. The substrate was transferred to .

On the ITO transparent electrode prepared as above, m-MTDATA (60 nm)/TCTA (80 nm)/each compound specified in Table 3 (40nm)/CBP + 10% (piq)2Ir(acac) (300nm)/BCP An organic electroluminescent device was manufactured by stacking in the following order: (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm).

The structures of m-MTDATA, TCTA, (piq)2Ir(acac), and CBP used are as follows.

[ Example 60 ~ 70] Red Organic electric field Fabrication of light emitting devices

An organic electroluminescent device was manufactured in the same manner as Example 59, except that the compounds listed in Table 3 below were used instead of Compound B-5, which was used as the red light-emitting layer material when forming the red light-emitting layer in Example 59.

[ Comparative example 3] Red organic electric field Fabrication of light emitting devices

A red organic electroluminescent device was manufactured in the same manner as Example 59, except that Compound B-5 was not used in Example 59.

[ Evaluation example 3]

For the organic electroluminescent devices prepared in Examples 59 to 70 and Comparative Example 3, the driving voltage, current efficiency, and luminescence peak were measured at a current density of 10 mA/cm2, and the results are shown in Table 2 below. .

Sample luminescent layer Driving voltage (V) Current efficiency (cd/A) Example 59 Compound B-5 4.9 11.9 Example 60 Compound B-10 5.1 12.1 Example 61 Compound B-15 5 14.8 Example 62 Compound B-20 5 17.5 Example 63 Compound B-21 5.1 11.5 Example 64 Compound B-22 5.1 11.9 Example 65 Compound B-23 5.2 12.4 Example 66 Compound B-24 5 12.3 Example 67 Compound B-25 5.1 15.2 Example 68 Compound B-61 5 14.6 Example 69 Compound B-62 4.9 14.1 Example 70 Compound B-63 4.9 13.6 Comparative Example 3 - 5.2 8.2

As shown in Table 3, the red organic electroluminescent device using the compound according to the present invention as the light-emitting material (the red organic electroluminescent device prepared in Examples 59 to 70, respectively) is the red organic electroluminescent device using only the conventional CBP as the material of the light-emitting layer. It was found that compared to the organic electroluminescent device (the organic electroluminescent device of Comparative Example 3), it exhibited better performance in terms of current efficiency and driving voltage.

[ Example 71] Blue Organic electric field Fabrication of light emitting devices

The compound synthesized in the synthesis example was purified to high purity by sublimation using a commonly known method, and then a red organic electroluminescent device was manufactured according to the process below.

First, a glass substrate coated with a 1500Å thin film of ITO (indium tin oxide) was washed with distilled water ultrasonic waves. After washing with distilled water, the substrate is ultrasonic cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech). Then, the substrate is cleaned using UV for 5 minutes and then vacuum evaporated. The substrate was transferred to .

On the ITO transparent electrode prepared as above, DS-205 (Doosan) (80 nm)/NPB (15 nm)/each compound specified in Table 4 (15nm)/ADN + 5% DS-405 (Doosan) ( An organic electroluminescent device was manufactured by stacking in the following order: 300 nm)/BCP (10 nm)/Alq ₃ (30 nm)/LiF (1 nm)/Al (200 nm).

The structure of the ADN used is as follows.

[ Example 72 ~ 94] Blue Organic electric field Fabrication of light emitting devices

An organic electroluminescent device was manufactured in the same manner as in Example 71, except that the compounds listed in Table 4 below were used instead of Compound A-1, which was used as the blue light-emitting layer material when forming the blue light-emitting layer in Example 71.

[ Comparative example 4] Blue Organic electric field Fabrication of light emitting devices

A blue organic electroluminescent device was manufactured in the same manner as in Example 71, except that Compound A-1 used in Example 71 was not used.

[ Evaluation example 4]

The driving voltage and current efficiency were measured at a current density of 10 mA/cm2 for each blue organic electroluminescent device manufactured in Examples 71 to 94 and Comparative Example 4, and the results are shown in Table 4 below.

Sample luminescent layer Driving voltage (V) Current efficiency (cd/A) Example 71 Compound A-1 4.3 9.2 Example 72 Compound A-2 4.5 7.1 Example 73 Compound A-3 4.6 8.3 Example 74 Compound A-4 4.2 9.6 Example 75 Compound A-5 4.7 6.5 Example 76 Compound A-6 4.9 7.1 Example 77 Compound A-7 4.5 8.6 Example 78 Compound A-8 4.7 7.5 Example 79 Compound A-9 4.9 7.6 Example 80 Compound A-10 4.6 8.6 Example 81 Compound A-11 5.2 7.1 Example 82 Compound A-12 5.3 5.6 Example 83 Compound A-13 4.5 9 Example 84 Compound A-14 4.8 8.2 Example 85 Compound A-15 4.7 8.2 Example 86 Compound A-16 4.7 7.5 Example 87 Compound A-17 4.9 7.6 Example 88 Compound A-18 4.6 8.6 Example 89 Compound A-19 5.2 7.1 Example 90 Compound A-20 5.3 5.6 Example 91 Compound A-21 4.5 9 Example 92 Compound A-22 4.8 8.2 Example 93 Compound A-23 4.7 8.2 Example 94 Compound A-24 4.2 9.6 Comparative Example 4 - 5.6 4.8

As shown in Table 4, the blue organic electroluminescent device using the compound according to the present invention as a light-emitting material (blue organic electroluminescent device prepared in Examples 71 to 94, respectively) is similar to the conventional blue organic electroluminescent device (comparison). It was found that it exhibited better performance in terms of current efficiency and driving voltage compared to the organic electroluminescent device of Example 4).

Claims (13)

A compound represented by the following formula (2):
[Formula 2]

In Formula 2,
L ₁ is a single bond,
L ₂ to L ₅ are each independently selected from the group consisting of a single bond, a C ₆ to C ₁₈ arylene group, and a heteroarylene group having 5 to 18 nuclear atoms;
R ₁ is hydrogen, a carbazole group, or a benzocarbazole group;
R ₂ may be selected from the group consisting of hydrogen and an aryl group of C ₆ to C ₆₀ or may be combined with an adjacent group to form a condensed ring;
R ₃ is hydrogen;
One of Ar ₁ and Ar ₂ is selected from the substituent group consisting of the following formulas F-2, F-4, F-6, F-8 and formula 13, and the other is a triphenylene group, phenanthrene group, carbazole group or It is a benzocarbazole group;

[Formula 13]

* refers to the part where the combination takes place;
l, m, n and u are each independently an integer from 0 to 4;
v is an integer from 0 to 3;
w is an integer from 0 to 2;
R ₆ And R ₁₀ to R ₁₃ 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 ₆ ~C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₃ to C ₄₀ cycloalkyl group, number of nuclear atoms 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ arylamine group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₆₀ aryl boron group, C ₆ It may be selected from the group consisting of ~C ₆₀ arylphosphine group, C ₆ ~C ₆₀ mono or diarylphosphinyl group, and C ₆ ~C ₆₀ arylsilyl group, or may be combined with an adjacent group to form a condensed ring. , when each of R ₁₀ is plural, they are the same or different from each other;
The arylene group and heteroarylene group of L ₂ to L ₃ , the carbazole group and benzocarbazole group of R ₁ , the aryl group of R ₂ , and the pyridine group, pyrimidine group, triazine group, and triphenylene group of Ar ₁ and Ar ₂ , phenanthrene group, quinazoline group and silane group and R ₆ and R ₁₀ alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, aryl Phosphine group, mono or diarylphosphinyl group, and arylsilyl group are each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of Alkynyl group, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryl Amine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl is substituted or unsubstituted with one or more substituents selected from the group consisting of a boron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group; , when substituted with a plurality of substituents, these may be the same or different from each other. delete delete delete delete delete delete delete According to paragraph 1,
Wherein L ₂ to L ₅ are each independently a single bond or a linker represented by any of the following formulas 14 to 16:
[Formula 14]

[Formula 15]

[Formula 16]

In Formulas 14 to 16,
* refers to the part where the combination takes place;
Y ₁ to Y ₈ are each independently N or C(R ₁₄ );
In Formula 14, at least two of Y ₁ to Y ₆ are C(R ₁₄ ), and in Formula 15, at least one of Y ₁ to Y ₄ is C(R ₁₄ ), and at least one of Y ₅ to Y ₈ is C(R ₁₄ ), and at least two of Y ₁ to Y ₄ in Formula 16 are C(R ₁₄ );
R ₁₄ is absent or represents 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 with 3 to 40 nuclear atoms, aryl group with C ₆ to C ₆₀ , heteroaryl group with 5 to 60 nuclear atoms, alkyloxy group with C ₁ to C ₄₀ , 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 selected from the group consisting of an arylphosphine group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylamine group, and when R ₁₄ is plural, 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, alkyl boron group, aryl boron group, Arylphosphine 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 to C ₆₀ aryl group, heteroaryl group with 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, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ Unsubstituted or substituted with one or more substituents selected from the group consisting of arylboron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and C ₆ ~ C ₆₀ arylsilyl group. And when substituted with a plurality of substituents, these may be the same or different from each other. According to paragraph 1,
The compound is represented by the following formula (17):
[Formula 17]

In Formula 17 above,
Each of L ₁ to L ₅ , Ar ₁ , Ar ₂ , l, n, R ₂ and R ₃ is as defined in Formula 2 above. According to paragraph 1,
The compound is 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,
An organic electroluminescent device, wherein at least one of the one or more organic layers includes the compound represented by the formula (2) of claim 1. According to clause 12,
The organic material layer containing the compound is an organic electroluminescent device selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron transport auxiliary layer, an electron injection layer, a lifespan improvement layer, a light emitting layer, and a light emitting auxiliary layer.