WO2016126031A2 - Organic compound and organic electroluminescent element comprising same - Google Patents

Abstract

The present invention relates to: a novel compound having an excellent light-emitting ability; and an organic electroluminescent element having improved characteristics such as light-emitting efficiency, driving voltage, and lifespan since at least one organic layer thereof contains the compound.

Description

Organic compound and organic electroluminescent device comprising the same

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

In the 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, excitons are formed, and when the excitons fall to the ground, they shine. 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 and the like according to its function.

In order to increase the luminous efficiency of the organic electroluminescent device, it is necessary to increase the color purity and to transfer energy. For this, a light emitting material mixed with a host material and a dopant material may be used. 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 phosphor can theoretically improve the luminous efficiency up to four times as compared to the fluorescent material, studies on phosphorescent hosts as well as phosphorescent dopants have been conducted. Currently, as a phosphorescent dopant material of the light emitting layer, metal complex compounds including Ir such as Firpic, Ir (ppy) ₃ , and (acac) Ir (btp) ₂ are known, and CBP is known as a phosphorescent host material.

However, the conventional materials do not have a satisfactory level in terms of lifespan in the organic electroluminescent device because of the low glass transition temperature and poor thermal stability. Therefore, there is a demand for the development of an organic EL device including a light emitting material having excellent performance.

The present invention can be applied to an organic electroluminescent device, and an object of the present invention is to provide a novel organic compound capable of preventing the diffusion of excitons.

An object of the present invention is to provide an organic electroluminescent device having improved characteristics such as driving voltage, luminous efficiency and lifespan, including the novel organic compound.

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

In Chemical Formula 1,

R ₁ and R ₂ are the same as or different from each other, and are each independently selected from the group consisting of hydrogen, an alkyl group of C ₁ to C ₄₀ , and an aryl group of C ₆ to C ₆₀ ;

m and n are each an integer of 0 to 3;

a and b are each independently an integer of 0 to 4,

R ₃ and R ₄ are each independently deuterium, halogen group, cyano group, nitro group, amino 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, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyl silyl group, C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl boron group, a phosphine group , C ₁ ~ C ₄₀ alkyl phosphine group, C ₆ ~ C ₄₀ aryl phosphine group, C ₁ ~ C ₄₀ alkyl phosphine oxide group, C ₆ ~ C ₄₀ aryl phosphine oxide group and C ₆ ~ C ₆₀ It is selected from the group consisting of an arylamine group;

Ar ₁ and Ar ₂ are the same as or different from each other, each independently represent a substituent represented by the formula (2),

* Is a moiety bound to Formula 1,

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

o is 0 or 1,

Z ₁ to Z ₅ are the same as or different from each other, and each independently N or C (R ₅ ), provided that at least one of Z ₁ to Z ₅ is N,

At this time, when a plurality of C (R ₅ ), a plurality of R ₅ are the same or different from each other, one or more R ₅ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ An alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a nuclear atom having 3 to 40 heterocycloalkyl groups, a C ₆ to C ₆₀ aryl group, heteroaryl of nuclear atoms of 5 to 60 aryl group, C ₁ ~ C ₄₀ of the alkyloxy group, C ₆ ~ C ₆₀ of the aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ aryl of C ₆₀ silyl group , C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, phosphine group, C ₁ ~ C ₄₀ Alkylphosphine group, C ₆ ~ C ₆₀ Aryl phosphine group, C ₁ ~ C ₄₀ An alkylphosphine oxide group, a C ₆ to C ₆₀ arylphosphine oxide group and a C ₆ to C ₆₀ arylamine group, or a condensed aromatic ring or a condensed hetero group in combination with another adjacent R ₅ or L; direction Can form a foot ring;

The alkyl group, aryl group, R ₃ to R ₅ alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl of R ₁ and R ₂ Group, arylsilyl group, alkyl boron group, aryl boron group, phosphine group, alkyl phosphine group, aryl phosphine group, alkyl phosphine oxide group, aryl phosphine oxide group and arylamine group, arylene group of L, heteroarylene group, Deuterium, halogen group, cyano group, nitro group, amino 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 , nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group, nuclear atoms aryl of from 5 to 40 heteroaryl group, a C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ aryloxy of C ₆₀ group, C ₁ ~ C ₄₀ alkyl silyl group, C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl boron group, a phosphine Group, C ₁ ~ C ₄₀ alkyl phosphine group, C ₆ ~ C ₆₀ aryl phosphine group, C ₁ ~ C ₄₀ alkyl phosphine oxide group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C Substituted or unsubstituted with one or more substituents selected from the group consisting of ₆₀ arylamine groups, wherein the substituents are the same or different from each other.

The present invention also includes (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer is one of the chemical formulas described above. It provides an organic electroluminescent device comprising the compound represented by 1.

Herein, the organic material layer containing the compound is preferably a light emitting layer. In this case, the compound represented by Formula 1 is a host of the light emitting layer.

In addition, the light emitting layer preferably contains a metal complex compound dopant.

Since the compound according to the present invention has excellent thermal stability, carrier transport properties and luminescent properties, it can be used as an organic material layer material of an organic electroluminescent device. In particular, in the case of the organic electroluminescent device including the compound according to the present invention as a light emitting layer material, it can have excellent light emission performance, low driving voltage, high efficiency and long life compared to the organic electroluminescent device comprising a conventional host material, Furthermore, the performance and lifespan of the full color display panel can be improved.

EMBODIMENT OF THE INVENTION Hereinafter, this invention is demonstrated.

The novel compound according to the present invention is an alkyl or aryl group introduced into the pyrimidine moiety of pyrazolo [1,5-a] pyrimidine moiety, and a phenylene group is introduced into the pyrazole moiety. Or a structure having a basic skeleton introduced with an arylene group or a hetero arylene group, characterized in that represented by the formula (1). The compound represented by the formula (1) has a high glass transition temperature not only excellent thermal stability, but also excellent carrier transport properties and light emission performance. Therefore, when the organic electroluminescent device includes the compound of Formula 1, the driving voltage, efficiency, lifespan, etc. of the device may be improved.

Specifically, in the compound of Formula 1, the pyrazolo [1,5-a] pyrimidine moiety is a high electron absorbing moiety, and the electron donating group (EDG) having a large electron donor is present in the moiety. When bonded, the entire molecule has a bipolar (bipolar) characteristics, it is possible to increase the binding force between the hole and the electron. As such, the compound of the present invention in which EDG is introduced into the moiety is excellent in excellent carrier transport properties and luminescence properties.

As such, the compound represented by Chemical Formula 1 may improve the light emission characteristics of the organic EL device, and also improve carrier transportability, light emission efficiency, driving voltage, lifetime characteristics, thermal stability, and the like. Therefore, the compound of formula 1 according to the present invention can be used as an organic material layer, preferably a light emitting auxiliary layer material of the organic electroluminescent device. The organic electroluminescent device including the compound of the present invention can greatly improve performance and lifespan characteristics, and the full color organic light emitting panel to which the organic electroluminescent device is applied can also maximize its performance.

In the compound represented by Formula 1 according to the present invention, R ₁ and R ₂ are the same as or different from each other, each independently selected from the group consisting of hydrogen, an alkyl group of C ₁ ~ C ₄₀ , and an aryl group of C ₆ ~ C ₆₀ do. Preferably, R ₁ and R ₂ are the same as or different from each other, and each independently may be selected from the group consisting of hydrogen, an alkyl group of C ₁ ~ C ₂₀ , and an aryl group of C ₆ ~ C ₃₀ .

At this time, the alkyl group and the aryl group of R ₁ and R ₂ are each independently deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group (preferably C ₁ ~ C ₂₀ alkyl group), C ₂ ~ C ₄₀ alkenyl group (preferably C ₂ ~ alkenyl group of _{C 20), C 2 ~ C} 40 alkynyl groups (preferably C ₂ ~ alkynyl group of _{C 20), C 3 ~ C} 40 cycloalkyl group (preferably of the Preferably a C ₃ to C ₂₀ cycloalkyl group), a heterocycloalkyl group having 3 to 40 nuclear atoms (preferably a heterocycloalkyl group having 3 to 20 nuclear atoms), and an aryl group having a C ₆ to C ₄₀ (preferably C ₆ to Aryl group of C ₂₀ ), heteroaryl group of 5 to 40 nuclear atoms (preferably heteroaryl group of 5 to 20 nuclear atoms), alkyloxy group of C ₁ to C ₄₀ (preferably of C ₁ to C ₂₀ Alkyloxy group), C ₆ to C ₆₀ aryloxy group (preferably C ₆ to C ₃₀ aryloxy group), C ₁ to C ₄₀ alkylsilyl group (preferably C ₁ to C ₂₀ alkylsilyl group) , C for ₆ ~ C ₆₀ O A silyl group (preferably C arylsilyl group of _{6 ~ C 30), C 1} ~ C 40 alkyl boron group (preferably C ₁ ~ alkyl boronic groups of the _{C 20), C 6 ~ C} 60 aryl boron group (preferably in the C ₆ ~ C ₃₀ aryl boron group), C ₁ ~ C ₄₀ Alkyl phosphine group (preferably C ₁ ~ C ₂₀ Alkyl phosphine group), C ₆ ~ C ₆₀ Aryl phosphine group (Preferably C ₆ ~ C ₃₀ aryl phosphine group), C ₁ ~ C ₄₀ aryl phosphine oxide group (preferably C ₁ ~ C ₂₀ alkyl phosphine oxide group), C ₆ ~ C ₆₀ aryl phosphine oxide group (preferably C ₆ to C ₃₀ arylphosphineoxide group) and C ₆ to C ₆₀ arylamine group (preferably C ₆ to C ₃₀ arylamine group) substituted or unsubstituted with one or more substituents selected from the group consisting of In this case, when the substituent is plural, they are the same as or different from each other.

In addition, a and b are each an integer of 0 to 4, and when a and b are each 0, it means that hydrogen is not substituted with substituents R ₃ and R ₄ , respectively, wherein a and b are 1 to 4, respectively. in the case of an integer, R ₃ and R ₄ are the same or different, each independently represent a deuterium, a halogen group, a cyano group, a nitro group, an amino group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C Alkynyl group of ₂ to C ₄₀ , cycloalkyl group of C ₃ to C ₄₀ , heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyl silyl group, C ₆ ~ aryl silyl group of C _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ aryl boron, phosphine group, C ₁ ~ C ₄₀ alkyl phosphine group, C ₆ ~ C ₄₀ aryl phosphine group C ₁ ~ C ₄₀ alkyl phosphine oxide group, C ₆ ~ C ₄₀ aryl phosphine Fin oxide group and C ₆ ~ C ₆₀ aryl It is selected from the group consisting of amine groups.

Preferably, when a and b are each an integer of 1 to 4, R ₃ and R ₄ are the same as or different from each other, and each independently deuterium, an alkyl group of C ₁ ~ C ₄₀ , an aryl group of C ₆ ~ C ₆₀ , It may be selected from the group consisting of a heteroaryl group of 5 to 60 nuclear atoms and an arylamine group of C ₆ ~ C ₆₀ .

At this time, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group of the R ₃ and R ₄ , Aryl boron group, phosphine group, alkyl phosphine group, aryl phosphine group, alkyl phosphine oxide group, aryl phosphine oxide group and arylamine group are each independently deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group (preferably C ₁ ~ C ₂₀ alkyl group), C ₂ ~ C ₄₀ alkenyl group (preferably C ₂ ~ C ₂₀ alkenyl group), C ₂ ~ C ₄₀ alkynyl group (preferably C ₂ ~ C ₂₀ of the alkynyl group), C ₃ ~ C ₄₀ cycloalkyl group (preferably a C ₃ ~ C ₂₀ cycloalkyl group), the nuclear atoms of 3 to 40 heterocycloalkyl group (preferably the number of from 3 to 20 hetero nuclear atoms Cycloalkyl groups), C ₆ -C ₄₀ aryl groups (preferably C ₆ -C ₂₀ aryl groups), nuclear atoms of 5 to 40 Heteroaryl group (preferably a heteroaryl group having 5 to 20 nuclear atoms), C ₁ ~ C ₄₀ alkyloxy group (preferably C ₁ ~ C ₂₀ alkyloxy group), C ₆ ~ C ₆₀ aryloxy group (Preferably C ₆ to C ₃₀ aryloxy group), C ₁ to C ₄₀ alkylsilyl group (preferably C ₁ to C ₂₀ alkylsilyl group), C ₆ to C ₆₀ arylsilyl group (preferably C ₆ to C ₃₀ arylsilyl group, C ₁ to C ₄₀ alkyl boron group (preferably C ₁ to C ₂₀ alkyl boron group), C ₆ to C ₆₀ aryl boron group (preferably C ₆ to C ₃₀ Aryl boron group), C ₁ ~ C ₄₀ alkyl phosphine group (preferably C ₁ ~ C ₂₀ alkyl phosphine group), C ₆ ~ C ₆₀ aryl phosphine group (preferably C ₆ ~ C ₃₀ aryl phosphine group ), C ₁ ~ C ₄₀ aryl phosphine oxide group (preferably C ₁ ~ C ₂₀ alkyl phosphine oxide group), C ₆ ~ C ₆₀ aryl phosphine oxide group (preferably C ₆ ~ C ₃₀ aryl phosphine oxide groups of the pin), and C ₆ ~ C ₆₀ aryl amine groups (preferably C ₆ ~ C ₃₀ Substituted by one or more substituent species selected from the group consisting of an amine group reel) or be unsubstituted, wherein when the substituent is plural, they are the same as or different from each other.

In addition, m and n are each an integer of 0 to 3, preferably m may be 1. At this time, the binding position of R ₃ and R ₄ is possible in all ortho-, meta-, para-.

In addition, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a substituent represented by the following formula (2). At this time, the binding position of Ar ₁ and Ar ₂ is possible in all ortho-, meta-, para-.

In Chemical Formula 2, * is a portion bonded to Chemical Formula 1.

L is a single bond or is selected from the group consisting of a C ₆ ~ C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms, preferably a single bond, or may be a phenylene group or a biphenylene group.

At this time, the arylene group and heteroarylene group of L are each independently deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group (preferably C ₁ ~ C ₂₀ alkyl group), C ₂ ~ C ₄₀ alkenyl group (preferably C ₂ to C ₂₀ alkenyl group), C ₂ to C ₄₀ alkynyl group (preferably C ₂ to C ₂₀ alkynyl group), C ₃ to C ₄₀ cycloalkyl group (preferably C ₃ -C ₂₀ cycloalkyl group), a heterocycloalkyl group of 3 to 40 nuclear atoms (preferably a heterocycloalkyl group of 3 to 20 nuclear atoms), an aryl group of C ₆ ~ C ₄₀ (preferably C ₆ ~ C An aryl group of ₂₀ ), a heteroaryl group of 5 to 40 nuclear atoms (preferably a heteroaryl group of 5 to 20 nuclear atoms), an alkyloxy group of C ₁ to C ₄₀ (preferably C ₁ to C ₂₀ alkyl) Oxy group), C ₆ to C ₆₀ aryloxy group (preferably C ₆ to C ₃₀ aryloxy group), C ₁ to C ₄₀ alkylsilyl group (preferably C ₁ to C ₂₀ alkylsilyl group), C ₆ ~ C ₆₀ Aryl silyl group (preferably C arylsilyl group of _{6 ~ C 30), C 1} ~ group alkylboronic of C ₄₀ (group preferably C ₁ ~ alkyl boron C _20), aryl boronic a C ₆ ~ C ₆₀ group ( Preferably C ₆ ~ C ₃₀ aryl boron group), C ₁ ~ C ₄₀ Alkyl phosphine group (preferably C ₁ ~ C ₂₀ Alkyl phosphine group), C ₆ ~ C ₆₀ Aryl phosphine group (preferably C ₆ Aryl phosphine group of ~ C ₃₀ , C ₁ ~ C ₄₀ aryl phosphine oxide group (preferably C ₁ ~ C ₂₀ alkyl phosphine oxide group), C ₆ ~ C ₆₀ aryl phosphine oxide group (preferably C aryl phosphine oxide groups of ₆ ~ C _30), and C ₆ ~ C ₆₀ aryl amine group (preferably a substituted from the group consisting of an arylamine group) in C ₆ ~ C ₃₀ with 1 substituent at least one selected or unsubstituted and ring In this case, when the substituents are plural, they are the same or different from each other.

Z ₁ to Z ₅ are the same as or different from each other, and each independently N or C (R ₅ ), provided that at least one of Z ₁ to Z ₅ is N.

In this case, when there are a plurality of C (R ₅ ), a plurality of R ₅ are the same or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, amino group, C ₁ ~ 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, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ to C ₆₀ aryl group, nuclear atom 5 To 60 heteroaryl group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, phosphine group, C ₁ ~ C ₄₀ alkyl phosphine group, C ₆ ~ C ₄₀ aryl phosphine group, C ₁ ~ C ₄₀ alkyl phosphine oxide Group, C ₆ ~ C ₄₀ aryl phosphine oxide group and C ₆ ~ C ₆₀ arylamine group, or combine with other adjacent R ₅ or L to form a condensed aromatic ring or condensed heteroaromatic ring Could Preferably selected from the group consisting of hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group of 5 to 60 nuclear atoms, and an arylamine group of C ₆ to C ₆₀ , or A condensed aromatic ring of C ₆ to C ₆₀ (preferably a C ₆ to C ₃₀ condensed aromatic ring) in combination with other adjacent R ₅ or L or N, O, S or Se containing 5 to 60 nuclear atoms; Heteroaromatic ring (N, O, S, or Se-containing condensed heteroaromatic ring having 5 to 30 nuclear atoms).

In this case, the alkyl groups of the R _5, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an arylboronic Group, phosphine group, alkyl phosphine group, aryl phosphine group, alkyl phosphine oxide group, aryl phosphine oxide group and arylamine group are each independently deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group (preferably C ₁ ~ alkyl group of _{C 20), C 2 ~ C} 40 alkenyl group (preferably C ₂ ~ alkenyl group of _{C 20), C 2 ~ C} 40 alkynyl groups (preferably C ₂ ~ C ₂₀ of An alkynyl group), a C ₃ to C ₄₀ cycloalkyl group (preferably a C ₃ to C ₂₀ cycloalkyl group), a nuclear atom having 3 to 40 heterocycloalkyl groups (preferably a nuclear atom having 3 to 20 heterocycloalkyl groups) , C ₆ ~ C ₄₀ aryl group (preferably a C ₆ ~ C ₂₀ aryl group), the number of nuclear atoms of 5 to 40 of the hete An aryl group (alkyloxy group of preferably C ₁ ~ C ₂₀₎ (preferably nuclear atoms of 5 to 20 heteroaryl group), C ₁ ~ C ₄₀ alkyloxy group, the aryloxy group of a C ₆ ~ C ₆₀ ( Preferably an C ₆ -C ₃₀ aryloxy group), a C ₁ -C ₄₀ alkylsilyl group (preferably a C ₁ -C ₂₀ alkylsilyl group), a C ₆ -C ₆₀ arylsilyl group (preferably C ₆ Aryl silyl group of ~ C ₃₀ , C ₁ ~ C ₄₀ alkyl boron group (preferably C ₁ ~ C ₂₀ alkyl boron group), C ₆ ~ C ₆₀ aryl boron group (preferably C ₆ ~ C ₃₀ Aryl boron group), C ₁ ~ C ₄₀ alkyl phosphine group (preferably C ₁ ~ C ₂₀ alkyl phosphine group), C ₆ ~ C ₆₀ aryl phosphine group (preferably C ₆ ~ C ₃₀ aryl phosphine group) , C ₁ ~ C ₄₀ aryl phosphine oxide group (preferably C ₁ ~ C ₂₀ alkyl phosphine oxide group), C ₆ ~ C ₆₀ aryl phosphine oxide group (preferably C ₆ ~ C ₃₀ aryl force Pinoxide group) and C ₆ -C ₆₀ arylamine group (preferably C ₆ -C ₃₀ aryl) Min group) is unsubstituted or substituted with one or more substituents selected from the group consisting of, wherein, when there are a plurality of the substituents, they are the same or different from each other.

Substituents represented by Formula 2 may be embodied by substituents represented by the following Formula C-1 to Formula C-15, but is not limited thereto.

.

In Chemical Formulas C-1 to C-15,

L, o and R ₅ are the same as defined in Formula 2, respectively,

p is an integer of 0 to 4, when p is 0, it means that hydrogen is not substituted with a substituent R ₆ , when p is an integer of 1 to 4, at least one R ₆ is the same or different from each other, Each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group (preferably C ₁ ~ C ₂₀ alkyl group), C ₂ ~ C ₄₀ alkenyl group (preferably C ₂ ~ C ₂₀ alkenes) Nyl group), C ₂ to C ₄₀ alkynyl group (preferably C ₂ to C ₂₀ alkynyl group), C ₃ to C ₄₀ cycloalkyl group (preferably C ₃ to C ₂₀ cycloalkyl group), nuclear atom 3 to 40 heterocycloalkyl groups (preferably 3 to 20 heterocycloalkyl groups), C ₆ to C ₆₀ aryl groups (preferably C ₆ to C ₃₀ aryl groups), nuclear atoms 5 to 60 heteroaryl Group (preferably a heteroaryl group of 5 to 30 nuclear atoms), an aryloxy group of C ₆ to C ₆₀ (preferably an aryloxy group of C ₆ to C ₃₀ ), C ₁ to C ₄₀ Alkyloxy group (preferably a C ₁ ~ C ₂₀ alkyloxy group of), C of ₆ ~ C ₆₀ aryl amine groups (preferably C for ₆ ~ C ₃₀ aryl amine group), C ₁ ~ C ₄₀ alkyl silyl group ( Preferably C ₁ ~ C ₂₀ Alkylsilyl group), C ₁ ~ C ₄₀ Alkyl boron group (preferably C ₁ ~ C ₂₀ Alkyl boron group), C ₆ ~ C ₆₀ An aryl boron group (preferably C ₆ Aryl boron group of ~ C ₃₀ , C ₆ ~ C ₆₀ aryl phosphine group (preferably C ₆ ~ C ₃₀ aryl phosphine group), C ₆ ~ C ₆₀ aryl phosphine oxide group (preferably C ₆ ~ C ₃₀ arylphosphine oxide group), and C ₆ ~ C ₆₀ arylsilyl group (preferably C ₆ ~ C ₃₀ arylsilyl group), or R ₅ adjacent to each other or adjacent R Can be combined with ₆ to form a condensed ring,

Alkyl group of the R _6, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, the arylphosphine oxide group, and the arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group (preferably C ₁ ~ C ₂₀ alkyl group), C ₂ ~ C ₄₀ Alkenyl group (preferably C ₂ ~ C ₂₀ alkenyl group), C ₂ ~ C ₄₀ alkynyl group (preferably C ₂ ~ C ₂₀ alkynyl group), C ₆ ~ C ₆₀ aryl group (preferably C ₆ Aryl group of ~ C ₃₀ ), heteroaryl group of 5 to 60 nuclear atoms (preferably heteroaryl group of 5 to 30 nuclear atoms), aryloxy group of C ₆ ~ C ₆₀ (preferably C ₆ ~ C ₃₀ the aryloxy group), C ₁ ~ C ₄₀ of the alkyloxy group (preferably a C ₁ ~ C ₂₀ alkyl group), an aryl amine of the C ₆ ~ C ₆₀ aryl amine groups (preferably C ₆ ~ C ₃₀ ), C cycloalkyl group of ₃ ~ C ₄₀ (preferably C cycloalkyl group of ₃ ~ C _20), nuclear atoms to C40 heterocycloalkyl group (preferably heterocycloalkyl group of nuclear atoms of 3 to 20), C ₁ a ~ C ₄₀ alkylsilyl group (preferably C ₁ ~ C alkyl silyl group of _20), C ₁ ~ C ₄₀ alkyl boron group (preferably C ₁ ~ C group ₂₀ of the alkyl boron), C ₆ ~ C ₆₀ of the Aryl boron group (preferably C ₆ ~ C ₃₀ aryl boron group), C ₆ ~ C ₆₀ aryl phosphine group (preferably C ₆ ~ C ₃₀ aryl phosphine group), C ₆ ~ C ₆₀ aryl phosphine oxide Substituted by one or more substituents selected from the group consisting of a group (preferably C ₆ ~ C ₃₀ aryl phosphine oxide group) and C ₆ ~ C ₆₀ arylsilyl group (preferably C ₆ ~ C ₃₀ arylsilyl group) Or unsubstituted, wherein when there are a plurality of substituents, they are the same as or different from each other.

The compound represented by Formula 1 according to the present invention may be embodied by the following compounds, but is not limited thereto.

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

In the present invention, alkenyl is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon double bonds. Non-limiting examples thereof include vinyl and allyl. (allyl), isopropenyl, 2-butenyl and the like.

Alkynyl in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having one or more carbon-carbon triple bonds, non-limiting examples thereof include ethynyl, 2-propynyl and the like.

Cycloalkyl in the present invention means monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons 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, wherein at least one carbon in the ring, preferably 1 to 3 carbons is N, O, S or Se Is substituted with a hetero atom such as Examples of such heterocycloalkyl include morpholine, piperazine and the like.

In the present invention, aryl means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms combined with a single ring or two or more rings. In addition, a form in which two or more rings are attached to each other (pendant) or condensed may also be included. Non-limiting examples of such aryls include phenyl, naphthyl, phenanthryl, anthryl and the like.

Heteroaryl in the present invention means a monovalent substituent derived from monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are pendant or condensed with each other may also be included, and may also include a form condensed with an aryl group. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but is not limited thereto.

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

In the present invention, aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms. Non-limiting examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.

In the present invention, alkylsilyl is silyl substituted with alkyl having 1 to 40 carbon atoms, and arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms.

In the present invention, the alkyl boron group means a boron group substituted with alkyl having 1 to 40 carbon atoms, the aryl boron group means a boron group substituted with aryl having 6 to 60 carbon atoms, and the alkylphosphine group is substituted with alkyl having 1 to 40 carbon atoms. A phosphine group, an aryl phosphine group means a phosphine group substituted with an aryl having 6 to 60 carbon atoms, an alkyl phosphine oxide group means a phosphine oxide group substituted with an alkyl having 1 to 40 carbon atoms, aryl phosphine oxide The group means a phosphine oxide group substituted with an aryl having 6 to 60 carbon atoms.

In the present invention, arylamine means an amine substituted with aryl having 6 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.

Compounds 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) ) And so on). Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.

On the other hand, the present invention provides an organic electroluminescent device comprising a compound represented by the formula (1).

Specifically, the present invention includes an anode, a cathode and at least one organic material layer interposed between the anode and the cathode, at least one of the organic material layer comprises an organic electric field comprising at least one compound represented by the formula (1) Provided is a light emitting device. In this case, the compound represented by Formula 1 may be used alone or in combination of two or more.

According to an example, the one or more organic material layers include a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein the light emitting layer (preferably phosphorescent light emitting layer) is represented by the formula (1) It includes a compound which becomes. In this case, the compound represented by Chemical Formula 1 is used as a light emitting layer material. If the compound represented by Formula 1 is included in the organic EL device as a light emitting layer material, preferably a phosphorescent host, the luminous efficiency, luminance, power efficiency, thermal stability and device life of the organic EL device may be improved.

The emission layer may include a metal complex compound dopant. Metal complex compound-based dopants usable in the present invention can be used without particular limitation as long as they are known in the art. In this case, the mixing ratio of the host and the dopant is not particularly limited, but when the ratio is 99: 1 to 70:30, the color purity and efficiency of light may be increased, and thus the luminous efficiency and lifespan of the device may be further improved. Can be.

The structure of the organic EL device of the present invention is not particularly limited. For example, the anode, one or more organic material layers and the cathode are sequentially stacked on the substrate, and an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer. Can be.

According to an example, the organic EL device may have a structure in which an anode, a hole injection layer, a hole transport layer, an emission auxiliary layer, an emission layer, an electron transport layer, and a cathode are sequentially stacked on a substrate. Optionally, an electron injection layer may be positioned between the electron transport layer and the cathode.

The organic electroluminescent device of the present invention is an organic material layer using materials and methods known in the art, except that at least one of the organic material layers (for example, the light emitting auxiliary layer) is formed to include the compound represented by Chemical Formula 1 above. And by forming an electrode.

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

The substrate usable in the present invention is not particularly limited, and non-limiting examples include silicon wafers, quartz or glass plates, metal plates, plastic films or sheets, and the like.

In addition, examples of the anode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), 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 and polyaniline; Or carbon black, but is not limited thereto.

Further, examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like, but are not limited thereto.

In addition, the material used as the light emitting layer, the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited as long as it is a conventional material known in the art.

Hereinafter, the present invention will be described in detail with reference to Examples, but the following Examples are merely illustrative of the present invention, and the present invention is not limited by the following Examples.

[ Preparation  1] Compound I-1 (5,7- Dichloropyrazolo [1,5-a] synthesis of pyrimidine

4,5-dihydropyrazolo [1,5-a] pyrimidine-5,7-diol (40.8 g, 0. 31 mol) and POCl ₃ (100 ml, 10.9 mmol) at 5 ° C. under nitrogen stream were added to dimethylaniline (120 mL, 0.94). mol) and stirred at reflux for 12 hours at 60 ° C. After the reaction was terminated, the mixture was cooled to room temperature and filtered to obtain a solid product. After dissolving the solid product in dichloromethane, ice water was added dropwise, stirred for 15 minutes, and neutralized with a solid NaHCO ₃ to pH 8-9. After that, the organic layer was extracted with dichloromethane and MgSO ₄ was added and filtered. The solvent was removed from the organic layer and purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain compound I-1 (46. 1 g, yield 77%).

1 H-NMR of compound I-1 (400 MHz, CDCl 3): δ 8.22 (d, J = 2.2 Hz, 1H), 6.99 (s, 1H), 6.40 (dt, J = 0.7, 2.2 Hz, 1H).

Preparation Example 2 Synthesis of Compound I-2

Step 1 Synthesis of 5,7-diphenylpyrazolo [1,5-a] pyrimidine

Compound I-1 (50.0 g, 0.26 mol), Phenyl boronic acid (65 g, 0.53 mol), Pd (OAc) ₂ (0.59 g, 0.003 mol) synthesized in Preparation Example 1 under nitrogen stream, Xphos (2.53 g, 0.005 mol) and Cesium carbonate (260 g, 0.79 mol) were mixed and then stirred at reflux in Toluene (400 mL) and EtOH (100 mL), H ₂ O (100 mL).

After completion of the reaction, the organic layer was separated with methylene chloride, and water was removed from the organic layer using MgSO ₄ . After removing the solvent from the organic layer, the water was removed, and purified by column chromatography [Hexane: MC = 5: 1 (v / v)] to give a compound 5,7-diphenylpyrazolo [1,5-a] pyrimidine (31 g, yield 43%).

<Step 2> Synthesis of Compound I-2

NBS (196 g, 0.11 mol) dissolved in acetonitrile (150 mL) under nitrogen stream was added dropwise to 5,7-diphenylpyrazolo [1,5-a] pyrimidine (31.0 g, 0.11 mol) dissolved in acetonitrile (150 mL). Then stirred for 20 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added and filtered. After removing the solvent in the organic layer obtained was purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to give the compound I-2 (31.2 g, 78%).

Preparation Example 3 Synthesis of Compound I-3

Compound I-2 (30 g, 0.086 mol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1, synthesized in Preparation Example 2 under nitrogen stream , 3,2-dioxaborolane) (28.3 g, 0.11 mol), Pd (dppf) Cl ₂ (3.2 g, 0.004 mol), KOAc (25.2 g, 0.256 mol), and 1,4-dioxane (450 ml) were mixed and then stirred at 130 ° C. for 12 hours.

After the reaction was completed, the organic layer was extracted with ethyl acetate, water was removed from the organic layer with MgSO ₄ , and purified by column chromatography [Hexane: Dichloromethane (MC) = 5: 1 (v / v)]. -3 (37 g, yield 84%) was obtained.

Preparation Example 4 Synthesis of Compound I-4

Step 1 Synthesis of 3,5,7-triphenylpyrazolo [1,5-a] pyrimidine

Compound I-2 (30.0 g, 0.086 mol), Phenyl boronic acid (32 g, 0.10 mol), Pd (PPh ₃ ) ₄ (2.96 g, 0.003 mol) synthesized in Preparation Example 2 under nitrogen stream, and potassium carbonate ( K ₂ CO ₃ ) (35.5 g, 0.26 mol) was mixed and then stirred at reflux in 1,4-dioxane (240 mL), and H ₂ O (60 mL).

After completion of the reaction, the organic layer was separated with methylene chloride, and water was removed from the organic layer using MgSO ₄ . After removing the solvent from the water-free organic layer, and purified by column chromatography [Hexane: MC = 5: 1 (v / v)] compound 3,5,7-triphenylpyrazolo [1,5-a] pyrimidine (23.5 g , Yield 79%) was obtained.

<Step 2> Synthesis of Compound I-4

3,5,7-triphenylpyrazolo [1,5-a] pyrimidine (30 g, 0.086 mol) and N-iodosuccinimide (19.4 g, 86 mmol) synthesized in Step 1 were mixed under a nitrogen stream, and then N, N- Dimethylformamide (300 mL) was added thereto and stirred at room temperature for 20 hours.

After completion of the reaction, the organic layer was separated with methylene chloride, and water was removed from the organic layer using MgSO ₄ . After the solvent was removed from the organic layer, the water was removed, and purified by column chromatography [Hexane: MC = 5: 1 (v / v)] to give the compound I-4 (23 g, yield 56%).

Preparation Example 5 Synthesis of Compound I-5

Except for using the compound I-4 (30.0 g 0.063 mol) synthesized in Preparation Example 4 instead of the compound I-2 used in Preparation Example 3, the compound I-5 ( 32.7 g 86%).

Preparation Example 6 Synthesis of Compound I-6

Except for using compound I-2 (30 g, 0.086 mol) synthesized in Preparation Example 2 instead of 3,5,7-triphenylpyrazolo [1,5-a] pyrimidine used in Step 2 of Preparation Example 4, Compound I-6 (16.3 g, 43%) was obtained by the same process as Step 2 of Preparation Example 4.

Preparation Example 7 Synthesis of Compound I-7

Compound I-6 (30.0 g, 0.05 mol) synthesized in Preparation Example 6 was used instead of Compound I-2 used in Step 1 of Preparation Example 4. Except for using the same procedure as in Step 1 of Preparation Example 4, Compound I-7 (15.7 g, 57%) was obtained.

Preparation Example 8 Synthesis of Compound I-8

Compound I-8 (28.3g 87%) was obtained in the same manner as in Preparation Example 3, except that I-7 (30.0 g 0.054 mol) was used instead of I-2 used in Preparation Example 3.

Synthesis Example 1 Synthesis of Compound 8

Compound I-3 (10.0 g, 0.025 mol), 2-bromo-4,6-diphenylpyrimidine (9.4 g, 0.030 mol), Pd (PPh ₃ ) ₄ (0.87 g, 0.001 mol) synthesized in Preparation Example 3 under nitrogen stream ), And potassium carbonate (10.44 g, 0.076 mol) were mixed and then stirred at reflux in 1,4-dioxane (80 mL) and H ₂ O (20 mL).

After completion of the reaction, the organic layer was separated with methylene chloride, and water was removed from the organic layer using MgSO ₄ . After the solvent was removed from the organic layer, the water was removed, and purified by column chromatography [Hexane: MC = 10: 1 (v / v)] to give the compound 8 (8.2 g, 63% yield).

HRMS [M] +: 501.62

Synthesis Example 2 Synthesis of Compound 9

Synthesis example except for using 2-bromo-4,6-diphenyl-1,3,5-triazine (9.43 g, 0.030 mol) instead of 2-bromo-4,6-diphenylpyrimidine used in Synthesis Example 1 Compound 9 (8.5 g, yield: 63%) was obtained in the same manner as 1.

HRMS [M] +: 501.62

Synthesis Example 3 Synthesis of Compound 11

Except for using 1-bromo-4-phenylisoquinoline (8.52g, 0.030 mol) instead of 2-bromo-4,6-diphenylpyrimidine used in Synthesis Example 1 Compound 11 ( 9.8 g, yield: 84%).

HRMS [M] +: 474.57

Synthesis Example 4 Synthesis of Compound 26

Compound 26 (9.7 g, yield) was carried out in the same manner as in Synthesis Example 1, except that 2-bromotriphenylene (9.2 g, 0.030 mmol) was used instead of 2-bromo-4,6-diphenylpyrimidine used in Synthesis Example 1. : 78%).

HRMS [M] +: 497.60

Synthesis Example 5 Synthesis of Compound 29

The same procedure as in Synthesis Example 1 except for using 2-bromo-9,9-dimethyl-9H-fluorene (8.2 g, 0.030 mmol) instead of 2-bromo-4,6-diphenylpyrimidine used in Synthesis Example 1 Compound 29 (9.4 g, yield: 81%) was obtained.

HRMS [M] +: 463.58

Synthesis Example 6 Synthesis of Compound 32

The same procedure as in Synthesis Example 1 except for using 2- (3-bromophenyl) dibenzo [b, d] thiophene (10.1 g, 0.030 mmol) instead of 2-bromo-4,6-diphenylpyrimidine used in Synthesis Example 1. The procedure was carried out to obtain compound 32 (11.65 g, yield: 88%).

HRMS [M] +: 529.66

Synthesis Example 7 Synthesis of Compound 36

Compound I-2 (10.0 g, 28.5 mmol), Carbazole (6.2 g, 37.1 mmol), Pd (OAc) ₂ (0.06 g, 0.3 mmol), P ( t- Bu) ₃ synthesized in Preparation Example 2 under nitrogen stream (0.12 ml, 0.6 mmol), NaO ( t- Bu) (8.23 g, 85.6 mmol) and toluene (100 ml) were mixed and stirred at 110 ° C. for 5 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain compound 36 (8.1 g, yield 65%).

HRMS [M] +: 436.52

Synthesis Example 8 Synthesis of Compound 38

The same procedure as in Synthesis Example 1 was conducted except that 9- (4-bromophenyl) -9H-carbazole (9.6 g, 0.030 mmol) was used instead of 2-bromo-4,6-diphenylpyrimidine used in Synthesis Example 1. Compound 38 (10.89 g, yield: 85%) was obtained.

HRMS [M] +: 512.62

Synthesis Example 9 Synthesis of Compound 39

Synthesis Example 1 except that 3- (4-bromophenyl) -9-phenyl-9H-carbazole (11.9 g, 0.03 mmol) was used instead of 2-bromo-4,6-diphenylpyrimidine used in Synthesis Example 1. The same procedure was followed to obtain compound 39 (11.6 g, yield: 79%).

HRMS [M] +: 588.71

Synthesis Example 10 Synthesis of Compound 98

Compound I-8 (10.0 g, 0.025 mol), 2-bromo-4,6-diphenylpyrimidine (7.8g, 0.025 mol), Pd (PPh ₃ ) ₄ (0.73 g, 0.001 mol) synthesized in Preparation Example 8 under nitrogen stream ), And potassium carbonate (8.75 g, 0.063 mol) were mixed and then stirred at reflux in 1,4-dioxane (80 mL) and H ₂ O (20 mL).

After completion of the reaction, the organic layer was separated with methylene chloride, and water was removed from the organic layer using MgSO ₄ . After the solvent was removed from the organic layer, the water was removed, and purified by column chromatography [Hexane: MC = 10: 1 (v / v)] to give a compound 98 (10.74 g, yield 88%).

HRMS [M] +: 577.69

Synthesis Example 11 Synthesis of Compound 100

Synthesis example except for using 2-bromo-4,6-diphenyl-1,3,5-triazine (9.43 g, 0.025 mol) instead of 2-bromo-4,6-diphenylpyrimidine used in Synthesis Example 10 Compound 100 (8.5 g, yield: 63%) was obtained in the same manner as 10.

HRMS [M] +: 578.68

Synthesis Example 12 Synthesis of Compound 101

Except for using 1-bromo-4-phenylisoquinoline (8.0 g, 0.025 mol) instead of 2-bromo-4,6-diphenylpyrimidine used in Synthesis Example 10, Compound 101 ( 9.77 g, yield: 71%).

HRMS [M] +: 550.66

Synthesis Example 13 Synthesis of Compound 116

Compound 116 (11.18 g, yield) was carried out in the same manner as in Synthesis Example 10, except that 2-bromotriphenylene (8.8 g, 0.025 mol) was used instead of 2-bromo-4,6-diphenylpyrimidine used in Synthesis Example 10. : 78%).

HRMS [M] +: 573.70

Synthesis Example 14 Synthesis of Compound 119

The same procedure as in Synthesis Example 10 except for using 2-bromo-9,9-dimethyl-9H-fluorene (8.0 g, 0.025 mol) instead of 2-bromo-4,6-diphenylpyrimidine used in Synthesis Example 10 Compound 119 (8.77 g, yield: 65%) was obtained.

HRMS [M] +: 539.68

Synthesis Example 15 Synthesis of Compound 122

Synthesis Example 10 Except that 2- (3-bromophenyl) dibenzo [b, d] thiophene (10.1 g, 0.030 mmol) was used instead of 2-bromo-4,6-diphenylpyrimidine, which was used in Synthesis Example 10. The procedure was followed to obtain compound 122 (13.3 g, yield: 88%).

HRMS [M] +: 605.76

Synthesis Example 16 Synthesis of Compound 128

The same procedure as in Synthesis Example 10 was carried out except that 9- (4-bromophenyl) -9H-carbazole (9.6 g, 0.030 mmol) was used instead of 2-bromo-4,6-diphenylpyrimidine used in Synthesis Example 10. Compound 128 (20.00 g, yield: 69%) was obtained.

HRMS [M] +: 588.71

Synthesis Example 17 Synthesis of Compound 126

Compound I-7 (10.0 g, 28.5 mmol), Carbazole (5.1 g, 30.4 mmol), Pd (OAc) ₂ (0.05 g, 0.2 mmol), P ( t- Bu) ₃ synthesized in Preparation Example 7 under nitrogen stream (0.10 ml, 0.46 mmol), NaO ( t- Bu) (6.76 g, 70.3 mmol) and toluene (100 ml) were mixed and stirred at 110 ° C. for 5 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain a compound 126 (7.8 g, yield 65%).

HRMS [M] +: 512.62

Synthesis Example 18 Synthesis of Compound 129

Synthesis Example 10, except that 3- (4-bromophenyl) -9-phenyl-9H-carbazole (11.9 g, 0.030 mol) was used instead of 2-bromo-4,6-diphenylpyrimidine used in Synthesis Example 10. The same procedure was followed to obtain compound 129 (10.8 g, yield: 65%).

HRMS [M] +: 664.81

Synthesis Example 19 Synthesis of Compound 138

Compound I-5 (10.0 g, 0.025 mol), 2-bromo-4,6-diphenylpyrimidine (7.8g, 0.025 mol), Pd (PPh ₃ ) ₄ (0.73 g, 0.001 mol) synthesized in Preparation Example 5 under nitrogen stream ), And potassium carbonate (8.75 g, 0.063 mol) were mixed and then stirred at reflux in 1,4-dioxane (80 mL) and H ₂ O (20 mL).

After completion of the reaction, the organic layer was separated with methylene chloride, and water was removed from the organic layer using MgSO ₄ . After the solvent was removed from the organic layer, the water was removed, and then purified by column chromatography [Hexane: MC = 10: 1 (v / v)] to give the compound 138 (10.74 g, yield 88%).

HRMS [M] +: 577.69

Synthesis Example 20 Synthesis of Compound 140

Except for using 1-bromo-4-phenylisoquinoline (1.89 g, 25.0 mmol) instead of 2-bromo-4,6-diphenylpyrimidine used in Synthesis Example 19, Compound 140 ( 9.77 g, yield: 71%).

HRMS [M] +: 550.66

Synthesis Example 21 Synthesis of Compound 144

Compound 144 (11.18 g, yield) was carried out in the same manner as in Synthesis Example 19, except that 2-bromotriphenylene (8.8 g, 0.025 mol) was used instead of 2-bromo-4,6-diphenylpyrimidine used in Synthesis Example 19. : 78%).

HRMS [M] +: 573.70

Synthesis Example 22 Synthesis of Compound 145

The same procedure as in Synthesis Example 19, except that 2-bromo-9,9-dimethyl-9H-fluorene (8.0 g, 0.025 mol) was used instead of 2-bromo-4,6-diphenylpyrimidine used in Synthesis Example 19. This carried out the compound 145 (8.77 g, yield: 65%).

HRMS [M] +: 539.68

Synthesis Example 23 Synthesis of Compound 148

Compound I-4 (10.0 g, 28.5 mmol), Carbazole (5.1 g, 30.4 mmol), Pd (OAc) ₂ (0.05 g, 0.2 mmol), P ( t- Bu) ₃ synthesized in Preparation Example 4 under nitrogen stream (0.10 ml, 0.46 mmol), NaO ( t- Bu) (6.76 g, 70.3 mmol) and toluene (100 ml) were mixed and stirred at 110 ° C. for 5 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain a compound 148 (7.8 g, yield 65%).

HRMS [M] +: 512.62

Synthesis Example 24 Synthesis of Compound 155

Synthesis Example 19, except that 3- (4-bromophenyl) -9-phenyl-9H-carbazole (11.9 g, 0.030 mol) was used instead of 2-bromo-4,6-diphenylpyrimidine used in Synthesis Example 19. The same procedure was followed to obtain compound 155 (10.8 g, yield: 65%).

HRMS [M] +: 664.81

Example 1 Fabrication of Green Organic Electroluminescent Device

Compound 8 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic electroluminescent device was manufactured as follows.

A glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried, and then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then wash the substrate using UV for 5 minutes The substrate was then transferred to a vacuum evaporator.

M-MTDATA (60nm) / TCTA (80nm) / 90% by weight of the compound 8 + 10% by weight of Ir (ppy) ₃ (300nm) / BCP (10nm) / Alq ₃ (30nm) on the prepared ITO transparent electrode / LiF (1 nm) / Al (200 nm) was laminated in order to manufacture an organic EL device.

The m-MTDATA, TCTA, Ir (ppy) ₃ and the structure of the BCP is as follows.

Examples 2 to 24-Fabrication of Green Organic Electroluminescent Device

A green organic EL device was manufactured in the same manner as in Example 1, except that the compound synthesized in Synthesis Examples 2 to 24 was used instead of the compound 8 in Example 1.

Comparative Example 1-Fabrication of Green Organic Electroluminescent Device

A green organic EL device was manufactured in the same manner as in Example 1, except that the following CBP was used instead of the compound synthesized in Synthesis Example 1.

[Evaluation Example 1]

For organic electroluminescent devices prepared in Examples 1 to 24 and Comparative Example 1, driving voltage, current efficiency and emission peak at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 1 below. .

	Luminous material	Driving voltage (V)	Emission Peak (nm)	Current efficiency (cd / A)
Example 1	Compound 8	5.80	519	47.5
Example 2	Compound 9	5.50	520	46.3
Example 3	Compound 11	5.20	521	49.5
Example 4	Compound 26	5.70	520	50.2
Example 5	Compound 29	5.50	521	46.0
Example 6	Compound 32	5.20	518	48.0
Example 7	Compound 36	6.50	520	43.3
Example 8	Compound 38	6.00	519	45.9
Example 9	Compound 39	5.80	519	47.5
Example 10	Compound 98	5.00	521	46.3
Example 11	Compound 100	4.80	520	49.5
Example 12	Compound 101	6.50	519	50.2
Example 13	Compound 116	6.00	520	46.0
Example 14	Compound 119	5.80	519	48.0
Example 15	Compound 122	5.00	520	43.3
Example 16	Compound 128	6.50	519	45.9
Example 17	Compound 126	6.00	520	47.5
Example 18	Compound 129	5.80	520	46.3
Example 19	Compound 138	5.00	519	49.5
Example 20	Compound 140	4.80	520	46.0
Example 21	Compound 144	5.20	520	48.0
Example 22	Compound 145	5.70	519	43.3
Example 23	Compound 148	5.50	519	45.9
Example 24	Compound 155	5.20	520	47.5
Comparative Example 1	CBP	6.93	516	38.2

As shown in Table 1, the green organic electroluminescent device of Examples 1 to 24 using the compound (Compounds 8 to 155) according to the present invention as the light emitting layer material, the green of Comparative Example 1 using the conventional CBP as the light emitting layer material It was found that the driving voltage is lower and the current efficiency can be further improved as compared with the organic EL device.

Example 25 Fabrication of Red Organic Electroluminescent Device

Compound 8 synthesized in Synthesis Example 1 After high purity sublimation purification by a conventionally known method, a red organic electroluminescent device was manufactured as follows.

First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 mm 3 was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried, transferred to a UV OZONE cleaner (Powersonic 405, Hwashin Tech), and then washed the substrate using UV for 5 minutes The substrate was transferred to a vacuum evaporator.

On the thus prepared ITO transparent electrode, m-MTDATA (60 nm) / TCTA (80 nm) / 90% by weight of compound 8 + 10% by weight of (piq) 2Ir (acac) (30nm) / BCP (10 nm) / An organic electroluminescent device was manufactured by stacking in order of Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm).

The structures of m-MTDATA, TCTA, CBP and BCP used were as described in Example 1, and (piq) ₂ Ir (acac) was as follows.

Examples 26 to 48-Fabrication of Red Organic Electroluminescent Device

A red organic EL device was manufactured in the same manner as in Example 25, except that the compounds synthesized in Synthesis Examples 2 to 24 were used instead of the compound 8 used as the light emitting host material in forming the emission layer in Example 25.

Comparative Example 2 Fabrication of Red Organic Electroluminescent Device

A red organic electroluminescent device was manufactured in the same manner as in Example 25, except that CBP was used instead of Compound 1 used as a light emitting host material in forming a light emitting layer in Example 25. The structure of CBP used was as described in Comparative Example 1.

 [Evaluation Example 2]

For the red organic electroluminescent devices manufactured in Examples 25 to 48 and Comparative Example 2, the driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured, and the results are shown in Table 2 below.

	Luminous material	Driving voltage (V)	Current efficiency (cd / A)
Example 25	Compound 8	4.40	12.5
Example 26	Compound 9	4.60	13.8
Example 27	Compound 11	4.40	11.5
Example 28	Compound 26	4.40	11.5
Example 29	Compound 29	4.30	12.8
Example 30	Compound 32	4.50	11.9
Example 31	Compound 36	4.40	11.5
Example 32	Compound 38	4.60	11.9
Example 33	Compound 39	4.60	12.8
Example 34	Compound 98	4.40	11.9
Example 35	Compound 100	4.30	12.8
Example 36	Compound 101	4.80	11.9
Example 37	Compound 116	4.30	11.5
Example 38	Compound 119	4.50	11.5
Example 39	Compound 122	4.40	12.8
Example 40	Compound 128	4.40	10.8
Example 41	Compound 126	4.30	12.8
Example 42	Compound 129	4.50	11.9
Example 43	Compound 138	4.40	12.8
Example 44	Compound 140	4.60	10.9
Example 45	Compound 144	4.60	11.1
Example 46	Compound 145	4.40	10.9
Example 47	Compound 148	4.30	11.2
Example 48	Compound 155	4.50	11.1
Comparative Example 2	CBP	4.80	10.5

As shown in Table 2, in the case of the red organic EL device of Examples 25 to 48 using the compound (Compounds 8 to 155) according to the present invention as the light emitting layer material, the red organic electroluminescence of Comparative Example 2 using the conventional CBP Compared with the device, it was confirmed that the efficiency and the driving voltage were excellent.

Although the preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and various modifications and changes can be made within the scope of the claims and the detailed description of the invention, which also fall within the scope of the invention. It is natural.

Claims (4)

1. Compound represented by the following formula (1):

   [Formula 1]

   

   (In Formula 1,

   R ₁ and R ₂ are the same as or different from each other, and are each independently selected from the group consisting of hydrogen, an alkyl group of C ₁ to C ₄₀ , and an aryl group of C ₆ to C ₆₀ ;

   m and n are each an integer of 0 to 3;

   a and b are each independently an integer of 0 to 4,

   R ₃ and R ₄ are the same or different, each independently represent a deuterium, a halogen group, a cyano group, a nitro group, an alkenyl group of an amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ of the group, C ₂ ~ C ₄₀ Alkynyl group, C ₃ -C ₄₀ cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C ₆ -C ₆₀ aryl group, nuclear atom 5-60 heteroaryl group, C ₁ -C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, a phosphine group, C ₁ ~ C ₄₀ alkyl phosphine group, C ₆ ~ C ₄₀ aryl phosphine group, C ₁ ~ alkyl phosphine of the C _40-pin oxide group, C ₆ ~ aryl phosphine oxide of the C ₄₀ group And it is selected from the group consisting of C ₆ ~ C ₆₀ arylamine group;

   Ar ₁ and Ar ₂ are the same as or different from each other, each independently represent a substituent represented by the formula (2),

   [Formula 2]

   

   * Is a moiety bound to Formula 1,

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

   o is 0 or 1,

   Z ₁ to Z ₅ are the same as or different from each other, and each independently N or C (R ₅ ), provided that at least one of Z ₁ to Z ₅ is N,

   In this case, when there are a plurality of C (R ₅ ), a plurality of R ₅ are the same or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, amino 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 number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to the 60 heteroaryl group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, phosphine group, C ₁ ~ C ₄₀ alkyl phosphine group, C ₆ ~ C ₄₀ aryl phosphine group, C ₁ ~ C ₄₀ alkyl phosphine oxide group , C ₆ ~ C ₄₀ aryl phosphine oxide group and C ₆ ~ C ₆₀ An arylamine group, or combine with other adjacent R ₅ or L to form a condensed aromatic ring or a condensed heteroaromatic ring Number It was;

   The alkyl group, aryl group, R ₃ to R ₅ alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl of R ₁ and R ₂ Group, arylsilyl group, alkyl boron group, aryl boron group, phosphine group, alkyl phosphine group, aryl phosphine group, alkyl phosphine oxide group, aryl phosphine oxide group and arylamine group and the arylene group and heteroarylene group of L, respectively Independently deuterium, halogen group, cyano group, nitro group, amino 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, nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group, a nuclear atoms of 5 to 40 heteroaryl group, C ₁ ~ alkyloxy group of C ₄₀ of the, aryloxy of C ₆ ~ C ₆₀ , C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl boron group, a phosphine , C ₁ ~ C ₄₀ alkyl phosphine group, C ₆ ~ C ₆₀ aryl phosphine group, C ₁ ~ C ₄₀ alkyl phosphine oxide group, C ₆ ~ aryl phosphine oxide of a C ₆₀ group, and a C ₆ ~ C ₆₀ Or an unsubstituted or substituted with one or more substituents selected from the group consisting of arylamine groups, wherein when the substituents are plural, they are the same or different from each other).
2. The method of claim 1,

   Substituent represented by the formula (2) is a compound, characterized in that selected from the group consisting of substituents represented by the following formula C-1 to C-15:

   

   (In Chemical Formulas C-1 to C-15,

   L, o and R ₅ are each as defined in claim 1,

   p is an integer from 0 to 4,

   A plurality of R ₆ are the same or different and are each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ cycloalkyl group, nuclear hetero atoms 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy 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 aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and C ₆ ~ C ₆₀ An arylsilyl group selected from the group consisting of, or to combine with adjacent groups to form a condensed ring Can and

   Alkyl group of the R _6, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, the arylphosphine oxide 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 alky Neyl group, C ₆ ~ C ₆₀ aryl group, C ₅ ~ C ₆₀ heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ arylamine aryl boron group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ of the group, substituted by C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide groups and one or more substituents selected from the group consisting of aryl silyl C ₆ ~ C ₆₀ of Is the case of an unsubstituted, wherein the substituents are plural, these are the same or different from each other).
3.  An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more layers of organic material interposed between the anode and the cathode,

   At least one of the at least one organic material layer comprises an compound represented by the formula (1) according to claim 1 or 2 characterized in that the organic electroluminescent device.
4. The method of claim 3,

   The organic material layer including the compound represented by Formula 1 is a light emitting layer,

   The compound represented by Formula 1 is an organic electroluminescent device, characterized in that the host material.