KR102703809B1 - Organic compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel organic compound and an organic electroluminescent device comprising the same, and more specifically, to an organic compound having excellent luminescence, hole injection/transport, electron injection/transport, and thermal stability, and an organic electroluminescent device comprising the compound having improved luminescence efficiency, driving voltage, and lifespan.

Description

ORGANIC COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME

The present invention relates to a novel organic luminescent compound and an organic electroluminescent device using the same, and more specifically, to a compound having excellent thermal stability, luminescent ability, hole injection/transport ability, and electron injection/transport ability, and an organic electroluminescent device having improved characteristics such as luminescent efficiency, driving voltage, and lifespan by including the compound in one or more organic layers.

When current or voltage is applied to two electrodes in an organic electroluminescent device (hereinafter referred to as an "organic EL device"), holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, excitons are formed, and these excitons fall to the ground state and emit light. At this time, the material used as the organic layer can be classified into a light-emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc., depending on its function.

Up to now, NPB, BCP, Alq ₃ , etc. expressed by the following chemical formulas have been widely known as the hole injection layer, hole transport layer, hole blocking layer, and electron transport layer, and anthracene derivatives have been reported as fluorescent dopant/host materials as luminescent materials. In particular, among luminescent materials, metal complex compounds containing Ir, such as Firpic, Ir(ppy) ₃ , (acac)Ir(btp) ₂ , etc., have been used as blue, green, and red dopant materials as phosphorescent materials that have a great advantage in terms of improving efficiency. Up to now, CBP has shown excellent properties as a phosphorescent host material.

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

The present invention is applicable to organic electroluminescent devices, and aims to provide a novel organic compound that has excellent thermal stability, luminescence, carrier transport ability, etc. and can be used as a light-emitting layer material, a hole transport layer material, an electron transport layer material, an electron transport auxiliary layer material, etc.

In addition, another object of the present invention is to provide an organic electroluminescent device having a low driving voltage, high luminous efficiency, and improved lifespan, including the novel organic compound.

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

(In the above formula,

n1 is 0 or 1, n2 is 0 or 1, and then n1+n2 is 0 or 1,

L ₁ is a single bond or is selected from the group consisting of an arylene group having C ₆ to C ₆₀ and a heteroarylene group having 5 to 60 nuclear atoms,

Ar ₁ is selected from the group consisting of an aryl group having C ₆ to C ₆₀ , a heteroaryl group having 5 to 60 nuclear atoms, and an arylamine group having C ₆ to C ₆₀ ,

a is an integer from 0 to 3,

b and c are each integers from 0 to 4,

R ₁ to R ₅ are the same or different and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C ₁ to C ₄₀ 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 heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ is selected from the group consisting of an arylboron group, an arylphosphine group having C ₆ to C ₆₀ , an arylphosphine oxide group having C ₆ to C ₆₀ , and an arylamine group having C ₆ to C ₆₀ , or is combined with an adjacent group to form a condensed aromatic ring or a condensed heteroaromatic ring,

The arylene group, heteroarylene group of L _{1 and} the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, _alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of R 1 to R 5 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, and aryl group having 5 to 60 nuclear atoms. (wherein the heteroaryl group is unsubstituted _or substituted with one or _{more substituents selected from the group consisting of a heteroaryl group, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group , a} C ₆ to C ₆₀ arylsilyl group, a C 1 to C ₄₀ alkylboron group, a C ₆ to C _{60 arylboron group, a C 6 to C 60 arylphosphine} group, a C 6 to C ₆₀ arylphosphine oxide group, and a C ₆ to C ₆₀ arylamine group, and wherein when there are plural substituents, they are the same as or different from each other.)

In addition, the present invention provides an organic electroluminescent device including the above-mentioned anode, cathode, and one or more organic layers interposed between the anode and cathode, wherein at least one of the one or more organic layers includes a compound represented by the chemical formula 1.

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

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

FIG. 1 is a cross-sectional view schematically showing an organic electroluminescent device according to an example of the present invention.
FIG. 2 is a cross-sectional view schematically illustrating an organic electroluminescent device according to another example of the present invention.

Hereinafter, the present invention will be described in detail.

<New compound>

The present invention provides a novel organic compound that has excellent thermal stability, carrier transport ability, and luminescence ability and can be used as a high-efficiency light-emitting layer material, hole transport layer material, electron transport layer material, electron transport auxiliary layer material, etc.

Specifically, the compound of chemical formula 1 according to the present invention has a core structure formed by condensing benzo-1,4-dioxane onto one carbazole of a 3,3'-biscarbazole moiety, and includes a structure in which a specific substituent is introduced at the N position of the carbazole portions on both sides.

In general, aryl-substituted 3,3'-biscarbazole moieties exhibit superior hole transport capabilities than biscarbazole moieties introduced at other positions (e.g., 3,9'-biscarbazole, etc.). This is because holes injected through the unshared electron pair of the amine in the substituted 3,3'-biscarbazole moiety exhibit superior hole stabilization due to the resonance effect, and thus can move to a more stable site than the biscarbazole moiety bound at other positions.

In addition, the compound of the present invention has benzo-1,4-dioxane condensed on the central phenyl ring portion of one-sided carbazole moiety. Here, benzo-1,4-dioxane has a large electron donating group (EDG) characteristic. Due to the condensation with benzo-1,4-dioxane, the central phenyl ring portion of one-sided carbazole becomes more electron dense than that of a typical 3,3'-biscarbazole moiety that is not condensed. Accordingly, the compound of the above chemical formula 1 is stabilized as holes injected through the unshared electron pairs of both amines move through sp2 bonds within the molecule by the resonance effect, and at this time, the central phenyl ring of carbazole, whose electron density is increased due to condensation with benzo-1,4-dioxane, exhibits a higher hole stabilization effect than general 3,3'-biscarbazole.

In addition, the compound of the present invention has excellent thermal stability, luminescence, hole transport ability, etc. because it has a high glass transition temperature and high triplet energy. When the compound of chemical formula 1 is applied to an organic electroluminescent device, the organic electroluminescent device has a low driving voltage, high luminescence efficiency and current efficiency, and a long lifespan.

The compound of the above chemical formula 1 has a structure in which an indolooxanthrene moiety is directly bonded to the 3-position of the carbazole moiety by condensing benzo-1,4-dioxane onto one carbazole of a 3,3'-biscarbazole moiety. This compound has a wide singlet energy level and a high triplet energy level due to the oxanthrene part of the indolooxanthrene moiety (i.e., dibenzo[b,e][1,4]dioxine). Therefore, the compound of the present invention can be used as a host material because the energy level of the lowest excited state can be adjusted to be higher than the energy of the lowest emission state of the dopant by introducing a specific substituent to the indolooxanthrene moiety.

In addition, in the compound of the above chemical formula 1, the carbazole moiety has electron donating group (EDG) characteristics with high electron donating and hole transport properties, and the indolooxanthrene moiety has high hole transport ability due to the oxygen atom. Therefore, the compound of the present invention has superior hole transport properties compared to conventional biscarbazoles.

The compound of the present invention can have a wide band gap and high carrier transport properties since the HOMO and LUMO energy levels can be controlled depending on the types of substituents introduced at the N position of both moieties. In particular, the compound of the present invention can be easily used as a hole transport layer material when an electron donating group (EDG) with high electron donating ability is bonded to the N position of the indolooxanthrene moiety. Meanwhile, when the compound of the present invention has a substituent having an electron withdrawing group (EWG) characteristic with high electron absorbing ability, the entire molecule has bipolar properties, which can increase the binding force of holes and electrons. Therefore, the compound of the present invention has excellent luminescence and can be usefully applied as a blue, green or red phosphorescent emitting layer material of an organic electroluminescent device.

In addition, since the compound of the above chemical formula 1 has high triplet energy, it can prevent excitons generated in the light-emitting layer from diffusing (moving) to the adjacent electron transport layer or hole transport layer. Therefore, when an organic layer (hereinafter, “electron transport auxiliary layer”) is disposed between the light-emitting layer and the electron transport layer using the compound of the above chemical formula 1, since diffusion of excitons is prevented by the compound, unlike a conventional organic electroluminescent device that does not include an electron transport auxiliary layer, the number of excitons contributing to light emission in the light-emitting layer substantially increases, so that the light emission efficiency of the device can be improved.

In addition, the compound of the chemical formula 1 has a glass transition temperature that is improved by significantly increasing the molecular weight of the compound by introducing various substituents, particularly an aryl group and/or a heteroaryl group, into the basic skeleton, and thus can have higher thermal stability than conventional light-emitting materials (e.g., CBP). In addition, the compound represented by the chemical formula 1 is also effective in suppressing crystallization of an organic layer. Therefore, an organic electroluminescent device including the compound of the chemical formula 1 according to the present invention can have significantly improved performance and lifespan characteristics. As such, an organic electroluminescent device with improved performance and lifespan characteristics can ultimately maximize the performance of a full-color organic light-emitting panel.

As described above, the compound represented by the chemical formula 1 according to the present invention can improve the phosphorescence characteristics of an organic electroluminescent device, and at the same time, improve the electron injection/transport capability, luminous efficiency, driving voltage, life characteristics, etc. Therefore, the compound of the chemical formula 1 according to the present invention can be used as an organic layer material of an organic electroluminescent device, preferably an emitting layer material (a blue, green and/or red phosphorescent host material), a hole transport layer material and a hole injection layer material, and more preferably a phosphorescent emitting layer material. In particular, when the compound of the chemical formula 1 according to the present invention is used as an electron injection/transport layer material or a blue, green and/or red phosphorescent host material of an organic electroluminescent device, the efficiency and lifespan of the organic electroluminescent device can be significantly improved compared to conventional organic layer materials (for example, CBP). Therefore, an organic electroluminescent device including the compound of the chemical formula 1 according to the present invention can have significantly improved performance and lifespan characteristics, and a full-color organic light-emitting panel to which such an organic electroluminescent device is applied can also have its performance maximized.

In the compound represented by the chemical formula 1, n1 is 0 or 1, n2 is 0 or 1, and provided that n1+n2 is 0 or 1. For example, in chemical formula 1, both n1 and n2 can be 0. In this case, the compound can be embodied as a compound of chemical formula 5, a compound of chemical formula 8, etc. As another example, in chemical formula 1, n1 can be 1, and n2 can be 0. In this case, the compound can be embodied as a compound of chemical formula 6, a compound of chemical formula 9, etc. As yet another example, in chemical formula 1, n1 can be 0, and n2 can be 1. In this case, the compound can be embodied as a compound of chemical formula 7, a compound of chemical formula 10, etc.

In addition, in the chemical formula 1, L ₁ is a single bond or is selected from the group consisting of an arylene group having C ₆ to C ₆₀ and a heteroarylene group having 5 to 60 nuclear atoms, and may preferably be a single bond.

In addition, in the chemical formula 1, Ar ₁ is selected from the group consisting of an aryl group having C ₆ to C ₆₀ , a heteroaryl group having 5 to 60 nuclear atoms, and an arylamine group having C ₆ to C ₆₀ , and preferably, Ar 1 may be a substituent represented by any one of the following chemical formulas S1 to S11. Here, the substituent of the following chemical formula S1 to the substituent of the following chemical formula S6 is EWG, and the substituent of the following chemical formula S7 to the substituent of the following chemical formula S11 is EDG.

In the above chemical formulas S1 to S11,

Y is O or S,

d, g, h, i, k and l are each integers from 0 to 4,

e and f are integers from 0 to 3,

j is an integer from 0 to 5,

R ₆ to R ₁₈ are the same or different and each independently represent hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C ₁ to C ₄₀ 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 heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ An aryl group selected from the group consisting of an arylboron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ arylphosphine oxide group, and a C ₆ to C ₆₀ arylamine group, or combined with an adjacent group to form a C ₆ to C ₆₀ fused aromatic ring or a 5- to 60-membered fused heteroaromatic ring. Here, the heterocycloalkyl group, the heteroaryl group, and the fused heteroaromatic ring each contain at least one heteroatom selected from the group consisting of N, S, O, and Se.

In addition, in the chemical formula 1, a is an integer from 0 to 3, and preferably, a can be 0 or 1.

Here, when a is 0, it means that hydrogen is not substituted by the substituent R ₁ . In addition, when a is an integer of 1 to 3, one or more R ₁ are the same as or different from each other, and each independently represent deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C ₁ to C ₄₀ 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 heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ ~C ₆₀ arylboron group, C ₆ ~C ₆₀ arylphosphine group, C ₆ ~C ₆₀ arylphosphine oxide group and C ₆ ~C ₆₀ arylamine group are selected from the group consisting of, or R ₁ -R ₁ are bonded to each other to form a C ₆ ~C ₆₀ fused aromatic ring or a 5- to 60-membered fused heteroaromatic ring. Here, the heterocycloalkyl group, the heteroaryl group and the fused heteroaromatic ring each contain at least one heteroatom selected from the group consisting of N, S, O and Se.

In addition, in the chemical formula 1, b is an integer from 0 to 4, and preferably b can be 0 or 1.

Here, when b is 0, it means that hydrogen is not substituted by the substituent R ₂ . In addition, when b is an integer of 1 to 4, one or more R ₂ are the same as or different from each other and each independently represent deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C ₁ to C ₄₀ 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 heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ ~C ₆₀ arylboron group, C ₆ ~C ₆₀ arylphosphine group, C ₆ ~C ₆₀ arylphosphine oxide group and C ₆ ~C ₆₀ arylamine group are selected from the group consisting of, or R ₂ -R ₂ are bonded to each other to form a C ₆ ~C ₆₀ fused aromatic ring or a 5- to 60-membered fused heteroaromatic ring. Here, the heterocycloalkyl group, the heteroaryl group and the fused heteroaromatic ring each contain at least one heteroatom selected from the group consisting of N, S, O and Se.

In addition, in the chemical formula 1, R ₃ and R ₄ are the same as or different from each other, and each independently represent hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C ₁ to C ₄₀ 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 heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C A heterocycloalkyl group is selected from the group consisting of an _arylboron group having a carbon atom, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ arylphosphine oxide group, and a C ₆ to C ₆₀ arylamine group, or R ₃ -R ₄ are bonded to each other to form a C ₆ to C ₆₀ fused aromatic ring or a 5- to 60-membered fused heteroaromatic ring, preferably a C ₆ to C ₆₀ aryl group, and more preferably a phenyl group. Here, the heterocycloalkyl group, the heteroaryl group, and the fused heteroaromatic ring each contain at least one heteroatom selected from the group consisting of N, S, O, and Se.

In addition, in the chemical formula 1, c is an integer from 0 to 4, and preferably, c can be 0 or 1.

Here, when c is 0, it means that hydrogen is not substituted by the substituent R ₅ . In addition, when c is an integer of 1 to 4, one or more R ₅ are the same as or different from each other and each independently represent deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C ₁ to C ₄₀ 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 heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ ~C ₆₀ arylboron group, C ₆ ~C ₆₀ arylphosphine group, C ₆ ~C ₆₀ arylphosphine oxide group and C ₆ ~C ₆₀ arylamine group are selected from the group consisting of, or R ₅ -R ₅ are bonded to each other to form a C ₆ ~C ₆₀ fused aromatic ring or a 5- to 60-membered fused heteroaromatic ring. Here, the heterocycloalkyl group, the heteroaryl group and the fused heteroaromatic ring each contain at least one heteroatom selected from the group consisting of N, S, O and Se.

In one example, when c in chemical formula 1 is 0, the compound of chemical formula 1 according to the present invention can be embodied as a compound represented by chemical formula 2 below. In another example, when c in chemical formula 1 is 2 and R ₅ -R ₅ bond to each other to form a C ₆ to C ₆₀ fused aromatic ring or a 5- to 60-membered fused heteroaromatic ring, the compound of chemical formula 1 according to the present invention can be embodied as a compound represented by chemical formula 3 below.

In the above chemical formulas 2 and 3,

n1, n2, L ₁ , Ar ₁ , a, b and R ₁ to R ₄ are each as defined in the chemical formula 1 above,

The A ring is a monocyclic or polycyclic alicyclic ring, a monocyclic or polycyclic heteroalicyclic ring, a monocyclic or polycyclic aromatic ring, or a monocyclic or polycyclic heteroaromatic ring, and in this case, when there are plural A rings, the plural A rings are the same or different from each other. According to an example, the compound of chemical formula 1 according to the present invention may be a compound represented by the following chemical formula 4, but is not limited thereto.

In the above chemical formula 4,

n1, n2, L ₁ , Ar ₁ , a, b, and R ₁ to R ₄ are each as defined in chemical formula 1.

The compound represented by chemical formula 1 according to the present invention can be embodied as a compound represented by any one of the following chemical formulas 5 to 10.

In the above chemical formulas 5 to 10,

L ₁ , Ar ₁ , b and R ₂ to R ₄ are each as defined in the chemical formula 1.

The compound represented by the chemical formula 1 according to the present invention described above can be further specified by the following exemplary compounds, for example, compounds A-1 to A-8, B-1 to B-8, C-1 to C-8, and D-1 to D-8. However, the compound represented by the chemical formula 1 according to the present invention is not limited to those exemplified below.

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

In the present invention, "alkenyl" means a monovalent substituent derived from an unsaturated hydrocarbon having 2 to 40 carbon atoms and a straight or branched chain having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, and 2-butenyl.

In the present invention, "alkynyl" means a monovalent substituent derived from an unsaturated hydrocarbon having 2 to 40 carbon atoms and a straight or branched chain having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.

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

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

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

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

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

In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.

In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and includes mono- as well as di- and tri-alkylsilyl. In addition, "arylsilyl" means silyl substituted with aryl having 5 to 60 carbon atoms, and includes polyarylsilyl such as mono- as well as di- and tri-arylsilyl.

In the present invention, “alkylboron group” means a boron group substituted with an alkyl having 1 to 40 carbon atoms, and “arylboro group” means a boron group substituted with an aryl having 6 to 60 carbon atoms.

In the present invention, the "alkylphosphinyl group" means a phosphine group substituted with an alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-alkylphosphinyl groups. In addition, the "arylphosphinyl group" in the present invention means a phosphine group substituted with a monoaryl or diaryl having 6 to 60 carbon atoms, and includes mono- as well as di-arylphosphinyl groups.

In the present invention, “arylamine” means an amine substituted with an aryl having 6 to 40 carbon atoms, and includes not only mono- but also di-arylamine.

<Organic electroluminescent device>

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

Specifically, the organic electroluminescent device according to the present invention includes an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, and at least one of the one or more organic layers includes a compound represented by the chemical formula 1. At this time, the compound may be used alone, or two or more may be mixed and used.

The organic layer of one or more layers may be at least one of a hole injection layer, a hole transport layer, an emission layer, an emission auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one of the organic layers among these includes a compound represented by the chemical formula 1. Specifically, the organic layer including the compound of the chemical formula 1 is preferably selected from the group consisting of a hole transport layer, an emission layer, an electron transport auxiliary layer, and an electron transport layer.

According to an example, the organic layer of one or more layers includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer, and the hole transport layer includes a compound represented by the chemical formula 1. In such an organic electroluminescent device, holes can quickly move from the hole injection layer to the light-emitting layer because of the compound of the chemical formula 1, and therefore the binding force between holes and electrons in the light-emitting layer is high. Therefore, the organic electroluminescent device of the present invention is excellent in luminous efficiency, power efficiency, brightness, etc.

According to another example, the organic layer of one or more layers includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, and the electron transport layer or the electron transport auxiliary layer includes a compound represented by the chemical formula 1. In such an organic electroluminescent device, electrons can quickly move from the electron injection layer to the light-emitting layer because of the compound of the chemical formula 1, and therefore the bonding force between holes and electrons in the light-emitting layer is high. Therefore, the organic electroluminescent device of the present invention is excellent in luminous efficiency, power efficiency, brightness, etc.

According to another example, the organic layer of one or more layers includes a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, and an electron injection layer, and the emission layer includes a host material and a dopant material, wherein the host material may include the compound of Chemical Formula 1. In addition, the emission layer of the present invention may further include a host material generally known in the art in addition to the compound of Chemical Formula 1. For example, in the present invention, the host may include a first host and a second host in a weight ratio of 1:99 to 99:1 (specifically, a weight ratio of 20:80 to 80:20), wherein the first host may be the compound of Chemical Formula 1. Here, the compound of Chemical Formula 1 is a P-type host and a hole transport host. Therefore, when the second host includes an N-type host, current loss can be minimized because holes and electrons recombine at the interface of the two hosts.

The above N-type host is an electron-transporting host material having N-type properties, which is a material having a high characteristic of injecting or transporting electrons at the LUMO (lowest unoccupied molecular orbital) energy level, that is, a material having high electron conductivity. As the N-type host usable in the present invention, any material having high electron conductivity generally known in the art can be used without limitation, and examples thereof include π-electron-deficient heteroaryl compounds, quinoxalines, triazine derivative compounds, etc., but are not limited thereto. Here, the π-electron-deficient heteroaryl compound means a compound including a heteroaryl group, and a compound in which the electron density of the delocalized π-bond of the heteroaryl group is reduced due to the high electron affinity of the heteroatom, etc.

In the present invention, the content of the host may be about 70 to 99.9 wt% based on the total amount of the light-emitting layer, and the content of the dopant may be about 0.1 to 30 wt% based on the total amount of the light-emitting layer.

The compound represented by the above chemical formula 1 is included in the organic electroluminescent device as a light-emitting layer material, preferably a green, blue and red phosphorescent host material, more preferably a red or green phosphorescent host material. In this case, since the bonding force between holes and electrons in the light-emitting layer is increased, the efficiency (luminescence efficiency and power efficiency), lifespan, brightness, driving voltage, thermal stability, etc. of the organic electroluminescent device can be improved. Specifically, the compound represented by the above chemical formula 1 is preferably included in the organic electroluminescent device as a green and/or red phosphorescent host, fluorescent host, or dopant material. In particular, the compound represented by the chemical formula 1 of the present invention is preferably a red phosphorescent P-type host material of the light-emitting layer having high efficiency.

The structure of the organic electroluminescent device of the present invention is not particularly limited, but for example, an anode (100), one or more organic layers (300), and a cathode (200) may be sequentially laminated on a substrate (see FIGS. 1 and 2). In addition, it may have a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic layer.

According to an example, the organic electroluminescent device may have a structure in which an anode (100), a hole injection layer (310), a hole transport layer (320), an emission layer (330), an electron transport layer (340), and a cathode (200) are sequentially laminated on a substrate, as illustrated in FIG. 1. Optionally, as illustrated in FIG. 2, an electron injection layer (350) may be positioned between the electron transport layer (340) and the cathode (200). In addition, an electron transport auxiliary layer (not illustrated) may be positioned between the emission layer (330) and the electron transport layer (340). The organic electroluminescent device of the present invention can be manufactured by forming the organic layer and the electrode using materials and methods known in the art, except that at least one of the organic layers (300) [e.g., the hole transport layer (320), the light-emitting layer (330), or the electron transport layer (340)] includes a compound represented by the chemical formula 1.

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

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

Further, examples of the anode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black.

Further examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and multilayer materials such as LiF/Al or LiO ₂ /Al.

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

[Preparation Example 1] Synthesis of BIBC-1

<Step 1> Synthesis of 3-(4-bromodibenzo[b,e][1,4]dioxin-1-yl)-9-phenyl-9H-carbazole

Under a nitrogen stream, 1,4-dibromodibenzo[b,e][1,4]dioxine (100.0 g, 292.4 mmol), 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (129.6 g, 350.9 mmol), Pd(PPh ₃ ) ₄ (16.9 g, 14.6 mmol), K ₂ CO ₃ (80.8 g, 584.8 mmol), and 1,4-dioxane/H ₂ O (1000 ml/200 ml) were mixed and stirred at 120 °C for 4 h.

After the reaction was completed, the organic layer was extracted with methylene chloride and filtered using MgSO ₄ . The solvent was removed from the organic layer obtained by filtration, and then purified by column chromatography (Hexane:EA = 6:1 (v/v)) to obtain 3-(4-bromodibenzo[b,e][1,4]dioxin-1-yl)-9-phenyl-9H-carbazole (110.6 g, yield 75%).

¹ H-NMR: δ 6.82 (d, 2H), 6.94 (dd, 2H), 7.20 (dd, 1H), 7.34-7.62 (m, 9H), 7.89 (s, 1H), 8.13-8.19 (m, 2H) ), 8.30 (d, 1H)

<Step 2> N -(2- chlorophenyl )-4- (9-phenyl-9H-carbazol-3-yl) Synthesis of dibenzo[b,e][1,4]dioxin-1-amine

Under a nitrogen stream, 3-(4-bromodibenzo[b,e][1,4]dioxin-1-yl)-9-phenyl-9H-carbazole (110.6 g, 219.3 mmol), 2-chloroaniline (33.6 g, 263.2 mmol), Pd ₂ (dba) ₃ (10.0 g, 11.0 mmol), X-Phos (10.5 g, 21.9 mmol), Cs ₂ CO ₃ (178.6 g, 548.3 mmol), and xylene (1000 ml) were mixed and stirred at 120 °C for 8 h.

After the reaction was completed, the organic layer was extracted with methylene chloride and filtered using MgSO ₄ . After removing the solvent from the obtained organic layer, it was purified by column chromatography (Hexane:EA = 5:1 (v/v)) to obtain N -(2-chlorophenyl)-4-(9-phenyl-9H-carbazol-3-yl)dibenzo[b,e][1,4]dioxin-1-amine (70.1 g, yield 58%).

¹ H-NMR: δ 5.50 (b, 1H), 6.82 (d, 2H), 6.94 (dd, 2H), 7.05 (d, 1H), 7.20-7.27 (m, 2H), 7.50-7.62 (m, 10H) ), 7.73 (d, 1H), 7.89 (s, 1H), 8.13-8.19 (m, 2H), 8.30 (d, 1H)

<Step 3> Synthesis of BIBC-1

Under a nitrogen stream, N- (2-chlorophenyl)-4-(9-phenyl-9H-carbazol-3-yl)dibenzo[b,e][1,4]dioxin-1-amine (70.1 g, 127.2 mmol), Pd(OAc) ₂ (2.9 g, 12.7 mmol), PCy ₃ ??HBF ₄ (9.4 g, 25.4 mmol), K ₂ CO ₃ (35.2 g, 254.4 mmol), and DMA (1000 ml) were mixed and stirred at 170 °C for 3 h.

After the reaction was completed, the organic layer was extracted with methylene chloride and filtered using MgSO ₄ . After removing the solvent from the obtained organic layer, it was purified by column chromatography (Hexane:EA = 4:1 (v/v)) to obtain BIBC-1 (34.0 g, yield 52%).

^1H -NMR of BIBC-1: δ 7.10-7.20 (m, 5H), 7.42-7.63 (m, 13H), 7.89 (s, 1H), 8.13-8.19 (m, 3H), 8.30 (d, 1H) , 8.42 (b, 1H) (m, 2H)

[Preparation Example 2] Synthesis of BIBC-2

Except that 9-(naphthalen-2-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (147.1 g, 350.9 mmol) was used instead of 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole in <Step 1> of Preparation Example 1, the same procedure as Preparation Example 1 was performed to obtain the target compound BIBC-2 (30.4 g, total yield 18.4%).

^1H -NMR of BIBC-2: δ 6.82 (d, 2H), 6.94 (dd, 2H), 7.19-7.20 (m, 2H), 7.36 (d, 1H), 7.50-7.63 (m, 7H), 7.83 -7.89 (m, 2H), 8.03-8.19 (m, 6H), 8.30 (d, 1H), 8.48 (b, 1H)

[Preparation Example 3] Synthesis of BIBC-3

Except that 1-bromonaphthalen-2-amine (60.0 g, 270.2 mmol) was used instead of 2-chloroaniline in <Step 2> of Preparation Example 1, the same process as Preparation Example 1 was performed to obtain the target compound BIBC-2 (30.5 g, total yield 18.5%).

^1H -NMR of BIBC-3: δ 6.82 (d, 2H), 6.94 (dd, 2H), 7.20 (dd, 1H), 7.50-7.62 (m, 12H), 7.89 (s, 1H), 7.99 (d) , 1H), 8.13-8.19 (m, 2H), 8.30 (d, 1H), 8.42 (b, 1H), 8.54 (d, 1H)

[Preparation Example 4] Synthesis of BIBC-4

Except that N,N-diphenyl-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole was used instead of 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole in <Step 1> of Preparation Example 1, the same procedure as Preparation Example 1 was performed to obtain the target compound BIBC-4 (38.4 g, total yield 19.3%).

^1H -NMR of BIBC-4: δ 6.82 (d, 2H), 6.94-7.24 (m, 17H), 7.45-7.63 (m, 6H), 7.89 (s, 1H), 8.13-8.19 (m, 3H) , 8.30 (d, 1H), 8.44 (b, 1H)

[Synthesis Example 1] Synthesis of Compound A-1

Under a nitrogen stream, BIBC-1 (3.4 g, 6.7 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol), NaH (0.16 g, 6.7 mmol), and DMF (25 ml) obtained in Preparation Example 1 were mixed and stirred at room temperature for 1 hour. After the reaction was completed, the solid salt was filtered and purified by column chromatography to obtain the target compound A-1 (3.5 g, yield 71%).

Mass (theoretical: 745.84, measured: 745 g/mol)

[Synthesis Example 2] Synthesis of Compound A-2

Under a nitrogen stream, BIBC-1 (3.4 g, 6.7 mmol), iodobenzene (1.63 g, 8.0 mmol), Cu (0.05 g, 0.67 mmol), K ₂ CO ₃ (1.85 g, 13.4 mmol), and nitrobenzene (25 ml) obtained in Preparation Example 1 were mixed and stirred at 210°C for 6 hours. After the reaction was completed, the solid salt was filtered and purified by column chromatography to obtain the target compound A-2 (3.1 g, yield 78%).

Mass (theoretical: 590.68, measured: 590 g/mol)

[Synthesis Example 3] Synthesis of Compound A-3

Under a nitrogen flow, BIBC-1 (3.4 g, 6.7 mmol), 2-chloro-3-phenylquinoxaline (1.9 g, 8.0 mmol), Pd(OAc) ₂ (0.15 g, 0.67 mmol), P-( t -bu) ₃ (0.33 ml, 1.34 mmol), NaO t -Bu (1.3 g, 13.4 mmol), and xylene (25 ml) were mixed and stirred at 140 °C for 3 h. After the reaction was completed, the solid salt was filtered and purified by column chromatography to obtain the target compound A-3 (3.6 g, yield 74%).

Mass (theoretical: 718.81, measured: 718 g/mol)

[Synthesis Example 4] Synthesis of Compound A-4

Except that 2-bromonaphthalene (1.7 g, 8.0 mmol) was used instead of 2-chloro-3-phenylquinoxaline used in Synthesis Example 3, the same procedure as in Synthesis Example 3 was followed to obtain the target compound A-4 (2.7 g, yield 62%).

Mass (theoretical: 640.74, measured: 640 g/mol)

[Synthesis Example 5] Synthesis of Compound A-5

Except that 3-bromo-1,1'-biphenyl (1.9 g, 8.0 mmol) was used instead of 2-chloro-3-phenylquinoxaline used in Synthesis Example 3, the same procedure as in Synthesis Example 3 was followed to obtain the target compound A-5 (3.0 g, yield 68%).

Mass (theoretical: 666.77, measured: 666 g/mol)

[Synthesis Example 6] Synthesis of Compound A-6

Except that 4-bromo-N,N-diphenylaniline (2.6 g, 8.0 mmol) was used instead of 2-chloro-3-phenylquinoxaline used in Synthesis Example 3, the same procedure as in Synthesis Example 3 was performed to obtain the target compound A-6 (3.7 g, yield 73%).

Mass (theoretical: 757.89, measured: 757 g/mol)

[Synthesis Example 7] Synthesis of Compound A-7

Except that 3-bromodibenzo[ b,d ]furan (2.0 g, 8.0 mmol) was used instead of 2-chloro-3-phenylquinoxaline used in Synthesis Example 3, the same procedure as in Synthesis Example 3 was performed to obtain the target compound A-7 (3.2 g, yield 71%).

Mass (theoretical: 680.76, measured: 680 g/mol)

[Synthesis Example 8] Synthesis of Compound A-8

Except that 3-bromodibenzo[ b,d ]thiophene (2.1 g, 8.0 mmol) was used instead of 2-chloro-3-phenylquinoxaline used in Synthesis Example 3, the same procedure as in Synthesis Example 3 was performed to obtain the target compound A-8 (3.0 g, yield 65%).

Mass (theoretical: 696.82, measured: 696 g/mol)

[Synthesis Example 9] Synthesis of Compound B-1

Under a nitrogen stream, BIBC-2 (3.4 g, 6.7 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol), NaH (0.16 g, 6.7 mmol), and DMF (25 ml) obtained in Preparation Example 2 were mixed and stirred at room temperature for 1 hour. After the reaction was completed, the solid salt was filtered and purified by column chromatography to obtain the target compound B-1 (3.6 g, yield 68%).

Mass (theoretical: 795.9, measured: 795 g/mol)

[Synthesis Example 10] Synthesis of Compound B-2

Under a nitrogen stream, BIBC-2 (3.4 g, 6.7 mmol), iodobenzene (1.63 g, 8.0 mmol), Cu (0.05 g, 0.67 mmol), K ₂ CO ₃ (1.85 g, 13.4 mmol), and nitrobenzene (25 ml) obtained in Preparation Example 2 were mixed and stirred at 210°C for 6 hours. After the reaction was completed, the solid salt was filtered and purified by column chromatography to obtain the target compound B-2 (3.0 g, yield 71%).

Mass (theoretical: 640.74, measured: 640 g/mol)

[Synthesis Example 11] Synthesis of Compound B-3

Under a nitrogen stream, BIBC-2 (3.4 g, 6.7 mmol), 2-chloro-3-phenylquinoxaline (1.9 g, 8.0 mmol), Pd(OAc) ₂ (0.15 g, 0.67 mmol), P-( t -bu) ₃ (0.33 ml, 1.34 mmol), NaO t -Bu (1.3 g, 13.4 mmol), and xylene (25 ml) obtained in Preparation Example 2 were mixed and stirred at 140°C for 3 hours. After the reaction was completed, the solid salt was filtered and purified by column chromatography to obtain the target compound B-3 (3.3 g, yield 65%).

Mass (theoretical: 768.87, measured: 768 g/mol)

[Synthesis Example 12] Synthesis of Compound B-4

Except that 2-bromonaphthalene (1.7 g, 8.0 mmol) was used instead of 2-chloro-3-phenylquinoxaline used in Synthesis Example 11, the same procedure as in Synthesis Example 11 was followed to obtain the target compound B-4 (3.3 g, yield 71%).

Mass (theoretical: 690.80, measured: 690 g/mol)

[Synthesis Example 13] Synthesis of Compound B-5

Except that 3-bromo-1,1'-biphenyl (1.9 g, 8.0 mmol) was used instead of 2-chloro-3-phenylquinoxaline used in Synthesis Example 11, the same procedure as in Synthesis Example 11 was followed to obtain the target compound B-5 (3.1 g, yield 64%).

Mass (theoretical: 716.83, measured: 716 g/mol)

[Synthesis Example 14] Synthesis of Compound B-6

Except that 4-bromo-N,N-diphenylaniline (2.6 g, 8.0 mmol) was used instead of 2-chloro-3-phenylquinoxaline used in Synthesis Example 11, the same procedure as in Synthesis Example 11 was followed to obtain the target compound B-6 (3.4 g, yield 63%).

Mass (theoretical: 807.95, measured: 807 g/mol)

[Synthesis Example 15] Synthesis of Compound B-7

Except that 3-bromodibenzo[ b,d ]furan (2.0 g, 8.0 mmol) was used instead of 2-chloro-3-phenylquinoxaline used in Synthesis Example 11, the same procedure as in Synthesis Example 11 was followed to obtain the target compound B-7 (3.3 g, yield 68%).

Mass (theoretical: 730.82, measured: 730 g/mol)

[Synthesis Example 16] Synthesis of Compound B-8

Except that 3-bromodibenzo[ b,d ]thiophene (2.1 g, 8.0 mmol) was used instead of 2-chloro-3-phenylquinoxaline used in Synthesis Example 11, the same procedure as in Synthesis Example 11 was followed to obtain the target compound B-8 (3.6 g, yield 72%).

Mass (theoretical: 746.88, measured: 746 g/mol)

[Synthesis Example 17] Synthesis of Compound C-1

Under a nitrogen stream, BIBC-3 (3.4 g, 6.7 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol), NaH (0.16 g, 6.7 mmol), and DMF (25 ml) obtained in Preparation Example 3 were mixed and stirred at room temperature for 1 hour. After the reaction was completed, the solid salt was filtered and purified by column chromatography to obtain the target compound C-1 (4.2 g, yield 78%).

Mass (theoretical: 795.9, measured: 795 g/mol)

[Synthesis Example 18] Synthesis of Compound C-2

Under a nitrogen stream, BIBC-3 (3.4 g, 6.7 mmol), iodobenzene (1.63 g, 8.0 mmol), Cu (0.05 g, 0.67 mmol), K ₂ CO ₃ (1.85 g, 13.4 mmol), and nitrobenzene (25 ml) obtained in Preparation Example 3 were mixed and stirred at 210°C for 6 hours. After the reaction was completed, the solid salt was filtered and purified by column chromatography to obtain the target compound C-2 (3.0 g, yield 71%).

Mass (theoretical: 640.74, measured: 640 g/mol)

[Synthesis Example 19] Synthesis of Compound C-3

Under a nitrogen stream, BIBC-3 (3.4 g, 6.7 mmol), 2-chloro-3-phenylquinoxaline (1.9 g, 8.0 mmol), Pd(OAc) ₂ (0.15 g, 0.67 mmol), P-( t -bu) ₃ (0.33 ml, 1.34 mmol), NaO t -Bu (1.3 g, 13.4 mmol), and xylene (25 ml) obtained in Preparation Example 3 were mixed and stirred at 140°C for 3 hours. After the reaction was completed, the solid salt was filtered and purified by column chromatography to obtain the target compound C-3 (4.0 g, yield 77%).

Mass (theoretical: 768.87, measured: 768 g/mol)

[Synthesis Example 20] Synthesis of Compound C-4

Except that 2-bromonaphthalene (1.7 g, 8.0 mmol) was used instead of 2-chloro-3-phenylquinoxaline used in Synthesis Example 19, the same procedure as in Synthesis Example 19 was followed to obtain the target compound C-4 (3.2 g, yield 70%).

Mass (theoretical: 690.80, measured: 690 g/mol)

[Synthesis Example 21] Synthesis of Compound C-5

Except that 3-bromo-1,1'-biphenyl (1.9 g, 8.0 mmol) was used instead of 2-chloro-3-phenylquinoxaline used in Synthesis Example 19, the same procedure as in Synthesis Example 19 was followed to obtain the target compound C-5 (3.1 g, yield 65%).

Mass (theoretical: 716.83, measured: 716 g/mol)

[Synthesis Example 22] Synthesis of Compound C-6

Except that 4-bromo-N,N-diphenylaniline (2.6 g, 8.0 mmol) was used instead of 2-chloro-3-phenylquinoxaline used in Synthesis Example 19, the same procedure as in Synthesis Example 19 was followed to obtain the target compound C-6 (3.4 g, yield 62%).

Mass (theoretical: 807.95, measured: 807 g/mol)

[Synthesis Example 23] Synthesis of Compound C-7

Except that 3-bromodibenzo[ b,d ]furan (2.0 g, 8.0 mmol) was used instead of 2-chloro-3-phenylquinoxaline used in Synthesis Example 19, the same procedure as in Synthesis Example 19 was followed to obtain the target compound C-7 (3.3 g, yield 67%).

Mass (theoretical: 730.82, measured: 730 g/mol)

[Synthesis Example 24] Synthesis of Compound C-8

Except that 3-bromodibenzo[ b,d ]thiophene (2.1 g, 8.0 mmol) was used instead of 2-chloro-3-phenylquinoxaline used in Synthesis Example 19, the same procedure as in Synthesis Example 19 was followed to obtain the target compound C-8 (3.5 g, yield 69%).

Mass (theoretical: 746.88, measured: 746 g/mol)

[Synthesis Example 25] Synthesis of Compound D-1

Under a nitrogen stream, BIBC-4 (3.4 g, 6.7 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol), NaH (0.16 g, 6.7 mmol), and DMF (25 ml) obtained in Preparation Example 4 were mixed and stirred at room temperature for 1 hour. After the reaction was completed, the solid salt was filtered and purified by column chromatography to obtain the target compound D-1 (4.0 g, yield 65%).

Mass (theoretical: 913.06, measured: 913 g/mol)

[Synthesis Example 26] Synthesis of Compound D-2

Under a nitrogen stream, BIBC-4 (3.4 g, 6.7 mmol), iodobenzene (1.63 g, 8.0 mmol), Cu (0.05 g, 0.67 mmol), K ₂ CO ₃ (1.85 g, 13.4 mmol), and nitrobenzene (25 ml) obtained in Preparation Example 4 were mixed and stirred at 210°C for 6 hours. After the reaction was completed, the solid salt was filtered and purified by column chromatography to obtain the target compound D-2 (3.1 g, yield 61%).

Mass (theoretical: 757.9, measured: 757 g/mol)

[Synthesis Example 27] Synthesis of Compound D-3

Under a nitrogen stream, BIBC-4 (3.4 g, 6.7 mmol), 2-chloro-3-phenylquinoxaline (1.9 g, 8.0 mmol), Pd(OAc) ₂ (0.15 g, 0.67 mmol), P-( t -bu) ₃ (0.33 ml, 1.34 mmol), NaO t -Bu (1.3 g, 13.4 mmol), and xylene (25 ml) obtained in Preparation Example 4 were mixed and stirred at 140°C for 3 hours. After the reaction was completed, the solid salt was filtered and purified by column chromatography to obtain the target compound D-3 (3.4 g, yield 58%).

Mass (theoretical: 886.03, measured: 886 g/mol)

[Synthesis Example 28] Synthesis of Compound D-4

The same procedure as in Synthesis Example 27 was followed, except that 2-bromonaphthalene (1.7 g, 8.0 mmol) was used instead of 2-chloro-3-phenylquinoxaline used in Synthesis Example 28, to obtain the target compound D-4 (3.0 g, yield 55%).

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

[Synthesis Example 29] Synthesis of Compound D-5

Except that 3-bromo-1,1'-biphenyl (1.9 g, 8.0 mmol) was used instead of 2-chloro-3-phenylquinoxaline used in Synthesis Example 28, the same procedure as in Synthesis Example 27 was performed to obtain the target compound D-5 (3.3 g, yield 59%).

Mass (theoretical: 833.99, measured: 833 g/mol)

[Synthesis Example 30] Synthesis of Compound D-6

Except that 4-bromo-N,N-diphenylaniline (2.6 g, 8.0 mmol) was used instead of 2-chloro-3-phenylquinoxaline used in Synthesis Example 28, the same procedure as in Synthesis Example 27 was performed to obtain the target compound D-6 (3.8 g, yield 61%).

Mass (theoretical: 925.11, measured: 925 g/mol)

[Synthesis Example 31] Synthesis of Compound D-7

Except for using 3-bromodibenzo[ b,d ]furan (2.0 g, 8.0 mmol) instead of 2-chloro-3-phenylquinoxaline used in Synthesis Example 28, the same procedure as in Synthesis Example 27 was followed to obtain the target compound D-7 (3.6 g, yield 63%).

Mass (theoretical: 847.98, measured: 847 g/mol)

[Synthesis Example 32] Synthesis of compound D-8

Except for using 3-bromodibenzo[ b,d ]thiophene (2.1 g, 8.0 mmol) instead of 2-chloro-3-phenylquinoxaline used in Synthesis Example 28, the same procedure as in Synthesis Example 27 was followed to obtain the target compound D-8 (3.7 g, yield 64%).

Mass (theoretical: 864.04, measured: 864 g/mol)

[Example 1] Fabrication of green organic EL device

Compound A-1 synthesized in the above Synthesis Example 1 was purified by sublimation to high purity using a commonly known method, and then a green organic EL device was manufactured according to the following process.

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

An organic EL device was fabricated by sequentially stacking m-MTDATA (60 nm)/TCTA (80 nm)/90 wt% compound A-1+ 10 wt% Ir(ppy) ₃ (300 nm)/BCP (10 nm)/Alq ₃ (30 nm)/LiF (1 nm)/Al (200 nm) on the prepared ITO transparent electrode. The structures of m-MTDATA, TCTA, Ir(ppy) ₃ , BCP, and Alq ₃ used here are as follows.

[Examples 2 to 4] Fabrication of green organic EL devices

A green organic EL device was manufactured using the same process as in Example 1, except that the compounds described in Table 1 below were used instead of Compound A-1, which was used as a light-emitting host material when forming the light-emitting layer in Example 1.

[Comparative Example 1] Fabrication of a Green Organic EL Device

A green organic EL device was manufactured using the same process as in Example 1, except that CBP was used instead of compound A-1, which was used as a light-emitting host material when forming the light-emitting layer in Example 1. The structure of CBP used here is as follows.

[Evaluation Example 1]

For each green organic EL device manufactured in Examples 1 to 4 and Comparative Example 1, the driving voltage, current efficiency, and luminescence peak at a current density of 10 mA/cm2 were measured, and the results are shown in Table 1 below.

Sample Host Driving voltage (V) EL peak (nm) Current Efficiency (cd/A) Example 1 A-1 6.21 516 42.3 Example 2 B-1 6.3 517 44.1 Example 3 C-1 6.11 517 41.3 Example 4 D-1 6.24 515 42.5 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1 above, in the case of the green organic EL devices of Examples 1 to 4 using the compounds (A-1 to D-1) according to the present invention as a green phosphorescent host, it was confirmed that the current efficiency and driving voltage were superior to the green organic EL device of Comparative Example 1 using conventional CBP.

[Example 5] Manufacturing of red organic EL device

Compound A-3 synthesized in the above Synthesis Example 3 was purified by sublimation to high purity using a commonly known method, and then a red organic electroluminescent device was manufactured according to the following process.

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

An organic electroluminescent device was fabricated by sequentially stacking m-MTDATA (60 nm)/TCTA (80 nm)/90 wt% of compound A-3 + 10 wt% of (piq) ₂ Ir(acac) (300 nm)/BCP (10 nm)/Alq ₃ (30 nm)/LiF (1 nm)/Al (200 nm) on the prepared ITO transparent electrode. The structures of m-MTDATA, TCTA, (piq) ₂ Ir(acac), BCP, and Alq ₃ used here are as follows.

[Examples 6 to 8] Fabrication of green organic EL devices

A red organic EL device was manufactured using the same process as in Example 5, except that the compounds described in Table 2 below were used instead of Compound A-3, which was used as a light-emitting host material when forming the light-emitting layer in Example 5.

[Comparative Example 2]

A red organic electroluminescent device was manufactured by the same process as in Example 5, except that CBP was used instead of compound A-3, which was used as a luminescent host material in forming the luminescent layer in Example 5. The structure of CBP used here is as follows.

[ Evaluation example 2]

For each organic electroluminescent device manufactured in Examples 5 to 8 and Comparative Example 2, the driving voltage and current efficiency at a current density of 10 mA/cm2 were measured, and the results are shown in Table 2 below.

Sample Host Driving voltage (V) Current Efficiency (cd/A) Example 5 A-3 4.34 13.6 Example 6 B-3 4.51 14.4 Example 7 C-3 4.62 15.8 Example 8 D-3 4.63 10.6 Comparative Example 2 CBP 5.25 8.2

As shown in Table 2 above, in the case of the red organic electroluminescent devices of Examples 5 to 8 using the compounds (A-3 to D-3) according to the present invention as a red phosphorescent host, it was confirmed that the current efficiency and driving voltage were superior to the red organic electroluminescent device of Comparative Example 2 using conventional CBP.

[Example 9] Manufacturing of red organic EL device

Compound A-2 synthesized in the above Synthesis Example 2 was purified by sublimation to high purity using a commonly known method, and then a red organic electroluminescent device was manufactured according to the following process.

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

An organic EL device was manufactured on the ITO transparent electrode prepared as described above in the following order: m-MTDATA (60 nm) / Compound A-2 (80 nm) / 95 wt% DS-H522 + 5 wt% DS-501 (30 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm).

DS-H522 and DS-501 used at this time are products of Doosan Electronics BG, and the structures of m-MTDATA, BCP, and Alq ₃ are as follows.

[Examples 10 to 32] Fabrication of red organic EL device

A red organic EL device was manufactured using the same process as in Example 9, except that the compounds described in Table 3 below were used instead of Compound A-2, which was used as a hole transport layer material when forming the hole transport layer in Example 9.

[Comparative Example 3] Fabrication of a Red Organic EL Device

An organic EL device was manufactured in the same manner as in Example 9, except that NPB was used as a hole transport layer material instead of compound A-2 used as a hole transport layer material in forming the hole transport layer in Example 9. The structure of NPB used at this time is as follows.

[Evaluation Example 3]

The driving voltage and current efficiency at a current density of 10 mA/cm2 were measured for the organic EL devices manufactured in Examples 9 to 32 and Comparative Example 3, respectively, and the results are shown in Table 3 below.

Sample hole transport layer Driving voltage (V) Current Efficiency (cd/A) Example 9 A-2 4.8 19.4 Example 10 A-4 4.6 20.1 Example 11 A-5 4.7 20.0 Example 12 A-6 4.4 22.0 Example 13 A-7 4.9 21.1 Example 14 A-8 4.3 22.1 Example 15 B-2 4.8 22.0 Example 16 B-4 4.8 22.9 Example 17 B-5 4.9 19.9 Example 18 B-6 5.0 19.5 Example 19 B-7 5.0 21.3 Example 20 B-8 5.1 18.9 Example 21 C-2 5.0 21.0 Example 22 C-4 4.5 21.1 Example 23 C-5 4.8 18.4 Example 24 C-6 4.9 18.9 Example 25 C-7 5.0 19.0 Example 26 C-8 5.0 18.9 Example 27 D-2 4.5 21.1 Example 28 D-4 4.3 22.3 Example 29 D-5 5.1 21.1 Example 30 D-6 5.1 19.2 Example 31 D-7 4.8 19.2 Example 32 D-8 5.1 21.1 Comparative Example 3 NPB 5.2 18.1

As shown in Table 3 above, it was found that the organic EL devices of Examples 9 to 32 using the compounds (A-2 to D-8) according to the present invention as hole transport layer materials exhibited better performance in terms of current efficiency and driving voltage than the organic EL device of Comparative Example 3 using conventional NPB.

[Example 33] Manufacturing of blue organic EL device

Compound A-1 synthesized in Synthesis Example 1 was purified by sublimation to high purity using a commonly known method, and then a blue organic electroluminescent device was manufactured as follows.

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

On the ITO transparent electrode prepared as described above, an organic electroluminescent device was manufactured by sequentially stacking DS-205 (80 nm)/NPB (15 nm)/95 wt% ADN + 5 wt% DS-405 (30 nm)/compound A-1 (5 nm)/Alq ₃ (25 nm)/LiF (1 nm)/Al (200 nm) on top of the electrode.

The DS-205 used at this time is a product of Doosan Electronics BG, and the structures of NPB, ADN, and Alq ₃ are as follows.

[Examples 34 to 36] Manufacturing of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 33, except that each of the compounds described in Table 4 below was used instead of A-1 used as the electron transport auxiliary layer material in Example 33.

[Comparative Example 4] Manufacturing of Blue Organic Electroluminescent Device

A blue organic electroluminescent device was manufactured in the same manner as in Example 33, except that the electron transport auxiliary layer was not formed and the electron transport layer material, Alq ₃ , was deposited at 30 nm instead of 25 nm.

[Comparative Example 5] Manufacturing of Blue Organic Electroluminescent Device

An organic electroluminescent device was manufactured in the same manner as in Example 33, except that BCP was used instead of compound A-1 used as an electron transport auxiliary layer material in Example 33. The structure of BCP used here is as follows.

[Evaluation Example 4]

For the organic electroluminescent devices manufactured in Examples 33 to 36 and Comparative Examples 4 to 5, the driving voltage, current efficiency, emission wavelength, and lifespan (T97) at a current density of 10 mA/cm2 were measured, and the results are shown in Table 4 below.

Sample Electron transport auxiliary layer Driving voltage (V) Current Efficiency (cd/A) EL peak (nm) Lifespan (hr, T ₉₇ ) Example 33 A-1 4.2 6.4 459 49 Example 34 B-1 4.6 6.1 460 49 Example 35 C-1 4.4 6.1 459 48 Example 36 D-1 4.1 6.4 459 49 Comparative Example 4 - 4.8 6.5 461 49 Comparative Example 5 BCP 5.3 5.9 458 28

As can be seen in Table 4, in the case of the blue organic EL devices of Examples 33 to 36 using the compounds (A-1 to D-1) according to the present invention as an electron transport auxiliary layer material, the driving voltage was similar to or slightly superior to that of the blue organic EL device of Comparative Example 4 not using an electron transport auxiliary layer, but the current efficiency and lifespan were greatly improved.

In addition, the blue organic EL devices of Examples 33 to 36 not only had superior driving voltage and current efficiencies compared to the blue organic EL device of Comparative Example 5 that used conventional BCP as an electron transport auxiliary layer material instead of an electron transport auxiliary layer, but also had significantly improved lifespan.

In this way, it was confirmed that when the compound according to the present invention is used as an electron transport auxiliary layer material, the driving voltage and current efficiency are improved, and further, the life characteristics can be greatly improved.

[Example 37] Manufacturing of blue organic EL device

Compound A-1 synthesized in Synthesis Example 1 was purified by sublimation to high purity using a commonly known method, and then a blue organic electroluminescent device was manufactured as follows.

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

On the ITO transparent electrode prepared as described above, an organic electroluminescent device was manufactured by stacking DS-205 (80 nm)/NPB (15 nm)/95 wt% of ADN + 5 wt% DS-405 (30 nm)/compound A-1 (30 nm)/LiF (1 nm)/Al (200 nm) in that order. The DS-205 used here is a product of Doosan Electronics BG, and the structures of NPB and ADN are as follows.

[Examples 38 to 40] Manufacturing of blue organic electroluminescent device

An organic electroluminescent device was manufactured in the same manner as in Example 37, except that each of the compounds described in Table 5 below was used instead of Compound A-1 used as an electron transport layer material in Example 37.

[Comparative Example 6] Manufacturing of a Blue Organic Electroluminescent Device

An organic electroluminescent device was manufactured in the same manner as in Example 37, except that Alq ₃ was used instead of compound A-1 used as an electron transport layer material in Example 37. The structure of Alq ₃ used here is as follows.

[Evaluation Example 5]

For the organic electroluminescent devices manufactured in Examples 37 to 40 and Comparative Example 6, the driving voltage, current efficiency, emission wavelength, and lifespan (T97) at a current density of 10 mA/cm2 were measured, and the results are shown in Table 5 below.

Sample Electron transport layer Driving voltage (V) Current Efficiency (cd/A) Luminescence peak (nm) Example 37 A-1 4.3 6 466 Example 38 B-1 4.4 6.3 461 Example 39 C-1 4.6 6.2 463 Example 40 D-1 4.5 6.4 464 Comparative Example 6 Alq ₃ 4.7 5.6 458

As can be seen in Table 5, the blue organic EL devices of Examples 37 to 40 using the compounds (A-1 to D-1) according to the present invention as an electron transport layer material showed improved driving voltage and current efficiency compared to the blue organic EL device of Comparative Example 6 using Alq ₃ as an electron transport layer material.

In this way, it was confirmed that when the compound according to the present invention was used as an electron transport layer material, the driving voltage and current efficiency could be improved.

100: positive, 200: negative,
300: Organic layer, 310: Hole injection layer,
320: hole transport layer, 330: light emitting layer,
340: electron transport layer, 350: electron injection layer

Claims (11)

An organic compound represented by the following chemical formula 1:
[Chemical Formula 1]

(In the above formula,
n1 is 0 or 1, n2 is 0 or 1, and then n1+n2 is 0 or 1,
L ₁ is a single bond or is selected from the group consisting of an arylene group having C ₆ to C ₆₀ and a heteroarylene group having 5 to 60 ring atoms,
Ar ₁ is selected from the group consisting of an aryl group having C ₆ to C ₆₀ , a heteroaryl group having 5 to 60 ring atoms, and an arylamine group having C ₆ to C ₆₀ ,
a is an integer from 0 to 3,
b and c are each integers from 0 to 4,
R ₁ , R ₂ and R ₅ are the same as or different from each other, and each independently represents deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C ₁ to C ₄₀ 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 heterocycloalkyl group having 3 to 40 ring atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 ring atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ selected from the group consisting of an arylboron group, an arylphosphine group having C ₆ to C ₆₀ , an arylphosphine oxide group having C ₆ to C ₆₀ , and an arylamine group having C ₆ to C ₆₀ , or combined with an adjacent group to form a condensed aromatic ring or a condensed heteroaromatic ring,
R ₃ and R ₄ are the same or different and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C ₁ to C ₄₀ 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 heterocycloalkyl group having 3 to 40 ring atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 ring atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ selected from the group consisting of an arylboron group, an arylphosphine group having C ₆ to C ₆₀ , an arylphosphine oxide group having C ₆ to C ₆₀ , and an arylamine group having C ₆ to C ₆₀ , or combined with an adjacent group to form a condensed aromatic ring or a condensed heteroaromatic ring,
The arylene group, heteroarylene group of L _{1 and} the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, _alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of R 1 to R 5 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 ring atoms, C ₆ to C ₆₀ aryl group having 5 to 60 ring atoms. (wherein the heteroaryl group is unsubstituted _or substituted with one or _{more substituents selected from the group consisting of a heteroaryl group, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group , a} C ₆ to C ₆₀ arylsilyl group, a C 1 to C ₄₀ alkylboron group, a C ₆ to C _{60 arylboron group, a C 6 to C 60 arylphosphine} group, a C 6 to C ₆₀ arylphosphine oxide group, and a C ₆ to C ₆₀ arylamine group, and wherein when there are plural substituents, they are the same as or different from each other.) In the first paragraph,
The compound represented by the above chemical formula 1 is a compound represented by the following chemical formula 2 or 3:
[Chemical formula 2]

[Chemical Formula 3]

(In the above chemical formulas 2 and 3,
n1, n2, L ₁ , Ar ₁ , a, b and R ₁ to R ₄ are each as defined in Article 1,
The A ring is a monocyclic or polycyclic alicyclic ring, a monocyclic or polycyclic heteroalicyclic ring, a monocyclic or polycyclic aromatic ring, or a monocyclic or polycyclic heteroaromatic ring, and when there are multiple A rings, the multiple A rings are the same or different from each other. In the second paragraph,
The compound represented by the above chemical formula 3 is a compound represented by the following chemical formula 4:
[Chemical Formula 4]

(In the above chemical formula 4,
n1, n2, L ₁ , Ar ₁ , a, b, and R ₁ to R ₄ are each as defined in Article 1). In the first paragraph,
The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 5 to 10:
[Chemical Formula 5]

[Chemical formula 6]

[Chemical formula 7]

[Chemical formula 8]

[Chemical formula 9]

[Chemical Formula 10]

(In the above chemical formulas 5 to 10,
L ₁ , Ar ₁ , b and R ₂ to R ₄ are each as defined in Article 1). In the first paragraph,
_L1 is a compound with a single bond. In the first paragraph,
Ar ₁ is a compound which is a substituent represented by any one of the following chemical formulas S1 to S11:

(In the above chemical formulas S1 to S11,
Y is O or S,
d, g, h, i, k and l are each integers from 0 to 4,
e and f are integers from 0 to 3,
j is an integer from 0 to 5,
R ₆ to R ₈ , R ₁₁ to R ₁₈ are the same or different and each independently represent deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C ₁ to C ₄₀ 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 heterocycloalkyl group having 3 to 40 ring atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 ring atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C A group selected from the group consisting of _an arylboron group of C ₆ to C ₆₀ , an arylphosphine group of C _{6 to C 60, an arylphosphine oxide group of C 6} to C ₆₀ , and an arylamine group of C ₆ to C ₆₀ , or combined with an adjacent group to form a condensed aromatic ring or a condensed heteroaromatic ring,
R ₉ and R ₁₀ are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C ₁ to C ₄₀ 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 heterocycloalkyl group having 3 to 40 ring atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 ring atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ (selected from the group consisting of an arylboron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ arylphosphine oxide group, and a C ₆ to C ₆₀ arylamine group, or combining with an adjacent group to form a fused aromatic ring or a fused heteroaromatic ring). In the first paragraph,
The compound represented by the above chemical formula 1 is a compound selected from the group consisting of compounds A-1 to A-8, B-1 to B-8, C-1 to C-8 and D-1 to D-8:

. An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode,
An organic electroluminescent device, wherein at least one of the organic layers of one or more layers comprises a compound according to any one of claims 1 to 7. In Article 8,
An organic electroluminescent device, wherein the organic layer containing the compound is selected from the group consisting of a light-emitting layer, a hole transport layer, an electron transport auxiliary layer, and an electron transport layer. In Article 9,
The above-mentioned light-emitting layer comprises a host and a dopant,
The above host is an organic electroluminescent device comprising the above compound. In Article 10,
The above host includes a p-type host and an n-type host,
The above p-type host is an organic electroluminescent device comprising the above compound.

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