TW202007764A - A plurality of host materials and organic electroluminescent device comprising the same - Google Patents

Abstract

The present disclosure relates to a plurality of host materials comprising at least one of a first host compound represented by formula 1 and at least one of a second host compound represented by formula 2 and an organic electroluminescent device comprising the same. By comprising the host materials, an organic electroluminescent device having low driving voltage and/or a high luminous efficiency and/or long lifespan can be provided.

Description

Various host materials and organic electroluminescent device containing the same

The present disclosure relates to various host materials and an organic electroluminescent device including the same.

An electroluminescence device (EL device) is a self-luminous display device, which has the advantage that it provides a wider viewing angle, a larger contrast ratio, and a faster response time. The first organic EL device was developed by Eastman Kodak in 1987 by using small aromatic diamine molecules and aluminum complexes as materials for forming the light-emitting layer [Appl. Phys. Lett. [Applied Physics Letters] 51, 913, 1987].

An organic EL device (OLED) converts electrical energy into light by applying power to an organic electroluminescent material, and generally includes an anode, a cathode, and an organic layer formed between these two electrodes. The organic layer of the organic EL device may include a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, an electron blocking layer, a light emitting layer (containing a host material and a dopant material), an electron buffer layer, a hole Barrier layer, electron transport layer, electron injection layer, etc. The materials used in the organic layer can be divided into hole injection materials, hole transmission materials, hole auxiliary materials, light emitting auxiliary materials, electron blocking materials, light emitting materials, electron buffer materials, hole blocking materials, depending on their functions Electron transport materials, electron injection materials, etc. In such an organic EL device, holes from the anode and electrons from the cathode are injected into the light-emitting layer by applying a voltage, and excitons with high energy are generated by recombination of holes and electrons. The organic light-emitting compound moves to the excited state by energy and emits light by the energy when the organic light-emitting compound returns from the excited state to the ground state.

The most important factor that determines the luminous efficiency in organic EL devices is the luminescent material. The luminescent material is required to have the following characteristics: high quantum efficiency, high mobility of electrons and holes, and uniformity and stability of the formed luminescent material layer. The light emitting materials are classified into blue, green, and red light emitting materials according to light emitting colors, and further include yellow or orange light emitting materials. In addition, in terms of function, the luminescent materials are divided into host materials and dopant materials. Recently, an urgent task is to develop organic EL devices with high efficiency and long life. In particular, considering the EL characteristics required for medium and large-sized OLED panels, there is an urgent need to develop highly excellent light-emitting materials superior to conventional materials. For this reason, it is preferred that, as a solid solvent and energy emitter, the preferred characteristics of the host material should have high purity and a suitable molecular weight for deposition under vacuum. In addition, the host material is required to have a high glass transition temperature and pyrolysis temperature to achieve thermal stability, high electrochemical stability to achieve long life, easy formability of amorphous thin films, good adhesion to adjacent layers, and No mobility between layers.

The luminescent material can be used as a combination of host and dopant to improve color purity, luminous efficiency and stability. In general, a device having excellent EL characteristics has a structure including a light-emitting layer formed by doping a dopant into a host. When using such a dopant/host material system as a light emitting material, since the host material greatly affects the efficiency and lifespan of the EL device, their selection is important.

Korean Patent Publication No. 2018-0012709 A discloses a compound having a condensed structure as a host material, the condensed structure including indolocarbazole and nitrogen; however, the reference does not specifically disclose that it has A variety of host materials in specific combinations.

Problems to be solved The objective of this disclosure is, first, to provide a variety of host materials capable of producing organic electroluminescent devices with low driving voltage and/or high luminous efficiency, and/or long lifetime, and second, to provide a Organic electroluminescent device of host material. Solution to the problem

As a result of in-depth research to solve the above technical problems, the inventors of the present invention have found that the above-mentioned object can be achieved by including a plurality of at least one first host compound represented by the following formula 1 and at least one second host compound represented by the following formula 2 The main material is implemented in order to complete the present invention.

HAr-(L ₁ -Ar ₁ ) _a --- (1)

In Equation 1,

HAr represents a substituted or unsubstituted nitrogen-containing (3 to 10 member) heteroaryl group;

L ₁ represents a single bond, or a substituted or unsubstituted (C6-C30) arylene group;

Ar ₁ represents a substituted or unsubstituted (C6-C30) aryl group;

a represents an integer from 1 to 3; and

--- (2)When a is 2 or more, each (L ₁ -Ar ₁ ) may be the same or different.

--- (2)

In Equation 2,

L ₂ represents a single bond, substituted or unsubstituted (C1-C30) alkylene, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, or Substituted or unsubstituted (3 to 30 members) hetero-extended aryl groups;

Ar represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloolefin Group, substituted or unsubstituted (3-member to 7-member) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-member to 30-member) heteroaryl, -NR ₁₆ R ₁₇ , or -SiR ₁₈ R ₁₉ R ₂₀ ; or may be connected to an adjacent substituent to form a ring;

R ₁₆ to R ₂₀ each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3 member to 30 member) heteroaryl Base; and

由下式2-1或2-2表示。

--- (2-1)

--- (2-2)

It is represented by the following formula 2-1 or 2-2.

--- (2-1)

--- (2-2)

In equations 2-1 and 2-2,

X ₁ to X ₂₅ each independently represent N or CR _a ; and

R _a independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3 members to 30 members) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl , Substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted(C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted Substituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamine groups, substituted or unsubstituted mono- or di-(C6-C30)aryl groups An amine group, or a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamine group; or may be connected to an adjacent substituent to form a ring. Invention effect

By using various host materials according to the present disclosure, an organic electroluminescent device with low driving voltage and/or high luminous efficiency and/or long life can be prepared.

Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present invention and is not meant to limit the scope of the present invention in any way.

The present disclosure relates to a variety of host materials and an organic electroluminescent device including the host materials, the plurality of host materials including at least one first host compound represented by Formula 1 above and at least one second host compound represented by Formula 2 above .

Herein, "organic electroluminescent material" means a material that can be used in an organic electroluminescent device and can contain at least one compound. If necessary, the organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material may be a hole injection material, a hole transmission material, a hole auxiliary material, a light emission auxiliary material, an electron blocking material, a light emitting material (including a host material and a dopant material), an electron buffer material, an electron Hole blocking materials, electron transport materials, or electron injection materials, etc.

Herein, "a variety of host materials" means a host material including a combination of at least two compounds, which may be included in any light-emitting layer constituting an organic electroluminescence device. It can mean the material before being included in the organic electroluminescent device (for example, before vapor deposition) and the material after being included in the organic electroluminescent device (for example, after vapor deposition). By. In one embodiment, the plurality of host materials of the present disclosure may be a combination of at least two host materials, and optionally, may additionally include conventional materials contained in organic electroluminescent materials. By methods known in the art, at least two compounds contained in the plurality of host materials of the present disclosure may be included together in one light-emitting layer, or may each be contained in a separate light-emitting layer. For example, the at least two compounds may be evaporated together or co-evaporated, or separately.

Herein, "(C1-C30)(extended)alkyl" means a straight or branched chain alkyl group having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 20, and more It is preferably 1 to 10. The above alkyl groups may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tertiary butyl and the like. "(C3-C30)(Extended)cycloalkyl" is a monocyclic hydrocarbon or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The above cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. "(C3-C30)cycloalkenyl" means a monocyclic or polycyclic hydrocarbon having a ring skeleton of 3 to 30 carbon atoms, which has one or more double bonds, wherein the number of carbon atoms is preferably 3 to 20 , And more preferably 3 to 7. The above cycloalkenyl group may include cyclopropenyl, cyclobutenyl, cyclopentenyl and the like. The "(3-membered to 7-membered) heterocycloalkyl group" has 3 to 7 ring skeleton atoms, preferably 5 to 7 ring skeleton atoms and at least one selected from B, N, O, S, Si and P The group consisting of, is preferably a heteroatom cycloalkyl group consisting of O, S, and N, and includes tetrahydrofuran, pyrrolidine, tetrahydrothiophene (thiolan), tetrahydropiperan, and the like. "(C6-C30)(Extended)aryl" is a monocyclic or condensed ring group derived from aromatic hydrocarbon having 6 to 30 ring skeleton carbon atoms, wherein the number of ring skeleton carbon atoms is preferably 6 to 20, more It is preferably 6 to 15, which may be partially saturated and may contain a spiro structure. Examples of aryl groups specifically include phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, stilbyl, phenylstilbyl, dimethyl Benzyl, phenyl, phenyl, phenyl, phenyl, phenyl, phenyl, phenyl, phenanthryl, phenanthryl, anthracenyl, benzoanthryl, Indenyl, benzophenanthryl, pyrenyl, naphthacyl, perylene, chrysenyl, benzoyl, naphthyl, fluoranthenyl, benzofluoranthyl, tolyl , Xylyl, cresyl, cumyl, spiro[茀-茀] group, spiro[茀-benzo茀] group, azulenyl (azulenyl) and so on. More specifically, the aryl group may be o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, tricresyl, ortho Propylphenyl, m-cumyl, p-cumyl, p-tertiary butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tertiary Butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m Terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl, 1-naphthyl, 2-naphthyl , 1-Cydyl, 2-Cydyl, 3-Cydyl, 4-Cydyl, 9-Cydyl, 9,9-Dimethyl-1-Cydyl, 9,9-Dimethyl-2-Cydyl Group, 9,9-dimethyl-3-stilbyl, 9,9-dimethyl-4-stilbyl, 9,9-diphenyl-1-stilbyl, 9,9-diphenyl-2 -Cylenyl, 9,9-diphenyl-3-yl-yl, 9,9-diphenyl-4-yl-yl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, 1-tenyl, 2-ethenyl, 3-ethenyl, 4-ethenyl, 5-ethenyl, 6-ethenyl, Benzo[c]phenanthryl, benzo[g]biyl, 1-benzophenanthryl, 2-benzophenanthryl, 3-benzophenanthryl, 4-benzophenanthryl, 3-fluoranthryl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, etc. "(3-membered to 30-membered) hetero (extended) aryl" is a group having 3 to 30 ring skeleton atoms Aryl group, wherein the number of ring skeleton atoms is preferably 5 to 25, including at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, P and Ge . The above heteroaryl group may be a single ring, or a fused ring condensed with at least one benzene ring; and may be partially saturated. The above heteroatoms may be connected to at least one substituent selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5 to 30 members) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkane Oxygen, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted(C1- C30) Alkyl di(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamine , Substituted or unsubstituted mono- or di-(C6-C30) arylamine groups, and substituted or unsubstituted (C1-C30) alkyl (C6-30) arylamine groups. In addition, the above heteroaryl group may be a heteroaryl group formed by connecting at least one heteroaryl group or aryl group to the heteroaryl group via one or more single bonds; and may include a spiro structure. Examples of heteroaryl groups may specifically include monocyclic heteroaryl groups, which include furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl , Oxazolyl, oxadiazolyl, triazolyl, tetrahydryl, triazolyl, tetrazolyl, furazyl, pyridyl, pyrazolyl, pyrimidinyl, carbazolyl, etc.; and fused ring hetero Aryl, which includes benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzene Bisoisoazolyl, benzazolyl, imidazopyridyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinoline Group, octinoline group, quinazoline group, quinoline group, carbazolyl group, azacarbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, phen㗁𠯤yl group, phenanthridinyl group, benzodiyl group Oxycyclopentenyl, indolizidine, acridine (acrylidinyl), silyl, germanium, etc. More specifically, the heteroaryl group may be 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidyl, 4-pyrimidyl, 5 -Pyrimidinyl, 6-pyrimidinyl, 1,2,3-tris-4-yl, 1,2,4-tris-3-yl, 1,3,5-tris-2-yl, 1- Imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizidinyl, 2-indolizilyl, 3-indolizilyl, 5-indolizilyl Pyridinyl, 6-indolizidine, 7-indolizidine, 8-indolizidine, 2-imidazopyridyl, 3-imidazopyridyl, 5-imidazopyridyl , 6-imidazopyridyl, 7-imidazopyridyl, 8-imidazopyridyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl Group, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6 -Isoindolyl, 7-isoindolyl, 2-furanyl, 3-furanyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl , 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-iso Benzofuranyl, 7-isobenzofuranyl, 2-quinolinyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl, 8 -Quinolinyl, 1-isoquinolinyl, 3-isoquinolinyl, 4-isoquinolinyl, 5-isoquinolinyl, 6-isoquinolinyl, 7-isoquinolinyl, 8-iso Quinolyl, 2-quinolyl, 5-quinolyl, 6-quinolyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9 -Carbazolyl, azacarbazol-1-yl, azacarbazol-2-yl, azacarbazol-3-yl, azacarbazol-4-yl, azacarbazol-5-yl, Azacarbazol-6-yl, azacarbazol-7-yl, azacarbazol-8-yl, azacarbazol-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3- Phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridine Group, 3-acridyl, 4-acridyl, 9-acridyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl Group, 3-furzanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2- Methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2- Tertiary butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2- Methyl-3-indolyl, 4-methyl-3-indolyl, 2-tertiary butyl-1-indolyl, 4- Tertiary butyl-1-indolyl, 2-tertiary butyl-3-indolyl, 4-tertiary butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzoyl Furyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothienyl, 2-dibenzothienyl, 3-dibenzothienyl, 4-dibenzothienyl , 1-siliconyl, 2-siliconyl, 3-siliconyl, 4-siliconyl, 1-germanium, 2-germanium, 3-germanium, 4-germanium, etc. Here, "halogen" includes F, Cl, Br, and I.

In addition, "o (o)", "m (m)", and "pair (p)" are meant to indicate the substitution positions of all substituents. The ortho position is a compound having substituents adjacent to each other, for example, at positions 1 and 2 of benzene. The meta position is the next substitution position next to the substitution position, for example, the compound has a substituent at positions 1 and 3 on benzene. The next substitution position for the meta position of the para system, for example, the compound has a substituent at the 1 and 4 positions on benzene.

Herein, "a substituted or unsubstituted ring formed by connecting to adjacent substituents" means a substituted or unsubstituted (3) formed by connecting or fusing two or more adjacent substituents (Member to 30 members) monocyclic or polycyclic alicyclic ring, aromatic ring, or a combination thereof; preferably, it may be substituted or unsubstituted (3 member to 26 member) monocyclic or polycyclic aliphatic Cyclic ring, aromatic ring, or a combination thereof. In addition, at least one carbon atom in the formed ring may be replaced by at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably N, O, and S. According to one embodiment, the ring formed by connecting to adjacent substituents may be a (5-member to 20-member) polycyclic aromatic ring, which may contain at least one hetero group selected from the group consisting of N, O, and S atom.

In addition, the expression "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced by another atom or a functional group (ie, a substituent). HAr In Formulas 1 and _{2, L 1, Ar 1, L} 2, Ar, R 16 to R _20, and R _a, the substituted (C1-C30) (extension) alkyl, substituted (C6-C30) (Extended) aryl, substituted (3 to 30 members) hetero (extended) aryl, substituted (C3-C30) (extended) cycloalkyl, substituted (C3-C30) cycloalkenyl, substituted ( 3 to 7 member) heterocycloalkyl, substituted (C1-C30) alkoxy, substituted tri (C1-C30) alkylsilyl, substituted di (C1-C30) alkyl (C6-C30) Arylsilyl, substituted (C1-C30) alkyl di(C6-C30) arylsilyl, substituted tri(C6-C30) arylsilyl, substituted mono- or di-(C1-C30) The substituents of the alkylamino group, substituted mono- or di-(C6-C30)arylamino group, and substituted (C1-C30)alkyl(C6-C30)arylamino group are each independently selected from At least one of the following group, the group consists of the following: deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C30) alkyl, halogenated (C1-C30) alkyl, (C2-C30 )Alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C3-C30)cycloalkyl, (C3-C30)cycloalkenyl, (3 Member to 7 member) heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, (C6-C30) aryl-substituted or unsubstituted (5 member to 30 member) heteroaryl Group, (5-membered to 30-membered) heteroaryl-substituted or unsubstituted (C6-C30)aryl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, di( C1-C30) alkyl (C6-C30) arylsilyl, (C1-C30) alkyl di (C6-C30) arylsilyl, amine, mono- or di-(C1-C30) alkylamine Group, (C1-C30) alkyl-substituted or unsubstituted mono- or di-(C6-C30) arylamino group, (C1-C30) alkyl (C6-C30) arylamino group, (C1- C30) Alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, di(C6-C30)arylboroncarbonyl, di(C1-C30)alkylboroncarbonyl, (C1- C30) alkyl (C6-C30) aryl borocarbonyl, (C6-C30) aryl (C1-C30) alkyl, and (C1-C30) alkyl (C6-C30) aryl, for example, the substituent may Is substituted or unsubstituted methyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted stilbene, substituted or unsubstituted carbazolyl , Substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted diphenylamino, or substituted or unsubstituted phenylbiphenylamino.

Hereinafter, the host material according to one embodiment will be described.

The host material according to the present disclosure includes at least one first host compound represented by Formula 1 above and at least one second host compound represented by Formula 2 above; and according to one embodiment, the host material may be included in an organic electroluminescence device In the light-emitting layer.

According to one embodiment, the first host compound as a host material may be represented by Formula 1 below.

HAr-(L ₁ -Ar ₁ ) _a --- (1)

In Equation 1,

HAr represents a substituted or unsubstituted nitrogen-containing (3 to 10 member) heteroaryl group;

L ₁ represents a single bond, or a substituted or unsubstituted (C6-C30) arylene group;

Ar ₁ represents a substituted or unsubstituted (C6-C30) aryl group;

a represents an integer from 1 to 3; and

When a is 2 or more, each (L ₁ -Ar ₁ ) may be the same or different.

In one embodiment, the HAr may be a substituted or unsubstituted nitrogen-containing (5 to 10 member) heteroaryl group, preferably an unsubstituted nitrogen-containing (6 to 10 member) heteroaryl group. For example, HAr may be pyrimidinyl, triazolyl, quinolinyl, quinolinyl, or quinazolinyl.

In one embodiment, L ₁ may be a single bond or a substituted or unsubstituted (C6-C25) arylene group, preferably a single bond or unsubstituted (C6-C20) arylene group. For example, L ₁ can be a single bond, naphthyl- or fluorenyl-substituted or unsubstituted phenylene, m-biphenylene, p-biphenylene, naphthyl, phenyl-substituted or unsubstituted phenylene Rhenyl, or phenyl-substituted or unsubstituted benzylenyl.

In one embodiment, Ar ₁ may be substituted or unsubstituted (C6-C25) aryl, preferably (C1-C6) alkyl- or (C6-C18) aryl-substituted or unsubstituted ( C6-C18) aryl. For example, Ar ₁ may be fluorenyl-substituted or unsubstituted phenyl, m-biphenyl, p-biphenyl, naphthyl, m-terphenyl, p-terphenyl, benzophenanthryl, phenanthrenyl, at least one benzene Group-or at least one methyl-substituted chloro group (for example, phenyl sulfonyl, diphenyl sulfonyl, or dimethyl sulfonyl), or at least one phenyl- or at least one methyl-substituted benzo Cisyl (for example, dimethylbenzylyl or diphenylbenzyl).

In one embodiment, a may be an integer of 2 or 3, where each (L ₁ -Ar ₁ ) may be the same or different.

--- (1-1)

--- (1-2)The compound represented by Formula 1 may be represented by the following Formula 1-1 or 1-2.

--- (1-1)

--- (1-2)

In equations 1-1 and 1-2,

Y ₁ to Y ₆ and Z ₁ to Z ₄ each independently represent CR ₄ or N, provided that at least one of Y ₁ to Y ₆ represents N, and at least one of Z ₁ to Z ₄ represents N;

R ₄ each independently represents hydrogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, or substituted or unsubstituted (C6-C30)aryl; or may Attach to adjacent substituents to form a ring; and

L ₁ , Ar ₁ , and a are as defined in Formula 1.

In one embodiment, in Formula 1-1, at least one of Y ₁ to Y ₆ may be N, preferably, at least two of Y ₁ to Y ₆ may be N, and more preferably , At least three of Y ₁ to Y ₆ may be N. For example, the compound represented by Formula 1-1 may be (L ₁ -Ar ₁ ) _a -substituted pyrimidine or tri 𠯤.

In one embodiment, in Formula 1-2, at least one of Z ₁ to Z ₄ may be N, preferably, at least two of Z ₁ to Z ₄ may be N. For example, the compound represented by Formula 1-2 may be (L ₁ -Ar ₁ ) _a -substituted quinoline, quinoline, or quinazoline.

In one embodiment, R ₄ each independently represents hydrogen, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C2-C20) alkenyl, or substituted or unsubstituted (C6-C18 ) Aryl; or two adjacent R ₄ may be connected to each other to form a substituted or unsubstituted (3-member to 30-member) monocyclic or polycyclic ring, preferably hydrogen or two adjacent R ₄ may Connect to each other to form an unsubstituted (3-member to 18-member) monocyclic or polycyclic ring, more preferably, hydrogen or two adjacent R ₄ can be connected to each other to form an unsubstituted (3-member to 10-member) Single ring. For example, R ₄ each independently represents hydrogen or two adjacent R ₄ may be fused to each other to form an unsubstituted benzene ring.

According to one embodiment, the first host compound represented by Formula 1 can be illustrated by the following compounds, but is not limited thereto:

[ 反應方案 2]

The compound having formula 1 according to the present disclosure can be produced by a synthesis method known to those skilled in the art. For example, the compound represented by formula 1-1 or 1-2 can be synthesized by referring to the following reaction scheme 1 or 2, But not limited to this: [ Reaction Scheme 1]

[ Reaction Scheme 2]

In Reaction Schemes 1 and 2, L ₁ , Ar ₁ and a are as defined in Formula 1, Y ₁ to Y ₆ and Z ₁ to Z ₄ are as defined in Formula 1-1 and 1-2.

As described above, an exemplary synthetic example of the compound represented by Formula 1-1 or 1-2 according to one embodiment is described, but they are based on the Buchwald-Hartwig cross couple Coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, Miyaura boronation reaction, Suzuki cross-coupling reaction, intramolecular acid-induced cyclization reaction, Pd( II)-Catalyzed oxidation cyclization reaction, Grignard reaction, Heck reaction, cyclic dehydration reaction, SN ₁ substitution reaction, SN ₂ substitution reaction, phosphine-mediated reductive cyclization reaction, etc. Those skilled in the art will understand that the above reaction will proceed even if other substituents defined in Formula 1-1 or 1-2 in addition to the substituents described in the specific synthesis examples are bonded.

--- (2)According to one embodiment, the second host compound as another host material may be represented by Formula 2 below.

--- (2)

In Equation 2,

L ₂ represents a single bond, substituted or unsubstituted (C1-C30) alkylene, substituted or unsubstituted (C6-C30) alkylene, substituted or unsubstituted (3 to 30 members) heteroalkylene , Or substituted or unsubstituted (C3-C30) cycloalkylene;

Ar represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloolefin Group, substituted or unsubstituted (3-member to 7-member) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-member to 30-member) heteroaryl, -NR ₁₆ R ₁₇ , or -SiR ₁₈ R ₁₉ R ₂₀ ; or may be connected to an adjacent substituent to form a ring;

由下式2-1或2-2表示。

--- (2-1)

--- (2-2)R ₁₆ to R ₂₀ each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3 member to 30 member) heteroaryl Base; and

It is represented by the following formula 2-1 or 2-2.

--- (2-1)

--- (2-2)

In equations 2-1 and 2-2,

X ₁ to X ₂₅ each independently represent N or CR _a ; and

R _a independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3 members to 30 members) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl , Substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted(C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted Substituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamine groups, substituted or unsubstituted mono- or di-(C6-C30)aryl groups An amine group, or a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamine group; or may be connected to an adjacent substituent to form a ring.

In one embodiment, L ₂ may be a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3 to 30 member) heteroaryl group, preferably a single bond , Substituted or unsubstituted (C6-C25) extended aryl, or substituted or unsubstituted (5 to 25 members) heteroaryl, more preferably single bond, substituted or unsubstituted (C6-C18) Extensive aryl groups, or substituted or unsubstituted (5 to 18 members) heteroextended aryl groups. For example, L ₂ may be a single bond, or substituted or unsubstituted phenylene, substituted or unsubstituted o-biphenylene, substituted or unsubstituted m-biphenylene, substituted or unsubstituted p-biphenylene Group, substituted or unsubstituted naphthyl, or substituted or unsubstituted carbazolyl.

In one embodiment, Ar may be hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3 to 30 members) heteroaryl, preferably hydrogen, deuterium , Substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5 to 25 members) heteroaryl, more preferably substituted or unsubstituted (C6-C18) aryl or substituted Or unsubstituted (5 to 18 members) heteroaryl.

Specifically, Ar may be substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted p-biphenyl , Substituted or unsubstituted naphthylphenyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted p-terphenyl , Substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted dibenzocarbazolyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted benzene Phenothienyl, substituted or unsubstituted benzonaphthienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzonaphthofuranyl, substituted Or unsubstituted chloro group, substituted or unsubstituted benzo sulfonyl group, substituted or unsubstituted spirobi stilbyl group, substituted or unsubstituted diphenylamine group, substituted or unsubstituted phenylbiphenylamine group , Substituted or unsubstituted naphthylphenylamino, substituted or unsubstituted naphthylbiphenylamino, substituted or unsubstituted diphenylamino, substituted or unsubstituted biphenyl stilbylamino , Or substituted or unsubstituted biphenyldibenzofuranylamino, for example, Ar may be substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted o-biphenyl, substituted Or unsubstituted m-biphenyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted p-terphenyl, substituted or Unsubstituted carbazolyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted stilbyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted Substituted spirobifulcyl, substituted or unsubstituted diphenylamine, substituted or unsubstituted phenylbiphenylamine, or substituted or unsubstituted naphthylphenylamine.

可以由下式2-1表示。

--- (2-1)According to one embodiment, in Equation 2,

It can be represented by the following formula 2-1.

--- (2-1)

In formula 2-1,

X ₁ to X ₁₂ each independently represent N or CR _a ; and

R _a independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3 members to 30 members) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl , Substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted(C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted Substituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamine groups, substituted or unsubstituted mono- or di-(C6-C30)aryl groups An amine group, or a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamine group; or may be connected to an adjacent substituent to form a ring.

In one embodiment, R _a may be each independently hydrogen, deuterium, or substituted or unsubstituted (C6-C30) aryl group; or may be connected to the adjacent substituent group to form a ring, preferably a hydrogen, Deuterium, or substituted or unsubstituted (C6-C25) aryl; or can be connected or fused to adjacent substituents to form substituted or unsubstituted (3 to 30 member) monocyclic or polycyclic alicyclic ring Ring, aromatic ring, or a combination thereof, more preferably hydrogen, deuterium, or substituted or unsubstituted (C6-C18) aryl; or may be connected or fused to an adjacent substituent to form a substituted or Unsubstituted (5 to 30 members) monocyclic or polycyclic aromatic rings, or a combination thereof. For example, R _a can be each independently hydrogen or a substituted or unsubstituted phenyl group; or may be fused to each other to form a substituted or unsubstituted aromatic ring.

In one embodiment, X ₁ and X ₂ may each independently CR _a, wherein R _a may be fused to each other to form a benzene ring.

--- (2-1-1)Specifically, according to one embodiment, Formula 2-1 may be represented by Formula 2-1-1.

--- (2-1-1)

In formula 2-1-1,

R ₄₁ to R ₄₃ each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted ( 3 to 30 members) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkane Based silyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, Substituted or unsubstituted tri(C6-C30)arylsilyl groups, substituted or unsubstituted mono- or di-(C1-C30)alkylamine groups, substituted or unsubstituted mono- or di-(C6-C30 ) Arylamine groups, or substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamine groups; or may be connected to adjacent substituents to form a ring;

ba represents an integer from 1 to 3, bb represents an integer from 1 to 4, and bc represents an integer from 1 to 5; and

When ba, bb, and bc are 2 or more, each R ₄₁ , each R _42, or each R ₄₃ may be the same or different.

In one embodiment, R ₄₁ to R ₄₃ may each independently be hydrogen, deuterium, or substituted or unsubstituted (C6-C30) aryl; or may be connected to adjacent substituents to form a ring, preferably Is hydrogen, deuterium, or substituted or unsubstituted (C6-C25) aryl; or can be connected or fused to adjacent substituents to form substituted or unsubstituted (3 to 30 member) monocyclic or polycyclic Cycloaliphatic ring, aromatic ring, or a combination thereof, more preferably hydrogen, deuterium, or substituted or unsubstituted (C6-C18) aryl; or may be connected or fused to an adjacent substituent to A substituted or unsubstituted (5-membered to 30-membered) monocyclic or polycyclic aromatic ring, or a combination thereof. For example, R ₄₁ to R ₄₃ may each independently be hydrogen or substituted or unsubstituted phenyl; or may be fused with each other to form a substituted or unsubstituted aromatic ring.

可以由下式2-2表示。

--- (2-2)According to another embodiment, in Equation 2,

It can be represented by the following formula 2-2.

--- (2-2)

In Equation 2-2,

X ₁₃ to X ₂₅ each independently represent N or CR _a ; and

R _a independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3 members to 30 members) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl , Substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted(C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted Substituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamine groups, substituted or unsubstituted mono- or di-(C6-C30)aryl groups An amine group, or a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamine group; or may be connected to an adjacent substituent to form a ring.

In one embodiment, R _a may be each independently hydrogen, deuterium, or substituted or unsubstituted (C6-C30) aryl group; or may be connected to the adjacent substituent group to form a ring, preferably a hydrogen, Deuterium, or substituted or unsubstituted (C6-C25) aryl; or can be connected or fused to adjacent substituents to form substituted or unsubstituted (3 to 30 member) monocyclic or polycyclic alicyclic ring Ring, aromatic ring, or a combination thereof, more preferably hydrogen, deuterium, or substituted or unsubstituted (C6-C18) aryl; or may be connected or fused to an adjacent substituent to form a substituted or Unsubstituted (5 to 30 members) monocyclic or polycyclic aromatic rings, or a combination thereof. For example, R _a can be each independently hydrogen or a substituted or unsubstituted phenyl group; or may be fused to each other to form a substituted or unsubstituted aromatic ring.

In one embodiment, X ₁₅ and X ₁₆ may each independently be CR _a, wherein R _a may be fused to each other to form a benzene ring.

In one embodiment, X ₁₇ and X ₁₈ may each independently be CR _a, wherein R _a may be fused to each other to form a benzene ring.

--- (2-2-1)Specifically, according to one embodiment, Formula 2-2 may be represented by Formula 2-2-1.

--- (2-2-1)

In formula 2-2-1,

R ₃₁ to R ₃₄ each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted ( 3 to 30 members) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkane Based silyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, Substituted or unsubstituted tri(C6-C30)arylsilyl groups, substituted or unsubstituted mono- or di-(C1-C30)alkylamine groups, substituted or unsubstituted mono- or di-(C6-C30 ) Arylamine groups, or substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamine groups; or may be connected to adjacent substituents to form a ring;

aa represents an integer of 1 to 3, ab and ac each independently represent an integer of 1 to 4, and ad represents an integer of 1 or 2; and

When aa, ab, ac, and ad are 2 or more, each R ₃₁ , each R ₃₂ , each R _33, or each R ₃₄ may be the same or different.

In one embodiment, R ₃₁ to R ₃₄ may each independently be hydrogen, deuterium, or substituted or unsubstituted (C6-C30) aryl; or may be connected to adjacent substituents to form a ring, preferably Is hydrogen, deuterium, or substituted or unsubstituted (C6-C25) aryl; or can be connected or fused to adjacent substituents to form substituted or unsubstituted (3 to 30 member) monocyclic or polycyclic Cycloaliphatic ring, aromatic ring, or a combination thereof, more preferably hydrogen, deuterium, or substituted or unsubstituted (C6-C18) aryl; or may be connected or fused to an adjacent substituent to A substituted or unsubstituted (5-membered to 30-membered) monocyclic or polycyclic aromatic ring, or a combination thereof. For example, R ₄₁ to R ₄₃ each independently represent hydrogen or a substituted or unsubstituted phenyl group; or may be fused with each other to form a substituted or unsubstituted aromatic ring.

According to one embodiment, the second host compound represented by Formula 2 may be more specifically explained by the following compounds, but is not limited thereto:

The compound having Formula 2 according to the present disclosure, specifically, the compound having Formula 2-1 can be synthesized by referring to the method disclosed in Korean Patent Application No. 2018-0021961 (February 23, 2018), and has the formula The compound of 2-2 can be synthesized by referring to the method disclosed in Korean Patent Publication No. 2018-0012709 (February 6, 2018), but it is not limited thereto. The compound can be produced by another synthetic method known to those skilled in the art.

Hereinafter, an organic electroluminescence device using the above-mentioned various host materials will be described.

The organic electroluminescent device according to the present disclosure includes a first electrode; a second electrode; and at least one organic layer interposed between the first electrode and the second electrode. The organic layer may include a light-emitting layer, and the light-emitting layer may include host materials including at least one first host compound represented by Formula 1 and at least one second host compound represented by Formula 2.

According to one embodiment, the first host compound represented by Formula 1 and the second host compound represented by Formula 2 may be contained in the same organic layer or may be contained in different organic layers, respectively.

The light-emitting layer is a layer from which light is emitted, and may be a single layer or a multilayer in which two or more layers are stacked. In the light-emitting layer, the doping concentration of the dopant compound based on the host compound may be preferably less than 20 wt%, preferably 17 wt%.

One of the first electrode and the second electrode may be an anode, and the other may be a cathode. Wherein, the first electrode and the second electrode may each be formed as a transmissive conductive material, a transflective conductive material, or a reflective conductive material. The organic electroluminescent device may be a top-emission type, a bottom-emission type, or a side-emission type according to the types of materials forming the first electrode and the second electrode. The organic layer may include a light emitting layer, and may further include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, an electron transport layer, an electron injection layer, an intermediate layer, The hole blocking layer, the electron blocking layer, and the electron buffer layer.

The organic layer may further contain an amine-based compound and/or an azide-based compound in addition to the light-emitting material according to the present disclosure. Specifically, the hole injection layer, the hole transport layer, the hole auxiliary layer, the light-emitting layer, the light-emitting auxiliary layer, or the electron blocking layer may contain an amine-based compound (for example, an arylamine-based compound and a styryl aryl-based compound Amine compounds, etc.) as hole injection materials, hole transport materials, hole auxiliary materials, luminescent materials, luminescent auxiliary materials, or electron blocking materials. In addition, the electron transport layer, the electron injection layer, the electron buffer layer, or the hole blocking layer may contain a compound based on acridine as an electron transport material, electron injection material, electron buffer material, or hole blocking material.

In addition, the organic layer may further include at least one metal selected from the group consisting of metals of Group 1 of the periodic table, metals of Group 2, transition metals of Period 4, transition metals of Period 5, and lanthanum The organometallic element and the d-transition element, or at least one complex compound containing such a metal.

According to one embodiment, an organic electroluminescent material can be used as a light-emitting material for a white organic light-emitting device. According to the arrangement of R (red), G (green), B (blue), or YG (yellow-green) light-emitting units, white organic light-emitting devices have shown various structures, such as a parallel side-by-side arrangement method, a stacked arrangement method, or CCM ( Color conversion materials) methods, etc. In addition, according to one embodiment, the organic electroluminescent material can also be applied to organic electroluminescent devices including QDs (quantum dots).

A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be used between the anode and the light emitting layer. The hole injection layer may be multiple layers to reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, where two compounds may be used for each layer in the multilayer. In addition, the hole injection layer may be doped with p-type dopants. In addition, an electron blocking layer can be placed between the hole transport layer (or hole injection layer) and the light emitting layer, and excitons can be confined within the light emitting layer by blocking electrons from overflowing from the light emitting layer to prevent light emission leakage. The hole transport layer or the electron blocking layer may be multiple layers, and multiple compounds may be used for each layer.

An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be used between the light emitting layer and the cathode. The electron buffer layer may be multiple layers to control the injection of electrons and improve the interface characteristics between the light emitting layer and the electron injection layer, where two compounds may be used simultaneously for each multilayer. The hole blocking layer or the electron transport layer may also be multiple layers, where multiple compounds may be used for each layer. In addition, the electron injection layer may be doped with n-type dopant.

The light emitting auxiliary layer may be placed between the anode and the light emitting layer, or between the cathode and the light emitting layer. When the light emitting auxiliary layer is placed between the anode and the light emitting layer, it can be used to promote hole injection and/or hole transport, or to prevent electron overflow. When the light emitting auxiliary layer is placed between the cathode and the light emitting layer, it can be used to promote electron injection and/or electron transport, or to prevent hole overflow. In addition, the hole auxiliary layer can be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can effectively promote or block the hole transmission rate (or hole injection rate), thereby enabling control Charge balance. When the organic electroluminescent device includes two or more hole transport layers, the hole transport layer further included may be used as a hole auxiliary layer or an electron blocking layer. The light emitting auxiliary layer, the hole auxiliary layer, or the electron blocking layer may have the effect of improving the efficiency and/or lifespan of the organic electroluminescent device.

In the organic electroluminescent device of the present disclosure, it may be preferable to place at least one layer (hereinafter, "surface layer") selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer on one or Two electrodes on one or more inner surfaces. Specifically, it is preferable to place a chalcogenide (including oxide) layer of silicon and aluminum on the anode surface of the electroluminescent medium layer, and it is preferable to place a metal halide layer or a metal oxide layer on the electrode On the cathode surface of the luminescent medium layer. The operational stability of the organic electroluminescent device can be obtained by the surface layer. Preferably, the chalcogenide includes SiO _X (1 ≤ X ≤ 2), AlO _X (1 ≤ X ≤ 1.5), SiON, SiAlON, etc.; the halogenated metal includes LiF, MgF ₂ , CaF ₂ , rare earth metal fluoride, etc. ; And metal oxides include Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO, and the like.

In addition, in the organic electroluminescent device of the present disclosure, the mixed region of the electron transport compound and the reducing dopant, or the mixed region of the hole transport compound and the oxidizing dopant may be placed on at least one of the pair of electrodes On the surface. In this case, the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to the electroluminescent medium. In addition, the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium. Preferably, the oxidizing dopant includes various Lewis acids and acceptor compounds, and the reducing dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, the reducing dopant layer can be used as a charge generation layer to prepare an organic electroluminescence device having two or more light-emitting layers and emitting white light.

According to one embodiment, the organic electroluminescent device may further include at least one dopant in the light-emitting layer.

The dopant contained in the organic electroluminescent material of the present disclosure may be at least one phosphorescent dopant or fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant material used in the organic electroluminescent device of the present disclosure is not particularly limited, but may be preferably one or more metallized complex compounds of one or more metal atoms selected from the group consisting of: iridium ( Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably one or more ortho-metallized complex compounds of one or more metal atoms selected from the group consisting of: iridium (Ir ), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably one or more ortho-metallized iridium complex compounds.

--- (101)The dopant included in the organic electroluminescence device may use a compound represented by the following formula 101, but is not limited thereto:

--- (101)

In equation 101,

--- 結構 (1)

--- 結構 (2)Where L is selected from the following structures 1 or 2:

--- Structure (1)

--- Structure (2)

R ₁₀₀ to R ₁₀₃ each independently represent hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted ( C6-C30) aryl, cyano, substituted or unsubstituted (3- to 30-membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; or R ₁₀₀ to R ₁₀₃ can be attached to One or more adjacent substituents to form a substituted or unsubstituted fused ring, for example, substituted or unsubstituted quinoline, substituted or unsubstituted benzofuropyridine, substituted or unsubstituted benzothienopyridine , Substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuroquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenoquinoline;

R ₁₀₄ to R ₁₀₇ each independently represent hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted ( C6-C30) aryl, substituted or unsubstituted (3-member to 30-member) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or R ₁₀₄ to R ₁₀₇ can be attached to One or more adjacent substituents to form a substituted or unsubstituted fused ring, for example, substituted or unsubstituted naphthyl, substituted or unsubstituted stilbene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted Dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuropyridine, or substituted or unsubstituted benzothienopyridine;

R ₁₁₁ to R ₁₂₁ each independently represent hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl; or may be attached to one or more adjacent substituents to form a substituted or unsubstituted fused ring; and

s represents an integer of 1 to 3.

Specific examples of dopant compounds include the following, but are not limited thereto:

In order to form each layer of the organic electroluminescent device of the present disclosure, dry film formation methods such as vacuum evaporation, sputtering, plasma, ion plating methods, etc., or wet film formation methods such as inkjet printing, Nozzle printing, slit coating, spin coating, dip coating, flow coating method, etc. When a wet film forming method is used, a thin film can be formed by dissolving or diffusing the material forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxin, etc. The solvent may be any solvent in which the material forming each layer can be dissolved or diffused and has no problem in terms of film-forming ability.

When a layer is formed by the dopant and the host compound of the present disclosure, co-evaporation or mixture evaporation can be used.

The co-deposition system is a mixed deposition method in which two or more isomer materials are put into a corresponding single crucible source and current is simultaneously applied to two cells to evaporate the material and mixed deposition is performed; A mixed deposition method in which two or more isomer materials are mixed in a crucible source before they are deposited and then a current is applied to a cell to evaporate the material.

According to one embodiment, the disclosed organic electroluminescent device can be used to manufacture display devices such as smartphones, tablets, notebook computers, PCs, TVs, or display devices for vehicles, or lighting devices such as outdoor Or indoor lighting.

In the following, a method for preparing an organic electroluminescent device including various host materials according to the present disclosure and its characteristics will be explained in order to understand the present disclosure in detail. [ Device Examples 1 to 8] Production of an OLED in which a first host compound and a second compound according to the present disclosure are deposited as a host

Production of OLED devices containing the compounds of the present disclosure. First, the transparent electrode indium tin oxide (ITO) film (10 Ω/sq) (GEOMATEC CO., LTD., Japan) used on the glass substrate of the OLED device was subjected to acetone, ethanol and distilled water in sequence The ultrasonic wave was washed and then stored in isopropyl alcohol. Then, the ITO substrate is mounted on the substrate holder of the vacuum vapor deposition apparatus. The compound HI-1 was introduced into the chamber of the vacuum vapor deposition apparatus, and then the pressure in the chamber of the apparatus was controlled to 10 ^-6 Torr. Thereafter, a current was applied to the cell to evaporate the material introduced above, thereby forming a first hole injection layer having a thickness of 80 nm on the ITO substrate. Next, the compound HI-2 was introduced into another cell of the vacuum vapor deposition apparatus, and the compound was evaporated by applying current to the cell, thereby forming a second electrode having a thickness of 5 nm on the first hole injection layer Hole injection layer. The compound HT-1 is then introduced into another cell of the vacuum vapor deposition apparatus, and the compound is evaporated by applying current to the cell, thereby forming a first hole transmission with a thickness of 10 nm on the second hole injection layer Floor. The compound HT-2 is then introduced into another cell of the vacuum vapor deposition apparatus, and the compound is evaporated by applying current to the cell, thereby forming a second hole transport with a thickness of 60 nm on the first hole transport layer Floor. After forming the hole injection layer and the hole transport layer, a light emitting layer is formed thereon as follows: the first host compound and the second host compound of Table 1 below are introduced as a host into a small chamber of the vacuum vapor deposition apparatus, and the Compound RD-39 was introduced into another cell as a dopant. The two host materials were evaporated at different rates and the dopant was deposited at a doping amount of 3 wt% to form a light emitting layer with a thickness of 40 nm on the hole transport layer. Next, the compounds ET-1 and EI-1 were evaporated and deposited at a rate of 1:1 to form an electron transport layer having a thickness of 35 nm on the light emitting layer. After depositing the compound EI-1 as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thus, OLED was produced. [ Comparative Examples 1 and 2] Production of OLEDs containing compounds not according to the present disclosure

An OLED was produced in the same manner as in the device example except that the compounds of Table 1 below were used as the host, respectively.

Table 1 below shows the driving voltage, luminous efficiency, power efficiency, and the operating voltage of the organic electroluminescent devices of device examples 1 to 8 and comparative examples 1 and 2 produced as described above at a brightness of 5,000 nits and at 5,000 nits. The result of the time (lifetime; T80) that is reduced from 100% to 80% under special brightness. [Table 1]

Referring to Table 1 above, it was confirmed that an organic electroluminescence device including a specific combination compound according to one embodiment as a host material has improved characteristics over conventional organic electroluminescence devices in terms of driving voltage and efficiency and/or lifetime.

The compounds used in the device examples and comparative examples are shown in Table 2 below. [Table 2]

no

no

no

Claims (8)

Various host materials including at least one first host compound and at least one second host compound, wherein the first host compound is represented by the following formula 1 and the second host compound is represented by the following formula 2: HAr-(L ₁ -Ar ₁ ) _a --- (1) where, HAr represents a substituted or unsubstituted nitrogen-containing (3 to 10 member) heteroaryl; L ₁ represents a single bond, or substituted or unsubstituted (C6-C30 ) Aryl; Ar ₁ represents a substituted or unsubstituted (C6-C30) aryl; a represents an integer of 1 to 3; and when a is 2 or greater, each (L ₁ -Ar ₁ ) may be Same or different;

--- (2) where L ₂ represents a single bond, substituted or unsubstituted (C1-C30) alkylene, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6 -C30) arylene, or substituted or unsubstituted (3 to 30 members) heteroarylene; Ar represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted Or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3 to 7 member) heterocycloalkyl, substituted or unsubstituted ( C6-C30) aryl, substituted or unsubstituted (3-member to 30-member) heteroaryl, -NR ₁₆ R ₁₇ , or -SiR ₁₈ R ₁₉ R ₂₀ ; or may be attached to an adjacent substituent to form a ring ; R ₁₆ to R ₂₀ each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3 member to 30 member) hetero Aryl; and

It is represented by the following formula 2-1 or 2-2;

--- (2-1)

--- (2-2) wherein X ₁ to X ₂₅ each independently represent N or CR _a ; and R _a each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) Alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3 to 30 members) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted Or unsubstituted (C1-C30) alkyl bis (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1 -C30) alkyl amine group, substituted or unsubstituted mono- or di-(C6-C30) aryl amine group, or substituted or unsubstituted (C1-C30) alkyl (C6-C30) aryl amine group ; Or may be connected to adjacent substituents to form a ring. The host material as described in item 1 of the scope of patent application, wherein the formula 1 is represented by the following formula 1-1 or 1-2:

--- (1-1)

--- (1-2) where Y ₁ to Y ₆ and Z ₁ to Z ₄ each independently represent CR ₄ or N, provided that at least one of Y ₁ to Y ₆ represents N, and Z ₁ to Z ₄ At least one of them represents N; R ₄ each independently represents hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, or substituted or unsubstituted (C6- C30) An aryl group; or may be connected to an adjacent substituent to form a ring; L ₁ , Ar ₁ , and a are as defined in item 1 of the patent application scope. The main material as described in item 1 of the patent application scope, wherein the formula 2 is represented by the following formula 2-1-1:

--- (2-1-1) wherein R ₄₁ to R ₄₃ each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6 -C30) aryl, substituted or unsubstituted (3 to 30 members) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, Substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted(C1-C30)alkane Bis(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamine, substituted or Unsubstituted mono- or di-(C6-C30) arylamine groups, or substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamine groups; or may be attached to adjacent substituents To form a ring; ba represents an integer of 1 to 3, bb represents an integer of 1 to 4, and bc represents an integer of 1 to 5; and when ba, bb, and bc are 2 or more, each R ₄₁ , each Each R ₄₂ or each R ₄₃ may be the same or different. The main material as described in item 1 of the patent application scope, wherein the formula 2-2 is represented by the following formula 2-2-1:

--- (2-2-1) where R ₃₁ to R ₃₄ each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6 -C30) aryl, substituted or unsubstituted (3 to 30 members) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, Substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted(C1-C30)alkane Bis(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamine, substituted or Unsubstituted mono- or di-(C6-C30) arylamine groups, or substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamine groups; or may be attached to adjacent substituents To form a ring; aa represents an integer of 1 to 3, ab and ac each independently represent an integer of 1 to 4, ad represents an integer of 1 or 2; and when aa, ab, ac, and ad are 2 or greater, Each R ₃₁ , each R ₃₂ , each R ₃₃ , and each R ₃₄ may be the same or different. The host material as described in item 1 of the patent application, where Ar represents substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted interlinked Phenyl, substituted or unsubstituted parabiphenyl, substituted or unsubstituted naphthylphenyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl Group, substituted or unsubstituted p-terphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted dibenzocarbazolyl, substituted or unsubstituted di Benzothienyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzonaphthienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, substituted or Unsubstituted benzylidene furanyl group, substituted or unsubstituted benzoyl group, substituted or unsubstituted benzyl group, substituted or unsubstituted spirobiryl group, substituted or unsubstituted diphenylamine group, substituted Or unsubstituted phenylbiphenylamine group, substituted or unsubstituted naphthylphenylamine group, substituted or unsubstituted naphthylbiphenylamine group, substituted or unsubstituted biphenylamine group, substituted Or unsubstituted biphenyl fulcylamino group, or substituted or unsubstituted biphenyl dibenzofuranyl amino group. The host material as described in item 1 of the patent application scope, wherein the compound represented by Formula 1 is selected from the group consisting of:

. The host material as described in item 1 of the patent application scope, wherein the compound represented by formula 2 is selected from the group consisting of:

. An organic electroluminescence device, comprising: an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein the at least one light-emitting layer includes as described in item 1 of the patent application scope A variety of main materials.