DE112020000524T5 - ORGANIC ELECTROLUMINESCENT JOINT AND THIS COMPREHENSIVE ORGANIC ELECTROLUMINESCENT DEVICE - Google Patents

Abstract

The present disclosure relates to an organic electroluminescent compound represented by Formula 1 and an organic electroluminescent device comprising the same. By incorporating the organic electroluminescent compound of the present disclosure, an organic electroluminescent device having improved operating voltage, luminous efficiency, lifetime, and / or current efficiency can be provided.

Description

Technical area

The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.

State of the art

An electroluminescent (EL) device is a self-light emitting display device that has advantages in that it provides a wider viewing angle, greater contrast ratio, and faster response time. The first organic electroluminescent device was developed by Eastman Kodak in 1987 by using small aromatic diamine molecules and aluminum complexes as materials to form a light-emitting layer (see Appl. Phys. Lett. 51,913,1987 ).

The most important factor that determines the light output in the organic electroluminescent device are light-emitting materials. As light emitting materials, fluorescent materials have heretofore been widely used. However, since phosphorescent light emitting materials theoretically increase the luminous efficiency by a factor of four (4) compared to fluorescent light emitting materials in view of electroluminescent mechanisms, phosphorescent light emitting materials have been extensively researched. Iridium (III) complexes are widely known as phosphorescent light emitting materials including bis (2- (2'-benzothienyl) pyridinato-N, C-3 ') iridium (acetylacetonate) [(acac) Ir (btp) ₂ ], Tris (2-phenylpyridine) iridium [Ir (ppy) ₃ ] and bis (4,6-difluorophenylpyridinato-N, C2) picolinatiridium (Firpic) as red, green and blue emitting materials, respectively.

In the prior art, 4,4'-N, N'-dicarbazole biphenyl (CBP) is the best known phosphorescent host material. Recently, Pioneer (Japan) et al. a high performance organic electroluminescent device using bathocuproin (BCP) and aluminum (III) bis (2-methyl-8-quinolinate) (4-phenylphenolate) (BAIq), etc. as host materials, which have been known as hole blocking materials.

Although these materials show good luminous properties, they have the following disadvantages: (1) Due to their low glass transition temperature and poor thermal stability, their degradation can occur during a high temperature deposition process in vacuum and the life of the device decreases. (2) The current efficiency of the organic electroluminescent device is given by [(π / voltage) × current efficiency], and the current efficiency is inversely proportional to the voltage. Although the organic electroluminescent device comprising phosphorescent host materials provides higher current efficiency (cd / A) than one comprising fluorescent materials, a significantly high operating voltage is necessary. Thus, there is no advantage in terms of power efficiency [Im / W]. (3) In addition, when these materials are used in an organic electroluminescent device, the service life of an organic electroluminescent device is short and the luminous efficiency is still to be improved.

In order to improve the light yield, operating voltage and / or service life, various materials or concepts have been proposed for an organic layer of an organic electroluminescent device. However, these were not satisfactory in practical use.

Disclosure of the invention

Technical task

The aim of the present disclosure is firstly to provide an organic electroluminescent compound with which an organic electroluminescent device with improved operating voltage, luminous efficiency, service life and / or current efficiency can be produced, and secondly to provide an organic electroluminescent device which comprises the organic electroluminescent compound.

Solution of the task

wobei
B₁ bis B₇ jeweils unabhängig nicht vorhanden sind oder für einen substituierten oder unsubstituierten (C5-C20)-Ring stehen, in dem das Kohlenstoffatom des Rings durch ein oder mehrere Heteroatome, die aus Stickstoff, Sauerstoff und Schwefel ausgewählt sind, ersetzt sein kann; mit der Maßgabe, dass mindestens fünf von B₁ bis B₇ vorhanden sind und die benachbarten Ringe von B₁ bis B₇ miteinander anelliert sind;
Y für -N-L₁-(Ar1)n, -O-, -S- oder -CR₁ R₂ steht;
L₁ für eine Einfachbindung, ein substituiertes oder unsubstituiertes (C1-C30)-Alkylen, ein substituiertes oder unsubstituiertes (C6-C30)-Arylen, ein substituiertes oder unsubstituiertes (3- bis 30-gliedriges) Heteroarylen oder ein substituiertes oder unsubstituiertes (C3-C30)-Cycloalkylen steht;
Ar₁ für ein substituiertes oder unsubstituiertes (C6-C30)-Aryl, ein substituiertes oder unsubstituiertes (3- bis 30-gliedriges) Heteroaryl oder -NR₃R₄ steht;
R₁ bis R₄ jeweils unabhängig für Wasserstoff, Deuterium, ein Halogen, ein Cyano, ein substituiertes oder unsubstituiertes (C1-C30)-Alkyl, ein substituiertes oder unsubstituiertes (C6-C30)-Aryl, ein substituiertes oder unsubstituiertes (3- bis 30-gliedriges) Heteroaryl oder ein substituiertes oder unsubstituiertes (C3-C30)-Cycloalkyl stehen oder mit einem oder mehreren benachbarten Substituenten zu einem oder mehreren Ringen verknüpft sein können; und
n für eine ganze Zahl mit einem Wert von 1 oder 2 steht; wobei dann, wenn n für 2 steht, jedes von Ar₁ gleich oder voneinander verschieden sein kann.In the present invention, it has been found that the above object can be achieved by a specific organic electroluminescent compound having a structure in which the residues of an 8-membered ring are fused several times and an organic electroluminescent device using the same . Specifically, the above object can be achieved by an organic electroluminescent compound represented by the following formula 1:

whereby
B ₁ to B _{7 are} each independently absent or represent a substituted or unsubstituted (C5-C20) ring in which the carbon atom of the ring can be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur ; with the proviso that there are at least five of B ₁ to B ₇ and the adjacent rings of B ₁ to B ₇ are fused to one another;
Y is -NL ₁ - (Ar1) n, -O-, -S- or -CR ₁ R ₂ ;
L _{1 stands} for a single bond, a substituted or unsubstituted (C1-C30) -alkylene, a substituted or unsubstituted (C6-C30) -arylene, a substituted or unsubstituted (3- to 30-membered) heteroarylene or a substituted or unsubstituted (C3 -C30) -cycloalkylene;
Ar _{1 represents} a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl or -NR ₃ R ₄ ;
R ₁ to R ₄ each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C6-C30) -aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl or a substituted or unsubstituted (C3-C30) -cycloalkyl or can be linked to one or more adjacent substituents to form one or more rings; and
n is an integer with a value of 1 or 2; wherein when n is 2, each of Ar _{1 may be the} same as or different from one another.

Advantageous Effects of the Invention

By using the organic electroluminescent compound of the present disclosure, an organic electroluminescent device having improved operating voltage characteristics, improved luminous efficiency, excellent durability characteristics, and / or high current efficiency can be manufactured.

Embodiment of the invention

The following describes the present disclosure in detail. However, the following description is intended to illustrate the invention and in no way limit the scope of the invention.

The term “organic electroluminescent compound” in the present disclosure means a compound that can be used in an organic electroluminescent device and, as required, can be contained in any layer from which an organic electroluminescent device is constructed.

The term “organic electroluminescent material” in the present disclosure means a material which can be used in an organic electroluminescent device and which can comprise at least one compound. The organic electroluminescent material can, as required, be contained in any layer from which an organic electroluminescent device is constructed. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light emitting auxiliary material, an electron blocking material, a light emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, and so on.

The organic electroluminescent material of the present disclosure may comprise at least one compound represented by Formula 1. The compound represented by Formula 1 may be contained in a light emitting layer, an electron transport layer and / or an electron buffer layer, but is not limited thereto. When used in the light emitting layer, the compound represented by Formula 1 may be contained as a host material. Here, the host material can be a host material of an organic electroluminescent device that emits green or red light. In addition, when the compound represented by Formula 1 is contained in the electron transport layer, it can be contained as an electron transport material. Further, when the compound represented by Formula 1 is contained in the electron buffer layer, it can be contained as an electron buffer material.

The term “multiple organic electroluminescent materials” in the present disclosure means one or more organic electroluminescent materials that comprise a combination of at least two compounds that are present in any organic layer from which an organic electroluminescent device is constructed , can be included. It can mean both a material before inclusion in an organic electroluminescent device (for example before vapor deposition) and a material after inclusion in an organic electroluminescent device (for example after vapor deposition). For example, several organic electroluminescent materials can be a combination of at least two compounds that are present in a hole injection layer, a hole transport layer, an auxiliary hole layer, an auxiliary light emitting layer, an electron blocking layer, a light emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer and / or an electron injection layer may be included. At least two compounds can be incorporated into the same layer or different layers with the aid of the methods used in the art, for example they can be evaporated as a mixture or evaporated together or deposited individually.

The term “multiple host materials” in the present disclosure means one or more host materials that comprise a combination of at least two compounds that can be contained in any light-emitting layer from which an organic electroluminescent device is constructed or can. It can mean both a material before inclusion in an organic electroluminescent device (for example before vapor deposition) and a material after inclusion in an organic electroluminescent device (for example after vapor deposition). For example, the multiple host materials of the present disclosure can be a combination of two or more host materials, and a conventional material incorporated into organic electroluminescent materials can also be optionally included. The two or more compounds contained in the multiple host materials of the present disclosure may be incorporated into one light emitting layer or each may be incorporated into different light emitting layers. For example, the two or more host materials can be evaporated as a mixture or evaporated together or deposited individually.

The term “(C1-C30) -alkyl (en)” here means a linear or branched alkyl (en) with 1 to 30 carbon atoms, from which the chain is built up, the number of carbon atoms preferably 1 to 20 and more preferably 1 to 10. The above alkyl may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and so on. The term “(C2-C30) -alkenyl” means a linear or branched alkenyl having 2 to 30 carbon atoms from which the chain is built up, the number of carbon atoms preferably being 2 to 20 and more preferably 2 to 10. The above alkenyl may include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, and so on. The term “(C2-C30) -alkynyl” means a linear or branched alkynyl having 2 to 30 carbon atoms from which the chain is built up, the number of carbon atoms preferably being 2 to 20 and more preferably 2 to 10. The above alkynyl may include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, and so on. The term “(C3-C30) cycloalkyl (en)” means a mono- or polycyclic hydrocarbon of 3 to 30 Ring skeleton carbon atoms, the number of carbon atoms being preferably 3 to 20 and more preferably 3 to 7. The above cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and so on. The term “(3- to 7-membered) heterocycloalkyl” means a cycloalkyl with 3 to 7 ring skeleton atoms, preferably 5 to 7 ring skeleton atoms, and at least one heteroatom from the group consisting of B, N, O, S, Si and P and preferably the group consisting of O, S and N. The above heterocycloalkyl may include tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran and so on. The term “(C6-C30) aryl (en)” means a monocyclic or fused ring radical which is derived from an aromatic hydrocarbon with 6 to 30 ring skeleton carbon atoms, preferably 6 to 25 ring skeleton carbon atoms and more preferably 6 to 18 ring skeleton. Derives carbon atoms. The above aryl or arylene may be partially saturated and may comprise a spiro structure. The above aryl can be phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, inyl, chrdenyl acenyl, phenylphenanthrenyl, nyl, chrdenra-phenyl, peryl, chrdenra-acenyl, peryl, chrdenra-acenyl, peryl, chrdenyl acenyl, naphthylphenyl, phenylnaphthyl, peryl, Fluoroanthenyl, spirobifluorenyl, azulenyl, etc. include. More specifically, the aryl can be phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, Pyrenyl, 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 4-chrysenyl, 5-chrysenyl, 6-chrysenyl, benzo [c] phenanthryl, benzo [g] chrysenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzofluorenyl, dibenzofluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 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-quaterphenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p-tert-butylphenyl, p- (2-phenylpropyl) phenyl, 4'-methylbiphenylyl, 4 "-tert-butyl-p-terphenyl-4-yl, 9,9-dimethyl-1 -fluorenyl, 9,9-dimethyl-2-fluoro enyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3- fluorenyl, 9,9-diphenyl-4-fluorenyl, and the like.

The term "(3 to 30-membered) heteroaryl (s)" is an aryl (s) with 3 to 30 ring skeleton atoms and at least one, preferably 1 to 4, heteroatoms from the group consisting of B, N, O, S, Si and P. The above heteroaryl (en) can be a monocyclic ring or a fused ring condensed with at least one benzene ring, be partially saturated, one by linking at least one heteroaryl or aryl group with a heteroaryl group via one or more single bonds be formed heteroaryl (en) and comprise a spiro structure. The above heteroaryl may be a monocyclic ring type heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazidazinyl, tetrazanyl, pyrimazidyl, pyrazidrazinyl, pyrimazidrazinyl, pyrimazidrazinyl, pyrimazidrazinyl , etc. and a fused ring type heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, benzolazolyl, benzoxazolyl, benzolazole, quinolyl, indolylochol, benzolazole, isoindolyl, isoindolzol, benzolylzol, benzo-thiazole, dibenzofuranyl, dibenzofuranyl, benzo-thiazole, , Quinoxalinyl, benzoquinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl and so on. More specifically, the heteroaryl can be 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolidinyl, 2-indolidinyl, 3-indolidinyl, 5- Indolidinyl, 6-indolidinyl, 7-indolidinyl, 8-indolidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 3-pyridinyl, 4-pyridyl, 1-indolyl 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7- Isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl lyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazolyl-1-yl, azacarbazolyl-2-yl, azacarbazolyl-3-yl, azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarbazolyl-6-yl, azacarbazolyl-7-yl, Azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1- Acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 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-tert-butylpyrrol-4-yl, 3- (2-phenylpropyl) pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1 -indolyl, 2-met hyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl 3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 4-fluorenyl, 3-silafluorenyl, 2-silafluorenyl, 2-silafluorenyl Silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl, etc. "Halogen" includes F, Cl, Br, and I.

In addition, “ortho (o-)”, “meta (m-)” and “para (p-)” are prefixes that indicate the relative positions of substituents to one another. Ortho indicates that two substituents are adjacent to each other and, for example, when two substituents occupy positions 1 and 2 in a benzene derivative, it is referred to as an ortho position. Meta indicates that there are two substituents in the 1 and 3 positions, and for example, when two substituents in a benzene derivative are in the 1 and 3 positions, it is referred to as the meta position. Para indicates that there are two substituents in the 1 and 4 positions, and for example, when two substituents in a benzene derivative are in the 1 and 4 positions, it is referred to as the para position.

Here, “substituted” in the term “substituted or unsubstituted” means that a hydrogen atom in a particular functional group is replaced by another atom or another functional group, i. H. a substituent. In the present disclosure, the substituents of the substituted (C1-C30) -alkyl (en), the substituted (C6-C30) -aryl (en), the substituted (3- to 30-membered) heteroaryl ( en) s, the substituted (C3-C30) -cycloalkyl (en) s, the substituted (C1-C30) -alkoxy, the substituted tri- (C1-C30) -alkylsilyl, the substituted di- (C1-C30) - alkyl- (C6-C30) -arylsilyl, the substituted (C1-C30) -alkyldi (C6-C30) -arylsilyl, the substituted tri- (C6-C30) -arylsilyl, the substituted mono- or di- (C1- C30) -alkylaminos, the substituted mono- or di- (C6-C30) -arylaminos and the substituted (C1-C30) -alkyl- (C6-C30) -arylaminos each independently by at least one from the group consisting of deuterium; a halogen; a cyano; a carboxyl; a nitro; a hydroxyl; a (C1-C30) alkyl; a halo (C1-C30) alkyl; a (C2-C30) alkenyl; a (C2-C30) alkynyl; a (C1-C30) alkoxy; a (C1-C30) -alkylthio; a (C3-C30) cycloalkyl; a (C3-C30) cycloalkenyl; a (3-7 membered) heterocycloalkyl; a (C6-C30) aryloxy; a (C6-C30) arylthio; a (C6-C30) -aryl which is unsubstituted or substituted by at least one selected from the group consisting of deuterium and one or more (3 to 30-membered) heteroaryl; a (3 to 30-membered) heteroaryl which is unsubstituted or substituted by one or more (C6-C30) -aryl; a tri- (C1-C30) -alkylsilyl; a tri- (C6-C30) -arylsilyl; a di- (C1-C30) -alkyl- (C6-C30) -arylsilyl; a (C1-C30) -alkyldi (C6-C30) -arylsilyl; an amino; a mono- or di- (C1-C30) -alkylamino; a mono- or di- (C6-C30) -arylamino which is unsubstituted or substituted by one or more (C1-C30) -alkyl; a (C1-C30) -alkyl- (C6-C30) -arylamino; a (C1-C30) -alkylcarbonyl; a (C1-C30) alkoxycarbonyl; a (C6-C30) arylcarbonyl; a di (C6-C30) arylboronyl; a di- (C1-C30) -alkylboronyl; a (C1-C30) -alkyl- (C6-C30) -arylboronyl; a (C6-C30) -aryl- (C1-C30) -alkyl and a (C1-C30) -alkyl- (C6-C30) -aryl. According to one embodiment of the present disclosure, the substituents are each independently at least one from the group consisting of deuterium; a (C1-C20) alkyl; a (C6-C25) -aryl which is unsubstituted or substituted by at least one from the group consisting of deuterium and one or more (5- to 30-membered) heteroaryl; a (5- to 30-membered) heteroaryl which is unsubstituted or substituted by one or more (C6-C25) -aryl; and a (C1-C20) -alkyl- (C6-C25) -aryl. According to another embodiment of the present disclosure, the substituents are each independently at least one selected from the group consisting of deuterium; a (C1-C20) alkyl; a (C6-C18) -aryl which is unsubstituted or substituted by at least one from the group consisting of deuterium and one or more (5- to 26-membered) heteroaryl; a (6- to 26-membered) heteroaryl which is unsubstituted or substituted by one or more (C6-C18) -aryl; and a (C1-C10) -alkyl- (C6-C18) -aryl. For example, the substituents can each independently be at least one from the group consisting of deuterium, a methyl, an unsubstituted phenyl, a phenyl which is substituted by one or more deuterium, a phenyl which is substituted by a (26-membered) heteroaryl is substituted, a naphthyl, a biphenyl, a dimethylfluorenyl, a terphenyl, an unsubstituted pyridinyl, a pyridinyl which is substituted by one or more phenyl, a triazinyl which is substituted by one or more phenyl, a dibenzothiophenyl, a dibenzofuranyl and a (26-membered) heteroaryl act.

In the formulas of the present invention, a ring formed by a linkage of adjacent substituents means that at least two adjacent substituents join together to form a substituted or unsubstituted mono- or polycyclic (3 to 30-membered) alicyclic or aromatic ring or the combination thereof, preferably a substituted or unsubstituted mono- or polycyclic (5- to 26-membered) alicyclic or aromatic ring or the combination thereof are linked or fused. In addition, the ring can contain at least one heteroatom selected from B, N, O, S, Si and P, preferably at least one heteroatom selected from N, O and S. For example, the ring can be a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted carbene ring, a substituted or unsubstituted benzene ring, etc.

Here, the heteroaryl (en) and the heterocycloalkyl can each independently contain at least one heteroatom selected from B, N, O, S, Si and p. In addition, the heteroatom at least one from the group consisting of hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C6-C30) -aryl, a substituted or unsubstituted (5- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30) -cycloalkyl, a substituted or unsubstituted (C1-C30) -alkoxy, a substituted or unsubstituted tri- (C1-C30) -alkylsilyl, a substituted one or unsubstituted di- (C1-C30) -alkyl- (C6-C30) -arylsilyl, a substituted or unsubstituted (C1-C30) -alkyldi (C6-C30) -arylsilyl, a substituted or unsubstituted tri- (C6-C30) ) -arylsilyl, a substituted or unsubstituted mono- or di- (C1-C30) -alkylamino, a substituted or unsubstituted mono- or di- (C6-C30) -arylamino and a substituted or unsubstituted (C1-C30) -alkyl (C6-C30) -arylamino be bound.

The following describes the compound represented by Formula 1 in more detail.

In formula 1, B ₁ to B _{7 are} each independently absent or represent a substituted or unsubstituted (C5-C20) ring, preferably an unsubstituted or unsubstituted (C5-C13) ring, in which the carbon atom or carbon atoms of the Ring can be replaced by at least one heteroatom selected from nitrogen, oxygen and sulfur, with the proviso that at least five of B ₁ to B ₇ are present and the adjacent rings of B ₁ to B ₇ are fused to one another are. Fusing the neighboring rings from B ₁ to B ₇ with one another means here that ring B ₁ and ring B ₂ , ring B ₂ and ring B ₃ , ring B ₃ and ring B ₄ , ring B ₄ and ring B ₅ , ring B ₅ and ring B ₆ or ring B ₆ and ring B ₇ are fused together. According to one embodiment of the present disclosure, when any of B ₁ to B _{7 is} a (C6-C20) ring, the adjacent ring may be absent or may be a C5 ring, the carbon atom (s) of the ring can be replaced by at least one heteroatom selected from nitrogen, oxygen and sulfur. According to another embodiment of the present disclosure, B ₁ to B _{7 can} each independently not be present or represent a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted pyrrole ring, a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring, a substituted or unsubstituted cyclopentadiene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted pyridine ring or a substituted or unsubstituted dibenzofuran ring. For example, B ₁ to B _{7 can} each independently be absent or represent a benzene ring which is unsubstituted or substituted by one or more phenyl, one or more naphthyl and / or one or more diphenyltriazinyl; a naphthalene ring; a cyclopentadiene ring which is unsubstituted or substituted by one or more methyl; a fluorene ring which is unsubstituted or substituted by one or more methyl; a pyrrole ring which is substituted by one or more unsubstituted phenyl, a phenyl which is substituted by one or more deuterium, one or more biphenyl and / or one or more pyridyl; a furan ring; a thiophene ring; a pyridine ring or a dibenzofuran ring which is unsubstituted or substituted by one or more diphenyltriazinyl.

In formula 1 Y stands for -NL ₁ - (Ar1) n, -O-, -S- or -CR ₁ R ₂ . According to one embodiment of the present disclosure, Y can be -NL ₁ - (Ar ₁ ) n.

L ₁ stands for a single bond, a substituted or unsubstituted (C1-C30) -alkylene, a substituted or unsubstituted (C6-C30) -arylene, a substituted or unsubstituted (3- to 30-membered) heteroarylene or a substituted or unsubstituted ( C3-C30) cycloalkylene. According to one embodiment of the present disclosure, L ₁ stands for a single bond, a substituted or unsubstituted (C6-C25) -arylene or a substituted or unsubstituted (3 to 30-membered) heteroarylene. According to another embodiment of the present disclosure, L ₁ stands for a single bond, an unsubstituted (C6-C18) -arylene or an unsubstituted (5- to 25-membered) heteroarylene. For example, L ₁ can represent a single bond, a phenylene, a naphthylene, a biphenylene, a pyridylene, a pyrimidinylene, a triazinylene, a quinoxalinylene, a quinazolinylene, a dibenzofuranylene, a benzofuropyrimidinylene, a benzothienopyrimidinylene, or a benzothienopyrimidinylene, an indolopyrimidinylene, or an indolopyrimidinylene.

Ar ₁ stands for a substituted or unsubstituted (C6-C30) -aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl or -NR ₃ R ₄ . According to one embodiment of the present disclosure, Ar ₁ stands for a substituted or unsubstituted (C6-C25) -aryl, a substituted or unsubstituted (5- to 25-membered) heteroaryl or —NR ₃ R ₄ . According to another embodiment of the present disclosure, Ar ₁ stands for a (C6-C25) -aryl which is unsubstituted or substituted by at least one from the group consisting of deuterium, a (C1-C6) -alkyl and a (3- to 30- membered) heteroaryl is substituted; a (5- to 25-membered) heteroaryl which is unsubstituted or substituted by at least one of the group consisting of deuterium, a (C6-C18) -alkyl and a (3- to 30-membered) heteroaryl; or -NR ₃ R ₄ . For example, Ar ₁ can represent an unsubstituted phenyl, a phenyl which is substituted by one or more deuterium, a phenyl which is substituted by one or more 26-membered heteroaryl, a naphthyl, a biphenyl, a fluorenyl which is substituted by one or more Methyl is substituted, a spirobifluorenyl, a terphenyl, a triphenylenyl, a pyridyl which is unsubstituted or substituted by one or more phenyl, a pyrimidinyl which is substituted by one or more phenyl, a substituted triazinyl, a substituted quinoxalinyl, a substituted quinazolinyl , a benzoquinoxalinyl which is substituted by one or more phenyl, a carbazolyl, a dibenzofuranyl, a dibenzothiophenyl, a benzofuropyrimidinyl which is substituted by one or more phenyl, a benzothienopyrimidinyl which is substituted by one or more phenyl, an indolopyrimidinyl which is by one or more phenyl-substituted, or -NR ₃ R ₄ . The substituted triazinyl, substituted quinoxalinyl and substituted quinazolinyl substituents can each independently be at least one selected from the group consisting of a phenyl which is unsubstituted or substituted by deuterium and / or a 26-membered heteroaryl; a naphthyl; a biphenyl; a terphenyl; a dibenzofuranyl; a pyridyl which is substituted by one or more phenyl; a dimethylfluorenyl and a dibenzothiophenyl act.

R ₁ to R ₄ each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C6-C30) -aryl, a substituted or unsubstituted (3- up to 30-membered) heteroaryl or a substituted or unsubstituted (C3-C30) -cycloalkyl or can be linked to one or more adjacent substituents to form one or more rings. According to one embodiment of the present disclosure, R ₁ to R ₄ each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C20) -alkyl or a substituted or unsubstituted (C6-C25) -aryl. According to another embodiment of the present disclosure, R ₁ and R ₂ each independently represent an unsubstituted (C1-C10) -alkyl and R ₃ and R ₄ each independently represent an unsubstituted (C6-C18) -aryl. For example, R ₁ and R _{2 can} be methyl and R ₃ and R _{4 can} be phenyl.

The above n stands for an integer with a value of 1 or 2; wherein when n is 2, each of Ar _{1 may be the} same as or different from one another.

Formula 1 can be represented by any of the following formulas 1-1 to 1-5.

In the formulas 1-1 to 1-5, Y ₁ , Y ₂ , Y ₃ and Y ₄ each independently correspond to the definition of Y in formula 1 and, if several Ar ₁ are present, each of Ar _{1 can be the} same or different from one another ; X ₁ to X ₁₂ each independently represent -N = or -C (R _a ) = and R _a each independently represents hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30) -alkyl substituted or unsubstituted (C6-C30) -aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl or a substituted or unsubstituted (C3-C30) -cycloalkyl or adjacent R _a can be linked to one another to form one or more rings and when a plurality of R _a are present, each of R _a can then be identical to or different from one another.

According to one embodiment of the present disclosure, R _{a is in} each case independently hydrogen, deuterium, a substituted or unsubstituted (C6-C25) -aryl or a substituted or unsubstituted (5- to 25-membered) heteroaryl or adjacent R _a can be one or be linked to several rings. According to another embodiment of the present disclosure, R _{a is in} each case independently hydrogen, an unsubstituted (C6-C18) aryl or a (5- to 25-membered) heteroaryl which is substituted by one or more (C6-C18) -aryl; or adjacent R _a can be linked to one another to form a benzene ring, an indene ring which is substituted by one or more methyls, or a benzofuran ring which is unsubstituted or substituted by one or more diphenyltriazine.

In each of Formulas 1-1 to 1-5, at least one of Ar ₁ and R _{a can be} one selected from those listed in Group 1 below:

In Group 1, D1 and D2 each independently represent a benzene ring or a naphthalene ring; X _{21 represents} O, S, NR ₅ or CR ₆ R ₇ ; X ₂₂ each independently represents CR ₈ or N, with the proviso that at least one of X _{22 represents} N, X ₂₃ each independently represents CR ₉ or N; L ₁₁ to L ₁₈ each independently represent a single bond, a substituted or unsubstituted (C6-C30) -arylene or a substituted or unsubstituted (3 to 30-membered) heteroarylene; R ₁₁ to R ₂₁ and R ₅ to R ₉ each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C6-C30) -aryl substituted or unsubstituted (3 to 30-membered) heteroaryl or a substituted or unsubstituted (C3-C30) cycloalkyl or linked to an adjacent substituent to form one or more rings; aa, ff and gg each independently represent an integer from 1 to 5, bb represents an integer from 1 to 7, and cc, dd and ee each independently represent an integer from 1 to 4.

According to one embodiment of the present disclosure, D1 can stand for a benzene ring; _{X 21} can represent O, S or CR ₆ R ₇ ; L ₁₁ to L _{18 can} each independently represent a single bond; R ₁₁ to R ₂₁ and R ₅ to R _{9 can} each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C20) -alkyl, a substituted or unsubstituted (C6-C25) -aryl or a substituted or unsubstituted (5- up to 25-membered) heteroaryl or linked to an adjacent substituent to form one or more rings; and aa, bb, ff and gg can each independently represent an integer from 1 to 5 and cc, dd and ee can each independently represent an integer from 1 to 4. For example, R ₁₁ can stand for hydrogen, deuterium, a phenyl, a biphenyl or a 26-membered heteroaryl; _{R 12} can be hydrogen or adjacent R ₁₂ can be linked to one another to form one or more benzene rings; R ₁₃ , R ₁₆ and R _{17 can represent} hydrogen; R ₁₈ and R _{19 can represent} hydrogen or phenyl; R ₂₁ can stand for phenyl; R ₆ and R _{7 can represent} methyl; R ₈ can or can represent hydrogen, a phenyl, a biphenyl, a dibenzofuranyl or a dibenzothiophenyl adjacent R _{8 may be} linked to one another to form one or more benzene rings; _{R 9} can represent hydrogen, an unsubstituted phenyl, a phenyl which is substituted by at least one deuterium, a phenyl which is substituted by one or more 26-membered heteroaryl, a naphthyl, a biphenyl, a dimethylfluorenyl, a terphenyl, a pyridyl , which is substituted by one or more phenyl, a dibenzofuranyl or a dibenzothiophenyl and can stand aa for an integer from 1 to 5, bb can stand for an integer from 1 to 4 and cc can stand for an integer with a value stand from 1.

In each of Formulas 1-1 to 1-5, at least one of Ar ₁ and R _{a can be} one selected from those listed in Group 2 below:

In group 2, L stands for a single bond, a substituted or unsubstituted (C1-C30) -alkylene, a substituted or unsubstituted (C6-C30) -arylene, a substituted or unsubstituted (3- to 30-membered) heteroarylene or a substituted or unsubstituted (C3-C30) -cycloalkylene and A ₁ to A ₃ each independently represent a substituted or unsubstituted (C1-C30) -alkyl or a substituted or unsubstituted (C6-C30) -aryl.

In each of Formulas 1-1 to 1-5, at least one of Ar ₁ and R _{a can be} one selected from those listed in Group 3 below:

The compound represented by Formula 1 can be exemplified in detail by the following compounds, but is not limited thereto.

The frameworks of formula 1 according to the present disclosure can be prepared by a synthetic method known to the person skilled in the art and can be prepared, for example, as shown in the following reaction schemes, but are not limited thereto:

In Reaction Schemes 1 to 4, Y ₁ to Y ₄ and X ₁ to X _{12 are} as defined in Formulas 1-1 to 1-5.

Although illustrative synthetic examples of the compound represented by Formula 1 are described above, it will be readily apparent to those skilled in the art that they are all based on a Buchwald-Hartwig cross-coupling reaction, an N-arylation reaction, an H-Mont-mediated etherification reaction, a Miyaura borylation reaction, a Suzuki cross-coupling reaction, an intramolecular acid-induced cyclization reaction, a Pd (II) -catalyzed oxidative cyclization reaction, a Grignard reaction, a Heck reaction, a cyclodehydration reaction, an SN ₁ substitution reaction, an SN ₂ substitution reaction, a phosphine-mediated reductive cyclization reaction, etc. and the above reactions proceed even if substituents which are defined in formula 1 above but are not given in the specific synthesis examples are bonded.

The present disclosure provides an organic electroluminescent material comprising the organic electroluminescent compound represented by Formula 1 and an organic electroluminescent device comprising the organic electroluminescent material. The organic electroluminescent material can consist exclusively of the compound according to the present disclosure or furthermore comprise conventional materials which are also used in the organic electroluminescent material.

The organic electroluminescent compound represented by Formula 1 of the present disclosure may be contained in a light emitting layer, a hole injection layer, a hole transport layer, a hole auxiliary layer, an light emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer and / or an electron blocking layer but can preferably be contained in the light-emitting layer. When used in the light emitting layer, the organic electroluminescent compound represented by Formula 1 of the present disclosure can be contained as a host material. The light-emitting layer can preferably further comprise at least one dopant. Optionally, the organic electroluminescent compound of the present disclosure can be used as a co-host material be used. That is, the light emitting layer may further contain an organic electroluminescent compound other than the organic electroluminescent compound represented by Formula 1 of the present disclosure (first host material) as a second host material. The weight ratio between the first host material and the second host material is in the range from 1:99 to 99: 1. When two or more materials are contained in one layer, mixed deposition may be performed to form a layer, or co-deposition may be performed separately to form a layer at the same time.

wobei
HAr_b für ein substituiertes oder unsubstituiertes (3- bis 30-gliedriges) Heteroaryl steht;
L_b1 für eine Einfachbindung, ein substituiertes oder unsubstituiertes (C6-C30)-Arylen oder ein substituiertes oder unsubstituiertes (3- bis 30-gliedriges) Heteroarylen steht;
R_b1 und R_b2 jeweils unabhängig für Wasserstoff, Deuterium, ein Halogen, ein Cyano, ein substituiertes oder unsubstituiertes (C1-C30)-Alkyl, ein substituiertes oder unsubstituiertes (C6-C30)-Aryl, ein substituiertes oder unsubstituiertes (3- bis 30-gliedriges) Heteroaryl, ein substituiertes oder unsubstituiertes (C3-C30)-Cycloalkyl, ein substituiertes oder unsubstituiertes (C1-C30)-Alkoxy, ein substituiertes oder unsubstituiertes Tri-(C1-C30)-alkylsilyl, ein substituiertes oder unsubstituiertes Di-(C1-C30)-alkyl-(C6-C30)-arylsilyl, ein substituiertes oder unsubstituiertes (C1-C30)-Alkyldi-(C6-C30)-arylsilyl, ein substituiertes oder unsubstituiertes Tri-(C6-C30)-arylsilyl, ein substituiertes oder unsubstituiertes Mono- oder Di-(C1-C30)-alkylamino, ein substituiertes oder unsubstituiertes Mono- oder Di-(C6-C30)-arylamino oder ein substituiertes oder unsubstituiertes (C1-C30)-Alkyl-(C6-C30)-arylamino stehen oder mit einem oder mehreren benachbarten Substituenten zu einem oder mehreren Ringen verknüpft sein können;
a für eine ganze Zahl von 1 bis 4 steht und b für eine ganze Zahl von 1 bis 6 steht; wobei dann, wenn a und b jeweils unabhängig für eine ganze Zahl mit einem Wert von 2 oder mehr stehen, jedes von R_b1 und jedes von R_b2 gleich oder voneinander verschieden sein können.The second host material can be selected from any of the known host materials. For example, the second host material may include, but is not limited to, a compound represented by the following Formula II.

whereby
HAr _{b represents} a substituted or unsubstituted (3- to 30-membered) heteroaryl;
L _{b1 represents} a single bond, a substituted or unsubstituted (C6-C30) -arylene or a substituted or unsubstituted (3 to 30-membered) heteroarylene;
R _b1 and R _b2 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C6-C30) -aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30) -cycloalkyl, a substituted or unsubstituted (C1-C30) -alkoxy, a substituted or unsubstituted tri- (C1-C30) -alkylsilyl, a substituted or unsubstituted di- (C1-C30) -alkyl- (C6-C30) -arylsilyl, a substituted or unsubstituted (C1-C30) -alkyldi (C6-C30) -arylsilyl, a substituted or unsubstituted tri- (C6-C30) -arylsilyl, a substituted or unsubstituted mono- or di- (C1-C30) -alkylamino, a substituted or unsubstituted mono- or di- (C6-C30) -arylamino or a substituted or unsubstituted (C1-C30) -alkyl- (C6-C30 ) -arylamino or with one or more adjacent substituents to one or more Ri can be linked;
a is an integer from 1 to 4 and b is an integer from 1 to 6; wherein when a and b each independently represent an integer having a value of 2 or more, each of R _b1 and each of R _{b2 may be the} same or different from each other.

Specifically, Formula 11 can be represented by either of the following Formulas 11-1 and 11-2.

In formulas 11-1 and 11-2, X _b1 to X _b7 each independently represent CR _b4 or N; at least one of X _b1 to X _{b3 is} N; stands at least one of X _b4 to X _b7 for N and corresponds to R _b3 and R _b4 each independently of the definition of R _b1 .

im Einzelnen wie folgt wiedergegeben werden.

In formulas 11, 11-1 and 11-2 can

can be reproduced in detail as follows.

The compound represented by Formula 11 can be exemplified in detail by the following compounds, but is not limited thereto.

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

The dopant contained in the organic electroluminescent device of the present disclosure may include, but is not limited to, the compound represented by the following formula 101.

R₁₀₀ bis R₁₀₃ stehen jeweils unabhängig für Wasserstoff, Deuterium, ein Halogen, ein (C1-C30)-Alkyl, das unsubstituiert oder durch Deuterium oder ein Halogen substituiert ist, ein substituiertes oder unsubstituiertes (C3-C30)-Cycloalkyl, ein substituiertes oder unsubstituiertes (C6-C30)-Aryl, ein Cyano, ein substituiertes oder unsubstituiertes (3- bis 30-gliedriges) Heteroaryl oder ein substituiertes oder unsubstituiertes (C1-C30)-Alkoxy oder können mit einem oder mehreren benachbarten R₁₀₀ bis R₁₀₃ zu einem substituierten oder unsubstituierten anellierten Ring mit einem Pyridin, z. B. einem substituierten oder unsubstituierten Chinolin-, einem substituierten oder unsubstituierten Isochinolin-, einem substituierten oder unsubstituierten Benzofuropyridin-, einem substituierten oder unsubstituierten Benzothienopyridin-, einem substituierten oder unsubstituierten Indenopyridin-, einem substituierten oder unsubstituierten Benzofurochinolin-, einem substituierten oder unsubstituierten Benzothienochinolin- oder einem substituierten oder unsubstituierten Indenochinolinring, verknüpft sein;
R₁₀₄ bis R₁₀₇ stehen jeweils unabhängig für Wasserstoff, Deuterium, ein Halogen, ein (C1-C30)-Alkyl, das unsubstituiert oder durch Deuterium oder ein Halogen substituiert ist, ein substituiertes oder unsubstituiertes (C3-C30)-Cycloalkyl, ein substituiertes oder unsubstituiertes (C6-C30)-Aryl, ein substituiertes oder unsubstituiertes (3- bis 30-gliedriges) Heteroaryl , ein Cyano oder ein substituiertes oder unsubstituiertes (C1-C30)-Alkoxy oder können mit einem oder mehreren benachbarten R₁₀₄ bis R₁₀₇ zu einem substituierten oder unsubstituierten anellierten Ring mit einem Benzol, z. B. einem substituierten oder unsubstituierten Naphthalin-, einem substituierten oder unsubstituierten Fluoren-, einem substituierten oder unsubstituierten Dibenzothiophen-, einem substituierten oder unsubstituierten Dibenzofuran-, einem substituierten oder unsubstituierten Indenopyridin-, einem substituierten oder unsubstituierten Benzofuropyridin- oder einem substituierten oder unsubstituierten Benzothienopyridinring, verknüpft sein.
R₂₀₁ bis R₂₂₀ stehen jeweils unabhängig für Wasserstoff, Deuterium, ein Halogen, ein (C1-C30)-Alkyl, das unsubstituiert oder durch Deuterium oder ein Halogen substituiert ist, ein substituiertes oder unsubstituiertes (C3-C30)-Cycloalkyl oder ein substituiertes oder unsubstituiertes (C6-C30)-Aryl oder können mit einem oder mehreren benachbarten von benachbarten R₂₀₁ bis R₂₂₀ zu einem substituierten oder unsubstituierten anellierten Ring verknüpft sein; und
n steht für eine ganze Zahl von 1 bis 3.In Formula 101, L is selected from the following structures 1 to 3:

R ₁₀₀ to R ₁₀₃ each independently represent hydrogen, deuterium, a halogen, a (C1-C30) -alkyl which is unsubstituted or substituted by deuterium or a halogen, a substituted or unsubstituted (C3-C30) -cycloalkyl, a substituted one or unsubstituted (C6-C30) -aryl, a cyano, a substituted or unsubstituted (3- to 30-membered) heteroaryl or a substituted or unsubstituted (C1-C30) -alkoxy or can be combined with one or more adjacent R ₁₀₀ to R ₁₀₃ to a substituted or unsubstituted fused ring with a pyridine, e.g. B. a substituted or unsubstituted quinoline, a substituted or unsubstituted isoquinoline, a substituted or unsubstituted benzofuropyridine, a substituted or unsubstituted benzothienopyridine, a substituted or unsubstituted indenopyridine, a substituted or unsubstituted benzofurochinoline, a or a substituted or unsubstituted indenoquinoline ring;
R ₁₀₄ to R ₁₀₇ each independently represent hydrogen, deuterium, a halogen, a (C1-C30) -alkyl which is unsubstituted or substituted by deuterium or a halogen, a substituted or unsubstituted (C3-C30) -cycloalkyl, a substituted one or unsubstituted (C6-C30) -aryl, a substituted or unsubstituted (3 to 30-membered) heteroaryl, a cyano or a substituted or unsubstituted (C1-C30) -alkoxy or can be combined with one or more adjacent R ₁₀₄ to R ₁₀₇ to a substituted or unsubstituted fused ring with a benzene, e.g. B. a substituted or unsubstituted naphthalene, a substituted or unsubstituted fluorene, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted indenopyridine, a substituted or unsubstituted benzofuropyridine, unsubstituted or unsubstituted benzofuropyridine or be linked.
R ₂₀₁ to R ₂₂₀ each independently represent hydrogen, deuterium, a halogen, a (C1-C30) -alkyl which is unsubstituted or substituted by deuterium or a halogen, a substituted or unsubstituted (C3-C30) -cycloalkyl or a substituted one or unsubstituted (C6-C30) -aryl or can be linked to one or more adjacent of adjacent R ₂₀₁ to R ₂₂₀ to form a substituted or unsubstituted fused ring; and
n stands for an integer from 1 to 3.

The specific examples of the dopant compound are as follows, but are not limited thereto.

The organic electroluminescent device according to the present disclosure includes a first electrode, a second electrode, and at least one organic layer between the first and second electrodes.

One of the first and second electrodes can be an anode and the other can be a cathode. The organic layer may comprise a light emitting layer and may further comprise at least one selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, an light emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer and an electron blocking layer. Each of the layers can also consist of several layers.

The first electrode and the second electrode can each be formed with a transmissive conductive material, transflective conductive material or reflective conductive material. The organic electroluminescent device may be of a top emission type, a bottom emission type, or a double emission type according to the types of the material from which the first electrode and the second electrode are formed. In addition, the hole injection layer can furthermore be doped with a p-type dopant and the electron injection layer can furthermore be doped with an n-type dopant.

The organic layer can further comprise at least one compound selected from the group consisting of arylamide-based compounds and styrylarylamine-based compounds.

In addition, the organic layer in the organic electroluminescent device of the present disclosure may further include at least one metal selected from the group consisting of Group 1 metals, Group 2 metals, 4th period transition metals, 5th period transition metals, lanthanides, and organic metals of d Transition elements of the periodic table or at least one complex compound comprising the metal.

The organic electroluminescent device of the present disclosure can emit white light by further including at least one light emitting layer including a blue, red, or green light emitting compound known in the art. In addition, it can optionally further contain a yellow or orange-colored light-emitting layer.

In the organic electroluminescent device of the present disclosure, preferably at least one layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter, “a surface layer”) may be disposed on an inner surface of one or both of the electrodes. Specifically, a layer of chalcogenides (including oxides) of silicon or aluminum is preferably disposed on an anode surface of a layer of an electroluminescent medium, and a metal halide layer or a metal oxide layer is preferably disposed on a cathode surface of a layer of electroluminescent medium. The surface layer can provide operational stability of the organic electroluminescent device. Preferably, the chalcogenide includes SiOx (1 X 2), AlOx (1 X 1.5), SiON, SiAlON, etc .; the metal halide includes LiF, MgF ₂ , CaF ₂ , a rare earth metal fluoride, etc., and the metal oxide includes Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO and so on.

A hole injection layer, a hole transport layer, or an electron blocking layer, or a combination thereof, can be used between the anode and the light emitting layer. In order to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer, the hole injection layer can be formed in a multilayered manner, it being possible for two compounds to be used simultaneously in each of the several layers. The hole transport layer or the electron blocking layer can also have a multilayer design.

An electron buffer layer, a hole blocking layer, an electron transport layer or 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 multilayered in order to control electron injection and improve the interface properties between the light emitting layer and the electron injection layer, and two compounds can be used simultaneously in each of the plural layers. The hole blocking layer or the electron transport layer can also be formed in a multilayered manner, it being possible for a plurality of compounds to be used in each of the plurality of layers.

The light-emitting auxiliary layer can be arranged between the anode and the light-emitting layer or between the cathode and the light-emitting layer. When the auxiliary light-emitting layer is arranged between the anode and the light-emitting layer, it can be used to promote hole injection and / or hole transport or to prevent electrodes from overflowing. When the auxiliary light-emitting layer is arranged between the cathode and the light-emitting layer, it can be used to promote electron injection and / or electron transport or to prevent holes from overflowing. In addition, the hole auxiliary layer may be disposed between the hole transport layer (or hole injection layer) and the light emitting layer and promote or block the hole transport rate (or the hole injection rate), whereby the charge balance can be controlled. Further, the electron blocking layer may be disposed between the hole transport layer (or hole injection layer) and the light emitting layer and block overflowing electrons from the light emitting layer and restrict the excitons in the light emitting layer to prevent light leakage. When an organic electroluminescent device contains two or more hole transport layers, the hole transport layer further included can be used as a hole assist layer or an electron blocking layer. The auxiliary light-emitting layer, the auxiliary hole layer or the electron blocking layer can improve the efficiency and / or the service life of the organic electroluminescent device.

In the organic electroluminescent device of the present disclosure, a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant is preferably disposed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, making it easier to inject and transport electrons from the mixed region into an electroluminescent medium. Furthermore, the hole transport compound is oxidized to a cation, making it easier to inject and transport holes from the mixed region into the electroluminescent medium. Preferably, the oxidative dopant includes various Lewis acid and acceptor compounds, and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. A layer of reductive dopant can be used as a charge generating layer to fabricate an organic electroluminescent device that has two or more light emitting layers and that emits white light.

An organic electroluminescent material according to an embodiment of the present disclosure can be used as a light emitting material for a white organic light emitting device. For the white organic light emitting device, various structures have been proposed such as a parallel arrangement method, a stacking method or a color conversion material (CCM) method, etc., according to the arrangement of red (R), green (G) , or yellowish-green (YG), blue (B) light-emitting units. In addition, the organic electroluminescent material according to an embodiment of the present disclosure can also be applied to the organic electroluminescent device including a quantum dot (QD).

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, etc., or wet film formation methods such as ink jet printing, nozzle printing, spray coating, spin coating, dip coating, flooding, etc. can be used. The first and second host compounds of the present disclosure can be co-evaporated or evaporated as a mixture.

Using a wet film forming method, by dissolving or diffusing the materials forming each layer in a suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc., a thin film can be formed. The solvent is not particularly limited as long as the material constituting each layer is soluble or dispersible in the solvents, which does not cause any problem of film formation.

It is possible to use the organic electroluminescent device of the present disclosure to display a display system, e.g. B. a display system for smartphones, tablets, notebooks, PCs, televisions or cars, or a lighting system, e.g. B. an outdoor or indoor lighting system.

In the following, the production method of the compound of the present invention and the properties thereof will be explained in detail with reference to the representative compounds of the present disclosure. However, the present disclosure is not limited to the following examples.

Example 1: Preparation of Compound C-1

1) Synthesis of Compound 1-1

In a flask, 96 g of (9-phenyl-9H-carbazol-4-yl) boronic acid (334.3 mmol), 71.8 g of 2-bromo-1-chloro-3-nitrobenzene (304 mmol), 15 g of Pd ₂ (dba) ₃ (16.71 mmol), 10.9 g of S-Phos (26.76 mmol) and 315 g of K ₃ PO ₄ (1.64 mol) were dissolved in 1500 ml of toluene, after which the mixture was added for 4 hours 130 ° C was stirred. After the completion of the reaction, the organic layer was washed with ethyl acetate and the remaining moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography, which gave 67 g of Compound 1-1 (yield: 56.6%).

2) Synthesis of Compound 1-2

In a flask were 23.5 g of compound 1-1 (58.9 mmol), 18.4 g (2-chlorophenyl) boronic acid (117.8 mmol), 2.7 g of Pd ₂ (dba) ₃ (2.95 mmol), 2.4 g of S-Phos (5.89 mmol) and 63 g of K ₃ PO ₄ (294.5 mol) were dissolved in 300 ml of toluene, after which the mixture was stirred at 130 ° C. for 12 hours. After completion of the reaction, an organic layer was extracted with ethyl acetate and the residual moisture was removed with magnesium sulfate. The residue was dried and separated by column chromatography, giving 14 g of Compound 1-2 (yield: 50%).

3) Synthesis of Compound 1-3

In a flask, 13 g of compound 1-2 (27.4 mmol) and 21.5 g of triphenylphosphine (82.1 mmol) were dissolved in 140 ml of o-DCB, after which the mixture was stirred at 220 ° C. for 7 hours. After the completion of the reaction, the reaction was distilled off and the residue was then separated by column chromatography, giving 4 g of Compound 1-3 (yield: 32%).

4) Synthesis of Compound 1-4

In a flask were 10 g of compound 1-3 (22.5 mmol), 505 mg of Pd (OAc) ₂ (2.25 mmol), 1.63 g of Pcy ₃ -HBF ₄ (4.5 mmol) and 22 g of Cs ₂ CO ₃ (67.5 mmol) dissolved in 113 ml of o-xylene, after which the mixture was stirred at 160 ° C. for 4 hours. After the completion of the reaction, the organic layer was washed with ethyl acetate and the remaining moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography, which gave 1 g of Compound 1-4 (yield: 11%).

5) Synthesis of Compound C-1

In a flask were 4.5 g of compound 1-4 (11.06 mmol), 4 g of 2-chloro-3-phenylquinoxaline (16.6 mmol), 67 mg of DMAP (0.553 mmol) and 10.8 g of Cs ₂ CO ₃ (331.8 mmol) dissolved in 60 ml of DMSO, after which the Mixture was refluxed for 4 hours at 140 ° C. After completion of the reaction, an organic layer was extracted with ethyl acetate and the residual moisture was removed with magnesium sulfate. The residue was dried and separated by column chromatography, which gave 2.5 g of Compound C-1 (yield: 37%). MG Fp. C-1 610.22 246 ° C

Example 2: Preparation of Compound C-29

4 g of compound 1-4 (9.84 mmol), 3.65 g of 3-bromo-1,1 ': 2', 1 "-terphenyl (11.8 mmol), 448 g of Pd ₂ (dba ) ₃ (0.492 mmol), 448 g of S-Phos (0.984 mmol) and 2.84 g of NaOtBu (29.52 mol) were dissolved in 50 ml of o-xylene, after which the mixture was stirred at 170 ° C. for 4 hours After the reaction, the organic layer was washed with ethyl acetate and the remaining moisture was removed by using magnesium sulfate, and the residue was dried and separated by column chromatography to give 1.5 g of Compound C-29 (yield: 24%). MG Fp. C-29 643.78 282 ° C

Example 3: Preparation of Compound C-196

1) Synthesis of Compound 3-1

60 g of compound A (283 mmol), 100 g of compound B (424 mmol), 16.3 g of tetrakis (triphenylphosphine) palladium (14.1 mmol), 276 g of cesium carbonate (849 mmol), 1400 ml of toluene, 350 g were placed in a reaction vessel ml of ethanol and 350 ml of distilled water were added, after which the mixture was stirred at 130 ° C. for 12 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and an organic layer was extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed on a rotary evaporator. The residue was separated by column chromatography, which gave 38 g of Compound 3-1 (yield: 41%).

2) Synthesis of Compound 3-2

38 g of compound 3-1 (117 mmol), 35 g of phenylboronic acid (234 mmol), 5.3 g of tris (dibenzylidene acetone) dipalladium (5.86 mmol), 4.8 g of S-Phos (11.7 mmol), 62 g of tripotassium phosphate (293 mmol), and 600 ml of toluene were added, after which the mixture was stirred under reflux for 2 hours. After the completion of the reaction, the reaction mixture was washed with distilled water and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed on a rotary evaporator. The residue was separated by column chromatography, which gave 31 g of Compound 3-2 (yield: 67%).

3) Synthesis of Compound 3-3

Into a reaction vessel were added 21 g of Compound 3-2 (53.7 mmol), 70 ml of triphenyl phosphite (268 mmol), and 180 ml of DCB, and the mixture was stirred at 200 ° C for 12 hours. After the completion of the reaction, the mixture was distilled under reduced pressure to remove DCB. Then the reaction mixture was washed with distilled water and an organic layer was extracted with ethyl acetate. The organic layer was dried with magnesium sulfate and the solvent removed on a rotary evaporator. The residue was separated by column chromatography, giving 10 g of Compound 3-3 (yield: 55%).

4) Synthesis of Compound 3-4

6.6 g of compound 3-3 (17.9 mmol), 0.2 g of palladium (II) acetate (0.89 mmol), 1.3 g of PCy3-BF4 (3.58 mmol), 17 g of cesium carbonate (53.7 mmol) and 90 ml of o-xylene were added, after which the mixture was stirred under reflux at 160 ° C. for 4 hours. After the completion of the reaction, the reaction mixture was washed with distilled water and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed on a rotary evaporator. The residue was separated by column chromatography, which gave 1.8 g of Compound 3-4 ((yield: 32%).

5) Synthesis of Compound C-196

In a reaction vessel were 1.8 g of compound 3-4 (5.43 mmol), 2.3 g of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (5.97 mmol), 0.2 g tris (dibenzylideneacetone) dipalladium (0.27 mmol), 0.3 ml tri-tert-butylphosphine (0.54 mmol), 1.3 g sodium tert-butoxide (13.5 mmol) and 30 ml Added toluene, after which the mixture was stirred under reflux for 3 hours. After the completion of the reaction, the reaction mixture was washed with distilled water and the organic layer was extracted with ethyl acetate. The organic layer was dried with magnesium sulfate and the solvent removed on a rotary evaporator. The residue was separated by column chromatography, which gave 3.3 g of Compound C-196 ((yield: 95%). MG UV PL Fp. C-196 638.21 410nm 522nm 240 ° C

Example 4: Preparation of Compound C-36

4.0 g of compound 1-4 (9.84 mmol), 3.2 g of 4-bromo-N, N-diphenylaniline (9.84 mmol), 0.45 g of Pd ₂ (dba) ₃ ( 0.5 mmol), 0.4 g of S-Phos (0.98 mmol) and 1.9 g of NaOtBu (19.7 mmol) were dissolved in 50 ml of o-xylene, after which the mixture was stirred under reflux for 5 hours. After the completion of the reaction, the organic layer was extracted with ethyl acetate. The residue was separated by column chromatography, which gave 2.67 g of Compound C-36 (yield: 42%). MG Fp. C-36 649.78 312 ° C

Example 5: Preparation of Compound C-32

4.0 g of compound 1-4 (9.84 mmol), 1.7 g of 2-bromodibenzo [b, d] furan (9.84 mmol), 0.45 g of Pd ₂ (dba) ₃ ( 0.5 mmol), 0.4 g of S-Phos (0.98 mmol) and 1.9 g of NaOtBu (19.7 mmol) were dissolved in 50 ml of o-xylene, after which the mixture was stirred under reflux for 5 hours. After the completion of the reaction, the organic layer was extracted with ethyl acetate. The residue was separated by column chromatography, which gave 1.68 g of Compound C-32 (yield: 30%). MG Fp. C-32 572.65 291 ° C

Device Examples 1-1 and 1-2: Manufacture of an OLED with deposition of a compound according to the present disclosure as a host

An OLED according to the present disclosure was manufactured as follows: A transparent thin electrode layer made of indium tin oxide (ITO) (10 Ω / sq) on a glass substrate for an OLED (GEOMATEC CO., LTD., Japan) was successively ultrasonic washing with acetone, ethanol and Subjected to distilled water and then stored in isopropanol. The ITO substrate was placed on a substrate holder attached to a vacuum vapor deposition apparatus. Compound HI-1 was placed in a cell of the vacuum vapor deposition apparatus, after which the pressure in the chamber of the apparatus was ^{adjusted to 10 -6} Torr. Thereafter, an electric current was applied to the cell to evaporate the above-charged material, thereby forming a first hole injection layer having a thickness of 80 nm on the ITO substrate. Next, Compound HI-2 was placed in another cell of the vacuum vapor deposition apparatus and evaporated by applying an electric current to the cell, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer. Then, Compound HT-1 was placed in another cell of the vacuum vapor deposition apparatus and evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer. Then, Compound HT-2 was placed in another cell of the vacuum vapor deposition apparatus and evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer. After the formation of the hole injection layers and the hole transport layers, a light emitting layer was formed thereon as follows: The host shown in Table 1 was put in a cell of the vacuum vapor deposition apparatus as a host, and Compound D-39 was put in another cell as a dopant. The two materials were evaporated at different rates, and the dopant was deposited in a doping amount of 3 wt% based on the total amount of the host and the dopant to form a light emitting layer with a thickness of 40 nm on the second hole transport layer form. Next, Compound ET-1 and Compound EI-1 were evaporated at a rate of 1: 1 in two other cells to deposit an electron transport layer with a thickness of 35 nm on the light-emitting layer. After Compound E1-1 was deposited as an electron injection layer with a thickness of 2 nm on the electron transport layer, an Al cathode with a thickness of 80 nm was deposited on the electron injection layer using another vacuum vapor deposition apparatus. This is how an OLED was made.

Comparative Example 1-1: Production of an OLED with the deposition of a comparative compound as host

An OLED was manufactured in the same manner as in Device Example 1-1, except that Compound A was used as the host of the light-emitting layer.

The results for the operating voltage, the luminous efficiency and the CIE color coordinates at a luminance of 1000 nit and the time until the luminance is reduced from 100% to 95% at a luminance of 5500 nit (service life; T95) of the device examples 1- OLEDs produced 1 and 1-2 and Comparative Example 1-1 are shown in Table 1 below. [Table 1] host Operating voltage [V] Light output [cd / A] CIE Lifetime (T95) [h] × y Comparative example 1-1 A. 9.0 12.5 0.651 0.342 0.3 Device example 1-1 C-196 3.1 18.2 0.657 0.342 13.9 Device example 1-2 C-1 3.2 27.1 0.659 0.341 91.6

It can be seen from Table 1 that the OLED comprising the organic electroluminescent compound according to the present disclosure as a host has a lower operating voltage, a higher luminous efficiency and a longer service life than the OLED comprising the comparative compound of the comparative example.

Without wishing to be bound by any theory, it is understood that the compound of the present disclosure has a rigid planar structure, thereby reducing the energy of steric hindrance. In addition, it is understood that the compound of the present disclosure can not only increase hole stability in an OLED, but also increase hole mobility by increasing HOMO energy levels, thereby achieving charge balance.

Device Example 2-1: Production of an OLED with Deposition of Multiple Host Materials According to the Present Disclosure

An OLED was fabricated in the same manner as in Device Example 1-1, except that a transparent indium tin oxide (ITO) (10 Ω / sq) electrode thin film on a glass substrate for an OLED (GEOMATEC CO., LTD., Japan) was one by one Was subjected to ultrasonic washing with acetone, trichlorethylene, ethanol and distilled water and then stored in isopropanol and a light emitting layer was formed as follows: The first and second host compounds shown in Table 2 below were introduced into the two cells of the vacuum vapor deposition apparatus as hosts, and Compound D -39 was introduced into another cell as a dopant. The two host materials were evaporated at a rate of 1: 1, and at the same time the dopant material was evaporated at a different rate and the dopant was evaporated in a doping amount of 3 wt% based on the total amount of the hosts and the dopant around a light emitting layer with a thickness of 40 nm on the second hole transport layer.

Comparative Example 2-1: Production of an OLED with the deposition of a comparative compound as host

An OLED was manufactured in the same manner as in Device Example 2-1, except that the compound shown in Table 2 below was used as the host of the light-emitting layer.

The results for the luminous efficiency and its rate of increase and the time to reduce the luminance from 100% to 97% at a luminance of 5,000 nit (lifetime; T97) of the OLEDs produced in device example 2-1 and comparative example 2-1 are shown in the table below 2 specified. [Table 2] First host Second host Light output [cd / A] Rate of increase in yield [%] Lifetime (T97) [h] Comparative Example 2-1 - H-2 17.8 - 24 Device example C-29 H-2 29.6 66 267 2-1

Device examples 3-1 and 3-2: Production of a red OLED with the deposition of several host materials according to the present disclosure

An OLED according to the present disclosure was manufactured as follows: A transparent thin electrode layer made of indium tin oxide (ITO) (10 Ω / sq) on a glass substrate for an OLED (GEOMATEC CO., LTD., Japan) was successively subjected to ultrasonic washing with acetone and isopropyl alcohol and then stored in isopropyl alcohol. The ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-3 shown in Table 4 below was put in one cell of the vacuum vapor deposition apparatus, and Compound HT-1 shown in Table 4 below was put in another cell of the vacuum vapor deposition apparatus. The two materials were evaporated at different rates, and Compound HI-3 was deposited in a doping amount of 3% by weight based on the total amount of Compound HI-3 and Compound HT-1 to form a first hole injection layer having a thickness of 10 nm on the ITO substrate. Next, Compound HT-1 was deposited on the first hole injection layer to form a first hole transport layer with a thickness of 80 nm. Then, Compound HT-2 was placed in another cell of the vacuum vapor deposition apparatus and evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer. After the formation of the hole injection layer and the hole transport layers, a light emitting layer was formed thereon as follows: The first host compound and the second host compound as shown in Table 3 below were placed in two cells of the vacuum vapor deposition apparatus as hosts, and Compound D-39 was placed in another Cell introduced. The two host materials were evaporated at a rate of 1: 1, and at the same time the dopant material was evaporated at a different rate and the dopant was evaporated in a doping amount of 3 wt% based on the total amount of the hosts and the dopant around a light emitting layer with a thickness of 40 nm on the second hole transport layer. Next, Compound ET-1 and Compound EI-1 as electron transport materials were evaporated in a weight ratio of 50:50, to form an electron transport layer with a thickness of 35 nm on the light emitting layer. After Compound EI-1 was deposited as an electron injection layer with a thickness of 2 nm on the electron transport layer, an Al cathode with a thickness of 80 nm was deposited on the electron injection layer using another vacuum vapor deposition apparatus. This is how an OLED was made. Each compound was used for each material after purification by vacuum sublimation under 10 ^{-6 torr.}

The results for the operating voltage, the luminous efficiency and the luminous color at a luminance of 1000 nit and the time until the luminance is reduced from 100% to 95% at a luminance of 5500 nit (service life; T95) of the device examples 3-1 and 3-2 produced OLEDs are shown in Table 3 below. [Table 3] First he host Second he host Operating voltage [V] Light output [cd / A] Luminous color Lifetime (T95) [h] Device example 3-1 C-36 H-2 3.0 30.8 Red 308 Device example 3-2 C-32 H-2 3.1 33.2 Red 705

It can be seen from Tables 2 and 3 that the OLEDs which comprise a specific combination of compounds according to the present disclosure as host material have a significantly improved efficiency and service life compared to conventional OLEDs.

Lichtemittierende Schicht

Elektronentransportschicht/ Elektroneninjektionsschicht

The compounds used in the device examples and the comparative examples are shown in Table 4 below. [Table 4] Hole injection layer / hole transport layer

Light emitting layer

Electron transport layer / electron injection layer

QUOTES INCLUDED IN THE DESCRIPTION

This list of the documents listed by the applicant was generated automatically and is included solely for the better information of the reader. The list is not part of the German patent or utility model application. The DPMA assumes no liability for any errors or omissions.

Non-patent literature cited

• Appl. Phys. Lett. 51, 913, 1987 [0002]

Claims (10)

Organic electroluminescent compound represented by Formula 1 below:

wherein B ₁ to B _{7 are} each independently absent or represent a substituted or unsubstituted (C5-C20) ring in which the carbon atom of the ring has been replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur can; with the proviso that there are at least five of B ₁ to B ₇ and the adjacent rings of B ₁ to B ₇ are fused to one another; Y is -NL ₁ - (Ar ₁ ) n, -O-, -S- or -CR ₁ R ₂ ; L _{1 stands} for a single bond, a substituted or unsubstituted (C1-C30) -alkylene, a substituted or unsubstituted (C6-C30) -arylene, a substituted or unsubstituted (3- to 30-membered) heteroarylene or a substituted or unsubstituted (C3 -C30) -cycloalkylene; Ar _{1 represents} a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl or -NR ₃ R ₄ ; R ₁ to R ₄ each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C6-C30) -aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl or a substituted or unsubstituted (C3-C30) -cycloalkyl or can be linked to one or more adjacent substituents to form one or more rings; and n is an integer with a value of 1 or 2; wherein when n is 2, each of Ar _{1 may be the} same as or different from one another. Organic electroluminescent compound according to Claim 1 , where B ₁ to B _{7 are} each independently absent or represent a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted pyrrole ring, a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring, a substituted or unsubstituted cyclopentadiene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted pyridine ring, or a substituted or unsubstituted dibenzofuran ring; with the proviso that there are at least five of B ₁ to B ₇ and the adjacent rings of B ₁ to B ₇ are fused to one another. Organic electroluminescent compound according to Claim 1 , where Formula 1 is represented by one of the following formulas 1-1 to 1-5:

where Y ₁ , Y ₂ , Y ₃ and Y ₄ each independently of the definition of Y Claim 1 and wherein when a plurality of Ar ₁ are present, each of Ar _{1 may be the} same as or different from one another; X ₁ to X ₁₂ each independently represent -N = or -C (R _a ) =; and R _a each independently represents hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C6-C30) -aryl, a substituted or unsubstituted (3- to 30- membered) heteroaryl or a substituted or unsubstituted (C3-C30) -cycloalkyl or adjacent R _a can be linked to one another to form one or more rings; and when plural R _a are present, each of R _{a may be the} same as or different from each other. Organic electroluminescent compound according to Claim 3 , where at least one of the variables Ar ₁ and R _{a is} selected from those listed in the following group 1:

wherein in Group 1 D1 and D2 each independently represent a benzene ring or a naphthalene ring; X _{21 represents} O, S, NR ₅ or CR ₆ R ₇ ; X ₂₂ each independently represents CR ₈ or N; provided that at least one of X _{22 is} N; X ₂₃ each independently represents CR ₉ or N; L ₁₁ to L ₁₈ each independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene; R ₁₁ to R ₂₁ and R ₅ to R ₉ each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C6-C30) -aryl, a substituted one or unsubstituted (3- to 30-membered) heteroaryl or a substituted or unsubstituted (C3-C30) -cycloalkyl or can be linked to one or more adjacent substituents to form one or more rings; aa, ff, and gg each independently represent an integer from 1 to 5; bb stands for an integer from 1 to 7 and cc, dd and ee each independently stand for an integer from 1 to 4. Organic electroluminescent compound according to Claim 3 , wherein the substituents of the substituted (C1-C30) -alkyl (en) s, the substituted (C6-C30) -aryl (en) s, the substituted (3- to 30-membered) heteroaryl (en) s and the substituted (C3-C30) -cycloalkyl (en) s in An ₁ , L ₁ , R ₁ to R ₄ and R _a each independently by at least one from the group consisting of deuterium; a halogen; a cyano; a carboxyl; a nitro; a hydroxyl; a (C1-C30) alkyl; a halo (C1-C30) alkyl; a (C2-C30) alkenyl; a (C2-C30) alkynyl; a (C1-C30) alkoxy; a (C1-C30) -alkylthio; a (C3-C30) cycloalkyl; a (C3-C30) cycloalkenyl; a (3-7 membered) heterocycloalkyl; a (C6-C30) aryloxy; a (C6-C30) arylthio; a (C6-C30) -aryl which is unsubstituted or substituted by at least one selected from the group consisting of deuterium and one or more (3 to 30-membered) heteroaryl; a (3- to 30-membered) heteroaryl which is unsubstituted or substituted by one or more (C6-C30) -aryl; a tri- (C1-C30) -alkylsilyl; a tri- (C6-C30) -arylsilyl; a di- (C1-C30) -alkyl- (C6- C30) arylsilyl; a (C1-C30) -alkyldi (C6-C30) -arylsilyl; an amino; a mono- or di- (C1-C30) -alkylamino; a mono- or di- (C6-C30) -arylamino which is unsubstituted or substituted by one or more (C1-C30) -alkyl; a (C1-C30) -alkyl- (C6-C30) -arylamino; a (C1-C30) -alkylcarbonyl; a (C1-C30) alkoxycarbonyl; a (C6-C30) arylcarbonyl; a di (C6-C30) arylboronyl; a di- (C1-C30) -alkylboronyl; a (C1-C30) -alkyl- (C6-C30) -arylboronyl; a (C6-C30) -aryl- (C1-C30) -alkyl and a (C1-C30) -alkyl- (C6-C30) -aryl. Organic electroluminescent compound according to Claim 3 Wherein at least one of the variables Ar and R _{1 a} is selected from those which are listed in the following Groups 2 and 3:

in group 2 L stands for a single bond, a substituted or unsubstituted (C1-C30) -alkylene, a substituted or unsubstituted (C6-C30) -arylene, a substituted or unsubstituted (3- to 30-membered) heteroarylene or a substituted or unsubstituted one (C3-C30) cycloalkylene; and A ₁ to A ₃ each independently represent a substituted or unsubstituted (C1-C30) -alkyl or a substituted or unsubstituted (C6-C30) -aryl. Organic electroluminescent compound according to Claim 1 , wherein the compound represented by formula 1 is selected from the group consisting of the following compounds:

A plurality of host materials comprising a first host material and a second host material, the first host material being the compound represented by Formula 1 after Claim 1 and the second host material comprises an organic electroluminescent compound other than the compound represented by Formula 1. Several host materials after Claim 8 wherein the second host material comprises a compound represented by Formula 11 below:

where HAr _{b represents} a substituted or unsubstituted (3- to 30-membered) heteroaryl; L _{b1 represents} a single bond, a substituted or unsubstituted (C6-C30) -arylene or a substituted or unsubstituted (3 to 30-membered) heteroarylene; R _b1 and R _b2 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C6-C30) -aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30) -cycloalkyl, a substituted or unsubstituted (C1-C30) -alkoxy, a substituted or unsubstituted tri- (C1-C30) -alkylsilyl, a substituted or unsubstituted di- (C1-C30) -alkyl- (C6-C30) -arylsilyl, a substituted or unsubstituted (C1-C30) -alkyldi (C6-C30) -arylsilyl, a substituted or unsubstituted tri- (C6-C30) -arylsilyl, a substituted or unsubstituted mono- or di- (C1-C30) -alkylamino, a substituted or unsubstituted mono- or di- (C6-C30) -arylamino or a substituted or unsubstituted (C1-C30) -alkyl- (C6-C30 ) -arylamino or with one or more adjacent substituents to one or more Ri can be linked; a is an integer from 1 to 4 and b is an integer from 1 to 6; wherein when a and b each independently represent an integer having a value of 2 or more, each of R _b1 and each of R _{b2 may be the} same or different from each other. An organic electroluminescent device comprising the organic electroluminescent compound of Claim 1 .