Organic electroluminescent compounds and organic electroluminescent devices containing the same

Abstract

To provide an organic electro-luminescent compound and an organic electro-luminescent device including the same.SOLUTION: The present disclosure relates to an organic electro-luminescent compound and an organic electro-luminescent device including the same. The organic electro-luminescent device having an improved drive voltage and / or improved power efficiency can be provided by using the organic electro-luminescent compound according to the present disclosure.SELECTED DRAWING: None

Description

[Technical Field]

[0001] This disclosure relates to organic electroluminescent compounds and organic electroluminescent devices containing the same. [Background technology]

[0002] Electroluminescent devices (EL devices) are self-emissive display devices that offer advantages such as wider viewing angles, higher contrast ratios, and faster response times. In 1987, Eastman Kodak developed the first organic EL device by using small aromatic diamine molecules and aluminum complexes as materials to form the emissive layer (see Appl. Phys. Lett. 51, 913, 1987).

[0003] Organic electroluminescent devices have a multilayer structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer to improve their efficiency and stability. In this case, the selection of compounds included in the hole transport layer, etc., is recognized as one means of improving device characteristics such as hole transport efficiency to the light-emitting layer, light emission efficiency, and lifetime.

[0004] In this regard, copper phthalocyanine (CuPc), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TPD), and 4,4',4''-tris(3-methylphenylamino)triphenylamine (MTDATA) have been used as hole injection and transport materials in organic electroluminescent devices. However, when such materials are used, there is a problem in that the quantum efficiency and lifetime of the organic electroluminescent device deteriorates. This is because when organic electroluminescent devices are driven with high current, thermal stress occurs between the anode and the hole injection layer, and such thermal stress significantly reduces the lifespan of the device. In addition, the holes in the organic materials used in the hole injection layer have very high mobility, which disrupts the hole-electron charge balance, thereby reducing the quantum efficiency (cd / A).

[0005] Therefore, there is still a need to develop hole transport materials that improve the performance of organic electroluminescent devices.

[0006] (Patent Document 1) discloses phenanthrene derivatives, but does not specifically disclose organic electroluminescent compounds according to this disclosure. [Prior art documents] [Patent Documents]

[0007] [Patent Document 1] Korean Patent Application Publication No. 1756611 Specification [Overview of the project] [Problems that the invention aims to solve]

[0008] The object of this disclosure is, firstly, to provide an organic electroluminescent compound effective for preparing an organic electroluminescent device having improved drive voltage and / or power efficiency characteristics, and secondly, to provide an organic electroluminescent device comprising the organic electroluminescent compound. [Means for solving the problem]

[0009] As a result of intensive research to solve the above technical problems, the inventors have come up with the following formula 1 [ka] (In the formula, R3 to R6 are, independently, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3 to 30 member) heteroaryl, substituted or unsubstituted (C3 to C30) cycloalkyl, substituted or unsubstituted (C1 to C30) alkoxy, substituted or unsubstituted tri(C1 to C30) alkylsilyl, substituted or unsubstituted di(C1 to C30) alkyl(C6 to C30) arylsilyl, substituted or unsubstituted (C1 to C30) alkyldi(C6 to C30) arylsilyl, substituted or unsubstituted tri(C6 to C30) arylsilyl, or the following formula A [ka] Represents the base represented by; At least two of R3 to R6 can be expressed independently by formula A, provided that R3 and R6 cannot both be expressed by A at the same time; L' independently represents a single bond, a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3-30 member) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene; Ar' and Ar'' each independently represent a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 member) heteroaryl, or a substituted or unsubstituted fused ring of an (C3-C30) aliphatic ring and a (C6-C30) aromatic ring; R1 and R2 may independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) 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 tri(C6-C30) arylsilyl, or -L3-N-(Ar5)(Ar6), or be linked to adjacent substituents to form a ring; L3 independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 member) heteroarylene; Ar5 and Ar6 independently represent hydrogen, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30) alkenyl, a substituted or unsubstituted condensed ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl; If a is an integer between 1 and 4, and b is 1 or 2, and a and b are each integers greater than or equal to 2, then R1 and R2 may be the same or different from each other; and If there are multiple substituents represented by the same symbol, each substituent represented by the same symbol may be identical or different from one another. The present invention was completed by finding that an organic electroluminescent compound represented by achieves the above objective.

[0010] Advantageous effects of the invention The present disclosure provides an organic electroluminescent device having improved driving voltage and / or power efficiency characteristics by using an organic electroluminescent compound according to the present disclosure.

Mode for Carrying Out the Invention

[0011] Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present invention and does not mean to limit the scope of the present invention.

[0012] The term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device and can be included in any layer constituting the organic electroluminescent device as needed.

[0013] The term "organic electroluminescent material" in the present disclosure means a material that can be used in an organic electroluminescent device and can contain at least one compound. The organic electroluminescent material can be included in any layer constituting the organic electroluminescent device as needed. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, a light emission auxiliary material, an electron blocking material, a light emitting material, an electron buffer material, a hole blocking material, an electron transport material or an electron injection material.

[0014] The organic electroluminescent material of the present disclosure can contain one or more types of compounds represented by Formula 1. The compound of Formula 1 can be included in one or more layers constituting the organic electroluminescent device and can be included in at least one layer of the layer constituting the hole transport band, but is not limited thereto. When the compound of Formula 1 is included in the hole transport layer, the hole auxiliary layer, the light emission auxiliary layer or the electron blocking layer, it can be included as a hole transport material, a hole auxiliary material, a light emission auxiliary material or an electron blocking material.

[0015] Hereinafter, the compound represented by Formula 1 will be described in more detail.

[0016] In this specification, the term "(C1-C30) alkyl" means a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, where the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10. Examples of the alkyls mentioned above include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, and the like. The term "(C2-C30) alkenyl" means a linear or branched alkenyl having 2 to 30 carbon atoms constituting the chain, where the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10. Examples of the alkenyls mentioned above include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbuta-2-enyl, and the like. The term "(C2~C30) alkynyl" refers to a linear or branched alkynyl having 2 to 30 carbon atoms constituting the chain, where the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10. Examples of the above alkynyls include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpenta-2-inyl, etc. The term "(C3~C30) cycloalkyl" refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms in the ring skeleton, where the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7. Examples of the above cycloalkyls include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, etc. The term "(3-7 member) heterocycloalkyl" means a cycloalkyl having 3 to 7, preferably 5 to 7, ring skeleton atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably at least one heteroatom selected from the group consisting of O, S, and N. Examples of the above heterocycloalkyls include tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, etc. The terms "(C6-C30) aryl(lene)" or "(C6-C50) aryl(lene)" may be partially saturated.This means a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 or 6 to 50 carbon atoms in its ring skeleton. The number of carbon atoms in the ring skeleton is preferably 6 to 25, more preferably 6 to 18. The above aryls include those having a spiro structure. Examples of the above aryls include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenantrenyl, phenylphenantrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracerenyl, perilenyl, crisenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, azlenyl, tetramethyldihydrophenantrenyl, and the like. More specifically, the aryl compounds mentioned above include 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-crisenyl, 2-crisenyl, 3-crisenyl, 4-crisenyl, 5-crisenyl, 6-crisenyl, benzo[c]phenanthryl, benzo[g]crisenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo[a]fluorenyl, benzo[b]fluorenyl Renyl, benzo[c]fluorenyl, 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-fluorenyl, 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, 11,11-dimethyl-1-benzo[a]fluorenyl, 11,11-dimethyl-2-benzo[a]fluorenyl, 11,11-dimethyl 3-benzo[a]fluorenyl, 11,11-dimethyl-4-benzo[a]fluorenyl, 11,11-dimethyl-5-benzo[a]fluorenyl, 11,11-dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 11,11-dimethyl-10-benzo[a]fluorenyl, 11,11-dimethyl-1-benzo[b]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl 11,11-dimethyl-3-benzo[b]fluorenyl, 11,11-dimethyl-4-benzo[b]fluorenyl, 11,11-dimethyl-5-benzo[b]fluorenyl, 11,11-dimethyl-6-benzo[b]fluorenyl, 11,11-dimethyl-7-benzo[b]fluorenyl, 11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[b]fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl-2 -Benzo[c]fluorenyl, 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c]fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]fluorenyl, 11,11-dimethyl-9-benzo[c]fluorenyl, 11,11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl,11,11-diphenyl-2-benzo[a]fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl, 11,11-diphenyl-4-benzo[a]fluorenyl, 11,11-diphenyl-5-benzo[a]fluorenyl, 11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl, 11,11-diphenyl-8-benzo[a]fluorenyl, 11,11-diphenyl-9-benzo[a]fluorenyl, 11,11-diphenyl-10-benzo[a]fluorenyl, 11,11-diphenyl-1-benzo[b]fluorenyl, 11,11-diphenyl-2-benzo[b]fluorenyl, 11,11-diphenyl-3-benzo[b]fluorenyl, 11,11-diphenyl-4-benzo[b]fluorenyl, 11,11-diphenyl-5-benzo[b]fluorenyl, 11,11-diphenyl-6-benzo[b]fluorenyl, 11,11-diphenyl-7-benzo[b]fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2-benzo[c]fluorenyl, 11,11-diphenyl-3-benzo[c]fluorenyl, 11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c]fluorenyl, 11,11-diphenyl-6-benzo[c]fluorenyl, 11,11-diphenyl-7-benzo[c]fluorenyl, 11,11-diphenyl-8-benzo[c]fluorenyl, 11,11-diphenyl-9-benzo[c]fluorenyl, 11,11-diphenyl-10-benzo[c]fluorenyl, 9,9,10,10-tetramethyl-9,10-dihydro-1-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-4-phenanthrenyl, etc. may be mentioned.,

[0017] The terms "(3-30 member) heteroaryl(len)" or "(3-50 member) heteroaryl(len)" refer to an aryl group having 3-30 or 3-50 ring skeleton atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P. The number of heteroatoms is preferably 1-4. The above heteroaryl(len) may be a monocyclic ring or a fused ring fused with at least one benzene ring and may be partially saturated. In addition, the above heteroaryl(len) may include forms in which at least one heteroaryl or aryl group is bonded to the heteroaryl group by a single bond, and may also have a spiro structure. The above heteroaryls include monocyclic heteroaryls such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetradinyl, triazolyl, tetrazolyl, flazanil, pyridyl, pyrazinyl, pyrimidinyl, pyridadinyl, and benzofuranil, benzothiophenyl, isobenzofuranil, dibenzofuranil, dibenzothiophenyl, dibenzoselenophenyl, naphthobenzofuranil, naphthobenzothiophenyl, benzofloquinolyl, benzofloquinazolinil, benzoflonaphtylidinyl, benzoflopyrimidinyl, naphthofyrimidinyl, benzothienocinolyl, benzothienocinazolinil, benzothienonaphtylidinyl, and benzothi Enopyrimidinil, naphthothienopyrimidinil, pyrimidoindolyl, benzopyrimidoindolyl, benzoflopyrazinil, naphthoflopyrazinil, benzothienopyrimidinil, naphthothienopyrimidinil, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinil, quinazolinil, benzoquinazolinil, quinoxalinil, benzoquinoxalinil, naphthilidinil, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinil, phenothiazinil, phenanthiazinil, phenanthiazinil, benzodioxolyl, dihydroacridinil,Condensed ring heteroaryls may include benzotriazolephenadinyl, imidazopyridyl, clomenoquinazolinyl, thioclomenoquinazolinyl, dimethylbenzoperimidinyl, indolocarbazolyl, and indenocarbazolyl. More specifically, heteroaryls may include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazine-4-yl, 1,2,4-triazine-3-yl, 1,3,5-triazine-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolidinyl, 2-indolidinyl, 3-indolidinyl, 5-indolidinyl, 6-indolidinyl, and 7-indolidinyl. Dinyl, 8-Indolidinyl, 2-Imidazopyridyl, 3-Imidazopyridyl, 5-Imidazopyridyl, 6-Imidazopyridyl, 7-Imidazopyridyl, 8-Imidazopyridyl, 3-Pyridyl, 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-benzofuranil, 3-benzofuranil, 4-benzofuranil, 5-benzofuranil, 6-benzofuranil, 7-benzofuranil, 1-isobenzofuranil, 3-isobenzofuranil, 4-isobenzofuranil, 5-isobenzofuranil, 6-isobenzofuranil, 7-isobenzofuranil, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 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-phenanthridine, 2-phenanthridine, 3-phenanthridine, 4-phenanthridine, 6-phenanthridine, 7-phenanthridine, 8-phenanthridine, 9-phenanthridine, 10-phenanthridine, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-flazanyl, 2-thienyl, 3-thienyl, 2-methylpyro 1-yl, 2-methylpyrrole-3-yl, 2-methylpyrrole-4-yl, 2-methylpyrrole-5-yl, 3-methylpyrrole-1-yl, 3-methylpyrrole-2-yl, 3-methylpyrrole-4-yl, 3-methylpyrrole-5-yl, 2-tert-butylpyrrole-4-yl, 3-(2-phenylpropyl)pyrrole-1-yl, 2-methyl-1-indolly, 4-methyl-1-indolly, 2-methyl-3-indolly, 4-methyl-3-indolly, 2-tert-butyl-1-indolly, 4-tert-butyl-1-yl 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, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho-[1,2-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho-[1,2-b]-benzofuranyl Nyl, 6-naphtho-[1,2-b]-benzofuranil, 7-naphtho-[1,2-b]-benzofuranil, 8-naphtho-[1,2-b]-benzofuranil, 9-naphtho-[1,2-b]-benzofuranil, 10-naphtho-[1,2-b]-benzofuranil, 1-naphtho-[2,3-b]-benzofuranil, 2-naphtho-[2,3-b]-benzofuranil, 3-naphtho-[2,3-b]-benzofuranil, 4-naphtho-[2,3-b]-benzofuranil, 5-naphtho-[2,3-b]-benzofuranil, 6-naphtho-[2,3-b]-benzofuranil,7-Naphtho-[2,3-b]-benzofuranil, 8-Naphtho-[2,3-b]-benzofuranil, 9-Naphtho-[2,3-b]-benzofuranil, 10-Naphtho-[2,3-b]-benzofuranil, 1-Naphtho-[2,1-b]-benzofuranil, 2-Naphtho-[2,1-b]-benzofuranil, 3-Naphtho-[2,1-b]-benzofuranil, 4-Naphtho-[2,1-b]-benzofuranil, 5-Naphtho-[2,1-b]-benzofuranil, 6-Naphtho-[2,1-b]-benzofuranil, 7-Naphtho-[2,1-b]-benzofuranil, 8-Naphtho- [2,1-b]-benzofuranyl, 9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-benzothiophenyl, 2-naphtho-[1,2-b]-benzothiophenyl, 3-naphtho-[1,2-b]-benzothiophenyl, 4-naphtho-[1,2-b]-benzothiophenyl, 5-naphtho-[1,2-b]-benzothiophenyl, 6-naphtho-[1,2-b]-benzothiophenyl, 7-naphtho-[1,2-b]-benzothiophenyl, 8-naphtho-[1,2-b]-benzothiophenyl phenyl, 9-naphtho-[1,2-b]-benzothiophenyl, 10-naphtho-[1,2-b]-benzothiophenyl, 1-naphtho-[2,3-b]-benzothiophenyl, 2-naphtho-[2,3-b]-benzothiophenyl, 3-naphtho-[2,3-b]-benzothiophenyl, 4-naphtho-[2,3-b]-benzothiophenyl, 5-naphtho-[2,3-b]-benzothiophenyl, 1-naphtho-[2,1-b]-benzothiophenyl, 2-naphtho-[2,1-b]-benzothiophenyl, 3-naphtho-[2,1-b]-benzothiophenyl, 4-naph To-[2,1-b]-benzothiophenyl, 5-naphtho-[2,1-b]-benzothiophenyl, 6-naphtho-[2,1-b]-benzothiophenyl, 7-naphtho-[2,1-b]-benzothiophenyl, 8-naphtho-[2,1-b]-benzothiophenyl, 9-naphtho-[2,1-b]-benzothiophenyl, 10-naphtho-[2,1-b]-benzothiophenyl, 2-benzoflo[3,2-d]pyrimidinyl, 6-benzoflo[3,2-d]pyrimidinyl, 7-benzoflo[3,2-d]pyrimidinyl, 8-benzoflo[3,2-d]pyrimidinyl,9-Benzoflo[3,2-d]pyrimidinyl, 2-Benzothio[3,2-d]pyrimidinyl, 6-Benzothio[3,2-d]pyrimidinyl, 7-Benzothio[3,2-d]pyrimidinyl, 8-Benzothio[3,2-d]pyrimidinyl, 9-Benzothio[3,2-d]pyrimidinyl, 2-Benzoflo[3,2-d]pyrazinyl, 6-Benzoflo[3,2-d]pyrazinyl, 7-Benzoflo[3,2-d]pyrazinyl, 8-Benzoflo[3,2-d]pyrazinyl, 9-Benzoflo[3,2-d]pyrazinyl, 2-Benzothio[3,2-d] This may include pyrazinyl, 6-benzothio[3,2-d]pyrazinyl, 7-benzothio[3,2-d]pyrazinyl, 8-benzothio[3,2-d]pyrazinyl, 9-benzothio[3,2-d]pyrazinyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, etc.

[0018] The term "(C3-C30) aliphatic ring and (C6-C30) aromatic ring fused ring" means the functional group of a fused ring of one or more aliphatic rings having 3-30, preferably 3-25, more preferably 3-18 carbon atoms in the ring skeleton and one or more aromatic rings having 6-30, preferably 6-25, more preferably 6-18 carbon atoms in the ring skeleton. For example, a fused ring of (C3-C30) aliphatic ring and (C6-C30) aromatic rings may be a fused ring of one or more benzenes and one or more cyclohexanes, or a fused ring of one or more naphthalenes and one or more cyclopentanes. In this disclosure, the carbon atoms of the fused ring of (C3-C30) aliphatic ring and (C6-C30) aromatic rings may be replaced by one or more heteroatoms selected from B, N, O, S, Si, and P, preferably one or more heteroatoms selected from N, O, and S. In this disclosure, the term "halogen" includes F, Cl, Br, and I.

[0019] In addition, "ortho (o-)", "meta (m-)", and "para (p-)" are prefixes that indicate the relative positions of substituents. Ortho indicates that two substituents are adjacent to each other; for example, if two substituents in a benzene derivative occupy positions 1 and 2, it is called the ortho position. Meta indicates that two substituents are at positions 1 and 3; for example, if two substituents in a benzene derivative occupy positions 1 and 3, it is called the meta position. Para indicates that two substituents are at positions 1 and 4; for example, if two substituents in a benzene derivative occupy positions 1 and 4, it is called the para position.

[0020] In addition, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a functional group is substituted by another atom or another functional group (i.e., a substituent), and this includes substitution by a group to which two or more substituents are attached. For example, a "substituent to which two or more substituents are attached" can be pyridine-triazine. That is, pyridine-triazine can be interpreted as a single heteroaryl substituent or as a substituent to which two heteroaryl substituents are attached. In the formulas of this disclosure, the substituents of substituted alkyl, substituted alkylene, substituted alkenyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted cycloalkyl, substituted cycloalkylene, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, and substituted condensed rings of an aliphatic ring and an aromatic ring are, each independently, deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; phosphine oxide; (C1-C30) alkyl; halo(C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3-7 member) hetero Cycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; Unsubstituted or (5-50 member) heteroaryls substituted with at least one of (C1-C30)alkyl, (C6-C30)aryl, and di(C6-C30)arylamino; Unsubstituted or (C6-C30)aryls substituted with at least one of (C1-C30)alkyl, (3-50 member) heteroaryl, and mono- or di-(C6-C30)arylamino; Tri(C1-C30)alkylsilyl; Tri(C6-C30)arylsilyl; Di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; Amino; Mono- or di-(C1-C30)alkylamino; Mono- or di-(C2-C30)alkenylamino;Mono- or di-(C6-C30)arylaminos unsubstituted or substituted with at least one of (C1-C30) alkyl, (5-30 member) heteroaryl, and di(C6-C30) arylaminos; mono- or di-(3-30 member) heteroarylaminos; (C1-C30) alkyl(C2-C30) alkenylaminos; (C1-C30) alkyl(C6-C30) arylaminos; (C1-C30) alkyl(3-30 member) heteroarylaminos; (C2-C30) alkenyl(C6-C30) arylaminos; (C2-C30) alkenyl(3-30 member) heteroarylaminos The substituent is at least one selected from the group consisting of loarylamino; (C6-C30)aryl(3-30 member)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; (C6-C30)arylphosphine; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl. According to one embodiment of the present disclosure, each substituent is at least one independently selected from the group consisting of deuterium, (C1-C20)alkyl and (C6-C25)aryl. According to another embodiment of this disclosure, each substituent is independently selected from the group consisting of (C1-C6) alkyl and (C6-C20) aryl atoms. For example, substituents may be methyl, phenyl, naphthyl, biphenyl, etc.

[0021] Equation 1 is the following Equation 1-1 or 1-2: [ka] (In the formula, L1 and L2 are each independently as defined by L' in Equation 1; Ar1 ​​to Ar4 are each independently as defined by Ar' and Ar'' in Equation 1; R7 is as defined by R1 and R2 in Equation 1; c is 1 or 2, and if c is 2, each R7 can be the same or different from one another; and R1, R2, a and b are as defined in Equation 1. It can be represented by:

[0022] In Formula 1, R3 to R6 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3 to 30-membered) heteroaryl, substituted or unsubstituted (C3 to C30) cycloalkyl, substituted or unsubstituted (C1 to C30) alkoxy, substituted or unsubstituted tri(C1 to C30) alkylsilyl, substituted or unsubstituted di(C1 to C30) alkyl(C6 to C30) arylsilyl, substituted or unsubstituted (C1 to C30) alkyldi(C6 to C30) arylsilyl, substituted or unsubstituted tri(C6 to C30) arylsilyl, or a group represented by Formula A. At least two of R3 to R6 are each independently represented by Formula A, provided that R3 and R6 are not both represented by Formula A at the same time. According to one embodiment of this disclosure, R3 to R6 not represented by formula A represent hydrogen.

[0023] Each L' independently represents a single bond, a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3-30 member) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene. According to one embodiment of the present disclosure, each L' independently represents a single bond or a substituted or unsubstituted (C6-C12) arylene. According to another embodiment of the present disclosure, each L' independently represents a single bond or a substituted or unsubstituted (C6-C12) arylene. For example, each L' may independently be a single bond, phenylene, or naphthylene.

[0024] Ar' and Ar'' can each independently represent a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 member) heteroaryl, or a substituted or unsubstituted condensed ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or they can be linked to adjacent substituents to form a ring. According to another embodiment of the present disclosure, Ar' and Ar'' can each independently represent a substituted or unsubstituted (C6-C25) aryl, a substituted or unsubstituted (5-20 member) heteroaryl, or a substituted or unsubstituted condensed ring of a (C3-C10) aliphatic ring and a (C6-C15) aromatic ring. According to another embodiment of the present disclosure, Ar' and Ar'' each independently represent an unsubstituted (C6-C25)aryl or (C6-C12)aryl substituted with at least one (C1-C6)alkyl and (C6-C12)aryl; an unsubstituted (5-20 member) heteroaryl substituted with at least one (C6-C12)aryl; or an unsubstituted or (C1-C6)alkyl fused ring of a (C3-C10) aliphatic ring and a (C6-C15) aromatic ring. For example, Ar' and Ar'' can each independently be phenyl; naphthyl; biphenyl; phenantrenyl; naphthylphenyl; phenylnaphthyl; unsubstituted or phenyl-substituted diphenylfluorenyl; substituted or phenyl-substituted dimethylfluorenyl; dimethylbenzofluorenyl; unsubstituted or phenyl-substituted dibenzofuranyl; unsubstituted or phenyl-substituted dibenzothiophenyl; benzonaphthofuranil; benzonaphthothiophenyl; unsubstituted or phenyl-substituted carbazolyl; 9,10-tetramethylphenantrenyl, etc.

[0025] R1 and R2 may independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) 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 tri(C6-C30)arylsilyl, or -L3-N-(Ar5)(Ar6), or be linked to adjacent substituents to form a ring. According to one embodiment of the present disclosure, R1 and R2 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C6-C15) aryl, a substituted or unsubstituted (5-15 member) heteroaryl, or -L3-N-(Ar5)(Ar6). According to another embodiment of the present disclosure, R1 and R2 each independently represent hydrogen; an unsubstituted or (C6-C15) aryl substituted with at least one (C1-C6) alkyl; an unsubstituted or (5-15 member) heteroaryl substituted with at least one (C6-C12) aryl; or -L3-N-(Ar5)(Ar6). For example, R1 and R2 each independently may be hydrogen, phenyl, naphthyl, phenantrenyl, dimethylfluorenyl, dibenzofuranyl, phenyl-substituted carbazolyl, diphenylamino, etc.

[0026] Each L3 independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 member) heteroarylene. According to one embodiment of the present disclosure, each L3 independently represents a single bond.

[0027] Ar5 and Ar6 each independently represent hydrogen, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30) alkenyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl. According to one embodiment of the present disclosure, Ar5 and Ar6 each independently represent a substituted or unsubstituted (C6-C12) aryl. According to another embodiment of the present disclosure, Ar5 and Ar6 each independently represent an unsubstituted (C6-C12) aryl. For example, Ar5 and Ar6 may each independently represent phenyl, etc.

[0028] According to one embodiment of the present disclosure, in Formula 1, R3 to R6 not represented by Formula A represent hydrogen; L' each independently represents a single bond or a substituted or unsubstituted (C6 to C12) arylene; Ar' and Ar'' each independently represent a substituted or unsubstituted (C6 to C25) aryl, a substituted or unsubstituted (5 to 20-membered) heteroaryl, or a substituted or unsubstituted fused ring of an (C3 to C10) aliphatic ring and a (C6 to C15) aromatic ring; R1 and R2 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C6 to C15) aryl, a substituted or unsubstituted (5 to 15-membered) heteroaryl, or -L3-N-(Ar5)(Ar6); L3 each independently represents a single bond; and Ar5 and Ar6 each independently represent a substituted or unsubstituted (C6 to C12) aryl.

[0029] According to another embodiment of the present disclosure, in Formula 1, R3-R6 not represented by Formula A represent hydrogen; L' each independently represents a single bond or a substituted or unsubstituted (C6-C12) arylene; Ar' and Ar'' each independently represent an unsubstituted (C6-C25) aryl or (C1-C6) alkyl and (C6-C12) aryl; an unsubstituted (5-20 member) heteroaryl or (C6-C12) substituted (5-20 member) heteroaryl; or an (C3-C10) aliphatic ring and (C6-C15) aryl. R1 and R2 each represent hydrogen; an unsubstituted or substituted (C1-C6) alkyl fused ring with a fragrant ring; an unsubstituted or substituted (C1-C6) alkyl (C6-C15) aryl; an unsubstituted or substituted (C6-C12) aryl (5-15 member) heteroaryl; or -L3-N-(Ar5)(Ar6); L3 each independently represents a single bond; and Ar5 and Ar6 each independently represent an unsubstituted (C6-C12) aryl.

[0030] In the formulas of this disclosure, if a substituent is linked to an adjacent substituent to form a ring, the ring may be a substituted or unsubstituted monocyclic or polycyclic (3-30 member) alicyclic or aromatic ring, or a combination thereof, formed by linking at least two adjacent substituents. In addition, the formed ring may contain at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably at least one heteroatom selected from the group consisting of N, O, and S. According to one embodiment of this disclosure, the number of ring skeleton atoms is (5-20 members), and according to another embodiment of this disclosure, the number of ring skeleton atoms is (5-15 members). For example, the condensed ring may be in the form of 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 benzene ring, or a substituted or unsubstituted carbazole ring.

[0031] In the formulas of this disclosure, heteroaryl and heteroarylene may each independently contain at least one heteroatom selected from B, N, O, S, Si, and P. Furthermore, the heteroatom may be bonded to at least one 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 (5-30 member) 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 tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, and substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino.

[0032] The compounds represented by Formula 1 are, but are not limited to, the following compounds. [ka] [ka] [ka] [ka] [ka]

[0033] The compounds of Formula 1 according to this disclosure may be prepared by synthetic methods known to those skilled in the art, for example, as shown in the following reaction schemes 1 to 3, but are not limited thereto. [Reaction Scheme 1] [ka] [Reaction Scheme 2] [ka] [Reaction Scheme 3] [ka]

[0034] In reaction schemes 1-3, L', Ar', and Ar'' are as defined in Equation 1, and R is as defined in Equation 1, R1 and R2.

[0035] Exemplary synthetic examples of compounds represented by Formula 1 are described above, and those skilled in the art will readily understand that all of them are based on reactions such as the Bukwald-Hartwig cross-coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, Miyaura boration reaction, Suzuki cross-coupling reaction, intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, cyclic dehydration reaction, SN1 substitution reaction, SN2 substitution reaction, and phosphine-mediated reductive cyclization reaction, and that the above reactions proceed even when substituents defined in Formula 1 but not explicitly stated in the specific synthetic examples are attached.

[0036] The hole transport band of this disclosure may consist of at least one layer from the group consisting of a hole transport layer, a hole injection layer, an electron blocking layer, a hole auxiliary layer, and a light emission auxiliary layer, and each layer may consist of one or more layers.

[0037] According to one embodiment of the present disclosure, the hole transport zone includes a hole transport layer. In addition, the hole transport zone may include a hole transport layer and further include one or more layers: a hole injection layer, an electron blocking layer, a hole auxiliary layer, and an luminescence auxiliary layer.

[0038] In addition, this disclosure provides an organic electroluminescent material comprising the organic electroluminescent compound of Formula 1 and an organic electroluminescent device comprising this material.

[0039] This material may be a hole transport material, a hole assist material, a light emission assist material, or an electron blocking material. For example, it may be a hole transport material, a hole assist material, a light emission assist material, or an electron blocking material in a red light-emitting organic electroluminescent device, and if there are two or more layers in the hole transport layer, it may be a hole transport material (hole assist material) contained in the hole transport layer adjacent to the light emission layer.

[0040] This material may consist solely of the organic electroluminescent compound according to this disclosure, or it may further include conventional materials contained in organic electroluminescent materials.

[0041] The organic electroluminescent device according to this disclosure comprises a first electrode, a second electrode, and at least one organic layer sandwiched between the first electrode and the second electrode, wherein the organic layer may contain at least one organic electroluminescent compound of formula 1.

[0042] One of the first electrode and the second electrode may be an anode, and the other may be a cathode. The organic layer includes a light-emitting layer and may further include one or more layers selected from hole injection layers, hole transport layers, hole auxiliary layers, light-emitting auxiliary layers, electron transport layers, electron buffer layers, electron injection layers, intermediate layers, hole blocking layers, and electron blocking layers.

[0043] The first and second electrodes may be formed from a transparent conductive material, a semi-permeable conductive material, or a reflective conductive material, respectively. The organic electroluminescent device may be top-emitting, bottom-emitting, or double-emitting depending on the type of material forming the first and second electrodes. In addition, the hole injection layer may be further doped with a p-type dopant, and the electron injection layer may be further doped with an n-type dopant.

[0044] According to one embodiment of the present disclosure, the organic electroluminescent device of the present disclosure may further include, in addition to the organic electroluminescent compound of the present disclosure, an azine-based compound as at least one of an electron transport material, an electron injection material, an electron buffering material, and a hole blocking material.

[0045] The organic electroluminescent compound represented by Formula 1 of this disclosure may be included in at least one layer of a light-emitting layer, a hole injection layer, a hole transport layer, a hole auxiliary layer, a 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. In some cases, preferably, it may be included in at least one of the hole transport layer, a hole auxiliary layer, or a light-emitting auxiliary layer. If there are two or more layers in the hole transport layer, it may be used with respect to at least one of them. For example, when used in a hole transport layer, the organic electroluminescent compound of this disclosure may be included as a hole transport material.

[0046] The emissive layer may include one or more hosts and one or more dopants. If necessary, the emissive layer may include co-host materials, i.e., two or more host materials.

[0047] The host used in this disclosure may be a phosphorescent host compound or a fluorescent host compound, but is not limited to these.

[0048] The dopants that may be included in the organic electroluminescent devices according to this disclosure may be at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent devices according to the present invention is not particularly limited, but may be selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt) metallized complex compounds, preferably from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt) orthometallated complex compounds, and more preferably from orthometallated iridium complex compounds.

[0049] The dopants included in the organic electroluminescent devices of this disclosure may be, but are not limited to, compounds represented by the following formula 101. [ka]

[0050] In Equation 101, L has the following structure 1-3: [ka] Selected from, R 100 ~R 103Each of these independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium and / or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3-30 member) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy, or may be linked to adjacent substituents to form a ring with pyridine, such as a substituted or unsubstituted quinoline, isoquinoline, benzophropyridine, benzothienopyridine, indenopyridine, benzophroquinoline, benzothienoquinoline, or indenoquinoline ring; R 104 ~R 107 Each of these can independently represent hydrogen, deuterium, halogen, unsubstituted or deuterium and / or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy, or be bonded to an adjacent substituent to form a ring with benzene, such as a substituted or unsubstituted naphthalene, fluorene, dibenzothiophene, dibenzofuran, indenopyridine, benzophropyridine, or benzothienopyridine ring; R 201 ~R 220 Each of these independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium and / or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl, or may be linked to adjacent substituents to form a ring; and 's' represents an integer between 1 and 3.

[0051] Specific examples of dopant compounds are as follows, but are not limited to these. [ka] [ka] [ka] [ka] [ka] [ka]

[0052] This disclosure provides, as an additional embodiment, compositions for preparing organic electroluminescent devices. These compositions are preferably for preparing hole transport layers, hole auxiliary layers, light emission auxiliary layers, or electron blocking layers of organic electroluminescent devices, and include the compounds of this disclosure. If two or more layers are present in the hole transport layer, the compounds of this disclosure may be included in a composition for preparing a hole transport layer (hole auxiliary layer) adjacent to the light emission layer.

[0053] In addition, the organic electroluminescent device of this disclosure comprises a first electrode, a second electrode, and at least one organic layer sandwiched between the first electrode and the second electrode, wherein the organic layer includes a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, or an electron blocking layer. The hole transport layer, hole auxiliary layer, light emission auxiliary layer, or electron blocking layer may include compositions for the organic electroluminescent device according to this disclosure.

[0054] The organic electroluminescent device of this disclosure comprises an organic electroluminescent compound of Formula 1 and may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.

[0055] Furthermore, in the organic electroluminescent device of this disclosure, the organic layer may further include at least one metal selected from the group consisting of Group 1 metals, Group 2 metals, Group 4 transition metals, Group 5 transition metals, lanthanides of d-transition elements of the periodic table, and organometallic or organic electroluminescent compounds of formula 1, as well as at least one complex compound containing the aforementioned metals.

[0056] In addition, the organic electroluminescent devices of this disclosure may emit white light by further comprising, in addition to the organic electroluminescent compounds of this disclosure, at least one light-emitting layer containing a blue, red, or green light-emitting compound known in the art. In addition, it may further comprise a yellow or orange light-emitting layer, if desired.

[0057] In the organic electroluminescent device of this disclosure, at least one layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as the "surface layer") may preferably be disposed on the inner surface of one or both electrodes. Specifically, a silicon or aluminum chalcogenide (including oxide) layer is preferably disposed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer is preferably disposed on the cathode surface of the electroluminescent medium layer. The surface layer may provide operational stability to the organic electroluminescent device. Preferably, the chalcogenide is SiO X (1≦X≦2), AlO X Examples of metal halides (1≦X≦1.5) include SiON and SiAlON; examples of metal halides include LiF, MgF2, CaF2, and rare earth metal fluorides; and examples of metal oxides include Cs2O, Li2O, MgO, SrO, BaO, and CaO.

[0058] A hole injection layer, hole transport layer, electron blocking layer, or a combination thereof may be used between the anode and the light-emitting layer. The hole injection layer may be multilayered to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer, and two compounds may be used simultaneously in each multilayer. The hole injection layer may also be doped with a p-dopant. The electron blocking layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer to block overflowing electrons from the light-emitting layer and to confine excitons in the light-emitting layer to prevent light leakage. The hole transport layer or electron blocking layer may be multilayered, and multiple compounds may be used in each multilayer.

[0059] Electron buffer layers, hole blocking layers, electron transport layers, electron injection layers, or combinations thereof can be used between the light-emitting layer and the cathode. The electron buffer layer may be a multilayer designed to control electron injection and improve the interfacial properties between the light-emitting layer and the electron injection layer, and two compounds can be used simultaneously in each of the multilayers. The hole blocking layer or electron transport layer may also be a multilayer, and multiple compounds can be used in each multilayer. In addition, the electron injection layer may be doped with an n-type dopant.

[0060] In this specification, a hole auxiliary layer or light emission auxiliary layer may be placed between a hole transport layer and a light emission layer and used to control the hole transport rate. The hole auxiliary layer or light emission auxiliary layer may provide the effect of improving the efficiency and lifespan of organic electroluminescent devices.

[0061] A luminescence auxiliary layer may be placed between the anode and the luminescence layer, or between the cathode and the luminescence layer. When the luminescence auxiliary layer is placed between the anode and the luminescence layer, it can be used to facilitate hole injection and / or hole transport, or to prevent electron overflow. When the luminescence auxiliary layer is placed between the cathode and the luminescence layer, it can be used to facilitate electron injection and / or electron transport, or to prevent hole overflow. In addition, a hole auxiliary layer may be placed between the hole transport layer (or hole injection layer) and the luminescence layer, and can be effective in facilitating or blocking the hole transport rate (or hole injection rate), thereby allowing the charge balance to be controlled. Furthermore, an electron blocking layer may be placed between the hole transport layer (or hole injection layer) and the luminescence layer, and can block electrons from overflowing from the luminescence layer, confining excitons within the luminescence layer and preventing light leakage. If an organic electroluminescent device includes two or more hole transport layers, additional hole transport layers may be used as hole auxiliary layers or electron blocking layers. The hole auxiliary layer and electron blocking layer have the effect of improving the efficiency and / or lifespan of organic electroluminescent devices.

[0062] In the organic electroluminescent device of this disclosure, it is preferable that a mixed region of an electron transport compound and a reducing dopant, or a mixed region of a hole transport compound and an oxidizing dopant, be located on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anion, making it easier to inject and transport electrons from the mixed region to the electroluminescent medium. Furthermore, the hole transport compound is oxidized to a cation, making it 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. An organic electroluminescent device having two or more light-emitting layers can be fabricated using a reducing dopant layer as a charge-generating layer, which emits white light.

[0063] An organic electroluminescent material according to one embodiment of the present disclosure can be used as a light-emitting material for a white organic light-emitting device. White organic light-emitting devices have been proposed in various structures, such as parallel side-by-side arrangement, stacked arrangement, or CCM (color conversion material) method, depending on the arrangement of R (red), G (green) or YG (yellow-green) and B (blue) light-emitting units. In addition, an organic electroluminescent material according to one embodiment of the present disclosure can also be applied to organic electroluminescent devices containing QDs (quantum dots).

[0064] To form each layer of the organic electroluminescent device of this disclosure, dry film formation methods such as vacuum evaporation, sputtering, plasma, and ion plating, or wet film formation methods such as inkjet printing, spin coating, dip coating, and flow coating can be used.

[0065] When using a wet film formation method, thin films can be formed by dissolving or diffusing the materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, or dioxane. The solvent is not particularly limited, as long as the materials forming each layer are soluble in or dispersible in the solvent without causing any problems in film formation.

[0066] By using the organic electroluminescent devices of this disclosure, it is possible to manufacture display systems, such as display systems for smartphones, tablets, notebooks, PCs, TVs, or automobiles, or lighting systems, such as outdoor or indoor lighting systems.

[0067] The following describes in detail, with reference to representative compounds of this disclosure, the methods for preparing the compounds and their properties, as well as the luminescence properties of organic electroluminescent devices containing them. However, this disclosure is not limited to the following examples. [Examples]

[0068] Example 1: Preparation of Compound A-100 [ka] Synthesis of compound 1-1 Compound A (4.0 g, 16.18 mmol), 9,9'-dimethyl-N-phenyl-9H-fluoren-2-amine (4.6 g, 16.18 mmol), tris(dibenzyridineacetone)dipalladium (0.74 g, 0.81 mmol), tri-tert-butylphosphine (0.8 mL, 1.62 mmol), sodium tert-butoxide (2.4 g, 24.27 mmol), and 81 mL of toluene were placed in a reaction vessel and stirred under reflux for 1 hour. After the reaction was complete, the mixture was washed with distilled water, and the organic layer was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, the solvent was removed using a rotary evaporator, and then the compound 1-1 (5.6 g, yield: 70%) was obtained by purification by column chromatography.

[0069] Synthesis of compound A-100 Compound 1-1 (5.6 g, 11.31 mmol), N-phenyl-[1,1'-biphenyl]-4-amine (3.6 g, 14.70 mmol), tris(dibenzyridineacetone)dipalladium (0.52 g, 0.57 mmol), tri-tert-butylphosphine (0.55 mL, 1.13 mmol), sodium tert-butoxide (1.63 g, 16.97 mmol), and 57 mL of toluene were placed in a reaction vessel and stirred under reflux for 1 hour. After the reaction was complete, the mixture was washed with distilled water, and the organic layer was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, the solvent was removed using a rotary evaporator, and then the compound A-100 (1.8 g, yield: 22%) was obtained by purification by column chromatography.

[0070] [Table 1]

[0071] Example 2: Preparation of Compound A-11 [ka] Compound A (5.0 g, 20.23 mmol), 9,9-dimethyl-N-phenyl-9H-fluorene-2-amine (12.7 g, 44.51 mmol), tris(dibenzylideneacetone)dipalladium(0) (1.9 g, 2.02 mmol), tri-tert-butylphosphine (1.9 mL, 4.04 mmol), sodium tert-butoxide (5.8 g, 60.69 mmol) and 100 mL of toluene were placed in a reaction vessel and stirred under reflux for 4 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, the solid was filtered and washed with ethyl acetate. The filtrate was distilled under reduced pressure and purified by column chromatography to obtain Compound A-11 (4 g, yield: 26%).

[0072] [Table 2]

[0073] Device Example 1: Manufacture of an OLED Containing a Compound According to the Present Disclosure An OLED containing an organic electroluminescent compound according to the present disclosure was manufactured as follows. First, an indium tin oxide (ITO) thin film (10 Ω / sq) (Dymatic Co., Ltd., Japan) on a glass substrate for the OLED was subjected to ultrasonic cleaning successively with acetone, ethanol and distilled water, and then stored in isopropanol before use. The degree of vacuum in the chamber was 10 -6After degassing until torr was reached, the ITO substrate was mounted on the substrate holder of the vacuum deposition apparatus. Compound HT-1 was placed in one cell of the vacuum deposition apparatus as the first hole injection compound, and compound HI-1 was placed in another cell. By doping with compound HI-1 at an amount of 3 wt% based on the total amount of compound HT-1 and compound HI-1, the two materials were evaporated at different rates to deposit a hole injection layer having a thickness of 10 nm. Subsequently, the material of compound HT-1 was evaporated into the first hole transport layer, thereby depositing a first hole transport layer having a thickness of 90 nm on the hole injection layer. Then, compound A-11 according to this disclosure was introduced into another cell of the vacuum deposition apparatus, and an electric current was passed through the cell to evaporate it, thereby depositing a second hole transport (or auxiliary) layer having a thickness of 60 nm on the first hole transport layer. After the hole injection layer and the hole transport (or auxiliary) layer were formed, an emissive layer was deposited thereon as follows. Compound RH was introduced into a vacuum deposition apparatus cell as the host for the emissive layer, and compound D-39 was introduced into another cell as the dopant. By evaporating the two materials and doping the dopant at a rate of 2 wt% based on the total amount of host and dopant, an emissive layer with a thickness of 40 nm was deposited on the second hole transport layer. Subsequently, compounds ET-1 and EI-1 in two different cells were evaporated at a rate of 1:1 to deposit an electron transport layer with a thickness of 35 nm on the emissive layer. After depositing compound EI-1 as the electron injection layer to a thickness of 2 nm, an Al cathode was deposited to a thickness of 80 nm using another vacuum deposition apparatus to produce an OLED.

[0074] As a result, the driving voltage based on 1,000 nits for the organic electroluminescent device of Device Example 1 was 3.1V, and the power efficiency was 28.8 lm / W.

[0075] Device Example 2: Manufacturing of an OLED containing the compound according to the present disclosure An OLED was fabricated in the same manner as in Device Example 1, except that compound A-100 was used as the material for the second hole transport (or auxiliary) layer.

[0076] As a result, the driving voltage based on 1,000 nits for the organic electroluminescent device of Device Example 2 was 3.5V, and the power efficiency was 28.4 lm / W.

[0077] Comparative example: Fabrication of OLEDs containing conventional compounds An OLED was fabricated in the same manner as in Device Example 1, except that compound B-1 was used as the material for the second hole transport (or auxiliary) layer.

[0078] As a result, the driving voltage based on 1,000 nits for the comparative organic electroluminescent device was 4.4V, and the power efficiency was 23.6 lm / W.

[0079] The power efficiency of organic electroluminescent devices containing the compounds of this disclosure in the hole transport (or auxiliary) layer was confirmed to be lower in drive voltage than that of conventional organic electroluminescent devices. In addition, the high power efficiency of organic electroluminescent devices containing the compounds of this disclosure is expected to reduce power consumption.

[0080] The compounds used in the device examples and comparative examples are shown in Table 1 below.

[0081] [Table 3]

Claims

1. An organic electroluminescent compound for use in at least one layer of the layers constituting the hole transport band of an organic electroluminescent device, The following equation 1-1: 【Chemistry 1】 (In the formula, L １ and L ２ Each of these independently represents a single bond, a deuterium-substituted or unsubstituted phenylene, or a deuterium-substituted or unsubstituted naphthylene; Ar １ ~Ar ４ Each of these independently represents a deuterium-substituted or unsubstituted phenyl, deuterium-substituted or unsubstituted naphthyl, deuterium-substituted or unsubstituted biphenyl, deuterium-substituted or unsubstituted phenantrenyl, deuterium-substituted or unsubstituted naphthylphenyl, deuterium-substituted or unsubstituted phenylnaphthyl, deuterium-substituted or unsubstituted 9,9-diphenyl-1-fluorenyl, deuterium-substituted or unsubstituted 9,9-diphenyl-2-fluorenyl, deuterium-substituted or unsubstituted 9,9-diphenyl-3-fluorenyl, deuterium-substituted or unsubstituted 9,9-diphenyl-4-fluorenyl, deuterium-substituted or unsubstituted 9,9-dimethyl-1-fluorenyl, deuterium-substituted or unsubstituted 9,9-dimethyl-2-fluorenyl, deuterium-substituted or unsubstituted 9,9-dimethyl-3-fluorenyl, and deuterium-substituted or unsubstituted 9,9-dimethyl-4-fluorenyl, dimethylbenzofluorenyl, or 9,10-tetramethylphenantrenyl; R １ , R ２ And R7 each independently represent hydrogen or deuterium; c is either 1 or 2, and if c is 2, then each R ７ They may be the same as or different from each other; a is an integer from 1 to 4, b is 1 or 2, and when a and b are each integers of 2 or more, R １ and R ２ each of which may be the same as or different from each other) An organic electroluminescent compound represented by [the specified formula / method].

2. The following compounds: 【Chemistry 2】 【Transformation 3】 An organic electroluminescent compound according to claim 1, selected from the above.

3. An organic electroluminescent material comprising the organic electroluminescent compound described in claim 1.

4. An organic electroluminescent device comprising the organic electroluminescent compound described in claim 1 in a hole transport zone.

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