Organic electroluminescent compound, organic electroluminescent material containing the same compound, and organic electroluminescent device

Abstract

To provide an organic electroluminescent device with low drive voltage and / or high luminous efficiency and / or a long life.SOLUTION: An organic electroluminescent material of Formula (1) is included in an organic electroluminescent device.SELECTED DRAWING: None

Description

Technical Field

[0001] The present disclosure relates to an organic electroluminescent compound, an organic electroluminescent material containing the compound, and an organic electroluminescent device.

Background Art

[0002] Among display devices, an electroluminescent device (EL device) is a self-luminous display device having advantages of providing a wider viewing angle, a higher contrast ratio, and a faster response time. In 1987, the first organic EL device was developed by Eastman Kodak by using a small aromatic diamine molecule and an aluminum complex as materials for forming a light-emitting layer (Non-Patent Document 1).

[0003] An organic electroluminescent device (OLED) has a multilayer structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. for improving its efficiency and stability. In this case, the selection of a compound contained in the hole transport layer etc. is recognized as one of the means for improving device characteristics such as the hole transport efficiency to the light-emitting layer, the light-emitting efficiency, and the 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), 4,4',4''-tris(3-methylphenylphenylamino)triphenylamine (MTDATA), etc. have been used as compounds contained in hole injection and transport materials in OLEDs. However, OLEDs fabricated using these materials have problems of reduced quantum efficiency and lifespan. This is due to the fact that when an OLED is driven at a high current, thermal stress occurs between the anode and the hole injection layer, and such thermal stress significantly reduces the lifespan of the device. Furthermore, since the organic materials used in the hole injection layer have a very high hole mobility, there has been a problem in that the charge balance between holes and electrons is disrupted and the quantum efficiency (cd / A) decreases.

[0005] Therefore, there is still a need to develop materials for the hole transport layer to improve the performance of OLEDs.

[0006] (Patent Document 1) discloses a compound in which tetramethylphenanthrene is used as a linking group of a carbazole-carbazole compound as an example of a host material. However, the said reference does not disclose examples of specific devices and the synthesis method of the said compound. In addition, the said compound in the reference has not been used as a material for the hole transport layer.

Prior Art Documents

Patent Documents

[0007]

Patent Document 1

Non-Patent Documents

[0008]

Non-Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0009] An object of the present disclosure is, firstly, to provide an organic electroluminescent compound and an organic electroluminescent compound capable of producing an organic electroluminescent device having a low driving voltage and / or a high luminous efficiency and / or a long lifespan, and secondly, to provide an organic electroluminescent device containing the organic electroluminescent compound.

Means for Solving the Problems

[0010] As a result of intensive research to solve the above technical problems, the present inventors have discovered that a compound represented by the following formula 1 having a dihydrophenanthrene moiety exhibits improved degradation characteristics, and completed the present invention.

Chemical Formula

[0011] In formula 1, R1 to R4 are each independently *-(L1) a -(Ar1) b , hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl, or may be linked to adjacent substituents to form a ring; R5 to R 12 are each independently *-(L1) a -(Ar1) b, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted condensed ring of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, 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, or substituted or unsubstituted tri(C6-C30)arylsilyl, or may be linked with adjacent substituents to form a ring; R1 to R 12 at least one of which is *-(L1) a -(Ar1) b on the condition that; L1 represents a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3-30 membered) heteroarylene; Ar1 represents substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, or -N-(Ar2)(Ar3); Ar2 and Ar3 each independently represent substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted condensed ring of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl; a represents an integer of 1 or 2, b represents an integer of 1-4, and when a and b are 2 or more, each L1 and each Ar1 may be the same or different; R5 to R 10 and R 12 are hydrogen and R 11 is a compound of formula 1 containing a substituted amino group is excluded.

[0012] Advantageous effects of the invention By including the organic electroluminescent compound according to the present disclosure and the organic electroluminescent material containing the same, an organic electroluminescent device having a low driving voltage and / or a high luminous efficiency and / or a long lifespan can be manufactured.

Mode for Carrying Out the Invention

[0013] 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 in any way.

[0014] The present disclosure relates to an organic electroluminescent compound represented by the above formula 1, an organic electroluminescent material containing the organic electroluminescent compound, and an organic electroluminescent device containing the organic electroluminescent material.

[0015] Furthermore, the present disclosure relates to an organic electroluminescent compound represented by formula 2 and an organic electroluminescent device containing this organic electroluminescent compound.

[0016] Furthermore, the present disclosure relates to an organic electroluminescent compound represented by formula 3 and an organic electroluminescent device containing this organic electroluminescent compound.

[0017] 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.

[0018] As used herein, the term "organic electroluminescent material" means a material that may contain at least one compound and can be used in an organic electroluminescent device. The organic electroluminescent material may be included in any layer constituting the organic electroluminescent device as needed. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole assisting material, a light emission assisting material, an electron blocking material, a light emitting material (including a host and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material, etc.

[0019] As used herein, the term "a plurality of host materials" means an organic electroluminescent material containing a combination of at least two host materials. It can mean both the material before being included in the organic electroluminescent device (e.g., before evaporation) and the material after being included in the organic electroluminescent device (e.g., after evaporation). The plurality of host materials of the present disclosure may be included in any light emitting layer constituting the organic electroluminescent device. Two or more compounds included in the plurality of host materials of the present disclosure may be included in one light emitting layer or may be included in different light emitting layers respectively. When at least two host materials are included in one layer, the at least two host materials may be co-evaporated to form a layer, or may be co-evaporated individually at the same time to form a layer.

[0020] In the present disclosure, 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 above alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, and the like. The term “(C2-C30) alkenyl” in the present disclosure 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 above alkenyl include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, and the like. In the present disclosure, the term “(C3-C30) cycloalkyl” means a monocyclic or polycyclic hydrocarbon having 3 to 30 ring-skeleton carbon atoms, where the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7. Examples of the above cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, and the like. In the present disclosure, the term “(3- to 7-membered) heterocycloalkyl” means a cycloalkyl having 3 to 7 ring-skeleton atoms, preferably 5 to 7 ring-skeleton atoms, and at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably from the group consisting of O, S, and N. Examples thereof include tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, and the like. In the present disclosure, “(C6-C30) aryl(en)” means a monocyclic or condensed-ring radical derived from an aromatic hydrocarbon having 6 to 30 ring-skeleton carbon atoms, where the number of ring-skeleton carbon atoms therein is preferably 6 to 20, more preferably 6 to 15, and may be partially saturated or may contain a spiro structure. Specific examples of aryl include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl,Examples include diphenylbenzofluorenyl, dibenzofluorenyl, phenanthrenyl, benzophenanthrenyl, phenylphenanthrenyl, anthracenyl, benzanthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, benzochrysenyl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, cumenyl, spiro[fluorene-fluorene]yl, spiro[fluorene-benzofluorene]yl, azulenyl, tetramethyl-dihydrophenanthrenyl, and the like. More specifically, aryl includes o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3, xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p-t-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-t-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, 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, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 4-chrysenyl, 5-chrysenyl, 6-chrysenyl, benzo[c]phenanthrenyl, benzo[g]chrysenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl,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, and the like. In the present disclosure, "(3 to 30-membered) heteroaryl(ene)" is an aryl having 3 to 30 ring backbone atoms containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, P, Se, and Ge, preferably at least one heteroatom selected from N, O, and S, and the number of ring backbone carbon atoms is preferably 5 to 25. The number of heteroatoms in the heteroaryl is preferably 1 to 4. The above heteroaryl may be a monocyclic ring,Alternatively, it may be a condensed ring fused with at least one benzene ring; it may also be partially saturated. In addition, the above-mentioned heteroaryl in the present specification may be formed by bonding at least one heteroaryl group or aryl group to the heteroaryl group by a single bond. Examples of heteroaryl specifically include monocyclic heteroaryls such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl; and condensed ring heteroaryls such as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, benzofuroquinolinyl, benzofuroquinazolinyl, benzofuronaphthyridinyl, benzofuropyrimidinyl, naphthofuropyrimidinyl, benzothienoquinolinyl, benzothienoquinazolinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthothienopyrimidinyl, pyrimidylindolyl, benzopyrimidylindolyl, benzofuropyrazinyl, naphthofuropyrazinyl, benzothienopyrazinyl, naphthothienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, indolizinyl, acridinyl, silafurenyl, germafurenyl, benzotriazolyl, phenazinyl, imidazopyridinyl, chromenoquinazolinyl, thiochromenoquinazolinyl, dimethylbenzoperimidinyl, indolocarbazolyl, indenocarbazolyl. More specifically, heteroaryl is 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-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-indolizinyl, 2-indolizinyl, 3-indolizinyl, 5-indolizinyl, 6-indolizinyl, 7-indolizinyl, 8-indole, dizinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 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, 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, azacarbazol-1-yl, azacarbazol-2-yl, azacarbazol-3-yl, azacarbazol-4-yl, azacarbazol-5-yl, azacarbazol-6-yl, azacarbazol-7-yl, azacarbazol-8-yl, azacarbazol-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-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-t-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-t-butyl-1-indolyl, 4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl, 4-t-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, 6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl, 8-naphtho-[1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl, 1-naphtho-[2,3-b]-benzofuranyl, 2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl, 4-naphtho-[2,3-b]-benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b]-benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl, 10-naphtho-[2,3-b]-benzofuranyl, 1-naphtho-[2,1-b]-benzofuranyl, 2-naphtho-[2,1-b]-benzofuranyl, 3-naphtho-[2,1-b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzofuranyl, 6-naphtho-[2,1-b]-benzofuranyl, 7-naphtho-[2,1-b]-benzofuranyl, 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, 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-naphtho[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-benzofuro[3,2-d]pyrimidinyl, 6-benzofuro[3,2-d]pyrimidinyl, 7-benzofuro[3,2-d]pyrimidinyl, 8-benzofuro[3,2-d]pyrimidinyl, 9-benzofuro[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-benzofuro[3,2-d]pyrazinyl, 6-benzofuro[3,2-d]pyrazinyl, 7-benzofuro[3,2-d]pyrazinyl, 8-benzofuro[3,2-d]pyrazinyl, 9-benzofuro[3,2-d]pyrazinyl, 2-benzothio[3,2-d]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-germafuorenyl, 2-germafuorenyl, 3-germafuorenyl, 4-germafuorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, or the like may also be used. The term "(C3-C30) aliphatic ring and (C6-C30) aromatic ring fused ring" in the present disclosure means a ring formed by condensing at least one aliphatic ring having 3 to 30 ring backbone carbon atoms (the number of carbon atoms therein is preferably 3 to 25, more preferably 3 to 18) and at least one aromatic ring having 6 to 30 ring backbone carbon atoms (the number of carbon atoms therein is preferably 6 to 25, more preferably 6 to 18). For example, the fused ring may be a fused ring of at least one benzene and at least one cyclohexane, or a fused ring of at least one naphthalene and at least one cyclopentane, etc. In the present specification, the carbon atoms of the (C3-C30) aliphatic ring and (C6-C30) aromatic ring fused ring may be replaced by at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S. The term "halogen" in the present disclosure includes F, Cl, Br, and I.,

[0021] In addition, "ortho (o)", "meta (m)", and "para (p)" all mean indicating the substitution positions of all substituents. The ortho position is a compound in which the substituents are adjacent to each other, that is, at the 1-position and 2-position on benzene. The meta position is the substitution position next to the directly adjacent substitution position. That is, a compound having substituents at the 1-position and 3-position on benzene. The para position is the substitution position next to the meta position. That is, a compound having substituents at the 1-position and 4-position on benzene.

[0022] The term "ring formed by linking with adjacent substituents" in the present disclosure means a substituted or unsubstituted (3- to 30-membered) monocyclic or polycyclic, aliphatic ring, aromatic ring, or a combination thereof, preferably a substituted or unsubstituted (3- to 26-membered) monocyclic or polycyclic, aliphatic ring, aromatic ring, or a combination thereof, formed by linking or condensing two or more adjacent substituents. Further, 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 the present disclosure, the number of atoms in the ring skeleton is 5 to 20; according to another embodiment of the present disclosure, the number of atoms in the ring skeleton is 5 to 15. The bonded or condensed ring can be, for example, 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, etc.

[0023] Furthermore, the term "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a specific functional group is replaced by another atom or another functional group, i.e., a substituent. Preferably, in the present disclosure, the substituents of substituted (C1-C30) alkyl, substituted (C2-C30) alkenyl, substituted (C6-C30) aryl(en), substituted (3-30 membered) heteroaryl(en), substituted (C3-C30) cycloalkyl, substituted (3-7 membered) heterocycloalkyl, substituted condensed ring of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, substituted tri(C1-C30) alkylsilyl, substituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted (C1-C30) alkyldi(C6-C30) arylsilyl, and substituted tri(C6-C30) arylsilyl are each independently deuterium, halogen, cyano, carboxyl, nitro, hydroxy, (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 membered) heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, unsubstituted or (C6-C30) aryl-substituted (5-30 membered) heteroaryl, unsubstituted or (5-30 membered) heteroaryl-substituted (C6-C30) aryl, tri(C1-C30) alkylsilyl, tri(C6-C30) arylsilyl, di(C1-C30) alkyl(C6-C30) arylsilyl, (C1-C30) alkyldi(C6-C30) arylsilyl, condensed ring of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, amino, mono- or di-(C1-C30) alkylamino, mono- or di-(C2-C30) alkenylamino, (C1-C30) alkyl(C2-C30) alkenylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, (C1-C30) alkyl(C6-C30) arylamino, mono- or di-(3-30 membered) heteroarylamino, (C1-C30) alkyl(3-30 membered) heteroarylamino, (C2-C30) alkenyl(C6-C30) arylamino,The substituent represents at least one selected from the group consisting of (C2-C30)alkenyl(3-30 membered)heteroarylamino, (C6-C30)aryl(3-30 membered)heteroarylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl, (C6-C30)ar(C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl. For example, the substituent may be methyl, phenyl, naphthyl, p-biphenyl, m-biphenyl, m-terphenyl, fluorenyl, phenanthrenyl, pyridyl, dibenzothiophenyl, or dibenzofuranyl.

[0024] In the following, an organic electroluminescent compound according to one embodiment is described.

[0025] The organic electroluminescent compound according to one embodiment is represented by Formula 1 below: [ka]

[0026] In Equation 1, R1 to R4 are each independently *-(L1) a -(Ar1) b , hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl, or may be linked to adjacent substituents to form a ring; R5~R 12 are each independently *-(L1) a -(Ar1) b, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, 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, or substituted or unsubstituted tri(C6-C30) arylsilyl, or may be linked to adjacent substituents to form a ring; R1~R 12 At least one of the following is *-(L1) a -(Ar1) b Provided that it represents; L1 represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30-membered) heteroarylene; Ar1 represents a substituted or unsubstituted (C6 to C30) aryl, a substituted or unsubstituted (3 to 30-membered) heteroaryl, or -N-(Ar2)(Ar3); Ar2 and Ar3 each independently represent a substituted or unsubstituted (C1 to C30) alkyl, a substituted or unsubstituted (C2 to C30) alkenyl, a substituted or unsubstituted fused ring of a (C3 to C30) aliphatic ring and a (C6 to C30) aromatic ring, a substituted or unsubstituted (C6 to C30) aryl, or a substituted or unsubstituted (3 to 30-membered) heteroaryl; a represents an integer of 1 or 2, b represents an integer of 1 to 4, and when a and b are 2 or more, each L1 and each Ar1 may be the same or different; R5~R 10 and R 12 represents hydrogen, and R 11 with the proviso that compounds of formula 1 containing a substituted amino group are excluded.

[0027] In one embodiment, R1 to R4 are each independently, *-(L1) a -(Ar1) b and may be substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl, preferably, *-(L1) a -(Ar1) b and may be substituted or unsubstituted (C1-C10) alkyl, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5-25 membered) heteroaryl, more preferably, *-(L1) a -(Ar1) b and may be substituted or unsubstituted (C1-C4) alkyl, substituted or unsubstituted (C6-C18) aryl, or substituted or unsubstituted (5-18 membered) heteroaryl. For example, R1 to R4 are each independently substituted or unsubstituted methyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, or *-(L1) a -(Ar1) b and may be such.

[0028] In one embodiment, R5 to R 12 are each independently, *-(L1) a -(Ar1) b and may be hydrogen, a substituted or unsubstituted condensed ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl; or may be linked with an adjacent substituent to form a ring, preferably *-(L1) a -(Ar1) b and may be hydrogen, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5-25 membered) heteroaryl; or may be linked with an adjacent substituent to form a substituted or unsubstituted (5-30 membered) monocyclic or polycyclic aliphatic ring, aromatic ring, or a combination thereof, more preferably *-(L1) a -(Ar1)b It may be hydrogen, substituted or unsubstituted (C6 - C18) aryl, or substituted or unsubstituted (5 - 18 membered) heteroaryl; or it may be linked to an adjacent substituent to form a substituted or unsubstituted (5 - 30 membered) monocyclic or polycyclic aromatic ring.

[0029] In Formula 1 above, at least one of R1 to R 12 is *-(L1) a -(Ar1) b For example, at least one of R1 to R4, at least one of R5 to R8, or at least one of R9 to R 12 may be *-(L1) a -(Ar1) b For example, R1 to R4 other than *-(L1) a -(Ar1) b may each independently be substituted or unsubstituted methyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl. For example, R5 to R 12 other than *-(L1) a -(Ar1) b of R5 to R 12 may each independently be hydrogen, unsubstituted or phenyl substituted with (C6 - C30) aryl or deuterium, substituted or unsubstituted m - biphenyl, or substituted or unsubstituted pyridyl, or the substituents adjacent to R5 to R 12 or the substituents adjacent to R9 to R 12 may be linked to each other to form a benzene ring, naphthalene ring, or phenanthrene ring.

[0030] According to one embodiment, Formula 1 may be an organic electroluminescent compound in which Ar1 represents a substituted or unsubstituted (3 - 30 membered) heteroaryl containing at least one N or -N-(Ar2)(Ar3); and L1 represents a single bond or a substituted or unsubstituted (C6 - C30) arylene.

[0031] According to one embodiment, the organic electroluminescent compound represented by Formula 1 can be represented by any one of the following Formulas 1-1 to 1-4.

Chemical formula

[0032] In Formulas 1-1 to 1-4, R1 to R 12 , L1, Ar1, a, and b are as defined in Formula 1 above.

[0033] According to another embodiment, the organic electroluminescent compound represented by Formula 1 can be represented by any one of the following Formulas 1-5 to 1-13.

Chemical formula

Chemical formula

Chemical formula

[0034] In Formulas 1-5 to 1-13, R1 to R 12 are as defined in Formula 1 above; R 13 to R 18 are each independently *-(L1) a -(Ar1) b, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, a substituted or unsubstituted condensed ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, 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, or substituted or unsubstituted tri(C6-C30)arylsilyl, or may be linked with adjacent substituents to form a ring; Among R1 to R in Formulas 1-5 to 1-7 14 At least one of them, among R1 to R in Formulas 1-8 to 1-10 16 At least one of them, and among R1 to R in Formulas 1-11 to 1-13 18 At least one of them is *-(L1) a -(Ar1) b on the condition that it represents; L1, Ar1, a, and b are as defined in Formula 1.

[0035] In one embodiment, Ar1 may be a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (5-30 membered) heteroaryl, or -N-(Ar2)(Ar3). Preferably, it may be a substituted or unsubstituted (5-25 membered) heteroaryl containing at least one N, or -N-(Ar2)(Ar3). More preferably, it may be a substituted or unsubstituted (5-25 membered) heteroaryl containing at least one N, or -N-(Ar2)(Ar3). Here, Ar2 and Ar3 may each independently be 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 membered) heteroaryl. Preferably, it may be a substituted or unsubstituted condensed ring of a (C3-C20) aliphatic ring and a (C6-C25) aromatic ring, a substituted or unsubstituted (C6-C25) aryl, or a substituted or unsubstituted (5-25 membered) heteroaryl. More preferably, it may be a substituted or unsubstituted condensed ring of a (C3-C10) aliphatic ring and a (C6-C18) aromatic ring, a substituted or unsubstituted (C6-C18) aryl, or a substituted or unsubstituted (5-18 membered) heteroaryl. For example, Ar2 and Ar3 may each independently be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted chrysenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted benzofluorenyl, or a substituted or unsubstituted dihydrophenanthrenyl.

[0036] In one embodiment, the substituted or unsubstituted (C6-C30) aryl in Ar1 may be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylenyl, or substituted or unsubstituted phenanthrenyl, preferably phenyl which is unsubstituted or substituted with deuterium or (5-30 membered) heteroaryl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted m-terphenyl, or substituted or unsubstituted naphthyl.

[0037] In one embodiment, the substituted or unsubstituted (C3-C30) heteroaryl in Ar1 may be substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzquinolinyl, substituted or unsubstituted benzquinazolinyl, substituted or unsubstituted benzquinoxalinyl, substituted or unsubstituted dibenzquinolinyl, substituted or unsubstituted dibenzquinazolinyl, substituted or unsubstituted dibenzquinoxalinyl, substituted or unsubstituted indenopyridyl, substituted or unsubstituted indenopyrimidinyl, substituted or unsubstituted indenopyrazinyl, substituted or unsubstituted benzofuropyridyl, substituted or unsubstituted benzofuropyrimidinyl, substituted or unsubstituted benzofuropyrazinyl, substituted or unsubstituted benzothiopyridyl, substituted or unsubstituted benzothiopyrimidinyl, substituted or unsubstituted benzothiopyrazinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, preferably substituted or unsubstituted pyridyl, carbazolyl substituted with unsubstituted or (C6-C30) aryl, substituted or unsubstituted benzocarbazolyl, quinazolinyl substituted with unsubstituted or (C6-C30) aryl and / or (5-30 membered) heteroaryl, quinoxalinyl substituted with unsubstituted or (C6-C30) aryl and / or (5-30 membered) heteroaryl, benzquinoxalinyl substituted with unsubstituted or (C6-C30) aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or triazinyl substituted with unsubstituted or (C6-C30) aryl and / or (5-30 membered) heteroaryl.

[0038] In one embodiment, L1 may be a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5-30 membered) heteroarylene, preferably a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (5-25 membered) heteroarylene, more preferably a single bond, a substituted or unsubstituted (C6-C18) arylene, or a substituted or unsubstituted (5-18 membered) heteroarylene. For example, L1 may be a single bond, or a substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthrenylene, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted triazinylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted quinoxalinylene, substituted or unsubstituted quinazolinylene, substituted or unsubstituted dibenzofuranylene, or substituted or unsubstituted benzquinoxalinylene, preferably a substituted or unsubstituted phenylene, substituted or unsubstituted p-biphenylene, substituted or unsubstituted m-biphenylene, substituted or unsubstituted o-biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted pyridylene, substituted or unsubstituted triazinylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted quinoxalinylene, substituted or unsubstituted quinazolinylene, substituted or unsubstituted dibenzofuranylene, or substituted or unsubstituted benzquinoxalinylene.

[0039] In one embodiment, a may be an integer of 1 or 2, b may be an integer of 1 or 2, and when a and b are 2, each of L1 and each of Ar1 may be the same or different.

[0040] According to one embodiment, the organic electroluminescent compound represented by the above formula 1 can be more specifically exemplified by, but not limited to, the following compounds.

Chemical formula

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

[0041] The organic electroluminescent compound of formula 1 according to the present disclosure can be prepared as shown in the following reaction schemes 1 to 3, but is not limited thereto. Furthermore, it can be prepared by synthetic methods known to those skilled in the art. [ka] [ka]

[0042] In the above reaction schemes 1 to 3, R1 to R 12 , L1, and Ar1 are as defined in Equation 1 above, and R 13 ~R 16 is R5~R in the above equation 1. 12 It is as defined above.

[0043] As described above, exemplary synthetic examples of the compounds represented by Formula 1 according to the present disclosure are described. These are based on, for example, Suzuki cross-coupling reaction, Backward-Hartwig cross-coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, Miyaura borylation 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, etc. It will be understood by those skilled in the art that the above reactions will proceed even when other substituents defined in Formula 1 other than the substituents described in the specific synthetic examples are bonded.

[0044] An organic electroluminescent compound according to another embodiment can be represented by the following Formula 2.

Chemical Formula

[0045] In Formula 2, R’1 to R’4 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl, or may be linked with adjacent substituents to form a ring; R’5 and R’6 each independently represent hydrogen or deuterium; L’1 to L’3 each independently represent a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3-30 membered) heteroarylene; Ar’ represents substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (3-30 membered) heteroaryl; BFL represents substituted or unsubstituted benzo[a]fluorenyl, substituted or unsubstituted benzo[b]fluorenyl, or substituted or unsubstituted benzo[c]fluorenyl; m represents an integer from 1 to 4, n represents an integer from 1 to 3, and when m and n are 2 or more, each R'5 and each R'6 may be the same or different.

[0046] In one embodiment, R'1 to R'4 may each independently be hydrogen, deuterium, substituted or unsubstituted (C1 - C30) alkyl, or substituted or unsubstituted (C6 - C30) aryl, preferably, substituted or unsubstituted (C1 - C10) alkyl, or substituted or unsubstituted (C6 - C25) aryl, more preferably, substituted or unsubstituted (C1 - C4) alkyl. For example, all of R'1 to R'4 may be methyl.

[0047] In one embodiment, all of R'5 and R'6 may be hydrogen, or all of R'5 and R'6 may be deuterium.

[0048] In one embodiment, L'1 to L'3 may each independently be a single bond, substituted or unsubstituted (C6 - C30) arylene, or substituted or unsubstituted (5 - 30 membered) heteroarylene, preferably, a single bond, substituted or unsubstituted (C6 - C25) arylene, or substituted or unsubstituted (5 - 25 membered) heteroarylene, more preferably, a single bond, substituted or unsubstituted (C6 - C18) arylene, or substituted or unsubstituted (5 - 18 membered) heteroarylene. For example, L'1 to L'3 may each independently be a single bond, or substituted or unsubstituted phenylene, or substituted or unsubstituted carbazolylene.

[0049] In one embodiment, Ar’ may be a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5-30 membered) heteroaryl, preferably a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5-25 membered) heteroaryl, more preferably a substituted or unsubstituted (C6-C18) aryl or a substituted or unsubstituted (5-18 membered) heteroaryl. For example, Ar’ may be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, p-biphenyl which is unsubstituted or substituted with deuterium, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzothiophenyl, or a substituted or unsubstituted dibenzofuranyl.

[0050] In one embodiment, BFL may be a substituted or unsubstituted benzo[a]fluorenyl, a substituted or unsubstituted benzo[b]fluorenyl, or a substituted or unsubstituted benzo[c]fluorenyl, and the substituents of these substituted benzo[a]fluorenyl, substituted benzo[b]fluorenyl, or substituted benzo[c]fluorenyl may be deuterium, (C1-C10) alkyl, or (C6-C18) aryl, for example, deuterium, methyl, or phenyl.

[0051] According to one embodiment, the organic electroluminescent compound represented by the above formula 2 can be more specifically exemplified by, but not limited to, the following compounds.

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0052] The organic electroluminescent compound of Formula 2 according to the present disclosure can be produced by referring to the reactions represented by the above Reaction Schemes 1 to 3, but is not limited thereto. Further, it can be prepared by synthetic methods known to those skilled in the art.

[0053] An organic electroluminescent compound according to another embodiment can be represented by the following Formula 3.

Chemical formula

[0054] In Formula 3, R’ 11 ~R’ 14 each independently represents substituted or unsubstituted methyl; R’ 15 and R’ 16 each independently represents hydrogen or deuterium; Ar’ 11 and Ar’ 12 each independently represents phenyl which is unsubstituted or substituted with deuterium, biphenyl which is unsubstituted or substituted with deuterium, terphenyl which is unsubstituted or substituted with deuterium, naphthyl which is unsubstituted or substituted with deuterium, a group of the following formula (a) which is unsubstituted or substituted with deuterium, or a combination thereof:

Chemical formula

[0055] In one embodiment, all of R’ 11 ~R’ 14 may be unsubstituted methyl.

[0056] In one embodiment, R’ 15 and R’ 16may all be hydrogen, or R' 15 and R' 16 may all be deuterium.

[0057] In one embodiment, Ar' 11 and Ar' 12 may each independently be unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted biphenyl, unsubstituted or deuterium-substituted terphenyl, unsubstituted or deuterium-substituted naphthyl, unsubstituted or deuterium-substituted group of the above formula (a), or a combination thereof, and preferably be unsubstituted phenyl, unsubstituted o-biphenyl, unsubstituted m-biphenyl, unsubstituted or deuterium-substituted p-biphenyl, unsubstituted o-terphenyl, unsubstituted m-terphenyl, unsubstituted p-biphenyl, unsubstituted group of the above formula (a), or a combination thereof.

[0058] According to one embodiment, the organic electroluminescent compounds represented by the above formula 3 can be more specifically exemplified by, but not limited to, the following compounds: [ka] [ka]

[0059] The organic electroluminescent compound of formula 3 according to the present disclosure can be prepared by referring to, but not limited to, the reactions shown in the above reaction schemes 1 to 3. Furthermore, it can be prepared by synthetic methods known to those skilled in the art.

[0060] The present disclosure can provide an organic electroluminescent material comprising the organic electroluminescent compound of Formula 1 and an organic electroluminescent device comprising the organic electroluminescent material.

[0061] Furthermore, the present disclosure can provide an organic electroluminescent compound of Formula 2 and an organic electroluminescent device including the same.

[0062] Furthermore, the present disclosure can provide an organic electroluminescent compound of Formula 3 and an organic electroluminescent device including the same.

[0063] According to one embodiment of the present disclosure, the organic electroluminescent material of the present disclosure may only include the organic electroluminescent compound of Formula 1, or may further include a conventional material included in the organic electroluminescent material. In one embodiment, the compound of Formula 1 may be included as a hole transport material in the hole transport zone. The hole transport zone may be composed of one or more layers selected from the group consisting of a hole transport layer, a hole injection layer, an electron blocking layer, and a hole assisting layer, and each of the layers may be composed of one or more layers. In another embodiment, the compound of Formula 1 may be included as an electron transport material in the electron transport zone. The electron transport zone may be composed of one or more layers selected from the group consisting of an electron transport layer, an electron injection layer, a hole blocking layer, and an electron assisting layer, and each of the layers may be composed of one or more layers. In another embodiment, the compound of Formula 1 may be included as a host material in the light emitting layer.

[0064] According to another embodiment of the present disclosure, the organic electroluminescent compound represented by Formula 2 and / or the organic electroluminescent compound represented by Formula 3 may be included as a hole transport material in the hole transport zone.

[0065] In addition to the organic electroluminescent compound of Formula 1, the organic electroluminescent material of the present disclosure may further include at least one host compound and at least one dopant.

[0066] The host material included in the organic electroluminescent material of the present disclosure may further include an organic electroluminescent compound different from the organic electroluminescent compound of Formula 1 (the first host material) as a second host material. That is, the organic electroluminescent material according to an embodiment of the present disclosure may include a plurality of host materials. Specifically, the plurality of host materials according to an embodiment may include at least one compound of Formula 1 as the first host material, and may also include at least one second host material different from the first host material. The weight ratio between the first host material and the second host material is in the ratio of 1:99 to 99:1, preferably in the ratio of 10:90 to 90:10, more preferably in the ratio of 30:70 to 70:30.

[0067] The second host material according to an embodiment includes a compound represented by the following Formula 11.

Chemical formula

[0068] In Formula 11, L a represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene; Ar a represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 membered) heteroaryl, R9 and R 10are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-50 membered) heteroaryl, 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, a substituted or unsubstituted condensed ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C2-C30)alkenylamino, substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, substituted or unsubstituted (C1-C30)alkyl(3-30 membered)heteroarylamino, substituted or unsubstituted (C2-C30)alkenyl(C6-C30)arylamino, substituted or unsubstituted (C2-C30)alkenyl(3-30 membered)heteroarylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, substituted or unsubstituted mono- or di-(3-30 membered)heteroarylamino, or substituted or unsubstituted (C6-C30)aryl(3-30 membered)arylamino, or adjacent substituents may be bonded to each other to form a ring; f and g each independently represent an integer from 1 to 4, and when f and g are 2 or more, each of R9 and R 10 may be the same or different from each other.

[0069] The second host material represented by Formula 11 according to one embodiment can be represented by the following Formula 12 or 13.

Chemical formula

[0070] In Formulas 12 and 13, L a, Ar a , R9, R 10 , and f are as defined in Equation 11 above; T1 and T2 each independently represent a single bond, O, or S; L b is as defined as L in Equation 11 above a ; Ar b is as defined as Ar in Equation 11 above a ; R 11 ~R 14 are each independently as defined as R9 in Equation 11 above; X1 represents O, S, or NR a ; R a represents substituted or unsubstituted (C6 - C30) aryl; g’ and h each independently represent an integer from 1 to 3, i and k each independently represent an integer from 1 to 4, j represents an integer of 1 or 2, and when g’, h, i, j, and k are 2 or more, each of R 10 , each of R 11 , each of R 12 , each of R 13 , and each of R 14 may be the same or different.

[0071] In one embodiment, L a and L b may each independently be a single bond or substituted or unsubstituted (C6 - C30) arylene, preferably a single bond or substituted or unsubstituted (C6 - C25) arylene, more preferably a single bond or substituted or unsubstituted (C6 - C18) arylene. For example, L a and L b may each independently be a single bond, phenylene, or biphenylene.

[0072] In one embodiment, Ar a and Ar bmay each independently be a substituted or unsubstituted (C6-C30) aryl, preferably a substituted or unsubstituted (C6-C25) aryl, more preferably unsubstituted or a (C6-C25) aryl substituted with a (C6-C30) aryl or a (5-30 membered) heteroaryl. For example, Ar a and Ar b may each independently be unsubstituted or phenyl substituted with at least one of methyl, cyano, triphenylsilane, phenyl, biphenyl, naphthyl, carbazolyl which is unsubstituted or substituted with phenyl, o-biphenyl which is substituted or unsubstituted, m-biphenyl which is substituted or unsubstituted, p-terphenyl which is substituted or unsubstituted, m-terphenyl which is substituted or unsubstituted, o-terphenyl which is substituted or unsubstituted, fluorenyl which is substituted or unsubstituted, naphthyl which is unsubstituted or substituted with phenyl, or triphenylenyl which is substituted or unsubstituted.

[0073] In one embodiment, R a may be a substituted or unsubstituted (C6-C30) aryl, preferably a substituted or unsubstituted (C6-C25) aryl, more preferably unsubstituted or a (C6-C25) aryl substituted with a (C6-C30) aryl or a (5-30 membered) heteroaryl. For example, R a may be unsubstituted or phenyl substituted with at least one of phenyl, biphenyl, naphthyl, carbazolyl which is unsubstituted or substituted with phenyl, o-biphenyl which is substituted or unsubstituted, m-biphenyl which is substituted or unsubstituted, p-terphenyl which is substituted or unsubstituted, m-terphenyl which is substituted or unsubstituted, o-terphenyl which is substituted or unsubstituted, naphthyl which is unsubstituted or substituted with phenyl, or triphenylenyl which is substituted or unsubstituted.

[0074] In one embodiment, R9 to R 14is, independently of each other, hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl, preferably hydrogen, substituted or unsubstituted (C1-C10) alkyl, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5-25 membered) heteroaryl, more preferably hydrogen, substituted or unsubstituted (C1-C4) alkyl, substituted or unsubstituted (C6-C18) aryl, or substituted or unsubstituted (5-18 membered) heteroaryl. For example, R9-R 14 may each independently be hydrogen, substituted or unsubstituted methyl, substituted or unsubstituted phenyl, or substituted or unsubstituted carbazolyl.

[0075] According to one embodiment, the compound represented by Formula 11 can be more specifically exemplified by, but is not limited to, the following compounds.

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0076] The compound of Formula 11 according to the present disclosure can be prepared by synthetic methods known to those skilled in the art.

[0077] The dopant contained in the organic electroluminescent material of the present disclosure can be at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant.The phosphorescent dopant material applied to the present disclosure is not particularly limited, but preferably can be a metal complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), optionally, a metal complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), more preferably an ortho-metal complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and even more preferably an ortho-metal iridium complex compound.

[0078] The dopant included in the organic electroluminescent device of the present disclosure may be, but is not limited to, a compound represented by the following formula 101: [ka]

[0079] In Equation 101, L is the following structure 1 to 3: [ka] is selected from In structures 1 to 3, R 100 ~R 103each 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, cyano, substituted or unsubstituted (3-30 membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; or adjacent substituents may be bonded to each other to form a ring, for example, a ring with pyridine, such as substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted benzofuropyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuroquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenoquinoline; R 104 ~R 107 each 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 membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or adjacent substituents may be bonded to each other to form a ring, for example, a ring together with benzene, such as substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuropyridine, or substituted or unsubstituted benzothienopyridine; R 201 ~R 220 each 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 adjacent substituents can be linked to each other to form a ring; s represents an integer of 1 to 3.

[0080] In particular, specific examples of the dopant compound include, but are not limited to, the following. [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula]

[0081] Hereinafter, an organic electroluminescent device to which the aforementioned organic electroluminescent compound and / or organic electroluminescent material is applied will be described.

[0082] An organic electroluminescent device according to an embodiment includes a first electrode, a second electrode, and at least one organic layer sandwiched between the first electrode and the second electrode. The organic layer may include at least one layer selected from a hole transport layer, a hole injection layer, an electron blocking layer, a hole assisting layer, a light emission assisting layer, a light emitting layer, an electron transport layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron assisting layer, and each layer may be further composed of a plurality of layers. Further, the organic layer may further include at least one compound selected from the group consisting of arylamine compounds and styrylarylamine compounds, and may further include at least one metal selected from the group consisting of metals of Group 1, Group 2, transition metals of the 4th period, transition metals of the 5th period, lanthanides, and organometals of d-transition elements in the periodic table, or at least one complex compound containing such a metal.

[0083] In the present disclosure, the compound represented by Formula 1 and / or the compound represented by Formula 2 may be included in one or more layers constituting an organic electroluminescent device. According to one embodiment, the organic layer includes a hole transport zone and / or an electron transport zone, and / or a light-emitting layer containing an organic electroluminescent compound according to the present disclosure, for example, a hole transport layer and / or a hole auxiliary layer and / or a hole blocking layer and / or an electron auxiliary layer and / or a light-emitting layer. For example, when the compound of Formula 1 is included in the hole transport layer and / or the hole auxiliary layer and / or the hole blocking layer and / or the electron auxiliary layer and / or the light-emitting layer, the compound of Formula 1 may be included as a hole transport material and / or a hole auxiliary material and / or a hole blocking material and / or an electron auxiliary material and / or a host material, respectively. The hole transport layer and / or the hole auxiliary layer and / or the hole blocking layer and / or the electron auxiliary layer and / or the light-emitting layer may include, for example, the organic electroluminescent compound of the present disclosure alone, or a mixture of at least two organic electroluminescent compounds, and may further include a conventional material contained in the organic electroluminescent material.

[0084] According to one embodiment, the hole transport layer may include at least one organic electroluminescent compound represented by Formula 1. For example, the hole transport layer may include at least one compound selected from Compounds C-1 to C-700 represented by Formula 1. According to another embodiment, the hole transport layer may include at least one organic electroluminescent compound represented by Formula 2. For example, the hole transport layer may include at least one compound selected from Compounds C1-1 to C1-69 represented by Formula 2. According to another embodiment, the hole transport layer may include at least one organic electroluminescent compound represented by Formula 3. For example, the hole transport layer may include at least one compound selected from Compounds C2-1 to C2-38 represented by Formula 3.

[0085] The light-emitting layer according to one embodiment may include a plurality of host materials including at least one first host material represented by Formula 1 and at least one second host material represented by Formula 11. According to one embodiment, the light-emitting layer may include at least one compound among Compounds C-1 to C-700 as the first host material represented by Formula 1 and at least one compound among Compounds H-1 to H-85 as the second host material represented by Formula 11. According to another embodiment, the light-emitting layer may include an organic electroluminescent compound represented by Formula 2. For example, the light-emitting layer may include at least one compound among Compounds C1-1 to C1-69 represented by Formula 2.

[0086] The hole blocking layer according to another embodiment may include at least one organic electroluminescent compound represented by Formula 1. For example, the hole blocking layer may include at least one among Compounds C-1 to C-700 represented by Formula 1.

[0087] The organic electroluminescent material according to one embodiment can be used as a material for the organic layer of a white organic light-emitting device. The white organic light-emitting device has suggested various structures such as the parallel side-by-side arrangement method, the stacked arrangement method, or the color conversion material (CCM) method, etc., depending on the arrangement of the light-emitting units of R (red), G (green), YG (yellow-green), or B (blue). In addition, the organic electroluminescent material according to one embodiment can also be applied to an organic electroluminescent device including QD (quantum dots).

[0088] One of the first electrode and the second electrode may be an anode, and the other may be a cathode. In this case, the first electrode and the second electrode can be formed as a transmissive conductive material, a semi-transmissive conductive material, or a reflective conductive material, respectively. The organic electroluminescent device can be a top-emitting type, a bottom-emitting type, or a double-sided emitting type depending on the types of materials forming the first electrode and the second electrode.

[0089] A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the light-emitting layer. The hole injection layer may be multilayered to reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, where each of the multilayers can use two compounds simultaneously. The hole injection layer can be doped with a p-type dopant. Also, the electron blocking layer can be disposed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can prevent light emission leakage by confining excitons within the light-emitting layer by blocking the overflow of electrons from the light-emitting layer. The hole transport layer or the electron blocking layer can be multiple layers, in which case each layer can use multiple compounds.

[0090] An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof can be used between the light-emitting layer and the cathode. The electron buffer layer may be multilayered to control the injection of electrons and improve the interfacial properties between the light-emitting layer and the electron injection layer, where each of the multilayers can use two compounds simultaneously. The hole blocking layer or the electron transport layer may be multilayered, where each of the multilayers can use multiple compounds. Also, the electron injection layer can be doped with an n-type dopant.

[0091] The light-emitting auxiliary layer can be disposed between the anode and the light-emitting layer or between the cathode and the light-emitting layer. When the light-emitting auxiliary layer is disposed between the anode and the light-emitting layer, it can be used to promote hole injection and / or hole transport or to prevent electron overflow. When the light-emitting auxiliary layer is disposed between the cathode and the light-emitting layer, it can be used to promote electron injection and / or electron transport or to prevent hole overflow. In addition, the hole auxiliary layer can be disposed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can be effective in promoting or blocking the hole transport rate (or hole injection rate), thereby enabling the control of the charge balance. When the organic electroluminescent device includes two or more hole transport layers, the additionally included hole transport layer can be used as a hole auxiliary layer or an electron blocking layer. The light-emitting auxiliary layer, the hole auxiliary layer or the electron blocking layer can have the effect of improving the efficiency and / or lifetime of the organic electroluminescent device.

[0092] In the organic electroluminescent device of the present disclosure, at least one layer (hereinafter referred to as "surface layer") preferably selected from a chalcogenide layer, a metal halide layer and a metal oxide layer can be disposed on the inner surface of one or both electrodes. Specifically, a chalcogenide (including oxide) layer of silicon and aluminum is preferably disposed on the anode surface of the electroluminescent medium layer, and a metal halide layer or a metal oxide layer is preferably disposed on the cathode surface of the electroluminescent medium layer. The operating stability of the organic electroluminescent device can be obtained by the surface layer. Preferably, examples of the chalcogenide include SiO X (1 ≤ X ≤ 2), AlO X (1 ≤ X ≤ 1.5), SiON, SiAlON, etc., examples of the metal halide include LiF, MgF2, CaF2, rare earth metal fluorides, etc., and examples of the metal oxide include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0093] Furthermore, in the organic electroluminescent device of the present disclosure, preferably, the mixed region of the electron transport compound and the reducing dopant or the mixed region of the hole transport compound and the oxidizing dopant can be disposed on at least one surface of the pair of electrodes. In this case, since the electron transport compound is reduced to an anion, injection and transport of electrons from the mixed region to the electroluminescent medium become easier. Furthermore, since the hole transport compound is oxidized to a cation, injection and transport of holes from the mixed region to the electroluminescent medium become easier. 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 and emitting white light can be fabricated by using the reducing dopant layer as a charge generation layer.

[0094] To form each layer of the organic electroluminescent device of the present disclosure, dry film formation methods such as vacuum evaporation, sputtering, plasma, ion plating methods, etc., or wet film formation methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating methods, etc., can be used.

[0095] When using a wet film formation method, the thin film can be formed by dissolving or dispersing the material for forming each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent in which the material for forming each layer can be dissolved or dispersed and there is no problem with the film-forming ability.

[0096] When forming a layer with an organic electroluminescent compound according to an embodiment, the layer can be formed by the methods listed above and can often be formed by co-evaporation or co-evaporation of mixtures. Co-evaporation is a co-evaporation method in which two or more materials are placed in their respective individual crucible sources, and current is passed through both cells simultaneously to evaporate the materials; co-evaporation of mixtures is a co-evaporation method in which two or more materials are mixed in one crucible source before evaporation, and then current is passed through one cell to evaporate the materials.

[0097] According to one embodiment, the organic electroluminescent device of the present disclosure can be used for the manufacture of display devices such as smartphones, tablets, notebooks, PCs, TVs, etc., or display devices for vehicles, or lighting devices such as outdoor or indoor lighting.

[0098] Hereinafter, in order to understand the present disclosure in detail, a method for preparing a compound according to the present disclosure will be described with reference to representative compounds or intermediate compounds.

Examples

[0099] [Example 1] Synthesis of Compound C1-14

Chemical formula

[0100] 2) Synthesis of Compound 2 Compound 1 (60.0 g, 250 mmol), H2SO4 (202 mL, 375 mmol), and 500 mL of benzene were placed in a flask, and then stirred under reflux at 120 °C for 2 hours. After the reaction was completed, the mixture was neutralized with sodium bicarbonate (NaHCO3), then extracted with MC, and then dried over MgSO4. Next, it was separated by column chromatography, and then MeOH was added thereto. Thereafter, the obtained solid was filtered under reduced pressure to obtain Compound 2 (50.0 g, yield: 90%).

[0101] 3) Synthesis of Compound 3 Compound 2 (20.0 g, 90.0 mmol) was placed in a flask and dissolved in a THF solution. Next, while filling with nitrogen, a solution of MeMgBr (3 M in THF) (45 mL, 135 mmol) was added dropwise at 0 °C, and then stirred for 2 hours. After the reaction was completed, the mixture was neutralized with isopropyl alcohol (IPA) and an aqueous NH4Cl solution, then extracted with MC, and subsequently dried using MgSO4. Next, it was separated by column chromatography, and then MeOH was added thereto. Thereafter, the obtained solid was filtered under reduced pressure to obtain Compound 3 (23.0 g, yield: 107%).

[0102] 4) Synthesis of Compound 4 Compound 3 (18.6 g, 78 mmol) and 78 mL of thionyl chloride (1 M in MC) solution were placed in a flask, and then stirred at 0 °C for 2 hours. After the temperature was lowered to -78 °C, 78 mL of trimethylaluminum (AlMe3) (2 M in toluene) solution was added thereto, then stirred for 3 hours, and subsequently reacted overnight at room temperature. After the reaction was completed, IPA and H2O were added to quench the solution, and then the layers were separated using MC. Next, it was separated by column chromatography, and then MeOH was added thereto. Thereafter, the obtained solid was filtered under reduced pressure to obtain Compound 4 (18.7 g, yield: 101%).

[0103] 5) Synthesis of Compound 5 Compound 4 (19.2 g, 81 mmol) and 200 mL of DMF were placed in a flask. While filling with nitrogen, N-bromosuccinimide (NBS) (26.0 g, 146 mmol) dissolved in 100 mL of DMF was added dropwise, and then the reaction was carried out overnight with stirring. After the reaction was completed, ethyl acetate (EA) and H2O were added thereto, and then the organic layer was separated and the organic solvent was removed. Next, this was separated by column chromatography, and then MeOH was added thereto. Thereafter, the obtained solid was filtered under reduced pressure to obtain Compound 5 (23.2 g, yield: 90%).

[0104] 6) Synthesis of Compound C1-14 Compound 5 (5.59 g, 24.8 mmol), N-([1,1'-biphenyl]-4-yl)-11,11-dimethyl-11H-benzo[b]fluorene-2-amine (10.2 g, 24.8 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (0.81 g, 0.89 mmol), tri-tert-butylphosphine (P(t-Bu)3) (0.359 g, 1.77 mmol), sodium tert-butoxide (NaOt-Bu) (3.41 g, 35.5 mmol), and 60 mL of toluene were placed in a flask and stirred at 120 °C for 1.5 hours. After the reaction was completed, the organic solvent was removed, and then the obtained solid was separated by column chromatography. Next, MeOH was added thereto, and then the obtained solid was filtered under reduced pressure to obtain Compound C1-14 (1.3 g, yield: 11%).

[0105] [Table 1]

[0106] [Example 2] Synthesis of Compound C-14 [Chemical Formula] Compound 5 (6.0 g, 19.0 mmol), 2,4-diphenyl-6-(3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-3-yl)-1,3,5-triazine (11.7 g, 22.8 mmol), Pd(PPh3)4 (1.10 g, 0.95 mmol), K2CO3 (7.9 g, 57 mmol), 50 mL of toluene, 25 mL of EtOH, and 25 mL of H2O were placed in a flask and stirred under reflux at 140 °C. After the reaction was completed, the organic solvent was removed, and the resulting solid was separated by column chromatography. Next, MeOH was added thereto, and then the resulting solid was filtered under reduced pressure to obtain Compound C-14 (2.4 g, yield: 20.3%).

[0107]

Table 2

[0108] [Example 3] Synthesis of Compound C-578

Chemical formula

[0109] 1) Synthesis of Compound 1-1 9,9,10,10-Tetramethyl-9,10-dihydrophenanthrene (34.0 g, 144 mmol), iodine (I2) (18.3 g, 71.9 mmol), iodic acid (12.7 g, 71.9 mmol), 280 mL of acetic acid (AcOH), 36 mL of H2SO4, 36 mL of water (H2O), and 15 mL of CHCl3 were placed in a flask and stirred at 65 °C. After the reaction was completed, the solvent was removed, and then it was separated by column chromatography. Next, MeOH was added thereto, and then the resulting solid was filtered under reduced pressure to obtain Compound 1-1 (56.0 g, yield: 107%).

[0110] 2) Synthesis of Compound 1-2 Compound 1-1 (35.0 g, 96.6 mmol), 5-chloro-2-formyl-phenyl)boronic acid (21.4 g, 116 mmol), Pd(PPh3)4 (5.58 g, 4.83 mmol), K2CO3 (33.4 g, 242 mmol), 300 mL of toluene, 100 mL of EtOH, and 100 mL of H2O were placed in a flask and stirred at 140 °C. After the reaction was completed, EA and H2O were added to the reaction mixture to separate the layers, and then only the organic layer was separated. The solvent was removed by vacuum filtration and then separated using column chromatography. Next, MeOH was added thereto, and then the obtained solid was filtered under reduced pressure to obtain Compound C1-2 (36.0 g, yield: 99.4%).

[0111] 3) Synthesis of Compound 1-3 Compound 1-2 (30.0 g, 80.0 mmol), chloro-(methoxymethyl)-triphenyl-λ5-phosphane (38.4 g, 112 mmol), and 370 mL of THF were placed in a flask and dissolved. Then, 112 mL of KOt-Bu (1 M in THF) solution was added dropwise thereto with stirring. After the reaction was completed, EA and H2O were added to the reaction mixture to separate the layers, and then only the organic layer was separated. The solvent was removed by vacuum filtration and then separated using column chromatography. Next, MeOH was added thereto, and then the obtained solid was filtered under reduced pressure to obtain Compound 1-3 (20.0 g, yield: 62.0%).

[0112] 4) Synthesis of Compound 1-4 Compound 1-3 (19.0 g, 47.2 mmol) and 250 mL of MC were placed in a flask and dissolved. Then, 17.8 mL of BF3·EtOEt solution was added dropwise thereto at 0 °C with stirring. After the reaction was completed, MC and NaHCO3(aq) were added thereto to separate the layers, and then only the organic layer was separated. The solvent was removed by vacuum filtration and then separated using column chromatography. Next, MeOH was added thereto, and then the obtained solid was filtered under reduced pressure to obtain Compound 1-4 (16.0 g, yield: 91.5%).

[0113] 5) Synthesis of Compound C-578 Compound 1-4 (6.0 g, 16.2 mmol), N-phenyldibenzofuran-3-amine (4.40 g, 17.0 mmol), Pd2(dba)3 (0.741 g, 0.809 mmol), sphos (0.664 g, 1.62 mmol), NaOt-Bu (3.11 g, 32.4 mmol), and 80 mL of o-xylene were placed in a flask and stirred under reflux at 180 °C. After the reaction was completed, the solvent was removed by vacuum filtration and then separated using column chromatography. Next, MeOH was added thereto, and then the obtained solid was filtered under reduced pressure to obtain Compound C-578 (2.3 g, yield: 23.9%).

[0114] [Table 3]

[0115] [Example 4] Synthesis of Compound C-470 [Chemical Formula]

[0116] 1) Synthesis of Compound 2-1 3-Bromo-9,9,10,10-tetramethyl-9,10-dihydrophenanthrene (30.0 g, 95.2 mmol), 4,4,4’,4’,5,5,5’,5’-octamethyl-2,2’-bi(1,3,2-dioxaborolane) (29.0 g, 114.1 mmol), PdCl2(PPh3)2 (3.34 g, 4.76 mmol), KOAc (23.3 g, 237.9 mmol), and 500 mL of 1,4-dioxane were placed in a flask and stirred at 140 °C for 3 hours. After the reaction was completed, the organic solvent was removed, and then the obtained solid was separated by column chromatography. Next, MeOH was added thereto, and then the obtained solid was filtered under reduced pressure to obtain Compound 2-1 (31 g, yield: 90%).

[0117] 2) Synthesis of Compound C-470 Compound 2-1 (6.0 g, 16.6 mmol), 2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (7.94 g, 18.2 mmol), Pd(PPh3)4 (0.960 g, 0.83 mmol), K2CO3 (6.88 g, 49.8 mmol), 40 mL of toluene, 20 mL of EtOH, and 20 mL of H2O were placed in a flask and then stirred at 140 °C for 2 hours. After the reaction was completed, the organic solvent was removed, and the resulting solid was separated by column chromatography. Next, MeOH was added thereto, and the resulting solid was then filtered under reduced pressure to obtain Compound C-470 (4.5 g, yield: 44%).

[0118] [Table 4]

[0119] [Example 5] Synthesis of Compound C-77 [Chemical Structure]

[0120] Compound 2-1 (4.5 g, 12.4 mmol), 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (4.65 g, 13.0 mmol), Pd(PPh3)4 (0.716 g, 0.62 mmol), K2CO3 (6.88 g, 31.0 mmol), 30 mL of toluene, 15 mL of EtOH, and 15 mL of H2O were placed in a flask and stirred at 140 °C for 2 hours. After the reaction was completed, the organic solvent was removed, and the resulting solid was separated by column chromatography. Next, MeOH was added thereto, and the resulting solid was then filtered under reduced pressure to obtain Compound C-77 (4.5 g, yield: 44%).

[0121] [Table 5]

[0122] [Example 6] Synthesis of Compound C-652 [Chemical Formula]

[0123] 1) Synthesis of Compound 3-1 10,10-Dimethylphenanthren-9(10H)-one (10.0 g, 45.0 mmol) was placed in a flask and then dissolved in a THF solution. Next, while filling with nitrogen, a solution of phenylmagnesium bromide (PhMgBr) (3 M in THF) (22.5 mL, 67.5 mmol) was added dropwise at 0 °C, and then stirred for 2 hours. After the reaction was completed, the mixture was neutralized with an aqueous NH4Cl solution, then extracted with MC, and subsequently dried over MgSO4. Next, this was separated by column chromatography. Then, MeOH was added thereto, and then the obtained solid was filtered under reduced pressure to obtain Compound 3-1 (12.5 g, yield: 92%).

[0124] 2) Synthesis of Compound C-652 Compound 3-1 (12.4 g, 41.3 mmol), N-([1,1'-biphenyl]-4-yl)-N-phenyl-[1,1'-biphenyl]-4-amine (65.6 g, 165 mmol), and 200 mL of MC were placed in a flask and then stirred at 0 °C. 6.7 mL of H2SO4 was added dropwise, and then reacted for 1 day. After the reaction was completed, the mixture was neutralized with K2CO3, then extracted with MC, and subsequently dried over MgSO4. Next, this was separated by column chromatography. Then, MeOH was added thereto, and then the obtained solid was filtered under reduced pressure to obtain Compound C-652 (8.6 g, yield: 31%).

[0125] [Table 6]

[0126] [Example 7] Synthesis of Compound C-469 [Chemical Formula]

[0127] 1) Synthesis of Compound 4-1 3-Bromophenanthrene-9,10-dione (60.0 g, 209 mmol) was placed in a flask and then dissolved in a THF solution (1 L). Next, while filling with nitrogen, a solution of MeMgBr (3 M in THF) (209 mL, 627 mmol) was added dropwise at 0 °C and then stirred for 1 hour. After the reaction was completed, MeMgBr was quenched with IPA, MeOH, and H2O and then neutralized with an aqueous NH4Cl solution. Next, the organic layer was extracted with EA and subsequently dried over MgSO4. Then, this was separated through a celite filter, and then MeOH was added thereto. Thereafter, the obtained solid was filtered under reduced pressure to obtain Compound 4-1 (74.0 g, yield: 110%).

[0128] 2) Synthesis of Compounds 4-2 and 4-3 Compound 4-1 (74.0 g, 232 mmol), H2SO4 (18.9 mL, 348 mmol), and 1,000 mL of MC were placed in a flask and then stirred under reflux at 80 °C for 1 hour. After the reaction was completed, H2O was added to the mixture to dilute H2SO4, and then the mixture was neutralized with NaHCO3. Next, this was extracted with MC and then dried over MgSO4. Then, this was separated by column chromatography, and then MeOH was added thereto. Thereafter, the obtained solid was filtered under reduced pressure to obtain Compounds 4-2 and 4-3 (60.0 g, yield: 85%).

[0129] 3) Synthesis of Compounds 4-4 and 4-5 Compound 4-2 and 4-3 (60.0 g, 199 mmol) were placed in a flask and then dissolved in a THF solution (1 L). Subsequently, while filling with nitrogen, a solution of MeMgBr (3 M in THF) (99.6 mL, 299 mmol) was added dropwise at 0 °C and stirred for 3 hours. After the reaction was completed, the mixture was neutralized with IPA and an aqueous NH4Cl solution, then extracted with MC, and subsequently dried using MgSO4. Then, this was separated by column chromatography, and then MeOH was added thereto. Next, the obtained solid was filtered under reduced pressure to obtain compounds 4-4 and 4-5 (63.2 g, yield: 100%).

[0130] 4) Synthesis of Compound 4-6 Compound 4-4 and 4-5 (63.2 g, 199.2 mmol) and 183 mL of thionyl chloride (SOCl2) (1 M in MC) solution were placed in a flask and then stirred at 0 °C for 2 hours. After the temperature was lowered to -78 °C, 183 mL of an AlMe3 (2 M in toluene) solution was added thereto, then stirred for 3 hours, and subsequently reacted overnight at room temperature. After the reaction was completed, IPA and H2O were added to quench the solution, and then the layers were separated using MC. Next, this was separated by column chromatography, and then MeOH was added thereto. Then, the obtained solid was filtered under reduced pressure to obtain compound 4-6 (59.0 g, yield: 94%).

[0131] 5) Synthesis of Compound C-469 Compound 4-6 (5.0 g, 15.7 mmol), N-([1,1'-biphenyl]-4-yl)-11,11-dimethyl-11H-benzo[b]fluorene-2-amine (8.45 g, 17.4 mmol), Pd2(dba)3 (0.719 g, 0.785 mmol), P(t-Bu)3 (0.318 g, 1.57 mmol), NaOt-Bu (3.02 g, 31.4 mmol), and 60 mL of toluene were placed in a flask and stirred at 130 °C for 1 hour. After the reaction was completed, the organic solvent was removed, and then the obtained solid was separated by column chromatography. Then, MeOH was added thereto, and then the obtained solid was filtered under reduced pressure to obtain compound C-469 (2.1 g, yield: 19%).

[0132]

Table 7

[0133] [Example 8] Synthesis of Compound C-317

Chem.

[0134]

Table 8

[0135] [Example 9] Synthesis of Compound C-400

Chem.

[0136] [Table 9]

[0137] [Example 10] Synthesis of Compound C2-31 [Chemical formula] Compound 5 (6.5 g, 20.6 mmol), Compound 10 (10.0 g, 20.6 mmol), Pd2(dba)3 (943 mg, 1.03 mmol), P(t-Bu)3 (1.0 mL, 2.06 mmol, 50% toluene solution), NaOt-Bu (3.0 g, 30.9 mmol), and 103 mL of toluene were placed in a flask and refluxed for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and then the solvent was removed by a rotary evaporator and purified by column chromatography to obtain Compound C2-31 (5.3 g, yield: 36%) as a white solid.

[0138] [Table 10]

[0139] [Example 11] Synthesis of Compound 2-8 [Chemical formula] Compound 1-1 (9.0 g, 24.8 mmol), di([1,1'-biphenyl]-4-yl)amine (9.6 g, 29.8 mmol), Pd2(dba)3 (1.1 g, 1.24 mmol), P(t-Bu)3 (1.2 mL, 2.48 mmol, 50% toluene solution), NaOt-Bu (4.8 g, 49.6 mmol), and 130 mL of toluene were placed in a flask and refluxed for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, then the solvent was removed by a rotary evaporator and purified by column chromatography to obtain Compound C2-8 (4.1 g, yield: 30%) as a white solid.

[0140] [Table 11]

[0141] [Example 12] Synthesis of Compound C2-32 [Chemical formula]

[0142] 1) Synthesis of Compound 12-1 Compound 1-1 (30.0 g, 82.8 mmol), 4-chloroaniline (21.7 g, 169.8 mmol), palladium(II) acetate (Pd(OAC)2) (1.3 g, 5.68 mmol), S-Phos (4.6 g, 11.3 mmol), NaOt-Bu (16.3 g, 169.8 mmol), and 566 mL of o-xylene were placed in a flask and refluxed for 3 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, then the solvent was removed by a rotary evaporator and purified by column chromatography to obtain Compound 12-1 (18 g, yield: 60%).

[0143] 2) Synthesis of Compound 12-2 Compound 12-1 (18.0 g, 49.7 mmol), phenylboronic acid (13.2 g, 74.6 mmol), Pd(OAc)2 (559 mg, 2.49 mmol), S-Phos (2.0 g, 4.97 mmol), NaOt-Bu (12 g, 124.4 mmol), 250 mL of o-xylene, 60 mL of 1,4-dioxane, and 60 mL of distilled water were placed in a flask and refluxed for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and then the solvent was removed by a rotary evaporator and purified by column chromatography to obtain Compound 12-2 (18.1 g, yield: 90%).

[0144] 3) Synthesis of Compound C2-32 Compound 12-2 (10.2 g, 25.2 mmol), Compound 12-3 (10.0 g, 25.2 mmol), Pd2(dba)3 (1.2 g, 1.26 mmol), P(t-Bu)3 (1.24 mL, 2.52 mmol, 50% toluene solution), NaOt-Bu (3.6 g, 37.8 mmol), and 126 mL of toluene were placed in a flask and then refluxed for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and then the solvent was removed by a rotary evaporator and purified by column chromatography to obtain Compound C2-32 (5.9 g, yield: 33%) as a white solid.

[0145] [Table 12]

[0146] [Example 13] Synthesis of Compound C-696 [Chemical formula] 3-Bromo-9,9,10,10-tetramethyl-9,10-dihydrophenanthrene (5.5 g, 10.4 mmol), 2,4-diphenyl-6-(8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenz[b,d]furan-1-yl)-1,3,5-triazine (4.3 g, 13.5 mmol), Pd(PPh3)4 (0.6 g, 0.52 mmol), K2CO3 (2.8 g, 20.8 mmol), 100 mL of toluene, 20 mL of H2O, and 20 mL of EtOH were placed in a flask and stirred at 150 °C. After the reaction was completed, EA and H2O were added to the reaction mixture to separate the layers, and then only the organic layer was separated. Then, the solvent was removed by vacuum filtration and subsequently separated using column chromatography. Next, MeOH was added thereto, and then the obtained solid was filtered under reduced pressure to obtain Compound C-696 (5.4 g, yield: 83%).

[0147] [Table 13]

[0148] [Example 14] Synthesis of Compound C-697 [Chemical formula]

[0149] 1) Synthesis of Compound 11 3-Bromo-9,9,10,10-tetramethyl-9,10-dihydrophenanthrene (13.3 g, 42.1 mmol), (9H-carbazol-2-yl)boronic acid (13.3 g, 63.1 mmol), Pd(PPh3)4 (2.43 g, 2.1 mmol), K2CO3 (11.6 g, 84.2 mmol), 210 mL of toluene, 40 mL of H2O, and 20 mL of EtOH were placed in a flask and stirred at 150 °C. After the reaction was completed, only the organic layer was separated by adding EA and H2O, and then the solvent was removed by filtration under reduced pressure. Then, this was separated by column chromatography and then MeOH was added thereto. Next, the obtained solid was filtered under reduced pressure to obtain Compound 11 (6.9 g, yield: 40.8%).

[0150] 2) Synthesis of Compound C-697 Compound 11 (6.9 g (15.9 mmol)), 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (6.8 g, 17.5 mmol), Pd(OAc)2 (0.18 g, 0.8 mmol), S-Phos (0.65 g, 1.59 mmol), NaOt-Bu (3.0 g, 31.8 mmol), and 160 mL of o-xylene were placed in a flask and then stirred at 180 °C. After the reaction was completed, only the organic layer was separated by adding EA and H2O, and then the solvent was removed by filtration under reduced pressure. Then, this was separated by column chromatography and then MeOH was added thereto. Next, the obtained solid was filtered under reduced pressure to obtain Compound C-697 (4.8 g, yield: 42.8%).

[0151] [Table 14]

[0152] [Example 15] Synthesis of Compound C-572 [Chemical Formula]

[0153] 1) Synthesis of Compound 12 9-Chloro-5,5,6,6-tetramethyl-5,6-dihydrobenzo[k]tetraphene (7.5 g, 20.2 mmol), 4,4,4’,4’,5,5,5’,5’-octamethyl-2,2’-bi(1,3,2-dioxaborolane) (10.3 g, 40.4 mmol), Pd2(dba)3 (0.92 g, 1.01 mmol), S-Phos (0.83 g, 2.02 mmol), KOAC (4.95 g, 50.5 mmol), and 100 mL of 1,4-dioxane were placed in a flask and then stirred at 180 °C. After the reaction was completed, only the organic layer was separated by adding EA and H2O, and then the solvent was removed by vacuum filtration. Then, this was separated by column chromatography and then MeOH was added thereto. Next, the obtained solid was filtered under reduced pressure to obtain Compound 12 (9.6 g, yield: 95%).

[0154] 2) Synthesis of Compound C-572 Compound 12 (9.6 g, 20.7 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.3 g, 19.7 mmol), Pd(pph3)4 (1.13 g, 0.98 mmol), K2CO3 (5.4 g, 39.4 mmol), 200 mL of toluene, 40 mL of EtOH, and 40 mL of H2O were placed in a flask and then stirred at 160 °C. After the reaction was completed, only the organic layer was separated by adding EA and H2O, and then the solvent was removed by vacuum filtration. Then, this was separated by column chromatography and then MeOH was added thereto. Next, the obtained solid was filtered under reduced pressure to obtain Compound C-572 (8.5 g, yield: 80%).

[0155]

Table 15

[0156] Hereinafter, in order to understand the present disclosure in detail, the light-emitting characteristics of an organic electroluminescent device including the organic electroluminescent compound of the present disclosure will be described.

[0157] [Device Example 1-1] Manufacturing of an OLED Containing an Organic Electroluminescent Compound According to the Present Disclosure An OLED was manufactured using the organic electroluminescent compound of the present disclosure. First, an indium tin oxide (ITO) thin film (10 Ω / sq) (Diomatech Co., Ltd., Japan) on a glass substrate for the OLED was sequentially subjected to ultrasonic cleaning with acetone, ethanol, and distilled water, and then stored in isopropanol and subsequently used. After evacuating until the degree of vacuum in the chamber reached 10 -6 Torr, the ITO substrate was mounted on the substrate holder of a vacuum evaporation apparatus. Then, Compound HT-1 was introduced into a cell of the vacuum evaporation apparatus, and Compound HI-1 was introduced into another cell of the vacuum evaporation apparatus. The two materials were evaporated at different speeds and deposited at a doping amount of 3 wt% each to form a hole injection layer having a thickness of 10 nm on the ITO substrate. Next, Compound HT-1 was introduced into a cell of the vacuum evaporation apparatus, and a current was passed through the cell to evaporate it, thereby forming a first hole transport layer having a thickness of 90 nm on the hole injection layer. Next, Compound C1-14 described in Table 1 below was introduced into another cell of the vacuum evaporation apparatus, and a current was passed through the cell to evaporate it, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, an emission layer was formed thereon as follows: Compound RH was placed in one cell of the vacuum evaporation apparatus as a host, and Compound D-39 was placed in another cell as a dopant. The two materials were evaporated, and the dopant was deposited at a doping amount of 2 wt% based on the total amount of the host and the dopant to form an emission layer having a thickness of 40 nm on the second hole transport layer. Next, Compound ET and Compound EI in another two cells were evaporated at a ratio of 1:1 to deposit an electron transport layer having a thickness of 35 nm on the emission layer. Next, Compound EI was deposited as an electron injection layer having a thickness of 2 nm, and then an Al cathode having a thickness of 80 nm was deposited on the electron injection layer using another vacuum evaporation apparatus. Thus, the OLED was manufactured.

[0158] [Comparative Example 1-1] Manufacturing of an OLED Containing a Conventional Compound An OLED was manufactured in the same manner as in Device Example 1-1, except that compound NPB was used as the material for the second hole transport layer.

[0159] The driving voltage, luminous efficiency, and color coordinates of the OLEDs according to Device Example 1-1 and Comparative Example 1-1 manufactured as described above at a luminance of 1,000 nits, and the time required for the light emission to decrease from 100% to 95% at a luminance of 10,000 nits (lifetime; T95) were measured, and the results are shown in Table 1-1 below:

[0160]

Table 16

[0161] [Device Examples 1-2 to 1-4] Manufacture of an Organic Electroluminescent Device Containing an Organic Electroluminescent Compound According to the Present Disclosure An OLED was manufactured in the same manner as in Device Example 1-1, except that compound RH-2 was used as the host of the light-emitting layer and the compounds described in Table 1-2 below were used as the materials for the second hole transport layer.

[0162] [Comparative Example 1-2] Manufacture of an OLED Containing a Conventional Compound An OLED was manufactured in the same manner as in Device Example 1-1, except that compound RH-2 was used as the host of the light-emitting layer and the compounds described in Table 1-2 below were used as the materials for the second hole transport layer.

[0163] The time required for the light emission to decrease from 100% to 95% at a luminance of 10,000 nits (lifetime; T95) of the OLEDs according to Device Examples 1-2 to 1-4 and Comparative Example 1-2 manufactured as described above was measured, and the results are shown in Table 1-2 below.

[0164]

Table 17

[0165] By including the organic electroluminescent compound according to the present disclosure in the hole transport zone, an organic electroluminescent device having a low driving voltage, high luminous efficiency, and long life characteristics can be provided.

[0166] [Device Examples 2-1 and 2-2] Manufacture of an OLED Containing the Organic Electroluminescent Compound According to the Present Disclosure An OLED according to the present disclosure was manufactured. First, an indium tin oxide (ITO) thin film (10 Ω / sq) (Diomatech Co., Ltd., Japan), which is a transparent electrode on a glass substrate for an OLED, was sequentially subjected to ultrasonic cleaning with acetone and isopropyl alcohol, then stored in isopropanol, and then used. Next, the ITO substrate was mounted on the substrate holder of a vacuum evaporation apparatus. Thereafter, Compound HI-1 was introduced into a cell of the vacuum evaporation apparatus, and Compound HT-1 was introduced into another cell of the vacuum evaporation apparatus. The two materials were evaporated at different speeds, and Compound HI-1 was deposited at a doping amount of 3% by weight based on the total amount of the two materials to form a hole injection layer having a thickness of 10 nm. Next, Compound HT-1 was deposited as a first hole transport layer having a thickness of 80 nm on the hole injection layer. Next, Compound HT-2 was introduced into another cell of the vacuum evaporation apparatus, and a current was passed through the cell to evaporate it, thereby forming a second hole transport layer having a thickness of 30 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, an emission layer was formed thereon as follows: The compounds shown in Table 2 below were introduced into one cell of the vacuum evaporation apparatus as a host, and Compound D-50 was introduced into another cell as a dopant. At the same time, the dopant material was evaporated at different speeds and deposited at a doping amount of 10% by weight based on the total amount of the host and the dopant to form an emission layer having a thickness of 40 nm on the hole transport layer. Next, Compound ET and Compound EI as materials for the electron transport layer were deposited at a weight ratio of 40:60 to form an electron transport layer having a thickness of 35 nm on the emission layer. After depositing Compound EI as a material for the electron injection layer having a thickness of 2 nm on the electron transport layer, an 80 nm thick Al cathode was deposited on the electron injection layer by another vacuum evaporation apparatus. Thus, an OLED was fabricated. Each compound used for all the materials was 10 -6It was purified by vacuum sublimation with toluene.

[0167] [Device Examples 2-3 and 2-4] Fabrication of an OLED Containing a Plurality of Host Materials According to the Present Disclosure An OLED was fabricated in the same manner as in Device Example 2-1, except that the compounds shown in Table 2 below were used as host materials, and two host materials were evaporated at different rates of 1:2 to deposit the light-emitting layer.

[0168] [Comparative Example 2] Fabrication of an OLED Containing a Conventional Compound as a Host An OLED was fabricated in the same manner as in Device Example 2-1, except that only compound CBP was used as the host material for depositing the light-emitting layer, compound BAlq was used as the hole-blocking layer material for depositing a 5-nm-thick hole-blocking layer on the light-emitting layer, and then compounds ET and EI as the electron-transporting layer materials were deposited at a weight ratio of 40:60 to form a 30-nm-thick electron-transporting layer on the hole-blocking layer.

[0169] The driving voltage, luminous efficiency, power efficiency, and emission color of the OLEDs according to Device Examples 2-1 to 2-4 and Comparative Example 2 fabricated as described above at a luminance of 1,000 nits, and the time required for the emission to decrease from 100% to 95% at a luminance of 20,000 nits (lifetime; T95) were measured, and the results are shown in Table 2 below.

[0170]

Table 18

[0171] By including the organic electroluminescent compound according to the present disclosure and a plurality of host materials contained in the light-emitting layer, it is possible to provide a long-life organic electroluminescent device having not only a low driving voltage and excellent light-emitting characteristics but also a significantly improved lifetime compared to an OLED containing a conventional host material.

[0172] [Device Example 3-1] Fabrication of an OLED Containing a Compound According to the Present Disclosure An OLED was fabricated using the organic electroluminescent compound of the present disclosure. First, an indium tin oxide (ITO) thin film (10 Ω / sq) (Diomatech Co., Ltd., Japan), which is a transparent electrode on a glass substrate for OLED, was sequentially subjected to ultrasonic cleaning with acetone, ethanol, and isopropyl alcohol, then stored in isopropanol, and then used. After evacuating until the degree of vacuum in the chamber reached 10 -6 Torr, the ITO substrate was mounted on the substrate holder of a vacuum evaporation apparatus. Then, compound HT-1 was introduced into a cell of the vacuum evaporation apparatus, and compound HI-1 was introduced into another cell of the vacuum evaporation apparatus. The two materials were evaporated at different speeds, and each compound was deposited at a doping amount of 3 wt% to form a hole injection layer having a thickness of 10 nm on the ITO substrate. Next, compound HT-1 was then introduced into a cell of the vacuum evaporation apparatus, and a current was passed through the cell to evaporate it, thereby forming a first hole transport layer having a thickness of 75 nm on the hole injection layer. Next, compound HT-3 was then introduced into another cell of the vacuum evaporation apparatus, and a current was passed through the cell to evaporate it, thereby forming a second hole transport layer having a thickness of 5 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light-emitting layer was formed thereon as follows: Compound BH-1 was introduced into one cell of the vacuum evaporation apparatus as a host, and compound BD was introduced into the other cell as a dopant. Then, the two materials were evaporated, and the dopant was deposited at a doping amount of 2 wt% based on the total amount of the host and the dopant to form a light-emitting layer having a thickness of 20 nm on the second hole transport layer. Next, compound C-14 was deposited as a hole blocking material to form a hole blocking layer having a thickness of 5 nm. Compounds ET and EI in another two cells were evaporated at a ratio of 1:1 to deposit an electron transport layer having a thickness of 30 nm on the hole blocking layer. After depositing compound EI as an electron injection layer having a thickness of 2 nm, an Al cathode having a thickness of 80 nm was deposited by another vacuum evaporation apparatus. Thus, an OLED was fabricated.

[0173] [Comparative Example 3-1] Fabrication of an OLED Containing a Conventional Compound An OLED was fabricated in the same manner as in Device Example 3-1, except that the hole-blocking layer was not deposited, and compounds ET and EI as the electron transport layer were evaporated at a rate of 1:1 to deposit an electron transport layer with a thickness of 33 nm on the light-emitting layer.

[0174] The driving voltage, current efficiency, and CIE color coordinates of the OLEDs according to Device Example 3-1 and Comparative Example 3-1 fabricated as described above were measured at a luminance of 1,000 nits, and the results are shown in Table 3-1 below.

[0175]

Table 19

[0176] [Device Examples 3-2 and 3-3] Fabrication of OLEDs Containing Compounds According to the Present Disclosure An OLED was fabricated in the same manner as in Device Example 3-1, except that compound BD-1 was used as the dopant material and the compounds shown in Table 3-2 below were used as the materials for the hole-blocking layer.

[0177] [Comparative Example 3-2] Fabrication of OLEDs Containing Conventional Compounds An OLED was fabricated in the same manner as in Device Example 3-1, except that the hole-blocking layer was not deposited, compound BD-1 was used as the dopant material, and compounds ET and EI were evaporated at a rate of 1:1 to deposit an electron transport layer with a thickness of 35 nm on the light-emitting layer.

[0178] The driving voltage, current efficiency, and CIE color coordinates of the OLEDs according to Device Examples 3-2 and 3-3 and Comparative Example 3-2 fabricated as described above were measured at a luminance of 1,000 nits, and the results are shown in Table 3-2 below.

[0179]

Table 20

[0180] By including the organic electroluminescent compound according to the present disclosure in the hole-blocking layer, an organic electroluminescent device having low driving voltage and / or high luminous efficiency characteristics can be provided.

[0181] [Device Example 4]: Manufacture of a red-emitting OLED according to the present disclosure The OLED according to the present disclosure was manufactured as follows: First, an indium tin oxide (ITO) thin film (10 Ω / sq) (Geomatec Co., Ltd., Japan), which is a transparent electrode on a glass substrate for OLED, was sequentially subjected to ultrasonic cleaning with acetone and isopropyl alcohol, then stored in isopropanol, and then used. Next, the ITO substrate was mounted on the substrate holder of a vacuum evaporation apparatus. Thereafter, compound HI-1 was introduced into the cell of the vacuum evaporation apparatus, and compound HT-1 was introduced into another cell of the vacuum evaporation apparatus. The two materials were evaporated at different speeds, and compound HI-1 was deposited with a doping amount of 3 wt% based on the total amount of the two materials to form a hole injection layer having a thickness of 10 nm. Next, compound HT-1 was deposited as a first hole transport layer having a thickness of 80 nm on the first hole injection layer. Then, compound HT-4 was introduced into another cell of the vacuum evaporation apparatus and evaporated by passing an electric current through the cell, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, an emission layer was formed thereon as follows: Each of the first host compound and the second host compound shown in Table 4 below was introduced into two cells of the vacuum evaporation apparatus as a host, and compound D-39 was introduced into another cell as a dopant. The two host materials were evaporated at a ratio of 1:1, and at the same time the dopant was evaporated at different speeds. The dopant was deposited with a doping amount of 3 wt% based on the total amount of the host and the dopant to form an emission layer having a thickness of 40 nm on the second hole transport layer. Next, compound ET and compound EI were deposited at a weight ratio of 50:50 as materials for the electron transport material layer to form an electron transport layer having a thickness of 35 nm on the emission layer. After depositing compound EI as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 80 nm was deposited on the electron injection layer by another vacuum evaporation apparatus. The OLED was thus fabricated. Each compound used for all the materials was purified by vacuum sublimation in toluene. -6 Purified by vacuum sublimation in toluene.

[0182] [Comparative Example 4] Manufacture of an OLED Containing a Conventional Compound as a Host An OLED was fabricated in the same manner as in Device Example 4, except that compound CBP was used alone as the host of the light-emitting layer.

[0183] The driving voltage, luminous efficiency, and emission color of the OLEDs according to Device Example 4 and Comparative Example 4 fabricated as described above at a luminance of 1,000 nits, and the time required for the emission to decrease from 100% to 95% at a luminance of 5,000 nits (lifetime; T95) were measured, and the results are shown in Table 4 below.

[0184]

Table 21

[0185] The compounds used in the above device examples and comparative examples are shown in Table 5 below.

[0186]

Table 22

[0187]

Table 23

[0188]

Table 24

[0189] Furthermore, in the organic electroluminescent compound represented by Formula 1 according to the present disclosure, the LUMO (lowest unoccupied molecular orbital) energy level, HOMO (highest occupied molecular orbital) energy level, and triplet energy level of the compound in which R5 to R 12 are linked to adjacent substituents to form a benzene ring or a naphthalene ring were measured respectively, and the results are shown in Table 6 below.

[0190]

Table 25

[0191] * The structure was optimized by applying hybrid density functional theory (hybrid DFT) (B3LYP) and the 6-31G(d) basis function system using the Gaussian quantum chemistry calculation program Gaussian16. The triplet state was calculated using TD-DFT (time-dependent DFT).

[0192] Referring to Table 6 above, in the organic electroluminescent compound represented by Formula 1 according to the present disclosure, even when R5 to R8 and / or R9 to R 12 are bonded to adjacent substituents to form a benzene ring or naphthalene, it can be confirmed that this has the energy level of the main core that can be used as a material for OLEDs according to the present disclosure. The present invention may include the following aspects. [Aspect 1] The following formula 1: [Chemical formula] [[ID=**3**]](In the formula, R 1 ~R 4 [[ID=**4**]] are each independently, *-(L 1 ) a -(Ar 1 ) b [[ID=**5**]], hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl, or may be linked to adjacent substituents to form a ring; R 5 ~R 12 [[ID=**6**]] are each independently, *-(L 1 ) a -(Ar 1 ) b [[ID=**7**]], hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted condensed ring of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, 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, or substituted or unsubstituted tri(C6-C30) arylsilyl, or may be linked to adjacent substituents to form a ring, provided that; R 1 ~R 12 [[ID=**8**]] at least one of is *-(L 1 ) a -(Ar 1 ) b [[ID=**9**]]; L 1 [[ID=**10**]] represents a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3-30 membered) heteroarylene; Ar 1 [[ID=**11**]] represents substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, or -N-(Ar 2 )(Ar 3 [[ID=**12**]]); Ar 2 [[ID=**13**]] and Ar 3 [[ID=**14**]] are each independently, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted condensed ring of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl; [[ID=**15**]] a represents an integer of 1 or 2, b represents an integer of 1 to 4, and when a and b are 2 or more, each L 1 [[ID=**16**]] and each Ar 1 [[ID=**17**]] may be the same or different; R 5 ~R 10 [[ID=**18**]] and R 12 [[ID=**19**]] represent hydrogen and R 11 [[ID=**20**]] represents a compound of formula 1 containing a substituted amino group, provided that it is excluded) The organic electroluminescent compound represented by [Aspect 2] Ar 1 is a substituted or unsubstituted (3-30 membered) heteroaryl containing at least one N, or -N-(Ar 2 )(Ar 3 ); L 1 represents a single bond or a substituted or unsubstituted (C6-C30) arylene, The organic electroluminescent compound according to Aspect 1. [Aspect 3] The compound represented by Formula 1 above is one of the following Formulas 1-1 to 1-4:

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Claims

1. Formula 2 below: 【Chemical 1】 (In the formula, R' １ ~R' ４ each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C3 to C30) cycloalkyl, substituted or unsubstituted (3 to 7 membered) heterocycloalkyl, substituted or unsubstituted (C6 to C30) aryl, or substituted or unsubstituted (3 to 30 membered) heteroaryl, or may be linked to adjacent substituents to form a ring; R' ５ and R' ６ each independently represents hydrogen or deuterium; L' １ ~L' ３ each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene; Ar' represents a substituted or unsubstituted (C6 to C30) aryl or a substituted or unsubstituted (3 to 30 membered) heteroaryl; BFL represents substituted or unsubstituted benzo[a]fluorenyl, substituted or unsubstituted benzo[b]fluorenyl, or substituted or unsubstituted benzo[c]fluorenyl; m represents an integer of 1 to 4, n represents an integer of 1 to 3, and when m and n are 2 or more, , each R' ５ and each R' ６ may be the same or different) An organic electroluminescent compound represented by the formula:

2. The compound of formula 2 is the following compound: 【Chemical Formula 2】 【Chemistry 3】 【Chemistry 4】 2. The organic electroluminescent compound according to claim 1, selected from:

3. An organic electroluminescent device comprising the organic electroluminescent compound of claim 1.

Images