COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THESE

Abstract

The present disclosure relates to a compound and an organic electroluminescent device comprising the same. By incorporating the compound according to the present disclosure as an organic electroluminescent material, an organic electroluminescent device can be provided having features of low drive voltage and / or high efficiency and / or long lifetime.

Description

Technical field

[0001] The present disclosure relates to a compound and an organic electroluminescent device comprising the same. State of the art

[0002] An organic electroluminescent device (OLED) is a self-emitting display device that has advantages such as a wider viewing angle, higher contrast ratio, and faster response time. In such an OLED, the application of an electrical voltage injects holes from the anode and electrons from the cathode into a light-emitting layer, and the recombination of the holes and electrons generates high-energy excitons. Due to the energy, the organic light-emitting compound enters an excited state and emits light from the energy when the organic light-emitting compound returns from the excited state to the ground state.

[0003] It has been pointed out that, unlike the high-efficiency red and green phosphors that have already been commercialized among OLED light-emitting materials, blue phosphors are unsuitable for long-term use, such as several years or more, due to the short lifetime and high drive voltage of blue phosphors, and thus, fluorescent materials are used instead. Therefore, conventional materials have failed to meet the light-emitting characteristics of OLEDs, so the development of an OLED containing an organic electroluminescent material with excellent performance is required.

[0004] Korean Laid-Open Patent Application No. 2015-0121394 discloses an organic electroluminescent device comprising a quinazoline derivative substituted by a heterocyclic group containing at least one nitrogen atom as a material for an electron-transport layer, and Korean Laid-Open Patent Application No. 2017-0105040 discloses a light-emitting device comprising a phenanthroline derivative as a material for an electron-transport layer. However, the references do not specifically disclose an organic electroluminescent device comprising a phenanthroline derivative as a material for an N-type charge generation layer according to the present disclosure. Disclosure of the inventionTechnical problem

[0005] The object of the present disclosure is, firstly, to provide a compound with which an organic electroluminescent device having features of a low driving voltage and / or a high efficiency and / or a long lifetime can be produced, and an organic electroluminescent material comprising the same, and secondly to provide an organic electroluminescent device comprising the compound and the organic electroluminescent material. Solution to the problem

[0006] As a result of intensive studies to solve the above technical problem, the inventors of the present invention have found that the above problem can be solved by a compound represented by the following formula 1, thereby completing the present invention.

[0007] In Formula 1 R1 represents hydrogen, deuterium, a halogen, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted (C1-C 30 )-alkyl or a substituted or unsubstituted (3- to 30-membered) heteroaryl; R2 to R8 each independently represent hydrogen, deuterium, a halogen, cyano, a substituted or unsubstituted (C1-C 30 )-alkyl, a substituted or unsubstituted (C2-C 30 )-alkenyl, a substituted or unsubstituted (C6-C 30 )-aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-cycloalkyl, a substituted or unsubstituted (C3-C 30 )-cycloalkenyl, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, a substituted or unsubstituted (C1-C30 )-alkoxy, a substituted or unsubstituted tri-(C1-C 30 )-alkylsilyl, a substituted or unsubstituted di-(C1-C 30 )-alkyl-(C6-C 30 )-arylsilyl, a substituted or unsubstituted (C1-C 30 )-Alkyldi-(C6-C 30 )-arylsilyl, a substituted or unsubstituted tri-(C6-C 30 )-arylsilyl, a substituted or unsubstituted fused ring of an aliphatic (C3-C 30 ) ring and an aromatic (C6-C 30 )-ring or -L-HAr; or they may be bonded to the adjacent substituent to form (a) ring(s); with the proviso that at least one of R2 to R8 is -L-HAr; L represents a single bond, a substituted or unsubstituted (C6-C 30 )-arylene or a substituted or unsubstituted (3- to 30-membered) heteroarylene and HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl containing at least one nitrogen atom; with the proviso that when R4 or R5 is -L-HAr, the compounds in which HAr is quinazoline are excluded. Advantageous effects of the invention

[0008] By using the compound according to the present disclosure and an organic electroluminescent material comprising the same, an organic electroluminescent device having features of a low driving voltage and / or a high efficiency and / or a long lifetime can be manufactured. Embodiment of the invention

[0009] The present disclosure is described in detail below. However, the following description is intended to illustrate the invention and is not intended to limit the scope of the invention in any way.

[0010] The present disclosure relates to a compound represented by formula 1, an organic electroluminescent material comprising the compound, and an organic electroluminescent device comprising the organic electroluminescent material.

[0011] 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, as needed, in any material layer from which an organic electroluminescent device is constructed.

[0012] "Organic electroluminescent material" herein means a material that can be used in an organic electroluminescent device and may comprise at least one compound. The organic electroluminescent material may be included in any layer constituting an 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-emitting auxiliary material, an electron-blocking material, a light-emitting material (containing host and dopant materials), an electron-buffering material, a hole-blocking material, an electron-transporting material, or an electron-injecting material, etc.

[0013] "(C1-C 30)-Alkyl(ene)" here means a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, the number of carbon atoms being preferably 1 to 20, more preferably 1 to 10. The above alkyl may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. "(C3-C 30)-Cycloalkyl(ene)" here means a mono- or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7. The above cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, etc. "(3- to 7-membered) heterocycloalkyl" in the present disclosure 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 and preferably the group consisting of O, S and N, and includes tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, etc. "(C6-C 30)-Aryl(ene)" in the present disclosure means a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring skeleton carbon atoms, wherein the number of ring skeleton carbon atoms is preferably 6 to 20, more preferably 6 to 15, and may be partially saturated and may comprise a spiro structure. Examples of the aryl include, in particular, phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthrenyl, benzophenanthrenyl, phenylphenanthrenyl, anthracenyl, benzanthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, Chrysenyl, Benzochrysenyl, Naphthacenyl, Fluoranthenyl, Benzofluoranthenyl, Tolyl, Xylyl, Mesityl, Cumenyl, Spiro[fluorenfluoren]yl, Spiro[fluoren-benzofluoren]yl, Azulenyl,Tetramethyldihydrophenanthrenyl etc ein. Insbesondere kann es sich bei dem Aryl um o-Tolyl, m-Tolyl, p-Tolyl, 2,3-Xylyl, 3,4-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]phenanthryl, 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, etc. “(3- to 30-membered) heteroaryl(ene)” in the present disclosure is an aryl having 3 to 30 ring skeleton atoms, which includes at least one heteroatom selected from the group consisting of B, N, O, S, Si, P, Se, Te and Ge, wherein the number of ring skeleton atoms is preferably 3 to 30,more preferably 5 to 20. The number of heteroatoms in the heteroaryl is preferably 1 to 4. The above heteroaryl may be a monocyclic ring or a fused ring condensed with at least one benzene ring, and may be partially saturated. Furthermore, the above heteroaryl or heteroarylene herein may be formed by linking at least one heteroaryl or aryl group to a heteroaryl group via one or more single bonds and may comprise a spiro structure. Examples of the heteroaryl may specifically include a monocyclic ring type heteroaryl including furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a condensed ring type heteroaryl including benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl,Dibenzoselenophenyl, Benzofurochinolinyl, Benzofurochinazolinyl, Benzofuronaphthiridinyl, Benzofuropyrimidinyl, Naphthofuropyrimidinyl, Benzothienochinolinyl, Benzothienochinazolinyl, Benzothienonaphthyridinyl, Benzothienopyrimidinyl, Naphthothienopyrimidinyl, Pyrimidoindolyl, Benzopyrimidoindolyl, Benzofuropyrazinyl, Naphthofuropyrazinyl, Benzothienopyrazinyl, Naphthothienopyrazinyl, Pyrazinoindolyl, Benzopyrazinoindolyl, Benzoimidazolyl, Benzothiazolyl, Benzoisothiazolyl, Benzoisoxazolyl, Benzoxazolyl, Imidazopyridinyl, Isoindolyl, Indolyl, Benzoindolyl, Indazolyl, Benzothiadiazolyl, Chinolyl, Isochinolyl, Cinnolinyl, Chinazolinyl, Chinoxalinyl, Carbazolyl, Azacarbazolyl, Benzocarbazolyl, Dibenzocarbazolyl, Phenoxazinyl, Phenanthridinyl, Benzodioxolyl, Indolizidinyl, Acridinyl, Silafluorenyl, Germafluorenyl, Benzotriazolyl, Phenazinyl, Imidazopyridinyl, Chromenochinazolinyl, Thiochromenochinazolinyl, Dimethylbenzoperimidinyl, Indolocarbazolyl,Indenocarbazolyl etc. einschließt. Insbesondere kann es sich beim Heteroaryl um 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-Indolizidinyl, 2-Indolizidinyl, 3-Indolizidinyl, 5-Indolizidinyl, 6-Indolizidinyl, 7-Indolizidinyl, 8-Indolizidinyl, 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-Chinolyl, 3-Chinolyl, 4-Chinolyl,5-Chinolyl, 6-Chinolyl, 7-Chinolyl, 8-Chinolyl, 1-Isochinolyl, 3-Isochinolyl, 4-Isochinolyl, 5-Isochinolyl, 6-Isochinolyl, 7-Isochinolyl, 8-Isochinolyl, 2-Chinoxalinyl, 5-Chinoxalinyl, 6-Chinoxalinyl, 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-Germafluorenyl, 2-Germafluorenyl, 3-Germafluorenyl, 4-Germafluorenyl, 1-Dibenzoselenophenyl, 2-Dibenzoselenophenyl, 3-Dibenzoselenophenyl,4-Dibenzoselenophenyl, etc. Furthermore, "heteroaryl(ene)" can be divided into a heteroaryl(ene) with electron properties and a heteroaryl(ene) with hole properties. A heteroaryl(ene) with electron properties is a substituent that is relatively electron-rich in the underlying nucleus and can be, for example, a substituted or unsubstituted pyridinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, or a substituted or unsubstituted quinolyl, etc. A heteroaryl(ene) with hole properties is a substituent that is relatively electron-poor in the underlying nucleus and can be, for example, a substituted or unsubstituted carbazolyl,a substituted or unsubstituted dibenzofuranyl or a substituted or unsubstituted dibenzothiophenyl. Here, the term "a fused ring of an aliphatic (C3-C, 30 ) ring and an aromatic (C6-C 30)-ring" means a ring formed by fusing at least one aliphatic ring having 3 to 30 ring skeleton carbon atoms, wherein the number of carbon atoms is preferably 3 to 25, more preferably 3 to 18, with at least one aromatic ring having 6 to 30 ring skeleton carbon atoms, wherein the number of carbon atoms is preferably 6 to 25, more preferably 6 to 18. For example, the fused ring can 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. Here, the carbon atoms in the fused ring can be an aliphatic (C3-C 30 ) ring and an aromatic (C6-C 30) 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.

[0014] In addition, "ortho-" ("o-"), "meta-" ("m-"), and "para-" ("p-") are intended to indicate the substitution position of all substituents. An ortho configuration describes a compound with substituents that are adjacent to each other, e.g., at positions 1 and 2 on benzene. A meta configuration describes the next substitution position from the immediately adjacent substitution position, e.g., a compound with substituents at positions 1 and 3 on benzene. A para configuration shows the next substitution position from the meta position, e.g., a compound with substituents at positions 1 and 4 on benzene.

[0015] The term "a ring formed upon linking to an adjacent substituent" herein means a substituted or unsubstituted (3- to 30-membered) mono- or polycyclic, alicyclic, aromatic ring, or a combination thereof formed by linking or fusing two or more adjacent substituents, and may preferably be a substituted or unsubstituted (5- to 25-membered) mono- or polycyclic, alicyclic, aromatic ring, or a combination thereof. Furthermore, the formed ring may include at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably N, O, and S. According to one embodiment 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.In one embodiment, the fused ring may 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 benzofluorene 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.

[0016] In addition, the term "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a particular functional group is replaced by another atom or functional group, that is, a substituent. Unless otherwise stated, the substituents in positions where the substituents may be substituted may not be limited to hydrogen, and when two or more hydrogen atoms in a functional group are replaced by a substituent, the substituents may be the same or different. For example, "a substituent to which two or more substituents are bonded" may be a pyridinetriazine. That is, pyridinetriazine may be heteroaryl or be interpreted as a substituent in which two heteroaryl groups are bonded.Preferably, the substituted alkyl, the substituted alkenyl, the substituted aryl(ene), the substituted heteroaryl(ene), the substituted cycloalkyl, the substituted cycloalkenyl, the substituted heterocycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl and the substituted fused ring of an aliphatic ring and an aromatic ring in the formulas of the present disclosure are each independently substituted by at least one element selected from the group consisting of deuterium, a halogen, cyano, carboxyl, nitro, hydroxyl, a (C1-C 30 )-alkyl, halogen-(C1-C 30 )-alkyl, (C2-C 30 )-alkenyl, (C2-C 30 )-alkynyl, (C1-C 30 )-alkoxy, (C1-C 30 )-alkylthio, (C3-C 30 )-cycloalkyl, (C3-C 30 )-Cycloalkenyl, (3- to 7-membered) heterocycloalkyl, (C6-C30 )-aryloxy, (C6-C 30 )-arylthio, (5- to 30-membered) heteroaryl, which is unsubstituted or substituted by a (C6-C 30 )-aryl, a (C6-C 30 )-aryl which is unsubstituted or substituted by a (5- to 30-membered) heteroaryl, a tri-(C1-C 30 )-alkylsilyl, tri-(C6-C 30 )-arylsilyl, di-(C1-C 30 )-alkyl(C6-C 30 )-arylsilyl, (C1-C 30 )-Alkyldi-(C6-C 30 )-arylsilyl, a fused ring of an aliphatic (C3-C 30 ) ring and an aromatic (C6-C 30 )-ring, amino, a mono- or di-(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di-(C6-C 30 )-arylamino, (C1-C 30 )-alkyl(C6-C 30 )-arylamino, mono- or di-(3- to 30-membered)-heteroarylamino, (C1-C 30 )-Alkyl-(3- to 30-membered)-heteroarylamino, (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino, (C1-C 30)-Alkylcarbonyl, (C1-C 30 )-Alkoxycarbonyl, (C6-C 30 )-Arylcarbonyl, (C6-C 30 )-Arylphosphinyl, Di-(C6-C 30 )-arylboronyl, Di-(C1-C 30 )-alkylboronyl, (C1-C 30 )-Alkyl-(C6-C 30 )-arylboronyl, (C6-C 30 )-Ar-(C1-C 30 )-alkyl und (C1-C 30 )-Alkyl-(C6-C 30 )-aryl.

[0017] If a substituent is not shown in the chemical formula or compound structure of the present disclosure, it may mean that all positions that can be present as substituents are hydrogen or deuterium. That is, in the case of deuterium, an isotope of hydrogen, some hydrogen atoms may be deuterium, which is an isotope, and the deuterium content may be from 0% to 100%. In the case where the substituent is not shown in the chemical formula or compound structure of the present disclosure, if deuterium is not explicitly excluded, such as when the deuterium content is 0%, the hydrogen content is 100%, and all substituents are hydrogen, hydrogen and deuterium may be mixed and used in the compound.Deuterium is an element with a deuteron consisting of a proton and a neutron as its nucleus, being one of the isotopes of hydrogen, and it can be represented by hydrogen-2, and the element symbol can be D or . 2 H. Isotopes have the same atomic number (Z) but different mass numbers (A) and can also be interpreted as elements with the same number of protons but different numbers of neutrons.

[0018] As used herein, "combinations thereof" means that one or more of the components of the corresponding list are combined to form a known or chemically stable arrangement that one skilled in the art could devise from the corresponding list. For example, alkyl and deuterium may be combined to form partially or fully deuterated alkyl groups, halogen and alkyl may be combined to form halogenated alkyl substituents, and halogen, alkyl, and aryl may be combined to form halogenated arylalkyl.For example, preferred combinations of substituents may contain up to 50 atoms excluding hydrogen and deuterium, or up to 40 atoms excluding hydrogen and deuterium, or up to 30 atoms excluding hydrogen and deuterium, or in many cases preferred combinations of substituents may contain up to 20 atoms excluding hydrogen and deuterium.

[0019] In the formula of the present disclosure, when a plurality of substituents are indicated by the same symbol, each of the substituents represented by the same symbol may be the same as or different from each other.

[0020] The connection according to one embodiment is described below.

[0021] The compound according to one embodiment of the present disclosure is represented by the following formula 1.

[0022] In Formula 1 R1 represents hydrogen, deuterium, a halogen, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted (C1-C 30 )-alkyl or a substituted or unsubstituted (3- to 30-membered) heteroaryl; R2 to R8 each independently represent hydrogen, deuterium, a halogen, cyano, a substituted or unsubstituted (C1-C 30 )-alkyl, a substituted or unsubstituted (C2-C 30 )-alkenyl, a substituted or unsubstituted (C6-C 30 )-aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-cycloalkyl, a substituted or unsubstituted (C3-C 30 )-cycloalkenyl, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, a substituted or unsubstituted (C1-C30 )-alkoxy, a substituted or unsubstituted tri-(C1-C 30 )-alkylsilyl, a substituted or unsubstituted di-(C1-C 30 )-alkyl-(C6-C 30 )-arylsilyl, a substituted or unsubstituted (C1-C 30 )-Alkyldi-(C6-C 30 )-arylsilyl, a substituted or unsubstituted tri-(C6-C 30 )-arylsilyl, a substituted or unsubstituted fused ring of an aliphatic (C3-C 30 ) ring and an aromatic (C6-C 30 )-ring or -L-HAr; or they may be bonded to the adjacent substituent to form (a) ring(s); with the proviso that at least one of R2 to R8 is -L-HAr; L represents a single bond, a substituted or unsubstituted (C6-C 30 )-arylene or a substituted or unsubstituted (3- to 30-membered) heteroarylene and HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl containing at least one nitrogen atom; with the proviso that when R4 or R5 is -L-HAr, the compounds in which HAr is quinazoline are excluded.

[0023] In one embodiment, R1 may be hydrogen, a halogen, a substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted (C1-C 10 )-alkyl or a substituted or unsubstituted (5- to 30-membered) heteroaryl, preferably hydrogen, a halogen, phenyl which is unsubstituted or substituted by a (C1-C 10)-alkyl or (5- to 30-membered) heteroaryl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted o-biphenyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted o-terphenyl, a (C1-C 10)-alkyl which is unsubstituted or substituted by deuterium, or a substituted or unsubstituted (5- to 25-membered) heteroaryl, more preferably hydrogen, a halogen, a phenyl which is unsubstituted or substituted by a (C1-C4)-alkyl or a (5- to 25-membered) heteroaryl, an unsubstituted p-biphenyl, unsubstituted m-biphenyl, unsubstituted o-terphenyl, (C1-C4)-alkyl which is unsubstituted or substituted by deuterium, or a substituted or unsubstituted (5- to 18-membered) heteroaryl.For example, R1 may be hydrogen, F, a phenyl which is unsubstituted or substituted by tert-butyl or benzotriazolyl, unsubstituted p-biphenyl, unsubstituted m-biphenyl, unsubstituted o-biphenyl, unsubstituted m-terphenyl, unsubstituted o-terphenyl, methyl which is substituted by deuterium, tert-butyl which is unsubstituted or substituted by deuterium, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl or a substituted or unsubstituted Benzotriazolyl.

[0024] In one embodiment, R2 to R8 may each independently be hydrogen, a substituted or unsubstituted (C6-C 30)-aryl or -L-HAr, and at least one of R2 to R3 may be -L-HAr, preferably hydrogen, a substituted or unsubstituted (C6-C 25 )-aryl or -L-HAr, more preferably hydrogen, a substituted or unsubstituted (C6-C 18 )-aryl or -L-HAr. For example, R2 to R8 can each independently be hydrogen, a substituted or unsubstituted phenyl, or -L-HAr.

[0025] According to one embodiment, the compound represented by formula 1 can be represented by any of the following formulas 1-1 to 1-7.

[0026] In formulas 1-1 to 1-7 R1, L and HAr are as defined in Formula 1 and R2 to R8 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C6-C 30 )-aryl or a substituted or unsubstituted (3- to 30-membered) heteroaryl.

[0027] In one embodiment, L may be a single bond or a substituted or unsubstituted (C6-C 30 )-arylene, preferably a single bond or a substituted or unsubstituted (C6-C 25 )-arylene, more preferably a single bond or a substituted or unsubstituted (C6-C 18 )-arylene. For example, L can be a single bond, a phenylene that is substituted or substituted by at least one phenyl, a substituted or unsubstituted biphenylene, or a substituted or unsubstituted naphthylene.

[0028] In one embodiment, HAr may be a substituted or unsubstituted (5- to 30-membered) heteroaryl containing at least one nitrogen, preferably a (5- to 25-membered) heteroaryl containing at least one nitrogen atom and unsubstituted or substituted by (C6-C 30)-aryl or (5- to 30-membered) heteroaryl, more preferably a (5- to 18-membered) heteroaryl containing at least two nitrogen atoms and unsubstituted or substituted by a (C6-C 25 )-aryl or a (5- to 25-membered) heteroaryl. For example, HAr can be a quinazolinyl that is unsubstituted or substituted by at least one phenyl or at least one pyridyl, a quinoxalinyl that is unsubstituted or substituted by at least one phenyl or at least one pyridyl, or a benzotriazolyl that is unsubstituted or substituted by phenyl or dimethylfluorenyl.

[0029] In one embodiment, HAr can be illustrated by the following formulas 1-a or 1-b.

[0030] In formulas 1-a and 1-b, - - represents a position linked to L; X1 and X2 each independently represent N or CR 12 represents; Y1 to Y3 each independently represent N or NR 14 represents; place R 11 and R 12 each independently hydrogen, deuterium, a substituted or unsubstituted (C6-C 30 )-aryl or a substituted or unsubstituted (3- to 30-membered) heteroaryl; place R 13 and R 14 each independently hydrogen, deuterium, a substituted or unsubstituted (C6-C 30 )-aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl or a site directly connected to L and a represents an integer from 1 to 4, where, when a is an integer of 2 or more, each R 13 can be the same or different from each other.

[0031] In one embodiment, X1 may be N, and X2 may be CR 12 be.

[0032] In one embodiment, X1 CR 12 and X2 can be N.

[0033] In one embodiment, R 11 and R 12 each independently represents a substituted or unsubstituted (C6-C 30 )-aryl or a substituted or unsubstituted (5- to 30-membered) heteroaryl, preferably a substituted or unsubstituted (C6-C 25 )-aryl or a substituted or unsubstituted (5- to 25-membered) heteroaryl, more preferably a substituted or unsubstituted (C6-C 18 )-aryl or a substituted or unsubstituted (5- to 18-membered) heteroaryl. For example, R 11 and R 12each independently represents a phenyl which is unsubstituted or substituted by deuterium-substituted methyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl.

[0034] In one embodiment, Y1 and Y3 may be N, and Y2 may be NR 14 act, where R 14 a substituted or unsubstituted (C6-C 30 )-aryl.

[0035] In one embodiment, Y1 and Y3 may be N, and Y2 may be NR 14 act, where R 14 can be a point directly connected to L.

[0036] In one embodiment, R 13 and R 14 each independently represents hydrogen, deuterium or a substituted or unsubstituted (C6-C 30 )-aryl, preferably hydrogen, deuterium or a substituted or unsubstituted (C6-C 25 )-aryl and more preferably hydrogen, deuterium or a substituted or unsubstituted (C6-C 18 )-aryl. For example, R 13 and R 14 each independently be hydrogen, deuterium, a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl or a substituted or unsubstituted fluorenyl.

[0037] According to one embodiment, the compound represented by Formula 1 may be more specifically exemplified by, but is not limited to, the following compounds: where D nin the above compounds means that a number n of hydrogen atoms are replaced by deuterium, where n is an integer of 1 or more and the upper limit of n depends on the number of hydrogen atoms that can be replaced in each compound.

[0038] According to another embodiment, the present disclosure provides a compound selected from the following compounds and an organic electroluminescent material comprising the same.

[0039] The compound illustrated by Formula 1 according to the present disclosure can be included in an N-type charge generation layer (CGL) of an organic electroluminescent device. In the compound of Formula 1 according to the present disclosure, the phenanthroline residue includes a nitrogen having a sp 2-hybrid orbital, which is relatively electron-rich. Specifically, the phenanthroline moiety has a structure in which two nitrogen atom(s) are adjacent to each other, allowing it to form a covalent bond with surrounding hydrogen or a coordinate bond with alkali metals or alkaline earth metals, such as Li and Yb. When the compound of Formula 1 containing such a phenanthroline moiety is applied to an N-type charge generation layer, the phenanthroline moiety can enhance electron injection and transfer capabilities by capturing doped alkali metals or alkaline earth metals and increasing the electron density within the molecule.Furthermore, when the compound of Formula 1 according to the present disclosure is applied to an N-type charge generation layer of an organic electroluminescent device, the nitrogen of the phenanthroline moiety can form a gap state by bonding to an alkali metal or alkaline earth metal, which is a dopant of the N-type charge generation layer. Accordingly, the energy level difference between the N-type charge generation layer and the P-type charge generation layer is reduced, allowing electrons to be easily transferred from the N-type charge generation layer to the electron-transport layer.

[0040] The organic electroluminescent device according to one embodiment of the present disclosure may be an organic electroluminescent device having a tandem structure. In the case of a tandem organic electroluminescent device, according to one embodiment, a single light-emitting unit (light-emitting unit) may be formed in a structure in which two or more units are connected by a charge generation layer. The organic electroluminescent device may include a plurality of two or more light-emitting units, for example, a plurality of three or more light-emitting units, having a first electrode and a second electrode opposed to each other on a substrate, and a light-emitting layer disposed between the first electrode and the second electrode and emitting light in a specific wavelength range.The multiple light-emitting units may emit the same color or different colors. Furthermore, a light-emitting unit may include one or more light-emitting layers, and the multiple light-emitting layers may be light-emitting layers of the same color or different colors. It may include one or more charge generation layers located between each light-emitting unit. The charge generation layer refers to the layer in which holes and electrons are generated when a voltage is applied. When there are three or more light-emitting units, a charge generation layer may be located between each light-emitting unit. The multiple charge generation layers may be the same or different from each other.By placing the charge generation layer between light-emitting units, the current efficiency in each light-emitting unit is increased, and charges can be easily distributed. Specifically, the charge generation layer is provided between two adjacent stacks and can be used to drive a tandem organic electroluminescent device using only a single pair of anodes and cathodes, without a separate internal electrode between the stacks.

[0041] An organic electroluminescent device using the above-mentioned organic electroluminescent material according to the present disclosure will be described below.

[0042] An organic electroluminescent device according to one embodiment of the present invention includes a first electrode and a second electrode opposite each other on the first electrode, a plurality of light-emitting units disposed between the first electrode and the second electrode, and at least one charge generation layer disposed between adjacent light-emitting units. The light-emitting units include at least one light-emitting layer, and the charge generation layer includes an N-type charge generation layer and a P-type charge generation layer. In this case, the N-type charge generation layer includes at least one compound selected from the compound illustrated by Formula 1 according to the present disclosure, for example, Compounds C-1 to C-332 or Compounds C2-1 to C2-38.

[0043] An organic electroluminescent device according to one embodiment comprises at least two light-emitting units, and a charge generation layer may be disposed between adjacent light-emitting units, thereby increasing the number of light-emitting units. According to one embodiment, at least one of the plurality of light-emitting units may include a first light-emitting layer and a second light-emitting layer that are adjacent to each other.

[0044] One of the first electrode and the second electrode may be a hole-injecting anode, and the other may be an electron-injecting cathode. The first electrode and the second electrode may each be formed of a transmissive conductive material, a transflective conductive material, or a reflective conductive material. The organic electroluminescent device may be of the top-emission type, bottom-emission type, or double-side emission type according to the types of materials from which the first electrode and the second electrode are formed.

[0045] According to one embodiment, each of the light-emitting units includes each of the hole transport layers, each of the light-emitting layers, and each of the electron transport layers.

[0046] The first light-emitting unit includes a hole injection layer disposed between the first electrode and the first light-emitting layer, a first hole transport layer disposed between the hole injection layer and the first light-emitting layer, and a first electron transport layer disposed between the first light-emitting layer and the charge generation layer.

[0047] The second light-emitting unit includes a second hole-transport layer, a second light-emitting layer, a second electron-transport layer, and an electron-injection layer. The second hole-transport layer is disposed between the charge generation layer and the second light-emitting layer, and the second light-emitting layer is disposed between the second hole-transport layer and the second electrode. Furthermore, the second electron-transport layer is disposed between the second light-emitting layer and the second electrode, and the electron-injection layer is disposed between the second electron-transport layer and the second electrode.

[0048] The hole-injection layer may be composed of multiple layers to lower the hole-injection barrier (or hole-injection voltage) from the anode to the first hole-transport layer or electron-blocking layer, and two compounds may be used simultaneously in each layer. Furthermore, the hole-injection layer may be doped with a p-type dopant. Furthermore, the electron-blocking layer may be disposed between the hole-transport layer (or hole-injection layer) and the first light-emitting layer and the second light-emitting layer to block the overflow of electrons from the light-emitting layers, thereby confining excitons in the light-emitting layers and preventing light leakage. The first hole-transport layer and the second hole-transport layer or the electron-blocking layers may be composed of multiple layers, and multiple compounds may be used in each layer.If the organic electroluminescent device comprises two or more hole transport layers, the additionally included hole transport layer can be used as a hole assist layer or electron blocking layer.

[0049] The organic electroluminescent device according to one embodiment may include an auxiliary light-emitting layer disposed between the anode and the light-emitting layer or between the cathode and the light-emitting layer. When the auxiliary light-emitting layer is disposed between the anode and the light-emitting layer, it may be used to promote hole injection and / or hole transport or to prevent overflow of electrodes. When the auxiliary light-emitting layer is disposed between the cathode and the light-emitting layer, it may be used to promote electron injection and / or electron transport or to prevent overflow of holes.In addition, the hole assist layer may be disposed between the hole transport layer (or hole injection layer) and the light-emitting layer and may be effective to promote or block the hole transport rate (or hole injection rate), thereby controlling the charge balance.

[0050] The first light-emitting layer and the second light-emitting layer are light-emitting layers including a host and a dopant, and they may be a single layer or multiple layers where two or more layers are laminated. Here, the host mainly functions to promote the recombination of electrons and holes and confine excitons in the light-emitting layer, and the dopant functions to efficiently emit excitons obtained by recombination. The dopant of the first light-emitting layer and the second light-emitting layer may be doped in an amount of less than 25 wt%, preferably less than 17 wt%, and more preferably less than 10 wt%, based on the total amount of the host material and the dopant material.

[0051] According to one embodiment, the first light-emitting layer and the second light-emitting layer may be an anthracene derivative compound as the host material, and the host material may be, for example, a fluorescent blue host material. Furthermore, the first light-emitting layer and the second light-emitting layer may further include one or more dopants. One or more phosphorescent or fluorescent dopants may be used as a dopant included in the organic electroluminescent device of the present disclosure. For example, the dopant material may be a fluorescent blue dopant.

[0052] According to one embodiment of the present disclosure, an organic electroluminescent device having a tandem structure includes a charge generation layer disposed between a first light-emitting unit and a second light-emitting unit to increase the current efficiency generated in each light-emitting layer and to easily distribute charges. The charge generation layer includes an N-type charge generation layer disposed adjacent to the first light-emitting unit, thereby supplying electrons to the first light-emitting unit, and a P-type charge generation layer disposed adjacent to the second light-emitting unit, thereby supplying holes to the second light-emitting unit.

[0053] That is, the charge generation layer is disposed between the first light-emitting unit and the second light-emitting unit, and the first light-emitting unit and the second light-emitting unit are connected by the charge generation layer. The charge generation layer may be a PN junction charge generation layer in which an N-type charge generation layer and a P-type charge generation layer are juxtaposed and connected.

[0054] The N-type charge generation layer supplies electrons to the first electron transport layer of the first light-emitting unit, and the first electron transport layer supplies electrons to the first light-emitting layer adjacent to the first electrode.

[0055] According to one embodiment of the present disclosure, the N-type charge generation layer includes the above-mentioned compound represented by Formula 1. The compound of Formula 1 exhibits excellent electron mobility and thus excellent electron injection and transfer capability. Therefore, when the compound of Formula 1 is applied to an organic electroluminescent device such as a material for an N-type charge generation layer, an increase in the progressive drive voltage of the device and a decrease in lifetime can be avoided.

[0056] According to another embodiment, the N-type charge generation layer includes at least one compound selected from the compounds C2-1 to C2-38.

[0057] In one embodiment, the N-type charge generation layer may further include an n-type dopant to improve electron injection properties into the N-type charge generation layer. For example, the usable N-type dopant may further include an alkali metal such as Li, Na, K, Rb, Cs, Fr, Yb, etc., an alkaline earth metal such as Be, Mg, Ca, Sr, Ba, Ra, etc., or one or more complex compounds including such metals generally used in the art. In the N-type charge generation layer, the doping concentration of the dopant may be 0.5% to 10% of the compound of Formula 1.

[0058] The P-type charge generation layer supplies holes to the second hole-transport layer of the second light-emitting device, and the second hole-transport layer supplies holes to the second light-emitting layer adjacent to the second electrode. That is, the P-type charge generation layer is used as a hole-injection layer and can include only a hole-injection layer material or a hole-injection layer material in a mixture of a hole-transport material.

[0059] In one embodiment, the P-type charge generation layer may be composed of a metal or an organic material doped with a P-type dopant. For example, the metal may be composed of one or more alloys selected from the group consisting of Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni, and Ti. Furthermore, commonly used materials may be used for the P-type dopant and the host material used in the doped P-type organic material.

[0060] The light-emitting devices according to an embodiment may further include a hole-blocking layer between the light-emitting layers and the electron-transport layers. The hole-blocking layer is a layer that prevents holes from reaching the cathode, thereby improving the probability of electron-hole recombination in the light-emitting layer. Multiple layers may be used for the hole-blocking layer or the first electron-transport layer and the second electron-transport layer, and multiple compounds may be used in each layer. Additionally, the first electron-injection layer and the second electron-injection layer may be doped with an n-type dopant.

[0061] The organic electroluminescent device includes a first electrode and a second electrode that oppose each other, and an organic layer disposed between the first electrode and the second electrode. The organic layer may include a first light-emitting unit, a second light-emitting unit, a third light-emitting unit, a first charge generation layer, and a second charge generation layer. In another embodiment, four or more light-emitting units and three or more charge generation layers may be disposed between the first electrode and the second electrode.

[0062] The first charge generation layer and the second charge generation layer are disposed between the first light-emitting unit and the second light-emitting unit, and the second light-emitting unit, or the third light-emitting unit and the first light-emitting unit, the first charge generation layer, the second light-emitting unit, the second charge generation layer, and the third light-emitting unit are sequentially laminated on the first electrode. That is, the first light-emitting unit is disposed between the first electrode and the first charge generation layer, the second light-emitting unit is disposed between the first charge generation layer and the second charge generation layer, and the third light-emitting unit is disposed between the second electrode and the second charge generation layer.

[0063] The first light-emitting unit may include a hole-injection layer, a first hole-transport layer, a first light-emitting layer, and a first electron-transport layer sequentially laminated on the first electrode. At this time, the first electron-transport layer is disposed between the first light-emitting layer and the first charge generation layer. The hole-injection layer, the first hole-transport layer, the first light-emitting layer, and the first electron-transport layer are each described above, and thus, their descriptions are omitted.

[0064] The second light-emitting unit may include a second hole-transport layer, a second light-emitting layer, and a second electron-transport layer. The second hole-transport layer is disposed between the first charge generation layer and the second light-emitting layer, and the second electron-transport layer is disposed between the second light-emitting layer and the second charge generation layer. The second hole-transport layer, the second light-emitting layer, and the second electron-transport layer are each described above, and thus, their descriptions are omitted.

[0065] The third light-emitting unit may include a third hole-transport layer, a third light-emitting layer, a third electron-transport layer, and an electron-injection layer. The third hole-transport layer is disposed between the second charge generation layer and the third light-emitting layer, the third electron-transport layer is disposed between the third light-emitting layer and the second electrode, and the electron-injection layer is disposed between the third electron-transport layer and the second electrode. The features of the third hole-transport layer, the third electron-transport layer, and the electron-injection layer may be similar to those of the second hole-transport layer, the second electron-transport layer, and the electron-injection layer above, respectively, and their descriptions are therefore omitted.Furthermore, the characteristics of the third light-emitting layer may be similar to those of the first light-emitting layer or the second light-emitting layer. For example, the third light-emitting layer may include a fluorescent blue host material and a fluorescent blue dopant material.

[0066] In the second charge generation layer, the N-type charge generation layer is disposed between the second electron-transport layer and the third hole-transport layer, and the P-type charge generation layer is disposed between the N-type charge generation layer and the third hole-transport layer. The first and second charge generation layers generate charges or separate charges into holes and electrons, thereby supplying electrons to the first light-emitting unit, the second light-emitting unit, and the third light-emitting unit. The features of the N-type charge generation layer and the P-type charge generation layer may be similar to those of the N-type charge generation layer and the P-type charge generation layer above, respectively, and their descriptions are omitted.

[0067] In one embodiment according to the present disclosure, the N-type charge generation layer and / or the N-type charge generation layer include the above-mentioned compound illustrated by Formula 1.

[0068] To form each layer of the organic electroluminescent device of the present disclosure, dry film formation methods such as vacuum evaporation, sputtering, plasma, ion plating, etc., or wet film formation methods such as spin coating, dip coating, flooding, etc. can be used. When using a wet film formation method, a thin film can be formed by dissolving or dispersing materials constituting each layer in a suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent in which the materials constituting each layer can be dissolved or dispersed and which does not pose problems in film formability.

[0069] When forming a layer by the compound of Formula 1 according to one embodiment, the layer can be formed by the methods listed above and can often be formed by simultaneous deposition or mixed deposition. Simultaneous deposition is a mixed deposition process in which two or more materials are placed in respective individual crucible sources, and a current is applied to both cells simultaneously to evaporate the materials and perform mixed deposition; mixed deposition is a mixed deposition process in which two or more materials are mixed in a crucible source prior to deposition, and then a current is passed through a cell to evaporate the materials.

[0070] In one embodiment, when the organic electroluminescent materials are present in the same or different layers within the organic electroluminescent device, they may be deposited individually.

[0071] According to one embodiment, the present disclosure may provide a display device comprising a compound illustrated by Formula 1. Furthermore, the organic electroluminescent device of the present disclosure may be used to fabricate display devices such as smartphones, tablets, notebooks, PCs, televisions, or automotive display devices, or lighting devices such as exterior or interior lighting.

[0072] Hereinafter, the method for producing the compound according to the present disclosure will be explained with reference to the method for synthesizing a representative compound or intermediate in order to understand the present disclosure in detail. [Example 1] Synthesis of Compound C-1

[0073] 2-Chloro-9-phenyl-1,10-phenanthroline (5.3 g, 13 mmol), 2,3-diphenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline (3.8 g, 13 mmol), PdCl2amphos (0.64 g, 0.91 mmol), Aliquat 336 (0.53 g, 1.3 mmol), Na2CO3 (2.8 g, 26 mmol), 50 mL of toluene, and 17 mL of distilled water were placed in a flask and stirred at reflux at 140 °C. After 17 hours, the mixture was cooled to room temperature, distilled water was added, and the organic layer was extracted with ethyl acetate. Next, the remaining moisture was removed with magnesium sulfate, and the residue was distilled under reduced pressure and separated by column chromatography to obtain compound C-1 (2.4 g, yield: 34%). MG SP . C-1 536,2 270 °C [Example 2] Synthesis of compound C-3

[0074] 2-Chloro-9-phenyl-1,10-phenanthroline (6.8 g, 23 mmol), 2,3-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline (9.5 g, 23 mmol), PdCl2amphos (1.2 g, 1.6 mmol), Aliquat 336 (0.89 g, 2.3 mmol), Na2CO3 (2.8 g, 27 mmol), 90 mL of toluene, and 30 mL of distilled water were placed in a flask and stirred at reflux at 140 °C. After 16 hours, the mixture was cooled to room temperature, distilled water was added, and the organic layer was extracted with ethyl acetate. Next, the remaining moisture was removed with magnesium sulfate, and the residue was distilled under reduced pressure and separated by column chromatography to obtain compound C-3 (8.8 g, yield: 70%). MG SP . C-3 536,2 227 °C [Example 3] Synthesis of Compound C-5

[0075] 2-Chloro-9-phenyl-1,10-phenanthroline (7.1 g, 24 mmol), 2,4-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazoline (10 g, 24 mmol), PdCl2amphos (1.2 g, 1.7 mmol), Aliquat 336 (1.0 g, 2.5 mmol), Na2CO3 (5.2 g, 49 mmol), 122 mL of toluene, and 41 mL of distilled water were placed in a flask and stirred at 140 °C under reflux. After 3 hours, the mixture was cooled to room temperature, and the resulting solid was filtered off and then separated by column chromatography to obtain Compound C-5 (8.3 g, yield: 64%). MG SP . C-5 536,2 292 °C [Example 4] Synthesis of Compound C-57

[0076] 2-Phenyl-9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthroline (7.0 g, 15.27 mmol), 5-bromo-2,3-diphenylquinoxaline (5.5 g, 15.27 mmol), Pd(amphos)Cl2 (0.8 g, 1.07 mmol), Aliquat 336 (0.6 g, 1.53 mmol), Na2CO3 (3.2 g, 30.54 mmol), 76 mL of toluene, and 25 mL of distilled water were placed in a flask and stirred at 130 °C under reflux. After 2 h, the mixture was cooled to room temperature, and the layers were separated. Next, it was filtered through silica and recrystallized to obtain compound C-57 (6.8 g, yield: 72.72%). MG SP . C-57 612,74 276 °C [Example 5] Synthesis of Compound C-4

[0077] 2-Chloro-1,10-phenanthroline (5.0 g, 23.3 mmol), 2,3-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline (10 g, 24.5 mmol), Pd(amphos)Cl2 (1.15 g, 1.63 mmol), Na2CO3 (4.94 g, 46.6 mmol), Aliquat 336 (0.188 g, 0.466 mmol), 50 mL of toluene, and 50 mL of distilled water were placed in a flask and stirred at reflux at 140 °C. After 12 hours, the mixture was cooled to room temperature, and the layers were separated. Next, this was filtered through silica and recrystallized to obtain compound C-4 (4.7 g, yield: 44%). MG SP . C-4 460,54 288 °C [Example 6] Synthesis of Compound C-137

[0078] 2-Chloro-9-phenyl-1,10-phenanthroline (8.6 g, 29.6 mmol), 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2H-benzo[d][1,2,3]triazole (11.4 g, 35.5 mmol), Pd(amphos)Cl2 (1.8 g, 2.48 mmol), Aliquat 336 (1.4 g, 3.55 mmol), Na2CO3 (7.5 g, 71.0 mmol), 177 mL of toluene, and 59 mL of distilled water were placed in a flask and stirred at 130 °C under reflux. After 3 h, the mixture was cooled to room temperature, and the layers were separated. Next, this was filtered through silica and recrystallized to obtain compound C-137 (3.5 g, yield: 26.35%). MG SP . C-137 449,52 194 °C [Example 7] Synthesis of Compound C-6

[0079] Compound 7-1 (10.0 g, 24.49 mmol), Compound 7-2 (7.8 g, 26.94 mmol), Pd(amphos)Cl2 (1.2 g, 1.71 mmol), Aliquat 336 (1.0 g, 2.45 mmol), and Na2CO3 (5.2 g, 48.98 mmol) were dissolved in 122 mL of toluene and 41 mL of distilled water in a flask and stirred under reflux at 130 °C. After 2 hours and 30 minutes, the mixture was cooled to room temperature, and the layers in the resulting solid reaction product were separated. This was filtered through silica and recrystallized. Afterward, separation was carried out by column chromatography to obtain Compound C-6 (3.5 g, yield: 26.63%). MG SP . C-6 536,62 283 °C [Example 8] Synthesis of Compound C-200

[0080] Compound 8-1 (8.0 g, 17.45 mmol), Compound 8-2 (5.3 g, 19.19 mmol), Pd(amphos)Cl2 (0.9 g, 1.22 mmol), Aliquat 336 (0.7 g, 1.74 mmol), and Na2CO3 (3.7 g, 34.90 mmol) were dissolved in 87 mL of toluene and 29 mL of distilled water in a flask and stirred under reflux at 130 °C. After 2 hours, the mixture was cooled to room temperature, and the layers were separated. Next, this was filtered through silica and recrystallized to obtain Compound C-200 (3.3 g, yield: 35.98%). MG SP . C-200 525,60 204 °C [Example 9] Synthesis of compound C-12

[0081] Compound 9-1 (7.8 g, 23.91 mmol), Compound 9-2 (7.7 g, 35.87 mmol), Pd(amphos)Cl2 (1.2 g, 1.67 mmol), Aliquat 336 (1.0 g, 2.39 mmol), and Na2CO3 (5.1 g, 47.82 mmol) were dissolved in 120 mL of toluene and 40 mL of distilled water in a flask and stirred at 130 °C under reflux. After 2 hours, the mixture was cooled to room temperature, and the layers were separated. Next, this was filtered through silica and recrystallized to obtain Compound C-12 (8.1 g, yield: 73.56%). MG SP . C-12 460,53 284 °C [Example 10] Synthesis of Compound C-82

[0082] Compound 10-1 (15.0 g, 32.72 mmol), Compound 10-2 (13.0 g, 35.99 mmol), Pd(amphos)Cl2 (1.6 g, 2.29 mmol), Aliquat 336 (1.3 g, 3.27 mmol), and Na2CO3 (6.9 g, 65.44 mmol) were dissolved in 165 mL of toluene and 55 mL of distilled water in a flask and stirred at 130 °C under reflux. After 3 hours, the mixture was cooled to room temperature, and the layers were separated. Next, this was filtered through silica to obtain Compound C-82 (13.0 g, yield: 64.83%). MG SP . C-82 612,72 251 °C [Example 11] Synthesis of Compound C-76

[0083] Compound 11-1 (17.0 g, 37.1 mmol), Compound 11-2 (12.0 g, 37.9 mmol), Pd(PPh3)4 (0.416 g, 1.85 mmol), SPhos (1.52 g, 3.71 mmol), and K2CO3 (15.4 g, 111 mmol) were dissolved in 340 mL of THF and 34 mL of distilled water in a flask and stirred under reflux at 70 °C. After 3 h, the mixture was cooled to room temperature and filtered through silica to obtain Compound C-76 (15.3 g, yield: 67.4%). MG SP . C-76 612,74 284 °C [Example 12] Synthesis of Compound C-151

[0084] Compound 12-1 (15.7 g, 49.0 mmol), Compound 12-2 (5.5 g, 22.1 mmol), Pd(amphos)Cl2 (2.42 g, 3.43 mmol), Aliquat 336 (1.98 g, 4.9 mmol), and Na2CO3 (10.4 g, 98.0 mmol) were dissolved in 200 mL of toluene and 50 mL of distilled water in a flask and stirred at 100 °C under reflux. After 18 hours, methanol was added, the resulting solid reaction product was cooled to room temperature, and the layers were separated. Next, this was separated with a silica filter to obtain Compound C-151 (7.5 g, yield: 59.9%). MG SP . C-151 566,63 327 °C [Example 13] Synthesis of Compound C-213

[0085] Compound 13-1 (8.8 g, 23 mmol), Compound 13-2 (8.5 g, 24 mmol), Pd(PPh3)4 (1.3 g, 1.1 mmol), and K2CO3 (6.3 g, 46 mmol) were dissolved in 125 mL of toluene, 25 mL of ethanol, and 25 mL of distilled water in a flask and stirred under reflux at 100 °C for 4 hours. After the reaction, the reaction product was cooled to room temperature, the organic matter was extracted with methylene chloride, and then distilled under reduced pressure. Afterward, it was separated by column chromatography to obtain Compound C-213 (9.0 g, yield: 73%). MG SP . C-213 536,64 180 °C [Example 14] Synthesis of Compound C-170

[0086] Compound 14-1 (8.8 g, 23 mmol), Compound 14-2 (8.5 g, 24 mmol), Pd(PPh3)4 (1.3 g, 1.1 mmol), and K2CO3 (6.3 g, 46 mmol) were dissolved in 125 mL of toluene, 25 mL of ethanol, and 25 mL of distilled water in a flask and stirred under reflux at 100 °C for 4 hours. After completion of the reaction, the reaction product was cooled to room temperature, the organic matter was extracted with methylene chloride, and then distilled under reduced pressure. After precipitation with ethyl acetate, it was separated by column chromatography to obtain Compound C-170 (7.5 g, yield: 61%). MG SP . C-170 536,64 230 °C [Example 15] Synthesis of Compound C-300

[0087] Compound 15-1 (5.0 g, 13.08 mmol), Compound 15-2 (4.6 g, 14.39 mmol), Pd(amphos)Cl2 (0.6 g, 0.91 mmol), Aliquat 336 (1.1 g, 2.61 mmol), and Na2CO3 (2.8 g, 26.16 mmol) were dissolved in 65 mL of toluene and 22 mL of distilled water in a flask and stirred under reflux at 130 °C for 5 hours. After the reaction, the mixture was cooled to room temperature, its layers were separated, and the residue was then filtered through Celite. Afterward, it was filtered through silica and recrystallized to obtain Compound C-300 (4.8 g, yield: 69%). MG SP . C-300 536,64 270 °C [Example 16] Synthesis of Compound C-302

[0088] Compound 16-1 (5.0 g, 13.08 mmol), Compound 16-2 (4.6 g, 14.39 mmol), Pd(amphos)Cl2 (0.6 g, 0.91 mmol), Aliquat 336 (1.1 g, 2.61 mmol), and Na2CO3 (2.8 g, 26.16 mmol) were dissolved in 65 mL of toluene and 22 mL of distilled water in a flask and stirred under reflux at 130 °C for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, the layers were separated, and the residue was then filtered through Celite. Next, it was filtered through silica and recrystallized to obtain Compound C-302 (3.5 g, yield: 49%). MG SP . C-302 536,64 268 °C [Example 17] Synthesis of Compound C-233

[0089] Compound 17-1 (5.0 g, 12.2 mmol), Compound 17-2 (3.9 g, 13.4 mmol), Pd(amphos)Cl2 (0.6 g, 0.91 mmol), Aliquat 336 (1.0 g, 2.44 mmol), and Na2CO3 (2.6 g, 24.4 mmol) were dissolved in 61 mL of toluene and 20 mL of distilled water in a flask and stirred under reflux at 130 °C for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, the layers were separated, and the residue was then filtered through Celite. Next, it was filtered through silica and recrystallized to obtain Compound C-233 (2.7 g, yield: 41%). MG SP . C-233 538,61 315 °C [Example 18] Synthesis of Compound C-235

[0090] Compound 18-1 (13.7 g, 33.4 mmol), Compound 18-2 (10.7 g, 36.7 mmol), Pd(amphos)Cl2 (1.6 g, 2.3 mmol), Aliquat 336 (2.7 g, 6.7 mmol), and Na2CO3 (7.1 g, 66.8 mmol) were dissolved in 167 mL of toluene and 55 mL of distilled water in a flask and stirred under reflux at 130 °C for 3 hours. After completion of the reaction, the mixture was cooled to room temperature, the layers were separated, and the residue was then filtered through Celite. Next, it was filtered through silica and recrystallized to obtain Compound C-235 (4.2 g, yield: 23%). MG SP . C-235 538,61 224 °C [Example 19] Synthesis of Compound C-299

[0091] Compound 19-1 (9.1 g, 30.2 mmol), Compound 19-2 (5.6 g, 23.3 mmol), Pd(PPh3)4 (1.3 g, 1.2 mmol), and K2CO3 (6.4 g, 46.5 mmol) were dissolved in 110 mL of toluene, 22 mL of ethanol, and 22 mL of distilled water in a flask and stirred under reflux at 100 °C for 3 hours. After the reaction was complete, the mixture was cooled to room temperature, the layers were separated, and the residue was then filtered through Celite. Next, it was filtered through silica and recrystallized to obtain Compound C-299 (9.4 g, yield: 88%). MG SP . C-299 460,5 253 °C [Example 20] Synthesis of Compound C-215

[0092] Compound 20-1 (16.3 g, 42.6 mmol), Compound 20-2 (7.5 g, 23.7 mmol), Pd(OAc)2 (0.3 g, 1.2 mmol), SPhos (0.93 g, 2.4 mmol), and K2CO3 (6.5 g, 47.3 mmol) were dissolved in 150 mL of THF and 15 mL of distilled water in a flask and stirred under reflux at 65 °C for 15 hours. After the reaction was complete, the mixture was cooled to room temperature, the layers were separated, and the residue was then filtered through Celite. Next, it was filtered through silica and recrystallized to obtain Compound C-215 (8.5 g, yield: 67%). MG SP . C-215 536,6 270 °C

[0093] In the following, the method for producing an organic electroluminescent device comprising the compound according to the present disclosure and the properties of this device are explained for a detailed understanding of the present disclosure. [Device Examples 1 to 7] Fabrication of OLEDs deposited with a compound according to the present disclosure as a material for an N-type charge generation layer

[0094] OLEDs were fabricated according to the present disclosure. First, a transparent electrode thin film of indium tin oxide (ITO) (10 Ω / sq) on a glass substrate for an OLED (GEOMATEC CO., LTD., Japan) was subjected to sequential ultrasonic washing with acetone and isopropyl alcohol, then stored in isopropyl alcohol, and then used. Afterward, the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 was then introduced into one cell of the vacuum vapor deposition apparatus, and Compound HT-1 was introduced into another cell. The two materials were evaporated at different rates, and Compound HI-1 was deposited at a doping amount of 3 wt% based on the total amount of Compounds HI-1 and HT-1 to form a hole-injection layer with a thickness of 5 nm.Next, Compound HT-1 was deposited as the first hole-transporting layer with a thickness of 30 nm on the hole-injecting layer. Then, Compound HT-2 was introduced into another cell of the vacuum vapor deposition apparatus and evaporated by passing an electric current through the cell, thereby forming a second hole-transporting layer with a thickness of 5 nm on the first hole-transporting layer. After the formation of the hole-injecting layer and the hole-transporting layers, a light-emitting layer was formed thereon as follows: Compound H-1 was introduced into one cell of the vacuum vapor deposition apparatus as a host, and Compound D-1 was introduced into another cell as a dopant. The two materials were evaporated at different rates, and the dopant was added in a doping amount of 2 wt.-% based on the total amount of the host and the dopant, thereby forming a first light-emitting layer with a thickness of 20 nm on the second hole-transport layer. Next, Compound ET-1 was deposited to a thickness of 5 nm as a material for the first hole-blocking layer. Then, Compound ET-2 was doped to a thickness of 10 nm as a material for an electron-transport layer, thereby forming a first electron-transport layer. After that, Li was deposited in an amount of 0.5 wt% in the compound of Table 1 below, thereby forming an N-type charge generation layer with a thickness of 4 nm. Next, Compound HI-1 was doped in an amount of 6 wt% based on the total amount of Compound HI-1 and Compound HT-1, thereby forming a P-type charge generation layer with a thickness of 10 nm.Subsequently, compound HT-1 was deposited to a thickness of 30 nm, forming a third hole-transport layer, and then compound HT-2 was deposited to a thickness of 5 nm, forming a fourth hole-transport layer. A second light-emitting layer was then deposited thereon as follows: After assembly, compound H-1 was introduced as a host into one cell in a vacuum deposition apparatus, and compound D-1 as a dopant was introduced into another cell. The two materials were evaporated at different rates, and the dopant was deposited in an amount of 2 wt% based on the total amount of the host and dopant, forming a second light-emitting layer with a thickness of 20 nm on the fourth hole-transport layer.Compound ET-1 as a second hole-blocking layer material with a thickness of 5 nm was deposited on the second light-emitting layer, and compounds ET-3 and EI-1 as materials for the second electron-transporting layer were each arranged in two cells in a vacuum deposition apparatus, and the two materials were deposited at a weight ratio of 2:1 to a thickness of 25 nm. Next, Yb as an electron-injecting layer with a thickness of 1 nm was deposited on the second electron-transporting layer, and then, using another vacuum vapor deposition apparatus, an Al cathode with a thickness of 80 nm was deposited on the electron-injecting layer. Thus, OLEDs were fabricated. Each compound used for all of the materials was prepared by vacuum sublimation at 10 °C. -6 Torr cleaned. [Device Comparative Example 1] Fabrication of an OLED comprising the conventional compound as an N-type charge generation layer

[0095] An OLED was fabricated in the same manner as in Device Example 1, except that the compound described in Table 1 below was used as a material for an N-type charge generation layer.

[0096] The driving voltage and efficiency at a luminance of 1000 nits and the time required to reduce the luminance from 100% to 95% (lifetime: T 95 ) of the OLEDs of Device Examples 1 to 7 and Device Comparative Example 1 manufactured as described above were measured, and the results thereof are shown in the following Table 1. Table 1 N-type charge generation layer Driver voltage [V] Power efficiency [cd / A] Lifespan [T 95 , h] Device example 1 C-57 6,4 7,5 175,0 Device example 2 C-137 6,4 7,5 172,0 Device example 3 C-82 6,4 7,4 158,1 Device example 4 C-151 6,4 7,4 172,0 Device example 5 C-200 6,5 7,4 177,7 Device example 6 C-76 6,4 7,4 171,0 Device example 7 C-235 6,4 7,5 164,1 Device comparison example 1 CG-0 6,6 7,4 152,0 [Device Examples 8 to 13] Production of OLEDs deposited with a compound according to the present disclosure as a material for an N-type charge generation layer

[0097] OLEDs were fabricated in the same manner as in Device Example 1, except that Yb was deposited in an amount of 2 wt% in the material for the N-type charge generation layer as shown in Table 2 below, thereby forming an N-type charge generation layer having a thickness of 8 nm, and the thickness of the P-type charge generation layer was changed to 5 nm. [Device Comparative Example 2] Fabrication of an OLED Containing the Conventional Compound as an N-Type Charge Generation Layer

[0098] An OLED was fabricated in the same manner as in Device Example 8 except that the compound described in Table 2 below was used as a material for an N-type charge generation layer.

[0099] The driving voltage and efficiency at a luminance of 1000 nits and the time required to reduce the luminance from 100% to 95% at a luminance of 1000 nits (lifetime: T 95 ) of the OLEDs of Device Examples 8 to 13 and Device Comparative Example 2 manufactured as described above were measured, and the results thereof are shown in Table 2 below. Table 2 N-type charge generation layer Driver voltage [V] Power efficiency [cd / A] Lifespan [T 95 , h] Device example 8 C-3 7,0 7,5 473,1 Device example 9 C-5 6,7 7,7 361,6 Device example 10 C-57 6,6 7,7 415,8 Device example 11 C-1 7,0 7,5 404,4 Device example 12 C-4 6,6 7,3 408,3 Device example 13 C-6 7,0 7,5 349,6 Device comparison example 2 CG-0 8,1 7,1 348,1

[0100] From the results in Tables 1 and 2 above, it can be confirmed that an organic electroluminescent device comprising the compound according to the present disclosure in an N-type charge generation layer has significantly improved characteristics of low driving voltage and / or high efficiency and / or long lifetime.

[0101] The compounds used in the device examples and comparative device examples are shown in detail in Table 3 below. Table 3 Hole injection layer / hole transport layer Light-emitting layer Electron transport layer / electron injection layer N-type charge generation layer [Device Examples 14 to 21] Fabrication of OLEDs deposited with a compound according to the present disclosure as an N-type charge generation layer

[0102] OLEDs were fabricated in the same manner as in Device Example 1, except that the thickness of the first electron-transport layer was changed to 12 nm, Yb was deposited in an amount of 2 wt% as the material for the N-type charge generation layer in the compound shown in Table 4 below, thereby forming an N-type charge generation layer with a thickness of 9 nm, and the thickness of the P-type charge generation layer was changed to 6 nm. [Device Comparative Example 3] Preparation of an OLED Containing the Conventional Compound as an N-Type Charge Generation Layer

[0103] An OLED was fabricated in the same manner as in Device Example 14 except that the compound described in Table 4 below was used as a material for an N-type charge generation layer.

[0104] The driving voltage, efficiency, and change in progressive driving voltage (ΔV) at a luminance of 1000 nits for the OLEDs according to Device Examples 14 to 21 and Device Comparative Example 3 fabricated as described above were measured, and the results are shown in Table 4 below. Table 4 N-type charge generation layer Driver voltage [V] Power efficiency [cd / A] Progressive drive voltage ΔV [%] Device example 14 C-12 7,0 7,6 102,4 Device example 15 C-213 6,5 7,9 102,0 Device example 16 C-170 6,5 7,9 102,5 Device example 17 C-249 7,9 7,7 101,6 Device example 18 C-299 6,8 7,5 102,3 Device example 19 C-215 6,8 7,5 102,6 Device example 20 C-300 6,8 7,5 102,0 Device example 21 C-302 6,7 7,6 102,6 Device comparison example 3 CG-0 8,0 7,4 102,6

[0105] From the results in Table 4 above, it can be confirmed that an organic electroluminescent device including the compound according to the present disclosure in an N-type charge generation layer has a low driving voltage and / or a high efficiency and / or a small change in driving voltage.

[0106] The compounds used in the device examples and comparative device examples are shown in detail in Table 5 below. Table 5 Hole injection layer / hole transport layer Light-emitting layer Electron transport layer / hole blocking layer / electron injection layer N-type charge generation layer QUOTES CONTAINED IN THE DESCRIPTION

[0000] This list of documents submitted by the applicant was generated automatically and is included solely for the convenience of the reader. This list is not part of the German patent or utility model application. The DPMA assumes no liability for any errors or omissions. Cited patent literature

[0000] KR 2015-0121394

[0004] KR 2017-0105040

[0004]

Claims

[1] Compound represented by the following formula 1:where R1 is hydrogen, deuterium, a halogen, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted (C1-C 30 )-alkyl or a substituted or unsubstituted (3- to 30-membered) heteroaryl; R2 to R8 each independently represent hydrogen, deuterium, a halogen, cyano, a substituted or unsubstituted (C1-C 30 )-alkyl, a substituted or unsubstituted (C2-C 30 )-alkenyl, a substituted or unsubstituted (C6-C 30 )-aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-cycloalkyl, a substituted or unsubstituted (C3-C 30)-cycloalkenyl, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, a substituted or unsubstituted (C1-C 30 )-alkoxy, a substituted or unsubstituted tri-(C1-C 30 )-alkylsilyl, a substituted or unsubstituted di-(C1-C 30 )-alkyl-(C6-C 30 )-arylsilyl, a substituted or unsubstituted (C1-C 30 )-Alkyldi-(C6-C 30 )-arylsilyl, a substituted or unsubstituted tri-(C6-C 30 )-arylsilyl, a substituted or unsubstituted fused ring of an aliphatic (C3-C 30 ) ring and an aromatic (C6-C 30 )-ring or -L-HAr or they may be bonded to the adjacent substituent to form (a) ring(s); with the proviso that at least one of R2 to R8 is -L-HAr; L represents a single bond, a substituted or unsubstituted (C6-C 30)-arylene or a substituted or unsubstituted (3- to 30-membered) heteroarylene and HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl containing at least one nitrogen atom; with the proviso that when R4 or R5 is -L-HAr, the compounds in which HAr is quinazoline are excluded. [2] The compound according to claim 1, wherein the substituted alkyl, the substituted alkenyl, the substituted aryl(ene), the substituted heteroaryl(ene), the substituted cycloalkyl, the substituted cycloalkenyl, the substituted heterocycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl and the substituted fused ring of the aliphatic (C3-C 30 ) ring and the aromatic (C6-C 30) ring are each independently substituted by at least one selected from the group consisting of deuterium, a halogen, cyano, carboxyl, nitro, hydroxyl, a (C1-C 30 )-alkyl, halogen-(C1-C 30 )-alkyl, (C2-C 30 )-alkenyl, (C2-C 30 )-alkynyl, (C1-C 30 )-alkoxy, (C1-C 30 )-alkylthio, (C3-C 30 )-cycloalkyl, (C3-C 30 )-Cycloalkenyl, (3- to 7-membered) heterocycloalkyl, (C6-C 30 )-aryloxy, (C6-C 30 )-arylthio, (5- to 30-membered) heteroaryl, which is unsubstituted or substituted by a (C6-C 30 )-aryl, (C6-C 30 )-aryl which is unsubstituted or substituted by a (5- to 30-membered) heteroaryl, tri-(C1-C 30 )-alkylsilyl, tri-(C6-C 30 )-arylsilyl, di-(C1-C 30 )-alkyl-(C6-C 30 )-arylsilyl, (C1-C 30 )-alkyldi-(C6-C 30 )-arylsilyl, a fused ring of an aliphatic (C3-C 30) ring and an aromatic (C6-C 30 )-Rings, Amino, Mono- or Di-(C1-C 30 )-alkylamino, mono- or di-(C6-C 30 )-arylamino, (C1-C 30 )-alkyl-(C6-C 30 )-arylamino, mono- or di-(3- to 30-membered)-heteroarylamino, (C1-C 30 )-Alkyl-(3- to 30-membered)-heteroarylamino, (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino, (C1-C 30 )-alkylcarbonyl, (C1-C 30 )-alkoxycarbonyl, (C6-C 30 )-arylcarbonyl, (C6-C 30 )-Arylphosphinyl, Di(C6-C 30 )-arylboronyl, di-(C1-C 30 )-alkylboronyl, (C1-C 30 )-alkyl-(C6-C 30 )-arylboronyl, (C6-C 30 )-Ar-(C1-C 30 )-alkyl and (C1-C 30 )-alkyl-(C6-C 30 )aryl. [3] A compound according to claim 1, wherein formula 1 is represented by any one of the following formulas 1-1 to 1-7: wherein R1, L and HAr are as defined in Formula 1 and R2 to R8 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C6-C 30 )-aryl or a substituted or unsubstituted (3- to 30-membered) heteroaryl. [4] The compound according to claim 1, wherein HAr is represented by the following formulas 1-a or 1-b:wherein represents a site linked to L; X1 and X2 each independently N or CR 12 represent; Y1 to Y3 each independently N or NR 14 represent; R 11 and R 12 each independently hydrogen, deuterium, a substituted or unsubstituted (C6-C 30 )-aryl or a substituted or unsubstituted (3- to 30-membered) heteroaryl; R 13 and R 14 each independently hydrogen, deuterium, a substituted or unsubstituted (C6-C 30)-aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl or a site directly connected to L and a represents an integer from 1 to 4, where, when a is 2 or greater, each R 13 can be the same or different from each other. [5] A compound according to claim 1, wherein the compound represented by formula 1 is selected from the following compounds:wherein D n in the above compounds means that a number n of hydrogen atoms are replaced by deuterium, where n is an integer of 1 or more and the upper limit of n depends on the number of hydrogen atoms that can be replaced in each compound. [6] An organic electroluminescent material comprising the compound illustrated by formula 1 according to claim 1. [7] An organic electroluminescent device comprising a plurality of light-emitting units disposed between a first electrode and a second electrode and at least one charge generation layer disposed between the adjacent light-emitting units, wherein the charge generation layer comprises a compound illustrated by formula 1 according to claim 1. [8] The organic electroluminescent device according to claim 7, wherein at least one of the plurality of light-emitting units comprises a first light-emitting layer and a second light-emitting layer adjacent to each other. [9] Compound selected from the following compounds: [10] An organic electroluminescent material comprising a compound according to claim 9. [11] An organic electroluminescent device comprising a plurality of light-emitting units arranged between a first electrode and a second electrode and at least one charge generation layer arranged between the adjacent light-emitting units, wherein the charge generation layer comprises a compound according to claim 9. [12] The organic electroluminescent device according to claim 11, wherein at least one of the plurality of light-emitting units comprises a first light-emitting layer and a second light-emitting layer that are adjacent to each other.