Organic electroluminescent compounds, multiple host materials, and organic electroluminescent devices containing the same

Abstract

To provide an organic electroluminescent compound, a plurality of host materials, and an organic electroluminescent device comprising the same.SOLUTION: The present disclosure relates to an organic electroluminescent compound represented by a formula 1, a plurality of host materials comprising a combination of specific compounds, and an organic electroluminescent device comprising the same. The organic electroluminescent device having an improved driving voltage, luminous efficiency and / or lifespan properties can be provided by including the organic electroluminescent compound or a specific combination of compounds according to the present disclosure as a host material.SELECTED DRAWING: None

Description

[Technical Field]

[0001] This disclosure relates to organic electroluminescent compounds, host materials comprising specific combinations of compounds, and organic electroluminescent devices comprising the same. [Background technology]

[0002] In 1987, Tang et al. at Eastman Kodak first developed a two-layer small molecule green organic electroluminescent device (OLED) consisting of a light-emitting layer and a charge transport layer, made of TPD / Alq3. Subsequently, OLED development progressed rapidly, and OLEDs were commercialized. Currently, organic electroluminescent devices mainly use phosphors with excellent luminescence efficiency to realize panels. For long-term use and high resolution in displays, OLEDs with high luminescence efficiency and / or long lifespan are required.

[0003] Various materials and concepts have been proposed for the organic layer of organic electroluminescent devices to improve luminous efficiency, drive voltage, and / or lifetime, but these have not been satisfactory in practical terms. Therefore, there has always been a need to develop organic electroluminescent devices with improved performance compared to known organic electroluminescent devices, such as improved drive voltage, luminous efficiency, power efficiency, and / or lifetime characteristics.

[0004] Patent Document 1 discloses a molten dihydrophenanthrene derivative, but does not specifically disclose a compound containing substituted dihydrophenanthrene. The development of organic electroluminescent materials to improve OLED performance remains necessary. [Prior art documents] [Patent Documents]

[0005] [Patent Document 1] Korean Patent No. 10-1577104 Specification [Patent Document 2] Korean Patent Application Publication No. 2017-0022865 Specification [Patent Document 3] Korean Patent Application Publication No. 2017-0051198 Specification [Patent Document 4] Korean Patent Application Publication No. 2018-0094572 Specification [Patent Document 5] Korean Patent Application Publication No. 2020-0026079 Specification [Overview of the project] [Problems that the invention aims to solve]

[0006] An object of this disclosure is to provide an organic electroluminescent compound having a novel structure suitable for application to organic electroluminescent devices. Another object of this disclosure is to provide an improved organic electroluminescent material that can provide an organic electroluminescent device having properties such as reduced drive voltage, improved luminescence efficiency and / or long lifetime. Another object of this disclosure is to provide an organic electroluminescent device having improved drive voltage, luminescence efficiency and / or lifetime properties by including a specific combination of compounds as a host material. [Means for solving the problem]

[0007] The present inventors have completed this disclosure by discovering that a compound represented by the following formula 1 achieves the above-mentioned objective. The compound represented by formula 1 of this disclosure can be applied to organic electroluminescent devices as a plurality of host materials in combination with the compounds represented by formulas 2, 3, or 4.

[0008] [ka] In Equation 1, R 11 ~R14 Each independently represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl, or may be bonded to adjacent substituents to form a ring, provided that R 11 ~R 14 at least one of which is neither hydrogen nor deuterium; R1 to R8 each independently represents hydrogen, deuterium or -L-Ar, or may be bonded to adjacent substituents to form a ring, provided that at least one of the pairs of R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6 and R7, and R7 and R8 is bonded to each other to form the following formula a:

Chemical formula

[0009] [ka] In Equation 2, X1 and Y1 are independent of -N= and -NR 67- represents -O- or -S-, where either X1 or Y1 represents -N= and the other X1 or Y1 represents -NR 67 -, -O-, or -S- represent; R 61 This represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 member) heteroaryl; R 62 ~R 64 and R 67 Each of these independently represents hydrogen, deutherium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted fused ring of an (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -L3''-N(Ar3'')(Ar4''), or may be bonded to an adjacent substituent to form a ring; Each L3'' independently represents a single bond, substituted or unsubstituted (C6-C30) arylene or a substituted or unsubstituted (3-30 member) heteroarylene; Ar3'' and Ar4'' each independently represent hydrogen, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30) alkenyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl; R 65 and R 66 Each of these independently represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 member) heteroaryl; L4 represents a single bond, substituted or unsubstituted (C6-C30) arylene or a substituted or unsubstituted (3-30 member) heteroarylene; and If a represents 1, b and c each independently represent 1 or 2, d represents an integer from 1 to 4, and b to d are integers greater than or equal to 2, then R 62 Each of ~R 64 Each of them may be the same as or different from one another.

[0010] [ka] In Equation 3, L a and L b Each of these independently represents a single bond, substituted or unsubstituted (C6-C30) arylene or a substituted or unsubstituted (3-30 member) heteroarylene; Ar a and Ar b Each of these independently represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl; R 301 ~R 304 Each of these independently consists of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted It represents a di(C1~C30)alkyl(C6~C30)arylsilyl, a substituted or unsubstituted (C1~C30)alkyldi(C6~C30)arylsilyl, a substituted or unsubstituted tri(C6~C30)arylsilyl, a substituted or unsubstituted fused ring of a (C3~C30) aliphatic ring and a (C6~C30) aromatic ring, or -L3'''-N(Ar3''')(Ar4'''), or can be bonded to an adjacent substituent to form a ring; L3'''' each independently represents a single bond, substituted or unsubstituted (C6-C30) arylene or a substituted or unsubstituted (3-30 member) heteroarylene; Ar3''' and Ar4''' each independently represent hydrogen, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30) alkenyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl; and If f and i each independently represent integers from 1 to 4, and g and h each independently represent integers from 1 to 3, and if f to i are integers greater than or equal to 2, then R 301 Each of ~R 304 Each of them may be the same as or different from one another.

[0011] [ka] In Equation 4, T represents -O- or -S-; HAr represents a substituted or unsubstituted nitrogen-containing (3-30 member) heteroaryl; L 51 This represents a single-bonded, substituted, or unsubstituted (C6-C30) arylene or a substituted or unsubstituted (3-30 member) heteroarylene; R 71 and R 72Each of these independently consists of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, and substituted or unsubstituted di(C1-C30)alkyl(C6-C30). Represents an arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, or may be bonded to an adjacent substituent to form a ring; and a 11 represents integers from 1 to 4, and b 12 represents integers from 1 to 3, and a 11 and b 12 If each of these represents an integer greater than or equal to 2, then R 71 Each of and R 72 Each of them may be the same as or different from one another.

[0012] Advantageous effects of the invention The organic electroluminescent compounds according to this disclosure exhibit suitable performance for use in organic electroluminescent devices. In addition, by including certain combinations of the compounds according to this disclosure as a host material, organic electroluminescent devices with lower drive voltage, higher luminescence efficiency, and / or longer lifetime characteristics are provided compared to conventional organic electroluminescent devices. For example, by including the compounds according to this disclosure, a red-emitting organic electroluminescent device with low drive voltage, high luminescence efficiency, and / or long lifetime characteristics can be provided. [Modes for carrying out the invention]

[0013] The present disclosure will be described in detail below. However, the following description is intended to illustrate the present invention and is not intended to limit its scope.

[0014] The term "organic electroluminescent compound" in this disclosure means a compound that can be used in an organic electroluminescent device and may, if necessary, be included in any layer constituting the organic electroluminescent device.

[0015] The term “organic electroluminescent material” in this disclosure means a material that can be used in an organic electroluminescent device and may contain at least one compound. The organic electroluminescent material may be included in any layer constituting the organic electroluminescent device, as necessary. For example, the organic electroluminescent material may be: a hole injection material, a hole transport material, a hole auxiliary material, a light emission auxiliary material, an electron blocking material, a light emission material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material.

[0016] The term “multiple organic electroluminescent materials” in this disclosure means organic electroluminescent materials comprising a combination of at least two compounds, which may be contained in any organic layer constituting an organic electroluminescent device. It can mean both materials before (e.g., before deposition) inclusion in the organic electroluminescent device and materials after (e.g., after deposition) inclusion in the organic electroluminescent device. For example, multiple organic electroluminescent materials may be a combination of two or more compounds, which may be contained in at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, an electron barrier layer, a light emission layer, an electron buffer layer, a hole barrier layer, an electron transport layer, and an electron injection layer. Such two or more compounds may be contained in the same layer or in different layers by methods used in the art, and may be evaporated as a mixture, co-evaporated, or instead deposited individually.

[0017] The term “multiple host materials” in this disclosure means host materials comprising a combination of at least two compounds, which may be included in any light-emitting layer constituting an organic electroluminescent device. It can mean both materials before inclusion in the organic electroluminescent device (e.g., before deposition) and materials after inclusion in the organic electroluminescent device (e.g., after deposition). For example, the multiple host materials in this disclosure may be a combination of two or more host materials and may optionally further include materials typically included in organic electroluminescent materials. The two or more host materials included in the multiple host materials in this disclosure may be included in one light-emitting layer or each may be included in different light-emitting layers. For example, the two or more host materials may be evaporated as a mixture, co-evaporated, or individually deposited.

[0018] The organic electroluminescent materials of this disclosure may include one or more types of compounds represented by Formula 1. The compounds of Formula 1 may, but are not limited to, be included in hole injection layers, hole transport layers, hole auxiliary layers, light emission auxiliary layers, electron barrier layers, light emission layers, electron buffer layers, hole barrier layers, electron transport layers, and / or electron injection layers. The compounds of Formula 1 may, but are not limited to, be included in light emission layers. If the compounds of Formula 1 are included in light emission layers, they are included as a host material. In that case, the host material can be a host material for blue, green, or red light-emitting organic electroluminescent devices.

[0019] Next, we will explain in more detail the compound represented by formula 1.

[0020] In this specification, the term "(C1-C30) alkyl(len)" means a linear or branched alkyl(len) having 1 to 30 carbon atoms constituting the chain, where the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10. Examples of the alkyls mentioned above include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and sec-butyl. The term "(C2-C30) alkenyl" means a linear or branched alkenyl having a chain composed of 2 to 30 carbon atoms, where the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10. Examples of the alkenyls mentioned above include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, and 2-methylbute-2-enyl. The term "(C2~C30)alkynyl" refers to a linear or branched alkynyl having a chain composed of 2 to 30 carbon atoms, where the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10. Examples of the alkynyls mentioned above include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, and 1-methylpenthinyl-2-nyl. The term "(C3~C30)cycloalkyl(lene)" refers to a mono- or poly-cyclic hydrocarbon having a ring main chain of 3 to 30 carbon atoms, where the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7. Examples of the cycloalkyls mentioned above include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, and cyclohexylmethyl. The term "(3-7 member) heterocycloalkyl" means a cycloalkyl having 3 to 7, preferably 5 to 7, ring main chain atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably at least one heteroatom selected from the group consisting of O, S, and N. Examples of the above-mentioned heterocycloalkyl include tetrahydrofuran, pyrrolidine, thiolane, and tetrahydropyran. The term "(C6-C30) aryl(lene)" means,This refers to monocyclic or fused ring groups derived from aromatic hydrocarbons having 6 to 30 ring-back chain carbon atoms, which may be partially saturated. The number of ring-back chain carbon atoms is preferably 6 to 25, more preferably 6 to 18. The aryls mentioned above also include those having a spiro structure. The aryls mentioned above include: phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenantrenyl, phenylphenantrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracerenyl, perilenyl, crisenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, azlenyl, tetramethyldihydrophenantrenyl, etc. More specifically, examples of aryls include: phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, 1-crisenyl, 2-crisenyl, 3-crisenyl, 4-crisenyl, 5-crisenyl, 6-crisenyl, benzo[c]phenanthryl, benzo[g]crisenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benz Zo[a]fluorenyl, benzo[b]fluorenyl, benzo[c]fluorenyl, dibenzofluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cuminyl, m-cuminyl, p-cuminyl,p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenylyl, 4''-tert-butyl-p-terphenyl-4-yl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 11,11-dimethyl-1-benzo[a]fluorenyl Renyl, 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 Zo[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-phenantrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenantrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenantrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-4-phenantrenyl, etc.

[0021] The term "(3-30 member) heteroaryl(len)" refers to an aryl or arylene group having 3 to 30 ring-chain atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P. The number of heteroatoms is preferably 1 to 4. The heteroaryl(len) described above may be a monoring or a fused ring fused with at least one benzene ring, and may be partially saturated. In addition, the heteroaryl(len) described above also includes forms in which at least one heteroaryl or aryl group is bonded to the heteroaryl group via a single bond, and further includes those having a spiro structure. Examples of the heteroaryls mentioned above include: monocyclic heteroaryls, such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetradinyl, triazolyl, tetrazolyl, flazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridadinyl, etc., and condensed ring heteroaryls, such as benzofuranil, benzothiophenyl, isobenzofuranil, dibenzofuranil, dibenzothiophenyl, dibenzoselenophenyl, naphthobenzofuranil, naphthobenzothiophenyl, benzofloquinolyl, benzofloquinazolinil, benzoflonaphthyridinil, benzoflopyrimidinil, naphthofyrimidinil, benzothienokinoquinol Lil, benzothienocinazolinil, benzothienonaphthilidinil, benzothienopyrimidinil, naphthienopyrimidinil, pyrimidoindolyl, benzopyrimidoindolyl, benzoflopyrazinil, naphthoflopyrazinil, benzothienopyrimidinil, naphthienopyrimidinil, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinil, quinazolinil, benzoquinazolinil, quinoxalinil, benzoquinoxalinil, naphthilidinil, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinil, phenothiazinil,Phenanthridine, benzodioxolyl, dihydroacridinyl, benzotriazolofenadinyl, imidazopyridyl, clomenoquinazolinyl, thioclomenoquinazolinyl, dimethylbenzopyrimidinyl, indolocarbazolyl, indenocarbazolyl, etc. More specifically, heteroaryls include: 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazine-4-yl, 1,2,4-triazine-3-yl, 1,3,5-triazine-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolidinyl, 2-indolidinyl, 3-indolidinyl, 5-indolidinyl, 6-indolidinyl Doridinyl, 7-Indolidinyl, 8-Indolidinyl, 2-Imidazopyridyl, 3-Imidazopyridyl, 5-Imidazopyridyl, 6-Imidazopyridyl, 7-Imidazopyridyl, 8-Imidazopyridyl, 3-Pyridyl, 4-Pyridyl, 1-Indolyl, 2-Indolyl, 3-Indolyl, 4-Indolyl, 5-Indolyl, 6-Indolyl, 7-Indolyl, 1-Isoindolyl, 2-Isoindolyl, 3-Isoindolyl, 4-Isoindolyl, 5-Isoindolyl, 6-Isoindolyl Lu, 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 Ryl, 4-isoquinoryl, 5-isoquinoryl, 6-isoquinoryl, 7-isoquinoryl, 8-isoquinoryl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazolyl-1-yl, azacarbazolyl-2-yl, azacarbazolyl-3-yl, azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarbazolyl-6-yl, azacarbazolyl-7-yl,Azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenanthridine, 2-phenanthridine, 3-phenanthridine, 4-phenanthridine, 6-phenanthridine, 7-phenanthridine, 8-phenanthridine, 9-phenanthridine, 10-phenanthridine, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-flazanyl, 2-thienyl, 3 -thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-tert-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolly, 4-methyl-1-indolly, 2-methyl-3-indolly, 4-methyl-3-indolly, 2-tert-butyl-1-indolly, 4-tert-butyl-1 -Indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 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 Lanyl, 6-naphtho-[1,2-b]-benzofuranil, 7-naphtho-[1,2-b]-benzofuranil, 8-naphtho-[1,2-b]-benzofuranil, 9-naphtho-[1,2-b]-benzofuranil, 10-naphtho-[1,2-b]-benzofuranil, 1-naphtho-[2,3-b]-benzofuranil, 2-naphtho-[2,3-b]-benzofuranil, 3-naphtho-[2,3-b]-benzofuranil, 4-naphtho-[2,3-b]-benzofuranil, 5-naphtho-[2,3-b]-benzofuranil, 6-naphtho-[2,3-b]-benzofuranil,7-Naphtho-[2,3-b]-benzofuranil, 8-Naphtho-[2,3-b]-benzofuranil, 9-Naphtho-[2,3-b]-benzofuranil, 10-Naphtho-[2,3-b]-benzofuranil, 1-Naphtho-[2,1-b]-benzofuranil, 2-Naphtho-[2,1-b]-benzofuranil, 3-Naphtho-[2,1-b]-benzofuranil, 4-Naphtho-[2,1-b]-benzofuranil, 5-Naphtho-[2,1-b]-benzofuranil, 6-Naphtho-[2,1-b]-benzofuranil, 7-Naphtho-[2,1-b]-benzofuranil, 8-Naphtho- [2,1-b]-benzofuranyl, 9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-benzothiophenyl, 2-naphtho-[1,2-b]-benzothiophenyl, 3-naphtho-[1,2-b]-benzothiophenyl, 4-naphtho-[1,2-b]-benzothiophenyl, 5-naphtho-[1,2-b]-benzothiophenyl, 6-naphtho-[1,2-b]-benzothiophenyl, 7-naphtho-[1,2-b]-benzothiophenyl, 8-naphtho-[1,2-b]-benzothiophenyl phenyl, 9-naphtho-[1,2-b]-benzothiophenyl, 10-naphtho-[1,2-b]-benzothiophenyl, 1-naphtho-[2,3-b]-benzothiophenyl, 2-naphtho-[2,3-b]-benzothiophenyl, 3-naphtho-[2,3-b]-benzothiophenyl, 4-naphtho-[2,3-b]-benzothiophenyl, 5-naphtho-[2,3-b]-benzothiophenyl, 1-naphtho-[2,1-b]-benzothiophenyl, 2-naphtho-[2,1-b]-benzothiophenyl, 3-naphtho-[2,1-b]-benzothiophenyl, 4-naph To-[2,1-b]-benzothiophenyl, 5-naphtho-[2,1-b]-benzothiophenyl, 6-naphtho-[2,1-b]-benzothiophenyl, 7-naphtho-[2,1-b]-benzothiophenyl, 8-naphtho-[2,1-b]-benzothiophenyl, 9-naphtho-[2,1-b]-benzothiophenyl, 10-naphtho-[2,1-b]-benzothiophenyl, 2-benzoflo[3,2-d]pyrimidinyl, 6-benzoflo[3,2-d]pyrimidinyl, 7-benzoflo[3,2-d]pyrimidinyl, 8-benzoflo[3,2-d]pyrimidinyl,9-Benzoflo[3,2-d]pyrimidinyl, 2-Benzothieno[3,2-d]pyrimidinyl, 6-Benzothieno[3,2-d]pyrimidinyl, 7-Benzothieno[3,2-d]pyrimidinyl, 8-Benzothieno[3,2-d]pyrimidinyl, 9-Benzothieno[3,2-d]pyrimidinyl, 2-Benzoflo[3,2-d]pyrazinyl, 6-Benzoflo[3,2-d]pyrazinyl, 7-Benzoflo[3,2-d]pyrazinyl, 8-Benzoflo[3,2-d]pyrazinyl, 9-Benzoflo[3,2-d]pyrazinyl, 2-Benzothieno[3,2 -d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[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. In this disclosure, "halogen" includes F, Cl, Br and I.

[0022] In addition, "ortho (o-)", "meta (m-)", and "para (p-)" are prefixes that indicate the relative positions of substituents. "Ortho" indicates that two substituents are adjacent to each other; for example, if two substituents in a benzene derivative occupy positions 1 and 2, this is called the ortho position. "Meta" indicates that two substituents are at positions 1 and 3; for example, if two substituents in a benzene derivative occupy positions 1 and 3, this is called the meta position. "Para" indicates that two substituents are at positions 1 and 4; for example, if two substituents in a benzene derivative occupy positions 1 and 4, this is called the para position.

[0023] In addition, the term "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced by another atom or another functional group (i.e., a substituent), and further includes substitutions by groups to which two or more substituents are attached. For example, a "substituent to which two or more substituents are attached" can be a pyridine-triazine. That is, a pyridine-triazine can be interpreted as either a single heteroaryl substituent or a substituent to which a heteroaryl substituent is attached. In the formulas of the present disclosure, each substituent of a substituted alkyl, substituted alkylene, substituted cycloalkyl, substituted cycloalkylene, substituted alkoxy, substituted aryl, substituted arylene, substituted heteroaryl and substituted heteroarylene is independently at least one selected from the group consisting of: deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; (C1-C30) alkyl; halo(C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3-7 member) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; unsubstituted or (C6-C30) aryls are (3-30 member) heteroaryls substituted with at least one (C6-C30) aryl; (C6-C30) aryls that are unsubstituted or substituted with at least one (C1-C30) alkyl and (3-30 member) heteroaryl; tri(C1-C30) alkylsilyls; tri(C6-C30) arylsilyls; di(C1-C30) alkyl(C6-C30) arylsilyls; (C1-C30) aryls Kildi(C6~C30)arylsilyl;amino; mono- or di-(C1~C30)alkylamino; mono- or di-(C2~C30)alkenylamino; unsubstituted or (C1~C30)alkyl-substituted mono- or di-(C6~C30)arylamino; mono- or di-(3~30 member) heteroarylamino; (C1~C30)alkyl(C2~C30)alkenylamino;(C1~C30)alkyl(C6~C30)arylamino; (C1~C30)alkyl(3~30 member)heteroarylamino; (C2~C30)alkenyl(C6~C30)arylamino; (C2~C30)alkenyl(3~30 member)heteroarylamino; (C6~C30)aryl(3~30 member)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)aryl(C1~C30)alkyl; and (C1~C30)alkyl(C6~C30)aryl. In one embodiment of the present disclosure, each substituent is independently selected from the group consisting of: (C1-C6) alkyl; (5-15 member) heteroaryl; or (C6-C15) aryl, either unsubstituted or substituted with at least one (C1-C6) alkyl. Specifically, each substituent may independently be at least one of methyl, phenyl, naphthyl, biphenyl, dimethylfluorenyl, tetramethyldihydrophenantrenyl, pyridyl, dibenzothiophenyl, dibenzofuranyl, and carbazolyl.

[0024] In the formulas of this disclosure, where one substituent is bonded to an adjacent substituent to form a ring, the ring may be a substituted or unsubstituted mono- or polycyclic (3-30 membered) alicyclic or aromatic ring, or a combination thereof, formed by the bonding of at least two adjacent substituents. In addition, the ring thus formed may contain at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S. In one embodiment of this disclosure, the number of ring back-chain atoms is 5-20, while in another embodiment of this disclosure, the number of ring back-chain atoms is 5-15.

[0025] In the formulas of this disclosure, heteroaryl, heteroarylene, and heterocycloalkyl each may independently contain at least one heteroatom selected from B, N, O, S, Si, and P. Furthermore, the heteroatom may be bonded to at least one selected from the group consisting of: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-30 member) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted Alternatively, unsubstituted di(C1~C30)alkyl(C6~C30)arylsilyl, substituted or unsubstituted (C1~C30)alkyldi(C6~C30)arylsilyl, substituted or unsubstituted tri(C6~C30)arylsilyl, substituted or unsubstituted mono- or di-(C1~C30)alkylamino, substituted or unsubstituted mono- or di-(C6~C30)arylamino, and substituted or unsubstituted (C1~C30)alkyl(C6~C30)arylamino.

[0026] In Equation 1, R 11 ~R 14 Each independently represents hydrogen, deutherium, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl, or may be bonded to an adjacent substituent to form a ring, provided that R 11 ~R 14 At least one of them is neither hydrogen nor deutherium. In one embodiment of the present disclosure, R 11 ~R 14 Each of these independently represents a substituted or unsubstituted (C1-C6) alkyl group. In another embodiment of the present disclosure, R 11 ~R 14 Each of these independently represents an unsubstituted (C1-C6) alkyl group. For example, R 11 ~R 14 All of them can be methyl.

[0027] In formula 1, R1 to R8 can each independently represent hydrogen, deutherium, or -L-Ar, or may be bonded to an adjacent substituent to form a ring, provided that at least one of the pairs R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6 and R7, and R7 and R8 are bonded to each other and fused to form the following formula a: [ka] The equation is formed, where X is NR 31 O, S, CR 32 R 33 or -CR 34 =CR 35 - represents, and R 31 This represents -L1-Ar1.

[0028] Here, R 32 and R 33 Each independently represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl, or may be bonded to an adjacent substituent to form a ring. In one embodiment of the present disclosure, R 32 and R 33 Each of these independently represents a substituted or unsubstituted (C1-C6) alkyl group. In another embodiment of the present disclosure, R 32 and R 33 Each of these independently represents an unsubstituted (C1-C6) alkyl group. For example, R 32 and R 33 All of them can be methyl.

[0029] R 34 and R 35 Each of these independently represents hydrogen, deutherium, or -L5-Ar5. In one embodiment of the present disclosure, R 34 and R 35 Each of these independently represents hydrogen or -L5-Ar5. For example, R 34 and R 35 These can each be independently hydrogen, -L5-Ar5, etc.

[0030] In equation a, R 21 ~R 24 Each of these may independently represent hydrogen, deutherium, or -L2-Ar2, or may be bonded to an adjacent substituent to form a ring. In one embodiment of the present disclosure, R 21 ~R 24 Each independently represents hydrogen or -L2-Ar2, or can bond with an adjacent substituent to form a substituted or unsubstituted aromatic ring. In another embodiment of the present disclosure, R 21 ~R 24 Each of these can independently represent hydrogen or -L2-Ar2, or bond with an adjacent substituent to form an unsubstituted aromatic ring. For example, R 21 ~R 24 Each of these atoms can independently be hydrogen or -L2-Ar2, or they can bond with an adjacent substituent to form a benzene ring.

[0031] In formulas 1 and a, L, L1, L2, and L5 each independently represent a single-bonded, substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3-30 member) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene. In one embodiment of the present disclosure, L, L1, L2, and L5 each independently represent a single-bonded, substituted or unsubstituted (C6-C15) arylene or a substituted or unsubstituted (5-15 member) heteroarylene. In another embodiment of the present disclosure, L, L1, L2, and L5 each independently represent a single-bonded, unsubstituted (C6-C15) arylene or an unsubstituted (5-15 member) heteroarylene substituted with at least one (C6-C12) aryl. For example, L can be a single bond, phenylene, quinazolinylene, quinoxalinylene, etc., L1 can be a single bond, phenylene, naphthylene, biphenylene, phenyl, pyridylene, quinazolinylene, quinoxalinylene, carbazoylene, etc., L2 can be a single bond, phenylene, quinazolinylene, quinoxalinylene, carbazoylene, etc., and L5 can be a single bond, quinazolinylene, etc.

[0032] In Formula 1 and Formula a, Ar, Ar1, Ar2 and Ar5 are each independently halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl or substituted or unsubstituted (C1-C30) alkoxy, or the following Formula b or c:

Chemical formula

[0033] In one embodiment of the present disclosure, Ar, Ar1, Ar2, and Ar5 each independently represent a substituted or unsubstituted (C6-C20) aryl or a substituted or unsubstituted (5-15 member) heteroaryl, or are represented by formula b. In another embodiment of the present disclosure, Ar, Ar1, Ar2, and Ar5 each independently represent an unsubstituted (C6-C20) aryl or an unsubstituted (5-15 member) heteroaryl or an unsubstituted (5-15 member) heteroaryl and an unsubstituted (C6-C15) aryl or an (C1-C6) alkyl-substituted (C6-C15) aryl, or are represented by formula b. For example, Ar may be: phenyl, phenyl substituted with carbazolyl, diphenyltriazinyl, triazinyl substituted with phenyl and dibenzofuranyl, quinazolinyl substituted with at least one phenyl, quinoxalinyl substituted with at least one phenyl, carbazolyl, diphenylamino, naphthylbiphenylamino, phenyldimethylfluorenylamino, phenyldibenzofuranylamino, phenyldibenzothiophenylamino, etc. Ar1 may be: phenyl, biphenyl, terphenyl, phenyl substituted with carbazolyl, diphenyltriazinyl, triazinyl substituted with phenyl and naphthyl, triazinyl substituted with phenyl and biphenyl, triazinyl substituted with phenyl and dimethylfluorenyl, triazinyl substituted with phenyl and tetramethyldihydrophenantrenyl, triazinyl substituted with phenyl and pyridyl, triazinyl substituted with phenyl and dibenzofuranil, triazinyl substituted with phenyl and dibenzothiophenyl, quinazolinyl substituted with at least one phenyl, quinoxalinyl substituted with at least one phenyl, carbazolyl, phenyl-substituted carbazolyl, diphenylamino, etc.Ar2 may include: phenyl, diphenyltriazinyl, triazinyl substituted with phenyl and dibenzofuranyl, quinazolinyl substituted with at least one phenyl, quinoxalinyl substituted with at least one phenyl, carbazolyl, carbazolyl substituted with phenyl, diphenylamino, phenylbiphenylamino, phenyldimethylfluorenylamino, phenyldibenzofuranylamino, phenyldibenzothiophenylamino, etc. Ar5 may include: biphenyl, diphenyltriazinyl, triazinyl substituted with phenyl and naphthyl, triazinyl substituted with phenyl and dibenzofuranyl, triazinyl substituted with phenyl and tetramethyldihydrophenantrenyl, phenyldibenzofuranylamino, phenyldimethylfluorenylamino, etc.

[0034] In equation a, [ka] This represents the binding site with R1 to R8.

[0035] In equations b and c, [ka] These represent binding sites with L, L1, L2, or L5, respectively.

[0036] In one embodiment of the present disclosure, formula 1 can be represented by at least one of the following formulas 1-1 to 1-6. [ka] [ka] In the formula, R1~R8, R 11 ~R 14 , R 21 ~R 24 And X are as defined in Equation 1.

[0037] In one embodiment of the present disclosure, Formula 1 can be represented by at least one of the following Formulas 1-11 to 1-13. [Chemical Formula] Wherein, R1 to R8 and R 11 ~R 14 are as defined in Formula 1; R 41 ~R 44 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted fused rings of (C3-C30) aliphatic rings and (C6-C30) aromatic rings or -L3-N(Ar3)(Ar4); L3 is each independently a single bond, substituted or unsubstituted (C6-C30) arylene or substituted or unsubstituted (3-30 member) heteroarylene; and Ar3 and Ar4 are each independently hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted fused rings of (C3-C30) aliphatic rings and (C6-C30) aromatic rings, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (3-30 member) heteroaryl.

[0038] In one embodiment of the present disclosure, R <, 41 ~R 44 can each independently be hydrogen.

[0039] In one embodiment of the present disclosure, formula a can be represented by at least one of the following formulas a-1 to a-3. [ka] During the ceremony, R 21 ~R 24 And X is as defined in Equation 1; R 51 ~R 54 Each of these independently represents hydrogen, deutherium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted fused ring of an (C3-C30) aliphatic ring and an (C6-C30) aromatic ring, or -L3'-N(Ar3')(Ar4'); L3' independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene or a substituted or unsubstituted (3-30 member) heteroarylene; and Ar3' and Ar4' each independently represent hydrogen, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30) alkenyl, a substituted or unsubstituted fused ring of an (C3-C30) aliphatic ring or (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl.

[0040] In one embodiment of this disclosure, R 51 ~R 54 Each of these can independently be hydrogen.

[0041] The compound represented by formula 1 may be at least one selected from the following compounds, but is not limited to them. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0042] This disclosure provides a plurality of host materials, including a first host material containing an organic electroluminescent compound represented by formula 1 and a second host material different from the first host material. In this case, the second host material may, but is not limited to, a compound represented by any one of the following formulas 2 to 4.

[0043] The compounds represented by Equation 2 will be described in more detail below.

[0044] In Equation 2, X1 and Y1 are independently -N= and -NR 67 - represents -O- or -S-, provided that either X1 or Y1 represents -N= and the other X1 or Y1 represents -NR 67 - represents -O- or -S-. In one embodiment of the present disclosure, either X1 or Y1 represents -N= and the other X1 or Y1 represents -O- or -S-. That is, X1 is -N= and Y1 is -O-; X1 is -N= and Y1 is -S-; X1 is -O- and Y1 is -N=; or X1 is -S- and Y1 is -N=.

[0045] In Equation 2, R 61 R represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 member) heteroaryl. In one embodiment of the present disclosure, R 61 However, R represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5-25 member) heteroaryl. In another embodiment of the present disclosure, R 61 This represents a substituted or unsubstituted (C6-C30) aryl or a substituted (5-20 member) heteroaryl. For example, R 61 However, these can be unsubstituted phenyl, unsubstituted biphenyl, unsubstituted naphthyl, methyl-substituted fluorenyl, methyl-substituted benzofluorenyl, unsubstituted dibenzofuranyl, unsubstituted dibenzothiophenyl, spiro[fluoren-fluoren]yl, spiro[fluoren-benzofluoren]yl, unsubstituted pyridyl, etc.

[0046] In Equation 2, R 62 ~R 64 and R 67Each of these elements independently represents hydrogen, deutherium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted fused ring of an (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -L3''-N(Ar3'')(Ar4''), or may be bonded to an adjacent substituent to form a ring. In this case, L3'' independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene or a substituted or unsubstituted (3-30 member) heteroarylene; and Ar3'' and Ar4'' independently represent hydrogen, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30) alkenyl, a substituted or unsubstituted fused ring of an (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl.

[0047] In one embodiment of this disclosure, R 62 ~R 64 and R 67 Each independently represents hydrogen or a substituted or unsubstituted (C6-C12)aryl. In another embodiment of the present disclosure, R 62 ~R 64 and R 67 Each of these independently represents hydrogen or an unsubstituted (C6-C12) aryl. For example, R 62 and R 63 It can be hydrogen, and R 67 This could be hydrogen, phenyl, or the like.

[0048] In Formula 2, L4 represents a single-bonded, substituted, or unsubstituted (C6-C30) arylene or a substituted or unsubstituted (3-30 member) heteroarylene. In one embodiment of the present disclosure, L4 represents a single-bonded, substituted, or unsubstituted (C6-C18) arylene. In another embodiment of the present disclosure, L4 represents a single-bonded, or unsubstituted (C6-C12) arylene. For example, L4 may be a single-bonded, unsubstituted phenylene, or an unsubstituted naphthylene.

[0049] In Equation 2, R 65 and R 66 Each independently represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 member) heteroaryl. In one embodiment of the present disclosure, R 65 and R 66 Each independently represents a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (3-20 member) heteroaryl. In another embodiment of the present disclosure, R 65 and R 66 Each of these is independently either unsubstituted or substituted with at least one deuterium (C6-C25)aryl, (C1-C6)alkyl, (C6-C25)aryl, (3-20 member) heteroaryl, (C3-C7) cycloalkyl, and (C1-C6) alkyl(C6-C12)aryl; or unsubstituted or (3-20 member) heteroaryl substituted with at least one of (C6-C12)aryl and (5-15 member) heteroaryl. For example, R 65 and R 66Each of these can independently be at least one of the following: substituted phenyl, naphthyl, biphenyl, phenantrenyl, dimethylfluorenyl, diphenylfluorenyl, naphthylphenyl, phenylnaphthyl, dimethylbenzofluorenyl, terphenyl, spirobifluorenyl, benzofuranil, benzothiophenyl, unsubstituted or phenyl-substituted dibenzothiophenyl, unsubstituted or phenyl or pyridyl-substituted dibenzofuranil, phenyl-substituted carbazolyl, benzonaphthofuranil, benzonaphthothiophenyl, benzophropyridyl, etc., where the substituent of the substituted phenyl can be at least one of phenyl substituted with at least one of deutherium, methyl and tert-butyl; anthracenyl; fluoranthenyl; phenylfluorenyl; cyclohexyl; phenyl-substituted pyridyl; phenoxadinyl; and phenyl-substituted benzimidazolyl.

[0050] In Equation 2, a represents 1; b and c each independently represent 1 or 2, preferably 1; d represents an integer from 1 to 4, preferably 1 or 2; and if b to d are integers of 2 or more, R 62 Each of ~R 64 Each of them may be the same as or different from one another.

[0051] The compound represented by formula 2 may be at least one selected from the following compounds, but is not limited to them. [ka] [ka] [ka] [ka] [ka] [ka]

[0052] The compound represented by formula 3 may be at least one selected from the following compounds, but is not limited to them. [ka] [ka] [ka]

[0053] The compound represented by formula 4 may be at least one selected from the following compounds, but is not limited to them. [ka] [ka] [ka] [ka]

[0054] At least one compound from C-1 to C-695 can be used in combination with at least one compound from H1-1 to H1-136, H2-1 to H2-35, and H4-1 to H4-65 for use in organic electroluminescent devices.

[0055] The compounds of Formula 1 according to this disclosure can be prepared according to synthetic methods known to those skilled in the art, for example, according to the following reaction schemes 1 to 4, but are not limited thereto. [ka]

[0056] In reaction schemes 1-4, R1-R4, R 11 ~R 14 , R 21 ~R 24 L1, L2, Ar1, and Ar2 are as defined in Formula 1, and Hal is a halogen atom.

[0057] The compounds represented by Formula 2 of this disclosure can be prepared by synthetic methods known to those skilled in the art, for example, by referring to the following patent documents: (Patent Document 2) (Published: March 2, 2017), (Patent Document 3) (Published: May 11, 2017), (Patent Document 4) (Published: August 24, 2018), etc.

[0058] The compound represented by formula 3 of this disclosure can be prepared by synthetic methods known to those skilled in the art.

[0059] Compounds represented by Formula 4 of this disclosure can be prepared by referring to (Patent Document 5) (Publication Date: March 10, 2020), but are not limited thereto.

[0060] The above lists exemplary synthetic examples of compounds represented by Formula 1, and those skilled in the art will readily understand the following: They are all based on reactions such as the Buchwald-Hartwig cross-coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, Miyaura boration reaction, Suzuki cross-coupling reaction, intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, cyclic dehydration reaction, SN1 substitution reaction, SN2 substitution reaction, and phosphine-mediated reductive cyclization reaction, and the above reactions proceed as defined by Formula 1, even if substituents not specified in the particular synthetic example are attached.

[0061] The organic electroluminescent device of this disclosure may include the compound of Formula 1. In this case, the compound of Formula 1 may be included in the light-emitting layer.

[0062] In addition, the organic electroluminescent device of the present disclosure includes an anode, a cathode, and at least one organic layer between the anode and the cathode, wherein the organic layer may include a plurality of organic electroluminescent materials, including a compound represented by formula 1 as a first organic electroluminescent material, and a compound represented by any one of formulas 2 to 4 as a second organic electroluminescent material. In one embodiment of the present disclosure, the organic electroluminescent device of the present disclosure includes an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein the at least one light-emitting layer may include a plurality of host materials, including a compound represented by formula 1 as a first host material and a compound represented by any one of formulas 2 to 4 as a second host material.

[0063] The electrodes may be semi-transparent or reflective, and depending on the material, they may be top-emitting, bottom-emitting, or double-sided emitting types. In addition, the hole injection layer may be further doped with a p-dopant, and the electron injection layer may be further doped with an n-dopant.

[0064] The luminescent layer contains a host and a dopant, and the host contains multiple host materials, wherein the compound represented by formula 1 may be included as the first host compound among the multiple host materials, and the compound represented by any of formulas 2 to 4 may be included as the second host compound among the multiple host materials. In this case, the weight ratio of the first host compound to the second host compound is about 1:99 to about 99:1, preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30, more preferably about 40:60 to 60:40, and even more preferably about 50:50. If two or more materials are included in one layer, the mixture is evaporated separately or co-evaporates simultaneously to form the layer.

[0065] In this disclosure, the light-emitting layer is a light-emitting layer, which may be a single layer or a plurality of layers stacked together. In the plurality of host materials of this disclosure, both the first and second host materials may be contained in one layer or each in a separate light-emitting layer. In one embodiment of this disclosure, the doping concentration of the dopant compound to the host compound in the light-emitting layer may be less than 20% by weight.

[0066] In the organic electroluminescent devices of this disclosure, a hole transport zone may be included between the anode and the light-emitting layer. This hole transport zone may include at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, and an electron barrier layer. Each of these hole injection layer, hole transport layer, hole auxiliary layer, light-emitting auxiliary layer, and electron barrier layer may be a single layer or a plurality of layers consisting of two or more layers stacked on top of each other. The hole injection layer may be multilayered for the purpose of lowering the hole injection barrier (i.e., hole injection voltage) from the anode to the hole transport layer or electron barrier layer, in which case two compounds may be used simultaneously in each of the multilayers. An electron barrier layer can be placed between the hole transport layer (or hole injection layer) and the light-emitting layer to prevent electron overflow from the light-emitting layer, confine excitons within the light-emitting layer, and prevent light leakage.

[0067] In addition, the hole transport zone may include a p-doped hole injection layer, a hole transport layer, and an luminescence auxiliary layer. A p-doped hole injection layer refers to a hole injection layer doped with a p-dopant. A p-dopant is a substance that contributes to p-semiconductor properties. P-semiconductor properties refer to the property of a substance that injects or transports holes to the HOMO energy level, that is, a substance with high hole conductivity.

[0068] In the organic electroluminescent devices of this disclosure, an electron transport zone may be included between the light-emitting layer and the cathode. This electron transport zone may include at least one of a hole barrier layer, an electron transport layer, an electron buffer layer, and an electron injection layer. Each of these, the hole barrier layer, electron transport layer, electron buffer layer, and electron injection layer, may be a single layer or a plurality of layers consisting of two or more layers stacked on top of each other. The electron injection layer may be further doped with an n-dopant. The electron buffer layer may be multilayered for the purpose of controlling electron injection and improving the interfacial properties between the light-emitting layer and the electron injection layer, in which case two compounds may be used simultaneously in each multilayer. The hole barrier layer or electron transport layer may be multilayered, in which case multiple compounds may be used in each multilayer. In one embodiment of this disclosure, at least one of the electron transport zones, preferably the electron buffer layer, may contain a compound represented by formula 1.

[0069] A light-emitting auxiliary layer is a layer placed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer. When a light-emitting auxiliary layer is placed between the anode and the light-emitting layer, it can be used to facilitate hole injection and / or transport or to prevent electron overflow. When a light-emitting auxiliary layer is placed between the cathode and the light-emitting layer, it can be used to facilitate electron injection and / or transport or to prevent hole overflow. In addition, a light-emitting auxiliary layer can also be placed between a hole transport layer (or hole injection layer) and the light-emitting layer to facilitate or block the hole transport rate (or injection rate), thereby enabling control of the charge balance. If the organic electroluminescent device contains two or more hole transport layers, the additionally included hole transport layers can also be used as hole auxiliary layers or electron barrier layers. Light-emitting auxiliary layers, hole auxiliary layers, or electron barrier layers may have the effect of improving the efficiency and / or lifetime of the organic electroluminescent device.

[0070] The dopants that can be included in the organic electroluminescent devices of this disclosure may be at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant. There are no particular limitations on the phosphorescent dopant material applied to the organic electroluminescent devices of this disclosure, but it may be selected from metallization complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), preferably from ortho-metallization complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and more preferably from ortho-metallated iridium complex compounds.

[0071] The dopants included in the organic electroluminescent devices of this disclosure may be, but are not limited to, compounds represented by the following formula 101. [ka]

[0072] In Equation 101, L' has the following structure 1-3: [ka] Selected from, R 100 ~R 103 Each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium and / or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3-30 member) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; or together with pyridine, may bond to an adjacent substituent, such as a substituted or unsubstituted quinoline, isoquinoline, benzophropyridine, benzothienopyridine, idenopyridine, benzophroquinoline, benzothienoquinoline, or indenoquinoline ring to form a ring; R 104 ~R 107Each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium and / or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or together with benzene, may bond to an adjacent substituent, such as substituted or unsubstituted, naphthalene, fluorene, dibenzothiophene, dibenzofuran, idenopyridine, benzoflopyridine, or benzothienopyridine rings to form a ring; 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 may be bonded to an adjacent substituent to form a ring; and 's' represents an integer between 1 and 3.

[0073] Specific examples of dopant compounds include, but are not limited to, the following. [ka] [ka] [ka] [ka] [ka] [ka]

[0074] Each layer of the organic electroluminescent device of this disclosure can be formed by any one of the following methods: dry film formation methods such as vacuum evaporation, sputtering, plasma, or ion plating; or wet film formation methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, or flow coating.

[0075] When using a wet film formation method, thin films can be formed by dissolving or diffusing the substances forming each layer in various suitable solvents, such as ethanol, chloroform, tetrahydrofuran, or dioxane. There are no particular restrictions on the solvent, as long as the substances forming each layer are soluble or dispersible in the solvent and do not cause any problems in film formation.

[0076] In addition, the compounds represented by formula 1 and any one of formulas 2-4 can be formed by the methods listed above, generally by a co-evaporation process or a mixture-evaporation process. The co-evaporation method is a mixed deposition method in which two or more substances are placed in separate crucible sources, and an electric current is applied to both cells simultaneously to evaporate them. The mixture evaporation method is a mixed deposition method in which two or more substances are mixed in one crucible source before deposition, and then an electric current is applied to one cell to evaporate the multiple substances. In addition, if the first and second host compounds are present in the same layer or different layers in an organic electroluminescent device, the two host compounds can be formed independently. For example, the first host compound may be deposited first, followed by the second host compound.

[0077] In addition, the organic electroluminescent materials according to this disclosure can be used as light-emitting materials for white organic light-emitting devices. For white organic light-emitting devices, various structures have been proposed, such as parallel-parallel structures, stacked structures, or color conversion material (CCM) methods, depending on the arrangement of R (red), G (green), or YG (yellow-green) and B (blue) light-emitting components. This disclosure can be applied to such white organic light-emitting devices. In addition, the organic electroluminescent materials according to this disclosure can also be used in organic electroluminescent devices containing QDs (quantum dots).

[0078] This disclosure can provide a display system using a plurality of host materials comprising a compound represented by formula 1 and any one of the compounds represented by formulas 2 to 4. That is, it is possible to manufacture a display system or a lighting system by using the organic electroluminescent compounds or plurality of host materials of this disclosure. Specifically, it is possible to manufacture a display system, such as a white organic light-emitting element, a display system for a smartphone, tablet, laptop, PC, TV, or automobile, or a lighting system, such as an indoor and outdoor lighting system, by using the plurality of host materials of this disclosure.

[0079] Hereafter, the methods for preparing the compounds of this disclosure, their properties, and the properties of organic electroluminescent devices comprising the organic electroluminescent compounds or multiple host materials according to this disclosure will be described in detail with reference to representative compounds of this disclosure. The following examples are solely for the purpose of illustrating the properties of organic electroluminescent devices comprising the compounds or multiple host materials according to this disclosure, and this disclosure is not limited to the following examples. [Examples]

[0080] Example 1: Preparation of compound C-26 [ka]

[0081] Synthesis of compound 1-1 3-Bromo-9,9,10,10-tetramethyl-9,10-dihydrophenanthrene (30 g, 95.2 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (29.0 g, 114 mmol), PdCl2(PPh3)2 (3.34 g, 4.76 mmol), KOAc (23.3 g, 238 mmol), and 500 mL of 1,4-dioxane were added to a flask and dissolved. The mixture was then stirred under flux at 140°C for 3 hours. After the reaction was complete, the mixture was cooled to room temperature and separated by passing it through a silica filter to obtain compound 1-1 (31.0 g, yield: 90%).

[0082] Synthesis of Compounds 1-2 Compound 1-1 (14.0 g, 38.6 mmol), 1-bromo-2-nitrobenzene (8.20 g, 40.6 mmol), tetrakis(triphenylphosphine)palladium(0) (4.47 g, 3.86 mmol), and NaOH (4.64 g, 116 mmol) were dissolved in a mixture of 130 mL of THF and 70 mL of H2O in a flask, and the mixture was stirred under flux at 110°C for 3 hours. After the reaction was complete, ethyl acetate and water were added to separate the organic layer, and compound 1-2 was obtained using a silica filter (17.0 g, yield: 116%).

[0083] Synthesis of Compounds 1-3 Compounds 1-2 (16.0 g, 44.8 mmol) and PPh3 (29.4 g, 112 mmol) were dissolved in 220 mL of o-DCB in a flask, and the mixture was stirred under flux at 230°C for 1 day. After the reaction was complete, the solvent was removed by distillation, and the compounds were separated by column chromatography to obtain compound 1-3 (6.50 g, yield: 45%).

[0084] Synthesis of compound C-26 Compounds 1-3 (2.50 g, 7.68 mmol), 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.13 g, 8.07 mmol), Pd2(dba)3 (0.350 g, 0.384 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos) (0.315 g, 0.768 mmol), and NaOt-Bu (1.85 g, 19.2 mmol) were dissolved in 70 mL of o-xylene in a flask and stirred at 180 °C for 1 hour under flux. After the reaction was complete, the solvent was removed by filtration under reduced pressure, and the compounds were separated by column chromatography to obtain compound C-26 (1.10 g, yield: 22.6%).

[0085] [Table 1]

[0086] Example 2: Preparation of compound C-582 [ka]

[0087] Synthesis of Compound 2-1 9,9,10,10-Tetramethyl-9,10-dihydrophenanthrene (34.0 g, 144 mmol), I2 (18.3 g, 71.9 mmol), iodic acid (12.7 g, 71.9 mmol), 280 mL of AcOH, 36 mL of H2SO4, 36 mL of H2O, and 15 mL of CHCl3 were added to a flask and stirred at 65°C. After the reaction was complete, the solvent was removed, and the mixture was separated by column chromatography, after which MeOH was added. The resulting solid was filtered under reduced pressure to obtain compound 2-1 (56.0 g, yield: 107%).

[0088] Synthesis of compound 2-2 Compound 2-1 (35.0 g, 96.6 mmol), (5-chloro-2-formylphenyl)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 added to a flask and stirred at 140°C. After the reaction was complete, ethyl acetate and water were added to separate the layers, and then only the organic layer was separated. The solvent was removed by filtration under reduced pressure, and then the layer was separated by column chromatography. MeOH was added to it, and the resulting solid was filtered under reduced pressure to obtain compound 2-2 (36.0 g, yield: 99.4%).

[0089] Synthesis of Compounds 2-3 Compound 2-2 (30.0 g, 80.0 mmol) and PPh3ClCH2OMe (38.4 g, 112 mmol) were dissolved in 370 mL of THF in a flask. 112 mL of a 1 M solution of KOt-Bu in THF was added dropwise, and the mixture was stirred. Once the reaction was complete, ethyl acetate and water were added to separate the layers, and then only the organic layer was separated. The solvent was removed by filtration under reduced pressure, and the residue was separated by column chromatography. MeOH was added to this residue, and the resulting solid was filtered under reduced pressure to obtain compound 2-3 (20.0 g, yield: 62.0%).

[0090] Synthesis of Compounds 2-4 Compound 2-3 (19.0 g, 47.2 mmol) was dissolved in 250 mL of methylene chloride (MC) in a flask, and 17.8 mL of BF3·EtOEt solution was added dropwise, and the mixture was stirred at 0°C. Once the reaction was complete, MC and NaHCO3 (aqueous solution) were added to separate the layers, and then only the organic layer was separated. The solvent was removed by filtration under reduced pressure, and the residue was separated by column chromatography. MeOH was added to this residue, and the resulting solid was filtered under reduced pressure to obtain compound 2-4 (16.0 g, yield: 91.5%).

[0091] Synthesis of compound C-582 Compound 2-4 (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), S-Phos (0.664 g, 1.62 mmol), NaOt-Bu (3.11 g, 32.4 mmol), and 80 mL of o-xylene were added to a flask and stirred under flux at 180°C. After the reaction was complete, the solvent was removed by filtration under reduced pressure, and the residue was separated by column chromatography. MeOH was added to the residue, and the resulting solid was filtered under reduced pressure to obtain compound C-582 (2.3 g, yield: 23.9%).

[0092] [Table 2]

[0093] Example 3: Preparation of compound H1-27 [ka]

[0094] Synthesis of Compound 1 Dibenzofuran-2-amine (20 g, 144.7 mmol), 2-bromodibenzofuran (23.8 g, 96.47 mmol), Pd(OAc)2 (1.1 g, 4.82 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos) (3.9 g, 9.65 mmol), NaOt-Bu (13.9 g, 144.7 mmol), and 485 mL of o-xylene were added to a flask and stirred at 160 °C for 3 hours. After the reaction was complete, the mixture was cooled to room temperature. The organic layer was extracted using ethyl acetate, and any remaining moisture was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound 1 (4.9 g, yield: 10%).

[0095] Synthesis of compound H1-27 Compound 1 (4.9 g, 12.76 mmol), Compound 2 (4.2 g, 14.0 mmol), Pd(dba3)2 (0.584 g, 0.638 mmol), S-Phos (0.523 g, 1.276 mmol), NaOt-Bu (1.8 g, 19.14 mmol), and 65 mL of o-xylene were added to a flask and stirred at 160 °C for 2 hours. After the reaction was complete, the mixture was cooled to room temperature. The organic layer was extracted using ethyl acetate, and any remaining moisture was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain Compound H1-27 (5.6 g, yield: 68.3%).

[0096] [Table 3]

[0097] Example 4: Preparation of compound H1-46 [ka] Compound 3 (25 g, 74.48 mmol), Compound 2 (42.58 g, 81.93 mmol), Pd(OAc)2 (0.16 g, 7.5 mmol), P(t-Bu)3 (0.28 g, 7.5 mmol), NaOt-Bu (14.31 g, 150 mmol), and 284.09 mL of o-xylene were added to a flask and stirred at 160°C for 2 hours. After the reaction was complete, the mixture was cooled to room temperature. The organic layer was extracted using ethyl acetate, and any remaining moisture was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound H1-46 (23.4 g, yield: 50%).

[0098] [Table 4]

[0099] Example 5: Preparation of compound H1-43 [ka] Compound 4 (20 g, 56.96 mmol), Compound 2 (18.8 g, 57.13 mmol), Pd(OAc)2 (0.13 g, 5.7 mmol), P(t-Bu)3 (0.22 g, 5.7 mmol), NaOt-Bu (11 g, 113.92 mmol), and 227.27 mL of o-xylene were added to a flask and stirred at 160°C for 2 hours. After the reaction was complete, the reaction mixture was cooled to room temperature. The organic layer was extracted using ethyl acetate, and any remaining moisture was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound H1-43 (12.5 g, yield: 34%).

[0100] [Table 5]

[0101] Example 6: Preparation of compound H1-123 [ka]

[0102] Synthesis of Compound 5 3-aminobiphenyl (54 g, 319 mmol), 3-bromoviphenyl (70 g, 301 mmol), Pd(OAc)2 (0.33 g, 1.47 mmol), tricyclohexylphosphine (0.84 g, 2.8 mmol), NaOt-Bu (57 g, 593 mmol), and 280 mL of toluene were added to a flask and stirred at 95°C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature. The organic layer was extracted using ethyl acetate, and any remaining moisture was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound 5 (60.23 g, yield: 85%).

[0103] Synthesis of compound H1-123 Compound 5 (60.23 g, 187.5 mmol), Compound 2 (60 g, 182.33 mmol), Pd(OAc)2 (0.41 g, 1.83 mmol), S-Phos (1.74 g, 4.23 mmol), NaOt-Bu (26.23 g, 272 mmol) and 300 mL of xylene were added to a flask and stirred at 110 °C for 10 hours. After the reaction was complete, the mixture was cooled to room temperature. The organic layer was extracted with ethyl acetate and the remaining moisture was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain Compound H1-123 (36.9 g, yield: 33%).

[0104] [Table 6]

[0105] Example 7: Preparation of Compound H1-136 [Chemical Structure]

[0106] Synthesis of Compound 6 Dibenzofuran-2-amine (29.24 g, 159.7 mmol), 2-bromodibenzothiophene (40 g, 152.7 mmol), Pd(OAc)2 (0.17 g, 0.75 mmol), tricyclohexylphosphine (0.43 g, 1.45 mmol), NaOt-Bu (29.22 g, 304 mmol) and 250 mL of toluene were added to a flask and stirred at 95 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature. The organic layer was extracted with ethyl acetate and the remaining moisture was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain Compound 6 (17.12 g, yield: 86%).

[0107] Synthesis of Compound H1-136 Compound 6 (17.12 g, 46.89 mmol), Compound 2 (15 g, 45.58 mmol), Pd(OAc)2 (0.05 g, 0.22 mmol), S-Phos (0.22 g, 0.535 mmol), NaOt-Bu (6.56 g, 68.2 mmol), and 75 mL of xylene were added to a flask and stirred at 110°C for 10 hours. After the reaction was complete, the mixture was cooled to room temperature. The organic layer was extracted using ethyl acetate, and any remaining moisture was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound H1-136 (10.2 g, yield: 34%).

[0108] [Table 7]

[0109] Example 8: Preparation of compound H1-85 [ka] Compound 2 (5.0 g, 15.2 mmol), di([1,1'-biphenyl]-4-yl)amine (4.9 g, 15.2 mmol), Pd(OAc)2 (0.2 g, 0.8 mmol), P(t-Bu)3 (0.8 mL, 1.5 mmol), NaOt-Bu (2.9 g, 30.4 mmol), and 76 mL of xylene were added to a flask and stirred at 160 °C for 5 hours. After the reaction was complete, the mixture was cooled to room temperature. The precipitated solid was washed with distilled water and methanol, and separated by column chromatography to obtain compound H1-85 (5.5 g, yield: 59%).

[0110] Example 9: Preparation of compound H1-51 [ka] Compound 2 (4 g, 12 mmol), bis(biphenyl-4-yl)[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]amine (6.8 g, 13 mmol), Pd(OAc)2 (0.3 g, 1 mmol), S-Phos (0.9 g, 2 mmol), Cs2O3 (11.5 g, 35 mmol), 60 mL of o-xylene, 15 mL of EtOH, and 15 mL of distilled water were added to a flask and stirred under flux at 150 °C for 3 hours. After the reaction was complete, the mixture was cooled to room temperature and washed with distilled water. The organic layer was extracted with ethyl acetate, and any remaining moisture was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound H1-51 (2.2 g, yield: 27%).

[0111] Example 10: Preparation of compound H1-68 [ka] Compound 7 (4.8 g, 11.34 mmol), N-(4-bromophenyl)-N-phenyl-[1,1'-biphenyl]-4-amine (5 g, 12.47 mmol), Pd(PPh3)4 (0.4 g, 0.34 mmol), Na2CO3 (3.0 g, 28.35 mmol), 57 mL of toluene, 14 mL of ethanol, and 14 mL of distilled water were added to a flask and stirred at 120°C for 4 hours. Once the reaction was complete, the mixture was added dropwise to methanol, and the resulting solid was filtered. The resulting solid was purified by column chromatography to obtain compound H1-68 (1.4 g, yield: 20.0%).

[0112] Example 11: Preparation of compound H1-15 [ka]

[0113] Synthesis of compound 8 Compound 2 (10.0 g, 30.3 mmol), [1,1'-biphenyl]-3-amine (6.7 g, 39.4 mmol), Pd(OAc)2 (0.34 g, 1.5 mmol), P(t-Bu)3 (1.5 mL, 3.03 mmol), NaOt-Bu (5.8 g, 60.6 mmol), and 150 mL of xylene were added to a flask and stirred at 160 °C for 6 hours. After the reaction was complete, the mixture was washed with distilled water. The organic layer was extracted with ethyl acetate and dried using magnesium sulfate. The solvent was removed using a rotary evaporator. The residue was separated by column chromatography to obtain compound 8 (10.8 g, yield: 36%).

[0114] Synthesis of compound H1-15 Compound 8 (5.0 g, 10.8 mmol), 3-bromodibenzofuran (3.2 g, 12.9 mmol), Pd2(dba)3 (0.5 g, 0.54 mmol), S-Phos (0.45 g, 1.08 mmol), NaOt-Bu (2.0 g, 21.6 mmol), and 60 mL of o-xylene were added to a flask and stirred at 160 °C for 6 hours. After the reaction was complete, the mixture was cooled to room temperature. The organic layer was extracted using ethyl acetate, and any remaining moisture was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound H1-15 (1.45 g, yield: 21%).

[0115] [Table 8]

[0116] Device Example 1: Manufacturing of a green light-emitting OLED containing the compound according to this disclosure An OLED containing an organic electroluminescent compound according to the present disclosure was fabricated. First, an indium tin oxide (ITO) thin film (10 Ω / sq) of a transparent electrode on a glass substrate (Geomatic Co., Ltd., Japan) for the OLED was subjected to ultrasonic cleaning using acetone and isopropyl alcohol in that order, and then stored in isopropanol before use. The ITO substrate was mounted on the substrate holder of a vacuum evaporation apparatus. Compound HI-1 was introduced into the cell of the vacuum evaporation apparatus, and compound HT-1 was introduced into another cell. The two substances were evaporated at different rates, and a hole injection layer having a thickness of 10 nm was deposited by doping compound HI-1 in an amount of 3 wt% based on the total amount of compound HI-1 and compound HT-1. Next, compound HT-1 was introduced into the cell of the vacuum evaporation apparatus and evaporated by applying a current to the cell, whereby a first hole transport layer having a thickness of 80 nm was deposited on the hole injection layer. Then, compound HT-2 was introduced into another cell of the vacuum evaporation apparatus and evaporated by applying a current to the cell, whereby a second hole transport layer having a thickness of 30 nm was deposited on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light-emitting layer was deposited thereon as follows: Compound C-26 was introduced into the cell of the vacuum evaporation apparatus as a host, and compound D-50 was introduced into another cell as a dopant. Subsequently, the dopant was doped in an amount of 10 wt% based on the total amount of the host and the dopant, and a light-emitting layer having a thickness of 40 nm was deposited on the second hole transport layer. Then, compound ETL-1:compound EIL-1 was evaporated at a weight ratio of 40:60, and an electron transport layer having a thickness of 35 nm was deposited on the light-emitting layer. After depositing compound EIL-1 as an electron injection layer having a thickness of 2 nm, an Al cathode having a thickness of 80 nm was deposited on the electron injection layer by another vacuum evaporation apparatus to fabricate an OLED. Each starting compound was purified by vacuum sublimation at 10 -6 torr and then used.

[0117] Comparative Example 1: Fabrication of a green-emitting OLED containing a conventionally used compound as a host An OLED was manufactured in the same manner as in Device Example 1, except that compound CBP (4,4'-N,N'-dicarbazole-biphenyl) was used as the host material for the light-emitting layer, Balq (aluminum(III) bis(2-methyl-8-quinolinate)4-phenylphenolate) was deposited as a hole barrier layer to a thickness of 5 nm, and on top of the hole barrier layer, an electron transport layer with a thickness of 30 nm was deposited by evaporating compound ETL-1 to compound EIL-1 in a weight ratio of 40:60.

[0118] Table 1 below shows the driving voltage, luminous efficiency, and light source color based on the brightness of 1,000 nits for Device Example 1 and Comparative Example 1, which were prepared as described above.

[0119] [Table 9]

[0120] The organic electroluminescent device using the host material according to this disclosure exhibited a lower drive voltage and higher luminous efficiency compared to the organic electroluminescent device using the host material of Comparative Example 1. In addition, the organic electroluminescent device using the host material according to this disclosure may have excellent lifetime performance.

[0121] Device Examples 2 and 3: Manufacturing of a red light-emitting OLED comprising multiple host materials according to the present disclosure An OLED was manufactured according to this disclosure. First, an indium tin oxide (ITO) thin film (10 Ω / sq) of transparent electrodes on a glass substrate for the OLED (Geomatec Co., Ltd., Japan) was ultrasonically cleaned using acetone and isopropyl alcohol in that order, then stored in isopropanol, and then used. The ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus. Compound HI-1 was introduced into a cell of the vacuum deposition apparatus, and compound HT-1 was introduced into another cell. The two substances were evaporated at different rates, and a hole injection layer with a thickness of 10 nm was deposited by doping with compound HI-1 at an amount of 3 wt% based on the total amount of compound HI-1 and compound HT-1. Next, compound HT-1 was introduced into a cell of the vacuum deposition apparatus, and evaporated by applying an electric current to the cell, thereby depositing a first hole transport layer with a thickness of 80 nm on top of the hole injection layer. Next, compound HT-3 was introduced into another cell of the vacuum deposition apparatus and evaporated by applying an electric current to the cell, thereby depositing a second hole transport layer with a thickness of 60 nm on top of the first hole transport layer. After forming the hole injection layer and the hole transport layer, an emissive layer was deposited on top of them as follows: The first and second host compounds shown in Table 2 below were introduced as hosts into two cells of the vacuum deposition apparatus, and compound D-39 was introduced as a dopant into another cell. These two host materials were evaporated in a 1:1 ratio, and the dopant was evaporated at a different rate, thereby doping the material with 3% by weight of the dopant based on the total amount of host and dopant, and depositing an emissive layer with a thickness of 40 nm on top of the second hole transport layer. Next, compound ETL-1:compound EIL-1 was evaporated in a 50:50 weight ratio, and an electron transport layer with a thickness of 35 nm was deposited on top of the emissive layer. After depositing compound EIL-1 as an electron injection layer with a thickness of 2 nm onto the electron transport layer, an Al cathode with a thickness of 80 nm was deposited on top of the electron injection layer using a separate vacuum deposition apparatus to produce an OLED. Each raw material compound was 10 -6 The material was purified by vacuum sublimation using a Torr device before use.

[0122] Comparative Examples 2 and 3: Production of red light-emitting OLEDs containing commonly used compounds as hosts An OLED was manufactured in the same manner as in Device Examples 2 and 3, except that compound CBP or compound H1-9 was used as the single host material for the light-emitting layer.

[0123] Table 2 below shows the driving voltage, luminous efficiency, and the time it takes for the light source color based on 1,000 nits of brightness and brightness based on 5,000 nits of brightness to decrease from 100% to 95% (lifetime: T95) of the organic electroluminescent devices of Device Examples 2 and 3 and Comparative Examples 2 and 3 prepared as described above.

[0124] [Table 10]

[0125] The organic electroluminescent devices using multiple host materials according to this disclosure exhibited lower drive voltage, higher luminescence efficiency, and superior lifetime performance compared to the organic electroluminescent devices using the host materials of Comparative Examples 2 and 3.

[0126] Device Example 4: Manufacturing of a green light-emitting OLED containing multiple host materials according to the present disclosure An OLED was manufactured according to this disclosure. First, an indium tin oxide (ITO) thin film (10 Ω / sq) of transparent electrodes on a glass substrate for the OLED (Geomatec Co., Ltd., Japan) was ultrasonically cleaned using acetone and isopropyl alcohol in that order, then stored in isopropanol, and then used. The ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus. Compound HI-1 was introduced into a cell of the vacuum deposition apparatus, and compound HT-1 was introduced into another cell. The two substances were evaporated at different rates, and a hole injection layer with a thickness of 10 nm was deposited by doping with compound HI-1 at an amount of 3 wt% based on the total amount of compound HI-1 and compound HT-1. Next, compound HT-1 was introduced into a cell of the vacuum deposition apparatus, and evaporated by applying an electric current to the cell, thereby depositing a first hole transport layer with a thickness of 80 nm on top of the hole injection layer. Next, compound HT-2 was introduced into another cell of the vacuum deposition apparatus and evaporated by applying an electric current to the cell, thereby depositing a second hole transport layer with a thickness of 30 nm on top of the first hole transport layer. After forming the hole injection layer and the hole transport layer, an emissive layer was deposited thereon as follows: Compounds C-26 and H2-2 were introduced as hosts into the cells of the vacuum deposition apparatus, and compound D-130 was introduced as a dopant into another cell. These two host materials were evaporated in different ratios of 2:1, and the dopant was evaporated at a different rate, thereby doping the material with 10% by weight of the dopant relative to the total amount of host and dopant, and depositing an emissive layer with a thickness of 40 nm on top of the second hole transport layer. Next, compound ETL-1:compound EIL-1 was evaporated in a weight ratio of 40:60, and an electron transport layer with a thickness of 35 nm was deposited on top of the emissive layer. After depositing compound EIL-1 as an electron injection layer with a thickness of 2 nm onto the electron transport layer, an Al cathode with a thickness of 80 nm was deposited on top of the electron injection layer using a separate vacuum deposition apparatus to produce an OLED. Each raw material compound was 10 -6 The material was purified by vacuum sublimation using a Torr device before use.

[0127] Comparative Example 4: Production of a green light-emitting OLED containing a commonly used compound as a host. An OLED was manufactured in the same manner as in Device Example 4, except that compound H2-2 was used as the single host material for the light-emitting layer.

[0128] Table 3 below shows the driving voltage, luminous efficiency, and light source color based on the brightness of 1,000 nits for Device Example 4 and Comparative Example 4, which were prepared as described above.

[0129] [Table 11]

[0130] The organic electroluminescent device using multiple host materials according to this disclosure exhibited a lower drive voltage and higher luminous efficiency compared to the organic electroluminescent device using the host material of Comparative Example 4. In addition, the organic electroluminescent device using multiple host materials according to this disclosure may have superior lifetime performance.

[0131] Speaking without being constrained by theory, the R in the dihydrophenanthrene backbone of Equation 1 11 ~R 14 In the case of a compound that is entirely hydrogen, irradiation with light readily converts it to a compound having a phenanthrene backbone (e.g., a phenantroindole structure). Compounds having a phenanthrene backbone (e.g., phenantroindole) can act like impurities because phenanthrene has a lower triplet energy gap than dihydrophenanthrene. In this case, the properties of the OLED may degrade. In this disclosure, R 11 ~R 14 We attempted to solve this problem by introducing a protecting group such as a methyl group. Specifically, the introduction of a methyl group does not affect the HOMO and LUMO energies.

[0132] Table 12

Claims

1. The following equation 1: 【Chemistry 1】 (In the formula, R １１ ~R １４ Each of these elements may independently represent a substituted or unsubstituted (C1-C30) alkyl group, or may be bonded to an adjacent substituent to form a ring; R １ ~R ８ each independently represents hydrogen, deuterium or -L-Ar, or may be bonded to adjacent substituents to form a ring, provided that R １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ５ and R ６ , R ６ and R ７ as well as R ７ and R ８ at least one of the pairs of is bonded to each other to form the following formula a: 【Chemistry 2】 It was fused as, in the formula, X is NR ３１ , O, S, or -CR ３４ =CR ３５ - represents; R ３１ is, -L １ -Ar １ It represents; R ３４ and R ３５ These are, independently, hydrogen, deutherium, or -L. ５ -Ar ５ It represents; R ２１ ~R ２４ These are, independently, hydrogen, deutherium, or -L. ２ -Ar ２ It may represent or be bonded to an adjacent substituent to form a ring; L, L １ , L ２ and L ５ Each of these independently represents a single bond, a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3-30 member) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene; Ar, Ar １ Ar ２ and Ar ５ Each independently represents a halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C1-C30) alkoxy, or the following formula b or c: 【Transformation 3】 It is expressed by, in the formula, R ａ１ , R ａ２ , R ｂ１ , R ｂ２ and R ｂ３ Each of these independently represents a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 member) heteroaryl, or a substituted or unsubstituted (C3-C30) cycloalkyl; In equation a 【Chemistry 4】 R １ ~R ８ Represents the binding site with; and In equations b and c 【Transformation 5】 These are L, L respectively. １ , L ２ or L ５ (Represents the binding site with) An organic electroluminescent compound represented by [the specified symbol].

2. Equation 1 is as follows: Equations 1-1 to 1-6: 【Transformation 6】 【Transformation 7】 (In the formula, R １ ~R ８ , R １１ ~R １４ , R ２１ ~R ２４ (and X is as defined in claim 1) The organic electroluminescent compound according to claim 1, represented by at least one of the following.

3. Equation 1 is represented by the following equations 1-11 to 1-13: 【Transformation 8】 (In the formula, R １ ~R ８ and R １１ ~R １４ This is as defined in claim 1; R ４１ ~R ４４ Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted fused rings of (C3-C30) aliphatic rings and (C6-C30) aromatic rings or -L ３ -N(Ar ３ ) (Ar ４ ) represents; L ３ Each of these independently represents a single bond, substituted or unsubstituted (C6-C30) arylene or a substituted or unsubstituted (3-30 member) heteroarylene; and Ar ３ and Ar ４ Each of these independently represents hydrogen, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30) alkenyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl. The organic electroluminescent compound according to claim 1, represented by at least one of the following.

4. Equation a is given by the following equations a-1 to a-3: 【Chemistry 9】 (In the formula, R ２１ ~R ２４ And X is as defined in claim 1; R ５１ ~R ５４ Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted fused rings of (C3-C30) aliphatic rings and (C6-C30) aromatic rings or -L ３ '-N(Ar ３ ')(Ar ４ ') represents; L ３ ' represents, independently, a single bond, a substituted or unsubstituted (C6-C30) arylene or a substituted or unsubstituted (3-30 member) heteroarylene; and Ar ３ 'and Ar ４ ' represents, independently, hydrogen, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30) alkenyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl. The organic electroluminescent compound according to claim 1, represented by at least one of the following.

5. R １１ to R １４ , L, L １ , L ２ , L ５ , Ar, Ar １ , Ar ２ , Ar ５ , R ａ１ , R ａ２ and R ｂ１ to R ｂ３ The substituents of the substituted alkyl, substituted alkylene, substituted cycloalkyl, substituted cycloalkylene, substituted alkoxy, substituted aryl, substituted arylene, substituted heteroaryl, and substituted heteroarylene are, each independently, deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; (C1-C30) alkyl; halo(C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy ; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3-7 member) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; unsubstituted or (3-30 member) heteroaryl substituted with at least one (C6-C30) aryl; unsubstituted or (C6-C30) aryl substituted with at least one (C1-C30) alkyl and (3-30 member) heteroaryl; tri(C1-C30) alkylsilyl; tri(C6-C30) aryl Lucilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; amino; mono- or di-(C1-C30)alkylamino; mono- or di-(C2-C30)alkenylamino; unsubstituted or (C1-C30)alkyl-substituted mono- or di-(C6-C30)arylamino; mono- or di-(3-30 member) heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30 ) arylamino; (C1-C30) alkyl(3-30 member) heteroarylamino; (C2-C30) alkenyl(C6-C30) arylamino; (C2-C30) alkenyl(3-30 member) heteroarylamino; (C6-C30) aryl(3-30 member) heteroarylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; di(C6-C30) arylboronyl; di(C1-C30) alkylboronyl; (C1-C30) alkyl(C6-C30) arylboronyl;The organic electroluminescent compound according to claim 1, which is at least one selected from the group consisting of (C6-C30)aryl(C1-C30)alkyl and (C1-C30)alkyl(C6-C30)aryl.

6. The following compounds: 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemistry 27】 【Chemistry 28】 【Chemistry 29】 【Transformation 30】 【Chemistry 31】 【Chemistry 32】 【Transformation 33】 【Transformation 34】 【Chemistry 35】 【Transformation 36】 【Chemistry 37】 【Transformation 38】 【Chemistry 39】 Organic electroluminescent compounds selected from the following.

7. A plurality of host materials comprising a first host material containing the organic electroluminescent compound described in claim 1 and a second host material different from the first host material.

8. The second host material is given by the following formula 2: 【Chemistry 40】 (In the formula, X １ and Y １ each independently represents —N═, —NR ６７ —, —O— or —S—, provided that either １ X １ or Y represents —N═, and the other of １ X １ and Y represents —NR ６７ —, —O— or —S—; R ６１ This represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 member) heteroaryl; R ６２ to R ６４ and R ６７ each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring or -L ３ ''-N(Ar ３ '')(Ar ４ '') or may be bonded to adjacent substituents to form a ring; L ３ Each of the symbols '' independently represents a single bond, substituted or unsubstituted (C6-C30) arylene or a substituted or unsubstituted (3-30 member) heteroarylene; Ar ３ '' and Ar ４ Each of the following independently represents hydrogen, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30) alkenyl, a substituted or unsubstituted fused ring of an (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl; R ６５ and R ６６ Each of these independently represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 member) heteroaryl; L ４ represents a single bond, substituted or unsubstituted (C6-C30) arylene or a substituted or unsubstituted (3-30 member) heteroarylene; and a represents 1, b and c each independently represent 1 or 2, d represents an integer from 1 to 4, and if b to d are integers of 2 or more, R ６２ Each of the above ~ Caution ６４ (Each of these may be the same as or different from the others.) A plurality of host materials according to claim 7, comprising a compound represented by [the specified compound].

9. The compound represented by formula 2 is the following compound: 【Chemistry 41】 【Chemistry 42】 【Chemistry 43】 【Chemistry 44】 【Chemistry 45】 【Chemistry 46】 A plurality of host materials according to claim 8, which are at least one selected from the above.

10. The second host material is given by the following formula 3: 【Chemistry 47】 (In the formula, L ａ and L ｂ Each of these independently represents a single bond, substituted or unsubstituted (C6-C30) arylene or a substituted or unsubstituted (3-30 member) heteroarylene; Ar ａ and Ar ｂ Each of these independently represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl; R ３０１ ~R ３０４ Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted fused rings of (C3-C30) aliphatic rings and (C6-C30) aromatic rings or -L ３ '''-N(Ar ３ ''') (Ar ４ ''') may represent or be bonded to an adjacent substituent to form a ring; L ３ Each of ''' independently represents a single-bonded, substituted, or unsubstituted (C6-C30) arylene or a substituted or unsubstituted (3-30 member) heteroarylene; Ar ３ ''' and Ar ４ ''' independently represents hydrogen, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30) alkenyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl; and f and i each independently represent integers from 1 to 4, g and h each independently represent integers from 1 to 3, and if f to i are integers of 2 or greater, R ３０１ Each of the above ~ Caution ３０４ (Each of these may be the same as or different from the others.) A plurality of host materials according to claim 7, comprising a compound represented by [the specified compound].

11. The compound represented by formula 3 is the following compound: 【Chemistry 48】 【Chemistry 49】 A plurality of host materials according to claim 10, which are at least one selected from the above.

12. The second host material is given by the following formula 4: [Transformation 50] (In the formula, T represents -O- or -S-; HAr represents a substituted or unsubstituted nitrogen-containing (3-30 membered) heteroaryl; L ５１ This represents a single-bonded, substituted, or unsubstituted (C6-C30) arylene or a substituted or unsubstituted (3-30 member) heteroarylene; R ７１ and R ７２ Each of these independently consists of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, and substituted or unsubstituted di(C1-C30)alkyl(C6-C30). Represents an arylsilyl, a substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30) alkyl(C6-C30)arylamino, or may be bonded to an adjacent substituent to form a ring; and a １１ b represents an integer from 1 to 4, １２ represents an integer from 1 to 3, and a １１ and b1 ２ If each of these represents an integer greater than or equal to 2, then R ７１ Each of and R ７２ (Each of these may be the same as or different from the others.) A plurality of host materials according to claim 7, comprising a compound represented by [the specified compound].

13. The compound represented by formula 4 is the following compound: 【Chemistry 51】 【Chemistry 52】 【Chemistry 53】 【Chemistry 54】 A plurality of host materials according to claim 12, which are at least one selected from the above.

14. An organic electroluminescent device comprising the organic electroluminescent compound described in claim 1.

15. The organic electroluminescent device according to claim 14, wherein the organic electroluminescent compound is contained in the light-emitting layer.

16. An organic electroluminescent device comprising an anode; a cathode; and at least one light-emitting layer between the anode and the cathode, wherein the at least one light-emitting layer comprises a plurality of host materials as described in claim 7.

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