Organic electroluminescent compound, multiple host materials and this comprehensive organic electroluminescent device

Abstract

The present disclosure relates to an organic electroluminescent compound, several host materials, and an organic electroluminescent device comprising these. By incorporating the organic electroluminescent compound according to the present disclosure, a long-life organic electroluminescent device could be produced, and by incorporating several host materials according to the present disclosure, a long-life organic electroluminescent device could be produced.

Description

Technical area

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

[0002] An organic electroluminescent (EL) device is a self-emission type display device with the advantages of a wide viewing angle, excellent contrast, and fast response. In 1987, Eastman Kodak first developed an organic EL device using a low-molecular-weight aromatic diamine and an aluminum complex as materials to form a light-emitting layer (see: Appl. Phys. Lett. 51, 913, 1987).

[0003] The light-emitting material of an organic electroluminescent device is the most important factor in determining the device's luminous efficiency. The light-emitting material should exhibit high quantum efficiency and high electron and hole mobility, and the resulting light-emitting layer should be uniform and stable. The light-emitting material can be functionally divided into a host material and a dopant material. Mixing a host and a dopant can be used to improve color purity, luminous efficiency, and stability. Desirable properties of the solid-state solvent and the energy-carrying host material should include high purity and suitable molecular weights to enable vacuum deposition.In addition, thermal stability should be ensured based on a high glass transition temperature and thermal decomposition temperature. High electrochemical stability is required for long lifetime. An amorphous thin film should be easily formed. Adhesion to materials of other adjacent layers should be good, but preferably no movement between layers is allowed. Since the host material has a major influence on the efficiency and lifetime of the light-emitting device when using such a dopant / host material system, its selection is important.

[0004] Various compounds are known as such host materials, but in the case of an organic electroluminescent device using a known material, the need for a new material has arisen due to high drive voltage, low efficiency, and short lifetime. Therefore, there is a need to develop a host material that enables the realization of an organic electroluminescent device with excellent lifetime even at low drive voltage and high luminance.

[0005] Korean Laid-Open Patent Application No. 10-2019-0013353 discloses an organic optoelectronic device using a compound having a benzonaphtho-based heteroaryl group as a skeleton with a compound having a carbazole-carbazole group as a host of a light-emitting layer, but does not disclose multiple host materials using a compound in which a 5-membered heteroaryl is condensed with a side benzene ring of a phenanthrene skeleton together with a compound having a carbazole-based heteroaryl group as a skeleton as in the present invention. Disclosure of the inventionProblems to be solved

[0006] The object of the present disclosure is to provide an organic electroluminescent compound capable of producing an organic electroluminescent device with a long lifetime, and an organic electroluminescent device comprising the same.

[0007] Another object of the present disclosure is to provide a plurality of host materials capable of fabricating a long-life organic electroluminescent device and an organic electroluminescent device comprising the plurality of host materials. Solution to the task

[0008] As a result of intensive research to solve the above technical problem, the present invention has found that the above-described problem can be solved by a compound represented by the following formula 1 and a plurality of host materials comprising a first host material containing a compound represented by the following formula 1 and a second host material containing a compound represented by the following formula 2, thereby completing the present invention.

[0009] It is important to note that in Formula 1 X1 and Y1 each independently represent -N=, -NR5, -O-, or -S-, with the proviso that one of X1 and Y1 is -N= and the other of X1 and Y1 is -NR5-, -O- or -S-; R1 represents a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl or the following formula 1-a: and R2 to R5 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri-(C1-C30)alkylsilyl, a substituted or unsubstituted di-(C1-C30)alkyl-(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi-(C6-C30)arylsilyl, a substituted or unsubstituted tri-(C6-C30)-arylsilyl, a substituted or unsubstituted fused ring of an aliphatic (C3-C30) ring and an aromatic (C6-C30) ring or the following formula 1-a, or may be linked to an adjacent substituent to form a ring, with the proviso that at least one of R1 to R5 is the following formula 1-a.

[0010] The rule is that in Formula 1-a L1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene or a substituted or unsubstituted (3- to 30-membered) heteroarylene; Ar1 represents a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3- to 30-membered) heteroaryl; Ar2 represents a substituted or unsubstituted (3- to 30-membered) heteroaryl; R6 each independently represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)-alkyl, a substituted or unsubstituted (C6-C30)-aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30)-cycloalkyl, a substituted or unsubstituted (C1-C30)-alkoxy, a substituted or unsubstituted tri-(C1-C30)-alkylsilyl, a substituted or unsubstituted di-(C1-C30)-alkyl-(C6-C30)-arylsilyl, a substituted or unsubstituted (C1-C30)-alkyldi-(C6-C30)-arylsilyl, a substituted or unsubstituted tri-(C6-C30)-arylsilyl, a substituted or unsubstituted fused ring of an aliphatic (C3-C30) ring and an aromatic (C6-C30) ring, a substituted or unsubstituted mono- or di-(C1-C30)-alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)-arylamino,a substituted or unsubstituted (C1-C30)-alkyl-(C6-C30)-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)heteroarylamino or a substituted or unsubstituted (C6-C30)-aryl-(3- to 30-membered)heteroarylamino or can be linked to an adjacent substituent to form a ring;, a and b each independently represent an integer having a value of 1 or 2, and c and d each independently represent an integer from 1 to 4; and then, if a to d represent an integer with a value of 2 or more, each of R2 to R4 and each of R6 may be the same or different.

[0011] It is important to note that in Formula 2 X2 stands for -O- or -S-; Ring A is benzene or naphthalene; R 21 and R 22each independently represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)-alkyl, a substituted or unsubstituted (C6-C30)-aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30)-cycloalkyl, a substituted or unsubstituted (C1-C30)-alkoxy, a substituted or unsubstituted tri-(C1-C30)-alkylsilyl, a substituted or unsubstituted di-(C1-C30)-alkyl-(C6-C30)-arylsilyl, a substituted or unsubstituted (C1-C30)-alkyldi-(C6-C30)-arylsilyl or a substituted or unsubstituted tri-(C6-C30)-arylsilyl or may be linked to a neighboring substituent to form a ring; L2 represents a single bond, a substituted or unsubstituted (C6-C30)arylene or a substituted or unsubstituted (3- to 30-membered) heteroarylene; HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl containing at least one nitrogen atom; n is an integer from 1 to 5 and m is an integer from 1 to 4; and then, if n and m are an integer with a value of 2 or more, each of R 21 and each of R 22 can be the same or different. Advantageous effects of the invention

[0012] By using the organic electroluminescent compound according to the present disclosure and a plurality of host materials comprising the same, a long-life organic electroluminescent device can be fabricated. Embodiments of the invention

[0013] The present disclosure is described in detail below. However, this is for illustrative purposes and should not be construed as a method of limiting the scope of the present disclosure.

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

[0015] The present disclosure also relates to a plurality of host materials comprising one or more first host materials comprising the compound represented by formula 1 and one or more second host materials comprising the compound represented by formula 2, and an organic electroluminescent device comprising the host materials.

[0016] Here, the term “organic electroluminescent compound” in the present disclosure refers to a compound that can be used in an organic electroluminescent device and can be included in any layer constituting the organic electroluminescent device as needed.

[0017] Here, the term "organic electroluminescent material" in the present disclosure refers to a material that can be used in an organic electroluminescent device, may comprise one or more compounds, and may be included, as needed, in any layer constituting an organic electroluminescent device. For example, the organic electroluminescent material may be a hole-injection material, a hole-transport material, a hole-assisting material, an auxiliary light-emitting material, an electron-blocking material, a light-emitting material (containing a host material and a dopant material), an electron-buffering material, a hole-blocking material, an electron-transporting material, an electron-injecting material, etc.

[0018] Here, the term "multiple host materials" in the present disclosure refers to a host material comprising a combination of two or more compounds that may be included in any light-emitting layer constituting an organic electroluminescent device, and may refer to both materials before (e.g., before deposition) or after (e.g., after deposition) incorporation into the organic electroluminescent device. For example, the multiple host materials of the present disclosure may be a combination of two or more host materials, and optionally, a conventional material incorporated into the organic electroluminescent material may be further included.The two or more types of compounds included in the multiple host materials of the present disclosure may be incorporated together into a light-emitting layer by methods commonly used in the art, or may be incorporated into different light-emitting layers. For example, the two or more types of compounds may be deposited as a mixture, co-deposited, or deposited individually.

[0019] Here, the term "hole transport zone" in the present disclosure means a region where holes move between the first electrode and the light-emitting layer, and may include, for example, a hole injection layer, a hole transport layer, a hole assist layer, an emission assist layer, and / or an electron blocking layer. The hole injection layer, the hole transport layer, the hole assist layer, the emission assist layer, and the electron blocking layer may each be single-layered, double-layered, multi-layered, or multi-layered with stacking of three or more layers. According to one example of the present disclosure, the hole transport belt may include a first hole transport layer and a second hole transport layer, and may further include a third hole transport layer.The second hole-transport layer and the third hole-transport layer may be one or more of a plurality of hole-transport layers and may include a hole-assisting layer, an auxiliary light-emitting layer, and / or an electron-blocking layer. Furthermore, according to another example of the present disclosure, the hole-transport ribbon may include a first hole-transport layer and a second hole-transport layer, the first hole-transport layer may be disposed between the first electrode and the light-emitting layer, the second hole-transport layer may be disposed between the first hole-transport layer and the light-emitting layer, and the second hole-transport layer may serve as a hole-transport layer, an auxiliary light-emitting layer, a hole-assisting layer, and / or an electron-blocking layer.The hole transport ribbon may include a first hole transport layer, a second hole transport layer, and a third hole transport layer, wherein the first hole transport layer may be disposed between the first electrode and the light-emitting layer, the second hole transport layer may be disposed between the first hole transport layer and the light-emitting layer, the third hole transport layer may be disposed between the second hole transport layer and the light-emitting layer, and the third hole transport layer may serve as a hole transport layer, emission assist layer, hole assist layer, and / or electron blocking layer.

[0020] Here, the term "(C1-C30)alkyl(ene)" in the present disclosure refers to a linear or branched alkyl(ene) having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. Specific examples of the alkyl are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.

[0021] Here, the term "(C3-C30)cycloalkyl(ene)" in the present disclosure refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 ring-skeleton carbon atoms, preferably 3 to 20 carbon atoms, and more preferably 3 to 7 carbon atoms. Examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.

[0022] Here, the term "(C3-C30)-cycloalkenyl" in the present disclosure refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 ring-skeleton carbon atoms and one double bond in the ring-skeleton, preferably 3 to 20 carbon atoms, and more preferably 3 to 7 carbon atoms. Examples of cycloalkenyl include cyclopropenyl, cyclobutenyl, cyclopentenyl, etc.

[0023] Here, the term “(3- to 7-membered) heterocycloalkyl” in the present disclosure refers to a cycloalkyl having 3 to 7 and preferably 5 to 7 ring skeleton atoms and comprising at least one heteroatom selected from the group consisting of B, N, O, S, Si and P, preferably O, S and N, for example tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, etc.

[0024] Here, the term “(C6-C30)aryl(ene)” in the present disclosure refers to a monocyclic or fused ring-based radical derived from an aromatic hydrocarbon having 6 to 30 ring-skeleton carbon atoms and may be partially saturated, and includes those having a spiro structure. The number of ring skeleton carbon atoms is preferably 6 to 20, more preferably 6 to 15. Examples of the aryl are specifically phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthrenyl, benzophenanthrenyl, phenylphenanthrenyl, anthracenyl, benzanthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, benzochrysenyl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, cumenyl, spiro[fluoren-fluoren]yl (spirobifluorenyl),Spiro[fluoren-benzofluoren]yl, Azulenyl, usw. Spezieller kann das Aryl o-Tolyl, m-Tolyl, p-Tolyl, 2,3-Xylyl, 3,4-Xylyl, 2,5-Xylyl, Mesityl, o-Cumenyl, m-Cumenyl, p-Cumenyl, p-t-Butylphenyl, p-(2-Phenylpropyl)phenyl, 4'-Methylbiphenyl, 4"-t-Butyl-p-terphenyl-4-yl, o-Biphenyl, m-Biphenyl, p-Biphenyl, o-Terphenyl, m-Terphenyl-4-yl, m-Terphenyl-3-yl, m-Terphenyl-2-yl, p-Terphenyl-4-yl, p-Terphenyl-3-yl, p-Terphenyl-2-yl, m-Quaterphenyl, 1-Naphthyl, 2-Naphthyl, 1-Fluorenyl, 2-Fluorenyl, 3-Fluorenyl, 4-Fluorenyl, 9-Fluorenyl, 9,9-Dimethyl-1-fluorenyl, 9,9-Dimethyl-2-fluorenyl, 9,9-Dimethyl-3-fluorenyl, 9,9-Dimethyl-4-fluorenyl, 9,9-Diphenyl-1-fluorenyl, 9,9-Diphenyl-2-fluorenyl, 9,9-Diphenyl-3-fluorenyl, 9,9-Diphenyl-4-fluorenyl, 1-Anthryl, 2-Anthryl, 9-Anthryl, 1-Phenanthryl, 2-Phenanthryl, 3-Phenanthryl, 4-Phenanthryl, 9-Phenanthryl, 1-Chrysenyl, 2-Chrysenyl, 3-Chrysenyl, 4-Chrysenyl, 5-Chrysenyl, 6-Chrysenyl, Benzo[c]phenanthryl, Benzo[g]chrysenyl, 1-Triphenylenyl, 2-Triphenylenyl,3-Triphenylenyl, 4-Triphenylenyl, 3-Fluoranthenyl, 4-Fluoranthenyl, 8-Fluoranthenyl, 9-Fluoranthenyl, Benzofluoranthenyl usw. einschließen.,

[0025] Here, the term "(3- to 30-membered) heteroaryl(ene)" in the present disclosure refers to an aryl group having 3 to 30 ring skeleton atoms and one or more heteroatoms selected from the group consisting of B, N, O, S, Si, P, Se, and Ge, and preferably having 5 to 25 ring skeleton atoms. The number of heteroatoms is preferably 1 to 4 and may be a single ring system or a fused ring system fused with one or more benzene rings, and may be partially saturated. Furthermore, the heteroaryl herein also includes a form in which at least one heteroaryl group or aryl group is linked to the heteroaryl group via a single bond. Examples of the heteroaryl are monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl,usw. und Heteroaryl mit anellierten Ringen wie Benzofuranyl, Benzothiophenyl, Isobenzofuranyl, Dibenzofuranyl, Dibenzothiophenyl, Benzoimidazolyl, Benzothiazolyl, Benzoisothiazolyl, Benzoisoxazolyl, Benzoxazolyl, Imidazopyridinyl, Isoindolyl, Indolyl, Benzoindolyl, Indazolyl, Benzothiadiazolyl, Chinolyl, Isochinolyl, Cinnolinyl, Chinazolinyl, Chinoxalinyl, Carbazolyl, Azacarbazolyl, Benzocarbazolyl, Dibenzocarbazolyl, Phenoxazinyl, Phenanthridinyl, Benzodioxolyl, Indolizinyl, Acridinyl, Silafluorenyl, Germanfluorenyl usw. Spezieller handelt es sich bei dem Heteroaryl um 1-Pyrrolyl, 2-Pyrrolyl, 3-Pyrrolyl, 2-Pyridinyl, 3-Pyridinyl, 4-Pyridinyl, 2-Pyrimidinyl, 4-Pyrimidinyl, 5-Pyrimidinyl, 6-Pyrimidinyl, 1,2,3-Triazin-4-yl, 1,2,4-Triazin-3-yl, 1,3,5-Triazin-2-yl, 1-Imidazolyl, 2-Imidazolyl, 1-Pyrazolyl, 1-Indolizinyl, 2-Indolizinyl, 3-Indolizinyl, 5-Indolizinyl, 6-Indolizinyl, 7-Indolizinyl, 8-Indolizinyl, 2-Imidazopyridinyl, 3-Imidazopyridinyl, 5-Imidazopyridinyl, 6-Imidazopyridinyl,7-Imidazopyridinyl, 8-Imidazopyridinyl, 1-Indolyl, 2-Indolyl, 3-Indolyl, 4-Indolyl, 5-Indolyl, 6-Indolyl, 7-Indolyl, 1-Isoindolyl, 2-Isoindolyl, 3-Isoindolyl, 4-Isoindolyl, 5-Isoindolyl, 6-Isoindolyl, 7-Isoindolyl, 2-Furyl, 3-Furyl, 2-Benzofuranyl, 3-Benzofuranyl, 4-Benzofuranyl, 5-Benzofuranyl, 6-Benzofuranyl, 7-Benzofuranyl, 1-Isobenzofuranyl, 3-Isobenzofuranyl, 4-Isobenzofuranyl, 5-Isobenzofuranyl, 6-Isobenzofuranyl, 7-Isobenzofuranyl, 2-Chinolyl, 3-Chinolyl, 4-Chinolyl, 5-Chinolyl, 6-Chinolyl, 7-Chinolyl, 8-Chinolyl, 1-Isochinolyl, 3-Isochinolyl, 4-Isochinolyl, 5-Isochinolyl, 6-Isochinolyl, 7-Isochinolyl, 8-Isochinolyl, 2-Chinoxalinyl, 5-Chinoxalinyl, 6-Chinoxalinyl, 1-Carbazolyl, 2-Carbazolyl, 3-Carbazolyl, 4-Carbazolyl, 9-Carbazolyl, Azacarbazolyl-1-yl, Azacarbazolyl-2-yl, Azacarbazolyl-3-yl, Azacarbazolyl-4-yl, Azacarbazolyl-5-yl, Azacarbazolyl-6-yl, Azacarbazolyl-7-yl, Azacarbazolyl-8-yl, Azacarbazolyl-9-yl, 1-Phenanthridinyl, 2-Phenanthridinyl, 3-Phenanthridinyl,4-Phenanthridinyl, 6-Phenanthridinyl, 7-Phenanthridinyl, 8-Phenanthridinyl, 9-Phenanthridinyl, 10-Phenanthridinyl, 1-Acridinyl, 2-Acridinyl, 3-Acridinyl, 4-Acridinyl, 9-Acridinyl, 2-Oxazolyl, 4-Oxazolyl, 5-Oxazolyl, 2-Oxadiazolyl, 5-Oxadiazolyl, 3-Furazanyl, 2-Thienyl, 3-Thienyl, 2-Methylpyrrol-1-yl, 2-Methylpyrrol-3-yl, 2-Methylpyrrol-4-yl, 2-Methylpyrrol-5-yl, 3-Methylpyrrol-1-yl, 3-Methylpyrrol-2-yl, 3-Methylpyrrol-4-yl, 3-Methylpyrrol-5-yl, 2-t-Butylpyrrol-4-yl, 3-(2-Phenylpropyl)pyrrol-1-yl, 2-Methyl-1-indolyl, 4-Methyl-1-indolyl, 2-Methyl-3-indolyl, 4-Methyl-3-indolyl, 2-t-Butyl-1-indolyl, 4-t-Butyl-1-indolyl, 2-t-Butyl-3-indolyl, 4-t-Butyl-3-indolyl, 1-Dibenzofuranyl, 2-Dibenzofuranyl, 3-Dibenzofuranyl, 4-Dibenzofuranyl, 1-Dibenzothiophenyl, 2-Dibenzothiophenyl, 3-Dibenzothiophenyl, 4-Dibenzothiophenyl, 1-Silafluorenyl, 2-Silafluorenyl, 3-Silafluorenyl, 4-Silafluorenyl, 1-Germanfluorenyl, 2-Germanfluorenyl, 3-Germanfluorenyl,4-Germanfluorenyl. Furthermore, "heteroaryl(ene)" can be divided into heteroaryl(ene) with electron properties and heteroaryl(ene) with hole properties. A heteroaryl(ene) with electron properties is a substituent with relatively abundant electrons in the parent nucleus and can be, for example, a substituted or unsubstituted pyridinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted quinolyl, etc. A heteroaryl(ene) with hole properties is a substituent with relatively few electrons in the parent nucleus and can be, for example, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl.

[0026] Here, the term "fused ring composed of an aliphatic (C3-C30) ring and an aromatic (C6-C30) ring" in the present disclosure refers to a functional group of a ring in which at least one aliphatic ring having 3 to 30, preferably 3 to 25, and more preferably 3 to 18 ring skeleton carbon atoms and at least one aromatic ring having 6 to 30, preferably 6 to 25, and more preferably 6 to 18 ring skeleton carbon atoms are fused. Examples include a fused ring composed of at least one benzene and at least one cyclohexane or a fused ring composed of at least one naphthalene and at least one cyclopentane.

[0027] The carbon atom of the fused ring of an aliphatic (C3-C30) ring and an aromatic (C6-C30) ring may be replaced by at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S. Here, "halogen" in the present disclosure includes F, Cl, Br, and I atoms.

[0028] In addition, “ortho (o-)”, “meta (m-)” and “para (p-)” mean substitution positions of all substituents, an ortho position means a compound in which a position of a substituent is immediately adjacent to it, for example, in the case of benzene it means 1 or 2 positions, a meta position means a position adjacent to an immediately adjacent substitution position, for example, in the case of benzene it means 1 or 3 positions, and a para position means a position adjacent to a meta position, for example, in the case of benzene it means 1 or 4 positions.

[0029] Here, the term "ring formed in conjunction with an adjacent substituent" in the present disclosure refers to a substituted or unsubstituted (3- to 30-membered) mono- or polycyclic, alicyclic, or aromatic ring, or a combination thereof, formed by linking or fusing two or more adjacent substituents, and may preferably be a substituted or unsubstituted (3- to 26-membered) mono- or polycyclic, alicyclic, or aromatic ring, or a combination thereof. Furthermore, the formed ring may comprise at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S. According to one embodiment of the present disclosure, the number of ring skeleton atoms is (5- to 20-membered), and according to another embodiment of the present disclosure, the number of ring skeleton atoms is (5- to 15-membered).

[0030] Furthermore, the term "substituted" in the description "substituted or unsubstituted" herein means that a hydrogen atom in a particular functional group is replaced by another atom or functional group (i.e., a substituent). Unless otherwise stated, the substituents may, without limitation, replace hydrogen in any position where the substituents may be substituted, and when two or more hydrogen atoms are replaced by each substituent in a particular functional group, each substituent may be the same or different from each other. The maximum number of substituents that can be substituted for a particular functional group may be the total number of substituted valence atoms of each atom constituting the functional group.It is preferred that the substituted alkyl, the substituted aryl(ene), the substituted heteroaryl, the substituted cycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, the fused ring of a substituted aliphatic ring and aromatic ring, the substituted mono- or dialkylamino, the substituted mono- or diarylamino, the substituted alkylarylamino, the substituted mono- or diheteroarylamino and the substituted arylheteroarylamino in R1 to R6, R. 21 , R 22, Ar1, Ar2 and HAr of the present disclosure are each independently substituted by one or more substituents 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- to 7-membered) heterocycloalkyl, (C6-C30)aryloxy, (C6-C30)arylthio, (5- to 30-membered) heteroaryl, which is unsubstituted or substituted by (C6-C30)aryl, (C6-C30)-aryl which is unsubstituted or substituted by (5- to 30-membered) heteroaryl, tri-(C1-C30)-alkylsilyl, tri-(C6-C30)-arylsilyl, di-(C1-C30)-alkyl-(C6-C30)-arylsilyl, (C1-C30)-alkyldi-(C6-C30)-arylsilyl, a fused ring of an aliphatic (C3-C30) ring and an aromatic (C6-C30) ring, amino, mono- or di-(C1-C30)-alkylamino, substituted or unsubstituted mono- or di-(C6-C30)-arylamino, (C1-C30)-alkyl-(C6-C30)-arylamino,Mono- or di-(3- to 30-membered)heteroarylamino, (C1-C30)-alkyl-(3- to 30-membered)heteroarylamino, (C6-C30)-aryl-(3- to 30-membered)heteroarylamino, (C1-C30)-alkylcarbonyl, (C1-C30)-alkoxycarbonyl, (C6-C30)-arylcarbonyl, (C6-C30)-arylphosphinyl, di-(C6-C30)-arylboronyl, di-(C1-C30)-alkylboronyl, (C1-C30)-alkyl-(C6-C30)-arylboronyl, (C6-C30)-Ar-(C1-C30)-alkyl and (C1-C30)-alkyl-(C6-C30)-aryl are substituted. For example, the substituents can be deuterium, a substituted or unsubstituted methyl, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted anthracenyl,a substituted or unsubstituted chrysenyl, a substituted or unsubstituted triphenylenyl, a substituted or unsubstituted fluoranthenyl, a substituted or unsubstituted dimethylfluorenyl, a substituted or unsubstituted diphenylfluorenyl, a substituted or unsubstituted pyridinyl, a substituted or unsubstituted spirobifluorenyl, a substituted or unsubstituted norbornenyl, a substituted or unsubstituted adamantyl, a substituted or unsubstituted carbazolyl, carbazolyl which is unsubstituted or substituted by phenyl, a substituted or unsubstituted dibenzofuranyl, dibenzofuranyl which is unsubstituted or substituted by deuterium, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzonaphthofuranyl or a substituted or unsubstituted phenanthrooxazolyl, etc.,

[0031] In the present disclosure, if a substituent is not shown in the formula or compound structure, it may mean that all positions that can be present as substituents are hydrogen or deuterium. This means that in the case of deuterium, an isotope of hydrogen, some hydrogen atoms may be deuterium, which is an isotope, in which case the deuterium content may be from 0% to 100%. In the case where the substituent is not shown in the formula or compound structure, unless deuterium is expressly excluded, hydrogen and deuterium may be mixed and used in the compound, such as when the deuterium content is 0%, the hydrogen content is 100%, and all substituents are hydrogen. Deuterium is one of the isotopes of hydrogen and is an element that has a deuteron consisting of a proton and a neutron as its nucleus.It can be expressed as hydrogen-2, and the element symbol can be written as D or 2H. Isotopes refer to atoms with the same atomic number (Z) but different mass numbers (A). It can also be interpreted as an element that has the same number of protons but different numbers of neutrons.

[0032] Here, "combinations thereof" in the present disclosure refers to one or more of the components of the corresponding list being combined to form a known or chemically stable arrangement that one skilled in the art could devise from the corresponding list. For example, alkyl and deuterium may be combined to form partially or fully deuterated alkyl groups; halogen and alkyl may be combined to form halogenated alkyl substituents; and halogen, alkyl, and aryl may be combined to form halogenated arylalkyl.For example, preferred combinations of substituents may contain up to 50 atoms excluding hydrogen and deuterium, or up to 40 atoms excluding hydrogen and deuterium, or up to 30 atoms excluding hydrogen and deuterium, or in many cases preferred combinations of substituents may contain up to 20 atoms excluding hydrogen and deuterium.

[0033] In the formula of the present disclosure, when a plurality of substituents are indicated by the same symbol, each of the substituents represented by the same symbol may be the same as or different from each other.

[0034] The host materials according to one embodiment are described below.

[0035] The plurality of host materials may, according to one embodiment, comprise a first host material comprising the compound represented by Formula 1 and a second host material comprising the compound represented by Formula 2, and may be included in at least one light-emitting layer of the organic electroluminescent device according to one embodiment.

[0036] The first host material, which is the host material according to one embodiment, may comprise a compound represented by Formula 1 below.

[0037] It is important to note that in Formula 1 X1 and Y1 each independently represent -N=, -NR5, -O-, or -S-, with the proviso that one of X1 and Y1 is -N= and the other of X1 and Y1 is -NR5-, -O- or -S-; R1 represents a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl or the following formula 1-a: and R2 to R5 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri-(C1-C30)alkylsilyl, a substituted or unsubstituted di-(C1-C30)alkyl-(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi-(C6-C30)arylsilyl, a substituted or unsubstituted tri-(C6-C30)-arylsilyl, a substituted or unsubstituted fused ring of an aliphatic (C3-C30) ring and an aromatic (C6-C30) ring or the formula 1-a, or may be linked to an adjacent substituent to form a ring, with the proviso that at least one of R1 to R5 is the following formula 1-a:

[0038] The rule is that in Formula 1-a L1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene or a substituted or unsubstituted (3- to 30-membered) heteroarylene; Ar1 represents a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3- to 30-membered) heteroaryl; Ar2 represents a substituted or unsubstituted (3- to 30-membered) heteroaryl; R6 each independently represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)-alkyl, a substituted or unsubstituted (C6-C30)-aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30)-cycloalkyl, a substituted or unsubstituted (C1-C30)-alkoxy, a substituted or unsubstituted tri-(C1-C30)-alkylsilyl, a substituted or unsubstituted di-(C1-C30)-alkyl-(C6-C30)-arylsilyl, a substituted or unsubstituted (C1-C30)-alkyldi-(C6-C30)-arylsilyl, a substituted or unsubstituted tri-(C6-C30)-arylsilyl, a substituted or unsubstituted fused ring of an aliphatic (C3-C30) ring and an aromatic (C6-C30) ring, a substituted or unsubstituted mono- or di-(C1-C30)-alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)-arylamino,a substituted or unsubstituted (C1-C30)-alkyl-(C6-C30)-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)heteroarylamino or a substituted or unsubstituted (C6-C30)-aryl-(3- to 30-membered)heteroarylamino or can be linked to an adjacent substituent to form a ring;, a and b each independently represent an integer having a value of 1 or 2, and c and d each independently represent an integer from 1 to 4; and then, if a to d represent an integer with a value of 2 or more, each of R2 to R4 and each of R6 may be the same or different.

[0039] In one embodiment, X1 and Y1 can each independently represent N, O or S, with the proviso that one of X1 and Y1 represents -N= and the other represents -O- or -S-.

[0040] In one embodiment, R1 may be a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, or Formula 1-a, and preferably, R1 may be a substituted or unsubstituted (C6-C25) aryl, a substituted or unsubstituted (3- to 25-membered) heteroaryl, or Formula 1-a. For example, R1 may be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, or Formula 1-a.

[0041] In one embodiment, R2 to R5 may each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) alkyl, or formula 1-a, and preferably, R2 to R5 may each independently represent hydrogen, deuterium, halogen, cyano, or formula 1-a. For example, R2 to R5 may each independently be hydrogen or formula 1-a.

[0042] In one embodiment, L1 can be a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene, and preferably, L1 can be a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (3- to 25-membered) heteroarylene. For example, L1 can be a single bond or a substituted or unsubstituted phenylene.

[0043] In one embodiment, Ar1 may represent a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3- to 30-membered) heteroaryl, and preferably Ar1 may represent a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5- to 25-membered) heteroaryl. For example, Ar1 may be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted naphthalenyl, a substituted or unsubstituted dimethylfluorenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl or a substituted or unsubstituted carbazolyl.Where the substituent of the substituted phenyl can be deuterium or methyl and the substituent of the substituted carbazole can be phenyl.

[0044] In one embodiment, Ar2 may be a substituted or unsubstituted (3- to 30-membered) heteroaryl, and preferably, Ar2 may be a substituted or unsubstituted (5- to 25-membered) heteroaryl. For example, Ar2 may be a substituted or unsubstituted dibenzofuranyl or a substituted or unsubstituted dibenzothiophenyl. Wherein the substituent of the substituted dibenzofuran may be deuterium, methyl, or phenyl.

[0045] In one embodiment, R6 may be hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) alkyl, or a substituted or unsubstituted (C6-C30) aryl, and preferably, R6 may be hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C25) aryl, or a substituted or unsubstituted (C6-C25) aryl. For example, R6 may be hydrogen, deuterium, methyl, or phenyl.

[0046] In one embodiment, a and b may each be an integer having a value of 1 or 2, c and d may each independently be an integer from 1 to 4, and when a to d are an integer having a value of 2 or more, each of R2 to R4 and each of R6 may be the same or different.

[0047] The compound represented by formula 1 can be represented by one of the following formulas 1-1 to 1-4.

[0048] In formulas 1-1 to 1-4, c' is an integer from 1 to 3; then, when c' is an integer having a value of 2 or more, each of R4 may be the same or different; X1, Y1, R1 to R4, R6, L1, Ar1, Ar2 and a to d are as defined in Formula 1.

[0049] In one embodiment, c' may be an integer from 1 to 3, and when c' is an integer having a value of 2 or more, each of R4 may be the same or different.

[0050] According to one embodiment, Ar2 in formula 1-a can be represented by one of the following formulas R-1 to R-4.

[0051] It applies that in the formulas R-1 to R-4 X is O, S, Se or N; and R 11 to R 18 each independently represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl or a substituted or unsubstituted (C6-C30) aryl.

[0052] In one embodiment, X may be O, Se or S.

[0053] In one embodiment, R 11 to R 18 each independently represents hydrogen, deuterium or a substituted or unsubstituted (C1-C10)-alkyl, preferably R 11 to R 18 each independently represent hydrogen or deuterium. For example, all of R 11 to R 18 be hydrogen.

[0054] In one embodiment, the first host material may be exemplified by, but is not limited to, the following compounds.

[0055] The compound represented by Formula 1 according to the present disclosure can be prepared by a synthesis method known to those skilled in the art, and in particular, a synthesis method disclosed in a number of patent documents can be used. For example, it can be synthesized by reference to the method described in Korean Patent Application Laid-Open No. 2017-0022865 (March 2, 2017), but is not limited thereto.

[0056] As a further host material according to one embodiment, the second host material may comprise a compound represented by formula 2 below.

[0057] It is important to note that in Formula 2 X2 stands for -O- or -S-; Ring A is a benzene or naphthalene ring; R 21 and R 22each independently represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)-alkyl, a substituted or unsubstituted (C6-C30)-aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30)-cycloalkyl, a substituted or unsubstituted (C1-C30)-alkoxy, a substituted or unsubstituted tri-(C1-C30)-alkylsilyl, a substituted or unsubstituted di-(C1-C30)-alkyl-(C6-C30)-arylsilyl, a substituted or unsubstituted (C1-C30)-alkyldi-(C6-C30)-arylsilyl or a substituted or unsubstituted tri-(C6-C30)-arylsilyl or may be linked to a neighboring substituent to form a ring; L2 represents a single bond, a substituted or unsubstituted (C6-C30)arylene or a substituted or unsubstituted (3- to 30-membered) heteroarylene; HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl containing at least one nitrogen atom; n is an integer from 1 to 5 and m is an integer from 1 to 4; and then, if n and m are an integer with a value of 2 or more, each of R 21 and each of R 22 can be the same or different.

[0058] In one embodiment, R 21 and R 22each independently represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)-alkyl, a substituted or unsubstituted (C6-C30)-aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30)-cycloalkyl, a substituted or unsubstituted (C1-C30)-alkoxy, a substituted or unsubstituted tri-(C1-C30)-alkylsilyl, a substituted or unsubstituted di-(C1-C30)-alkyl-(C6-C30)-arylsilyl, a substituted or unsubstituted (C1-C30)-alkyldi-(C6-C30)-arylsilyl or a substituted or unsubstituted tri-(C6-C30)-arylsilyl; or ; preferably R 21 and R 22each independently represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C25)-alkyl, a substituted or unsubstituted (C6-C25)-aryl, a substituted or unsubstituted (3- to 25-membered) heteroaryl, a substituted or unsubstituted (C3-C25)-cycloalkyl, a substituted or unsubstituted (C1-C25)-alkoxy, a substituted or unsubstituted tri-(C1-C25)-alkylsilyl, a substituted or unsubstituted di-(C1-C25)-alkyl-(C6-C25)-arylsilyl, a substituted or unsubstituted (C1-C25)-alkyldi-(C6-C25)-arylsilyl or a substituted or unsubstituted tri-(C6-C25)-arylsilyl or be linked to a neighboring substituent to form a ring. For example, R 21 and R 22each independently be hydrogen, deuterium, a substituted or unsubstituted phenyl, a substituted or unsubstituted phenylnaphthyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted naphthylphenyl, a substituted or unsubstituted phenanthrenyl or a substituted or unsubstituted benzoxazolyl.

[0059] In one embodiment, L2 can be a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene. Preferably, L2 can be a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene. For example, L2 can be a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted phenylnaphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted naphthylphenylene.

[0060] In one embodiment, HAr can represent a substituted or unsubstituted (3- to 30-membered) heteroaryl having at least one nitrogen atom; preferably, HAr can represent a substituted or unsubstituted (5- to 25-membered) heteroaryl having at least two nitrogen atoms. For example, HAr can represent a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted triazenyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted benzoquinoxalinyl, a substituted or unsubstituted benzoquinazolinyl, or a substituted or unsubstituted naphthoquinoxalinyl. The substituent of the substituted pyrimidine can be phenyl or pyridinyl substituted by a phenyl.The substituent of the substituted quinoxalinyl may be phenyl, biphenyl, naphthyl, dimethylfluorenyl, diphenylfluorenyl, dibenzothiophenyl or carbazolyl substituted by phenyl; the substituent of the substituted quinazolinyl may be phenyl, biphenyl, naphthyl, dimethylfluorenyl or dibenzothiophenyl; the substituent of the substituted benzoquinoxalinyl may be phenyl or naphthyl; the substituent of the substituted benzoquinazolinyl may be phenyl; and the substituent of the substituted naphthoquinazolinyl may be phenyl.

[0061] In one embodiment, the compound represented by Formula 2 may be represented by any of Formulas 2-1 to 2-16.

[0062] It applies that in formulas 2-1 to 2-16 L3 and L4 can each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene or a substituted or unsubstituted (3- to 30-membered) heteroarylene; Ar3 and Ar4 each independently represent a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered) heteroaryl; X2, R 21 , R 22 , L2, n and m are as defined in formula 2; n' is an integer from 1 to 3; and then, if n' is an integer with a value of 2 or more, each R 21 can be the same or different from each other.

[0063] In one embodiment, L3 and L4 can each independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene. Preferably, L3 and L4 can each independently represent a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (3- to 25-membered) heteroarylene. For example, L3 and L4 can each independently represent a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted phenanthrylene.

[0064] In one embodiment, Ar3 and Ar4 may each independently represent a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5- to 30-membered) heteroaryl; preferably, Ar3 and Ar4 may each independently represent a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5- to 25-membered) heteroaryl. For example, Ar3 and Ar4 may each independently be a substituted or unsubstituted phenyl, phenyl which is unsubstituted or substituted by methyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted naphthylphenyl, a substituted or unsubstituted phenanthryl,a substituted or unsubstituted anthracenyl, a substituted or unsubstituted chrysenyl, a substituted or unsubstituted triphenylenyl, a substituted or unsubstituted fluoranthenyl, a substituted or unsubstituted dimethylfluorenyl, a substituted or unsubstituted diphenylfluorenyl, a substituted or unsubstituted spirobifluorenyl, a substituted or unsubstituted carbazolyl, carbazolyl which is unsubstituted or substituted by phenyl, a substituted or unsubstituted dibenzofuranyl, dibenzofuranyl which is unsubstituted or substituted by deuterium, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzonaphthofuranyl or a substituted or unsubstituted Phenanthroxazolyl, and the substituent of the substituted phenyl, the substituted biphenyl,of the dibenzofuranyl or the substituted benzonaphthofuranyl may be at least one selected from deuterium, norbornenyl and adamantyl, and the substituent of the substituted naphthyl may be at least one selected from deuterium, biphenyl and naphthyl.

[0065] In one embodiment, the second host material may be exemplified by, but is not limited to, the following compounds.

[0066] The compound represented by Formula 2 according to the present disclosure can also be prepared by a synthesis method known to those skilled in the art, and in particular, a synthesis method disclosed in several patent documents can be used. For example, the synthesis according to Korean Patent Application Laid-Open Nos. 2021-0124018 (October 14, 2021) and 2021-0006283 (January 18, 2021) can be carried out by referring to the method disclosed in the disclosure, but is not limited thereto.

[0067] The following describes an organic electroluminescent device to which the organic electroluminescent compound, a plurality of host materials, and the organic electroluminescent compound are applied.

[0068] Fig. 1 shows a connection according to an embodiment of the present invention.

[0069] The organic electroluminescent device according to one embodiment comprises a first electrode, a second electrode, and one or more organic layers disposed between the first and second electrodes, and according to one example, the first host material comprising the compound represented by formula 1 and the second host material comprising the compound represented by formula 2 may be contained in the same organic layer or may be contained in different organic layers.

[0070] The organic layer may comprise at least one light-emitting layer, and the at least one light-emitting layer may contain a plurality of host materials comprising one or more first host materials comprising the compound represented by Formula 1 and one or more second host materials comprising the compound represented by Formula 2. According to one embodiment, the light-emitting layer may comprise at least one of the compounds H1-1 to H1-171 as a first host material represented by Formula 1 and at least one of the compounds H2-1 to H2-795 as a second host material represented by Formula 2.

[0071] According to one embodiment, the organic electroluminescent device may comprise a hole transport band between the first electrode and the light-emitting layer. According to one embodiment, the hole transport band may comprise at least two layers, for example, at least three layers.

[0072] One of the first electrode and the second electrode may be a positive electrode (anode), and the other may be a negative electrode (cathode). In this case, the first electrode and the second electrode may be formed of a transparent conductive material or formed of a transflective or reflective conductive material. The organic layer may further comprise, in addition to the light-emitting layer, one or more layers selected from a hole-injection layer, a hole-transport layer, a hole-assisting layer, an auxiliary light-emitting layer, an electron-transport layer, an electron-injection layer, an intermediate layer, a hole-blocking layer, an electron-blocking layer, and an electron-buffering layer.

[0073] The organic layer may further contain an amine-based compound and / or an azine-based compound in addition to the light-emitting material of the present disclosure. Specifically, the hole-injection layer, the hole-transport layer, the hole-assisting layer, the light-emitting layer, the auxiliary light-emitting layer, or the electron-blocking layer may comprise an amine-based compound, such as an arylamine-based compound, a styrylamine-based compound, etc., as the hole-injection material, the hole-transport material, the hole-assisting material, the light-emitting material, the auxiliary light-emitting material, and the electron-blocking material. Furthermore, the electron-transport layer, the electron-injection layer, the electron-buffer layer, and the hole-blocking layer may comprise an azine-based compound as the electron-transport material, the electron-injection material, the electron-buffer material, and the hole-blocking material.In addition, the organic layer may further comprise at least one metal selected from the group consisting of Group 1, Group 2 organic metals, Period 4 transition metals, Period 5 transition metals, lanthanide metals, and d-transition metals, or one or more complex compounds containing these metals.

[0074] The multiple host materials can be used as a light-emitting material for a white organic light-emitting device according to one embodiment. Various structures have been proposed as a white organic electroluminescent device, such as a side-by-side type, a stacking type, or a color conversion material (CCM) type according to a manner of arranging red (R), green (G), yellowish-green (YG), or blue (B) light-emitting units. Furthermore, the multiple host materials can also be used in an organic electroluminescent device comprising a quantum dot (QD) according to one embodiment.

[0075] A hole-injection layer, a hole-transport layer, an electron-blocking layer, or a combination thereof can be used between the anode and the light-emitting layer. Multiple layers can be used in the hole-injection layer for the purpose of lowering a hole-injection barrier (or hole-injection voltage) from the anode to the hole-transport layer or electron-blocking layer, and two junctions can be used simultaneously in each layer. The hole-injection layer can also be doped with a p-type dopant. The electron-blocking layer can be disposed between the hole-transport layer (or hole-injection layer) and the light-emitting layer and block the overflow of electrons from the light-emitting layer to confine excitons in the light-emitting layer, thereby preventing light emission leakage.Multiple layers can be used as hole transport layer or electron blocking layer, with multiple compounds being used in each layer.

[0076] An electron buffer layer, a hole-blocking layer, an electron-transport layer, an electron-injection layer, or a combination thereof can be used between the light-emitting layer and the cathode. Multiple layers can be used in the electron buffer layer to adjust electron injection and improve the interfacial properties between the light-emitting layer and the electron-injection layer, and two compounds can be used simultaneously for each layer. Multiple layers can be used for the hole-blocking layer or the electron-transport layer, and each layer can use multiple compounds. The electron-injection layer can be doped with an n-type dopant.

[0077] The auxiliary light-emitting layer is disposed between the anode and the light-emitting layer or between the cathode and the light-emitting layer. When disposed between the anode and the light-emitting layer, the auxiliary light-emitting layer can be used to promote the injection and / or transfer of holes or to block the overflow of electrons. When disposed between the cathode and the light-emitting layer, the auxiliary light-emitting layer can be used to promote the injection and / or transfer of electrons or to block the overflow of holes. Furthermore, the auxiliary hole layer is disposed between the hole-transport layer (or hole-injection layer) and the light-emitting layer and can exhibit an effect of smoothing or blocking the transfer rate (or injection rate) of holes, thereby adjusting the charge balance.If the organic electroluminescent device comprises two or more hole-transport layers, the additionally included hole-transport layer can be used as a hole-assisting layer or electron-blocking layer. The light-emitting auxiliary layer, the hole-assisting layer, or the electron-blocking layer can improve the efficiency and / or lifetime of the organic electroluminescent device.

[0078] In the organic electroluminescent device of the present disclosure, it is preferable to dispose one or more layers selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as a "surface layer") on at least one inner surface of a pair of electrodes. Specifically, it is preferable to dispose a chalcogenide layer (including oxides) of silicon and aluminum on the surface of the anode on the light-emitting medium layer side, and a metal halide layer or a metal oxide layer on the surface of the cathode on the light-emitting medium layer side. Drive stabilization for the organic electroluminescent device can be obtained through the surface layer. Preferred examples of the chalcogenide include SiO. X (1≤X≤2), AlO X(1≤X≤1.5), SiON, SiAION, etc.; preferred examples of the metal halide include LiF, MgF2, CaF2, rare earth fluorides, etc.; and preferred examples of the metal oxide include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0079] The organic electroluminescent device according to one embodiment of the present disclosure may be an organic electroluminescent device with a tandem structure. In the case of the tandem organic electroluminescent device, according to one embodiment, two or more individual light-emitting units may be connected by a charge generation layer.The organic electroluminescent device may include two or more light-emitting units, for example, three or more light-emitting units, each having a first and a second electrode opposed to each other on a substrate, and a light-emitting layer stacked between the first electrode and the second electrode, which emits light of a specific wavelength band, wherein each light-emitting unit may include a hole transport band, a light-emitting layer, and an electron transport band, wherein the hole transport band may include a hole injection layer and a hole transport layer, wherein the electron transport band may include an electron transport layer and an electron injection layer, and according to one embodiment, the light-emitting unit may include three or more light-emitting layers.The multiple light-emitting units may emit the same color or different colors. In addition, one light-emitting unit may also include one or more light-emitting layers, and the multiple light-emitting layers may be light-emitting layers of the same color or different colors. One or more charge generation layers may be included between each light-emitting unit. The charge generation layer refers to a layer in which holes and electrons are generated when a voltage is applied. When there are three or more light-emitting units, a charge generation layer may be located between the light-emitting units. In this case, the multiple charge generation layers may be identical to or different from each other.Because the charge generation layer is positioned between the light-emitting units, the current efficiency in each light-emitting unit can be increased, and charges can be easily distributed. Specifically, the charge generation layer can be provided between two adjacent stacks and can be used to drive the tandem organic electroluminescent device with only one pair of anodes and cathodes, without a separate internal electrode positioned between the stacks.

[0080] According to one embodiment, the organic electroluminescent device may comprise two or more organic layers and further comprise one or more charge generation layers. The charge generation layers may be disposed between the organic layers. When two or more organic layers are included, the charge generation layers may be the same or different. Because the charge generation layer is located between the organic layers, the organic electroluminescent device can be driven with only one pair of an anode and a cathode, without a separate internal electrode disposed between the organic layers.

[0081] The charge generation layer may include an n-type charge generation layer or a p-type charge generation layer, the n-type charge generation layer may be doped with an alkali metal, an alkaline earth metal, or a compound of an alkali metal and an alkaline earth metal, the alkali metal may include one selected from the group consisting of Li, Na, K, Rb, Cs, Fr, Yb, and a combination thereof, and the alkaline earth metal may include one selected from the group consisting of Be, Mg, Ca, Sr, Ba, Ra, and a combination thereof.

[0082] Furthermore, in the organic electroluminescent device of the present disclosure, it is also preferable to dispose a mixed region of an electron-transport compound and a reducing dopant, or a mixed region of a hole-transport compound and an oxidizing dopant, on at least one surface of a pair of electrodes. Since the electron-transport compound is reduced to anions by this method, it becomes easy to inject and transport electrons from the mixed region into the light-emitting medium. Furthermore, the hole-transport compound is oxidized to a cation, making it easy to inject and transport holes from the mixed region into the light-emitting medium.Preferred oxidizing dopants include various Lewis acid and acceptor compounds, and preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. Furthermore, by using the reducing dopant layer as a charge generation layer, a white-light-emitting organic electroluminescent device with two or more light-emitting layers could be fabricated.

[0083] According to one embodiment, the light-emitting layer of the organic electroluminescent device may be a single layer as the layer from which light is emitted, and may be multilayered with stacking of two or more layers. The light-emitting layer may further contain one or more dopants, and the doping concentration of the dopant compound may be less than 20 wt.%, preferably less than 10 wt.%, based on the host compound of the light-emitting layer.

[0084] As the dopants included in the organic electroluminescent device of the present disclosure, one or more phosphorescent or fluorescent dopants can be used, and a fluorescent dopant is preferred. The phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particularly limited, but it may be a complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt). In some cases, it may preferably be an ortho-metalated complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt). In some cases, it may further preferably be an ortho-metalated iridium complex compound.

[0085] As the dopant contained in the organic electroluminescent device of the present disclosure, a compound represented by the following formula 101 can be used, but the present disclosure is not limited thereto.

[0086] It is important to note that in Formula 101 L stands for a structure selected from the following structures 1 to 3: R 100 to R 103each independently represents hydrogen, deuterium, halogen, a (C1-C30)alkyl which is unsubstituted or substituted by deuterium and / or one or more halogens, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, cyano, a substituted or unsubstituted (3- to 30-membered) heteroaryl or a substituted or unsubstituted (C1-C30)alkoxy or are combined with adjacent substituents to form a ring, e.g. B. an unsubstituted or pyridine-substituted quinoline, a substituted or unsubstituted benzofuropyridine, a substituted or unsubstituted benzothienopyridine, a substituted or unsubstituted indenopyridine, a substituted or unsubstituted benzofuroquinoline, a substituted or unsubstituted benzothienoquinoline or a substituted or unsubstituted indenoquinoline; R 104 to R 107each independently represents hydrogen, deuterium, halogen, a (C1-C30)alkyl which is unsubstituted or substituted by deuterium and / or one or more halogens, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, cyano or a substituted or unsubstituted (C1-C30)alkoxy or can be combined with one or more adjacent substituents to form a substituted or unsubstituted ring, e.g. B. naphthyl which is unsubstituted or substituted by benzene, a substituted or unsubstituted fluorene, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted indenopyridine, a substituted or unsubstituted benzofuropyridine or a substituted or unsubstituted benzothienopyridine; R 201 to R 220 each independently represents hydrogen, deuterium, halogen, (C1-C30)-alkyl which is unsubstituted or substituted by deuterium and / or one or more halogens, a substituted or unsubstituted (C3-C30)-cycloalkyl or a substituted or unsubstituted (C6-C30)-aryl or may be linked to one or more adjacent substituents to form a substituted or unsubstituted ring; and s is an integer from 1 to 3.

[0087] The specific examples of the dopant compound are as follows, but not limited to them.

[0088] The respective layers of the organic electroluminescent device of the present disclosure can be formed by any dry film forming method such as vacuum deposition, sputtering, plasma, ion plating, etc., and wet film forming methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating, etc. For the wet film forming method, the materials constituting each layer are dissolved or dispersed in a suitable solvent such as ethanol, chloroform, tetrahydrofuran, or dioxane to form a thin film. This solvent can be any solvent in which the materials constituting each layer can be dissolved or dispersed and in which there is no problem with filmability.

[0089] In the formation of the first host material and the second host material according to one embodiment, the film can be formed by the method listed above, and preferably, the film can be formed by a co-deposition or mixed deposition method. Co-deposition is a method in which two or more isomeric materials are added to each crucible source and evaporated and mixed by applying current to two cells simultaneously, and mixed deposition is a method in which two or more isomeric materials are mixed and deposited in one crucible source before deposition, and the materials are then evaporated and mixed by applying current to one cell.

[0090] According to one embodiment, if the first host material and the second host material are present in the same layer or different layers in the organic electroluminescent device, the two host materials could be deposited separately. For example, a second host material can be deposited after the deposition of a first host material.

[0091] According to one embodiment, the present disclosure may provide a compound obtained by depositing an organic layer in a manufacturing process for an organic electroluminescent device, and then recovering and purifying a material of the organic layer adhering to the deposition means. The recovered compound may be subjected to a purification and / or recrystallization process, and the purity of the purified and / or recrystallized compound obtained therefrom may be 99.9% or more.

[0092] According to one embodiment, the present disclosure provides a method for recovering multiple host materials, the method comprising: depositing multiple host materials containing at least a first host material comprising a compound represented by Formula 1 and at least one second host material comprising a compound represented by Formula 2; recovering the multiple host materials adhered to the deposition means; and purifying and / or recrystallizing the recovered multiple host materials to obtain the multiple host materials having a purity of 99.9% or higher.

[0093] According to one embodiment, the present disclosure can provide the display devices such as a smartphone, a tablet, a laptop, a PC, TV, or display devices for a vehicle or a lighting device such as an outdoor or indoor light by using a plurality of host materials comprising a compound represented by Formula 1 and a compound represented by Formula 2.

[0094] Hereinafter, for a detailed understanding of the present disclosure, a production method for the compound according to the present disclosure will be explained using the synthesis method for a representative compound or intermediate of the present disclosure as an example.

[0095] Compound CPPO (4 g, 12.1 mmol), Compound 1 (4.4 g, 13.3 mol), Pd2(dba)3 (553 mg, 0.6 mmol), 2-dichlorohexylphosphine-2',6'-dimethoxybiphenyl ("S-Phos") (397 mg, 0.968 mmol), and sodium tert-butoxide ("NaOt-Bu") (2.3 g, 24.2 mmol) were dissolved in 60 mL of xylene, after which the mixture was stirred at 160 °C for 4 h. After completion of the reaction, the mixture was cooled to room temperature, filtered with Celite to give a solid, and separated by column chromatography to give Compound H1-3 (4.0 g, yield: 52.5%). MG Fp. H1-3 628,72 251,2 °C

[0096] Compound CPPO (7.0 g, 21.22 mmol), Compound 2 (7.8 g, 23.34 mmol), tris(dibenzylideneacetone)dipalladium ("Pd2(dba)3") (0.97 g, 1.061 mmol), NaOt-Bu (5.0 g, 53.05 mmol), and S-Phos (0.87 g, 2.12 mmol) were dissolved in 106 mL of o-xylene, after which the mixture was stirred under reflux at 160 °C for 1 h. After completion of the reaction, the mixture was cooled to room temperature, filtered with Celite to give a solid, and separated by column chromatography to give Compound H1-14 (4.3 g, yield: 33%). MG Fp. H1-14 628,72 215,2 °C

[0097] 5.1 g of Compound A (15.6 mmol), 6 g of Compound B (15.5 mmol), 0.71 g of Pd2(dba)3 (0.776 mmol), 0.64 g of S-phos (1.55 mmol), and 3.7 g of NaOt-Bu (38.8 mmol) were dissolved in 80 mL of o-xylene in a reaction vessel, after which the mixture was stirred under reflux at 160 °C for 2 hours. After the reaction, the mixture was cooled to room temperature, methanol was added, stirred for 30 min, filtered, dried, and separated by column chromatography to give Compound H1-1 (6 g, yield: 62%). MG Fp. H1-1 628,73 250 °C (1) Synthesis of compound D

[0098] Compound C (15 g, 61 mmol), (4-chlorophenyl)boronic acid (12 g, 73.2 mmol), potassium carbonate (21 g, 153 mmol), Pd(PPh3)4 (3.6 g, 3.1 mmol), and 200 mL of THF were dissolved in 70 mL of water in a reaction vessel, after which the mixture was heated to reflux at 130 °C for 5 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, the organic phase was extracted with ethyl acetate, residual moisture was removed with magnesium sulfate, dried, and separated by column chromatography, yielding compound D (15 g, yield: 88%). (2) Synthesis of compound H1-2

[0099] Compound D (7 g, 25.1 mmol), N,2-diphenylphenanthro[3,4-d]oxazol-10-amine (11 g, 27 mmol), Pd2(dba)3 (1.2 g, 1.3 mmol), [2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl] ("X-Phos") (1.1 g, 2.5 mmol), and NaOt-Bu (6.0 g, 63 mmol) were dissolved in 150 mL of xylene in a reaction vessel, after which the mixture was stirred under reflux at 160 °C for 1 h. After completion of the reaction, the reaction mixture was cooled to room temperature, the organic phase was extracted with ethyl acetate, residual moisture was removed with magnesium sulfate, dried, and separated by column chromatography to give compound H1-2 (7 g, yield: 45%). MG Fp. H1-2 628,73 258 °C

[0100] Compound E (5.5 g, 9.69 mmol), bromobenzene (3 g, 19.3 mmol), Pd2(dba)3 (443 mg, 0.48 mmol), X-Phos (318 mg, 0.775 mmol), and NaOt-Bu (1.4 g, 14.5 mmol) were dissolved in 50 mL of xylene in a reaction vessel and heated to reflux at 160 °C for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, the organic phase was extracted with ethyl acetate, residual moisture was removed with magnesium sulfate, dried, and separated by column chromatography, yielding compound H1-6 (2.8 g, yield: 44%). MG Fp. H1-6 644,78 272,2 - C (1) Synthesis of compound G

[0101] In a reaction vessel, compound F (30 g, 121.41 mmol), (4-chlorophenyl)boronic acid (20.88 g, 133.55 mmol), Pd(PPh3)4 (4.21 g, 3.64 mmol), and K2CO3 (41.95 g, 303.53 mmol) were dissolved in 607 mL of toluene, 152 mL of ethanol, and 152 mL of water, after which the mixture was heated to reflux at 130 °C for 24 hours. After the reaction, the mixture was cooled to room temperature and filtered with Celite to give a solid, which was separated by column chromatography to give compound G (26.3 g, yield: 77.7%). (2) Synthesis of compound I

[0102] Compound G (26.3 g, 94.35 mmol), [1,1'-biphenyl]-2-amine (15.97 g, 94.35 mmol), Pd2(dba)3 (4.32 g, 4.72 mmol), S-Phos (3.87 g, 9.44 mmol), and NaOt-Bu (13.60 g, 141.53 mmol) were dissolved in 472 mL of xylene in a reaction vessel and heated to reflux at 130 °C for 4 h. After the reaction, the mixture was cooled to room temperature and filtered with Celite to give a solid, which was separated by column chromatography to give Compound I (30 g, yield: 77.2%). (3) Synthesis of compound H1-56

[0103] Compound H (8 g, 24.26 mmol), Compound I (9.98 g, 24.26 mmol), Pd2(dba)3 (1.11 g, 1.21 mmol), S-phos (1 g, 2.43 mmol), and NaOt-Bu (3.50 g, 36.39 mmol) were dissolved in 122 mL of xylene in a reaction vessel and refluxed at 130 °C for 4 hours. After the reaction, the mixture was cooled to room temperature and filtered with Celite to give a solid, which was separated by column chromatography to give Compound H-156 (6 g, yield: 35.09%). MG Fp. H1-56 704,8 208,6 °C

[0104] In the following, for a detailed understanding of the present disclosure, a method for producing an organic electroluminescent device comprising a plurality of host materials according to the present disclosure and the properties thereof are described. Device Examples 1 to 3: Fabrication of an OLED on which the first host compound and the second host compound according to the present disclosure are co-deposited

[0105] OLEDs were fabricated according to the present disclosure. First, a transparent thin electrode layer of indium tin oxide (ITO) (10 Ω / □) on a glass substrate for an OLED (GEOMATEC CO., LTD., Japan) was subjected to sequential ultrasonic washing with acetone and isopropyl alcohol and then stored in isopropyl alcohol. The ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 from Table 7 was charged into one cell of the vacuum vapor deposition apparatus, and Compound HT-1 was charged into the other cell. The two materials were evaporated at different rates, and Compound HI-1 was deposited in a doping amount of 3 wt% based on the total amount of Compound HI-1 and Compound HT-1 to form a first hole-injection layer with a thickness of 10 nm.Compound HT-1 was then deposited on the first hole-injection layer to form a first hole-transport layer with a thickness of 80 nm. Next, compound HT-2 was introduced into another cell of the vacuum vapor deposition apparatus and evaporated by applying an electric current to the cell, thereby depositing a second hole-transport layer with a thickness of 55 nm on the first hole-transport layer. Compound HT-3 was then introduced into another cell of the vacuum vapor deposition apparatus and evaporated by applying an electric current to the cell, thereby depositing a third hole-transport layer with a thickness of 5 nm on the second hole-transport layer.

[0106] After forming the hole injection layer and the hole transport layer, a light-emitting layer was deposited thereon as follows: After respectively introducing the first host compound and the second host compound listed in Table 1 as hosts into two cells in the vacuum deposition apparatus and compound D-39 as a dopant into another cell, the two host materials were evaporated at a rate of 1:1, and simultaneously, the dopant material was evaporated at a different rate to dopant in an amount of 3 wt% based on the total amount of the host and the dopant, thereby depositing a light-emitting layer with a thickness of 40 nm on the second hole transport layer.Next, Compound ET-1 and Compound EI-1 were deposited as electron-transport materials in a weight ratio of 50:50 on the light-emitting layer to form an electron-transport layer with a thickness of 35 nm. Compound EI-1 was then deposited as an electron-injection layer to a thickness of 2 nm on the electron-transport layer, and then an Al cathode was deposited to a thickness of 80 nm on the electron-injection layer using another vacuum deposition device, thus completing the fabrication of the OLED. For each material, each compound was purified by vacuum sublimation under 10°C. -6 Torr is used. Comparative Device Example 1: Preparation of an OLED comprising a comparative compound as a host

[0107] Except for using the compound in Table 1 below as the first host compound, an OLED was fabricated in the same manner as in Device Example 1.

[0108] The driving voltage based on a luminance of 1000 nits, the emission color, and the time until the light intensity decreases from 100% to 95% (lifetime; T95) based on a luminance of 10,000 nits for Device Comparative Example 1 and Device Examples 1 to 3 fabricated as described above were measured, and the results are shown in Table 1 below. Table 1 First host Second host Driver voltage (V) Emission color Service life T95 (h) Device comparison example 1 H3-1 H2-28 3,0 Red 65 Device example 1 H1-3 H2-28 3,0 Red 94 Device example 2 H1-1 H2-28 3,0 Red 178 Device example 3 H1-2 H2-28 3,0 Red 198

[0109] From Table 1, it can be seen that the organic electroluminescent device comprising the compound of a specific combination according to the present disclosure as a host material has significantly better lifetime characteristics compared to the organic electroluminescent device used as a host material in combination with a conventional host compound. Device Examples 4 to 6: Fabrication of OLEDs on which the first host compound and the second host compound according to the present disclosure are co-deposited

[0110] Except for using the first host compound and the second host compound in Table 2 below as hosts for the light-emitting layer, OLEDs were fabricated in the same manner as in Device Example 1. Comparative Device Example 2: Preparation of an OLED comprising a comparative compound as a host

[0111] Except for using the first host compound in Table 2 below as a host for the light-emitting layer, an OLED was fabricated in the same manner as in Device Example 4.

[0112] The driving voltage based on a luminance of 1000 nits, the emission color, and the time until the light intensity decreases from 100% to 95% (lifetime; T95) based on a luminance of 10,000 nits for the organic electroluminescent devices of Device Comparative Example 2 and Device Examples 4 to 6 prepared as described above were measured, and the results are shown in Table 2 below. Table 2 First host Second host Driver voltage (V) Emission color Service life T95 (h) Device comparison example 2 H3-1 H2-515 3,2 Red 129 Device example 4 H1-3 H2-515 3,1 Red 159 Device example 5 H1-1 H2-515 3,2 Red 214 Device example 6 H1-2 H2-515 3,2 Red 253

[0113] From Table 2 above, it can be seen that the organic electroluminescent device comprising the compound of a specific combination according to the present disclosure as a host material has significantly better lifetime characteristics compared to the organic electroluminescent device used as a host material in combination with a conventional host compound. Device Examples 7 to 9: Fabrication of OLEDs on which the first host compound and the second host compound are co-deposited according to the present disclosure

[0114] Except for using the first host compound and the second host compound in Table 3 below as hosts for the light-emitting layer, OLEDs were fabricated in the same manner as in Device Example 1. Comparative Device Example 3: Preparation of an OLED comprising a comparative compound as a host

[0115] Except for using the first host compound in Table 3 below as a host for the light-emitting layer, an OLED was fabricated in the same manner as in Device Example 7.

[0116] The driving voltage based on a luminance of 1000 nits, the emission color, and the time until the light intensity decreases from 100% to 95% (lifetime; T95) based on a luminance of 10,000 nits for the organic electroluminescent devices of Device Comparative Example 3 and Device Examples 7 to 9 fabricated as described above were measured, and the results are shown in Table 3 below. Table 3 First host Second host Driver voltage (V) Emission color Service life T95 (h) Device comparison example 3 H3-1 H2-409 3,2 Red 104 Device example 7 H1-3 H2-409 3,1 Red 128 Device example 8 H1-1 H2-409 3,1 Red 171 Device example 9 H1-2 H2-409 3,1 Red 217

[0117] From the above, it can be seen that the organic electroluminescent device comprising the compound of a specific combination according to the present disclosure as a host material has significantly better lifetime characteristics compared to the organic electroluminescent device used as a host material in combination with a conventional host compound.

[0118] Furthermore, as a result of measuring the luminous efficacy of the fabricated organic electroluminescent device based on a luminance of 1000 nits, a value of 30.4 cd / A was obtained for Device Comparative Example 3, and values ​​of 30.9 and 30.7 cd / A were obtained for Device Examples 8 and 9, respectively. It can be seen that the organic electroluminescent device according to the present disclosure has improved efficiency compared to an organic electroluminescent device using conventional combinations of host compounds. Device Examples 10 to 12: Fabrication of OLEDs on which the first host compound and the second host compound according to the present disclosure are co-deposited

[0119] Except for using the first host compound and the second host compound in Table 4 below as hosts for the light-emitting layer, OLEDs were fabricated in the same manner as in Device Example 1. Comparative Device Example 4: Preparation of an OLED comprising a comparative compound as a host

[0120] Except for using the first host compound in Table 4 below as a host for the light-emitting layer, an OLED was fabricated in the same manner as in Device Example 10.

[0121] The driving voltage based on a luminance of 1000 nits, the emission color, and the time until the luminous intensity decreases from 100% to 95% (lifetime; T95) based on a luminance of 10,000 nits for the organic electroluminescent devices of Device Comparative Example 4 and Device Examples 10 to 12 fabricated as described above were measured, and the results are shown in Table 4 below. Table 4 First host Second host Driver voltage (V) Emission color Service life T95 (h) Device comparison example 4 H3-1 H2-388 3,0 Red 308 Device example 10 H1-3 H2-388 2,9 Red 372 Device example 11 H1-1 H2-388 3,0 Red 415 Device example 12 H1-2 H2-388 3,0 Red 368

[0122] From Table 4, it can be seen that the organic electroluminescent device comprising the compound of a specific combination according to the present disclosure as host materials has significantly better lifetime characteristics compared to the organic electroluminescent device used as host material in combination with a conventional host compound. Device Example 13: Fabrication of an OLED on which the first host compound and the second host compound according to the present disclosure are co-deposited

[0123] Except for using the first host compound and the second host compound in Table 5 below as hosts for the light-emitting layer, an OLED was fabricated in the same manner as in Device Example 1. Comparative Device Example 5: Preparation of an OLED comprising a comparative compound as a host

[0124] Except for using the first host compound in Table 5 below as a host for the light-emitting layer, an OLED was fabricated in the same manner as in Device Example 13.

[0125] The driving voltage based on a luminance of 1000 nits, the emission color, and the time until the light intensity decreases from 100% to 95% (lifetime; T95) based on a luminance of 10,000 nits for the organic electroluminescent devices of Device Comparative Example 5 and Device Example 13 fabricated as described above were measured, and the results are shown in Table 5 below. Table 5 First host Second host Driver voltage (V) Emission color Service life T95 (h) Device comparison example 5 H3-1 H2-26 3,1 Red 91 Device example 13 H1-4 H2-26 3,1 Red 183

[0126] From Table 5, it can be seen that the organic electroluminescent device comprising the compound of a specific combination according to the present disclosure as a host material has significantly better lifetime characteristics compared to the organic electroluminescent device used as a host material in combination with a conventional host compound. Device Examples 14 and 15: Fabrication of OLEDs on which the second hole transport layer compound is deposited according to the present disclosure

[0127] OLEDs were fabricated in the same manner as in Device Example 1, except that compound HT-4 of Table 7 was used as the first hole injection layer and the first hole transport layer, the compound of Table 6 below was deposited thereon to a thickness of 60 nm as the second hole transport layer, and compound ET-2 was used as the electron transport layer material. Comparative Example 6: Preparation of an OLED comprising a comparative compound as a second hole transport layer

[0128] An OLED was fabricated in the same manner as in Device Example 14, except that the compound of Table 6 below was used as the second hole transport layer.

[0129] The driving voltage based on a luminance of 1000 nits, the emission color, and the time until the light intensity decreases from 100% to 95% (lifetime; T95) based on a luminance of 10,000 nits for the organic electroluminescent devices of Device Comparative Example 6 and Device Examples 14 and 15 prepared as described above were measured, and the results are shown in Table 6 below. Table 6 Second hole transport layer Driver voltage (V) Emission color Service life T95 (h) Device comparison example 6 H3-1 2,9 Red 52 Device example 14 H1-4 2,8 Red 97 Device example 15 H1-6 2,8 Red 78

[0130] From Table 6, it can be seen that the organic electroluminescent device comprising the compound according to the present disclosure as the second hole transport layer material has significantly better lifetime characteristics compared to the organic electroluminescent device using a conventional hole transport material.

[0131] The compounds used in the device examples and comparative device examples are shown in Table 7 below. Table 7 Hole injection layer / hole transport layer Light-emitting layer Electron transport layer / electron injection layer QUOTES CONTAINED IN THE DESCRIPTION

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

[0000] KR 10-2019-0013353

[0005] KR 2017-0022865

[0055] KR 2021-0124018

[0066] KR 10.2021

[0066] KR 2021-0006283

[0066] Cited non-patent literature

[0000] Appl. Phys. Lett. 51, 913, 1987

[0002]

Claims

[1] Several host materials, including: a first host material comprising a compound represented by the following formula 1: where X1 and Y1 each independently represent -N=, -NR5, -O-, or -S-, with the proviso that one of X1 and Y1 is -N= and the other of X1 and Y1 is -NR5-, -O- or -S-; R1 represents a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl or the following formula 1-a: where L1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene or a substituted or unsubstituted (3- to 30-membered) heteroarylene; Ar1 represents a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3- to 30-membered) heteroaryl; Ar2 represents a substituted or unsubstituted (3- to 30-membered) heteroaryl; and R6 each independently represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)-alkyl, a substituted or unsubstituted (C6-C30)-aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30)-cycloalkyl, a substituted or unsubstituted (C1-C30)-alkoxy, a substituted or unsubstituted tri-(C1-C30)-alkylsilyl, a substituted or unsubstituted di-(C1-C30)-alkyl-(C6-C30)-arylsilyl, a substituted or unsubstituted (C1-C30)-alkyldi-(C6-C30)-arylsilyl, a substituted or unsubstituted tri-(C6-C30)-arylsilyl, a substituted or unsubstituted fused ring of an aliphatic (C3-C30) ring and an aromatic (C6-C30) ring, a substituted or unsubstituted mono- or di-(C1-C30)-alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)-arylamino,a substituted or unsubstituted (C1-C30)-alkyl-(C6-C30)-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)heteroarylamino or a substituted or unsubstituted (C6-C30)-aryl-(3- to 30-membered)heteroarylamino or can be linked to an adjacent substituent to form a ring;, R2 to R5 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri-(C1-C30)alkylsilyl, a substituted or unsubstituted di-(C1-C30)alkyl-(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi-(C6-C30)arylsilyl, a substituted or unsubstituted tri-(C6-C30)-arylsilyl, a substituted or unsubstituted fused ring of an aliphatic (C3-C30) ring and an aromatic (C6-C30) ring or the formula 1-a or can be linked to a neighboring substituent to form a ring, with the proviso thatthat at least one of R1 to R5 is represented by formula 1-a;, a and b each independently represent an integer having a value of 1 or 2, and c and d each independently represent an integer from 1 to 4; and then, when a to d represent an integer having a value of 2 or more, each of R2 to R4 and each of R6 may be the same or different, and a second host material comprising a compound represented by the following formula 2: where X2 stands for -O- or -S-; Ring A is a benzene ring or a naphthalene ring; R 21 and R 22each independently represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)-alkyl, a substituted or unsubstituted (C6-C30)-aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30)-cycloalkyl, a substituted or unsubstituted (C1-C30)-alkoxy, a substituted or unsubstituted tri-(C1-C30)-alkylsilyl, a substituted or unsubstituted di-(C1-C30)-alkyl-(C6-C30)-arylsilyl, a substituted or unsubstituted (C1-C30)-alkyldi-(C6-C30)-arylsilyl or a substituted or unsubstituted tri-(C6-C30)-arylsilyl or may be linked to a neighboring substituent to form a ring; L2 represents a single bond, a substituted or unsubstituted (C6-C30)arylene or a substituted or unsubstituted (3- to 30-membered) heteroarylene; HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl containing at least one nitrogen atom; n is an integer from 1 to 5 and m is an integer from 1 to 4; and then, if n and m are an integer with a value of 2 or more, each of R 21 and each of R 22 can be the same or different. [2] A plurality of host materials according to claim 1, wherein the substituted alkyl, the substituted aryl(ene), the substituted heteroaryl, the substituted cycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, the fused ring of a substituted aliphatic ring and aromatic ring, the substituted mono- or dialkylamino, the substituted mono- or diarylamino, the substituted alkylarylamino, the substituted mono- or diheteroarylamino and the substituted arylheteroarylamino are each independently substituted by one or more substituents selected from the group consisting of deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C30)alkyl, Halogen-(C1-C30)-alkyl, (C2-C30)-alkenyl, (C2-C30)-alkynyl, (C1-C30)-alkoxy, (C1-C30)-alkylthio, (C3-C30)-cycloalkyl, (C3-C30)-cycloalkenyl, (3- to 7-membered) Heterocycloalkyl, (C6-C30)-aryloxy, (C6-C30)-arylthio,(5- to 30-membered) heteroaryl which is unsubstituted or substituted by (C6-C30)-aryl, (C6-C30)-aryl which is unsubstituted or substituted by (5- to 30-membered) heteroaryl, tri-(C1-C30)-alkylsilyl, tri-(C6-C30)-arylsilyl, di-(C1-C30)-alkyl-(C6-C30)-arylsilyl, (C1-C30)-alkyldi-(C6-C30)-arylsilyl, a fused ring of an aliphatic (C3-C30) ring and an aromatic (C6-C30) ring, amino, mono- or di-(C1-C30)-alkylamino, substituted or unsubstituted mono- or Di-(C6-C30)-arylamino, (C1-C30)-alkyl-(C6-C30)-arylamino, mono- or di-(3- to 30-membered)heteroarylamino, (C1-C30)-alkyl-(3- to 30-membered)heteroarylamino, (C6-C30)-aryl-(3- to 30-membered) heteroarylamino, (C1-C30)-alkylcarbonyl, (C1-C30)-alkoxycarbonyl, (C6-C30)-arylcarbonyl, (C6-C30)-arylphosphinyl, di-(C6-C30)-arylboronyl, di-(C1-C30)-alkylboronyl, (C1-C30)-alkyl-(C6-C30)-arylboronyl, (C6-C30)-Ar-(C1-C30)-alkyl and (C1-C30)-alkyl-(C6-C30)-aryl are substituted., [3] A plurality of host materials according to claim 1, wherein formula 1 is represented by any one of the following formulas 1-1 to 1-4:wherein c' is an integer from 1 to 3; then, when c' is an integer having a value of 2 or more, each of R4 may be the same or different; and X1, Y1, R1 to R4, R6, L1, Ar1, Ar2 and a to d are as defined in claim 1. [4] A plurality of host materials according to claim 1, wherein Ar2 of formula 1-a is represented by one of the following formulas R-1 to R-4:wherein X is O, S, Se or N; and R 11 to R 18 each independently represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl or a substituted or unsubstituted (C6-C30) aryl. [5] A plurality of host materials according to claim 1, wherein formula 2 is represented by any one of the following formulas 2-1 to 2-16:wherein L3 and L4 can each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene or a substituted or unsubstituted (3- to 30-membered) heteroarylene; Ar3 and Ar4 each independently represent a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered) heteroaryl; X2, R 21 , R 22 , L2, n and m are as defined in claim 1; n' is an integer from 1 to 3; and then, if n' is an integer with a value of 2 or more, each R 21 can be the same or different from each other. [6] A plurality of host materials according to claim 1, wherein the compound represented by formula 1 is selected from the following compounds: [7] A plurality of host materials according to claim 1, wherein the compound represented by formula 2 is selected from the following compounds: [8] An organic electroluminescent device comprising a first electrode, a second electrode, and at least one light-emitting layer between the first electrode and the second electrode, wherein at least one light-emitting layer comprises the plurality of host materials according to claim 1. [9] The organic electroluminescent device according to claim 8, further comprising a hole transport belt disposed between the first electrode and the light-emitting layer, the hole transport belt comprising at least two layers. [10] Organic electroluminescent compound represented by the following formula 1:wherein X1 and Y1 each independently represent -N=, -NR5, -O-, or -S-, with the proviso that one of X1 and Y1 is -N= and the other of X1 and Y1 is -NR5-, -O- or -S-; R1 represents a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl or the following formula 1-a: where L1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene or a substituted or unsubstituted (3- to 30-membered) heteroarylene; Ar1 represents a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3- to 30-membered) heteroaryl; Ar2 represents a substituted or unsubstituted (3- to 30-membered) heteroaryl; and R6 each independently represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)-alkyl, a substituted or unsubstituted (C6-C30)-aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30)-cycloalkyl, a substituted or unsubstituted (C1-C30)-alkoxy, a substituted or unsubstituted tri-(C1-C30)-alkylsilyl, a substituted or unsubstituted di-(C1-C30)-alkyl-(C6-C30)-arylsilyl, a substituted or unsubstituted (C1-C30)-alkyldi-(C6-C30)-arylsilyl, a substituted or unsubstituted tri-(C6-C30)-arylsilyl, a substituted or unsubstituted fused ring of an aliphatic (C3-C30) ring and an aromatic (C6-C30) ring, a substituted or unsubstituted mono- or di-(C1-C30)-alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)-arylamino,a substituted or unsubstituted (C1-C30)-alkyl-(C6-C30)-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)heteroarylamino or a substituted or unsubstituted (C6-C30)-aryl-(3- to 30-membered)heteroarylamino or can be linked to an adjacent substituent to form a ring;, R2 to R5 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri-(C1-C30)alkylsilyl, a substituted or unsubstituted di-(C1-C30)alkyl-(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi-(C6-C30)arylsilyl, a substituted or unsubstituted tri-(C6-C30)-arylsilyl, a substituted or unsubstituted fused ring of an aliphatic (C3-C30) ring and an aromatic (C6-C30) ring or the following formula 1-a or may be linked to a neighboring substituent to form a ring, with the proviso thatthat at least one of R1 to R5 is represented by formula 1-a;, a and b each independently represent an integer having a value of 1 or 2, and c and d each independently represent an integer from 1 to 4; and then, when a to d represent an integer with a value of 2 or more, each of R2 to R4 and each of R6 may be the same or different. [11] The organic electroluminescent compound according to claim 10, wherein formula 1 is represented by any one of the following formulas 1-1 to 1-4:wherein c' is an integer from 1 to 3; then, when c' is an integer having a value of 2 or more, each of R4 may be the same or different; and X1, Y1, R1 to R4, R6, L1, Ar1, Ar2 and a to d are as defined in claim 10. [12] The organic electroluminescent compound according to claim 10, wherein Ar2 in formula 1-a is represented by one of the following formulas R-1 to R-4:wherein X is O, S, Se or N; and R 11 to R 18 each independently represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl or a substituted or unsubstituted (C6-C30) aryl. [13] An organic electroluminescent compound according to claim 10, wherein the compound represented by formula 1 is selected from the following compounds: [14] An organic electroluminescent material comprising the organic electroluminescent compound according to claim 10. [15] An organic electroluminescent device comprising the organic electroluminescent compound of claim 10.

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