Multiple host materials and organic electroluminescent devices containing the same
By using a variety of host materials with specific compounds in an organic electroluminescent device, the problem of insufficient luminescence efficiency and lifetime in the prior art is solved, and an organic electroluminescent effect with a higher efficiency and longer lifetime is achieved.
Patent Information
- Application Number
- CN201980041619.8
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2019-04-18
- Filing Date
- 2019-05-13
- Publication Date
- 2025-05-16
- Estimated Expiration
- 2039-05-13
AI Technical Summary
Existing organic electroluminescent devices have shortcomings in terms of luminescence efficiency and life, and it is difficult to meet the needs of high efficiency and long life.
A variety of host materials including a specific combination of compounds are used, specifically, the first host material consists of a compound represented by Formula 1 and the second host material consists of a compound represented by Formula 2, which are used to constitute the light emitting layer of the organic electroluminescent device.
By using the host material combined with these specific compounds, higher luminescence efficiency and longer lifetime characteristics than conventional organic electroluminescent devices are achieved.
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Abstract
Description
Technical Field
[0001] The present disclosure relates to a variety of host materials and an organic electroluminescent device comprising the same. Background Art
[0002] In 1987, Tang et al. of Eastman Kodak first developed a small molecule green organic electroluminescent device (OLED) consisting of a TPD / Alq3 double layer consisting of a light-emitting layer and a charge transport layer. Since then, research on OLED has been rapidly launched and it has been commercialized. At present, OLED mainly uses phosphorescent materials with excellent luminous efficiency in panel implementation. In addition, the long-term use and high resolution of the display require OLEDs with high luminous efficiency and / or long life.
[0003] Korean Patent Application Publication No. 2017-0022865 discloses a benzoxazole derivative compound for improving OLED performance. However, there is still a need to develop materials for improving OLED performance. Summary of the invention
[0004] Technical issues
[0005] The object of the present disclosure is to provide a variety of host materials comprising specific compound combinations suitable for producing organic electroluminescent devices having higher luminous efficiency and / or longer life characteristics.
[0006] Solution to the problem
[0007] The inventors of the present invention have found that the above objects can be achieved by a plurality of host materials comprising a first host material and a second host material, wherein the first host material comprises a compound represented by the following formula 1, and the second host material comprises a compound represented by the following formula 2:
[0008]
[0009] in,
[0010] Ar represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing at least one of nitrogen, oxygen and sulfur;
[0011] L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group;
[0012] X 1 To X 8each independently represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, -NR 5 R 6 , or -SiR 7 R 8 R 9 ; or X 1 To X 8 Adjacent ones in can be connected to each other to form one or more rings; the premise is that X 1 and X 2 , X 2 and X 3 , X 3 and X 4 , X 4 and X 5 , X 5 and X 6 , X 6 and X 7 , and X 7 and X 8 At least one pair of may be connected to each other to form one or more rings, wherein the ring has 1 to 5 single rings;
[0013] R 5 To R 9 each independently represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3- to 30-membered)heteroaryl; or R 5 To R 9 Adjacent ones of may be connected to each other to form one or more loops; and
[0014]
[0015] in
[0016] X represents -N=, -NR 10 -, -O-, or -S-;
[0017] Y represents -N=, -NR 11 -, -O-, or -S-, provided that when X represents -N=, Y represents -NR 11-, -O-, or -S-, and when X represents -NR 10 -, Y represents -N=, -O-, or -S-;
[0018] HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing one or more nitrogen atoms;
[0019] L 2 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group;
[0020] R 1 represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered)heteroaryl group;
[0021] R 2 To R 4 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl( or R 2 To R 4 Adjacent ones may be connected to each other to form one or more loops;
[0022] R 10 and R 11Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl (C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino;
[0023] a' represents an integer of 1; b' and c' each independently represent an integer of 1 or 2; d' represents an integer of 1 to 4; wherein if b', c', and d' each independently represent an integer of 2 or greater, then R 2 To R 4 Each of can be the same or different.
[0024] Advantageous Effects of the Invention
[0025] By including a specific combination of the compounds disclosed herein as a host material, an organic electroluminescent device having higher luminous efficiency and / or longer life characteristics than conventional organic electroluminescent devices can be provided, and a display system or a lighting system using the organic electroluminescent device can be manufactured. DETAILED DESCRIPTION
[0026] Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present disclosure and is not intended to limit the scope of the present disclosure in any way.
[0027] In the present disclosure, the term "organic electroluminescent material" means a material that can be used for an organic electroluminescent device and can contain at least one compound. If necessary, the organic electroluminescent material can be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, a luminescence auxiliary material, an electron blocking material, a luminescent material (containing a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, and the like.
[0028] In the present disclosure, the term "multiple organic electroluminescent materials" means an organic electroluminescent material as a combination of at least two compounds that can be included in any layer constituting an organic electroluminescent device. It can mean both the material before being included in the organic electroluminescent device (e.g., before vapor deposition) and the material after being included in the organic electroluminescent device (e.g., after vapor deposition). For example, a plurality of organic electroluminescent materials can be a combination of at least two compounds, which can be included in at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a luminescent auxiliary layer, an electron blocking layer, a luminescent layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. At least two compounds can be included in the same layer or in different layers by the method used in the art (e.g., mixed evaporation or co-evaporation, or individually evaporation).
[0029] In the present disclosure, the term "multiple host materials" means an organic electroluminescent material that is a combination of at least two host materials. It may mean both a material before being included in an organic electroluminescent device (e.g., before vapor deposition) and a material after being included in an organic electroluminescent device (e.g., after vapor deposition). The multiple host materials of the present disclosure may be included in any light-emitting layer constituting the organic electroluminescent device. At least two compounds included in the multiple host materials may be included in one light-emitting layer at the same time, or may be included in different light-emitting layers, respectively. If at least two host materials are included in one layer, for example, they may be mixed and evaporated to form a layer, or may be co-evaporated at the same time to form a layer, respectively.
[0030] Here, the term "(C1-C30) alkyl" means a straight or branched alkyl having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 10, and more preferably 1 to 6. The above alkyl groups may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. Here, the term "(C3-C30) cycloalkyl" means a mono- or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The above cycloalkyl groups may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. The term "(3- to 7-membered) heterocycloalkyl" means a cycloalkyl having 3 to 7 ring skeleton atoms and including at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, and preferably the group consisting of O, S, and N. The above heterocycloalkyl can include tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc. The term "(C6-C30) aryl" or "(C6-C30) arylene" means a monocyclic or condensed ring group derived from an aromatic hydrocarbon with 6 to 30 ring skeleton carbon atoms, wherein the ring skeleton carbon atom number is preferably 6 to 20, more preferably 6 to 15. The above aryl or arylene can be partially saturated and can include a spiro structure. The above aryl can include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, peryl, The term "(3- to 50-membered) heteroaryl" or "(3- to 30-membered) heteroarylene" refers to an aryl group having 3 to 50, or 3 to 30 ring skeleton atoms, wherein the number of carbon atoms in the ring skeleton is preferably 3 to 30, more preferably 5 to 20, and includes at least one (preferably 1 to 4) heteroatom selected from the group consisting of B, N, O, S, Si, and P. The above heteroaryl or heteroarylene group may be a monocyclic ring, or a condensed ring condensed with at least one benzene ring; may be partially saturated; may be a heteroaryl or heteroarylene group formed by connecting at least one heteroaryl or aryl group to a heteroaryl group via one or more single bonds; and may contain a spiro structure. The above heteroaryl groups may include monocyclic heteroaryl groups, such as furanyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc.; and condensed ring heteroaryl groups, such as benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophene ... furanyl, benzonaphthofuranyl, dibenzothiophenyl, benzonaphthothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, phenoxazinyl, phenanthridinyl, phenanthro-oxazolyl, benzodioxolyl, etc. In addition, "halogen" includes F, Cl, Br, and I.
[0031] Here, in the expression "substituted or unsubstituted", "substituted" means that a hydrogen atom in some functional group is replaced by another atom or another functional group (i.e., a substituent). 2 , X 1 To X 8 , X 11 To X 33 , and R 1 To R 15wherein the substituents of the substituted alkyl, substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted mono- or di-alkylamino, substituted mono- or di-arylamino, or substituted alkylarylamino are each independently at least one selected from the group consisting of: deuterium; halogen; cyano; carboxyl; nitro ; hydroxy; (C1-C30) alkyl; halo (C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3- to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (3- to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; unsubstituted or substituted by at least one of (C1-C30) alkyl, (C6-C30) aryl, and di(C6-C30) arylamino - to 50-membered) heteroaryl; (C6-C30) aryl unsubstituted or substituted by at least one of cyano, (C1-C30) alkyl, (3- to 50-membered) heteroaryl, di(C6-C30) arylamino and tri(C6-C30) arylsilyl; tri(C1-C30) alkylsilyl; tri(C6-C30) arylsilyl; di(C1-C30) alkyl(C6-C30) arylsilyl; (C1-C30) alkyldi(C6-C30) arylsilyl; amino; mono- or di-(C1-C30) alkyl -C30)alkylamino; mono- or di-(C6-C30)arylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylborylcarbonyl; di(C1-C30)alkylborylcarbonyl; (C1-C30)alkyl(C6-C30)arylborylcarbonyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl. According to one embodiment of the present disclosure, these substituents are each independently at least one selected from the group consisting of: (C1-C20)alkyl; (C6-C25)aryl, unsubstituted or substituted by at least one of one or more (C1-C20)alkyl, one or more (3- to 30-membered)heteroaryl, and one or more di(C6-C25)arylamino; (3- to 30-membered)heteroaryl, unsubstituted or substituted by at least one of one or more (C1-C20)alkyl and one or more di(C6-C25)aryl; and di(C6-C20)arylamino.According to another embodiment of the present disclosure, the substituents are each independently at least one selected from the group consisting of: (C1-C10)alkyl; (C6-C20)aryl, unsubstituted or substituted with at least one of one or more (C1-C10)alkyl and one or more di(C6-C18)arylamino groups; (5- to 25-membered)heteroaryl, unsubstituted or substituted with one or more (C6-C18)aryl groups; and di(C6-C18)arylamino groups. For example, these substituents are each independently at least one methyl group; tert-butyl group; phenyl which is unsubstituted or substituted by at least one of pyridyl, diphenyltriazine, phenylquinoxalinyl, phenylquinazolinyl, biphenylquinazolinyl, dibenzofuranyl, dibenzothiophenyl and diphenylamino; naphthyl which is unsubstituted or substituted by at least one diphenyltriazine; biphenyl; naphthylphenyl; terphenyl; dimethylfluorenyl; phenylfluorenyl; diphenylfluorenyl; dimethylbenzofluorenyl; phenanthrenyl; triazinyl; pyridyl; triazinyl substituted by at least one of phenyl and naphthyl; substituted by at least one phenyl substituted indolyl; benzimidazolyl substituted by at least one phenyl; quinolyl; quinazolinyl substituted by at least one of phenyl and biphenyl; quinoxalinyl substituted by at least one phenyl; unsubstituted or substituted carbazolyl; dibenzofuranyl; dibenzothienyl; benzonaphthothienyl; benzocarbazolyl unsubstituted or substituted by at least one phenyl; dibenzocarbazolyl; triphenylthienyl; diphenylamino; dimethylfluorenylphenylamino; and substituted or unsubstituted (16- to 33-membered) heteroaryl containing at least one of nitrogen, oxygen and sulfur.
[0032] In the formula of the present disclosure, "adjacent ones can be connected to each other to form one or more rings" means that at least two adjacent substituents are connected to each other or fused to form a substituted or unsubstituted mono- or polycyclic (3- to 30-membered), preferably (3- to 26-membered) alicyclic or aromatic ring, or a combination thereof. In addition, the formed ring may contain at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S.
[0033] Here, the heteroaryl group, the heteroarylene group, and the heterocycloalkyl group may each independently contain at least one heteroatom selected from B, N, O, S, Si, and P. In addition, the heteroatom may be bonded to at least one selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, and substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino.
[0034] In Formula 1, Ar represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing at least one of nitrogen, oxygen and sulfur. According to one embodiment of the present disclosure, Ar represents a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5- to 25-membered) heteroaryl group containing at least one of nitrogen, oxygen and sulfur. According to another embodiment of the present disclosure, Ar represents an unsubstituted or (C6-C18) aryl group substituted with one or more (C1-C30) alkyl groups, or an unsubstituted or (C6-C18) aryl group substituted with one or more (C6-C18) aryl groups and containing nitrogen, oxygen and sulfur (5- to 20-membered) heteroaryl groups. Specifically, Ar represents substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted triphenylene radical, substituted or unsubstituted benzonaphthofuranyl, or substituted or unsubstituted benzonaphthothiophenyl. For example, Ar can represent phenyl, naphthyl, biphenyl, terphenyl, dimethylfluorenyl, dimethylbenzofluorenyl, triphenylene radical, dibenzofuranyl, dibenzothiophenyl, unsubstituted or carbazolyl substituted with one or more phenyl groups, or benzonaphthofuranyl.
[0035] In formula 1, L 1represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group. According to one embodiment of the present disclosure, L 1 represents a single bond, a substituted or unsubstituted (C6-C25)arylene group, or a substituted or unsubstituted (5- to 25-membered)heteroarylene group. According to another embodiment of the present disclosure, L 1 represents a single bond, an unsubstituted (C6-C18)arylene group, or an unsubstituted (5- to 20-membered)heteroarylene group. 1 It may represent a single bond, phenylene, naphthylene, biphenylene, or phenanthroxazolylene.
[0036] In formula 1, X 1 To X 8 each independently represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, -NR 5 R 6 , or -SiR 7 R 8 R 9 ; or X 1 To X 8 Adjacent ones in can be connected to each other to form one or more rings; the premise is that X 1 and X 2 , X 2 and X 3 , X 3 and X 4 , X 4 and X 5 , X 5 and X 6 , X 6 and X 7 , and X 7 and X 8 At least one pair of X can be connected to each other to form one or more rings, wherein the ring has 1 to 5 single rings. According to one embodiment of the present disclosure, X 1 To X 8 Each independently represents hydrogen; or X 1 and X 2 , X 2 and X 3 , X 3 and X 4 , X 4 and X 5 , X5 and X 6 , X 6 and X 7 , and X 7 and X 8 At least one pair of X may be connected to each other to form one or more rings, wherein the ring has 1 to 5 monocycles, preferably 2 to 5 monocycles. 1 and X 2 Each other is connected to form an indole ring, wherein the ring has 2 monocyclic rings. The ring may be a substituted or unsubstituted mono- or polycyclic (3- to 30-membered) aliphatic or aromatic ring, or a combination thereof; preferably a substituted or unsubstituted mono- or polycyclic (3- to 20-membered) aliphatic or aromatic ring, or a combination thereof; and more preferably a substituted or unsubstituted monocyclic (3- to 8-membered) aromatic ring. Specifically, the ring may be a ring in which 1 to 5 monocyclic rings, preferably 2 to 5 monocyclic rings, are fused. In addition, the ring may contain at least one heteroatom selected from B, N, O, S, Si and P; preferably, at least one heteroatom selected from N, O, and S; and more preferably, at least one heteroatom selected from N and S. When X 1 To X 8 When X can be connected to adjacent substituents to form a ring, the compound represented by Formula 1 may be a fused carbazole-based compound, a fused azulene-based compound, etc. For example, 1 To X 8 Each independently represents hydrogen; or may be connected to one or more adjacent substituents to form a benzene ring, an indole ring substituted with one or more phenyl groups and / or one or more biphenyl groups, a benzothiophene ring, a benzoindole ring substituted with at least one of one or more phenyl groups and one or more naphthyl groups, a 15-membered polycyclic ring, a nitrogen-containing 18-membered polycyclic ring, or a nitrogen-containing 22-membered polycyclic ring.
[0037] R 5 To R 9 each independently represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3- to 30-membered)heteroaryl; or R 5 To R 9 Adjacent ones may be connected to each other to form one or more rings.
[0038] According to one embodiment of the present disclosure, Formula 1 may be represented by any one of the following Formulas 1-1 to 1-10.
[0039]
[0040]
[0041] In Formulae 1-1 to 1-10, the substituents are defined as follows.
[0042] Ar and L 1 is defined as in Formula 1.
[0043] V and W each independently represent CR 12 R 13 NR 14 , O, or S. According to one embodiment of the present disclosure, V and W each independently represent NR 14 , O, or S. For example, V can represent NR 14 or S, and W can represent S.
[0044] R 12 To R 14 , X 11 To X 23 , and X 31 To X 33 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl (C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino.
[0045] According to one embodiment of the present disclosure, R 12 To R 14 Each independently represents a substituted or unsubstituted (C1-C20) alkyl group, a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5- to 25-membered) heteroaryl group. According to another embodiment of the present disclosure, R 12 To R 14 Each independently represents an unsubstituted (C6-C18) aryl group. 12 To R 14 Each independently may represent a phenyl group or a biphenyl group.
[0046] According to one embodiment of the present disclosure, X 11To X 23 , and X 31 To X 33 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5- to 25-membered) heteroaryl. According to another embodiment of the present disclosure, X 11 To X 23 , and X 31 To X 33 Each independently represents hydrogen, deuterium, or unsubstituted (C6-C18)aryl. 11 To X 23 , and X 31 To X 33 Each independently may represent hydrogen or phenyl.
[0047] X 24 To X 30 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl( or X 24 To X 30 Adjacent ones in X can be connected to each other to form one or more rings. According to one embodiment of the present disclosure, X 24 To X 30 each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C20)alkyl, substituted or unsubstituted (C6-C25)aryl, or substituted or unsubstituted (5- to 25-membered)heteroaryl; or X 24 To X 30 Adjacent ones in X can be connected to each other to form one or more rings. According to another embodiment of the present disclosure, X 24 To X 30 Each independently represents hydrogen, deuterium, or unsubstituted (C6-C18)aryl; or X 24 To X 30 Adjacent ones in X can be connected to each other to form one or more rings. 24 To X30 Each independently represents hydrogen; or X 24 To X 30 Adjacent ones may be connected to each other to form a benzene ring.
[0048] a, e to i, k, 1, o, p, s, u, y, and z each independently represent an integer of 1 to 4; b to d, j, and m each independently represent an integer of 1 to 6; n and r each independently represent an integer of 1 to 3; q represents an integer of 1 or 2; t represents an integer of 1 to 5; in the case where a to u, y, and z each independently represent an integer of 2 or more, X 11 To X 33 Each of can be the same or different.
[0049] In Formula 2, X represents -N=, -NR 10 -, -O-, or -S-; Y represents -N=, -NR 11 -, -O-, or -S-; provided that when X represents -N=, then Y represents -NR 11 -, -O-, or -S-, and when X represents -NR 10 -, then Y represents -N=, -O-, or -S-. According to one embodiment of the present disclosure, X represents -N=, -NR 10 -, -O-, or -S-; Y represents -N=, -NR 11 -, -O-, or -S-; provided that either X or Y represents -N=.
[0050] R 10 and R 11 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino. According to one embodiment of the present disclosure, R 10 and R 11Each independently represents a substituted or unsubstituted (C1-C20) alkyl group, a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5- to 25-membered) heteroaryl group. According to another embodiment of the present disclosure, R 10 and R 11 Each independently represents an unsubstituted (C6-C18) aryl group. 10 and R 11 It may be phenyl.
[0051] In Formula 2, HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing one or more nitrogen atoms. According to one embodiment of the present disclosure, HAr represents a substituted or unsubstituted (5- to 25-membered) heteroaryl group containing one or more nitrogen atoms. According to another embodiment of the present disclosure, HAr represents a (5- to 20-membered) heteroaryl group containing one or more nitrogen atoms, unsubstituted or substituted by one or more (5- to 25-membered) heteroaryl groups and / or one or more (C6-C25) aryl groups. Specifically, HAr represents a substituted or unsubstituted triazinyl, a substituted or unsubstituted pyridinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted benzoquinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted benzoquinoxalinyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted benzoquinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted benzoisoquinolyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted naphthyridinyl, or a substituted or unsubstituted benzothienopyrimidinyl. For example, HAr may represent a substituted triazinyl, a substituted pyrimidinyl, a substituted quinoxalinyl, a substituted quinazolinyl, or a substituted naphthyridinyl. The substituents of these substituted triazine groups, substituted pyrimidinyl groups, substituted quinoxalinyl groups, substituted quinazoline groups, and substituted naphthyridinyl groups may be at least one of unsubstituted or substituted phenyl, naphthyl, biphenyl, dimethylfluorenyl, dimethylbenzofluorenyl, dibenzothiophenyl, dibenzofuranyl, benzonaphthothiophenyl, phenylcarbazolyl, and phenylbenzocarbazolyl groups.
[0052] In formula 2, L 2 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group. According to one embodiment of the present disclosure, L 2 represents a single bond, a substituted or unsubstituted (C6-C25)arylene group, or a substituted or unsubstituted (5- to 25-membered)heteroarylene group. According to another embodiment of the present disclosure, L 2 represents a single bond, an unsubstituted (C6-C18)arylene group, or an unsubstituted (5- to 20-membered)heteroarylene group. 2It may represent a single bond, a phenylene group, or a pyridylene group.
[0053] In formula 2, R 1 represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group. According to one embodiment of the present disclosure, R 1 represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (5- to 25-membered) heteroaryl group. According to another embodiment of the present disclosure, R 1 represents an unsubstituted or (C6-C29)aryl group substituted by one or more (C1-C10)alkyl groups and / or one or more (C6-C18)aryl groups; or an unsubstituted or (5- to 25-membered) heteroaryl group substituted by one or more (C6-C18)aryl groups. For example, R 1 It may be phenyl, naphthyl, phenylnaphthyl, biphenyl, dimethylfluorenyl, dimethylbenzofluorenyl, spirobifluorenyl, spiro[fluorene-benzofluorenyl]yl, phenylcarbazolyl, phenylbenzocarbazolyl, dibenzofuranyl, or dibenzothiophenyl.
[0054] In formula 2, R 2 To R 4 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl( or R 2 To R 4 Adjacent ones in R can be connected to each other to form one or more rings. 2 To R 4 It may be hydrogen.
[0055] In Formula 2, a' represents an integer of 1; b' and c' each independently represent an integer of 1 or 2; d' represents an integer of 1 to 4; wherein if b', c', and d' each independently represent an integer of 2 or greater, then R 2 To R 4 Each of can be the same or different.
[0056] According to one embodiment of the present disclosure, Formula 2 may be represented by any one of the following Formulas 2-1 and 2-2.
[0057]
[0058] In formulas 2-1 and 2-2, X, Y, and R 1 To R 4 , L 2 , and a′ to d′ are defined as in Formula 2.
[0059] In formulas 2-1 and 2-2, Y 1 To Y 5 , and Y 11 To Y 17 Each independently represents N or CR 15 According to one embodiment of the present disclosure, Y 1 To Y 5 At least one of the CR 15 , and Y 11 To Y 17 At least one of the CR 15 .
[0060] R 15 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl( or R 15 Adjacent ones in R can be connected to each other to form one or more rings. According to one embodiment of the present disclosure, R 15 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5- to 25-membered) heteroaryl. According to another embodiment of the present disclosure, R 15Each independently represents hydrogen; deuterium; (C6-C18)aryl which is unsubstituted or substituted by one or more (C1-C10)alkyl and / or one or more di(C6-C18)arylamino groups; or (5- to 20-membered) heteroaryl which is unsubstituted or substituted by one or more (C6-C18)aryl groups. For example, R 15 Each may independently represent hydrogen, unsubstituted or substituted phenyl with one or more diphenylamino groups, naphthyl, biphenyl, dimethylfluorenyl, dimethylbenzofluorenyl, dibenzothienyl, dibenzofuranyl, benzonaphthothienyl, phenylcarbazolyl, or phenylbenzocarbazolyl.
[0061] The compound represented by Formula 1 includes the following compounds, but is not limited thereto.
[0062]
[0063]
[0064]
[0065]
[0066]
[0067] The compound represented by Formula 2 includes the following compounds, but is not limited thereto.
[0068]
[0069]
[0070]
[0071]
[0072]
[0073]
[0074] A combination of at least one of Compounds C1-1 to C1-94 and at least one of Compounds C2-1 to C2-125 can be used in an organic electroluminescent device.
[0075] The compound represented by Formula 1 according to the present disclosure may be prepared by a synthetic method known to those skilled in the art. For example, the compound represented by Formula 1 can be prepared by referring to the following reaction scheme 1 and the following: Korean Patent Application Publication Nos. 2015-0135109 A (published on December 2, 2015), 2015-0032447 A (published on March 26, 2015), 2016-0099471 A (published on August 22, 2016), 2018-0012709 A (published on February 6, 2018), 2012-0132815 A (published on December 10, 2012), 2015-0077513 A (published on July 8, 2015), and 2017-0129599A (published on November 27, 2017), and Korean Patent No. 1478990 B (published on December 29, 2014), but are not limited thereto.
[0076] [Reaction Scheme 1]
[0077]
[0078] In reaction scheme 1, Ar, L 1 , X 28 To X 30 , r, s, and t are as defined above in Formulas 1-9.
[0079] The compound represented by Formula 2 according to the present disclosure can be prepared by a synthesis method known to those skilled in the art. For example, the compound represented by Formula 2 can be prepared by referring to Korean Patent Application Publication No. 2017-0022865 A (published on March 2, 2017), but is not limited thereto.
[0080] The organic electroluminescent device according to the present disclosure comprises an anode, a cathode, and at least one organic layer between the anode and the cathode. The organic layer may comprise a plurality of organic electroluminescent materials, wherein the compound represented by Formula 1 is included as the first organic electroluminescent material, and the compound represented by Formula 2 is included as the second organic electroluminescent material. According to one embodiment of the present disclosure, the organic electroluminescent device comprises an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, and at least one layer of the at least one light-emitting layer comprises a compound represented by Formula 1 and a compound represented by Formula 2.
[0081] The light-emitting layer comprises a host and a dopant. The host comprises a plurality of host materials. A compound represented by Formula 1 may be included as a first host compound among the plurality of host materials, and a compound represented by Formula 2 may be included as a second host compound among the plurality of host materials. The weight ratio of the first host compound to the second host compound is in the range of about 1:99 to about 99:1, preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30, even more preferably about 40:60 to 60:40, and still more preferably about 50:50.
[0082] The light-emitting layer is a layer from which light is emitted, and may be a single layer or a multilayer in which two or more layers are stacked. In the various host materials according to the present disclosure, the first and second host materials may be simultaneously contained in one layer or may be respectively contained in different light-emitting layers. According to one embodiment of the present disclosure, the doping concentration of the dopant compound relative to the host compound in the light-emitting layer is less than 20wt%.
[0083] The organic electroluminescent device of the present disclosure may further include at least one layer selected from the following: a hole injection layer, a hole transport layer, a hole auxiliary layer, a luminescent auxiliary layer, an electron transport layer, an electron injection layer, an intermediate layer, an electron buffer layer, a hole blocking layer, and an electron blocking layer. According to one embodiment of the present disclosure, the organic electroluminescent device may further include an amine-based compound other than the various host materials of the present disclosure as at least one of the hole injection material, the hole transport material, the hole auxiliary material, the luminescent material, the luminescent auxiliary material, and the electron blocking material. In addition, according to one embodiment of the present disclosure, the organic electroluminescent device may further include an azine-based compound other than the various host materials of the present disclosure as at least one of the electron transport material, the electron injection material, the electron buffer material, and the hole blocking material.
[0084] The dopant included in the organic electroluminescent device of the present disclosure may be at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant material is not particularly limited, but may be preferably selected from metallized complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably ortho-metallized complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably ortho-metallized iridium complex compounds.
[0085] The dopant compound included in the organic electroluminescent device of the present disclosure may include a compound represented by the following Formula 101, but is not limited thereto.
[0086]
[0087] In Formula 101, L is selected from the following structures 1 and 2:
[0088]
[0089] R 100 To R 103 Each independently represents hydrogen, deuterium, halogen, unsubstituted or substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3- to 30-membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; or may be connected to an adjacent R 100 To R 103 The pyridine and substituted or unsubstituted quinoline rings are combined to form one or more rings, such as substituted or unsubstituted quinoline, substituted or unsubstituted benzofuranopyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuranoquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenoquinoline rings;
[0090] R 104 To R 107 Each independently represents hydrogen, deuterium, halogen, unsubstituted or substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or may be connected to an adjacent R 104 To R 107 Together with benzene, the above-mentioned amines form one or more rings, such as substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuranopyridine, or substituted or unsubstituted benzothienopyridine rings;
[0091] R 201 To R 211 Each independently represents hydrogen, deuterium, halogen, unsubstituted or substituted by deuterium and / or one or more halogen (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl; or may be connected to an adjacent R 201 To R 211 to form a ring; and
[0092] n' represents an integer from 1 to 3.
[0093] Specific examples of the dopant compound are as follows, but are not limited thereto.
[0094]
[0095]
[0096]
[0097]
[0098] To form each layer of the organic electroluminescent device of the present disclosure, a dry film forming method such as vacuum evaporation, sputtering, plasma and ion plating methods, or a wet film forming method such as inkjet printing, nozzle printing, slit coating, spin coating, dip coating, and flow coating methods can be used.
[0099] When a solvent is used in the wet film formation method, a thin film can be formed by dissolving or diffusing the materials forming each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent may be any solvent in which the materials forming each layer can be dissolved or diffused and in which there is no problem in film forming ability.
[0100] In addition, the compound represented by Formula 1 and the compound represented by Formula 2 can be subjected to film formation in the above-listed methods, usually by a co-evaporation method or a mixed evaporation method. Co-evaporation is a mixed deposition method in which two or more materials are placed in a corresponding single crucible source and current is applied to two chambers at the same time to evaporate the materials. Mixed evaporation is a mixed deposition method in which two or more materials are mixed in a crucible source before evaporation and current is applied to the chamber to evaporate the materials.
[0101] The present disclosure can provide a display system by including multiple host materials. In addition, it is possible to produce a display system or a lighting system by using the organic electroluminescent device of the present disclosure. Specifically, it is possible to produce a display system, such as a display system for a smart phone, a tablet computer, a notebook, a PC, a TV, or a car, or to produce a lighting system, such as an outdoor or indoor lighting system, by using multiple host materials of the present disclosure.
[0102] Hereinafter, the luminous efficiency and lifespan characteristics of the OLED according to the present disclosure will be explained. However, the following examples only explain the characteristics of the OLED according to the present disclosure in detail, but the present disclosure is not limited to the following examples.
[0103] Device Examples 1, 2, and 5 to 12: Fabrication of OLEDs by co-evaporation of first and second host compounds according to the present disclosure
[0104] The OLED according to the present disclosure was produced as follows: a transparent electrode indium tin oxide (ITO) thin film (10Ω / sq) (GEOMATEC CO., LTD., Japan) on a glass substrate for OLED was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water in sequence, and then stored in isopropyl alcohol. The ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 was introduced into a chamber of the vacuum vapor deposition apparatus, and the pressure in the chamber of the apparatus was then controlled to 10 -6 Support. Thereafter, an electric current is applied to the chamber to evaporate the above introduced materials, thereby forming a first hole injection layer with a thickness of 80nm on the ITO substrate. Compound HI-2 is then introduced into another chamber of the vacuum vapor deposition device, and evaporated by applying an electric current to the chamber, thereby forming a second hole injection layer with a thickness of 5nm on the first hole injection layer. Compound HT-1 is then introduced into another chamber of the vacuum vapor deposition device, and evaporated by applying an electric current to the chamber, thereby forming a first hole transport layer with a thickness of 10nm on the second hole injection layer. Compound HT-2 is then introduced into another chamber of the vacuum vapor deposition device, and evaporated by applying an electric current to the chamber, thereby forming a second hole transport layer with a thickness of 60nm on the first hole transport layer. After forming these hole injection layers and hole transport layers, a light-emitting layer is formed thereon as follows: the first host compound and the second host compound shown in Table 1 are respectively introduced into two chambers of the vacuum vapor deposition device as the main body, and compound D-39 is introduced into another chamber as a dopant. The two host materials are evaporated at a rate of 1:1, and the dopant material is evaporated at different rates simultaneously, and a doping amount of 3wt% based on the total amount of the host and the dopant is deposited to form a light-emitting layer with a thickness of 40nm on the second hole transport layer. Then, compound ET-1 and compound EI-1 are evaporated at a rate of 1:1 in two other chambers to deposit an electron transport layer with a thickness of 35nm on the light-emitting layer. After compound EI-1 is deposited on the electron transport layer as an electron injection layer with a thickness of 2nm, an Al cathode with a thickness of 80nm is deposited on the electron injection layer by another vacuum vapor deposition device. Thus, an OLED is produced.
[0105] Device Example 3: Fabrication of an OLED by mixed evaporation of first and second host compounds according to the present disclosure
[0106] An OLED was produced in the same manner as in Device Example 2, except that the first host compound and the second host compound described in Table 1 were deposited in one chamber of the vacuum deposition apparatus instead of two chambers.
[0107] Device Example 4: Fabrication of an OLED by co-evaporation of first and second host compounds according to the present disclosure
[0108] An OLED was produced in the same manner as in Device Example 2, except that Compound D-78 was used as a dopant instead of Compound D-39.
[0109] Comparative Examples 1 and 2: OLEDs manufactured without following the present disclosure
[0110] An OLED was produced in the same manner as in Device Example 1, except that only the second host compound described in the following Table 1 was used instead of the two hosts.
[0111] Results of luminous efficiency at a luminance of 5,000 nits and time taken for 100% initial luminance to decrease to 97% luminance at a luminance of 5,000 nits under a constant current (T97) for OLEDs produced in the device examples and comparative examples are shown in Table 1 below.
[0112] [Table 1]
[0113]
[0114] It can be confirmed from Table 1 that the organic electroluminescent device including the specific compound combination according to the present disclosure as a host material has higher luminous efficiency and / or longer life characteristics than conventional organic electroluminescent devices.
[0115] The compounds used in the device examples and comparative examples are provided in Table 2 below.
[0116] [Table 2]
[0117]
Claims
1. A plurality of host materials, the plurality of host materials comprising a first host material and a second host material, wherein the first host material comprises a compound represented by the following Formula 1: in, Ar represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing at least one of nitrogen, oxygen and sulfur; wherein the (3- to 30-membered) heteroaryl group in Ar represents a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group L1 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene group; X1 to X8 each independently represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, -NR5R6, or -SiR7R8R9; or adjacent ones of X1 to X8 may be connected to each other to form one or more rings; provided that at least one pair of X1 and X2, X2 and X3, X3 and X4, X4 and X5, X5 and X6, X6 and X7, and X7 and X8 may be connected to each other to form one or more rings, wherein the ring has 1 to 5 monocyclic rings; R5 to R9 each independently represent hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3- to 30-membered)heteroaryl; or adjacent ones of R5 to R9 may be linked to each other to form one or more rings; and The second host material includes a compound represented by the following formula 2-1: in, X means -N=; Y represents -O-; Y2 and Y4 represent N; Y1, Y3 and Y5 each independently represent CR 15 ; R in Y1 15 represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group; R in Y3 and Y5 15 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl (C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; L2 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group; R1 represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; R2 to R4 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) aryl silyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or adjacent ones of R2 to R4 may be linked to each other to form one or more rings; a' represents an integer of 1; b' and c' each independently represent an integer of 1 or 2; d' represents an integer of 1 to 4; wherein if b', c', and d' are each independently an integer of 2 or more, each of R2 to R4 may be the same or different.
2. The plurality of host materials according to claim 1, wherein: In Ar, L1, X1 to X8, R1 to R9, R 15 The substituents of the substituted aryl, the substituted arylene, the substituted heteroaryl, the substituted heteroarylene, the substituted alkyl, the substituted cycloalkyl, the substituted cycloalkenyl, the substituted heterocycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, the substituted mono- or di-alkylamino, the substituted mono- or di-arylamino, or the substituted alkylarylamino in , HAr, and L2 are each independently at least one selected from the group consisting of: deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; (C1-C30) alkyl; halo (C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3- to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) aryl thio; (3- to 50-membered) heteroaryl which is unsubstituted or substituted by at least one of (C1-C30) alkyl, (C6-C30) aryl, and di(C6-C30) arylamino; (C6-C30) alkyl which is unsubstituted or substituted by at least one of cyano, (C1-C30) alkyl, (3- to 50-membered) heteroaryl, di(C6-C30) arylamino, and tri(C6-C30) arylsilyl; 30) aryl; tri(C1-C30) alkylsilyl; tri(C6-C30) arylsilyl; di(C1-C30) alkyl(C6-C30) arylsilyl; (C1-C30) alkyldi(C6-C30) arylsilyl; amino; mono- or di-(C1-C30) alkylamino; mono- or di-(C6-C30) arylamino; (C1-C30) alkyl(C6-C3 0)arylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylborylcarbonyl; di(C1-C30)alkylborylcarbonyl; (C1-C30)alkyl(C6-C30)arylborylcarbonyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl.
3. The plurality of host materials according to claim 1, wherein: This formula 1 is represented by any one of the following formulas 1-1 to 1-10: in, Ar and L1 are as defined in claim 1; V and W each independently represent CR 12 R 13 NR 14 , O, or S; R 12 To R 14 , X 11 To X 23 , and X 31 To X 33 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl (C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; X 24 To X 30 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl( or X 24 To X 30 Adjacent ones of may be connected to each other to form one or more loops; and a, e to i, k, l, o, p, s, u, y, and z each independently represent an integer of 1 to 4; b to d, j, and m each independently represent an integer of 1 to 6; n and r each independently represent an integer of 1 to 3; q represents an integer of 1 or 2; t represents an integer of 1 to 5; in the case where a to u, y, and z each independently represent an integer of 2 or more, X 11 To X 33 Each of can be the same or different.
4. The plurality of host materials according to claim 1, wherein: Ar represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group.
5. The plurality of host materials according to claim 1, wherein: The compound represented by Formula 1 is at least one selected from the group consisting of the following compounds:
6. The plurality of host materials according to claim 1, wherein: The compound represented by Formula 2-1 is at least one selected from the group consisting of the following compounds:
7. An organic electroluminescent device comprising an anode, a cathode and at least one light-emitting layer between the anode and the cathode, wherein: At least one of the light-emitting layers comprises a plurality of host materials according to claim 1 .
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